Only done it twice. Both cheesy and surprised how much I got into it. The first, she was a professional masseuse, into sports massage. She was seeing to a thigh injury I had and she couldn’t help but turned on (I’m that attractive obviously). She got closer and closer to my cock and started touching it but kept feeling guilty as she was married. Then things got more risqué, and she started sucking my cock and stopping through guilt and to keep checking the door to see if her boss was coming. Obv we ended up fucking and she was acting nervous as she was worried about getting caught. Escort was really good and threw herself into it.
Second was more risqué/niche. Escort posed as an unexperienced virgin - just turned 18. No idea who I was supposed to be. She confided in me that she was planning on fucking her boyfriend but was worried about what to do. It was a pool party and we started with her trying on swimming costumes to try and find the sexiest. She was coy during this, trying to hide her body. When we found one, she asked if I could show her to kiss. Then progressed into her sucking my cock to practice and then involved sex so she can try it. Was a fun scenario.