The Dress-Up Game

By Pamela

([email protected])

Jill and I rode the F train to Manhattan from Forest Hills. I was taking her to ice skate at the Wollman rink in Central Park. This was our third date. Every time I’ve asked her out she’s said “Yes” and I found that hard to believe. To my mind she’s very pretty and I adore her long light brown hair. She’s graceful and has a feminine delicacy like one sees in ballet dancers. She had taken some ballet lessons when she was younger, but decided to give it up in favor of piano lessons.

I don’t see myself as good looking and I’m definitely uncomfortable around girls, especially pretty girls. I have the damnedest time speaking to Jill on the phone. Just building up the courage to call her takes me days. Then when I call my mouth is as dry as a desert. I have to keep a cup of water next to me or else I’d only make croaking sounds when I talk. Then, when I speak I’m sure I sound like a robot. Short, clipped sentences. I’d quickly run out of things to say except I keep a list of topics in front of me. Despite all this, Jill seems happy to go out with me. She and her mother are invariably smiling when I show up at the door of their apartment.

Before we left for Manhattan, Jill and her mom had a muffled conversation across the room and I saw her mom hand her some cash. The mystery was solved when on our way to the subway Jill asked me if I would mind if we had time after we skated to do a bit of shopping on our way home. “If we get off the subway one stop earlier, then there’s a little shop on Queens Boulevard that my mom’s friend owns. I have to get a new bra and panty to go with my new pretty dress. It’s for my cousin’s wedding tomorrow. Just before you came to pick me up my mom decided that my usual bras don’t look right under the dress. So it’s kind of a last-minute emergency to get a new bra. Is this okay with you?”

Is this okay with me? My mind raced to come to grips with the many ramifications of what Jill had just said to me. Accompanying her to a shop selling lingerie? Confiding in me that her current bra doesn’t look right under her new dress? What does her new, pretty dress look like? What would be the right bra for her to wear with her new dress? What will I do in the store while she’s buying her bra? Would there be many women there? Would I be the only guy? Should guys even be in a lingerie store? Can I control how nervous I’m going to be in the store? Will I be able to not stare at the lingerie? Will my own desire for bras and panties not be obvious? Will I be able to contain my envy of Jill and the other women? I could go on and on.

Jill was looking at me waiting for my answer and I said, “Sure.”

“You’re not just trying to be polite?”

I felt my face getting hot. “No, Jill. Um, it’s okay.”

“Good, Greg. This is so last minute and will save me from curtailing our date.”

“I appreciate that, Jill. We’ll have an extra-long walk back to your apartment. That should be fun.”

Jill smiled at me. I tried to smile naturally in return, though my mind was already imagining what her unseen bra looked like. The one that wasn’t appropriate to her new dress. I also had to fight a desire to fantasize what it will feel like to be in a lingerie shop. As the day progressed I found myself often returning to the thought that underneath her clothing, Jill was wearing a bra. She was lucky and I envied her. I did get the courage to hold Jill’s hand while we skated and then later walking back to the subway. Of course, we were both wearing gloves. I had the feeling that she liked holding hands with me.

When we left the subway at the station before her usual stop, I felt anxious. The lingerie shop was going to be uncharted territory. I had never been in one before. What would it be like to be surrounded by girls underwear? Even a picture of a teenage girl modeling a bra and panty or panty girdle in a magazine could cause me to stare with rapture. Besides wishing that the model could become my girlfriend, I was jealous of her opportunity to wear lingerie. I longed to be the model. To have her figure, to have her hair style and her pretty face.

I’ve long had a crush on Jill and being on a date with her is the nicest thing that has ever happened to me. I’d love to be able to kiss her and to hold her. I wish that I might see and touch her body. At the same time I can’t stop myself from envying her girl’s body and the easy way she must wear her girl’s underwear and skirts. I’ve walked past the display windows of lingerie shops and snuck guilty sideways glances lest someone observe my hunger for what I see inside. I once waited for a bus at a stop that was in front of a lingerie shop with a large display of bras and girdles in the window. For fifteen minutes I was transfixed pacing back and forth and stealing looks at the bras. One bra in particular my eyes went over dozens of times and I coveted it. What I wouldn’t have given to get that bra. To own that bra. To know that that bra was mine. And then if I could be a girl who woke up in the morning and wore it. A girl who’d wake up in the morning and sit on the edge of her bed. My beautiful breasts would be nestled in front of me jutting out from a feminine chest and I’d arrange my bra getting it ready to put on. I’d arrange the cups behind me and clip the wings in front. I’d swivel it around and then lift it up aiming to catch both of my breasts in the cups. I’d have to use my hands to arrange each breast gently and delicately in their cup. When they were snug and comfortable I’d make sure the straps were in the right place. I’d feel around on my back making sure that the tags were tucked under the bra strap. Then, my bra would be on and I’d be ready to put on a dress or a blouse over it. And all day long I’d know which of my bras I was wearing. Every so often, when I shifted my position or bent over I’d feel a gentle shift of my breasts within the bra.

It's only been in the last year, since I turned thirteen, that I realized that I had a longing for bras and panties. I knew I loved being with girls. My first close friend, Betty, was a girl. For several years we were buddies until I moved away. Then my friends were boys, but if I had an opportunity to play with girls I would play with them. My coveting of bras and panties has grown within my desire for girls and has left me unable to sort out exactly what my feelings are. I passionately love and desire girls yet at the same time I’m supremely envious of them. It seems like a contradiction.

***

Jill didn’t seem to be the slightest bit concerned about taking me into the lingerie shop. Considering how jumpy I felt, it’s a bit surprising that she was oblivious to my discomfort. On the other hand, I’m pretty sure that the proprietor, Ms. Rutherford, the close friend of Jill’s mom saw my anxiety. She greeted Jill heartily when we entered. Ms. Rutherford was just ringing up a purchase by a middle-aged woman. On the counter were a half-dozen lacy bras and what appeared to be a lacy, white, corset. One by one she put the bras carefully into a paper bag. The woman’s desire for lace bras led me to imagine that she and I share the same feminine urge to be pretty. I wondered what kind of bra Jill wanted to go with her pretty dress. I hoped that it would be quite girlish with lace and a bright, sexy color. Looking at the many bras surrounding me, it shouldn’t be hard for her to find the perfect bra. I hoped she did find it.

After the woman left, Ms. Rutherford turned her attention to Jill who by way of introduction said, “This is my friend Greg. We were just ice skating in Central Park. It was so much fun.”

Ms. Rutherford and I exchanged greetings. I was sure that I sounded stiff, but at least managed to say something. I felt overwhelmed by the lingerie that surrounded me in every direction.

“How’s your mom?” Ms. Rutherford asked Jill.

“She sends her greetings.”

“What can I do for you Jill?”

Jill took out her phone and scrolled to a picture and showed it to Ms. Rutherford. “This is my pretty new dress that I’m going to wear tomorrow to my cousin’s wedding.”

Ms. Rutherford studied the picture for a minute and said, “How pretty!”

Jill turned to me and held up the phone so I could see the dress. In the photo she was wearing a pink dress that was so pretty that I almost gasped aloud looking at it. It was a dress fit for a princess. Exquisite lace details, a shirred bodice and pleated full skirt. I could not envision a prettier and sexier dress than that one. Jill and her mom had the greatest taste in dresses!

“My mom wants me to get a new bra and panty that go well with the dress.”

“I think we can do that. Let’s see now,” Ms. Rutherford said observing Jill, who had taken off her overcoat. “You were a 34A if I remember correctly, but I wonder if you’re now a B. I should measure you.”

Jill smiled and said, “You really think so? That’s great!”

Ms. Rutherford got a tape measure and Jill asked me if I would hold her coat. This delighted me no end. Just to have it in my hands and feel the warmth coming from her body was a treat. I watched as Ms. Rutherford measured Jill both across the widest part of her chest and then just underneath it. Since Jill had been wearing her coat for most of the day, it was just now that I had an opportunity to gaze upon the breast mounds within her blouse. With all the wonderful things about Jill that I was crazy about, I would now have to add her sexy bust. She had a girl’s chest. That explained – as if I needed an explanation – why she wore bras and why they were important to her. Ms. Rutherford said, “Just like I thought. You need to go up a cup size my dear. 34B.”

I could sense how happy this made Jill. Her happiness was infectious and I found myself silently cheering her accomplishment in bust size the same as if Ms. Rutherford had told us that Jill had scored a record number of points in a basketball game. Way to go girl, I thought. How nice it must be to be a girl and watch your breasts form. As they come in you’re forced to think of needing a bra. One day you look at your chest and you see increased fullness around the nipples and maybe some puffiness. Then maybe you don’t really need a bra in a functional sense, but you think that it would be a good idea to start wearing one so you get accustomed to having one on. You get trained in bra wearing. But part of that is in forming an ever-deeper assimilation of your femininity until you identify with the female half of humanity. I’m having breasts grow on me so this is my fate to become a girl and then a woman. This is what it means to be a girl. I’m developing this way into knowing that this is who I am.

But what of girls who resent their breasts coming in? Who wish they never got them. Or boys who wish beyond anything that one day they would see themselves getting breast buds that grew over time into real breasts. Except for them the breasts never come. But bras don’t have to have breasts. One can always wear bras. One doesn’t need breasts to feel like a girl.

“I’ve got three different bra and panty sets that should go very nicely with your dress,” Ms. Rutherford said. She went about the room looking for and selecting three bras that she brought back to Jill. All three bras were pink in one way or another. They had lace cups and little bows.

Jill held up the bras and said, “Oh wow. These are so much prettier than my normal bras.”

Ms. Rutherford laughed. “Don’t you remember when we fitted you for your first bra? You were sure that you didn’t want a pretty bra. You wanted the kind of athletic type bras that were similar to what your friends were wearing.”

“Like I’m wearing now.”

“Now that you’re turning into a woman, it’s quite natural to expand out your notion of what kind of bras you want to wear. Athletic ones are good for the times you’re very active, but a girl’s life has many moments where conventional bras are the better choice. They also effect how your clothing looks on you. That’s exactly why your mom sent you here today. A pretty pink dress with that styling is begging for a bra like these ones. They’ll create a very nice shape and position in your breasts that will go smashingly under your dress.”

I was fascinated by Ms. Rutherford’s comments. I hadn’t known that there was a connection between bra and outer clothing. But it made sense to me.

“Well, these bras are equally pretty. I’ll find out which one fits me most comfortably.”

Jill headed to a small changing room that was through a curtain. When she was out of sight Ms. Rutherford looked at me smiling and said, “You seem nervous about being in here. Are you?”

“I guess I am.”

Ms. Rutherford laughed. “You know Greg, maybe I shouldn’t say this, and I’m not implying anything, but I’ve noticed that many of the boys and men that enter my shop accompanying their wife or girlfriend are nervous about being around lingerie. Some are not. At the same time, men sometimes come in here to buy lingerie for themselves. These men are almost always nervous. That’s made me wonder if nervousness is a clue to a man’s secret desire for lingerie. I suppose they feel embarrassed for liking lingerie because real men are not supposed to have a feminine side.”

“Do you think I want to buy lingerie??”

“No, Greg, not at all.”

“I didn’t even know that boys buy lingerie for themselves.”

“Yes, some do. Not every nervous boy does so, but a lot do.”

“You mean I might be that kind of boy?”

“I’m sorry, Greg, I’m not really trying to insinuate that you’re one of those boys. I don’t know you well enough but I can see that the presence of all this intimate, female clothing is unnerving you. I have to say that you must feel threatened in some way.”

“I’m sorry.”

“No, no, no. There’s nothing to be sorry for. I’m just thinking that by talking about this it might help you feel a bit more comfortable being in here.”

“That’s nice of you.”

“The question is: Is your nervousness because you like lingerie – you like how pretty it is – and you think that only girls should feel that way?”

It was amazing how well Ms. Rutherford knew me. I blushed and Ms. Rutherford said, “I’ll take that as a yes. Please don’t be ashamed of yourself. I can see that it’s hard for you to acknowledge your feelings. Afterall, you’re worried how Jill will react to knowing that you like pretty lingerie.”

“Yeah.”

“Just remember that it’s okay if you like lingerie. I think that there’s nothing for a boy to be ashamed about if they like lingerie. It’s just who they are.”

“I see.”

“I bet I’m the first woman you’ve met who has said this to you. So certainly it’s going to take you some time before you absorb what I’m saying and even believe it.”

Jill called from the changing room. “I love this bra, Ms. Rutherford, can I show you?”

Ms. Rutherford looked at me and said, “Let me take a peek at Jill’s bra.” She went to the changing room and behind the curtain I heard her say, “So pretty on you Jill! The bra holds your breasts in the perfect location. You say it’s comfortable?”

“Yes. I love this bra.”

“Try on the other two and let’s compare them.”

Ms. Rutherford left the changing room and returned to me. “Jill is so pretty in that bra.”

My imagination of what that looked like was running wild.

“So getting back to what I was saying. Pretty lingerie is designed to be liked and especially by men for its sexuality. It’s lacy and many girls tend to like lace. Pretty colors like pink are used which is the stereotypical girl color. Then there are the little bows that the designers put on because many women feel prettier wearing bras with bows.”

“Bows?”

“Let me show you.” Ms. Rutherford took a bra off of a nearby rack and showed me the bows

“I see.”

“Pretty, aren’t they?”

“Yeah.”

“Some boys like lingerie so much that they act on their desires and buy themselves a bra and panty. Some love stockings and so they buy either a garter belt or a girdle to hold them up. The feel of stockings on one’s legs is very sensual and some men love that feeling the same as many women do.”

“I’ve never done anything like that!”

“I’m talking in general terms here. The truth is it makes me sad to see nervous boys enter the store and ask me for a bra. They’re suffering so much. I do my best to make them relax and assure them that I’m not judging them.”

I wondered if Ms. Rutherford said this to let me know that I could come back by myself to buy a bra and she would be supportive of me. I whispered to Ms. Rutherford, “Can Jill hear us?”

“I don’t believe she can. I see, I’m sorry. You think that if Jill knew that you like pretty lingerie she might not want to date you anymore.”

“Jill might think I’m a creep.”

“You’re not a creep, though I guess you’re right in the sense that some women prefer men who are not interested in lingerie. Some don’t want any blending of the male and female roles so that a man with a taste for lingerie would be violating their world order. From everything I know, however, about Jill’s mom she’s quite liberal as far as these things go. I assume that Jill is the same way, though I can’t be certain …”

“I’m the same way?” I heard Jill say. We both turned and saw that unbeknownst to us Jill had left the changing room. She was wearing a bra with the tags hanging off it and her jeans.

The sight of her absolutely beautiful chest sporting a pretty bra nearly caused me to faint. I had never known that life was capable of providing sights that were so beautiful. My heart ached with desire for Jill. At the same time I felt a pang of envy.

“I’m sorry Jill,” Ms. Rutherford said, “I should have checked up on you in the changing room.”

“No problem. I realized that there is no real reason I need to hide my bra from Greg. Do I, Greg?”

I stared at Jill desperately trying to say something other than “Oh my God!!!” Finally I squeaked “No. It’s okay.” Luckily, I stopped myself from saying, “I don’t mind.” Imagine being offended by seeing Jill in her bra? Whew, that’s a crazy thought.

“When I came out of the changing room Ms. Rutherford, you were saying that I’m the same way. About what?”

Ms. Rutherford said, “Greg and I were talking about the fact that some boys and men like pretty lingerie. Some of these boys come to the shop to buy themselves bras and panties. I mentioned that some women might not like that but many have no objection. It doesn’t bother them and they may even be supportive of such men.. I was saying to Greg that I’m pretty sure that your mom doesn’t have a problem with men who wear lingerie and I said that I didn’t know if you felt the same way as your mom.”

Jill looked at us puzzled and said, “I guess I never thought about that.” She thought a few seconds and added, “How did that topic even come up?”

Thankfully, Ms. Rutherford jumped in to save my neck. “I was talking to Greg about boys who enter the shop feeling nervous. They often are the ones that have a great affinity to lingerie.”

I wondered if Jill had noticed my nervousness. This whole time I was having an impossible time trying to pry my eyes from staring at Jill’s bra. Though I didn’t exactly know for sure, I could see that my love for the kind of bra that Jill was wearing was so intense that I would very likely one day want to take advantage of Ms. Rutherford’s barely disguised invitation for me to buy myself lingerie at her shop. Then, out of nowhere it occurred to me that I didn’t have to wait so long before I began experimenting with bras. In fact, opportunities would come when I could surely “borrow” one of my mom’s bras and wear it around the apartment. I wondered why I hadn’t thought of doing that before.

Jill laughed. “That’s a pretty funny conversation the two of you were having. Anyway, Ms. Rutherford what do you think of the bra I’m wearing now?”

Ms. Rutherford critiqued the bra for Jill. She thought that it didn’t fit her as well as the first one. Jill went back to the changing room to try on the last bra. Just before she reached the curtain I saw her hands on her back undoing the strap of her bra. Oh to have been in front of her to see what it looked like as the bra fell away from her.

When Jill was gone, Ms. Rutherford said, “Jill is just reaching an age where she’ll start understanding what kind of boys she likes. They very well may be boys who wear bras, or maybe not.”

“Thank you for not telling her I like lingerie. She doesn’t have to know does she?”

“Not at this point. In the future, when you’re in a serious relationship with a woman that could turn into a commitment, then you probably ought to make sure that they know your predilection. If you don’t it might lead to friction later on.”

“That sounds like good advice.”

“I can see that you’re a very smart boy, Greg. I think it’s lovely that Jill and you are dating.”

Ms. Rutherford went to the changing room and I could hear her discussing the third bra with Jill. Apparently there wasn’t going to be a show this time. A few minutes later Jill and Ms. Rutherford reappeared. It turned out to be the first bra that was the best of the three and Jill paid for it and a matching panty and we were off. Before I left Ms. Rutherford said to me that if I ever needed her help she would be happy to provide it. A day that had started with me having no thought about trying to get a bra to wear, was going to end with me plotting how I would get myself a bra. No doubt I’d begin by investigating my mom’s underwear, but I’m sure that I’ll also be thinking about Ms. Rutherford’s offer to help me get a bra.

***

While Jill and I were walking home I was pleasantly surprised when she initiated our hand holding. This was a first for me and I felt giddy with happiness. Jill said to me, “I never knew that some boys like to wear bras. Why would they want to do that?”

“I’m not an expert, but I suppose that they feel, at least partly, that they’re a girl? Like they are a boy with some feminine feelings in them.”

“That’s interesting. I know a couple of girls who can get really scary when they’re mad. It’s like that they become a tough boy. So a boy who can sometimes feel like a very feminine girl is the opposite of that.”

“I suppose that’s true.”

“You were nervous going to the lingerie store?”

“I guess so.”

“Did Ms. Rutherford think that that meant that you liked lingerie?”

“Sort of. I told her that I appreciate the fact that lingerie can be pretty. She said that pretty lingerie is meant to be pretty so people will like it. Girls and, oftentimes boys, as well.”

“I like pretty lingerie.”

“And dresses! I thought that you were pretty in the picture you showed me. You and your mom picked out a very pretty dress.”

“Thank you, Greg. I absolutely love that dress. I knew it would be flattering even before I put it on. I’m so lucky that my mom realized that my bra didn’t look right with it. I’m so excited about the bra I bought and I can’t wait to see how the dress looks when I’m wearing it.”

We walked on in silence. The image of Jill wearing a bra in the store kept coming back into my mind. The fact that she had been so casual about letting me see her that way piqued my curiosity. What did it mean about how much she liked me? Would she have done that for any boy? She had even asked me if there was a reason she should hide her bra from me. What reason did she think that might be?

I thought about everything that had gone on this day. How much closer I felt to Jill. The thought that I’d have to wait several days to find the nerve to call her up again for a date was more that I could stomach. I girded myself for rejection and said, “I had so much fun today. I hope we can go out again.”

I glanced at Jill and she turned toward me and said, “I’d love to go out with you again, Greg. When should we see each other?”

I was so happy that I could have cried. “Next weekend?”

“Sure. Come over to my house on Saturday right after lunch and we’ll decide what we want to do.”

“Great, Jill!”

***

During the week I daydreamed about my date with Jill and made-up fantasies of what we would be doing. Staring me in the face every day was also the thought that I could investigate my mom’s bra drawer and see what I could see. I held back out of guilt that neither my mom nor Jill would approve of me pursuing my mom’s lingerie. Unfortunately on Wednesday evening I would be alone in the apartment. My mom would be away to play bridge with her friends and wouldn’t be back until midnight. I’d have five hours to fight off my desire to see my mom’s underwear.

I lost the battle in the first half hour after she had left. The allure and mystery of my mom’s lingerie was too powerful to resist. I opened her dresser drawer and was rewarded with a view of panties on the left side and bras on the right side. Why had I never thought of going here before? I rifled through the bras which were of several different styles and colors. A lacy one near the bottom most attracted me and I gently took it out. It seemed like the bras were not situated with any notable precision. My mom would never know that I had taken out a bra to try on.

The bra was light blue and was made by Prima Donna. I noted the size of 36 DD. The intensity of emotion in me was so strong that I felt like a prospector hitting a vein of pure gold. I turned my attention to the panties and found a light blue one in the disordered panty pile and took it out. I closed the drawer and went back to my bedroom and undressed. My boner was painfully hard. It was as if my penis was way out in front of my mind. It was expressing its opinion of why I needed to put on the bra and panty. When I had them on I looked at myself in the bathroom mirror. Though my chest lacked breasts to fill the expansive cups of my mom’s bra, I thought that there was a definite femininity to my appearance that was not unlike the way Jill looked like in her bra. Well, of course her breasts were real and B cup and filled the bra cups in a delightful way.

An overwhelming desire to rub on myself descended on me and I came in a matter of a minute. I sat panting on the closed toilet seat feeling like I had let Jill down. I took off the underwear and put it back in my mom’s drawer and swore that this would never happen again. Thank goodness Jill would never know about this side of myself.

An hour later I was back at my mom’s drawer borrowing the same bra and panty. Once again I put them on and once again relieved myself. Once again I swore this was the last time and once again I felt relief that Jill would never know what I had done.

***

On my way to see Jill on Saturday afternoon I decided that the reason I had worn my mom’s underwear was because I wasn’t with Jill. Her absence drove me to act out both halves of our relationship. By wearing my mom’s bra and panty I became both her and myself at once. Of course, this was wishful thinking.

Jill was radiant when I showed up at her apartment. She was wearing a white blouse and dark blue, pleated skirt and seemed happy to see me. For the afternoon she had devised a plan. We’d walk in a nearby park, then visit an ice cream parlor. Then we would hang out in her room for a while. It was a mild late winter’s day and for the first time we held hands without wearing gloves.

I asked Jill how the wedding was and she said that it was a beautiful ceremony. She liked the reception and especially dancing to YMCA. “Did everyone like your dress?” I asked.

Jill laughed. “Right! My dress. I think many people thought it was prettier than the bride’s wedding gown. Thank you so much for allowing me to squeeze in our bra shopping last week. It was a lifesaver. It made such a difference with my dress. I got many compliments about my figure. I’m sure that with my usual bra that wouldn’t have happened.”

“That’s neat.”

“I also got to wear pantyhose. There aren’t many occasions where my mom lets me wear them. I guess I’m a bit of a strange girl because I like the way that pantyhose feels on my legs. I also got to wear the heels my mom bought that went with my dress. They’re okay but I wished that the heel were another inch higher. That’s one thing I really want to get one day. Some spike heels. They’re so pretty.”

“I guess for boys it’s kind of boring what we wear.”

“That’s true. Maybe that’s a reason why some boys like to wear girl’s clothes. There aren’t enough choices in picking out boy clothes.”

I laughed, and said, “Maybe that’s it.”

“Have you thought any more about why some boys like to dress in girl’s clothing? I’m still curious about that.”

“I can’t say anything more than I said before. I just think some boys have a girl side to them. They need to express it by wearing girl’s clothes.”

“Do you have a girl’s side to you?” Jill asked. She sounded like she was being funny

“To be honest, I think that all boys have some girl in them and all girls have some boy in them.”

“That makes sense. How much girl is in you?”

“That’s hard to tell. How much boy is in you?”

Jill laughed. “Not very much, I would guess.”

I don’t know where I got the courage to say it, but I said, “How much girl do you think I should have? How much would you like me to have?”

I saw some emotions pass through Jill’s face. Perhaps surprise, perhaps intrigue. I’m pretty sure that she knew as well as I did that we were getting onto some risky ground in our conversation. Jill looked at me and smiled. I felt her hand tighten a bit on mine and she said, “I do think it’s kind of fascinating that some boys want to wear bras and panties. Dress like girls.”

“I suppose it is a strange thing about some boys,” I said, wondering where in the world Jill was going with this.

“Anyway, I thought about it and I realized that I’m one of those girls who doesn’t feel bad about it. In fact, …”

Jill hesitated. My ears were focusing on any words she might now utter. “Actually, I’m a little afraid to say what I realized. I like you, Greg. You’re fun to be with and I enjoy our conversations and I think you’re cute. I don’t want to upset you.”

“Upset me?”

“What I’m trying to say is that when you asked me how much girl I would like to be in you, the answer that came to my mind is that you should have enough girl so that I could get to see what you looked like wearing a bra. For some crazy reason I’m curious about that.”

“Really? You want to see me wearing a bra?”

“Yeah, but a bit more than that. I want that you have a girl side, and that that part of you is happy to wear a bra.”

“That won’t freak you out?”

“Not me! What I’m afraid of is that you’ll be mad at me for saying that. You won’t want to see me again!”

“I’m not mad at you. I’m glad that you’re honest with me. I like you a lot. You’re very interesting and very pretty. I like that I’ve gotten to know you well enough that I’m not so nervous around you as I had been.”

“I know! I felt so sorry for you during our phone conversations. You seemed so nervous and I didn’t know what I could do about it.”

“It’s okay. Anyway, to respond to what you said about me having a girl side, I confess that part of me does feel feminine. That part of me wouldn’t mind wearing a bra if that’s what you’d like me to do.”

“Really? That’s so sweet of you!”

“I’m just being honest.”

“The thing is Greg, while I’d like to see your girl side wear a bra, I really, really, want your bra to be the same as my bra. I want us to have the same bra. Maybe a different size for you, but still the same. You saw my new bra. That’s by far the prettiest bra I own and that’s the bra I’d like to see you wearing with me.”

We continued our walk, though I must admit that it was hard for me to think about anything else other than how I was going to obtain the bra that Jill wished me to wear.

***

Jill and I had ice cream and returned to her apartment. There was a note on the table saying that her mom was on an errand and would be back in a couple of hours. Jill took me into her bedroom and she told me to make myself at home while she went to the bathroom.

I gazed around the room. It was clearly that of a girl. About as neat as my own room. The wallpaper was a pale pink with some slight decoration of flowers on a vine. There were some stuffed animals on her bed and a couple of dolls. She had a bookshelf and I was reading the titles when she came back. I went to pee myself and when I returned Jill was relaxing on her bed. “Come sit here,” Jill said indicating the spot next to her at the top of the bed.

I took my shoes off and joined her. Thus far, our earlier conversation had served to smooth my nerves so that I wasn’t terribly nervous. I knew Jill really liked me and I really liked her. But now I wondered if I were supposed to initiate physical contact or would she get upset with me. We sat side by side for a while and I looked at Jill and she laughed. “You’re nervous, Greg, aren’t you?”

I reached out and held her hand, figuring that this was not pushing the envelope as would be if I tried to kiss her. We sat like that a minute and I said, “I can’t help but wonder why you like me to have a girl side.”

“That’s a good question, but hard to answer. I mean it’s like something I just feel within me rather than something that I thought about.”

“It’s okay if you don’t know why.”

“No, you deserve some kind of answer. It is a lot to ask of you. That’s why I was worried about asking you that. Anyway, let me see.” Jill turned to look at my face. “I think your face is not quite that of a boy and not quite that of a girl. So I feel sometimes that I see a girl in you and sometimes I see a boy.”

“Really?”

“I hope that doesn’t upset you. Either way your face is pretty or handsome in my opinion. It’s a pleasing face to look at.” Jill thought some more and said, “When we ice skated together I thought you were graceful in the way girls are, though I could see the boy in your body.”

“So my body seems like that of a girl and a boy?”

“Yeah. That’s true.” Jill laughed, and said, “Take off your shirt. I want to see something.”

I wondered what Jill was up to as I pulled my shirt off over my head. When I was sitting next to her with my bare chest she said, “Just like I suspected, Greg. Your chest is smooth and delicate like that of a girl. Not muscular. A pretty bra would look really nice on your chest. It would look very much like the way a bra looks on a girls chest.”

“You think so?”

“Do you remember what my chest looked like last week? When I left the changing room wearing the bra?”

“Yes.” Boy did I ever remember that!

“Then you can see the similarity. If you were wearing the same bra as me, all you’d need would be something to fill up the cups. Obviously, you don’t have breasts like a girl does, or like I do.”

“I see.”

“I know that they sell silicone breast forms. Often for women who had cancer and want to replace their breast after surgery. If we got them and put them in your bra, we’d both have a girl’s chest.”

I had arrived at a place where I was mentally paralyzed and could not talk. My mind was processing over and over Jill’s statements. I was so wound up with excitement wondering when the time would come when Jill would dress me in a bra with breast forms.

“You’re such a great sport, Greg, that you allow me to go on like this. You’re sure you don’t feel threatened by what I’m saying.”

I shook my head and croaked out, “Not at all.”

“Good. That’s one thing I really like about you, Greg. You’re so willing to be open minded about new experiences. That’s the way I am also. We really have that in common.”

I calmed down enough to ask, “Should I put my shirt back on?”

I saw a flash of disappointment in Jill’s face, “If you want to. I was thinking that before you did, you could put on a bra so we could see what that looks like.”

“No, I’m happy to do that. I just didn’t know that you meant that we should do this today.”

“My mom won’t be back for a while. So I’m thinking that one of my mom’s bras should fit you. She’s a thirty-six. I’m just a thirty-four and that might be tight on you. Just a second.”

Jill got up and left the bedroom. My pants were in turmoil. My poor penis was all over the map in its response to my conversation with Jill. Boners were coming and going. I was sure that I was leaking a bit. A minute later Jill came back holding a white, lacy bra and she said, “My mom wears mostly white or black bras. Most of them aren’t very pretty. I think this is her nicest bra. I’ll help you on with it. Hold out your hands. She aimed the shoulder straps to go over my hands and pulled them up to my shoulders. She reached behind me and fastened the clip. “How does that feel? Not too snug at all. I think it’s a great fit.”

I was now fully catatonic. In a state of delirious ecstasy. The lace design of the bra was beautiful. Jill leaned back to look at her handiwork. “Absolutely adorable, Greg. Just like I thought. Your chest is so pretty when you’re wearing a bra.”

“Can I see?”

“Come to the mirror with me.”

We went to her bathroom and I looked in the mirror at myself wearing the bra. Jill was next to me looking at the bra. Then she looked up at me and smiled. “I’ll take my top off and we can compare ourselves.” She unbuttoned her blouse and took it off to reveal the bra that she had bought the previous week.

“It’s your new bra!” I said.

“Yeah. I guess I’ve had a sudden change in attitude. I’ve decided that I like this pretty bra so much more than my old bras. My mom promised me that we’d go back to the shop and get me a variety of pretty bras. I’ll just wear my old bras in gym class. That kind of thing.”

With her blouse off we looked at each other in the mirror. Me in her mom’s white bra and she in her fancy pink bra. “It’s just like I imagined,” Jill said. “Your chest with a bra is just as pretty as mine.”

I had to admit that there was a feminine delicacy to my chest that was accentuated by the bra. “I see what you mean.”

“This is so much fun. To make it better you have to get a bra like mine. It would be so cool if we both wore the same bra!”

“I could go back to the shop and I’m sure that Ms. Rutherford could fit me for the same bra.”

“Would you? That would be fantastic.” She thought a minute and said, “You should get a C or D cup. And see what Ms. Rutherford says about getting breast forms to fill the cups. She either sells them or knows where you can get them.”

“I’ll try and do it this week.”

“That’ll be so great, Greg. What a marvelous adventure for the two of us!”

I’m almost two inches taller than Jill. I turned to face her and she turned to face me. I looked down into her eyes and out of nowhere I knew I had to kiss her and I moved in toward her. My arms embraced her and her arms embraced me. We held each other tightly, my bra pushed up against her bra and breasts and we kissed. I was transported to a dreamland of happiness that I had never thought possible. The feeling of her breasts pushed into my bra was electric.

We kissed for a few minutes until Jill said, “I should put my mom’s bra back and we should get dressed. Sometimes Mom comes home earlier than she thinks. I took off the bra, gave it to Jill, and put my shirt back on. She returned the bra and put on her blouse again. We sat together in the living room and resumed kissing each other. I would like to have touched her breasts but was afraid to be so forward.

When we were resting from a long kiss, Jill said, “I can’t wait until we have a chance to wear our bras together again.”

“I feel the same way.”

“So your girl side is happy with this. I mean she likes wearing a bra?”

“I think that’s pretty clear.”

“I was thinking that you should make sure to get the matching panties with the pretty bra.”

“Oh sure. I’ll do that. Can I ask you a question, Jill?”

“What’s that?”

“If we were two girls wearing the same bra in the mirror would you feel the same as you did with me?”

“No. Not at all. Greg! I’m the kind of girl who only wants to kiss boys. What happened is that I thought about what Ms. Rutherford said about some boys wearing bras. Then I realized that boys who wear lingerie must have a girl part. Then it occurred to me that any boy who would honestly reveal his girl part to me had to be a boy I could trust. When I told you that I wanted you to be enough of a girl to wear a bra, you were honest about it. It’s very important for me to be with a boy I can trust. I don’t like to ever talk about it, but my dad ran away with a young girl and left me and my mom to fend for ourselves. So having a boy who is trustworthy means everything to me!”

I felt a few tears form in my eyes from Jill’s speech. I had figured she wasn’t living with her dad, but I hadn’t known that she had been abandoned by him. Jill saw my tears and held me. “You’re a treasure, Greg. So empathetic.”

“I just hate to think of you being abandoned.”

“You’re such a dear.”

“My own mom and dad are divorced. Soon after the divorce my dad got offered a great job in California and he moved there. I see him maybe twice a year now. He calls me every month.”

“That’s a shame. So both of us live with just our moms.”

***

After Jill’s mom came home I stayed a little longer. Before I left I told Jill that I’d make sure to go to Ms. Rutherford’s shop after school one day and buy the bra and panty. I’d also one way or another get breast forms for the bra. I had some savings that I could use. Jill hugged me and said that I’ve made her so happy. I should call her and let her know that I’ve bought the lingerie and then we’ll both think of when we could be alone together in our bras.

***

Mid-week I paid a visit to Ms. Rutherford’s shop. Before I entered I made sure that passersby wouldn’t see me. I prayed that I’d be alone in the shop and as luck would have it, the only other customer was just leaving as I came in. “Look who’s back,” Ms. Rutherford said. “I had the feeling that I’d see you again.”

“You seemed to suggest that you wouldn’t mind helping me …”

“Buy lingerie. Over the years I’ve seen a number of boys like you. Once they get the idea they could own their own bras and panties, they can’t resist purchasing them.”

“I don’t know what to say.”

“You don’t have to say anything. There’s nothing illegal about boys buying bras so we’ll just concentrate here on getting you bras that you’re happy with.”

“Thank you.”

“Does Jill know about your trip here?”

“Yes. She thought a lot about what you said that some boys like lingerie and she decided that she’s the kind of girl who doesn’t mind that they do. In fact, she and I agree that it would be good for me to buy myself a pretty bra. Actually we hope that you can fit me for the same bra that she bought. But it should be a C or D cup.”

“The two of you look so nice together. I’m glad that you’ve been able to be honest with each other. That’s something that even many adult couples can’t do. I’ll be happy to fit you with the bra that she bought. First I should measure your bandwidth.”

“I think I’m 36.”

“Perhaps. Let’s check. Take off your shirt, please.”

Ms. Rutherford measured the length over my nipples and said, “You’re right. Thirty-six is your bandwidth.” I followed her to a rack containing the same bra that Jill had bought. She went through it and said, “I only have 36D, no 36C.”

“Then I’ll get the 36D. Also the matching panties.” Ms. Rutherford looked me over and said, “I think you’re a size 6 panty.” She fetched one and said, “You should try them on. The bra also if you would like.”

“I can go in the changing room?”

“Yes, of course. Do you know about ... Let me show you.”

I entered the small changing room and Ms. Rutherford joined me. She showed me that there were paper liners that I should place in the panty before I put it on. She left and I took off all my clothes, put on the bra and then following her instructions I put the panty on with the liner. It seemed to fit me well. I stuck my head out of the curtain and asked Ms. Rutherford if she would like to check the fit. “Come here,” she said.

I checked that there was no one in the store and gingerly left the changing room and came to her. The panty liner rustled inside the panties as I walked. “My oh my, you are beyond cute,” Ms. Rutherford said. “The bra and panty fit you perfectly. You have such a nice, graceful figure. I could think of any number of girls that would wish to have a figure like yours.”

I blushed and said, “I love how the bra feels.”

I flattened the fabric of the empty cups next to my skin and Ms. Rutherford said, “That will look so much better once you get breast forms.”

“You don’t sell them?”

“No, I don’t. But there is a medical supply store two blocks from here where you can get them.” She wrote out the address and gave it to me. “Is there anything else of interest to you in the shop? Do you have any questions?”

I looked around the shop wishing I could own everything. “There are so many pretty things here.” My eye caught a manakin wearing a white lace bra and a white girdle. I pointed to the girdle and said, “That’s really neat. Is that a girdle?”

“Yes, Greg. It’s a girdle made in France. Actually an open-bottom girdle. Very sexy isn’t it?”

“Yes. I love the lace. Why do girls wear girdles instead of panties?”

Ms. Rutherford laughed. “Girls usually wear panties underneath their girdles. A girdle is worn for a different purpose than panties.” She could see that I didn’t understand and she said, “A girdle helps a girl get a perfect shape in her hips and butt. They’re made to create that shape out of the fleshy thighs and butt. Girdles are what are known as shapers. They can make a girl’s bottom part look pretty and curvaceous.”

“What are those little dangly things?”

“Garters. The other purpose of a girdle is to hold up a girl’s stockings.”

“Wow. Jill says she likes to wear pantyhose. Can she also wear a girdle?”

“Pantyhose is just the stockings attached to a panty. For some pantyhose the panty part is made a bit stronger so it acts a little like a girdle. If you wear a girdle, then you have to attach your stockings to the garters to hold them up. If you get pantyhose then you don’t have to do that. Each has its advantages and disadvantages. Some girls prefer one or the other, but every girl will usually have some pantyhose in case she needs it and a girdle or two in case she needs that. Of course, instead of a girdle, a girl can wear a garter belt. That doesn’t do any shaping but it has garters that also hold up stockings.”

“Do you think I would need a girdle to help my shape?” I asked.

“Your butt is a bit small compared to girls. But some girdles can be bought which have built in padding that make the derriere seem a bit larger. You have exactly the kind of figure that would benefit from a nice, padded girdle.”

“Does that girdle come with a padded bottom?” I said pointing to the manakin.

“It does, but I’d have to special order it.”

“I’ll have to talk it over with Jill.”

“Of course.”

I continued gazing about the store. In a far corner I saw several racks holding outfits that looked like one-piece bathing suits. “Those are pretty,” I said pointing to them. “What are they?”

“Those are called body shapers or bodysuits.”

“Why do ladies wear them?”

“A bodysuit tries to shape a woman’s whole torso, not just the hips and thighs as in a girdle.”

“What if a girl wants to wear stockings with her body shaper?”

“Some versions of it have attached garters.”

“Wow.”

Ms. Rutherford laughed. “You find girls underwear to be quite fascinating.”

“I thought you said that it’s okay if boys like lingerie?”

“Sorry. I’m not criticizing you. It’s just that I find it cute the way you love lingerie. You’re like a little boy in an ice cream shop or a toy store!”

“It’s just so amazing to me that girls get to wear such pretty clothing. All that lace and the gay colors. And then with the bra, the way it holds you. It must be really nice to wear a girdle and feel like it’s holding you like that.”

“I think women who wear girdles might not feel that way. After twelve hours in a girdle, women are joyous when they get to take them off. You might feel the same way if you had one.”

“Maybe.”

I changed back into my clothes. Ms. Rutherford rang up the bra and panty and I thanked her for her help. I left the shop and went to find the medical supply store.

***

The medical supply store was filled with walkers, crutches, and all kinds of strange devices. A middle-aged man in a suit and tie who had a resemblance to my dad asked me what I needed. “Ms. Rutherford, you know from the lingerie shop, she said …”

“Who are you talking about? What lingerie shop?”

“It’s her shop, two blocks away.”

“All right. What about your Ms. Rutherford?”

I contemplated running from the store, but I so very much wanted to call up Jill and tell her I got the bra and breast forms. “I’m sorry, she said that I could buy um … size D breast forms here.”

The man stared at me for the longest time.

“You know, silicone,” I said.

“What do you mean size D?”

“For a bra with D cup.”

“How old are you?”

“Thirteen.”

“What do you want with the breast forms?”

I could see that this man was freaking out so I said, “My aunt has cancer and my mom sent me here to get the D sized silicone breasts so she’ll have them when she comes out of the hospital.”

“Usually we fit the breasts.”

“Yeah. She’s not going to want to come here for a fitting. That’s not her.”

Without saying anything the man went to a back room and a few minutes later returned with two boxes. He opened them up to show me that there was one breast in each box. I had never been this courageous in my life, but the thought that I was fulfilling Jill’s request gave me the strength I needed. They cost almost my entire savings. If I were to be able to afford a girdle or a bodysuit, I’d have to save a bunch more money.

***

That night I called Jill. I whispered into the phone, “I got you know what.”

“Everything?”

“Everything.”

“We’ll have to see when we should meet. My mom might go out this weekend. I don’t know.”

***

It was the following weekend on Sunday afternoon that Jill and I had a chance to be alone together so I could try out my bra. I had brought the bra, panty and breast forms home in my backpack and hid them in an attic crawl space that was accessible through my closet. I would have little to worry about getting caught. I had several opportunities before Jill and I got together to try on the panty and bra and see how the breast forms looked and felt. Each time I looked at myself in the mirror the more anxious I was to get approval from Jill that I looked the way she hoped I would look. I prayed that I did and then I’d find out what she’d like to do together while we’re dressed in our bras.

When the following Sunday afternoon finally rolled around, I made a beeline to Jill’s apartment. “My mom’s at a matinee with her friend. We’ve got plenty of time to play with our lingerie.” Jill led me to her bathroom where she told me to take off my top. I took my bra out of my backpack and Jill said excitedly, “Oh how great. You were able to get the same kind of bra as mine. She read the tag and said, “36D, that’s so neat!”

“Ms. Rutherford said she didn’t have a C cup, so I got the D cup.”

“I think I’ll rather enjoy you having big breasts like my mom. She’s a DD cup. Of course, in a couple of years I might be a D cup myself. Or even bigger. I’m still growing.”

I put the bra on and then took out the breast forms. Jill lifted one up and said, “These are really hefty boobs! They do look to be about the same size as my mom’s!”

“You’ve seen your mom’s breasts?” I said.

“Of course. We often walk around the apartment naked or just wearing our panties. We are both girls, silly.”

“Of course. My mom is always dressed in the apartment.”

Jill laughed and said, “I hope so!” I put the breast forms into my bra cups. “Yay, Greg! You look so grown-up. Your chest is so pretty! So feminine! I love it!” Jill pulled her top off exposing her bra which was identical to mine. “Look at that!” Jill exclaimed. We stared into the mirror at the reflections of our chests side by side. Her B cup chest and my D cup chest. The scene was beyond beautiful.

“Oh my God, Jill, don’t we look cute together.”

“Cute and pretty!” Jill reached out her hand and gently touched my bra cups feeling my breasts. “So cool.”

I figured that Jill wouldn’t mind if I reciprocated so I gently touched her boobs in her bra the same way she was touching mine. I saw Jill smiling in the mirror. She was really enjoying this.

After a while Jill turned me around so she could see my back. She said, “You have such a pretty back, Greg, and I love the way the bra strap goes right across it. If I didn’t know you were a boy I would definitely think that you were a girl.”

Jill took off her skirt so she was wearing just her bra with the matching panties. “Now you should put on your panties!”

I had a rigid boner at this point. Who wouldn’t? “About my panties. The thing is … you know how boys have a different thing inside their underwear.”

Jill looked at me strangely and then laughed, “Oh, you mean you have a penis.”

“Yeah.”

“What about it?”

“It can be a problem for the panties.”

“Oh, you mean a bulge?”

“Or a tent.”

“Tent. Oh, you mean … I see. I never thought of that.”

“Yeah. I can put the panties on, but there’ll be a tent.”

“Let me see.”

I turned around and pulled down my pants and underpants and put on the panty and turned to face Jill. The front of the panties was sticking straight out. Jill laughed and said, “What can we do about that!”

“I was thinking that … I mean Ms. Rutherford’s shop sells very pretty French girdles. I’m pretty sure if I wore a girdle instead of panties it could tame my boner.”

“That’s such a great idea, Greg. Bravo! I could get the same girdle as you so we still look alike!”

“Sure, that would be fun. Ms. Rutherford said the girdles can come with padding that would make my butt a bit rounder.”

“Oh, definitely Greg. It would be great if we could both have rounded butts like girls have.”

“Tomorrow I’ll tell Ms. Rutherford I want to buy the padded girdle.”

“When my mom takes me bra shopping, I’ll tell her I want the girdle. I think she’ll let me buy it. I’ll also get some stockings. You should get some too. Ms. Rutherford will help you pick out ones that fit you.”

Jill took my hand and led me to her bed. She had me lay down on my back and she climbed on top of me so that our bras were touching each other and she was staring into my face. “I’ve always wanted to be bra to bra with my girlfriend,” Jill said.

I laughed. “So I’m your girlfriend?”

“When we play dress-up you are. Is that okay?”

“Sure.”

“And when we go ice skating you’re my boyfriend.”

“Really? We’re boyfriend and girlfriend now?”

“Do you want to be?”

“Boy do I ever.”

“This is so perfect.”

We lay like this for a while and then Jill said, “It should be fun to rub our nipples against each other’s.” She began moving the breasts in her bra up and back against my breast forms in my bra. “This is so much fun. Do you like this?”

“I love it, Jill.” I felt Jill pushing her breasts against mine slowly and steadily.

“I never felt anything so pleasurable before,” Jill said. “My nipples feel like they’ve gotten so hard. Holy cow!”

Jill kept forcefully sliding her bra over my identical bra. I put my arms across her waist and held her as she moved. After a while, Jill got off me and took me to the living room so we could sit side by side and kiss each other. While we did I felt Jill feeling me up and so I used my hand to feel the breasts within her bra.

When Jill thought the time was getting close to when her mother might return we went back to her room and got dressed. I left before her mom came back and we agreed that we’d get our girdles and once again find time to dress up together.

***

I was fortunate that I didn’t have to wait too long for the special order of a padded girdle to arrive at Ms. Rutherford’s shop. When I had ordered it she had measured me for the girdle and when I tried it on after it arrived, it fit me just right. Not too snug, but definitely supportive. In the mirror I admired my enhanced derriere. It was nice to have a girl’s tush. The fabric of the girdle was definitely going to give my boners a run for the money. If the girdle permitted a bulge, it would be small and manageable.

Jill also had luck getting her girdle. Her mother didn’t give her a hard time about it, though she did think it was an oddball request for a girl who had a beautiful figure and didn’t need any help. Ms. Rutherford knew that something was up and when she was helping Jill in the dressing room she asked her in a whisper if she and I were purposefully getting the same girdle. Jill whispered to her, “Greg and I are playing dress-up games in which we look alike. It’s so much fun.”

“I can imagine,” Ms. Rutherford said.

Now that Jill was determined to get prettier lingerie, she also bought a half-dozen bras and cute panties. In choosing each bra and panty set she tried to visualize how nicely she and I would look wearing the same bra. It would be a bit expensive for me to catch up to her, but she planned to give me a list of the bras she had bought so that I could order them for myself, one by one.

***

A week later Jill and I had a half day at school and went to her apartment where we could be alone while her mom was at work. We were excited as we put on our bras, panties, and girdles. As I had hoped the fabric of my girdle was strong enough to force my boner to stay out of sight. We spent some time admiring ourselves in the mirror. We turned around and snuck peeks at our butts. They were remarkably similar in the lacy white girdle. “I think we’re twins,” Jill said.

“Do we put on our stockings now?”

“Yes. Watch what I do and then you can put on yours. My mom gave me a lesson on putting pantyhose on the first time I wore it. That was very helpful. It’s easy to get the legs on wrong and then when you pull it up, it doesn't feel right. Stockings are a little easier but you still have to be careful to get your toes and heel in the right spots in the stocking, or else it won’t be right on your leg.”

Jill took brand new stockings out of a package. The stockings looked like flat legs. She showed me how she rolled up the stocking with her fingers until just the foot part remained. She raised her leg up on the edge of the bed and I said, “You have the prettiest toenails, Jill.”

“They’re pink so they match my fingernails. Now that you mention it, one day when we have time I should paint your finger and toenails so we both have the same color. Would you like that?”

“Sure. I agree that we should try and look as identical as possible! That’s really fun!”

“I agree. Now I put the stocking over my toes. But you have to remember to line up the stocking with your toes which means turning the stocking outwards a bit to line up the toe and heel with your own toe and heel.” Jill put the stocking on her foot and then slowly unrolled it up her leg. “See how carefully I bring the stocking up my leg? You don’t want to be rough with it or you’ll get a run.”

“I know. I was once going out with my mom and just before we left the apartment she said ‘Damn’ and that she had a run. I then had to wait while she changed her pantyhose.”

“It’s not easy being a woman!” Jill said.

“It might not be easy, but it sure is fun!” I said and Jill laughed.

“Now watch as I clip the top of the stocking to my garter.” I watched in fascination until Jill said, “Fasten the back garters so you know what to do.”

“Really?”

Jill nodded her head. I got down on my knees behind her and took one of the garters dangling from the back of her girdle and attached it to the top of the nearby stocking. Then I did the same thing for her other leg. To be so close to her beautiful rear end was intoxicating.

“See. My stockings are on and feel so comfortable. Now I’ll watch you as you put on your stockings.”

I took my stockings out of the package, rolled them up, and put the stocking toe over my foot. Jill had me rotate a bit more. “Always align the toe and heel. It’s very important if you want to be comfortable!”

“Right. I think I see what to do.” I pulled up the stocking, hooked the front garter and then put on the second stocking and hooked its front garter.

“Now reach behind yourself through your legs and hook the rear garters.” It was a bit awkward at first but I got the hang of it and in short order we were both dressed in our identical bras, girdles, and stockings.

“Now for the best part,” Jill said. She didn’t have to tell me. I lay down on the bed and she climbed on top of me, so our bras were touching each other’s bra. Our matching girdles lined up over each other. Now Jill began rubbing her bra on mine the way she loved to do the other day. This time, our loins were pressed hard against each other’s and our stockinged legs intermingled. The nylon rubbing against nylon, girdle against girdle and bra and breasts against bra and breasts was a feast of sensations and feelings. I hugged Jill tightly and then we found that we could also kiss while we did it.

Jill stopped and said, “My friend at school told me about French kissing. Do you know about it?”

“No. What’s that?”

“She says it’s a much better way to kiss. You just open your mouth a little and I put my tongue in your mouth or you put your tongue in my mouth.”

“That sounds so neat,” I said. “I think that’s how older people kiss in the movies.”

“Good. Let’s try it.”

Jill lowered her lips on top of mine and we opened our mouths and I felt Jill place her tongue into my mouth. My own tongue stroked her tongue and then I instinctively sucked gently on her tongue. I was so aroused I was sure that I might just spontaneously explode. We tongue kissed for ten minutes and then rested. “Can I try being on top?” I asked.

“Sure,” Jill said. She slid off of me and then I gently lay on top of her.

“This is so great. I can push my breasts down onto yours like you were doing.”

“Yeah, isn’t that fun?”

I imitated what Jill had done by sliding my larger breasts in my bra over her bra. Then I resumed French kissing with Jill while also feeling my girdle move over Jill’s. Ten more minutes of that and I slid off of Jill and we faced each other lying on our sides.

“Oh my God, Greg. You’re such a great kisser. That was so delightful. I could kiss you all day.”

“I’m crazy about you, Jill.”

“You’re so sweet, Greg. I love that about you.”

We lay quietly looking into each other’s eyes and occasionally kissing and fondling each other’s breasts. Then Jill said, “I’ve been thinking. I bought my pretty dress, the one I wore to the wedding at Vivian’s Boutique. It cost a hundred dollars. I wish that you had the same dress as me. Wouldn’t it be super if we dressed like we are now, both the same, and then put on the identical pretty dress. It would sort of complete everything, don’t you think?”

“Oh my God, Jill. That’s such a great idea. The two of us in the same dress. That would be the ultimate fun dress-up game!”

“Next Saturday I’ll take you to Vivian’s and we’ll get you the dress.”

“I can hardly wait.”

“Me too.”

“What about shoes? I remember that you said that your mom bought you heels to go with the dress.”

“Let me see your feet.” We sat up and compared our stockinged feet with each other’s. “Yours are a little bigger than mine. We’ll make an extra stop and buy you heels like mine. Then we’re going to be identical!”

“I can hardly wait.” I exulted in the thought of how our dress-up game would enfold as soon as I could get the dress and shoes. “There’s only one problem left. I’ve been growing my hair out, but it’ll take a while until it’s as long as yours. My mom actually is happy about it because she likes the idea of saving on haircuts. Also, she was a hippie in the sixties and likes men with long hair.”

“Your mother sounds really nice. I’d like to meet her.”

“Sure. You should come to my apartment one day.” A minute later I added, “I bet our moms would be friends if they met. Your mom reminds me a lot of my mom.” I laughed.

“What’s so funny?”

“I was thinking that they both have DD cup bras!”

“You’ve looked at your mom’s bras?”

“Yeah. After visiting Ms. Rutherford’s shop, I was curious to see what lingerie my mom owned. It was pretty interesting. In fact, her bras are also 36DD though she has bras in many different colors, not mostly black and white.”

“Then we should figure out a way for them to meet. That might give you and I more opportunities to be together.”

“Boy would l love that!”

***

We had great luck in getting me the same pink dress as Jill’s. That there were even any unsold was lucky and then we were overjoyed to see that a size 8 was available and on sale for 25% off. Jill’s was a size 6, and she was convinced that the 8 would fit me. The only other sizes available were 2 and 12, neither of which would have fit me.

After buying the dress, we went shoe shopping. I think that Jill and I felt so close to the goal line in my getting an outfit identical to hers, that we threw all caution to the wind with the salesperson in the shoe store. “My boyfriend would like to get these heels,” Jill said, pointing to the shoe that she had gotten herself.

Far from giving me a smirk, the salesperson measured my feet and decided that he could fit me into a 9D shoe. He left us to fetch them from the back room.

“My shoes are 7½ B,” Jill said. “Boys feet are always a little bigger.”

“Is it hard to wear high heels?”

“At the start. But after a little practice I’m sure you’ll be comfortable wearing them.”

“I must admit this is so exciting.”

“Isn’t it!”

The salesperson came back and helped me on with the shoes. They had little, cute, straps that he buckled, and I stood up. “Whoa!” I said as I tottered around a bit.

“Take a good walk across the shoe area and back,” the salesperson said. I did as he said and stopped in front of a mirror angled at the ground that let me look at myself in the shoes. I was pleased with the way they looked. I walked back and sat down. The salesperson asked me how I felt walking in the shoes and we agreed that the heels fit me quite well.

On our way back to Jill’s apartment with our packages we thought of when we might next get together to play our ultimate dress-up game. Both of us in the same bra, panties, girdles, stockings, heels, and dresses. We were going to have a grand time!

***

It took a couple of weeks but finally Jill and I would have almost a whole day together on the weekend. Jill’s mom was going to some estate sales with a friend who liked to collect porcelain figurines. They would have lunch and be back in the late afternoon.

Jill and I were buzzing with excitement as we put on our panties together. Then our bras, then our girdles and stockings. Before we put on our dresses, Jill suggested that we put on makeup and she put some lipstick and rouge on herself and then on me. I loved the feeling of lipstick on my lips and I said to Jill, “It’s another one of those wonderful things that girls get to do.”

She laughed. “Lipstick is fun when you don’t have to wear it every time you leave the house. The same with the other makeup.”

“I see.”

“Now we’re ready for our dresses!”

Jill put hers on first and I helped zip her up. Then we lowered my dress over my head. I was thrilled and excited and after Jill had zipped me up and smoothed my skirts, I felt a bit weepy like I would cry. “You’re about to cry, Greg!” Jill said.

“I know. I feel so pretty, girlish, and happy. This is the greatest game ever invented!”

Jill took my hand and led me to the bathroom mirror and we looked at ourselves side by side in the same pretty pink dress. I loved the way the sexy and prominent shapes of our busts were accentuated by the bodice of our dresses. “I just love you like this, Greg. You are as pretty as you think you are!”

We spent five minutes looking at each other. It was hard to break away. Finally Jill said, “Now we put on our heels!” Once our shoes were on, we walked to the living room and sat side-by-side on the sofa. Jill put her arm across my shoulders and leaned in and we began kissing. I welcomed her delicious tongue as it found its way into my mouth. I rested one of my free hands on Jill’s lap and the other gently felt her breasts.

I’m sure we were like this for almost an hour. Then Jill got up and put a Frank Sinatra CD on the player and she took my hand and had me dance with her. To a long series of slow, romantic songs we clutched each other tightly and danced. Our eyes were closed and we were both in a dream world when we heard Jill’s mom saying, “Jill? Who’s your girlfriend? In the same dress? What is this …Oh, my goodness. Is that Greg?”

We turned to face Jill’s mom still holding hands. “Why are you home so early?” Jill asked.

“Shirley wasn’t feeling well and she had to go home. But what in the world is going on here?”

“I’m sorry,” I said.

Jill cut me off and said, “Greg and I have invented a dress-up game. We try to look as much alike as possible. Today we’re playing it with my pretty dress.”

“Dress-up game my foot,” Jill’s mom said. “You both know that boy’s don’t get dressed up like girls. What have you got on underneath? I see stockings. What’s holding them up?”

We both held up our skirts showing our girdles.

“Girdles! So that’s why you wanted the girdle.”

“Everything has to match.”

“You’re wearing the same bra?”

“Yes, Mom.”

“Look. The first thing I need to do is call Greg’s mom.” She got out her phone and I dictated to her my mom’s phone number. When she answered, Jill’s mom said, “You’ve got to come over here to Jill’s apartment.” “Yeah, Greg’s okay, but you’ve got to see him.” “Ok, in fifteen minutes.”

She hung up the phone. “She’ll be here in fifteen minutes.”

Jill and I sat down on the sofa side-by-side continuing to hold hands. Jill’s mom sat facing us in an easy chair. A couple of times Jill’s mom started to say something and then stopped. “Let’s wait until Greg’s mom is here.”

After fifteen minutes of silence, the doorbell rang and Jill’s mom got up to answer it. Jill and I could hear the two mom’s introducing themselves to each other. Then my mom said, “Is Greg all right?”

“You be the judge,” Jill’s mom said.

My mom entered the living room and saw us. “Where’s Greg? I don’t understand. This is Jill and her girlfriend. How funny, you’re both wearing the same dress.”

“That’s Greg,” Jill’s mom said.

“Holy shit!” my mom said. She looked like she’d been hit by a cannonball. “Greg? What are you doing dressed like a girl?”

“Jill and I invented a fun dress-up game. We try to look exactly like each other.”

Jill and I stood up and my mom came over to look at me. “Lipstick, rouge? Bosoms? They’re as big as mine!”

“No, mom. They’re D cup.”

“What? You know my bra size?”

“It’s DD isn’t it?”

“You’ve been looking at my bras?”

“My mom wears the same size bras as you do,” Jill said to my mom. My mom looked at Jill in disbelief.

My mom lifted up the skirt of my dress. “Holy moly. Stockings held up by the garters of a girdle? Really Greg? And high heels?”

“Jill and I are wearing the identical bra also.”

My mom sat down in a chair and Jill and I sat back down on the sofa and her mom sat down. The four of us faced each other. “I want an explanation, Greg,” my mom said.

“Jill and I realized that I had a girl side to me. My girl side loves to be pretty and dress up in pretty clothes. Jill likes me as both her boyfriend and her girlfriend. We figured out that she loves each part of me. My girl part is kind of new and we’re just starting to get familiar with it. Our dress-up game is a fun way for me to get in touch with my girl feelings. Those are feelings that Jill really loves so it’s great for both of us. It makes us both happy.”

“This must be because your father left us,” my mom said.

“I don’t think this has anything to do with dad. Isn’t it true that boys can have a girl side and vice versa?”

“I suppose so. Aren’t you too young to know anything about that?”

“Kids grow up faster today than when you were young.”

“Look Greg. This is a shock. You never came to me and said that you’d like to wear a bra and a pretty dress. Had you said so, I probably would have thought about it and then maybe helped you nurture your girl side. You were obviously afraid of what I’d think which is why you hid this.”

“You’re right mom. I’m sorry. But I’m just a kid, aren’t I? Kids make a lot of mistakes. We also lack the good judgement that adults have.”

“Okay, okay. Enough with the sarcasm.”

“And what about you, young girl?” Jill’s mother said to her. “Greg is trying to become your boyfriend and you dress him up in your clothes. That’s a fine how do you do!”

Jill and I both laughed. “I didn’t have to twist Greg’s arm!”

“She didn’t!”

Our moms looked at each other. Jill’s mom said to Jill, “Take Greg to your room and let Greg’s mom and I have a talk.”

I was expecting my mom to chime in that I should take off the dress, but she didn’t say anything. When Jill and I were back in her room she said, “What do you think is going to happen? Your mom won’t forbid you from coming over here anymore, will she?”

“I don’t think so. My mom will probably try to understand me better. Where I’m coming from. Ask me about my girl side. Want to get to know it better. She wants me to be happy. I want her to be happy. We’ve always had a good relationship.”

“You’re a nice person Greg. I’m so happy that I’m your girlfriend. You give me everything that I could want. I love both the boy and girl side of you.”

Jill’s statement made me wonder if I wanted her to have a boy side beside her girl side that I adored. I knew without having to think that I wouldn’t want us to be boys together. On the other hand, it was possible that my girl side wouldn’t mind being with Jill’s boy side, if she had one. I’d have to do some more thinking about that.

***

After a while we could hear our moms laughing and talking together downstairs. About the time when I thought my mom would tell me it was time to go home, she instead stuck her head in Jill’s bedroom and said that Jill’s mom had invited us to stay for dinner. She asked me if that was okay with me and I said of course it was. I was surprised that she didn’t ask me to change into my boy clothes for dinner. Jill and I were joyous by the way things seemed to be turning out.

Dinner was served an hour later. Jill and I in our identical dresses sat facing our two moms. The two of them were fast becoming very good friends. They complimented Jill and I for looking like two cute, identical twin girls. I looked at the moms thinking how they both wore the same size 36DD bras. Their dress sizes were probably the same also. We were all made to be with each other.

***

Our moms hit it off even better than Jill and I had anticipated. By the time my mom realized that it was time for us to go home she told me to not bother changing my clothes. She thought that I looked enough like a girl that we could make the fifteen-minute walk at night without raising attention. My mom held my hand the whole way home. I was a little slow walking in my heels but by the time we got to our apartment building I could honestly say that I walked in heels as well as any woman did.

In the light of the elevator my mom hugged me. “This has been quite a day. I must admit that I was shocked before, but now, looking back, I have to honestly admit that there has always been a girl side to you. I’m so very happy that you found a sweet girl to help you nurture that. Not all girls might be as enthusiastic about your girl side as Jill is.”

“You’re the best mom ever,” I said.

“I don’t know about that. It wasn’t a hard call today. You and Jill are so cute together. How could any mom want to break that up?”

“She’s the best.”

“One thing we’ll have to talk about is your future. Do you want to be a girl all the time?”

“Oh, no, Mom! I only want to be a girl when Jill wants me to be a girl. She and I are boyfriend and girlfriend. But sometimes, like today, we like to be girlfriend and girlfriend. She likes the fact that I’m happy to dress up as a girl even though I’m a guy. It proves to her that I’m someone she can trust.”

“The two of you are something else!” My mom thought a minute and said, “There are times that I’d like you to be my girl, be my daughter. Would the girl side of you object to that? Is it only to Jill that you’ll give your girl side?”

“I haven’t thought about that, Mom. But I don’t see any reason why I should only be a girl for Jill. It might be really nice being a girl for you too. As mom and daughter we could do things that we can’t do as mom and son.”

We entered the apartment and my mom gave me a big hug. “I love you Greg.”

I went to my room and just as I took off my dress, Mom came in. “I’m sorry. I wanted to see what’s under your dress. That’s a very pretty bra.” She laughed softly and inspected my breast forms. “You’re as busty as me!” Then she added, “I love your padded girdle. It gives you a girl’s butt, that’s for sure. And your legs are pretty in the stockings.”

“Thanks, Mom. It means a lot to me that you like my choices.”

“You’ve got a good instinct for pretty lingerie and dresses. When your girl side feels like shopping one day, let me know and we could go together. I’d be happy to buy you any clothes you might want. Some more bras and panties. A slip and definitely a pretty nightie. You need some skirts, blouses, and dresses. Just say the word.”

“Thank you, Mom. I’d love to go shopping with you.”

Just before I went to bed, I called up Jill. “I just wanted to say that I miss you already.”

“I miss you too, Greg. We had so much fun today.”

“My mom would like to take me shopping to buy lingerie, but also dresses and skirts. Also a pretty nightie.”

“That’s so cool. It means that we’ll have so many more ways of playing our dress-up game!”

“I can hardly wait until we play together again.”

“Me too!”

The End