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Strap-On

It’ll probably surprise you that I’ve only worn a strap-on dildo once in my life. I’ve also only received anal once in my life. Balance and moderation.

I’ve never been sure about my gender for too long, but I know I love men, and I love being fucked

Fucking, on the other hand, as in being the active fucker in the situation – usually makes me feel gross. Fucking is something I want to do equally, or to have done to me. When I do it to others, it makes the others look to me, well, like pussies. Nowhere did I learn this lesson harder than I did with the strap-on dildo. Hence the one hit wonder.

I had a boyfriend who was a good man, whose only sin was a lack of self-confidence that led to a childhood of substance abuse and eventually a binge alcoholism justified by him in its relative sobriety to his earlier years. Well. Maybe that wasn’t his only sin.

So this guy, well, he was sweet and kind and treated me well almost always. He also was rough, street savvy, and not at all homophobic. Straight as they come, but certainly not afraid of his own ass or of exploring sexuality. He liked it when I’d give him a little anal pressure while he fucked me. 

And anyone who knows me knows that I’ve experimented with gender identity. I’ve done drag boylesque and bound my chest and wore suits and ties to high school. 

So wearing a fake cock, why not?

I have used a butt plug on men, with my hand, and used my fingers. Just never actually strapped it on. I will again continue to be fine with anal pleasure, it’s a different thing from a strap-on dildo.

We discuss it and decide that a strap-on dildo is the way to go, not handheld. I want the feeling of actually having a cock and fucking him. And he is into it. He likes being fucked up the ass, just not by men. And so together we visit the Pleasure Chest in Los Angeles to pick out something that will fit us both.

Mind you this was in the late 1990’s when the choice of harness wasn’t as broad as it is now. I remember all the dildoes seemed too big. His dick was small. Did he really want to be fucked in the ass with a dick bigger than he fucks my pussy with? That seemed off, somehow, AND it’s not like he was into regular anal training, so they all were way too big.

We find a harness that allows a range of strap-on dildo attachments and finally after asking they bring out a small dildo that fits it from the storeroom.

Strap-On

And so there he is, my hot, rugged lover, face down, ass up, lubed up. He has a great ass. Medium frame body, proportional. Good balance, a really great fuck.

And there I am, looking at the milky white curves of his rear end, staring down past the dangling silicone dong, trying to take it all seriously. This ridiculous thing hanging from my hips that isn’t at all a part of my body and doesn’t at all feel like one 

I lube up the dildo in quick strokes, and then lube up his cock. I notice how much more slowly and intentionally I stroke his cock than I do the dildo and take a deep breath and get into it. Imagining my silicone dick as the most sensitive part of me. Creating a tight circle with my hand and ringing the tip of his dick with it as I tease his asshole with the lubed up dildo. 

He sucks in his breath and I see his muscles tense and then relax as he surrenders himself to pleasure. 

I smile at being able to give it to him and it distracts me for a moment, and I’m annoyed that I actually have to use my hand on my fake dick to be precise with it. In my fantasies I just use my hips and everything goes where I want. My idea of a strap-on was that it would simulate having a dick attached to my body, and most of my experience is centered around annoyance that it’s nothing like that. I try to make the best of it, and use my hand to get that precise depth and pressure I seek.

Years later I fuck a man who has learned the same thing, and holds his cock like a paintbrush, carefully and precisely using it as the instrument of pleasure he’s trained it into being. But now – I chalk it up to the equipment and don’t think that perhaps men have to use their hands on their cocks too to get the kind of results I’m looking for.

And so I let him fuck my hand while I slowly, gently fuck his ass. I hold the base of my fake cock and grip his cock with my hand, leaning over him. It’s awkward, and he soon helps me by putting his hand on his own cock. 

I get more creative with my strap-on dildo. Scooping up into his prostate and jacking him faster with the other hand. Deeper and deeper into his ass with the dildo. The sight of it disappearing into him makes me feel oddly lesbian.

I’ve had experiences with women before and it just isn’t a thing that turns me on enough to pursue. I really like being fucked by a man. And this fucking of a man, of a man-hole, is not working for me. Though it is hot to see how turned on it gets him, and how quickly, it’s not as if I have the best view of that. Rear vantage point gives me the back of his head.

Which I pull back to avoid as his body goes rigid, bucking back into me and holding his breath. He moans through a tight throat and then he’s screaming as he shoots jets. 

“Oh my fucking God” he says “I came so fucking hard.”

I know he’s saying this to encourage more of this kind of play, but as look down at him, sweating, lube dripping out of his ass, messed up, it again triggers the wrong buttons for me. I like men messing themselves up messing me up, but not for me to remain cool, calm and collected while he loses it at and in my hand. 

Speaking of losing it he runs to the bathroom for some spluttery shits, as I too would if I’d been fucked up the ass by a strap-on dildo. And at that I swear I’ll never strap it on again, and still haven’t since.


Yes, it was the same dude. Definitely into butt stuff.

Other posts about butt stuff:

Hot Sex I Didn’t Have: Pegging the Palace Guard

Anal Sex


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2 replies on “Strap-On”

Oh Zoe… this is so insightful! The detail is telling… thank you for sharing the awkwardness and the journey of this with us!

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