Why I Had Sex With a Man in Drag— Just Once
By: Danika Bloom
Tags: Self, Relationships, LGBTQ, Sex, This Happened To Me

It was a helluva year, the year I turned 40. I waited all of three weeks before I started to date after my husband of 14 years surprised me after a business trip with the declaration that he’d fallen in love with another woman.

They’d known each other three weeks… I thought if he can fall in love in three weeks, I can fall out of love just as fast.

My friends all begged me not to date, told me that I needed time to heal. One quoted Dr. Phil’s advice that I should wait one month for every year I was married. That sealed it for me — I created a profile on LavaLife that very night.

Pete was not the first man I met. In fact, I met him towards the end of the period I called my Year of Dating Dangerously. Nor was he the most dangerous man I dated — but he was one of the most interesting. A lawyer and single dad who lived in the most religious and socially conservative city in my region, he had an unexpected hobby.

Pete lived 90 minutes from downtown and I lived 15 minutes by transit, and for our third date he asked if he could come to my place and get ready for a show—a drag show. He’d not mentioned his hobby until then.

I gave him an enthusiastic, Hell, yeah!

He showed up with a hockey bag — for non-hockey players, these bags are big enough to carry an adult male body inside. It was filled with dresses, shoes, wigs, and make-up. I kid you not, he had more women’s clothing and high heeled shoes in that bag than I’ve owned in my whole life. Granted, I am a woman who only wears skirts that look good with Doc Marten boots.

I sat on my bed watching him dress and put on make-up, a process that took over an hour and four bottles of Strongbow cider between us. One thing to know about Pete, something that made him attractive to me, is that he is 6 foot 4 inches tall. When he put on his three-inch, size 14 heels, his head almost touched my ceiling.

In his sequinned dress, size 40 D-cup bra, curly blonde wig and garish make-up he was one of the least attractive drag queens I have ever seen. But, he got full points for confidence!

Pete left for downtown without me since he needed to get to the bar early to warm up and hang out in the green room with his buddies. I showed up with two friends who knew the bar well. The show was fun. The songs were drag queen, lip sync classics: I Will Survive by Gloria Gaynor, Tainted Love by Soft Cell, something by Cher… And the performers ranged from excellent to a little bit cringey.

When the show ended I bought Pete a drink and he sat with us for a while then said he wanted to hang out with the guys and get changed. My two friends and I decided to go to a nightclub and meet up with him later.

Turned out it was gay dance night. My friends and I fit right in, they being lesbians and me, looking passably lesbian, in my usual going-out attire — jeans, t-shirt, and combat boots. With my height, weight, hair length and lack of make-up, I was never offended when people said, “Excuse me, Sir.”

The things I saw that night included a fully naked man with a huge erect penis walking about like a celebrity, just strutting his stuff. If anyone had told me this kind of fun was happening in boring Vancouver I would have scoffed. I danced until the last bus — which was just around midnight.

Pete called two hours after I’d already gotten home, apologizing that he’d missed us at the dance club.

It had already been a night of firsts for me so when he asked if he could crash at my place, I said sure. I was feeling empowered and…ummm…a bit horny.

As Pete took off his heels, dress, and fishnets I asked if he’d be willing to keep the wig and make-up on and have sex with me. Since I’d been such a conservative lover in my marriage I was keen to see what my “thing” might be.— if I even had “a thing.”

I really wanted to have “a thing.”

Pete was as enthusiastic as I was as we got started. We kissed. I tried to enjoy it but the lipstick? It tasted and felt disgusting. Remember, I was the forty-year-old who never learned to wear make-up or high heels.

Without going into the truly banal details of sex that was exactly as conservative and boring as I was familiar with in my marriage, we woke up the next morning and agreed that there was no chemistry between us.

No problem. Except that he told me in one of those, ‘I’m not really thinking before I speak’ moments,

“having sex with you made me wonder why I ever stopped sleeping with men.”

That was the first Pete had mentioned he was bisexual.

And me… well, after that night I finally realized that maybe I really did need some time to heal before jumping back on the horse, as it were.