am writing to you because I know 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 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
What do I do, Dan? 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.
One Real To Hold
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
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.
Finally, NORTH, if doing sex work makes you feel this way—ashamed
and dirty—please 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?
With The Menses
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
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 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, 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, Dan. Please help?
’N’ Completely Unexperienced Teen
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 highly 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.
a new Savage Love podcast every Tuesday at www.thestranger.com/savage.