I only had anal once with a guy. I was staying in a hotel outside of Atlantic City, NJ, alone about 10 years ago, after an unpleasant breakup. While I was in the lobby, a Chinese man began chatting me up for some reason. (It's always surprising to me when men start chatting me up). We decided to get a drink and while at the hotel bar he told me about himself. He was born in China, but had gotten US citizenship; he lived in NYC and was a bus driver. He was in AC because he had relatives visiting from out of town and they wanted to see the sights. They were driving from NYC to Washington, DC and had stopped in AC for a day or two.
This guy was really interesting to me and I liked him because he was so plainly open and honest. He had a clean, handsome face and eventually our chatting got more personal. He asked if I had a husband, a bf, why was I in AC, etc. I told him I was newly single, had gone through a tough separation with my ex gf and needed some vacation time away from life and that I was just hanging out alone by the beach and the casino for a few weeks. He said he really wanted to get married, but had a hard time finding a gf who was interested in doing the things he was interested in, such as going to see baseball and basketball games, going dancing, seeing live music, cooking a nice meal together, going to museums together, etc., which are all things I enjoy doing. We hit it off immediately. I had never found Asian men attractive before this guy and I am sure it was this guy in particular that made the attraction happen.
He said he was really shy around women and had a hard time getting intimate because he felt that his penis was too small and also that he had the problem of losing his erections. He got them ok, he said, but he lost them quickly and couldn't come. Bear in mind, this conversation evolved over several hours, during which we drank a little, danced together (he was a really good dancer) and were enjoying just hanging out as "pals". We did not touch at all, except for when we were dancing. Eventually, I asked him if he would like to have sex with me. He said he was concerned about the things he had already told me, but yes, he wanted to. I told him to go back to his room and wait for me, that I would be there in an hour, and not to worry about those things.
I went back to my room, did a quick Fleet enema, showered and got dressed. I was completely flying on impulse and not thinking too deeply about it. I had no doubt that it was going to be good, for some reason, although I hadn't been with a man in at least 10 years by that time and I certainly had never picked a man up at a bar and fucked him before, or since. But, I was really turned on by the guy and the thought of actually having a partner, a bf, to go to basketball games with and who could dance and who was very respectful, and who appreciated art and enjoyed cooking with his woman, well all of that turned me on, too.
His size concern also didn't trouble me for I knew that most women, the ones that I was friends with, didn't really enjoy a man with a huge package in reality as much as they may have in fantasy. For many women, a real big dick just hurts, especially if you haven't given birth or have only had a C-Section (not a vaginal delivery).
When I got to his room he, too, had showered and changed his clothes. He had put on a suit. This touched me because he clearly seemed to think that we would go out before we had sex. I would have been turned off if he had been in bed with his junk out already, actually. But, the fact that he had put on a fresh shirt and dress pants, etc., just made me want him even more. He wasn't a pig, you know?
I put on some music and we started dancing a bit again and I began to undress us both. We started messing around and I could see he was getting hard. I kissed him and we got passionate and I put a condom on him (another big turn-on for me) and we began to have sex, but sure enough, as soon as he entered me I could feel him begin to lose his erection. I could see him begin to get upset and he started mumbling to himself and he seemed like he wanted to crawl off and die but I took him in my hand and started kissing him again, pushing my breasts into his chest and putting his hands on my ass. He got hard again. As soon as he did, I put some ky on his cock, grabbed a pillow and turned onto my stomach, the pillow beneath me. I told him to lay on me and let me guide him in. I doubt he knew what I was going to do because as I gently guided him into my ass I could feel him stiffen and he quickly sucked in a breath as I pushed back against him. He stood rock hard and still as a statue with his dick in my ass. I tightened my muscles and squeezed him in me and he groaned and moaned, but didn't move. I think he was either afraid to move or just stunned like a deer in headlights, so I pushed back against him and rocked back and forth until he got the idea. He fucked my ass really well and my word, the sounds he made when he finally came in my ass! It was so hot, it felt so good and I reached beneath me and touched myself as he fucked me in the ass and as soon as he began to come I also let myself go and it was amazing. The feeling of a man coming in my ass was indescribable. The post-coital throb, his affection afterwards, the deep penetration, the things he was saying to me, all of it was just great. That was the first and only time I had anal with a man. It would take a special man to get me to do it again, although I certainly would be up for it under the right circumstances. Getting fucked with a toy just pales in comparison to the sensation of having a real cock in your ass. It's like comparing freshly whipped cream to Cool-Whip.