Scratch one off of the ol’ bucket list [mf]…another bloated story of my experiences so far.

I think it’s normal to have a sexual bucket list. Maybe it’s not, but hell, everyone likes to think they’re normal, right? The point is, I have one. Over the years I’ve added and scratched off items on my list. Some of those things being: A threesome involving two women, a threesome with another guy and a girl, get laid two by women within the same day, sleep with a tall girl (I’m an average 5’7″ white guy), and many others. I’ve been lucky enough to achieve all but one of the items that are listed above, and this is the story of how one of them happened:
I’ve been able to make some money over time playing music in bars and restaurants. I would guess that 90% of my sexual encounters are a result of this (seriously guys, learn to play 25 to 30 popular songs decently, and start playing them out). The other 10% is pure dumb luck. 100% of the time its a total surprise. I’m on the shorter end of an average in every way white guy with no game.
I was playing at a restaurant when I met a nice woman named, Sarah. She was a middle aged lady who came into the restaurant. She seemed to really like the songs I played, I knew almost all of the ones she requested, and I would learn the ones I didn’t. Sometimes she was with her husband and kids, and sometimes she would just come in with her girlfriends. Eventually she asked if I played private parties. I sometimes did, and she arranged for me to play at her house.
Sarah is a doctor, as was her husband, and they lived in a GIANT house. They would throw little parties with their friends every month or so, and I became the regular entertainment. It was always fun.
Christmas time comes around and it turns out that the country club that Sarah belonged to was doing a fundraiser for who-knows-what and wanted some live acoustic music during the dinner. I had agreed, since it’s always fun getting paid to be the loudest person in the room.
The day of the fundraiser arrives and I’m told to talk to a “Cindy” about where to set up my equipment. I find her. The thing that struck me about Cindy was she was clearly in her mid-to-late forties, but everything else about her was “young”. She was a very attractive woman, with a chin length hair, platinum hair. She was in great shape and was wearing a little glittery pink dress with purple swirls all over it. It looked sort of plastic, but I have no idea what it was really made of.
Cindy shows me to the hall where I’m gong to set up and informs me that the check from the country club is in her office and to not let her forget to give it to me before I leave.
I start to play, and it’s going well.