That reminds me of a previous FWB. We were equal such that neither of us was submissive though we mutually agreed to do anything either of us could think of. One time she said we could try her ass. Her ex had been there before but it always hurt her. Quite brave, I thought, that she would want to do it again. I took my time. I always do. Afterwards, she was quite overwhelmed. She wasn't sore, which pleased me. Then she said it was totally different from before. From when I began to enter, it felt strong and then intense. She couldn't speak or move and, she said, the only thing she was aware if was the intense feelings and me thrusting in long and slow. And she loved it. She loved being powerless, immobilised. Her ex had pinned her down to stop her moving. I hadn't. It became a regular thing for a while and it was great for me too. I wasn't dominating her; just was doing the same motion as normal but at a different angle. But it had an amazing effect on her and she wanted it more than vaginal sex for about a month. Then we included it as a variation to all else we did. Uh, I'm ready to do it now
If we’re doing doggy, you can be sure my thumb is entering her anus. She is very conservative sexually and it took along time for her to admit liking it. I don’t go in far….perhaps I should
I was seeing this one woman who looked a lot like Paris Hilton. 5'10" blonde, lean, with legs for days. She said she loves anal. I can usually control how long I last.* We lubed up and went straight to anal. I pounded away for approximately one hour in every conceivable position. I think she could have gone for more. I was exhausted. *I can go for an hour+ of penetration no problem. I think this probably contributed to some occurrences of "Retarded ejaculation" that took me 2-4 hours to blow my load.
My wife loves to have her asshole gently fingered and rimmed, she can cum from feeling my tongue licking and probing her backdoor...and it's a huge turn on for me, which to be honest, I didn't expect. When I took her anal virginity with my cock, she said feeling my cock enter her ass made her cum almost instantly and she loves it when I cum in her ass....
If you get most of your thumb in there then you will probably be teasing the g-spot between her pussy and ass, it isn't very deep. My baby has been doing that to me for several years and I always have great orgasms. Though I don't really know for sure if everyone has that anal g-spot or not, so I may be wrong about this for some people.
When we were in the lifestyle, I made it a point to make sure my playmates would cum, multiple times if possible....and would do whatever they wanted....or not do what they didn't want. One playmate said she didn't do anal and didn't really want her backdoor touched...while I had another that loved anal and would tell me to be sure to save some for her ass lol. When things got really hot, I would ask if they wanted me to gently finger their back door, and most of the time the answer was yes, at which point I would lube a finger and gently slip it in their tight little hole while softly kissing and caressing their ass cheeks....they seemed to love it.....and it made my cock rock hard lol...