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I am 27 years old and still a virgin; I don’t think I know much about sex, except in theory.  I have a crush on a former Facebook friend’s boyfriend; he flirts with me sometimes, calling me “darling” and saying I’m “sexy” and “pretty”.  We have not met in person yet, because he’s Canadian and I’m a Hindustani living in South Africa, but he recently sent me a picture of his penis and told me he’s about 19 cm long, and that scares me.  Is sex painful the first time?  I kind of dread ever having to have it in real life; I’d much rather just fantasize about it.  However, I really love this boy; I dream about him all the time, and I wish he would bring me to Canada, marry me and give me a baby so we can live happily ever after.  He’s younger than me (only 21) but very mature for his age; he really is my dream man!  But I don’t know where I really stand with him; it seems like he only talks to me when he’s bored, and he punishes me by ignoring me when I make him upset.  I’d really like to know what you think about online relationships; I value your opinion very much since you’re so sexually experienced.

I wish I could tell you that sex isn’t painful the first time, but it very often is and every factor you’ve mentioned – his size, his (much too young) age, your (advanced for a virgin) age, your inexperience and your fear – will tend to exacerbate that.  So will the fact that he is NOT, despite what you think, mature for his age; punishing love-interests by ignoring them or just using them to alleviate boredom are NOT the marks of a mature or caring man, and frankly neither is sending out dick pics to women he isn’t actually involved with.  I know that you won’t believe me when I tell you that you aren’t in love with him; you’re infatuated  with him, which is a horse of a different color.  You aren’t especially drawn to this man for his personality or self, but because he pays attention to you, and for a woman who hasn’t had that kind of attention often enough, it can be extremely intoxicating and judgment-eroding.  I’m not saying relationships that start on the internet can’t work because I know some that have, but I am  saying that such relationships involve many difficulties that you, inexperienced as you are, are unlikely to handle well.  My suggestion is that you open yourself to meeting men locally in whatever way is acceptable in your culture; you still might fall in love too quickly and end up with a man who treats you badly, but if that happens you’ll at least be close to friends and family rather than stranded on another continent with a man you’re completely dependent upon.  Ironically, you’re afraid of the part – the physical sex act – that is really no big deal, yet ready to rush pell-mell into the part – marriage and childbirth – which can really get you badly hurt or even killed.  Sure, first-time sex can hurt; in fact, ten-thousandth time sex can hurt, and since my vagina is quite small I experience pain nearly every time I have sex with an unusually large or rough partner.  Sometimes it’s even a lot of pain.  But physical pain is transitory and, unless severe and chronic, doesn’t really have much effect on one’s life.  Emotional pain, by contrast, can be both devastating and have long-lasting and far-reaching effects.  I suggest you re-examine your priorities, try not to dwell on fear or simple physical pain, and instead think long and hard about the real and profound danger of severe emotional and spiritual (and sometimes physical) pain that accompanies a bad, hastily-made marriage to a poorly-chosen man.

(This question originally appeared in the form of a comment on a very old post, “All Shapes and Sizes”; some of you may find it interesting to compare the original with the edited version, and understand that this is typical of the way in which I prepare questions for publication.  One difference: I usually leave out location, but since this lady already shared it in the comments it seemed pointless to leave it out here.)

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)

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I recently started dating an escort that I’ve been seeing professionally for a while, but I found out that all of her escort friends are warning her away from me.  Why are they so skeptical about my feelings toward her?

Relationships with escorts are fraught with complications for a number reasons, including but not limited to:OLYMPUS DIGITAL CAMERA

  • Clients trying to get free sex by promising “love”, just as men have done to amateur women for millennia;
  • Clients who are turned on by whores qua whores, and not really attracted to the women as individuals;
  • Guys who really think they love a whore, but are not  prepared for the social stigma or the burden of having to keep her secret from employers, family, friends, etc;
  • Men who really are in love with whores, but let jealousy destroy the relationships;
  • Men who fancy themselves pimps and try to manage their girlfriends’ work, even to the point of abusive and controlling behavior;
  • Boyfriends or husbands who demand that the sex worker give up her work and either become economically dependent (“barefoot and pregnant”) or go to work in a shitty non-sex “straight” job that will wear her down;
  • Clients who think they’re in love with a woman, but are actually just infatuated with her business persona;
  • Guys who imagine that sex workers’ sex drives are higher than those of amateur women, or that they’re always more open-minded about preferences and kinks that they’re not being paid to indulge.

Those last two are probably the most insidious, because they may be hard for either party to tell apart from real affection and only reveal themselves once the couple is cohabiting and he discovers that he doesn’t like her relaxed, yoga-pants-wearing, housework-hating, menstruating, bad-hair-day-having, moody, personal-problem-suffering, family-drama-experiencing, opinion-expressing, not-always-in-the-mood, idiosyncratic self.  And this is just a start; if I sat here for a while I could probably think of half a dozen more, and I invite sex workers to include others in the comments.  I’m not saying a relationship with a sex worker is impossible; most of us do indeed have intimate partners, most of whom are male and some fraction of whom were formerly clients.  But there are special difficulties inherent in such relationships that require patience, wisdom and love to overcome or circumvent, and because several of those only apply to partners who started as clients, many sex workers are of the opinion that it’s better to minimize problems by eliminating those potential avenues of difficulty through the strategy of never, ever becoming emotionally involved with clients in the first place.

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)

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My boyfriend and I make each other happy and I want to continue thus, but our socioeconomic roles are blurry.  Both of us bring money to the table and I’m thinking about becoming an escort, which he has assured me he’s OK with because he understands it’s just a job.  Because of his fear that he would chase me away by being too aggressive, I at first had to initiate most intimate contact (though now he initiates it plenty).  He’s discussed getting married once our financial situations improve, and thanks to your advice and that of some friends, I’ve held my tongue on proposing.  Could a long-term relationship work between the two of us when both of us bring money and sex to the table?

The single most important factor in a long-term relationship, outweighing all others, is compatibility.  It’s totally possible for a marriage which flies in the face of many of the “rules” to succeed, as long as everyone involved is really OK with that.  Now, the trick is that they really have to be OK with it; they can’t just say they are in order to make their partners (or themselves) comfortable.  It’s possible to believe one is OK with an unusual condition – say, a husband who doesn’t bring money in – only to find later that it was not actually so, deep down.  Most of us will mentally downplay potential trouble-factors because we’ve been told such concerns are “shallow” in comparison with “true love”.  But the truth is that erotic feelings arise from a mysterious and subtle alchemy that is very hard to predict, and even small factors might over time change that alchemy so one no longer feels “in love” with a partner.  Many a relationship – some of mine included – has ended to the awful sound of the words, “I love you, but I’m not in love with you any more.”  And conventional people find that absurd statement to be reason enough for breaking up, mostly because they think that being “in love” was enough to base a relationship on in the first place.

What this boils down to is this:  you need to figure out what it is that attracts you to your boyfriend, and ask yourself whether it would change if you felt that you were supporting him (which could very well happen if you’re good at escorting and he’s not making a good bit more than you are right now).  Then ask yourself if you could continue a relationship with a man that you loved, but weren’t especially attracted to any more.  And finally, you need to ask if the two of you could part amicably if things do eventually go wrong; despite the fairy tale formula, not everybody lives “happily ever after” with the first person he or she tries to live with, and paradoxically a relationship has a better chance of success if neither person tries to keep the other one locked in a cage…unless you’re both into that, of course.

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)

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I’m extremely curious about Asian massage parlors; the media portrays these businesses as pure human trafficking operations, in the sense that the girls are essentially indentured servants who are brought to this country in debt and pressed to work off the debt without any hope of actually doing so.  What is the truth of the situation? 

Asian massage parlorThere are several different ways that Asian women come to the US to work; the most common is via family connections, as is the case with restaurants, nail parlors and other Asian-owned businesses.  Some women do indeed borrow heavily to migrate, but the “indentured servitude” aspect is exaggerated and mischaracterized.  First of all, few of them are trapped in the slave-like conditions of police and media wanking fantasies; it’s just that they have debts to pay and want to pay them as soon as possible rather than letting them drag out for years and years as many Americans are wont to do.  Far from being passive “victims” who are “brought” to the US like cargo, these are young women who took stock of their situations at home and decided that moving to the US was worth the debt and hardship.

Next, there is no moral difference between a sex worker taking out a loan to emigrate to a wealthier country and a student taking out tens of thousands of dollars in loans  – except that the former has a guaranteed job and the latter doesn’t.  Here’s another comparison: poor people who take out high-interest “payday loans” because they can’t get better deals from somewhat-less exploitative finance companies or regular banks.  It’s absolutely true that sometimes migrants are tricked into worse deals than they expected, but as anyone with poor credit can tell you the exact same thing is true of American financing deals, which can sometimes result in paying back many times the sum that was borrowed and carry a bewildering load of unfair and excessive fines and penalties.

Lastly, the reason these girls go into debt is that immigration into Western countries is incredibly expensive now, and the reason for that is the “authorities” have erected so many barriers to it; many thousands in fees, bribes, permits, paperwork and other squeeze is required to get into the US, and that money has to come from somewhere.  If US authorities really wanted to “combat human trafficking”, they would remove all artificial barriers to immigration…but that would stop the flow of lovely money to the politicians and corporations who profit from the restriction of international travel for work.  Forget all the nonsense about gangster “traffickers”; these crony capitalists – and the police departments who receive huge “sex trafficking” grants to harass them and rob their businesses – are the real “pimps” who profit from the labor of migrant sex workers.

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)

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When I was 21 I fell in love with a beautiful 25-year-old escort; I became her regular and after five months we started unpaid dating.  We fell in love with each other and planned to marry; I had no objection to her work, and she appreciated my support.  But not very long after we moved in together, she was diagnosed with a virulent cancer and died nine hard months later.  As you can imagine, I was emotionally devastated and started to see a psychiatrist who helped me a lot.  Seven years later, I’m successful in my business but don’t feel anything for any of the women I’ve tried to date.  When one of them questioned my emotional distance I told her about my dead girlfriend; she mocked me and then left me.  So eventually I decided to start seeing escorts again; for the last six months I’ve regularly seen a wonderful girl.  I’m so comfortable with her; we can talk about anything, and she’s the first woman I’ve been able to actually have sex with since my girlfriend died.  I have very strong feelings for her, but I don’t know if she feels the same.  I don’t want to lose her; can you give me any advice?

The Ghost Bride by Dienel96 (2011)Humans are creatures of habit, and sometimes we fall into destructive patterns of behavior without realizing that we’re doing it.  For example, a woman may get out of an abusive relationship, only to find she keeps unconsciously attracting or seeking other abusive men.  Or a man may keep dating women who all look eerily like his high school sweetheart.  It’s a well-known observation that people often marry partners who resemble (physically or behaviorally) their opposite-sex parent, and so on.  What it looks like to me is that you are unconsciously trying to bring your lost love back from the dead.  The two of you were so much in love and then she was suddenly snatched from you at a tragically-young age, so you haven’t really been able to accept that despite years of therapy; because of that and the bad experiences with amateurs, you seem to have convinced yourself that you can only be in love with another escort.  But while it may be true that escorts are easier to talk to than amateur women, and for most men we’re certainly less sexually intimidating, it is actually much harder for most men to have romantic relationships with us due to jealousy, stigma, cultural baggage and everything else.  Most escorts won’t even consider dating men they meet as clients, and though there are occasional exceptions your good luck in finding one in your first love may have blinded you to just how uncommon a situation it actually is.

It’s OK to keep seeing escorts for your sexual needs, but you mustn’t expect lightning to strike twice; it’s very unlikely that you’ll easily find another one to replace your lost love.  Do date amateur women, but do not under any circumstance tell them you even see sex workers, much less that you were emotionally involved with one; most amateurs are utterly clueless on this subject and will react like that one girl you tried to date, or maybe even worse.  And most of all, you need to return to therapy so you can get help in finally letting go of your beloved, so you’ll stop trying to replace her with someone who may share nothing in common with her except a profession.

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)

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For Love

I’m in love with a sex worker, and we’ve decided we are going to live together and she is going to retire and pursue a “normal” career.  Despite having a degree and being intelligent and capable, she’s concerned about getting work; I’ve told her I don’t have a problem with her seeing her more trustworthy regulars from time to time until she feels financially comfortable.  I’d be willing to support her completely, but financial independence is very important to her and she has said she doesn’t want to rely on me for support.  She reads your website avidly, so I wonder if you have any advice for us?

My biggest concern about the situation as described is that it’s nearly always a bad idea for a sex worker to stop working for love.  I did it, and it set the stage for two separate financial debacles in 2004 and 2008; we still haven’t yet recovered from the second one.  I’ve also seen others do it, with results ranging from OK to disastrous.  If your lady wants to quit sex work for other reasons that have nothing to do with you, well and fine; but if the sole reason she’s quitting to pursue a relatively low-paying “normal” job (in a bad economy, yet) is because of your relationship, she is making a mistake (potentially a very serious one).  The stress, drudgery and inadequate compensation of a “straight” job are likely to lead to resentment against you even if she makes the choice of her own free will, and if y’all get into dire financial straits because of the lesser income that resentment will be quadrupled.  Obviously, the choice should be hers and hers alone; neither you nor I nor her non-sex worker friends have any right to push her in either direction.  But she needs to deeply consider the potential consequences to her, to you, to your finances and to your relationship if she leaves a well-paid job for which she’s temperamentally suited in favor of a less-remunerative one for which she isn’t.

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)

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The Missing Piece

Before my divorce I was at a very bad stage in my life.  While going through that, I became emotionally involved with one of my business contacts; after we had sex he became kind of distant and doesn’t talk to me as much.  I love him so very much, and he made me feel like a worthwhile person at a time I was so low I didn’t want to go on any longer.  I don’t want to steal him from his family because I wouldn’t wish that kind of pain on anyone; I just want to be his mistress.  Is there any way to keep him interested?

puzzle with missing pieceThe reason I advise married men to only cheat on their wives with professionals is that other women fall in love much too easily, as you have done.  There is no magic formula for winning a man’s heart; women have been looking for this since the beginning of time and it simply doesn’t exist.  A married man may have an affair with you, but the chances of him leaving his wife and family for you is essentially nil; I know you love this man, but it seems pretty obvious to me that he lost interest in you as soon as he got the sex he wanted.  I can also predict with confidence that the more you demonstrate your love, the further he’ll distance himself because he doesn’t want a divorce.  I know you don’t want to hear this, but you need to leave off pursuing him; if you continue it will surely result in pain for everyone involved.  I also know that you feel very lonely right now, but you must learn to live with yourself before getting into a new relationship; after my first husband left me, I was alone for six years before becoming involved again.  Oh, I had commercial sex with men and casual sex with women (and a very few men), but I kept everyone at arms’ length because I knew I was not yet ready for a relationship.  We like to imagine that a romantic partner can “complete” us, can fill up gaps in our own personalities like jigsaw puzzle pieces fitting together, but the fact of the matter is that two broken people nearly always create a broken relationship.  I’m not telling you that both parties have to be in perfect mental health; if that were true, I could probably fit every healthy couple in the whole world in this room.  But what I am telling you is that you can’t use another person to “patch” whatever’s wrong with you; he can help you with problems, but the hard work of psychic self-repair is still your own responsibility.  It won’t be easy to be by yourself, but I think it’s imperative for the time being.  Seek professional help (and/or the help of friends you aren’t having sex with) in dealing with whatever caused that “bad stage”, and once you’ve begun to heal then you can open your heart up again to the possibility of a new relationship with someone who isn’t already taken.

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)

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