Absolutely not... if it bothers you, then he should be respectful of your boundaries and not be pressuring you to provide a service. I hate when people spend money and then act like they own you-- they are giving you money for services rendered, they didn't give it to you out of the kindness of their heart. You wouldn't see an accountant for 5 years and then say, hey dude so you I paid you to do my taxes for five years how about you do them for free this year? I had tons of clients like that when I was a stripper, after months of spending money they would expect that I would sleep with them outside. And I'm sure I'll be getting similar clients as an escort once I have regulars.

You have to go with what you are comfortable with, because otherwise you're going to feel like shit about it afterwards if it's not your decision, you're going to violated and like you were used. It's clear from your posts this service he is asking for makes you uncomfortable and you are only considering it because he is pressuring you... tell him to go do bareback with someone who actually offers it and not to come back and see you anymore as he is clearly not a respectful client to begin with! Asking for it once after months of seeing you, I would still frown and hold it against him but wouldn't drop him-- asking you repeatedly is disgusting!

I think some clients deliberately try and 'groom'some escorts...spending alot of time with them, flattering them, fussing over them etc to manipulate them into giving more than they normally would. He sounds like one of those types...jog him on.

id been asked for bareback and told  they had a certificate for their disease free cock. still no thanks. I don't see why any of us should be pressured to do this or other sex acts we arnt advertising.
he is pushing his luck and in the end you might not see him if he carries on like this.
ive also had clients think its ok to push their uncovered cock near the entrance of my v  which at this point ive pulled away fast and then said put a condom on. some even loose the erection and blame it on the condom and expect us to ride bareback its still no. I just find myself repeating I don't do bareback, they get the message in the end and I don't end up feeling worried about catching something.

★★I wouldn't do without under no circumstances do unprotected penetration not even for 100,000 pounds as my health is priceless. I will say sure though will do owo providing it meets my ocd standards. :-)★★

it doesn't matter how many times he sees you or what money he 'invests' that's always been his choice. you never said see me more and down the line I will give you bareback so don't let him get in your head and make you feel bad! He is trying to take advantage don't let him!

xx