**at all relevant times all parties involved were 18 or older**
This is a true story, written to the best of my recollection.
*
So my first time with a guy happened around 10 years ago. At that time, my friends (who were all about the same age) and I were into a specific kind of music. One of my friends started bringing this other guy around, we will call him "Nate." It was kind of odd because "Nate" was several years older, and didn't seem to have many friends closer to his age. Anyway, Nate would take us to local concerts in the nearby big city almost every weekend. We loved it since he was our "in" so to speak for the local music scene, of which we knew nothing. This continued for a month or two, so naturally we all became good friends with Nate, and we would often all stay over at one friends house from the group.
As friends tend to do, occasionally one (or more) of use would stay at Nate's, or he would stay at our house without the rest of the group. One night when Nate was staying at my house, I was sleeping on my back, with a few covers on. I woke up in the middle of the night feeling something RIGHT next to my penis, almost touching the side (over the covers and outside my clothing). Groggy and confused I looked down in time to see Nate remove his hand. Realizing he had been groping me, I had a sudden adrenaline rush and was very excited. Hoping he would do it again, I laid back down and pretended to sleep for almost 2 hours before actually falling asleep. He didn't try anything again that night. But while laying there I was very confused, I had never been attracted to guys I didn't see anything sexual about guys at all. In fact, I was often too busy chasing girls to have even considered the "other side." In the morning, neither of us said anything and things continued as normal.
The next weekend Nate stayed the night again. This time I was awoken very late at night feeling something in my hand. I had been sleeping on my stomach with my arm hanging off the side of the bed, hand barely touching the floor. As the feeling in my hand started to wake me up, I also heard something I recognized as someone masturbating. I came to the realization that Nate was masturbating while holding my hand. Again I was hit with an adrenaline rush which caused me to tense up and slightly squeeze his hand. He immediately froze, as did I, and pulled his hand out of mine. I again pretended to be asleep, never moving my arm except for the momentary tensing.
After a few moments, I heard him continue to please himself, slowly at first, but gaining speed. Once he resumed his original pace, he placed one finger into my hand. After a few moments of me not moving, he stuck another finger in my hand. This time I tensed up again, and for reasons I still do not understand, I tightened my hand on his fingers and held them softly enough that he could have removed them but firmly enough that he could feel pressure. He immediately froze again, but did not try to remove his fingers, instead he went back to masturbating and left them there. Again, for reasons I don't understand, I started to very slowly mimic the masturbation motion on his fingers. He froze again as I kept doing it for a few moments. When I stopped, he pushed his fingers down against the first joint of my fingers, still gripping his hand. I took this as a sign he wanted me to do it again, so still "sleeping," I resumed jacking off his fingers. he pulled his hand out and I could hear him reposition himself on the floor. I figured I had either done something wrong or he had finished.