I met Bobbi in eighth grade. She was a beautiful freckled redhead, soft and curvy, and physically developed far beyond what a 13 year-old girl should be. She managed to be beautiful despite the fact that I never saw her in makeup, or in any clothes more feminine than jeans and a tee-shirt. At 13 years old, however, there's nothing remarkable about tomboys.
I had actually skipped third grade, so I was only 12.
We started hanging out when we were seated next to each other in Health class the first semester of that year. We wrote and passed entire conversations back and forth in a composition book, which soon became sitting together at lunch. We talked about almost everything. We'd make fun of our fellow students, and talk endlessly about anything we thought of.
Second semester that year, we had Introduction to Computers together, and she wasn't much of a techie. This led to the first time I visited her house. She would need help with a project now and then. It didn't happen often because she lived in the next county and shouldn't technically have been attending my school, but her parents paid the tuition to enroll her in the better school in my county.
The extra familiarity brought us even closer. We became nearly inseparable "“ talking on the phone in the evenings as well as our notes during class and lunch period conversations.
Things really started to change between us that summer. We found ourselves on the phone more and more, and I realized something that was a new experience for me: I missed being with her every day. I worked up my nerve and asked my father what I should do.
"Ask her on a date, " he told me. "Take her to see a movie, or to go skating. I'll take care of the ride and all."
Later that afternoon, I called her up. I was nervous, and thought I was going to puke, but I finally managed to stammer out, "Bobbi, would you like to go out with me?"
She laughed lightly, like bells ringing, and replied, "Of course!"
I wanted everything perfect, and found the perfect spot. There was a roller skating rink in her town that was adjacent to a pizza parlor and Dollar Theater. They were playing Back to the Future 3 at 1 pm, so I was looking forward to spending most of that day with her.
I was terribly nervous as Dad drove over to pick her up, and very anxious. My first date! I stuck myself on the thorns of the rose I'd bought her, and when I got out of the car, I nearly passed out.
I knocked on her door, and her father answered. He invited me to sit on the couch, and we made small talk about sports as she finished getting ready.
Finally, I heard her start walking down the stairs, so I looked up. I couldn't believe my eyes! Bobbi was gorgeous! She was wearing makeup! Her long, thick, wavy red hair was loose and came halfway down her back, as opposed to her standard ponytail. But what nearly knocked me over was her outfit: She was wearing a skirt! A plaid knee-length pleated skirt in the schoolgirl style with a white blouse, even stockings! She smiled at me, and I grinned back inanely.
We made it into the movie about an hour early, and we sat in the back while the ads were playing and started talking about everything, like we always do. I put my arm around her as we talked, and she edged a little closer to me. I was in heaven.
Only a few minutes later, I noticed that she seemed uncomfortable. She was fidgeting, tugging at her skirt, pulling at her stockings, and brushing the hair back out of her face with her fingers.
I asked her, "Are you okay?"
"I just feel really weird in these clothes. My mother insisted that I wear them, but you know I hate wearing this girly stuff. I mean, I can tell you like it, but it's really not me," she told me, adjusting her skirt once again.
"I wondered if you even owned any stuff like that. I hate that you're uncomfortable, though. If I could do anything to help, I would," I replied.
"Don't worry about it, Jesse. I'll get by."
We still had 45 minutes left before the movie started, so we went to the concession stand to get drinks and popcorn. We chatted in line, and she was still fidgeting, smoothing her skirt and toying with her hair. Her edginess was like a barrier between us, so I thought I'd try to break the tension with humor.
"You know, we're almost exactly the same size. Why don't we just switch clothes so you can relax?"
She looked in my eyes, and I could see her eyes brimming with tears. :"You'd really do that for me?" she asked me timidly. So much for a joke. How could I refuse?
"Sure, Bobbi."
She flashed me one of her room-brightening smiles and lead me to the ladies room. After ducking in to make sure it was empty, she pulled me inside. She gestured towards a handicapped stall and told me to strip.
A few seconds later, I passed her my pants and sweat shirt under the door. "Boxers, too, Jesse," she told me. I passed them to her, as well.
I waited patiently in the stall, naked, as she changed her clothes and washed her face. She knocked on the stall door. "I'm coming in," she announced.
I covered myself with my hands as she entered, looking like she always does, but without her bra, her chest looked a lot smaller. Still there, but not quite in my face. Her hair was pulled back into her usual ponytail, and her face was scrubbed. With my clothes and shoes on, she looked exactly like the Bobbi I'd known for 2 semesters.
The first thing she handed me was some weird white contraption of satin, straps, clips, and buckles that I now know is a garter belt. She helped me get it around my waist and fastened. Every time she touched me, my body tingled, and I could feel my member stirring down below. How embarrassing!
She didn't say anything about it, however. She motioned for me to sit and she gently rolled the stockings up each leg, where she clipped it to the garter belt. Then she handed me her white stretch satin panties. I stood and stepped into them, and pulled them up onto my hips. Except for the unusual feeling of being so restrained in the crotch, I was amazingly comfortable. I was starting to wonder what exactly I'd gotten myself into, but it was too late. Bobbi was already guiding me into her bra. After fastening the hooks and adjusting the straps, she started filling the cups up with tissue.
The blouse was next, and the buttons were backwards. It took me a few minutes to get them all buttoned. She held the skirt out for me next, and adjusted it on my waist and zipped it. Amazingly, our feet were the same size as well, so slipping into her little black flats was no problem at all.
Now that I was dressed, Bobbi pulled a few plastic cases out of her purse. She brushed some makeup on my face, then let my hair down. Thankfully, my hair was shoulder length, and I was just glad that this wasn't my town. No one here would know me. She clasped her necklace around my neck, slipped her watch on my wrist, and put her rings on my fingers.
"Close your eyes," said Bobbi, as she opened the stall door and led me towards the mirror. "Open 'em!"
I couldn't believe my eyes. The girl in the mirror could easily have taken my breath away. As I realized the girl was me, I passed out.
And Bobbi caught me!
She led me back to the concession stand so we could get our drinks and popcorn. We still had 15 minutes!
By the time we were back in our seats, which was even before the previews started, I had forgotten that I was dressed up like a girl... until her hand caressing my stocking-clad thigh under my skirt reminded me halfway through the movie. She leaned towards me, and kissed me, sweetly and deeply.
Here I was, on my first date with a girl, and had my first kiss, and I was wearing her clothes.
And enjoying it!
We left the movie, both grinning like maniacs. We went into the ladies room to touch up my makeup, and wash hers off again. Ahhh... The joys of your first make-out session.
Our next stop was the skating rink, where much more fun was had. We skated, talked, and generally hung out for hours. Eventually, we got hungry and headed over to the pizza parlor.
During dinner, we got lost in conversation about the movie, and the whole series, when I looked at my watch. Her watch. Whatever. My Dad was going to be here to pick us up in less than 5 minutes!
"Shit!" we exclaimed in unison, and headed for the girls room. We hopped into the stall, and started stripping as quickly as possible. "Keep the underwear "“ we don't have time!" I had to agree with her. I dumped the stuffing and just threw my sweatshirt over the bra and pulled my pants over the garter belt set. We swapped shoes and headed out of the bathroom, just in time to see Dad pull into the parking lot.
The trip to her house was uneventful, but we were both still buzzed with excitement. I walked her to her door, and even got the goodnight kiss. On my first date! After the kiss, she reached around and tugged on my bra strap. "I've had a lot of fun tonight. I hope we can do it again," she whispered in my ear.
I was so tired I didn't bother changing when I got home. I slept in her underwear that night, and dreamed of her.
Our next date was the following weekend. It was pretty much the same thing we'd do all summer "“ except she'd convinced her mother to let her wear her normal clothes. More often than not, however, Bobbi's mom would insist that she dress up.
On our third date, she was wearing a small white top and black miniskirt with a silver belt.
She made it through the movie, but less than 20 minutes into our skates, she was getting antsy again.
"Jesse, would you do me a HUGE favor?" she asked me, boring into my soul with those deep green eyes.
"Anything," I replied.
About 10 minutes later, I was in drag again.
We had many dates that summer, and Bobbi made quite an effort to adapt to girly clothes. Ironically, I didn't understand what the problem was. I was perfectly comfortable with them. We'd swap clothes in the middle of the date, when she'd get antsy. Usually, however, I was in drag for the whole date.
After 4 dates, Bobbi brought along some extra supplies allowing her to bind her breasts so she looked like a guy. She started shopping via catalog, ordering padding, falsies, so that I could wear the more revealing clothes her mother was trying to dress her in. While Bobbi was fairly well-endowed, my falsies were only A-cups (anything bigger looked ridiculous without the hips to match). Therefore, I ended up with my own bra collection.
A few times, we experimented with different ideas: Matching outfits and the like. We had a lot of fun with it, and Bobbi convinced me to swap underwear with her even when we didn't change the rest of our clothes. I went home in her underwear after every date, until I had run out my own! Thankfully, I'd been doing my own laundry for a few years by then, so no one noticed that my underwear drawer was heavy on the Victoria's Secret and light on the Fruit of the Loom.
I also noticed that Bobbi never seemed to have a problem wearing girly clothes as long as I was dolled up right along with her.
Bobbi apparently had quite a sense of adventure, as she constantly seemed to get more and more daring. There were about 4 weeks left of summer before we started high school, and we were at the skating rink in matching outfits, exactly like she had worn to and I had worn during our first date. Bobbi spotted a blonde girl about our age wearing an outfit exactly like ours! Bobbi waved her over.
She introduced herself as Amy. We spent the next few hours hanging out with her, but I was very nervous because I was worried about being "found out." This was the first time I'd ever had a conversation while dressed, and I wasn't sure I could deal with the scrutiny up close. I was so self-conscious that I wasn't listening to what Bobbi and Amy were talking about.
"Let me just call my parents," Bobbi told Amy, and she headed for the wall of pay phones, dragging me in tow.
"Well, what do you think?" Bobbi asked me.
"About what?"
"Going to Amy's slumber party tonight. What is wrong with you? Weren't you listening?"
"Hey! That's the first time anyone but you has seen me up close. I was nervous, okay."
"But do you want to go?"
"I don't know. Don't you think it's a bit risky?"
"Nah," Bobbi waved dismissively. "She seems nice. Besides, I want to know what the surprise is."
"I mean about someone finding out I'm a guy. Wait, what surprise?"
"She said she has something really cool to show us when we get there. Doesn't it sound like fun?" she giggled.
A few minutes later, she wore me down and I agreed to go. Of course, all it took was a reminder that she and I would be spending the night together. I called my parents with some excuse to stay out, Bobbi did the same with her folks. Arrangements were made for my dad to pick us up from the skating rink the following day. Bobbi rented a locker, and stuffed my book bag with my regular clothes in it. Slipping the key into her purse, she told me, "Just so you can't leave them at Amy's." We hung out with Amy until her parents came to get her. By that time, I was at ease and had once again forgot I was in drag.
"Don't you all look so adorable!" Amy's mother exclaimed when she saw the three of us. "Did you girls plan the matching outfits?" My anxiety kicked back in as I endured my first extended encounter with an adult. I was lost in my nervousness the entire drive.
I'd guess it was about 5 or 6 when we hopped out of the back of Amy's mom's minivan in front of a red two-story house. As Amy led us to the door, her mom ticked off a standard "be good and not too loud or late" speech.
In the living room, Amy turned on the TV, sat down in the recliner, and motioned towards the couch. We all sat and chatted while waiting for the other guests to arrive. It was just starting to occur to me that while I'd be spending the night with Bobbi, we weren't likely to do much making out. I wasn't so sure I wouldn't regret coming to the party.
Just as I was about to pull Bobbi aside and try to find a way to bail out, the doorbell rang. Amy answered the door, and in walked 3 girls wearing outfits identical to ours!
"Jesse, Bobbi, this is Tina, Lisa, and Jen," Amy introduced. "Girls, this is Jesse and Bobbi. I met them while I was skating, and they were wearing the same outfits we all bought for tonight! I thought it would be so cool to bring them." She turned to us. "This is the surprise I was telling you about."
All of us file up the stairs after Amy, to a suite of two rooms with a bathroom. The room at the top of the stairs was arranged as a sitting room, with an equally-huge bedroom to the right. Bobbi and I sat in the love seat, Amy took the armchair, and Tina, Lisa, and Jen took the couch.
I started getting a little nervous again as I looked around the room. I was surrounded by 5 girls, all almost exactly the same height, wearing identical outfits that made me think of naughty schoolgirls. I was nervous, and a bit turned on, as we all started talking and getting to know each other.
Of course there's Bobbi, my girlfriend. I already mentioned that she was 13, but most of the time she looks about 15 or 16. It's gotta be those curves! She fills out a C cup rather well, and that red hair drives me wild!
Amy, as it turns out, is a cheerleader. She's a stereotypical 14 year old blonde. Her hair is a little wavy and hangs just past her shoulders. She's trim and athletic from the cheering and gymnastics, while being curvy enough to properly fill a B cup. She's really bubbly in personality, and I thought she was really superficial at first. This whole matching-outfit party was her idea from the start. She has never lived anywhere but here, and is really into horses. She's trying to get her family to give her one.
Tina is the Mexican girl. She was born in Vera Cruz, and her family moved here when she was 7. She's 15, speaks perfect English with a faint accent, but is fluent in Spanish as well. While she, like the rest of the girls, is absolutely gorgeous, she manages to do it while being no more curvy than I look. An A cup at most.
Lisa is the real athlete here. She's on the soccer, softball, and volleyball teams at her school. She's of average build, about a B cup, but in amazing physical condition. She's really strong, really fast, and almost intimidating. No wonder she's a freshman but on the varsity teams. Her hair is dark brown, nearly straight, and usually in a ponytail that just hangs to her neck.
Jen's 16, and was born close to here, but her family emigrated from Laos just before she was born.
She's trim and fit, and on the swim team for her school. She's got that compact cuteness that most people stereotypically attribute to Asian girls. She doesn't talk much, so I didn't really learn that much about her right off the bat. She's probably a B cup, and I think she's the musical type.
And of course, there's me. I've got blonde hair, just down to my shoulders. I'm padded to fill out an A cup bra, and the only other person here who knows I'm really a boy is Bobbi. I'm 12 years old, but I seem to look about 15 or so as a girl.
Imagine yourself in this situation... What would you do if you were about to spend the night with 5 girls, and the catch was that 4 of them can't know you're a boy?
It was more fun that I'd have ever thought, though. We played "Truth or Dare," watched movies, and just talked about random nonsense. Despite what I've always thought about girls, the topic of boys never really came up. Before we went to bed that night, Bobbi and I agreed to do this again with the girls next week.
Bobbi and I slept in Amy's bed that night, because we were the only ones who weren't prepared for the party. Amy loaned us some of her pajamas, and we all crawled into the bed. I ended up in the middle. Nothing happened that shouldn't have happened that night, but it felt really good to hold Bobbi while we slept.
The next morning went off without a hitch. We were dropped off at the skating rink where I managed to change into guy clothes just in time for the ride home.
I can't wait for next weekend!
