Older Bi Guys First Ass Fuck

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.

A moment later, he grabbed his rock hard cock and rubbed his fat head against my asshole. I pushed back, trying to get him into me. He used his weight to help penetrate me and slowly got his fat dick inside of me. I swear I could feel his cockhead "pop" into me and then each inch of his shaft as he slowly slid deeper. He pulled back before the whole thing was in and slowly did it again, letting me adjust to his girth. It took just a bit to know I wanted the whole thing slamming into me. The next time he slid in, I pushed back and his cock was fully buried inside. I clenched my asshole around the base of his shaft (those kegel exercises really help!) and tried to hold him in as he pulled back. I relaxed as he pushed himself into me and then clenched again. He started to fuck me faster and I tried to keep up with his rhythm clenching my asshole around his fat dick.

Soon he was really pounding me, grabbing my hips to help him thrust. At one point, he slipped out and I reached back to keep him from putting his dick back into me. I turned over onto my back, raised my legs into the air, and spread them wide. He guided his dick back to my now stretched and ready hole and pushed the whole thing as deep as he could. I rested my legs on his shoulders and he put his hands on my thighs to help him pump his cock into me. I tried to clench him, but I couldn't keep up, so I just tightened my buttocks to give him more friction. He asked me if he could cum in my mouth and I said no, so he kept fucking me and soon I could tell he was blowing his load into the condom. I held the condom on the base of his cock as he slid it out of my ass. It was a big load, much more than I had ever shot.

He went over to check on his phone while I started to masturbate on the bed. I have a trouble staying hard when anything is in my ass (dildo usually), but I can get there once it's out. I thought he might have taken a picture of me on the bed and I said please don't. He showed me his phone and said he had not, and I believed him. I asked him if he had to go and whether he thought he could fuck me again. He grabbed his cock and started to stroke it, and said, "Maybe." Turns out, he could!

That is exactly how my second (really my first) meetup went. I really should have set up a follow-up, and tried on the hook-up site, but we never managed to do it again. He did write a very nice review of our encounter, which helped set up my next meet-up. The next guy became a semi-regular, where we met at least 5 times. We got to the point of intimacy which included cuddling after getting fucked. He even got me to suck him off bare after showing me a clean STD test. Because of my constraints at the time, I never lingered after we had sex, but I knew I could have.