The third guy that I had ever been sexual with was a 65 year old lawyer that I met in an online AIM chat room when I was 19 years old. The first time we met up was at his law firm that was in the city of the county I lived in. He was one of the main bosses of the law firm and we had arranged to set an appointment time with his secretary at about 3:30 so he could see a “potential” client. He would usually do this with a lot of younger guys and everyone in his law firm—which happens to be a lot of people, didn’t have a clue. So I made an appointment and showed up and talked to his secretary, who went and got him and we introduced ourselves to each other. He gave me oral sex while I was wearing a condom because I was an extremely paranoid person.
We would continue to speak online after this occurred and several months later we decided to meet up to have sex in a motel in the city. I had to get really stoned before hand to go through with this and to also get in the mood. So before I met him at the motel room he had rented, I sat in my car across the street and got really stoned. I arrived at the motel room and knocked on the door and was greeted by him. After we chatted for a bit about how shitty the room was, I told him I had to use the bathroom. In the bathroom I anxiously got completely naked and walked out of the bathroom to which he was very surprised that I was naked. I lay in the bed naked and watched as the 45 year old lawyer got naked in front of me, he had a 6 inch cut penis that was normal girth, and my cock is 7 inches very thick cut. He proceeded to give me oral sex without a condom on this time, after a while, I turned around and laid on my stomach, this indicated to him that I wanted him to fuck me in the ass.
He put on a condom while I lubed up my asshole and fingered it for a moment, his cock was about 6 inches thin if I remember correctly. When he penetrated my asshole is hurt for a brief moment while putting it inside me and about 3 seconds later I hear him cry a moan loudly and fall on top of me. It was a bit awkward to have a guy get off that fast almost embarrassing if you ask me, but before that could go any farther he told me it was my turn. So I put a condom on, he lubed up and turned onto his stomach, this is the first time I have ever fucked a man in his ass. I pushed it in fairly easy and fast to when he moaned/screamed as I did it, it was very tighter and warmer than a pussy. I fucked him very hard and fast for a few minutes with the goal of getting off as fast as I could because this wasn’t like sex with women; I was in it for myself. I whispered into his ear, almost biting it at the same time, and kept asking him if he liked it. After a bit I felt a huge amount of pleasure and pressure from my cock, I scream into his ear that I am cumming and I orgasm inside of him very hard and fast for about 30 seconds while also collapsing on top of him. I laid there for a good minute moaning and without moving before I finally took my dick out of his ass and got up. To my disgust I see the condom is covered in shit and when the lawyer see’s it he tells me be careful taking it off. I carefully take it off and flush it in the toilet. I get back in the bed with him and we talk naked for a few minutes before we get up and I start to put my clothes on. He walks me to the door naked and we say goodbye, as I walk away I see he’s still standing at the door naked watching me. As I am leaving the motel to my car I see police at the door of one of the motel rooms, which is a reminder I just had gay sex in a shithole motel. This was the last time I saw the lawyer, however, we would continue to talk on AIM over the years. This was not the last time I had sex with a man top or bottom. Hope you enjoyed.