I am writing to you because my boyfriend reads your column religiously. I don't know what to do. 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 e-mails and saw that I was answering ads, putting ads up, sending photos. We had been planning a future together, talking about getting married, having kids, etc., and then this happened.
I know I 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 anything to make him happy. It took a toll on me, and I couldn't support myself. Then a friend recommended I start escorting again. And then this guy e-mailed saying he would give me $3,000 to sleep with him, and I couldn't say no.
I can't eat, sleep or even do anything. All I want is to hold my boyfriend and to be held. How do I make things better? I am disgusted with the person I am and feel so dirty.
No One Real To Hold
I don't want to salt your wounds, 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, 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 to 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 too great, 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, at least that, before your ex could begin to think about taking you back.
Finally, if doing sex work makes you feel ashamed and dirty, stop doing sex work.
What's the etiquette for having sex when you're a guest in another person's house? 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
Your guests had to know -- if your sheets were a bloody mess, so were they -- and they should have offered to replace your sheets. If you believe your friends are selfish and inconsiderate, confront them, ask for replacements and cultivate other friendships. But if you know your friends to be deeply sex-negative, it's possible they were mortified by the mess -- evidence that they'd had sex! -- and 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 a 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 that towel in the wash -- with extra bleach if the towels are white -- without unfurling and inspecting. Be warned: An unwise host who unfurls a balled-up white towel may find herself staring at what looks like the flag of imperial Japan. And if your guests are courteous enough to strip the bed before they leave, those balled-up sheets go straight into the wash, too.
I'm a young-adult, gay virgin. Recently, though, an incredibly sweet, incredibly intelligent guy expressed a desire to blow me (among many other things). He also happens to be the hottest guy I've ever met. 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 first-time jitters, we will be working together all day, every day, through the fall. Which could be awkward. 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 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, but my friend's opinion has me worried beyond reason. Please help?
Uncircumcised 'N' Completely Unexperienced Teen
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.
Gay men are much less likely to be squeamish; indeed, lots of gay men prefer uncut cock. My God, there are enough gay men out there with a fetish for foreskins to support a foreskin-specific porn genre. And even if this guy doesn't have a strong preference for uncut cock, it's highly unlikely that he'll be turned off by your clean, uncut cock.
As for any potential awkwardness, 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, 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 feelings of awkwardness by being civil to him, and that you would appreciate the same from him.
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