This prompt is inspired by this sissy caption: https://www.redgifs.com/watch/imperturbablefaintabyssiniancat

This setup is that we are roommates hanging out late one night and drinking. I'm straight but you're bi and are regaling me with a story of how the last guy you had hooked up with had cum so hard he had passed out just from you fucking his ass. I roll my eyes, thinking that you're exaggerating and tell you that it's impossible for a guy to cum without anything touching his cock. You're adamant that it is possible, but I maintain that the entire idea is ridiculous. You ask if I want to put my money, or more accurately my cock, where my mouth is.

You propose a bet that if you can make me have a hands free orgasm, then you get to lock my cock away in chastity since you will have proven that I don't need it anymore. You explain to me that you would tie my hands behind my back so that there is no possible way that I can actually touch me cock, then put a prostate massager up my ass. If I don't end up cumming within 30 minutes then you'll pay my half of our rent for the rest of the year, but for each time I do cum in that time period, that's another month I'm locked in chastity. To keep track of how many times I cum, you'll put a condom on my cock and swap it out whenever I blow my load so there can be no debate over how long I need to stay locked up. And just for added flavor, you say that I need to dress in one of your ex's thigh-highs, skirt, and croptop to help me get in the mindset of cumming like a girl.

I think this entire idea is completely unhinged, but I can't pass up the opportunity to live rent-free for over half of the year. It might just be the alcohol talking, but I end up agreeing to your terms not realizing that it would change the rest of my life.

Dm me if you are interested. My discord is screamacrossthesky#1867. I'm thinking to make this a longterm rp, I will keep begging you remove the cage and you can use that as an opportunity to feminize me. Maybe you say that you'll bump a couple of weeks off my sentence if I start shaving my body hair and dressing like a girl while I'm locked up. Maybe you let me make another bet that's double or nothing and I end up prolonging my sentence or needing to wear an even smaller cage. I get so desperate to cum that you eventually turn me into your freeuse sissy slut that you can fuck whenever you want and I end up thanking you for it.

Kinks: noncon/dubcon, forced fem, forced gay, straight to gay, chastity cages, bondage, ring gags/ball gags, collars and leashes, uniforms, outfit control, rough anal, throat fucking, toys, slavery, edging, public, humiliation, free use, creampies, breeding, blackmail, sounding, beast, incest, hypno

Limits: scat, gore, watersports, vomit, vore, snuff, inflation, mpreg