First time bottom

It was 2009 and I was a 24 year old virgin. Horny all the time and tired of jerking off I decided to check out the Craigslist personals to try and find a girl. Needless to say I didn't find any women, but my curiosity got the best of me and I clicked on the M4M tab. There was a ton of posts by guys who wanted to suck and fuck. I figured why not, a blowjob is a blowjob. I responded to an ad of a guy in his early 30s who wanted to give head. After a brief chat with him I went over to his place, he blew me, I came pretty quick, then I left. It was so easy. Over the next few months I answered more ads for guys who wanted to suck. Eventually one guy looked up at me and asked if I wanted to fuck him. I told him that I had never fucked a guy before and he grabbed some lube from his nightstand and told me to go slow at first. It felt so good being inside him. He became my regular hookup. After a few times I asked him if he would fuck me. I saw how much he enjoyed it and became curious how it felt. He said no. He was strictly a bottom. The next day I posted my first personal. It said I was looking to bottom for the first time. I received a lot of replies. I didn't realize how in demand my 24 virgin asshole was. Most of the replies were from men much older than me. Eventually I got a reply from a guy in his mid 40s. He said he was divorced, discreet, and he could host. When I showed up at his house I was super nervous. He could see it. He said, "wow you really are a virgin." I nodded. He offered me a drink, which I declined. We went to his bedroom. I sat on the edge of his bed and took a deep breath. He smiled down at me and said,"we'll take it nice and slow. You decide what we do." That put me at ease a bit. I took my shirt off and got on my knees in front of him. I pulled his pants down and wrapped my lips around his cock. I couldn't believe that I was actually sucking dick. It felt so right. I should have been doing this my whole life. I eagerly suck on his nice, thick, 6 inch cock for a few minutes. Then he put his strong hand under my chin and tilted my head up so we made eye contact. He told me to get on the bed. I did. He pulled my pants off and positioned me at the edge of the bed, knees bent, feet flat on the bed. He dropped to his knees and started licking my asshole. I moaned with pleasure. After a few minutes I looked down and noticed I had the biggest erection of my life. I was 7 full inches, hard as a rock, dripping precum. We made eye contact again. He got up and smiled. He kissed me on the lips. The taste of my own ass drove me wild. He grabbed the lube and asked if I was ready. I bit my lower lip and nodded. I was more than ready, I wanted this so bad. He applied a generous amount of lube and gently rubbed my asshole. Then he slowly penetrated me with one finger. He fingered me nice and slow for a minute then he added another finger. After another minute he put some lube on his cock and placed the tip against my hole. "Just relax" he said. He pushed the head in and waited for a couple seconds. A rush of ecstasy passed through my whole body. It was the same feeling as have cock in my mouth times 1000. This is what I had been missing in my life. He slowly worked his cock into me little by little. Before I knew it he was thrusting into me balls deep. He knew exactly what he was doing. I thought about how clumsy I was when I topped. He flipped me over and took me doggy style for a while. I looked back at him and said, "let me ride that cock." He got on the bed and I straddled him. I reached back and positioned the head of his cock on my asshole and sat on it. I started slow, but soon found the motion to make his cock hit my spot. I started riding harder. I was sitting straight up, arching my back slightly. I felt my cock twitching. Holy shit, I was about to cum handsfree. Then I felt his cock pulsing inside me as I rode him. As he came he reached up and grabbed my cock. Two quick strokes and I came harder than I ever have. The first rope of cum shot out and hit the headboard of the bed. The next few spurts on landed on his chest. I collapsed onto his chest. My face landed in my own cum. I felt his cock slide out as I fell forward and cum dripped out and down my thigh. I was breathless, my whole body was shaking. He wrapped an arm around me and rubbed my back. He asked if I was okay. I said I was more than okay. I picked my head up off his chest, wiped the cum off my face and licked it off my hand. I proceeded to lick the cum off his chest then kissed him. He smiled and asked if I wanted to use the shower before I left. I said I will as soon as my legs stop shaking. We snuggled for another minute then he got up. I went to the shower. I was glowing, smiling ear to ear. I discovered myself. From now on I was going to be a naughty cum slut. But life has a funny way of working out. Three days later I started a new job. I met a girl there. She just broke off her engagement because her fiance was cheating on her. She flirted with me, we hooked up, fell in love, got married 3 years later. My wife and I have a great sex life, but I'll never forget the orgasm that guy gave me. Best sex of my life.

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Anon Sex September 29, 2026 at 11:24 am 0 0