"I think our Lilly is in love, "Marci taunted me gently, "or else she got laid last night. Do you have a boyfriend now, sweetie?"
I just gave her a big hug and said, "Maybe it's just all those female hormones flooding my helpless brain, or maybe I learned that people can care for me."
"Oh shit, I better get you to employee health, I think you must have had a stroke, or estrogen poisoning, or something."
On Monday morning I arrived at work thirty minutes earlier than usual. Cynthia and I had decided that our relationship had to remain secret and so we wouldn't arrive at work or leave there together. She was usually in before me, but since I was essentially the office girl now, I had to get the coffee ready for everyone else.
I was wearing my standard suit and tie, the only differences from the week before were my new haircut (I blew it out so it hung by my face, rather than using mousse to comb it back - I liked it this way the best), neatly manicured (though now colorless) nails, and the two studs in each of my ears. Oh yeah, the eyebrows, almost forgot about the eyebrows, their shape was the feature that most clearly revealed my life's new direction. They really made my face look girlish.
Of course, I was wearing lingerie as well, and Cynthia had added a corset. But I had long worn lingerie on my own, so only the corset was new, new and uncomfortable. My waist started off that morning at not quite 30 inches. She vowed it was going to be a lot smaller than that real soon and tightened me until I was more than two inches smaller. I liked how I looked, but hated how I felt.
Then the door opened and as I turned to see who was there I heard a gasp. It was Heather Wilkes staring at me like I had just arrived from outer space. She looked searchingly at my face and said, "turn your head, I want to see your ears".
I flipped the hair out of my eyes and brushed it behind my ear with my fingers. I turned my head so she could see my studs. "Two piercings, cool. Get my coffee and bring it to my desk."
"Yes Miss Wilkes."
She threw me her jacket, "hang it up," then turned and left the break room. Before I could get her coffee, Betsy and Sylvia showed up. Betsy was agog, Sylvia just appraised me coolly, like I was a piece of spoiled meat at the butcher counter.
"You really are a little pansy aren't you? As a girl you might be cute, but as a guy, you're pitiful." She spit that out. "No man would let this happen to him. Don't you have any pride at all?"
What a bitch! "Yes Sylvia," I said as evenly as I could. Then I flicked my hair to the side and looked right at her. "I have pride, but one thing that all this has finally forced me come to terms with is that I'm really a girl, a woman, I'm not a man. I never was. I'm going to transition. This," I ran my fingers through my hair and shook it out, flipping it back away from my eyes again, "is just the first small step." Before she could say anything else, I added, "I'm glad to hear you think I might end up being cute. Would you like coffee?"
I held up her cup in a conciliatory gesture. A giggle spluttered out of Betsy's mouth and through the fingers she had pressed to her lips to try to prevent just that. Her eyes went wide with embarrassment, and both Sylvia and I knew Betsy was laughing at her and not me.
"Give me my coffee, you little bitch," she spit the words into my face, barely able to contain her anger, and you better make sure I don't run out."
"Yes, Mrs. Denton." I poured quickly. "May I take your coat?"
"No, I'll keep it."
I turned to Betsy. "I'll be right back. I have to take this to Heather. I held up her cup.
When I got back she was sitting at our small table, her fingers wrapped around a coffee cup that already had a lipstick stain on it. "Sit with me for a moment," she said, looking up into my face. I sat.
"Did Cynthia do this to you?"
Cynthia and I had already decided what I would say. "No, I did it. Once everyone in the office had seen my shaved body and panties, there didn't seem to be any more point in keeping who I was a secret. I've wanted to do this for a long time. This is my silver lining for the dark cloud that Cynthia created for me last week."
"Holy shit, I never would have guessed." Then she reached out her hand and ran it through the longish hair. She fingered the two studs in my right ear, and traced the arch of my eyebrow. "Good luck, honey, you're going to need it. By the way, what's your name?"
"Lilly, well Lillian" I said quietly, Cynthia had given me permission to use her grandmother's name, but retained the right to retract it if I misbehaved.
"How sweet." She reached out her right hand, angled downwards to shake mine. I grabbed it as gently as I could, using only my fingers. "Nice to meet you Lillian, maybe we can become friends."
Instead of dropping it right away after we had shaken, I held her hand in mine as if it was a valuable object. Then I looked up into her eyes. "Thank you Betsy, I'd like that."
"That's a beautiful ring, where did you get it?"
"From a dear friend."
"Wow, she...." she stopped suddenly and looked at me questioningly, "he?"
"She..."
"She must really like you."
I just nodded my head.
By 8:30 everyone was in and no one was working, People just had to talk about me. Cynthia called me into her office. She closed the door and we stood behind it. "How'd it go?"
"Well, just fine actually, Miss Morrison. Sylvia was a little nasty, but everyone else has been fine with this." I pointed to my face. Betsy asked my name. I told her it was Lillian.
"That's OK, honey, it wouldn't do to have people calling you Sissy" she whispered it with an exaggerated hiss, "in the office. I think I had better go talk to the girls or they'll never get any work done. You need to talk to Thornton. I had Kathleen call him, he's waiting for you now. He only knows it's something personal. This part will be easy, don't worry."
I started to get really scared. "Cyn...Ms. Morrison, I can't...this is all going too fast. I'm not sure I want..."
She cut me off. "SHUT UP, you little twit. You seem to have forgotten. You don't have a CHOICE."
"But you're turning me into a girl. You can't just take over my life and turn me into a girl."
"You seem to have forgotten last week already" Her voice had a hard edge that made me cringe. "I can turn you into some serial rapist's prison wife, if I want to." Then she lowered her voice and took my hand. "Besides you want this to happen. Just relax and go with the flow. You'll love it." She swatted my butt. "Now, off you go." She said that with a singsong rhythm in her voice, like mothers use with their toddlers.
Fear and longing battled within me. I was pleased she was telling me what to do, but I just couldn't give up control over my own life. I hated having to take care of myself, but was afraid to let anyone else do it. How's that for a conflict? So, I got ready to leave, but a feeling of foreboding was growing within me. I said, "yes Mistress, is there anything else Mistress?"
"Come to mommy," she said. I stepped forward and she enveloped me in a big, warm hug, holding me to her chest for a few moments. Then she pulled back and gently grabbed my head in both of her hands. "Don't agonize so, Lilly, I'm in charge now, I'll take care of you. Trust me." Then she put one hand on my shoulder, turned me towards the door, and swatted me on the butt again. "Now scoot."
I gave her a wan smile, flipped my hair off my eyes, and left. As I walked to Thornton's office, a memory from my childhood came back to me. My father was an abusive drunk. When I was nine he disappeared for several months without any warning. I had tried to stand up to him that morning when he was yelling at my mother.
He just shouted me down. "Don't make me do anything you'll regret, you little pansy. You're not big enough to stand up to a Girl Scout. You're no man. You're not worth the effort it takes to raise you."
I was too skinny and too short. He always accused me of being a girl when he got mad at me. He sneered when he said it. Weeks later, my mother found me crying on the couch. Using kiddies logic, I had concluded that dad had left because of me. I wasn't worth raising, so he left. My mother hugged me for a few moments and then told me, "I'm in charge now, I'll take care of you. Trust me."
My mother betrayed my trust more times than I could count. She took care of me only rarely. She generally treated me like I was in her way, especially after my father died and she went on the prowl for men, which was often. There were many nights when she assured me she would be home by 11:00 or 12:00 or whenever, but didn't come home at all. I would lie in my bed listening to sirens. I was sure they were ambulances that were taking her to the hospital... or the morgue. I hated her for the way she treated me, but was scared to death that something would happen to her, as it had to my father. On nights like that, I drifted off only when sleep finally overtook my emotionally exhausted brain.
I longed to trust my mother, longed terribly to be able to do that, but over time, she taught me that I couldn't. I longed to have her take care of me, to hold me to her breast and comfort me, but she rarely did. Over the next 5 years or so, it was I who had to take care of her. I did everything I could think of to make her love me, but nothing seemed to work. I got to college still looking for someone I could trust. Had I finally found that person, or was Cynthia going to betray me too?
All of a sudden, I found myself in front of Thornton's office. I composed myself, smiled grimly, tossed my hair out of my face, and went in. His administrative assistant, Tammy Wright, glanced up briefly and started to say, "He'll be with you in a minute Mr. Miller...." and then the new me actually registered in her brain. She stared for a few moments and then nodded to the couch across the room from her desk. "Or is it Ms. Miller now?" she asked sarcastically.
"Not yet," I said coldly, "but keep watching this space."
I looked directly at her, until she looked away, embarrassed by her own staring. We fell into an awkward silence and she went back to her work. Thornton treated her quite badly, but instead of turning to the other people who worked at North State for help and support, she herself treated us just like Thornton did. Ten minutes later he buzzed for me.
Cynthia had been right. Thornton was friendly and professional, though obviously curious as well. He heard me out, told me he hoped it wouldn't affect my work, and that we would see what we would see. He complimented me on my lovely ring. I left to walk back to my office.
As I opened the door to the hallway, Tammy said, "Bye sweetie. Maybe we can go out clubbing together some time. What kind of guys do you like, anyway?" She raised a single eyebrow at me and smiled in false friendliness.
When I got back to the office, Kathleen told me to get my "cute little pantied butt" down to HR. I had a long discussion with the manager there about rights and responsibilities. My job would be protected if I kept performing adequately, anyway that was the law. The reality was that everyone would be watching me like a hawk. If I screwed up, I could end up in trouble in the blink of an eye. I was in a very vulnerable position, especially with respect to my boss, Bob Thornton.
The truth was that anyone who is different, and I was surely different now, had to be above reproach in their behavior. Everyone would have an eye on me. I no longer had a life of my own. I finally got back to my office just before lunch time. It was done. I was out.
A week ago I hadn't even considered going outside of my apartment dressed in a single article of female clothing (well, at least not any that you could see). Now I could hardly believe I was out to the world as a transsexual. I was slightly stunned.
Everyone in the office, which was just about everyone I knew, now believed I was going to become a woman. My hair, face, hands, and jewelry announced it to anyone willing to pay attention. How had this happened? How had my life changed so quickly and so completely?
In my admittedly brief experience with life, I had learned that things that happen quickly and easily usually did so because someone had prepared for them carefully. I had just changed from a lonely, closeted crossdresser to a declared transsexual over the course of a weekend. That was way too quick and way too easy.
Had I prepared myself for this? I knew the answer as soon as I asked the question. I hadn't actively prepared anything, but my life had prepared me for this as surely as tilling a field prepares it for planting. Maybe Cynthia forced the issue and it otherwise would have taken much longer (much, much longer, I'm sure), but looking back on my life, I could see that the path I had taken, or was sometimes forced to take, led pretty unerringly to where I now was. It was something that would have happened as surely as a row of dominos falls once the first one has been knocked over.
And maybe that domino metaphor was a good one because the next few months turned out to be remarkably easy. Despite the many world-altering changes that Cynthia introduced so quickly, my life actually fell into a comfortable pattern for a while.
First of all, now that I was under Cynthia's guidance and protection, and, even more importantly, was the object of her love, my mood improved considerably. Although I was still far from mentally healthy, I was spending less and less time being totally miserable. I mean, like how miserable can you be when you're in love and that love is returned?
Work didn't change all that much in some ways, although it changed entirely in others. After the first couple of weeks, when I was an object of curiosity for the entire company, people's responses fell into two main groups. Most people just lost interest in me because I wasn't really part of their daily life and they didn't have the time to bother with me.
The other group though was a big problem. They were almost all men, and for them I became an object of derision. Once they started taunting me, they never stopped. They did their best to make my life miserable. For many months going to the men's room was provoked anxiety because I was repeatedly teased, threatened, and even physically accosted when there were no witnesses around.
This was one of my biggest problems; each time it happened my fragile decision to allow Cynthia to lead me into femininity fell apart again. Once I started on hormones, it got even worse because my mood was all over the place. I spent a great deal of time in tears and often felt humiliated by my mixed-gender appearance. Once those men discovered they could make me cry, they became even crueler and were rarely satisfied unless they left me in tears. I felt like a wimp, even by girl standards. Still, I mostly remained in the background at work, where I had been anyway since Thornton had arrived.
I diligently did my job, though now there were frequently irritating interruptions by the girls in the office who needed coffee, or some other small errand. I really did try to make up for my horrible behavior of the previous year but at first it never seemed enough. Still, I did their bidding cheerfully and with care. I treated them all as if they were important, the way I should have been treating them all along.
The break room had never been cleaner or the coffee fresher. I was a better housekeeper than most people anyway, and I even kept all their desks supplied with fresh flowers. Slowly the environment in our small office became warm and friendly again. We all looked forward to seeing each other when we arrived at work each morning.
Taking an interest in other people and being nice despite all the problems I faced made me feel better about myself, and being treated like a friend in return was icing on the cake. The mood in the office had changed so much that one of the girls was almost always willing to comfort me when I came back from my misadventures in the men's room either in, or close to tears. Having friends to care for me also made me realize just how angry, bitter, and lonely I had been.
Of course, the women didn't let me off the hook just because I was being nicer to them. They talked constantly about my underwear, they teased me about my carefully plucked eyebrows and polished nails, and often called me a sissy or pansy. If someone was having a bad day, like a painful period or fight with a boyfriend, they were just as likely to take it out on me as not. "Even if you eventually become a girl you'll never experience the joys of a period," Sylvia bitched dismissively during one of hers.
But I wasn't getting back nearly what I had dished out, so I didn't complain. For the most part there was little cruelty in their voices, except for Sylvia, who apparently hated me.
The three youngest girls Kathleen, Betsy, and Heather seemed to grow in confidence as they learned that they could boss me around at will. At first that was difficult to accept, but one day I realized that it would help them grow in the long run so, I started to view myself as their mentor, and took some small pride in being able to help them learn how to be someone's supervisor.
I became increasingly close to Marci, Kathleen, and Betsy, who mostly treated me like a slightly stupid girlfriend. I didn't mind their teasing too much. I even went so far as to play straight man for them, setting up jokes at my own expense, acting obsequiously, and overreacting to their teasing.
At home, I was Cynthia's companion, attentive maid, and lover when she would have me (which, thank god, was often). I cooked, and took care of the apartment, making both our beds and keeping both our rooms neat and clean (aside from the great sex, one of the bonuses to sleeping with Cynthia was that there would be only one bed to make in the morning).
She insisted that I wash all our lingerie by hand and do the ironing too. She was a little nuts about wrinkles, so I ironed everything, napkins, curtains, towels - there wasn't a wrinkle in the entire apartment after a few weeks. In effect I was a housewife, who happened to have a full-time job, not so unusual these days I guess. I changed into woman's clothes as soon as I got home, and didn't change back until I had to go to work the next morning.
Cynthia would decide during the day whether I would spend the evening as Lilly (she only called me Lillian when she was angry with me, or when we were at work), her companion, or Sissy, her maid. As her companion, I dressed more or less normally, although I was always dressed up, as if I was going to work in a fancy office (like ours) or out to dinner at an expensive restaurant. I rarely got to wear jeans, or denim skirts, or tee shirts, or even flat shoes. It was suits and heels, or dresses and heels, or whatever and heels. Really, I loved it.
Cynthia was my Mistress and teacher. She was giving me an intensive course in womanhood. "I won't let you start to go to work as a girl until you can really pull it off. I don't want anyone laughing at you. It will hurt my plans to get Thornton if you become an object of ridicule."
I looked hurt when she said that.
She looked at me for a second and then laughed, "OK, I don't want anyone laughing at MY girlfriend for any reason, although I don't much care what people think of Mr. Miller."
This time I laughed with her.
So I was in a one-girl finishing school. Cynthia worked me with real intensity; Lillian would become a sophisticated young woman or be crippled in the attempt. Sometimes I wasn't sure whether Cynthia cared which. Every move I made, every word I spoke, every position I ended up in when I was still was critiqued and refined by Cynthia. We practiced for an hour or two almost every evening. On some nights I was near tears from the criticism Cynthia heaped upon me when I didn't respond as she wanted. She was unrelenting and my behavior changed inexorably. Within a couple of months, I could act as sweet and feminine as any real girl, when I wanted to.
What I really appreciated was Cynthia's attention to detail. Because of that, I eventually learned to move and act like a real young woman. I wasn't a swishy drag queen, or a bimbo, or hooker, or any kind of joke. I looked like a real girl from the real world, one who had perhaps had taken to be a modeling or dancing lessons at some point in her life.
My posture was more upright (even without my corset, which wasn't often), my shoulders were held a little further back, and my arms swung from my body differently. There was a definite, but modest sway to my hips, and my hands seemed to take on a life of their own, my fingers were more extended and held differently than ever before. I loved wearing skirts and fiddled with them constantly. I also loved to slide my stocking-covered legs against one another, and Cynthia kept telling me that I was going to get into trouble with some guy if I kept moving them around so provocatively. I had to really concentrate to keep them still. I was falling in love with the way Cynthia's Lilly was turning out.
Cynthia also demanded that we stay in shape using her collection of workout tapes. Like everything else we did, she used our exercise sessions as a training opportunity. We would exercise several times each week with three or even four sessions on the weekend. Again, my movements were analyzed and shaped until no one would have any doubt about the girl doing her exercises.
She took me shopping for workout gear and I ended up with separate outfits for Lilly and Sissy. Lilly's stuff was no-nonsense, dark, color-coordinated, and sexy in an understated way. The colors were mostly in several shades of the main color. Sissy's outfits were prissier, with feminine prints and pastel colors mixed and matched a little too obviously. Her stuff was slightly overdone, almost like her personality.
Eventually, I felt like I was sharing my body with two different women. One was Sissy the maid. Cynthia trained her to be somewhat swishy and sissified. I moved with a mincing walk courtesy of the death defying 4" heels she insisted I wear, and my responses to her request were slightly breathy and exuberant. At the same time, she saw to it that I was demure and submissive. I wasn't allowed to initiate conversations or activities, and slowly learned to be passive, but always ready to respond quickly to her demands.
My other persona was Lilly, the young professional woman. I was learning the manners, mannerisms, and behavior needed in offices and at fancy affairs. I was to be like any young woman, at least any young woman who had been sent to a finishing school as part of her growing up. I acquired excellent manners and a fine sense of etiquette, but I still retained a kind of submissive status, which suited me just fine. Cynthia assured me that once I had figured out how to appear as a young woman, that my confidence would grow and my assertiveness would increase hand in hand with that. I could wait. Right now I was thriving under Cynthia's protective wing.
Cynthia had a really wide circle of friends and occasional lovers when I first met her, and she continued to see them. Often she would go out for the evening, sometimes staying out all night. At first she wouldn't always tell me what her plans were, and I sometimes felt scared or even panic-stricken when she failed to come home. Her nights out were a big source of anxiety to me, but it wasn't because I was afraid to lose her to someone else.
One night she came in just after one in the morning and found me curled up on the couch, crying. She was tired and cranky. "What's your problem?" She challenged.
I looked up at her and through tear stained eyes, I blubbered, "I was worried about you. I didn't know where you were."
"Listen," she said curtly, "You don't own me, I own you, or did you forget? If I want to stay out that's my business. If you can't deal with it, that's just too bad." She turned to go to her room.
"Wait," I said, a little too abruptly. I regretted it almost instantly because she whirled around with fire in her eyes.
"What did you say?" She stared down at me angrily.
I knew I had made a mistake, but I pressed on, "I'm sorry Mistress, I didn't mean to be so abrupt. You can punish me, but please let me explain. I love you, I can't help worrying about you."
I looked down, embarrassed that I had been so blunt about my feelings. She said nothing, so I quickly continued, "My mother used to leave me alone and I worried about her too. I used to be scared to death when I heard sirens during the night. I thought they were ambulances taking her to the hospital..., or the morgue. Then one night my nightmare came true, a day after I turned 16, a policeman came to the door to tell me she had been killed in a car wreck. That night had been filled sirens. Tonight was too. Please, I can't help it if I worry when I don't know where you are."
I was crying openly now, but I could see that she was listening so I added, "please punish me so I can go to bed."
"Fine get your butt over here," she said in a tired voice. She spanked me six times for being rude to her and sent me to bed. I felt strangely comforted by the whole scene.
Twenty minutes later, she came in, sat on the edge of my bed, and began stroking my hair. As I looked into her eyes, she caressed my cheek and then kissed me softly on the forehead.
"I'm sorry for the way I behaved; I was cruel to blow you off the way I did."
I nodded, grateful for her apology. She continued,
"Here's what I'll do. I promise to try to let you know when I'll be home late. It may take me a while to remember to do it every time, I haven't had to tell anyone where I was going for 15 years. But I have no objection to doing it, and now that I understand how much it means to you, I want to do it."
I reached up and pulled her down into a hug. I wasn't prepared for such a warm gesture on her part.
"Oh, thank you Mistress. That would help so much," I said. The gratitude I felt in my heart was beginning to choke me up. No wonder people liked her so much.
"You're welcome, and just to be sure you don't worry too much, maybe I should spend more time at home. I think I'll start bringing my friends here. "Your friends Mistress?" I replied, beginning to grow a little apprehensive.
"Yes, my friends. This may be difficult for you, but at least you won't have to worry about where I am. But just remember, if you speak to me like that again, you can count on being punished again. Now slide over, I'm tired,"
I relinquished the warm side of the bed to her and she fell asleep almost instantly. I cuddled her firm body tightly and didn't let go. I felt so loved, I didn't want to fall asleep and lose that feeling.
Cynthia was serious about punishing my indiscretions, and as much as I tried to do what she asked, something always seemed to happen to get me in trouble. Sometimes I was late getting home from work, and I often couldn't get the apartment clean on time, but my biggest problem was that I just couldn't stop questioning Cynthia's orders and decrees, especially when I was feeling moody, and I was often moody once my hormone dosage was increased from its starting level.
During those first few months, I would frequently slip from my proper role despite the prospect of punishment. On occasion Sissy would become Lilly or visa versa, but the biggest problem was that Brad would pop up just about anytime or anywhere. Cynthia knew what she wanted from me, however, and was always there to redirect me and keep me obedient and under control.
One of Cynthia's punishments was to tighten my corset an extra inch for a day or two. "This will be good for you," she would say with mock sincerity, "your waist will be trimmed even faster." My waist really had slimmed once I donned corsets on a regular basis and Cynthia had taken charge of my diet, but that extra inch always meant discomfort during the day and lack of sleep at night. Cynthia knew that.
For more minor infractions, or when she thought I needed immediate feedback about my bad behavior, Cynthia just spanked me. This had now taken on a ritualistic pattern. First, I had to fetch my long handled hairbrush and then stand and present to it to her like a precious object.
"Mistress I deserve to be punished," I had to say.
"Yes Sissy you do," she indicated her legs as she sat down. I then draped myself as gracefully as I could over her legs. She would pull my skirt up and spank me with the brush through my thin panties. While she was doing this, I was to kick my legs and scream, "oh no Mistress, please don't hurt me. I promise to be good." I was also to squirm around on her lap, so she could feel my erection.
After a half dozen or more strokes, depending on what I had done, I had to stand, curtsey again, and thank her for my punishment. Sometimes I would be told to fetch a pair of very high heels and be forced to stand in the corner and not to rub my rear for a full hour. She rarely hit me very hard and the whole scene was designed to humiliate me rather than hurt me. I always felt like a stupid child when she did this, but when she occasionally did it in front of someone else, I felt truly and wholly mortified.
People began to see my punishments when Cynthia did what she had promised and started bringing lovers home. Almost everyone who saw it laughed out loud. It certainly wasn't funny to me, although I could see how it would be to others. Of course, I always had to be Sissy, and there were more than a few times when I wasn't too pleased about it.
Here I was, helplessly in love with her, and she would be necking and petting on the couch while I stood by quietly waiting for orders. I was jealous. I mean how would you feel? She did have the good sense to keep all her really heavy sex in the bedroom, and I was allowed to go to sleep once she had gone there. But I always had to be up early to serve breakfast to her and her guest when they got up in the morning. If it was a weekend, this often including running baths, washing and ironing yesterday's clothes, and staying in service until the guest left, if she did. More than a few stayed more than just one night.
Those late nights and early mornings robbed me of sleep and after a long weekend, I became tired, cranky and resentful. Sometimes that resentment spilled out, like the cup of cold coffee that accidentally ended up on the breasts of one lover I really didn't like. That incident earned me two dozen really hard swats on the butt and two hours in the corner. I didn't often cause trouble, but Cynthia always made sure I knew who was in control.
And all the time, we worked very hard on my voice. "You must change the pitch of your voice," she said early in my transformation, "it's too deep."
She encouraged me to try different approaches to intonation, pitch, and timbre. Now and again, I would sound good but it was hard to reproduce that sound every day. I found that if I could move the place my voice came from in my throat and allow it to resonate differently it was possible to create a voice that would sound pleasing coming from any woman.
Cynthia often reminded me that the alternative to developing my own voice was surgery, and that kept me eager to work hard to produce a woman's voice. After awhile, I could pretty much do it at will. I was a little throaty, and felt best when I was almost "singing" my sentences. I really loved to do "valley speak," and discovered that if I started there and toned things down a little, I really sounded like a throaty young woman.
Starting about a month after my coming out, Cynthia began to throw a series of parties for the girls from our office at her "new" condo. I, of course, was the maid and the women loved to have me serving them.
As they came to the door, each woman in turn was astonished at the way I was dressed and made up. I think this is when they really started to believe that I was serious about becoming a woman. Still, they delighted in having their old jerk of a male boss in such a submissive role and made sure that he paid his dues. This made me an easy target for their derision and invective.
Except for Marci and Kathleen, this was the first time the others had actually seen me as Sissy. Even though I had been in the office every day with my feminine hair and eyebrows, most had a hard time reconciling their working image of me with the saucy, feminine maid who served them drinks and snacks. They were quite amused with my Sissy character, who displayed all the sexy moves needed to attract an old-fashioned macho-type guy, but really had no idea how those moves looked to others. All this ensured that I was the main focus of the evening. They watched me relentlessly, laughing as I made little mistakes, and having a great time ordering me to perform feminine tasks, like fixing my makeup, or straightening my stockings. After the first party my status in the office was changed for good. I would always be lower than the lowest secretary. Talk about payback.
It was a joyous party as the girls reveled in ordering me around, and much like that first night with Marci and Kathleen, I was also groped, fondled, felt up, and made fun of. I was reminded repeatedly of the change in my status, from boss to maid, and it appeared to me that these women were getting even for every slight any man ever made towards them.
The one redeeming feature was that except for Sylvia, who found me repulsive, the others took the whole thing with good humor. They were having fun at my expense, but they weren't being overly unkind or cruel. They certainly intended to make fun of me, but they obviously had no intention of destroying me. It was almost like we were all in on a big joke together. The only problem was that I was the joke.
But I found that I could easily accept any of the jokes they made at my expense just to have all these women pay attention to me. After a short while, I didn't mind be fondled at all, not one little bit thank you. As soon as I felt a hand on my leg or my ass, I backed into it and wiggled shamelessly.
And then, a couple of hours into the second party Sylvia lost it. I had been bent deeply at my knees picking up some garbage from the floor when I lost my balance. I squeaked loudly as I fell, drawing every eye to me. I ended up sitting on the floor with my legs straight out in front of me, like a toddler. Unfortunately, I tried to get up as if I weren't wearing a short skirt and ended up on my hands and knees with my ruffled panties pointing right at Sylvia. The other girls were laughing hysterically, many had tears in their eyes they were laughing so hard, others could hardly sit up straight. Sylvia didn't react that way.
She grabbed my arm and stood me straight up. "Don't you have any pride? You're just disgusting. Flaunting your skinny little ass in front of us like this. You let these women fondle you like some cheap whore. I have never seen anything so repulsive in my whole life." She was so upset, she was spitting.
Marci stopped her. "Sylvia," she cut in, "this is a game, we're having fun. No one is getting hurt. Sure we're making fun of Sissy.... Brad, but he agreed to this. Chill out, will you."
"You're no better than he is, you little tramp. I've seen you and that lesbian Kathleen. Have you no shame either?" Sylvia banged her glass down on the table for emphasis.
Then Cynthia stepped in and took control, "Sylvia, if you can't accept us for what we are, perhaps you'd better leave. Brad Miller had been treating all of us like dirt, or did you forget? He agreed that his behavior was abominable. Sissy here has agreed to take the punishment for Brad. Before too long, both Brad and Sissy will be gone and only Lillian will be left. You can help in that transition or you can leave, it's your choice."
"You're all perverted lesbians." Sylvia shouted, "Except you," she turned on me angrily, "you're even worse. You'll burn in hell."
She grabbed her bag and stormed out of the apartment. For a moment there was stunned silence. Then, in the sweetest, most innocent voice I had ever heard from an adult, Heather, who loved men as much as life itself said, "I didn't know I was a lesbian, did I miss something?"
Everyone burst out laughing. Betsy gave me a big hug and whispered into my ear, "forget about that bitch, I think you're adorable." Shortly after that Sylvia was transferred to another division and we never saw much of her after that.
Three months and a few parties later, I was finally invited as Lillian. Cynthia asked everyone to dress up. I had on a long, bright red rayon dress that swirled enchantingly around my ankles. The top was fitted rather closely, but the skirt was softly pleated, which is why it flowed so nicely. I had strappy, red, three-inch sandals on my feet, and my toenails sparkled bright red through my sheer stockings.
I sported one medium size and one big hoop in each ear, and a bright red ribbon in a big bow in the middle of my head. My makeup now incorporated many of the techniques I had learned at the salon. I felt really good about myself and with my beard virtually gone, my appearance was quite convincing. I studied my face in the mirror before the girls arrived, and thought that with a little surgery on my nose and chin I could really look good.
The sight of Lillian that night really did impress the girls. Shortly after everyone arrived Cynthia made a big announcement. "Girls, I want you all to know that Lillian's period of punishment in the office is over. You can't order her around any longer, and if you tease her, she's allowed to tease you back, even if she's dressed like Brad." Everyone giggled. "Do you have anything to say Lilly?"
I thought for a second and then made a heartfelt, but potentially risky declaration. "I just want you all to know that I will treat each of you like an equal and continue to do my share of the chores around the office. If I start to sink back into my bad old habits, you can bring Sissy back. You can even have her work at the office."
Everyone laughed and applauded at the same time. It all seemed like a dream; they gathered around me as if I had just gotten engaged or something and simply accepted me as Lillian. There were hugs and kisses all around. In fact, it seemed as if there were more hugs that night than I had received in my entire life up until then. I had never felt so accepted by a group of people and told each of them that and thanked them as sincerely as I could for their friendship. I was near tears the entire night as they told me they would support me in the difficult months ahead. I was so overwhelmed at their generosity.
After the first couple of weeks of training, Cynthia had also begun to introduce Lillian to her friends. She would invite two or three of them over for drinks or dinner on different evenings and in this way I got to meet a remarkable group of women. A number of them were involved in business, but there were a couple of lawyers and doctors as well, with a few artists thrown in. They, in turn, were part of a larger network of women who supported each other's careers. A good old boys network, if you will, except they were young and they were girls (I know, I know, they were women, but they called themselves girls).
Cynthia told me that as long as I behaved myself, I could come as Lillian, but if she got angry with me, it could just as easily be Sissy instead. I was as well behaved as I could be, like a youngster who has been allowed to stay up late when friends were coming to visit her parents. Cynthia wanted me to meet them so I could learn how smart, young, professional women spoke and acted around one another. They knew just who I was, even though some thought the whole situation was rather amusing, or even grotesque, they quickly integrated me into their group
At first, I was quite shy, but very few of these women were unkind and most were at least curious about Cynthia's young man who wanted to be a young woman and tried to draw me out in one way or another, so I could never stay in the background for long. And once they discovered I was a financial analyst, they were all over me to explain market trends, different ways to analyze stocks, and how to read between the lines in annual reports. These were wonderful interactions because we weren't talking about typical "girl" stuff, we were talking business. But they would gently correct me if I started to behave too "manly," and never hesitated to give me suggestions for more feminine ways of saying and doing things. They turned out to be a great set of role models and tutors for me.
They shared make-up and clothing tips and some even were kind enough to give me little presents, like scented soap or interesting lipsticks. But all this was seamlessly woven into complex conversations about other things, and I absorbed these lessons painlessly and effortlessly in this safe, friendly environment that Cynthia had created with her friends.
One of these women in particular took great interest in me right away. Her name was Amanda White and she was Cynthia's gynecologist. She was to become mine as well. About a week after the first time she visited, which was only a week after I had come out, she dropped in alone, surprising the hell out of me. I learned later that Cynthia had set the whole thing up. She had led me to believe that she would be home before Amanda actually arrived, but she finally arrived a good two hours after Amanda.
"Amanda! I...uh...I mean Dr. White. Hi! It's so nice to see you won't you come in. Cynthia should be home in a few minutes," I said, a little tongue-tied at seeing her at the door.
Amanda just played along with me, "Hi Lillian, or is it Lilly?"
I nodded my head indicating yes to Lilly, and then added, "at least my friends call me Lilly."
"I'd like to call you Lilly, but you'll have to call me Mandy," she smiled to make me at ease, "that's what my friends call me."
"Oh thank you yes, Mandy," I said, slightly surprised at myself. For some reason I was embarrassed to call her that. I guess she intimidated me.
"Don't you look cute tonight, you almost make me wish I liked girls," she said plucking at my twin set and straightening the bow in my hair. Bows were almost becoming a trademark with me. I liked them because they were cute, something most girls my age had outgrown. But I was different. Although I was in my mid twenties, I usually felt and acted more like a teenager. In "girl-years" I guess I was still pretty young and trying to discover who I was. In the eyes of most of the adult women I met, I wasn't a grownup yet, and it was liberating.
"Thank you," I said, blushing.
She continued without hesitating, "I spoke with Cynthia a little while ago and she said just to come on over. Do you have any Chardonnay?"
"Sure," I said, trying to relax myself. I quickly went and opened a bottle and poured her a drink and then one for myself.
After I had poured our drinks, she asked if it was OK if we sat in my "girly room," as everyone now called my feminine sitting room.
"I just love this room," she gushed, "did you really design it yourself?"
"Yes," I blushed as I answered. I was pleased at her compliment, but still somehow embarrassed that this room was so "me." It was stupid of me to feel that way at this point, but that's how I felt.
"How did you do it?" She asked. Her manner was so comforting it's easy to see why she had a busy practice.
"I didn't do anything special, I said, "it's what I like." I looked down for a moment trying to understand my feelings. Then I looked into her eyes again. "I was always dressed when I was working on it. Really, it's the rest of the apartment that is less like me. I intentionally made it more masculine to hide my real self.
The conversation simply continued and after a few minutes we were chatting about all sorts of seemingly inconsequential things. After a while, Mandy gently redirected the conversation to why I wanted to become a woman. I learned much later that she was getting to know me to make herself comfortable with prescribing hormones. She just wanted to be able to talk with me alone when I had no idea what her goal was. I was just chatting; she was probing my soul.
Under her seemingly casual questioning, I admitted that I absolutely adored what was happening to me but that I was confused and didn't really know what I wanted in the long run, even though right then I wanted to become a girl. I told her how I had begun dressing myself in my mother's clothes well before I was ten and how I continued to do that all through high school. I told her how Rachel had completely taken over my life and how Cynthia was now the dominant influence, and that I had a hard time resisting her (Oh alright, I told her the truth, that I did whatever Cynthia said). I was embarrassed to talk about it at first, but once she got me going, I went on at length about my fervent wish to have my own breasts. I told her about my need to be cared for. I cried when I did.
"If I'm to be your doctor," she finally told me in a soft ladylike manner, then I will be morally bound to do what is best for you, no matter what Cynthia wants. She told me you want to go on hormones and you pretty much confirmed that. It's obvious, however, that she dominates you completely."
I blushed and smiled ruefully, "yes that's true."
"I'll need independent confirmation of your psychological status from an expert. So I'm arranging for you to see Dr. Beverly Wells, a psychologist who is a specialist in gender dysphoria," She said handing me Dr. Wells' card. Since you are to be my patient, I am bound to protect your confidentiality. I will not tell Cynthia anything unless you direct me to," she said. "From what I've seen, I'm willing to start your treatment quickly, but you must go into therapy with Dr. Wells. If you stop, or if I get reports from Beverly, that this isn't for you, then I will terminate your treatment."
"Yes Mandy," I said gulping air like a drowning man, which, metaphorically, I was.
"I'm sure that won't happen though," she said to reassure me.
From then on, both Mandy and Dr. Wells became huge parts of my life, and hugely positive influences on me. They were simply wonderful women. They were clever, and insightful, and supportive, but most importantly they were truly empathetic. They really seemed to know how I was feeling. When Cynthia had me dizzy, or too much teasing at the office had me hurt and confused, I could go to either of them to talk. Dr. Wells especially was brilliant at separating my real feelings and motives from the tangled rationalizations, evasions, and poorly thought out wishes that were my conscious thoughts and feeling.
After two meetings with Doctor Wells, I started on my hormone therapy. The more time I spent with her the more it became obvious to me that Cynthia, whatever her motives might have been, had actually forced me to do something that was right. I really felt that this was healthy for me now, although Doctor Wells said that we would have to wait and see about how far I would go. The circumstances that led to my transition, and my reasons for wanting to do it, disturbed her, which I guess isn't too surprising. So we would take things slowly and see how they went.
The following week, I started myself on a course of electrolysis. I hated my beard and simply decided it had to go. It was the start of many long, uncomfortable sessions in the chair in a local salon, but it's obvious now that it was worth the effort.
Six months after Cynthia had taken over my life, I was as happy as I'd ever been. Our relationship was fantastic, for me at least. She was in charge, there was no question about that, and, she took care of me. I gained more confidence in those months than I could ever have thought possible. It's not that she did anything special to try to heal my damaged psyche, but she was so nurturing, even when she was disciplining me, that it began to repair itself.
I, in turn, took care of our home life. I was the wife, if not the maid. I loved to tend to her body, to bathe her, to brush her hair, to give her massages, and to help her dress and undress. I adored her and couldn't suppress my joy in being around her unless I really concentrated on doing so. I could see in her face, and in her behavior, and in her words, just how much she appreciated my love for her.
Despite the hormones, we had wonderful sex together, and it was clear she was in charge of that too. We made love whenever she wanted and whenever I could nudge, sweet talk, or seduce her into it (She always accused me of wanting to get her to sleep with me so I only had to make one bed in the morning. That's not true, I just wanted to be with her, only having to make one bed in the morning was simply a side benefit..., really.)
Cynthia often said no to me if she wasn't interested in sex, but I would never say no to her. My basic insecurity and love for her wouldn't let me, so I never learned whether I could or not. The standard sex roles were exactly reversed in our household, and you know what, I was in heaven. I was so in love with her that I would do anything for her, especially anything that took place between her legs.
That's how Cynthia started fucking me with her dildo. I was rapturous one evening after she, on top as usual, had ridden me to a magnificent climax. I was cleaning her wonderful pussy with my tongue when she asked me, "have you ever wondered how women feel when they had sex?"
I looked up. "Well, yeah, of course," I replied.
"How would you like to experience it?
I licked her pussy, thoughtfully and looked up again, "I do want to become a woman so of course I want to experience it."
"I can help, you know."
I looked up at her and saw that she was holding a rubber strap on dildo. All of a sudden I understood. I panicked immediately.
"Oh Mistress, you don't mean...?"
"Yes I do sweetie. You have a pussy too, you know." She patted me on the butt. "I think it's time we started to use it for sex. What do you think?"
"I think it will hurt. I know it will hurt. I've already been fucked in the ass," I confessed, blushing and looking away.
"Really? You never told me about that," she said looking surprised," Would you?"
"It was Josh." I said, that night leaping into my awareness. "Remember I told you about the guy who read me and made me behave like I was in love with him or else he would out me at the bar?"
"Yes, I do," she said.
"Well, then he talked Rachel into a threesome. He fucked us both, on more than one occasion. He wasn't that gentle. Rachel loved it, but it really hurt me the first time."
"How about the other times?" Cynthia waited, raising an eyebrow to force me to respond.
"Well, I guess it did get easier, but I never really loved it. I guess I felt forced. I didn't really want to do it. I was scared of being gay in those days. Plus, he was kind of "wham, bam, thank you ma'am" in his approach. Satisfying me was not on his agenda." I paused, remembering the feel of his prick up my ass. Actually, it wasn't that bad. I might have enjoyed it, if Josh had been a little more generous.
"Do I satisfy you?" Cynthia raised that eyebrow again and cocked her head questioningly.
"Oh Mistress, I'm in heaven when I'm with you. I never, ever imagined sex could be so wonderful."
"Do you think I could make you feel better with a cock than that mean old Josh?" It wasn't hard to see where this was heading. I blushed, although I wasn't sure why. "Women have always used dildos, we use them on ourselves, and we use them on each other. If I use one on my darling Lilly, does that make her gay?" She had to ask.
"Well, I guess gay and straight don't make much sense as categories for me any more do they?"
"That's very perceptive of you, honey. I don't think they do. So how do you feel about it now?" She asked.
"I would do it if you are gentle" I replied, "will you be gentle?"
"Aren't I always?" She laughed.
"Well, you do get a little carried away at times." I replied a little timidly, hoping she would laugh.
When she gently hit me on the head with the dildo, I realized that she was happy with my reply.
Two days later there was a gift basket on my bed when I got home from work. It was beautifully made up with pastel colored tissue paper, ribbons, and flowers, There was bubble bath and perfumed soap. It also contained a Fleet's enema, two bottles of Massingale's douche, and a tube of KY jelly. A note from Cynthia was clipped to the handle. I smelled the flowers and then I read the note.
Darling,
Tonight's the night. I want you to be as sweet as a flower for me. Use the Fleet's and then one of the Massingale's. If you don't feel completely clean at that point, use the other. Lube your insides well. Then put on your favorite nightie and wait for me in your bedroom.
I'll be home at 8:00.
Love,
Cynthia
Oh god, she was going to do it and I was going to prepare myself for her. I was going to take a bubble bath and clean out my pussy with a flowery smelling douche and get into a sexy nightie and wait for her on my bed. She was going to come home and fuck me like I was really a girl.
I was very anxious when I started to get out of my work clothes and took a big glass of wine to calm my nerves. I put the bottle and an extra glass on the nightstand next to my bed, thinking Cynthia and I might want some later. I turned on the audio system and let the voices of Bonnie Raitt, Melissa Ethridge, and Deborah Harry fill the apartment.
Then, I went to my bathroom and following the instructions did the enema, followed by the douche. When it was obvious that I was cleaned out, I decided that one douche would be enough. It seemed quite erotic to know I was getting myself ready for my lover. I settled into my bathtub with a second glass of wine, and settled in for a nice long hot soak. Even with the help of the wine, I could barely sit still in the bathtub. I was so nervous I was almost vibrating. My mind wouldn't concentrate on anything but what was to come.
So I got out of the tub a lot sooner than I had anticipated and shaved my face while my remaining whiskers were still soft from the steam in the bath. I took an inordinate amount of time trying to select my nightgown before finally deciding on a pale lacy, almost transparent lavender chemise. Cynthia had always liked it and I adored the lace border around its bodice, and the two spaghetti straps that ran over my shoulders to hold it up. My just budding breasts barely peeked out over the top of the lace, while the hem came to mid thigh.
After I pulled it over my head and let it fall, I slipped on my highest mules, and sat down to do my makeup. Thank god for makeup. I really enjoyed applying it, and it takes concentration and skill to do it correctly. Staring at my face in the mirror that evening really convinced me that my decision to get electrolysis was the right one.
With my eyes and lips done, my face looked sexy, but I decided I had to change the chemise. I changed into a new black gown that was longer and more dramatic. I pulled on a pair of stockings, a frilly black garter belt, and a pair of black silk panties. I wanted to wear stockings and heels, just like Cynthia had that first night. She had worn black. I was going to wear black. I wondered how she would react when she saw me in nothing but stockings and heels and panties.
I decided against a ribbon for my hair, but put in a pair of dangly earrings that she liked. They were gold and onyx and after gently inserting them, I spritzed myself with Opium perfume. I knew she loved it on either of us. So I put it on my wrists, behind my ears, and between my darling little breasts. Finally, I decided to put some behind my knees.
I watched in the mirror as I lifted my foot onto a small stool to reach behind each knee. I felt soooooo sexy, I forgot to pay enough attention to my posture though, and with only one heel supporting my weight, almost fell. Then, I lifted my nightdress, lowered my tight panties and dabbed some perfume behind my scrotum. I remembered how Cynthia had smelled that first night. She had obviously perfumed her pussy. I really wanted to see if she could resist the sexy smell any better than I did, which as I recalled, was not at all.
Finally, I started to lube my ass with the KY jelly. I pushed it in gently with my finger, being careful because of my long nails. I reamed myself a few times and then went for some more. I just kept putting it in until I was really slippery inside. Then I put a panty liner inside my panties and pulled them back up. I was sure I could feel the KY oozing out.
I was ready and waiting for Cynthia's arrival by 7:30pm so I tried to find something to do that would take my mind off what was going to happen in an hour or so. I tried to read Allure but was so distracted that I flicked through it in just a few moments. Then I had an idea! I went into Cynthia's room and found two of her dildos. Then I went back to my bed, pulled my legs up above my head and started to work the smaller one into my slippery rear. I figured that if could loosen myself up a little, I might have more fun and less pain later. The little one was easy, so I let it sit there for five minutes while I applied some KY to the bigger one, which was clearly larger than my own standard size cock.
I was very careful and pushed it in very slowly, but still it hurt a little. I was entranced with what I was doing and focused all my attention of the feelings being created by this lifelike invader penis. Because of that, and the volume of the music, I didn't hear Cynthia when she opened the front door and walked in.
"Well," she said abruptly, "couldn't wait could you, you little slut."
I looked up at her, startled. I was frozen in place with my legs up in the air and the dildo halfway into my asshole. My nightgown was gathered up around my waist and my black stockings stood out starkly against my pale legs. Despite my fear, I all I could think of was the sight that greeted me as I looked towards Cynthia.
She was wearing a figure hugging black leather suit, black stockings, and matching high heels. She had bright red panted lips and smoldering dark eyes. She looked as sexy as anyone I had ever seen, but she didn't look pleased as she stalked over to the bed. I suddenly understood what the male black widow spider sees when the female turns on him. This was one giant spider heading my way.
"Cyn...Mistress!" I blurted out, as I started to pull the dildo from my rear.
"Oh no you don't," she said as her leather gloved hand quickly pushed it in even further.
"Owww," I screamed in response.
She grabbed my hand, wrapped it around my leg and placed it over the dildo. "Don't move," she ordered as she poured herself a glass of wine, "stay just like that." She looked at me and took a long drink from her glass. "Now, tell me just what the hell is going on here. You made an awful big stink about how this was going to hurt, and here I find you doing it to yourself, with my toys, no less. You better have a damn good explanation."
"I do Mistress, I do have an explanation," I whined.
I told her everything I had done since I got home and how I thought this would make things go easier later. She looked at me sternly for the longest time and then started to laugh.
"You have a lot to learn about how to look when your lover arrives home," she said pointing at me and laughing out loud. "You silly girl."
Then I started to giggle a little too. I guess I did look rather funny - raunchy and debased for sure - but funny.
"Don't move, I'll be right back," She said putting her glass on my bedside table. A few moments later she returned with something in her hand but I couldn't see what it was. "Take your hand away from your pussy," she said. Then she grabbed the slippery dildo and pumped it in and out a few times, penetrating me much more deeply than I had dared. She pulled it out suddenly and plunged something else inside me before my asshole could close up again. I felt it stretch wide as the object seated itself. She let it go and I was surprised that it didn't slip out
"Feel," she said.
I carefully put my hand between my cheeks but found no handle protruding out like I had anticipated. Whatever it was, it was all the way inside me.
"That's a butt plug. You'll be wearing it for a while, so get used to it," she said. Then she crossed her hands under her breasts and pursed her lips. "OK, you nitwit, listen up. You've spoiled my mood with your fooling around. So I'm going in the other room to sit down, have a glass of wine, and something to eat. The only chance you have of getting that thing" she nodded at my butt, "out tonight is to seduce me later. You, my fine young man, are going to have to seduce your lover into fucking you in the ass. But for now, pull up your panties and make me something to eat."
She simply turned and walked out of the room. I started to lower my legs, feeling the plug in my asshole and trying to figure what, if anything I had done wrong and more importantly how I was going to make it better.
As I thought about it some more, I realized it was Sissy who was being trained to be the sex kitten, maybe it should be Sissy who seduces her. Yeah, that was it. I jumped up and ran for the closet, at least for the one step it took for the butt plug to make its presence known. Then, moving much more carefully, I pulled my nightgown off and put on my maid's uniform. I quickly brushed out my hair, put on the frilly panties that went with the uniform and minced into the room where Cynthia was sitting, reading a magazine. She didn't look up.
"Good evening, Mistress, I'm sorry I wasn't here to greet you but Lillian had me running an errand for her," I said starting a deep curtsey that was quickly aborted when the butt plug pushed hard against my insides. As I straightened up I tried a different tack, "that is a magnificent suit you are wearing Mistress. It just exudes power and it makes me feel small and weak."
I turned my head away as demurely as I could and shuddered a little bit at the delayed reaction to the butt plug, which was now proving to be rather... intrusive.
Cynthia looked up with more than a little surprise in her eyes, gazed at me for a few moments and then smiled to herself. "Yes, you should have been here. I'll have to talk to Lillian, she should know better. It will definitely cost her a spanking."
She was playing the game with me! OK.
"Oh, Mistress, I'm sure Miss Lillian wouldn't like that. But I guess she does forget who is in charge sometimes. She just has to do things her way. Is there anything I can get you?" I quickly bobbed up and down at the end of my question, no way I was going to try a full curtsey again.
Cynthia pointed to her wineglass and then gestured towards a bottle on the kitchen counter. I really did mince to the counter to refill her glass because the butt plug gave me little choice. I reflexively clinched my ass cheeks together to keep the plug in even though I knew it wouldn't come out until Cynthia withdrew it.
I put her glass on a little silver serving tray I always kept handy, and carried it back into the room with as much wiggle as I could put into my walk without spilling the wine. Then, keeping my knees straight I bent over at the waist right in front of Cynthia, so she got a good view of my face.
"Mistress, your wine," I said softly
When she took the glass, I shivered sending my breast forms into a slight back and forth movement within my dress. It was time for the seduction to begin, but I knew I had to be clever.
"Oh Mistress, I'm sorry," I said trying to sound appalled that my breasts were jiggling in front of her face, "I just got a little chill."
I still hadn't stood up. Cynthia tried to look at me harshly, but she couldn't prevent her amusement from showing in her eyes. I almost giggled in response.
"You look tired Mistress, may I rub your back?"
"That would be nice Sissy, why don't you."
So I walked around the couch and stood behind her. I was going to make sure she liked this and I gently pulled out the two combs she wore to keep her hair out of her eyes.
Then I began to run my fingers through her lustrous hair. After a couple of moments, I pulled her hair up with one hand and began to caress her neck with the other. Then I leaned over and began to kiss her neck and shoulders as if they belonged to a goddess. As I did that, I moved my hands down to her shoulders and kneaded gently through the leather. Her suit was so soft and supple that it seemed part of her body instead of just covering it. We both moaned as I worked.
After ten minutes, I went around the front of the couch again, kneeled in front of her, took off her shoes and gave her a repeat performance of the toe and leg licking that I had given her that first night in her apartment. It took about 15 minutes before I had reached her pussy and had her squirming around on the couch. After a couple of minutes of gentle licking and kissing, I stuffed my tongue as far up her pussy as it would go. She squealed with delight so I started licking and sucking with abandon. She came a few minutes after that. I kept my head in her lap, licking gently, savoring her juices.
I finally looked up and asked, "Mistress, may I ask you a favor?"
She looked down at me but it was obvious that she had not yet fully come down from her orgasm.
"Would you fuck me please?" I continued and I wiggled my butt around to indicate where. "You are a wonderful Mistress, but you never fuck me." I pouted. "Don't you like me?"
She smiled.
I looked up at her through my lashes, adoringly. She looked down at me with mild amusement. I got up on my knees, so I was closer to eye level.
"Sissy's not a virgin you know, she's been fucked by nasty men. But Sissy has always wanted to see how a woman does it. And Mistress, you are the most incredible woman," Her smile grew wider when she heard that.
I threw myself at her and kissed her fervently all over the face and neck. She just lay back and let it happen. I snaked my hand back down to her pussy and started rubbing there too. I pushed my tits into hers and rubbed them together as well. She was breathing hard.
"Make me cum with your mouth once more and I'll do it for you, but only if you're really good," she whispered.
"Oh Mistress, I will be." I sank back to the floor as sinuously as I could, keeping my hands on her breasts for as long as I could. Then I went to work on her pussy, as if my life depended on it. But, I refused to touch her clit. She started squirming and moaning, but I kept away from it and sucked her labia deep into my mouth.
Then she started to beg, "please Sissy, suck my clit, please..."
"Will you fuck me?" I asked knowing I had the upper hand for a change.
"What!? I said I would! I will! Don't stop you little whore!" It certainly didn't take her long to take back control.
Fifteen minutes after she had come the first time she was shuddering again to another orgasm. When she had settled down, I lay my head on her thigh for a few minutes. All the time I could feel that butt plug and before too long, I just had to get up, I straightened my skirt and started to wiggle off to my bedroom. I stopped at the door.
"Mistress can I get you anything else?" I asked looking at her as two beads of sweat rolled down her forehead.
"What? No I'll be fine," she said with a sigh.
"Please Mistress you look tired, please come to bed, I need you in me so bad," I replied and then rushed to my room.
I hurried into my room, pulled off the maid's uniform and untied the corset. Then I sat at my vanity, cleaned my face, and redid my makeup, which was a total mess. I ran a brush through my hair, applied more perfume and lay down on the bed with my head propped on the pillows. I then proceeded to get anxious, very anxious. That whole scene in the other room had taken all my courage and now that it was over, I felt totally lost. Thank god Cynthia didn't keep me waiting too long. She came into the room wearing her black high heels, a silky black robe, and a double dildo sticking out from her waist.
It looked unnatural on her but I knew that by using it on me she was going to enjoy it too. She didn't look or behave like a man, but then it would be impossible for her to look like a man under any circumstances. I smiled to myself realizing I had that problem too.
"You little slut," she said to me as she walked over to the bed. "You never told me you had been fucked by more than one man. How many have you had, 10, 50, 100? I know your kind, come on all shy and timid, but get on your knees for anyone with anything manly between their legs."
"I...," I tried to reply.
"Don't talk. You say you need it, you're going to get it. Then we'll see if you ever want a man again. Lick me," she commanded.
She presented the life-like dildo to me as she stood by the side of the bed. I sat up languorously, keeping my eyes on hers and feeling the butt plug deep inside me. When I was directly in front of her crotch, l looked down at it and began to kiss, lick, and suck her fake penis, moving it around in her as much as possible. She let me go on with that for a while and then took my face in her hands and lifted me up. She lowered her head to meet mine and ravaged my mouth with needy, hungry kisses. I thought she would suck the breath out of me with her intensity.
"Roll over onto your back Sissy and lift your knees up to your shoulders." Then she stood straight up and shrugged the robe off her otherwise naked body. God she was gorgeous. Her breasts were by no means large, but they rode almost defiantly from her narrow chest. She had softly taut muscles and luscious curves in all the right places.
Then she knelt on the bed and put a couple of pillows under my ass. As soon as she had me set she gently twisted the butt plug out of my ass and then leaned in over me, her hands on either side of my body, so we were face to face.
"Now, my sweet little Sissy, it's time to give you what you've been begging for. Don't you find it interesting, that yesterday you were afraid of this, and then today you begged me to give it to you? You're just lucky I'm so nice to you," she spoke softly.
She bent over and kissed me tenderly on the lips. Then she pulled her body up so she was squatting on her knees again, and positioned her dildo at the entrance to my asshole.
"I want you to love this, so you have to guide me in," she took a deep breath and leaned over me again, her breasts hanging down. I could look down between them and see the large penis that was about to invade my body. "That was a smart thing you did earlier, loosening yourself up. You're going to love this so go ahead, grab my dick and guide it into your little pussy. Then talk to me and tell me what to do, this has to go at your rate."
So I did what she said, and I was thankful for her gentleness because I really was apprehensive, although I wasn't sure why. As I grabbed the rubber phallus and it touched the entrance to my pussy, my mind raced back to the first person who had taken me like this. He was Kyle Marcus, a rather handsome, muscular, oversexed young gay man my mother had forced me to date. She had gotten fed up trying to humiliate me simply by forcing me to dress up when she finally realized just how much I enjoyed it. Instead, she figured that forcing me into a homosexual relationship would be something fun for her to try.
"Listen, you little pansy," she spit at me, "I told you that if I found you had been into my clothes again, you were going to get it. Well, sweetie pie, you want to dress like a girl, you're going to go out on dates as one. I've found you a boy friend." She was so proud of herself. "I think that he will be just your type, he's a faggot too." There was venom in her voice.
By the time my first big date rolled around, she had bought me a complete outfit of my own to wear and made sure I looked my part. She first sent me to the bathroom to shower and shave. I had no beard yet, but I had to do my legs and underarms. Then to enhance my humiliation, she shaved around my penis and balls, first trimming my still sparse pubic hair so it wasn't too long and then shaping it into a narrow V. I felt shamed when I saw what was happening, but got hard when she manipulated my penis. When she saw the confusion on my face, she mocked me.
"You really are a faggot aren't you? Getting all hard because I'm shaving you to look like a girl." Can you imagine, your own mother doing that to you.... (of course, this is the woman who accused me of killing my own father).
She went on, just dripping insincerity, "you're going to be so adorable." She slipped a pair of high cut black panties up my legs and fastened a matching padded bra around my chest. She filled it with foam pads.
"You're kind of flat-chested aren't you darling? Hope your boyfriend doesn't mind. But then you're only 14 so what's he expect. I just hung my head, a hot blush rising to my cheeks, although I wasn't sure what I was ashamed about. Then came pantyhose, a really lacy black slip, and a red sleeveless dress that just came to mid thigh. She really did a great job with my makeup and hair, and even put a hot red polish on my nails. It complimented the dress rather nicely. When she added a couple of bracelets, a small necklace and a white sweater for me to put over my shoulders, I was adorable. At least I thought so.
As I waited for Kyle to show up, I stood in front of the mirror, twirling back and forth to make myself feel girlish. I was loving it; it aroused me terribly. At the same time, my mother was doing her best to humiliate me and make me feel ashamed of myself. And as soon as I let myself become aware of what was happening, I got downright scared about going out with this guy, who was bigger and older than I was, and could certainly make me do whatever he wanted.
Fear, humiliation and sexual arousal, that's a heady combination, let me tell you. My mother really was an idiot. She thought this was going squash my desire to dress? Hell, this was like throwing gasoline on a fire. I really loved what was happening to me, at least until Kyle arrived.
Mom wanted me out in public with him, so he took me to a dance at his high school. He set the tone as soon as we got into his car. He turned to me and said, "Listen, princess, here's the deal. You're my girlfriend and you better behave like it or I'll out you and leave you right where it happens."
Oh, great, that would be perfect. I would be a guy dressed as a girl at a dance at a strange high school. No thank you, I would behave. I didn't say a word, I just nodded at him to let him know I understood.
"I'm in charge of this 'relationship,' sarcasm dripped from the word, "and you'll do whatever I say. Is that clear?"
I nodded again, too afraid to speak.
"Good," he said, "now slide over here and let me put my arm around you while I drive."
So I slid over next to him and we drove to the dance with his arm around my shoulder. It actually felt kind of comforting, so I very tentatively allowed my head fall onto his shoulder.
"Very good," he told me, and kissed my head. "You have good instincts, let's see what else you can come up with to show your love for me.
I thought for a few moments and then put my hand on his leg.
"That's a girl," he actually sounded appreciative, "you keep this up and we're going to have a great time together."
When we got to the dance, he actually helped me out of the car, so I gave him a little curtsey in thanks. His smile showed that he approved. As we were walking to the door, he had his arm so tightly around my waist and was holding me so close that I had to put my arm around his waist as well because there wasn't any place else to put it, he asked, "Hey, what's your name, your femme name?" Despite all the times I had dressed in my mother's clothes, I hadn't yet come up with a name I liked, and had no ready reply. But it didn't matter, he broke in to my thoughts almost immediately.
"Fuck it, I don't care. I've always wanted to date someone called Brittany, you'll be Brittany."
"OK, that's a nice name, I like it," I replied in a small voice.
All of sudden, he turned on me and grabbed my hand, bending my wrist backwards into a painful position that forced me down in front of him.
"Owww." I looked up at him with pleading eyes. I had no idea what had happened.
"You listen to me you little bitch. I don't care what you like. You're here to please me and that's all you need to think about." He glared down at me for a few moments and then released my hand. "You do that, and well get along just fine. Let's go."
With that he put his arm around my shoulder and led me into the dance. I was really scared now, he had gone from sweet to angry to sweet in less than a minute. He was a dangerous guy and I had to figure out how to keep him happy.
Walking into the gym where the dance was being held made me feel like a Christian who had just been thrown to the lions. I was lucky not to pee in my panties I was so scared. I clung to Kyle, like he was a life preserver in a rough sea. Fortunately, that was just what he wanted.
Once we got inside, I got really lucky. Someone had brought a bottle of vodka, so we got to drink spiked punch. That really calmed me down and by the middle of the evening Kyle and I were dancing close, with my hands draped around his neck and my head on his chest. With each step in my submission to him, he raised the stakes. Only a little while later, he lifted my head off his chest, tilted it up to his face, and kissed me. When his lips first touched mine, I froze like I had just put an electrical cord into my mouth.
He pulled back and glared at me, "don't you dare freeze up when I kiss you, remember who and where you are."
I wasn't sure whether he meant that I was supposed to remember that I was his loving girlfriend or that I was a crossdressed boy at a strange high school. It didn't matter. Either way I knew what I had to do. I turned my head to the side and tilted my face up towards his. Then I reached up with both my hands, putting them in his hair on either side of his face, and pulled him down to my lips. Then I closed my eyes and let him kiss me.
Let me tell you, I never expected to feel the way I did, but it was damn erotic. Here I was, as thrilled as I could be because I was dressed like a cute high school sweetheart, humiliated because my hunky date was treating me like I was a mere object, and scared nearly witless because he was a potentially dangerous guy who wanted me to behave like his honey. And I was kissing another guy and liking it. Erotic touching, fear, and humiliation fueled my arousal.
By the end of the evening, he had both his hands on my ass and was rubbing his rather hard erection into my tummy. It was amazing, there it was sticking straight up from his groin towards his belly and it was almost like there was another person there with us. Although I had never considered having sex with a guy before, his erection got me even further aroused and I not only rubbed back, but I was starting to consider what that penis might feel like in my hand. I really didn't know what was going on.
At the end of the evening, as I was collecting my bag and sweater to get ready to leave, I was starting to believe that being scared had been a good thing. It kept me close to Kyle and attentive to his needs. I wouldn't have (at least I don't think I would have) chosen to behave like I had on my own, but being forced had been incredibly exciting in a strange way that I couldn't understand at all. I had never felt so vibrant or alive. Every nerve ending in my body was tingling.
Then, all of a sudden, the dance was over. All the other guys took their girls for something to eat, but Kyle had another need. He took me to a local lover's lane, got me into the back seat of his car, and forced me to have sex with him. Really, he just overpowered me physically, and then looming up over me as I lay on my back, he reminded me that I was his loving girlfriend and started to kiss and fondle me. In this new situation, I froze up like I had before on the dance floor. He stopped for a moment, looked into my eyes, and said, "you love me, or did you forget. It's a long way home from here, and if I kick you out of the car, I'm keeping your dress."
OK, I get it. I started to respond to him, and you know what, just like before, I was getting pretty excited, so I went with it. After about 15 minutes, he rose up over me, pushed my knees up to my shoulders and grabbed something from the front seat. It was, thank god, KY jelly. He lubricated himself and then said, "put it in."
For a moment I didn't understand what he meant, but it dawned on me like the sun breaking through the clouds. I was aghast and didn't move.
He just growled at me, "either you do it or I will, and if I do it's gonna hurt more."
So I reached between my legs and grabbed the base of his penis with my right hand. It isn't that big, I remember thinking to myself. He allowed me to pull him towards me and aim the head of his dick at my virgin asshole. I let my head fall back until I was staring up towards the roof of the car. He was in shadow, and his silhouette blocked my view almost entirely. I took in that image for a moment, then closed my eyes and focused my attention on my hand, his erection, and my asshole. I still have a supernaturally clear image of me on my back, with my legs splayed out and pushed up to my shoulders. I was about to get fucked like a girl in the back seat of a car, and on my first date no less.
As soon as I had placed the head of his dick against my hole, he started to force his way forward. It hurt! I started to whimper, and then to cry. He just kept pushing, slowly, but without let up. Really, he could have made it much worse, but he could have made it much easier as well. It hurt the whole time and at one point, just as he finally pushed himself all the way in with one final lunge, I felt a searing pain right in my rectum. I didn't learn what had happened until later, but he had stretched the skin so quickly, it tore. I spent the rest of the evening in tears and ran right into the apartment when he finally dropped me off.
I don't think my mom knew what he would do to me, but when I told her, she just laughed and said welcome to womanhood. She was nice enough to get me a Tampax to stop my bleeding and to wash the blood out of my panties. But the fact that he had raped me didn't stop her from sending me out with him every time he wanted to take me.
We had many dates after that and the truth is, he did treat me better as time went on. We actually started having fun with each other. There was one great weekend when we drove upstate to the Dutchess County fair and then spent the night at a nearby motel.
We walked around the midway hand in hand, kissed on the Ferris wheel, and clung to each other and screamed on the roller coaster. He even won a couple of large stuffed animals that he dutifully presented to me. What could be more girlish than wandering around a fair with your boyfriend, carrying the stuffed animals he had won for you. Even though I felt rather overdressed in my full makeup, slinky red minidress with the flared skirt and shoes with chunky 21/2 inch heels, I was just in heaven.
That night we made love for hours. He always wanted to fuck me when we went out; sometimes that's all we did. Usually it wasn't very fulfilling for me because he came so fast I barely had time to get excited. He usually left me feeling used and abused, which I guess is how lots of teenage girls end up feeling when they have sex with their inexperienced dates. The night after the fair was different. He paid some attention to my needs. We sucked on each other's cocks and after he had come a couple of times, he was able to fuck me until I came just from that. In fact, that was the night I finally had an orgasm through anal intercourse. I could barely walk the next day, I was so sore, but I did learn that sex with a guy could be fulfilling, if the guy was willing to put in the effort.
That's what flashed through my mind as I drew Cynthia's dildo to my rectum. But this experience was nothing like that first time with Kyle. She changed my opinion of anal sex entirely before I had even come. She was masterful with her dildo. She was as patient as I needed her to be, and we took our time getting her all the way in. Then she taught me about rhythm, rate, depth, speed, and all kinds of other things that I, as a guy with his own cock, had never really considered before.
Let's face it, when a young guy is ready to penetrate, he is already wound up and aching for climax. His brain is in his dick. A woman doesn't have that...distraction, and Cynthia fucked me with care, with tenderness, with empathy, and finally with urgency only when one of us was nearing climax. I had my second orgasm from anal intercourse that night. We did it the second time with me sitting on top of her. I loved that too, but decided that I preferred to be on the bottom. It would take me quite some time before I got over the electric thrill of lying on my back with my legs spread so that I could present my special pussy to my lover. I still just love even the thought being in that wonderfully vulnerable position.
After that night, I let her have me whenever she wanted. Sometimes I begged her for it. We were so lucky to have so many ways to make love to each other. I could make love to her pussy with my penis, and she could make love to mine with her dildo. Or, we could just act like two women and make love without any penetration at all. Maybe it was because I was getting so much sex, but my need to penetrate her lessened considerably and I was more than content no matter how we made love to each other.
By the end of my first sixth months with Cynthia, so many things were going so well, that I actually started to feel good about myself. The combination of diet, hormones and the corset had really changed my shape. The beginnings of a real hourglass figure were beginning to emerge on my body, and I noticed that my trousers no longer fit well. My waist was down three inches, to 27 and my hips were up to 32. Cynthia took the opportunity to buy me some man-tailored women's pants. They were a soft gabardine, with front pleats, a fly, and cuffs. But, they were cut with a narrower waist and wider hips, with darts giving them their shape.
The change was subtle, but real if you were looking for it. I got some women's oxford shirts and a couple of ladies pants suits as well. We purposely selected suits that were also very man-tailored, but they were women's suits nonetheless. Everyone who knew anything about clothes knew what they were, but I was less flamboyantly dressed than a number of the openly gay men at North State.
My breasts had started to swell and puff out and became annoyingly sensitive. I now wore a soft cotton and lycra sports bra most of the time at work. My hair continued to grow and except for a trim to keep the ends even, Cynthia made it clear that it was going to grow longer still. That was just fine with me because I had no interest in cutting it either. I wanted long hair. When I brushed it out it came half way to my shoulders. At work I usually wore it back and often in a ponytail.
Cynthia insisted that my nails be kept perfectly manicured, although social correctness prevented me from growing them as long as I wanted, which was probably just as well because I faced certain punishment if I broke one or showed up somewhere with a chip or sloppily applied polish.
I always wore small gold hoops in my ears and of course my ring from Cynthia. With all this, it was becoming harder and harder to keep feminine mannerisms out of my work life, so Thornton told me he didn't want me at any more meetings with clients. I gratefully ceded that role to Cynthia who was a natural anyway.
I often ate lunch with Marci, Kathleen, and Betsy, and we talked about girl stuff and went shopping together. They even got me thinking about what kind of man I might find attractive (which was kind of weird because neither Marci nor Kathleen had much interest in them). That was a hard one for me, I hadn't really thought about that at all, but once they planted the idea, I started to wonder... I knew he had to be bigger than me, but not too muscle bound, and certainly not too hairy, and definitely not macho, ugh. Probably blonde was better, but...but...oh hell, I didn't know.
Then, one day, out of the blue, Marci solved my "guy" problem. She point blank asked me if I wanted to go out on a date with a "really cute" guy. He was the gay brother of one of Cynthia's woman friends, just a couple of years older than me. He was on the fast track to become partner at a big law firm and needed a date for a fancy affair that his company was throwing in honor of a new client. He was still in the closet at work, and often took Cynthia or one of her lesbian friends when he needed a date for appearances sake. But these women were mostly older than he was, and he felt uncomfortable about it. Cynthia had suggested Kathleen, but Marci, knew right away who should go on this date.
" Kathleen's not really sophisticated enough for that crowd, how about Lilly?"
"Oh, what a great idea," squealed Cynthia. My fate was sealed.
Marci was the one who broached the subject to me.
"A date? With a guy? You've got to be kidding." I truly was taken aback. "Cynthia would never..."
Marci cut me off, "Cynthia thinks it's a great idea. She says it will give you a chance to work on the kind of etiquette and manners that you can only learn at fancy affairs. Besides, this guy is adorable and he's almost as nice as you are. If I liked guys, I would be chasing him like he was the last man on earth.
She leaned over and kissed me on the cheek. I blushed with pride and hugged her back, remembering how much she despised me just a few months ago.
"Thank you Marci, I'm so glad you're not mad at me any more."
"She laughed for a moment and then said, "Sissy darling (she just loved to call me Sissy), I really liked you when you first came to work with us. You were one of the nicest men I had ever met, and so cute." She pinched my cheek in jest. "Then you became a jerk and I started to hate you. But no one could ever stay mad at someone as sweet and submissive as you've become. I'm only sorry we didn't rescue you sooner from the clutches of that stupid Brad Miller. So what do you say, will you do it?"
"I guess so, but I'll need some help," I replied.
"Oh! I know that's the best part. We're going to have so much fun. We have to shop for a dress and shoes, and get your hair done and....," she was gushing with enthusiasm.
"Marci, what kind of a date is this?" I asked, now unsure what I had committed myself too.
"Didn't I tell you? It's a black tie party in honor of a new client. It will be held in the penthouse at Trump Tower. Very ritzy, and there are sure to be lots of celebrities there."
My eyes opened wide and my jaw dropped, a fancy dress party? Oh no, what did I get myself into. As it turned out, I got myself into quite a lot. Michael Butler was indeed a very sweet, gorgeous guy. A dirty blonde, sort of like I thought I might have preferred, and big, but not muscle bound at all. I'm sure all the straight girls who knew him, thought, "what a waste," when they discovered he was gay, but you couldn't tell that by looking at him. He dressed conservatively, behaved impeccably, and played every sport imaginable.
It also turned out that he had as many misgivings about this as I had. His were actually more serious. He was afraid that if anyone even suspected I was not a real girl that it would damage his reputation beyond repair. As a result, even though he loved the idea of going with a guy instead of a real girl, he wouldn't take me to the party unless he was sure I could pull it off. So he made a deal with Cynthia. If she could get me ready to pull this off, I would be his date and he would buy her dinner at the restaurant of her choice. Knowing Cynthia, that would be one expensive meal. But, if I wasn't ready in time, she would have to go to the party with him instead and buy him that expensive dinner.
"Hey, what about me?" I said, "isn't anyone buying me dinner?"
"Lillian Miller," Cynthia shot back,
Oh no, I should have kept my mouth shut. I was in trouble again. But Cynthia broke into a huge grin.
"You win no matter what happens. You'll get to wear all kinds of pretty dresses, you'll learn more about being a woman, and you'll have all of us paying attention to you so you'll be ready on time. Besides, you're the one who will get to go to the penthouse at Trump Tower. So don't be selfish!" Her voice rose and she threw her magazine at me, though it was obviously in jest. Then she turned serious again (at least she looked liked she was serious). "If you blow it, however, and you're not ready in time, you'll be Sissy 24/7 for a month. Now shut up and sit down. Michael and I have details to work out and this is no time for your childish shenanigans.
Hhmmph, shunted off like a little girl again. I sat on the couch and pouted (Brad would have fumed, but Lillian and Sissy pouted; somehow it seemed more appropriate). Still, I hated it when people talked about me like I wasn't there, which is just what Cynthia and Michael were doing now, although Cynthia was in one of her take charge moods and Michael hardly got a word in edgewise. Then, during a brief lull in their conversation, Michael caught my eye, gave me a fake pout of his own, and winked at me. For a moment I thought he was making fun of me, but then I realized he was really commiserating with me instead, like maybe he and I were sharing a secret and Cynthia was the one being left out. I thought hat was sweet and it made me feel better and warm to Michael.
They eventually decided on a series of dates before the big night to allow Michael and I to get to know each other and to make sure I knew what I needed for such an upper crust function. That's how I ended up going out with Michael for a casual dinner one evening, to a fancy dinner and dancing on a second date, and to the opera for the third.
Cynthia, Marci, Kathleen, and several of Cynthia's friends immediately went to work to get me ready. They decided it was time for an all out effort on several aspects of the feminine me. It was almost like Christmas, and I was the tree they were going to decorate. The most exciting part of the whole thing for the old crossdresser in me was ball gown training. They borrowed some formal gowns for me to practice in, and a couple of nights a week, I was dressed like a princess and run through my paces like a big puppy getting ready for the annual show of the Westminster Kennel Club. In addition to the gorgeous gowns, there were elbow-length gloves, jewelry, upswept hair, and different kinds of wraps. One week I got to practice with a white mink stole. It was just luscious against my bare shoulders, and so much fun to cuddle in and twirl around.
We started with really basic stuff, like how to walk and sit down, and moved to more advanced lessons, like eating hors d'oeuvres while standing up with your bag on your shoulder (my idea of slinging it over one should and under the opposite arm, so the strap lay between my breasts was hooted down by all the women together - Geeesh). Then there was the really hard stuff, like holding up a long skirt so you can walk, especially up and down stairs, and even using the ladies room. I mean, there was a lot of dress and underwear to deal with in one of those little cubicles. No wonder the lines are always so long outside the women's rest rooms. There was one dress that I enjoyed wearing, but with a long slim skirt, it was a real bitch on stairs. I had to turn partly sideways to come down, and take such small steps that I never quite felt in control, much to the amusement of Cynthia and her friend Haley, who let me borrow the gown.
Then, one evening while we were practicing eating and drinking while standing up, and I was trying to be on my best behavior, Cynthia asked out of the blue, "So Lillian, tell me about yourself."
"Huh?" I replied, being as clever as I could be.
"My dear," she said as haughtily as she could, "I don't think 'huh' is used in polite conversation. I stood there looking stupid while the other women in the room laughed uproariously.
"Really," Cynthia teased, "correct me if I'm wrong, but it seems to me that if you plan to go out as Lillian, it might be a good idea to create an identity and life history for you. You know, where you grew up, went to school, and whom you work for. "
We quickly decided that the easiest and safest thing to do was to keep my real life, changing only the names, to protect the innocent. Then Cynthia decided I should be a consultant. "Of course, if you're going to be a hotshot consultant, you'll need business cards, won't you?" It wasn't really a question. "If you're going to get cards made, you should have a feminine middle name. All my friends use their middle names or initials on their cards, and you will too."
I knew whose name I wanted right away, there was only one woman in my family who had loved me unconditionally, my mother's mom, Grandma Samantha. I liked that, being named after both Cynthia's and my own maternal grandmothers. So the cards would read Lillian Samantha Miller, which I thought was a bit much for a simple charade. But I was so delighted with my name, I didn't even think to ask about the name of the fictitious company that was to be my employer.
But I was Lillian Samantha nonetheless, and I both feared and hoped that it wouldn't be long before my driver's license would contain that name as well. A few days later, Kathleen started calling me Sammi and the first time she did, I cried with joy and hugged her as hard as I could. What a sweet, touching thing to do! I was still not used to people treating me so nicely. Each time it happened, I choked up. My heart felt so full, I just couldn't contain my emotions. Of course, by this time, the hormones were probably amplifying every emotion I had, but no matter, I was really touched.
One night, Roberta Watts, a friend of Cynthia's who worked at Saks Fifth Avenue, loaned me a long black sequined gown to practice in, and Cynthia decided that it was the one I had to wear to Michael's party. It was sleeveless, with shirred fabric gathered at the neck in front, so it looked almost demure. The back, however, was only a set of six criss-crossing rhinestone studded straps, leaving me exposed to the top of my derriere. I would have to wear this without a bra. It also had a side slit that went at least half way up the thigh. Mandy, who was over to help that night, pointed out that a "young thing" like me would be expected to be sexy, and I'll tell you, between the back and the slit, this dress should leave every guy who saw it with a hard on.
I was secretly delighted with just how sexy and feminine it made me feel, but figured I had to object to wearing something so overtly hot just for show. "Cynthia," I practically whined, "This dress exposes too much. Wearing it would embarrass me."
She just snorted at me derisively, "My dear girl," she sounded like some very proper British lady's maid, "don't be such a prude. You'll have men lining up all across the room trying to get you to pay attention to them. Besides you have no judgment in matters like this." She stopped for a moment and looked at me with her head slightly tilted, then she resumed talking in her normal voice, "besides, I know you're lying. You'd do just about anything to wear this dress wouldn't you?"
I smiled at her and nodded meekly. "Yes! It's wonderful." I minced over to Roberta as quickly as my little steps would carry me and threw myself into her arms. "Thank you so much for loaning it to me."
"Oh, I'm not loaning it to you, but I will let you buy it at my discount. Let's see, where's the tag," and she went rummaging through her purse. "Oh here it is, she said brightly, "only $795, retail, with my discount it'll cost you $640.
"What?" I almost choked on the drink I was sipping and ended up spraying some of it on Cynthia, who for some reason started to laugh, so did Rachel. I just looked at them horrified.
Once Cynthia had gotten herself under control, she told me that she and Michael had decided to split all the costs with me three ways. I had to dress up, but I didn't have to go broke, although once I had added shoes and accessories, and threw in a trip to the salon so Shelly could work her magic on me, I would end up spending more than $750 for this little charade.
What the hell, I thought, in for penny, in for a pound. I drove the cost out of my mind and got back to my practicing. I certainly wasn't going to risk ruining a dress that was so expensive. With everyone in high spirits, I spent the rest of the evening vamping for them, showing as much leg as possible and practicing sexy looks over my shoulder that emphasized my bare back. Cynthia threatened to spank me at one point if I didn't behave myself. We all had a wonderful evening
Cynthia also forced me to sign up for some ballroom dancing lessons because a sophisticated young woman like myself would of course know how to dance the waltz and foxtrot. I would indeed be Michael's partner in all respects. Kathleen agreed to go with me for moral support, and you know what, It was fun. We really loved it! Then, after my first date with Michael, I convinced him to join me and he brought along a friend to dance with Kathy.
Men commonly bond by sharing activities, and the dancing lessons were the activity that helped cement my friendship with Michael. While we were dancing, we talked to each other about all sorts of things, including our feelings, something I had never done with another man, not that I ever had many male friends anyway. It was great, we were getting along so well that even when I got confused or made mistakes, we both just laughed. I decided that as soon as I had the time I was going to learn to tango. It's such a sexy dance, and Cynthia was definitely going to be my partner. She would be so hot, I was getting excited just thinking about it.
One evening I told him about my new middle name, and why I had picked Samantha. He in turn told me that he loved the name Samantha. He had a childhood fantasy from an old TV show about having a girlfriend named Samantha, who he called Sam. At that point I decided to take a chance.
"You could call me Sam, if you like," I said as he spun me on my toes under his strong left arm. Although I started talking with some confidence, by the time I finished, I sounded like a rather shy 14 year old.....and felt like one too. I was surprised to feel so vulnerable just because I made such a little offer. The fear of rejection was strong in me.
But by then I was back in both his arms and he held me away from him a little and said, "Really?" And when I nodded yes, he just lit up, "I'd love that, Sam." And he kissed me briefly on the lips. I blushed so hard I felt like a flash bulb.
But I was driven by the moment. In the low heels I was wearing to learn to dance, I could only reach his cheek if I stretched up on my tiptoes, so I did, kissing him in return and leaving a plum colored lipstick mark. I pulled my head back and smiled at him. He looked into my eyes for a moment and then pulled me to him with his right hand, which was already on my back to guide me as we danced. His left hand came up to the side of my head and holding it gently, he kissed me again, this time lingering on my lips for a quite a while. I felt a little breathless, but wonderful being with him and in his arms. When I noticed the other six couples in the class staring at us, I blushed again and buried my face in his chest.
On the first of our dates, Michael had arranged to pick me up at the apartment, and when he arrived, I was struggling to get ready. I was anxious because I couldn't decide what to wear and Cynthia was being no help at all. In fact I'm sure she was torturing me just for the fun of it. She simply said that she liked everything I had and when I came running out to the living room to show her how one outfit looked, she looked up blandly, and said, "fine."
Fine? Fine? What the hell does that mean? I wanted to look great, and the way she said fine, it sounded like terrible. I mean, why have girlfriends if they won't help you dress for a date? I was so frustrated I stamped my foot. Cynthia just laughed.
Since this was meant to be an informal evening, for a while I considered jeans with a white cotton blouse, and black flats. Then I decided I just had to wear a skirt or dress, but I didn't really have anything that was particularly casual. So I finally decided on the long red rayon skirt and the long pale yellow cotton sweater I had worn the Sunday morning of that first weekend all those months ago, when Cynthia had just moved in and taken over my life.
Of course, by the time I finally decided, Michael was almost due, so I was still dressing when he arrived. Thank god I had done my hair and makeup and was wearing French nails. When I finally entered the living room, he was chatting with Cynthia, like the old friends they were. He rose from his seat with an expectant look that turned into a warm, admiring smile as soon as he saw me.
"You look wonderful Lillian," he said, sounding completely sincere. He was dressed in jeans and a turtleneck, with a muted plaid sports jacket of some wonderfully soft wool.
"Thank you Michael," I said, a bit breathlessly. "I'm sorry it took me so long to get ready, but my girlfriend here was no help at all." I threw a pouty look at Cynthia.
She just rolled her eyes and Michael and laughed. "She's insufferable, you'd think she'd never been out on a date with a guy before, and at her age.
Trying to ignore her pointedly, I turned back to Michael, "you look very handsome tonight." I couldn't believe I had said that in front of Cynthia! It just came out. I was soooo embarrassed. I sounded like a 16 year old. I lowered my eyes and could feel my face heat up as I blushed. All of a sudden I was feeling a little unsteady in my heels. Thank god my hair covered my face so well!
"You're blushing," he said with genuine surprise in his voice. He had no trouble looking down at me even though I was 5'10" in my heels. "Come on, lets' go, I'm looking forward to this evening, I think we're going to have fun."
I threw a long woolen coat over my shoulders to protect me from the October chill that descended on Manhattan after the sun set, grabbed my purse and went to give Cynthia a kiss before I left. Doing that made me feel like a teenager saying goodbye to her mom. I shivered with delight at the feeling. I got off on the strangest stuff. Then again, my relationship with my own mom was so bad, that I almost never got to feel anything positive from her, maybe I was just having a second childhood.
"Now you two behave yourselves," she said with mock seriousness. "If she comes home pregnant, you're both in big trouble."
"Moommmm," I bleated, "how could you say that? You're so embarrassing. I told you I'm on the pill, did you forget already?" I couldn't resist teasing her now that I had Michael by my side to protect me.
"You're what?" She shouted back. "Why you little tramp. Get out of here before I ground you altogether."
We waved over our shoulders as we laughed our way out the door. Michael put his arm around my waist and led me to the elevator. As the door opened, Mrs. Marks stepped out.
"Hi Mrs. Marks," I chirped.
I guess I was still giddy from joking with Cynthia. Instead of being embarrassed because my neighbor had caught me wearing a skirt and in the arms of a guy, I was teasing instead. Of course she had seen me that first night when I let Marci and Kathy in my door while I was wearing only lingerie, and a few other times as well, but we had never talked. She looked up at me, but it took a moment for her to figure out just who I was.
Her eyes went wide and her mouth opened and closed a couple of times, but only a very squeaky, "is that you Brad?" came out.
"It's Lillian now," I said, as the elevator door closed.
Michael started to snigger.
"Whhaat?" I looked up at him with wide, innocent eyes. Then I giggled along with him. What was a great start to a first date; my mood was buoyant.
From then on the whole evening went great. We went to one of those cozy little neighborhood Italian restaurants that dot New York City. We shared wine, we shared food, and we shared ourselves with each other. It was almost as if we were buddies, which sort of makes sense since we're both guys, even if I didn't look like one and did my best not to act like one.
I decided about half way through the evening that I really wanted to attend the big affair with him and did my very best to behave like the kind of sophisticated young woman he would want to take. I desperately wanted to flirt with him, although I wasn't sure why. Besides, I wasn't sure if I wanted to go where that might lead, so I restrained myself. Well, at least I restrained myself most of the time, really, no one's perfect..., right?
We had always planned for this to be a short evening, but after we ate, neither one of us wanted to go home. I wanted him to take me to a gay bar for a drink or two, but he wasn't up for that, "what happens if one of my friends sees me out with a girl?" he exclaimed, his voice rising as he finished, "it could ruin my reputation." We both just laughed, but I couldn't let it go.
"But I am a guy," I insisted.
"Well, maybe you are," he said, "but you sure don't look like one. What do you plan to do, pull your skirt up and show everyone your dick?"
I hit him playfully on the arm, "well I could you know?"
"Oh no you couldn't," he shot back, "you'd have every guy in the place after your ass in 10 seconds, and I don't know you well enough yet to promise to protect you against some of those body builders."
Our conversation continued in that light mood as we strolled aimlessly around the west village and chatted.
His childhood was not terribly unlike mine, although his parents were quite affluent. His father was a workaholic, who was seldom home, and then walked out on his wife altogether when Michael was only 13. His mom was not warm and focused much of her attention on his two younger sisters anyway. When she found out he was gay, she tuned him out altogether and shipped him off to an expensive prep school for his last two years of high school.
The prep school turned out to be a treat for Michael because his gay self was able to bloom among like-minded friends and a staff that turned a blind eye. But, because his mom cast him out, from the time he was 15 he rarely saw his family, and ended up feeling like an orphan. Like me, he believed he was escaping an intolerable situation when he finally headed for college.
As we shared the intimate facts of our lives, I began to warm to him. I was sure I knew how he felt growing up. So I told him my story, and he behaved like an absolute dear, actually getting a little tear in his eye. We both felt comforted by being able to walk hand in hand with each other.
Then an unexpected thing happened; the warmth between us started to turn into sexual arousal. I don't know, maybe it was pheromones, or maybe any sign of affection turns guys on, or maybe Cynthia just had me in such a high state of sexual arousal that I was turned on all the time anyway. By 10 o'clock we were headed down Sixth Avenue towards my apartment. He had his arm around my shoulder and I had mine around his waist and I was snuggled as close to his body as I could get. As we crossed 12th Street, a couple walking the other way noticed us, and as they passed the girl innocently said, "don't they look like they're in love," as if there were no question about it.
Sixth Avenue and Twelfth Street, this is where Cynthia had kissed me that first Sunday afternoon we were together, maybe this is a lucky spot for me. So a few steps after we had hopped back up onto the sidewalk, I stopped, grabbed Michael's hand, and guided him in front of me.
"Kiss me," I said softly, telling him exactly what I wanted. But it sounded somehow wrong that way, so I added a submissive, "pleeease?" to soften my already plaintive sounding command into a request.
He only said, "Oh yes." It came out as kind of a moan, but he had his lips on mine so quickly, and I was so hungry for them, I never really heard what he said anyway. I melted into him and hung on for dear life. This guy could kiss. It was so different than kissing a girl, even though many of the girls I had kissed had been in charge, just like Michael was now. He was strong and insistent, he had bristles on his face, and very much unlike me now, he smelled so much like a man. I simply received his kiss as openly and joyfully as I could. And when he put his arm around my back and pulled me closer to him, I had no choice but to let it happen. I was glad to do it.
When we finally stopped, I was breathless. "I had no idea," I groaned, and looked up into his eyes, "that it could be so good to kiss a man."
"You're exquisite," he said. "And you taste delicious."
I thought of the tiramisu we had shared for desert and stupidly licked my lips to see if I could taste it. Of course the only taste there was lipstick..., and Michael. We stood there for a few moments, not knowing what to do, and then turned towards my apartment. We didn't say a word the rest of the way back, but we held onto each other tightly.
When we got to the door, I said, "do you want to come in?" Then I giggled, "I'll show you my Barbie doll collection."
He simply leaned down and kissed me. I put my arms around his neck and enjoyed his tongue in my mouth. He stopped after a few moments and then said, "you are remarkable Sam. I don't think I've ever felt this way about anyone with tits."
He reached inside my jacket and rubbed my left breast with real curiosity. "In the past when I've felt them push into my chest during a kiss, they turned me off. I have never been so turned on by anyone who looks and behaves so much like a woman." He held me at arm's length. "You are a guy aren't you?" I nodded affirmatively, trying to look as feminine as possible.
We already had that dinner and dancing date set for 10 days from now, but we both wanted to see each other sooner than that, and we both knew it.
I looked into his eyes, "Call me tomorrow, I think I need to talk this over with Cynthia. I didn't anticipate being so attracted to you either." I looked away and blushed. I was feeling so weak and out of control. My heart was beating rapidly in my chest and my breathing was rapid and shallow, and for a moment, I thought I might faint. "I've had only trouble with men in the past and I'm a little scared." I looked back up, "Please kiss me again."
I have never felt more like a girl than during that kiss, and I reveled in the feeling. When I finally opened the door and went in I was thoroughly confused. If it hadn't been for my gaffe, I would have had a hard on that would have torn my skirt (well maybe not, it was a loose skirt after all).
It was dark inside the apartment with only the glow of the outside lights of the city to see by. I took my heels off of my slightly sore feet, and dangling them from my left hand by their ankle straps, walked quietly towards Cynthia's bedroom. I looked inside and saw that she was already asleep. The rule was that if she was asleep, I wasn't allowed to wake her. I wandered back to my room, completely dejected. I washed up, changed into a short nightie, and then went back to her room. So what if I get punished. I really needed her now. I got into bed next to her and cuddled up as closely as I could get. Not surprisingly, she woke up. The surprise was, she didn't look angry, she looked worried.
She sat up and put her hand on my cheek. "Are you okay Lilly?" Those four words almost made me cry.
It was such a simple thing, but I believed with all my heart that it revealed her true feelings about me. She really was concerned about my well being. I felt so lucky to have her. So I stroked her hair to relax her.
"I am now that I'm in bed with you. The evening was wonderful but now I'm totally confused. I just needed to feel you near me. Please go back to sleep, we can talk tomorrow," I said staring into her eyes. She closed them and went back to sleep. I lay there for quite awhile before I was able to join her. What a night it had been.
When Cynthia's alarm went off, we awoke together. She started to get out of bed but I grabbed her hand and wouldn't let her go.
"Cynthia, do you remember last night?" I asked.
She was back to normal, and glib, "sure, you were scared, I let you sleep here. I should have thrown you out on the street for waking me after I'd gone to sleep. I might just tighten your corset down to 14" as punishment." Her eyes crinkled with glee, showing she wasn't upset.
I pushed on, undaunted. She had to make fun of me, that was part of her role in our relationship. I was going to tell her how much she meant to me, whether she wanted to hear it or not.
"I'm sorry I woke you up. But you saw something was wrong and you put your hand on my cheek and asked me if I was okay. My heart almost burst with joy because your concern was so obvious. No one ever...." I tried to continue but she put a long-nailed finger over my lips.
"Shush, come here, I'll give you a hug...."
I almost leapt at her, I was so grateful. For no reason I could understand I cried in her embrace and then felt much better - must be the hormones.
"I told you that you would like Michael," she finally said, breaking off the hug.
"You were right, too," I blubbered. "Now what am I going to do?"
"You're going to explore that part of your life, that's what. I told you that you had a lot to learn about yourself. I'm going to see that you do."
I hugged her fiercely. "Oh Cynthia, you are the best thing that has ever happened to me. I never before knew anyone who was actually willing to put my needs in front of theirs."
She let me cry for a minute while she held me and patted me as if I was a baby. Then she said, "come on, let's get ready for work."
"No, wait, tell me why. Why are you so nice to everyone?"
She looked at me sharply for a moment and then sighed. She got a slightly far away look in her eyes as she looked out the window towards the Riverside Park. She started talking without looking back. "My parents were born again Baptists. They were fanatical about religion, but very cold. They had no empathy for other people at all, including their own kids. It was almost as if they didn't see the people around them as people. We were all objects, like furniture." She shook her head as if she were ridding herself of an unpleasant thought.
Then she slumped down on the bed and went on, "they were unforgiving of anyone who sinned, including their six children. I was the third and the second girl. We all longed desperately to be loved, but we weren't, and each of us in turn fled home as soon as we were old enough. I felt terrible leaving my younger brother and sisters behind, because for all intents and purposes I was their mother. The only nurturing they got came from Hannah, our older sister, and from me. Hannah was the first to leave, and when my turn came, I knew I had to go if I was to survive." She had started to tear up and now began to sniffle. I grabbed the box of tissues and handed it to her. She smiled at me feebly in thanks.
I dropped down on the bed right down next to her and grabbed her hand. "You don't have to go on," I said, "I never intended to cause you pain." I was feeling guilty because her feelings were so obviously intense. She was dredging up deeply buried memories and I was getting worried about where this story might go.
"No," she replied through now red eyes. You really do need to know this. It might change how you feel about me."
My eyes widened a little and I could feel my heart rate start to accelerate. Her words scared me, but I kept silent.
She went on. "I had joined ROTC in high school and went into the army as soon as I graduated, that's why I'm so good at discipline." She threw me a crooked smile and went on, "the Army saw my potential and sent me to college. I could never have afforded it otherwise."
I had no idea where this story would lead and I guess she saw the confusion on my face. She just pushed ahead, "I swore when I was 13 that I would never treat anyone the way my parents treated their children. I can't stand to see people suffer emotionally, and for some reason, I seem to know just how to keep that from happening."
"But you take care of so many people. How can you do it, don't we all drain you dry."
She smiled at me sweetly, like I was a ten year old who had just asked where babies come from. "You don't know much about love do you?"
I dropped my shoulders and shook my head. "I guess not, it's never been part of my life." Then I lit up and grabbed her in a hug. Pulling back I smiled as brightly as I could. "Until I met you, that is." In some ways, I guess I was like a ten year old.
"There's one more thing you need to know, Lillian." That startled me, she never called me Lillian except when she was angry, but this time she said my name with obvious affection. I started and looked into her eyes. "It wasn't just my grandmother who was named Lillian. I had a sister named Lillian. She was only a year and a half younger than me. We called my Grandma Lillian and my sister Lilly so we all knew who we were talking about."
The look on her face filled me with foreboding, but I said nothing. "For some reason my parents were really hard on her and she just hated them." She could obviously tell I was scared because she patted my hand. Without looking up she said, " But Lilly and I adored each other, we were inseparable..., we did everything together. She begged me not to leave, but I assured her everything would work out just fine." She gave a big sigh and I could see determination fix itself on her face.
Six months after I left home for the army, just after her 17th birthday, she ran away. Two weeks after that they found her body in a ditch only ten miles from our house. She had been raped and murdered.
I gasped, horrified, although the real horror of it was beyond my understanding. I started to cry anyway. "Oh Cynthia," I blurted out and grabbed her to me. She was now crying openly as well. We clung to each other for a few moments before she collected herself. She pushed me away, holding me at arm's length.
"When you first told me your femme name was Lillian, my heart almost burst. I had felt so guilty about leaving home to begin with, and that guilt just exploded in intensity when I heard that Lilly had been killed. I was overseas and was given a week to go back home for her funeral. I was sure she ran away because I wasn't there to protect her from my parents. I blamed myself for her death. At her coffin I promised her that I would never let anything like that happen again."
"My sister Lilly loved Laura Ashley, she talked about it constantly, telling me how she would decorate her bedroom, but we could never afford it. Then I walk into your bedroom, and it's all done up in Laura Ashley. The site of it hit me like a lightening bolt. I thought I could use you to replace my Lilly. I felt right away that I could assuage my guilt by helping you to mend. That wasn't fair of me. I've been so presumptuous. Please forgive me."
And she fell back into my arms crying again. I was stunned. I had no idea, how could I. But I was just as surprised that she was asking me forgiveness as I was appalled by what had happened to her sister. As I tried to understand my feelings, it became clear to me that I loved her, no matter what her motives might have been. I had never been happier than I'd been over the past six months. This woman, who was begging my forgiveness, was a blessing for me. As I held her, I told her so.
"Cynthia, I don't care what your motives are. No one has ever given me more love or nurturing than you. I feel honored if you think I'm even a pale shadow of your sister. I'm embarrassed to call myself Lilly after what you've told me. You don't need to ask for my forgiveness, after the way I've behaved, I should be begging for your tolerance and understanding."
She looked up at me through red-rimmed eyes, her cheeks wet with tears. "Now let me tell you the real reason I gave you the ring." She lifted my hand and ran her fingers over the emeralds. "I wanted to remind myself how important it was for me to take care of you. I could never forgive myself if I lost another Lilly."
That just choked me up completely and I started to cry yet again. I had never felt like I was important to anyone. I started to get scared. I wasn't sure I could bear being this important to Cynthia. But then I began to see that if I really loved her I would have to bear it. If she needed another chance to raise her sister, I would gratefully give her that chance. Lord knows, I still had a lot of growing up to do.
We sat there wrapped in our own thoughts for a couple of more minutes and then Cynthia stood up, dragged me off the bed, looked deeply into my eyes and kissed me. Then she gave me a big smile, and shoved me towards the bathroom. "The girls will be pissed off if there's no coffee when they get in, and I'm not going to protect you from their wrath. You better hurry young lady."
I seemed to spend much of the day floating on air. My friends teased me gently when they noticed the mood I was in.
"I think our Lilly is in love, "Marci taunted me gently, "or else she got laid last night. Do you have a boyfriend now, sweetie?"
I just gave her a big hug and said, "Maybe it's just all those female hormones flooding my helpless brain, or maybe I learned that people can care for me."
"Oh shit, I better get you to employee health, I think you must have had a stroke, or estrogen poisoning, or something." She laughed and hugged me back.
Betsy and Kathleen also assumed that I was behaving like a love-struck teeny bopper because of Michael, which of course was only partly true. Everyone was so happy for me and no one really knew what had happened. I opened Thornton's computer and transferred more of his money to each of the accounts I had set up for the girls. I was almost euphoric. The only problem was, if we exposed Thornton as an embezzler, everyone would lose the bonuses I was so carefully building up for them. Maybe I could find a way to launder the money through accounts of his and have it disappear into the accounts of my friends. I'd have to check that out.
Michael called at around 10:30. I wanted to see him again, and he offered to take me to dinner again, but I had a dance class that evening. I decided to convince him to join me. "No, Michael, I have to go to class. Cynthia will just kill me if I don't." Then I put on my best pout, and hoping he could hear it over the phone, I continued, "Pulleeaase Michael, will you come with me? Then I brightened, "I'll make it worth your while."
"Why you little tramp," he teased back, "just what are you offering me?"
We settled on a late dinner after class. I would buy. Somehow that seemed backwards, but I didn't care. I was getting what I wanted, time with Michael.
When we left the studio at 10:00pm, I was flushed from the activity and thrilled from all the contact with Michael. He could really dance and he led me beautifully. When he first put his right arm around me, placing his hand on my left shoulder blade, I felt a thrilling jolt. I graciously laid my right hand in his left and for just a moment savored the feeling of being in his arms.
From then on, he was completely in control. That by itself made me more breathless even than twirling rapidly under his fingers. I felt like a teenager at a first dance, and I got such a kick out of the spins and turns. I felt so feminine twirling around under his arm, throwing my hair around my head, as he spun me elegantly with his hand above my head, my fingers swirling under his. I couldn't wait to try this in three inch heels. For now, however, I was sticking to low-heeled dancing shoes for safety.
At dinner we talked more about ourselves and I told him about my longing to become a woman. Neither one of us understood why we found the other attractive. He was usually into big buff guys with hard, muscular bodies, and I was into girls, and all their soft curvy parts. We agreed that it was perhaps a little easier for him because I, at least, was a guy.
"I like you a lot Sam," he said with a huge grin. "Now I can tell my gay friends I went out with Sam last night, and won't have to explain anything else. They'll just assume you are a guy."
We both giggled. This conversation went everywhere and nowhere, and we each learned bits and pieces about each other. But more importantly, we both really enjoyed the time we spent talking. We were fast becoming good friends, but as the evening wore on, I found myself wanting more.
I reached across the table and grabbed his hands. "Do you want to sleep with me?"
"Girls aren't supposed to be so blunt," he countered, smiling gently and looking into my eyes. I could tell he didn't want to put me off.
"Point being?" I parried his thrust, "I'm not your ordinary girl, remember, I'm a guy, and I want to know."
Oops! That was a little too loud. I had said it with a great confidence, as if I was showing four aces in a poker game, but the couple at the next table both looked over, startled. They had heard me! What the hell, I blew them a kiss. The guy sat goggle eyed, the girl just giggled. At least they were cool enough to be embarrassed for staring at me, and they turned away, which is a good thing because I was nearly breathless at my own audacity. A few months ago, I would have been mortified with shame if something like this had happened. What remarkable changes had overtaken my life.
I turned back to Michael. His face had a little blush left on it. I had embarrassed him too. I started to apologize, "Mi..."
He cut me off, "Yes. Yes, I do." He looked right into my eyes when he said that.
I knew immediately what he meant and decided to bare my soul. "I'm scared, guys have only hurt me before."
"Well, there's no rush. I do relish the thought of getting you naked, on your hands and knees on a bed, but I'm no high school lothario. In fact, just to make sure you don't feel forced, you'll have to beg me to get it." He gave me a huge grin, like he had pulled a straight flush to beat my aces. Now, he was the one feeling proud.
"I don't think that's how a gentleman acts," I said, pouting. "A gentleman should do whatever a lady asks of him." I tried to sound haughty and self-important. "She shouldn't have to beg. It's unseemly." I tried to look down my nose at him, but he was too tall.
"Well, when you become a lady, I'll become a gentleman." He laughed. I tried to look insulted, but laughter sputtered out of my lips despite my efforts. He picked up my hands and kissed them.
We necked in the hallway outside my apartment for 10 minutes before I went in. It was so delicious, his kisses weren't just on my lips and tongue, they were reaching into my guts. I was sure I knew exactly how a teenage girl being kissed by her first real love feels. I wasn't ready to go to bed with him yet, but I knew that one of these days I would. Yes, I was sure this was how a young girl must feel as she plans to lose her virginity with her boyfriend (those that get to do any planning, anyway).
And for some reason, kissing in the hallway, as if we were hiding from my mother, made it even more exciting, and made me feel even more like a teenager just beginning to experiment with sex. The memory of those kisses is still sweet.
That night I didn't need to wake Cynthia to comfort me, and I fell asleep easily. My life was far richer than I ever could have imagined. I was in my own version of heaven on earth. I had Cynthia to take care of me and to be my Mistress and lover. I had all the girls at work as my friends and I had Michael, my good buddy, and I hoped, soon to be lover.
I had Mandy White and Beverly Wells, who were almost like fairy godmothers to me, they took such good care of me. I had a 26 inch waist and almost 33 inch hips, and a cute butt with much more padding than I ever dreamed I could have. My hair was well below my chin, now cut into a sleek pageboy, which, still parted in the middle, framed my face in a way that made me look both innocent and sexy. I was totally comfortable as a girl in any social situation, and I couldn't imagine how I could pass as a guy.
And oh, I had breasts. Yes, real breasts! I was so excited when they started to form and now they were beginning to fill an A-cup bra. I was just thrilled with them and couldn't keep my hands off them. Neither could Cynthia, and she really knew how to use her hands.... and her lips..., and her tongue.
Although she was the only one besides me who actually got to play with them, the rest of the girls were so happy for me. They all noticed my expanding chest at work because I did my best to make them notice. When I showed them my new little boobs in the women's room one day, everyone giggled and hugged me. I had no shame about them whatsoever, I even managed to embarrass Cynthia one night as I bubbled on about them when she had friends over. She spanked me afterwards to teach me some modesty. Then she made me lick her until she joyfully came twice, and then mounted and rode me until I came as well.
That was one of the really good parts about having Mandy oversee my medication. I was developing a nice female shape, but not losing too much of my sexual appetite or ability (not that estrogen does anything to your ability to use your tongue). It is true that I didn't feel the need to get Cynthia into bed every ten minutes, like I did before I started hormones, but she had a really healthy sexual appetite anyway. Sex was one thing we had plenty of. And being the careful doctor that she is, Mandy made sure that I had stored away several sperm samples just in case my fertility was affected and we wanted something small and wiggly later.
With things having progressed as far as they had, everyone agreed that it was past time for me to start working as a woman, and I was about to take that major step. One of Mandy's lawyer friends had worked it all out. So I would no longer be Mr. Bradley Lawrence Miller. I would be Miss Lillian Samantha Miller. My social security number, school records, driver's license and birth certificate were all set to be changed and just this week, the company Human Resources office received a letter detailing my change in status and gender.
On the Saturday night before the big legal change Michael took me to the opera. He didn't know it yet, but I also intended to get myself laid by him afterwards.
The opera was at Lincoln Center. It is just the most amazing scene. The Metropolitan Opera House is one of three great performance halls arranged on three sides of a huge open plaza facing Columbus Avenue. There's a large fountain in the middle of the plaza and a broad set of stairs leading up to it from Columbus Avenue. The New York State Theater, which houses the New York Ballet is on the left and Avery Fisher Hall, home of the New York Symphony is on the right. The "Met" is straight ahead, its very tall arched windows sparkling with all the hundreds of lights that hang in its huge entrance hall.
As you arrive after dinner at some cutesy little bistro that's within walking distance, there are all kinds of limos lined up along Columbus Avenue letting their terribly well to do riders out. And yellow New York taxis buzz in and out from the curb like yellow jackets at a fall picnic, letting out the merely affluent.
The men are in dress suits and dinner jackets, and they escort women in fancy dresses, immaculately coiffed hair, and fur coats. You walk up the grand stairway from the curb, across the plaza (upwind from the fountain when it's windy - that's one way you can tell the first-timers; they're downwind), and towards the doors of the opera hall. There's usually enough jewelry on display to pay off the national debt.
Needless to say, I spent the entire day getting ready. By 5:00, there was almost a party at the apartment, so many people had come to help and to watch me get ready for my "big date". Marci and Kathleen were there, and so was Mandy. Betsy stopped over for a little while with her current boyfriend, but our place was so drenched in over-heated estrogen that he was too uncomfortable to stay long.
Cynthia was stalking around the entire afternoon, too nervous to sit still. I finally called one of her old lovers, Jessica Moore, who came over and settled her down. Like Cynthia, Jessica was a strong woman, and could handle her in a way none of the rest of us could. Jessica was a VP at North State, and was one of Cynthia's mentors. She was one of the reasons Thornton was rather more careful with Cynthia than with the rest of us.
Anyway, I had been to the salon at lunchtime and was back at the apartment by 3:00 looking radiant, completely coifed, waxed, polished, and made over. Shelly had given me some auburn highlights around my face, something I had really, really wanted, but had refused to get while I still had to work as a man. More importantly, she had changed my hair so that it was now parted on the side, instead of in the middle. My hair now fell over one eye unless I really worked to keep it out. I just loved the look - very simple, but elegant, and all the women cooed over it as if I were the first girl ever to wear her hair that way.
My hair was sleek, smooth, and glistening. The makeup was done in the way that only pros can do it, and I had never looked prettier, although I now appeared more sophisticated than cute. I think it was the way she did my cheeks and eyes. When I got back from the salon, all I really had to do was bathe and dress. With all those women around, however, teasing and laughing and telling stories about ''memorable" dates, great and horrible, I was becoming increasingly anxious as the minutes ticked slowly away.
Finally, I couldn't take it any longer and retreated to my bedroom to take comfort in my cozy Laura Ashley world. Before I did anything else, I douched twice, so I would be clean for Michael. Then, I ran the tub, putting in the same bath oils that Cynthia had insisted I use to prepare for her first...., well the first time she fucked me with her dildo. When I had been in the hot steamy bath for about 15 minutes, I heard a gentle knock at the door.
It was Cynthia. She told me I had better hurry, so I wouldn't be late. Then she asked, rather timidly I thought, "May I help you dress?"
"Are you kidding? I thought you'd never ask. Get in here."
So, wearing a happy smile, she grabbed a big fluffy towel and wrapped it around me to pat me dry. She powdered me all over with a big powder puff that held a lightly scented powder, tickling me between my legs and making us both laugh. Then she held out my favorite satin robe and after she had me snuggled into it, we went into the bedroom. Next, unfortunately, came my gaff to conceal my penis. No way I was going to show an erection at the opera (really, I'm very proper), and knowing Michael, I wouldn't have been surprised if he had tried to give me one just when some old matron was looking. Then I slid into a pair of high cut, dark gray panties made out of some kind of silky-lycra blend, with black lace trim covering the entire front panel.
Cynthia walked me over to the mirror so we could study me carefully. She stood behind me as we appraised the way I now looked. She described what she saw, running her hands over the parts of my body as she described them, using her fingertips to highlight her words,
"Mmmm, you have such smooth, sleek, hairless legs, plenty long enough for anyone's needs, lightly rounded hips, and a cute round butt that seems to defy gravity. And that just brings us to your small, tight waist. Aren't you glad I make you wear that corset?"
She stopped for a moment and circled my waist with her hands. I could only nod yes in response to her question. Then she ran her hands up from my waist to my chest, on either side of my breasts. "Look at these adorable little breasts, almost A cup, I'll bet, with small dark nipples riding out front like they are just so proud to be there. And she tweaked them gently. I squealed anyway. And I just love your smooth dark hair that hangs down past your chin in such a glistening curtain."
She didn't say anything about my face, which was now the only thing that even hinted at my former manhood. But I knew it looked sophisticated and sexy, even without lipstick.
"Look at yourself," she was like a proud mom. "Look at the young beauty you have become. Think of your friends in the next room. Think of your date on his way here to pick you up. Think of me."
Then she nipped me on the neck with her teeth, and snaked her hands around my chest to cup my little breasts, molding them sensuously in her hands.
"Why are all these people so fond of you Lilly? Do you know?"
I just waited silently, reveling in her touch.
"You are a special young lady my dear. You are sweet and pretty. You treat people with consideration and care. You're generous with your affection, you're funny, and you have the most breathless sense of wonder about the world. You do seem like a 16 year old girl getting ready for her first big date. You are giving each of us a treat by allowing us to share this with you and to relive, at least a little, what was fun about our own childhoods. Whatever you might have thought about yourself in the past, you must now come to understand that you have touched our hearts, we value your friendship and love, and we want you to stay in our lives."
That was quite a speech and I was struck dumb by her words. I was so overcome with emotion I started to tear up. I turned in Cynthia's arms and hugged her to my chest, my naked chest with boobs on it. I was speechless.
Cynthia only let me linger there a moment before she gently pushed me away and said, "Don't you dare ruin your makeup." She grabbed a tissue and started to dab at the corners of my eyes. Once I had gotten myself under control, she hugged me again and whispered, "I love you, you are a joy to me. Whatever is best for you is what we will do. Now, let's get you dressed. I have a surprise for you."
I knew that she had given me permission to open my heart to Michael if it came to that. More importantly, she had taught me that love could grow to include more people, the more of it you give. She was going to let me fly away if I wanted to, and would see if I came home on my own. What a precious gift.
"Here look." I drew myself back from my thoughts and looked at her hands. She held a bra and two small breast forms. "We're getting rid of your old breast forms," she giggled. "We're going to push your new breasts up and out for the world to see, and these," she held up the hand with the forms in it, "will do that just perfectly."
In a couple of minutes it was obvious what she meant and I was ecstatic with my new look. The small forms went in the bottom outside edge of the bra and forced my own breasts up and in. I had real cleavage! And I didn't need makeup to do it! Oh, this was too good. I couldn't take it any more; I had to finish getting dressed so I could see what I looked like.
I sat on the bed and rolled my sheer seamed stockings up both legs and attached them to my garter belt (no way I was going to wear pantyhose on this night) . I had to be careful because my nails were longer than I was used to and filed into serious points.
Needless to say, we had debated the selection of my go-to-the-opera dress almost as hotly as the congress had debated campaign finance reform. But in the end only one choice was really considered. We all knew what this date called for. It just had to be a little black dress, even if it was getting awfully close to winter.
I refused to go sleeveless even though I was outvoted by every single person who was asked. But I knew that everyone would stare at the scar on my arm and I didn't want to have to deal with that on this night. So now I had the most darling dress. It had long sleeves which arose from shirred fabric that was sewn to look like broad shoulder straps that criss-crossed the outside half of each breast, revealing almost all of the middle half of each of my glorious, pale white globes. The right strap passed over the left and went down to my waist, where it circled around my waist as a thick band of fabric, almost like a belt. Two big rhinestones buttons attached the loose end to the point where it had started to run around my waist. The skirt was formed from a layer of opaque rayon with a separate layer of organza over it. Both were gathered at the waist, enhancing the difference in size between my waist and hips. Both layers also swirled out slightly at the hem, so the whole skirt swung alluringly about three inches above my knees. It would take some concentration on my part to keep my stocking tops concealed and I pulled the garters as tight as they would go.
I wore a diamond stud in each ear, and drop earrings, with emerald-colored stones. They looked simply terrific when I pulled my hair behind my ear, a flirty move that I just adored. I had a golden chain holding one fairly hefty fake emerald that matched the earrings and hung down between my breasts to draw everyone's eyes to what I now saw as my irresistible cleavage. A couple of golden bracelets on my right wrist and a dress watch on my left completed my jewelry.
Of course, the ring Cynthia gave me never left my finger. When Cynthia first gave it to me, the gold was scarred and unpolished. I had it cleaned it up and the whole thing now glistened. I always selected any other jewelry I wore to compliment the ring, the beautiful gold and emerald ring that my dear, sweet girlfriend, Mistress, mother, and mentor had given me all those months ago. God, I just adored her. I kissed the ring.
My shoes were elegant three inch black pumps. They were cut very low at the sides and had a strap around the ankle. I just had to have ankle straps; they're so sexy. I had a small, beaded black clutch bag that came with a long thin strap, and a long black silk scarf to wear with my coat. If I got chilly in the theater, I could wrap the scarf around my shoulders.
I emerged from my bedroom feeling glorious, but suddenly felt very shy when I got in front of all my girlfriends. But they proved to be true friends. They met me with dead silence and somber faces, clearly designed to scare me to death, like maybe I was wearing a "kick me" sign. My initial rush of shyness started to turn to panic, but only for a moment, because in the second moment, a chorus of praise serenaded me. That simply released all the tension I had been accumulating throughout the afternoon, and I felt so good I did a twirl before anyone even asked me to.
This elicited a wolf whistle from Marci, and "Oh honey you look gorgeous," from Kathy, and applause from Mandy. I twirled on my toe to spin the skirt and my hair. I put one hand over my head, fingers pointed outwards like a ballet dancer and trailed the scarf in the other hand so it flowed around me as well. I was feeling almost drunk, but it was from happiness. I hadn't had a drop of alcohol.
When Michael arrived 10 minutes later, he too was more than impressed. He gave me a big hug, and an air kiss, so as not to ruin my lipstick. He was so thoughtful. But he was in a rush to get out of there, just like Betsy's boyfriend. Even gay men can be driven off if there's enough estrogen in the atmosphere. I went to grab my only warm coat so he could help me put it on.
Mandy stopped me though, "no don't wear that. Take the one that's in the garment bag on the left."
I unzipped the bag and gasped, astonished by what I found there. It was a pale gray full-length fur coat, it must have been fox, with a big, floppy fold-down collar and a sash to hold it closed. I was so surprised I stepped back.
"Oh Mandy, I couldn't possibly..."
"Oh yes you could," she said, "in fact, as your doctor, I insist, we can't have you catching cold now can we?"
I started to panic a little. "No, I'd be afraid. I might ruin it or lose it. I could never make it up to you."
"Well," she said in a fake huff, "if you won't let me loan it to you, I may just have to give it to you. Then you wouldn't have to worry about anything happening to it."
She looked at me like she had just trumped my ace. I still couldn't move, but Michael made the point moot by hanging up my coat and grabbing the fur. He held it open and looked at me. I had no choice, so I slipped my arm in, turned slightly and put in the other. I wrapped the silk scarf around my neck and threw one end over my shoulder, allowing the other end to hang down in front. I picked up my purse, turned back to the room and curtsied. Everyone applauded again, and Michael and I headed out the door.
Mandy shouted after us, "don't you dare lose that coat!" I blanched for a moment, until everyone else laughed.
The restaurant was a standard, have-a-quick-dinner-before-the-show kind of place. The food wasn't anything special, but it was overpriced anyway. The décor at least, was nice, kind of country French - very warm and cheery, but formal with softly padded chairs, white tables cloths, fine china, and napkins stuck in the water glasses to look like flowers. It had to be expensive-looking with all of the expensively dressed people who were there.
I have to admit I was watching to see what kind of reception I would receive, and the men at the restaurant didn't disappoint me. Heads turned as I walked by. As far as I can recall, I always checked out every cute woman in a fur coat, and that rule seemed to hold for me. But interest really picked up when I took the coat off. The dress, heels, and stockings would have been eye magnets for any guy who merely caught a glimpse of me from behind, but the view from the front, especially my revealing décolletage, and best every cleavage (I had used some makeup to enhance it even though it was real) just overwhelmed them when they got the opportunity to see it. I was a little shy about the whole thing at first, but as I relaxed over first few minutes, I started to get into the whole idea of being a desirable girl with many male admirers. I even flirted with some of the guys who couldn't keep their eyes off me. This was so much fun!
Michael thought the whole thing was a rip. We leaned close to each other and whispered. To others we looked like lovers sharing intimate secrets, but we were really reviewing the responses of the guys who were eyeing me. We were like two fraternity brothers goofing on the townies.
I was sky high over the response I was getting and just had to ask Michael what he thought." Michael, do you find me attractive?"
"You know I do Sam."
"But how, why? You're gay, you've told me you're attracted to manly looking men. I'm doing my best to look like a sexy woman, what actually do I do for you?"
He looked at me for a moment with his head slightly cocked. "I'm not sure.... but I like it. Just because I'm gay doesn't mean I can't appreciate feminine beauty, and while you don't have the looks to be a super model, you are very attractive." He gave me a warm smile to show me that he meant he thought I was really very, very attractive. "Tonight you look simply fabulous."
I blushed and looked away demurely. It was time to flirt seriously with him. I wanted him to be hot later. He was going to beg, not me I had decided
"But there's something else about you... I'm not sure what it is. I certainly like the idea that you have a cock under that dress... you do don't you? I've never really checked." He smiled like a two year old who had just gotten the square peg into the square hole.
In return, I pouted at him like I was insulted. "Yes but not for much longer if Cynthia has her way. Would you like to see it before it goes?" I started to stand up. Thank god he put is hand on my arm before I got too far. I was only bluffing.
He gave me a condescending smile. "Later you tease."
"Really?" I lit up. "I'd like that. Can we go to your place?" So much for flirting, why bother, when you can simply throw yourself at your man instead.
He continued, " I really like that we're both fooling all these people. You're unreadable and I'm out with a guy I really like and I don't look gay to the world. Don't get me wrong, I don't mind being gay; I'm comfortable with myself. But it is stressful sometimes, even in a liberal city like New York. People give you dirty looks; they treat you shabbily, and you never know when someone is going to turn on you. This is just so much easier."
He paused for a moment and looked at me critically, as if, perhaps, he were a casting agent and I was a model looking for a job. Then he went on. "And besides, you are absolutely charming. You are intelligent, you know a lot stuff so you're easy to talk to, and I'm comfortable with you in a guy to guy kind of way. Yet..., you come across like a 16 year old girl, completely naive and innocent. You flirt shamelessly," I tilted my head and batted my eyelashes at him, "and frankly, I find it absolutely thrilling that you are attracted to me. You really make me feel good about myself and how I behave. I'm so tired of people evaluating and judging me by all sorts of lame standards. You know: is he gay enough, is he straight enough? Fuck it! You seem to like me because I'm me." He picked up my hand and kissed it.
"Oh, Michael, you are so nice to say that." I felt gooey inside and tightened my grip on his hands. I was afraid I was going to cry again (thank you for that, estrogen. I always wanted to be able to cry whenever someone said something nice to me).
I don't really remember much of what we ate for dinner, and stopped caring about whether people were checking me out or not. I only had eyes for Michael, and I desperately wanted to understand why I was attracted to him. Maybe I was gay, or bi, or something. But after a little while, I gave up. I decided just to go with the flow.
When we had just about finished our coffee, Michael pulled something from his pocket and told me he had a present for me from Cynthia. It wasn't much bigger than a business card, but rather thicker, and wrapped simply in gold foil and a cute little red satin ribbon. I opened it. It was a business card case in dark brown alligator leather, very elegant and very feminine. It had my initials, LSM embossed on the leather. I opened the case pulled out a card to read it. My eyes almost popped out of my head. It said,
Lillian Samantha Miller, MBA
Partner
M & M Financial Consulting Services
"What does this mean?" I asked Michael, a little worried about the implications of this card.
"It's part of your new identity as my steady girl." He grinned at me like the cat that ate the canary.
"I....." I must have looked panicked, I felt like a deer paralyzed by headlights.
"Just wait," he said, "calm down." He patted my hand. "We know we both like each other and you know I often need to take a woman to various social affairs. That's what got us together in the first place."
I nodded my head, still waiting to see where he was going.
"In my work, I run with a pretty exclusive crowd, and my date," he nodded at me, "has to be their equal or she will be dismissed as a bimbo or social climber. You, my dear are my new investment councilor."
"I am?" I squeaked out. "How?"
"Yes, you can talk financial analysis with anyone. You might even find some clients among this group - rich clients, if you are interested. If you don't want to go there, simply tell them you have no room for new clients at present. They'll be sucking up to you instead of looking down on you."
"Now listen carefully," he continued, even though I wasn't sure I was still with him. "You are not my 16 year old high school sweetheart. You are a mid twenty-something close friend and business associate. You can't hang all over me like you've been doing and you can't flirt with me every time you catch my eye. You have to be sophisticated, your own woman. Otherwise these people will eat you for lunch. They are arrogant, nasty, and dismissive - old money you know." He said that with a very bad English accent. "You have to be able to meet them on their own terms.
At least a few of my partners will be at the opera tonight. You will have a big advantage with the guys," he leered at my breasts, "so they should be no problem. The women, however, may be another story. Just watch for their claws and expect them to treat you like a rival."
All of a sudden I was starting to worry. Could I really pull this off? I licked my lips and realized that since I had just eaten I would have to freshen my lipstick. What if I had forgotten? It's one thing to be a ditzy little girl with your friends, who would find all your social mistakes amusing, but to be a sophisticated young woman with other women who will not like you the minute they meet you, because, well because you have nicer tits than they do, well.....
But my worries weren't going to get me out of this, so 15 minutes later, my heart thumping to match the clicks my heels were making on the sidewalk, we were walking hand in hand down 67th Street towards Columbus Avenue. A strange thought popped into my head.
I pulled Michael up short. "Michael, what does M & M stand for?"
"You're smart, Sam, you figure it out."
"Michaaeelll," I whined, "stop teasing me." I stamped my foot, just because it was a move I had always wanted to try and thought it might look cute just then. In fact my feet were already freezing and it hurt.
He looked at me with an innocent grin curling his lips. "Morrison and Miller, silly."
Oh no, she was actually going to do it, Cynthia was going to start a company with me. But we couldn't, we had to get Thornton.
Thankfully, Michael interrupted that thought before it could really form. "Come on," he said, "we'll be late." And he grabbed my hand and started to lead me down the street towards Lincoln Center.
Comments
The New Job
Wow, for a first story the detail is outstanding, I can't wait to see what happens to Lilly and the crew.
Keep up the wonderful and brilliant work.
Jayme Ann
The answers to all of life's questions can be found in true friendship
The answers to all of life's questions can be found in the face of a true friend
Excellent session
Lillie's on her way, what a ride!
Well done Ms Kelly.
LoL
Rita
Age is an issue of mind over matter.
If you don't mind, it doesn't matter!
(Mark Twain)
LoL
Rita
Rita, You have no
Rita,
You have no idea!
better fasten your seat belt.
Thanks for commenting
KAR
This just keeps on getting better...
So, Brad has more-or-less disappeared, to be replaced by Lillian (and occasionally Sissy).
Courtesy of Michael, Lillian has adopted the demeanour of a lovestruck teenager.
Now she's got to start acting like a mature, confident woman. Quickly.
Meanwhile the "creative accounting" continues, and Lillian's investigating ways she can both follow through on Cynthia's scheme to trap Thornton, whilst also preserving the bonuses she's built up for the girls over the past couple of years...
Whatever next?!
As the right side of the brain controls the left side of the body, then only left-handers are in their right mind!
I'm reading this in 2017, but
I'm reading this in 2017, but this was a first story ? I'm slightly jealous!
Great story, it's great to be able to read the next chapter right away.
Karen