growing up

I grew up in a f****y where there was my mom, my s****r
and myself. My dad was never around, he was always out
on a flight or some other business. It got worse when
my mom and dad got divorced. My dad moved away and I
hardly ever saw him.

I lived with my mom and my s****r for the next few
years, with the only changes being when my grandma came
to live with us for a while and then when my aunt came
to live with us at another time. This wasn't bad, but I
knew money was tight in our little f****y. The c***d
support check was always on time, but that plus what my
mom made wasn't always enough. I always had clothes to
wear, but they weren't always new or the best.

Until my mom got her promotion, sometimes I got hand-
me-downs. Most people wouldn't complain, but I didn't
like the fact that on the weekends my mom would have me
wear a dress so I could have my regular clothes during
the week. All my mom would tell me was that I was fine,
and not to worry about it, it wasn't anything new for
boys to wear dresses.

I did know that wearing diapers was not normal,
however. I had been in diapers constantly until I was
the age of four, and had worn diapers to bed until
after I was six. On and off, I had regular spells of
bed-wetting, so a box of diapers always sat in my
closet. When my mom and dad got divorced, it became two
boxes--one out and one in reserve; I wasn't just
wetting the bed anymore, I had to go back to wearing
diapers during the day. This eventually dropped back to
one, but I had a hard time with my s****r ribbing me
about it.

When I was eight, my mom met a man that she eventually
ended up marrying. My stepfather already had two
daughters of his own, and it seemed as though he never
really was a father to me. f****y outings always were
the worst. My s****r and my two step-s****rs always
ganged up on me since I was the boy. If I went to my
parents about it, they just said, "Tell them to knock
it off." That was all the intervention they gave, and
it seemed like they didn't care much from there.

When puberty hit, I began to question things a lot. Why
was it my s****rs always seemed to get more attention?
Why didn't my parents care one way or the other if they
singled me out or not? What was it about being a girl
that made them so special? I wanted to know in a way
that was beyond just asking my parents why. I wanted
that which had been denied me for so many years--the
attention that had been paid the girls, the feeling
that I belonged in the f****y.

So I thought about how to do it. Why not be a girl?
That was the only thing that seemed to stand in my way.
How do I do it? I didn't know anything about being a
girl, and I didn't want to ask any of my s****rs or any
of the girls at school. The laughter would be
unbearable. So I did a little research on my own,
looking through my mom's medical books, reading a
little from my s****rs magazines when she wasn't home,
and got some ideas on what I wanted to find out about.
Then I asked the one person who I figured wouldn't
laugh at me--my mom.

I waited until the night my stepfather was out of town
on a trip, and my s****r was babysitting and house
sitting for a few days one summer. It took me quite a
while to get my courage up, but a commercial for
women's hygiene products set me off.

"Mom, what's it like to be a girl?"

"A girl? What do you mean?"

"Well, there's so many things that are so different
about it."

"Like what?"

"Everything from the clothes that you wear to things
like a period, makeup, and stuff like that."

"Well, I don't know how to describe it, you just do

"Oh, okay."

We sat for a few minutes. My mom looked over at me and
asked, "Do you really want to know what it's like?"

"Yeah, I guess."

"No, I don't want an I guess or anything like that. You
either say yes or no. Nothing in between."


"Okay. I'll let you know later tonight, after I've
thought it over some more. Sound good?"


"Good. I need to run to the store for some things, why
don't you take a bath while I'm gone?"


I was in the bath when my mom got home from the store.
"Where are you?" she called to me.

"Upstairs in the bath."

My mom came upstairs and walked in the bathroom with a
grocery bag. She looked at my clothes on the floor
while I covered myself in the tub, then grabbed them
and walked out. I quickly got out and grabbed a towel.
I had it around me when she walked back in carrying a
bra and a pair of panties.

"Good, you're out of the tub."

"Yeah, what did you do with my clothes?"

"Those were boy's clothes."

"Yeah, they were."

"You wanted to know what it was like to be a girl. Like
I said, you just do it. So, I thought you would just do
it. I got all the things you would need to be a girl
for a while, all the stuff for your period and so on,
except you're going to have to borrow some of my

"Oh, well what are we going to do about the slight
difference in anatomy?"

"I thought about that. If a man takes the part of a
woman when having sex, like when two men go at it, what
gets used in the place of the vagina?"

"Okay, what am I going to have to do?"

"Well, first thing is that I don't want you going at
this half-hearted. You either go at this whole-hog or
not at all. If you want to do this, I want you to try
to become a girl as much as possible."

"Okay, what do I do first."

"First, take that towel off. I've seen everything under
there before. Girls aren't ashamed of being nude in
front of other women, especially their mothers. We are
the same sex you know."

I took the towel off as my mom pulled a douche out of
the bag. "Douching is a not so regular thing to do.
Usually you do it at the end of your period, if at all.
I'm having you do it so that you know how to do it.
Twist the little top off, screw on the plastic tube and
sit down on the toilet. Okay, now insert the tube in
your vagina, and gently squeeze the water into your
vagina. It's probably a little cold. Now let the water
flush out of your vagina. Great."

Next she pulled out a box of tampons. "Since this is
your first period, I got you slender tampons. As you
get older, you'll probably flow a lot heavier, so
you'll need the super and super plus tampons. Okay,
take one, take the wrapper off, and pull the string to
make sure it's attached. Now, I'll help you with this
first one, garb it like this, and let's slowly insert
it into your vagina, good, now push the tube in to make
sure it's all the way in, great! Now pull the tube out
and throw it away, tug on the string gently so you know
it's in there right, good."

Pads were next. "These stick in the crotch of your
panties, so start to pull your panties on, now take off
the backing and stick your pad directly in the middle,
good. I got you Stay-free maxi pads since it's what I
use, but you can get pads that are smaller. The only
drawback is that you go through more of them. Now pull
your panties on. Okay, now this is how you put your bra
on." She went through it with me. "Now let's go find
you a nice dress."

The rest of that night was uneventful. My mom had me
put on a nightgown, change my tampon, and then I went
to bed. When I woke up the next morning, I got dressed
and went downstairs.

"What are you wearing?" my mom demanded.


"No, let's go upstairs and get you a better outfit. A
summer dress would be nice. Did you change your tampon
this morning?"

I knew then that this wasn't just a one night thing.
"No, I didn't know this was going to be more than just
one night."

"Your period lasts about an average of a week. Come on,
let's go."


I learned how to put on make-up and other things of
being a woman the rest of that day. The following day,
I made sure I was dressed right going downstairs.

"We need to do some shopping today. Are you ready?"

We went to the store, and then out to lunch at Burger

"Mom, I have to go to the bathroom."

"Well, go. The ladies room is right over there."

I did my business.


When my stepfather got home from his business trip, I
could tell my mom had talked with him about it. He
looked at me, and then slowly looked me over again.
"Not bad," he said, "I think you look better dressed
that way. You have my approval and recommendation to
continue." I was happy that I was accepted.

My s****r's reaction was similar. "Now you know what I
deal with. Just don't think you can borrow all of my


At the end of the week, My mom put me back in my
regular clothes. Initially, I was disappointed. I
didn't mind though. I was a little bit more accepted
than I had been before. Three weeks later, I got a
surprise. We went shopping and my mom got an extra box
of tampons, and a box of pads. "It's that time of month
again," she said to me. When we got home I changed.

It continued this way for a few months. When school
started, I was grateful that I only had to wear panties
to school when I was on my period (in addition to the
usual tampon and pad). When I was at home, I put on my
full outfit. We had gone shopping for clothes for
school when I was on my period, so the actual clothes I
wore to school were not new, but I now had my own
outfits. I no longer had to borrow my mom's panties,
bras or dresses. I now felt comfortable going out in
public dressed as a girl; going into the ladies room
didn't bother me, nor did buying my tampons and pads.

Finally, my mom approached me about something new.
"When you first start having your period, you really
should get a check-up within the first few months by a
gynecologist. I got you an appointment."


"You have an appointment with a gynecologist."

"What about..."

"Don't worry, it's made for you under your s****r's
name. Just go to the appointment, and stop worrying." I
went to the appointment. I was nervous as hell, and
when they called my s****r's name, I went into the exam

"Okay miss, your first gynecological exam?"

"Yes, ma'am," I told the nurse.

"Don't worry, it's not that bad. Here's a gown for you
to put on. Take off your clothes, put on the gown and
sit up on the table. The doctor will be in shortly."

I did as I was told. Soon, a woman doctor walked in.
"Hi," she said, "I'm going to be examining you and
talking to you today. Just a routine exam. First, how
long have you been on your period?"

I told her.

"Okay, great. Now what I need you to do is lie back on
the table, good. Now put your feet up in the stirrups
here so I can examine your vagina."

I started to get very nervous when she lifted up the
gown to see my naked crotch. She put on a pair of
gloves and began feeling around down below. "Everything
looks healthy. Now, I'm going to reach up inside and
feel for your cervix." I felt her finger slide in.
Soon, that was over.

"Great," she said, "Now, I'm going to take these," she
held up something that looked like salad tongs, "and
insert them into your vagina in order to open it up so
I can get a better look."

I was a bit more relaxed since I knew she knew the
truth, and the rest of the exam was easy, other than
the discomfort. Finally, it was over.

"You're a perfectly healthy female." I smiled as I
pulled on my panties. "Have you thought anything about
birth control methods yet?"

"No," I said as I put on my bra, "I know about them,
but I haven't used any yet because I haven't had to."

"Well, there are many different things you can use. The
one that is most effective is the pill, and used in
conjunction with condoms, is the most effective mode of
birth control. If you ever want to be sexually active
in the future, even if you think you don't want to
right now, I would still recommend starting to practice
some method of birth control right now, so you don't
get taken by surprise."

"Okay, what would you say is best?"

"Like I said, the pill is most effective, used in
conjunction with a condom, though it still is the best
without the condom. It allows some degree of
spontaneity, as you take one pill daily, and don't have
to worry about it in the heat of passion. I have a
sample pack here, good for one month, and can write you
a prescription for more if you want. I know your
mother, I'm a good friend with her, so it's okayed."

"Sure," I said, "When do I have to take these?"

"Start the pack the day your period ends. Take one pill
a day at approximately the same time each day, and when
the pack runs out, start a new pack right away."

By the time I was dressed, she had finished the
prescription. I took it and went out to meet my mom. I
told her I needed to get it filled and showed it to

"Birth control pills, huh?"

"Yes. She said I should probably be on them, just in
case I ever decide to be sexually active."

"Okay, let's go get them, then."


I made sure I took my pills every day, quite regularly.
After two months, I noticed the muscles on my chest
felt a little sore. I asked my mom about it. "Well, the
birth control pills are basically female hormones.
What's happening is that you're starting to develop
breasts as a consequence. I'd say it's time to stop
stuffing your training bra. The only thing is that you
should wear a training bra every day now, no matter
what clothes you wear."

I asked my mom if I should stop taking them. "Do you
want to?" she asked me.

"Well, I don't want to be a woman for the rest of my
life. I just enjoy it every so often."

"There's one last thing about being a woman that I
didn't have you do. Everything else is basically the
annoying day to day stuff that nobody likes doing at
all. This one thing makes everything else worthwhile."

"Really? What is it? Why didn't you have me do it

When will you show me?"

"Hold on. You don't even know what I'm talking about

"I really enjoy being a woman. My period, my clothes,
everything, even being on birth control pills. Now you
tell me these are the lousy things, and one good thing
makes it all worthwhile. I don't care what it is, I
want to do it."

"Well, the reason I haven't done it before is because I

The thing I'm talking about is sex."


Later that day my mom approached me. "You know what we
were talking about earlier?"


"Do you really want to do it?"

"It sounds good."

"Let me see what I can do. Keep taking your birth
control pills for now."


Over the next two weeks I saw my breasts begin to grow
more. I was filling out an A cup on my own when my mom
came up to me again. "Are you still wanting to have
sex?" she asked.


"Well, I had a long talk with your stepfather, and he
said he would help out, if you want."

"Okay, I guess. I don't really know what to do."

"Well, what I was thinking you could do is have one
time with me coaching you, and then go a second time on
your own. Do you want to?"



That night after dinner, my mom had me douche. Then I
walked into their bedroom, and saw my stepfather and my
mom there. My mom started talking about foreplay as he
and I kissed. She had me unzip his pants and undress
him, and then started to tell me how to suck on his
dick. I complied, getting horny myself, and went
faster, doing the best I could. I was surprised when I
felt hot sperm shoot in my mouth, and stopped.

"So far, so good," my mom said, "How do you like the

"I like it."

"Then swallow, otherwise, spit it out."

I swallowed, smiling. Next, we started another round of
foreplay, and I began to suck again when I was stopped.
"This is the best part," my mom said. My stepfather
came around behind me and stuck his dick inside me. It
hurt at first, but after a few thrusts, the pain gave
way to pleasure. I soon realized I was moaning and
asking for more. Soon, I reached orgasm. Not long
after, my stepfather came inside me. "Enough for
tonight," my mom said.

I went to bed happy. I lay there with my nightgown on,
remembering the events that had transpired. My asshole
was a little sore under my diaper, but I didn't mind.

The next day my stepfather was home early from work. I
got my second time with him on my own. God, it felt


I continued my time as a girl on and off, one week out
of four, for the next year. I had now been acting the
part of a female for almost two years. After I had
learned about sex the first time and had a repeat on my
own, no more was done or said with my stepfather. I had
stopped taking birth control pills, and found my male
hormones beginning to take charge over the development
of my body.

The next thing I knew, my stepfather had a new job
halfway across the state. This would require us to move
in a few months, and I wasn't looking forward to it.
What happened is that my mother and stepfather moved
down early, and my s****r and I had to stay with my
grandparents for a couple of months until school was
finished. This didn't pose a problem with my dressing
up--my mother left specific instructions with my
s****r. What I really wondered about was my mom talking
about me finally going one way or the other once we

Fortunately, once we moved, I stayed at partial
dressing, going only the one week in four for most of
the time. I also got to dress up when I felt the urge
to, or when my parents felt it was a special enough
occasion. I soon found my wardrobe of dresses and other
women's clothes growing, soon as large as my men's
clothes. This stopped for a short time, though.

I went away to college for six months to a military
school. After finding out I truly hated the military, I
returned home. One of the talks that my parents and I
had before I came back was an attempt to make me stay
with the military, but I still left.


I had gone home to visit for Thanksgiving, and was
talking with my f****y.

"If you come back, you know that you'll have all your
old stuff back," my mom said.

"If you mean my girl clothes and stuff, that's fine, I
can deal with it," I replied.

"Well, we think a final decision needs to be made as to
which way you're going to go," my stepfather

"OK," I said, "I'll think about it."

"Well," my mom said, "I think the whole f****y should
have some say in it. We have to live with the decision
made, too."

"Sounds fair."

"Here's the way we'll do it then--each of us gets one
vote which way you go. Don't worry--you get two votes
since you're the one who has to do it," my mom

"So what it amounts to is that I go which way the vote
goes, huh?"


"And you get one, you get one," I said looking at my
parents, "and I get two. What if there's a tie?"

"Your s****r gets to vote too--she lives in this house
also," my stepfather told me.

"Fine. Any word on how the votes are going right now?"

"Yes," my mom said, "you seem to fit better in women's
clothes than in men's, and you just look and act so
much like a woman, I think that you should be one. I
vote for you being a girl."

"OK," I looked at my stepfather, "And what do you

"I always liked daughters better than sons. Also, you
know I prefer you dressed as a girl. You look more
natural in a dress, more so a girl than you look like a
man dressed in men's clothes."

"And what about my s****r? Based on what you just told
me, if she votes female, I don't have a choice."

"She hasn't decided yet," my mom said.

I talked to my s****r before I went back to the Academy
for my final few weeks. I had decided I liked my
primary gender, and wanted to keep it, and tried to
talk to my s****r to convince her of the same. She said
she hadn't made a final decision yet, but she also
liked me as a boy.


When I came home, I was greeted warmly by my f****y. My
mom informed me that a final decision would be made
that night, and I should at least get back on schedule
with my period. I complied when I got home, changing
into proper attire.

We had our f****y vote later that night. I knew my
parents would find some way of talking my s****r into
the way they wanted to vote, but it didn't faze me. I
had hated the military enough to leave it for the
situation in front of me. The vote went the way I
expected, and as such, I was not surprised by the fact
that my male clothing had been removed from my room and
hidden away before I came home.

I protested at first, but after the first week, gave up
and decided to go with it. My parents had agreed to pay
for my rent and food, as well as buying me clothes. The
only thing I had to worry about was a car, if I wanted


I spent two weeks dressed as a girl before my mom
informed me that I was due for another gynecological
exam. I didn't have a problem, and found this lady
doctor as the one before--treating me as a female,
making me undergo a full examination.

"Any irregularities with your period?" she asked.


"Are you on birth control?"

"No. I was once, but stopped."

"Have you ever been sexually active?"

"Once, and I was on birth control at the time."

"Well, we should get you back on it."

I was soon back in my full routine as a female, only
this time, it wasn't only part time. I soon found
myself growing breasts again, and found men noticing


A friend that I knew from high school was moving to our
town. We had been best friends until the point that I
moved, and he was the only person who I had trusted
enough to talk with about my dressing up. I remember
asking my mom one time if he could stay over one
weekend night at our house.

"Isn't that when you're supposed to be on your period?"

"Yes, but..."

"Does he know about it?"


"You told him?"

"Yes--he though it was a fun idea. I guess he talked
about doing the same type of thing with his mom after
he found out what I do."

"Well, I guess it's OK."

"Can he dress up when he's over here?"

"I don't know. I need to make sure it's OK with his
parents first."

"If he showed up at least part-way dressed up, would
that show you it was OK?"

"Yes. He needs to bring at least his own panties and

Then I'll know it's OK."

My friend had talked with his mom about it before, but
she only gave him one night in a dress, and never let
him have a period. My friend had no problem smuggling
out a pair of panties and a bra from his house, and
when he pulled them out of his bag to show my mom, we
giggled and ran off to get dressed. We spent all night
in our dresses, and I taught him all about having a


This friend was now attending a local college, and had
come over for a night when my parents were out of town.
We had been drinking some of my parents' alcohol when
he brought up the subject of my dressing up.

"I see you still dress up."

"I don't get much choice anymore."

"How far have you ever gone as a woman? I mean, I know
you taught me about having a period and such, but have
you ever gone farther?"

"You mean sex?"

"Well, yeah..."

"Only once. I never found a boyfriend, I guess I just
don't look that good as a woman."

"You look great," he said.

"No, I don't," I looked away.

He reached over and kissed me on the mouth. "Yes you
do," he said firmly.

I didn't say anything. I just looked at him. When he
kissed me again, I didn't hold back this time. I soon
found myself deeply kissing him, tongues inside each
other's mouths, hands slowly caressing each other. I
could feel the bulge in his crotch growing. I caressed

His hands slid under my dress and started to hook on my
panties. "No," I said, "I'm not ready for that yet." He
looked a little crestfallen. "Don't worry," I told him,
"I'll make sure this is satisfied tonight." I grabbed
his crotch.

We kissed more and more. I unbuttoned his jeans and
began fondling his erection. I stopped kissing and
smiled at him. He smiled back, and his eyes got wide as
I sank down onto my knees.

"I told you I'd satisfy you," I said, as I began to
lick the head of his cock. Soon I had the whole thing
in my mouth, slowly stroking up and down, stopping now
and then to lick the head a bit more. I speeded up as I
heard him begin to moan and soon felt him come in my
mouth. I swallowed quickly, sucking out all that I
could from his penis, finally pulling off and smiling.

We sat on the couch for a short time, hugging. Soon we
started kissing again, and I found him rock hard once
more. I moved down to his cock, sucked for a few
minutes and stopped. I stood up, looked at him and
asked him if we could go in the bedroom. He obliged,
and as we entered, I turned around and kissed him long
and hard. I felt his hands on my ass, and reached
around and grabbed them. I slid them up under my skirt
and hooked his fingers on my panties. He looked at me
in amazement. "I thought you didn't want to do that?"

"Before I wasn't ready. I'm ready now."

He slid my panties off. I moved onto the bed and he got
behind me. He was still slick from the blow job I had
started, and he pushed in easily. I gave a slight moan
as he sank in all the way, and he stopped short.

"Does it hurt?"

"No! It's the best thing I've ever felt. Fuck me,

He pumped away behind me for a few moments, and then I
felt him come deep inside me. He pulled out, and laid
down next to me. I smiled at him and winked. "Don't
worry, I'm on the pill," I said.

He laughed.


The next morning I woke up and looked around. We were
nude next to each other and I saw my clothes on the
floor. I climbed out of bed and began to dress. I had
my bra and panties on when he woke up.

"Good morning."

I sat down on the bed next to him. He looked at me and
smiled. I smiled back and reached for my dress. That
was when he asked me his question.

"Will you dress me up again? Like we did those couple
of times in high school?"

"On one condition."

"What's that?"

"Last night..."

"We can forget it if you want, I understand."

"No, it's not that. I don't remember much of it at all.
I just remember that I enjoyed it. I'll dress you up
only if we can repeat what we did last night."

He kissed me and smiled. "Of course." He looked away
and said, "If you want to, you can do it to me also, I

"Wait a minute. Who's wearing the panties here?"

"You are."

"That's all I want. Just let me be your woman."

We kissed again, long and hard. My hand worked its way
down to his penis, and found it already hard. I broke
off our kiss and began to suck him off once more. When
he finally came in my mouth, I looked up and smiled. I
opened my mouth to show him what I had in it, then shut
my mouth and swallowed. He sighed, and I laid down next
to him.

We began to kiss again once he had caught his breath,
and he was hard in only a matter of minutes. I sucked
on him for a couple of minutes before I removed my bra
and panties. He got behind me and slid it in.

This time, sex lasted longer than it had before. I
never knew just how many little orgasms his screwing my
behind could give me. When he finally came, I had not
ejaculated, but I felt as though I had come ten times.
We laid down once more.

We screwed one more time, longer still before we headed
for the shower. While washing up, his hard on enticed
me to give him one more blow job. We got out and headed
into my room to get dressed.

When he finally returned to his dorm, he had changed
back into his normal clothes, but one last kiss told me
there might still be more. There wasn't, as he found a
girlfriend who was actually a female, but I still
remember those times fondly.


Six months later, my s****r moved out. After some
protesting with my parents, I convinced them that since
my s****r no longer lived in the house the vote was a
tie. I got my original clothes back and stopped taking
the pill before anymore physiological damage could be
done. I moved out six months later, and took only my
men's clothes with me.
82% (20/5)
Categories: FetishFirst TimeTaboo
Posted by beanflik81
3 years ago    Views: 3,336
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3 years ago
Definitely one of the most bizarre stories I've read.