A little background: While I grew up in a small town with a religious family, I moved away for college and quickly discovered a world outside of those origins. I very quickly out grew my original repressions and fully embraced my sexuality.
Just like so many bad ideas turned sexy college stories have started – I was on break for either thanksgiving or christmas and back in my local area under the pressure of time. I had been having a streak of luck with the earlier days of Tinder (2012 or 2013 back when it really was the best) and so gave it a shot at home. I wasn’t having too much success in my age range so I expanded it to all ages for up to 100 miles.
After swiping right for some time, eventually I caught someone’s eye because a match appeared and immediately messaged me. At first she just asked if I was really looking for someone in her age range (late 30s) but after we moved to kik and began exchanging pictures, I knew this was the real deal. She was an honest to god milf. She was white, definitely shorter than me, and had a shorter haircut which I thought was very complimentary. (honestly some women cannot pull off short hair). She was brunette and more sweet than sassy but here’s as close as I can find: Example. I could spend a whole paragraph describing her body but one of the pictures that will forever be stuck in my mind was a full body pic of her up against the shower glass and showing off her curves.
We eventually made plans to meet really late at night since it was over an hour away from my parents much more rural home. I remember feeling the anticipation of the experience building up inside me when I pushed our truck down the driveway in neutral so that I wouldn’t be starting it right outside the house. On the drive there we kept exchanging messages in a rising haze of lust:
“are you coming?”
“yes, I’m on the way – about an hour out.” etc.
She had only given me a general area and when I got a bit closer, she sent me a description of the place and a maps pin. When I arrived, it was just as described. An unopened storefront on the second floor with sheets covering the windows, just like any other you commonly find across suburban areas. It was also hands down the sketchiest place I’d ever seen. I was there at 11:30pm at night trying to get my dick wet while home on break. I think back now and shake my head. My legs were definitely shaking but I tried to carry myself confidently as I knocked on the glass and sent her a final message. I was definitely thinking that my parents were never gonna hear from me again when she emerged from behind the plastic sheets behind the windows and unlocked the door. The top of her head only came to my shoulder when she nervously opened the door and gave me a hug.
Inside was literally an air mattress, a floor lamp and some towels. This was going to be strictly business. I can’t even remember if she offered me a drink before we were kissing and making out as hard as teenagers. We took our time because there wasn’t really any rush and we both had so much pent up frustration. (I hadn’t jerked off for 2 days which was a huge sacrifice for me at 19 haha) We spent about 30 minutes giving each other oral and just letting our nerves calm down, realizing that this was really happening. When we finally started having sex, I’ll always remember how balanced we were. You know how when you have sex, sometimes it’s more love making than fucking and sometimes the other way around? We were so balanced in our needs. Just enough affection and lust. Maybe it was just her experience or that she was so wet – it was exactly what we both needed. It was definitely the nerves and not my experience that allowed me to last even as long as I did because when she told me, begged me to finish inside her – no condom – I didn’t even hesitate. It was my first creampie experience and I remember cumming for 20 seconds while we hugged each other tightly and her legs wrapped around me to go deeper.
After we came down from our sexual high (that post-nut clarity), we started dealing with the reality of our situation. I realized just how sketchy of a situation I’d walked into and that there was now the possibility that she might get pregnant from this encounter. She revealed to me that she was married and that situation was the result of her getting married early and not taking time to sleep around in her younger years as another member of the repressed religious group that I was. After spending some time talking and getting cleaned up, we tried to go for round 2 but it was at least 1am at that point and both of us were exhausted.
After driving home we attempted to stay in touch and did for the next 2 years but we’ve since gone our separate ways and I haven’t reached out in a few years. Since that moment and moments like that, I’ve realized how possible it is to share an entirely vulnerable experience with a complete stranger and never forget that person. More stories to come.
TLDR: Horny college guy makes midnight trip to creampie milf under sketchy circumstances
Source: reddit.com/r/sexystories/comments/bgz59v/an_unprotected_milf_mf_milf
Wow good story