For context, we’ve been exclusive for a bit over two years, she’s 41F, I’m M37. Sex has always been very good, and I’ve spent months slowing introducing gentle butt stuff.
It started out with rubbing her asshole while she was on top, or touching her ass while we showered together, etc.
She is very shy and most of the time doesn’t verbalize what she wants sexually. I did my best to coax her into telling me if it felt okay or not. Over a period of a few months, I started getting a finger deeper and deeper into her ass during normal sex. Eventually, she let me get my entire thumb all the way inside her butt.
Then, a month or so back, she let me know that she was willing to let me try and fuck her ass for real. I was really excited, and we watched a few videos about how to have great anal sex, mostly just to put her mind at ease. I bought a buttplug training set and we started experimenting with leaving the smallest plugs in her ass for a few hours at a time.
Finally, we made a few attempts to get my dick into her ass, and every time I would get too excited but feeling her wiggling around that I would come too fast. Also, I was circumcised as a baby, and I have very little sensitivity on my glans, so it’s difficult to “find” the right opening, especially with anal.
This past New Year’s weekend we actually made it happen. We were having amazing sex, and I got her ass warmed up with some deep thumb penetration and plenty of lube. Then I had her lay on her side, and I straddled her semi-doggy style, and slowly pushed the head inside her. It took a LOT more effort than I expected. We stopped pretty quick, not wanting to cause any pain the first time.
She said there really wasn’t pain the first time, just a lot of tightness. The next day we tried again, this time experimenting with reverse cowgirl and doggystyle. Nothing was really working, so she tried lying face down, legs flat, so I could get plenty of leverage. After another very difficult session of applying pressure, I got inside her ass and managed to stay hard long enough for her to get used to the sensation, and then got a nice rhythm of thrusts while she played with her clit.
She had a very intense orgasm, and I came shortly after that. We both enjoyed the whole experience quite a lot, and I’m sure it will just get better over time.
Thanks for reading.
Source: reddit.com/r/gonewildstories/comments/kpxqtz/im37_fucked_my_gfsf41_ass_for_the_first_time_mf