Kinky Confessions

First Time Strap-On Sex for a Straight Man

Woman in Black Stockings

Getting My Man to Try a Strapon for the First Time

I have a fantasy that I shared with my lover after 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 up my strap-on fantasy, 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 turn-ons.

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 together as strap-on beginners. I let him choose a dildo size he was comfortable with, and he let me pick out the harness I thought was sexiest.

Our First Time Strapon Experience

Was he nervous? Hell yes, but so was I. It was my first time too! 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 strapon 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 to try something new—two things that make for spectacular exploration and results!

Are you interested in meeting women into strap-on sex? Be sure to see our Pegging Dating Guide for the best strap-on dating sites.

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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Kink Lovers is the online magazine for kinky people into BDSM, fetish, and kink. If you want to explore your kinky side, spice up your love life, or meet new kinky partners - enter the world of Kink Lovers. Enjoy D/s relationship advice, kink education and resources, BDSM and kink dating tips, fetish facts, and reader confessions.

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