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Introduction:

not a true story my best friend helped me write this
Chapter 2 of 5


As an afterthought, she emptied out an old purse and asked me for my wallet and keys. She dropped them into it, along with her lipstick, and handed it to me.

"You'll need this tonight," she explained. I carried her purse awkwardly as I followed her down the stairs into the kitchen.

For the next half hour, I almost forgot that I was dressed as a girl as I helped Hillary set the table and watched her microwave some leftovers. We chatted while we ate about classes and friends, and when we were through I offered to help her with the dishes. Hillary found an apron for me and giggled as she tied it around my dress. I was standing at the kitchen sink when her parents walked in.

"Hello, dear," her mother said. I was so startled that I almost dropped a dish. I turned around and faced them nervously. "What's going on?" her mother asked.

"We're going to the dance tonight," Hillary replied.

"I thought you had a date," her father said.

Hillary started to laugh as I blushed bright red. "Daddy, this is my date, Jim Taylor."

Her father stared at me as her mother looked me up and down. "She's a boy?" her mother finally asked.

"No way!" her father said.

Her mother came up to me and studied me like a stuffed animal in a museum. "I thought that dress looked familiar," she said. "If you hadn't told me, I would never have believed it. Jim, you look adorable."

"How about me," Hillary asked. "Don't I look handsome?"

"You look like a pretty girl dressed up as a guy," her father said. "Your friend looks like the real deal. How long have you been dressing this way, young man?"

"Never, except one Halloween when I was a kid," I said defensively. "It was Hillary's idea," I added lamely.

"Unbelievable," her father said with a shrug as he started to leave us.

"Wait, Daddy, can I have the keys?"

"You mean she doesn't drive?" her father asked sarcastically as he handed them over. Hillary stuck out her tongue and put the keys in her pocket.

"We'd better get going, Jim." Grateful to escape, I took off my apron and picked up my purse

"Don't you think she needs a nicer name?" her mother asked as we headed for the door. "You can't very well expect a pretty girl to answer to Jim."

We left in a hurry, and I was still blushing when Hillary opened the passenger door and looked at me expectantly. It dawned on me that my date was waiting for me to take my seat. When I climbed into the Fowlers' car, my dress rose all the way up, revealing my slip and panties. Hillary giggled as she closed the door.

We drove in silence for some time. Finally she said, "You know, my mother has given me an idea."

"You want to give me a name?"

"Not just that. Jim, look at yourself. There is no way anybody at the dance is going to recognize you as Jim Taylor. Why don't we pretend that you're really a girl?"

"Why would we want to do that? What if the kids find out? Besides, if I were really a girl, then I'd need a costume." I desperately tried to think of another excuse.

"I'll bet only half the kids there are really in costumes. You're just a sophomore, so you wouldn't know that. Jim, you could fool everybody. Wouldn't you rather do that than have all your friends thinking that you like to dress up as a girl?"

That made sense. "Do you really think we can pull it off?"

"I know we can. Nobody knows I asked you to the dance, except Janet. Will she be there tonight?"

"Uh, no."

"Great, then it's settled. Who do you want to be?"

"What?"

"Let's make you a friend I met this summer at the beach. You're visiting for the weekend from LA. Your name is Jamie."

"Jamie," I repeated.

"Now, you've got to work on your voice. Try to talk as little as possible, and smile a lot. When you do have to open your mouth, keep it short and sweet. This is going to be so great!"

I was shaking when Hillary pulled into the school parking lot. I started to open my door when she put her hand on my knee. "Jamie, you're a girl, remember? Wait for your date to open the door for you. And when you get out of the car, slide your legs out first, so you don't put on a show. Got it?"

I nodded and waited for her to open my door. Emerging gracefully, I swung my purse over my shoulder and followed her into the dance. There was an ID check at the door, but the vice principal didn't even look up as I handed him my wallet, and then we were inside. The dance was in the gym, and it was already crowded with kids, dancing and trying to talk above the loud music. Hillary led me onto the floor and we started to dance.

Once again, I almost forgot that I was dressed as a girl as Hillary and I danced together. When it was time for a slow one, she gently took the lead, and as we pressed against one another, she whispered in my ear. "Having a good time?"

"The best," I said. I had just gotten laid by my dream girl, who actually seemed to like me. So what if the circumstances were totally bizarre?

"I really like you as a girl," she said.

Shocked, I pulled away and looked up at her. "What do you mean?"

"I mean I dig girls, Jamie. Guys too, but girls more."

"And you like me more as a girl?"

"Totally. What we did back in my room, with me as the guy and you as the girl, was such a turn on."

My mind was spinning as the dance ended and a group of Hillary's friends came up to us. "Hey, Hill, who's your friend?" one of them asked.

"Carol, this is Jamie, from LA. Jamie, meet Carol and the guys."

Carol was taller than Hillary, and she was dressed up as a Hells Angel, totally butch. "The guys" were a collection of girls in similar costumes. "Next dance, Hill?" one of them asked.

"Why not? You're on your own, Jamie," she said, and I watched my date go off with another girl, also dressed as a man. I was still reeling when I felt a tap on my shoulder.

Turning around, I found myself face to face with Josh Arnold, the captain of the football team. Well over six feet tall and built like a Greek god, Josh towered over me.

"Hey," he said, "wanna dance?"

What could I do? Tell him I was really a guy? It was a fast dance, so I nodded and followed him out to an opening on the floor. I tried to concentrate on dancing as femininely as possible, telling myself "You're a girl. You're a girl." Josh was a good dancer, and I caught him staring at my legs as they twisted and turned under my short dress. When the music ended, I was about to break away when a slow dance started, and before I could react, Josh put his left hand on my right shoulder and brought his other hand around my back. He held me close, and I rested my chin on his shoulder as we moved across the floor. I could feel his erection pressing against my stomach, and when his hand dropped down to my ass, I felt an ache in my groin as my captive penis truggled against its silken restraints.

Suddenly Josh took his hand off my ass and put it under my chin, lifting my mouth towards his. I stood transfixed as he started to kiss me. The world stopped.

The next thing I knew, the music was over and Josh was leading me by the hand over to the refreshment table. He got us each a Coke and asked me if I needed a ride home.

"No thanks," I said in a girlish voice, the only words I spoke to him that evening.

When he finished his Coke, he thanked me for the dance, and I smiled demurely as he turned and walked away. I was standing there trying to get a grip on what had just happened when I heard a familiar voice.

"How was your walk on the wild side?" Hillary had a huge grin on her face.

"You saw?"

"Everything. Do you know, when he kissed you, you actually lifted one of your feet off the ground, just like a girl."

I was beyond blushing by this point. Tears started to well up in my eyes.

"Come on, Jamie," she said. "Let's fix that pretty face."

She led me towards the girls' room, and when I stopped short at the door she literally pushed me inside. Half a dozen girls were standing in front of a large mirror, fussing with their costumes, and none of them paid any attention to me as I took my lipstick out of my purse and freshened my makeup.

Hillary and I danced several more times, but a gulf had formed between us, and I was relieved when she said it was time to drive me back to her house. We rode in silence until she parked in the driveway.

"You know, Jamie," she said, "the hardest thing is to find out who you really are."

"What do you mean?"

"Before tonight, I was a girl who wondered whether she might be transgendered. I got the answer to my question tonight. Did you?"

"What question?"

"A few hours ago, you were a geeky guy with a crush on an older girl. Now you're a beautiful girl, and Josh Arnold is going to jerk himself off tonight dreaming of you. Which do you like better?"

"I don't know."

"I think I do. But don't rush it. Let's go. It's time for Cinderella to turn back into a pumpkin."

We managed to evade her parents, and she helped me scrub off my makeup before I got back into my clothes. Hillary walked me to the door and followed me outside. She kissed me gently on the lips, but I felt no trace of arousal.

"Good night, Jimmy or Jamie," she said.

I slowly walked back home, suddenly aware of how tired I was.

I tossed and turned for a long time before I got to sleep. In one night, I had lost my virginity, been kissed by a boy, and made a profound discovery. I liked being a girl. I liked everything about it. I liked the way it felt to wear dresses and stockings. I liked the taste of lipstick on my lips. I liked the way people treated me, and the way I felt about myself.

As I lay there in the darkness, I knew I had two choices. Give in, or fight it. I decided then and there to fight it.

2000

"We're leaving now, Jim. See you Sunday night."

"Bye Mom and Dad, have a good time."

I waited until I heard the garage door come down, and then I jumped out of the sofa and ran upstairs to my room. I watched their car back out of the driveway, and after they pulled away, I drew my curtains tightly shut and walked into Emily's old room.

I was alone for two whole days. Mom and Dad would be spending Parents Weekend at USC with Emily and Janet, leaving me to watch the house. And indulge my secret fantasy.

Captain of the varsity swim team, vice president of my class, and an A- student, I was on a fast track to success. A scholarship to USC or even Stanford was not out of the question if I nailed my SATs in a few weeks. That would certainly help my family. My father had grown noticeably older-looking, with two daughters in an expensive private school and a disappointing business career. I could see what the pressures were doing to him, and I could also see the concern on my mother's eyes as she watched it happening.

Tonight, those concerns were out of mind as I went into the bathroom and started to fill the tub with bubble bath. While the tub filled, I stood in front of the sink and gave my face a close shave. Then, armed with a double-edged razor and a pack of blades, I climbed into the tub and lowered myself into the swirling water. After soaking for a few minutes, I began the familiar ritual of shaving off my body hair.

The ostensible purpose for doing this was the swim team, and in fact I had to do it, but I had an ulterior motive. Once the hair was off, my inhibitions would be undermined, and I told myself that it would be a shame not to engage in a little harmless fun. And so I shaved my body, and then washed and conditioned my hair, all the while convincing myself that it was for this night only. After all, I had resisted the temptation for two whole years, and surely one night was not going to do any harm.

After I dried myself off, I wrapped a towel around my head into a turban, and walked into Emily's room. As an afterthought, I returned to my room and fished a condom out of my desk drawer. I took it out of its package and rolled it up my still-flaccid penis.

After drawing Emily's shades, I took a bra out of her dresser drawer and snapped in on like I had been doing it all my life. I filled the cups with a handful of knee-highs. Then I went into Janet's room and found a pair of flesh colored tights, the kind cheerleaders wear under their skirts in cool weather. Sitting on Janet's bed, I lovingly pulled the tights up my hairless legs, and then I returned to Emily's room and put on a pair of her white tennis panties. Then to her closet, where her old cheerleader uniform hung where she had left it. I pulled on the sweater and short pleated skirt.

I returned to my room and retrieved a pair of old white Keds from my closet floor. My feet had grown too big for my sisters' or mother's shoes, but the Keds were a suitable complement to Emily's uniform. I sat down on the floor of my room and tied them on, feeling my penis come alive with excitement as I rested my chin on a silky knee.

Not yet, I told myself. Back to the bathroom, where I blow dried my hair and then brushed and braided it into pigtails, which I tied with red yarn bows to match the letter on my sweater and the piping on my white skirt. Then to my parents' bathroom and my mother's makeup, which I applied sparingly to my eager face.

Done! Finally I allowed myself to stand in front of a full-length mirror, and my knees buckled as I beheld my reflection. After two years of denial and frustration, I was overwhelmed by sheer joy. The cheerleader looking back at me in the mirror was incredible, and at that moment I wanted nothing more than to stay that way forever. I performed a little pep cheer, watching my skirt flip as I kicked up my heels, and I felt myself coming closer and closer to climax.

Not yet, I told myself again. I returned to my room and took a thesaurus out of my bookcase. Pressed between the pages were a photograph and a newspaper clipping.

The photograph I had spirited out of one of our family albums. It showed a pretty young girl in a green dress, seated at our kitchen table in front of a bag of candy. Her legs were tucked under her dress, and a froth of lacy slip showed between her knees. She was totally preoccupied with the candy, and her face was radiant. The clipping was from our high school paper, taken exactly two years earlier. A handsome boy was facing the camera, dancing with a girl in a short dress and ponytail. His hand was on her ass, pulling up her dress to reveal a pair of gorgeous legs.

I pulled a chair up in front of the mirror on Emily's closet door, and seated myself carefully in my short skirt. The cute cheerleader in the mirror studied the two pictures until she couldn't hold out any longer. With a cry of despair, I finally yielded to a shattering orgasm, filling the condom with gobs of hot semen. Tears fell down my face as the pulsing went on and on before finally subsiding.

When it was over, I was overwhelmed by feelings of shame and self-loathing, and I vowed once again to conquer my strange compulsion. Even as I did, I knew in my heart that it was not going away, and indeed was only getting stronger.

2001

The leaves rustled beneath my feet as I walked across Sproul Plaza towards my psychology class. Even though there was no real change of seasons at Berkeley, nobody had informed the oak trees.

I did not encounter a single familiar face as I passed through the crowded plaza. One of the advantages of Berkeley was total anonymity if I wanted it, and right now, that was exactly what I wanted. Although my dreams of attending Stanford had died with my father the preceding spring, I had been happy to get into Berkeley, where tuition for California residents was a much-needed bargain for our grieving family. As I entered the psychology building and took my seat in a crowded lecture hall, I somehow knew that fate had brought me to this place and time, just as fate had prepared me for the decision I was about to make.

Professor Kleinberg bounded up to the lectern and adjusted his horn-rimmed glasses. A youthful sixty, he fumbled with his notes while he waited for his students to quiet down. When he started to speak in his faint German accent, a hush fell over the auditorium.

"Good morning. Today we are going to continue with our discussion of sexual deviations, or what used to be called deviations before it became politically correct to refer to them as alternative lifestyles. Mind you, I offer no judgment here, simply a reflection on the emerging mood of our popular culture, at least here in the Bay Area. I daresay, what is tolerated and even welcomed here at Berkeley and across the Bay in San Francisco might be totally repudiated in other parts of the country, such as Alabama, Mississippi, or Orange County."

I laughed along with my fellow students at this dig at my home. Looking around the lecture hall, I observed an astonishing diversity of young men and women, of every ethnic background, type of dress, and standard of grooming. If some of these kids turned up on a street corner in a small town in Texas, they would probably be shot on sight. With my shoulder-length hair, Cal sweatshirt and jeans, I looked like a straight arrow compared to most of them.

"In any event," Professor Kleinberg went on, "today we are going to discuss the transgender phenomenon. I know all of you have done your reading, and also studied the questionnaire, which was handed out at the end of last Friday's lecture. That questionnaire included a space for volunteers to fill out if they were interested in participating in a little experiment. I am not asking those who volunteered to identify themselves now, indeed that would defeat the whole purpose. But for those of you who did, and I believe it was three of you, please report to my office on the fourth floor at the conclusion of today's lecture."

The professor droned on for the next fifty minutes about the current theories on the causes and treatment of transvestism. I heard nothing that I did not already know, having long ago devoured every book and article I could find on the subject. When the class was finally over, I grabbed my backpack and headed for the fourth floor.

Professor Kleinberg's secretary showed me into his cluttered office, where another guy was already seated. He was dressed in a leather miniskirt and boots, and his head had been shaved except for a purple Mohawk. As I tried to think of something to say to him, a girl walked in, dressed in a black leather jacket and jeans and carrying a motorcycle helmet. An enormous ring pierced her nose. The three of us sat in awkward silence until the professor came in.

He surveyed the three of us quickly, and then said, "Mr. Lupo and Ms. Stoga, I want to thank you for volunteering. However, based on my review of your credentials, I am afraid you are not quite right for this experiment. I assure you this will not effect your standing in my class, and in fact as a result of your volunteering, you have already guaranteed that your final grade will automatically jump a whole point after your papers and examinations have been completed. I thank you both for coming."

They both shrugged and walked out. When we were alone, the professor closed the door and sat on the edge of his desk.

"Mr. Taylor, tell me why you volunteered for this."

Without hesitation, I told him the truth. "When I was in seventh grade, my mother and sisters forced me to dress up as a girl on Halloween. Ever since, I have been fascinated by women's' clothing. I find it incredibly arousing. Once, when I was in high school, my girlfriend took me to a Halloween dance after dressing me up in her clothes. It was the most exciting night of my life. I have been trying for years to get this out of my system. Nothing seems to work. I was hoping you could help me."

The professor took off his glasses and polished them with his necktie, deep in thought. "Mr. Taylor, I may be able to help you, but not perhaps in the way you are thinking. Have you ever considered taking this obsession of yours to the limit? To explore the depths of your fixation, and perhaps uncover the reason for it?"

~~~~~~~~~~~~~~~~~~~~~~~~SEE next chapter~~~~~~~~~~~~~~~~~~~~~~
3 comments

oldmaleReport

2009-10-29 09:11:56
sounds great waiting for part 3

READERReport

2008-03-16 10:55:43
Very interesting story so far, waiting for the next chapter.

READERReport

2008-03-16 00:58:38
mmmmmmmmmmm, getting fun, cant wait for #3

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