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I got inspired to type this out as a story for you all to read by another redditor.
Going back to my early twenties, I spent a lot of time hanging out in bars and having wild hookups here and there. There was one night where me and a bunch of friends went out in NYC for some girls night fun. The night went on and we were at some rooftop bar having a great time and this older guy, probably mid 40s has been chatting with me, buying drinks and the usual. As the night progressed he and I got into a full on flirty mode and eventually I ended up leaving my friends and going with him to his hotel room which was only a few blocks away. Probably not the best choice but I was young and living in the moment. We got to his hotel room and it was incredible, it has these open windows facing this walkway where anyone who looked up could see what was going on in the room. It don’t take long before he and I were putting on a show in that window, some people would point, stop and stare and we both put on our best performance. I must also say, this guy was incredible, great body, nice dick, great at foreplay and putting me in positions that were amazing. We put on our show for probably 45 minutes before taking the action to the bed. The night was amazing, this guy by far had been the best guy I’d been with based on sexual skill. We got it on one more time in the morning before, again an amazing time. He offered to drive me home but I had him drop me at a friends house instead just in case he was some stalker. He told me how he was married and had kids and didn’t want to really have any connection beyond that night but we did exchange numbers… fast forward about 1 years and I meet this guy at a bar, super nice, had a great job and overall he was a great guy. We got to dating, the sex life was meh but I was looking for a slower pace at this time in my life.
We had been dating for a few months and it’s getting close thanksgiving and he convinces me to go and meet his parents. We get to his house and first I meet his mom, who is really nice and telling me how she’s so happy to meet me. She mentions to my boyfriend that his father had just ran to the store to get some wine for dinner and would be back shortly. We go on chit chatting, and I’m getting asked like 5000 questions and that’s when his dad walked in. My heart almost stopped when I saw it was the guy I had the hookup with a year ago. He looked at me and it took him a minute or so to fully figure out how he knew me. He popped the cork on the wine and I guzzled the first glass to relieve my anxiety. The night went on and on, it was super awkward in the beginning but eventually things got more comfortable with the help from the wine.
Eventually the father and I were left alone in the kitchen and he asked me if I remember, it was one of those brief yup, let’s not talk about it.
Eventually the son and I broke up but every time I would be at his parents house I got more turned on being around the dad then the son… I always wondered or sort of hoped he would try and reconnect with me but he never did.
The disappointing part was the sex skills and penis gifts were not passed down 🫢
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- 11 months ago
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