I'm A Gay Man Who's Been Intimate With Many Women

I tried to hide my identity.

I'm A Gay Man Who's Had Lots Of Sex With Women VGstockstudio / Shutterstock

By Dennis Milam Bensie

Growing up, I never fantasized about having sex with a woman. I wanted to have sex with a man. I believed that, because I wasn’t attracted to women, they wouldn’t be attracted to me.

I was wrong.

My very first sexual encounter occurred with a woman when I was eighteen years old. I thought Jessica and I were “just friends” when she seduced me.

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My first kiss came while we were watching television. She got closer and closer until she was on top of me and kissing me.

I felt obliged to accept her advances that evening and she took my virginity.

For the next several nights, we slept together. It became the perfect storm: I would learn to tolerate the sex so that I could be in the relationship and deny my homosexuality.

For three years, I was an untried homosexual living the life of a heterosexual. I hadn’t been with a man yet, so I didn’t have any way of comparing the sex.

I grew to love Jessica as a person. But I searched my soul to find something enjoyable about sex with her. I did the best I could, but I was putting on an act. I didn’t want her to stop liking me.


Here’s a shock: when I was a teenager, I had no problem getting an erection. With enough stimulation, I could achieve a hard-on with Jessica.

The first few times we had intercourse, I pumped and pumped and pumped.

My new girlfriend was having the time of her life and enjoyed multiple orgasms.

That was nice for her, but I was miserable. The situation wasn’t sexy to me, so I couldn’t ejaculate.

The expectation that I would orgasm never went away.

I hoped that with practice, it would… just happen.

In order to fulfill my duty, I would have to pull out and masturbate until I was close to orgasm, and then penetrate her at the last minute and shoot.


It was humiliating. Eventually, I just lied and said I came inside her without the need of my hands. She believed me or claimed to.

Things got tense. I felt like Jessica needed to check my homework.

In spite of the fact that the first few months of our relationship had been a sexual disaster, Jessica became my wife.

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Even making out with Jessica was never arousing for me. I didn’t mind a quick, affectionate kiss from her, but to go to the next level, tongue and all, was uncomfortable. I avoided kissing her.

Things got more and more desperate in our bedroom. I tried anything to enjoy sex.


Jessica had big breasts. I had no interest in breasts in the first place, so shoving myself between them didn’t make me like them anymore. I’d go limp. It was a bad idea all around because I had no way to fake an orgasm.

I resented her breasts and started cartoonishly poking and pinching them. She seemed to enjoy the attention. Perhaps the groping was better than nothing.

Jessica often asked me to go down on her. I just ignored her request: I’m sure the look on my face gave her my answer. She offered to shower right before we had sex. No deal. I couldn’t even look at her vagina, let alone stick my whole face down there.

Getting a blow job from my wife was unnerving. I found it best not to watch Jessica do it to me.


Seeing someone that you have no sexual attraction to with your penis in their mouth is daunting.

I was pretending to enjoy her blow jobs, but was nervous she could tell just how much I hated the experience. 

I hated sex. I felt like a complete failure. At the age of twenty, I decided no sex was better than sex with my wife. The marriage crumbled and we divorced.

When I was finally single and came out of the closet, I was ready to have tons of gay sex.

But it didn’t happen quite that way for me.

The first few months of my sexual freedom were disappointing. I developed a crush on a straight man named Stanley (whom I suspected to be gay).

Then another woman started chasing after me. Mary was a year younger and everyone knew she was still a virgin. She and Stanley had dated a few months before.


For over a month, it seemed like wherever I went with Stanley, she also happened to be there.

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I made it clear to her that I was gay, but she also knew I was freshly divorced from a woman.

Perhaps Mary thought she could show me something that my ex-wife couldn’t. She was certainly more obtainable than Stanley was. My relationship with him would end in sexless heartache.

On the rebound, one thing led to another and Mary kissed me… only this time I liked it. Despite the braces on her teeth, she was a very good kisser.

I was still attracted to men. I didn’t want to be sexually curious about Mary but I had trouble resisting the intimacy. There was still no man in my life, so I allowed her to spend the night with me.


Being in bed with Mary was very different than being in bed with Jessica.

For one thing, I found Mary prettier. Something in her soul aroused me a bit. I had an opinion on her body. I found myself liking her curves

My rapport with Mary was wonderful. Yet I was so conflicted about lying in bed with a naked woman again. I knew she was a virgin and I worried about her losing it to a gay man.

After a few weeks of pillow talk, I had to admit to myself that I was just experimenting with Mary. If I wasn’t in the heat of the moment with her, I had no real sexual desire towards her. I found her attractive, but I just wasn’t that attracted to her.

Mary was still a virgin when she and I parted ways.


When you are gay, it feels like you have two virginities: one for each gender. I lost my second virginity with a guy a few months after Mary and I stopped sleeping together.

That was twenty-five years ago. I never had sex with a woman again, but I’ve had plenty of fun with guys in the last twenty-five years.

Just recently, I heard some young gays refer to each other as “gold stars”. I later found out that a gold star is a gay man who has never had sex with a woman.

My friends just call me “old star.”

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Dennis Milam Bensie is a writer and author of Shorn: Toys to Men. His short stories have been published by Bay Laurel, Everyday Fiction, and This Zine Will Change Your Life and his essays have been seen in The Huffington Post and The Good Men Project.