I grew up in a college town, Gainesville, Florida, home of the Gators, and my high school friends and I played basketball on our high school team. We were good, but not good enough to earn college scholarships.
My name is James, and my four friends and I all had good enough grades to get into the University of Florida and we took advantage of the intramural program to continue playing basketball, which helped us stay in shape. We also played pick-up games when the intramural games were out of season, often playing with older, married alumni in their thirties and forties who still lived in the Gainesville area and had passes to use the college gym.
I had a normal college experience, dating girls and hanging out with my friends, until I met the girl of my dreams in January of my junior year. I won’t use her real name, because it would be recognizable to many people, and I’ll call her Jillian for purposes of this story, for reasons I’ll explain.
We’re married now and still in living in Gainesville, and this story describes an event that presaged and continues to influence our very active cuckold lifestyle.
Jillian is from Orlando and was on a full basketball scholarship with the Gators. She was a power forward, and at six feet and one inch tall, and weighing one hundred and fifty-five pounds, she was fit, athletic, and physically imposing, in addition to having, for a female athlete, unusually large, D-cup, breasts. She’s also pretty, in a slightly masculine way, and in the face looks a lot like the fitness guru, Jillian Michaels, which is why I’m calling her Jillian in this story.
I’ve always been attracted to strong, dominant women, like the actress, Jennifer Garner, playing the role of Sydney Bristow in the ‘Alias’ television series, or her more recent movie, ‘Peppermint’, and Jennifer Lawrence in her role as Katniss Everdeen in ‘The Hunger Games’ movies. Jillian has a strong and confident personality and has a take-no-prisoners and live-life-to-the-fullest attitudes towards life, just like those characters.
I closely followed Gator basketball and was aware of Jillian’s aggressive playing style and success on the court, but I didn’t meet her until a party a couple of months after the end of the season in our junior year. I was immediately attracted to her outgoing and vivacious personality, and for some reason, that I’m forever grateful for, she was attracted to me.
After dating her, non-exclusively, for a while and hanging out with some of her friends from the women’s team, I found out that she was open about being sexually active with other boys, at the same time she was fucking me. I even found out that she was having trysts with several of the lesbian players, and they would sometimes kiss, hug, and rub each other’s tits, right in front of everyone at parties.
I’m a big guy, at six feet and three inches tall and weighing two hundred and ten pounds, and decently hung with a circumcised, thick, seven-inch cock. But I knew from things she and the other girls said that she loved fucking guys with bigger cocks. I think I had one advantage, though. Since beginning in my junior year in high school I had developed an obsession with and talent for sucking pussy, and she always loves it when I eat her out. None of the other boys would suck her pussy, given her reputation as a slut.
I tried to be with her as much as possible, and from the taste and sliminess of her pussy sometimes, I knew that I sucked it after she had recently been fucked by other boys. I think it excited her knowing that I was slurping down the slime from other boys. But for some reason that I don’t understand and can’t explain, it aroused me knowing that she was a free spirit and fucking other boys, and I didn’t mind swallowing their cum, since I was used to eating my own cum anyway.
We dated for the next year and fell in love, getting engaged after the basketball season in our senior year. We got an apartment together then, and she was trying to stay true to me, but I knew that she was still seeing one boy on the side, who has an especially large, nine-inch cock, and suspected that she was also fucking two others.
The primary and most interesting incident in this story occurred shortly after we were engaged, one a night when my friends, Kevin, Michael, Craig, and George and I were scheduled to play a pick-up game with five older guys in their early forties, named Chet, Brian, Doug, Jeff, and Dave. Jillian went with us to watch, and it seemed kind of funny that a dominating, college, female athlete, in her prime, would go to watch once-good high school guys and older married men play.
George, my fourth friend, hadn’t showed up as planned, and Jillian couldn’t resist warming up with us while we waited. My friends and the men we would be playing couldn’t keep their eyes off Jillian, and the older guys had no idea that Jillian and I were engaged. She was wearing tight, black leggings and a midriff t-shirt. Her ass and prominent camel toe looked delicious her tight pants, and the t-shirt flopped up enough that they saw the rounded bottoms of her big, braless breasts when she jumped to take shots.
We had been waiting for George for over twenty minutes, and the apparent leader of the older guys, named Chet, expressed their frustration. He said, “Come on guys, this is bullshit. Where’s your other guy?”
There wasn’t anything I could do about George not showing up, and I replied, “Sorry, Chet, I guess we’ll have to cancel. Maybe we can use our time to shoot around a little.”
It was reasonable to assume those men followed Gator basketball and should have recognized Jillian, but apparently, they didn’t, or Chet wouldn’t have wanted her to play. He asked, “Wait, what about your lovely lady friend? She looked pretty good warming up. Maybe she can keep us with us guys and take the place of the other guy.”
I knew that we’d beat them badly with Jillian on our team, but there was one problem. We had agreed that my team would be skins, since one of the older guys was embarrassed about being overweight and showing his body, and I knew we’d have to change that.
So, I responded, “We’ll need to ask Jillian if she wants to play, and we’ll also need to make my team shirts.”
I didn’t know if Chet was dead serious about not changing to skins, or if he just wanted to have a little fun teasing Jillian, but he said, “No way we’re changing. I guess the lady will just need to find a bra or something.”
Jillian had been listening to everything and was feeling a little feisty. My friends and I looked at her with our mouths gaped open when she answered for me, saying, “I’d like to play, mainly so I can kick your asses, but I don’t have a bra with me. But what the hell, Chet? If you’ll take off your shorts then I’ll take off my t-shirt, an we can play that way.”
Chet thought for a few seconds and smiled before replying, “Yeah, well, that’s a tempting offer, sweetie, especially after seeing those melons of yours moving under your t-shirt when you were warming up. But I’m going commando right now, and not wearing any underwear.”
Everyone was in rapt silence and amazed as she took it farther, and said, “Yeah, I noticed some bulges a few times, flopping in your shorts when you were running around. Fair is fair, though, and if I’m bare on top then you should have to be bare on the bottom.”
I wasn’t sure where their conversation was leading or if Jillian was serious about taking off her t-shirt, or even what might happen if she did. But knowing her the way I did, nothing would’ve surprised me. My friends knew her reputation and sometimes teased me about dating and then becoming engaged to such a slut, so they were likely getting excited at the chance to see her breasts too.
The gym was becoming sexually charged in anticipation as we waited for Chet to answer. We had the last court time of the night, and the gym was empty except for us, so I knew that if they did follow through with it, no one else was around to see them, except maybe for a janitor.”
Chet finally smiled and said, “Okay, sweetie, I’ll show you mine if you show me yours.”
He started pushing down his shorts as Jillian took off her t-shirt, and there was an audible gasp in the gym when her big, shapely, melon-sized breasts swayed and jiggled in front of her. While everyone else was focused on Jillian, I glanced at Chet and was impressed with his package. Even though I had eaten plenty of other boy’s cum from her pussy and had seen other boys in the showers many times, it was an unwritten guy’s rule to not stare at other guy’s junk, and I had never even thought about playing with other boy’s dicks.
Jillian was staring at his package too, and smiling, and I couldn’t help thinking that his still soft, thick, veiny, uncircumcised cock with a mushroom head looked attractive hanging there, with a plum-sized set of hairy balls hanging down as far as his cock, which looked over six inches long. Knowing how much Jillian likes big cocks, she had to be impressed with his meat.
We all stared, Jillian and me at Chet’s cock, and everyone else at Jillian’s tits, for what seemed like minutes, but was probably only a few seconds. Then I refocused and said, “Well, uh, it’s interesting, but a little surprising that both of you really stripped down, and I’m sure that everyone is happy about it. But we’d better start the game before this gets any more uncomfortable.”
It was arousing watching Jillian’s breasts swinging and shaking and Chet’s cock and balls swinging as we went back and forth on the court, and they took shots. That made it hard for everyone to concentrate on the game. Jillian was merciless on defense, and scoring basket after basket on offense. It didn’t help their concentration that they were staring at her breasts swaying and bouncing either.
I so much enjoyed watching Jillian playing bare-breasted, and even took some long looks and Chet’s huge genitals. As the game went on and the men got more and more frustrated trying to defend and score on her, I noticed that the older men found opportunities to not so subtly touch her breasts and ass under the guise of defending against her charges to the basket, and my friends started trying to do the same.
Then things heated up when we were taking a break after the first quarter. As Chet stared at Jillian, shifting his gaze from her breasts to her nice ass and camel toe, he started getting an erection. And because she had been focusing on his cock and balls flopping around anyway, she noticed and just had to be a smartass.
She asked, in a teasing way, “My oh my, Chet, am I causing that thing to get bigger? Do you really like seeing my bare tits and big, shapely ass that much?”
Remember that Chet didn’t know that Jillian was engaged to me, and he wasn’t holding back his words. After being embarrassed at first, when everyone looked down at his half-hard cock, he smiled and recovered, saying, “Damn, girl, you’re such a beautiful fucking tease, and you know fucking well how you affect men. Maybe you’d like to help my lady pleaser get bigger. I’ve never had any complaints, and I know that I could please you.”
Jillian was never one to pass up a challenge or a big cock, and probably everyone except me was surprised when she stepped in front of Chet and gripped his hardening cock. The gym was silent, except for the slight squishy sound as the precum started flowing and his thick foreskin slid back and forth over his big, mushroom cock head, as she began stroking his thick, veiny shaft.
I didn’t think she would take it farther, and even I was shocked as she dropped to her knees, saying, “My, Chet, it’s nice and big now, but I bet I can make it bigger.”
She opened wide to take his huge, oozing cock head into her mouth, and began sucking and licking and swallowing his precum. All the other men, including me and my friends began rubbing our cocks, and Chet began moaning loudly and holding her head on his cock. I was even more aroused when I saw that Chet’s cock is between nine and ten inches long. With nothing more being said at that time, the others, including my friends, sensed that a gangbang was about to happen, and they got involved.
Jillian was gripping and pulling on Chet’s ass, helping to pull his cock into her mouth as he began fucking it, and Brian and Doug got on either side of Jillian, and began fondling and sucking her breasts, as my friend, Kevin got behind her and began rubbing her ass, pushing deeper and deeper down into her ass cleavage, until he was rubbing her pussy from behind.
I had never seen Jillian having sex with anyone else, although I had cleaned up the tasty, juicy remnants of her fornications many times, and I wanted to see her truly fucked. My two other friends, Michael and Craig, ran over to the corner of the gym and brought back four of those thick, gymnastic mats, and they stacked them right in front of the bleachers, next to where Jillian was still sucking Chet’s cock.
The mats were stacked about two feet high, and when Jillian pulled off Chet’s cock, and just before lifting his big balls to her mouth and sucking them, she looked at me with pure lust in her eyes.
The other men found out we were a couple then when she said, “Sorry, honey, but I just can’t pass up this big, beautiful cock, or any other of the cocks here for that matter. You’ll be a good boy and help me, won’t you? I still love you very much and want to marry you.”
I wasn’t sure what all she had in mind about me helping her, but I wrongly assumed that it just meant me cleaning her pussy with my mouth. She sucked Chet’s cock for another minute or so, and then Chet’s friends pulled her away and pushed her onto her back on the mats. They pulled her tight leggings down and she spread her legs as Chet moved between them, with his rock-hard cock and huge cock head poised in front of her pussy.
All the men had taken off their shorts, underwear, and jock straps, and my friends and Dave were standing there stroking their cocks, waiting for their turns at doing something with Jillian. Brian and Doug moved beside her and resumed sucking and fondling her breasts, as Jeff straddled her face and fed her his balls. I got between Jillian’s and Chet’s legs, and watched in amazed arousal as the fat head of his huge cock spread her labia and disappeared into the depths of her womanhood. He began fucking her as his balls slapped noisily on the mat and against her thighs, and I was jealous of his big cock, and being able to give her that kind of pleasure.
With all the visual stimulation beforehand, and then having Jillian sucking his cock, Chet didn’t last long in her pussy. Nobody had said anything about the men wearing protection or whether she was on birth control, and just at the last moment, when I saw his perineum throbbing and balls drawing up, I knew Chet was inseminating her, just as I heard her choking on Jeff’s big load in her mouth.
Chet moaned and said, “I hope the fuck you’re not on birth control, you fucking whore, because I’m breeding you sweet pussy. I’ve got plentiful, motile sperm and shoot big loads, and have always been successful knocking up my wife on the first try. I’d love nothing better than to give you my baby.”
I knew from talking to her friends, and other rumors, that Jillian loved to be fucked hard and talked to rough during sex, and she and some of her friends liked to enhance the experience for boys by sometimes telling them they’re unprotected and close to their fertile times. But I knew for sure that she was on the pill and was always conscientious about taking them.
So, I wasn’t surprised, when after swallowing Jeff’s load and he pulled away, she acted upset and said, “Oh fuck, no, Chet, I was so aroused by your big cock that I didn’t think about that! It’s been a week and a half since my last period ended, and I felt the huge load you pumped into me! Pull out now and give James a chance to suck your baby batter out of me.”
My friends and the other men were amazed when they saw me move between Jillian’s legs, and Kevin told me later that Craig looked like he was going to throw up when he saw Chet’s cum running out of Jillian’s gaping pussy before I covered it with my mouth and began sucking and licking it. Chet had shot a big load, and in addition to the tasty cum I was eating, a lot of his cock milk had already drained out of her and onto the mat.
I sucked her pussy clean as Brian and Doug continued sucking her breasts, and when I pulled back, Kevin was moving between her legs. Jillian looked at me and I found out how she was going to handle the being-fertile guise, and what else she meant about me helping her out.
She said, “Kevin, go ahead and fuck me, since if I was going to get knocked up, Chet probably would have already done it. I love bare, cum shooting cocks in my pussy, so fill me to overflowing with your juicy seed. And, James, be a good boy and clean up Chet, to thank him for the good fucking he gave me.”
I had never even thought about having homo sex, but in the context of the gangbang, and with her telling me to, I took Chet’s slimy cock into my mouth to suck and lick it clean. Kevin was already busy fucking Jillian when Chet said, “Damn, guys, we hit the jack pot with these two lovers. I love her cunt and mouth, and he’s doing a fine job on my cock with his mouth. And I really would like for one of us to knock up this cunt.”
Kevin was fucking Jillian, with what I found out was an average length, but very thick, soda-can-sized cock, and when he saw me sucking Chet’s cock, he said, “Holy fucking shit, James, if I had known you suck cocks, I’d have let you suck me a long time ago.
I sucked Kevin’s cock clean after he inseminated Jillian, and that was the beginning of round after round of my friends and the older men fucking her, while at the same time taking turns sucking and fondling her big breasts.
By the time it was over, Jillian had either sucked off or fucked each of my three friends and the five men twice, and three of them three times, and I had swallowed all the loads that were pumped into her pussy. And even with me cleaning her pussy after each fucking, the top, plastic-upholstered mat was slimy with their cum and her juices, and the gym wreaked of the aroma of sex. Jillian seemed to enjoy sliding around in their cum, and her ass and thighs were slimy with it.
I could hardly believe her stamina at taking those nineteen loads in either her mouth or pussy, and I loved seeing her pure, animalistic lust when satisfying all of them. This might sound strange, but I felt closer than ever to Jillian that night and had gained a new respect for her unbridled passion and libido. I knew then, more than ever, that I wanted to be a part of her life.
It was also clear that I had crossed a line and was beginning to enjoy cleaning their cocks and eating their cum so much, that I even became Jillian’s fluffer, sucking their balls and cocks to get them hard for her.
We continued playing pick-up games with those men, and always scheduled our weekly court times to be the last in the evenings, so we’d have the privacy to continue the orgies. My friends also visited our apartment whenever they were horny, which was most of the time, and they had free access to her big tits and pussy.
Kevin was my best man at our wedding, with Michael, Craig, and George being groomsmen, and Chet and his friends attended the wedding. The other guests had no idea that Jillian was fucking all of them, and in fact, the remnants of Kevin’s cum were oozing out of her pussy and down her inner thighs during the ceremony.
We are now married and living in Gainesville. Jillian has a degree in physical education, and she became and assistant coach for the girl’s team. She has lesbian sex with one of the other coaches and two of the girls on the team, and we have continued our cuckold lifestyle with my friends, the older men, and other men that have come into our lives.
