Only in October

by Nom de Plume
 © 2002

 

1989

 

"Come on, Jimmy, it’s time to get ready!"

I bounded up from the family room floor and raced as fast as my twelve-year-old legs would take me. Halloween! Trick or treat! Next to Christmas Eve, it was every kid’s best day of the whole year.

Even if this year, I would be stuck going around the neighborhood with my stupid sisters. We had just moved to California from New York, and my parents didn’t know my new friends well enough to trust me to go outside with them at night. Looking back on everything that followed, I am sure they wish now they had taken that risk.

Emily and Janet were 16 and 14, and they had promised that they would come up with a cool costume for me. My dad was out of town on a business trip, another fateful decision, because if he had been home, I doubt if he would have stood for what was about to happen to me. As I bounced into my bedroom, I found my mother and sisters waiting for me with odd grins on their faces. Emily was already dressed up as a cheerleader, and Janet looked like Princess Lea having a bad hair day.

"What’s my costume?" I asked excitedly.

"Jimmy, you’re going to be a girl tonight," my mother said matter-of-factly.

I stared at her in shock as my sisters started to giggle. "We have your outfit all picked out," Emily said. "You and Janet are exactly the same size."

"No way!" I protested. "I won’t do it! Please, Mom, don’t make me do it!" I started to cry as I backed away from them.

"Oh Jimmy, don’t be such a baby!" my mother scoffed. "I’ve always wondered what you would have looked like as a girl, and this is my one chance to find out. Be a good sport, okay?"

"No!" Tears streamed down my face.

"What a baby," Janet said. "Crying just like a girl. You should have to wear dresses all the time."

"That’s enough!" my mother said sharply. "Girls, you promised me that you wouldn’t make fun of Jimmy."

I looked at her through watery eyes. "How long have you been planning this?" I managed to ask.

"It was my idea," Emily said. "When Mom said you had to go out with us, I thought gee, wouldn’t it be cute if Jimmy came along as a girl. That way he’d fit right in with our other friends."

"Other friends?" I wailed.

"Yes, and we don’t have time to waste. We’re meeting the girls in half an hour."

"Mom, I won’t go!" I cried.

"Then you’ll just have to stay home and help me hand out candy to the children, if that’s the way you feel. I do think you’re making a mistake, dear. Go ahead, let the girls dress you up and have some fun."

I hung my head in misery. What could be worse than being stuck home all night with my mother doling out treats to the neighborhood brats? "Do I really have to?" I asked meekly.

"Hooray!" Janet cried. "Come on, Jimmy, let’s get you ready!" Before I could protest, she took my hand and let me into her bedroom. I stopped short when I saw the clothes arrayed before me on Janet’s bed: panties, slip, stockings, training bra, and the dress that Janet had worn to our cousin Ginger’s wedding earlier that year.

"No way! You can’t make me wear that?" I said in panic.

"What did you expect, Jimmy?" my mother asked. "Come on, get with the program." I was so stunned, I let her gently remove my shirt, and then she told me to take off my shoes and pants. Standing there half naked, I looked up at my sisters, who had their eyes glued on my shorts.

"All right, girls, leave us alone for a few minutes, okay? You can help with the final touches." Without a word, Emily and Janet left us alone, closing the door behind them. "Now, Jimmy, take off your underwear."

"Mom, I’ll put on the dress, but why do I have to put on all this other junk?"

"Please, Jimmy, just this once, do it for me, okay?"

Resigned to my fate, I turned around and took off my shorts. My mother reached over my shoulder and dropped the panties into my trembling hands. I stood there for a moment, and then I stepped into them and pulled them on. When I turned around to face her, I was shaking like a leaf.

"Don’t be scared, Jimmy. Your sisters and I have to dress like this every day. Think of it as an adventure," she said as she deftly guided my arms through the straps of Janet’s bra. After she fastened it behind my back and stuffed a few tissues into the cups, she stroked my longish hair for a moment. "When we get you dressed and put your hair in a ponytail, nobody will recognize you!"

With that, she took the slip off the bed and asked me to raise my arms. When the cool, silky fabric fluttered down over my smooth skin, I felt a strange stirring in my panties. I must have turned a bright red, but my mother mistook my blushing for simple embarrassment as the slip concealed the beginnings of my first ever erection.

"Now, sit down on the bed, and we’ll put on your pantyhose." Without a word, I hiked up my slip and sat on the edge of the bed, and she kneeled down in front of me and began to slide the stockings up my hairless legs. As the nylon moved up my calves, the unfamiliar sensation in my panties intensified, and I found myself holding my slip down to cover up a growing bulge. She seemed not to notice as she asked me to stand up and finish pulling my stockings up to my waist. When I did so, I felt lightheaded as I looked down at my stockinged feet, framed by the lacy hem of my slip. The feeling of the sheer nylon against my skin was like nothing I had ever experienced.

"Okay, honey, time to put on your dress," she said. By now, I was so stunned by what was happening to me that I simply held up my arms again, and she laughed as she spun me around and dropped Janet’s green taffeta dress over my head and arms and pulled it snug. I heard a zipper sliding up my back, and then felt a tug as she fastened the clasp. "Turn around, Jimmy," she said, and I meekly obeyed. "Oh Jimmy, you look beautiful! Come in girls, and meet your new sister!"

The door bust open and Emily and Janet practically fell into the room. "Oh, my God! Look at him! He’s so cute!" Emily cried.

"You mean look at her," Janet laughed. "How do you like my dress, Sis?"

"Come on girls, that’s enough of that. Emily, will you please do something with Jimmy’s hair before I put on his makeup?"

Makeup? That snapped me out of my trance. "Aw, Mom, not makeup!" I said half-heartedly.

"Just a little, appropriate for a girl your age. And Janet, will you find a pair of shoes for Jimmy? Try those black skimmer flats on him." As Emily brushed my hair back into a ponytail and fastened it with a velvet bow, Janet went into her closet and returned with the shoes. They were tight, but with the stockings, my feet were able to slide into them. I took my first tentative steps in them as my mother guided me into Emily’s room and sat me down at her vanity.

For the first time, I was able to see myself in a mirror, even though it was just my head and shoulders, and I watched in fascination as my mother took a little eyeliner and lipstick and applied it carefully to my now girlish face. When she was finished, she produced two clasp earrings and a gold necklace, and after she fastened them, she surprised me with a spritz of cologne behind each ear. I could only sit there in shock as my mother and sisters stared at me.

"Stand up, let’s get a good look at you," Emily finally said, and she led me by the hand to the full length mirror on her closet door. When I saw myself for the first time, my jaw dropped and I heard myself gasp. Looking back at me with wide eyes was the cutest girl I had ever seen, with budding breasts and pretty legs shimmering beneath her knee-length dress. As she twirled this way and that to study her ponytail and tug the hem of her dress down over her slip, the strange sensation in my panties came back with a vengeance. Suddenly I felt the most delightful throbbing, and my young body shivered as I experienced my first orgasm.

My mother and sisters never knew. The rest of the night was a blur as I came down to earth and coped with the practicalities of walking and sitting in a dress, trying to talk like a girl, and pretend that I wasn’t having too good a time. When we returned from trick or treating, I lingered in the kitchen with my mother and sisters, curling my legs up under my dress and rubbing my aching toes through my nylons as we divvied up our haul of candy. I was praised for being such a good sport, pictures were taken that I treasure to this day, and then it was time for bed. After I finally drifted off to sleep, I dreamed that when I woke up the next morning, a kilt, blazer and knee sox would be waiting for me at the foot of the bed.

 

1992

 

"Mom! Dad! I made the team!" I shouted as I ran through the front door.

My father looked up from his newspaper and said, "I thought you weren’t even going to try out."

"Not the wrestling team, Dad. The swim team! I’m the only sophomore to make the varsity!"

My mother joined us and gave me a hug. "That’s wonderful, Jimmy! When do you start practice?"

"Tomorrow afternoon."

Janet came down the stairs and asked my father for the keys to his car. "Did you hear Jimmy’s news?" my mother asked her.

"Yeah, that’s great, Jimmy. When are you going to shave your legs?"

"Shave his legs?" my mother and father asked in unison.

"I dated a guy on the team last year, and he had to shave his whole body for the season. Didn’t you know, Jimmy?"

"Sure, it’s no big deal. All the guys have to do it."

"Sounds fruity to me," my father grumbled as he buried his nose back in his paper. He had never gotten over my unwillingness to try out for the football team earlier that year, even though he must have known that at 5’8" and 130 pounds, I would have spent the practices as a glorified tackling dummy with no chance of making the traveling squad.

"Who are you taking to the dance?" Janet asked as she opened the door.

"Nobody."

"Hillary Fowler thinks you’re cute. Why don’t you ask her?"

The joys of having an older sister in the same high school. Hillary Fowler! Tall, beautiful, and unapproachable. She was a junior, and I had two classes with her, but I had never been able to screw up the courage to talk ask her out.

"Yeah, right," I said hopefully.

"I mean it. Give her a call tonight," Janet said as she walked out the door.

* * *

She said yes! Hillary Fowler said yes! I was going to the Halloween dance with my dream girl! She even laughed when I told her I had no idea what I was going to come up with in the way of a costume. "Why don’t you come over early, and I’ll figure out something for you," she told me.

Which was just as well, because the next morning I was preoccupied with getting ready for swim team practice. The coach had instructed us to shave down before the first workout, and I spent over an hour in the shower, tediously removing the forest of hair that had grown over my chest, arms, and legs when I hit puberty. Before I came downstairs for breakfast, I self-consciously dressed myself in jeans and a long-sleeve sweatshirt, even though it was going to be a warm day with Santa Ana winds.

Practice was grueling, with endless repetitions, back and forth down the crowded lanes. With my long hair tucked into a cap, I was amazed at how my hairless body seemed to slide through the water, and I now understood now why competition swimmers put up with the hassle of shaving down. When the coach finally turned us loose, I dragged myself back home and collapsed onto the sofa in the family room. Janet was at a football game, and my parents were out playing golf. In retrospect, there is no doubt that my utter exhaustion set the stage for the events that were about to unfold.

The telephone rang and I could barely lift the receiver. "Hello."

"Jim? This is Hillary."

I snapped to attention. "Hi."

"When are you coming over?"

"I just got back from practice. Any time is good."

"How about now? We’ll need some time to find a costume for you. I can fix us something to eat before we go to the dance."

"On my way!" I said, my fatigue momentarily overcome by the excitement of seeing her. Hillary lived about a half a mile away, and after leaving a note for my parents that I would be back after the dance, I dragged my weary body to her house.

When Hillary opened the door, I was surprised to see her dressed in army fatigues and combat boots, with camouflage paint smeared on her pretty face. Her hair was tucked up under an army field cap, and she had glued a fake mustache above her desirable mouth. "Wow," I said, "I didn’t know I was going out with a guy."

She laughed and led me to the stairs. "My parents are up in LA, so we have the house to ourselves," she said. "Come on up, and we’ll find you something to wear." My heart skipped a beat at the thought of being alone with Hillary, even if she was dressed as a combat soldier. Her bedroom was not what I expected: whereas my sisters’ rooms were filled with cuddly animals and pictures of rock stars, the only decoration in Hillary’s room was a poster of Judy Garland wearing a top hat and tails.

I waited awkwardly at the threshold of her room as she went to her closet and sifted through her hangers. "I thought I had an old prison suit in here that I wore one year, but I guess my mom gave it to the church thrift store," she said. She emerged from the closet and sized me up. "Hmm," she said. "Take off your shirt."

Needless to say, I complied. She walked around me and asked me to take off my jeans. Not believing my good fortune, I unbuckled my belt and let my jeans drop to the floor. "Oh my, look at those legs. I think I have the perfect costume for you."

Suddenly I remembered my hairless state, and I started to stammer an explanation. "I know you’re a swimmer, Jim, that’s how you got that beautiful body. Have you ever dressed up as a girl?"

"Once," I blurted out, "my sisters made me do it, on Halloween."

"Would you let me try to dress you up for the dance?"

What could I say? Here I was, practically naked, alone with my dream girl in her bedroom, and she wanted me to wear her clothes. The fact that she was dressed as a man only made it more surreal. "Can’t you think of anything else?" I said lamely.

"Come on, Jim, it will be fun. Whaddaya say?"

"I guess, if you really want me to," I said. Before I could change my mind, Hillary returned to her closet and started searching through the hangers. She found what she was looking for and pulled out a short wool jumper. She tossed it on her bed and looked through the closet some more until she found a white blouse with a high ruffled collar. "These have always been too big for me, but they should fit you perfect," she said as she started pulling lingerie and stockings out of her dresser drawers.

It is hard to describe my feelings at that moment. On the one hand, I was mortified that my dream date had turned into a freak show. But as I watched her selecting a bra and panties for me, long-suppressed memories of a magical Halloween night, years ago, flooded back. She broke my reverie when she sniffed my hair and said, "Yuck. Do you shampoo with Clorox?"

"I’ve been in a pool all afternoon."

"Well, I’m not going to smell that all night. Report to the bathroom down the hall and await further instructions."

"Yes, sir!" I saluted my man in uniform. She followed me into the bathroom and handed me her father’s razor. "Get that peach fuzz off your face, and then get into the shower. My shampoo and conditioner are in there, use them both. And you can dry yourself off with my towel. Any questions?"

"No, sir!" I saluted again as she closed the bathroom door. I did as I was told, and as I was drying off with her towel, the door opened a few inches and her hand appeared with a pink robe and a pair of panties. "Put these on and report back to the bedroom." The door closed before I could respond. As I put on Hillary Fowler’s panties, I felt a stirring in my loins, and I hurriedly wrapped her robe around myself and returned to her bedroom. She was waiting for me with a hair dryer in her hand.

Hillary had me sit down at her vanity, and as she methodically dried and brushed my long hair, I closed my eyes in anticipation of what was to come. For the second time in my life, my hair was fashioned into a ponytail with a scrunchie, and then she started in on my makeup. After she sponged on some foundation, she went to work with powders and brushes, and I watched in fascination as my face became more and more feminine. When she started to apply some lipstick, my penis suddenly jerked in my panties, and I pulled Hillary’s robe over my growing erection. "This is so much fun!" she said as I stared at myself in a daze.

"Okay, time for phase two," she instructed me, and I followed her back into her bedroom. She handed me a pair of suntan pantyhose. "Do you know how to put these on?"

"I wore them once on Halloween," I said.

"Then you know there’s nothing to it. Be careful not to get them all twisted when you pull them on." I sat down on her bed and began to slide her stockings up my legs. Once again I experienced the exquisite feeling of sheer nylon against my smooth skin. I stood up and did a knee-bend to pull them tight. Hillary did a double-take when see saw my raging hard-on.

"Whoa, Mister, where did that come from," she said as she picked up a padded bra. I tried to think of something to say while she fastened the bra behind my back and adjusted the straps. "Here, put this on, maybe it will help," she said, handing me a short white half slip. I stepped into it, relishing the sensation as the silky fabric brushed against my nylons. The outline of my engorged cock was clearly visible as it pressed against my slip.

"I think this is turning you on," Hillary said.

"You’re what’s turning me on," I managed to say. "I’ve been dreaming of going out with you since the first day I saw you."

She took my face in her hands and kissed me on the lips. She was taller than I was, and I had to stand on my toes as I kissed her back. Suddenly she pushed me down, and I fell back onto her bed, my legs in the air. Hillary unfastened her belt and let her trousers and boxer shorts drop to her ankles. Then she fell on top of me and started to kiss me again. I felt her pulling my pantyhose and panties down to my knees, and I couldn’t believe it when she straddled me and lowered her pussy onto my erect penis. She started to hump me, faster and faster, and I cried out in ecstasy as I exploded into her.

Hillary lay on top of me, panting from the exertion. "Was that your first time?" she asked at length.

"Yes." It occurred to me that I had just lost my virginity, wearing women’s clothing, to a girl who was dressed as a guy. What was happening to me?

"That was awesome," she said. She rolled off me and disappeared into the bathroom, leaving me to my confused thoughts. When she returned, she was holding her lipstick. "I’ve never had to wipe a guy’s lipstick off before. Here, your face is a mess. Let’s see what you can do with it."

I stuffed my now limp penis between my legs, straightened my panties and hose, and walked over to the full length mirror on her closet door. I was entranced by the reflection of a girl wearing a slip and stockings, applying lipstick to her pretty face. "Not bad, Missy," Hillary said. She watched me put on her blouse, fumbling with buttons that were backwards for me, and then she helped me into her jumper, tying the bow in the back for me. It came to mid-thigh, and my legs looked terrific in the mirror. Hillary rummaged through her closet for a pair of weejuns and asked me to try them on. With in effort, I was able to wedge my feet into them.

She stood back and admired her creation. "If I didn’t know you were a guy, I would never believe it. This is so cool. Let’s go downstairs and I’ll fix us something to eat." 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 struggled 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 was gay. 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.

 

1994

 

"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.

 

1995

 

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 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 womens’ 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?"

"I’m not sure I know what you mean."

"Mr. Taylor, I excused those two other students on sight because they are obviously exhibitionists. You, on the other hand, are what was once referred to as a closet queen. Suppose you had the opportunity to come out of that closet. To experience life as a member of the opposite sex. Not just for a night. For the rest of the quarter."

This was not what I had in mind. "Professor, this is crazy. How could I possibly get away with something like that? My roommates would throw me out of the dorm."

"Do you have any close friends here at Cal, Mr. Taylor?"

"Not really. A couple of guys in the dorm, I guess, but no friends from high school or anything like that. I’ve only been here a month."

"Exactly. What if I were to offer you a place to live." He held up his hand as I started to stand up. "Don’t jump to conclusions! You would be living alone. My daughter has an apartment in Emeryville which she has temporarily vacated. It is fully furnished, with a view of the Golden Gate Bridge, I might add."

I sat back down. Part of me wanted to run out of his office as fast as I could. But another part, just below the surface, desperately wanted to learn more. "What do you want me to do?" I heard myself say.

The professor got off the desk and began to pace around his office. "If I tell you my reasons, it will destroy the integrity of the experiment. I can only tell you this. If you agree to participate, you will move this weekend into the apartment in Emeryville. You will be given an allowance of $1000 to purchase a complete feminine wardrobe. Starting next Monday, you live 100% as a woman for the balance of the quarter. Do you have plans to leave Berkeley between now and December?"

"No."

"Is your family planning to visit you between now and the end of the quarter?"

"No." Money was tight, and I had assured my mother that it would be okay if I spent Thanksgiving alone.

The professor produced a two page legal document. "Read this carefully. Think it over. Your decision will not affect your grade in any way, and like the other two students, you have already assured yourself a higher grade just for volunteering." I stuffed the paper into my backpack and I was halfway out the door when he spoke again. "Mr. Taylor," he said softly, "I don’t want to influence your decision, but I think you might find some answers from this. Answers that you might otherwise spend the rest of your life searching for."

I took the document out of my backpack, scanned it quickly, signed it, and handed it back to him.

* * *

As agreed with the professor, I told my roommates that I had to drop out of Cal and hoped to return in January. On Friday afternoon, we loaded my meager possessions into the trunk of his car and he drove me to a stylish apartment complex on a marina overlooking San Francisco Bay. He pulled into a garage under the complex and pointed out a red Honda Prelude. "That’s yours whenever you want to drive it," he said as he parked next to the elevators and helped me carry my stuff up to the third floor. When we went inside, I could not believe the situation I had fallen into. The apartment had a smartly furnished living area, a well equipped kitchen with a pass through counter and two barstools, a bedroom with a queen size bed and an immaculate adjoining bathroom. I doubt if any freshman in the history of Berkeley has enjoyed a sweeter setup.

Professor Kleinberg led me out onto the balcony, which as promised offered a spectacular view of San Francisco and the Golden Gate Bridge. "Mr. Taylor, you are about to embark on a great adventure. I am counting on you not to let it interfere with your studies, and I have confirmed with your other professors that so long as you continue to attend lectures and sit for the exams, there will be no affect on your grades. If you encounter any problems outside the classroom, here is my home number." He handed me a scrap of paper, and then dug into his pocket and produced ten hundred dollar bills and a set of keys for the apartment and the Prelude. "See you in class on Monday, Miss Taylor."

After he left, I checked out the refrigerator and pantry, which had been stocked with more food than I had seen since I left home. I called my mother to give her my new phone number, explaining that I had found a way to save some money by apartment sitting for a professor, and then set out in the Prelude for the nearest shopping center.

* * *

Away from the cacophony of dorm life, I slept until almost noon on a beautiful Saturday morning. The late October sun sparkled off San Francisco Bay as I puttered about the kitchen in my new nightgown, fixing myself a mug of coffee and a bowl of Special K.

My foray to a strip mall in Emeryville had yielded the bare minimum: besides the nightgown, I had been able to find a few pairs of panties, a padded bra, a denim skirt, and two tops at Ross, a pair of smart brown flats from a shoe outlet, and makeup and pantyhose from a large drugstore. My face hidden by dark sunglasses, I ignored the stares from curious salespersons.

I had almost $900 left to spend on a wardrobe that would have get me through the next six weeks. My first decision had already been made: I was not going to grunge around the campus in jeans and sweatshirts. If I had to live as a girl, I was going to be all girl, and within the limits of my budget, I was going to dress like I was pledging one of the sororities on Bancroft Way.

All of my guy clothes were stored in boxes in the hall closet. Before going to bed, I had drawn a hot bath and completely shaved my body, leaving only a small triangular patch of pubic hair, and for the first time in my life, I had filed and polished my fingernails. I even trimmed my eyebrows, feathering each one into a feminine arch.

Now it was time to make the transition, and my heart was pounding as I finished my coffee and lit a cigarette, a habit I had picked up from my roommates after it became apparent that Cal swimming was over my head. Jim Taylor’s hopes and dreams would have to be put on hold. Jamie Taylor was about to meet the world.

My hair had grown over my shoulders since I arrived in Berkeley. I shampooed and conditioned it during a long, hot shower, and after giving my face a close shave and applying moisturizing crème to my arms and legs, I went to work with a blowdryer. I thought about trying to create a hairdo, then decided just to pull it into a ponytail until I could get some professional help. The professor’s daughter had a supply of scrunchies in her dresser, which I borrowed along with some inexpensive jewelry.

My hair attended to, I sat down on a tuffet in the bathroom and started in on my makeup. Furtive hours spent reading my sisters’ and mother’s magazines had prepared me well. Moisturizer first, then foundation, powder, blusher, eyeliner, shadow, mascara and lipstick. I had learned that less was better, and when I inspected the final product in the mirror, I found myself face to face with a stunning young woman.

The spell was broken when I realized that my penis was standing at full attention. Almost mechanically, I stroked it a few times until it spewed jism all over the bathroom mirror. The usual euphoria was followed by a momentary wave of revulsion, but with another look at my pretty face in the mirror, the feeling soon dissipated. I had reached the point of no return.

When my penis softened and shrank, I felt feminized, almost emasculated. My heart was racing as I tore the tags off a new pair of panties. I stuffed my limp penis between my legs and pulled them over my waist. The padded bra came next. With the illusion of breasts and my telltale genitalia concealed, for the first time my body looked like a woman’s. Incredibly, I felt my penis beginning to stir again as I admired the slim physique of the girl wearing a bra and panties in the full length mirror on the bedroom wall.

My hands were shaking as I tore a pair of L’eggs out of their package and began to pull them carefully up my legs. Sitting on the edge of the bed in front of the mirror, I was transfixed by the site of the gorgeous girl putting on her nylons. Knowing that she was me was an indescribable rush, and my penis struggled desperately to break free. With a sigh, I pulled down my panties and hose and stroked it a few times. Once again, it erupted, and the pleasure was so intense that I actually fell to my knees.

This time, there was no revulsion, only impatience for my penis to return to its flaccid state so I could finish getting dressed. After it complied, I readjusted my panties and nylons and got back to business. I selected a white top, which I pulled over my head and down over my pert breasts. It hugged my slim hips, and looked sensational on me. Then I took my new skirt off its hanger, and stepped into it. I had to twist it around to button and zip it, then lift it up to tug my top into place before I straightened it out. It fell about six inches above my knees, and I realized that my short skirt and long legs would attract guys like a magnet. As I stepped into my dainty shoes, there was no question about it. Jamie Taylor was absolutely devastating.

The rest of the day was a kaleidoscope of new sensations. Pressing my knees together as the man in the toll both on the Bay Bridge stared at my legs. Trying on skirts and dresses in the Macy’s on Union Square. Flirting with two guys at the next table while I lunched on a salad at a sidewalk café. The pampered feeling of having my hair cut and styled. The sting as piercing needles went into my ears. Having my foot caressed by a shoe salesman when I tried on my first pair of high heels. Juggling my purse and packages while I tottered back to my parking place in my new heels.

By the time I started driving back towards the Bay Bridge, I was exhausted and exhilarated, and I never saw the other car coming.

 

 1996

 

$8 MILLION AWARD FOR HALLOWEEN ACCIDENT

San Francisco – After deliberating for less than an hour, a jury awarded James Taylor $8 million for injuries suffered in a traffic accident on Mission Street last October 31^st. The Irvine resident, now 19, was a student at UC Berkeley when his Honda Prelude was broad sided by a Mercedes driven by Daryl DelMonico, 38, of Hillsborough. Both drivers were dressed in Halloween costumes, DelMonico as a circus clown and Taylor as a girl. Lawyers for Taylor argued successfully to the jury that DelMonico’s red nose interfered with his visibility and caused the accident.

I tossed the newspaper onto the floor and started to laugh. After three weeks in a coma, eighteen stitches on my forehead, two operations including painful rhinoplasty on my nose, and almost six months of agonizing physical therapy, the nightmare was finally behind me. My mother had gone through most of her savings to make sure I had the best medical care and legal representation, and now our financial future was secure.

She had been waiting at my bedside when I finally came around in my hospital room. I had no memory of the accident, but my recollection of my experiences in the hours before I lost consciousness were still vivid. When I finally realized where I was, I desperately tried to explain. She just held my hand and told me to get some rest.

When I came around again, Professor Kleinberg was standing nervously by the door. My mother, he said, was getting a bite to eat. He told me about concocting a story for her, and the police, that I had dressed as a girl in preparation for an elaborate costume party. He assured me that my reputation was safe. I suspected that he was more concerned about repercussions to his faculty standing as a consequence of his unorthodox experiment. When I apologized for wrecking the Prelude, he told me that was the least of his concerns.

Now, almost a year after the accident, my body was sound again. Swimming progressively longer distances every day, I was lean and lithe, without an ounce of body fat. My stitches had vanished, my nose was smaller, and my hair had grown well over my shoulders. With all of my friends away at school, I had a lot of time to think as I whiled away the lonely days in my room.

At least now my mother would be able to quit her secretarial job. Not that I intended to spend any more time living at home. I was ready to spread my wings again, only now it would require more courage than I had ever mustered. If my father were still alive, I doubt if I would have been able to go through with it. Telling my mother would be hard enough.

When my lawyer called us with the news about the verdict, we had been too stunned to celebrate. Tonight, when my mother got home from quitting her job, we planned to go out for dinner at the Ritz Carlton. I dressed in a coat and tie for the last time, and I was pacing the house nervously when she got home from work. She sensed that I was preoccupied with something while we drove to the restaurant, and after we were seated at a quiet booth, she broke the silence.

"Tell me what’s wrong, Jim."

She was a strong woman, and I respected her too much to play games. "Mom, I love you and I don’t want to hurt you, but I have made a decision about my future that is going to be very hard to understand."

She had a stricken look on her face, and I took her hand and squeezed it gently.

"Jim, if you don’t want to go back to college, you don’t have to. You can stay home as long as you want to."

"That’s not it, Mom." There was no point in delaying it any longer. "Mom, I want to become a woman."

She gasped and blinked her eyes. Tears started to roll down my cheeks as I pressed on. "I’ve been fighting this for years, Mom. It’s not something that I want to do. It’s something that I have to do."

She sat back in the booth and stared down at her shaking hands. "This is such a shock. How long have you felt this way?"

How could I tell her that it all started with an innocent Halloween costume? "This has nothing to do with you, Mom. I love you, and I just hope you’ll try to understand."

"I just want you to be happy, Jim. I just want you to be happy."

 

* * *

 

"Are you sure you don’t want me to come along this afternoon, dear?" She wrung her hands nervously as she watched me carry my shopping bags up the stairs.

I paused on the first step and kissed her on the forehead. "No thanks, Mom. Just give me a little space now, okay? When I come back downstairs, I’ll introduce you to your new daughter." I turned and walked up the stairs before she could respond.

My body was already hairless from months of swimming therapy, and I had allowed my fingernails to grow quite long. After filing them and covering them with a coat of quick dry polish, I methodically laid out some of my purchases. It was unseasonably warm for late October, with the same Santa Ana winds that were blowing the day Hillary Fowler introduced Jamie Taylor to the world, and I was quivering in anticipation when I spread my new sundress carefully upon my bed.

In a few months, I hoped that my hormonal balance would be radically altered, but today, as always, a raging erection anticipated my transformation. I took care of it with a few quick strokes while I was in the shower. I watched my seed swirling into the drain and wondered if I would ever have children. Not likely, I said to myself, and I indulged in melancholy thoughts as I shampooed and conditioned my long hair, which months at the pool and in the sun had lightened into a golden auburn. After drying it, I took my time with one of my sisters’ magazines and fashioned it above my head with a French braid.

I shaved and put on a little makeup. My new pug nose made my face look even more feminine than it had before my accident, especially after I played with my hair until it fell in soft bangs above my eyes. I had surreptitiously maintained the holes in my earlobes, and a pair of Emily’s hoop earrings completed the picture.

My long legs were deeply tanned, and although I loved to wear stockings, I decided against them. A wonderbra, panties, the sundress and a pair of strappy sandals would have to do. I would be undergoing a physical examination in less than an hour, and I wanted to keeps things as simple as possible. I became aroused again as I lowered my dress over my head and watched the beautiful girl in the mirror reach behind her back and tie it in a bow. But I might need to provide a sperm sample today, so I concentrated on adjusting my sandals and organizing the contents of my purse.

I paused in front of the mirror before heading downstairs to confront my mother. Was I doing the right thing? Once I walked down those stairs, there would be no turning back. The beautiful girl in the mirror smiled at me, and told me the answer to my question. Still, I had knots in my stomach as I slowly descended the staircase, my dress billowing around my knees. When I reached the landing, my mother was waiting for me with a strange look on her face. She seemed to be surprised, even a little relieved, and something else. It was the same look I had seen on her face when I was accepted at Cal. My mother was proud.

 

* * *

 

I nervously flipped through a dog-eared copy of Redbook while I waited for the doctor. My God, I never knew womens’ magazines were so sexually explicit. The article I was reading described different positions for making love on the kitchen table, in an airplane lavatory, and other places I had never imagined. I had a lot to learn about being a modern woman.

Fortunately, I had the waiting room to myself, and the receptionist had seemed nonplussed when I presented her with my insurance card in the name of James Taylor. When she called me, my knees were shaking as she escorted me down a short hall into an examination room. She instructed me to remove my dress and shoes and put on a paper gown. I had just done so when I heard a rap on the door, and the doctor entered with a clipboard in her hand.

She was about thirty, with pretty legs beneath a short white coat. She appraised me with her piercing brown eyes for a moment, and then she asked me to sit down on the examining table. She studied her clipboard, and then she started asking me questions.

"Shall I call you Jim?"

"I prefer Jamie."

"Very good. How are you feeling, Jamie?"

"I feel fine."

"You’ve been in an automobile accident, I see. Are you experiencing any pain or difficulty?"

"No, I’m just fine now."

She put down her clipboard. "How long have you wanted to be a woman?"

"I guess since I was a sophomore in high school. Maybe even before then. I fought it for a long time."

"When did you decide that this was what you wanted?"

"Last year, after the accident. I had a lot of time to think. I know this is what I want. What I need."

"How about your family?"

"My father died two years ago. Telling my mother was very hard."

"When did you tell her?"

"Last night."

"What did she say?"

"She cried last night. But she wants me to be happy. Today, when she saw me for the first time, as Jamie I mean, she hugged me and she wouldn’t let me leave the house until I put on her favorite perfume."

The doctor smiled. "She sounds like quite a lady."

"I’m sure it’s hard on her, but she wants what’s best for me. I also have two older sister."

The doctor raised an eyebrow and wrote something on her clipboard. "Tell me about your childhood."

I knew where she was going. "I was a normal kid. My dad always seemed disappointed that I wasn’t more of an athlete, and I spent a lot of time with my mother and sisters because he traveled a lot. But I wasn’t feminine or anything. I had a lot of guy friends, and I lettered three years on the swim team."

"Can you remember your first orgasm?"

"Yes. I was wearing my sister’s dress."

She made of note of that. "Did you date a lot in high school?"

"Off an on."

"When did you lose your virginity?"

"Sophomore year. I was wearing her clothes. She was dressed as a man."

The doctor took it in her stride. "That’s a first for me."

"It was Halloween."

"Did you see her again?"

"No, just as friends."

"When was your next experience?"

I paused as painful memories came back. "I dated a lot of other girls, but I never made love to any of them. Most of the girls I went out with weren’t that way. And the few times I had the chance, uh, I couldn’t make it happen."

The doctor nodded and jotted something down. "When did you have your last orgasm?"

"An hour ago."

"Does it stimulate you to wear womens’ clothing?"

"Incredibly."

"How do you feel after you have an orgasm."

"Sad, depressed. Revolted with myself."

"For dressing like a woman?"

"For being a man."

She put down her pen and pulled on a pair of latex gloves. "Please stand up and remove your gown." When she saw my bra and panties, she asked me to remove them also. I had never been examined by a female doctor, and I was embarrassed as she began to probe my body. "You are in wonderful condition," she observed. She took my penis in her fingers and pulled and squeezed it, and she spent a lot of time with my testicles, but I was not aroused.

"Do you think you could give me a sperm sample?" she asked. I nodded and she handed me a glass jar. "You can leave it with the receptionist after we’re finished. Jamie, let me take you through your treatment options. You can undergo therapy to explore the reasons for your desire to become a woman, and perhaps even overcome it." I shook my head firmly. "I didn’t think so. You can continue dressing as a woman occasionally, and make it a part of your life without more drastic changes." I shook my head again. Been there, done that.

"Or, we can begin now on a path that may or may not lead to your becoming a woman, but which will result in profound changes for you, some of which may be irreversible." I nodded as she went on. "The first step, which I am prepared to initiate today if you agree, is to put you on female hormones, combined with another hormone that will block your body’s production of testosterone. This will begin to change your body in several ways. Your skin will become softer. The hair on your head may become thicker, but the hair on your body will become thinner and you will probably have to shave your beard less often. Your muscle tone will be affected, and you are going to create some body fat, particularly around your hips and your backside. Most noticeably, you will begin to develop breasts. And your ability to have erections and ejaculate will be severely affected. You may lose your ability to perform as a man altogether. Do you understand all that?"

I nodded affirmatively. "I understand."

"Are you sure that’s what you want, Jamie?"

"With all my heart."

"Very well. I will leave a prescription with the receptionist. To get you started, I can give you an injection now that will hasten the process. Are you ready to begin?"

I told her yes, and the doctor filled a large hypodermic syringe with amber fluid and injected it into one of my ass cheeks. After she left, I put on my bra and panties and slipped on my dress. As I reached down to strap on my sandals, the stimulation required for a sperm sample presented itself, and I quickly pulled down my panties and held up my dress as I squeezed an orgasm into her jar. This time, I did not experience revulsion, only intense pleasure and profound relief.

 

1997

 

"Jan, I need a little help."

I was standing before a dressing mirror in the master bedroom of my new condominium in Newport Beach. My beautiful breasts peeked over a pushup bra, and my legs glistened in sheer white stockings through a slit in my long half slip. My hair and nails had been professionally done that morning, and my makeup was perfect.

Janet, who had been waiting impatiently downstairs, came into my room and shook her head. "I don’t think I’ll ever get used to you like this," she said as she watched me struggle into my lavender bridesmaid dress, identical to the one she was wearing.

"Zip me up, please," I asked her. Janet complied, and she watched in fascination as I stepped into my three inch heels and fussed with my matching white purse. "I still can’t believe Emily’s getting married on Halloween."

"There’s something I’ve got to ask you, Jamie."

"Anything, Sis."

"Do you remember that Halloween when we were kids and Mom, Emily and me forced you to dress up as a girl? Did that have anything to do with this?"

"Promise you’ll never tell Mom?"

"Oh, my God!"

"I mean it, Jan, don’t ever tell her. I don’t want her blaming herself for the life I’ve chosen. This probably would have happened sooner or later anyway, but yes, I’ve never gotten over that night." I crossed to a bookcase above my desk and pulled out my old thesaurus. Janet smiled sadly when I showed her the creased photograph of the girl in the green dress.

The yellowed clipping from our high school paper fluttered onto the floor, and I stooped with difficulty in my long dress to pick it up. "What’s that?" she asked me.

"Do you remember when you set me up with Hillary Fowler?"

Janet got a funny look on her face. "Yeah."

"Hillary dressed me up in her clothes and made love to me before the dance. If you hadn’t gotten us together, maybe none of this would have happened, but I doubt it. It was just meant to be, Jan. And I’m glad. I’m really glad that I found out in time to make a new life for myself. I’ve got you to thank for it."

Janet handed the clipping back to me. "Hillary Fowler will be at the wedding."

"Really? She’s in for a surprise."

"She’s not the only one."

* * *

Emily’s wedding was beautiful. Janet stood beside her as maid of honor, and I cried throughout the ceremony as I sat next to my mother. The hormones had affected me in a lot of ways, emotionally and physically, although my body had finally reached a happy equilibrium. I felt wonderful, and the wedding pictures show three radiant young women surrounding their beaming mother. The close friends and family who were in attendance were unbelievably kind and considerate to me.

At the reception, while mother, Emily and Janet were out on the dance floor, I was seated alone at the head table sipping a glass of champagne when a handsome young man approached me. He looked vaguely familiar.

"Jamie?"

I studied his face. He was tall, with delicate features and thick black hair which came just over his ears. Oh my God, it couldn’t be! But it was! "Hillary?"

She sat down next to me and kissed me on the cheek. "You look wonderful."

"So do you! I can’t believe you! You look just like a guy."

"Coming from you, that’s quite a complement."

I laughed and touched the sleeve of Hillary’s navy blue suit. "Tell me all about it."

"You first."

She looked up and saw my mother and sisters staring at us from the dance floor. "Let’s go outside, okay? I’ll meet you out in the garden in a few minutes." Before I could respond, Hillary got up and walked towards the door. I waited a minute and then made my way out to the garden, where she was waiting for me under a white gazebo covered with brilliant flowers.

I lifted my long skirt and walked carefully up the gazebo steps. "I remember when I had to do that," Hillary laughed. I sat down next to her and we started to talk. For over an hour, we alternated between my story and hers, sharing experiences that few men and women have ever known.

"How did you get so buff?" I asked her at one point.

"Steroids and testosterone."

"Isn’t that dangerous?"

"Look at the East German Olympic team."

"Are you going to have an operation?"

"I don’t know. Are you?"

"I think so. I want to have a family some day, but they’ve already frozen a lot of my sperm."

Hillary leaned forward and kissed me on the lips. I responded with passion, and for the first time in almost a year, I felt something below my waist. The doctor had told me that once my hormones were reduced to a maintenance dose, I might regain the ability to have erections, although my penis and testicles had atrophied considerably.

We heard a commotion outside the reception hall, and I realized that Emily and her new husband were getting ready to leave for their honeymoon. I gathered up my long dress again and ran across the lawn in my heels, with Hillary loping along behind me. Emily’s husband was a great guy who had accepted me instantly, and I hugged him and my sister as they stood outside their car.

"Be a good girl," Emily told me.

"Be a good wife," I told her, and they were on their way. Hillary offered to give me a ride home, and I said goodbye to Janet and my mother and walked with her to her car. Once again, Hillary Fowler opened her passenger door for me, only this time I acted like a lady, smoothing my long dress under myself before I swung my legs into her car. We chatted about nothing in particular as she drove me to my condo.

"Would you like to come inside," I asked her after I opened my front door.

Suddenly, Hillary picked me up and carried me across the threshold. "And you thought your big sister got to have all the fun today," she said as she carried me up the stairs and lowered me gently onto my bed.

That night I became a woman. Between passionate kisses, Hillary and I undressed each other and explored our new bodies. When she took my limp penis into her mouth, I felt once again a delightful arousal, and although I did not become erect, I ejaculated again and again as she pushed my buttons and I pushed hers. The last time, she took the vibrator I had been using on her and gently inserted it up my ass. She sucked on my breasts and nibbled on my nipples with her teeth as she slid the vibrator in and out, each time bringing it a little closer to my sapped prostate gland. When I finally came, it was a woman’s orgasm that tingled throughout my whole body.

We lay in bed together all night, talking about the future. Maybe we should stay just as we were, a man with a woman’s body and a woman inside a man, so we could make love together every night and even have children some day. Or maybe we could find a doctor who would be able to transplant my organs onto her, and give her ovaries to me. With modern medical science, anything was possible. But that’s another story.

© 2002 by Nom de Plume

 

 

 

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© 2002 by Nom de Plume. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.