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The Bet

Shemale
2005-11-30

I've always been quite the ladies man. Eversince high school I've always had all the pussy I could ever want.   Given a little time I could fuck any girl I wanted.   Until I met Irene.
Irene was a tall brunette, long legs, full figure, and the most gorgeous eyes you ever saw.   I met her at a social dinner at the college.   She had showed up with some of her girlfriends and I thought she was the hottest thing ever.
One of my frat buddies said, "Forget it pal, she's a straight up lesbian.   Won't even look at men. "
"Fifty bucks says I can fuck her," I replied.
"You're on!"
So I grabbed a couple of drinks and headed over to where she sat momentarily alone.   At first she tried to blow me off, but I worked my magic and soon we were lost in conversation.   Finally the conversation got around to sex and I asked her why she didn't date guys.   She said it was because she was gay.   I asked how she knew she wasn't bi-sexual if she'd never tried it.   I knew lots of girls who were bi.

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    She said that she had never tried, she was just different.   Long story short, I convinced her to come back to my apartment with me.
Once back at my place I got us another drink and settled in on the couch.   I live alone because it gives me greater freedom with my "relationships. "  Also it spares the girls from taking the infamous "walk of shame. "  I could tell Irene was nervous so I made small talk to help her relax.   When I sensed the time was right, I leaned in and kissed her.   She responded by wrapping her arms around me and thrusting her tounge inside my mouth.
Slowly I kissed down her neck and bared her perfect breasts.   I sucked first one and then the other of her nipples, gently tugging them with my teeth.   She pushed me onto my back and undid my pants.   Pulling off my pants and boxers in one motion, she seized my cock and began sucking on it like a fiend.
I was in ecstacy.   This was positively the best blowjob I had ever had, bar none.   It wasn't long before I was jetting my cum into her mouth.

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    She swallowed my load and continued sucking until she had drained every last drop of cum from my cock.
Sitting up she licked her lips and said, "That was fun. "
"It's your turn now," I replied.
"I should go now. "
"Why? Because you're a lesbian?  I can still give you a good time. "
"You don't understand," she pleaded, "I'm different. "
Taking her hand I said, "It doesn't matter. "  I kissed her lips in an attempt to relieve her tension.   I laid her back on the couch and began gently kissing her neck.   While continuing to kiss her neck, I pushed her dress off of her hips and pulled off her panties.   Rubbing the inside of her thigh I slid my hand upward toward her crotch.   And recieved the biggest shock of my life!
"Holy Shit!!" I cried as my hand grabbed a huge hard on.
"I tried to tell you," she said as tears began to fill her eyes.
Recovering from my initial shock I just stared, completely transfixed.   She tried to get up but I held her down.

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    Slowly I took her cock in my hand and gave it a gentle squeeze.   She let out a low moan so I began to stroke it.   She moaned louder and started to thrust her hips with each stroke of my hand.
What the hell was I doing?  Here I was with my hand on someone else's cock!  It was absurd!  I couldn't control myself anymore.   In a trance like state I lowered my head towards her cock, gingerly touching my tounge to the head.   There was a drop of pre-cum and I could taste its salty sweetness.
Slowly I took the head of her cock into my mouth.   I couldn't believe it, I was actually sucking cock!  I worked more and more of it into my mouth until I had the entire length of it and her balls were resting against my chin.   I withdrew it slowly before plunging all the way back down again.
Irene placed her hand on my head and began moving her hips back and forth, fucking my mouth as if it were a pussy.   She increased tempo and began burying her cock in my throat with each thrust.   Her breathing became ragged and she thrust  deep into my mouth, shooting her cum down my throat.   I swallowed all of it and continued sucking until she went limp.
Releasing her, i moved up and kissed her lips.   I carried her into the bedroom and laid her upon the bed.

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    Taking her cock in my mouth once again I began sucking until She had a rigid hard on again.   Irene leaned forward and kissed me and had me lay on my back.   She started sucking my cock again but quickly moved down to my ass hole.   She licked my sphincter for a minute, lubing it with her saliva.
When I was good and lubed, she lifted one of my legs over her shoulder and placed her cock at the entrance to my ass.   Very gently she pushed forward until my hole gave way and allowed her to penetrate me.   I cried out in pain but she very slowly began to move back and forth, going a little deeper with each stroke.   After she was all the way in she began to fuck me very slowly.  
At first the pain was almost unbearable but it soon faded and was replaced with sheer pleasure.   She continued to fuck me, moving faster and faster until she was pounding my ass like a cheap whore.   Reaching down I grabbed my cock and began stroking it in time with her thrusts.   It wasn't long before I shot my load all over my chest.   Almost immediately Irene drove all the way into my hole, let out a deep groan, and filled my ass with her cum.   Collapsing on my chest, she kissed me passionatley, and we drifted off to sleep.   This was one hell of a way to win a bet.

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