I took one of the socks out of his mouth and put it over his dick and started stroking him. He was moaning through the sock that was still in his mouth, and before I knew it, the sock was hot and sticky. I pulled it off slowly and cleaned up his dick with the sock that was still in his mouth.
At this point, he was completely naked and trying to catch his breath.
“Are you ready for bed yet?” I asked.
“Absolutely,” he said, and we went to sleep.
The next morning, I woke up, showered, got dressed, and headed out all before he even woke up. I wore Dillon’s shoes that Ben wore on his flight in.
A few hours later, I got a text message, “Hey, I didn’t even hear you leave this morning. You fucked me into a coma lol,” he said.
“I took a shower and stole Dillon’s shoes and everything,” I said.
“I noticed, but that’s okay because now I’m wearing your shoes,” he said as he sent a picture of his feet, showing me that he was wearing my shoes.
“Nice,” I said. “I’ll be back up around 6:00, and then I’m all yours again for the evening. Go explore and have fun, and I’ll see you tonight,” I said.
“Sounds good. See you tonight,” he responded.
I went about my day, struggling to stay awake throughout the boring conference and endless lectures. For lunch, I decided to go back up to my room on the off chance he’d be in there.
I walked into the room and found him in bed, watching TV, still wearing my shoes. Only my shoes.
“I wasn’t expecting to find you in here,” I said.
“Yeah, you really took it out of me. I’m still exhausted,” he said.
“Technically, I think I put a lot in you,” I said with a smirk.
“Yeah, yeah. How much time do you have?” he asked.
“Well, lunch is 90 minutes, and I was just going to hide out in here for a bit,” I said.
“Perfect, because all I’ve been able to think about is getting fucked against that window. We’re on the 54th floor,” he said.
“I think we can manage that,” I said.
He took the covers off and got out of bed. The only thing he was wearing was my Jordan 1’s. He walked over to the floor-to-ceiling window, put his hands on the glass, and stuck his ass out a little.
“Fuck me,” he said as he spread his legs.
“Fuck yes,” I said as I undid my pants and got behind him. I was instantly hard and just spit on his ass and my dick and rammed it in him. I fucked him hard and fast. I reached around and grabbed his dick and started to jerk it while I fucked him.
“Don’t worry about that this time,” he said. “Just use me.”
That was such a huge turn-on that he just wanted to be used like a fleshlight. I stopped stroking him, put one hand on his waist and the other one on the back of his neck. I pressed him up against the window and fucked him until I came.
I pulled out, and he turned around to kiss me. Then he got down on his knees and cleaned me off with his mouth. I pulled my pants back up and told him he should go see some of the city since he wasn’t old enough to gamble. I took some cash out of my wallet and put it on the dresser.
“Thanks, slut. The money’s on the dresser,” I said.
“Shut up!” he said with a laugh. “And thank you.”
“For the fucking or the money?” I asked.
“Why not both?” He asked with a mischievous smirk.
“Fair enough,” I said. “I’m gonna head back down, and I’ll see you around 6:00?” I asked.
“Yeah. I’ll text you if I’m not back by 5:45,” he said.
“Sounds good,” I said as I kissed him.
I went back down to finish out the day at the conference and came back up to the room at 6:00. This went on all week. I fucked him every morning, at lunch, and after dinner. One night we went shopping, and I bought him a pair of shoes just because I liked how they looked on him. He got naked and put them on as soon as we got back to the room. I liked them so much, I went back and got two more pairs.
At the end of the conference, we checked out of the hotel and headed to the airport together.
“What time do you land?” he asked.
“Same time as you. We’re on the same flight,” I said.
“Oh, really? I didn’t even pay attention,” he said.
“Yup. We’re sitting next to each other,” I said.
“Nice,” he said.
“Yup,” I said, “and I arranged for Dillon to pick us up. Since we’re getting home so late, maybe he should spend the night.”
“Definitely,” he said with a grin.
Once we landed, Dillon was waiting by the baggage claim. We all hugged and said hello, and the first thing Dillon said was, “Nice shoes.” We were both wearing the new shoes I had bought.
We got our luggage and headed to the car.
Once we got home, I opened my suitcase and pulled out a shoebox, and handed it to Dillon.
“What’s this?” he asked.
“It’s a box of dicks,” I said. “We’re going to make you airtight tonight.”
He opened the box, and it was the same pair of shoes that Ben and I were wearing.
“Aww, thanks!” Dillon said.
“We couldn’t be the only ones with matching shoes,” I said. “Did I get the right size?” I asked.
“Uh, we’re all exactly the same size,” Dillon said confusedly.
“That’s the joke, idiot. Put them on,” I said.
Dillon kicked his shoes off, sat down on the couch, put the new shoes on, laced them up, and tied them. For anyone who’s wondering, they were the Jordan 1 Retro Chicago.
“Thanks, man. These are sick,” he said.
“It’s the least I could do for the ride,” I said. “Speaking of rides, I think it’s time for me to take you for one,” I said. “You good to spend the night?” I asked.
“I didn’t bring anything,” he said.
“Guess you’ll just have to be naked,” I said.
“Wouldn’t be the first time,” Ben said with a grin.
“Won’t be the last time,” Dillon said as he took off his shirt.
“But seriously, do you want to? You can obviously borrow whatever you need,” I replied.
“That sounds great,” Dillon said. “I know you two have been fucking non-stop all week.”
I gave Ben a look.
“What? I didn’t say anything,” Ben said defensively.
“You just did,” Dillon said with a laugh. “Show me all the nasty shit you did in the hotel room.”
We all went to the bedroom and fucked each other for over an hour, wearing only our shoes. We ended it by giving Ben a facial. After Dillon and I finished on Ben’s face, we got Ben to lay on his back, picked his legs up so he was almost bent in half, and then we took turns jerking him off and holding his legs up until Ben came on his own face.
Then we all cleaned up and called it a night. I wish every business trip could be like that.