By: Britney Cachin

That’s kind of cool looking, I thought absently, as my eye caught a small fuschia sculpture sitting nearby on the desk. I kept getting glances at it over the raised posterior of the woman between my legs.

It reminded me of a sculpture featured on a postcard that a friend once brought me from her native Romania. In the postcard it had been yellow, standing proudly against a cobalt sky, with the words, “The Endless Column” written elegantly on the other side.

This one was much less dignified, somehow, and I figured, a shitty modern reinterpretation. While I liked this girl, it was pretty obvious from looking around her room that her brief stint at Mass Art had imparted a devotion to garish, cringeworthy modern pieces.

“You ok?” She asked, surfacing to grab a sip of water from the glass being offered by her boyfriend. I didn’t mind him being there, but had made my intentions for the evening very clear. He was not a part of them. They shared a quick kiss-- then she followed my gaze to the sculpture-- and looked back at me with renewed interest.

She had rowed in high school, and was built for it. Now, she was happily engaged to a  bi-sexual male partner who towered even above her six feet, and between them earlier at the bar, I had felt lilliputian. I mention all of this to explain how quickly she was able to flip me over onto my stomach from a lounging position even as that interested look completed its survey.

I snarked internally, Ooh, ok, she’s an ass man, as I gave a little wiggle for her benefit, positioning myself for optimal arch and optimal eye contact avoidance with her boyfriend sitting on the couch 5 feet from my face.

He had the best view in the house when said face registered what was actually going on.

From his position, he had seen, let’s call her Michelle, scoop up the ‘sculpture’ slather it in lube, and pop it right into my butt.

HHHHNNNNNNNN, I inhaled sharply, eyes popping in surprise. Michelle gave my ass a playful smack as a response, lustily whispering, “You like that, huh?”

In my shock, all I could say was, “I….think so?” Desperately hoping that her boyfriend would never tell her of the pure horror and confusion that must have been all over my face at the moment of….impact.

Gently, and with practiced finesse, she maneuvered what I now knew to be an anal toy--not a tacky sculpture-- in a way that was not at all unpleasing, but still,  incredibly panic inducing.

I didn’t prepare for this.
How do you prepare for this?
Oh God, are you SUPPOSED to prepare for this?

I couldn’t think of a single man I’d ever been with (this was at the tail end of my pansexuality exploratory phase, which had been preceded by a monogamous hetero sexual period, which had been preceded by what I thought was a bisexual awakening) who hadn’t at least suggested we try anal, but I had never agreed. I had always found the whole prospect an unsettling combo of degrading, potentially disgusting, and completely unnecessary.

But here I was, and while still breathless from shock, I didn’t feel at all degraded-- so far, so good. I realized, my aversion to this kind of sex was really about my aversion to male pleasure at the expense of their female partner. With cumbersome power dynamics replaced by a focus on my experience, I was quickly starting to relax and enjoy myself.

Michelle played my body like a cello, one arm wrapped around front driving me towards orgasm, the other busily working the bright pink toy. It was weird, wonderful, and absolutely a fluke that I hadn’t reacted differently and walloped her upside the head reflexively. The slender design was also, without a doubt in my mind, a perfect match for what I now knew to be my limit before pleasure turned into discomfort and pain.

This could have gone really wrong, I thought finally, as we laid in a tangled heap in the afterglow, but I liked it.

The FUQS

• It is imperative that you keep your sex toys clean and safe, especially when you’re having sex with multiple partners.

• It is safest to use a condom with sex toys that penetrate….anything, just like when you do it au naturale.

• Most sexual miscommunications do not go this well. Whether you view consent as sexy, or merely a requirement, find a way to work it into every new act you want to engage in. Remember, she may be eyeing the anal toy you left out as a hint, or she could be thinking about Romania. You won’t know until you ask.