When to tell your part­ner you’re think­ing of es­cort work. Plus: “Do some women ac­tu­ally en­joy anal?”

The Coast - - SAVAGE LOVE -

QI’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

ALet’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— 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.

QI’m a 30-year-old sin­gle monogamist and I re­cently re­al­ized I’m bi­sex­ual. I feel much hap­pier. Ex­cept I re­cently crossed a line with a very close friend of mine, a man I’ll ad­mit to hav­ing some ro­man­tic feel­ings for. Af­ter he broke up with his ex, I started get­ting ran­dom late-night text mes­sages from him. And a cou­ple weeks ago, we hooked up sans pen­e­tra­tion. We ac­knowl­edged that we both have feel­ings but nei­ther of us is in a good place. He’s still deal­ing with the end of his LTR, and I am only just com­ing out as bi­sex­ual. I love this per­son and our friend­ship is im­por­tant to me, but I can’t stop think­ing of the pos­si­bil­ity of us be­ing to­gether. I’m con­fused by the tim­ing and I won­der if this is real or just some­thing I’ve al­lowed to dis­tract me—or both! Also, what would this mean for my bi­sex­u­al­ity? I’ve been to this rodeo be­fore—mean­ing op­po­site­sex re­la­tion­ships—but what about the part of me I haven’t fully ex­plored? —Be­tween Ev­ery

Thorn Soli­tude Yearns

AYou 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.

QI’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-hot­poker-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

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

AIf 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. PS 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.

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