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ANN
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When I was a teenager, I was heavily involved in school sports. As a result
of this involvement, my hair style was normally either the old fashioned
flat top or a crew cut. But about graduation time in my senior year, the
Beatles were making their debut in the United States and longer hair was
rapidly becoming the "In Thing".
When my hair had grown to approximately 2 1/2 inches to 3 inches on top, my
mother began suggesting I get it cut. Being a typical spoiled teenager, I
ignored mom and continued to let it grow. As the hair on the top of my head
began approaching 4 inches, Mom began telling me that if I didn't get it cut
soon, she was going to put me into a skirt.
Again I ignored the warning and, once again just let it grow. I didn't have
too much to worry about because Dad had passed away a few years earlier and,
being an only child, I had Mom wrapped around my little finger, or so I
thought.
Since I had graduated, I was free for the summer and didn't have any school
schedules or anything else to worry about, all I needed to do was enjoy my
summer as a High School Grad. Besides that, my mother and I had talked about
going on a long deserved vacation that summer to get away from it all and to
celebrate my graduation.
About three or four weeks after she began making these threats, my mother
suddenly stopped. That was when I knew that I had won that round and since I
had won I would begin thinking about getting a hair cut like Mom had
requested, this time though it was on my terms, not hers. But just to drive
home the point that I had won, I thought I would go ahead and let it grow
just a bit longer.
One hot summer afternoon, about a week later, I had just finished working on
my car and was super hot and sweaty. Since I had a date later that evening,
I decided to grab an early shower then just relax and catch some sun by our
backyard pool until it was time to get ready for my date.
As I headed for the shower, Mom asked me to just leave my dirty clothes on
the floor outside the bathroom so that she could get started on the laundry.
I did as she asked without thinking too much about it. After all, the layout
of the house afforded me reasonably good cover to go from the bathroom to my
bedroom with just a towel anyway, besides, Mom had seen me before and
wouldn't be too offended if I slipped and let her catch a glimpse again. She
would just jokingly scold me about being more modest and careful in the
future.
Once finished with the shower, I returned to my room and went to the closet.
What I found was a newly installed padlock on the closet door. Extremely
puzzled, I then went to my dresser to get out a pair of swimming trunks so I
could go down and ask Mom what was going on.
I opened my underwear drawer and found six brand new pair of girl's panties,
two pair of pantyhose, a padded bra, a full length slip and a girls one
piece swim suit. All of my underwear and even my swim trunks were gone.
By now I was quite shook and quickly looked around the room. Laying on my
bed was a very pretty dress and a note. The note was to me, from my mother.
It read "A promise is a promise, now you can wear these clothes, and when
you get dressed - wear panties, bra, slip and dress, then get your new shoes
from under the bed and come down so we can talk. Your only other choice is
to go naked - Mom. P.S. Fix your hair too, Ann, we will discuss the makeup
and jewelry later."
I was totally shocked, to say the least. With my mother, once she got to a
point like this, I had learned that you don't cross her again. You just take
your licks and then regroup. Every time, in the past, when I had tried to
"one up" Mom, I would always end up losing even more ground. Besides, I had
asked for this by not heeding her earlier advice, or even extending her the
courtesy of discussing it with her, she deserved to have her fun.
I reluctantly got dressed, as instructed. I wore the dress, panties, bra,
slip and even the shoes from under the bed. The shoes were a pair of women's
pumps with about a two inch heel. I even went into Mom's room and got one of
her hair bows and some of her makeup, just to pick on her a bit and tell
her, symbolically, that she had won and that I was sorry. Maybe that would
calm her down a bit and make my sentence a bit shorter. I then went down to
the kitchen to face the music. I wasn't ready for what else I found.
I had expected to walk in and see my mother washing dishes and then sit down
at the table and listen to her complain about my hair, my overall appearance
and my obligation to look as nice as possible because of my reputation. What
I found instead, was my girlfriend, Kelly, also sitting at the table when I
walked in. I was completely immobilized, looking at the two of them and them
staring back at me, trying to figure out how I was going to handle this one
with Kelly, but it was too late, I had been seen.
I just stood there, frozen in the doorway, until Mom finally said, "Have a
seat, Ann". As I sat down, Kelly said "We have a surprise for you, Ann, and
all you have to do is just sit there and relax, listen and watch, OK?" Kelly
also calling me Ann added to my feelings of doom and total helplessness, so
I just sat there as I had been instructed.
As I sat down, not knowing what to expect next, Kelly got up and began
working with my hair, complimenting me on my "Pretty Hair Bow" and my choice
of lipstick color. As Kelly worked on my hair, Mom began applying more
makeup to my face, and then added nail polish, as she continued her
conversation with Kelly. To this day I still don't remember what they were
talking about. Not once did Mom mention my hair. She was acting in a manner
I had never seen before, almost as if I had actually been born a girl and
this were a common occurrence.
I sat there, totally humiliated and still in a state of shock, letting them
do these things to me, when I was brought rudely back to reality by a
comment from my mother.
She said, "Ann, I hope you enjoy these clothes because you are going to be
wearing them until you decide to become my son again. It's too late today to
get your hair cut, and since today is Saturday and the Barber Shop is closed
on Sunday, it looks like you are going to be spending a little time with me
as my daughter." Kelly quickly added, "And my girlfriend too", as she began
stuffing pillow filling into my bra to give me a little more feminine shape.
As the time passed, I began to get more comfortable with my new attire and
was even beginning to really enjoy the feel of it when Kelly suddenly asked
if I would take her to the Drive in tonight. Before I could even think of a
response, Mom said - "I'm sure she would love to, wouldn't you Ann?" All I
could do was nod my head in agreement, wondering just how I was going to
pull this one off.
As I started to get up from the table, Kelly stopped me and said, "Not just
yet, Ann, we have one more thing to do first." With that, Kelly stood on
side of me and Mom on the other, they each grabbed an earlobe and pinched,
then "OUCH" they each pushed a needle though my ear lobe and installed a
pair of pierced earrings.
The two of them then spent the next couple of hours teaching me how to act
feminine and appear as ladylike as possible, so I wouldn't get caught at the
drive in. As evening approached, a cool breeze began to stir and I finally
ventured to the back yard with Kelly. I was amazed at how neat and even how
sexy it felt to have a cool breeze blowing up my dress, I was beginning to
get into this female thing and was enjoying every minute of it, now.
When we went back into the house, to get ready for our date, Mom presented
me with my own purse, stocked with cosmetics, my wallet and my keys.
At the drive in, things were going without a hitch, until I got to the point
that I needed to go to the restroom, quickly. I didn't know what to do until
Kelly finally suggested that I go ahead and use the ladies room, which I
did, alone. (I was too embarrassed to have Kelly go with me.)
Once I got back to the car, Kelly was all over me, like an octopus. She said
that she had decided to take advantage of this situation and show me, first
hand, what it was like to be on the receiving end for a change, and how much
work it was to keep the dress down. I fought her off with only token
resistance and soon had her panties and bra off, then I allowed her to win
the match and get mine off too. With that we got into one really wild love
scene of our own. We had to have looked like a couple of lesbians, both of
us wearing nearly identical dresses, but I didn't care.
What I did learn to appreciate though, was the additional cover that we were
able to get from the material of the dresses, this realization came at about
the same time I began to exceed my control limits and Kelly began exceeding
hers. Damn this dress was handy. I had never gotten that far with Kelly
before, no matter what I tried. But now, with the dress, I had managed to go
all the way. After we cooled down a bit, I took Kelly home then I went home
and went to bed. It had been one hell of a day.
As I walked into my bedroom, I saw that Mom had placed a pair of Baby Doll
pajamas on the bed for me to wear along with another note. This note read,
"Ann, after you get into your pajamas, come down for some hot chocolate so
we can talk - Mom". I eagerly changed then went down to the kitchen.
As we sat there talking, Mom began explaining how to properly remove all of
the makeup and how to clean my ears, where they had been pierced, to prevent
infection. I was also informed that, as long as I was "Ann", I was required
to sit every time I had to go to the toilet, as Mom put it, "If you are
going to look like a girl, you're going to have to act like a girl at all
times, and in every way imaginable, otherwise you are going to blow your
cover by accident."
With that, she presented me with a package of feminine napkins and
instructed me in how to wear them. I was to wear them for the next two day,
both as a lesson on what women have to deal with, as well as a reminder to
act like a lady, or until I had had enough and decided to get my hair cut.
With this big bulge between my legs, who could forget. At least she hadn't
chosen tampons as part of the lesson, although I have secretly experimented
with tampons since and have had some interesting reactions which have not
been altogether unpleasant.
The next morning when I woke up, I had this strange feeling that I had been
having one hell of a dream, and a very sexy one to boot. Then I looked down
at the foot of the bed and saw that Mom had put out another dress for me to
wear, plus I found too, that I was, in fact, wearing girls pajamas.
I quickly and eagerly put on the new outfit, very carefully reapplying my
makeup and cleaned my ears., as Mom had instructed me the night before, then
I attached one of the napkins to the inside of my panties and went down to
breakfast. As I helped Mom finish washing the breakfast dishes, Kelly came
over and we all sat down and talked. That was when I learned how this whole
thing came about.
I found that Kelly had been the prime instigator of this setup ever since I
had told her about Mom's threats. She had approached Mom and convinced her
that it would be a lot of fun. Then, as the planning proceeded, Mom began to
actually get into the swing of things and began dreaming about me being born
a daughter instead of a son, she had decided to find out for herself what it
would have been like. A little while later, Mom went to the store and Kelly
and I decided to go swimming. We both went to my room to change, after all,
now it was just us girls.
I damned near lost control of myself inside my new swim suit when I turned
around to see Kelly standing there watching. As I glanced down at her
crotch, I could see that she too had a similar reaction to seeing me in my
new suit.
I found out later, that Kelly had been experiencing occasional feelings that
she thinks are "lesbian in nature" and that this way, she could somewhat
release some of those urges without actually doing it with another girl. The
idea of doing it with another, genetic girl, seemed to really scare her, I
have never found out why, unless it was the stigma that would go along with
the title. I was just happy to have been there to help her through that
period. Oh Boy, was I happy, I was totally ecstatic about being there to
help her out. I have also developed a very valued insight into the problems
women face as a result of this experience.
Since it was summer, and I didn't have to worry too much about school or any
of my friends coming over, I decided then and there to spend the next two
weeks as Ann. I was having the time of my life, and Mom and Kelly seemed to
be enjoying it too, it would be a shame to end it too soon, for their sakes.
Besides, I was finally getting all the sex I wanted with Kelly and I wasn't
ready to give that up now.
It finally happened, the two week time limits I had set had come to an end
and it was time for me to get the hair cut. Mom and Kelly had other plans
though, they had refused to let me have my boy clothes back until after my
hair had been cut. They bluntly refused to give in, which told me that they
were enjoying this thing almost as much as I was.
I was also afraid of the reactions I would get from the guys at the barber
shop, with me walking in wearing a dress. I was really getting into a panic
over the thought of going that route. As a result, the two weeks extended
into seven. Mom and Kelly finally gave in and agreed to give me a hair cut
at home, but I still wasn't allowed to have my other clothes back until
after it was done.
Mom, Kelly and Ann still spend a lot of time together, but now Ann keeps her
natural hair short and wears a wig. Even though Kelly and I have a somewhat
guarded sex life together, Kelly and Ann definitely have the hots for each
other and do almost everything one can imagine on a regular basis. In a
couple of months, Kelly and I are getting married. We have already made
arrangements for Ann to live with us on a somewhat permanent basis.