Meeting an Older Woman from the Internet [MF]

Back many years ago in college, I had an account with OkCupid since it was many years before Tinder. For those that don’t know what it is, it was a dating website where you could certainly find people to hook up with. One Sunday, I was bored at work so I would flip through and message a few people. Sometimes there would be no response, sometimes a conversation would happen and this time it led to a meet up.

Now this meet up was not meant as a hook-up. I was bored that night and a little lonely. It has been a long time since I had a girlfriend or a FWB so maybe this would be fun. I was in my early twenties while she was 31. Despite the large age difference, she agreed that coffee would be fine because I was funny. At minimum, it would be a good story to tell. We meet at a local coffee shop and chat for a bit.

I am your average guy. I am decently attractive (not a model, but not unfortunate either). She was a little nerdy, but in a cute way. She was maybe 5’2, short brown hair that was a little poofy since it was humid. She had some freckles and was quite petite. She was quite cute, but a bit more conservative.

While chatting, I made a comment about her coming to get coffee to hook up and winked. She thought it was funny and kicked me under the table. As we get up to leave, I walk her to her car. She had driven, where I walked to the “date,” if you can call it that. Like any other date, we had the awkward moment of how to say goodbye. So she gives me a hug goodbye and I whisper in her ear, “are you sure you’re not using me for a hook-up?” I admit, I was being an asshole and not very funny, but she looked at me a little differently, so I took my chance and kissed her. That kiss lingered for a bit, longer than I expected. We kissed a few more times as I pin her up against her car. I feel her push her hips against mine as I let my one hand wander up her thigh.

Breathless, she offered me a ride home as it just started to rain. In the car, when she went to grab the shifter, she grabbed the now noticeable bulge in my pants. “Oh sorry, wrong stick.” She drove me home and we made out in her car like horny teenagers. I asked if she would like to come up into my apartment.

She obliged and came up. I put on a movie, no clue what it was in retrospect, as a way to appear as if I had different intentions. We made out again and let our hands wander. We get into boxers and bra and panties. She had modest underwear on, a cream bra and white cotton underwear, the type that only some women would wear on laundry day. She proudly stood up and spun around. She pulled down her underwear. She stated that shaving was not of interest to her, a stark difference to the women I normally would be with. She climbed on me and said, “you keep those on” as she grabbed my boxers. She proceeded to grab my thighs as she rubbed her clit against my cock in my boxers. While it was definitely unique, it was hot to see her take care of herself using me. She thrusted for a few minutes until I felt her shake on me as I held on to her hips. She reached under the boxers and stroked me until I finished on her belly. Despite being older by almost 10 years, she seemed so innocent, but knew what she wanted.

We watched a few minutes of the movie while she absentmindedly played with herself. She rolled over and kissed me goodbye. I got her number and we ended up meeting a few times.

Does any one want to hear more? Do you have any stories like this? Feel free to comment or PM me!

Source: reddit.com/r/gonewildstories/comments/bnvzml/meeting_an_older_woman_from_the_internet_mf