On Breaking a Cherry
by Autumn | Jun 9, 2025 |
Let’s talk about virgins.
Not their first time with sex in general, I’m not interested in that. I prefer grown men these days. No, I mean their anal virginity. There’s nothing like being the first one to push into a man’s ass.
He always acts surprised, like he’s discovering something about himself for the first time. That little gasp, the wide eyes, the way he half-resists while his body begs for more. And then, once I start grinding into his p-spot? It’s game over.
I’ve had more than one virgin boy cum hands-free while I fucked him for the first time. It’s raw. It’s messy. It’s real. And it is so much fun. Breaking a new hole is a special kind of experience. You get to feel him stretch and open, feel that mix of fear, shame, and craving swirl together.
I like taking my time. Teasing, taunting, pressing in slowly until he’s squirming under me. Watching a man come undone when he realizes he loves it. When he realizes he was made for it. That’s power.
Now here’s the wild part. I’ve found out that we have anal virgins among our ranks of volunteer subs. Boys, what are you waiting for? It is time to put away excuses, find a strong woman who knows how to use her cock, and surrender your anal virginities!
Then tell me all about how it felt to finally submit completely.
I’ll be waiting.
It is certainly something that sits on my bucket list of things to experience. Has to be near the top too.
One day I might be able to say those 3 words…. “Be our guest”. 😉
It’s a work in progress Miss Autumn but I’ll tell you all about it when it happens.
It is definitely something I want to experience Miss Autumn. It’s finding dominate woman to peg me. But at sometime in the future it will happen.
I got you, Miss.
haha guys better watch out or they’ll issue you a Conclave command…