Only in October
(c) 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 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 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 to speak in his faint German accent, a hush
fell over the auditorium.
"Good morning. Today we are going to continue with our
discussion of sexual deviations, or what used to be called
deviations before it became politically correct to refer to
them as alternative lifestyles. Mind you, I offer no
judgment here, simply a reflection on the emerging mood of
our popular culture, at least here in the Bay Area. I
daresay, what is tolerated and even welcomed here at
Berkeley and across the Bay in San Francisco might be
totally repudiated in other parts of the country, such as
Alabama, Mississippi, or Orange County."
I laughed along with my fellow students at this dig at my
home. Looking around the lecture hall, I observed an
astonishing diversity of young men and women, of every
ethnic background, type of dress, and standard of grooming.
If some of these kids turned up on a street corner in a
small town in Texas, they would probably be shot on sight.
With my shoulder-length hair, Cal sweatshirt and jeans, I
looked like a straight arrow compared to most of them.
"In any event," Professor Kleinberg went on, "today we are
going to discuss the transgender phenomenon. I know all of
you have done your reading, and also studied the
questionnaire, which was handed out at the end of last
Friday's lecture. That questionnaire included a space for
volunteers to fill out if they were interested in
participating in a little experiment. I am not asking those
who volunteered to identify themselves now, indeed that
would defeat the whole purpose. But for those of you who
did, and I believe it was three of you, please report to my
office on the fourth floor at the conclusion of today's
lecture."
The professor droned on for the next fifty minutes about
the current theories on the causes and treatment of
transvestism. I heard nothing that I did not already know,
having long ago devoured every book and article I could
find on the subject. When the class was finally over, I
grabbed my backpack and headed for the fourth floor.
Professor Kleinberg's secretary showed me into his
cluttered office, where another guy was already seated. He
was dressed in a leather miniskirt and boots, and his head
had been shaved except for a purple Mohawk. As I tried to
think of something to say to him, a girl walked in, dressed
in a black leather jacket and jeans and carrying a
motorcycle helmet. An enormous ring pierced her nose. The
three of us sat in awkward silence until the professor came
in.
He surveyed the three of us quickly, and then said, "Mr.
Lupo and Ms. Stoga, I want to thank you for volunteering.
However, based on my review of your credentials, I am
afraid you are not quite right for this experiment. I
assure you this will not effect your standing in my class,
and in fact as a result of your volunteering, you have
already guaranteed that your final grade will automatically
jump a whole point after your papers and examinations have
been completed. I thank you both for coming."
They both shrugged and walked out. When we were alone, the
professor closed the door and sat on the edge of his desk.
"Mr. Taylor, tell me why you volunteered for this."
Without hesitation, I told him the truth. "When I was in
seventh grade, my mother and sisters forced me to dress up
as a girl on Halloween. Ever since, I have been fascinated
by women's' clothing. I find it incredibly arousing. Once,
when I was in high school, my girlfriend took me to a
Halloween dance after dressing me up in her clothes. It was
the most exciting night of my life. I have been trying for
years to get this out of my system. Nothing seems to work.
I was hoping you could help me."
The professor took off his glasses and polished them with
his necktie, deep in thought. "Mr. Taylor, I may be able to
help you, but not perhaps in the way you are thinking. Have
you ever considered taking this obsession of yours to the
limit? To explore the depths of your fixation, and perhaps
uncover the reason for it?"
"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 cr?me 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 caf?. 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
women's' 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 women's' 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