Boarding school fucking sucks. I'm 16 and the Captain of the Rugby team, build like a real man. Short cropped Blonde Hair and Blue eyes. Could get any woman I wanted.Locked away at an all boys school constantly. My parents live a long way out of the city so its not really practical to even go home on the weekends. It was a pretty posh school and so I just spent most of my time either studying or messing around in the gym.

I was privileged in that I only had to deal with a dual room with only one other boy. He was 16 as well but very different from me.Reasonably intellectually minded and not at all sporty he was a fair bit smaller than me, his head only came up to my chin. He wore his brown hair at the maximum length that was allowed at the school, just down to his shoulders.

I didn't have much contact with girls because of the nature of the school and being a boarder so I'd kind of noticed myself checking him out occasionally as he had a beautiful almost perfect ass, nice and round, beautiful.Truth be told I'd cracked one off to it more than once. He know I know he did and he always would wander about our room in just his underwear when we were alone.This was just the run of things until one day on a long weekend, almost everyone else had gone home for the weekend and it was pretty much just us and a few international students left in the whole huge building.

We were watching TV it was some psudo porn bullshit and it was obvious we both had the horn. It was getting close to the time where we had to retire to our rooms. "I'll see you upstairs" he said to me brightly and got off of the couch I watched his ass sway out the door but he turned and looked me straight in the eyes and smiled as he left.

I was left there on my own for a little while and vaguely considered having a quick wank but fuck where would I put the cum?I relaxed there for the half hour I had left and then when it was time I headed up to our room. I noticed something a little odd about my room mate when I went in. Were his lips too red? I don't know. I just stripped my kit off and jumped into bed.The Master came round and checked us but the lights were off so he just headed out.Usually they patrol a little but I knew this would be the last we saw of him tonight.I was still pretty horny so I figured I'd just wait for a little while then have a bit of a wank and go to sleep.

I had my eyes closed but I heard my room mate padding about then the lights turned on I opened my eyes and there was my room mate dressed in a tiny skirt and stockings and blouse.I looked at his face fuck me I thought he's wearing makeup. I got an instant erection but I was also pretty angry."I've seen you looking at me you know" He said "It kind of turns me on"I just looked at him a little blankly. "Fucksake I thought you knew. Why have you got these clothes though?" I asked him. 'I know you want a girlfriend really badly, but the thought of your strong arms around me just makes me so fucking horny' He replied "I could be a girl for you until you are able to find a real one for yourself.

My erection just wouldn't fucking quit I could feel the heat radiating off it and clouding my mind. He came close to me, I looked straight into his limpid brown eyes and he drew closer to kiss me.I grabbed him by the back of the head. He was startled but I'd fantasied about this before and knew exactly what I wanted.

I held him firmly by the back of the head as I kissed him. Dominating him. His initial shock passed and I could tell that he loved it.He melted into my body and we spent a moment there just letting all of the mutual lust from the last few months be consummated by our actions.I felt his small hand reach onto my package and start to massage. It felt really fucking good.

I let him know that he was doing the right thing by breaking off our kiss and rolling him over onto the other side of the bed.I pulled of my jocks to let him marvel at my 8 inch uncut beast. He looked at it wantonly and moved towards it.

'Wait' I said and to his quizzical expression I beckoned him over to me and easily picked him up by his hip and chest positioning him so that he was bent over the bed.This was how I'd always imagined it would go. I looked at his arched back and those fantastic asscheecks. I lifted up his skirt and saw some really cute girls knickers underneath. He's really gone all out hey."wait there's some lube in my top drawer." He said it was only a meter behind me so I quickly grabbed it.I pull his knickers down and finally grope his ass a little feeling the pertness and softness under my hands.I spread some onto my fingers and started to put it onto his little hole. He clenched unconsciously from the cold. I slowly slip a finger in and feel the warmth of him begin to over take the cold of the gel.He shudders, he looks so vulnerable.

I take my finger out and am conscious to smear some lube on the outside of him.He raises himself towards me and I position my cock at his entrance.He looks back at me reasuringly. I start to slowly push forwards, careful to give him time to expand. Its so tight and I can tell that's he's in a massive amount of pain.He pushes his front into the mattress and groans with the strain. He is so incredibly tight and it feels amazing on my cock.The warmth of his entire being seems concentrated on the end of my cock. The lube is working its magic and even though I am going slowly its not too long until all 8 inches of my shaft are buried in him.

He's been going a little spastic and I can see that he's shed a few tears (there is a dark part of my that is turned on by this) i'm pretty concerned however and so I ask him if he's ok.He just moans and pushes back into me softly.I take this as a que to speed up and so I finally build up a bit of a rythem slamming my hips into his cheeks. He starts to moan in pleasure and I'm starting to really enjoy myself.

I know that he is a virgin and the thought that I am claiming him for myself gets me really wired up.I grip onto the top of his ass just where the skirt is and start to give him all I've got.He's writhing underneath me and he starts to cry out softly as he cums onto the bed. I take this as my que and fill his ass with my seed.It feels phenomenal and I feel him quiver underneath me as it fills him up. I withdraw and watch fascinated as some semen dribbles out of his ass. Looks fucking hot.I am a little winded by now and so I grab him by his stomach and pull him into me.

I can smell his hair as I kiss the side of his neck.He turns around and tilts his head up so that I can access his mouth.The passion is unbelievable in our embrace. I play with his little dick a bit milking the last of his cum out. then grab the back of one of his legs and lower him down onto the bed.I move on top of him and continue to kiss him. I break off and just look into his beautiful brown eyes and he raises his groin towards my crotch. The feel of his cock under the skirt and his lithe body underneath me begins to make me hard again.

There is a twinkle in his eye, he knows what is coming.

I raise his left leg over my shoulder and begin to rub my cock on his exposed hole until I become fully hard again.This time it happens a little easier and the entry is helped by the slickness of my cock and the semen already inside of him. Its an amazing turn on to be able to look him in the eyes as I enter him in one long thrust.His face betrays both the pleasure and pain that he feels but I can tell that he is just happy to have me inside of him again. I slowly thrust into him and as I reach as deep as I am able he leans forward and we kiss again he small tongue flickering over my own.

I pull back a little and grab his other leg lifting it as well and start to slowly and methodically pump into him, I watch as my cock is swallowed by his amazing looking ass over and over again. Its a massive turn on.He is hard as well by now and I know that he is feeling the head of my shaft rub into his prostate again and again. He is lowly moaning the whole time as I penetrate him again and again.The heat from inside his body and the tightness of his hole drives me into an ecstatic state as I look into his beautiful eyes and cum into him once again.He twitches like a mad thing as my second load buries itself deep inside of him and reaches up to me.

I lower his legs to my side and snuggle up to him spooning him. Whispering nonsense in his ear.I feel the contentment radiating off of him and I understand that this will now be a regular thing for us. For a while at least.