Bet with Roommate Leads to Cuckold

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I’m Jeff and this is how I got cuckolded for the first time. At the time I was a sophomore in college and lived in three bedroom house with two other guys. Nick who was an easy going nice guy and Dwayne, an arrogant black guy who thought he was the greatest thing on earth, especially when it came to women.

I had dated my girlfriend Jen since our senior year of high school. After graduation we both went to local schools, me the local state university and Jen went to the local two year school to get some of her prerequisite classes out of the way while living at home.

Jen was raised in a religious household with strict parents and a strong sense of good girl behavior. When we started dating in high school Jen had never even been felt up. Although we didn’t really have a sexual relationship, we had a very intimate relationship. I respected her values and didn’t pressure her because she was special. I never met anyone quite like her before or since. She lit up the room when she walked in.

After a while she began to loosen up and we began to fool around more and more. Finally on our 2nd anniversary she told me she was ready to lose her virginity. It was the best sex I had ever had, it was the only time I ever loved the girl I was with. Not to mention Jen was the most beautiful girl I had ever seen too. She is 5’5″ with long straight golden blonde hair, blue eyes, soft silky smooth skin, perky b-cup breasts with big pointy nipples and a perfectly toned athletic body. She couldn’t be more perfect if she were sculpted by Michelangelo.

So anyway back to the story. Dwayne was always making smart ass comments and bragging about how big his cock was, He never came in that he didn’t talk about some girl that was begging for it. He even whipped it out and made comments to Nick and me about its size and how we probably wanted it too. In spite of his attitude Dwayne could be fun to hang out with sometimes and could be generous or helpful too.

Jen didn’t like Dwayne at all. She said he always looked at her like she was his prey and he was waiting for the right moment to pounce. Although he never said anything in front of her, he often made remarks to me about “did you see how Jen was looking at my cock? She wants it bro, she’s got a fever and nigga dick is the cure.”

Of course I blew him off when he would start up, it was just his way of having fun trying to get me riled up. Little did he know Jen found him repulsive? If she had a fault, it would be that sometimes she got a kind of high and mighty attitude with some people. Especially people she thought couldn’t control their urges. She viewed sex as very special and meant to be experienced in love, not animalistic lust.

One night after going out with Jen it was like Dwayne was waiting for me to come home to give me hell about her. As soon as I walked in the house he started, “hey Jeff, did you see how hot Jen was for me today? Man! I can’t believe she didn’t jump me right here on the couch.”

“Yeah whatever man, she really wants you, and you’re all she talks about.”

“If she wants me in her that bad maybe I should give her some”

“Dude, seriously. It’s kind of getting old hearing this all the time. She doesn’t like you, want you, or care anything about you. She thinks you are a jerk and is only semi cordial to you because you’re my roommate.”

“Jeff buddy, keep telling yourself that, but I can see these things in a hoe’s eyes, and Jen wants it bad. I could have her anytime I want, and she will beg me to fuck her harder and cum deep inside her.”

“You are so full of shit, not even for money, she’s not like the whores you always bring in here”

I have to admit, it was getting a little heated and I was losing my temper. Dwayne new it and loved every minute of it. The more he enjoyed it the more pissed off I got. Finally I without thinking first I blurted out, “I know she wouldn’t fuck you no matter what. I bet you can’t seduce her, even if the two of you are alone she won’t let you anywhere near her.”

“Really; then prove it. Get her sexy little ass over hear and we’ll find out which of us knows her better”

“Fine, what are the stakes? You name it”

“Anything I want?”

“I’m going to win, so name it. It don’t matter what you want from me cuz I won’t lose”

“Ok, if I can’t get up in her I’ll give $1000 and you can drive my convertible for two weeks. When I get done fuckin her you will owe me $1000 and I get you motorcycle for two weeks”

“I don’t have a $1000, you know that”

“Ok, since I’m risking a grand and my car, I want value for value. If I get my dick in her even for five seconds with her consent I get your bike, if she lets me bust in her cunt you owe me a bj”

“What! Fuck you”

“Come on buddy, what do you got to lose? You know for certain that I won’t be able to get near your precious perfect Jen. Don’t bitch up now, show your faith in her”

“Fine, it’s a bet.”

We shook on it and it was settled. If I was wrong he would get more than he knew, not only would I lose the love of my life, I would lose my dignity and self respect along with her.

Dwayne asked “when are we going to do this and how will you know what happens?”

“Tomorrow night and I don’t know. If you’re as great as you say I should be able to hear her outside your window”

“I have a better idea, come on and let me show you”

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