This happened a few years ago, but I recently found we had each other on Facebook and tried to reconnect. It spurred some memories, most of which are NSFW and I’ll enjoy sharing them below.
I was in my 20s, had just moved to a major northern city, and was very cold and lonely at the time. Most Tinder dates were really off and girls my age seemed to care too much about things I didn’t care too much for. So I was excited to learn that my family was staying in Miami for the holidays. After buying my ticket, I changed my dating app location and started doing some early recon, but I capped the lower age range at 35.
The match was simple and straightforward. No pointless text game. I’d pick her up that Wednesday night for some drinks at Wynwood. Sounds trivial, but that was already a sign of good chemistry for me.
I knew the vibe was on as soon as she got in the car. The mutual desire felt instinctive and non-verbal. I’m not really into astrology, but she was, and at some point during our drive into the city she seemed pleasantly surprised that our signs were compatible. Probably compatible in a sexual sense because of the purring tone that escaped her when she told me about it. In my head, it also didn’t hurt that she was this olive-skinned recent divorcée with wild blonde hair and the body you would expect from a gorgeous 38 year-old Brazilian lady. Most of all, she was shy. She didn’t seem to enjoy leading the conversation, she just made room for me to drive it. But once we touched on something she cared for, she opened up with her hippie-like passion for it.
She didn’t dress like a hippie though. She was wearing a light white dress that fit her figure perfectly. It let out a little side-boob and hugged her hips well.
We drew looks at the bar and we both enjoyed it. We could tell people wondered about our age difference and so we made out to rub it in. I remember her giggle and faux-prudence recoil when I grabbed her ass. There was always a sort of mischievous connection between us.
A few drinks in, we were both horny as dogs. She let loose a bit more. I used my belt to strap my erection against my belly in an attempt to hide it. She obviously noticed and started dancing in front of me, grinding her light-dress-covered cheeks against it. I proposed the bathroom, she shook her head laughing at me. That seemed to remind her of my age or something. I knew there was a Holiday Inn close to where we were both staying. She had kids, I was with my family, and we both wanted to smoke some weed.
Back in the car, I played with her breasts through the side of her dress while we waited for a drug dealer she knew. She kept smacking her lips on mine and moaning, but signaled that I had to wait for the room for more. Of course, the ride there seemed so long. To add to my impatience, we didn’t have a lighter and I only noticed once we had checked in. So I told her to wait for me in the room while I went out to buy one at some gas station. But my tone came off a little imperative because of my impatience. I noticed and tried to correct it. She, with a calmness that comes with age and experience, told me she liked to be spoken to in that way.
Finally at the room, we got high until even the touch of a finger felt pleasurable. I still had my belt-contraption and she started doing that dance again. This time I was able to take my pants off. She hiked up her dress and kept doing it while she slowly took her black thong off. I felt myself against her cheeks, flesh on flesh, but only for a few seconds. She let out a giggle, jumped into bed, facing me, sat against the wall and opened her legs with a playful smile that came off as innocent despite her age and what she wanted me to do. She showed me her barely trimmed-enough pink lips as she hiked up her dress a little more, sweetly with a hint of sensual malice. I was salivating. When she motioned me to dive in head first I went wild and kneeled on the side of the bed. It was as if I let out my munchies on her. I licked and sucked on it like a mango. She writhed and moaned, high as fuck, feeling every detail of my tongue’s motion. She couldn’t stay still and moved around the bed so she could lie down to take it all lying on the bed.
I kept going until I couldn’t take it anymore, I was too hard. I stood before her as she laid there and she knew I was going for it, straight in, as she stared at my erection. But she had a different idea and caressed me into it. That’s when I realized that she had been quietly in charge of the situation at all times, despite the shyness or saying she liked my imperative tone.
She sat me down on the bed, sat on top of me, facing me, guided me in slowly as we both communicated the pleasure of it with sweet nothings. Then she threw herself back, held by her arms, and we both thrusted away in an open lotus position. She kept interrupting her moans with a smirk as she looked at our genitals and called me “gostoso.”
After a while we got tired and I asked her to blow me. I felt so much pleasure at the smack of her lips on my balls as she jacked me off with her free hand. Taking another puff, she blew the smoke across my shaft. She was crouching beside me and I grabbed her by the legs to complete the 69. I loved feeling her breasts bumping lightly against my pelvic area. I was so turned on, so ecstatic, and so high that after a few licks on dripping lips I went straight for her ass. I didn’t know if she was into that but I started slurping all over it. She loved it.
The night went on. We came and smoked, came and smoked, came and smoked. I don’t know what time it was when she said she was taking an Uber before her kids woke up. She had to take them to school. I slept in and just told my brother I had a good night.
We stayed in touch for a while. She kept telling me about her experiences with ayahuasca, about astrology, about “zuko verde,” and many other things. She said she loved our night together, but ultimately, we were in different cities. We hadn’t talked in years until last week. I’m in a happy relationship now, but I told her I still jack off to her sometimes.
Source: reddit.com/r/gonewildstories/comments/diayd8/dating_app_cougs_a_miami_night_with_a_shy_cougar
“I used my belt to strap my erection against my belly” stfu