A gay sex story: Business Trip Surprise
To set the scene a little, I’m required to travel for work several times per year. Most of the time, it’s a conference of some sort where I sit in a hotel ballroom for six or so hours to try and learn something new about my industry and network with my peers. The conference organizers almost always inevitably chose Las Vegas as the conference location. After many years of attending these things, I have cultivated a healthy dislike of Sin City. I couldn’t be bothered to hit the town after dinner every night, and I always went back to my room to watch TV, catch up on e-mail, and go to bed at a reasonable hour. This brings us to the start of our story.
The decision to send me to this conference was made at the last minute (I only got about five days’ notice), which wasn’t uncommon. I always had things ready to go so I could pack and be out the door within an hour if needed. I completely forgot to mention it to my cousin until the day before when he saw me packing and asked where I was going.
“Vegas, remember?” I asked.
“No? You never mentioned going anywhere,” he responded.
“Oh. I could’ve sworn I did. Sorry about that. It was last minute, and they just told me a few days ago,” I said.
Sometimes I would know months in advance, and I usually told him as soon as I knew.
“What am I supposed to do?” He asked.
“About what?” I responded.
“Everything!” he exclaimed.
“Like..?” I asked.
“I don’t know. Groceries?” He said.
“Well, I don’t leave until tomorrow, so we can make sure you have everything you need today,” I said. “We can go now if you want, or I can leave you some money, and you can go get whatever you want when you have time.”
“Money is fine,” he said.
I finished packing, we had dinner, hung out on the couch watching TV, and started getting ready for bed. A typical evening.
While he was in the shower, I set out a chastity cage, jockstrap, and a pair of his baseball socks. He always got dressed in his bedroom.
I was in my room, making sure I had everything I’d need packed and ready to go the next day when I heard his voice from his room.
“Oh, really?” He asked.
“Yup. I need a reminder of what I’m going to be missing all week,” I said.
“Hah, fine,” he said.
He came into my room wearing the jockstrap and baseball socks, and I could see the bulge of the chastity cage under the jockstrap. He got under the covers and said, “You better fuck me good tonight. It’s gonna have to last me until you get back.”
“I think I can manage that,” I said.
I pulled his arms to the edge of the bed so he was on his back with his head hanging off the side of the bed. I stuck my dick in his mouth, and he immediately started sucking. I played with his balls and started to finger his hole. He moaned around my dick and then I flipped him over onto his stomach. I got on top of him and slowly pushed the tip of my dick into his tight asshole. As soon as I felt the pop pushing into him, I went balls deep in a single stroke.
“Oh, fuck,” he moaned as I started pumping inside him.
“Right there. Keep going,” he said.
I kept fucking him just like he told me to, and he said, “Fuck. I think I’m gonna cum.”
I flipped him over, felt up his chest, and pinched his nipples as I continued to drill him. He put his feet on my shoulders, allowing me to go even deeper.
“Fuck! I’m coming!” he said breathlessly as he erupted through his cage, all over his stomach and chest. Watching him blow his load all over his tight abs and smooth chest made me lose it, and I came deep inside his ass just seconds after watching him cum.
I sat with my dick in his ass for a few minutes while we both caught our breath. “So… are you going to pull out anytime soon?” he asked. I slowly pumped in and out of his ass and asked, “Do I have to?”
“No, he said, but if you want to go again, you should make it quick. It’s getting late,” he said.
“Fine,” I said in mock disappointment as I slowly pulled out of his ass. “Go clean up so we can go to bed.”
He wiped his semen off his belly and put his fingers in his mouth while locking eyes with me.
“Hot,” I said.
He got up and went to the bathroom. I quickly got up and went to his room to find the keys to his cage and put them in my backpack. I got back in bed before he came out of the bathroom.
“Holy shit, bro. You blew your load DEEP inside of me. I couldn’t even push it out,” he said as he got into bed with me.
“Don’t get pregnant,” I said jokingly.
“It’s kind of hot, knowing that your load is still inside me and probably will be most of tomorrow,” he said as he started to fall asleep.
“Don’t worry,” I said, “you know I’m gonna fuck you again in the morning since you’re wearing all my favorite things to sleep in.”
“Yeah, only because you’re leaving. You know I hate waking up locked with morning wood,” he said.
“I know. I think it’s super gay that you’re doing that for me,” I teased.
“Shut up,” he said with a smirk. “You just came inside a dude. Your cousin.”
“That makes me a degenerate,” I said as I kissed him, pushing my tongue between his lips and grabbing his crotch.
We went to sleep after a little bit of groping and fingering.
The next morning, I woke up to my alarm and already had a huge erection. I set my alarm a little early so I’d have time to fuck him before I had to leave for the airport. He was sleeping on his stomach, with one knee up, the jockstrap framing his ass perfectly. I grabbed the bottle of lube from the bedside table and lubed up. I slowly climbed on top of him and started to push into his ass. He woke up right as I felt the pop, and I started pumping slowly.
“Oh, fuck,” he said in surprise.
“Good morning,” I said with a smirk, and then I kissed him. We made out while I fucked him, and then I grabbed his arms and pinned them behind his back. I fucked him harder until I came deep inside his ass again. I squeezed out as much as I could from my dick, and then I reached over to the bedside table to get a jeweled butt plug. I put the butt plug in his mouth to lube it up with his spit and warm it up a little as I slowly pumped his ass with my dick again.
I pulled out of his ass and took the butt plug out of his mouth, and put it in his ass.
“I gotta start getting ready, or I’m going to be late,” I said as I got out of bed. He rolled onto his back, and I climbed back on top of him, sitting on his chest and putting my dick in his mouth. He sucked on it for a little bit, and then he said, “Go take a shower. Don’t be late.”
“Feel free to join me,” I said.
“It’s so early,” he complained.
“You don’t have to,” I said. “I just thought I’d offer.”
“You don’t need to offer. I know I can join you whenever I want,” he said.
“That’s right!” I responded as I climbed off of him and headed to the bathroom.
I got in the shower, and a few minutes later, I heard the door open.
“I smell like sex,” he said.
“I wonder why?” I asked sarcastically.
“Shut up and move over,” he said with a laugh.
We showered together and got out together. As we were drying off, he asked, “Do you need me to do anything before you go or while you’re gone?”