Shemale
2006-01-11
My sophomore year I began dating this girl named Jan. Jan was blonde, slender, and absolutely gorgeous. She lived in this two bedroom apartment with her roommate Samantha. Sam, as she liked to be called, was a redhead, with dark green eyes and a nice chest. While not as beautiful as Jan she was still attractive.
One day while visiting Jan at their apartment she had to go out on an errand. She said she would be gone for almost an hour and to make myself comfortable. Sam wasn’t around so I grabbed a beer and flopped on the couch. As soon as Jan was gone I decided to “shop for souvenirs. ” As I had been into Jan’s drawers several times I decided to check out Sam’s room. A black lace bra was hanging from the edge of the drawer. Sam had good taste. Pulling open the drawer I was rewarded by mounds of silky thongs piled next to slips of various colors.
Carefully rummaging through the drawer I selected a pair of lace covered bikini bottoms. My cock was fully erect and begging to feel them. Dropping my pants I pulled off my shirt and boxers and slowly slid them up my legs.
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I savored their silky smoothness and was about to reach for the bra when a voice behind me said, “What are you doing?”
I froze, horrified at being caught. Slowly I turned around to face Sam. I tried to think of something to say but could only manage a meek stammer. Sam just stood there with her arms folded, staring at me. Her eyes lingered on my erection and a devilish grin came to her face.
“So you like to wear panties do you?” she asked. “Well I think I’ve got something we can have some fun with. Will you do that for me? After all you are wearing my panties. ” Not waiting for a reply she said, “Stand in the corner and don’t turn around. ” Silently I obeyed her. She knew that I was going to be pathetically easy to control from now on. As I faced the corner I could hear her going through drawers behind me. Finally she commanded me to turn around.
When I did I saw that she had laid out a slutty outfit on the bed. It was a red lace thong with matching bra and garter belt, black lace-trimmed pantyhose, and three inch stiletto heels.
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“Put it on Ray,” she commanded. Slowly I lowered her panties to the floor and picked up the red thong. As I pulled it on my erection sprang back to life. “It would appear that you like this,” she commented. “Hurry up with the hose and belt. ”
As quickly as I could I donned the garter belt and slid on the hose. I’m on the swim team so I keep my body shaved and the hose felt incredibly rich against my smooth skin. I hooked the garter belt straps to the hose and put on the bra.
Sam stepped over with some silicone pads and slipped them into the bra. She ran her fingers through my shoulder-length hair (the one vice I’d allowed myself since I could tuck it up under swim cap). “You look pretty in that whore’s outfit,” she said. “Step over here please. ”
I sat on the stool so she could apply makeup, blush, eyeliner, mascara, and lipstick, feminizing my soft features to the fullest. “Turn around, let me look at my whore. ”
I complied, twirling slowly so she could see her handiwork.
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My hardon was standing out beside the thong and she gently squeezed the head. She threw her arms around me and began kissing me. She pulled her tank top over her head and guided my mouth to her bare breasts. I sucked first one and then the other, rolling the nipples gently in my teeth. Pushing me down on my knees she said, “Close your eyes. ” I did and waited patiently as I heard her unzip and slide out of her jeans. When she commanded me to open my eyes I got the shock of my life. Staring me in the face was a nine-inch erection. I could only stare in disbelief. She flexed it up and down, breaking my trance.
“Do you like it?” I nodded. “Then kiss it, take it in your mouth. ”
Slowly I extended my tongue to the head of her cock. I licked up a drop of pre-cum and savored its salty-sweetness. I took the head into my mouth and began to slowly suck on it.
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I could only take about six inches so I concentrated on that, wrapping my hand around the base of her shaft and jerking her into my mouth. While I worked on her cock she was running her fingers through my hair and telling me that I was a good cocksucker.
Soon her breathing became ragged and she said, “If you’re not careful I’m going to cum in your mouth. ” My response was to increase my tempo, sucking her with a vigor I didn’t know I possessed. Soon I was taking all of her into my mouth, working my swallowing muscles on her cock head while her balls slapped my chin. Finally she could hold it no longer. She came with a rush, shooting her load down the back of my throat. I swallowed as fast as I could but it was more than I could handle.
I continued sucking her cock until I had every last drop. Then I let her go with an audible pop. She smiled and leaned over to lick up the cum that had dribbled down my chin. Then she kissed me.
“Your turn,” she said and pushed me onto my back. She grabbed my seven inch cock and parted her lips. She plunged down the length of my cock, taking it all in at once.
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I moaned softly as she expertly worked on my cock. Her left hand held the base of my cock, her fingers lightly massaging my balls, and her right hand probed my ass. The sensation of receiving a blowjob while dressed up like a cheap whore and having my ass finger fucked was too much. With a loud groan I came, filling Sam’s mouth with my cum. She drank all of it, and then moved up to kiss me. She had saved a mouthful of my cum and she now shared it with me.
Sitting up she licked her lips. “Mmm…” she said, “that was fun, but I’ve got more to give you. ” Reaching down she stroked her fully revived nine inch cock a few times. Pushing me onto my back she said, “I’m going to fuck you like the horny little slut you are. ”
Grabbing my knees she forced them up to my chest, completely exposing my ass hole. Placing the head of her cock at the edge of my sphincter she paused to apply some personal lubricant. Then she slowly pushed forward until the head of her cock disappeared into my ass, causing me to cry out in pain.
Sam waited patiently until my ass had ceased to spasm around the head of her cock. Then she began to move her hips back and forth, working deeper and deeper into me with every stroke.
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When she had about half of her cock inside me she withdrew all but the head then in one smooth motion she pushed in all the way to the base of her cock.
The pain was excruciating, but the intense feeling of pleasure was even greater. Slowly Sam fucked my ass, sliding almost completely out, and then gliding back in one fluid motion. I lost all track of time, intent only on the great fucking I was receiving. Then we heard a voice say, “Well, well, well. What do we have here?” Sam and I turned as one to look. Jan was standing in the door wearing one of those extremely short skirts and a red halter top. Here I was dressed like a horny slut with my legs wrapped around a shemale buried up to her balls in my ass with my girlfriend looking on. What a fix.
“It looks like Sam found herself a slut,” Jan said while walking over to the bed. Leaning in she kissed Sam deep and passionately. Hiking up her skirt she dropped her panties to the floor. Hopping up on the bed she straddled me and said, “I like fucking sluts!” With that she plunged herself down on my shaft, causing me to gasp.
The three of us fell into a frenzied rhythm of fucking. It wasn’t long before Sam tensed up and unloaded her balls into my ass.
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I in turn came inside of Jan who was busy riding me like a jockey. She came also and the three of us collapsed together in a pile on the bed. It was the single greatest life changing performance for any of us.
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