The Reunion

© 2015 by Nom de Plume

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.

It had all started that magical night. I’d always thought I was just another heterosexual crossdresser, until Andy kissed me. It was like somebody threw a switch! As I tossed and turned, I wondered whatever happened to him? Was he still in the Marines? Had he gotten married? Or was he alone, like me? Did he remember me too? Before I drifted off to sleep, I decided to find out.

* * *

It took me a few days to clear my schedule, and I spent most of them surfing the web. The reunion was that coming Saturday, featuring a luncheon at Grover Cleveland, followed by a dinner dance at the same country club where I had posed as a tipsy coed. Next, I searched for any information about Andy’s whereabouts. And came up empty. His mother was still living in the same house, but Andy seemed to have vanished from the face of the earth. My parents couldn’t help – they were long gone, having moved into a retirement home I bought for them in Scottsdale in return for promising not to tell anyone where the money came from. But Audrey Forrest was still in town, divorced and working as a real estate agent.

I packed two suitcases and flew first class to Cincinnati, where I had to rent a car and drive for almost an hour. It was a beautiful spring day, and I sprang for a convertible, which made the drive almost enjoyable. When I finally pulled into Dullsville, it was like the hands of time had turned back twenty years – nothing had changed. I found the street where Andy’s mother still lived, pulled into the driveway, and strode to the front door. When she opened it, I hardly recognized her: the sixty something woman standing before me was older, of course, and there was a sadness in her face that I did not remember. But it vanished as soon as she realized who I was. “Jay!” she cried, and we hugged for a long time before she sat me down in the living room. “You look wonderful! I can’t believe you’re here. Your parents disappeared without a trace years ago. What are you doing back in Dullsville?”

“Believe it or not, I’m here for our twentieth reunion.”

She laughed out loud. “Oh Lordy, what a surprise. I never thought you’d show your face again after the prom.”

“To tell you the truth, I got so drunk that night, I can’t even remember how I got home.”

“You didn’t! When Andy dragged you back here, I helped you take off your dress and clean off your makeup, and put you to bed on that couch you’re sitting on. Your folks were very unhappy the next morning.”

“So was the rest of the town. Where is Andy these days?”

The sadness returned to her face. “Let me get us some coffee.”

* * *

It took some time before she was ready to talk about it. Andy had gone into the Marines right after graduation, and fought in the Gulf War. He was almost killed in an ambush, and although his wounds were not life-threatening, he was never the same after that. “Post Traumatic Stress Disorder, they called it. When he got out, he came back here for a while, and spent hours staring off into space. He sat right there, or in his room, for days on end. At first I thought it was only temporary, but as time went by and he didn’t get any better, I started to give up hope. I tried and tried to get through to him, but nothing seemed to work. Until I showed him that picture.”

“What picture?”

She got up and returned with a photo album. “You probably don’t remember this,” she said as she flipped through it, until she found an old color photograph of a boy in a white tuxedo, standing awkwardly next to a gorgeous girl in a long formal gown. It was Andy and me, on our way to the senior prom. “You were so precious! When I showed him that picture, he brightened up immediately, and we talked for hours about the good old days. ‘What ever happened to Jay?’ he’d ask me, over and over.

“Eventually he got well enough to leave home, and he enrolled in community college, but that didn’t last long. He got a job, and met a girl, but that didn’t last long either.” She wiped a tear from her eye. “But he refused to just stay here. He’s working for some county down in Kentucky, it’s a nothing job really, but it keeps him outdoors and he doesn’t have to wear a tie.”

“That sounds like Andy.”

“At least it keeps him fit. Do you know, he could still wear the clothes he wore in high school? I have a closet full of them.”

“So he still looks the same?”

“I wish! That last time I saw Andy, which was Christmas last year, he looked like a homeless person – scraggly hair and a long beard. Although I know he has a small apartment in Cincinnati. His disability checks from the Marines go there.”

“So he drives across the river to Kentucky every day?”

“He rides the bus.”

“Do you mind if I ask for his address?”

“Of course not! I’m sure he’d love to see you. And it might be the best thing for him. The doctors tell me that reliving happy experiences might help to bring him back.” She hesitated. “There’s one thing I haven’t told you.”

“Yes?”

“That day I showed him that picture, he said something. ‘The only girl I ever loved, and she wasn’t even a girl.’ Do you know what he meant?”

“Yes, I think I do.”

* * *

On the drive back to Cincinnati, I tried to process what I’d learned about Andy. He looked like a bum, he was living in poverty, and he remembered me as a girl. More than remembered – he told his mother he loved me. It doesn’t get much heavier than that!

I parked a block away from the address his mother gave me and cased the neighborhood. Andy lived in a scruffy garden apartment complex full of bikes and strollers. His apartment was on the first floor, and I could stake out the entrance from a park bench just outside. I left, checked into the Hyatt Regency downtown, and unpacked one of my suitcases. The one filled with women’s clothing, shoes and accessories.

I hadn’t anticipated this kind of date when I packed my suitcase in Portlandia! Fortunately, I’d thrown in a khaki skirt and knee sox, in case I needed to do some shopping – one of the many things I’ve learned after years of crossdressing is that the easiest way to blend as a woman is to wear what the women wear, and most of the dressy outfits I brought would have been totally out of place at a place like a mall. Although my hair was marginally long enough to wear as a woman, I had a wig that was very similar to the one I wore to the senior prom, and I wanted Andy to see me the way he remembered me. After a quick bath, I put on a body briefer and slip, some makeup, and did my nails. Memories of the only time I did this for Andy came flooding back. I wouldn’t have his mother’s help this time! After I padded myself up, I tugged on my wig, which instantly made me look ten years younger. I pulled on a girly mock turtleneck, stepped into my skirt, and pulled on my knee sox. So cute! Ballet flats completed the look.

I put my car keys and stuff into a casual purse, retrieved my car from the valet (nobody seemed to notice that I dropped it off as a guy and picked it up as a girl) and drove back to Andy’s neighborhood. The sun was low on the horizon, so I wore sunglasses, and this time I parked as close as I could – it would be dusk soon, and I always felt very vulnerable as a single woman after the sun went down. I tried the phone number that his mother gave me, but there was no answer, so I returned to the park bench and sat down to wait.

I didn’t have to wait for long. A municipal bus pulled up, and a tall, middle aged man shuffled off and started walking towards the apartment building. His jeans and flannel shirt looked like they hadn’t been washed in decades, which may have been the last time he had a shave and a haircut. It was Andy, all right. I put two fingers in my teeth and gave him the shrill whistle that we used to use to signal each other when we were kids.

He stopped instantly and slowly turned around. Then he just stood there, staring at me, for a minute at least, maybe longer, before he took a few tentative steps in my direction, and then stopped. I waved at him and motioned for him to join me. A few more baby steps, another pause, and eventually he was standing in front of me, looking down at his feet, his face flushed with embarrassment. He didn’t smell very good, but I stood up and hugged him, and he hugged me back. “Jay,” he finally said in a halting voice, “is it really you?”

“It’s Jayne, remember?” I replied, in a voice he hadn’t heard in twenty years. I took his hand and guided him to my bench. He collapsed next to me and began shaking and sobbing, tears streaming down his ruddy face. I just let him go, rubbing his shoulders occasionally, and saying over and over, “It’s okay, Andy. It’s okay.”

* * *

We sat on that bench until way after dark. Once Andy stopped crying, he started talking, and with a little prompting from me, he took me through what he could remember of the past twenty years, which wasn’t much. He vividly recalled his induction into the Marines, how he almost washed out of basic training but refused to give up and eventually became a squad leader. He also recalled his service in Iraq, up to the moment when a roadside ambush killed two of his buddies and almost him. He remembered next to nothing about his agonizing recovery, and the endless meetings with doctors and shrinks before he was finally eased out of the corps. His inability to bring back unpleasant memories seemed like some kind of defense mechanism to me, because he had no trouble remembering the good times at Grover Cleveland High. Especially the senior prom.

“You were so fucking hot,” he said. “That night, after you pulled down your dress, I was lucky to get you out of there alive.”

“I have no recollection of that. I was so drunk! Yesterday your mother told me I spent the night on your sofa.”

“Yep, when you weren’t talking to Ralph on the big white phone. Why did you call my mom?”

“To find you.”

He paused for a moment to digest this. “I think about you all the time.”

“And I couldn’t get to sleep the other night, thinking about you.”

He looked me up and down. “So when did you go under the knife?”

“Me? I’m still a guy, Andy.”

“No shit! You just dress up like that?”

“Sometimes. And sometimes I don’t. Call me a flibbertigibbet,” I shrugged.

“What do you do when you’re not making pretend you’re a girl?”

I laughed. “It’s a long story. I was hoping maybe you’d take me out to dinner, and we could get to know one another again.”

Now he laughed. “Uh, I might be able to afford Taco Bell.”

“My treat then. On one condition. No, make that two.”

“Yes?”

“Do some laundry and take a bath!”

* * *

We agreed to meet the following night, which was Friday, the day before the reunion. I hadn’t even mentioned the reunion to Andy, and I was so focused on my date with him that I wasn’t even sure I wanted to go. Still, it would be good to have a ticket, just in case. So before I went to bed, I logged onto the Grover Cleveland website and signed myself up. I got a ticket for a guest too, in case Andy felt like going. If he didn’t, I could always bail out. Now that Andy was back in my life, going to the reunion as a woman was the farthest thing from my mind.

I slept until almost noon, thanks to the 3 hour time difference, and treated myself to a room service breakfast in my nightgown and robe. Then I took care of business calls and emails before I spent some time surfing the web. For some reason I checked out the reunion blog, and found this post by Audrey Forrest:

Guess who just signed up for our reunion? Jay Fawcett, our class clown! Is the circus in town? Did he buy a new dress? We’ll find out Saturday night!

I was regretting my decision not to sue her for slander. Then I took another look at the itinerary for the reunion, and came up with the beginnings of a plan. I spent the next couple of hours scrutinizing real estate sites for information about Audrey Forrest’s listings, and was surprised when I finally looked at the time. Almost time to get dressed for my date with Andy! I spent a few minutes looking at the hotel guide, found the Cincinnati yellow pages in one of the nightstands, and jotted down some numbers and addresses. Then I called Andy’s mother to ask her a quick question, and got the answer I was hoping for.

It was time for Jay to become Jayne. First, a long, hot bubble bath. I took my time shaving off every bit of body hair, from head to toe, then I added some more hot water and just luxuriated in the sensation of sheer femininity before I toweled myself off and put on my wig and makeup. It was always a rush for me, dressing myself as a woman, but knowing that I was getting dressed for a date with a man sent my dopamine levels through the roof! The outfit I’d selected looked best with an “all in one” body briefer underneath to nip my waist, with lovely silicone breast forms and hip pads to round me out. Sheer nylons made my legs look and feel wonderful, a camisole and a lacy half slip would help my tie-back top and swirly skirt look like they were made for me, and my designer flats were very cute. A necklace, hoop earrings with built-in clips, a classy woman’s watch and a few rings completed the look.

I grabbed a matching purse and collected my car for the drive to Andy’s. He was waiting for me at our park bench, looking just the same as he had the night before, only it was obvious that he had scrubbed himself and put on some clean bum clothes. Why was I so attracted to him? Part of it had to do with our remembered past, and how totally cool he’d been the night of the prom. On another level, I felt genuine compassion for him after all he’d been through, risking his life while I was making millions and living la vida loca. But beyond all that, Andy had an animal magnetism, which brought out my female instincts to make a project out of him.

The attraction was mutual. “Wow,” he said when he climbed into my car. “I still can’t believe it’s really you.” It was a warm spring night, and I had the top down which made conversation difficult, but we were content just to be in each other’s presence. Twenty years is a long time, but it seemed like only yesterday when he was driving me to the senior prom. Now I doubted if he even had a driver’s license, let alone a car. Why was I so attracted to him?

I pulled up at the Hyatt and he followed me into the majestic lobby, drawing stares of disapproval from some of the staff and guests. Andy never seemed to care what people thought of him, and I took his hand as we rode the long escalator up to the mezzanine and found the fancy restaurant. The maître d’ blinked when he saw us, but maybe he thought Andy was a rock star, because he showed us to an out-of-the-way table. Andy asked for a beer, and I ordered a vodka tonic for old times’ sake. We sat there in our little booth, staring into each other’s eyes, for the longest time.

“I called my mom this morning. She told me you’re in town for some kind of reunion.”

“Yes, can you believe it? Twenty years since we left Grover Cleveland.”

“I can’t believe you’d want to go back.”

“It’s not important to me now.” I explained how I’d come across Audrey Forrest’s insults, and was so pissed I decided to come back and rub everyone’s noses in my improbable success. As we sipped our drinks, I took him through it, nice and slow: how I’d gotten in on the ground floor at an unknown company, inspired their groundbreaking marketing campaigns and ridden the wave. How I’d piled up millions of dollars. And how I was exploring my feminine side. The waiter came, and with some urging from me, Andy ordered a huge steak. I had pasta, and several glasses of wine, while Andy ate like a Biafran child.

When we were done, the waiter brought Andy the check. I asked him to hand it to me, and charged it to my room while Andy looked on. “Room 921/2,” he said. “You have two rooms?”

“It’s a suite, actually.”

“It’s probably bigger than my apartment.”

“Come see.”

* * *

The next morning, when I finally woke up, I looked over at the snoring hunk of man next to me and sighed. What a night!

Most of the men in my life had been fey Portlandia boytoys. There was something raw and genuine about the way Andy made love to me, although at first I didn’t think he had it in him. When we got to my suite, he looked around nervously while I kicked off my shoes and curled up on the sofa in my parlor.

Eventually he sat down next to me, and I could tell that he was staring at my legs. “I never saw them that night,” he finally said.

“Huh?”

“Your legs. You were wearing that long dress. And yesterday you had on those long sox. They’re really nice.” I took his hand and slid it up my nylons, feeling a spike of arousal while he began to explore under my skirt. I looked up at him expectantly and he kissed me, which felt funny at first because of his fuzzy beard, but he was very tender and gentle, almost tentative in the way he teased me with his tongue while his fingers continued to probe. I reached down to feel him through his trousers, and was surprised that he wasn’t hard. He broke things off and stammered, “I’m not much of a man anymore. Haven’t made it with a woman in so long…I’m sorry….”

“Is it because I’m really a guy?”

“No! You’re more of a woman than any woman I’ve ever made it with. It’s just been so long….”

“That’s okay, baby. We can just cuddle and talk, as far as I’m concerned. You want to know something? That kiss just now, it reminded me of the time you kissed me at the senior prom. So nice.”

He reached into his pants pocket and pulled out his wallet. “Want to see something? I’ve been carrying this around for twenty years.” It was an old, creased picture of my face, cut out from a photo like the one his mother had shown me the day before, taken the night he took me to the prom.

“I was a sweet young thing, wasn’t I?”

“You blew my mind that night. Messed me up real good, too. I mean, I made it with some girls after that, but it never felt right….”

“I’m so sorry, Andy! I never meant to fuck with your mind. It was all supposed to be just a stupid prank.”

“Don’t apologize.” He kissed me again, and I thought I could feel him stirring through his trousers. He looked into my eyes and said, “Maybe we could try.” I started to unbutton his shirt, and after he finished I unfastened his belt. He stood up and dropped his trousers, then I helped him pull off his boxers and sox. I was surprised to see that he was almost at half mast. I stood up and slowly stepped out of my skirt. Then I untied the bow behind my blouse and pulled it over my head. My lacy half slip was next. I sat back down beside him and let him kiss me, again and again, gently stroking him while he fondled my fake breasts through my camisole, and caressed my legs through my stockings.

Then I bent over and took him into my mouth, teasing his quivering penis with my teeth. “Oh baby,” he moaned. “Please don’t stop.” I kept at it, nibbling and sucking, and he got harder and harder, until I could tell that he was past the point of no return. “Oh God,” he cried out, and then he was cumming in my mouth, wave after wave, which I slurped down as best I could. I was so into pleasing him, which turned me on too, and when he was finally done I sat up and kissed him, a long, deep kiss that had me smoldering. He pulled down my pantyhose and started to fumble with my body briefer, confused that he couldn’t just pull it down like panties.

I stood up and took his hand, leading him into the bedroom. I pointed to the king sized bed and said, “Wait there.” Then I took a babydoll nightie, thong, garterbelt and stockings out of my suitcase and went into the bathroom to change. My wig was a mess, so I brushed it back into shape, then I took off my lingerie and nylons and pulled on my nightie and thong. The stockings were a nuisance to fasten, but I hoped they’d turn him on.

“Wow,” he said when I pranced back into the bedroom and hopped onto the bed next to him. “Look at you!”

“My turn,” I said, and I pushed him down and threw myself on top of him, sliding my silky legs against his while we locked in another deep kiss. My penis was getting hard, straining against my thong, which Andy pulled off me. Then he started to play with me, tugging and teasing as I got harder and harder. I reached down to find him stiff as a board – after so many years, his body was making up for lost time! I slid my ass over him and guided him into me while he lay back on the bed, not quite believing what was happening to him. He was still plenty slick from his first orgasm, and I was able to ease myself onto him, a little at a time, until I was impaled on his rock hard shaft, humping him up and down, up and down. His eyes rolled back in his head as he felt the beginnings of another orgasm beginning to well up in him, and I took his hand and placed it on my penis, which was almost ready too. Up and down, up and down, faster and faster, until he gritted his teeth and I could feel him throbbing inside me, which triggered my own orgasm, spewing gobs of semen on his chest as the waves of sweet ecstasy washed over me.

We collapsed into each other’s arms, and when we got our breath back, we talked for hours. It was like Andy hadn’t had any human companionship, intimate female companionship, for years, and once he got going, I couldn’t turn him off, not that I wanted to. So I mostly listened as he bared is soul about how he’d wasted his life, and when I told him things were going to be different from now on, he didn’t believe me. But the more I said it, the less he protested. Finally, we fell into a blissful sleep.

* * *

“Wakey wakey,” I whispered. Andy sat up with a start, looked at me, and smiled.

“So it wasn’t a dream, I’m really here, and you’re really you.”

“Yep.”

I gasped as he rolled me over on my back and wrapped my stockinged legs behind his neck. And I gasped again as he entered me, which hurt at first since we were both dry, but soon he was in me again and I was rocking to his rhythm, slowly at first, then faster and faster as he huffed and puffed, losing himself in unbridled joy at being a man again, with me as his woman, and when he came it was with a rush, and although I didn’t feel it coming, I came too, wicked spasms that I felt all the way down to my toes, sheer delight that went on and on and on….

When it was finally over, he spooned me and whispered over and over, “I love you. I love you.”

“I love you too,” I told him, “and things are gonna be different from now on.”

“Like how?” he asked me.

“Well, for starters, you’re gonna move out of that disaster apartment and come home with me. And you’re gonna get a haircut, and shave off that beard, and be my Andy again.”

I waited for him to say no, but he didn’t. He just cuddled me, kissed my neck and said “We’ll see.”

We showered together – he saw me without my wig for the first time, but my hair was long enough for a girl and he didn’t seem to mind – and then we wrapped hotel bathrobes around ourselves and enjoyed a room service breakfast. I told him about my plans for the day, and at first he resisted. But I wore him down, and I was holding all the cards, so he reluctantly agreed.

I changed myself back into Jay. Andy frowned when he saw me. “I don’t know how to say this, but for some reason, when you’re a guy, it isn’t the same. The way I feel about you, I mean.”

“And when I’m a guy, I’m not particularly attracted to you. Weird, huh?”

“So where are we going with this?”

“Sweetheart, after last night, I could change my flight from Portland to Bangkok and have the operation tomorrow.”

“Really? You’d do that for me?”

“For us, Andy. For us.”

* * *

It was amusing to pick up my car as a guy this time – I did get a double-take from the valet – and we drove to Andy’s house first. His mother was overwhelmed, but she finally composed herself and served us coffee while we talked about old times. I excused myself at one point, found the package she had waiting for me by the front door, took it out to the car and stored it in the trunk. Andy didn’t notice a thing.

Then it was off to Grover Cleveland for the reunion luncheon. No tickets were required for this event, and we were both surprised by how many people were already milling around the lunchroom. As prearranged, Andy and I separated, and he started to mingle with startled classmates, who probably thought he was a homeless person who had wandered into the room looking for a free meal. Meanwhile, I made my way towards Audrey Forrest, who was holding court over a small knot of well-dressed men. In my jeans, outrageous tee shirt and sneakers, with long hair hanging over my ears, I was decidedly out of place. It didn’t take long for Audrey to spot me, and I’m sure she didn’t recognize me at first. I stood by myself, listening to snippets of conversation, until her curiosity got the better of her. “Who’s this mysterious stranger?” she asked.

“Hi Audrey. You’re looking good. Don’t you recognize me?”

It’s a truism that although people age at different rates, our voices stay the same (unless we’re changing genders) and Ashley’s eyes widened as she realized who I was. “Jay? Jay Fawcett?”

“You sound surprised to see me.”

“More like shocked. The last time I saw you, you looked a little different….”

“That was a fun night.”

“And what are you doing with yourself these days?” The guys she had been presiding over were staring at me too.

“Counting my millions.”

She laughed out loud. “So where do you live?”

“I have three homes.”

“Still the class clown.” She pulled a business card out of her purse. Audrey Forrest, Realtor. With a picture that made her look many years younger. “Looking for a fourth?” she taunted me.

“Not right now. But I know someone who could use your help. He’s right over there.” I pointed to Andy, who was hunkered down at the appetizer table, shoveling pretzels into his mouth.

“He looks like he sleeps under a bridge.”

“He’s not long on cash, but he has a small income. Maybe you could help him find something?”

“I don’t think so.” She looked away from him.

Just then a familiar voice came over the PA system. “Welcome to the Class of 95! Will you please find seats so that lunch can be served.” Who was that voice? My God, it was Mrs. Dumphrey!

“I can’t believe that old bag is still a guidance counsellor. Hasn’t she poisoned enough young minds?” I said.

Audrey was shocked. “You really have been away, Jay. Mrs. Dumphrey has been the principal of Grover Cleveland for years.”

“You’re shitting me, right?”

I could feel her presence behind me before I turned around. Twenty years older, with the same dour face and dumpy figure, Mrs. Dumphrey was fit to be tied. She glowered at me like I was some kind of truant before she said, “You’ve got some nerve, Mr. Fawcett, showing up here looking like a bum and using such language.”

“You haven’t changed a bit,” I told her. “What a buzzkill.”

Smoke was coming out of her ears. “You were a waste of a desk and a chair twenty years ago, and I can see that nothing has changed.” A crowd was gathering, and Andy joined us, pretzel crumbs in his beard. Mrs. Dumphrey rolled her eyes. “And who is this creature? Another sad commentary on Grover Cleveland High School before I became principal.”

“Maybe if I made a contribution to your college scholarship fund for worthy students, you’d feel differently?”

“That’s a laugh. You’ll probably need to pass the hat for bus fare home.”

“Suppose I were to raise a million dollars? On one condition?”

“Ha! That you don’t get caught robbing the bank?”

“No. That you resign and drag your sorry ass out of Dullsville.”

There was dead silence. The other alumni were gaping in shock, except for Andy, who was taking it all in with amusement. Then Audrey Forrest whispered something in Mrs. Dumphrey’s ear, and a wicked smile came over her toadlike face. “If you can raise the money by tonight, you’re on. Provided you meet one condition: you will have to dress as a woman, every day, for an entire year!” Peals of laughter rocked the lunch room.

* * *

Andy returned to his pretzels, and I found a quiet corner to make two calls on my cell phone. The first was a quick call to my personal banker. The second was a longer, more difficult call to my boss. When I was through, I signaled Andy, and we bailed out before lunch was served. He waited until we got back to my car before he started in on me. “You really stepped in it back there, bro.”

“Yeah, I guess I kind of lost my cool with that bitch.”

“Could you really come up with that kind of money?”

“That’s no problem. Tell me, did anybody recognize you in there?”

Andy laughed. “Hell no, they all thought I was a panhandler.”

“Perfect.” He asked me what I meant, but we were pulling up in front of the barbershop I’d found in the yellow pages. “Follow me,” I said.

Andy got out of the car and stood outside the door. “Are you getting a haircut?”

“No. You are.”

“No fucking way.”

“And you’re losing that awful beard, too.”

“You’re starting to piss me off.”

“Are you forgetting about last night already?”

“Wait, what?”

I raised my voice to Jayne’s. “How good it felt to hold me? To be inside me?”

“No, but….”

“No buts, Mister. You’ve got one shot at me, and it’s decision time, right now. Do you think I want to spend the rest of my life kissing a bear?”

“The rest of your life?”

“You heard me. If you don’t want that, if you don’t want me, just say so right now, and I’ll be on my way.”

“Jay…Jayne, I think I do want that. I think I do.”

“Then get your ass in there!”

* * *

I gave the barber $200 and made sure Andy was planted in a chair before I left to shop for something to wear to the reunion. I’d planned to wear a sweet little dress with a matching bolero jacket, but after my run-in with Audrey and Mrs. Dumphrey, I figured something a bit sexier was called for.

It’s always easier to shop for women’s clothing when you’re dressed as a woman, and I had some other projects too, so my next stop was the Hyatt, where I changed back into Jayne. I toyed with the idea of putting on my khaki skirt and knee sox again, but for some reason I felt like wearing that sweet little dress – I’m such a girl! – which wouldn’t be too dressy for downtown Cincinnati. With navy nylons and a matching purse and heels, I was every inch the career woman as I walked the few blocks to Saks Fifth Avenue, turning the heads of several well-dressed men along the way.

I love to shop, but I didn’t have all day, so I made a beeline for the Misses department and started my search for something hot. It didn’t take long for me to spy a black tank top that was just dressy enough to wear to a special occasion. Before I tried it on, I searched fruitlessly for a cute skirt to wear with it. Nothing seemed right! In desperation, I tried my luck in the Juniors department – I can’t get away with Juniors tops, but my hips are so slim that Juniors skirts sometimes work for me, and sure enough there it was: a short pencil skirt with turquoise leaves and pink flowers on a white background with black trim. It was darling! I found a fitting room, hurriedly took off my jacket and dress, and pulled on the top and skirt. They were perfect on me! The skirt was unlined, so I’d need a short half slip, and of course my blue nylons looked ridiculous, but I didn’t intend to wear nylons that night, and after I took off the skirt and top I peeled them off.

Then it was back into my dress and heels, off to the lingerie department to find a slip, and on to shoes and purses. Where I came up empty! So I paid for the skirt, slip and top and raced across the street to Macy’s. Success! In short order I scored a cute pair of strappy heels, a little black and white purse that would be perfect for evening, and my last acquisition: a statement necklace that matched the flowers on my new skirt. I was laden down with shopping bags when I returned to the Hyatt, just in time for my appointment at the nail salon. A manicure and pedicure in hot pink, please!

After a quick word with the hotel concierge, it was off to a local branch of my bank, where I picked up the check I’d ordered earlier that afternoon. I had to show my ID, of course, and it was amusing to observe the double-takes from the teller and two bank officers before they were satisfied I was really me. This type of episode used to unnerve me, but I figured I was never going to see these people again, and I certainly gave them something to talk about!

I didn’t have time to return to my room before I picked up Andy. I was dying to see what he looked like, and I wasn’t disappointed: standing outside the barber shop was a devastatingly handsome man, who looked like I’d imagined Andy to be in my dreams – tall, with a full head of neatly trimmed hair, dark without a hint of gray. And his face! Now that I could see it again, I wanted him more than ever. Of course, he was still dressed like a bum, but that was going to change next. He climbed into the car and started to grumble as we drove back to the hotel. “I can’t believe you made me put up with that shit! The barber said he was calling Guinness Book of World Records. I look like I’m in seventh grade!”

I just smiled sweetly while he unloaded on me. When we got to the hotel, I gathered up my shopping bags, and handed Andy the package which his mother had given me. “What’s this?”

“You’ll see. Follow me.” He kept grumbling all the way down the hall and up the elevator, until we got to my suite. Where I pointed him towards the powder room and told him, “Put on the clothes in that package.” Then I closed the door to the bedroom before he had a chance to protest, and hung up my new skirt and top. I took off my jacket, and I was fixing us drinks in the parlor when Andy came back into the room. In a perfectly fitting suit, shirt and tie. Even his shoes were polished – his mother was a saint. He looked like a male model on the cover of GQ, and he knew it, too: that old, dashing smile that I remembered from his youth was back. My Andy was back!

I handed him a beer and sat down demurely in my little dress. “Cheers!” I said, lifting my glass of Chardonnay.

“You’re looking very prim and proper tonight.”

“Not for long. You know what’s funny? You made a much bigger transformation than I did today.”

“Hardly.”

“No, it’s true! Ever since last night, you’ve been changing, can’t you see it?”

“So I look a little different. I’m still a guy.”

“It’s not just the way you look, sweetheart. Yesterday you were a whipped dog. Now you’re an alpha male.”

“Maybe I can score with a real woman now?”

I punched him on the arm. “Don’t be such a brat!”

“You think you have me wrapped around your little finger, don’t you?”

“Um hmm.” I leaned over and kissed him, gently on the lips. “Shall I tell you what we have planned for tonight?”

“We can stay right here, as far as I’m concerned.”

“No, in a few minutes I’m going to put on a ridiculously hot outfit, and you are going to take me to our twentieth reunion.”

“I was afraid of that.”

“Here are our tickets.” I handed them to him. “You just be yourself. Everybody will be talking about you. I’ll just be your hot date. Nobody will guess who I am.”

* * *

I’ve been dressing as a woman long enough to know when I pass, but for the first time since the senior prom twenty years before, I could tell that something special was happening. Then, it was Andy’s mother who’d put me over the top, but that night, it was twenty years of trial and error that guided me through my hair, my makeup, and by the time I’d changed into my new outfit, I was pretty sure I was smoking hot. Any doubt was erased when I saw the look on Andy’s face when I returned to the parlor. “Holy shit,” he said, “is that really you?”

“You Tarzan, me Jayne. Pour me a vodka tonic, please.” I had to be careful sitting down in my tight little skirt.

He poured me a stiff one and popped another beer for himself. “Better be careful. Remember what happened the last time you got started on those?”

“Yes. I was the prettiest girl at the senior prom, to quote someone I know.”

“I want to fuck you right now.”

“I’ve created a monster!”

“Let’s do it before you’re too drunk to drive.”

“That won’t be a problem tonight.” As if on cue, the telephone rang. It was the concierge. “Your limousine is here, madam.”

“Thanks, we’ll be right down.” Then to Andy, “Showtime!”

* * *

I wasn’t expecting a gold stretch limo, but that’s what we got. Andy was in hysterics at first, then he tried to molest me, and I had to fight him off all the way to Dullsville. In between rounds, I drilled him on what to say, and what not to say, at the reunion: I was just a “friend.” He worked out of state, and didn’t want to discuss his business. Turn every conversation around onto what the questioner was doing with his/her life. The bar in the limo was stocked, and by the time we rolled up to the country club, we were both half bombed.

There was a crowd standing outside the front entrance, and they all gaped and stared as the best-looking couple at the reunion climbed out of their ride. You would think Donald and Melania Trump had just pulled into Dullsville. I took Andy’s arm, and the throng parted as we marched into the lobby.

A dumpy looking woman whom I remembered as a munchkin in high school was sitting at a card table, taking tickets. Andy handed her ours, and when she asked for our names, he said, “Andrew Parsons and friend.” She scratched her head as she looked through the list on the table. Of course I’d purchased our tickets in my name, so she had a mystery on her hands. But she remembered Andy, so she took the tickets and waved us into the ballroom. An open bar beckoned, and Andy went off to reload while I looked around the room.

Every eye seemed to be on me. They looked away quickly, which told me that they didn’t recognize me. I was simply the most beautiful woman at their reunion, the date or trophy wife of some lucky guy. Then Andy returned with our drinks, and the focus of the room shifted onto him. Who was that? Was that Andy Parsons? He hadn’t aged a bit in twenty years! Where had he been? How did he afford that limousine? Where did he meet that beautiful woman? I could feel the buzz sweeping through the room, although Andy seemed oblivious. Until Audrey Forrest made her way up to us. “Andy? Is that really you?”

“Oh, hi Audrey. You look nice.” Which was a stretch: she’d obviously spent all day getting her hair and nails done, and maybe had a facial too. Her legs weren’t bad under that dress, which was way too young for her, so her little belly was straining against the seams. And her arms had started to go to fat, I observed. Meow!

“You look fantastic, Andy.” She acknowledged me with a nod, then tried to steer him away. “So what have you been doing with yourself all these years? Nobody even knew you were coming.”

Meanwhile, a middle-aged man in a plaid sport coat was making a move on me. He looked vaguely familiar…the captain of the football team? Could be. His bad comb-over and bulging gut made it difficult to be certain. “You must be Andy’s date,” he said confidently.

“Um hmm.”

“He didn’t make much of a splash at Grover Cleveland.”

“Were you the big man on campus?”

“So they tell me.” He launched into an epic description of his high school exploits, while I watched Audrey pour the charm on Andy. As he related to me later, she started by trying to sell him a house, and moved on to suggesting that he dump me and come home with her. Meanwhile, my admirer continued to pour it on. “That top is very becoming on you. If I was on you, I’d be coming too.”

I looked down at his wedding ring and laughed. “You really are a first class piece of shit,” I told him. His mouth opened in shock. “Is your wife here tonight? Or do you just wear a wedding ring to fool people into thinking you’re not really gay?”

“I’m not gay!” he stammered, in a voice so loud that people turned their heads to stare at him.

“Then why are you hitting on a transgendered woman?” He recoiled in shock, and melted into the crowd. I was pretty sure he wasn’t going to tell any of his classmates that he’d just tried to pick up a man. I returned to Andy and Audrey, who was clinging to his arm. “Aren’t you a little old for him, sweetie?”

“You’ve got some nerve,” Audrey scowled at me.

“Take your hands off my man, bitch!” A crowd started to gather as Audrey and I squared off. Cat fight!

The crowd parted to make way for Mrs. Dumphrey, who had been watching it all with displeasure. “What is the meaning of this?”

“This bimbo insulted me!” Audrey pouted.

“I’m going to have to ask you to leave,” Mrs. Dumphrey told me imperiously.

“You can’t kick out a member of the class. This is my reunion, we’re on private property, I paid to be here, and I’m sure you didn’t.”

“You’re not a member of the Class of 1995!”

I reached into my purse and pulled out a business card. Jay Fawcett, Executive Vice President of a household name. Mrs. Dumphrey blanched when she read it. Then her eyes slowly raised, as she studied me intently, from my painted toes and killer legs to my shapely physique and striking face. She was still staring at me when I pulled something else out of my purse: a cashier’s check in the amount of $1,000,000 payable to The Grove Cleveland College Scholarship Fund. Mrs. Dumphrey fainted dead away.

* * *

In the limo on the way back to Cincinnati, Andy asked me if I’d lost my mind. “I don’t think so, baby. All in all, it’s been a pretty amazing couple of days: I found you, made you into my dreamboat, screwed Mrs. Dumphrey and did some good for the kids in Dullsville.”

“What makes you think she’ll really resign?”

“She has no choice. When the Board of Education reads the letter I send them, stipulating that my contribution is contingent on her keeping her promise, she’ll have to go.”

“How about you? How can you go back to work, dressed as a woman?”

“That was the hard part. But I’ve been meaning to step away – I’ve got all the money I’ll ever need – so I told my boss this afternoon. Although he’s so cool, I could probably stay anyway.”

“But you’ll still have to dress as a woman for a year.”

“Who’s complaining?” I pushed the button that raised the privacy screen between us and the driver.