Kinky Confessions

First Time Strap-On Sex for a Straight Man

Woman in Black Stockings

I have a fantasy that I shared with my lover of six months. It usually takes about this long to start divulging my dark thoughts and kinks that I’d like to try. I wanted to try a strap-on with him.

When I first brought it up, he thought I was kidding and laughed it off. The second time he made it clear that he didn’t want anything going up his behind.

I mentioned it a third time while we were watching porn together. This is something we like to do as part of our foreplay. We take turns picking clips, favorites that we’ve watched individually and others we find randomly.

I chose a sexy strap-on video that I’d carefully selected, one which I thought might change his mind. It featured a sexy brunette with a similar body to mine, and she did a striptease which is one of his biggest turnons.

He was hard before the porn vixen even brought out the strap-on gear. While he watched the quintessential scene, I took his cock in my mouth and left it there while the video played out. He could barely contain himself until the end, when he came inside my mouth. I swallowed and smiled up at him.

He not only changed his mind, he bought me a damn strap-on! We went shopping online together at the Kink Lovers BDSM & Sex Toy Store.  I let him choose a didlo size he was comfortable with, and he let me pick out the harness I thought was sexiest.

Was he nervous? Hell yes, but so was I. I’ve always talked a much bigger game than I was willing to play, and this was new to both of us. We shared a bottle of wine to lower our inhibitions, and I began with a sultry striptease, leaving only my high heels on.

I then let him watch as I secured my harness and dildo. I channelled my inner dominatrix and commanded him to get on all fours like a good little doggie. He obeyed.

I lathered him with lube before gently pushing the tip of my new cock inside his asshole. I thought I was going to come right there and then. He shuddered twice, before I slid the dildo inside as deep as I could. In and out, in and out, I rode him from behind.

He made sounds that I’d never heard before, and we had simultaneous orgasms. Using the strap-on has become a special treat for both of us.

I was patient and my lover was willing—two things that make for spectacular exploration and results!

Kinky Confessions is a bi-weekly post on Kink Lovers. We want readers to share their tantalizing tales of kink, fetish, and fantasy. SUBMIT YOUR STORY HERE! These stories don’t have to be real, they can be fiction that you’d like turned into reality.

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curtis conner
2 years ago

I too have wondered about this, but I’d prefer her to use a small size strap-on. But I can’t even find a woman who will spank good and proper, so I don’t want to take on another empty wish. I’ve been needing a spanking woman my whole life and have been sad and lonely regarding such. I can’t even meet a lady who will share a few minutes role play that entails her giving me a very rear spanking share, so what the hell is the use. It would be another broken dream. I call my wishful thinking “MY haunts”… Read more »

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