"So, bad boy, I notice this bench is spreading your cheeks pretty wide," Chandler says. "Ever picture doing anal like this?"
"Yes," you say, "All the time." You wonder if that means he's going to do the same.
"Your ass is self-cleaning and self-lubricating," says Chandler. Then Chandler started undressing. You can barely see him behind you and it hurts to crane your neck. The bench doesn't have a spot to rest your head either, being long enough to hold your chest up, but no longer. This was going to start to hurt after a while. You'd always wanted to see a woman in this position, but she would be free to use a safeword and get out. Chandler didn't give you a safeword.
Your roommate is naked now, and you'd never expected to see that much of him. Chandler is 25, the same as you, and he works out a hell of a lot more than you. Chandler's abs make you jealous. His cock is hard too, although not as big as what you have now.
"Chandler, come on, I don't want to have gay sex, please," you say. "If you're gay, cool, I guess, wish you'd told me, but don't take it out on me."
"The girls you want to fuck aren't gay either," he says. "And they probably don't want to take it up the ass. You should know what it feels like to get pounded before you do your own backdoor invasion."
Before you can object, you feel the strangest sensation of your life: a firm, warm cock resting on top of your butt crack, throbbing slightly. Chandler's hands run down your sides.
"Dude, you need to lose a little weight," says Chandler. "You now have visible abs like me, and slightly bigger muscles everywhere else too."
A warm, relaxing sensation flows through your body, and you can feel your gut tightening up, your skin stretching out ever so slightly.
Is it wrong that you kind of want to check yourself out in a mirror? Some guy's dick is on you, but you want to know if you look hot? You tell yourself to get your priorities straight.
"Yeah, much nicer," says Chandler, rubbing your sides again. His cock is removed from where it was resting, and you have a brief moment of hope, before you feel something even more strange: Chandler's circumcised, spongey cockhead pressing against your anal ring, along with something runny.
"Yeah, dude, you're leaking some kind of lube," says Chandler. "I think you're ready for it."
"I'm not ready for anything you sick- Oooh, oh god!" Chandler's dick broke through your ring while you were bitching, and now you can feel it pressing, pressing, pressing, deeper inside, stretching you out, and it hurts, but not as bad as you were expecting.
"How's it feel?" Chandler asks.
"Like, full, or like, taking a dump, I don't know, it feels weird, but like, not that bad?" You don't know how to answer honestly.
"I'll let you think it over," says Chandler, as he keeps on pressing. Hairy balls make contact with your butt, and you think it's all the way in, then Chandler pushes a little harder, his body along your legs warming you up, and somehow he's able to fit a little bit more into you.
"Oh, man," you say, knowing how stupid you sound. Like a porn slut.
Chandler gives another command. "You can orgasm from anal sex very easily." Chandler laughs. "I won't make it not hurt, that wouldn't be fair, but I think you should get something out of it."
"I don't want an orgasms, I want- ahh!" You gasp as he slides back out, then grunt as he drives it back in, still slow and steady.
Chandler doesn't take a break, he's obviously got the endurance for this, and you wonder if he's got experience too. Chandler keeps on fucking you, and you realize you are indeed getting fucked by a man, by your roommate. This wasn't what you expected when you bought that collar.
"God damn, this feels amazing, tightest ass I've ever fucked, but all the lube you could ask for," Chandler says, beginning to gasp himself.
You save yourself the indignity of responding, afraid your words will be broken up as his rhythm picks up, faster and faster, pain and pleasure mingling inside you as you get fucked for the first time. Your cock is still hard, as Chandler commanded, but you're beginning to think it'd be hard anyway.
You can feel an orgasm building, tense and pleasureful, and when Chandler thrusts one last time, as deep as he can go, you pull tight against your cuffs, straining hard, as your orgasms wracks your body and you start to shoot cum, shot after shot after shot hitting the bench, and oddly, your first thought is: Am I going to get cum on the floor?
Chandler slaps your ass, making you snap out of your post-orgasm fuzzy thoughts. Your hole aches when Chandler's cock pops out.
"That was great, bad boy," he says.
"That was torture, asshole," you say, full of spite, but you aren't allowed to lie, so you're compelled to add, "And also felt incredible, best orgasm I've ever had."
Chandler laughs, and how dare that traitor laugh at you?
Chandler begins to ask another question.