The delicious irony of being a dyke trans woman and pegging a man for the first time

It may seem funny to think that one of the first sex acts I perform as a woman, a recently minted woman, is with a strap-on and pegging a man, and it is.  I didn’t even know how to put the darned thing on.  Thankfully I was surrounded by ladies who knew what they were doing and could strap me in.

And yes, it felt partially weird, but mostly just hysterical, that I was walking around the room with a big black rubber truncheon jutting from my pudendum.  Of course I was wearing knickers anyway, and hot pants.  I even needed help sliding on the condom.  The things I need to learn!

It took me a while to get it in, as his hole was rather tight, and he was whimpering, “its so big, oh, it’s so big.”

“Yes, baby, and you’re going to take all of it,” I purred, but spared him the pained entry and teased him with one rubber finger first, tons of lube, then two, then three…all while I caressed his perineum and said sinful things to him.

I could have pinched myself a thousand times when I finally slid it in and felt his kneels buckle underneath me.  He buried his face in his hands and whimpered at the girth.  I loved it.

My little bitch was amazed afterwards to learn that I had never done it before.  Totally surprised.

“I’m just a natural, baby,” I demurred.  Despite my husky voice, I didn’t want to break the spell I had cast over this poor soul as he got to see me cavorting around in a bikini all day.  I could see the hunger in his submissive eyes as he served me throughout the day.  I could see him taking my long, gazelle-like legs…snatch waist, and I could already imagine myself with my legs wrapped around his face, pinioning him in place.

And when I say, break the spell, I fucked him with an experience that comes from a lifetime of being a straight man.  I knew how to use the real thing.  Even if I didn’t like it most of the time, the bad boy was in demand.  “The loss of your cock is a loss for women everywhere,” said one former partner who knew it would land well.  She was full shit.  As a woman I am much more trouble.  And much more fun.

When I couldn’t get sufficient purchase on this man, I mounted him true and proper, arching one leg over him, and grabbing him around the torso, leaning into him fully, pulling his hair with my other hand and thrusting him with all of my body, all of my muscles, eager for the workout, and practically crawling onto his back.

I pounded him mercilessly and I could tell he had to use all of his strength to not collapse.  He was whimpering in desire and ecstacy.  His cum was leaking from his caged cock as my rubber cock impaled him and milked him and made him sing in falsetto.  He was making a mess of the puppy pad.  Maybe I was going to ask him to lick up his own spunk.  Maybe.

“Would you like to be made to lick up your own spunk baby?”

“Yes, Mistress.”  Oh lordy, you can say that to me again and again.

I asked another domme looking on with lust in her eyes if she wanted to strip in and spit roast him.

“You bet I do,” she said and was in harness in seconds.  Clearly she knew what she was doing.

When I pulled out, he moaned, and she stepped in where I left off, giving him a flood of dirty talk.  Calling him her bitch, her sissy, her cuck, her slave and smacking his ass.  I lay at his head and watched the action, harness now off, and invited him to look at my crotch, the feminine expanse of the infinite that now lies between my legs.

Even I could smell my perfume.  And I don’t mean synthetic.  My pussy is very present to me.  I can smell her clearly wherever I go, but especially when I am aroused, exercising, or peeing.  I might as well have been doing all three.  The distinctive smell of pineapple, funk, and maple syrup tinged with the rose scented oil I anoint my skin with is very present.  I’m not the only one who can’t get enough of it.

Ever since I strapped on a strap-on I haven’t been able to stop thinking about.  How joyful it was to wear it.  How fun it was to look down and see it.  I didn’t mind that it was smaller than the original, though I think it would also be fun to wear one that is larger.  Why does a strap-on feel good when having an actual penis not feel good?  This is the peculiar state of life for a trans woman…perhaps any woman, though I can think of many women who genuinely would love to have a dick, at least for a while.

Did it emphasise that I am not a man?  Quite possibly.  I was wondering if it would be triggering to me in a negative way, remind me of something that I had wanted to leave behind my whole life.  But no chance.  It was just fun.  Really, really fun.

There is something else.  Mounting that man and not feeling anything in the shaft, but instead feeling the pressure on my clitoris, my vulva, felt strangely affirming…the whole thing did.  That I didn’t feel it.  And that made the physical sensation more abstract.  That I could perform an act that we associate with the male of our species but finding it made me feel more female…

And some of that has to do with how it also feels to inhabit an increasingly femme body—specifically that my musculature has changed, that I am not as strong, that I needed to find a body rhythm in sync with his in ways where had I been a man I might have been able to force.

Of course, what I really want to do is to fall into the arms of a woman and if we penetrate each other I am not too fussed, but do like the symbolism of it.

When we were done with him we bade him go and clean himself up and revelled in the post-coital glow.  There are few things I think I have done that have been more fun.