Disable your Ad Blocker! Thanks :)
Chapter 119 by SophiePert
What's next?
The Spectrum
Straight. Gay. They're two ends of a spectrum.
And I've dipped my toe into the waters enough to know that neither side is bad and neither side is good and all of it is just people. I may not know where exactly I lie on that scale, but I know that I'm not at either end.
And I know that being labeled as one or the other doesn't have the power over me that it once did.
I'm terrifed of anal sex, because I'm worried that it'll already confirm something that I already know about myself. I'm not a straight cis man anymore.
I'm something new, and I'm more than ready to explore.
So it's fucking ridiculous to be worried about this, to be fearful of it. It means, in the end, nothing. It's just the dying gasps of a life I don't have to live anymore. Of a person I don't have to be.
And so maybe I can ignore that second excuse. Maybe I can see it for what it really is, nothing more than a cop out.
Of course even though the second excuse is bullshit, that doesn't mean the first is magically wiped away in the process.
"Won't it hurt?" I ask, my brow furrowing as my voice quavers with a real and true fear.
He knows he has me then.
Victory is won by degrees, by inches. In this case literally.
I feel him release his hold on me. He's still playing with my asshole but he reaches over, moving to grasp the lube that he set aside. There is the telltale sound of him uncapping it followed by the indecorous one of a dollop being squeezed out. Something wet and cold hits me just beneath my tailbone and his thumb leaves my asshole to guide it down between my cheeks, working it around and around until I'm well and slick.
"Not going to lie," he says, "It does. So I'm told, at least. I wouldn't know from personal experience. I mean I've never had it done to me, I've done it plenty of times."
Another dollop squeezed out, this one onto his cock no doubt. Once more his hand leaves my cheeks and I hear the wet squelch of him twisting his fist around the head of himself to make sure that he's just as lubricated as I am.
What a gentleman. He wants this to be as good as possible for me.
What an asshole. He wants this to hurt.
But when the head of his cock slips between the cheeks of my ass and presses right at the button of my asshole where his thumb just was, all of my worries fade away. The touch of him awakens the same desires I'd felt when he played with me and when Rachel played with me earlier still. A curiosity that just might kill the cat, bringing me to the point of regret for the first time since I became Emily, but that isn't going to stop me now.
"Oh god," I moan in disbelief, "You're going to fuck my ass. I'm going to let you fuck my ass."
Join my Patreon for only $3 a month and get early access to new chapters and over a years worth of exclusive content. https://www.patreon.com/SophiePert
What's next?
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.
Updated on Dec 31, 2024
by SophiePert
Created on Nov 1, 2022
by SophiePert
- 4,183 Likes
- 1,175,785 Views
- 920 Favorites
- 632 Bookmarks
- 650 Chapters
- 142 Chapters Deep
Comments moved below the chapter.

Comments