Taking It Like a Man

By William I. Fitzgerald , AlterNet. Posted April 24, 2008.

The first time my girlfriend fucked me in the ass it was with a small purple strap-on dildo that her ex-girlfriend had shipped from Ohio. Like any lady should before taking her man's anal virginity, my girlfriend took me for a night on the town beforehand. Walking home, after dinner and a long stop at a bar, we decided it was about time I made good on an earlier promise to let her screw me for a change.

Butt sex wasn't my idea. As far as anal is concerned, I'm not exactly a connoisseur. That goes for giving as well as receiving. Aside from a female college friend turned one night stand who demanded it and the occasional forefinger while I'm going down on a woman I haven't thrown much up anybody's (to quote a friend back in junior high) dirt spider. And, aside from receiving the occasional stinky pinky while a girl went down on me, not much had been up mine.

That all changed when I met Mac. Not right off the bat, of course. Our first date, scheduled a few months after meeting through mutual friends, started off as American as apple pie. We met near her downtown office after she clocked out of her 9 to 5 and I took her to her second-ever baseball game. The San Francisco Giants were facing off against Texas. The sun was setting over the bay. We had hot dogs, popcorn, and cold lemonades. American. Ok, the lemonades were spiked with rum. But the rum was from a bottle I had smuggled into the stadium in my left cowboy boot, so the theme still fits. It was probably the most wholesome date I had been on all year.

Toward the end of the game Mac brought up that she had a girlfriend. I'd been living in San Francisco for more than a year, so I tried to hide my disappointment and act like girls brought that up on first dates all the time. Mac quickly made it clear that she was in an open relationship with her girlfriend, who actually lived in Ohio. Emboldened by that information, the cowboy boot rum, and the fact that I had already fallen in love with her in the 5th inning I decided not to let a girlfriend deter my efforts. Mac did the same; after the game we ended up in bed.

It was early on in our relationship when Mac asked if I would let her fuck me in the ass with a strap-on, and I was drunk. But that wasn't the reason I agreed to her proposition. Neither was the fact that we seemed to be half joking at the time. I was curious, but that wasn't it either. I've been curious about more than a few things that I've never actually gotten around to doing. As for it being the first step on a closeted path of desire toward experimenting with men, that just wasn't the case. Same goes for repressed fetishes: Being fucked in the ass was never on my list of secret dirty wishes.

But Mac had been sleeping with women since high school and she and her ex-girlfriends had screwed each other with strap-ons. I thought, given that she asked me about it, she might miss giving someone the business. Mac is a beautiful, intelligent, and supportive woman. I was head over heels for her, and I wanted to make her happy. I thought that along with pretty flowers and little cupcakes, letting her fuck me in the brown eye would be a way to show my appreciation for her. Ignoring the fact that societal standards don't exactly align with a straight male taking it up the ass, I agreed to let her nail me. Besides, I got to fuck her all the time; it only seemed fair.

Trying to be the world's best boyfriend wasn't my only motive. I also was in some weird competition with her exes in my mind. Mac had been able to fuck her incredibly butch ex-girlfriends with a strap-on, so why not me? Sure, they didn't take it up the ass, but I don't have a vagina so my options seemed limited. If those bull-dykes were man enough to get fucked by Mac wearing a strap-on, then so was I.

Or so I thought. After I surprised Mac by agreeing to take it in the ass she asked her now ex-girlfriend, who apparently wasn't as open to their open relationship clause as she had let on, to be sure to send her dildo and harness along with the other personal items she was shipping from Ohio. All of this was new to me, so I was a little nervous. But after the strap-on arrived in its small Fed Ex box I was feeling more confident. It was not big. A few straps, a few metal rings, and a veiny, purple, dick-shaped piece of plastic about the size of two fingers. Taking that thing up the ass, it seemed, would be a cake walk.

We hadn't planned it the night it happened. "Take a dildo in the back door" wasn't written on my calendar. A few weeks had passed since the literal and figurative package had arrived and we were joking about it while eating dinner by candlelight. After some ravioli, a bottle of wine and heavy drinking at a bar near Mac's house, the joking took a serious turn. We had been bantering about our butt sex pact with a friend of mine we had run into at the bar after dinner. The guy was laughing hysterically. But he also kept looking at me as if to ask, "Are you serious?"

And that's when it dawned on me. I was serious. I was going to do it. At that point it seemed clear to both of us that that night was the night. We excused ourselves and rambled home. Soon I found myself bent over on Mac's bed, my chest pushed up against the mattress, while she strapped the harness around her long legs and smooth hips.

When she penetrated me for the first time I tensed up and let out a long succession of soft, high-pitched "ow"s. I was not off to a manly start.

See more stories tagged with: sexuality, gender, sex, masculinity

Liked this story? Get top stories in your inbox each week from Sex and Relationships! Sign up now »