Both me and my friend were 18 at the time of this story and we had been friends for about 5 years before this happened. This is my first time writing on here so I don't know how long this is gonna be or how good it's going to be lol.

Me and my friend, lets call him B, had been friends since around 7th grade and had finally made it to our senior year of high school. Near the end of the year our school rewards the seniors with a 4 day long trip to NYC. I had always had a fantasy about jerking off with other guys but had never had the balls or the opportunity and try it out but I saw this trip as the perfect chance. We would be staying in a hotel and it would be 2 to a room with two twin beds and roommates sharing a bathroom. It was a no-brainer that me and B would be rooming together and I was really nervous but excited to see if I could get him to jerk with me.

We spent the first day out with our class doing the usual touristy things people do in NYC. We were out until about 8pm when we finally got back to the hotel. When we got back to our room I told B I was gonna go take a shower and the first part of my plan was set into action.

When I got out of the shower I made sure I was wearing the tightest pair of boxers that I own and that that was the only thing I was wearing. We had seen each other in our underwear before so it wasn't completely foreign but I could still be a look of surprise on his face when I walked out. He was wearing a pair of shorts and a tank top since it was late May and the hotel AC wasn't great. I decided to see if I could get him in the mood to try and get him more comfortable with the semi formed tent I had in my boxers.

"Did you see those shorts Abby was wearing today?" I started with.

"Yea dude half her ass was hanging out of them. She's such a slut. I love it though."

"Yea it was making me so horny seeing her dump truck just hanging out like that."

"I can see that haha" He said as he gestured to the now fully erect cock my underwearing was a doing a terrible job at hiding.

"Haha sorry dude I haven't jerked off in a while and she just makes me so horny. She get you horny too?"

"Ha yea she does! I haven't jerked off in a while either."

I remember thinking that it was now or never and I told him that we should jerk off so we weren't walking around all day with boners tomorrow. He agreed but said that we should do it underneath the covers so it wasn't too gay. Surprisingly he said we should do it in the same bed so we could look at pics on his phone while we did it. I obviously didn't say no and we both got underneath the covers, pulled down our boxers and started stroking.

We did this for about 5 minutes looking at pics of girls we found hot and commenting on them and what we wanted to do to them. I was having a great time and I could tell he was enjoying it too but I wanted to see if I could take it a bit further.

"Ugh the sheets I terrible they're lowkey scratching up my dick. Do you care if I take off the covers?"

"Umm yea it's probably fine." He replied.

That was the only answer I needed and I pulled my cock out from under the sheets almost instantly. I'm a but over 7" uncut, clean shaven, but I don't have much girth. I started stroking slowly going up and down while twisting my wrist trying to put on a show. I tried to get him to be a bit more comfortable too.

"Come on man now that you've seen mine it's only fair that I see yours. Take it out I won't judge."

He was a bit hesitant but he agreed. He pulled his out and I had to stop stroking because I almost came. He was smaller than me, about 5.5" cut, bush trimmed, but he was girthy as hell.

"Holy shit dude nice cock" I blurted out.

"Thanks man yours is good too"

We continued to jerk but the moment was so exciting I wasn't even looking at the girls anymore. We both began to speed up and our breathing got heavier.

"Fuck dude I'm close" he said.

"Me too bro"

We both picked up the speed and were going at light speed up and down our cocks. He let out a small grunt and a moan and I watched as cum oozed out of the head of his cock. That was all I needed to finish as I felt my cock start to throb and cum shot out of my dick and onto my chest and the pillow behind me.

"Dude that was so hot." I said after we both waited a bit to calm down.

"Fuck yes dude I don't know why we waited so long to do this together."

"Yea we should definitely try this more though"

"Totally."

We both cleaned up a bit and went to bed. I couldn't sleep for a while though as I could only replay what had just happened over and over in my head. Eventually I did go to sleep though and when I woke up I was eager to try more.

Let me know if you guys want a part II! We ended up doing more on this trip and I would love to write about it!