I am a 19-year-old college freshman and my stepbrother is 14. We share the same bedroom, I have never masturbated in front of or with him nor has he masturbated in front of me. The closest I have come however is when I pretended to be sleeping when he had some friends over. Lets call the friends Kenny and Kalvin, I actually knew them before my stepbrother was on the scene and I introduced them to him and they became good friends. I could not get to sleep this particular night and it was around midnight but I lay in bed with my eyes closed trying to fall asleep. Then I hear my stepbrothers voice 'OK cool he's asleep' then I realized he was going under my bed now under my bed I had a small collection of porno magazines. Anyway they get the magazines and start talking about them and the conversation goes to sex which goes to jacking off which goes to penis sizes. So Kenny says 'well show yours Kalvin' and I hear my brother say 'Oh dude yours looks like a rocket' Then my stepbrother says 'C'mon Kenny it was your idea lets see yours' and the whole time I am tempted to get up and see but don't know how they'd react. So I am laying there and they are talking about their genitals. 'Have you seen your stepbrothers' I hear Kenny's voice say and my stepbrother says 'Yeah but its a lil smaller than mine' now since he said that I was heck a curious about what my own stepbrothers looked like but I still resisted the urge to get up.
Truth or Dare
This is the most exciting part of the story. Eventually the show and tell turned into truth or dare some of the dares I heard them do were; I dare you to suck Kalvins penis, I dare you to kiss my butt, I dare you to Kiss Kenny's testicles, etc. and the one that came at the end was Kalvin said 'I dare you to ejaculate on your stepbrother's face while he's sleeping' when I heard this I was hard as a rock hoping that he would take the dare and after some convincing he said he would do it on my pillow next to my head. So I lay there uncomfortable from not changing positions but very much stimulated by what was being said and more so by what was going to happen. I heard his friends giggling and the sound of him masturbating after about I don't know 10 minutes I heard him say 'look guys its getting ready to come out' and seconds later I felt some warm semen get on my face and assuming there was more on my pillow i rolled my face into it and I heard Kenny and Kalvin and my brother laugh uncontrollably and then make a pact to never tell me what happened but I already knew, The light went out and they got in bed and while they were in bed I sampled a large amount of my stepbrothers semen and made some of my own.