A Wandering Hand in the Night

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The story of my first time with another guy.
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CLZero
CLZero
3 Followers

**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.

Since I sleep with my shirt off, he started to lightly rub my stomach and chest, and pinch my nipples while he continued to thrust slowly. After a few moments, I grabbed his hand and moved it to my rock hard cock. He grabbed it without hesitation and took me to the most powerful orgasm I have ever had. All the while rubbing his cock between my thighs. After I came, he backed away and I heard him masturbating. I pulled my jeans back up and heard him finish just before I fell asleep.

Again, the next morning we didn't say a word to eachother about the night's events, either through not knowing what to say, or not wanting to bring it into the light. Instead we continued on in this fashion with much more frequency than we had previously, as winter break had approached and were nolonger limited to the weekends . In the following months, and even several times after concerts, when a group would stay at his house, we would still make sure we slept next to eachother, waiting patiently for our friends to all fall asleep before I would feel his wandering hand either on my hand, or on my ass - depending on which way I was facing.

After months of this, several times while he was thrusting his cock between my thighs, he would pull back a little too far and his cock would slide up and find its way against my ass. While this surprised me at first, over time I began to enjoy it, even look forward to it. I even started to push back against him when this happened. Instead of following my lead, he would quickly pull away, and resume what he had been doing. All the time we continued these sleepovers, he never once would take my lead. However, we didn't stop there.

As I became more bold, as our system was completely ironed out and silently understood by both of us, I became curious about blowjobs. Frequently during nights when the signal was his finger in my hand, I tried grabbing his finger and pulling it to my mouth. Each time, he would pull his hand away before I got it between my lips. After numerous failed attempts, I decided I was going to make a move one night we stayed at his place. Before turning the lights out, I waited for him to lay down, and I positioned myself facing him, but not parallel with his body, instead I laid down noticeably lower. As soon as the light was out, I moved my hand into the normal position. After I responded appropriately to his fingers, and he pushed his cock into my hand, I began jacking him a little slower than normal.

As I worked up the nerve, I slowly inched my way down until his cock was in front of my face. Frozen with nervous fear, it took me probably 10 minutes to build up the nerve to make my move. Once I did, I closed the couple of inches that separated my lips from his cock and took him into my mouth for the first time. While I expected him to pull away, he didn't. Instead he stayed perfectly still while I very slowly took more and more of him into my mouth, exploring the taste and sensation of having another man in my mouth with my tongue.

I am still not sure if he initiated the movement, or if I did, but after a few minutes, he moved from his side to his back, and I moved over him so I was laying next to him, but still sucking his cock. This time he didn't make a sound or even move. Thinking I may have been doing something wrong, I pulled him out of my mouth and started jacking him off. Apparently just in time too, because only a few moments after I stopped sucking his cock he came all over his stomach.

The next time I stayed at his place, I initiated the same move, but made sure he stayed on his side. After a few moments of sucking his cock for the second time, I got up and turned around so my cock was in his face. I pulled him back in my mouth again and could feel him jacking me off. After a few minutes of me sucking him while he jacked me, he worked up the nerve and took me into his mouth. Because I am a bit larger than average, he wasn't able to get much more than my head in his mouth, but still we laid there sucking eachother for almost 10 minutes before I pulled him out of my mouth and he came (again without notice). I am still not sure what I would have done if he came in my mouth. After he came, he rolled over and went to sleep, leaving me to finish myself (as was the normal protocol between us).

After this second encounter that led to oral sex, we had probably 3 more "sleepovers" before he stopped returning my calls. For reasons unknown to me he became somewhat hostile only toward me, and began to spread rumors among my friends.

Despite the sour ending to everything, thinking back to those sleepovers still gets me rock hard. I have not had any sexual contact with another guy before or since, although occasionally I now find myself looking at a different "flavor" of porn than I used to. Quite often I find myself wishing I could go back and relive one of those nights just one more time.

*

That's my story. I have never told anyone about this, not even in an anonymous setting. While writing it out for the first time, I was amazed at the number of details that flooded back to me in such vivid detail.

CLZero
CLZero
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4yourpleasureiam4yourpleasureiam5 months ago

I will do that for you and thank you. Please pm me. Central AR.

AnonymousAnonymous6 months ago

Very well told story of how one man gets into sex without any over the top 'dressing' for the story. If one took the comments of every man's 'first time', the over all results would quite probably sound much like this. Elegantly, tastefully written in which a continued series of similar finally form a story. Very well done.

AnonymousAnonymousover 1 year ago

Very nice, i really liked it. Though, too close to home for me. I do suck cock, and love a couple loads in my ass and tummy before sleep now, then new.

AnonymousAnonymousover 2 years ago

This is a good story that probably happens to a lot of horny young guys. I had always wanted to jack off another guy and feel his hard cock pulsate as he spurts, and spurts hot sperm all over my hand...

AnonymousAnonymousalmost 3 years ago

Does anyone know a porn like this

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