Q My boyfriend of almost two years broke up with me yesterday over the fact that I used to be an escort. He went through my emails and saw that I was answering ads, putting ads up, sending photos. We had been planning a future together, talking about moving in, getting married, having kids. And then this happened.
I know I either should've told him about my past or shouldn't have succumbed to temptation. I started doing this again a year ago because I got fired from my job and couldn't find anything. I was so in love with this guy that I didn't mind staying at home waiting for him all day, doing everything and anything to make him happy. It took a toll on me, and I couldn't support myself. Then a friend recommended that I start escorting again. And then this guy emailed me saying he would give me $3,000 to sleep with him, and I couldn't say no.
What do I do, Dan? I feel so dirty. —No One Real To Hold
A I don't want to salt your wounds, NORTH, but your boyfriend didn't find out that you "used to be an escort." He found out that you are an escort. Even those of us who believe that sex work should be legal, and that sex workers shouldn't be stigmatized, also believe that a sex worker's romantic partners have a right to know about the sex work. Just as people have a general right to know when their partners are sleeping with others, sex workers' romantic partners have a right to know about the sex work---and consent to it---because it places them at heightened risk of sexually transmitted infections.
There's probably no salvaging this relationship. The scale of the betrayal is just too great, NORTH, and your efforts to shift blame---it's your friend's fault for suggesting you get back into sex work, it was that guy's fault for offering you $3,000, it was your boyfriend's fault (!) for occupying all your time (?)---demonstrate that you have yet to take full responsibility for your actions. You would need to do that, NORTH, at least that, before your ex could begin to think about taking you back.
Q What's the etiquette for having sex when you're a guest? Friends spent the night and shared some passion. I don't have a problem with this. However, this was period sex, and I was left with bloody, sex-stained sheets. Am I wrong to be annoyed? Can I ask them to replace the sheets? —Hostess With The Menses
A Your guests had to know---if your sheets were a bloody mess, so were your guests---and they should have offered to replace your sheets. You're right to be annoyed. If you believe your friends are selfish and inconsiderate---if you think they didn't care about they mess they left for you---confront them, ask for replacements and cultivate other friendships. But if you know your friends to be deeply sex-negative, HWTM, it's possible they were so mortified by the mess---evidence that they'd had sex!---and were paralyzed by shame. If that's the case, let it slide, buy your own replacements and cultivate other friendships.
The etiquette for having sex when you're a guest in another person's house goes like this: Polite guests do not leave a bloody, spunky or santorumy mess for their hosts to clean up. Staying in the guest room and desperately horny? Sounds like the perfect opportunity for an extended---and tidy---oral-sex session. Staying in the guest room and want to fuck? Fuck on the desk, fuck standing up, fuck in the shower. If your partner is one of those only-in-bed, only-on-my-back types, lay a towel down on your host's sheets---or, better yet, a couple of your own t-shirts---and fuck away.
Thoughtful hosts purchase dark sheets and towels for guest suites. And if guests leave a towel on the floor of the bathroom in a neat little ball, toss it in the wash---with extra bleach if the towels are white---without unfurling and inspecting.
Q I'm a young-adult gay virgin. Recently, though, an incredibly sweet, incredibly intelligent guy expressed a desire to blow me. He also happens to be, without exaggeration, the hottest guy I've ever met in my life.
I lusted after him for the better part of a year before I found out he was gay. So, naturally, I want to pursue this.
There are complications. Along with my obligatory first-time jitters, I have to deal with the reality that we will be working together all day, every day, through the fall. Which could be awkward if there's any awkwardness after the fact. Which brings me to my main worry: I'm not circumcised. I've always been a little insecure about it. The one friend I trust enough to ask about this basically said that she would immediately abort oral if she realized a guy was uncut. If I don't do this, I'll regret it for the rest of my life (he really is that hot), but my friend's opinion has me worried beyond reason. I'm at a loss. Help? —Uncircumcised 'N' Completely Unexperienced Teen
A You shouldn't put too much stock in one friend's opinion about uncut cock, UNCUT, particularly if that friend isn't all that experienced either and---I hope all the sex-and-foreskin-positive single ladies will forgive me for this---when that friend is a lady girl. Some young women are squeamish about oral generally, and foreskins particularly, because they don't have much experience with cock, cut or uncut.
Gay men are much less likely to be squeamish about uncut cock; indeed, lots of gay men prefer uncut cock. My god, UNCUT, there are enough gay men out there with a fetish for foreskins to support a foreskin-specific porn genre for gay men. And even if this guy doesn't have a strong preference for uncut cock, UNCUT, it's unlikely that he'll be turned off by your clean, uncut cock.
As for any potential awkwardness after the fact, UNCUT, if the hottest guy you've ever swapped blowjobs with in your life---presuming the exchange of blowjobs goes down---is cold and distant, or even hostile, it might be because he doesn't want to get with you again. And like an idiot/asshole/amateur, he believes that being a dick is the only way to keep you from getting the wrong idea. If that happens, UNCUT, you'll have to be the grown-up. Get him alone and tell him that, hey, it's totally cool if he doesn't want to mess around again, but you don't want things to be weird. Tell him you intend to burn through any lingering feelings of awkwardness by being civil and polite to him, and that you would appreciate the same from him.