Only in October
© 2002 by Nom de Plume
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 later wished 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 an
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 31st. 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?”