I am continuing my trend of posting wild stories from my crazy single years. Some of these were previously posted under a different account that was deleted when I started dating a recent partner- so if it sounds really familiar you’re not going crazy.. that probably was actually me!
All that being said- this happened like a year or so a go. I got out of a committed relationship at like 27 or 28, so I did a LOT of getting around between then and the time I turned 31 lol.
This particular instance started, as one would expect, on tinder. It was one of those profiles that I’d normally swipe left on because it looked shady or fake. No face pictures, just a few grainy body shots and then those sex memes people put up as pictures instead of showing themselves. No idea why I swiped right, because that’s definitely the kind of shit I’d normally skip.
But, for whatever reason we matched and she messaged almost immediately. Red flags all around- she refused to tell me her real name, didn’t want me to see her face, and said she was in town on business but wouldn’t say where from. She claimed that this was a kink for anonymous sex/free use, which I know people are into but she definitely gave off “Yeah, I’m cheating on my husband/wife” vibes. Still, the pictures of her body were sexy and I sort of figured if I didn’t bang her someone else would anyways.
We sexted for a couple of days, aiming to hang out on the weekend whenever she was done with her conferences on whatever the fuck she did for a living. She made her ground rules incredibly clear- I wasn’t going to know her name, I wasn’t even going to see her face. I was going to come to her hotel, wear a condom, and then use her body however I wanted as long as I never saw her face. I admittedly didn’t understand the logistics of this, but I was a horny young man and wasn’t going to ask too make questions as long as I was going to get to put my dick in someone.
The agreed upon day arrived, and I made my way to the hotel. She’d let the front desk know that I’d be stopping by to get an extra key (which I was told needed to be left on the nightstand when I was done) which made me nervous. I kept imagining getting accused of stealing some shit from her room or something… but once my dick gets an idea in its head there’s rarely any room responsible, rational thought in my brain.
I got the key without issue and the dude at the front desk of the hotel looked pretty amused. I’m not entirely sure that I was this lady’s first visitor, which was slightly off-putting but did at least calm my fears she was going to try to get me arrested or murder me and wear my skin as a suit or some shit. I’m a little early and still a little nervous, so I go to the hotel bar for a shot of tequila or two far too inappropriately early in the day then go to let myself into her room at exactly the agreed upon time- this was something else she was VERY specific about.
And when I went into the room, it became immediately obvious why. The woman was already on all fours with her face down in the sheets, a bath towel covering her head so that her naked body was only visible from the neck down. On her ass was a sticky note that had *u/capitalforce’s holes*. I’d given her a fake name (since I didn’t ever get to know hers), but still the thought was hot as fuck. Next to her on the nightstand were various types of condoms (jerk didn’t trust me to bring my own, apparently), a couple different types of lube, and a couple different sizes of buttplug.
All apprehension on my part disappeared in my excitement, and I was pretty much instantly hard. From what I could tell, she looked maybe 10 years older than me but it’s sort of hard to tell with only seeing a pussy and ass in the air… but it was obvious her body at least was hot. A little bit of a mom bod and kind of chunky, but honestly I’m kind of into that so I was ALL about it.
I’ll just straight up say- normally I’m a big fan of eating ass and hers did look great, but considering she was an utter stranger and I wasn’t sure how many other dudes had been through her room recently I decided against it. Instead, I started by licking and fingering her pussy from behind and, to my delight, I realized she was already wet as fuck by the time I even touched her.
In real life I’m not much of a braggart, but bragging seems like the entire point on this sub so I’ll admit I’ve been told that I’m rather skilled with my fingers and mouth… so it didn’t take long for there to be a sizable wet spot on the sheets below her. There were a few times I thought that she was going to cum before I even fucked her, but she managed to hold it together. The sexiest part of the whole thing, in my opinion, is the way she moaned and involuntarily shuddered when she heard me undoing my belt- she seemed so excited to get fucked that she could barely contain herself.
Of course, that just made me excited as hell so as soon as I had my cock out I pressed it up against her pussy threatening to let it go in but not quite slipping it into her yet. The first words I said to the lady was “Hard or slow?” To which she replied “hard”. I didn’t need told twice; I grabbed ahold of her hips and pulled her back onto my cock all in one deep thrust, which prompted another long moan and lots of squirming from her. After that, I did my best to make her regret her decision to ask for it rough. There was plenty of spanking and lots of grab her by her shoulders to pull her back onto my cock and rail her as hard as possible- and she seemed to be loving it. I’m not sure if she came as hard as it seemed like or if she was just really good at faking it, but I didn’t catch any coherent words in the English language besides “YES” and “Oh Fuck”. Besides that, it was just a ton of moaning and borderline screaming.
After a while, I noticed that while she was getting fucked she’d occasionally reach back and spread her ass and giving me a great view of her other right hole. Being able to take a hint- and being a guy that aims to please- I didn’t waste too much time grabbing one of her bottles of lube and putting applying a generous amount to her ass. This prompted another shudder of excitement, and I teased her while still fucking her pussy by using my finger to spread the lube around her ass. She was clearly getting frustrated by the teasing, as her ass got higher in the air and she spread herself wider and wider the more I touched her. She froze like a deer in the headlights when my first finger slid in, and then reached down between her legs to rub her own clit when I got the second in.
After giving her some double penetration like that for a while, I pulled my cock out of her pussy and she heard the lube bottle opening again.
“I’m not sure I can do the dick but you can try.” Romantic second words to say to someone but I did plan to make her try. Unfortunately, any time my cock got more than halfway in, she’d start to have trouble and I’d need to stop. It somewhat sucked for me, because I really wanted to fuck it, but I still got enough of it in that it was noticeably spread open every time I pulled out… and thats extremely hot to me. Eventually, we gave up on it and I changed my condom to go back to fucking her pussy while simultaneously sliding her smaller plug into her ass.
After knowing I wasn’t getting my buttstuff, all bets were off and I started to pound her pussy as hard as I could humanly manage and she seemed to be loving every moment of it. Eventually it became clear I wasn’t going to last much longer and I told her as much. “Pull out if you can, just in case. You can cum on my back or tits if you want.” Now, I’m an ass guy for sure.. but there’s something definitely hot about seeing a nice pair of boobs covered in cum, so I pulled out and told her to roll over. She obliged somewhat awkwardly, as she took careful care to keep her towel covering her identity. I knelt on top of her and she didn’t even wait for me- she took manners into her own hands, pulled off my condom, and jerked me off until came all over her chest.
I took a moment to catch my breath and, when she didn’t comment further, got up and told her that her key was on the table as requested and took my leave. The next day I got a message from her randomly telling me that her pussy was still sore, which I apologized for.
“Not necessary, it was a compliment not a complaint.”
For a couple of days after that she’d still send me pictures or clips of her naked (still no face, of course). Then randomly one day I looked at my phone and she’d unfriended me from messaging app that I can’t name here, presumably going back to where ever the fuck she came from originally and I’ve never heard from her again.
So, random married redditor, apologies if I made your wife my little slut when she was in the Midwest on business. Unless, like, you’re into that I guess. In which case, you’re welcome?
Source: reddit.com/r/gonewildstories/comments/s2fpey/mf_the_one_time_i_banged_an_almost_certainly