First time for me just sort of happened. GF and I were having a good fuck with me doing her doggy. We weren’t in a rush and I was spending time rubbing her asshole while thrusting into her pussy. I then reached over for some lube and stuck a finger in her ass. I stopped thrusting and asked her, “so do you want to try it?”. She said yes. She always wanted to try it at least once. I got her ass prepped good with lub and finger probing. Then slowly inserted my cock. Just a bit at a time. In a bit, withdraw, and back in untill I was fully in. Had a nice slow pace. Felt great and different because of the tightness. She was really enjoying it. Eventually shot stream after stream of my cum into her ass. I collapsed on her. When my head finally cleared. I cleaned her up so she could walk to the bathroom without cum dripping out of her ass. It was fun.
I was dating a girl who teased me about how much of an ass guy I was and she was shocked I had never had anal sex before. So she just flipped up her skirt right there and said ‘come on try it out’. So I dropped my pants and lube it up and went to town and she started fingering herself and we both came hard.
All my gfs beforehand flipped out at me when the topic came up. even my kinky ones were anti-anal.
We know that there is a different feeling for a woman vs a guy getting ass fucked. Always wondered how some, not many, women really enjoy anal on a regular basis.
Planned, she was on her period so we bought some lube and decided to try anal. We spend more time that we’d like to admit adjusting the amount of lube and stimulating her ass until I could penetrate her asshole. But the sensation was awesome for both of us. She always says the insertion is painful, but the sensation of my dick ramming her asshole is amazing. While we haven’t made anal our “main” form of sex, we like to do it when we feel adventurous or when we can’t use her pussy. She’s always afraid of the insertion, but loves the fucking once my dick is inside.
