Gay Guilt: How I Lost My Virginity And Why It Still Bothers Me

The complexities of self-acceptance, gay guilt, and the lasting impact of societal expectations.
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I lost my virginity in high school to a boy on the floor of his closet.

The irony of that experience is not lost on me. However, that would not be the last time I humped a stump.

Confession: I have had sex with men. Lots of sex with lots of men, actually. Confusing? Yes, most definitely — especially for me.

I Didn’t Know I was a Lesbian

As I’ve said in previous columns, when I was growing up, I didn’t know that I was a lesbian. In fact, I didn’t even know the word “lesbian.” I certainly had never heard of women having sexual feelings for each other. No one in my small town was out of the closet. Not even Ellen was out, for God’s sake. I was pretty positive that I was absolutely the only person on Earth with feelings like that.

The default setting in my hometown was heterosexual.

Add my sexual confusion together with the complete void of information and mix in the notorious conversation with my dad, wherein he convinced me that demons cause homosexuality. What formed was a special, straight-making cocktail that led me to throw myself full-force into being a man-eater, a heartbreaker, and a chaser of boys.

All of My Formative Sexual Encounters Were with Guys

Thanks to a string of boyfriends all over the world from England to Tennessee, I never lacked in male affection. I became very good at faking it. Being a perfectionist, I always turned out a star-making performance, complete with screaming fake orgasms. I devoured Cosmopolitan, memorizing articles like “Top 10 Tips for the Most Electrifying Blowjob Ever.” Giving head was super convenient for me, because the boys seemed to like it a lot, and I didn’t have to have a penis shoved into my bone-dry vagina.

A major threat to my cover was my pesky and persistent habit of staring at girls’ boobs. During my teens and early 20s, changing clothes in front of friends was mortifying, and I remember having to stare up at the ceiling, forcing myself not to glimpse at their breasts, because I feared my friends might think I was a dirty lesbian.

My Gay Guilt: I Still Have Nightmares About Sex with Men

Quite often the landscape for those unpleasant dreams is my closet. Just last week I dreamed that I was with an old boyfriend, and we laid down in the closet at the house where I grew up. Once I was on top of him, I started thinking, “Wait… something’s wrong here. What’s happening? Why am I having sex with a man?! Oh, dear god, I’m supposed to be gay. Shit! My wife is gonna kill me!”

Seeking answers about this unrelenting guilt, I turned to my friend, sex guru Carlin Ross. “Women have guilt about their sexuality, period,” she told me. “Our cultural obsession with virginity, the slut stigma, gay guilt — it’s all part of the same continuum. Female sexuality is discouraged and repressed at every turn. A recent study found that 75 percent of women like to drink a glass of wine or two immediately before getting into bed with their husband or boyfriend. Six percent of women have never had sober sex. Women are expected to be virginal, and they’re expected to have sex with men. So they need a little social lubricant like alcohol to allow themselves to be sexual. Take that sex guilt, add gay guilt, and you have even more shame on top of something that should be beautiful and revered.”

Working to Get Over the Sexual Shame

Being consciously aware of the fact that it’s my upbringing and society’s norms that caused me to have so much man-sex, it still seems so hard for me to get over the sexual shame as well as the gay guilt. I asked Carlin what to do about it, and she explained, “When I counsel women on releasing themselves from sex guilt, I tell them to imagine a big, blue box, and every time they have a negative thought about themselves to imagine pulling that thought out of their heads, putting it in the box, and placing the cover on top. I tell them to then walk away from that box a free woman. It takes time, but eventually you’ll stop having those thoughts.”

Well, you better believe that tonight I’ll be thinking about a big, Tiffany box and throwing all my old boyfriends inside it. Only kidding.

Originally published in The Huffington Post on November 16, 2011

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