**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.
Instead I felt a finger being slid into my hand again, this time from a different angle. As I had done moments ago, I gripped it and started jerking off his finger. After a few motions, he stuck two fingers in. Having a sudden moment of "what the fuck am I doing?" I just laid there and didn't respond. He then pushed down against the first joint of my fingers a few times and I again gripped his fingers and started to jack them off. He then pulled his fingers out of my hand and I felt the strangest and most exhilarating sensation on my hand I had ever felt. As he pressed his penis into my hand, I was absolutely amazed and excited by just how hot (temperature-wise) it felt. I couldn't get my mind around the silky smooth skin covering the contradictory sensations of such rigidity, yet such softness.
I must have been contemplating these sensations a bit too long because I felt him turn his hips and mimic the pushing down sensation in my hand he had done with his fingers. Knowing what it was he wanted me to do, I squeezed his cock and jacked him off. As I did this, I could hear him occasionally let out a very quiet moan as he bucked against my hand VERY slowly, as if not to wake me. A few times, be bucked a little to hard and I would have to reposition my hand on his cock. It only took 3 or 4 minutes of squeezing that amazing contradiction before I felt him tense up and start to buck against my hand even harder. Knowing what was coming, I quickened my pace and felt his cock pulse in my hand while he shot rope after rope of cum onto the carpet. Once his climax had ended, I slowed my pace considerably and kept jacking him until he pulled out of my hand, rolled over and went to sleep. In the morning neither of us acknowledged in any way what had happened, and went on as normal yet again. He probably had stayed over 2 or 3 more times before the next leg of the story, each time starting our encounter with just one finger, then moving on to 2, and on from there.
After several weeks of this, something occurred where I ended up sleeping at his place again. For whatever reason when we stayed at his place, we slept on the floor of the finished basement. The first time I stayed there after we had started this little nighttime game, I laid down with my back to him. While most nights it was close to 30 minutes after lights out that he made a move (that time limit seemed to shrink with every encounter), this night he seemed a lot bolder. About 7 to 10 minutes after laying down, I felt a light touch on my ass. As I laid there I felt more of his hand as he lightly groped my ass. I pushed back against him a little, and felt him retract his hand, only to reposition and start to lightly hump me. I laid there, slightly pushing back against him while he grinded against my ass for maybe 5 minutes before I decided to get bold. I pulled down my jeans and boxers. As soon as I finished this, I felt his cock pushing against the back of my thighs, JUST below my ass. He grabbed my hip and gently thrusted his cock in and out of the area between my thighs, just barely touching the back of my balls.
