Like Father Like Son
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This is a work of fiction.
Any similarity between the characters in this story and any actual
persons, living or dead, is purely coincidental. This story is
copyright 2019 by Ayn Ryan.
Permission is hereby given to share this story on the World Wide Web,
provided that (a) no charge of any kind, including, but not limited to,
subscription fees, is made in connection with access to the story, (b)
the story is reprinted in its entirety, including this notice, and (c)
proper credit is given to the author at the time of posting. All other
rights, including, but not limited to, those of adaptation to other
media
and formats, reserved to the author.
Contact: [email protected]
Like Father, Like Son
I was nine when my mother died. I was hardly old enough to understand
what "breast cancer" was. I remember her growing weaker and weaker. I
remember her losing her hair. She still looked beautiful to me even
without hair. At first, she wore a wig, then as she grew worse, a long
floral scarf. In the weeks before she passed, I am not sure who looked
worse, my dad or my mom. When she passed, we both grieved. But I know
there was a part of both of us that was relieved. Both of us tried to
remember her as she was, rather than remember the end.
We both grieved in our own way. Dad focused on taking care of me. I
suppose the life of a single father is a lonely one. He threw himself
into work. After work, raising me was the only other thing he cared
about. I was too young to notice, but he didn't have any kind of social
life in the years after mom died. I wouldn't say we were still
grieving, but everything seemed "too soon."
I discovered my growing sexuality when I was eleven. It was late at
night, I could not sleep. It had seemed like every brush of the sheets
aroused me. Of course, I didn't know that's what it was. I had this
tingling feeling in my privates. I touched myself and felt it grow
stiff. It was instinct really, I took hold of my penis and stroked it.
It only took a few pulls and suddenly I stiffened, my toes curled as
wave after wave of the most amazing tingling feeling washed over me. I
was a little scared, all I knew was that it was the most intense
feeling, and I wanted more.
One evening not long after, I was watching TV with my father. There was
a commercial, to this day, I ccouldn't tell you what the product was,
but there was a woman in a red and black dress with a large belt
accentuating her wasp thin waist. Her legs were clad in black nylons
and red high heel pumps. She stood with her legs slightly spread and
all her weight on right leg. Her left hand was resting on her thrust-
out hip. Her blonde hair in a pony tail. I felt a stirring as my
sexuality awakened, I blushed uncontrollably. The show soon started,
and I doubted my father even noticed. That night I thought of that
woman and what she was wearing, and I stroked myself until my elbow
hurt.
From then on, I was obsessed. My penis twitched at the sight of high
heels. In public, it was the first thing I noticed about a woman.
Girls my own age were still wearing flats, I only cared about women's
shoes. Their legs in stockings or pantyhose, skirts and dresses. I
loved them. I loved long boots and short skirts. I loved strappy
sandals and flowy sundresses. I loved tight pencil skirts and pumps.
In the night, alone in my bed, my imagination ran wild. I began to
envision not only being with the women I saw, but then wearing those
clothes. I needed to feel why they were so sexy to me.
I was twelve when my father decided I was old enough to have the house
to myself until he got home from work rather than stay at the neighbor's
house as I had been doing. As soon as my chores and homework were done,
I was on my bed stroking into tissues. It took two weeks before I had
an idea. I felt terrible for thinking it, but I couldn't help myself.
I quietly went to my parent's room. The bedroom set my parents had was
the same. I went over to my mother's long dresser with the mirror and
opened the drawer. Inside were panties. Soft cotton everyday panties,
smooth satiny panties, silky lace panties. I was enthralled, and my
penis hard as a rock. I touched them and chose the softest and quickly
unzipped my pants took them off and practically ripped off my underwear.
Slipping on the silky panties, was a revelation. Before I pulled them
over my penis, I came the first time. Any guilt I had in raiding my dead
mother's wardrobe was pushed back in my mind. I cleaned up and padded
over to the walk-in closet. There inside next to my father's shirts and
suits were a row of dresses and tops, skirts and the occasional pant
suit. On the floor were racks of heels of all kinds. I just sat on the
floor and grabbed a pair of black pumps. They were too large, but I
didn't care. I tried standing, and like a new born foal, wobbly stood
up on the 4" high heels. Looking around the closet I shifted
precariously on my toes, too nervous to put any weight on my heels.
I looked through the rack of clothes until I saw it. A red and black
dress with cap sleeves. I took it off the rack and turned to the mirror
on the inside wall. I held the hanger up and looked at myself in the
mirror. My heart pounded in my chest. I could not wait to get these
treasures back to my room. I stepped to leave and stepped too far and
collapsed. Laughing, I kicked off the pumps, gathered them up along
with the dress and headed to my bedroom.
Once there I unzipped the back of the dress and stepped into it. I was
shaking as I slipped my arms into the sleeves and lifted the dress to my
shoulders. The dress was too big on my preteen frame. I reached around
and struggled with the zipper. Once it was mostly zipped, I stepped
into the heels. I looked at myself in the full-length mirror on the
back of my door. I looked like a boy in a dress and high-heels. The
dress was too wide in the shoulders, and too wide in the chest and hips,
but I was wearing it. I was wearing high heels. I was tenting the
panties, it ached and demanded attention. I hitched the dress up and
started stoking myself just standing there. I stroked myself to
completion, and for some reason, in heels it felt even better. I
collapsed on my bed.
It took a few minutes for the high of my orgasm to dissipate. When it
did the guilt of raiding my mother's wardrobe hit me. Looking at the
clock I realized I only had fifteen minutes before my dad would be home.
I kicked off the heels and gathered them up and rushed to the closet. I
put the shoes back where I'd found them. Then I tried to unzip myself.
I couldn't reach it. Panic started setting in and ended up on the floor
wriggled out of the dress from the bottom. My heart pounding, I hung
the dress back up where I found it. Stripping off the panties I put
them back in the drawer and gathered my clothes and underwear to race
back into my bedroom.
My father walked into the living room where I was watching TV, just
minutes after I sat down with a cold drink.
"Hey, kid," Dad said as he dropped his stuff at the door. "How was your
day?"
"Fine," I answered flied to the show.
"Great, good talk," he replied sarcastically. "I'll need your help with
dinner in ten."
"OK," I said. Once he was out of earshot I sighed and began to breathe
again.
I'd pulled it off. From then on, my weekday afternoons after school
were an exploration of my femininity through my mother's wardrobe.
There were stretches of time, sometimes weeks, when I actively avoided
going in there. There were other times when the closet called me like a
siren. I could not help myself. I learned to dress completely, filling
the bra pockets with rolled up socks. The heels began to fit better but
were still too large. I discovered I liked wearing strappy sandals I
could tighten them around my ankles to fit snuggly. I was learning how
foundation garments worked. I also started trying on my mother's old
wigs and then putting on makeup. I literally had no clue what I was
doing with the makeup. But it felt good on my skin.
I was home from school for spring break. Dad was at work and I was
looking forward to dressing all day. Dad got me up at normal routine.
"What's your plan today?" Dad asked as we had breakfast.
"Uh, I'm not sure," I replied.
"Well, don't spend the day watching TV," Dad admonished.
"I won't," I assured him.
Dad's cell phone rang. "This is Kevin Ryan...All right I'm on my way
in." He hung up. "I gotta run."
I continued to eat my cereal as dad stood, tussled my hair as he headed
out.
"Love you," he called as he gathered his stuff and left.
"Loved you too," I mumbled with a mouth full of food.
I went to the living room and watched tv for an hour. I just wasn't
comfortable going right to the closet. But my anticipation made that
hour drag on for what seemed like days.
Finally, I went to the bedroom. I picked out a matching lavender lace
bra and panty set. I took these treasures into the bathroom and started
the shower. Once warm, I got in and washed all over. Then using my
father's razor, I shaved my legs and under pits. What peach fuzz was on
my face I shaved as well. I finished, the shower and dried myself off.
There was some powder I'd discovered in the medicine cabinet as well as
a Secret deodorant. I powdered my body and used the deodorant.
Smelling nice and feeling refreshed I slipped on the panties and tried
tucking for the first time. Then I put the bra on. A couple of weeks
before I'd found a set of breast forms that my mother must have used.
These were a fabulous find as they moved so much more naturally than the
socks I had been using.
I padded barefoot to the closet and picked out a maroon A-line skirt and
a pinstripe blouse with three quarter sleeves. After putting them on I
put on black knee-high boots with a four-inch wedge heel. I decided
that I didn't want to mess with too much makeup, so I simply put on the
darkest lipstick I could find, which matched the maroon skirt perfectly.
The finishing touch was the long blond wig I put on. I the gathered it
up in pony tail.
By this point it was about 11 am, and I didn't want to jerk off and ruin
all the hard work I'd just put in despite the constant, almost
irritating pleasure. I practiced walking in the boots. The wedges were
much easier to walk in. I twirled in front of the mirror, enjoying the
way my skirt flared out. Then I returned to the living-room and
smoothed my skirt udder me as I sat down to watch TV. I flipped through
the channels and settled on a soap opera. I figured, I'd watch the
actresses and imitate them. The stories were actually engrossing, and
it wasn't until my tummy rumbled, I realized it was lunchtime.
I was busy making a sandwich when I heard my father say, "Well, don't
you look cute," I whirled around in surprise. "Oh my God! DAD!" I
cried.
"Hi," he said with a small smile. "I thought I'd come home to take you
to lunch. I see you already made some."
"Dad...I can explain."
"No need. I have eyes," Dad said.
"Dad, I know I shouldn't be wearing Mom's clothes," I said pleadingly.
"You aren't," Dad said.
"I know I.... Wait, what?"
"I donated all your mother's clothes a couple months after she passed
away. It was too painful to have them around. I could smell your
mother all around, even..." he said haltingly. "Even in my sleep. Those
clothes, they're mine."
I sat down on a kitchen chair with the piece of bread from my incomplete
sandwich still in my hand. The shock of being discovered was just
exploded by this new revelation. Suddenly, things made sense.
"Mom's" dresses were still a little too big despite my growing teenage
body. The selection of shoes in the closet was still fitting me despite
my growth spurt that had required a new pair of sneakers every few
months.
My dad pulled out a chair and said, "Like father, like son, I guess," as
he sat down.
"You knew all this time?" I asked.
"No, I had a few suspicions, but I didn't know for sure."
"So, when do you dress? I never even suspected."
"Ah, well every day for underwear and sleeping. I don't own any men's
underwear," Dad answered. "Fully dressed? Katrina is a night owl on
weekends."
"Who?" I asked.
"Katrina, is my female name. What, you don't have one?"
"Uh, no," I said. "That's not something I thought about," I confessed.
"I can imagine what a boy your age does," Dad said.
I blushed beet red.
"Yeah, I was fourteen once too," he said. "I have to say you were very
good at keeping everything clean an orderly, there were only a few
little hints, and even then, like I said, I wasn't sure. I also need to
compliment you on your makeup today, you look really good."
"I'm only wearing lipstick."
"Well in the day time, that's usually all some girls wear. I'm glad you
don't feel the need to go overboard."
I shrugged.
"So are you ready to go to lunch? You are dressed for a nice place, I
was thinking fast-food originally, now I'm thinking a nice sit-down
place."
"WHAT?!" I cried.
"Honey, there is nothing to worry about. You are at an age where you
are completely passable. You'll look like a teenage girl with her
father. We will just need to get you a few things to complete your
look."
Dad went to his room and came back a few minutes later with a black
purse with a long thin strap. He showed me he'd put a few things
inside. The lipstick I was wearing, powder for my nose and blush. Dad
supervised as I lightly powdered my face and nose. Then rouged my
cheeks. It was still a very clean and natural look.
Finished, he offered his hand for me to stand and lead me to the door
with his hand on the small of my back. I walked slowly, and rather
steadily I thought, to the door despite my knees feeling like jelly.
Dad guided me to the passenger side of the car where He opened the door
for me. "You are doing great," he said. "Now turn and face away from
the car, sweep your skirt up and sit back in the car." I followed his
instructions and looked up at him. "Now, sit back and swing your legs
into the car keeping your knees together. Always keep your knees
together, Honey."
"Ok, I'll remember."
"Now place your purse in your lap." Which I did demurely. Daddy closed
the door and walked around to the driver side. He jumped in. "Ready."
"Ha. Are you kidding? No."
"You're doing great," he assured me.
Daddy drove us to a nice restaurant. My heart was pounding as the
hostess led us to our table. I walked slowly, swaying my hips slightly
as I walked. Daddy had coached me in the car to walk slow and to sit
lightly as if there was an egg on the seat that I didn't want to crush.
Once sitting I was to cross my legs at the knee. The restaurant was
filled with stylishly dressed women lunching. I knew every eye was on
me. I know it probably wasn't true, but that's how I felt. Daddy pulled
out my seat and I sat down as he advised and crossed my legs then
allowed him to push me forward.
Dad sat down across from me and the bus boy filled our glasses with
water. I glanced up at him and saw him staring at me. It made me
blush, and my Father smile. When he left, Daddy, leaned forward, "Get
used to that, you are going to break men's hearts," I blushed all the
harder and took a sip of the water to wet my suddenly bone-dry mouth.
"Daddy!" I said somewhat shocked.
"It's up to you, but I can tell you it's fun," Dad said straight-faced.
"Are you saying you've gone out with men?" I whispered incredulously.
"Yeah, well Katrina has."
"Oh. My. God, I can't take anymore surprises today," I said.
"All right, we'll take it slowly," Daddy assured. "I'm just so happy I
can finally share this with you."
The waiter came over and took our order. I ordered a salad with grilled
chicken on it. Daddy ordered a pasta dish.
Unconsciously, I shifted my weight and recrossed my legs. Daddy noticed
and winked his approval at my deportment. "You're a natural. So, what
should your name be?" Daddy asked after the waiter left.
"I don't know," I said. "Should you be involved?"
"Hey, I helped name you in the first place," Daddy reasoned. "Pick
something you like. I happened to choose a name that shared my
initials, but you can choose whatever you like."
I thought for a while, absentmindedly munching on a bread stick.
"Careful how you eat, sweetie," Daddy quietly warned. I snapped out of
my reverie and chewed with my mouth closed.
"I think I'd like to honor Mom," I said. Dad's eyebrows went up in
surprise. "But I don't want to be 'Viki'," I reasoned. "I'll use her
first initial though. I think I like Veronica."
Dad smiled a big smile. "That's the title of one of my favorite songs
from the 80s."
"Yeah?"
"Yeah. I like it. It suits you," Daddy said.
Our meals arrived, and we thanked the waiter. Daddy and I sat and ate
and talked over the future. "Well, I can't have you borrowing all my
stuff. "he said. "A girl your age should have her own wardrobe. You
will develop a style all your own, and I'm in my forties and you are a
teen, you can't be using your mother's clothes," Daddy said. "We can
take care of that this week and weekend. For now, you can supplement
with my stuff, and you can have access to my wigs and such," I nodded
agreement, still astonished at the turn of events from the morning. Now
we were going to me a wardrobe of girl's clothes of my own. "I'll teach
you what you need to know in the evenings, but it looks like you are a
quick learner already."
I blushed. "I'm already looking forward to it," I said was we finished
our lunch and the waiter came over with the check.
Dad looked at his watch. "Damn, I've got to get back to work. We are
going to have to rush home."
Even though we were hurrying, I didn't rush out of the restaurant, not
in those heels. Daddy got he door for me, which was strangely
thrilling, and once again opened the car door for me. I sat down,
ladylike, and swung my legs in without instruction this time. Dad
smiled his approval and closed the door. On the drive home Daddy gave
me permission to remain dressed the rest of the day. We pulled up to
the house and pulled into the drive.
"I need to scoot back to work, can you get in?"
"Uh, I don't have my keys," I said.
"Check your purse, Dear," I opened the purse and sure enough Daddy had
placed my key in it. "Never leave the house without your keys in your
purse."
I smiled and got out of the car. Nervous being dressed in daylight in
my own neighborhood, I ran to the door in the tiny steps I'd seen women
using when rushing in heels. I'm not sure that I got there any faster,
but it was another thrill as I felt the breeze and short hem of my skirt
on the bare skin of my thighs. I quickly unlocked and opened the door
and turned and waved to Daddy as he pulled back out of the drive. I
closed and locked the door as he drove off. And immediately went to my
room. I pulled down my panties and relieved my aching penis from the
thrill of the past few hours.
That done, I cleaned up with a tissue and put my panties back on, then
set to work around the house doing my normal chores while still dressed.
Vacuuming was simple enough for example, but loading the dishwasher was
embarrassing. Every time I bent over, I could feel my ass being exposed
by the short skirt. Daddy came home just as I was bent over once more.
"A woman bends at the knees, sweetie," he said as he came into the
kitchen. "Modesty, honey, unless you are trying to tease a boy."
"Daddy! Please don't say that. Ewww," I protested.
"You never know," he said. "You might find you like it someday, or not,
that's up to you to find out."
"Whatever," I said.
"Listen, I'm going to change," Daddy said. "I've waited a long time to
be comfortable in my own house, and now that you know, I see no reason
to hide. In the meantime, Please, put on an apron so you don't ruin my
clothes, and start dinner.
"OK," I said.
I was well into prepping the vegetables when I heard the clicking of
heels on the floor behind me. I put the knife down and paused, steeling
myself for yet another of the day's revelations. I turned slowly and
looked at Katrina for the first time. I gazed down, as was my habit,
and saw she was wearing tan pumps I would learn later were called
"Nude". They had a low platform and when she turned to show off her
outfit, I saw they had red soles. She was wearing black skinny jeans,
and a gold anklet. A thin metal chain was being used as a belt. Her
top was scarlet top with a plunging neckline that really showed off
her...cleavage? How was that possible? I'd later learn and imitate.
Her wig was medium length auburn that cascaded to her shoulders. Her
makeup was light, just the scarlet on her lips to match her top. I was
unaware at the time, just how much makeup she used to look like she
wasn't wearing any makeup. At her neck was a dainty gold chain, the
pendent resting between her breasts.
"Well?" Katrina asked sheepishly hand on her hip.
"I...I...You...look amazing," was all I could squeak out.
"Thank you honey." She smiled.
"So...uh, what should I call you, when..." I asked gesturing to her
outfit. "You know."
"Call me Mom, silly," Katrina answered.
"But..."
"I know what you're going to say, don't worry about it. Veronica's mom
is Katrina. It doesn't affect Kevin being your father or Viki being your
mother," Katrina said reassuringly.
"Mom," I said, trying out the word. "I haven't called anyone 'Mom' in a
long time. Feels nice, actually."
"OK sweetie I've worked you enough, I'll take over dinner, you can go in
and watch TV."
Dismissed I headed toward the living-room, but I turned as I was about
to leave the room, and sat down in the kitchen. I was simply too
curious about Mom and how things were going to work now.
"Mom, when did you first start dressing?" I asked.
"Well, I guess I was about your age," Mom answered. "More or less. I
used to steal your Aunt Maddie's panties and jerk off in them. Which is
what you've been doing isn't it?
Embarrassed about being questioned about my masturbation habits, I
simply nodded.
"Yeah, I know. Look you will find, that your story is typical. A lot
of Crossdressers, transvestites and trans girls started that way. I
don't know why some boys are attracted to women's clothing, but suffice
to say, it attracts us. If it makes you feel good, then... I'm glad. I
don't want you to feel embarrassed talking to me about anything.
ANYTHING. We share this secret, nothing could be so terrible that you
couldn't share it with me or your Father. I love you no matter what."
"Ok," was my weak reply. "So, mom knew you dressed?"
"Yes, she knew. I told her," she answered. "I kept no secrets from
your mom. Things were different though. For one, I didn't go out once
we were married. I also restricted myself to lingerie. Your mom kind
of liked it. She loved my smooth legs, and sexy underwear. You should
have seen what I was wearing the night you were conceived."
"Mom!" I cried. "TMI!"
She laughed. "I think you will find I'm more uninhibited as a woman. On
a purely selfish level, I guess I can be more open about my dating
habits."
"Oh?" I said. "Have you always dated men?"
"HA! Now who is being nosy. I'm not going to discuss my sex life with
my fourteen-year-old daughter. Or my son for that matter. But to
reassure you, no, that was something I explored only after your mother
died and I couldn't bring myself to date women. But I guess, thinking
back, I've always been bisexual," She said. "Eventually, you will find
your own way. But not for years," Mom warned.
"Ok," I said skeptically.
The conversation continued through dinner. I discovered that Mom was
seeing a man. She was willing to allow him to come over now that I
knew. We discussed what I wanted from my dressing. Was it just sexual,
did I feel like there was a girl inside me? Right now, I was satisfied
with the situation as it was. Twenty-four hours earlier I was jerking
off in panties, now I'd gone out in public and was completely accepted
as a girl. It was a lot to digest for a kid. Mom informed me that I
had a lot to think about.
We cleaned up after dinner and then as mother and daughter we sat and
watched some TV. It was interesting that as girls we decided to watch a
drama that the day before I would have considered a "girls" show. But I
liked it, and I liked the intimacy I shared with Mom. It was different
than what I'd shared with Dad.
After the show Mom said it was time for bed. I protested, but she
patted my thigh and shooed me upstairs. "Besides I have a surprise for
you."
Reluctantly, I went upstairs followed by Mom. She had me stop at my
door as she went inside her bedroom. She came back with a small garment
box. "I stopped on the way home for a gift," Handing it to me, she
continued, "Once you are changed bring my clothes back to the bedroom,
and I'll show you something else."
Taking the box I did as I was told. I sat on my bed and unzipped my
boots and pealed them off. My toes rejoiced at their freedom. Then I
took off my clothes. Naked, I opened the box and took out the contents.
I held up the silky nylon cami and the matching tap pants. The cami was
pale blue with spaghetti straps, with lacey cups at the breast and a
tiny bow between. The tap pants matched and had lace on the hips and
another tiny bow at the front. Slipping them on was pure sensuality,
and I couldn't help myself I jerked off immediately. I was just,
cleaning up with my mother called. "Veronica! Did you fall asleep?"
"Ah, No," I said breathlessly. "I'm coming."
"I bet," Mom answered.
I gathered up the clothes I'd borrowed from Mom and padded down the hall
in my cute pajamas.
"There you are," Mom said as I entered. "I was afraid you were too
busy."
I blushed in embarrassment, obviously confirming her suspicion.
"Come sit up on the bed with me," Mom said patting the mattress next to
her. She was dressed for bed herself, wearing silk pajamas so dark
green they looked almost black. "Pick a color," she offered as she
swept her hand over a wide variety of nail polishes. "I've always
wanted to have a slumber party and do one another's' nails," Not having
school for a week, I was game. I smiled and hopped up next to her.
"You look adorable," she said.
"So, do you, those look very comfortable," I replied.
"They are," she replied, subtly adjusted herself. I ignored it.
I picked a color, a very feminine pink called "Coral." Mom complimented
my choice and I placed my feet in her lap. She used a foam thing to
separate my toes, which I found out was called a "Toe separator," And
she went to work on my feet. We chatted and giggled as she worked.
Finished, she had me sit up and took my hand in hers and did my fingers.
First, she filed and smoothed them. I wasn't a nail-biter, so I had a
small amount of length. Then she painted them the same color as my toes.
Finished she had me hold my fingers apart and my hands up and out. My
wrists were limp. Mom reached in between my outstretched arms and took
my face in her hands and drew me in for a kiss. "You really are
adorable," She said.
"Thank you," A replied, blushing.
"OK, off to bed sweet girl. But careful with those fingers and toes for
another twenty minutes."
"What about you?" I asked.
"I have to work this week, I can't," she said with a melancholy smile.
I kissed her one more time and headed out of the bedroom. I struggled
with the door and my toes felt weird as I walked back to my room. Once
there, I sat at my desk and opened a school book as delicately as
possible. In the quiet of the house, I heard Mom moaning in her room, a
barely audible squeal, and then silence. I smiled as I took the
separators off my feet and climbed into bed. I was tenting my tap pants
yet again at the thought of Mom enjoying her pjs as much as I enjoyed
mine.
Bree
- 17.02.2022
- 18
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