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Chapter 21
by SophiePert
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Technically Not Breaking My Rules
It wasn't fucking. Technically at least.
Isn't that the idea. In the eyes of God or whatever you're still technically a virgin if you take it up the ass?
But staying a virgin was hardly the reason for my hesitation.
God, it does feel dumb to say it but when he presses his thumb against the button of my ass I just tense and I tense in large part because I am unnaturally fearful of anything happening down there. And I know that it's dumb, that it's animal brain stupid societal conditioning unnatural reflex trained into me by homophobic assholes who are so afraid of anything that even remotely might make them seem gay that they hesitate to even think about their own asshole but that doesn't change the fact that when I feel it happen, when I feel him press just the tiniest bit inside of me through that hole, I tense and fight between two instincts.
Giving up and giving in.
And in the end all I can do is find some kind of middle ground here because I moan and press back for just an instant, letting just a bit of him inside of me. And I feel it stretch me out and my body melts around it. The sensation of being penetrated there sends a shock running through my body and makes me clench the seat beneath me and grind my teeth, my eyes rolling into the back of my head as what can only be described as a minor climax washes over me almost instantly and all driven mostly because this does feel wrong in the best possible way and it feels so delightfully naughty and it pushes all the right buttons, flicks all the right switches and triggers in my mind. It feels so warm and so invasive and so goddamn good and for that instant when I'm pressing back all I want is more.
Before I pull away.
Falling forward and falling off of him. Collapsing into a puddle on the seat and struggling to catch my breath as I tuck around and spin, dragging back and pushing my back up against the door behind me while I draw my knees up to my chin and shoot daggers over at him on the other side of the cab.
And the asshole, the absolutely cocky and arrogant asshole who just fingered my asshole, just grins and shrugs.
"I mean you didn't say I couldn't," he says.
I narrow my eyes even more, trying to catch my breath as I point out, "I didn't say you could either."
"Well then you better set limits," he leers at me, "Otherwise I just might assume something else is on the table."
"Look but don't touch isn't on the table I'm guessing," I ask, but he just rolls his eyes, "Fine then. Hands, obviously."
"I can touch anywhere with my-" he starts, but I hold up a hand to cut him off.
"I can touch with my hands," I tell him, "I'll jerk you off."
"Lovely," he says, "Look, darling. I know you just got out of high school but some of us here haven't been satisfied with a hand job in a good few decades."
"I didn't say just that," I stick my tongue out, "My mouth too. I'll blow you. And you can touch my ti- my breasts too. You can touch my breasts. You can touch... anywhere above the waist."
He raises an eyebrow, "A blowjob and a fondle? That's it?"
Reaching slowly I slide over and tap my index finger against the glass of the display.
"Seems to me that's still plenty, as far as market rate is concerned."
It's a bluff, and one that I don't know that I'm accurate on. While the number I owed was hardly high, it wasn't exactly low either and I figured he probably had a far better grasp on the going rate for ladies of the night than I did.
Still, it just might work.
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My Second Chance
A Gender Swap Story
When a man with regrets gets a second chance at life he winds up getting far more than he could have ever imagined. Sent back in time to his first day of college he finds himself back in his old body, with a twist. He’s a girl now, the feminine version of himself, and all his old friends and all his old enemies have designs and ideas on just what he should do with the second chance he’s been given.
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Updated on Dec 31, 2024
by SophiePert
Created on Nov 1, 2022
by SophiePert
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