My First Time

Back in 2015 when Craigslist was still a thing, I would browse the postings to see if any piqued my interest. Sometimes if I was feeling adventurous, I would post. I prefer older daddy type guys so my post would reflect that; I would get a lot of responses but the majority of them were dead-ends.

One night, I did get a response from an older guy, in his 40's with a muscular dad bod which was just my type. He kept things pretty short in his responses and asked if I wanted to meet. I was so horny so I decided to meet up with him in his car around 10PM. I walked across the street and he picked me up in his car. He seemed pretty friendly and asked if I knew of any places where we could go but I wasn't too sure so we ended up driving around for a bit. Eventually. we ended up in an apartment complex parking lot where we parked in a spot at the far end. Once he parked, he pulled down his pants and showed off his hard thick 7'' cock. I leaned across the center console and slowly licked his dad dick. He moaned and ran his hand down my back, eventually grabbing my ass. His thick cock felt so good in my mouth and feeling his pubes as I swallowed his dick made me so hard. He leaned back, closed his eyes and kept rubbing my ass. It must have felt good because shortly after, I felt his hot load shooting down my throat. His moaning turned me on that I shot a load into my pants, running down my leg.

He sat there for a second and eventually pulled his pants back up and shot me a cute smile before driving me back. I got out of the car and thanked him for the ride. I didn't know if I would meet him again but I definitely hoped so.

He eventually did hit me up again and asked if I was doing anything tonight. I dropped basically everything to go meet him at his hotel. I got to his door and he invited me in where we both sat on the couch. Normally, I wouldn't do a lot of talking but he seemed fairly normal and nice so I indulged him in a little conversation. He was a surgical doctor in the area and liked to meet up with people from Craigslist for "massages" and fun. After talking for a little while longer, I eventually got turned on by his voice and hands, so I knelt in-between his knees while he was on the couch and started to suck on that hot thick daddy dick. He moaned how good it felt and ran his hand through my hair. He got more into it and pushed my head down until I was choking on his dick. He started to take off his clothes and I did the same. He stood over and put his hands on my waist, walking me over to the bed. He went over the dresser where he got a condom and some lube before coming back. I was laying on my back, looking at him smiling while he rolled the condom on his thick cock and lubed it up. He rubbed some lube on my hole before pressing the head of his dick against it. He went slow and eventually got the tip inside which made me gasp and moan. Slowly, he pushed a little more, gradually going deeper and deeper. I kept trying to stifle my moaning but eventually, he was slamming his dick into me and all I could let out was "yes, please, fuck me". He grunted and moaned as I felt his dick pumping in me which turned me on so much. As he got close, he pulled out, took off the condom and shot a load all over my face. I loved to see his face in pleasure as his salty load painted my face. As he looked down, he shot me another smile and we both got cleaned up. It was late so I stayed the night with him at his hotel.

For a first time, I'll never forget it.