I [M] 20 hooked up with my [F] 30 coworker

While I was in college I used to work in a fine dining restaurant on weekends to pay rent and bills. This was a pretty classy place that had cloth linen and long wine lists. We constantly had high rollers come in and it was easy to make some serious cash.
One of my coworkers was about 10 years older then me and was a total knock out. Let’s call her Tiff. She was slim with shoulder length black hair, B cup breast and a perfect ass. I had such a crush on her it was embarrassing. Since I was young and dumb Id do things like clean her car off of snow after work, help run her food and basically anything she needed. Tiff knew exactly what she was doing and would play it up enough to keep me on the hook. Give me sexy winks while we worked, touch my shoulder while walking by and say things like “only if you were a little older”. It would drive me wild!

[MF] no condom

I had been in a long term relationship for a few years and we had mutually decided to break up. She was ultra Christian and we never had sex and I was starved for that feeling. I talked to friends and everyone told me to get on tinder. It was pretty new at that time so I thought I’d give it a try. I had gone out with a few woman at this point when I matched with “Kiera”. We chatted over the app for a bit and switched numbers. It was awful. Every time we were supposed to meet something came up. I almost gave up. Long story short, my buddy told me to give her one more shot. I said screw it and just asked if she wanted to come over to my house. Kiera agreed but seemed a little reluctant, she was defiantly nervous.