Cuckolded on a Bet

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?”

Dwayne didn’t respond, he just smiled and had a chuckle to himself. As Jen knocked on the door Dwayne came around the corner, he didn’t say anything, just watched her. When I didn’t answer the door Jen called my cell. It rang and I realized that I had forgotten to silence the ringer.

Dwayne thinking quick on his feet said “that’s why he didn’t call. He left in such a rush he forgot his phone.”

“Oh well, I guess I’ll go. Tell him I came by and I’m not happy about this”

I could almost taste sweet victory when Dwayne said “well don’t rush to leave; Jeff said he would hopefully be back soon. You don’t want to waste all that sexy and just go home. Wait a while and see if he comes back.”

“I think I’ll just go; it’s probably best if I go.

I was so stoked that I almost let out a cheer. Luckily I remembered just in time to keep quiet. As near as victory was for me it was not to be that easy after all. Dwayne wasn’t going to lose a bet or the chance to turn my sweet Jen into another one of his black cock addicted sluts without pulling out all his little tricks.

“Ok Jen, please don’t go. I know you want to get out of here as quick as possible since Jeff is gone because you don’t like or trust me. I guess I don’t blame you, not with the way I stare at you every time you come around. It’s just that you are so beautiful, I can’t help myself. I have never seen a woman with so much confidence and strength. It’s really sexy, not to mention your big blue eyes and gorgeous body.”

“Uhm, uh, I don’t know what to say. Uhm, I guess thanks for acknowledging your behavior, and for the compliments. But I know you, and you only care about gettin in whatever pretty girl is in front of you.”

“That’s fair enough, now that we’ve cleared the air how about you hang around and see if Jeff gets back soon. You can watch tv in the living room.”

“Ok, as long as you understand that I’m not one of your sluts and you won’t be sticking anything in me, not tonight and not ever.”

“I wouldn’t try to do anything with you, Jeff is my friend and that’s a line I won’t cross.”

I loved every minute of it. Jen was proving me right, she shut down every one of Dwayne’s moves, except that she had agreed to stay and wait a while for me. But I wasn’t concerned about that; she had after all just laid down a brutal opinion of Dwayne that came from the heart.

I watched the living room via the camera we placed next to the TV. It was working so far; Jen was watching some movie and didn’t appear to notice the camera in the least. She sat there alone on the couch for nearly an hour. I thought that she would give up at any minute and head home.

Then I saw Dwayne walk into view to stand in front of Jen but to the side enough that I could still see her past him. He was still wearing nothing but his box/briefs. They were so tight nearly everything was exposed as if he were naked.

As much as I hate to admit it because he is such an asshole, Dwayne has a perfectly chiseled body, and his cock is larger than any I have seen including porn stars. Jen noticed too, her eyes were glancing from his to his cock. She must have been thinking the same as me. What a shame that something that looks so beautiful could be so ugly.

“Dwayne, why are you not wearing pants? You think you can walk in here and show off your body and I will change my mind and beg you to fuck me with your big black dick? That may work on the kind of girls you usually go for, but I told you I’m not one of your sluts.”

“I’m just trying to be comfortable. I am at home, not out in public or at your place. I just thought I would keep you company while you wait for Jeff.”

“If you want to keep me company why are you almost nude standing with your junk in my face? Why don’t you get decent and come and sit next to me and have a conversation?”

“I’ll sit with you, but I’m not going to change. If you aren’t interested in it why do care so much that I’m in my draws? I think you want it and you’re afraid you won’t be able to control yourself.”

“You really believe that?”

Dwayne nodded, “yep, I can see it in your eyes. If I tried you would let me fuck you right here on this couch and by the end you would beg me to fill you with my hot sticky nigger cum”

“You’re a sick bastard, how can anybody be so arrogant? You make me sick, you will never, ever; ever; fuck me anywhere, nor would I ever beg you for your hot sticky nigger cum”

“Denial is the first sign that you are under the spell. Its ok, I know its power well. You would be added to a long line of white girls that couldn’t resist the black cock. But I have to admit, I have never wanted to spread a pair of legs and mount a bitch as much as I want you; here; now”

“Ah…how sweet. I’ve never had a guy tell me he wanted to spread my legs and mount me. And that pet name, bitch, I’ve never been so: repulsed! What’s the matter with you? That’s exactly why you will never get me, or any girl like me. Women with decency and class don’t respond positively to your childish disgusting advances.”

At this point I was proud of Jen for ripping into Dwayne and his immature bullshit. I was kind of gettin concerned with the tone of the conversation. If it wasn’t for the stupid bet and pretending to be gone I would have gone out and stopped it, but I had to sit back and watch instead.

“Jen baby, come on. Admit you want my cock and let’s do this, the sooner you let down your guard and stop fighting your desire the sooner I can make you feel things you never knew you could. I’m going to get up in you sooner or later, if not today then tomorrow, or next week, or the next. Soon your willpower will fade and you be begging me to fuck you. you will do anything for some of this” as he rubbed his cock and squeezed the huge head”

Jen just sat there silent for several minutes watching him. She watched him stroke his cock, she looked him in the eyes, and she looked down at her lap and closed her eyes. Finally she sighed;

I was watching and listening so intently I didn’t miss a thing. I saw ever stroke, every squeeze of the head on the giant trouser snake. I heard every breath, every sigh, and every noise Dwayne’s sweaty dark skin made against the leather couch as he stroked his cock. I was suddenly sure that I had lost the bet with this big dicked bastard. But surprisingly I wasn’t completely unhappy. There were feelings of fear, nervousness, anger, excitement, and arousal. I can’t believe it, but I actually deep down began pulling for Dwayne to succeed. I wanted to see him shove all 12 inches of dark meat into her tight little twat.

Jen looked up, starting at her lap going to the floor, then to Dwayne’s muscular thighs settling briefly on his hand stroking the full length of his monstrous baby maker. As she looked into his eyes, cocky eyes that said she wasn’t special just another conquest, she knew there was only one way to win this argument. She wanted to help him see the truth in her words. Jen wanted to help Dwayne find happiness and live a full life, unlike the empty lustful existence he so far had suffered.

“If I weren’t with Jeff I would lie back on this couch and let you do your best to turn me. Afterward when you saw that you failed your ego would be crushed and you would see that your way is wrong and there is more to life than sex.”

“Don’t use your boyfriend as an excuse to hide behind your fear. All you have to is surrender to your desire and experience otherworldly pleasure.”

“Damn…! You are such an ass. Is that all you think of? You think sex is everything. It’s not! Sex is a beautiful thing meant for lovers, not for animals consumed by lust. Your kind of sex is nothing; it pales in comparison to making love to your soul mate. If I were single I swear I would let you take me in anyway for as long as you would to show you that without love and a spiritual connection to you that your dirty lust may get you off, but I would not enjoy it more than mildly at best. Having the body of a Greek god and a cock that would shame an elephant’s trunk doesn’t make up for the lack of a connection and intimacy”

I couldn’t believe my ears. Jen saying she would let this big sweaty dark skinned black jerk fuck her senseless just to prove a point. Did she have any idea what she was saying? How could she? What kind of sacrifice is it to let a man of such size and strength unleashes his full lustful fury on her beautiful petite innocent body.

Dwayne said again, “don’t use an excuse, give in and let me show you what you are missing. If you need to believe it to be for my benefit then so be it. But you will be the one to realize how wrong you are.”

As he stood up and slid his briefs down he stepped toward Jen to reveal the unhindered glory of his size. Jen just watched as with each step it came closer to her face, standing straight as an arrow. Stiff as a board and radiating sexual heat like a forest fire. Dwayne stepped up onto the couch and put both hands on Jen’s head to pull her forward.

He aimed he massive chocolate sex at her gorgeous little mouth. As the fist sized head pressed up against her lips Jen opened her mouth to grant entrance to the large shaft. As Dwayne slowly slid in further Jen began to gag, spit blew out around her lips and the shaft of his giant dick. When she gagged he slowed his advance but never stopped. Steadily with each gentle thrust of his hips Dwayne got an inch or so deeper into her throat until he had nearly all of his length beyond Jen’s full pink lips.

Dwayne softly and comfortingly praised Jen for how good she was with a dick in her throat. That’s as sweet as the black bastard ever got after he had caught his prey. He was an animal, sly and cunning. He lured them in with whatever bait it would take, but once he had them they were at his mercy. And he showed none.

With her mouth stretched beyond what she thought possible and a mouth and throat full of huge black dick, I zoomed in on jen’s face. She had a look of disbelief in her beautiful blue angel eyes. It was like she couldn’t figure out how she got herself into this situation or maybe she couldn’t believe that a man could be that well endowed and that she could engulf the entire length between her lips.

Her blue eye shadow was beginning to run down her eyelids and cheeks a little. Her eyes were watering from the choking and gagging. Dwayne took her by her ponytail and began to fuck her face with a faster pace than before. It was a relentless pace that Dwayne set. Each powerful thrust caused Jen to grunt and gag.

“Yeah bitch, I told you I would show you things you never new were possible. Oh…fuck! Take that nigger dick hoe, take it!”

Jen couldn’t respond even if she wanted to. I was so hard it felt like my cock might explode. I had never been involved in anything like that. Now not only was I involved I had been mostly responsible for it happening. It was so erotic to see my Jen being ravaged by this asshole that I couldn’t stand that I blew two loads myself jacking off watching

Almost in rhythm with my third load Dwayne’s thrusts got erratic and then he pulled back and left just the head in Jen’s mouth. He stroked the exposed length a few times.

“I’ma fill your mouth with my nut! Swallow it baby. Yeah…that’s it. That’s my girl. I bet Jeff don’t ever fuck your face like that.”

“No. he doesn’t quite do it like that.”

“I need a short rest and then we’ll get to the real fun” I’m going to give you the best dick you’ve ever had.”

As he turned, Dwayne looked right at the camera, grinned an arrogant grin and then winked at me before he turned to sit next to Jen.

She was wearing a short navy blue skirt that came to a few inches above her knees, a thin white tank top that showed a nice amount of cleavage and allowed her nipples to poke through. She had a thin gold chain around her neck with a small gold heart and a matching gold chain around her left ankle. To finish the sexy little outfit she had on a pair of thick soled sandals with white straps and cork sole.

After a short rest Dwayne sat up and stared right at the camera again, with the same taunting I got you grin. The joke was on him, he didn’t know that I was more excited than I had ever been. My cock was harder than if I was the one on the couch fuck Jen’s face.

As he turned Dwayne got down on his knees in front of her; a little moan escaped Jen’s lips as Dwayne reached up and pulled the thin straps of her tank top off her shoulders exposing her perky, little breasts. When aroused her nipples give her breasts a nice pointy shape. As hard as they were, as Dwayne tweaked them both between his thumbs and fingers they grew even longer.

As I watched Dwayne rub and pinch her nipples Jen really never seemed to be into it mentally or emotionally. The look in Jen’s eyes said that even as Dwayne tweaked her nipples and fondled her breasts that she was true to her word so far. She hadn’t become another of his cock obsessed sluts.

Dwayne continued to pinch, squeeze and suck Jen’s pointy nipples until she finally began to squirm under his weight. Encouraged by her movement Dwayne continued mauling her tits with a renewed effort. As hard as she tried Jen could no longer deny the pleasure she felt. Moaning and squirming she grabbed the back of his head and pulled him into her embrace. The look in her eyes no longer revealed indifference, now they held the wild fire of lust and desire.

“Oh….uhm….that’s it baby. uah…. I love it when you bite me.”

Jen pulled his head in tighter to her breasts and guided his face over each and pulled it away as he help each nipple gently in his teeth, stretching them.



“Right there baby….”

I had just witnessed first hand the transformation of my sweet innocent Jen, no longer was she my beautiful classy girlfriend. She had experienced lustful desire and succumbed to it. By the end of this night she would no doubt be one Dwayne’s sluts. She would be his greatest conquest, a good girl in love with someone else, raised to control her urges and look down on those who indulge in there desires. He had done that which most would think impossible.

Jen still having Dwayne’s head in her hands pushed him back onto his knees and stood in front of him. She lifted her skirt over waste and slid her lacey g-string panties down her tan athletic legs. As she stood over him she looked down and said, “Well this is what you’ve been wanting, don’t keep me waiting.”

By now we’re hours into the whoring of my girl. I’ve beat my dick sore and came so many times I lost count. But I never lost my arousal even for a minute. Now I couldn’t wait to see Dwayne penetrate my petite hard bodied girlfriend. It was like I was in a trance. Jen also seemed to be interested in only one thing and that was about twelve inches and a pound and a half a nigger dick.

Dwayne went down on Jen like bear eatin a honey hole. the sight of his coal black skin against her golden tan skin was so erotic I blew two loads just on the contrast of their skin color.


“Don’t stop, oh…yeah… fuck me with your tongue!”

“Uhm..slp…slp… you’re pussy is sweet as honey, slp…slp… you’re so hot baby, I can’t’ wait to get in your tight little fuck tunnel.”

“Oh yeah baby…put that big nasty nigger shaft in my pussy…”

“You think you can handle it? You really want to take a big nasty nigger dick in your pretty white pussy?”

“Put it in me… please put it in baby…”

“You got to convince me you really want it and you handle it”

“Baby please fuck me…please please stick the long fat baby maker in my tight pink lust hole”

That’s what Dwayne was looking for. He licked from her ass through her slit up to her mouth and slipped his cock head into her pussy in one fluid motion.

When the tip slid in Jen whole body tensed. He pulled out and reinserted the head a little deeper this time. Each time his cock split her lips he pushed a little deeper.

“Oh god girl your shit is tight….! Fuck this is good pussy! Oh my…fuck this pussy is tight…”

“Please be easy… oh god you’ve got me so full…oh baby please go slow…. it hurts so good baby don’t stop…!”

With his first several strokes Dwayne couldn’t get much more than his big cock head past the tight opening of Jen’s cunt. But using slow steady thrusts he gradually pumped more and more of his massive lust muscle inside her. Each pull left her wanting more while each thrust left her wandering if she could take any more. The harder Dwayne fucked Jen the harder I beat off.

Dwayne carried on with the slow steady fuckin for what seemed like hours until he got the entire shaft in her pussy and his big balls were slapping her ass when he bottomed out.

This is when Dwayne takes control and does it his way. He stretched Jen out nice and slow, he was gentle and attentive. Now she was stretched open and ready to be mounted and bread. Even if there was a condom big enough to cover his massive girth and length he wouldn’t wear it. This was Dwayne’s pussy now, to do with as he pleased when he pleased, how he pleased.

That’s exactly what he did too.

“Now I’m going to show you what a man fucks like, you just a slut like the rest of em. I told you I was going to fuck you and I told you would beg me for this dick before we were through.”

Then he unleashed the beast. Jen was laid on the couch with top pulled down below her tits, her skirt up around her waste, her feet on the floor with her legs spread wide as they could and her ass hanging over the edge of the cushion.

Jen’s ponytail was all but completely loose. Her makeup had faded and ran, she was covered in sweat. Her tits and neck had bite marks all over and her nipples were so pink and swollen they looked like cherries.

As Dwayne started his final assault on my girl’s pussy i began my final assault on myself. With every furious thrust of his cock Jen’s whole body was shook. Her tits bounced. Her head bobbed. Her legs flailed wildly around his waste and she screamed, moaned, and begged for more. He fucked her so hard I thought he would drive his cock through her and out her belly. After 20 minutes of furiously pounding Jen’s pussy Dwayne picked up speed and lost a little of his rhythm.

“Oh god baby you’re going to break me….! Oh fuck yes fuck yes fuck yea….! Don’t stop till I’m knocked up! Yes you big dicked nigger! Oh god damn fuck that pussy…! Don’t stop till there’s a little black bastard growing in me…!”

“Uh..uh..uhm..uh..oh fuck…! You wanna nigger baby huh…! You wanna little big dick baby boy in you…! Oh fuck bitch…oh fuck.. Uhm… it cums bitch..! Here’s your baby you god damn whore….! Oh fu…….ck….! Yea….uh.uh.uh.uh.uhm…….now that’s some good pussy.”

“That’s some good dick. Whoa shit I can’t believe that just happened. Whoa my god that was unreal. How can any mere man fuck that good? You must be some kind of god you big dick nasty bastard.”

I passed out from exhaustion in my room. When I woke up Jen and Dwayne were laid out asleep in his bed with the door wide open. In the floor outside my door was a piece of paper with my name on it. It was a note from Jen.

It said, “Hey baby, if you’re reading this we must still be asleep. Well don’t wake us; we had a hell of a night fuckin. But you already know that since you were in your room watching the whole thing. Dwayne told me everything. It’s sweet that you believed in me that much. I guess I let you down. But I want you to know that I love you and hope that we can make things work. Oh yeah, as far as the debt from you losing the bet last night, it’s not as hard to deep throat it as it looks. I’ll help you with it.”