My first meetup was almost a complete waste of time, but the second was stunning. I found the guy on a hook up site and we chatted for a bit. Getting comfortable is really hard when you think about getting naked with a guy who's going to be behind you fucking your ass. Things could turn out very badly with getting left for dead the worst case. He had a couple of good reviews and said the right things (recently tested, ok with condoms including oral, able to meet at a hotel). I booked the hotel and knew that there were cameras in the parking lot and the hallway, making me feel better knowing he'd be recorded coming into my room. The cameras weren't hidden, so it would be obvious to him as well.
He had asked me to be naked when he got there, which somehow actually relaxed me. I got there early, cleaned myself out with an enema, put a syringe full of silicon lube up my ass and waited on the couch. My heart was nearly bursting out of my chest when I heard the knock at the door. I looked through the peephole and saw his face for the first time (just body pics on the hookup site). Pretty good looking older guy (60's...I was in my 50's). 6' tall, gray hair, and in dad-bod good shape. One deep breath and I opened the door. He looked me over, and I asked him if I was OK. He said, "absolutely." I grabbed his hand and pulled him into the room.
I asked if I could take him into the shower. I helped him undress, making sure to kneel before him to help with his shoes. My face was near cock level and I rubbed against him with my face. I was even more impressed when he was undressed as his cock was nearly as big as the 7" dildo I was using at the time. I fondled his balls and then grabbed his cock and pulled him to the bathroom. We got into the tub as soon as the shower warmed and I soaped him up from head to toe, making sure to wash his balls and cock with my soapy hand and then my tongue after he was rinsed. I also slipped my soapy hand between his ass cheeks and used a fingertip to clean his asshole. Once he was clean and I was convinced he didn't have any visible STD symptoms, I turned my back to him and let him wash me, even though I was clean. He ran his big, rough hands over my whole body and slid his soapy dick up and down between my ass cheeks (no penetration).
I was hard at this point and he jerked me off a little, but I stopped him (I get post-nut clarity pretty bad), shut off the water and got a towel to dry him off. I used the same one and when done, leaned into his chest and licked and sucked his nipples while fondling his cock and balls with my hand. I had never done this to another guy, but I knew what I would want and just went with it. Once he was hard, I led him to the bed and put a clean towel down. I had brought condoms and had put a few on the bed. I opened one and was able to get it onto his dick despite my hands shaking. As soon as I had part of it on, I used my mouth to push it down further. I sucked him off for a bit, then grabbed his ass and pulled him deeper into my mouth, causing me to gag. I had practice on my dildo, but it wasn't as hard as his cock. After a bit more, I asked him if he wanted to fuck me. I handed him the bottle of lube then turned around and bent over the bed with my legs spread. He put some lube on his hand and then onto the condom, and finally dripped some between my ass cheeks. I spread them with my hands as he pushed a finger into me. Then two, sliding them slowly in and out of my hole as I loosened up for him.
