The Prom Dress

By

Pamela

(pamelapamela@hotmail.com)

My dad is what one would describe as macho – muscular, kind of hairy, overburdened with testosterone. As masculine as my dad is, my mom is ultra-feminine. She obviously loves being a woman, though she hasn’t discussed that with me! She wears pretty dresses and fancy lingerie, high heels, and makeup. One could say she’s a throwback to the 1950’s mom.

My older brother, Kevin, is the spitting image of my dad in every way. He was born with a great musculature. He could do ten pullups the first time he hung from a chinning bar! I wouldn’t call the two of us close. He’s kind of a monosyllabic guy. Doesn’t talk much – likes to play sports.

I’m sixteen now and the first time I hung from a chinning bar all I could do was hang from it. I couldn’t do one pullup. My dad tried to be sympathetic but quickly lost patience with me after I was unable to do more than one pullup after months of trying. I heard him one night telling my mom that I had girl arms. Instead of defending me she laughed.

Every facet of my physical body is more like my mom than my dad. My face has echoes of her though I do look like a boy, I have scant body hair as compared to my father and Kevin and I’ve already mentioned how I’ve got muscles that are as strong as those of a typical girl.

I have a thirteen year old sister, Kathy, who is quite pretty and does look a lot like my mom. She’s a bit tall for her age so that she and I are close in height. If there’s one thing about my sister it’s that she is as feminine as my mom. She has a closet full of pretty dresses and shoes and everything and anything to do with looking pretty.

So here’s my big secret: for as long as I can remember, I’ve enjoyed wearing Kathy’s clothing. Before she even hit puberty I’d try on her panties and her dresses and flounce around the house. Unfortunately, opportunities to wear her clothes have been far and few between. Later, when she got her first bra, it became my first bra too on those times when I was able to sneak into her room to try it on.

I can only dream about getting my own girl clothes and being able to wear them as much as I want. That’s waiting for another part of my life. It won’t be happening until after college.

***

There’s a wonderful quaint shopping area a short drive from our home. It’s got some nice clothing stores. One specializes in lingerie. Its window displays I’ve often enjoyed looking at. There’s also a few dress shops catering to all kinds of dress styles for women and girls.

One day I noticed in the window of one of the shops a pink prom dress that just about stopped my heart cold. God did I want to wear that dress! It had the most delicate lace, pearl buttons, and silk ribbons. It had beautiful underskirts that gave the dress a marvelous poufy look from the waist outwards. Sadly, I died a thousand deaths looking at that dress. I wanted it so badly!

I spent a lot of time plotting how I could buy the dress, but none of my plans made sense. There was no way in the world I could hide the dress in the house, even if I could come up with the money to buy it. Buying it would be impossible. How many boys my age buy pretty pink prom dresses?

***

It so happened that Kathy is graduating from junior high and she and her friends have dates for the junior high prom. My mom became operation central in planning the evening for Kathy and her friends Cindy and Krissy. She would take them to the stores to buy all that they needed for the prom. Of course, they needed prom dresses, but also bras, panties, pantyhose, and new heels. Mom and the girls had planned this outing for weeks.

Two days before the excursion was to occur, my grandma took a bad fall and my mom could no longer take the girls shopping. She had to travel to Grandma’s house to help out for a week or so. Suddenly, without my mom to shuttle the kids to the shopping area and to pay for their dresses and other clothes – besides offering advice on what were good styles, prices, and bargains – hysteria took hold. Kathy, Krissy, and Cindy were besides themselves with frustration and even suicidal about showing up at the prom in old dresses!

The three moms put their heads together to see if they could figure out a solution. Krissy and Cindy’s moms couldn’t break prior commitments and the dads all had to work or otherwise take care of other business. Besides, the dads are utterly incapable of helping teenage girls pick out prom dresses!

Then, somewhat spontaneously, the moms realized that I am the perfect person to escort the girls. I have a driver’s license. I’m remarkably level-headed and mature for my age, and I have a great reputation for being trustworthy. My mom came to me with a proposal that I take the girls. Would I mind? Would that be a problem for me?

The moment my mom explained what she wanted me to do, I realized that she had given me a pathway to get Kathy to select the pretty pink dress I’d seen in the window. If she picked that dress, then it would end up being one I could wear also. This is the kind of thing that makes me take the idea of God seriously. I mean, come on, how could a path toward wearing the pink dress happen just randomly? Huh?

Kathy and her friends were beside themselves with joy when it was announced that the shopping trip wouldn’t be cancelled. Before my mom was to depart for Grandma’s house, she and Krissy’s and Cindy’s moms met with me to explain what I needed to do.

Krissy’s mom gave me a credit card and said, “Besides a pretty dress, I’ve told Krissy she could buy one or two new bras and a couple of matching panties. Do you know what I mean by matching?”

“I think so.”

“In the bra department you’ll find that some bras are matched with panties. They have the same lace pattern and colors. That’s called a set, as against bras that are sold without matching panties and vice versa.”

“I understand,” I said. “Are there any kind of bras I shouldn’t buy her?”

“Good question. She’s a 34B going on a 34C right now. So it’s important for her to make sure that she buys bras that are both supportive but also allow for a bit more growth.”

I got out a pencil and paper and wrote down what she had told me. “I’ll have to take her word for it when she tries on the bras.”

“Yes, but please remind her. Don’t be shy about asking her how her bras fit.”

My mom interjected, “Greg, do you know about bra sizes?”

“I guess … I mean … maybe?”

“Krissy’s mom said she wears 34B or 34C bras. Do you know what that means?”

Before I could say anything, my mom went to her bedroom and came back holding one of her bras. “Bras have a number and letter size. See here?” Mom showed me a tag attached to the end of the wing. “Read that.”

She handed the bra to me and I looked closely at the label. “It says 36D.”

“That’s my bra size,” my mom said. “The D refers to the size of the cup. The bigger a woman’s breasts the further into the alphabet is the cup size. A are small breasts. D are much bigger breasts. The number is the distance around a woman’s chest just underneath her breasts.”

“I got it,” I said.

My mom took the bra back from me. “Good Greg. Now you know in case there’s a problem with size at the lingerie shop.”

“Okay.”

“As far as Krissy’s dress is concerned,” Krissy’s mom continued, “she has strong views of what she wants so let her pick that whatever it is. She should come out of the dressing room and show you so you can at least flag an awful choice. As a boy she might take your two cents to heart!”

“I’ll be happy to do all these things.”

“She’ll also want heels to match her dress. If necessary you can ask a saleswoman if the shoes match correctly. Also, she’ll try and get very high heels – please talk her out of that!”

“I’ll do that.”

“Thank you, Greg. You’re a marvelous and brave boy for helping out!”

Next Cindy’s mom gave me a credit card. She said, “Almost everything for Cindy should be like you’ve just heard for Krissy. One main difference is that Cindy wears 34A bras now. She’s going to want you to buy her a bra with a lot of padding. Please try and steer her away from fully padded bras to push up bras. Push up bras also have padding, but only in part of the cups to help raise the bust. I’ve gone over this many times with her, but she gets confused or mistakenly thinks that more padding means a bigger bust.”

I wrote this down for my notes for Cindy. “I’ll remind her to buy push up bras.”

“Two other things. She can get whatever panties she wants. They don’t have to match. I know that the girls intend to get three different color dresses. For sure one will be pink and I suppose one will be a shade of light blue. That leaves some other color. It could be yellow, or a light green shade, or even a lavender or wine color or even red.”

“I’m glad you mentioned that,” Krissy’s mom interjected. “Which dress color each girl ends up with could be a battleground. You might have to steer them to an equitable arrangement. One in which all three girls are happy.”

“Ok, I’ll try and do that!” So if I say or do nothing then I’ve got a one third chance that Kathy gets the perfect pink dress – assuming that’s a dress the girls will fall in love with as much as I have. If it looks like Kathy won’t be getting the pink dress, I’ll have to intervene somehow. Convince the girls to let Kathy have it or convince Kathy that she wants it! How sad it would be if Krissy or Cindy got it!”

Now that I was up to speed on shopping instructions for Krissy and Cindy it was my mom’s turn to tell me what she wanted for Kathy. She gave me a credit card and said, “Your sister wears 34D bras and size six panties. Make sure she tries on everything before buying them. She can buy just one thong. The rest of the panties should have more coverage.”

“Excuse me Mom, but what is a thong?”

Mom laughed and called out to Kathy to come. When she appeared Mom said, “Would you fetch your thong to show your brother what it looks like. Also bring a regular panty. Thanks.”

Kathy returned holding two panties. Mom took them from her. “See this one is a full coverage panty. In other words, it covers most of Kathy’s butt. The thong doesn’t cover any butt.” Mom held up the thong and showed how it only had a narrow gusset that went up between the butt cheeks.

“I see, Mom. That’s interesting.”

“Let’s see, what else? Kathy does need to buy a new full length slip so make sure she gets one. She’s been bugging me to buy her a particular pink, lacy, gartered panty girdle that she’s seen in the lingerie store. So you might as well let her buy that. Also get her stockings and a couple pairs of pantyhose. Kathy is leaning toward a lavender dress, but I think pink is her second favorite. Whatever dress she buys, I don’t want her bra or bra straps to be visible. She can get stiletto heels if she wants. They’re not good for girl’s feet, but once she walks around in them at the prom she’ll get it out of her system to ever want to wear them again.”

“I’ve got all this written down as notes.” I said.

“Good. You’re an angel for doing this, Greg,” she said. “I know most boys would be quite squeamish to be buying girls clothes. Even to be in the lingerie department makes men blush. Your father gets downright weird as we approach the racks of bras!” My mom laughed. “You’d think the bras would leap off the racks and eat him like piranhas!” She and I laughed heartily. Suddenly mom’s face got serious. “Can I ask why you’re not shy about buying bras for your sister and her friends?”

Her question caught me off guard, “I, I mean you, you asked me …”

She gave me a Larry David type stare deep into my eyes as if we were on Curb Your Enthusiasm and she was trying to probe my mind. I was expecting her to ask me if I liked bras or saw myself as wanting to be feminine and instead she said somewhat mysteriously, “I understand, Greg. The world is filled with all types.”

***

The day of my big adventure with the girls was bright and sunny. It matched my mood. Little did the girls or their moms know how much delight I was expecting to have helping the girls pick out bras, panties, dresses, shoes, and anything else they set their minds to. I had determined to be open to any purchases they might want to make. Stockings, garter belts, slips, all in ones, even girdles should they want one. I was going to be as supportive as I could be.

With the three girls sitting in the back seat of the car as I drove to the shopping area, I heard Cindy ask Kathy, “Your brother doesn’t mind helping us buy prom dresses?”

Her tone of voice was what I expected – it had an implication of ‘what’s wrong with your brother?’

“Greg is easygoing,” Kathy said, “so being with girls doesn’t make him uptight. Besides that he’s happy to help my mom. It’s the way he is, he’s not selfish.”

“I wish my older brother was like that,” Krissy said. “He gets freaked out by anything to do with girls except wanting to kiss them.”

“That’s like my brother Kevin,” Kathy said. “He would never have helped us. He doesn’t care if we go to the prom wearing old dresses!”

“What does Greg think about that?” Cindy asked.

“You girls know I can hear you?” I said.

The girls laughed. “I was wondering when you were going to speak up,” Kathy said, and the girls laughed again.

“I’m happy to help you girls. I know how much the prom means to you.”

“Did you go to your junior high prom?” Cindy asked.

“Not exactly. I was too shy to ask a girl to go with me.”

“That’s so sad,” Krissy said.

“Some boys are shy. I suppose some girls are shy. It’s just the way they are,” Cindy said.

“But you’re not shy about taking us shopping?” Kathy asked.

“A little bit shy, but mom asked me to take you and I like being helpful. It makes me feel good.” Of course I had a hidden reason for going that I would keep to myself!

“Do you have a girlfriend now?” Krissy asked.

“I don’t have a steady girlfriend. I have gone on a few dates with a girl I really like and maybe she’ll become my girlfriend one day. I don’t know.”

“I hope she becomes your girlfriend,” Krissy said. “You’re a nice boy and you should have a girlfriend.”

“That’s very kind of you,” I said. It was true that I’d been on some dates, but for reasons I didn’t understand my relationships with the girls I’ve dated do not progress. The girls never end the date saying something like, “This was fun, we should go out again.” No, they seem noncommittal, but when I call them again they agree to go out again. Getting a girlfriend seems like the hardest thing to do on earth. “So what do you want to buy first? Lingerie or dresses?”

“Dresses!!” the girls said in unison.

I parked close to the dress shop with my pink dress in the window. I was relieved to see that it was still there. The girls and I stood looking at it and other dresses displayed near it.

“That’s such a pretty pink dress,” Krissy said.

“I was thinking the same thing,” Cindy said.

“I love it,” Kathy said. “Maybe they have it in lavender.”

Suddenly I was put on high alert. It might be difficult to steer Kathy to that dress. We entered the shop and an older woman came up to us and said, “I bet you three girls are looking for prom dresses!”

“Yes, yes, yes,” they said.

“I love the pink one in the window,” Krissy said.

“Isn’t it a wonderful, feminine, creation?” the saleswoman said. She led us to a rack where several of those dresses were hanging. I knew that a size ten like Kathy normally bought would fit me.

“We’re all size 10,” Krissy said.

That was a relief. We’d end up with three size ten dresses which would enable easy swaps between the girls.

The saleswoman found a size ten of the pink dress and handed it to Krissy. I could see Kathy watching with interest. “That’s such a pretty dress,” Kathy said. “It doesn’t come in any other colors, does it?”

“No, just pink. But we have many dresses that are as pretty but in other colors.”

“I’m going to try on this dress,” Krissy said.

“Too bad we all can’t have a pink dress that pretty,” Cindy said.

“I think the three of you girls should decide together on three dresses,” I said. “Once that’s determined, then you can figure out which one of you gets which dress.”

The girls looked at me and I worried they were going to laugh at me, but instead Kathy said, “That’s a good idea. We decide on three dresses first.”

“I like that idea, too,” Krissy said.

“Okay, so I think the pink dress that Krissy’s holding should be one of them,” Cindy said.

“After one of us tries it on and make sure it looks good!” Kathy said.

“Of course,” Krissy said.

“So you girls need two more dresses. I assume different colors!” the saleswoman said.

The girls wandered through a dozen clothing racks containing prom dresses of many different styles and colors. Some were stylistically like the pink one and the three girls gravitated toward those. “Here’s a pretty lavender one,” Kathy said.

“Isn’t that a lovely shade?” the saleswoman said. “A classic, feminine, prom dress.”

“I love it,” Cindy said.

“So do I,” Krissy said.

The girls decided that this would be the second of the three dresses. I had to admit that the lavender dress was pretty. I imagined myself wearing it and I knew that I’d enjoy it immensely, but it would still leave me longing for the pink dress. The pink dress was the pinnacle of everything I wanted about being a girl. I was heartened by the fact that Cindy and Krissy liked the lavender dress. If I had to nudge one of them to it, it wouldn’t be that traumatic would it?

In short order, Kathy and Cindy became equally excited by a pale blue dress they had found. It’s crinolines were fuller than the other two, besides having some lovely embroidery.

“So, are these the three dresses? Kathy?” I asked.

“Yes, Greg.”

“Cindy?”

“Yes, Greg.”

“Krissy?”

“Yes Greg.”

“So you need to try them on! Please don’t forget to step outside the room so I can see them. Your moms told me that I should make sure they’re okay!”

“Yes, Greg! You’ll get to see us in our prom dresses!” Kathy said.

After escorting the girls into the dressing room, the saleswoman came out and stood with me. “They’re such pretty girls!”

“Aren’t they!”

“It’s so nice of you to take them shopping!”

“My mom was going to but she got called away. I’m happy to help out.”

“You’re such a fine boy.”

“Do many girls like the pink dress?” I asked. “The one in the window.”

“Oh my God, the feminine ones do. You know the ones who enjoy being a princess for the night. I’ve sold a bunch of them.” She looked at me and smiled, “Do you like that dress?”

I don’t know what came over me, but I said, “I saw the dress a few weeks ago in the window and it stuck in my mind. I’m glad the girls like it too.”

The saleswoman smiled at me. “It seems like you share a feeling that girls get when they see a dress they love. It’s hard to describe – sort of a sense that wearing the dress will make them feel beautiful, make them feel one hundred percent like a girl.”

“Huh,” was all I managed to say. What the woman had said dug deeply into my mind. She was definitely describing the way I felt.

“There’s no shame in loving the dress,” the woman said and laughed. “I’m sorry, it’s not a laughing matter. I can sympathize with the frustration of boys who fall in love with pretty dresses.”

I smiled wanly. It was amazing how this woman could see so clearly into my soul.

“The girls were chattering in there about their boyfriends,” the saleswoman said. “Wondering which dress their particular boyfriend would like. I told them that it was unusual for boys to even notice the dress that their girlfriend was wearing.”

I would notice! I felt a twang of jealousy. How nice it would be to have a girlfriend wearing a prom dress like one of these. And then maybe she’d invite me to wear one with her. The two of us could pretend to be girlfriends.

The girls came out of the dressing room together to show off the dresses. I was disappointed to see Krissy wearing the pink dress even though I had already figured that she’d be the one to wear it. Kathy was wearing the lavender dress and Cindy the light blue dress. Even more painful was how absolutely beautiful Krissy looked in the dress. Actually, I wasn’t sure if I was so smitten because Krissy was beautiful or because the dress was beautiful. Surely the two together was an incredible sight. How I would love to be wearing the dress myself! Could I magically be made into Krissy? Obviously not but seeing the dress up close being worn by a girl made me feel even more motivated to somehow steer the dress toward Kathy.

“What you do you think, Greg?” Kathy asked. She stood in front of me twirling in the lavender dress.

“You look so pretty! I can’t believe how nice all three of you girls look. You’re going to be the queens of the prom!”

The saleswoman, joined in with me telling the girls that in all her years she’d never seen three such pretty girls together. “I can’t decide which of your dresses is the prettiest and I can’t decide which of you girls is the most beautiful!”

I wanted to say that it was definitely the pink dress, but I held my tongue. “I guess we’ve found our prom dresses, haven’t we?” I said to the girls and they said yes indeed.

The girls were on their way back to the dressing room when in desperation I took Kathy aside and I said, “Don’t you prefer having the pink dress?”

She looked at me quizzically and said, “No. I like the lavender one, besides Krissy really loves the pink one.”

“Yes, but realistically wouldn’t any of you be happy in any one of the three dresses?”

“True. I’d also be happy to wear the light blue, and pink dresses.”

“So you can’t ask Krissy to switch with you?”

Kathy looked at me with a strange look. “Why do you care so much about me wearing the pink dress?” She laughed and said, “You’re not going to the prom with me.”

“I know that, Kathy. It’s just that I personally think the pink dress is prettier than the other two, not that the other two aren’t pretty. They clearly are.”

Now Kathy was really looking at me like I was weird and crazy. “I’ll ask Krissy, but I doubt that she wants to switch.”

“Thank you, Kathy.”

Kathy joined the other girls in the dressing room. A short time later they left with each one holding a dress. Krissy was still holding the pink dress and Kathy came up to me and said, “I’m sorry Greg.”

I quickly went up to Krissy in desperation and said, “Are you sure you won’t switch dresses with Kathy?”

“Pink has always been my favorite color,” Krissy said. “I’m sorry, Greg.”

The tone of her voice was warning me that she thought I was crazy.

Under my breath I said, “It’s my favorite color also.”

Krissy heard me and said, “Greg, if I switched the dress would be for Kathy, and you won’t be at the prom. So why get so passionate about the pink dress?”

“You’re right,” I said. “I’m terribly sorry, Krissy. I don’t know what’s come over me.”

I took out the credit cards and paid for the dresses. The girls happily carried them outside to put in the trunk of the car before we walked over to the lingerie shop. As I was putting the dresses in the car I got to hold the pink one in its see-through plastic protective garment bag and something came over me. I began to cry. I wanted the dress so badly. I ached from being so close to it but not having it. I closed the trunk.

Kathy looked at me and said, “Why are you crying Greg?”

Krissy and Cindy heard her and came over. The three girls watched me crying. Kathy took my hand and led me to a nearby bench where we sat down. Crying in front of the girls had the effect of making me cry harder. Finally, Kathy handed me a dainty girl’s handkerchief and I blew my nose.

“I’m so sorry. I don’t know what’s come over me,” I said. This was so embarrassing I wished the ground would swallow me up.

“Is it because Krissy wouldn’t swap dresses with me?” Kathy said.

I nodded my head and continued to cry.

“But why? The dress would be for me, not for you,” Kathy said. “Am I missing something.”

Suddenly Krissy said, “I’ve heard of boys who like to dress like girls. Maybe your brother wants to wear the pink dress.”

“Greg, do you want to wear the pink dress? I mean if I had it in our house, would you then wear it?”

I nodded my head.

“Oh, wow,” Cindy said.

“I had no idea,” Kathy said.

“I’m so embarrassed,” I said as I continued crying.

Krissy stood directly in front of me and said, “Please don’t cry Greg. I hate that I’ve made you so sad. It’s no big deal for me to switch dresses with Kathy.”

“Thank you, Krissy,” I said, “but as bad as I’ll feel if I can’t wear the pink dress, I’ll feel worse for using my tears and your pity to sway you into letting Kathy have it. No. You really want the dress so you should have it.”

“You’re sure?” Krissy said.

“I insist. I couldn’t live with myself for coercing you. If you swapped the dress it wouldn’t even be mine, it would be Kathy’s and I’d have no right to wear it.”

“Greg!” Kathy said. “Please stop crying. You’re my big brother and I don’t like seeing you so sad.”

“I’m sorry Kathy,” I said trying to gain control over my emotions.

“Have you been wearing Kathy’s clothes?” Krissy said to me. “It just occurred to me that if you like wearing girls clothes, maybe you’ve been doing it for a while.”

“I won’t lie,” I said. “I have been wearing Kathy’s clothes.”

“Oh, wow!” Kathy said.

“Her panties?” Krissy asked.

“Yes.”

“My bras?” Kathy asked.

I nodded my head. “And your dresses.”

“I never even knew,” Kathy said.

“I’ve always been careful with your clothes. I put them back exactly as I found them. I’m so sorry Kathy. I can’t stop myself from wanting to wear girls clothes. I think about it all the time. I wish …”

“What do you wish?”

“I wish I could be a girl like the three of you. That would make me so happy. I’d wear a pretty dress every day. I’d wear nail polish like you girls do and I’d have nice long hair like you girls do. And it would be so nice to wear panties and a bra every day. I’d somehow get breasts like you girls have.”

“Wow, Greg,” Cindy said.

“You make me feel lucky to be a girl,” Krissy said.

I hung my head in misery. I felt naked and horribly embarrassed.

The three girls walked away and fell into a discussion just out of earshot. When they came back, Krissy said, “Look at me Greg.”

I raised my head and gazed into her eyes. I used the handkerchief to wipe tears off my cheeks.

“Greg, there’s a very simple answer to your problem.”

“What could that be?” I asked.

“The prom is in a week. I’m going to wear the pink dress to the prom. But after the prom, I’ll exchange my dress for Kathy’s dress. Then it’ll be in her closet if you want to wear it. How’s that sound?”

“You would really do that for me?”

“Sure, Greg,” Krissy said. “It’s a prom dress and I doubt if I’d ever wear it again. Well, if I need a pretty dress like that, say for Easter, or for a wedding or communion, I’ll have the lavender dress which is equally pretty.”

“I can’t thank you enough.”

“And Greg,” Kathy said, “Cindy had a great idea. I’ll designate some of my clothes for you and we’ll keep them in a special place in my closet for you. You can have your own panties and bra, and dresses too. Like Krissy said, I probably will never need to wear a prom dress again after the prom. So If Krissy swaps dresses with me, the pretty pink dress can be yours to wear whenever you can or want to.”

I reached out and hugged my little sister. It was a struggle not to cry any more. The thought that in a week’s time I’d have the pink dress to wear made me beyond happy. My tears evaporated.

“I’m so sorry I put you girls through this,” I said. “This is supposed to be your fun day and I’ve put all my weirdness upon you. Please forgive me!”

“We might be young girls,” Kathy said, “but we can still understand that you are who you are. You’re not feeling any differently than you’re meant to feel. You’ve never been like Kevin; you’ve always been a gentle boy and now I see why.”

“I’m going to cry again,” I said. The three girls surrounded me and hugged me.

“As far as we’re concerned, you’re a girl just like us!” Krissy said.

“I agree,” Cindy said.

“Me too,” Kathy said. “From now on I’m going to think of you as my older sister!”

“Okay, now that this is done,” Krissy said, “let’s go buy our bras and panties!”

As we walked the couple of blocks to the lingerie store, Kathy said to me, “I’d love to see you wearing the pink dress, Greg.”

“You would?”

“When just you and I are home alone, I won’t mind if you wear the dress.”

“Thank you! You’re the best sister a boy ever had!”

“A girl ever had!”

“Right. A girl ever had!”

***

In the lingerie shop I detected a change in how the three girls related to me. It was like I was one of them now and had the same knowledge of bras and panties that they did.

I took out my notes and said to the proprietor, Nancy, “The girls would like to buy bras and panties. Their mom’s gave me instructions. Let’s see, for Krissy her mom would like her to get one or two bra and panty sets. She’s a 34B going on a 34C right now. Her bras should be both supportive and allow for some growth. I’m supposed to ask her how her bra fits.”

“Got it,” Nancy said.

“As for Cindy,” I said. “She wears 34A bras. Her mom wants her to buy only push up bras, and not fully padded bras. She can get whatever panties she wants.”

“This is so efficient,” Nancy said and laughed. “I love how seriously you take lingerie shopping.”

“Their moms entrusted me with the responsibility and I want to please them.”

“I think your attitude is lovely.”

“As for my sister Kathy, her bras are 34D and her panties are size six. She’s supposed to try on all her bras and panties before buying them. She’s allowed to buy one thong and the rest should have more coverage. Also Kathy needs a full length slip. There’s a pink, lacy, panty girdle with garters that Kathy covets and my mom said she could buy that. Also, all three girls need stockings and pantyhose.”

“Do you see the panty girdle that your brother mentioned?” Nancy asked Kathy.

Kathy wove her way through some displays and found the panty girdle. “This is it.” She brought it back to Nancy.

One look at the panty girdle and I knew that I was going to want to wear it myself.

“I think you’re supposed to buy two of them,” I said.

My comment startled Kathy and she looked at me without comprehension until suddenly it clicked and she gave me a thumbs up. She went back to the rack and got a second one.

Nancy asked the girls what kind of bras they wanted. “The prettiest you have!” Krissy said. “We’re going to wear them with our prom dresses!”

“We just bought the cutest prom dresses,” Cindy said. “We need the prettiest bras to go with them.”

“Our most feminine styles are over there,” Nancy said pointing to a section of the store overflowing with bras in many sexy shades with lacy cups and straps. Kathy, Krissy, and Cindy went on ahead to root through the bras. Nancy and I walked over behind them. I watched as the girls ran their fingers over the bras and held some up to get a better look at them.

In front of me I noticed an especially fetching pink bra with matching panty. I leaned over to see the bra sizes.

“Like that bra?” Nancy asked me.

Caught off guard I said, “I was checking to see if there’s a 34D.”

Nancy looked through the bras and pulled one out. “Here, you’re in luck. It’s a set. Are you a size six panty?”

My mouth fell open and I said, “Me a size 6?”

“Do you need me to measure you?”

I lamely said, “I thought that my sister Kathy might want it.”

Kathy was busy with Krissy and Cindy going through some bras and discussing them on the other side of the room.

“You suggest bras for you sister?” Nancy said and laughed. “That’s a new one on me.” I was speechless and Nancy continued, “What do you like about the bra?”

“It’s pink.”

“I can see that.”

“It’s got lace.”

“True. So it’s lacy and pink. Why do you want to show it to your sister?”

“I think she likes pink, lacy bras.”

“How do you know that? I’m curious. I have brothers and I never discussed my preference in bras with them.”

The emotions I’d had earlier seem to be coming back. I was exhausted from trying to parry Nancy’s questions. I felt tears coming on again. How much fear of humiliation must I go through today I wondered.

“I’m sorry,” Nancy said, “it was rude of me to make you cry. Only …”

A few stray tears came out of my eyes and Nancy said, “I’ve had many boys come in here wanting to buy a bra and panty for themselves. I commend them. It takes courage to be who you want to be.”

“Yeah,” I said.

“I know you want that bra and panty set,” Nancy said, “and there’s no reason for you to be embarrassed about it. Do you want to be a girl?”

I nodded my head.

“You poor dear. I’ve seen that frustration many times in the boys that come in here. But buying yourself a pretty bra and panty certainly can go a long way toward assuaging your feminine desires.”

“You’re right, and …,” I said.

“And?”

“You see, the girls got their prom dresses and after the prom they’re going to allow me to wear the prettiest one.”

“How kind of them!” Nancy said. “So you need a specially pretty bra and panty to go with the dress?”

“Yes.”

“You can’t make a better choice than this one.”

The girls had selected several bras and panties each and joined Nancy and me. “Is that a bra you would like, Greg?” Kathy asked me.

“Yeah,” I said sheepishly.

“Oh my God, it’s such a pretty one,” Krissy said.

“Would you like to try one of them also?” Nancy said.

“I would!”

“Me too,” Cindy said.

“You might as well include me,” Kathy said.

“So, we need a 34A for Cindy, a 34C for Krissy, and a 34D for Kathy, the same as Greg’s bra size.”

Nancy handed the bras to the girls. “So now it’s time to try on your bras and panties! The dressing room is over there.” She pointed to the entrance.

Nancy waited a few minutes and then joined the girls in the dressing room. I heard conversation and some laughter. After a while, Nancy emerged laughing.

“The girls are wondering why you’re not trying on your bra and panty.”

“Seriously?”

“No one else is in the shop,” Nancy said. “Come into my office and try it on.”

She didn’t wait for my response and I followed her into an office. “Take off your shirt and put on the bra. Do you know how to put on a bra?”

“I think so.”

“Show me.”

I took off my shirt and held the bra thinking about what I needed to do.

Nancy said, “Let me help you. You know, if you fancy yourself to be a girl, you should learn how to do things the way that girls do.”

Nancy gave me a quick lesson on putting on the bra.

“Thank you,” I said, when it was on.

Nancy laughed, “I often give the same lesson for girls getting their first bra.”

“It feels fine,” I said.

“It’s comfortable?”

I nodded.

“Do you have breast forms at home?”

“Breast forms? What are they?”

“They’re artificial breasts that women may wear after a mastectomy, or men may wear who want to feel like they have breasts the same as a woman.”

“Where could I get them?”

“Hold on, Greg,” Nancy said. She went into the backroom and returned holding two foam breast forms. “These are good for stuffing in your bra. They’ll give you breasts. Alternatively, but it will cost you money, you can get silicone breasts – they have the feel and heft of real breasts.”

“I had no idea,” I said.

“I don’t have a mirror in here, unfortunately. You look cute and pretty in that bra.”

The office door was a jar and Kathy entered wearing a bra and panty with her arms crossed over her chest to partially hide herself.

“We had some questions,” Kathy said. She stared at me wearing the same bra she was wearing. “You look adorable, Greg. That’s such a wonderful bra for you.”

“Thank you, Kathy.” The partial view of Kathy’s figure in lingerie had the effect of showing me what my goal was. Some day in the future I wanted to have a body like hers, I wanted to look the same as she does in lingerie, I wanted to have curves like she does.

“You have breasts?” Kathy said to me.

Nancy laughed. “No, Kathy, I gave Greg some foam breast forms to use. Obviously, with a D cup bra he needs some help.”

“Do you have more of those breast forms?” Kathy asked.

“Sure. Why do you ask?”

“Wait one second,” Kathy said. She left the room and came back a minute later with Cindy and Krissy, who had put their tops back on.

“See, Cindy. Greg has breasts filling out his D cup bra. They’re foam breasts that Nancy gave him.”

“Wow,” Cindy said. “Do you have foam breasts I can use with my A cup bra? Or could I even get a B cup bra?”

Cindy turned to me and asked, “Is it okay if I get a B cup bra?”

“Your mom never mentioned that to me, but what the heck. Go ahead and get at least one B cup bra as an experiment to see if you like it.”

“Thanks.”

“You’re still growing, aren’t you?” Nancy asked Cindy.

“Yeah. My mom says I’ll end up a B or C cup like her.”

“I know how much young girls are proud of their newly developing busts,” Nancy said. “It makes you feel like you’re becoming women and there is absolutely nothing wrong in that! I’ll get you some breast forms.”

Nancy left and when she returned with two breast forms she said, “See how these fit in you’re A cup bra. Also take a B cup bra and try them with that." The girls headed back to the changing room.

Nancy led me to a mirror where I got to see how I looked in the bra. I was enthralled to say the least. I felt sure that my torso had more in common with that of girls – apart from the absence of real breasts – than that of boys.

“I can easily see you wearing skirts and blouses, or dresses, Greg. There’s a softness, a femininity about your body. I hope you get to one day be fulfilled in your quest to be feminine.”

“That’s so kind of you Nancy,” I said getting choked up once again.

“Remember, that anytime you’re in the mood to buy a new bra or panty or anything else – we have some lovely foundation garments here – then come in and I’ll take care of you with no recrimination or shaming.”

“You’re going to make me weep!”

Nancy smiled. “Let’s check on the girls.”

I took off my bra and joined Nancy outside the dressing room where the girls had assembled with the bras and panties they had selected.

“So, Krissy, do your bras fit?” I asked.

Krissy laughed, “Yes, Greg, my bras fit!”

“Your mom told me to ask you!”

“And Cindy. Did you buy just push up bras?”

“Yes, Greg, all my bras are push up. I’m wearing the B cup push up bra right now with the breast forms. Can I wear it home?”

It was true that Cindy’s bust was substantially larger now than it was when we entered the store.

“Of course you can. Just make sure that Nancy charges us for it! Now, how do your bras fit, Kathy?”

“Beautifully, Greg.”

“Did you get one thong and some other panties?”

“I did!”

“What about your slip?”

“I’ve got that too!”

“Great. So all we need now are stockings and pantyhose for all three girls!”

Nancy helped us select stockings and pantyhose. I paid for each girl’s lingerie with their mom’s credit card. Then we headed to a shoe store after once more putting our packages in the trunk of the car. I had a glance at the pink dress and this time I felt a buzz of excitement. In a little over a week, I might be wearing it. I knew that I’ll be obsessing every day waiting for the dress to show up in Kathy’s closet and then waiting for the time when I might be able to wear it.

***

At the shoe store Kathy predictably wanted stiletto heels.

“Mom says that your feet will ache so much at the prom that you’ll never wear them again,” I said.

“A chance I’m willing to take!”

“I’m happy with 2 inch heels,” Cindy said.

“Me too,” Krissy said. “Any higher and we might be the same height as our dates!”

“My date is tall enough that I’m going to get 3 inch stiletto heels,” Kathy said.

The girls went about the business of finding shoes they liked. While they were looking I saw a Brannock device and surreptitiously measured my foot size. I could wear 8.5 women’s shoes. Was there a way I could buy a pair of heels? If I used my mom’s credit card she’d easily know that two pairs were bought and I’d be up shit creek without a paddle.

The more I thought about the pretty high heeled shoes displayed around me and the more I watched the girls walking back and forth trying out their heels the more envious I felt. Then it occurred to me that wearing the pink dress without heels would be less than perfect. I needed heels and I racked my brain trying to figure out what to do about it when I thought of Nancy. Maybe she could help me get them somehow.

I went up to Kathy and said, “I’ll be back in five minutes. I forgot to say something to Nancy.”

I ran down the block to the lingerie shop and entered only to find Nancy with another customer. She saw me and smiled. “What can I do for you Greg?”

“Sorry for interrupting, but can I ask you a question?”

“Sure.”

Nancy excused herself and joined me. “What’s the matter Greg. You look distressed.”

“I’m sorry, but, you see, I saw the many pretty heels in the shoe store down the street and realized that I need to get heels to wear with the prom dress that Kathy will let me wear.”

“Good for you!”

“The thing is ..”

“How do you buy them?”

“Yes. I know this is crazy, but when I wear the dress I want it to be perfect. I’ve got the perfect bra and panty, and stockings. Everything is perfect, but I need the heels.”

“You’d like me to buy them for you?”

“Yes, would you? I’ll pay you for your time!”

Nancy laughed. “Annette, the manager of the shoe store is a good friend of mine. How about I call her and she’ll put the shoes you want aside until you can pay for them?”

“I can’t thank you enough.”

By the time I returned to the shop, Annette introduced herself to me. “What shoes are you interested in?”

“I have a pink dress; it’s like a prom dress.”

“We could go with white, nude, or pink shoes. There’s a lovely pair of pink shoes here.”

I immediately saw that the pink heels were to die for. “Oh my God, I love these shoes.”

Annette looked at my feet and said, what are you, eight, eight and a half, or nine?”

“I’m an eight and a half, I think.”

Annette went to the storeroom and came back with a box. “Try these on.”

I looked around. Besides the girls who were still trying on shoes, there were a few other women shopping in the store.

“Here?” I asked.

“As good a place as any. Are you embarrassed?”

“A little I guess.”

“Don't be. You need to wear these when trying on shoes.” Annette handed me a pair of footsies – short stockings covering just my feet. I took off my shoes, put on the footsies and Annette helped me put on the pink heels.

“I’ve never walked in high heels before,” I said. Even though I was in a public place my excitement at wearing women’s heels overrode my caution and fears. This was a moment I would always treasure.

Kathy noticed me taking a few halting steps with Annette holding my hand to steady me and she and the other girls came over to watch.

“I love your shoes, Greg,” Kathy said.

“And who are you?” Annette asked.

“This is my sister, Kathy, and these are her two friends Krissy and Cindy. I’ve taken them shopping for their prom outfits.”

“I love the choices you girls have made for your heels,” Annette said looking at their shoes. “What color dresses are you wearing?”

“My dress is lavender,” Kathy said.

“Silver shoes are totally appropriate. Good choice.”

“My dress is pink,” Krissy said.

“Yes, white shoes are very nice. And you, Cindy?”

“My dress is light blue.”

“Nude color will be quite nice in showing off your dress.”

I continued to stumble a bit in my heels and Kathy laughed. “Greg, I’m going to have to give you some lessons on walking in heels!”

“That will be great!”

I paid for the shoes for the girls. My own pink heels, Annette put aside until I returned with money to pay for them. I promised her I’d be back within a week. There was no way I wouldn’t have the shoes ready the first day that I’d be able to wear the pink dress.

***

I dropped off Krissy and Cindy at their houses and arrived home. Kevin and my dad weren’t home. Kathy invited me into her room with the packages. She opened up her closet and on the top shelf she removed some of her sweaters.

“This will be your shelf, Greg. First of all we can put your panty girdle and the bra and panty set you bought today. I’ll look through my bra and panty drawer and find some old bras and panties for you. You’ll need stockings. I can give you a pair that we bought today.”

“You don’t think mom will wonder what these clothes are?”

“You’re right.” Kathy moved the sweaters back so they were covering the lingerie.

“Good idea.”

“She’ll never look up there,” Kathy said. “When you get your shoes, you can put them at the back behind the sweaters.”

“I can’t thank you enough, Kathy. You’re the greatest sister a boy ever had.”

Kathy laughed. “You’ve always been kind to me and my friends. It’s the least I can do to help make you happy. Besides, it makes me sad to think how frustrated you must be not being able to be a girl whenever you want.”

“You’re going to make me cry yet again!” I said.

***

A few days later my mom returned and thanked me profusely for having taken the girls shopping. “Krissy and Cindy’s moms told me they’re very pleased with the prom outfits. The dress, the shoes, the lingerie are all perfect.” My mom laughed and added, “Cindy’s mom said you allowed Cindy to buy a B cup bra and falsies. She thinks that was a stroke of pure genius since Cindy is now so proud of her bust she’s stopped complaining to her mom about having smaller breasts than her friends.”

“I’m glad to hear that. Krissy, Cindy, and Kathy were so sweet and fun to be with. I really wanted to make sure they were happy with their prom outfits.”

“Your dad and I were wondering if you’d be willing to drive the girls and their dates to the prom? You can use your dad’s SUV.”

“Sure, I’d love to.”

“Good. Krissy and Cindy's mom will drive them to our house at seven on Saturday night.”

“Great.”

***

On the night of the prom, I was introduced to the girl’s dates. Standing next to the girls in their prom dresses, I watched the boys fidgeting in their suits and ties. I was almost overcome with envy looking at Krissy in her pink dress. With her extravagant hair style, her perfect makeup, her stockinged legs, and the easy way she stood in her heels, with the skirt of her dress swaying, I was mesmerized. Cindy and Kathy were equally beautiful. It frustrated me that the three boys didn’t seem to be impressed by how pretty the dresses were.

I dropped the kids off at the school gymnasium and watched Krissy walking to the entrance. That I’d get this dress in a matter of days overwhelmed me with excitement. I prayed that she’d take good care of it at the prom. Like, not spill grape juice on it!!!

***

At one in the morning when I picked up the girls and boys, Krissy whispered “Are you excited about getting my dress?”

After collecting my breath I nodded vigorously.

“I hope you have as much fun wearing it as I’ve had.”

“I can’t thank you enough, Krissy. You’re the greatest.”

***

Kathy kept me in the dark as to how or when she’d exchange her lavender dress for Krissy’s pink dress. All I know is that one afternoon when only she and I were home, she came to my room and said, “Follow me.”

She led me to her room where the pink dress was lying on her bed. “Oh my God, Kathy, you exchanged dresses?”

“Yes, dear sister. Now it will always be hanging in my closet for you to wear when you want to. Kevin has late football practice today; mom is at her book club until dinner time and dad won’t be home until dinner. You know what that means?”

“I can wear the dress now!”

“Kathy laughed. Go for it Greg. Pretend you’re going to the prom. Getting ready for your date to pick you up!”

Shaking like a leaf I fetched my new bra, falsies, and panty from Kathy’s closet and put them on. Then I put on pantyhose. I lowered the dress over my head and put my arms through the sleeves. Kathy zipped me up. I stepped into my pink heels and with Kathy holding my hand to steady me, we walked to the full length mirror in my parent’s bedroom.

There I was in the pink dress. Like a modern day Narcissus I stared at my image overwhelmed by love for the beautiful sight of myself so perfectly feminine in the mirror. I reveled looking at the dress whose beauty had haunted me all these weeks and that I had never believed I would ever wear.

As I stared gaping at myself, Kathy said, “I’ll leave you to yourself, Greg. I recommend that you practice walking around the house in your heels. You’ve got a ways to go before you’re steady on your feet.”

“Thank you, Kathy,” I said, half listening to her.

After the longest while, I took Kathy’s advice and slowly and carefully walked through the house. Down the stairs into the living room. Sitting down spreading out my skirts, gracefully getting up, walking to the kitchen, then back up the stairs. I walked into Kathy’s room and thanked her again.

“You’re so pretty Greg,” Kathy said. “It’s a shame you can’t be a girl all the time.”

“I don’t know about being pretty, but I feel pretty, and I do wish I could be a girl all the time.”

I walked downstairs and stood next to the front door. I thought for a few minutes about what I ought to do. Then I opened the door and stood on the threshold looking out onto the street. It’s a quiet neighborhood – only an occasional car passing by. Down the block a neighbor was mowing the lawn, some kids were playing. A couple of women were walking. A man jogged by. I didn’t care if anyone saw me. I was free.

A breeze came up and blew my skirts around me. I looked down at my dress, at my breasts, and smiled. I felt a giddy happiness unlike any I’d ever known before. It was nice to be myself. One hundred percent who I was. And what that was, was a boy whose world was completed by the chance to wear the pink prom dress.

The End