and the "best" one so far was when I slept with one of my best buddies girl-friends... she had discovered that he had cheated on her and I was a friend to both and ended up in the "shoulder-to-cry-on" roll... we shared a few glasses of wine during the crying... which turned into Gin and Lime Juices... and then we went at it... she also was in such a vindictive mood that she wanted it anally as well as vaginally because she had never let him do it to her that way, and wanted to get him back by letting me have the "first go at her dumper"...

oddly enough he and I are still friends... (he got me back later but that is a different story)...

she and I are not friends any longer...

the second I will tell of was during a trip... early 20s... Spring Break kind of thing to Mexico...

I met this girl and over the first few days kept trying to pick her up at the hotel bar... but kept getting turned down...

as what was starting to happen at the time, when I failed out with girls while on a trip, I would then look around for interesting guys... found an attractive older guy in his early 40s... let him blow me... it was very good... complete with well talented rimming...

he wanted to keep what had happened on the "down low" and I did as well since I was still trying to deal with being bi at the time... and wanted to "score" a girl before the end of the trip... but would politely say "hi" etc when I saw him... a few days later saw him sitting with that girl I was trying to hit on at the beginning of the week as they were getting in a cab to the airport and found out that he was her dad... he was divorced and had offered to take her and a few of her friends on a trip as a way to patch up relations with her post-divorce - but had pretty much only had breakfast and lunch with her all trip letting them "run around and party" as it were...

Several... but the first I will tell of was my ex-gf's mom at the end of high school...

(may not be as odd once you hear the details, but it still felt a little forbidden in hind-sight...)

I was working a part-time job at a clothing store in my last year of high school and this high-roller MILF type kept coming in and buying stuff from me... I met her by fluke one afternoon at a coffee shop... we got to chatting... she took me home and it was OK sex... but as I got up to use the bathroom I saw some of the family photos in the hall and one was a girlfriend I used to date... I met her parents before and this lady was not the "mom" I met... so I asked her who the girl was (without saying I used to date her but that used to see her at the store, etc)... and found out that my ex-gf lived with her dad and step-mom and this was her real mom...

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