Hey everyone this is going to be a long winded one, I’ll put a TL;DR at the bottom.
So about a year ago 22 year old me was having some issues. I was in a long term relationship with a woman I loved, but she was not interested in sex. Back in high school I had lost my virginity to her and we were pretty sexually active until her Sophomore year of college. A lot was going on and I understood. But, that didn’t change how horny I was. I didn’t want to look for someone else and I was sure any female friend I asked for a sexual favor from wouldn’t keep it quite.
So…I looked for an escort. After a few days of looking through web ads I found one I thought would work. She was attractive, plump C cups and a thick ass as well as around 10 years older then me. She also always used protection and as the two biggest fears I had where contracting a disease or being found out, I figured she checked all the boxes. After a light screening we set up a meeting at a local hotel. At this point I’ve got major nervous shivers. I’ve never cheated on my GF before and I’ve never had sex with anyone else. About an hour later, still shivering I pull up to the place and she waves me over. She looks good in person as well, wearing a sweater to cover her lingerie.