How to treat an Escort I will see regularly

I know she is not to be treated like a girlfriend, How often to text, etc....

also, I have a fantasy to be pegged. How should I bring that up?

 

Be straight forward! Communication is key!!

 

You only text when you want to hook up. Basically when initiating the next visit, conforming time and place, maybe that you've arrived, and nothing more until initiating the next visit. Mention your fantasy during the after glow period or as you prepare to leave next time. Just ask if it would be part of her services. She'll let you know.

Depending on how active she is in the business she may have as many as 20 or more regulars plus what she can schedule as one time visitors. If half of those wanted to carry on a texting relationship it would take away from her time used to conduct her business much less her personal life.

 

Also, she may not be a "girlfriend" but if you provide wine and treat her like a queen, she's likely to have you become a favorite. You'll be treated well.

 

There are more than just you in her life so respect that and her privacy. Beyond that, treat her well...maybe even better than she was expecting. Don't ask about her personal life unless she starts first. Even then, no probing for details. If you have preferences, mention them and ask if she has anything that she likes to do. One of the people I see wants me to talk dirty to her during sex and it helps her climax. Another likes to be watched masturbating and every session starts with her getting off while I undress and stroke. It's fun when you don't have to talk much and you just know what works.

 

To win her over? I would guess tip, tip, and more tip. Nothing wrong with that. I had a friend who went through a divorce, seen a lady on a regular basis, claimed that was much cheaper than getting married again, and going through same thing again.

 

I used to be an escort before I transitioned! My advice is to be upfront about what you like, be clean (ideally, get a quick rinse right before starting), be punctual and respectful of her time, and make sure she knows that even if you paid, she's still in charge and allowed to set boundaries. My favourite clients weren't necessarily the biggest tippers, but clean guys who communicated their desires clearly and didn't push me to do things I didn't want to do. I also found that with regulars like that, I could relax and even enjoy myself. I didn't always cum, but I did sometimes. Can't do that if you're nervous lol.