u/New-Routine390

I (29f) was hanging out with a guy friend of mine when we started talking about sex. He asked me if I’ve ever had anal sex and I said yes and he asked me if I liked anal sex and I said yes. He then asked if he could fuck my ass and I tell him sure, if he wants. So he begins kissing me and taking off my clothes. Then I help him take off his clothes and his dick comes out and It. Is. Huge. The biggest dick I’ve ever seen. I begin sucking it and I’m thinking maybe he’ll just let me suck him off to completion lol, but nope. He has me get up and then he bends me over, lubes up his dick, and slides it in my ass. Anal hasn’t hurt that bad since my very first time. As he pounded my ass I felt like I was going to pass out from the pain. After like 15 minutes, he finally came and I just collapsed onto the bed and didn’t move, even as he got up and jumped in the shower. My ass was legit on fire. Immediate regret.

I (29f) went to the beach with some friends. My one friend’s family was also there, to include her younger brother who is still in college. My idea of a beach day is a skimpy bikini, laying on a towel, and walking around some. I ended up going on a walk with my friend’s brother (20m). He was cute. He kept trying to hide his stares of my body but it was super obvious, especially him looking at my ass in what was essentially a thong bikini. We ended up walking to the Airbnb we were all staying at, and no one else was in there. I told him I was going to shower to get the sand off me and said I would probably keep my bikini on if he wanted to join me. He said yes. So we are both in the shower and I’m washing the sand off me and I’m trying to wash out some that’s irritating me in my bikini top, and I just decide to take it off. He has a very visible erection at this point and I just ask him if he wanted to fuck (I mean, why not?). He immediately says yes lmao. So we each take off our swim bottoms and begin kissing, I turn around, bend over, and guide his dick into my pussy. Be begins fucking me and it’s nice. After a couple of minutes, I ask him how he’s doing and he tells me he feels like he’s going to cum soon. I try to be the cool slutty woman and I’m like “you can cum in my ass if you want.” And he immediately tries to put his dick in my ass haha. I tell him to use his spit to lube up his dick some, and I use my spit to lube up my ass, then I slowly guide his dick in. As soon as it’s in, he just begins fucking my ass hard (ow lol). And he cums after like 5 minutes of that. We then clean up, put back on our swimsuits, and go back to the beach lol

I (29f) hooked up with a friend of mine (25m). I love his stamina and his enthusiasm. He spent like 15 minutes eating my pussy before moving to fucking me. He always puts me in doggie while he fucks me which is good with me because I like how much more intense he feels in that position. After fucking my pussy for like 10 minutes, he accidentally slips out and as he goes to line his dick back up to put it back in, he lines up with my ass. And as soon as he found a hole, he just slides right in without hesitation. In the moment I honestly didn’t know if it was intentional or not but as he began fucking my ass the initial shock of him just putting his dick in my unprepared ass wore off a little and it felt mostly ok, so I just went with it. Apparently he didn’t realize immediately it was my ass, and it wasn’t until when he was about to pull out to cum that he looked and saw his dick was in my ass, and then just decided to cum in there. He apologized after for accidentally putting it in, and I said it hurt a little bit but it was ok since he didn’t do it on purpose. But it still feels particularly slutty of me to have spontaneous anal, even if it wasn’t intentional.

I (29f) first had anal sex when I was 21 with my bf at the time (25m). I was at my apartment feeling horny one night so I asked my bf to come over. He said he couldn’t, but I said I’d rock his world if he did. He asked for specifics and I said “whatever you want.” So he agrees and comes over. I answer the door in a bra and thong and we get to it pretty immediately. He eats me out then fucks me fast and hard. But then he stops suddenly, and flips me over so I’m on my hands and knees. He tells me he needs a sec to put on some lube. I think about that for a sec and then ask him why he needs lube. He answers and says to help with fucking my ass, and before I could respond his dick is pressed up against my ass and he tells me to relax and breathe as he slides his cock in, all in all in one smooth motion. I just remember being completely overwhelmed, like I couldn’t catch my breath, and as he began to fuck my ass I just had my head on my pillow starring at my wall like I was having an out of body experience. He snapped me out of it when he started fucking my ass harder and talking dirty, asking me if I liked his cock in my ass. I answered yes and began to focus on the parts that feel good, trying to make pleasure moans to encourage him. He fucks me even harder, but then quickly cums. He collapsed on top of me and why just laid there, me on the bed, him on top of me, his dick in my ass, for like 5 minutes. He then pulls out, rolls off of me, and thanks me for letting him do whatever I wanted - saying he was eager to try out my ass, which was news to me since he never brought it up.