Savage Love 

My boyfriend of almost two years broke up with me yesterday over the fact that I used to be an escort. We had been planning a future together, talking about moving in, getting married, having kids, etc., 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 e-mailed me saying he would give me $3,000 to sleep with him, and I couldn't say no.

What do I do, Dan? I can't eat, sleep, or even do anything. How do I make things better? I am disgusted with the person I am and feel so dirty.

No One Real To Hold

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 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 — 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.

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?

Hostess With The Menses

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, 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 mortified by the mess and were paralyzed by shame. If that's the case, let it slide, buy your own replacements and cultivate other friendships.

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 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.

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, without exaggeration, the hottest guy I've ever met in my life. 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.

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.

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 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 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.

Speaking of Savage Love

Latest in Savage Love

More by Dan Savage

Readers also liked…


Never miss a beat

Sign Up Now

Subscribe now to get the latest news delivered right to your inbox.


© 2016 Orlando Weekly

Website powered by Foundation