The Peeping Tom
by Anonymous

 I was sitting on the bed in my room. I was reading Penthouse Forum and
read a letter about a peeping tom who became a sex slave after being
caught when I began to hear voices coming from next door. My house is
only 5 steps away from our next door neighbour's so in my room I could
hear anything from loud music to sex. To investigate the noises I ran up
to the window and moved the curtain slightly to see what was going on
through the next door neighbour's window. To my shock I saw a man and a
woman having sex. The man happened to be my neighbour, Dan. He is tall
man about 6'3" and very muscular with a short crew cut hairstyle. The
woman, however, was not recognizable perhaps just one of his girlfriends.
The woman was mounted on top of Dan with her knees on the bed
as she rode his dick. Her back was facing toward me and I thought since
no one was around I would jerk myself off since I was getting really
turned on by this whole scene. As I stroked they continued to fuck when
the mysterious woman with long red hair wearing white silk stockings and
red 4" pumps removed herself from his organ and stood up on the bed. She
turned herself around in my direction to reveal her breasts and what I
thought was a penis. My eyes widened as I saw a penis on this woman or
man or whatever. I couldn't believe it, Dan was fucking a she-male,
transsexual or transvestite, whatever you call them. She bent over held
onto Dan's bedposts with both hands as Dan lifted himself from the bed
to her behind all the while holding his own tool. What a tool it was, it
was about 8" cut and looked well proportioned to his muscular body. Dan
inserted his cock into the "woman's" ass and pumped her ass long and
hard. "Yeah, baby -- come on -- yeah!!!" he screamed as he fucked her.
Before long, Dan withdrew from her and drenched her ass cheeks with his
white cum. As he did that I stroked myself even harder and before I knew
it I stained the curtains with my own cum. Just as I was about to turn
and walk away, he looked through the window and looked right into my
eyes. Great, I was caught red handed thinking I'm going to be in trouble
but instead he smiled and gave me a wink. I draped the curtain across
the window and ran to the bathroom and toweled myself dry.

 I couldn't believe any of it. Dan was having sex with what looked like
a woman but was really a man who looked like a woman and Dan who caught
me looking only smiled and winked at me. I had watched x-rated videos
featuring transsexual acts before but it didn't turn me on. I wondered
why that whole scene really turned me on considering I'm not into that
kind of sexual activity. But somehow, it made me horny. I've been
straight all my life, "What's happening to me?" I thought to myself. Why
am I having these feelings. Just recently my girlfriend of 2 years and I
broke up. It was nothing  horrible, we just realized that we were
different, wanted to reach different goals and objectives. I then asked
myself "why did Dan not scream and attempt to cover the window with the
curtains as I was looking?  Maybe he was just turned on that I was
peeping -- or maybe I just turned him on." I felt confused, I had never
thought a guy would want to have me in any way. After all I'm only 5'5",
130 pounds and I have an average sized penis of 6". I'm not muscular or
tall, just average looking.

 A couple days later I went to the adult video store located within 5
minutes of walking from my home. My house was empty for the whole
weekend because my parents were out of town on vacation. I walked into
the store and began to browse around. I went through various sections of
the store from big boobs to orgies where I soon found myself in the
transsexual section. I glanced the wall at the titles of some of their
videos. Some of the videos had really weird names such as TV Panty
Party, Single White Shemale and TRANScontinental Debutantes. The titles
of these videos were weird, but funny I thought I would rent one seeing
that just a couple of days ago I saw my neighbour Dan fucking a
transsexual. I reached over to pick up the video Sizzling Shemale
Surprise when another hand reached over to pick up the same video. The
strange hand and my hand grabbed the video at the same time. As we both
struggled for the video I looked up and saw my neighbour Dan. He to
wanted to rent the same video, we looked at each other and we both said
"Hi" to each other. "I see you want to rent the same video I want to rent."
He said "I guess -- if you want -- go ahead and rent it." With no other
word he let go of the video and began to walk to another video section
of the store. Without thinking I turned around, stopped Dan and asked
him if he would like to come over and watch the video with me. "Sure,
that sounds cool with me." He said "I'll bring the popcorn and beer."
What on earth was I thinking, I had just asked a man to come over and
watch a porno video with me. That was something I never did before and I
don't know why I did that. I paid for the rental of the video and walked
out of the store with Dan by my side. "I'll be by around 7 o'clock
tonight -- is that all right?" he asked.
"Yeah, sure -- come on by." I said.
With those final words we both walked away in opposite directions. I
walked back to my house and he walked somewhere unknown to me. Upon
arrival at my house I walked downstairs to my living room where I
cleaned up making the house look livable. Seven o'clock rolled around
and there was a loud knock on my door. I  ran to the door, I still don't
know why to this day, and opened the door. There stood Dan with a bowl
of popcorn and a 12-pack of beer in his hands. "Come on in." I said to
him. He walked in, removed his shoes from his feet and walked downstairs
to the living room. He made himself comfortable sitting on the couch as
I turned on the television set. I turned on the VCR and popped the video
in. As the video played, I sat next to Dan and we began to talk about
transsexuals, crossdressing, bondage, etc. There wasn't any sexual
activity we didn't discuss while the movie was playing. Then all of a
sudden during one scene involving a man and a "woman" fucking, Dan
unzipped his pants and pulled out his cock. I was shocked but just sat
there staring at him as he started to pull it. I don't know why I didn't
say anything, I guess it turned me on. He stroked harder and harder,
then he asked me to bend over and suck him. I reached over with my hand
and wrapped it around his shaft. His eyes rolled back and I began to
stroke his cock. He was getting even more turned on as I slowly moved
head lower. I don't know why but I needed to taste him in my mouth. My
saliva dripped all around his head as I began to suck and suck like a
vacuum. Then suddenly he stopped me, removed my mouth from his organ and
lifted my head. "What's wrong?" I asked "Am I doing it wrong?"
"No, I want you to dress up like they do in the video." Dan said.
"What? Dress up like them. Like the shemales? I think I would make an
ugly woman." I said to him
"I think you'll look great." Dan explained "Let's go to my house next
door."

We both got up and walked over to his house which was next door. He took
me into his room and went into his closet and pulled out a large
suitcase. "Here, go into the bathroom and change into this stuff." Dan
ordered. I don't know why, but I thought what the hell. I just sucked
this guy's dick which I never did to any other guy in my life, maybe its
a turn on for him, besides I was depressed and felt like letting it all
out. I grabbed the suitcase and walked into the bathroom which was just
across from the bedroom. I locked the door and looked at myself in the
mirror. "Shit, I have hair on my face, not to mention my legs. How the
hell am I ever going to pull this off?" Dan walked by and yelled out,
"Take your time in there Vince, I want you to look just like a woman.
Take a shower, shave if you have to, all the stuff is in the suitcase!"
Great, I thought to myself, oh well here goes nothing. I turned on the
faucet to the bathtub and let the tub fill with water while I placed the
suitcase over the covered toiled seat. I quickly unzipped the suitcase
and opened it. I examined the contents of the suitcase, in it I found a
red garter belt with straps, a pair of black fishnet stockings, 5" pumps
with a golden spiked heel, a black lacy bra, 2 silicone breast enhancers
about size 36C (so the box said), a long brown wig, black lace panties,
and a box containing makeup, a razor and hair removal cream. I quickly
removed all my clothes and hopped in the bathtub. I took the soap and
lathered myself up and rinsed off. Next, I took the razor and shaved all
the hair from my legs and my armpits. Next I stood up in the bathtub and
shaved the hair near my crotch. I don't know why, but I shaved the hair
around my cock in a V shape making it look like a pussy. I stepped out
of the tub, drained it and walked over to the sink. There I took out
some shaving cream and shaved my facial hair. Then I took the hair
removal cream and spread it all across my chest and stomach. After
waiting about five minutes, the hair fell off my body to the bathroom
floor. I was completely hairless except for that which was on my head.
Now came the fun stuff. I took the red garter belt and snapped it around
my waist. Slowly I slipped the fishnet stockings over my legs while
sitting on the edge of the bathtub. I hooked both stockings onto the
straps. My cock got bigger, I couldn't believe the feeling I felt as the
stockings were on my legs. I got so turned on I wanted to stroke it
right then and there but I stopped myself and continued to dress up.
Next, I fitted the black bra around my chest. I took the silicone breast
enhancers out of the box and slipped each one into the cups of the bra.
I looked at myself in the mirror, I was amazed at how beautiful I
looked, as a woman. The next thing I did was my makeup. I remembered
watching my ex-girlfriend apply it once and I did exactly what she did.
I first applied concealer all over my face, then I applied eyeliner and
mascara across my eyelids and eyelashes, then I dabbed blush on my
cheeks and smeared lipstick on my lips, to top it all off I slipped on
the long brown wig over my head. "Wow, I can't believe this, I look like
a woman!!" I then slipped my silky feet into the heels and looked again
at myself in the mirror "Okay, I hope he likes it."

 I unlocked the bathroom door and walked out into the hallway. There
stood Dan, his eyes widened as he stood there naked watching me all
dressed up. I could see his cock get bigger with excitement. "Wow, you
look great, I want you so bad. Come here!" I slowly walked over with my
hips moving left and right with every step. As soon as I approached, he
grabbed my hips and pulled me closer to him where he embraced me
passionately on my lips. I waved my arms and hands in the air and pushed
him away from me "What's wrong?" Dan asked with confusion "Don't you
want that?"
"Dan, don't you know how to kiss someone?" I leaned over and kissed him
with a mad passion and then French kissed him. He lifted me up off the
ground and I wrapped my legs around his waist. We both fell on top of
the bed with him on top of me and my legs still wrapped around his
waist. We continued to kiss as he fondled my stocking legs. He then
continued kissing and caressing me with his tongue. His moved his tongue
all across my body, first starting at my "breasts" and ending at my
stiff panty covered "pussy". He snapped the panties off my body and
immediately engorged my cock with his wide mouth. He began to suck my
shaft going up and down slowly and then more quickly. I was getting so
turned on, I grabbed my "breasts" and squeezed them harder every time he
sucked harder on my "pussy". I couldn't take it anymore that I ordered
him to stop. "What's wrong?" Dan asked
"It's my turn, I want that cock in my mouth now!" I exclaimed.
Dan sat on the edge of the bed as I walked over in my heels to face him.
I first began to fondle his masculine chest with my small hand and then
took his hands and placed them on my "breasts". I straddled myself on
top of him and kissed him passionately and deeply. Then I dropped to my
knees on the floor and grabbed his balls. I spread his legs wider so
that I could face his cock. I slowly began to stroke his cock. "Do you
want your cock in my mouth?" I asked him
"Yeah, take it in your mouth -- I want it in there" Dan said as I
continued to stroke him.
"What if I don't want it in my mouth? What are you going to do?" I asked
him
"Oh please--" Dan said sarcastically and pushed my head forward slipping
his dick into my mouth. I took his cock in my mouth and encircled his
head with my tongue. With my right hand I stroked his shaft and my left
hand squeezed his balls ever so gently all the while sucking him off and
looking right into his eyes. I continued sucking him for what felt like
an eternity. As I sucked he began to grab my "breasts", harder and
harder every time I sucked on his prick. He lifted my head from his dick
and looked right into my eyes. "I want to fuck you -- I want to fuck you so
bad!!" Dan said and with that he lifted me on to the bed. I lied down
with my back on the mattress, lifted my legs and spread them wide. He
reached over to a drawer that was near his bed, opened it and removed
some lubrication. I kept my legs spread apart, caressing the stockings
with my hands and stroking my hard "pussy" as Dan lubricated his dick.
Then he slowly slipped his lubricated cock into my virgin ass. I
screamed as he pushed it in. I had never felt so much pain before, I
took a pillow and bit into it as he began to fuck me with a slow rhythm.
As he pumped my ass, the pain was going away as my body adjusted to
pumps. I felt no more pain and encouraged him. "Oh baby -- yeah -- fuck me
hard -- yes -- oh yes -- oh Dan -- fuck me!!!" I screamed to Dan in ecstasy.
"You like it bitch, do you like?" Dan asked with anger in his voice
"Yes.. I do!!!" I said
"I can't hear you, do you like it?" Dan asked again
"YES!!" I screamed
"Do you want me to fuck you from behind?" Dan asked
"Yes, I want it from behind!" I said
"I can't hear you slut, I asked, do you want it from behind?" Dan asked
angrily
"YES, I want it from behind!" I screamed and with that he slipped out of
my ass and turned me around. I was on all fours when he came into my ass
from behind me with his cock. "Ohh!" I yelled as he plunged into me. Dan
pumped me slowly at first from behind and began pumping faster and
faster. His left hand was grasped firmly on the back of my garter belt
and his right hand on my cock as he stroked it faster and faster with
every pump. I moaned and screamed in ecstasy as he fucked me. Then I
asked him if I could sit on top of his hard prick. "I want to sit on
your cock!!" I yelled. He then removed his hard cock and lied down on
his back on the bed. I crawled over him and straddled him. I reached
over and kissed him ever so passionately. As we embraced, he slowly
slipped his cock in my hole. He pumped me slowly and then quickly. He
held onto my "breasts" and fucked me hard. I couldn't believe the
sensation I was feeling. Then he pushed me off his dick and rolled me
onto my side. As I lied on my side he plunged me once again and fucked
me faster and faster. I closed my eyes and shuddered in pain and ecstasy
as he fucked me in a spoon position. He held my silky leg in the air and
fucked me as I stroked my own cock. "I'm going to cum!!!" Dan yelled as
he removed his cock from my ass. He turned me around and sat on top of
me stroking his cock near my face. Within moments he dropped his wide
load all over my face. I engulfed his wet cock in my mouth and swallowed
all of his cum until he was completely drained.

Ever since that encounter, I have been meeting Dan every week. I would
wear different types of clothes for our sex sessions. After three months
had passed, I decided to see a doctor and he placed me on a hormone
therapy system. Now, I'm developing real breasts and Dan loves it very
much. I've moved out of my house and now Dan and I live together. Now
the next thing is perhaps removing my "pussy" for a real one.