Crossdressing gone bad
story by Anonymous
I am a heterosexual male who has crossdressed since childhood. I started
by wearing my mothers pantyhose and have progressed slowly over the years.
Now that I am married I am able to dress routinely, but only for short times
while my wife is out. These sessions usually hold me over until my wife or I go out of town. When this happens I am able to fully transform into
a semi-passable woman. I do not go out publicly while dressed, but have
ventured out for a late night drive or walk on occasion. Over the years
I have been very cautious about dressing and have never had any problems.
However, that all changed on a recent business trip.
I arrived in North Carolina for a week long trip and could barely wait to
get to the hotel, drop my bags, and start shopping for my female items.
I never take anything home from trips, so I must buy everything every time
I travel. I started my shopping adventure at a local wig shop that I saw
while driving to the hotel. This was fortunate, because wig shops are usually
the hardest places to find. Luckily, I was able to quickly find this shop
and bought a shoulder link conservative brunette wig. My next stop was a
thrift shop for clothes and shoes. I like shopping at thrift shops because
there is such a wide variety of clothes in one location and the shoes are
always interesting. While I am pretty comfortable shopping for womens clothes,
I still get a rush when I sneak off to the dressing room with an arm full
of womens clothes. I get the same feeling when I am shopping for shoes,
bras and panties and a women takes notice. They never say anything, but
I know they want to ask. I was able to a great assortment of dresses, skirts,
and blouses at the thift store, but no shoes or undergarments. My next stop
was a department store where I purchased my make-up, nails, wax, and pantyhose.
Again, I get a spectacular rush when I take all of these items to the young
girl at the counter. Finally, I went to a discount shoe store and bought
a nice pair of black high-heels. To finish off my shopping day I made a
stop at a local sex shop for some condoms, a dildo, and some bondage gear.
While I don't care for men, I do fantasize about being taken by a man while
dressed as a woman and like to throw some self-bondage in the mix as well.
With all of my shopping done, I eagerly rushed back to my hotel room to
start my evening. I begin by waxing my legs. I have done this before and
my wife doesn't seem to mind. Transforming my normally hairy legs into silky
smooth feminine legs is a bit painful, but the hard-on I get when I am done
is worth it. Next I give my face a very close shave and finally apply a
ton of moisturizer to my whole body. With my body ready, I fill two condoms
with hair conditioner to make a nice set of realistic C-cup breast implants.
I am now ready to become a woman.
I start by slipping on a shiny pair of nude Hanes Solutions pantyhose. They
have a fench cut panty with a lace waistband and are totally sexy. As I
slip the shiny hose up my smooth legs I have trouble holding back a pre-mature
orgasm. The hose feel so good on my freshly waxed legs and I spend some
time enjoying the experience. Next I put on a white satin bra and place
my new implants inside the cups. Finally, I put on a white satin body slip
that stops just above my knees. The feeling of the slip rubbing on the hose
is so exhilarating that I again almost cum. I am now ready for hair and
make-up. I start with a thick coat of foundation, apply heavy, but conservative
eye color, black mascara, and finish with a nice layer of powder. Finally,
I carefully apply a shiny layer of red lipstick that fills out my lips and
completes my look. With my wig on, I can't even see my old self and feel
like I have transformed into a sexy woman.
With my transformation complete, I pick out an outfit for the night.
I try on everything I bought, but settle on a black pencil skirt that
just covers the slip above my knee and a conservative long sleeve white
blouse. I get an unbelievably sexy feeling as I slip my nylon covered
feet into my four-inch high heels. After examining myself in the mirror
for quite some time, I begin to walk around my hotel room and re-learn
my feminine mannerisms. By now it is nearly 10 pm and I begin to contemplate
going for a drive. I made sure my hotel room was at the end of the hall
and checked out the stairs and back exit when I arrived. With my car parked
in back of the hotel, I knew I had a good chance of getting in and out
of the building without being seen. However, when I looked out the window
I saw a group of four men standing around a pick-up truck drinking beer.
I paced around the hotel room for a while contemplating my options. While
the men were not in view of my car, I was still reluctant to take the
risk of running into them. Finally, after seeing they were preoccupied
and not going anywhere for a while I decided to make my move.
I grabbed my keys and approached my hotel room door. Opening the door slightly,
I could tell no one was in the hall way. As I stepped out into the hall,
the butterflies were going crazy in my stomach. I was both nervous and excited
at the same time. I quickly made my way to the stairway and started to slowly
walk down to the ground floor. Every step I took in the high heels raised
my sexual excitement and I felt good about my decision. At the back door,
I looked out and saw no one in sight. With a final surge of fear and sexual
excitement I opened the door and began the long fifty meter walk to my car.
As soon as I cleared the building I could hear the men on the side of the
building. They were clearly drunk and being obnoxious, but I was happy to
at least know they were out of sight. I continued to move towards the car
and thought I was home free. Then, just as I made it to the car a man shouted
"hey sexy where you going?" from the corner of the building. It
was one of the four drunks that must have been going to pee. I just kept
walking and ignored his question. As I reached the car door the guy shouted
again in a harsher tone. He said "hey, I am talking to you." I
could tell he was drunk and just focused on getting into the car. As I fumbled
with the key I heard the man approaching from behind me. It was at that
point that I knew I was in trouble....
As the man approached I knew I was in trouble. I desperately tried to
open the door, but he put out his hand and pushed it shut. The man again
asked where I was going. It was kind of dark near the car, so when I turned
around he couldn't tell I was a man. To defuse the situation I came right
out and said I was on my way to a costume party and I didn't want any
trouble. He was clearly surprised and pissed that he was checking out
a guy and said "what the fuck?" I turned and tried to open the
door again, but he pushed it closed and said "not so fast, sexy?"
I again told him that I didn't want any trouble. He said "then maybe
you shouldn't be walking around the back of a hotel at night dressed like
a slut." I think he believed I was a prostitute servicing someone
at the hotel. Then the worst happened, he shouted out to his three friends
and they quickly came around the building. The first guy told the rest
of the guys that he found a hot little slut all by her lonesome. I tried
to explain myself to the group, but they were as equally surprised and
pissed as the first guy. As the guys gathered around I felt things were
going to get worse and could smell the booze on their breathe. I tried
to explain to the guys that I was going to a costume party, but they didn't
believe me.
They accused me of being a prostitute and threatened to call the cops.
As I envisioned an embarrassing police fiasco, and the end of my career
and marriage, I pleaded with the men to let me leave. Sensing my fear,
one of the men suggested that we work out the situation another way. The
rest joined in and together they decided that I needed to work my way
out of the situation. One of the men said I looked like a slut and should
be treated like one. I argued with the men that I was not a prostitute
and I was a straight guy. One of the men laughed and said "not anymore."
Then another guy pulled out his phone and started to dial the police.
I quickly stopped him and accepted an uncertain fate. I asked the men
what they wanted.
One of the men reached out and grabbed my breast and commented that it
felt real. Then another guy grabbed the other one and agreed. Now they
had me up against the car and completely helpless. As the two men groped
my breasts, another stepped in and told me to get on my knees. Sensing
my reluctance the guy with the phone held it up in a threatening manner
and I slowly dropped to my knees. I felt completely helpless as my pantyhose
covered knees touched the cold concrete and the four men surrounded me.
The men then began to discuss who was going to go first and at that time
I truly accepted my situation.
One of the guys stepped up, pulled his semi-rigid cock out of his pants
and announced that he would sample the goods. As I looked at his cock
in front of my face I couldn't believe what was happening. I was about
to suck my first real cock. The man stepped forward and touched my red
lips with the head and said "suck it bitch." I slowly parted
my lips as he pushed the first few inches of his dick into my mouth. The
first thing I noticed was the taste of salt and the smell of sweat from
a guy who had been working all day. Then, as he pushed in deeper, I felt
my mouth fill up as his eight inch cock became fully erect. I quickly
felt the head of his cock hit the back of my throat and I pulled back
to avoid gagging. He thrusted forward again and forced his cock back into
my mouth. Accepting my fate, I began to slowly move my red lips up and
down his shaft and placed my hands on his hips to control the motion.
As I looked up at the man with my shameful eyes I suddenly realized that
I was living out a fantasy that had been urning deep in my body for many
years. I had played out some of this fantasy with my wife, but this was
real.
As the man continued to fuck my mouth I realized I was becoming aroused.
With my red lips working his shaft and the other men watching eagerly,
I realized that he was picking up the rhythm. This dirty man was about
to cum in my mouth and there was nothing I could do about it. He gave
me the most degrading look I have ever experienced and encouraged me to
keep sucking. After a few more strokes I felt his cock swell and felt
the first shot of his hot cum hit the back of my throat. I tried to pull
back, but the man grabbed my head and thrusted his cock deeper into my
mouth. He let out a moan as he dumped load after load of cum into my mouth.
I couldn't believe the size of it and now knew what it is was like to
be a woman. Deep inside I was extemely aroused, but did not want to show
it to the men. His cum tasted disgusting and as he pulled his cock out
of my mouth I let his load spill out of my red lips onto my skirt and
shiny hose.
The other men cheered with delight and commented on my performance. I
wiped my chin on my shirt and looked up at the men. I began to stand up
thinking that I was done, but one of the men asked what I was doing. He
said "your not done yet slut" as he pushed me back down. I was
actually exhausted from the experience and silently wondered how women
do it. The man who just finished with my mouth said he enjoyed the experience
and suggested everyone else have a try. One of the men, feeling exposed,
suggested they take me up to my room and party all night. I protested
but again, out came the cell phone. I couldn't believe it, but the night
was just begining....
Story posted by Anonymous
on Sunday, June 01, 2008 @ 01:00:00 PDT
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