While we have quite a stockpile of questions to answer on Formspring, this one really jumped out at us. We have views of monogamy that some would consider unorthodox. At the same time, we are completely committed to one another emotionally. While cheating isn’t really our style, neither of us would ever judge someone for cheating. Most people’s relationships are none of our business.
We considered opening this post with a picture of Newt Gingrich, but decided not to go the political route despite the fact that Newt seems to be the epitome of the hypocritical cheating scumbag politician. Oh, fuck it; here he is:
Believes gay marriage is a threat to marriage itself, yet doesn’t see the irony in being a serial cheater.
Have you ever cheated on a partner?
Jack’s Answer
Yes, once. At age sixteen, I was in my first long-term relationship. Newly-relieved of my virginity, I was suddenly imbued with a newfound confidence. The summer after my junior year of high school, I found myself in Southern California for a few days, as one of my parents was attending a work-related seminar. Without much to do during the day, I met and befriended a girl whose parent was attending the same seminar. She was my own age or very close, her name lost to time. (This was nearly twenty years ago.)
She and I spent the first day hanging around the hotel, swimming in the pool and watching TV in her room. On the second day, we had sex. Unlike my girlfriend, who was sweet and very attractive but not quite as sexually imaginative as I would have liked, this girl was open-minded and experienced. She was the first person I ever did doggy style with. She’s the first person who ever rode me in the reverse cowgirl position. And for that matter she was the first person who ever gave me oral sex. My girlfriend wasn’t into any of these things.
Over the next three days, we had sex numerous times, in countless positions. We showered together. She asked to be spanked. She said that she enjoyed having her ass fingered. I didn’t indulge her on that one, as she never requested it of me, just mentioned that she was into it, and being sixteen I was too stupid to take the hint. Beyond that, we talked about our lives, discussed our favorite movies, as well as the music we liked. We went out to lunch. It was nice. I never felt anything beyond physical attraction to her, but I acknowledged that she was someone I could have considered a friend, and if we lived closer – and for that matter if I wasn’t in a relationship already – perhaps something deeper might have blossomed. But when I left L.A. after the seminar there was no exchange of phone numbers, no promises to keep in touch. I don’t even think there was a good-bye.
I had enjoyed the tryst; it was sexually gratifying and it left me with the sort of ego boost a geeky, sometimes awkward sixteen-year-old often needs. But I knew that what I had done amounted to a flagrant violation of the trust that my girlfriend had in me. Rather than unburdening myself to her, I kept silent. I’d used condoms with the other girl, and the sex had been meaningless, so I reasoned that there was no point in upsetting her. I found that this justified my not telling her. In reality, however, I felt remendously guilty over my transgression.
My girlfriend attended a different high school than I did, and our relationship was such that we didn’t see each other every day, or even talk on the phone every night. It was 1993; cell phones weren’t the sort of thing that teenagers commonly possessed, and text messaging was about a decade away from being a familiar concept to most people. I’d just gotten my first pager, but my girlfriend didn’t page me much as she didn’t want her parents to know that I had it, ostensibly because because pagers were associated with drug dealers at the time.
In time, my guilt gave way to paranoia that she would somehow find out, but she never did. Ironically, I indignantly broke up with her around a year later, after she admitted to having cheated on me. This probably wasn’t my finest hour.
Jill’s Answer
I had been dating a guy for a few months. He was extremely self-centered, and the kind of person whose only compliments were backhanded. I didn’t like him all that much, actually, but his friend was dating my friend, and his and my relationship sprung up out of convenience. I guess he was pretty good in bed.
We’d gone to his friend’s house to hang out and drink. It was him and I, the friend whose place it was, and a few others. My boyfriend spent the whole night ignoring me while he socialized with everyone else. His friend, on the other hand, was showing me plenty of attention. We began to flirt back and forth, aided and abetted by lots of alcohol. Eventually we ran out, and my boyfriend offered to walk to a nearby liquor store to get some more. While he was gone, the flirtation continued.
My boyfriend returned from the liquor store with a couple bottles of Jack Daniels, which he knew I didn’t like. (I still don’t. I would much rather drink vodka than whisky.) I decided to have some anyway, if only to spite him. When my boyfriend pointed out that I don’t drink Jack Daniels, I said, “Tonight I do,” and spent the next couple hours drinking Jack and Coke.
The bathroom had two doors, one leading to the hallway and the other leading to the bedroom. I had gone to use the bathroom, and when I was finished my boyfriend’s friend came in from his bedroom. He pretended that he didn’t realize I was in there, but quickly shut the door behind him. He came over and kissed me, and I kissed him back. I got very wet, not only because the friend excited me, but because I felt like I was getting back at my asshole boyfriend. In seconds we were making out, and although I wanted things to go further right there in the bathroom, he eventually snuck back out through his bedroom. My boyfriend had no idea.
We flirted back and forth for the rest of the evening. As we were leaving his house, I gave him a hug good-bye. He used this opportunity to whisper that I should come back later, and as soon as I dropped my boyfriend off at home I returned. We had sex all night, and the friend was even better than my boyfriend was. Not only that, but he appreciated me in ways my boyfriend never did. He did things to my body that my boyfriend never could. When the sun came up, I was a sweaty, quivering mess on the floor of his bedroom, satisfied in every possible way. But so was he.
Eventually someone told my boyfriend that the other guy and I had been in the bathroom together the night of the party. By then, of course, he and I had hooked up a few times. My boyfriend said that he thought we should see other people. I told him that I already was.
If you want to ask us anything, drop us a line on Formspring, or use the handy Formspring widget on the right-hand side of our blog. We like sexy questions!
Good for opening a picture with Newt. It’s fine if you have a different view towards marriage than others, but if you’re partner doesn’t want it, then it’s cheating. I think both of your answers were great, situations that occur in real life.
Both of your stories were awesome! I found myself hooked on every word, wondering how it would turn out. Thanks for sharing.
Thoughtful and interesting as always. Keeping secrets is hard and it sucks. You are both so open; it’s wonderful.
A teen just coming into his sexuality and a woman who deserved more attention than she was getting. I give you both passes.
Very interesting stories. I wouldn’t really consider Jack’s true cheating…I mean you were 16! Jill you didn’t say how old you were, but the boyfriend sounded like a jerk and you were clearly better off without him.
I would never encourage someone to cheat, but in both of these stories I certainly don’t blame you!
I really liked these stories. I particularly enjoyed the irony of the discovery of Jack’s girlfriend having cheated on him after he carried all that guilt. The reverse cowgirl reference is the best and the naughtiness of Jill’s story is really fun.