About as well as a guy being ass-fucked against his will for the first time can.

"Noooo, nononononono...aaaaah...", is what spills out from Bitch 2's mouth as his backdoor is stretched forcefully by the intrusion of your monstrous cock, the words tinged with pain and panicked panting as he tries not to crack under the fact that he is being anally **** by a super-powered convict right at this moment.

You, however, couldn't care less if he cracks or not. Your bitch's mental state didn't matter to you in the least. All that mattered to you was the fact that his ass was nice and tight and completely yours to fucking wreck with a brutal fucking. Like you'd said, you weren't going to be gentle. Not in the least.

As if to reaffirm that fact, you gripped his hips tight and pulled him backwards at the same time you thrust forward, forcing more of your rock-hard prick into his anal passage. He cried out breathlessly as he was filled with even more throbbing dick, his body tight and his back arching as though he was trying to somehow arch his way away from you. It was a useless gesture, however, as your strength was implacable and your will to get as much as your cock inside of his virgin ass was unshakable.

"I said fuckin' relax, bitch! Unless you want to die wrigglin' on my dick like a gutted fish.", you growl at him as you get a foot of dick-meat inside of his clenching asshole.

"No-no-no-no...aaarrrrgh...fuuuuuck. T-toooo biiiiig. In my...fucking....gutssssss....", he babbles in response and you scoff as you reach around to grasp the upper part of his combat armor and rip it away as you had to the woman, reaching down to run a hand over his taut belly.

"Bullshit...wait...maybe not. I think I can feel me pressin' up against your guts here! Well, don't that fuckin' take the fuckin' cake...let's see how much more you can take of that, huh?", you say to him, not really feeling a sign of your dick pressing into his abdomen, but liking the shiver of fear and the moan of pain and panic that leaves your bitch's mouth at the words.

"Nooooo....", he groans out, but then words are lost to him as you slide your dick almost completely out of him, only to drive it back inside his stretched anal passage once more. He can only cry out as you begin to truly fuck his ass, pistoning your cock in and out of his clenching asshole with hard decisive thrusts.

"Fuckin' hell, that's a good bitch.", you growl as you grab a handful of his short hair and pull back roughly, looking down at his face and seeing a glazed look and gaping mouth looking back at you in return as you seem to have fucked the senses out of him already, "You got a good career as a prison bitch ahead of you, slut. I think I might keep ya 'round, if only to pass ya 'round to all my convict friends and let 'em have a turn at this nice fuckin' ass o' yours."

"Noooo....aaaaahhh....noooo...", he murmurs senselessly and you laugh as you pound his ass relentlessly, driving yourself even more deeply inside of him until you have almost hilted yourself inside of his ass. Only a few inches are still outside of his ass now and you could swear you actually can feel your cockhead pressing against his belly from the inside as you fuck him so very roughly. You're definitely roughing his guts up, that's for sure, but you don't give a shit so long as you get off.

So you truly ravage his ass, not giving him a chance to breathe as you ram yourself into his tight asshole over and over and draw pained gasps from him every single time. You work yourself into a frenzy, grunting with exertion as you well and truly **** his ass to make sure he knows who owns him. Life on the inside has made this sort of domination second nature to you and so, while fucking the female guard had been rough on her but still pleasurable in its way for the recipient of the fucking, this was all about power. This was about letting this guard know that he belonged to you now and that there was not a goddamn thing he could do about it. He was yours and he would accept that fact by feeling your cock fill him and ruin that asshole of his.

And, of course, by taking your cum wherever you decided to give it to him when you were done.