Some of my best and most memorable experiences were with a prostitute. When I was in my 20s I met a woman in her 40s working at one of the brothels in my hometown by the name of Jasmine. She could tell I genuinely fancied her and after our first session she gave me her private number. She eventually stopped working at the brothel, and for the next 10yrs I'd meet her every other month at her flat. She basically became my sex teacher and after about 4yrs I felt at ease enough with her to ask if we could do it bareback and she said yes. As a bonus she didn't charge me extra for it. We'd usually meet in a pub and have a couple of drinks before going back to hers, where I'd stay the night. I never felt bad about it, in fact I always thoroughly enjoyed it and so did she. We just had the most exquisite, intimate and mutually explosive unprotected sex. We'd eventually fall asleep, then wake up, have sex again, shower together and kiss each other goodbye until the next time. She never fucked for free, but she was a very nice lady, we kept in contact in between meets, and I got to fuck her without a condom AND cum inside her EVERY SINGLE TIME. What wasn't to love? Sadly I moved away seven years ago and we lost contact. I still have her number on my phone, but the last time I was back in my hometown I tried to call her and it had been disconnected.