Hello all,
I’m not sure what is making me share this now. I’ve been a long-term lurker of the sub and have a huge cuckold fantasy. The reason for that will become very obvious in my post below. I hope you enjoy the story. All this is 100% true as I remember it.
Back in the mid 2000s I was starting college at small Division III school in the Midwest. I went there to play football. They can’t give out scholarships for football in Division III but they were able to put together a very nice package for me to go to school for almost free. Since my family could not pay for college I accepted.
Let me tell you about Jennifer. I met Jennifer the first week of school and orientation. We were both biology majors and so were put in the same group. To this day I swear it was love at first sight. Jennifer is the kind of beautiful that when you see her you never want her to walk away because then you can’t look at it any longer.
She’s medium height and petite with long straight dark brown hair midway down her back. She is the biggest blue doe eyes you’ve ever seen in your life. And on that late summer day she had a little sundress on that made her body look amazing.she’s one of those girls that carries her self in a way that makes you believe you could never get her. That’s certainly what I believed. she’s one of those girls that carries her self in a way that makes you believe you could never get her. That’s certainly what I believed.
I remember my first stupid lying to her. I found out she went to a country day school from the same hometown is me although we have never met. When I heard that I said “so did daddy bring the Bentley or the BMW down to school for you, or was it both?”
Looking back that’s douchey as hell but it did make her laugh and started a bit of a back and forth between us. We flirted throughout the first week as we shared multiple classes together due to our majors. We began hanging out to study and got to know each other very well.
Now, what was interesting is that both of us had very similar backgrounds. We are raised in a relatively small town by fairly religious families. We both had one “high school sweetheart” Who we lost our virginities to (I had actually hooked up with a couple girls over the summer before college but didn’t necessarily share that on day one.). We were both the first and our families to go to college.
Jennifer’s personality was infectious. She was incredibly smart (smarter than me), incredibly beautiful, and actually really witty and funny. What was interesting is that while both of us came from religious families we are actually both fairly open-minded both about sex and life in general. She was fairly quiet overall but had no issue talking about sex, drugs, and rock and roll.
I know you’re wanting me to get to the good part of the story so let’s fast-forward a bit. By mid fall I was busy with football and school and Jennifer and I had begun to date. By the way, Jennifer always demanded that she not be called “Jen.” There was apparently a girl she went to high school with who was a total bitch named Jen. Whatever.
Well Jennifer and I were dating. I remember the first time we had sex like it was yesterday. She was so quiet that even while being open-minded I thought I’d have to do most of the work in bed. However, midway through Jennifer turned the tables on me and rolled me over and rode me until I came (and it didn’t take long once she got going).
She continue to surprise me overtime. She had a very vanilla relationship back in her hometown. She actually only had sex with her high school sweetheart about six times. But she wanted to try new things. We tried toys, we watched porn together, we talked about experimenting with one of her friends, tried anal, and had her dress up in all sorts of sexy outfits. She has the perfect body for lingerie… thin and toned with long legs and just enough boobs to fill them out.
Needless to say as a 19 year old horny guy I was like a kid in the candy store thinking of all the possibilities with this girl that I never thought I could get before.
***********
I remember the first time I mentioned watching Jennifer have sex with another guy. We were having sex on the couch in her dorm room. She was in the really nice honors dorms that actually had a common area. So what we’d do is when her roommates were gone we’d actually watch a movie on the regular couch in the common area, then afterwards put on porn (or if Jennifer had her choice one of those soft core Cinemax things) and have sex on the couch while we watched it.
Well anyway, we were right in the middle of it and Jennifer said “tell me something you want me to do, anything dirty, and I’ll make it happen.” I don’t even know what made me say it bc at that point I wasn’t even into cuck or hotwifing or any of it.”
“What if another guy was here, and while I was fucking you you sucked his cock at the same time?” As I said it the idea did turn me on, watching her shared like that.
“I don’t know…”
“Or what if I pulled out and you sucked my cock while another guy fucked you with his big dick.”
“I don’t know if I’m into that babe… what about something else?”
I can’t remember what we ended up doing. Maybe fucking on her roommates bed or something. But we talked after and she just said she liked having sex/making love to me and that’s what it was for her and she had no desire to do that with another guy.
Well time went on as it always does. At some point in the future I came up again. She again said she wasn’t into it but if she was she promised she’d tell me and make my fantasy happen.
To be honest I never really had a specific guy in mind. I’m straight so it def wasn’t any attraction to the guy for me, but there was something that turned me on about imaging just watching Jennifer. I think that’s how it started. I just wanted to see how hot she looked when she fucked. And we had made a couple sex tapes but it just wasn’t the same.
So a few months went by and nothing. After football ended she finally got to meet more of my football buddies since we weren’t so busy.
I’m a big guy, always have been. In college I played defensive end. I played at 6’4 245 lbs. you could call me “husky” but I was extremely strong back then and didn’t have a lot of flab. I have short blonde hair and blue eyes. And yes since it matters for the story, I’m just under six inches and probably average girth.
Well by spring time Jennifer knew my buddies enough to get invited on spring break with us. She accepted which kind of surprised me. She’s laid back and everything yes, but she’s not much of a kegs, beer bongs, and blare music in the hotel room type. She’s more have a bottle of wine, cook dinner at night, and have sex until morning type.
But she went. We got down there and did the basics of what spring break is. Parties, drinking, a rule that the one adjoining room could be “reserved” for sex at any point by leaving a beach towel outside of it.
About the third night in we were partying and drinking when Jennifer came to me. “You know how you have that fantasy of me being with someone else?”
My spine tingled. Holy fuck, where did this come from? I nodded.
“I want to fuck Darius.”
Darius was one of the guys with us on the trip and was another defensive end on the team. We had become good buddies over the summer because we were both d line freshmen. He was a super nice guy and cool as hell.
Darius had an interesting story. He was black (called himself “middleskinned” because light skinned black guys called him dark skinned and dark skinned back guys called him light skinned), 6’6 and weighed around 240 (that was his playing weight anyway). He kept his hair short. He was a physical specimen, one of those chiseled guys where you see extra muscles you didn’t even know humans had. He also had that impossibly thin waist with tree trunk legs you see in athletes. He had actually had a scholarship to a d 1 school but lost it due to legal trouble that he didn’t even get charged with. He then came to our school where he started as a freshman and led our team in sacks. He became VERY popular around school.
And now Jennifer wanted to fuck him.
I brought up that she had been drinking but she said she had been thinking of this since the day we got to Florida. I asked her how she wanted to go about making it happen and she just said “leave it to me.”
She went and talked to Darius. Twenty minutes later I saw her put the towel in front of the spare room door and motiontonme. I entered the room, a typical shitty two double bed hotel room.
“So here’s the deal, we’re gonna start and Darius is going to come through the other door. I want to make your fantasy happen but I don’t want the entire world knowing about it when we get back.”
My heart was pounding. Holy fuck we were going through with this. I considered calling it off right then but I couldn’t. I felt like for her to go all the way from saying no to this to actually setting it up I couldn’t let her down now.
We started making out, a look of excitement in Jennifer’s eyes as we started. She was wearing a royal blue bikini, her tanned body accentuated by the bright colors. Her bright blue eyes were the only thing more striking than the bikini. I had on swim trunks as did Darius when he walked in.
“Didn’t miss the party did I?” Darius said as he walked in the front door.
“I’m not that fast” I tried to joke.
Darius was actually really cool about things. He asked if I was 10% okay wth this and I said yes.
Jennifer and I started kissing again. Darius came up behind her and untied her top. I watched as it fell down, her 34C perfect boobs now exposed to Darius, a guy who I hadn’t so much as told about Jennifer and I’d sex lives to this point. And now I’m watching as he reaches his hands around and plays with Jennifer’s breasts.
We continued this way for a while, Darius eventually helping himself to removing Jennifer’s bottoms as well. Jennifer got down on her knees and began giving me head while Darius watched. It’s funny, Jennifer was good in bed but giving head wasn’t necessarily her strong point. Never enough enthusiasm.
She reached to the side and undid Darius’s bathing suit and it dropped to the floor. In front of us was a cartoonishly large black cock. He was semi hard but already longer and thicker than me. I had probably seen it in the locker room but obviously didn’t take note previously. Jennifer began stroking him while continuing to suck on me.
All at once she pulled off of me and turned to Darius. It was almost hilarious the size difference. Jennifer took him on her mouth and began sucking his cock while stroking mine. Her hands looked tiny on him. He became fully erect within a few seconds. I didn’t take out a ruler but he had to be close to 9 inches. And thicker than anyone I’ve ever seen.
She could barely get past the head of his dick with her mouth but she went for it. She was sucking and licking, using her hands and tongue like she was trying to win a contest. Darius was loving it, using his hands on the back of her head to guide her, but not being so forceful as to make her gag. She seemed to love it. She was sitting back on her legs now going to town.
This is where I first noticed something different. I mentioned how she gives not so enthusiastic head. Well, with Darius it was different. It was like she was trying to impress someone. And I don’t know maybe she was. She was working it with mouth and tongue, with one hand all the way at his base and one stroking him. She kept looking up at him, making eye contact as if she wanted some non verbal approval. What she got was verbal approval. Darius was very verbal. I’m not shy in bed but I think because Jennifer was quiet I had become fairly quiet. But not Darius. “Oh fuck yeah girl you’re so good.” “Yeah Jennifer, fuckin take that baby girl.”
She loved it. After a few minutes Darius suggested taking it to the bed which we did. We laid Jennifer back. Yeah began to kiss around her perfectly shaved pussy. Jennifer had a true “innie,” a beautiful tight little pussy which she kept shaved or waxed at all times.
Darius positioned himself at the head of the bed where he began kissing and sucking on Jennifer’s tits. I was surprised to find Jennifer already soaking wet. Jennifer was a huge fan of oral and I had always known how to get her off. Being that she was tight she pretty much required oral before sex because it was otherwise painful for her. I was used to having to get her wet but she was soaked tonight.
I kissed her clit and began licking it, using my fingers to tease her pussy and her thighs. Looking up I could see her squirming and quietly moaning. She had pushed Darius up and grabbed his cock once again and had it in her mouth. He kept playing with her tits and pinching her nipples (which I knew she loved).
I wanted to get her off orally but she was ready. “Tyler just fuck me already,” she groaned out as she momentarily took Darius cock out of her mouth.
Now here’s where things get really interesting. I’d love to say me and Darius went thrust for thrust but that would be a lie. The moment just overcame me. For one, when I pushed into Jennifer Darius looked at me and said “could you not come in her? It would just be weird man because… you know.”
Secondly, the scene was fucking unreal. Jennifer is on her back looking incredibly sexy, taking my cock and sucking Darius like there’s no tomorrow. I lasted somewhere between one and two minutes. I told Jennifer I was close. I pulled out and came on her stomach, the intensity killing me.
Jennifer cleaned up as I took a breath. She asked if it was okay for “us to continue” pointing towards Darius. What the fuck was I gonna say guys? I said yes…
Darius confidently moved down the bed. “Hey y’all got a condom?” I knew there was a drawer full next to the bed. This was the sex room after all. I motioned to the drawer. He grabbed one and put one on. He pulled Jennifer’s legs apart. “Last chance Ty, you 100% you’re cool with this?” I nodded.
Darius began to push his cock into my girlfriend.
“Oh shit! Slow down!” Jennifer gasped.
The scene was laughable. Jennifer is lean, with nice curves but is still thin and petite. She had an amazing ass, but this was before the days of yoga pants and daily squat routines. Her butt was small but tight. And Darius’s huge body and his monster cock just made her look tiny under him.
He slowed down and pushed inside her. I watched her wiggle and gasp as inch by inch disappeared. She smiled once he was all the way in (he actually couldn’t fit all the way in but close enough). He began slowly thrusting in and out of her.
I began stroking my cock at the scene. Holy fucking shit, I’m actually sitting here watching Jennifer fuck another guy. I thought about going over and trying to get involved but I was frozen in place.
Jennifer was slowly swaying in motion with him. As he picked up the speed Darius reached down and played with her tits, sending her into a frenzy.
Now, I’d had lots of sex with Jennifer. While she was enthusiastic in bed she was never porn star loud. I actually appreciated that about her. She’d generallly just breath hard and moan slightly even when she came. A couple of times I got her to scream out a bit or say my name. She was intense but quiet.
But not today. As Darius fucked her, picking up speed constantly, she moaned out loudly. “Oh fuck, fuck, yes fuck me!” She was saying, her mouth much dirtier than I’d heard her be when we were together.
Darius turned her sideways a bit and spanked her ass several times as he thrusted quickly in and out of her. I could see her face twist as she began to cum. She grabbed Darius’s thigh and squealed (“fuck I’m cumming!”) and bit down on her hand as the waves of orgasm washed over her.
I watched as the orgasm subsided and Darius without much effort flipped her over on her belly. He reentered her in doggy style a perfect little ass pointing up in the air. He grabbed her ass with both hands begin thrusting in and out of her. She was already biting the pillow and moaning as he pounded into her.
“God he’s so fucking big” she shouted towards me with clenched teeth.
“You like it babe?”
“Oh my god so. Fucking. Good.”
They continued in doggy until she came again. Two orgasms already matched my record with her.
“Oh shit,” I heard Darius say. He pulled out and I could immediately see the problem. The condom was hanging half off his dick, practically shredded to pieces. To be fair, it hasn’t really fit right to begin with.
“Fuck,” he said looking at me, “I’m clean man I swear. What should we do?”
Jennifer answered for us. “I’m on the pill, just let me fuck you…”
It was true, Jennifer had been on the pill since just after we started dating. We both hated the feeling of condoms and he whole rigamorole of putting one on and stopping in the middle of passion. Plus, I figured if we were protecting from stds Darius had already been fucking her for lord knows how many minutes with a broken rubber.
I shrugged in a “do whatever you want” sort of mannerism.
Jennifer smiled and motioned for Darius to roll over on his back. He happily obliged. I watched her climb on top of him and expertly reach behind her self and guide his dick back into her. She pushed her pussy down onto him slowly but surely.
I watched her lean back, her near perfect body arched backwards she began to ride him. She used her hands the balance on his chest and she picked up speed, taking his cock more and more rapidly. She was now pretty much bouncing up-and-down on top of him riding him like crazy.
It was at this point that I realized. I had made love to Jennifer, I had had sex with Jennifer, but I never really FUCKED Jennifer. Not like this anyway. Not like two animals just enjoying the rawness of it.
“Fuck you’re so good Darius,” she said, looking at him then me. She leaned forward and they made out as she used her hips to keep thrusting on him. The site of them kissing was jarring but hot. I had pictured her fucking other guys a lot but watching them passionately kiss was a whole different level.
They made out for several minutes with her very sensually riding him, her hips arising almost a foot off of him each time to accommodate his giant cock.
She finally leaned back and we can bounce and harder and faster. He reached up and grab her tits and play with them, pinching each nipple back-and-forth. He began grunting. She was moaning more loudly than she ever had with me.
“Fuck I’m gonna cum,” Darius said. “Where do you want me to cum?”
Jennifer looked straight at me. “Cum in my pussy babe.”
“Oh shit….” was all he could muster.
Jennifer took her high speed bouncing down to a very purposely slow grind with her hips. Darius used his hands to guide her ass up and down on him, thrusting his dick deep inside of her as he came.
“Oh fuck. Fuck FUCK,” he said as he slapped her ass and finally both of them collapsed, she on top of him as they hugged and kissed as their orgasms slowed.
I didn’t even cum standing there. I was in shock and awe of what I just saw. It was amazing and sexy and scary and crazy.
Eventually Jennifer rolled off of him and they laid there. We shared a few jokes and chatted for a while before Darius returned to the party.
If you guys like the story I have plenty more I can share. Jennifer and I did it for another six months or so after that I have plenty of other stories up to when we broke up. Let me know if interested. I’m glad to answer any questions.
Source: reddit.com/r/gonewildstories/comments/8gzsbg/mfm_back_in_college_i_shared_my_girlfriend_with
Reads like something from literotica, in both a good (well written) and bad (almost too perfect of a cuckold fantasy to be real) kind of way.
How did your sex life change after that?
Wow
No sloppy seconds for you? Hot story!
????
That sounds fucking hot! Was your relationship strained in anyway after that though?
Yeahhhhh wowwww!!! ?
Did you break up so she could pursue bigger cocks?
Coming back to this one.
What ever happened Jennifer?
That’s hot. I was hoping she’d stay on her knees for more. maybe next time.
Very nice I would love to read more
Did you two only have threesomes with guys or did you have any with her friends?
Did you two only have threesomes with guys or did you have any with her friends?
hot story op. definitely share more stories if you’re into it. im a big fan
any videos or pictures of the times you’ve played?
Thanks. This is one of the best stories that I’ve read on here in quite some time. More stories would be most appreciated.
Damn that’s hot, hope you share more
Tell us more please.
Holy shit. You better write more stories. Don’t leave us hanging now..