My next experience with Jack - Sharing a hotel room on a school trip

This is a true story, all individuals involved were 18+ when it took place. If you're here from my first post about Jack, this will be a follow up of the next experience I had with him.

I'll give a brief update as to what happened between our first encounter and this one before I dive into the story. After the party, I messaged him and told him that I had fun and to let me know if he ever wanted to do something like that again. He replied pretty coldly and told me not to get attached. Pretty typical Jack behavior if I'm honest, but I wasn't ever attached to him--just horny and thought he was hot. Otherwise our friendship went back to the status quo aside from me trying to flirt here and there.

Now we jump ahead about six months or so. We were going on a multi-day field trip for one of the groups at school we were both involved in. Each of the hotel rooms had 3-4 people of the same gender assigned to them with two beds per room. Jack and I were assigned to be with one of our other good friends.

The day we were leaving for the trip, we were waiting on the bus for everyone to show up and our other friend was the last person we were waiting for. The teacher who was in charge of the trip got a call from his parents saying he was being grounded and wasn't allowed to go on the trip anymore. We then left campus and started driving to the destination. I was disappointed about my friend not coming, but my heart started to race a bit knowing that it would just be Jack and I sharing a hotel room together.

When we got to the destination, we dropped our bags in the room and then headed out to do activities we planned for the trip. It was a state wide festival we were involved in, so there wasn't really any structure, we just got to free roam and do whatever we wanted. There were also students from all over the state there that we interacted with.

Our friend group was pretty much the same from the party in my previous story. At lunch, Jack talked all the guys in the group into having a bit of a competition on tinder to see who could match with the most people while we were there. We agreed to it and long story short, Jack had by far the least messages (idk why, Jack is pretty damn hot) and one of the other guys and I had roughly the same amount and pulled ahead of Jack pretty quickly on our first day there.

I kept giving Jack a bunch of shit about him having so few matches. I was trying my best to rile him up. I also kept showing him any of the hot girls I matched with to make him jealous. It definitely worked, i could tell i was getting under his skin. At one point Jack, the other guy, and myself were showing each other some hot pics we got on snapchat from some of our matches. At one point, Jack started to pop a bit of a tent from one of the girls I was going back and forth with. We teased him and gave him shit about it as he adjusted himself to hide his boner since we were in public.

At the end of the day, Jack and I got back into our hotel room. I was still chatting with a few of the girls on Snapchat and Jack kept looking over my shoulder to see some of the pics I was getting. I could tell he was getting pretty horny, but after how cold he was to me after our first experience together, I wasn't going to give him the satisfaction of trying to make a move on him. After a bit he got up and headed to the bathroom saying that he was gonna get ready for bed. I teasingly said that I bet he was just gonna go beat his meat and he denied it.

After a few minutes he came back out shirtless, but still wearing his shorts and boxers. He got in his bed and I was already in mine. He started asking me questions about the girls I was talking to and if I was planning on trying to meet any of them while we were there. I told him I might and he started to practically beg me for a pretty wild request. He said if I hooked up with the one girl he thought was really hot that I should try to record it so I could show him the video. I protested because I wouldnt ever film someone or show a video like that of someone without their consent. Then I started teasing him more saying stuff like "sounds like you just wanna see my dick, bro. Pretty fuckin gay if you ask me." And we bickered back and forth like that for a bit.

That's when Jack grabbed his water bottle and started to take a drink from it. He then suddenly dropped the open bottle on his bed and water went everywhere. I looked at him confused because the way he dropped it looked pretty intentional. He said "oh fuck, my beds absolutely soaked now. How am I supposed to fall asleep in this bed now?" I immediately had a feeling that he was hoping I'd tell him to just share my bed with him. I was still feeling vindictive about him being cold to me and was just like "damn, I don't know. That sucks. Oh well, goodnight" and then I laid down.

I didnt look over at him, but there was awkward silence for a bit as he tried to plan what he'd do next. He then timidly asked "you think it would be alright if I just moved over to your bed for the night?" I replied with "im sure theres enough of a dry spot in your bed for you to make it work over there." He grew frustrated and told me that the whole bed was completely soaked. I rolled my eyes at him and did my best to hold back a smirk, but I ultimately told him that i guess he could share my bed for the night.

He got all giddy and hopped out of his bed and walked over to mine. I moved over from the center of the bed to make room and he laid down on top of the covers. I asked what he was doing and he said that he didnt want to make it weird and I said that him laying on top of the covers was the only weird thing that was happening. He chuckled and got under the covers with my approval. We just laid there for a bit and then he asked "I normally can't fall asleep unless im just in my boxers." I did my best to quell any sort of excitement in my voice and replied "as long as you're not naked, it doesnt make a difference to me."

He immediately pulled down his shorts and tossed them out of the bed. He talked me into messaging the girls on snap again, which I did, but it was pretty late and they weren't replying. Then after a few minutes of silence he says "God, im so fucking horny." I turned my head to him and raised my eyebrows and said "yeah?" He nodded his head at me with a sexy smirk across his face. I then said "well its pretty hard to fall asleep when your horny, so feel free to take care of that however you want." He asked if he should just go to the bathroom and I replied saying "you can if you want to, but the bed would be much more comfortable."

I felt the covers move as he grabbed his boxers and pull them down. I could see his hand start to make the comforter go up and down as he started to stroke himself. I kept glancing over and my bulge started to lift the covers a bit as I got hard. "Mind if I do the same?" I asked him and he told me to go for it. I pulled my shorts and boxers off and tossed them to the side. He then grabbed his boxers and pulled them all the way off and he tossed them onto my face as a joke. I let them sit there for a few seconds before pulling them off and tossing them back onto his face, both of us were laughing at it.

He then pulled his phone out and pulled up pornhub. When he saw me look over at his phone, he angled it so I could see it better and asked what my favorite category was. I don't even recall what I told him, but he pulled some of it up and we started watching it together. I was more focused on watching him jerk off under the covers than I was watching his phone.

Jack then pulled the covers down and kicked them to the foot of the bed, uncovering us both. He said "i see you trying to look, if you want to watch me the least i can do is give you a better view." At this point, he still had the porn on his phone, but both of us were mostly looking at each other's cocks. After a bit more of this, I let go of my dick and reached out for his. He looked over at me and smiled as he let go of his cock and let me take over. He did the same for me and we started jerking each other off. He slid over next to me so our legs, hips, and torsos were touching.

With my free hand, I started to feel up his body starting with his bicep, then made my way to his pecs and nipples, before running my hand down his abs. I felt my hand raise and lower across each of his abdominal muscles as I made my way to his happy trail and trimmed pubes. After that, my hand slid down to his balls, cupping them in my hand. I gave them occasional tugs and rubbed them with my thumb. He started to thrust into and out of my hand just like he did at the party, but this time he didnt have to try to control himself like last time. We were both dripping so much precum onto each other's hands, it was obvious we were both really turned on.

He was much more vocal this time around since we were alone. He kept moaning and talking dirty, asking me if I loved touching his bbc. I told him that I loved doing it. Then I said "if you like how my hand feels, bet you'd love how my throat feels." His eyes widened and he said "oh fuck, I'm gonna cum!" And immediately started shooting rope after rope all over himself, my hand/arm, and the bed. I was pretty surprised as I didn't think we were quite to that point yet, but I stifled my laughter not wanting to be rude.

After he was finished cumming his face turned red embarrassed that I made him cum when I offered to suck his dick. I started to tease him and a bit and he let go of my dick, since he was finished. I told him that just cause he came early doesnt mean he gets to abandon my handy early. He started to jerk me off again and play with my balls as he laid there covered in his own cum. My hand was still on his cock, which was still throbbing from time to time. After a minute or two, I started to slowly jerk his cock off again. I squeezed it a bit more than earlier, milking the blood into it to keep him hard. Id also spin my hand a bit when id go over his head. He was moaning pretty loud and his whole body would jerk from time to time from the over stimulation.

I told him that he wouldnt have to deal with that of he didnt cum so early. He tried to act unbothered by it, but by the looks he gave me I could tell he loved being put in his place by me. We kept going for a bit and when I was getting close to finishing, I let him know and asked if I could cum on him. He looked nervous but nodded 'yes.' I rolled over and got on my knees straddling his waist a bit. I put his hand on my cock and told him to keep going. As he tugged on it, I started to shoot my load across his body. I shoot pretty far though, especially when im turned on, and I was very turned on. My first shot of cum hit up to the headboard with the rope going across his face, neck, and upper chest. Each consecutive shot from there covered his jaw, neck, chest, and abs with even more cum.

When I was finally finished I, he milked the last few drops out of my cock and then I laid back down next to him. I looked over at him covered in cum and said something like "damn you're a whore." He laughed and said "coming from the guy who offered to deepthroat my dick." We both chuckled and I asked him if he'd ever been deepthroated balls deep before, which he said he hadn't. At that point, I already deepthroated someone who was slightly bigger than him and told him that and confirmed that I could definitely take him balls deep in my mouth and that it was a shame he had to cum so early in the night (I wasn't gonna let him live that down lol).

I suggested for us to clean up and try to sleep and he agreed. The way he decided to clean up though, was by just rolling his body across the sheets and wiping himself clean. I was horrified and asked why the fuck he did that when that was the only bed we could use. He then told me he lied about making his whole bed wet, it was only one little spot and was using it as an excuse to get in bed with me. At his urging, I also cleaned myself off in the sheets (Im so sorry hotel workers, I was a dumb teen) and we both moved over to his bed and slept there together.

We both ended up sleeping naked, but nothing much else happened that night. In the morning when we woke up he was almost unintentionally spooning me, I could feel his cock slightly touching me in the morning, but that was about it. The next day (and the remainder of the trip) we wore each other's boxers and acted like nothing was going on with each other when we were in public together. It was definitely my favorite school trip I ever went on, thats for sure.
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Thanks for reading if you made it this far, I know it was a pretty long story lol. Hope you enjoyed it, I may continue to post more stories with Jack and other guys in the future. I've had a lot of pretty fun experiences that are in my spank bank, its fun to think that others are getting some enjoyment out of these memories too. Feel free to ask questions or hmu ;)