June 24, 2009

I am a fairly successful man. I don’t make bank like Wall Streeters back in the day, but I haven’t been hungry since college. My girlfriend is younger. We met when she was in grad school. Like many recent grads, she isn’t steadily employed, she’s in debt, and she’s driving an unsafe car. So I support her, house her, feed her, and pay her bills (medical, etc.). She needed to pay off her credit-card debt—28 percent interest rate!—so she took work stripping and later as an escort. Through escorting, she was able to pay off her credit-card debt in a month.

Now some guys would find this distressing, but I found it kind of hot. Here’s the thing: After she paid off her credit-card debt, she stopped escorting. I’d like her to continue part-time until she finds a career. She’s mixed on this. We would like to buy a house and make things more permanent, but our income isn’t enough to do that if she’s making waitress wages. I guess it boils down to this: I would prefer to be with a sex worker than a waitress. I’d rather she make $200/hour on her back than $10/hour on her feet. She says she has issues with sex work. What do you think?
Perhaps I’m Mildly Perverted

I don’t think it’s up to me, PIMP, or you. And I would hope that your girlfriend, who’s financially dependent on you at the moment, doesn’t return to sex work because she feels coerced.

But I can certainly appreciate your point of view. There are men out there who’re turned on by the idea of their girlfriends/wives having sex with other men; some men are turned on by the idea of their girlfriends/wives being paid for sex. You’re clearly one of those guys. And you’re within your rights to share this information with your girlfriend and to try to convince her to return to sex work. Because your fantasies of sex work—of her doing sex work—turn you on. And, again, that’s fine. But you could make a more convincing case, PIMP, if you were better acquainted with the realities of sex work.

You should start sucking off strange men for money.

You’ll have to service men, I’m afraid, as there’s not much of a market for male prostitutes who service female clients. While lots of men fantasize about being paid to have sex with women, there’s a fatal supply-and-demand problem. Simply put: There are just too many men out there willing to give it away for free. That created a glut on the supply side, which has distorted the market, as there’s more than enough free straight cock out there to meet the needs of straight women.

So you’ll be giving head to dudes, PIMP. And after you’ve choked down a few hundred loads, you can go back to the girlfriend and say, “Sex work isn’t so bad!” with some credibility. And if you keep doing sex work after you’ve sucked off scores of men you’re not attracted to—men who may or may not have treated you with respect, men who may have very different standards of personal hygiene than you do—that might convince your girlfriend to continue to pursue sex work for your amusement.

Good luck.

Hello! I have been in a relationship with my boyfriend for about a year and a half. It is amazing! We are both very GGG, and it is by far the best sexual relationship I have ever had. But there is one thing that has been bugging me, and it’s the only thing I feel like I can’t share with him. My boyfriend really enjoys tossing my salad. I enjoy it! We love it! Here’s the problem: He kisses me when he is done.

Now I am not one of these people who is grossed out about sex-related things. I love it messy and sloppy. If he kisses me after eating my pussy, I’m fine with that. But kissing me after he eats my ass? I hate it! It tastes awful! It ruins the rest of the sex for me! I’ve heard the old “Well, imagine what it tastes like for him” adage, but he really does enjoy it, and I do, too… just not the kissing after. I’m not sure what to do about this. I am afraid that telling him would offend him and that he will stop doing it. (I do like having my salad tossed!) Am I being selfish? Should I tell him? Suck it up?
Bad Taste In My Mouth

One never permits one’s boyfriend—or one’s youth pastor or one’s president—to place his tongue in one’s butt if that butt isn’t clean and fresh. Because when one allows one’s boyfriend to stick his tongue in one’s butt, BTIMM, one is vouching for the edibility of one’s ass. When one consents to having one’s salad tossed—are people referring to anilingus in that way again?—one is saying to one’s partner, “My ass is clean enough for your mouth. Have at it.”

It is entirely reasonable for one’s boyfriend—or one’s youth pastor or one’s president—to assume that if one’s butt is clean enough to receive his tongue, his tongue is clean enough, post-salad-tossing, to be received in the mouth of the person whose salad he has just tossed.

So are you are being selfish? Perhaps you are. But we are, each of us, allowed a hang-up or two. You should inform the boyfriend that you’re not into kissing after anal-oral contact. But you must present this news to him as your problem, not his, as a hang-up of yours. If he likes you well enough, and enjoys eating your ass as much as he seems to, he may be willing to take a few extra steps—mouthwash on the nightstand? A quick swipe with a warm washcloth?—to accommodate your squeamishness.

What is the proper condom etiquette for threesomes?

In my case, I’m a guy and it would be with two girls. Do I change condoms when I go from one girl to the other? It seems like that would be a hassle. It’d kill the spontaneity.
No Clever Acronym

First, a general point: Spontaneity is overrated. The best sex often requires advance planning; the more people involved, or props involved, the more planning required. Although threesomes, for example, can sometimes “just happen” (often when three young people “just happen” to get drunk), most threesomes require some advance planning, particularly when adults want to have them. Finding the third, vetting the third, establishing the ground rules, talking about safety, etc.—all of that requires advance planning.

On to your specific question, NCA: You are going to have to change condoms when you hop from one girl to the other. Unless, of course, you’re a total asshole and you only care about protecting your own health, and you don’t give a shit about exposing Girl A to any sexually transmitted infections that Girl B might have, or vice versa. Neither girl should sleep with you if you refuse to swap out condoms, and you should remind yourself that, just as Paris was worth the hassle of a mass, realizing the number-one straight-male fantasy of all time is worth the hassle of swapping out condoms.

But you do have another option: the female condom. It’s a condom that she wears. I’ve used them—with dudes—and once you get past the slightly creepy trash-can-liner aspect of using them, they work fine. Stuff one in each girl, and you’ll be able hop back and forth to your heart’s content without pausing to change condoms. There’s more info about the female condom at femalehealth.com.

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