I’ve got a question I doubt you’ve ever gotten before. It has a bit of everything: sex-work etiquette, long-distance phone interaction, and a het cis chick anxious not to lose her tolerance badge. Here it goes: A few months ago, I started getting hang-up calls from numbers I didn’t recognize in Boston. Then weird texts started showing up, trying to set up “dates.” I responded to the first few because I figured someone was giving out a fake number that just happened to be mine. (I kept my cell phone when I moved from Boston to Seattle.) But after the fourth or fifth call/text from a different unknown number, I turned to the Internet. Google informed me that my phone number is identical, except for area code, to a trans escort working in Boston. I’m getting one or two calls or texts per week meant for this other woman. They’ve started to get more explicit. Because of the time difference, they come at weird hours. I don’t know what I should do. I can ask my phone company to block each number individually, but that’s a pain in the ass. I can text the correct area code to the men who are writing to me looking for the trans escort, but I don’t really want to help people too stupid to read a phone number correctly. I suppose I could report the whole thing to the Boston police, but I doubt they’d care. I don’t have any moral objections to sex work, I just don’t want people to call/text me asking for it. Aside from changing my phone number, which has been my sole number for almost eight years, anything else you can suggest? —Stupid Phone And Messages
You claim to have no moral objections to sex work, and you say you’re a tolerant person. But you’re thinking of siccing the police on a trans sex worker—and for what? One or two calls or texts per week. As pains in the ass go, SPAM, that sounds like a pretty piddling one.
You know what constitutes a major pain in the ass for a sex worker? Being harassed by the police and swept up in the criminal-justice system. You’re right, the police are unlikely to drop everything to solve your problem. But you shouldn’t call the cops on this woman regardless, SPAM. If your call was answered by a lazy cop who would rather hassle trans sex workers than go after criminals who are actually hurting people, this woman—a woman who hasn’t really harmed you in any way—could wind up getting badly hurt. The criminal-justice system is rough on sex workers generally, SPAM, and it’s absolutely brutal to trans women who do sex work.
Here’s another idea, SPAM, and a better one: Call the trans escort and have a conversation with her. You’ve got her phone number. Talk to her.
As distressed as you are to receive these calls and texts—and, again, one or two a week doesn’t seem like that big of a deal—that sex worker will probably be more distressed to learn that she’s losing so many potential (and numerically illiterate) clients. I have known and loved a few sex workers—loved in a strictly platonic sense—and most would change their professional phone numbers regularly to rid themselves of time-wasters and clients they didn’t want to see again. The sex worker whose calls you’re getting may be willing to change her number, SPAM, or at the very least emphasize the correct area code in her ads.
The best way to demonstrate that you don’t have a moral objection to sex work is to assume sex workers are reasonable human beings and treat them accordingly. Because sex workers are human beings, SPAM, and most human beings are perfectly reasonable. If we were talking about a Fox News personality, my advice might be different—but we’re not talking about a Fox News personality, are we? —Dan
I’m a happily married woman in my 30s. My husband and I are interested in exploring anal sex. We enjoy finger play, but so far we haven’t tried anything larger. He’s afraid of hurting me and wants to start with toys and plugs. But I want to jump right in. He’s not that big and, in all honesty, I take shits that are longer and thicker than his erect penis. (Sorry to be gross.) Do you think we need to start slow? Why won’t he even try? —Anal Novice Anxiously Lusting
When I hear from straight couples just starting to explore buttsecks, ANAL, it’s usually the boy who wants to “jump right in” and the girl who is afraid of getting hurt. I tell these straight boys that they are obligated to take their partner’s feelings into account—they must take it slow, they must use lots of lube, they must start with fingers and toys and plugs, etc. Those are Buttsecks Best Practices. My advice for you is the same: You are obligated to take your partner’s feelings into account. His fear of hurting you is just as valid as a woman’s fear of being hurt. So while you may not need plugs and toys for your own comfort, ANAL, you should use them for his. It’s possible, of course, that his concern is misplaced—you’ve taken shits that are longer and thicker than his erect penis. But unless you’ve taken shits that have jumped out of the toilet and jammed themselves back into your ass, and then proceeded to pound away at you for 20 minutes, you really don’t know what it’s like to get buttfucked. —Dan
I am a 43-year-old female who’s in a six-month relationship with a 26-year-old male. At first it was a FWB arrangement, but after about two months we decided to be exclusive. We explore many things that he wasn’t able to explore with younger women. But he does not orgasm from vaginal or anal sex. He comes only if he masturbates. He says he has reached orgasm only once during vaginal. He agreed to stop masturbating to see if that would help. No change. I suggested a urologist, but he’s a college student with no insurance. Please help me to help him. It’s not a big issue, but he’s going to need to be able to do this when he gets married and wants to start a family. —He Can’t Come
He can so come—he just needs to crank himself over the edge using his fist. Needing his own fist to finish may be the result of death-grip masturbation techniques, and he could retrain his dick with some time and effort. But it’s not fair to say that “he can’t come.” He can and he does. If a woman can’t come from vaginal intercourse alone, which 75 percent of women can’t, but can come during oral sex or when mixing fingers or a vibrator into vaginal intercourse, we don’t say, “She can’t come.” We say, “This is what she needs to come.”
This is what he needs to come. Maybe that will change with time, experience, and some effort to mix up his masturbatory routine (get that boy a Fleshlight), but it’s possible that this is how his dick works. Women who need oral or a vibrator to climax shouldn’t be made to feel bad or be told they’re somehow damaged, HCC, and guys who need a little jack at the end shouldn’t be treated like they’re damaged either. His dick works.
And when it comes time to have kids, he fucks his wife until she’s satisfied, pulls out, jacks himself past the point of no return (aka “orgasmic inevitability”), shoves his dick back in, and blows his load all over her egg(s). No problem. —Dan