Wendi's Beginning
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Douglas's Story In the Beginning
I not gay or have any desire to change my sex. I'm a happily married
man who discovers I like to play dress up and play out some pretty
weird sex fantasies.
I have been keeping my little deviate behavior a secret for almost 40
years. Like most it started as a curiosity, I was confused growing up
being raised in a dominate female home with a spinster nanny who found
unruly male behavior corrected by a stern lectures on proper behavior
and a sound spankings. Being forced to apologize for my unruly
behavior. Mrs. Brown was very strict and demanding. She made sure I
had housekeeping chores. She often would made sure I wore an apron so
I wouldn't soil my clothes. One of my many duties was folding the
laundry and since I was the only male in the house I spent my time
folding my mothers and Mrs. Browns lingerie and other clothes.
My Mother was an executive with a large cosmetics company and was on
the road 15 to 20 days out of the month. She was always dressed
business like and her job was very demanding of her time. She never
objected to Mrs. Brown's methods of correcting a young boys behavior
which meant I had no alias which made me obedient and submissive to
both women.
My best friend was a girl named Carol Baker. She was our nabour, she
always intrigued me because she was what you'd call a girly girl. She
always wore dresses and petticoats. Her mother also wore dresses and
nylons high heels everyday, she reminded me of Donna Reed the perfect
housewife and mother who kept her daughter as a sweet innocent little
girl always clean and proper and she was so shy and demure. We would
play on the swings or playhouse it was never rough and tumble like
kids often do. I found myself going over to play and somewhat jealous
and envious of her and her mother and often wondered what it would be
like to trade places with her. Her father wasn't what I'd call a he-
man. Mr. Baker would do what I thought was the normal things fathers
did like the what I did cleaned and did laundry and did as he was
told. I remember once I got up to go the bathroom and looked outside
to see Mrs. Baker putting out the garbage. It was strange because she
hid behind the hedge when a car pasted by and almost ran back to the
house. I didn't think much about it and went back to bed.
I knew something was strange one summer's night when I convinced my
mother I could camp in the back yard. My friend Johnny and I where
sleeping out when nature called. I crawled out to go pee in the
bushes. I saw the Bakers light on and snuck over to peek in, I saw
Mrs. Baker sitting on the chair, she had a wooden spoon in her hand
and Mr. Baker came into view wearing a girls shorty nightgown and I
could see he had on girls panties too and he took the position I had
taken so many times with Mrs. Brown. Over her lap and was spanked I
was shocked even when a boy grows up he still can get away from being
spanked. As for the nightie and panties I really never gave it much
thought.
Some of the older boys at school teased me and called me a mommies boy
and a sissy because of the way acted and seemed to fit in with the
girls better then the boys. What did I know I was 7 years old and
didn't know any better.
I soon out grew of my “sissy” stage and started to grow and was soon
6' 2”and an athletic 155lbs. Since I would run away from the bullies
at school I became very quick and had set the city record in track and
field well in my senior years of elementary school. I was still
popular with the girls because I was understanding and caring and
someone they could confide in, but now the boys had a healthy respect
for me as well.
It was the summer before high school. I was 14yrs old. We had moved to
a new house and I was exploring the basement of the house moving some
things around and I discovered a box of my mothers the top read
younger clothes. I opened it discovered lacy panties and bras, fancy
slips and garter belts, nylons and some very sensuous dresses.
I sort of froze in time staring at these clothes. Now I had seen my
mother in lingerie and had seen girls at school in dresses and never
thought twice about it.So why was I staring into this box with an over
whelming desire to put on a pair of baby pink transparent lace trimmed
panties with two little bows on each hip. I actually wanted to try
them on and see what I looked like wearing panties. I shook my head,
thinking you faggot, what are you gay or something, I closed the box
up and put it with the stuff being sent to the Salvation Army.
That night I couldn't really sleep thinking of what if I had put on
those panties and my penis fell off and I sprouted breasts after all
these where girls clothes and if I wore them you'd become one. Why did
I wanted to do this? Why would I ever want to wear women's panties?
Was I crazy, Is this what happens to boys when they reach puberty they
want to wear girls clothes like Mr. Baker did or was I gay did I want
to just coming out of the closet maybe I had a deep seeded desire to
become a girl. What the hell did I know I was 14 and didn't know
anything about sex or sexuality? I just knew I wanted to wear those
panties and see what it felt like.
The next day the Salvation army truck pulled up and I was told to load
up the boxes to be shipped off, but for some reason I didn't put mom's
box of clothes on the truck and hid the box and then managed to hide
it into my bedroom closet.
Mom had left that morning on a business trip and that night after Mrs.
Brown had gone to bed. I opened my closet and opened the box again and
lifted the pink lacey panties out of it. Breathing deeply I told
myself No one will know I tried on panties. It will only be once then
it will be over done and I will get rid of the box of clothes.
I was in my shorts only and slipped them off, figured out which was
the front and the back and stepped into them. I was shaking as I
pulled them up my legs passed the knees and over my hips. I recall
thinking do girls get same feeling when they put on their panties that
I felt putting on these panties. Wow they felt different, slippery,
soft filmy, dainty not like my cotton shorts. I looked in the mirror
and gave a sigh of relief, I hadn't magically grown breasts and my
penis didn't fell off. Actually my penis was somewhat engorged I sort
of giggled and thought this was kind of wild. I ran my hand over my
pantied cover bottom and over my growing penis. I felt nice and
strangely stimulating. Did girls get this hot and horny wearing silky
lacey things like this, did they get these same feelings of wonder and
excitement. Wow what a feeling, I hadn't realize how turned on I was
and then it happened.
I felt strangely light headed and then my balls seemed like they
exploded. My penis started to squirt a white stream of liquid out the
end of it, over and over what saw happening. My God was my penis
falling off and did my balls explode. My chest was heaving my god I
was sprouting tits. I braced myself on my dresser and was weak in the
knees, I wasn't sure what was happening I had never experienced
anything like it as wave after wave made me whimper and moan my eyes
closed until my waves of pleasure pasted. I opened my eyes I was
sweating breathing like I just ran the four minute mile I felt
something running down my leg and looked in the mirror to see a large
wet area with white liquid oozing out of the leg openings of the
panties. My god! I reached down my penis and balls still there! no
breasts I was still me a dude.
I heard Mr. Brown walking down the hall. I pushed the box in the
closet and jumped under the covers as she opened the door. She looked
in why aren't you asleep , its very late. I told her I just had a bad
dream and woke up. She walked over to the bed and I was so afraid she
would pull the covers back and discover me in pink panties with this
white liquid all over my legs. I knew she'd scold and spank me for
wearing girls panties.
She would surly make me wear them and more girls clothes as punishment
for doing this. I was so relieved when she just pulled my covers up
and told me to go to sleep.
After she left I sighed again and pulled back the covers to realize I
was hard again. I was so turned on by the thought of almost being
caught wearing girls panties I was ready to squirt again.
I spent another night tossing and turning, this time dreaming about
being dressed and caught wondering what would happen to me. I woke up
with a raging hard on still I the pink lacey panties crusty with my
dried cum. I knew I wouldn't be thowing out the box of clothes anytime
soon.
Chapter 2
I spent my summer vacation trying on all of the things in the box. I
figuring how a bra worked and nylons, garter belts . I became more
aware of girls and their clothes and manners and how they walked ,
talked and moved in dresses and heels and all. I also had convinced
myself I was the only little perverted teenage boy who has ever worn
girls clothes. I would go and visit Carol and since we had moved I had
to sleep over. Many times I got a chance to sneak a pair of Carol's or
Mrs. Bakers panties and masturbate in them. I was now very jealous of
Carol's wardrobe and longed to try some of her dresses on.
In August I was in a book store shopping for school supplies and saw
stack of used books and magazines. I asked the clerk about them and
she told me they where to be trashed and to be recycled and if I saw
something to help myself . Well one book did interest me it was called
Variations by Penthouse but I just couldn't ask for it so I told her
I'd like the comics and she said I could have them if I toke the rest
of the books and magazines out the back to the dumpster. I agreed and
while dumping them I scooped the book I really wanted.
I hid it my room and waited until I knew it was safe, I told mom and
Mrs. Brown I was going to do some reading for my choices for high
school courses and went to my room. I opened the cover and read the
index bondage and discipline, S&M , transvestites, adult babies,
threesomes, gay sex. It was all there all the abnormal sexual behavior
I had heard about in the locker rooms and other places.
It was strange, my thoughts were strange, I actually wanted to get all
dressed up in a pretty dress and lingerie to read this book, but
fought the urge just incase someone walked in.
I flipped to transvestites and read the first letter, it was about a
guy who dressed like a woman to attract men to have sex with. Was that
what I wanted to become some faggot, dressing up like a girl and have
sex with men? I read the next letter about a guy who lost his job and
his wife forced him to dress like a girl and turned him into her maid.
Wow! Forced to be a woman's maid dressed like one and treated like
one. I continued to read more forced womanhood , being dressed and
spanked and made to act like a girl . Amazing bondage and discipline
forced to obey… I didn't like the stories on S&M or gay sex but turned
my attention to the chapter on adult babies.
I could believe what I was reading , this woman complained her husband
couldn't satisfy her sexual desires so she dressed her husband in
diapers and lacey plastic panties a dress and bonnet locked him a
stroller and paraded him in front of his friends and family until he
was completely turned into what she wanted and then started having
sex with his best friend well he had watch from his stroller with a
pacifier in his mouth.
This was twisted and totally weird and I was so turned on reading this
stuff , I just had to masturbate. I went to bed with all these strange
things running through my head and I was stiff all night picturing
myself in all the situations I had read about. My new dress up games
where me being forced to be a baby girl, then forced to be girly girl
and finally a woman.
My best friend in the whole world at 14 was Carol we could talk about
everything and anything but not this. Her mother still kept her
dressed like a girly girl and was an out cast by most of the girls
from school and told me she only wanted to be a normal teenage girl
for high school. I knew we could convince her mom to give her some
space and develop into a normal teenage girl.
Since we had moved we didn't see each other to often and I'd spend a
week-end at her place and she'd come stay with me for a weekend. It
was one of these visits Carol and I convinced her mother that Carol
need to upgrade her wardrobe to something more fitting a high school
girl and we went shopping , I tried my best to feel out of place in
woman's shops, but secretly loved it . After Carol got her new
wardrobe. Carol and I boxed up her girly girl fussy dresses and
petticoats and all. I commented on how pretty she looked in her old
dresses, she started to tease and held up some of her dresses to me,
telling me what a pretty girl I was and how the colour brought out my
eyes. I pushed the dresses away and tried to appear embarrassed and
humiliated by her comments but secretly wanted her to order me to put
on her old clothes and tell her I was a sissy and a girl.
Her mom said she felt bad sending these beautiful clothes off to some
thrift shop, I told her some other lucky little girl would get to wear
these pretty dresses and things. She agreed with me and said she'd
drop them off on Monday. I was heading home Sunday evening and told
Mrs. Baker I could drop the boxes of stuff off at the thrift store for
her since it was closer for me. We put the boxes in my mothers car and
drove off. I put the boxes in the basement at home and told my mother
I'd drop them off the next day.
Mom was packed and heading out of town for a few days. Mrs. Brown said
she had to do some shopping. I was told the lawn was to be cut and the
gardens watered laundry was to be hung out and the dishes from
breakfast needed to be done. I stood there fantasizing I was in a
maids uniform and curtseying to the women. Mom told Mrs. Brown she'd
drop her off at the mall. I waved good-bye and made a mad dash to the
basement and the boxes of Carol's old clothes.
I found the one I wanted to try on the yellow satin and white lace
with the white petticoats, it would take Mrs. Brown at least 2 hrs to
shop and walk back to the house. I put the dishes in the sink to soak,
tossed in a load of laundry and laid out the lingerie and dress on my
bed to put on. I was so excited and didn't waste time, white full
satiny panties with lace trim a waist nipper and nylons,a training bra
with enough padding to hint girly breasts the petticoats and finally
the dress.
Oh my !!!!! I looked at the girl in the mirror bobbed a curtsey and
twirled. Shoes, I needed shoes, I raced to mom's room her yellow
stiletto's and her blonde curly wig she wore last Halloween. Perfect
looking at myself I looked every bit a girl a little girl dressed for
a party. I was lost in fantasy of girlhood as I twirled and minced
about unaware of the time.
Hello, Douglas! An amused Carol stood in the doorway. I figured you'd
choose the yellow satin, you seemed very embarrassed when I held it up
to you. But your bulge in your pants told me you like it more then you
let on and did you really think I didn't know you would steal my
panties when you stayed over. I turned red faced with humiliation Its
alright Carol said I knew you had a thing for my clothes and knew you
wouldn't give them away but try them on so I came over to see you and
explain that it was alright if you wanted to. We started to laugh, you
actually do look very cute and girly in my old dress. We started to
talk about my dressing and acting out fantasies until Mrs. Brown came
home and Carol ran interference until I could change.
Carol helped me clean up the house and we went to the mall in the
afternoon and continued to discuss my little diversion and like always
I told her everything knowing she'd never tell.