I was out at boarding school, and didn't really have any problems with it, apart from one group of friends/roommates who were openly hostile and taunted me sometimes. Once, when I was 15, me and my roomates had to be dispersed to other rooms for 2 weeks or so, because of some building work . As luck would have it, I ended up with the jerks.
The first 2 days we just kept our distance, and didn't talk much to each other. But on the second evening. when I was lying in bed, one of them sat down next to me, and started "playfully" slapping my face. I said "what the hell are you doing?" and told him to piss of, but he continued. I grabbed his hand, but he wrested it free, and then gave me a real, hard slap. I shouted "What the fuck?" - then he said "Now!", and 2 of the others grabbed me.
He said "Turn him over",which they did. One held me down at my arms and shoulders, the other held my feet. He stuffed a pair of socks in my mouth, and I heard him slip out of his bottoms. Then he straddled me, pulled down mine, and said "Let's see how good you are, faggot". He lubed himself with spit, and fucked me in the ass. Me being a virgin, and him using just spit (though lots of it), it took him a while till he had successfully entered me. But the others held me down till he had achieved his mission to completion. After pulling out, he said, "Thank you, baby", which got a laugh.
When he was done, the one holding my feet took his place (and the fourth guy, who'd just been watching until then, took over my feet). I got fucked by all 4 of them, one after the other. As the third guy was fucking me, I came, which they noticed -they snickered and one of them said "I think he likes you best" to the one fucking me. When they were all done and finally let go of me, I got a slap on the ass, and then they all went to bed as if nothing had happened.
The next day, I had to wash cum and shit stains out of my bottoms.
They left me alone the rest of the 2 weeks. Until the last evening before I returned back to my old room, when they all lined up at my bed. One of them had a tube of cream in his hand (having learned from the first experience). The boy who had busted my cherry said "Turn over and pull down your trousers; we're stronger than you, anyway". So I did it, and they gang-raped me for the second time. This time only three of them fucked me, though. The fourth had decided he wasn't that keen on anal, so I had to suck him off (and swallow his cum) instead. (Afterward, still panting, he said "Good job" and "How did you like the taste of me, faggot?".)
On the one hand, I obviously hated the whole experience - because I hated them, and because it was degrading and somewhat painful. But on the other, I was - and still am - turned on by it, because I was physically attracted to all of them to one degree or another (and also [italic]because[/italic] it was degrading...)