My first time having anal sex was about two years after I got divorced. At the time I had a very good male friend that used to accompany me to functions and events. He works with me and I had known him for quite a couple of years already. He also used to be married so we had common ground so to speak. My first husband was very conservative so the sex used to be lights off, eyes shut type of event. One evening when he was visiting the talk turned to sex and porn. He said that he noticed that in a lot of movies there is always some anal sex as well and if I have ever tried it. I said no and asked if he has done it before. He said he tried it once with his ex, but she was not keen on it. After a couple of glasses of wine I told him jokingly maybe we should try it, I mean nothing romantic will flow out of it, because at that stage neither of us was interested in a new relationship. He laughed and said, "sure, why not?" I asked him if he was serious and he said he was.

I told him we should get cleaned up first and take it from there. He jumped into the shower and when he came out of the bathroom he just had a towel around him and told me he will wait in the bedroom. I went to shower and when I came into the bedroom he was already lying on the bed, naked. He works out everyday so he is quite well built and when I looked down I saw that he was quite well endowed as well, nicely trimmed with smooth balls and shaft. He was uncut, and already semi erect. I must admit at that stage I was quite apprehensive, wondering if he will be able to fit into me, seeing that he was big. I removed my towel and he told me that we should get some lube, and if he should use a condom. The only lube I had was a tube of KY and I told him the condom we can give a skip, seeing that I was allergic to latex. I lay down to him and he started kissing my neck and breasts. He moved down to my pussy, which is also clean shaven, and I nearly came when I felt his tongue and lips on me, this was the first time since my divorced that I had sex again. I told him to turn around in the classic 69 position, proceeding to suck him. He was even bigger when fully erect and I must admit I had my doubts. Some of my female friends had anal sex before and said it hurt like hell. I could feel his one finger rubbing my ass and every now and then I felt his tongue there as well. He then told me to to lie on my stomach. I turned around and saw him reach for the lube. I felt him opening my cheeks and then he started kissing and rubbing my ass, slipping his lubed finger in. He only slid the tip in, telling me to relax. It was quite a nice sensation and I started relaxing, feeling his finger going deeper. He slipped in another finger and and asked me if I am ready. I told him he must just go slowly. I felt the tip of his cock against me and slowly he started moving into me. I could feel his foreskin sliding back as he entered me and then felt his whole tip popping into me. It was actually a funny feeling, not sore, but I could feel he was big. The whole time he asked me if it still feels ok, I told him if feels quite hot. I could feel him going deeper and stretching me, but it was quite a pleasurable feeling. I felt him starting to slide in and out and at one stage felt his balls against me, thinking to myself that his whole length went in. He moved faster and faster, rubbing my clit and nipples as he slid in and out of my ass. I knew he was close to cumming and told him he can shoot in me. I heard him groaning and then felt the warm liquid being shot into me, and then I felt myself starting to orgasm. I could feel my ass contracting around his penis as I orgasmed. I felt him sliding out of me, his dick making a popping sound when it flopped out. As we lay on the bed afterwards we both both agreed that it was quite the experience, I looked down and thought to myself that I would have never thought that such a big cock could fit into my ass. It was another 6 years before I got remarried again, but in that time we had quite a bit of anal sex, as well as other sex. We are still good friends and I still visit him often, but that is a story for another time. I would recommend anyone to have anal sex, it is one of life's guilty pleasures, and it is a lot of fun. less