I am a fairly successful man. I don’t make bank like Wall Streeters back in the day, but I haven’t
been hungry since college. My girlfriend is younger. We met when she
was in grad school. Like many recent grads, she’s not steadily
employed, in debt, and driving an unsafe car. So I support her, house
her, feed her, and pay her bills (medical, etc.). She needed to pay off
her credit-card debtโ28 percent interest rate!โso she took
work stripping and later as an escort. Through escorting she was able
to pay off her credit-card debt in a month.
Now some guys would find this distressing,
but I found it kind of hot. Here’s the thing: After she paid off her
credit-card debt, she stopped escorting. I’d like her to continue
part-time until she finds a career. She’s mixed on this. We would like
to buy a house and make things more permanent, but our income isn’t
enough to do that if she’s making waitress wages. I guess it boils down
to this: I would prefer to be with a sex worker than a waitress. I’d
rather she make $200/hour on her back than $10/hour on her feet. She
says she has issues with sex work. What do you think?
Perhaps I’m Mildly Perverted
I don’t think it’s up to me, PIMP, or you.
And I would hope that your girlfriend, who’s financially dependent on
you at the moment, doesn’t return to sex work because she feels
coerced.
But I can certainly appreciate your point of
view. There are men out there who’re turned on by the idea of their
girlfriends/wives having sex with other men; some men are turned on by
the idea of their girlfriends/wives being paid for sex. You’re clearly
one of those guys. And you’re within your rights to share this
information with your girlfriend and to try to convince her to return
to sex work. Because your fantasies of sex workโof her doing sex
workโturn you on. And, again, that’s fine. But you could make a
more convincing case, PIMP, if you were better acquainted with the
realities of sex work.
You should start sucking off strange men for
money.
You’ll have to service men, I’m
afraidโwhile lots of men fantasize about being paid to have sex
with women, there’s a fatal supply-and-demand problem. Simply put:
There are just too many men out there willing to give it away for free.
That created a glut on the supply side, which has distorted the market,
as there’s more than enough free straight cock out there to meet the
needs of straight women.
So you’ll be giving head to dudes, PIMP. And
after you’ve choked down a few hundred loads, you can go back to the
girlfriend and say, “Sex work isn’t so bad!” with some credibility. And
if you keep doing sex work after you’ve sucked off scores of men you’re
not attracted toโmen who may or may not have treated you with
respect, men who may have very different standards of personal hygiene
than you doโthat might convince your girlfriend to continue to
pursue sex work for your amusement.
Good luck.
Hello! I have been in a
relationship with my boyfriend for about a year and a half. It is
amazing! We are both very GGG, and it is by far the best sexual
relationship I have ever had. But there is one thing that has been
bugging me, and it’s the only thing I feel like I can’t share with him.
My boyfriend really enjoys tossing my salad. I enjoy it! We love it!
Here’s the problem: He kisses me when he is done.
Now I am not one of these people who is
grossed out about sex-related things. I love it messy and sloppy. If he
kisses me after eating my pussy, I’m fine with that. But kissing me
after he eats my ass? I hate it! It tastes awful! It ruins the rest of
the sex for me! I’ve heard the old “Well, imagine what it tastes like
for him” adage, but he really does enjoy it, and I do, too… just not
the kissing after. I’m not sure what to do about this. I am afraid that
telling him would offend him and that he will stop doing it. (I do like
having my salad tossed!) Am I being selfish? Should I tell him? Suck it
up?
Bad Taste In My Mouth
One never permits one’s boyfriendโor
one’s youth pastor or one’s presidentโto place his tongue in
one’s butt if it isn’t clean and fresh. Because when one allows one’s
boyfriend to stick his tongue in one’s butt, BTIMM, one is vouching for
the edibility of one’s ass. When one consents to having one’s salad
tossedโare people referring to anilingus in that way
again?โone is saying to one’s partner, “My ass is clean enough
for your mouth. Have at it.”
It is entirely reasonable for one’s
boyfriendโor one’s youth pastor or one’s presidentโto
assume that if one’s butt is clean enough to receive his tongue, his
tongue is clean enough, post-salad-tossing, to be received in the mouth
of the person whose salad he has just tossed.
So are you are being selfish? Perhaps you
are. But we are, each of us, allowed a hang-up or two. You should
inform the boyfriend that you’re not into kissing after anal-oral
contact. But you must present this news to him as your problem,
not his, as a hang-up of yours. If he likes you well enough, and
enjoys eating your ass as much as he seems to, he may be willing to
take a few extra stepsโmouthwash on the nightstand? A quick swipe
with a warm washcloth?โto accommodate your squeamishness.
What is the proper condom
etiquette for threesomes? In my case, I’m a guy and it would be with
two girls. Do I change condoms when I go from one girl to the other? It
seems like that would be a hassle. It’d kill the spontaneity.
No Clever Acronym
First, a general point: Spontaneity is
overrated. The best sex often requires advance planning; the more
people involved, or props involved, the more planning required.
Although threesomes, for example, can sometimes “just happen” (often
when three young people “just happen” to get drunk), most threesomes
require some advance planning (particularly when adults want to have
them). Finding the third, vetting the third, establishing the ground
rules, talking about safety, etc.โall of that requires advance
planning.
On to your specific question, NCA: You are
going to have to change condoms when you hop from one girl to the
other. Unless, of course, you’re a total asshole and you only care
about protecting your own health and you don’t give a shit about
exposing Girl A to any sexually transmitted infections that Girl B
might have or vice versa. Neither girl should sleep with you if you
refuse to swap out condoms, and you should remind yourself that, just
as Paris was worth the hassle of a mass, realizing the number-one
straight-male fantasy of all time is worth the hassle of swapping out
condoms.
But you do have another option: the female
condom. It’s a condom that she wears. I’ve used themโwith
dudesโand once you get past the slightly creepy trash-can-liner
aspect of using them, they work fine. Stuff one in each girl, and
you’ll be able hop back and forth to your heart’s content without
pausing to change condoms. There’s more info about the female condom at
www.femalehealth.com.

I think Dan’s advice to PIMP is right on. Nearly every sentence in PIMP’s letter mentions MONEY, not sex. Money is obviously power in his world.
He can’t understand why she’d turn down a $200 an hour job for a $10 an hour “on your feet, working your ass off” job. So Dan reminded him of the icky details that go into earning that $200 an hour. It’s not all about getting paid to “lie on your back and have orgasms all day”.
@96
“(“All the sex workers-” uhh, what, all two or three of them? And they speak on behalf of all sex workers. Right.)”
If even three sex workers say that they are able to maintain control of who they see, then that means that Dan’s assertion that all sex workers will have no choice but to see men they find dirty and disrespectful is 100% wrong.
It is not necessary to my argument that these three women speak for all sex workers. However, it is necessary for Dan’s argument that all sex workers necessarily lose control simply by being a sex worker. Dan is presenting a black and white argument, while I am saying that his view of sex work is too narrow.
Use of the female condom in this situation presumes that the women won’t want to have themselves some unobstructed fun in each other’s woo-hoos. In my experience, quite a misplaced assumption. Prepare to swap it up NCA.
@96
Read it one more time. I was referring “to all the escorts THAT enjoy their job”
I did NOT write THAT “all escorts enjoy their job”
See the difference?
I’m a bit disturbed by some of the erroneous ass eating tips especially those coming from “health professionals.” Eating an ass, dirty OR clean, will expose you to any diarrhea type pathogens from giardia to E Coli to salmonella. Diseases are passed by miniscule amounts of shit (eg food touching the hand of an infected chef) so being clean won’t eliminate risk. It will also put you at risk for hepatitis A (NOT B or C, unless there is blood or come/vag secretions to mucous membrane contact). You can also easily pick up HPV, herpes, + syphilis, and you can get gonorrhea or chlamydia or LGV. You WON’T get HIV. You can’t give someone something from their own ass by kissing, they would already have it. All of this has to be put in perspective of course.
An ass can be rendered perfectly clean by some douching to effect. I am perfectly happy to suck the LTR penis that occasionally alternates front to back in me. Anyone who’s turned off by stinky kisses after being rimmed needs some presex hygiene, stat.
I’m an MD who teaches LGBs and MD’s STD facts, FYI.
Hahaha. Your advice to PIMP was one of the best in ages, Dan. 100% spot on.
To those of you quibbling over the use of the term “mixed”: stop it. Yes, some sex workers enjoy their job. Or at least feel like it is worth the money. I have no problem with that at all. But this woman clearly doesn’t like it. If she did, she wouldn’t give it up for a job that pays a tiny fraction of what she made as an escort. If she gave up $200 an hour to work minimum wage as a waitress, then she obviously really didn’t like escorting. “Mixed” is his term, because it absolutely doesn’t describe her actions.
OK, just one thing, and I know it’s stupid simple, but I didn’t figure it out till late: in the shower, SQUAT when you wash your butthole. It stretches out those little wrinkles & just makes it easier to get your soapy fingers in close. SQUAT when you wash it. Enjoy.
My partner and I solved the problem encountered by BTIMM simply by the application of baby wipes before beginning our encouters.
My partner and I solved the problem of the squeamishness BTIMM encounters by the application of baby wipes before we begin our play. Really any moist towelette will do, but we appreciate the whimsy of baby wipes
@4: RIGHT ON, KS!!!!
I couldn’t have put it better myself.
@93: Right fucking ON!!!
Spot on call, too to PIMP, Dan!
You continue to rock!!!
ITA with Dan on the PIMP response..all details aside, it comes down to, “why don’t YOU try it for awhile, THEN get back to your GF, who has expressed a reluctance to continue doing it”. And maybe support her in finding work more suited to her educational and intellectual level.
On the anal/mouth issue, spec. wrt hep C, yes, it is spread through the blood, and according to the CDC, the risk of sexual transmission even after “a lifetime of monogamous sex with an infected partner” is less than 3%. They do not even advise the use of condoms in the case of an infected and uninfected partner.
Now hep A or B, different matter.
Never been much into ass-play myself, but y’all be clean and have fun with it!
As a former social service worker and sex-educator…
Just my two cents about m/f/f three-ways and/or two or more women sharing toys; even if everyone is disease / infection / yeast free and no-one sticks anything in anybody else’s ass, there is still a strong risk of PID – pelvic inflammatory disease – an immune reaction by one womans body to the vaginal/uterine cells of another.
Besides being painful, PID can result in sterility!
PID usually occurs in women who unknowingly share a male lover who’s not very careful about washing between sexual encounters
As to anal-lingus you wouldn’t put a dick in your ass and then in your vagina would you? A dental dam/saran-wrap should be used no matter how minty-fresh/clean as a whistle it seems ๐
Like Irena, I enjoyed Dan’s response to PIMP so much I too had a cigarette. Then I thought, what if PIMP wanted calls Dan’s bluff… another cigarette.
Go for it PIMP! Do it for love, seriously. Maybe you can score some bi curious guys and bi couples together?
Meanwhile, back on Wall Street the bonuses are flowing, the health care lobbyists are working, the campaign contributions are happening, the whores are spreading, the GOPer are adulating and apologizing, and were all about to get fucked again.
Go for it, PIMP! Call Dan on his bluff. Do it for love.
I’m pretty sure I read somewhere that when two people are living and sleeping together, they end up having most of the same anal flora anyhow. I don’t think there is a huge health risk here if you use common sense (don’t eat ass from someone with the stomach flu, for example).
Don’t they vaccinate for hep a?
Besides, the issue was ass-taste, not disease. This has gone way overboard. The solution to both of these problems is laughably simple –
if this girl doesn’t want to escort, she shouldn’t escort, and her bf should shut up.
if that girl doesn’t like the taste of her ass, she shouldn’t taste it, and her bf should shut up (and brush his teeth, get a breath mint, use a barrier, not kiss her, stop going down).
@ 113– I don’t have any idea where you get that notion about PID being “an immune reaction by one womans body to the vaginal/uterine cells of another.” PID is a result of untreated sexually transmitted illness, usually chlamydia or gonorrhea. It makes no sense that it would be caused by an immune reaction of one woman’s body to another woman’s cells– if this were true, there’d be an astronomically higher incidence of PID in the lesbian population. In reality, the incidence of PID and other STIs is actually lower among lesbians.
If you have a source supporting the theory that PID is caused by an immune reaction of one woman’s cells against another, I’d very much like to know, both for my patients and for myself. Do you have the PMID of the pertinent studies?
@64 “Transmission from the outside of a condom is not likely enough to make using dozens of condoms/female condoms worth it.”
are you f#cking kidding?! i almost forgot, in MFF threesomes, the point of wearing condoms is to only protect the M from ‘transmission’! you don’t deserve sex w/ 2 women or anyone for that matter… you’re putting ur dick in 2 different holes on 2 different bodies… that means 2 different people getting transmitted to from ur selfish dick… don’t even deserve internet porn…
Dan, right on with the comments! I like how you eased Pimp into a reasonable response, and busted out the truth. Same thing with the threesome dude. Lure them in, and mention wtf, you need to be protecting everyone’s health! (duh)
Nice work. And yeah, the pimp dude sounds like he got what he deserved.
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To #38:
You had <<…oral sex….>> but << got [a disease] without any sexual contact whatsoever. >>
The thing is, that IS sexual contact, BIG-time! It isn’t genital-genital contact, it isn’t penetration/sexual intercourse…but it’s every bit enough sexual contact to transmit all manner of sexually-transmitted diseases.
We have a tremendous confusion in our culture on the linguistics of sexual activity. We euphemistically say “have sex” instead of “have intercourse” [as in, “I did not have sex with that woman!” — which was ABSOLUTELY ACCURATE according to the prudish usage prevalent among those who impeached a president for exactly that statement!] — whereas we can be and are sexual in many different ways all our lives [even though those same people didn’t want Jocellyn Elder telling that to teen-agers, even to cut down on the teen-pregnancy rate].
“Being sexual” through the use of oral sex as opposed to sexual intercourse is a great way to prevent pregnancy.
To prevent transmitting certain diseases…not so good at all.
Dan, I wish you hadn’t damned the so-called FEMALE CONDOM with such faint praise. I’ve used it lots of times as a bottom for anal sex, and the tops have given it rave reviews, at least in part because its material holds body heat better than latex. It’s also great for guys who find latex condoms constricting. Whether for anal or vaginal sex, it’s always recommended to use lots of lubricant on the penis — and since the condom isn’t latex, oil-based lubricants work as well as water-based without compromising the condom. If the top/fucker wants to pull out & reinsert, it has to be done carefully, but it can be done. For the bottom in anal sex, using the “female” condom can reduce the need to meticulously douche. When we’re finished fucking, I’ve found it best to excuse myself to remove it in private in the bathroom, in case of any santorum-ish mess. All in all, it’s been a great addition to my sexual repertoire….
Came late to this one, but… (in fact, butt…) I usually agree with most of the advice on here, but the advice about ‘salad tossing’, well… it left a bad taste in my mouth.
The idea that by ‘allowing’ someone to lick your ass you are automatically vouching for its cleanliness is pretty patronising. It’s up to the individual to decide what they’re comfortable with – and if he’s fine with the taste of a little by-product then that’s his to choose, but he doesn’t have the right to inflict it on her. I’d be saying precisely the same if was a question about eating garlic.
In terms of risk, I know that my attitude to risk is not identical to that of all my partners, and some activities are essentially one-way in this sense. Letting someone lick my anus may give them a stomach ache, but is unlikely to adversely affect me (and since I have a rubbish immune system, it’s unlikely ever to happen the other way around). I’ve seen people who are into blood-drinking as a kink set up situations where infection-risk was essentially zero for one person and (hypothetically) extreme on the other, using sterile medical kit. I see nothing wrong with that either. As long as everybody is aware of the risks, balanced or no, then it’s up to each person involved to set their own level.
@18: hypocritical much? Maybe you should also add “labeling people” to your list of do-not-do’s
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