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 say no.
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.
No One Real To Hold
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—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.
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?
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—if you think they didn’t care about the 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 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, 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?
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, 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 fuct, 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.

Nice, Dan
Preference, I can understand. But aversion to foreskin?
Excellent advise on the balled up linens on the floor. Only a very foolish (or naive) host un-does those little gems….
Sorry UNCUT’s so shy about his foreskin- I’ve never been put off by those babies. Wish I still had mine. Key note on the CLEAN and FRESH part, tho. A good foreskin’s hard to beat, but pass on the cheese.
Great advice, I really like your guest etiquette though I am shocked people would be that selfish. Either way probably not great friends.
The last line for the escourt is perfect, I have tell many girls the same thing but with relation to one night stands. It shocks me how recusive this behavour is.
One advice about foreskin: I once knew a guy who didn’t know that foreskin could be pulled all the way back for cleaning. So his cock was always immaculately clean, but under the foreskin was a forest of smeg. I implore UNCUT to not make the same mistake and clean under the foreskin. After that, he should be fine.
I want the first letter writer to have her boyfriend back. So sad. She’s been a reckless, lying, delusional moron. Don’t care. It’s heartbreaking.
Great response to UNCUT, Dan. As a just-the-way-I-was-born guy, let me add that no girl has ever had a problem with my turtleneck (though I do take extra care to keep it squeaky clean).
Long live the foreskin!
I love uncut cocks. They way they feel, the way they taste, how sensitive they are. And I’m a lady-type girl. I think Dan’s right–a lot of teenagers are insecure about sex in general, so they’ll be super negative about anything they’re unsure of, for whatever reason. I remember being super snarky about a college boyfriend who wanted to wear my panties. Now I think it’s adorable.
P.S. Three grand? Out of the blue from some random dude on Craig’s List? She may have lost her boyfriend, but she should start playing the lottery–girlfriend’s got some serious odds-beatin’ luck going there.
As a girl dating an uncut guy . . . he’s the best lover I’ve ever had, and giving him oral is AWESOME because I don’t have to cover him in unsexy slobber or (sugar-laden and thus yeast infection inducing) flavored lube to give a good blowjob. His extra sensitivity in the glans means he’s extra sensitive to what I’M feeling! Girls: You gotta try it. And if it’s smelly or gross? Tell them to wash!
Isn’t the host usually doing the houseguest a favor? Stripping the bed is such an easy way to say thanks. Actually getting the linens into a washer, if possible, should be standard–especially if they have seen some action. Ditto for dirty dishes. And a useful hospitality gift (food, booze, etc.) never hurts.
Oh yeah, and not menstruating all over someone else’s stuff. What? How is that not obvious?
How does HWTM know that the blood is from sex and not just from sleeping? I would *never* have menstrual sex in a guest bed, but I might have sex, then go to sleep, have my period start, and end up with messy sheets in the morning.
NORTH = TROLL
to UNCUT: don’t even worry about it. well, i know that no matter what anyone says, you will worry, but here’s what to do: don’t announce before he sees your dick that “i hope you’re okay with this, but i’m not circumcised, and i’m embarrassed by it.” that just draws attention to the fact and draws attention to your insecurity about the fact, which is more attractive than anything. just act like being uncircumcised is completely normal. and if he has any questions or wonders about how it works, just show him. but pretend you’re confident about it.
just make sure to keep it clean (wash it everyday in the shower).
chances are, he’ll love it. or like it. but he won’t hate it. i’m also uncut, and i’ve never had anyone express any fear or reticence about my dick. granted, i’ve (mostly) been with women, so our situation could be a little different. but there’s never been a problem, and after awhile, they start to think it’s fun to move your foreskin up and down (i’ve had several partners tell me this).
regarding that one girl’s comment, like everyone else has said—she’s just insecure or not very knowledgeable about sex. so to her, hearing about anything that slightly deviates from the norm kind of freaks her out. trust me, she wouldn’t “abort” if she were really in that situation. she’s be too in the moment.
okay, so maybe she might abort, but who cares? love your cock.
What adult woman doesn’t know that when you start your period during the night and bleed all over the sheets (yours or a guest’s) that you strip the bed, at least, and put them in the washer? Or at least rinse them in cold water so they don’t stain! For Christ’s sake, woman! Didn’t your mother teach you how to take care of your sheets? Or are you a complete moron?
I’m a straight girl, and I don’t mind an uncut penis, I just like penis, but PLEASE KEEP IT CLEAN!!!
Female children (of many ages, admittedly) are freaked out by foreskin. I’ve never met a sexually mature person who disliked foreskin in a mate.
The one and ONLY thing I regret about meeting my soulmate is that he’s circumcised, and I’ll never have a chance to experience lovely, lovely foreskin-fuckin’!
Go get him, UNCUT!
UNCUT, if you’re worried you can always just tell the guy that you would LOVE to exchange BJs. But you’re a virgin and you’re uncircumcised, and you weren’t sure how he feels about that.
If he shies away, then he’s an asshole, albeit a hot one, and still not worth a microsecond more of your time.
The letter from North is sooo fake. I can pretty much see the dude jerking off to writing it. How did you publish this Dan? It is obvious that some 40 something man bored with his life wrote you in between posting adds on craigslist about being a hot 20-nothing college girl looking to get gang banged.
Miss Manners recently addressed the issue of guest bedroom sex, too! Her (in my opinion, quite reasonable) ruling was that the permissibility of having sex “is conditional on [the guests] not making it known to others in the house, before, during or after the event.” Sounds like HWTM’s guests seriously violated that rule.
(The Miss Manners column: http://www.washingtonpost.com/wp-dyn/con… )
Straight female here… I actually prefer uncut, as long as it is clean.
Many years ago, a sexually active couple stayed a few days with my girlfriend and me.
My gf and I had pet gerbils and frequently gave them the empty cardboard cores of toilet paper rolls. (They love to chew them up and run through them.)
I got up one morning, saw an empty toilet paper tube in the bathroom trash and gave it to the gerbils, thinking, “Oh, my friends don’t know about our cute little practice of recycling the cardboard tubes this way.”
Later, my gf asked, “Why are the gerbils playing with a condom?”
Am I the only one who was thinking that NORTH is a guy? It didn`t occur to me that the letter-writer might be female until I got to the comments.
NORTH sounds fake.
I wish all the pain and suffering imaginable upon NORTH because I am a guy who has been cheated on and it is quite literally the worst pain in existence. All the people calling troll are adorably naive of how many guys are out there who are seriously that desperate to fuck a decent looking girl. I bet you could find NORTH with a quick google search.
HWTM made me laugh like hell, though, because I’ve had this problem before. Friends would come over and drink, they’d stay the night because they were too sloshed to drive, 2 of them would shack up, and I’d come down to a sticky couch. Eventually I just had to tell them they weren’t welcome to stay over anymore.
@17 — Plenty of “sexually mature” people don’t like foreskins, just as plenty of them do. Please don’t make blatant generalizations that could make someone feel ashamed of their sexuality for NOT liking foreskin as much as they could for liking it.
And for what it’s worth, I’m “sexually mature”, and prefer circumcised men, mostly because, without exception, every uncut man I’ve ever been with has broken the condom. YMMV.
yeah, of course NORTH’s a fake. She says she’s been hooking again for already a year, “and then some guy offered me $3,000 to sleep with him”. And what’s the significance of that tidbit again? Or does she mean this was her first trick in the entire year? And how could such a hot babe who could pull a $3,000 trick be so hopelessly unemployed for so long and broke? Maybe, but if she was so hot, she’d likely either have her own income or the bf would be paying for her.
I want to say for the record that unlike UNCUT’s one friend, I (a straight female) would not immediately abort oral, I would immediately thank god. Uncut cocks are the best.
@27 – you speak truth re. condom breaking. Best sex, worst day afterwards.
“As for any potential awkwardness after the fuct,”
Dan, I’m not sure how I feel about you in that Fruedian slip.
Having lived all my adult life in Europe, I’m completely mystified by this aversion to foreskins. For fucks sake, it’s not some alien growth, its a natural part of male anatomy! Think how ridiculous it would sound to have someone be squeemish about earlobes, or how awful it sounds when men in other parts of the world reject women with labia.
Granted, I’ve never been with a cut man, so I guess there could be some advantage I’m missing out on, but I tend to doubt it. I really don’t see how genital mutilation of babies can make sex more enjoyable. I guess I can see it as some sort of an esthetic preference, like some people like more muscular builds and others thin or others fat, though I’d personally categorize any esthetic preference that requires sharp cutting objects as a bit extreme for my taste.
Thank you, 20 (14thblackbird). It is high time there was a link on The Stranger to Miss Manners. She might seem to some to be on a different plant from the typical Savage Lover, but in fact they are on the same wavelength in many, many ways. And for God’s sake, ditch that nasty Prudie. She is so, so wrong. I hope no one ever takes her fool advice.
Uhh, Dan, you mention that the whore’s boyfriend is “at heightened risk of sexually transmitted infections.” That is true, but perhaps more to the point he is at heightened risk of his girlfriend getting fucked by other guys! For any normal man that is just a non-starter. Next.
Puty (7), would you feel the same way if you found out your girlfriend was a whore?
I married a retired escort. Dan, your advice was spot on.
NORTH was pretty lame for an April Fool’s joke. Come on Dan, you can do better!
Lynx, I moved to Europe as a virginal young thing too, and I also have no issues with foreskins.
Cut cock however… is really, really hot. Maybe it is just the novelty I guess. But, superhot.
@32: I live in Australia, and have never encountered anything remotely resembling the obsession with foreskins (discussing them, debating them, being grossed out by them, praising them to the skies) that exists in America. Why is it such an obsession, and moreover, why is it that more baby boys in your country have their foreskins sliced off than not? (This is a genuine question, does anybody know? There must be some historical reason.)
And I completely agree with the comparison to earlobes and labia. People, they’re just a normal part of the body! Move on.
I agree with #24; I assumed NORTH was a dude until I read #7; now I’m not sure either way.
I suppose it doesn’t really matter in the long run but…do we have any way of knowing the writer’s gender?
@RoseX, from what I know it started as a combination of a belief that circumcision leads to less infections and a belief that not having foreskins discouraged masturbation. You can find an overview here:
http://en.wikipedia.org/wiki/Circumcisio…
After it became an established custom, parents started forcing it on their baby boys because of social pressures. People with irrational disgust for natural men exist, but I doubt there are remotely as many people with an irrational disgust for circumcised men.
Noteworthy however is that according to that wiki link, up to 32% of Aussie men are circumcised, so its not quite a mutilation-free zone.
@ 27 and 30,
It could be that, since being circumcised used to be a rule and being intact was an exception, those men had nowhere to learn how to put on condom properly if you have foreskin. The trick is to pull back the foreskin before putting on condom. Next time maybe you can put it on for him, in case he doesn’t know this?
@ 39,
I suspect it had something to do with curbing masturbation in young boys… nothing easier than sliding your foreskin up and down.
N.O.R.T.H. sounds even more hack with that token $3,000 ‘Pretty Woman’ reference going on. I thought it sounded like a guy, too. You pick that one out of the presumably hundreds of submitted questions weekly? What’s that all about? 🙂
Dan, you nailed it with that past one in particular. Great advice. Thanks for the good reads once again.
First gal needs to get her shit together. What, she didn’t think that would end badly?
39: ” why is it that more baby boys in your country have their foreskins sliced off than not?”
Because this country is fucked up, that is why.
If we were chopping up female babies’ junk like that, there would be rallies at every college campus, with tear-soaked testimonies from young women blaming all manner of sexual and emotional dysfunction on the patriarchy that mutilated their bodies without consent.
And you know what? Those women would be right to be pissed. Who the fuck would we be to presume to cut their junk without consent?
But boys? Meh. We treat them like disposable kleenex any way.
And yes, I am aware that Jews follow this barbaric ritual as part of their relgion. I don’t give shit; I would outlaw it just like I we outlaw female genital mutiliation without regard to religious tradition.
Seriously people, just because it is common does not mean it is sane, ethical or acceptable. Leave people’s bodies–especially their genitals–alone unless you have permission from them and they are an adult. If that is true for sex, it would seem to be absolutely vital when talking about cosmetic surgery.
If you rule out foreskin, you are basically ruling out all of the hot dudes in Europe.
Jus’ Sayin’
And who’s to say that UNCUT’s hot prospect is circumcised?
Giving the house guest the benefit of the doubt, it is possible that having sex stimulated the start of her period or caused spotting after she thought it was over(like the Sex and the City episode where Samantha gets her monthly visitor on her date’s expensive sheets). You can’t always prevent messy sheets and accidents do happen (even if you put a towel down).
That said, it’s the guest’s responsibility to leave things as they were found. The guest should have cleaned the sheets immediately.
I think Dan’s guess about shame and denial setting in sounds about right. What’s done is done, though, so maybe just don’t invite them back as houseguests? I’m sure they will know why.
I am a gay guy and I agree with all the above responses to UNCUT. I personally have a fetish for intact dicks. Your hottie friend might take one look at your foreskin and get boned right away. In any case, it’s highly unlikely that he’ll be that put off by it. Good luck!
#42, you’re 100% correct. My boyfriend is uncut and before we switched birth control methods, we used condoms. He always pulled back his foreskin when he put it on, and never once did it break. We tested this method many, many, many times.
And uncut guys with dirty cocks? Seriously? My understanding was that it’s pretty uncomfortable for a guy who doesn’t keep clean. And surely their fathers are supposed to show them how to keep themselves clean???
@42: Although to note, my BF says he can’t pull it all back or it’s uncomfortable inside the condom. Yes, he’s uncut, has impeccable genital hygiene, and we’ve never had any problems with condoms. And blowjobs are awesome.
So, UNCUT … just fucking own it. If anybody else ever makes a remark like that, push back. It’s remarkably easy.
@32: EXACTLY. I can understand aesthetic preference, but only to an extent. That said, I would never make any man feel bad about his cut or uncut junk — that’s just so sad. Cocks should be celebrated and loved.
@50: Since traditionally circumcision was the rule, it’s pretty likely a lot of dads just didn’t know anything about foreskin upkeep because they didn’t need to themselves.
Also, do not underestimate the power of sheer squeamishness.