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.