The Kinkiest Thing I've Ever DonebyDaveinMO©
This is a true story about the kinkiest thing I ever did and, most likely, ever will do. It happened seven years ago, when I was a junior in college. I changed everyone's names, but otherwise everything really happened.
I went to a large Midwestern university. During my first year there, I became good friends with another of the guys on my floor in the dorm, Jeff. We didn't have a great deal in common – I was a suburbanite who grew up ten minutes away from the downtown of a decently sized city, whereas he had grown up on a farm in a town with a population in the low thousands – but we hit it off really well, and soon I was mostly hanging out with him and his friends.
During sophomore year, Jeff, myself, and a couple other guys rented a condo near the university. Jeff was a really outgoing, friendly guy who knew a ridiculous amount of people, so parties at the condo were not a rare occurrence, and it was at just such a get-together that I met my first really serious girlfriend, Jenny. Pretty soon, to the major consternation of my friends, I was spending more time at Jenny's than at the condo, and the next year we got an apartment together.
Jenny was an interesting girl. Like Jeff, she had grown up in a small town and, though she would never admit it, a lot of the conservative values of the area had rubbed off on her – she rarely drank to excess, never did drugs, had never slept around (she had only had sex with one other guy before me – a boyfriend in high school), and kept to her studies. At the same time, she had a real disdain for all things rural, was gung-ho about finding her way to a big city after school, and generally tried to cultivate a cosmopolitan and sophisticated personality, double-majoring in Women's Studies, even though she had no aspirations toward academe and wanted nothing other than to become a successful businesswoman.
In any case, we were a fairly typical college couple – a little too young and immature to be forging a serious relationship at that point in our lives and thus doomed to an eventual break-up, but still a good couple – we didn't fight a lot, we were never unfaithful to each other, and we generally had a good time together.
The best thing about the relationship was the sex. Jenny knew practically nothing about sex when we first got together (the first time I turned her over during sex, she thought I was going to try to fuck her ass – she didn't know what doggystyle was). I was your average 21-year-old horndog, and I made her cum for the first time in her life (and many times thereafter). Despite her borderline-prudish nature, she came to trust my mildly kinky exploits, and eventually I bought a pair of faux-fur-lined handcuffs and a blindfold, and gave her her first bondage experience. She really enjoyed it, but not in that animal-lusting kind of way you sometimes get when a girl is exposed to her most taboo desires. I think she mainly just liked the fun, kinky idea of it.
Jenny didn't know just how kinky I could really be. I've always had a thing for making women cum. It's not just the seeing the pleasure on a woman's face – though that is a big part of it. It has to do with the idea of her relinquishing complete control over her body. Being in complete control of a woman to the point that her own body is doing things involuntarily. Given this fetish, I pretty naturally progressed from the idea of the simple idea of the female orgasm to the idea of the forced female orgasm. Making a woman cum against her own will.
Now, whatever you may be thinking of me, I'm no rapist. Submitting another person to humiliation or pain has always just been a turn-off for me, and I'm not so stupid as to think that fucking another woman against her will would be anything but a painful and humiliating experience. So that gave rise to a dilemma – how could I ever explore my fetish to its full potential? Self-denial would be the obvious answer, and is basically what I've resigned myself to since college, but discipline in sexual matters is not necessarily the forte of a 21-year-old guy, and I thought hard about how I could explore this desire with Jenny.
Eventually I figured out something of a solution. Given that Jen was living with me and all, actually making her cum against her will was something of an impossibility – consent was more or less inextricably bound up in the entire arrangement. It would have to be another man. It figured it would take a lot to get her beyond the point of reluctance (to put it mildly), so the guy would have to be really good looking. I thought immediately of Jeff. I'm not gay, but guys can sometimes tell if another guy is good-looking, and Jeff was one of those guys. He had the blonde hair and blue eyes that you find a lot in that part of the country (originally populated by Scandinavians) and his face was sort of a combination of boyish, fresh-faced good looks and more of what I assumed to be "macho" features (strong chin, e.g.). And, between working on the farm in the summer and going to the gym practically every day during the school year (he eventually gave up on trying to drag me there every single time), he had a pretty strong, fit physique. And, if I needed any other indication I could just look at some of the girls he brought home, who were generally smoking hot. Also, Jeff and I were good enough friends and he was a good enough guy that I knew he wouldn't go around telling people about it. My own reputation wasn't that big of a deal – finding out that a college-age guy is a horny perv is no big news flash – but the last thing I wanted was for people to be talking about Jenny.
Jeff and I were hanging out one night after a pretty decent amount of booze when I broached the subject. Unfortunately, he declined, telling me how he wanted us to stay friends and going on to talk about how he'd ruined his friendship with another guy we both knew by sleeping with that guy's ex (even though they were long broken-up, the guy still got really sore about it). But he was pretty cool about it – he didn't call me weird or anything, it was more of a polite decline.
I think it was about two more months that passed without anything happening in regard to my little fetish. Actually, this was a good thing, as I'd continued to build on the fantasy in my head, and had more of the minor details worked out. I can only speculate on what changed Jeff's mind, but he had recently gotten out of this very brief and troubled relationship with a pretty head-case and had been taking a break from girls and the night scene. So he'd been kind of stewing in his own juices, so to speak. Also, I know if it was me, and I knew for a fact that, at any time of my choosing I could have sex with a girl I'd never been with, no strings attached, and in a way I'd never done it, that would eat at me over time. But, as it happened, we were hanging out again a couple months or so later when he asked me if I was still interested in what I'd talked about before. I said most definitely. I just asked Jeff that he never tell anyone and that he follow exactly the plan I was going to lay out to him. My biggest concern is that he'd deviate from what we'd talked about, the whole thing would go awry, and I'd be in a ton of trouble. Even if things went perfectly, there was a chance I could be in trouble, but I was too much of a slave to my desires by that point to back away. But Jeff agreed to do what I asked.
The next day I went to the adult store and bought a better blindfold and a pair of ridiculously overpriced leg braces – the kind where the leather fits around the knees and connects to straps that can be secured around the frame of the bed. By that time the school year was already over, and Jenny worked evenings, always getting home later than me, so I had time to set everything up perfectly. I even went out and got some little tea light candles to sort of set the mood in the bedroom – there was always the chance that Jen just wouldn't feel like having some kinky sex that night, so I figured that if she saw I had gone to some trouble she would be less likely to decline (though she was usually fairly good at not denying me). That evening, after she got home, she saw the bedroom and asked what I had in mind. I told her I wanted to tie her up, and that I wanted her to put on her lingerie first. She had this negligee that was like a slip that ended just below her pussy and had basically a bodice top with strings that could be untied to let out the breasts. She said to give her a little time to unwind and then she'd meet me in the bedroom. I said okay and got on the computer, pretending to check my e-mail. In actuality, the plan was for me to e-mail Jeff the time he was supposed to come over (he was to be checking his e-mail every few minutes). When Jenny appeared in the doorway of the computer room in her slip, I quickly sent the e-mail I'd already typed, telling Jeff to leave for our place in about ten minutes. Jenny and I went to the bedroom.
She was a little surprised by the leg straps, which I'd already strapped to the frame, but she went along with it good-naturedly. I handcuffed her wrists to the bedposts and, after a little struggling, managed to get her legs securely in the straps, which forced her legs apart, exposing her naked pussy. I kissed her on the mouth and the neck and sucked her earlobes. I untied the bodice part of her slip and played with her tits. I ran my hands up and down her inner things and eventually started rubbing her pussy. Jeff took a little longer to show up than I'd expected, which actually wasn't that big of a problem as I had time to work Jen up pretty good.
Other than being about ten minutes late, Jeff executed his part of the plan perfectly. I had left the door unlocked and he came in so quietly that even I didn't know he was there until I saw the light enter the room when he eased the bedroom door open. Jen didn't know a thing. And, just as I'd asked him, he'd already taken his clothes off in the living room. It was kind of weird to see my friend standing there butt-naked, but, then, the whole thing was kind of weird.
I started licking Jen's clit while Jeff watched. I didn't want to make her cum yet – she had a really hard time having more than one orgasm, and I didn't want to ruin it – but the idea was to get Jeff hard before he got on top of her. After about a minute, I looked back, and he was silently stroking himself, already fully erect. I remembered when a girl Jeff had been with a long time ago had gotten drunk and told me he had a huge dick, so I was kind of disappointed it wasn't this monster cock I'd worked up in my imagination, but it was a little longer and thicker than mine. All in all, a pretty good size.
The whole time I had kept my clothes on, so it would seem natural when I got off the bed momentarily. Just as we'd planned, after I'd taken off my clothes, Jeff got up on the bed kneeling between her parted legs. I remember that the first think he did was play with her tits, just sort of squeezing them and moving them around in circles. Jen didn't act like anything was up; I'm sure she never knew what was going on before the blindfold came off. Just as I'd asked him, he made sure not to kiss her yet or get to close to her face, as I'd worried that would give everything away. Then he started licking her pussy. It was really weird watching another man lick my girlfriend's pussy while she made little sighs of pleasure. To be honest, I actually did feel a pretty strong twinge of jealousy, then and throughout the whole thing. But the hotness of it all really outweighed that. I remember that my heart was pounding so hard I was worried Jen would hear it and figure out something was up.
But everything went exactly according to plan. Jeff stopped licking her pussy before she came and got on top of her. Just like I told him, he was teasing the opening of her pussy with the tip of his cock. Jeff wasn't wearing a condom – I hadn't really mentioned it one way or the other. It was at about this point that the feelings of jealousy became really strong, but I kept them under control, and just stood off near the closet, watching the whole thing. I was so engrossed in it that I didn't even think about the weirdness of standing there naked, my dick hard as a rock, with my good friend right there in the room.
So Jeff was on top of Jenny, his cock just teasing her. Then he pulled the blindfold off her face with the hand he wasn't using to prop himself up. I'll never forget Jenny's reaction. Immediately, she screamed – not like one of those long, drawn-out horror-movie screams, but more of a startled yelp, like when someone pops out from around a corner and you didn't know they were there. Her face was pretty much the epitome of shock. She said, "Jeff?!" in a way that was less angry or upset than just confused. And she started looking around the room for me, and quickly saw me there by the closet. I'd told Jeff to give her a second after he took off the blindfold before he started fucking her, so he was still just propping himself up on top of her, his cock just about to enter her. Jen and I locked eyes for just a split second before Jeff thrust himself all the way inside her.
It couldn't have worked out better, because I actually got to look into Jenny's eyes as another man's cock plunged inside her. I just wish I were an expert writer so I could fully convey how it looked. She let out a gasp, and her face was a mixture of fear, confusion, and – the more I think about it the more I'm sure – a little pleasure. I only got to look into her eyes for a second before she whipped her head back around and looked up at Jeff.
Jeff and I hadn't discussed anything that would happen after this point. I just assumed he would pretty much know what to do after that, and I was right. But that first minute or so was really touch-and-go. Jenny said, and I quote her exactly, "What the fuck are you guys doing?!" and that sort of shocked me as she almost never cursed. And she really started to look pissed off in those first few moments. I was seriously worrying that she would start screaming and the night would end with Jeff and I in jail, our futures in doubt and my relationship with Jen shattered.
But Jeff played it well. He didn't say anything; he just stared into her eyes. And he didn't just start fucking her like crazy. He would sort of drag himself out of her and plunge himself back grinding his pelvis against hers. He wasn't thrusting savagely, but it looked like he was doing his best to get himself all the way inside her every time. The weird thing was that, after that initial outburst, Jenny stopped talking. I talked to her about it later and she said she really didn't know what to do. And when I asked her later why she didn't yell at us or something, she said she guessed she was just too much in shock.
It's kind of embarrassing to admit this, but I actually learned some things from Jeff that night. I think, like some guys I had bought into that Hollywood idea that sex is supposed to be this beautiful gentle thing. I wouldn't say that I was pussy in bed, but I had never fucked Jen really hard, even when we did our bondage thing. It's hard to explain, but, despite my thing about orgasms and control, the sex act as a whole was never really about domination to me, so I had never really taken it to that level.
But Jeff was different. He just kept staring at her at first while he fucked her, and his whole look said "I am dominating you". Jenny was stone silent at first. But after just a little bit, every time he would do one of those long, grinding thrusts, I started to hear a little sort of muffled whimper from Jenny. I remember she had her lips shut tightly early on, so I was just hearing these little whimpers from her throat. Eventually, on one of his thrusts, she opened her mouth and let out this soft gasp, just kind of a puff of air with a little whimper mixed in.
This must have been some kind of cue for Jeff, because that's when he really started fucking her hard. I remember, he got in this position so that his knees weren't even touching the bed and he was just supporting himself over her on his hands and feet. And on every thrust he would basically drop his pelvis on her, making the whole bed groan and emitting this sharp slapping sound from where their pelvises collided. And every time, that little gasp.
It went on like that for awhile. They were just staring into each other's eyes. Jenny had this look on her face like she was about to cum, but I think it was still just sort of an expression of shock because she didn't cum right away. It was just that slapping and those gasps. To this day I have no idea what Jenny was thinking as she stared into Jeff's eyes while he fucked her so hard, though I pressed her afterward to no end. It was inscrutable.
Somewhere along the way Jeff got really into it, more so than even I was comfortable with. Bear in mind I didn't think this was exactly how sex was supposed to go. Because even though he had his knees back on the bed and was no longer basically piledriving Jenny's poor pussy, he had grabbed the bedposts and was using his arms to pull himself up into Jenny really hard. I thought he might be hurting her, but she was getting more vocal and it didn't sound like pain. And Jeff started talking dirty to her. I can't remember everything he said, but I do remember him saying "You like having my dick inside you?" and "You wanna be my slut?" Jenny didn't respond except for the little cries she was making as he fucked her so hard.
Finally, Jeff got to fucking her like an animal, I mean he was going at like jackhammer speed. We just had this cheap aluminum bedpost and I thought he was going to yank it off the frame. In fact, as I saw later, it did bend a little bit where the screws fit into the frame, and the slight angle of the bed frame was always a bit of a reminder afterward of what had happened that night.
But, as I was saying, Jeff was really fucking my poor girlfriend without abandon at this point, and I could tell she was on the verge of cumming. This was no small feat because I had learned that the way to make Jenny cum was to eat her out almost to the point of cumming before starting to fuck her, and Jeff had not really licked her pussy that long. But I had asked him not to because I wanted to see her cum while she was being fucked and I knew that if she came solely from being fucked it would mean she was really turned on, which, in turn, would only turn me on more.
The next part is pretty much seared into my brain for eternity. Jeff is on top of my girlfriend, fucking her like a beast, she's about to cum, and he says, "How does it feel to get fucked by a real man?" I'm not kidding. I was really shocked, because it was a pretty hurtful thing to say with me in the room, even if it was just "dirty talk". But I don't think Jeff was out to humiliate me; he was just really, really into the moment. But that was like a trigger for Jenny. We all have our little orgasm quirks and when Jenny came she always tilted her head back a little bit. Well, immediately after Jeff said that her head flipped back like he had just flipped a switch or something. I mean, her throated was literally arched. And she fucking came. When I was thinking about how things would go beforehand, I had focused on the "forced" aspect of the orgasm, so I always sort of imagined it like she would be trying to hold everything back but cumming nonetheless. But Jenny made, like, zero attempt to hide how hard she was cumming. She was making the same little yelping noises she made when she was with me, but louder and more abandoned. I had planned to try to cum on her face or something when she came, but I forgot and just unloaded all over the floor. Honestly, I think that was the hardest I've ever cum. I asked Jenny later if that was the hardest she had ever came and she just said, "I don't know, maybe" but she was usually not really forthcoming about sex.