I didn’t have my first anal sex until I was 45 or 46. I got married at 25 and broached the subject with my wife sometime during the first two years but she wasn’t interested at all (don’t get me started).
However, when I had my first affair, my AP specifically asked me if there were any sexual things I hadn’t tried but wanted to try. She wanted to give herself to me in a way no one else ever had. It was the first experience with anal sex for either of us. We went slow and used lots of lube, but I think it was still at least a little bit uncomfortable for her.
I always waited until after I made her come at least twice before moving to anal. Our best time was once when she was lying flat on her stomach and I was on top of her with my hard cock deep inside her tight ass. I reached around and slid my hand between the bed and her thigh. Then I rubbed her clit until she came again while at the same time filling her ass with my hot cum.
My second miss (if you count my wife) was with a South African woman. We had a pretty long cyber affair, but we only had actual sex three times. During one of those times I ended up lying on my stomach and she was kissing down my back. She kind of lingered around my butt cheeks, so I lifted my ass up in the air for her. Little did I know that she was trying to tell me that she LOVED anal sex and had the hardest orgasm from doing it. I found that out after we stopped the physical part of our relationship.
My second hit was another dalliance. She was a Due Diligence Officer for a big commercial real estate company, and she traveled to Atlanta a few times a year. Her sex life with her husband was pretty bland and she really wanted to experiment. For example, she was OK with me recording us having sex (she had me send her a copy). Another time she wanted to record us as she gave me a blow-job with my hands bound behind me and a blindfold on. We did that. She also wanted us to go to a strip club posing as husband and wife, and have me get a lap dance while she sat beside me holding my hand (and try for a blow-job). We didn’t get to do that.
When DDO and I were ready to try anal sex, I realized that I left the lube in my truck. That meant totally blowing the mood, getting completely dress, walking all the way to the truck and back, or going dry. I went with option B. I was rubbing the head of my cock up and down her ass crack and when I finally went to enter her, the second my head started to press into her ass, I exploded.
My third hit was the best (so far). You may know her as the Church Lady, if you’ve read some of my other posts. She said that she’d never done anal before, but if not, she took to it right off the bat. The first time (I think) was in my office. She was sitting on her knees, backwards, in an office chair as I grabbed her hips and pounded my cock deep inside her ass. I filled her up with hot cum. Another time, at a hotel, we did simultaneous ass play with our lubed fingers before I rolled her onto her stomach and ass-fucked her.
The last time we had anal sex, we were in my other office, on the couch in the break room. We had already had oral sex and intercourse (cowgirl) and she had cum twice. We were just resting and talking, but I was still hard because I hadn’t cum yet. She turned around away from me, took my cock in her hand and guided it into her ass. She then proceeded to ride me reverse Cowgirl until I came hard up her ass.
Source: reddit.com/r/gonewildstories/comments/394hl8/m4f_my_anal_adventures_hits_and_misses