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”
As we walked into Dwayne’s room he started to tell me how he was a real tech guru. He always got the newest and best of anything tech related. His newest toys were a set of high definition spy cameras that had a wireless connection to feed a recorder. He explained that the recorder could receive up to six different camera signals and record them all at once. The cameras were concealed in different things to make them inconspicuous. One was a smoke detector, another was a picture frame, and then he had various other hidden cams as well.
Dwayne proceeded to tell me his plan. I was to get Jen to wear something sexy and come over to go out with me to dinner and dancing. When she got there I would be in my room hiding with the recorder attached to my TV so I could see the “action” as he called it. Since I wouldn’t be there as far as Jen knew, Dwayne would have his chance to seduce her and I could see the whole thing from six different views. Of course the only action would be Jen shredding his ego with him not getting even a second’s worth of a chance to get her under his spell.
Just as we had planned, we put the cameras in place, one in the living room on the TV stand facing the couch and the rest strategically in Dwayne’s bedroom. I called Jen and made plans to go out and asked her to wear something sexy but not too sexy.
At about 7:00pm Jen texted me that she would be over in a half hour or so. I didn’t respond as part of the plan. When she knocked on the door I went in my room and locked the door. When I turned on the TV I saw Dwayne open the door wearing a pair tight white boxer/briefs and nothing else.
“Hey Dwayne. Is Jeff ready to go?”
“Jeff? He didn’t call you? He got an emergency call and had to take off”
“Whatever, I saw his car outside, where is he?”
“He’s not here, really. He told me he had to run out and that you were on your way and for me to tell you what happened and keep you entertained until he got back if you wanted to hang around and wait for him to get back.”
“Are you serious? He never called”
As she walked past to go to my room to check for herself she squeezed by Dwayne in the doorway. She noticed he was looking at her exposed cleavage as she went by.
“Really Dwayne! You don’t see enough from your whores? You got to look down my shirt as I walk by?”
(more…)
