A first-time young prisoner about to spend some time learning.

You are an 18 year old boi, entering a five year stretch of prison for the first time. Not for the first time, you curse your shitty luck, and even even shittier taste in girls. You should have known you couldn't trust Heather. Even from the beginning, she was two faced and selfish. She was the little rich bitch with the good girl reputation and you were the poor trash bad boi with a rep of getting into fights and dealing . Sure, you DID get into fights on a regular basis, mostly due to people questioning if you were one of those sissy bois just because you were on the short side, and you DID deal , but at least your reputation was earned, where as Heather was as wicked as they come.

Not that you ever got to cum with her. You never even got past first base with her. She just teased and promised a little more the next time, and all you had to do was help her move massive weight of heroin that her 'ex'boyfriend was trying to unload. You should have seen it the frame up coming as you were supposed to be his competition, and now due to one traffic stop, you go directly to jail, and do not collect 200 dollars.

The only bright side is that since the bimbug hit the prison population, has practically become nonexistant. Even with the sissies segregated to their own cell blocks, there are ample opportunities to smuggle one over to gen pop, and they never say no. You've always hesitated to fuck a sissy, not because you seriously doubt your manhood, but because you don't see why you should risk it even if it is an infintesimal chance of infection just to fuck some worn out whore with a gaping hole.

So imagine your surprise when you arrive at your cell on your first day and find it filled with hardened convicts surrounding a soft sissy. One turns to you, his face marred by a gnarly scar that he futilely tries to mask with a snake tattoo. "Hey, I'm your 'roomie', Snake. Since it's your first day, you want to take a stab at this sissy? We might not get to smuggle another one in for a week or more."

You look at the pink haired punk in the middle of the cell. She has two cocks in her ass, is jerking off another two as they cover her tits and face in cum, and bobbing between three shafts surrounding her flushed face. You have been tense and pent up lately, and even though she looks a little worse for wear, your cock is swelling in your jumpsuit. You see the convicts sizing you up, and you get the feeling your status will be determined in the next few moments.