1/10/2020
My girlfriend and I had been dating for a few weeks at this point. We were in love but hadn’t said it yet, and at that point in our relationship where every word out of their mouth is the most important thing anybody has ever said, and everything about their body is the most incredible thing you’ve ever seen (though in all honesty that hasn’t changed much since then). My girlfriend is about 5’6”, small boobs, cute reddish/brownish curly hair and the cutest face with these big glasses that I love (just look at the picture in our account if you’re curious). I’m about 3 inches taller, and you can just… fill in the rest of the details with yourself since you are probably projecting anyways.
We decided to call it an early night and go to bed around midnight, and were cuddled up, naked, in a twin bed talking about life, our pasts, our friends, our exes and everything we do and ever have found interesting, with the conversation being broken up by making out. Remember when I said it was an early night; right about now is when we checked the clock and noticed it was about 6am. Up until this point we had done a good amount of oral, but never had sex because of a surgery she had had a few weeks prior meaning the doctor said nothing inside until after her next visit which wasn’t for another week. As the night went on, the conversation turned naughtier as it often does and we were getting way hornier and making out was taking up more and more time between thought.
Eventually we decided that while she couldn’t have anything in her pussy, her ass was perfectly okay. Neither of us had ever tried anal before, and like any other people born in the 21st century, we googled what to do. I quickly went upstairs to get a bottle of lube I had in my room. I came back down and she had cleaned up and gotten ready.
I started off by giving her a back massage (which when done properly causes her to melt into a pile of pure moans and pleasure) to get her to relax as best as possible. She sucked me off to make sure I was turned on and it wouldn’t take too long for me to finish. She was still new to giving head but she is truly gifted when it comes to that, and with the added turn on of knowing that I would get to fuck her in the ass in a matter of minutes, it felt incredible.
After she did that, I took a bit of lubricant and put it onto my pinky and slid it into her asshole, all along checking to make sure she felt good and wanted to continue. She moaned, as I let my finger sit for a minute before eventually letting it glide back and forth inside her ass. She prompted me to switch to the next finger up, and only wanted to use this one for a few seconds before she asked for my thumb. Her pussy was dripping wet and she was super calm and turned on. She wanted me but I continued fingering her ass for a while longer, stepping up to 2 fingers at once. Eventually though, she was ready.
She got on her hands and knees, and I put a lot of lube on myself and slid in slowly. It felt amazing. It was tight and warm and a completely different sensation than any of the (albeit limited amount of) sex I had had with a previous partner. What felt especially good was the lack of condom (she was on bc). It was just really fucking good. She loved the feeling too. [I asked my gf to write the next sentence and it has been 2 minutes and she has been staring at the keyboard struggling, if she takes any longer I may have to remind her what it feels like myself ;) ] She’d never before had anything so deep in her. It elicited moans of ecstasy so loud that she practically had to suffocate herself in a pillow just to keep the neighbors from hearing.
Eventually it was too much and we went back to fingering for a few minutes, but with some more lube and a quick break she was quickly able to get back to the main event. With even more lube, I was able to pick up the pace. I grabbed her hips and found a really good rhythm as I pumped in and out of her. She had a finger on her clit while I continued and after 5 or 6 more minutes of this, I whispered in her ear that I was about to cum, prompting her to shove her head down into a pillow to suppress her screams of joy as I filled her ass with cum. Somehow, we managed to go through about half of a 5oz bottle of lube, the rest of the bottle we managed to make last 3 more sessions of anal, and a semester of sex. We cleaned up and slept without clothes and with limbs intertwined, knowing full well we would be exhausted in the morning.
Source: reddit.com/r/gonewildstories/comments/l0epg9/our_first_time_anal_mf