I've never had anal sex with a woman either. I only had one opportunity, and ironically I wasn't trying to have anal sex with my girlfriend at the time. She had a really sexy ass, and I always tried to get my lips on it any chance I got. So one night after sex, she rolled over on her stomach to go to sleep. I started kissing the back and side of her neck, then her back, kissing my way down her back until I got to her ass. Then I started kissing and licking her ass cheeks for several minutes. I was firmly content to kiss and lick her sexy ass for a half-hour if I could. Then she slowly raised her ass up in the air and spread it really wide, putting her anus in the perfect anal sex position. So I assumed she wanted to do anal. I asked if she had any lube (we were at her place), but she said no. I knew that without lube, anal sex could really hurt a woman and damage the anus, and I didn't want to risk doing that to her. When I asked subsequent girlfriends about trying anal, they all refused to do it because they said they'd tried it before with other guys and it hurt like hell. But they all agreed to do regular sex doggy-style, so for me that's pretty close to anal because when I thrust into a woman from behind, her ass pushes back and forth against me and I can sort of imagine that I'm fucking her ass.
One girlfriend actually asked me to do doggystyle on her. It was within our first month of having sex with each other and after doing it cowgirl style, she said I had to promise her that we would do doggystyle next time. When I asked why, she said it was because she loved how deeply the penis could get into her pussy. So I usually did doggystyle or cowgirl with her. She was short and petite and super-tight because she'd never had kids, so that that it hurt my dick to do missionary-style sex with her. Most of the time it was doggystyle, which was great since I got to feel her ass slapping against my lower torso while thrusting deep into her pussy.
First time i asked and it hurt while penetrating so we stopped. The next time i i wait till she was trash drunk and i acted like i was lubing her pussy but was really lubing her ass then i slowly snuck it in there. She took it a lot easier drunk
Just gave a guy his first time inside a woman's ass. Needless to say we both enjoyed it. It had been a while for me, I forgot how good it feels
There wasn't much talk my first time, more moaning. He got me wet, started with his fingers one then two then he slid right in.
Discussed it at length on several occasions with my first wife before following through with it. Our first time was better for me than her. After the second time some months later she was addicted to me fucking her in the ass. We'd created a monster but damn she could work my cock with her ass just as good as she did with her vagina. 20 years of nailing her ass and it only loosened up slightly...the way she clamped down and loosened up was amazing.
He wanted to have sex but he didn't have a condom and I wasn't on bc. He suggested anal. We talked about it for a few mins I guess
I was 20 we both talked about it before. But with some drinks in us we had some courage and went for it
