This week in Savage Love: Stressfest

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

Let’s set the escorting issue aside for a moment. You don’t want the same things (he wants monogamy and a defined relationship, you don’t want any of that shit), you don’t feel for him the way he feels for you (he’s in love, you’re not), and you’re a busy single mom and full-time student—all perfectly valid reasons to end a relationship, NTE. You aren’t obligated to tell him that something you were thinking about doing but haven’t yet done, i.e., escorting, factored into your decision to cut him loose.

While I definitely think people have a right to know if their partners are escorts, I don’t think people have an absolute right to know if their partners were escorts. So if the sex is really good, and you think there’s a chance you could one day feel as strongly for him as he does for you, and you’re planning to escort only until you get your degree, NTE, you could tell him you want to take a break. Explain to him that you don’t have the bandwidth for a boyfriend just now—kid, school, work—but you’re open to dating him after you’re out of school if he’s still single and still interested.

You describe yourself as a monogamist—so, yeah, entering into a committed relationship with this man would prevent you from exploring your bisexuality. And the timing feels off: He may be on the rebound, and you’re still coming to terms with your bisexuality. So don’t enter into a committed relationship with him, BETSY, at least not yet. Date him casually and keep hooking up with him, with the understanding—with the explicit and fully verbalized and mutually consented to understanding—that you will be “exploring” your bisexuality, i.e., you’ll be getting out there and eating some pussy.

P.S. Do some women actually enjoy anal? After my experiences, I find that really hard to believe.

If you’re still interested in exploring anal after all those red-hot-poker-in-your-ass painful experiences—and you are by no means obligated to explore any further—focus on anal stimulation, BUTT, not anal penetration. Try rimming, try a vibrator pressed against your anus (not shoved into it), try running his lubed-up dick up and down your crack (across your anus, not into your anus), and try all of these things during masturbation, vaginal penetration, and oral sex. Having a few dozen orgasms—or a few hundred—while your anus’s sensitive nerve endings are pleasurably engaged could create a positive association between anal stimulation and sexual pleasure.

It’s going to take some time to create a positive association powerful enough to supplant the negative association you have now—an association with echoes of regicide (google “Edward II and red hot poker”)—so your husband shouldn’t expect to get his dick back into your butt anytime soon, if he ever will at all. Some people, for reasons physiological or psychological or both, just can’t experience pleasure during anal intercourse. If you’re one of those people, BUTT, your husband will just have to grieve and move on.

P.S. I find it hard to believe that a woman could possibly enjoy, say, a Donald Trump rally. But some women do, BUTT, and we have video to prove it. The same could be said about anal.

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?