I like it, but I have a small ass, which I have already shown in my profile. So it can be hurt sometimes.
I was in my mid 20s. I met this guy and his friend at a party. They weren’t particularly great guys or anything but it didn’t matter. It was just a hook up. They were attractive and in their late 20s or early 30s, I believe. I had already had a few threesomes by this time but only done blowjobs or let guys take turns with me. I was already into anal sex by this time.
We left and went to one of their homes. I sucked their dicks first and got fingered. I let one guy in my pussy while I continued on with sucking the other guys dick. They used condoms the entire time and began to switch off in my pussy a few times before I told them they could use my ass too.
One of them had already had anal before and the other hadn’t. The one who was experienced went first. It hurt a bit but not too much for me. I was already into anal by this time but still adjusting. He came while in my ass. I stayed in a doggy position for the next guy and he was more nervous about it but entered my ass. He went slow and awkwardly. He eventually came in my ass too.
I stuck around for the night and we all hooked up again a few hours later. That’s when it happened. I was having sex with the nervous guy again. I was on top and he was in my pussy. The other guy came up and I sucked his dick a bit while I rode his friend. He went behind me and was reaching around to squeeze my tits and just generally rubbing my body. I wasn’t expecting it but he pushed on my back to put me in a more leaned down position.
I felt his dick rubbing against my ass. I didn’t tell him no so he began trying to get his dick into my ass. I was so nervous and tensed up but willing. He continued to try and force himself into my closed ass and eventually got the tip in.
It hurt a lot more than anal usually did for me. I was basically frozen on top of his friend as my body tried adjusting to what was going on. He eventually got a flow going in and out of my ass and I raised my body a bit so his friend could enjoy himself in my pussy too instead of just having me sit on him with his dick in my pussy.
It hurt the entire time. My body never relaxed for them but I wanted it and I wanted them to enjoy themselves more than anything so I continued on letting them use both my holes. They never got rough with me but both eventually finished in me again.
We didn’t use lube. It probably would have gone easier if we did but none of it was planned.