The Orchid The Storyteller
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Teddy?s Story free porn video
Teddy's Story
In which a medical condition causes Teddy to develop breasts and begin
dressing as a girl - with his mother's help, of course.
OK. Before I talk about my current situation, let me back up a little and
give you a little history.
Things were pretty much "normal" with me till I was about 11 or 12 years
old, or so. I had gotten a set of weights the previous Christmas and had
begun to exercise every other day. I was at that stage where boys became
more aware of their bodies and the opposite sex. Clearly not all of us
developed at the same rate and I wanted to make sure that I didn't stay
one of the "skinny ones." At first the weightlifting didn't seem to make
much difference and after about six months I was thinking about quitting.
Shortly after that, while my arms hadn't changed, my chest seemed to be a
little fuller. "Great" I thought, and increased the duration and
intensity of my workouts.
But after several more months, it became apparent that what I thought was
happening, in fact wasn't happening. While my chest had gotten a little
fuller, it now appeared not to be the muscles I had thought I was
developing. In particular, the area around my nipples seemed to be
getting thicker and softer as if I was developing a layer of fat there. I
wasn't sure whether the exercise was causing this but I was startled by
the development and decided to break off the daily exercises.
Over the next several months the development of my chest continued. In
addition to becoming fuller my nipples had grown larger and turned a
lighter shade of pink instead of the flat brown "boy's nipples" that they
had been a year or so ago. As I examined myself in the mirror, it almost
looked as though I was developing two small breasts. During my yearly
pre-school physical examination, the doctor commented that it was not
unusual for boys to develop slightly enlarged breasts as they entered
puberty and basically told me not to worry about it as they would
eventually return to normal. And after he mentioned it, I checked out
some of the other guys during gym classes and sure enough, some of them
even had nipples and breasts larger than mine.
By the following summer though, my breasts hadn't shrunk any and had
continued to increase in size. They now stuck out maybe an inch or so
from my chest and were quite noticeable. I got through that summer by
wearing large floppy shirts and not undressing in front of anyone else.
My parents couldn't understand why I was avoiding the community swimming
pool that summer and I really didn't want to confide in them.
At my next physical exam the doctor expressed some concern as to the size
of my breasts and scheduled a conference with my parents. He basically
told us that while all my other areas of development were normal, that he
was concerned about the size of my breasts, and that if they continued to
enlarge, that we might want to consider surgery to reduce their size.
What he didn't realize what that my parents' religion forbids any kind of
medical intervention such as surgery so that suggestion went over like a
lead balloon. He did agree to write a note to the school so that I'd be
excused from gym class.
I talked it over with my parents later that week and was told that I was
"In God's hands" and that his will, whatever it was, would be done. In
short, I had to "suck it in" and live with what was happening to my body.
While my parents could be OK, I have to admit that they could be really
annoying at times. Like, our house has three bedrooms. My parents have
one, of course. And my younger brother Jimmy and I share one. And the
third is for my older sister Annie. Now that wouldn't be so bad but Annie
is, like, eight years older than I am, and she's finished college and
living in Los Angeles and working for some software company. But do you
think that my parents will let me move into her bedroom so that I can
have a little privacy? Oh, hardly. Annie's bedroom, and all of her
clothes and stuff have to be left just as they were when she moved out
three years ago when she graduated from college. Mom is like, "Well,
she's planning on coming home for Christmas this year, and I know that
she'd like to sleep in her own bedroom." And I'm thinking, "Mom, Annie
hasn't been home for two years. And the only place I can get a little
privacy to jerk off is in the shower in the morning?" But of course I
didn't say that.
Over the next several years, my breasts continued to enlarge. I had seen
pictures of girl's breasts (my parents never did learn that I had a
pretty good collection of girlie magazines out in the garage) and while
most of the breasts that I had seen (at least for the younger girls)
seemed to "stick out" from their chests, kind of like "cones" or
something, my breasts seemed to sag more. This didn't bother me as it
allowed me to keep my "problem" hidden by avoiding tight-fitting shirts
and sweaters. I won't say that I had a really active sex life as my only
partner was my right hand but I did date several girls in high school -
just had to be careful during the make out sessions.
So anyway, that's my history. And that brings me up to last week - which
was in the middle of the summer between my Junior and Senior years. My
breasts were very large by this time. I'm not sure but I'm guessing that
they were a "C" or maybe a "D" cup. And they sagged down about six inches
on my chest. My nipples are large and pink - and very sensitive (but
that's another story). After initially being very supportive, I think
that my parents are trying to pretend that I don't have a problem and
that everything is normal on the home front. The subject of my breasts is
never discussed and any of my clothes that they buy seem designed to hide
the shape of my body as much as possible.
I've got to admit to having mixed feelings about the situation. As a
teenage boy it's really nice to be able to fit in with your group of
friends - but that can be tough in my case because I have to be very
careful to keep my body hidden. On the other hand, it may seem strange
but the feeling of the weight of my breasts and the way they rub my
stomach as they swing back and forth as I walk along is very pleasurable.
And did I mention how sensitive my nipples are? I can make myself come
just by playing with my breasts and gently massaging my nipples.
Things came to a head last week when we were on vacation at the beach. It
was one of the hottest days of the year and there I was with a heavy
sweatshirt covering up the upper half of my body. Sure I could wade in
the ocean but I couldn't go for a swim as that would make the wet
sweatshirt cling to my body and expose the breasts that lurked beneath
it. So my younger brother and I are walking along the boardwalk, and I'm
sweating like a pig in my sweatshirt, and I'm thinking: "Is that what the
rest of my life is going to be like? Spending all my time trying to keep
my body hidden from the world?"
"Oh, fuck this shit!" I loudly said and pulled off my sweatshirt and
threw it down on the ground as I kept walking down the boardwalk. But now
my two large, soft white breasts were fully exposed for the world to see.
Hell, if girls and women can go topless why can't I? Well of course their
situation is a little different and if I had expected to receive some
attention, I wasn't disappointed. As I walked along people turned and
stared at me, and I don't even want to repeat some of the comments they
made. But you know? I DON'T GIVE A FUCK! I am the way I am and I don't
care what other people think.
But boy did the shit hit the fan when I got back to the apartment my
folks had rented. I walked in the door, "topless," and my father's jaw
dropped and after an initial gasp my mother screamed at me, "You can't
walk around like that! Cover yourself up!" Well, things kind of went
downhill from there after I yelled back at her that I was " . . . . .
tired of fucking walking around with a sweatshirt on in the middle of
summer just so folks can't see my tits." And then my dad chimed in and
started yelling at me. And Jimmy's over in the corner laughing his
fucking head off. So anyway, that was the end of that vacation.
At home the next day, I'd decided that I wasn't going to let my folks run
my life any longer so when I got ready to go out to mow the lawn in mid-
morning, I just had on a pair of old khaki shorts, and a pair of beat up
jogging shoes. I was almost out the front door when mom asked me to wait
a minute. At least she wasn't screaming at me so I hesitated and heard
her say, "You should really cover up a little. Let's go upstairs and see
what we can find." I thought she was going to go into my bedroom but she
led me into Annie's bedroom, when over to the dresser and began rummaging
around in one of the drawers. "Here," she said, "This should fit you,"
and handed me some thing in a dark fabric. As I examined it I realized
that it was one of Annie's tube tops. Well, I wasn't wild about putting
on a piece of Annie's clothing but I was tired of arguing with Mom so I
struggled into it. I guess that Annie was, well, "smaller" that I was as
it was pretty tight on me. But it did both compress and support my
breasts, and the dark color helped to make them less noticeable. So you
could still tell that I had "something" on my chest, but I guess it was
better than showing everything off to the world, so I wore it as I mowed
the lawn that morning. And actually, other than being a little tight it
really wasn't that uncomfortable so I kept it on the rest of the day.
After supper the next day, I had a negotiating session with my parents. I
kind of hinted that I'd keep myself "covered up" but like, I was going to
be a Senior in high school and I thought that I should really have a room
of my own, and in return for my dressing more discreetly they had to let
me move into Annie's old bedroom. Of course Jimmy's like, "Oh wow! So
I'll have a room of my own now?" And of course that didn't hurt my
argument. So mom wasn't too wild about the idea, but dad just shrugged
his shoulders, so she reluctantly agreed. Man, I was so happy to get a
room of my own that I just grabbed all the clothing from my old bedroom,
tossed it in a pile on the floor of my new bedroom and slept in Annie's
bed, oops - my bed now - that night. Oh, Mom did have one condition, she
didn't want to throw Annie's old clothes out or redecorate her old
bedroom for me, but I figured that was a small price to pay for getting a
bedroom of my own. "Man, this is so great," I thought as I snuggled down
into the scented silken sheets that night, "A room of my own at last!"
When I awoke the next morning, I got out of bed and began rooting through
the pile of my clothes on the floor, trying to decide what to wear that
day. The problem was that my clothes were all wrinkled from lying on the
floor, and dirty clothes were mixed in with the clean ones, and I found
myself thinking, "Wonder if any of Annie's clothes would fit me - at
least they're better organized and clean." So I looked through her closet
and found a pair of white shorts and a tan blouse that looked like they
would fit me pretty well. "As long as I'm doing this," I thought, "I
might as well go all the way," and I picked out a pair of Annie's white
panties. As I looked at myself in the mirror, I noticed that my breasts
were visible through the thin blouse and I knew that mom wouldn't like
that. I was going to wear one of Annie's bras but I couldn't find one
that was a comfortable fit - I think she must have been only a B-cup - so
I just put on one of her light colored tube tops under the blouse - and
that did a fairly good job of minimizing and hiding my breasts. "Why
Teddy, you look so nice," Mom said as I walked into the kitchen for
breakfast. I just blushed.
Well, for the first couple of days I was pretty uncomfortable to be
wearing girl's clothing but after awhile it just got to seem more and
more natural to me and within a couple of weeks, I really had no desire
to wear my old clothing and was enjoying going through Annie's closets
and dresser and trying on her different outfits. Yeah, well, except for
her bras, that is. Finally I was getting tired of wearing tube tops most
of the time and wanted to try a real bra. So I got up my courage and
asked mom if she'd mind buying a couple of bras for me. She had me take
off the blouse that I was wearing (I was just planning on staying in the
house that day and hadn't put on a tube top), and she got her tape
measure and made several measurements over and under my breasts. Man, did
it feel really strange to feel her hands on them as she measured me -
that was the first time that anyone else had ever touched them - well,
except for the doctor and school nurse and those guys don't really count.
So anyway, she figured out that I needed a size 38 with a D-cup - and so
that's what she bought me. Man, did I struggle the first couple of times
I put on those bras, and Mom's helping me arrange the cups and she's
touching my breasts as she helped me "adjust" things, and I'm looking in
the mirror and getting all turned on by the sight of me wearing a bra and
the feel or her hands on my breasts. Lucking I had put on a really baggy
pair of shorts that morning so she couldn't see my erection.
A couple of weeks before school started, mom and dad decided to take a
long weekend and go to the beach one more time. When I heard their plans,
I was, like, "Oh come on. You know what happened last time. And I'm not
going to wear a sweatshirt again. Maybe, like, I could stay here and just
spend the weekend with a friend?" Mom got this little smile on her face
and handed me a small package and said that she thought that this would,
". . . . . solve the problem." I opened the package and found that she
had bought me - TWO BIKINI BATHING SUITS! Oh wow, I ran up to my bedroom
to try them on. Gosh did I look great in them - the tops really supported
my breasts and lifted them up and emphasized their size and revealed all
this cleavage. The only problem was that the bottom just barely covered
up my dick and as I looked at myself in the mirror I got turned on and
got this big erection and my dick popped out of the bikini bottom and of
course it wouldn't be too cool to be walking along the beach with my dick
danging out, so I managed to get it, like, stuffed back in the bikini
bottom and tucked back between my legs so that you could hardly tell I
had anything "down there" at all.
The weekend at the beach was a lot of fun. And a couple of times I caught
guys looking at me to "check me out" and that was so funny that I giggled
a little.
The first couple of weeks at school were tough. I was getting a lot of
stares and comments about the girl's clothing that I was wearing. But
after awhile things quieted down and I was pretty much accepted by the
other kids. It was really funny, though, to be talking to one of my
friends and realize that he wasn't talking to my face, he was talking to
my tits.
Well, other than the clothes, Annie had left behind a bunch of jewelry in
her bedroom (now "my" bedroom). I was looking at it and wondering whether
it would be okay with mom if I tried on a couple of the smaller pieces.
When I broached the subject with mom she said that she didn't think that
Annie would mind - and mom even took me to the mall to get my ears
pierced so that I could wear some of Annie's earrings. While we were
there she suggested that she take me to her beauty parlor to have
something done with my hair. I had to admit that my hair was just this
kind of shaggy boy's cut and I really didn't like it anymore, and luckily
the beauty parlor wasn't busy that day and they could work me in. Several
hours later, my dirty blonde hair had been changed to a dark brown, and
styled with a part on the left that let it sweep down over the right side
of my face and partially covering my right eye. Mom bought me a pair of
dark sunglasses that rally went well with my new hairstyle.
Jimmy was teasing me about my hair and clothes several weeks later,
"Teddy looks like a girl with his clothes and hair. Can I kiss the little
girlie," and he made kissing noises at me. That made me so mad that I
slapped the little brat, and of course Jimmy ran crying to mom and she
got mad and sent me up to my bedroom for the rest of the afternoon. While
I was there I kept looking at myself in the mirror. I really did like my
new hairstyle, and I tried on several different pairs of earrings before
I found one that I liked, but there was still something "wrong" with my
look. I guess that it was a combination of my heavy eyebrows, short
eyelashes, and lack of any makeup at all. Now Annie had left behind a
pretty good assortment of makeup but, like, most of it was dried out or
all caked and unusable. I did find a set of tweezers and managed to thin
my eyebrows so that they looked more girlish.
A couple of weeks after that, mom suggested that since Jimmy and dad were
going on a scout camping trip that weekend, that she and I could spend
some time together. "Yeah mom, whatever," I thought. Right after Jimmy
and Dad left on Friday night, mom led me into the bathroom and had me
shower and then she showed me how to shave the hair from my legs and
armpits without nicking myself too badly. First thing on Saturday, she
showed me how to manicure my fingernails, and then she helped me apply
some extensions to make them, like, over an inch long. And then she
painted them with bright red fingernail polish, and used the same polish
on my toenails. Then she had me put on a pair of Annie's sandals with
three inch spike heels and practice walking around in them - man, was
that a challenge! Later in the morning my makeup lessons began and
continued into the afternoon. Oh man, when supper time came I couldn't
believe how beautiful I looked with the eye shadow and mascara making my
eyes look huge and luminous and the bright red lipstick that matched my
fingernails.
Finally she dabbed on a little perfume and then dressed me in a revealing
hot pink miniskirt over my black lace pantyhose, and a tight, lowcut
blouse over my pushup bra. Wow, as I looked at myself in the mirror I was
getting really turned on and all of a sudden I had this big erection
tenting out the front of my miniskirt - and didn't that really spoil the
look? I didn't want to take a chance on breaking off one of my
fingernails so mom reached down into my panties and grabbed my shaft and
stroked me till I ejaculated. As I softened and shrank back to normal
size, she tucked me back between my legs so that nothing was showing. As
I looked at myself in the mirror, I couldn't believe how beautiful I had
become! I was so happy that I cried a little, and of course that made my
mascara run, and she had to reapply it. Finally she said, "Okay, you look
wonderful. Let's go out to supper and I'll enjoy watching my beautiful
daughter turn the boy's heads," as she led me to the car. "Oh, this is
going to be so much fun," I squealed and giggled.
Maddy
- 17.07.2022
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