Q: I’m a recently divorced single mom and full-time student. I’m really beginning to hurt financially and have decided to start working as an escort. I am at a point of great emotional stability, happiness, and confidence–all reasons that led to my decision–and I’m surrounded by people who love me and won’t judge me. (Not that I will be telling most of them.) I’ve been seeing a man who I like, but I’ve made it clear that I am not committed to him and can see him only once a week. I’ve explained that I don’t think I can ever be monogamous and I do not want a relationship. He has struggled with this and told me early on he was in love with me. We have AMAZING sex, and I think this causes him to have a hard time understanding why I don’t want a relationship. I do not want to tell him I am escorting. I feel the fewer people who know, the better. And I don’t know him that well, as I have been “seeing” him for only six months. I know he would want to know, and a huge part of me feels that the right thing to do is be honest with him if I am going to continue seeing him. I also know that cutting him loose would hurt and confuse him, especially without being able to give him a reason. How do I handle this? What is the right thing to do? My site goes live in three days, and what’s keeping me up at night is not how best to verify clients, it’s what to do about the man in my life who I respect and love, even if I am not in love with him.—New To Escorting
Q: I’m a 37-year-old woman married for eight years to a wonderful man. We’re happy and GGG to the point where his kinks have become my kinks and vice versa. However, he loves anal sex and I cannot do it. No matter how much lube we use or how slowly we go, it’s not just uncomfortable, it’s red-hot-poker-in-my-ass painful. Can you give me any concrete, practical advice to get to a point where I can enjoy anal? —Beyond Uncomfortable Tushy Trauma
A: Here’s an idea, TENSE, but please run it by your therapist before giving it a try: find a guy you like and propose a different kind of friends-with-benefits arrangement. You will be in charge—you will do all the initiating—and while he can say no to anything you ask, he isn’t to ask for or initiate anything himself. You set the menu, you make the rules, you give the orders. He’ll need to be someone you trust, and it’ll help if he’s someone who thinks following orders is sexy—and trust me, TENSE, those guys are out there. You said that normal sexual situations aren’t working for you. Maybe an abnormal one would? v
