I'm asking this because i would love to try it with my regular escort, but i don't know if she's up for it. I'm afraid i’ll ruin our relationship if i ask her directly.

If i were you, i would do it this way. When you notice that she becomes boring or that things are stagnating, then you will have nothing to lose and it'll be a win - win situation. If she says no - ok you'll find another one as it already became dull, if she says yes - it will spice up the intercourse and it will be whole another story.

Be honest. If she's so good to become a regular, then she must possess some good qualities, and i think she appreciates honesty. Offer her extra and mention STD tests. That's the best way. 

I did and it ruined the relationship i had with her. The first time we did it, it was cool. But as the time went by i started asking myself if it's right call, because at that moment she was seeing a lot of guys and had a lot of regulars. So if she let me do BB, she probably let a dozen other guys too. So, i asked her once if she did a STD test lately, and she got mad, kicked me out of her apartment and told me to never call her again.

Find yourself a girl, NSA relationship, let her use the pills and cum inside her as many times as you want.

I'd been offered once, but for a steep extra money so i refused the offer. It was tempting, but it wasn't worth that money, as it wouldn't last for more than 5 minutes.

Wouldn't do that. If she does it with you then she does it with every regular guy. And getting the least harmful STD is pain in the ass, not to mention HIV, hepatitis. Don't play with your life for a few minutes of fun.

@Virgam

That's exactly my thought and i keep repeating it in my head in the hours prior to the session in order not to fall into temptation and do the BB.

Was offered once. She got carried away, told me that she doesn't like rubber as it makes her sore. But i convinced her to give me BBJ and CIM instead of BB penetration.