This happened a couple of years ago on a business trip to Sydney. I had just started at a new company and had to travel over to Sydney for an induction and training. Prior to this I had only been part time so had plenty of spare time. I took this time to start getting into performing on Chaturbate. I was never hugely successful but earnt some tokens on there and had some regulars who I would chat with on Snapchat or Kik outside of the shows. There was one guy, J, who was a regular in most of the shows and often tipped quite well. He had told me he was married but his wife didn’t know he was bi. I knew he was from Sydney and he was one of few who knew where I was actually from.
I flew into Sydney on the Wednesday morning and checked into the Hilton Hotel and freshened up before heading to the first induction session. Very boring, out of there by 3:30 so went for a walk around the city just looking at the the sites and had some dinner before heading back to my hotel room about 7:30pm. I was watching terrible tv and decided to jump on Chaturbate for a couple hours and chatted to my regulars, no J though. Very uneventful show. Came after the camera was off alone.
Thursday went much the same, got out of the induction early and headed back to the hotel room. We had a group dinner that night at 7 so I had a few hours to kill. I loaded up Chaturbate again and it was better, this time J was on and we were chatting. He noticed the different room and I mentioned to him I was in a hotel room in his city. He instantly started messaging me off of Chaturbate saying we had to catch up. I declined as it was almost time to head to dinner. All through dinner I had messages from him asking to catch up, even just for coffee. I kept declining. Dinner carried on and everyone had too many drinks and it wrapped up about 11:30 and I headed back to my hotel room. I was still getting messages from him, he had now started to offer money to meet. I was politely declining, until he made an offer that intrigued me. A live Chaturbate show in my hotel room just for him, Friday morning for an hour for $500. A Chaturbate show usually consisted of me sitting in front of the camera, playing with myself and dancing, talking shit with a vibrating toy in my ass.
I had a shower and climbed into bed, sat there staring at the offer, I accepted. He asked my room number and told me he would be there at 7. It took me a while to fall asleep after that with nerves and excitement. I set my alarm for 6:30 sat there nervously waiting for a knock on the door. I thought I heard one a few times and was constantly looking through the peep hole, my heart racing. Bang on 7 there was a knock on the door. I nervously opened the door in the hotel supplied robe. There he stood in his gym clothes holding his suit on a coat hanger, he had to tell the wife he was heading in early to go to the gym before work. He was about 45, greying hair, quite handsome, a little solid around the midriff but not fat. He came in and we made awkward small talk.
I walked around the bed and grabbed the toy and the lube so it was easy to reach, he positioned himself in an armchair facing the bed, I started to slip off the robe, slowly revealing that I was naked underneath. My cock already hard, I turned around and climbed onto the bed revealing my ass to him, spreading one cheek so he could see my hole. I rolled over onto my back to start rubbing my hard cock teasing him. He asked if he could get naked and I said sure, he stood up and started to get undressed, I paused and watched him. He released his hard cock, around 5 inches but very thick. He sat back down as I started teasing him again, rubbing the toy over my body and cock, spreading my ass for him. I lubed the toy up and got on all 4s facing him, making sure he had a great view of my open hole. I felt his hand touch my ass cheek, I let it linger before pulling away. I inserted the toy into my ass and let out a moan as it entered me. My cock leaking massive amounts of pre cum now. I took some on my finger and held it out for him, he took my finger in his mouth and moaned how good it tasted. I continued the show, fucking my ass with the toy while stroking, him getting more and more vocal. I asked him to join me on the bed so he could get a better view. He climbed on right next to me, our cocks inches apart both stroking.
The show had been going on like this for just over half an hour. I was super turned on, I could tell he was. He got the courage up to ask me if he could touch me, and that he would pay me more just to stroke me. I let him take my cock in his hand and he began to stroke me. He moved his head down to start sucking me but I stopped him. He said he’d pay more, I let him continue. We never agreed on figures but I was so turned on at this stage I would have done it for free. He continued to suck me, he was not the best at it but serviceable if I’m being honest.
After about 10 minutes of him sucking me he sat up and asked me if I would fuck him. He would pay me anything I wanted. I wasn’t going to be able to finish from his blow job so I agreed. Now this is not something I would usually do, but I didn’t have any condoms and neither did I, so I lubed up my cock some more and lubed his ass with him on his back, legs up. I slowly pushed my cock into his tight ass, he moaned out, and told me to go slow. I worked my cock deeper into him till I was all the way in. I started to fuck him, deep and slow. He was moaning under me. I built up the speed and his moans got louder, I felt his ass tense around my cock and his cock start to squirt cum on his belly, this only egged me on to go faster and harder. His cock continually leaking his cum, I could feel my orgasm building and asked him where he wanted me to cum. He told me he wanted to feel me cum inside him. I fucked him as hard as I could till I buried my cock in him as deep as I could, filling his ass with my cum.
I let my cock go soft and removed it from his ass and my cum leaked out and down onto the sheets. We both stood and made our way into the bathroom where he climbed into the shower first, I waited my turn and he said I could jump in, we switched places and he dried himself and headed out of the bathroom. A few minutes later he came back in, in his suit and said he had to head off to work. We said our goodbyes and I heard him leave the room. I stayed in the shower for another 10 minutes or so before jumping out and drying off. I found an envelope on the bed and inside was $2500.
The next time I jumped on Chaturbate he was in there. I have never received so many tips as I did that show.
Source: reddit.com/r/gonewildstories/comments/psdqts/paid_for_sex_because_of_chaturbate_mm