Her First Time Trying Anal [m/f] | 2016

I had this pretty little FWB a while back. We'll call her Sofia. She was 21, Mexican, and just one of the finest looking girls you've ever seen. Curvy, pretty eyes, sexy accent. I've dated plenty of pretty girls, and been friends with plenty more, but I've never seen a girl who got so much male attention just walking down the street. Guys would scowl at me, no doubt mad that I was taking this beautiful little creature off the market.

She was amazing in bed, and totally open with me about all her desires and fantasies. But the first night I was with her (which is another story all in itself) she told me, "Don't ever ask me for anal, I don't do that." Fine with me. I like anal, it's fun as something a little different, but I don't especially crave it. Pussy feels better anyway, and Sofia's pussy was amazing. I was certainly not getting bored with that.

Normally, I'd just go over to her house a couple nights a week. We'd watch TV for a bit (she was always making me watch The Golden Girls), then I'd fuck her senseless, spend the night, drop her off at work the next morning. She wanted to be more of a normal couple, but I don't really like monogamy, and I'm terrible at relationships. Every now and then, she'd convince me to take her out on a "real date" and, well, she could be very charming.

So we're out drinking one night. I don't remember exactly what we were doing, but after getting a few drinks in us, we start getting pretty touchy-feely. And once certain ideas get in our heads, we decide to get back to her place as quick as possible. We barely make it through the door before the clothes start flying off. I'd never even seen her drunk before, but She's always really uninhibited even when she's sober, so I didn't imagine it would be any different.

My cock is throbbing as she's undoing my pants, and I'm imagining how hard I'm going to fuck her. Normally, the very first thing I do every time is bend her over and fuck her doggy style. (She loves it when I smack her ass really hard and when I pull her hair.) But tonight she surprises me, bringing her face close to mine, and saying in that sweet, innocent voice, "I want to try anal sex." I am okay with this. I ask her is she's ever had it before, she says no. So this is a bit of a thrill, exploring virgin territory.

I ask if she has any lube, and she does not. "Just use spit," she tell me. I don't know what brought this desire for anal on, but I can tell she is really anxious to get fucked in the ass. Normally, we use condoms, but with no risk of pregnancy, and being pretty drunk, I just bend her over and line up my bare cock against her asshole. I muster up as much saliva as I can, getting her hole and my dick wet. I start to push in slowly, but I slide in more easily than expected. I've had anal before where the girl was really tense and it makes it difficult to get inside. But tonight, due to Sofia's drunk and horny state, I get entirely inside her without much trouble.

Her moans are even louder than usual, and I can tell she is loving it. I am too. It's a different sensation fucking her ass, plus I am bareback inside her for the first time. That, coupled with her loud moaning, and the thought that I'm first one to ever fuck this ass, gets me quickly to the point of no return. I grab her hips, hard, and push my cock all the way inside her. I grunt as I let out a huge load deep in her ass. But I know I'm not done yet.

Lucky for me, I can stay hard even after I cum. I pause for a second to catch my breath, but I don't pull out. I know Sofia needs more, and I wouldn't let her down. After a minute, I start to slowly fuck her again. Pretty quickly, I'm back to full strength, pounding her ass hard. She is absolutely loving it, and she starts talking dirty. "I can feel it!" she cries out, obviously referring to my cum I had already shot in her. "Oh yeah, you like that, don't you? You're a dirty little girl, aren't you?" She readily agrees, but is incapable of forming entire words. I'm in awe of how turned on she is. She's always told me how I give her the best orgasms she's ever had, but I've never seen her as ecstatic as she is now.

"You love having my cock in your ass, don't you?" I say, as I continue pounding her hard. "You're a little slut, aren't you? You're MY little slut." I don't normally talk this dirty with her, but my drunken state and the amazing hotness of this whole situation has really loosened us up. I can tell she is just fucking loving it. The more dirty talk I give her, the more I tell her she's my little slut, the more she loves it. I'm fucking her as hard as I can, trying to get to a second orgasm inside that ass. Pretty soon, I can hear the telltale signs of her about to cum. This gets me going even more. "Are you gonna cum for me?" I ask. "I want you to cum from this cock pounding your ass." This gets me right up to the edge, and it's all I can do to hold on as she starts to cum. She's moaning and convulsing, and holy shit, this is about the hottest thing I've ever witnessed. This sends me over the edge, and I cum inside her ass for a second time.

We collapse into a big sweaty mess. "Wow," she says in amazement. "An anal orgasm." I laugh and kiss her. After we catch our breath, she says, "I can't believe I let you say those things to me." I guess she's a little sensitive about things that might be degrading. But we both know how hot it was. I hold her close and kiss her to let her know that it was all in good fun. After a little, she gets up to pee, and I go wash my dick in the sink. I'm sitting on the bed, admiring this beauty as she comes back. She kneels down in front of me, takes my cock and puts it in her mouth. Now, there's no way I'm gonna cum right now, but I do get hard and let her suck me for a couple minutes. Just a lovely little submissive maneuver; her showing me how much she loves that cock that was just pounding her ass. Then we go to bed and fall asleep with my arms around her.