I've had a little game going with my housemate. We've always had a mutual attraction but we're good friends so we've never let it go anywhere. But we've been living together (with two other mates) for three years now and I have to admit I've listened to him jerking off in his room numerous times.
I always masturbate in bed, I do it other times too but I've been masturbating myself to sleep since I was about 12. I lie on my stomach with my hands down my pyjama bottoms and rub myself. I don't always reach orgasm, a lot of times I drop off with my hands still down there, but I'm usually pretty wet by the time I fall asleep. If I do come then you can pretty much guarantee my pyjama bottoms have a sticky, wet spot about the size of a saucer.
A few weeks ago I came in from lectures and went straight up to my room, expecting my housemate to be in his. I heard a clank come from my room and as I opened the bedroom door, he was putting the desk lamp back on. I asked him how his day went, assuming he was grabbing something from my room (we're always in and out) and he seemed flustered, but answered and quickly left. Shortly after a series of low grunts from his room indicated I'd interrupted something and when I looked over at the bed, my pyjama bottoms were no longer folded on my pillow, but in a heap. He knew what I did in them, clearly.
The next morning after he'd left, and after I'd brought myself to a morning climax lying in bed, I took the bottoms, freshly wet, knowing he'd be back in a few hours, and put them on his bed. Sure enough at lunch he returned, and I waited inpatiently in my room for him to go upstairs. When he did, there was silence for about 30 seconds and then a moan of pleasure. I heard him hurriedly unbuckle his belt and the springs on his mattress squeak, and he was obviously humping his bed. I sat on my own bed with my jeans around my knees and fingered myself listening to his frantic grunts. When he was done there was silence for a long time and I fell asleep half naked on top of my covers, fingers still covered in my juices.
When I woke up a few hours later he'd gone out again, but he'd left my pyjama bottoms folded outside my door with a note saying 'Thanks'. He'd ejaculated in them. Ever since we've been swapping cum-soaked pyjamas or underwear, and secret smiles around our other friends.
Last night it finally went a bit further. I got in late, about 1am, and he was watching a movie in his room. I peeked my head in to say hi and it happened to be a movie I really like. I asked if I could come watch and he said yes, but my clothes were damp from the rain (stupid British weather) so I went and put my pyjamas on. Not unusual, we all walk around in our pyjamas, but now I was sitting beside him on a single bed in pyjamas he'd creamed twice since they were last washed. Within about 3 minutes he shifted uncomfortably and I knew he was rock hard.
'L... Lauren' he stammered eventually, just as I was about to explode with pent up sexual tension
'I'm sorry, I got to...' I nodded, knowing what he was saying, and we both lay down. His hand immediately went down his pants and he let out a moan. I turned on my side to watch him and whispered for him to take it out. He did so readily, too horny to think twice, and I settled lying half on top of him and half on the side, grinding myself against his hip. We were kissing gently and moaning into each others mouths, and I stopped only to take my top off and push my bottoms down to my knees as I began to increase my pace, growing close. His hand was moving quickly up and down his shaft and my hands were gripping his torso when he tensed. I knew before he said it.
'I'm going to come' he groaned, and I felt a hot splatter of semen against my breasts, then stomach. Feeling him unload all over me was enough to finish me off and every muscle in my body contracted as my climax washed over me. I let out a small cry and he hugged me closer as I kept bucking against him, covering his right hip in my own cum. We lay in silence for a few minutes and he kissed my head.
'I think those pyjamas could become infamous' he whispered. I laughed, and we fell asleep right there.