College friend helped me hookup with my crush [MF]

First time I met my college fwb Anna, she was sitting with a group of her classmates at the on-campus Starbucks. I needed to charge my phone and the nearest plug was behind their table. The group was friendly, and Anna and I clicked. Overtime we would become friends and eventually more. Both of us were single, horny college students; plus, we were compatible.

The sex was astoundingly great, we complemented each other mentally and physically. To this day, she’s been my best sexual partner, the relationship lasted about a year, until I graduated and moved away for work.

Fast forward 5 years or so, Anna reached out through FB chat and we begin catching up on lost time. Doesn’t take long for the texts to become NSFW. At this time we are both single, but living many hours away, plus both heavily entrenched in work.

At some point one of her old college friends comes up in a convo, Maribel. She was a looker. Very attractive woman who had gone back to school in her late 30’s while Anna and I were studying. I had a huge crush on her, she basically checked all the boxes for my milf fantasy. Great body, attractive face, beautiful smile, and a playful personality. But, she was married when I met her, so I never flirted with her or made a move. Just not my style.

Hooking up with my boss’s Mom. [MF]

I checked out this sub-Reddit a few weeks ago after hearing about it from a friend and have enjoyed the stories so much that I was inspired to share something that I’ve kept under lock and key for over a decade, circa 2011. I have not told a soul, not even my wife.

Let me start with the setting and backstory, then I will share everything else (****), down to the granular details, as memory serves best. It’s a bit long, but it gives context to the event. All the names used in this story are changed to prevent someone from being recognized.

By the end of summer of my Senior year, at a state college in south Texas, I was dealing with the heart break of being dumped by my girlfriend of two years. It happened over Skype a few days after I helped her move to Austin, to attend a more “prestigious” university. I was quite smitten with her and in total denial that the relationship would end after she decided to transfer. I thought she was THE ONE, but life had different plans. I’m sure some of you can empathize.