A Gay Man’s Sex With Women


An intimate look at a man pretending to be heterosexual. 

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. 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.

When you are gay, it feels like you have two virginities: one for each gender.

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.

Come Inside

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 come inside my girlfriend’s vagina during intercourse 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 myself 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 when she repeatedly asked me to come on her face and tits. She gave me her permission to finish in her mouth, too. I’d already been through the guilt of fucking her and pretending to enjoy it. I could never provide her with a good come shot. We never talked about the void.

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

The Marriage Bed

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, and I experimented with titty-fucking. I had no interest in tits in the first place, so shoving myself between them didn’t make me like them any more. 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 to make sure it was clean. 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. There was a fear that she would bite my cock off if she knew the truth.

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 HOT gay sex.

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

An Empty Closet

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. 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.

The Virgin Mary

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. Her tits were perky and I (strangely) enjoyed fingering her pussy.

My rapport with Mary was wonderful. Yet I was so conflicted 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. This concern didn’t stop me from parking my hardness just outside her vagina. I loved rubbing my erection all over her pussy. I really, really wanted to slide it inside her and bring her pleasure. But I didn’t want another messy relationship with a woman.

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.

No Gold Star

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 star”. 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”.


Photo by Kevin Hutchinson.

About Dennis Milam Bensie

Dennis Milam Bensie grew up in Robinson, Illinois where his interest in the arts began in high school participating in various community theatre productions. Bensie’s first book, Shorn: Toys to Men was nominated for the Stonewall Book Award, sponsored by the American Library Association. It was also a pick in the International gay magazine The Advocate as “One of the Best Overlooked Books of 2011″. The author’s 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. One Gay American is his second book with Coffeetown Press, which was chosen as a finalist in the Next Generation Indie Book Awards and the Indie Excellence Book Awards. He was a presenter at the 2013 Saints and Sinners Literary Festival in New Orleans and at the Montana Gay Pride Festival. Dennis lives in Seattle with his three dogs.


  1. Alex Smith says:

    I’m attracted to women, I can hardly find men attractive, yet I can’t have ejaculation with women and I avoid relationships. People don’t come with technical handbooks.

  2. I suspect my 18 year old son is gay. I love and accept him unconditionally. He is very shy and timid and has never even kissed a girl before. He has had female friends but no interest in dating. He is a virgin, never having been with anyone! His Father is judgmental and I could understand him being apprehensive to be open with his Dad but he and I are close. My son has very low self esteem lately and agitated. How can I reassure him that I won’t reject him and I love him no matter what his orientation is?

  3. For the love of god. I’m 27 and never had a relationship…all the guys….now even gay guys can get a woman…I hate myself…he has a nice girl and throws her away. How sad.

  4. As former wife of a closeted gay man, I lost all respect for him as a person for his lack of honesty. Our daughter, lives her life openly as a lesbian. I am so very proud of her.

  5. Oh being just one year divorced and finding out my ex was gay, this tears at my heart. As a straight spouse we question everything and it hurts to think my last 19 yrs were like Jessica’s. It’s unfair what you did. Just say it out loud, we deserve the truth.

  6. Scott K says:

    Thank you, Dennis, for sharing your thoughts. I am presently married, and I’ve known I am bisexual for quite some time. It wasn’t until I moved to a larger city where I could explore same sex experiences, so I thought I would have the best of both. Mostly all I feel is shame for cheating on my wife to fulfill myself sexually. My biggest mistake was not being truthful with her about my identity from the get-go.

    • Dennis Milam Bensie says:

      You are very welcome. You have to be truthful with yourself or it will come back to haunt you.

    • Do you still do this? Do you have unprotected sex with other men and bring that home to your wife? I’ve had to get HIV tested before because my man couldn’t keep it in his pants, and i’ts a terrible thing to do to a person. It’s not okay just because you are having a hard time.

      • Terry, you ask:

        Do you still do this? Do you have unprotected sex with other men and bring that home to your wife?

        Perhaps you’d find answers to your question if you read the article rather than projecting:

        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.

      • Indigo Love says:

        Your comments continue to be rather offsetting. Implying the negligence of safe-sex practice and HIV stereotypes is rather insulting.

  7. People are afraid, deathly afraid, of bisexual feelings, and the social pressure within the gay community is conducive to that fear, just like the straight majority.

    • I don’t really consider myself bisexual. I guess technically I am. It is interesting that you mention that the gay community fears bisexuality. Perhaps that is because I don’t know very many people who are practicing bisexuals who admit it: someone who frequently flips back and forth between interest in both sexes.

      I think my friends would all be shocked it I started having sex with women again. I would be shocked but I guess it is not out of the question.

    • LOL the man is gay, not bisexual, leave him alone idiot

  8. Poor Jessica!!!!!!!! This is so sad. You didn’t have to come out as a full on homosexual, but you would have at least broken up with her. Knowing the whole time you hated sex with her? I can’t imagine the hurt of giving head to a guy who secretly hated it the whole time. She did it FOR you. I’m sorry you struggled so much, but sad you left a trail of pain in your wake. You’re like the general Sherman of love dude.

    • *could have (not would have)

    • Indigo Love says:

      It’s not quite straight forward growing up as a closet gay. Sure things didn’t end well, but does anyone’s first intimate relationship end well? Typically it doesn’t. Being in the closet is very complex, and many aren’t accepting of themselves yet. Hence trying to be in a hetero relationship. I experienced a bit of this growing up, trying to be with a girl, for a year, but nothing ever really materialized. We never really got sexual, the most that happened was me being in her pants some, but even that felt really weird and I only did it out of social pressure. I was highly against her getting in mine. The relationship itself was all sorts of backwards, but I tried so hard to just fit in and be ‘normal’ at the time and try to go with it. I can’t stress enough how unnatural one can feel being closeted, and the pressures of trying to be ‘normal.’ Sure it can end messy; it can be really unfortunate. Mine never got quite that way, but did go on for a long time like I said. A year after that I accepted my ‘curiosity’ and another year later finally accepted being gay. Funny thing is, me and my one ever girlfriend a couple years later ended up being good friends via a mutual friend (my best friend Christian, RIP) and were ok with everything.

      My point is, it’s really a lot more complicated than you think. You can’t really just hop to the bottom line of a messy ending; there’s a LOT more to it than that.

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