Sort of a long story, but hopefully it pays off in the end for you. Back in high school, I had a best friend who I had known since 1st grade. We basically grew up together. We were both straight, however I was a little curious. We never really messed around though. He was the smart, nerdy type, never had a girlfriend before. One night he spent the night while my parents went out. We were going out to the hot tub to just relax, but I told him we had to shower real fast first because we were muddy. We showered with our swim suits on and lights dim, but I thought I noticed a slight rise out of him.
We went out and got in the hot tub, and started playing truth or dare. It was snowing, so we thought itd be funny to jump out, lay in the snow, then get back in. Things escalated, and we dared each other to take our shorts off, get out and run a lap around the tub and get back in. When he went, I thought I saw a little bit of a hardon, but wasnt sure since it was dark. We got back in, and the next dare was to put the other persons foot in your crotch. We were on opposite sides of the hot tub facing each other, and we each put each others foot into our crotches. I could feel he was hard. It was the first time I ever felt his cock.
We later went back inside, still without our suits, just in towels. We laid on the couch and watched some movies, under the covers. I bet him he couldnt throw his towel and stick it on the TV corner. He obliged and we found ourselves under the cover on the big couch with nothing else. I remember playfully saying can I hold your middle finger? and he gave me one of his fingers, confused. Then I said no, your other middle finger and he reached over and held out his finger. Then I said no your *other* middle finger. This went back and forth a couple times, he was obviously a little nervous and didnt know how to react.
My friend was laying on his back, but then rolled onto his side facing me, and kind of pushed his waist out. I reached over and grabbed his cock, and was surprised it was super hard. It was definitely a little smaller than mine. We just laid there, me holding his cock, not moving. About 2 or 3 minutes later, after just holding on to it, not even stroking, I heard him start breathing funny. Then he blew his load right on my hand, on the couch. Judging by his face, Im pretty sure thats the first time he ever had an orgasm. After he was done, and started to soften up, he pulled away, we got dressed, and never said anything about it.
The next morning, we found ourselves laying on the couch again. It was early and my parents had not woken up yet. We had breakfast, played some video games, and were watching some tv or a movie on the couch, under the covers. I sneakily reached over and started to slowly unzip his fly, maybe hoping he wouldnt notice. I tried for a while to unzip his fly, but no luck. I was thirsty, and got up to go get a drink, trying to hide my raging boner.
When I came back, I got laid down and got under the covers. But as I got under, I looked over and noticed his pants were unzipped and open. I could see his little bulge pushing on his underwear. Green light! I slowly reached back over, rubbed my hand on his underwear for a minute or so, then tried to reach into his waist band. He raised his hips up a little, giving me access to pull his underwear down. So I pulled out his little hardon and started stroking it slowly.
After a minute or so I kind of moved up a little closer, and pulled his arm down and out his hand on my pants on my cock that was just itching to come out and play. He immediately pulled his arm back away. Oh well, I guess this will just be one way, which I was fine with.
I pulled the cover up over my head, so I could see what I was doing. I wanted to see his dick in my hand. Once I got the cover situated I could see his wonderful penis. Not very big, pretty slender, and a surprisingly small amount of hair. For a few minutes I just slowly stroked, felt, and caressed his penis. He put the cover over his head so he could also see what was going on. It was then obvious that he had never played with his dick like this, and wanted to see how to do it.
A minute went by and his breathing started to become laborious. He kind odd whispered oh, oh yeah and then blew his load again. We were both breathing hard at this point. I rubbed it gently until he was too soft and tender to be touched.
We had one more encounter like this a few months later, but then never got the opportunity to do it again. Weve never spoken of it to each other.
We went out and got in the hot tub, and started playing truth or dare. It was snowing, so we thought itd be funny to jump out, lay in the snow, then get back in. Things escalated, and we dared each other to take our shorts off, get out and run a lap around the tub and get back in. When he went, I thought I saw a little bit of a hardon, but wasnt sure since it was dark. We got back in, and the next dare was to put the other persons foot in your crotch. We were on opposite sides of the hot tub facing each other, and we each put each others foot into our crotches. I could feel he was hard. It was the first time I ever felt his cock.
We later went back inside, still without our suits, just in towels. We laid on the couch and watched some movies, under the covers. I bet him he couldnt throw his towel and stick it on the TV corner. He obliged and we found ourselves under the cover on the big couch with nothing else. I remember playfully saying can I hold your middle finger? and he gave me one of his fingers, confused. Then I said no, your other middle finger and he reached over and held out his finger. Then I said no your *other* middle finger. This went back and forth a couple times, he was obviously a little nervous and didnt know how to react.
My friend was laying on his back, but then rolled onto his side facing me, and kind of pushed his waist out. I reached over and grabbed his cock, and was surprised it was super hard. It was definitely a little smaller than mine. We just laid there, me holding his cock, not moving. About 2 or 3 minutes later, after just holding on to it, not even stroking, I heard him start breathing funny. Then he blew his load right on my hand, on the couch. Judging by his face, Im pretty sure thats the first time he ever had an orgasm. After he was done, and started to soften up, he pulled away, we got dressed, and never said anything about it.
The next morning, we found ourselves laying on the couch again. It was early and my parents had not woken up yet. We had breakfast, played some video games, and were watching some tv or a movie on the couch, under the covers. I sneakily reached over and started to slowly unzip his fly, maybe hoping he wouldnt notice. I tried for a while to unzip his fly, but no luck. I was thirsty, and got up to go get a drink, trying to hide my raging boner.
When I came back, I got laid down and got under the covers. But as I got under, I looked over and noticed his pants were unzipped and open. I could see his little bulge pushing on his underwear. Green light! I slowly reached back over, rubbed my hand on his underwear for a minute or so, then tried to reach into his waist band. He raised his hips up a little, giving me access to pull his underwear down. So I pulled out his little hardon and started stroking it slowly.
After a minute or so I kind of moved up a little closer, and pulled his arm down and out his hand on my pants on my cock that was just itching to come out and play. He immediately pulled his arm back away. Oh well, I guess this will just be one way, which I was fine with.
I pulled the cover up over my head, so I could see what I was doing. I wanted to see his dick in my hand. Once I got the cover situated I could see his wonderful penis. Not very big, pretty slender, and a surprisingly small amount of hair. For a few minutes I just slowly stroked, felt, and caressed his penis. He put the cover over his head so he could also see what was going on. It was then obvious that he had never played with his dick like this, and wanted to see how to do it.
A minute went by and his breathing started to become laborious. He kind odd whispered oh, oh yeah and then blew his load again. We were both breathing hard at this point. I rubbed it gently until he was too soft and tender to be touched.
We had one more encounter like this a few months later, but then never got the opportunity to do it again. Weve never spoken of it to each other.
........ 
