16 year old Darren Peterman comes home from school to find his mother has bought him a new outfit, befitting of a middle aged woman. Can he face his father and little brother for the first time in a dress?

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Chapter 3
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I found it hard to concentrate in school because I couldn't stop thinking about my mother and what she might be buying for me. I knew it would need to be enough for me to wear to the salon on Saturday. And after that, she said we were going shopping for some more clothes. I thought about the old phrase that says you have to have money to make money. It was kind of like that with women's clothes. I need to dress like a woman in order to buy women's clothes. I was very cool with that.

Whenever I wasn't thinking about my mother and her purchases, I was checking out the girls in my classes. Looking at girls wasn't a new thing for me, but now I was almost studying them. Because they were born as females, becoming women would be easy for them. It would be second nature, something they didn't think about, the way I never gave much thought to becoming a man.

I compared their mannerisms to my mother and her friends. It was very similar in that they moved their hands around the same way when they talked, but teenage girls are much more giggly than older women. I didn't want to be giggly. I also didn't want to wear the kinds of jeans and tops they wore. Their clothes were trendy and I suppose there's nothing wrong with that, but the older women I knew wouldn't be caught dead wearing such things. I hoped my mom would buy me a nice wool skirt and a sweater top or maybe even a pant suit.

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My coach yelled at me a lot during football practice. He said my head wasn't in the game and he was right. Until today I had loved going to football practice and cracking helmets with my teammates, but now it didn't seem the same. I kept thinking there were so many other things I could be doing, like playing Bridge with my mom and her friends.

Tonight when I got home, my mom would have some new clothes for me. Tomorrow night our team would play at home against Wesley High School. Just last week my coach had taken me aside and told me there'd be some college scouts at the game. Even though I was only a junior they were interested in keeping tabs on me. I remember being so excited when he told me that, but at the moment I couldn't care less.

The next seven months were supposed to be a dry run for when I got my own boobs in the summer. I was supposed to use the time to decide whether or not it was how I wanted to live my life for real. Even though I'd never worn a dress in public, I knew in my heart that regardless of how things played out, there would never be a time in my life when I didn't want to wear women's clothes. So why should I waste my time going back and forth between boy and woman?

Thoughts of female hormones loomed large in my head. My mother had talked about the possibility of my starting female hormone replacement therapy even before summer. She knew as well as I did that the longer I delayed taking them the more masculine I would look in later years. Did I really want to risk that? I didn't think so.

My dad warned me not to rush into things. He couldn't comprehend my feelings but I think he could tell I was thinking with my dick. Don't let your dick make an appointment that your ass can't keep. Speaking of my dick, I haven't given a lot of thought to what I'm going to do about sex once I become a woman.

I was well aware of the effects female hormones has on penis size. I'd read a lot about it on the web, even though I never had any intentions of taking them. I knew that transexuals could still get erect with the help of Viagra, but what would I do as a woman with a stiff dick?

I considered my options. I could become a limp dick lesbian or I could beat my soft meat to climax, or I could take up sex with men and let them take me in the ass. Out of those three options, masturbation seemed like the only one I could live with. It wasn't as if I didn't enjoy having sex with girls, because I definitely did enjoy it. But being a woman seemed to take precedence over sex. I honestly thought masturbation would be enough for me.

I left the stadium and drove home. The anticipation was killing me. What had my mother bought? How much of a woman was I going to be tonight? And still, I wasn't convinced that I was doing it for the right reasons or if it would even be in my best interest. All I knew was that I wanted womanhood and damn the reasons for wanting it. I just wanted it to happen and I'd deal with the consequences later.

******

My mother was waiting for me when I came home. She was every bit as excited as I was. There were several bags and boxes sitting on the couch and on the coffee table. She told me that Dad had taken Sammy to dinner and to see a movie. She told me that we had the house to ourselves. I was elated.

I usually shower after practice in the locker room, but I had decided against it due to my lack of body hair. I knew I could handle a little ribbing from the guys and eventually it would probably happen, but I was stressed enough without putting more on the plate. My mom gave me a pair of panties and told me to put them on after I took a shower. "Hurry," she said. She didn't have to tell me twice.

Although I probably didn't need to shave again, I did it anyway. I wanted to look good but I also wanted the clothes to feel good on me. After drying off, I stepped into the pair of silk panties and pulled them up to my waist. The silk felt heavenly against my erect penis, but I did my best to think my erection away. I think that was the first time I realized that my penis was going to get in the way and it made me want to start female hormone therapy that much more.

The panties were exactly the kind I wanted. I knew from looking at pictures on the internet that panties came in a lot of shapes and sizes. I think a lot of guys think skimpy thong panties are sexy, but those are for young girls with slender bodies. The panties I was wearing were made for women with big bottoms. I wrapped a towel around myself and went downstairs to meet my mother.

My mom was waiting for me in the living room. She looked excited as she stood with her hands on her hips and a lit cigarette between her fingers. She was wearing a knee-length gray wool skirt with a blue v-neck sweater. The string of peals which had become a part of her daily ensemble years ago graced her neck. Her eyes danced behind her glasses and her highlighted hair swung as she asked what took me so long.

"I wanted to shave my legs again." I said.

"Well I hope you did under your arms too," she said as she took the lid off a box and removed a single large breast form. "I guess you know what this is. Don't you?" she asked.

"Its so big!" I said.

"It fits a D cup, the same size as mine," she said. "Now you'll know why I'm always complaining about my back."

I pinched it with my fingers and laughed. "I won't be complaining," I said.

My mother told me to lose the towel so that she could put some glue on my chest. It felt cold and sticky. I told her about the stories I read about breast forms sticking too well. "Will I be able to get these off before I go to school tomorrow."

"Don't worry about it," she said as she positioned the right boob in place. "We're not using super-glue. It should come off fairly easily in the shower."

"So I'm not going to be able to take them off before Dad and Sammy get home?" I asked.

"You could, but why would you want to?" my mother asked as she positioned the left boob in place. "Now comes the bra," she said as she pulled one out of a shopping bag. I watched as she adjusted the straps so that it wouldn't cut into my shoulders. She handed it to me and I put it on by hooking the clasps in the front and rotating it before slipping my arms into the straps.

"Are you ready for a bigger ass and hips?" she asked as she showed me a padded girdle.

"Its like the girdle pad I wear for football," I said as I took it from my mom and stepped into it.

"I suppose it is," my mother said. "But I wouldn't wear it in the game tomorrow. You're going to love this," she said as she pulled a top and a skirt out from another bag. The top was gold with black print and buttoned up from the front. The skirt was black polyester. "You'll need to wear nylons when we go out on Saturday." She laid them on the couch and gave me a black half-slip that she'd gotten from another bag.

I pulled the slip up over my padded girdle and my mom helped me with the zipper on the skirt. As I was buttoning up the gold top, my mother took a pair of black sandals from a shoe box and put them on the coffee table.

"Don't get to used to sandals," she said, "because I'd rather you wear heels. We'll get you some on Saturday. You'll need to practice walking on them but you'll love them because they'll make your legs look longer and slimmer."

I suspected that the next thing my mother had for me was a wig and I was right. It was ash blonde and looked like it would hang past my shoulders. I couldn't wait for my mother to get it on my head.

My mother told me it was made from human hair and that Brenda could put some highlights on it when we went to the salon. "Last but not least," I got you some glasses," she said as she placed them on the bridge of my nose.

I was afraid they'd make everything blurry but they didn't change a thing. My mother told me they were just for show and not prescription lenses. "They're for women who can still see but want to look smarter," she said.

I didn't know what I looked like but I sure felt feminine. "Can I look in a mirror?" I asked.

"Sure you can, but lets go upstairs and put a little make-up on you. I'm sure Brenda will give us something different to help you look older, but I can get you started. Would you like that."

"You know I would," I said excitedly as I grabbed her arm.

My mom led me up stairs to her bathroom and had me sit down in front of her mirror. I watched her in the mirror as she removed a cigarette from her Louis Vouitton case and lit it. I had watched my mother put on her make-up at least a thousand times or more and each time she did she always smoked, so I wasn't surprised she felt the need to smoke while she helped me with my make-up.

The night before, my mother had confessed her excitement over feminizing me, and judging by the look on her face, she hadn't been exaggerating. I don't think I'd ever seen my mother any happier than she was at that moment.

She explained what she was doing with the brushes and why she was doing it. She even had me try my hand at repeating the steps. I had never tried to use make-up in the past because I'd been intimidated by it, but my mother showed me that it was an art and not rocket science.

The smoke from her cigarette drifted toward my face and my mother waved it away with her hand and apologized. I told her it was okay and that I didn't mind because I really didn't. As a matter of fact, I wished I was smoking with her. Of course I didn't tell her that because I didn't think she'd take it very well.

Even though she smoked, my mother was a bit of an anti. She had always preached to my brother and I about never starting. I had confessed a lot of embarrassing things to my mother over the past 48 hours, but wanting to smoke like her wasn't one of them. I kept those thoughts and feelings to myself because I didn't want to rock the boat and upset her.

I had fantasized about being a smoker for as long as I had fantasized about being an older the woman. The two things went together for me and I could never separate them.

The funny thing is that even thought I thought about smoking all the time, I'd never been brave enough to try it because I was afraid of getting caught, that and I didn't think it looked right for guys to smoke. I probably feel that way because my dad doesn't smoke. Its always been a woman thing to me.

After my mother finished putting on my lipstick, she placed her hands on top of my shoulder and admired her work. "What do you think?" she asked. "You don't look my age but you look like a woman and a very pretty woman at that! Don't you think?"

My mother was right. I did look good, but I wasn't surprised because I'd been there for the total transformation. I just hadn't said anything about it until now. I told her I loved it. "I can't believe its really me," I said. "I don't even recognize me. I look like I'm in my thirties."

"I can't wait for your father and brother to see you like this" she said. "Are you scared?"

I wanted to bite my lip but I refrained because of the lipstick. I was almost afraid to move for fear that I'd mess up my mother's work. I told her I was scared to death.

My mother suggested that we go down stairs and have a glass of wine. "I don't want you to get the wrong idea about drinking," she said, "or make a habit of it. But I think it will help you relax."

"That sound like a good idea," I said as I got up from the mirror and followed my mother downstairs.

We went into the kitchen and I got two glasses out of the cabinet while my mother took a bottle of open wine from the fridge. She poured our wine and we took it into the living room.

I watched my mother as she lit a cigarette and forced myself to say something about it. "Is smoking good for relaxing too?" I asked as I took a sip of wine.

My mother frowned as she exhaled and said, "Yes it is. Its very relaxing, but it will kill you, but you don't have to worry about that because I'll kill you first if I ever catch you doing it."

That wasn't the reaction I was hoping for but at least she didn't sound mad at me for asking so I decided to try another question. "How old were you when you started?"

My mother groaned and shook her head. "I'm embarrassed to tell you this, but I started smoking when I was 11. However, I didn't smoke in public until I turned 14. That's when my parent's gave me their permission. I know that sounds young, but you have to understand that back then, everybody smoked. My high school even had a designated smoking area for the students. It wasn't like it is today."

I was blown away by her answer but I did my best to keep a poker face. I couldn't believe she was actually talking to me about it and being so casual. It made me wish I had asked her sooner. "If you don't mind me asking, didn't you know it was bad for you health back then."

"I did but I was in a hurry to grow up, kind of like you are," she said. "Isn't that why we're having this conversation, because you're thinking about taking up smoking?"

I told her that I didn't know what she was talking about, but the heat from my face and the stutter in my voice betrayed me.

She grabbed my hand and told me it was okay. "You don't have to be embarrassed," she said. "I'd be worried if you weren't thinking about things like smoking, and drinking, and sex. That's why we need to talk so that I can help you figure things out."

My mother hadn't set a trap for me and she wasn't angry. I was relieved but I was far from calm. "I guess I'm still trying to figure out the rules," I said.

Mom laughed and said, "Good luck with that. This isn't like football or having curfews," she said. "There aren't any rules when it comes to being an adult woman. Its all about the decisions we make. Some are better than others and they all have consequences." She took a sip of wine and asked if liked it.

"Its good," I said. "Kind of sweet."

"You know deciding whether to drink or not is one of those decisions you'll have to make. That's one of the reasons I offered you a glass."

"What? "Was it some kind of a test?"

Mom shook her head. "No Honey. Not at all. I know your father and I have had talks with you before about drinking, smoking, sex, and drugs, but those talks were meant for a teenage boy- not a middle aged woman."

"So does this mean I can make my own decisions from now on?" I asked.

"I suppose it does, but I'll still give you my two cents whether you ask for it or not. I can tell you right now that I'm not going to agree with every decision you make, but I'll try my best to understand and respect it. So what do you think? Do we have a deal?"

I nodded and wiped a tear from my eye. "Thank you," I said.

"So what kind of decisions are you working on right now" my mother asked.

"I shrugged my shoulders because I didn't want to say it.

Mom sighed and said, "If I had to guess, I'd say you were thinking about taking up smoking. Am I right?"

I answered her by nodding shamefully.

"Does this have anything to do with your becoming a woman?" she asked.

I cleared my throat and caught my breath. "Yes," I said.

"Is that why you asked if smoking was good for relaxing?" she asked. "Because if you're nervous about the transition, we could ask the doctor to prescribe a mild tranquilizer for you. That would be a healthier alternative to taking up smoking."

"Look Mom, this isn't about healthier alternatives," I said. "This is about me gaining confidence as a woman and feeling good about myself. Pills and wine can't do that for me," I said as I hoisted my glass, "but cigarettes can."

"I don't understand Darren. Where did you get this idea that smoking will give you more confidence?" my mother asked.

"From watching you," I said. "When you walk into a room and light a cigarette, you look so strong and powerful, like you could take on the world and win. But at the same time you're sweet and feminine, the way a mom and a wife should be. I've wanted to be that kind of woman all my life. That's why I need to smoke so I can be like you."

"I don't know what to say. I never knew you felt that way."

"So its okay with you if I start smoking?" I asked.

"I didn't say that. You're only 16," my mother said.

"But I'm about to be a 46 year old woman," I countered.

"Look Darren. I'm flattered to know you think so highly of me, but instead of being a carbon copy of me, shouldn't you be your own woman?"

Before I could answer her, the front door pushed open and my dad and brother walked in.

The logical part of my brain assured me that everything was going to be okay. My father had announced his support and we had already broken the news to Sammy. In some ways, them seeing me dressed as a woman was a period at the end of a sentence that had already been spoken.

However, there was another part of my brain that wasn't so logical. I was a scared 16 year old boy who was on the verge of humiliating himself in front of the little brother who used to look up to him and the father who had wanted a son he could be proud of.

It felt like another walk to the electric chair. How many times would my pride have to be executed?

"Hold your head up high and don't slouch," my mother said as we stood to our feet.

On any other night my mother would have asked Dad and Sammy how the movie was or what they had for dinner. But this wasn't like any other night. She stepped out of the way so that I was in full view of Sammy and my dad. I saw her arms swing sideways as if she was presenting me, which was exactly what she was doing. "So what do think?" my mother asked. "This is Nancy Peterman."

So there I stood in front of my gawking father and brother. I didn't feel like a beautiful woman. I felt like a scared boy who had just gotten caught wearing his mother's clothes. But the clothes I was wearing were mine. They belonged to me. My mother had bought them for me, and in some ways, that made it that much worse.

My father was the first to speak. "You look gorgeous Darren."

"I think it would probably be best if we called him Nancy when he's in woman mode," my mother said.

Dad shook his head and mumbled something about my mother being right. "I'm sorry," he said. "Its just a lot to take in. I thought I'd know what to expect but you look so much better than I thought you would. You really are beautiful Honey."

"Thanks Dad," I said sheepishly.

"You know I've been thinking about this," my mother said. "And its definitely not a good idea for you to call your father Dad when you're dressed like this in public. Its fine for right now when we're home, but we should probably tell people that you are your father's sister and that would make you Sammy's aunt."

"I think your mother is right," my father said. "You should probably call me Bill when we're out in public."

"And I should call him Aunt Nancy?" Sammy asked.

My father squeezed Sammy's shoulder and told him he was right.

"You're not going to go to school tomorrow like that. Are you?" Sammy asked.

"No Honey," my mother said. "Your Aunt Nancy is going to be your brother Darren tomorrow morning. I know this has to be confusing for you because its confusing for your father and I, but it will get easier for all of us in time. And when summer get here, your brother will be gone forever."

"So he's going to be a real woman like you for the rest of his life?" Sammy asked.

"That's right Honey. Just like me forever and forever," my mother said.

My mother's words hit me hard and I felt as if I was going to pass out so I took a seat on the couch before I could fall. Oh my God, I thought. What have I done?