Taking [F]iona – [M]y cougar fantasy come true (long)

(F44) + (M26)

Before I get started, three points:

1. Yes, this is real and using an obvious throw-away account. Events detailed happened over a year ago. This will be the first and only post im making (long-time lurker of this sub, first time poster!)
2. Obviously I changed names, locations and what not. I am sincerely trying to avoid giving any identifiable information here.
3. I realize this post is long, feel free to jump to the action, I marked where it starts.

This starts before I ever started my new job. Just like every other young 20-year-old, I’ve always had a serious cougar fantasy. I dated a girl that was a little bit older than me during my master’s degree, which was amazing. And not just sexually, she really helped me grow as a person and sexual adult, something I had made a point to mention and thank her for. All things end though: at the end of my education I was moving back home and our time was simply over; never any hard feelings between the two. Still, I had never really had a true cougar experience. At that point I moved home and took a place-holder type job while I readied for another run through graduate school (different degree this time). While I prepped for the entrance test, I worked at a financial firm that would not only look good on a resume but get some income in while I got myself ready.