Cheating Confessions, Part 2: His Best Friend’s Penis

Cis-men – especially heterosexual cis-men – are widely assumed to be fiercely competitive, and in my experience this assumption has frequently proven true. In my poly lifestyle I find my male partners often take a long time becoming accustomed to one another and realizing they don’t have to fight for dominance. Mostly, though, this competition is subtle: scrutinizing each other’s behavior, being possessive of me, that sort of thing. I have only once, in my lifetime sexual history (which, I admit, is less than a decade), had a man directly ask me to compare his sexual performance, and specifically the size of his cock, to that of another man. True story.

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I’m really enjoying posting photos corresponding to the phases of my life I write about. This is from fall 2006, at a friend’s birthday party.

The fall of my sophomore year of college, I came back to campus (after a very eventful summer which is a subject for another story) and to my boyfriend Alex who was at this time unaware of my sexual indiscretions. We only stayed together about two weeks into the school year; just enough time for one more cheat before the break-up. When I say this is “part 2” I’m really not speaking chronologically: there were two other men in the interim, but this story is related to part 1 so I’m telling it first. Yes, I hear you, get on with it. Right, so where was I. Just got back to campus for sophomore year of college, Fall 2006.

Scott had gone back to his parents’ house in north Florida to go to another college, and I found myself becoming closer with his best friend, Tyler. I had gotten to know Tyler pretty well the previous year, and our friendship was quite similar to the one I had with Scott. Tyler, though, was more fickle in his affections, and the year before I often found myself ignored by him for a month or more at a time. When he was interested, however, we spent a lot of time together, and I spent quite a few nights in his bed (which was, conveniently, across the hall in the dorms). Like Scott, we didn’t have sex at first; unlike Scott, I didn’t have sex with Tyler until sophomore year, and we then had the opportunity for repeat performances.

Only the first time he and I had sex was while I was still with Alex, so I suppose this is only partly a cheating story, and mostly just a bad-fucking story.

Tyler knew throughout our friendship that I was involved with Scott, and sometimes looking back on it I think they might have talked about me quite a lot, possibly even turned the whole thing into a game between them. I find myself wondering about that because the first time I saw Tyler’s cock he outright asked me if it was bigger/better than Scott’s. I figure he was hoping for an answer he could rub in his best friend’s face. Well, to be perfectly honest, I only ever interacted with Scott’s penis one time, the room was dark, and I didn’t get a very good look. That was my answer, and it was the truth.

Tyler, though, was damned proud of his equipment and wanted it flattered: not without reason, as it was sizable and very interesting looking when it was hard. That sounds like a left-handed compliment, but I generally don’t have a lot of comments to offer about the aesthetics of a penis. Interesting means I liked to look at it, and that’s about the best compliment I’ve got in that department. I was nonetheless a bit flabbergasted by his directness in asking about his best friend’s package in opposition with his own.

Unfortunately for Tyler, his cockiness (see what I did there?) got the better of him, and he failed to actually figure out how a woman’s body works. Apparently someone informed him that big dicks gave women orgasms, and he stopped reading the manual after that. Obviously he wasn’t completely hopeless or I wouldn’t have spent so many nights in bed with him before getting formally introduced to the aforementioned penis. Tyler was extremely seductive and arousing before he got into my pants – hell, with the amount of time and effort he put into being with me at that time, he was practically my boyfriend. And he was a good one, then. We spent loads of time together, often in his car (a Tiburon, which at the time I thought was bitchin’ but now I realize is the staple vehicle of douchebags…though he and Scott both had absolutely beautiful sound systems in their cars, and we would often just drive around with the windows open listening to music. I sometimes think that their cars seduced me as much as they did. Beautiful music and vibrating engines will do that to a girl. Aaaaanyway, this was the longest parenthetical ever.) since we were college students with no money for real dates. In public, he was affectionate – in private, he was very physically attentive. He could get me panting and desperately wet with his touch.

This part of the story is depressing for me - allow me to soften it with this funny picture of me climbing a dead tree. Also from fall 2006.

This part of the story is depressing for me – allow me to soften it with this funny picture of me climbing a dead tree. Also from fall 2006.

All that completely turned around when our relationship became directly – which is to say penetratively – sexual. His idea of sex was to kiss me long enough to get me naked, then the condom went on and it was time for penetration. I often wasn’t wet at all, because, well, why would I be? This was yet another reason I grew to hate condoms over the years – if I’m not moderately lubricated already, the condom will effectively parch me completely. And then, bad friction. Bad friction while he pumped away on top of me, in missionary position, on a squeaky dorm bed. I did my best to tighten my muscles around him to get some deeper sensation, but with no warm-up my vagina would have none of it. I have never in my life faked an orgasm, but I admit I played up my enjoyment with him quite a lot.

After we had sex a few times, our relationship changed drastically. No longer courting me, he didn’t go out of his way to see me or be kind to me. And apparently dissatisfied with my sexual performance, he would openly mock me in front of our mutual friends, saying that I would “just lie there.” I’m pretty sure the phrase “dead fish” came up once or twice (which, for anyone other than him who has ever had sex with me, is obviously laughable). Generally he was a complete jerk, and then would ask if I was coming up to his room at night – though he often sent me back to my own room afterwards, which this semester wasn’t even in the same building as his. I admit, I went up to that room more than once after this behavior started. It took some time for it to sink in that he really was going to go ahead and treat me like crap now.

Tyler also asked me about his sexual abilities compared with Scott’s, and I don’t remember what I told him, but in hindsight comparing the experiences is amusing to me. When Scott left our college, he told me that he regretted not being around to pursue a real romantic relationship with me. After I started having sex with Tyler, our relationship became significantly less intimate than it was before. Funny things.

The only overall positive experience of having sex with Tyler that I can remember was a threesome that we had with my best girlfriend at the time. She and I had a sexually active friendship, and on several occasions had threesomes with guys that I was involved with. We had a lovely sexual chemistry, so the experiences were universally pretty awesome, and this was no exception. I think we managed to get Tyler caught up enough in our pheromones that the encounter was a satisfying one for everyone. She later theorized that he was using me to get into bed with her, but I don’t necessarily buy that. I briefly considered posting one of the many photos I have of her and me together, but unlike the men in these stories I still care about her enough to be interested in preserving her privacy.

As usual, with these little stories and glimpses, there’s no moral or nice little tie-in to end the story. Though I think I will end that story with this one: not long after Tyler and I stopped having sex (which was less a direct break-up and more a tapering off of contact), Scott came to visit us on campus. We were sitting outside smoking, and I headed inside to go to bed. Scott got up, and gave me a hug, and we were generally happy to see each other and catch up that night. Tyler got up to hug me, and I blew him off. He said something about why didn’t he get a hug, he thought he was my friend, something meant to be comical but also was a little petulant. I told him of course we’re not friends, you’re not even nice to me. BA-ZING! Yeah, no, not a great burn, but I almost never say anything mean to anyone, so being honest like that felt really good. It was really nice to place being honest about my feelings over not being rude.

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