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Finally fucked my first boyfriend - 35 years later
My husband and I are separated and working through counseling, but likely headed for divorce. A few weeks ago, my very first boyfriend from high school was in town to attend to some family business. We had dated for about a year back in the late '80s and things ended amicably enough that we remained friends. Our relationship was somewhat tame, all things considered. We had made out and played some touchy-feely, but had never really done anything more than that. We are friends on Facebook, so I had seen he was back in town and reached out to him to see of he wanted to grab a coffee or cocktail and catch up, as we hadn't seen each other in probably 15 years or so.
We chatted and decided to do dinner at a nice but casual place down close to the waterfront. I don't know why (or maybe I do) but I wanted to look nice for him, so I wore a skirt with a blouse that showed more cleavage than I normally show. (Hey, I'm 50 and have two grandkids now, lol!)
It was great seeing him, and we easily fell into conversation about remembering old times and where life had taken us since we last talked. He had never married and said he'd had a few longer term relationships but nothing that had ever lasted longer than a few years. He'd put on some weight (as have I) and was balding, but still had a handsome face with a quick smile and his easy-going personality. After dinner, we sat enjoying the music and he asked me if I wanted to dance. We danced a few slow dances and spent more time staring into each other's eyes than we did talking. I'm not sure which of us leaned in first, but a kiss happened. Afterwards, he said "I should apologize for that, but I'd be lying if I said I was sorry." I pulled him back towards me and kissed him again and said "Then don't apologize if you don't mean it." We shared another dance and went back to our table. He paid the bill and we walked out.
In the parking lot, we both fumbled with words trying to find something to say, only to both end up laughing at us acting like lovestruck teenagers again. Finally, he looked at me and asked "So, should we really do this?" I answered truthfully, saying "We probably shouldn't, no, but we're going to do it and we're going to enjoy it." We went back to the AirBNB he was staying at and as soon as the door closed we starting going at it. Within a few minutes we were in bed, him down to just his boxers and me down to just my pantyhose and bra, lol! We made love three times over the course of the night and thoroughly enjoyed each other.
I'm not sure where it will go from here, if anywhere at all. He finished up his business and headed back home (a few states away) and I'm still trying to figure out what my future is with my marriage. But I enjoyed finally being with him, and I think he enjoyed being with me. And even if it ends up being just a one night fling with an old boyfriend, it is something I'll always cherish in my heart and soul.
I posted an update to this in early July, where I was flying down to visit him for a few days for the 4th of July. He took me to do some sightseeing (he lives in Charleston, SC) and also took me out on his boat. Honestly, we also spent quite a bit of time in bed. He's been back up to visit me (outside of Washingron DC) once more, and we're thinking about taking a trip together to Florida or the Bahamas for New Year's.
Lovely story - good luck to you for the future whatever it holds.
I would love to meet up with my old mistress after an enormous number of years - guess it will never happen.
After graduating, getting married, and then living abroad for 22 years, I moved back home. Still married but in not the greatest place with him. I met a guy that I had semi dated in HS, he had also moved after graduating, moved out of state and was a successful lawyer. He was back home settling his parents estate. Our history was that in HS we were going with other people, but would flirt like crazy with each other, we never had sex, a lot of kissing, exploring each other bodies, one time we had oral with each other, It was fantastic, I got to a spot where it was one orgasm after another, and actually enjoyed his cum.
Anyway we arranged to meet and catch up, ended up spending the night together, the sex was great. He left to back to his wife and home, my husband finished his work and moved back and we bought a house. I felt empty for a long while then took a vacation near his house and we spent the day and night together. That was 20 years back and we find at least 2 occasions a year to meet up