Trying anal again [M/F]

A couple of weekends ago, I was at home, admittedly a little more than buzzed, having some fun with myself. I had thought about texting my FWB, but I decided I just wanted to have a night on my own instead. I had candles going, porn on the TV, a couple of toys, the whole nine.

I was about 15 minutes into my fun little masturbation session, when my phone buzzes. I was going to ignore it, but I noticed it was a text from my FWB so I grabbed my phone. We went back and forth for a bit (screenshots here and here), and of course, he wanted to come over. I had already let go of the idea of taking care of myself so it was a foregone conclusion that he was coming to my place at this point. However, he brought up the topic of anal.

My FWB has been begging me to let him fuck my ass pretty much since we first hooked up last year. I tried anal years ago and did not enjoy it at all, so never tried it again. I've let him use a finger a couple of times but that's as far as it has gone. Well, lucky for him, I was in such a horny mood that I told him that tonight, I would let him fuck my ass. The truth is, I've been kind of building up to this for a while now. It had been so long since I had actually tried it, and it was with someone who obviously didn't know what he was doing, that I felt like I needed to give it another shot.

It wasn't long before there was a knock on my door. I answered in an open robe and a thong which he seemed to appreciate greatly. He was a little more disheveled than I expected but that wasn't going to discourage me. We walked straight to my bedroom. He looked around and smiled.

"You weren't kidding about having some fun tonight huh?" he said.

"Just come here" I said and pulled him towards me as I fell onto the bed.

He got on top of me and pushed my robe aside, fondling my tits as we made out. I took off his shirt and desperately fumbled with his belt. He eventually got the hint and got up to take the rest of his clothes off. His hard dick was a sight for sore eyes. I was going to have to wait a while longer though as he proceeded to shove his face between my legs, licking my already wet pussy after pushing my panties to the side. His licks were long starting from as low as he could get and licking up my slit all the way to top of my mound. He kept trying to get his tongue to my ass but was only able to tease it due to a combination of the angle my hips were at and my thong getting in the way.

Eventually he just slipped the panties off of me and lifted my legs up, getting much better access to my ass. He started to eat my asshole with fury. He's eaten my ass in the past but I think the prospect of actually fucking my ass gave him some additional motivation. I could feel his tongue trying to probe my tight ass but he also made sure not to ignore my pussy as his right hand played with my clit.

After a while of warming me up with his tongue, he moved things along and started to use his finger. He slipped it in and worked it slowly. By the way he went about it, I could tell this wasn't his first time doing this. He went from one finger to two, and tried three but that's when it went from feeling good to a little too much discomfort. It was time to bust out the lube. He turned me around and with my ass up in the air, he lubed up his fingers and my ass. It took some time but sure enough, he was able to work a third finger into my tight asshole. The discomfort subsided and thought it wasn't a familiar sensation, I was starting to enjoy it.

He also started to fuck me though he did so very slowly so as as not to overwhelm me. The combination of both sensations was amazing and was actually getting me close to orgasm. Just when I was getting there though, he withdrew from both my ass and my pussy.

"Are you ready?" he asked.

I'm not sure if he had done it on purpose or not, but him stopping right as I was about to cum had me yearning to get fucked, no matter what hole.

"Yeah, just do it" I said in desperation.

He lubed up his cock (which I personally didn't think was necessary given how wet my pussy was) and lined himself up with my ass. He moved very, very slowly. I thought I wasn't going to have a problem taking him given that he had worked three fingers into it already, but I was wrong. I could feel the pressure against my ass.

"Wait, wait, wait" I reacted.

"Okay, just let me know when you're ready" he said as he stopped.

I tried to relax.

"Okay, go slow"

He started to push, being very careful. "Play with your clit" he instructed. I did as I was told and it did help. It took some time, and a bit of coaching, but eventually his cock was engulfed by my asshole. It felt so stretched out that it may as well have been a soda can in my ass. But once he was inside of me, the feeling of him thrusting in and out of me went from stressful to pleasurable. This was nothing like the first time I had tried it when my clumsy ex-boyfriend just shoved his cock up my ass. I never knew this could actually feel good. Of course I continued to play with my clit which helped. I have to hand it to my FWB, I'm sure he wanted nothing more than to start plowing my ass with all his might, but he remained slow and steady.

After a while he pulled out and turned me on my back, putting my legs over his shoulders and fucked my ass while I was on my back. He quickened his pace a bit in this position but still not aggressive. This allowed him to play with my pussy while he fucked me though.

On top of everything else, he was actually talking dirty to me, something he really hadn't done. He'll moan and say a few things here and there, but never really talks dirty. Now he was saying things like "Your ass is so fucking tight" and even calling me a little slut. I was loving it.

Eventually he was ready to cum. He pulled out and came on my stomach and tits. As much as I enjoyed it, I wasn't used to the new sensation and wasn't able to cum from him fucking my ass and he knew it. Him, being the great FWB that he is, reached for one of my dildos and used it on me while he licked my clit until I came. I should mention that he also sneaked a couple of fingers in my ass while he did so.

After I came, we laid in bed and talked through the whole thing again. He wouldn't stop saying how badly he had wanted to do that and kept thanking me for letting him do it. Of course he asked if I thought I would want to do it again. "We'll see" is all I told him but I definitely plan on making that happen again. I feel like it's a part of sex that I've missed out on for too long.

Source: reddit.com/r/gonewildstories/comments/38hd1l/trying_anal_again_mf