Love & Sex

5 Stories: I Cheated and Didn’t Regret It

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Our readers on betraying trust, and being glad you did.

Now or never

I met Drew on the first day of college. We were moving in — each accompanied by our parents — and I was pretty much taken from the get-go. He was tall and narrow, nerdy in the truest sense of the word, but also delicate and beautiful.

Three drinks and forty-five minutes (plus three unfulfilled years), I finally told him how incredibly into him I’d been when we were freshmen.

Apparently, everyone could tell I was smitten; my oddly pro-sex father even slapped me on the arm and winked when they drove off, as if to say, “Have at it, young daughter!” I surely would have had at it, in the movie version of my life. In the real one, Drew was a very sweet 100% virgin from North Dakota who dodged my kisses, giggled at my jokes, and frustrated my every intention. 

He would have broken my heart, if I hadn’t met and started seriously dating someone else. Drew remained a friend, stayed a virgin, and got cuter every day.

When senior year rolled around, that “see everyone one last time” nostalgia caught onto me big time. I was still with my boyfriend, terrified of graduation, and overcome with a weird preemptive regret, worried that I’d look back and miss not having done the things I wasn’t doing. That feeling, mixed with the final throes of college alcoholism, meant I started calling everyone in my phone and asking them out for drinks. One such night, I ended up at the local bar with Drew.

Three drinks and forty-five minutes (plus three unfulfilled years), I finally told him how incredibly into him I’d been when we were freshmen. He looked down, blushed, and then looked up again. Fifteen minutes later, he lost his virginity lying on his back on the ugly brown street-sofa in my apartment.

I never told a soul. I’m still dating my boyfriend, and have no inclination to tell him, since to do so would make us both very unhappy. And that'd be no good, since it’s a very happy memory. — Katie Brandon

Peculiar Dating Stories: Love Overseas. Half the fun of traveling is hooking up with strangers you meet. The other half is telling people your stories when you get home. Tell us the story of your most peculiar hook-up abroad, and we'll publish it in our next round-up. Send your 300-500 word story to submissions@nerve.com or click here for more information.

The end of a dry spell

After college, I moved to New York to be with my boyfriend of five years, who was starting graduate school there. I was at the point where I assumed we’d have a life together, and I felt really lucky about it, and pretty smug. There were issues, sure — our fights were toxic, I had a sneaking suspicion he’d never have moved to a faraway city for me like I’d done for him, once I’d thrown a bottle of pasta sauce at his head — but those were things we could Work Out, Like Mature Adults. The way we had after he’d cheated on me, two years earlier. We’d gotten over that; we could get over anything.

Then, six months into my tenure in New York, my sexual attraction to him disappeared. I couldn’t stand to let him touch me. One day we were having fine — not great, but fine — sex. The next, I was sleeping balanced on the edge of the bed so we wouldn’t brush against each other in the night.

I was sleeping balanced on the edge of the bed so we wouldn’t brush against each other in the night.

I couldn’t figure out what was going wrong. I felt like a crazy person. Who would do this sort of blatantly relationship-destroying thing — and I knew it was relationship-destroying — and just not care? I read my Dan Savage; I knew what I was doing, and where it would end, but I didn’t know why. I thought my sex drive was dead and this was the new reality I was going to have to live with. I felt like the worst, most broken girlfriend in the history of girlfriends. I literally flinched when he touched me.

Then I got a few hundred dollars for Christmas, and decided to spend it on a writing class at a university, just for fun. As soon as I got there and saw the triceps muscle flexing inadvertently on the back of my classmate’s arm, I knew I was fucked, and preferably by him. My sex drive was far from dead. It was just redirected.

Days later, the classmate (let’s call him Chris) and I were making out. A few days later, I told my boyfriend we needed to go on a break.

The catch: I did this knowingly, specifically in order to be able to have sex with Chris without feeling like I was such a scumbag I’d be forced to jump off the Brooklyn Bridge.

When we finally did it, the sex was a shock, like a real, licking-the-battery shock, all the way through my body. I realized that I hadn’t been withholding from my boyfriend just because I was screwed up in the head. I’d been doing it, subconsciously, to tell myself — and him — that it was over. I just didn’t get the message I was sending to us both.

A year later, Chris is my new boyfriend. I feel bad about what I did, and I talk about it sometimes, when I’m drunk. But would I go back and undo it? Let’s put it this way: I want to eat Chris alive. His arm muscles drive me up the wall, sometimes literally. The sex is still spectacular. — Christina

Peculiar Dating Stories: Love Overseas. Half the fun of traveling is hooking up with strangers you meet. The other half is telling people your stories when you get home. Tell us the story of your most peculiar hook-up abroad, and we'll publish it in our next round-up. Send your 300-500 word story to submissions@nerve.com or click here for more information.

College

It had only been three months but my girlfriend and I were certain of one thing: we were in love. It was that mushy, make-people-want-to-throw-up love that you can only get from two misguided kids. I was twenty-two and she was barely over eighteen.

She went the prestigious route  — college in Fort Collins  — while I went to a community college in Denver so that I could run their newspaper. But I made the drive north every night to stay with her in her dorm room. Luckily, she was an RA and so she had her own room.

She had become very good friends with a guy down the hall and I became very good friends with doubt.

Near the three-month mark, things began to take a turn for the worse. I found myself not making the trek up to Fort Collins. She had become very good friends with a guy down the hall and I became very good friends with doubt. But I sucked it up and went out nearly every weekend to hang out with her — and some new friends I’d made out there.

One Friday night, I found myself waiting for her at a party, when she told me she wasn’t
going to show up. Lo and behold, after a few drinks, I hooked up with a girl on the couch of the random frat house we were at. She suggested that we go back to her dorm room and I agreed, knowing that there was a good chance my girlfriend would find out about it.

Stumbling drunk, we made our way into her dorm room and made out very, very loudly, until her roommate finally got up and turned on the television because she couldn’t sleep. Within minutes, there was a knock on the door and the announcement of “RA on duty.” The voice sounded familiar. Her roommate got up to answer the door.

At first, I hid in bed with my new female friend — until I heard the sound of another guy’s voice with her. I turned the corner to find my girlfriend, with her arm draped around her friend from down the hall, both in their pajamas. Drunken me decided now was a good time to confront the situation as only he can: like a complete asshole.

I wrapped my arm around the roommate. The girl I’d hooked up with, who apparently did not like my girlfriend, decided to make the most of it and came up and grabbed me from the other side. I stood in the doorway with a girl on either side. Then I asked the new guy how my dick tasted as I shut the door on a part of my life. — Ben

Peculiar Dating Stories: Love Overseas. Half the fun of traveling is hooking up with strangers you meet. The other half is telling people your stories when you get home. Tell us the story of your most peculiar hook-up abroad, and we'll publish it in our next round-up. Send your 300-500 word story to submissions@nerve.com or click here for more information.

Pancake makeup

I had been dating this girl Ashley on and off for a little over a year. She was my first real, “serious relationship” girlfriend. She was a flawed individual — she wore pounds of caked-on makeup, drank a lot, and was very hot and cold. Once the initial infatuation was over, those things were all I could see. She'd get wasted at the most inappropriate times — work functions or around my parents. She'd lead me on and then get "tired" or "not in the mood" and leave me with the bluest of balls. But the worst of all — we'd be kissing and her makeup would get all over my face and clothes. It genuinely grossed me out, and the dry cleaning was expensive.

Then I met Susan, a girl so comparatively normal that it turned me on. We could hang out without getting into fights, and everything was just much more relaxed. She had a very natural look. No sloppy foundation that I'd end up tasting.

Once the initial infatuation was over, those flaws were all I could see.

On New Year's Eve, I was so fed up with Ashley that I convinced her to go to her girlfriends' party and that I would meet up with her later — leaving me free to go to a party with Susan. I wasn't planning on hooking up with Susan — honestly, I just enjoyed spending time with her.

But it was New Year's Eve. We got champagne wasted and ended up having sex. It was great, fun, and when I woke up to a barrage of drunken texts from Ashley, I didn't feel the least bit of guilt. In fact, I was glad to be waking up next to Susan and her dewy morning skin. Ashley never found out — and we actually dated for a while longer, before breaking up in a fight over who was the bigger alcoholic. — Andy DeLuca

Peculiar Dating Stories: Love Overseas. Half the fun of traveling is hooking up with strangers you meet. The other half is telling people your stories when you get home. Tell us the story of your most peculiar hook-up abroad, and we'll publish it in our next round-up. Send your 300-500 word story to submissions@nerve.com or click here for more information.

Photo by Cindy Ho

Internet nerd

I really liked Troy. He was kind and funny and nicer to me than any guy ever has been. We had recently become exclusive when a guy I’d met online came into town. I was too lazy to cancel the plans we'd made, so I went. We met up at a bar that a lot of my friends frequented  my choice  figuring it would be a friendly drink and nothing more.

The second I saw George, I got worried.

The second I saw my internet friend, George, I got worried. I'm not terribly shallow, but I definitely have a type, and George was made from the fabric of perfection. It was like he was summoned from a floppy-haired, sweaty-handed, Converse-wearing Garden of Nerdy Eden to tempt me. And did I mention he could barely speak? I love a good nervous stutter. He was nervous because he had social-anxiety problems, and I was nervous because I knew that if there was a pause too long and awkward I would probably just jump his bones right then and there. So we did what any two nervous people on a date in a bar do: drink ourselves stupid.

By the time last call came around we were like old friends. Old, horny friends. Any vision of being true to my darling Troy vanished and I whisked George off to my apartment, stumbling ever so slightly and all the while laughing, laughing like the treacherous wanton woman I had become. If there was any opportunity for me to feel guilty about this indiscretion it vanished the second we got up to my place. George ceased being a shy, polite nerd from New Jersey and turned into a traveling salesman from Pleasure Town. Troy may have been nice, but George gave me multiple orgasms, and a girl has to prioritize. He went home the next day (but not before giving me one sober romp that morning). I never told Troy about it, but we only stayed together for about a month afterward.

I don’t regret it one bit. And I would regret it less if George came to the city more often. — Jennifer

Peculiar Dating Stories: Love Overseas. Half the fun of traveling is hooking up with strangers you meet. The other half is telling people your stories when you get home. Tell us the story of your most peculiar hook-up abroad, and we'll publish it in our next round-up. Send your 300-500 word story to submissions@nerve.com or click here for more information.