The Reunion


© 2015 by Thrillerauthor

Twenty years! It's hard to believe that much time has gone by since I limped out of Grover Cleveland High, at the bottom of my class, prospects zero. My sole achievement was the dubious designation as Class Clown, in recognition of outrageous pranks which got me suspended twice and almost expelled. The last, which nearly ruined the senior prom for everyone, featured me disguised as a girl in a long halter gown. More on that later.

College was out of the question, and my long-suffering parents made it clear that I'd have to start paying room and board if I could hang onto a minimum wage job. By then I'd had my fill of Dullsville, USA. So I loaded a backpack and headed west, hitchhiking over the Rockies and all the way to Oregon. Where I fell in with a bunch of guys who were trying to break into the sneaker business. I started out sweeping the floors, living in a converted carport and putting every penny I could spare into company stock.

Which took off like a rocket, thanks to a zany marketing campaign which I helped to inspire. Before long I was running the marketing department, working with people who were as off-the-wall as I was. Remember Bo Jackson and Bo Diddley? My baby. Stock options, promotions, and more stock options followed, and by the time I was 30 I was a millionaire, many times over, with a cool condo in Portland, a ski chalet in Bend, and a beach house on the Oregon coast.

As for my love life, let's just say that Portlandia really is the epicenter of weirdness. Amongst all the Johnny Appleseeds and Rachel Carsons, there were gorgeous girls, beautiful boys, and everything in between. With a full head of long blonde hair, and a body lithe and lean from aerobics and yoga, I found my niche....

Surfing the Internet one night, I stumbled upon a website for Grover Cleveland High, and a link to a blog about an upcoming reunion for my class. I hadn't thought about those losers in twenty years, and I doubted if any of them had an inkling of my success. I was about to move onto more fertile ground when I spied this post:

Remember Jay Fawcett? Our class clown, who almost gave Mrs. Dumphrey a heart attack at the senior prom? He sure looked hot in that dress! Wonder if he's had a sex change operation? Come to the reunion and find out!

Those bastards! Using my most memorable prank to hype their stupid reunion! They made it sound like I was coming, as a woman! The post was written by Audrey Forrest, a cheerleader who never gave me the time of day. Miss Popularity trashing the Class Clown! I was reaching for the phone to call my lawyer when a better idea came to me.

* * *

Before I go any further, I'd better explain something: when I was growing up in Dullsville, I used to dress up in my sister's clothes. All the time, whenever I could. She was several years older, and after she left for college, her closet became my amusement park. I don't think she ever knew, and I'm sure my parents never had a clue. While they were both off at work, I would try on my sister's bras and panties, skirts and dresses, shoes and stockings, makeup and jewelry. I made a pretty girl, which was an incredible rush. But it remained a deep dark secret, until the end of my senior year....

"Do you have a date for the prom?" my best friend, Andy Cooper, asked me one spring day at the lunch table.

"Nope. After I put that cherry bomb down a boy's room toilet, my parents took away my driver's license. No wheels, no dates."


"How about you?"

"Looks like I'll be sitting it out too. Julie dumped me last week, and it's too late to line up a girl I'd want to be seen with."


"So I guess we can play pool and watch TV."

"Sure, I'll come over."

"By the way, did you hear what Mrs. Dumphrey said about us?"

Mrs. Dumphrey was our guidance counsellor, who had done nothing but discourage me for four years. "No, what?" I asked.

"She told one of the girls that we're the worst students she ever worked with, and she'd be shocked if any of the girls would want to be seen with us at the prom."

"Shocked, huh?" I was steaming. Mrs. Dumprey was probably the biggest reason why my future looked so dim. And now she was kicking me and Andy when we were down! Slowly, a newfound courage came to me. "Andy," I said at length, "I want you to go ahead and rent a tux for the prom."


"I have a date for you."

"A date? Who?"


* * *

It took a lot of persuading, but eventually Andy went along. He was going into the Marines as soon as we got out of high school, and he didn't really care what the kids thought about him. Still, it wasn't till I showed him a few Polaroids of me as a girl that he decided what the hell, let's go out with a bang.

The day of the prom, I cut my last class and got home early. I spent a long time in my sister's closet, finally selecting a long gown with a halter top that she had worn as a bridesmaid to a friend's wedding. She still had the matching clutch and heels, and I found a wig that she used to wear too. Then to her dresser drawers for lingerie, nylons and bling. I scooped up some of her makeup and put everything in a duffle bag, along with two nerf balls. Then I drew a hot bath and carefully shaved my arms, legs and chest. I had never done this before, and I was amazed by how soft and feminine my body looked after I dried myself off. My parents were both still at work when I put on sweats and sneakers, slung the duffle bag over my shoulder, and walked the few blocks to Andy's house.

His mother opened the door. From the wicked smile on her face, I could tell that she was in on the secret. "Hello princess," she giggled. "Can I help you with your nails and makeup?" Andy's mom was one of the coolest ladies I've ever met, and my pulse was almost down to normal by the time Andy joined us. He looked gorgeous in his white tuxedo, and I felt very silly thinking of myself as his date. What in the world was I getting myself into?

By then, it was too late to turn back. "Sure, Mrs. Cooper, that would be great. Can I have a little privacy first before we get started?" Without a word, she led me into the master bedroom and gently closed the door behind me.

I was shivering with anticipation as I took off my sweats and laid out the contents of my duffle bag on the queen size bed. Although I'd put on my sister's clothes countless times, I'd never seen the light of day in them, and now my first public appearance would be at a formal dinner dance! My panties slid easily up my hairless legs, and for the first time I experienced the delight of nylon against smooth skin. Heaven! I savored the sensation for a few moments, sitting down on a corner of the bed and crossing my sleek legs, before I tried on the long half-slip I'd selected to wear under my dress. It felt so sexy against my stockings! Before things got out of hand, I went into the master bathroom to work on my makeup. A half-boy half-girl looked back at me in the mirror above the vanity, all silk and lace below the waist. I went to work on my boyish face: a bit of foundation, some eye liner and lip gloss were the limits of my expertise. Then the wig, a cute layered shag that instantly transformed me into a pretty girl.

My heart was racing as I hurried back into the bedroom to put on my dress. I had to step into it, sliding the straps up over my shoulders, and it took me a few tries before I was able to tie them behind my neck in a bow. The final challenge: I picked up the two small nerf balls I'd brought and tucked them into my dress. Success! They nestled snugly into the built-in bra, and gave me the illusion of a figure. I was almost in a trance as I stepped into my pumps, and at first I didn't hear the soft tapping on the bedroom door. "Jay, can I come in?"

It was Andy's mom. "Okay," I whispered, and watched as she poked her head into the room. I'll never forget the look on her startled face: surprise, concern and amusement all registered as she took me in. I busied myself with a necklace while she closed the door behind her and took me in.

"Oh my," she finally said. "If I didn't know you were a boy, I'd have never believed it. How long have you been doing this?"

"Please don't tell anyone. My mom and dad would disown me."

"All right, nuff said. I sent Andy off to get you a corsage, so we have a little time. Not that you need any help...."

"Do I really look like a girl?"

"Are you kidding? Sweetheart, you're adorable. Here, why don't you let me find you something a bit nicer to wear with that dress." She rummage through the jewelry chest on her dresser and found a simple diamond pendant. "This will be perfect," she said, and she also found some pretty clip-on earrings that sparkled and dangled. "I haven't worn these in years," she went on. "And don't worry, these aren't real diamonds -- cubic zirconium," she explained as she fastened the pendant behind me and clipped on the earrings. "Now, let's do something about your makeup. It's cute, perfect for a girl your age, but this is a big night. Mind if I jazz it up a bit?"

I nodded yes, and followed her into the bathroom, where she went to work with some eye shadow, mascara and blush. Then she wiped off my lip gloss and carefully applied a darker shade of lipstick. "Here, you'll want to have this in your purse," she said, handing me her lipstick. "Oh oh, your nails! We just have time." I stood there while she filed them down and applied a coat of quick dry polish that matched my lipstick. While we waited for them to dry, she fussed with my wig a bit, and finished me off with a few spritzes of what smelled like very expensive cologne.

"Okay Cinderella, time to go to the ball," she said. I followed her back into the bedroom, and watched as she dropped her lipstick into my clutch. "A woman my age would need an arsenal to get through an evening like this, but a sweet young thing like you doesn't need any more help from me. I'm a little worried about my son," she added.

I was trying to tell her she had nothing to worry about when we heard Andy come in the front door. "We're in here," his mother said, and we both watched as Andy came into the room. If his mother was surprised, Andy was shocked, and he stood there with an open mouth for what seemed like forever.

"Holy shit," he finally said. "Jay, is that really you?"

"I think you need to think up a better name for her tonight, don't you? Nobody at the prom is ever going to recognize her. How about Jayne?" she suggested.

* * *

Sitting in the passenger seat of Andy's car, I admired my wrist corsage while Andy rambled on nonstop about the mess I'd gotten him into. "I can't believe you look so like a girl. My mom must have helped you big time, right? We're gonna leave right after dinner. No way I'm gonna dance with you, okay? Jay?"

"It's Jayne," I said softly, practicing my female voice.

"Right, Jayne, I'll remember that. And so will you. If we're lucky, nobody will know you were there."

"So who am I? I mean, who's Jayne?"


"Come on, Andy, you have to have a cover story for me. Who's that hot chick you're with? Where did you meet her?"

"This was your idea, genius. You come up with something."

"Hmmm...I was a finalist in Miss Teen USA, you met me at a bar in Vegas, and when you told me you were going into the Marines I agreed to go to your senior prom with you. How's that?"

"Fucking ridiculous," he steamed.

"Oh dear. Well, how's this then: we met at a church retreat, your parents invited me to stay with them while my mom and dad are away, and when your girlfriend dumped you I took pity on you and agreed to be your date for the prom?"

"Better. Still fucking ridiculous, but better," he relented.

"Can I have one of those pictures?"

"What are you talking about?"

"The pictures that your mother took of us before we left."

"No way. I'm gonna destroy that camera." We both laughed nervously, and as we continued to talk, I began to feel a little more comfortable in my female persona. Until Andy turned off the road to the country club where the prom was being held, into a suburban neighborhood with big, rich people's houses.

"Uh, Andy, where are we going?"

"Prom pre-party at Dave's. Everyone will be there."

"I thought you didn't want to be seen with me?"

"I never said that. Anyway, you're looking and sounding pretty good, and I need a drink." Before I could object, we were pulling into a long driveway crowded with other kids' cars. Andy got out, and he was halfway to the front door before he turned around and looked back to see me still sitting in the front seat. He came back, and I lowered my window and said, "You go in, I'll wait here."

"Come on, Jayne. You could use one too."

He was right. "Okay, but on one condition."

"What's that?"

"You're going to treat me like a lady. Starting now, by opening my door, mister." Which he did, with a flourish, and he watched in amusement as I struggled to my feet in my long dress and tried to keep up with him in my heels. "Slow down!" I scolded him, and he took my hand and walked beside me to Dave's house.

The party was in full swing, and we headed straight for the bar downstairs. "Whoa, did you see Andy's date?" I heard one of the guys say as we went. "Who's she?" one of the girls asked. We kept moving, and I had to hike up my dress on the narrow staircase, but as soon as we were in the dimly lit basement, we were both able to relax a bit. Andy got himself a beer and a vodka tonic for me, and I threw it down so fast he got me another, and then another, as I kept to the shadows. I caught several glances from guys and girls who obviously didn't recognize me, and I played the stuck up girl who couldn't be bothered with them. Andy nursed his beer as he mingled with some of our friends, and after my third drink, I started to loosen up.

"Are you here with Andy?" a girl asked me. It was Audrey Forrest, who had never spoken to me in her life. She was pretty bombed too.

"Um hmm."

"How did you guys hook up?"

"Long story," I smiled. My female voice seemed to be working, as long as I kept it short and sweet."

"So where are you from?"


"Big city girl. Where do you go to school."

"Ohio State."

"Wow. Are you in a sorority?"

"Tri Delta." The rich, pretty girls. Audrey Forrest had just met her match. She was trying to think of something cool to say when Andy came up to us. "Hi Audrey. Would you like another drink, Jayne?"

"Yes, thanks." I followed him to the bar, leaving Audrey to wonder about the mystery woman. "I just upgraded us," I whispered in his ear.

"You what?"

"You're now dating a college girl. As in me, Miss Ohio State. Oh, and I'm a member of Delta Delta Delta."

He shook his head as he handed me my fourth vodka and tonic. "This is your last one. If I don't cut you off, you'll be Miss Fucking America next."

* * *

I was feeling no pain by the time we got to the prom. Andy opened my door this time, and I made him wait while I freshened my lipstick in the mirror on my visor. By the time we got to the country club, the receiving line was long gone, and most of the kids were sitting down to dinner. Andy found our table and escorted me to my chair, which he pulled back while I sat down demurely. A quick glance around the table found friendly, curious faces. Who's the new girl? Andy introduced me as his friend Jayne, and I said a few words to the guy on my left before he turned his attention to his date, and I turned my attention to Andy. "This is fun," I said as I smoothed my linen napkin over my dress.

"You're shitfaced," he said in a low voice.

"Indeed, sir. You were a very good boy."

"I'm driving, remember?"

"You're an excellent driver," I slurred as our soup was presented. I took a dainty sip and glanced around the room. There she was, at the head table: our esteemed guidance counselor, Mrs. Dumphrey, sitting in between the principal and the superintendent of schools. Just then, the band began to play, and all of the other kids at our table got up to dance. I tugged on Andy's sleeve, but he gave me withering look, and we sat there morosely sipping our soup while the dance floor filled. "You're no fun," I pouted when we were alone.

"We have a deal, remember? I should never have let you have so much to drink."

"Am I embarrassing you?"

"You're fucking killing me! You're the most beautiful girl here -- do you know how many guys have told me that? And I can't even touch you...."

The most beautiful girl at the prom! Was he really talking about me? My big, strong Marine...I leaned over and kissed him gently on the lips. He pulled back for a moment in surprise, then he surprised me by kissing me back, a deep soulful kiss that sparked a fire in my panties. We broke it off before anyone noticed, and sat there staring at each other for the longest time. Then the band broke into "Wooly Bully" and everybody on the dance floor started going wild. I gave him a pleading look, and he surprised me again by asking me if I'd like to dance. I was up before he could finish the sentence, and he followed me out onto the dance floor and watched in amusement as I started to gyrate in my long dress and heels. I totally lost myself in the moment, shaking and swaying to the pounding rhythm, the prettiest girl at the senior prom....

The song went on and on, as we moved our way around the floor, until we were standing a few feet away from the head table. My eyes locked on Mrs. Dumphrey She kept staring at me, and the longer she did, the surer I was that she had seen through me somehow. She was going to spoil my charade, humiliate Andy and ruin everything! Not if I beat her to it! I stood there, towering over her in my heels, feeling the eyes of hundreds of kids staring at me, as I reached behind my back and untied the straps of my halter dress. A collective gasp spread through the ballroom as my dress fell down to my hips. The Ohio State coed is topless! At the senior prom! The nerf balls tumbled out, one of them bounced on the head table and plopped into Mrs. Dumphrey's soup. Then I tore off my wig and tossed it into the air, like a cadet at a military graduation. Another gasp from the crowd as they recognized me at last! Mrs. Dumphrey fainted dead away.

* * *

I never set foot in Grover Cleveland High School again. My spectacular appearance as a boozy, topless bimbo at the senior prom touched off a near riot which got me suspended for the rest of the year, and it was only because the powers-that-be never wanted to see me again that they let me graduate with my class. My "date" enlisted in the Marines, I headed west to make my fortune, and Dullsville USA was soon forgotten.

Until I came across a blog hyping our upcoming 20th reunion, harkening back to my outrageous masquerade and speculating on whether I'd had a sex change operation! My immediate reaction was to sue for slander, but that would only bring attention to me. Evidently nobody in Dullsville was aware of the fact that I was now a multi-millionaire, with a very private lifestyle in Portlandia, and I wanted to keep it that way.

So I logged off my computer and went to bed. Normally I fall into a dreamless sleep almost immediately, but that night I stayed awake for a long time. It wasn't Audrey Forrest's inane comments about me on the reunion blog that kept me from sleeping. It was the memory of that night, twenty years ago, which I'd all but forgotten: how it felt to wear a fancy dress, how it felt to be the prettiest girl at the prom, how it felt when Andy kissed me....

I'd had my share of good-looking guys since then, and more beautiful women than I cared to remember. After twenty years of searching, I had settled somewhere between the B and the T on the GLBT rainbow. I was very selective, and very safe. And I only made love to a guy when I was dressed as a woman. My condo had two bedrooms, one with a closet full of women's clothes, and I'd perfected the art of female impersonation to the point where I could pass effortlessly as a woman. A woman who was attractive to discriminating men.

Report Story

bythrillerauthor© 13 comments/ 25664 views/ 51 favorites

Share the love

Report a Bug

4 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: