Never Have I Ever: Had an Affair

We Spoke to Someone Who Had a Real-Deal Affair About What They’re Like

Have you ever played “Never Have I Ever” before? Here are the rules: Everyone puts up ten fingers, and you go around in a circle and one by one share something sexy or scandalous that you’ve never done before. When someone else shares something you have done, you have to put one finger down — and of course, drink. The first person to put all 10 fingers down loses (or wins, depending on how you look at it).

Well, AskMen is still playing Never Have I Ever, and the rules are simple: In each edition of this column, we speak to someone about doing something new in bed, whether it’s a long-time fantasy, something that just happened, or even something they regret. They tell us everything so you get an inside look at what some sexual experiences are actually like.

Are affairs salacious but hot as hell and something we should all experience once? Or evil acts? The answer, of course, falls somewhere in the middle.

We’ve talked about what it’s like to cheat in this column before, but this time, we wanted to dig into what having a full-blown, ongoing affair is like as opposed to a one-off indiscretion. So, we chatted with Michael, a genderqueer person living in Chicago.

Michael enjoyed, and yes, that’s exactly the right word, an affair with a handsome older man with a fabulous body (in all of the places) who also had a posh apartment.

Prior to this affair (you know it’s an affair if you stay with your partner throughout and after), Michael “hated” affairs, desiring a monogamous relationship.

Keep reading to learn why the sex was so good; they now think cheating’s bad rap is “old, outdated, restrictive,” but prefer ethical non-monogamy frameworks to address the realistic nature of sexual appetites while telling the truth.

AskMen: What is your experience with having an affair?

Michael: In my late 20s, I was in a relationship and was trying hard to make it work. But things fizzled out sexually, and I was bored. This led me to seek sex outside of my relationship, which turned into a several-month affair with someone else.

How did it start?

One day, I started talking to someone on Grindr, and maybe it was just impulse and excitement or a full need for satisfaction that I went over to his house. I was a bit nervous but also excited by the fantasy of doing something I shouldn’t. I think that was also a bit of the turn-on.

Before you had one, what did you think about affairs and cheating?

Haha, I hated them! I wanted a monogamous relationship with my partner. I thought affairs and cheating were a death sentence and total betrayal. I had ended relationships in the past with exes who I caught cheating on me.

Did you have prior experience with cheating before the affair?

Yes — I had been with other men who were cheating on their partners in the past, and I had had a drunken night or two in other relationships of my own.

Tell me about how hot it was!

It was super hot. Physically, he was very much my type. He was a handsome older man, great body.

His place was also the right atmosphere — there was a poshness and elegance to it that I enjoyed. And we just had intense sexual chemistry. There was passion and electricity in our sex, and also this kind of tenderness.

What I thought would be a one-time situation ended up becoming more and more regular, lasting for several months.

What do you think of the stigma around cheating?

I think it’s old and outdated — and restrictive. In my experience over the years, I think it is just unrealistic now to think that we can be completely sexually satisfied with one person. Especially in your 20s when you are figuring out all your interests. I think that cheating is natural and will continue to happen on some level when pushing monogamy.

I think that the most realistic thing to do, at least for me, is to keep newer relationships closed to establish initial intimacy, and then slowly open them up based on each other’s comfort levels.

First, introduce new partners to play together, and eventually open up fully. This, of course, takes a lot of communication and is not the easiest, but I feel it ultimately leads to better intimacy within that relationship.

How did the experience of the affair live up to the fantasy?

It was hot — on every level. The secrecy was hot. The sex was hot. I don’t regret any of it. Eventually, there became more than just physical lust. We began to chat a bit more during our sessions, either before or after.

He knew that I was in a relationship and cheating, and there was also a sense of empathy from him — that I was clearly unhappy in my relationship and that I should be happy. The only thing I would regret is staying in a relationship that wasn’t working for as long as I did.

How did it end?

He ended up relocating to Florida, and we lost touch over the years. I remained in my relationship for another two years out of habit, and we eventually parted ways early in the pandemic. I’m happily single and focusing more on me.

Would you have done it again?

With him? In a minute — some of the best sex of my life! Have another affair? I’d like to say no. I’d like to say that in my next relationship, I’d follow my own advice from a few questions ago and make sure that I am with someone that feels the same about opening up over time.

The Different Levels of Cheating, ExplainedShould You Admit to Your Partner That You’ve Cheated on Them?Can Cheating Be Healthy For a Relationship?

Source: AskMen