This story is about me and my long time friend. To paint a bit of a picture, I’m tall and thin, with short hair and a beard, and she’s much shorter and thick in all the right places, with big tits, butt-length hair and nice wide hips and ass. We are both late 20s.
We live really far apart but had been flirting and sexting for quite a while so when she had the chance to spend a few days in my area on the way back from a work trip we jumped on it. As part of all the sexting we had discussed many of our fantasies and she brought up anal a lot. She had done it a couple times and really liked it, I never had, and she eagerly expressed wanting to change that while she was in town.
We were fucking pretty much immediately after she arrived and during every spare moment we had. Lots of great sex that was fulfilling all the horny promises we had made to each other over the internet. A couple of times while I was pounding her from the back and watching her big sexy ass jiggle I’d put my finger up against her asshole and circle it, put a little pressure on it, just gauging her reaction. She loved it and would moan and grind her ass on me so I knew I’d be fucking that before long.
On our third night together, we were laying in bed after a long day and making out. I was playing with her tits and rubbing her pussy lightly, just teasing her a bit with my fingers. I ran them all the way down and teased her ass a bit too, and she moaned and kissed me really hard. She liked to put her tongue deep in my mouth, which I was happy to oblige. After we broke the kiss she looked me in the eyes with a super horny expression and asked if I wanted to do anal tonight. Of course I was more than okay with that so I got up to get the bag of horny tricks.
I had never done anal prior to that night but I’d done my research and I wanted to make it as fun and comfortable for her as I could. Not to toot my own horn too much, but my cock is well above average size and I knew I needed to warm her ass up and take things slow. We’d bought a few fun toys to use while she was here, including a few different sizes of buttplugs and plenty of lube. I grabbed them and set the three plugs in order of size on her stomach and asked which one she wanted. She eagerly pointed to the biggest, so I grabbed it and poured out a generous quantity of lube onto her ass and pussy, getting the whole area nice and slick. Her pussy was soaking wet at this point, so I gave it a quick fingering while she moaned and quivered under me.
Then I shifted my hand down a bit and slipped a finger into her asshole, which accepted it easily. I slid it in and out a bit, enjoying how tight it was and her appreciative moans. After a moment, I pulled my finger out and pushed the tip of the plug against her. She was so tight I really had to push to get it inside her, which definitely made me a little nervous. She reassured me she was fine, though, and encouraged me to push it deeper with her eager moaning. Pretty quickly the thick plug was entirely swallowed up and I switched back to fingering her pussy (with my other hand of course, be safe folks). She was loving getting both holes filled and pretty soon was begging for me to fuck her. My cock was rock hard at this point and I was only too happy to help, so I grabbed a condom, put it on and rubbed my cock up and down her dripping lips while she played with her clit. I love teasing a girl before I slide into her and she was really into it, grinding against me and rubbing herself. Before long though I needed to be inside her so I angled it in and entered her fully.
I could feel the plug through the back wall of her pussy while I stroked slowly in and out and it was a massive turn on. She was loving it too, grinding under me and pulling me down to kiss her. We stayed like that for a couple minutes as I slowly picked up the pace and started fucking her hard. Unfortunately my bed is very squeaky and I had a roommate sleeping in a nearby room so I had to restrain myself a bit and not just go to town on her like I wanted to. Having to be quiet did make the whole thing more sensual in a lot of ways though, and we were whispering dirty things to each other and using some strategic kissing to muffle the worst of the moaning. Before long the dirty whispering lead to me asking if she was ready for my cock in her ass, which she whimpered yes to. I reluctantly pulled myself out of her wonderful wet pjssy and flipped her over onto all fours with her big ass presenting itself nicely to me. She pulled out the plug and I immediately put in first one, then two fingers. They went in so easily that I knew she was ready to get fucked, so after a minute or two of fingering I positioned myself behind her and got ready.
At this point my cock had gotten a little soft since being outside her and I knew I needed it to be really hard to get into her tight asshole. I slipped it into her pussy instead, just to get warmed up again, and she moaned and rammed her hips back against me. I was rock solid and ready to go within a few thrusts so I pulled out, poured a bunch more lube over her ass, and set my cock against her hole. She was so tight as I pushed in that I was worried I was hurting her, but she reassured me she wasn’t and I kept going. After about half of my cock was inside her, she asked me to stop and wait a moment while she adjusted to it. I was loving the tight grip her ass had on my cock and was happy to sit there all night. After a moment she asked me to keep going and within a few seconds I was balls deep inside her.
I grabbed her neck and bent her head back towards me, asking if she liked having my cock in her ass. She whimpered yes and I planted a quick kiss on her lips before pushing her back down and starting to move inside her. I went slowly, pulling my cock almost all the way out of her before pushing it back in as deep as I could. She was loving it, moaning as loud as she dared and reaching back between her legs to play with her clit. I slowly increased my speed and before long I was giving her an honest ass pounding, fucking her as deep as I could and loving the feel of her big ass slapping against my hips. Her tight asshole was really working my cock and I could tell I wouldn’t last too long. From her whimpering and moaning it sounded like she wouldn’t either, and sure enough before long she whispered that she was coming and started shaking and quivering beneath me. That was all it took to push me over the edge and I let out a huge load inside the condom, balls deep in her ass. I slowly slid out of her and we both collapsed on the bed.
I kissed her, rubbed her ass and complemented her on how good it felt. She laughed and said she had loved it too, and she just hoped she wouldn’t be too sore the next day. Thankfully she wasn’t, so my technique must have been decent! It was an insanely hot experience and the next time we see each other we are definitely going for round two. And maybe three or four if we have time.
Source: reddit.com/r/gonewildstories/comments/wd2wj3/first_time_fucking_a_girl_in_the_ass_mf