Of course it’s going to hurt. 

Since you are a fag, you need to get used to it.  For the rest of your life, real men are going to be shoving dicks in your ass.  Now I suggest that you suck it first and get it as wet as you can.  Your drool and a couple of wads of my spit are the only things that are going to lubricate this fuck. 

I am going to ram this slab into you in one hard stroke.  Your cherry will not only be popped it will be obliterated, and it will hurt.  But after about forty five minutes of hard pounding you will feel the relief of a warm creamy load of jizz shooting deep into your new cunt.  That spunk will make it much easier for you to take my cock the second time.

A group photo of the exhibition rugby team that visited the school last week.  You pinned it up over your bed to remind you of the good times.  Your roommate looks at it and remembers a wild weekend of drinking and hanging out.  He comments that they were a great group of guys. 

What your roommate does not know is that after he passed out, you let these men run a train on your ass.  You look at the same photo and remember the feeling of thick cocks twitching and swelling as they dump load after load of ball juice into your hole.  You remember the guy in the green towel had a massive 11″ slab of cock and that he used your ass three times and your mouth twice.  You also remember that his orgasms were massive, flooding your cunt like a firehose.  You just nod and agree with your roommate that they were a great group of guys.

Dude you have been checking me out for weeks.  I have seen you staring at my thick meat in the locker room.  Right now your jock pouch is fully stretched out with the raging hard on you got watching me shower.  Stop being so shy.  Time to man up and get on your knees.

Late night in the dorm toilets is a great time to catch your roommate stroking his cock.  The first time was an accident, but now you fake sleep so you can catch him sneaking out of the room. 

Each night you watch, secretly hoping he will catch you and force you to help him drop a load.

The rookie was told that this was part of a bet with the Trojan wrestling team.  He had to remain on his knees in the visiting team locker room for one hour in his wrestling singlet, as a form of humiliation.  It was his responsibility to fulfill the requirements of the bet since he was a rookie and he had lost his match, which cost them the wrestling meet.  He knew it would be embarrassing, but he thought to himself, at least I don’t have to be naked.

As the Trojan’s entered the locker room he heard them say “Good, the faggot is already here and waiting.  He must really want our loads.  Think that’s why he lost the match?”