My cute, crossdressing flat mate

'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.