Category Archives: Sex Work

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Hi Dr Dick,
Happy (belated) New Year! I have two questions for you:
1. I am taking a long time to cum when I’m given a blowjob or hand job and eventually I need to stroke off on my own (for a pretty long time as well). However, I cum pretty quickly when I masturbate while watching porn. Am I masturbating to porn too much? I have also masturbated to porn for years before I started having sex recently (I’m not sure whether this could be a reason as well).
2. You mention that we shouldn’t use soup while cleaning our anus. Why is that so? I just read about douching but I have been cleaning my anus with warm water, soap, and finger. Is that ok?
Thanks in advance!  — Ken

Can’t hardly say if you are masturbating to porn too much.  I mean, what is too much anyway?  And since you don’t go into detail; I’ll let that issue rest.

What I can tell you is that partnered sex, regardless of the activity (blowjobs, hand jobs or full-on fucking) is a whole lot different than solo sex (with or without porn).  I can also assure you that your body has become sensitized to your particular grip and stroke over the years of you pullin your own pud.  Another person’s grip and stroke (pussy or asshole) will rarely satisfy in the same efficient manner.  This is not a bad thing, necessarily, but you do have to keep that in mind.  And perhaps your sexual response will change with time as you enjoy more and varied partnered sex.

In terms of you taking too long (whatever that means) to cum when you are with a partner, maybe you need to quit trying so hard to get off and lay back and enjoy the sensations you’re getting from your partner.  And here’s a tip; use your biggest sex organ, your brain, to replay some of that hot porn action in your head while you are gettin head.  That will surely hasten things along, if ya know what I mean.

In terms of your next question about keeping your hole clean; you may have misunderstood previous comments I’ve made about anal douching.  Soap and water is the preferred method of keeping the outside of your ass clean.  And while you’re scrubbin’ your crack, you could use your fingertip to clean out your rosebud.  But don’t force soap beyond your sphincter.  You have delicate membranes in your rectum that will be irritated by the soap, even a mild soap.

If you need to douche, I suggest a solution of a few drops of lemon juice in warm water.   Some men prefer the convenience of a shower bidet.

Name: Mike P
Gender: Male
Age: 25
Location: Los Angeles
My girlfriend needs to watch lesbian porn to get off and sometimes kicks me out of the bedroom to masturbate by herself.  Initially I was turned on by her desire to watch porn — but now — it’s become a blockage.  She always needs porn.  I am frustrated and to make things worse — she has started abusing me through financial manipulation. I have to pay her rent — pay for her food, pay everything — and she never gives me nookie.
Should I leave this woman?

Time to wake up, fella!  Your “girlfriend” — and I use that term very loosely — is decidedly not YOUR girlfriend, and possibly not any man’s girlfriend.  I’m gonna go way out on a limb here and say; I think your “girlfriend” is a certifiable, died-in-the wool, muff-divin’, coochie-lovin’ lesbiterian.  All that remains for her to do, to make the picture perfectly clear…even for you, is to show up one day in a mullet and a flannel shirt.  Holy cow, Mike, how is it that you are missing the obvious?

Listen, bub, you’re excess baggage.  Your “friend” keeps you around for comic relief…oh and to foot the bill.

Should you leave this woman; you ask.  Honey, she’s beaten you to the punch on that one.  She’s long gone and done left you way behind, at least emotionally and sexually.  All you need to do is find the door, say good-bye to this sorry situation and make a hasty exit.

Name: Michelle
Gender: Female
Age: 22
Location: Canada
Tips to help when the man you’re sleeping with has a small penis.

Tips?  No pun intended, I hope.

Ok, here goes — Tip #1, grin and bear it.  Tip #2, find a guy with more pork.  Tip #3, get a dildo.  Tip #4, find a sexual position, like doggie style, that will make the most of every little bit of pecker the poor guy’s got.  Tip #5, remember it ain’t always da meat, but it is always da motion.

Ok, seriously I do have a couple of suggestions beyond the flippant ones I just mentioned.  For example, Tip #3 still stands.  Find yourself a dildo, one that your partner can wield when he’s around.  If you introduce the concept in a positive way, you may find that Mr. Mini-meat will go for it big time.  You see, most guys with small endowments already know they may have a problem satisfying some women (or men for that matter).  But most guys, regardless of cock size, are always interested in pleasuring their partner, even when it’s not with their own magic wand.

May I suggest that you check out the swell array of dildos available at Dr Dick’s Stockroom?  You’ll find a link to this treasure trove on the top of this page.  Hey, you may even want to shop online together.  You may be surprised at the one your guy picks out for you.

While you lovebirds are checking out the dildo section at Dr Dick’s Stockroom, take a moment to search for a Cyberskin Penis Extension.

You’re gonna love this.  The new Cyberskin line of products represents a significant advance in pecker extensions that feel like the real thing. The rubber on the surface of this extension feels hauntingly like human skin. But the inside part of the (1.5″ or 3″) extension is much firmer.  It is soft and supple on the surface, but hard and rigid inside.  Mmmm, hard and rigid!

Visually, the shape, texture, and coloration of these extensions are designed to create a realistic effect as well.  They look realistic and they feel realistic.

There’s a trick to putting on one of these puppies, don’t ‘cha know.  You roll up the sleeve until it’s all the way up around the extension. Then place it against the head of your guy’s stiff dick.  Roll the bugger down snugly around his unit, sealing his peanut inside the sleeve.  A partial seal will form, helping keep the extension on during the fuck-fest.

Wearing this extension will add both length and thickness to his precious willie. It will of course reduce the sensation in his cock, but that’s not always bad thing.  Guys with a short fuse may find the decrease in stimulation an aid to controlling his ejaculation, while he’s giving more and longer pleasure to his partner.  And a lot of guys love the feeling of having their cock sealed inside the rubbery sleeve.  Mmmm, sealed inside rubbery sleeve!

Name: Jack
Gender: Male
Age: 42
Location: Milwaukee
I’ve been dating this guy for over a year.  He is the love of my life.  I love him so much, but he treats me like shit.  I met him on vacation in Florida.  He’s 26 a stunning, 6’3” 200lbs, blond surfer Adonis.  And excuse me for being so graphic; he has the biggest dick I’d ever seen.  The first time we had sex I saw stars.  He filled me up like no other person has.
When I got home we exchanged emails nearly every day and even had some hot phone sex a couple of times.  He was down on his luck, because he lost his barista job for coming to work stoned too many times.  I know I shouldn’t have, but I invited him to come live with me.  I flew him up, but I told him that this wouldn’t be a free ride, he’d have to stop smoking so much dope and get a job and he agreed.
The sex was fantastic for the first couple of months, but once he established himself as a star at the gym he found his own friends and now I don’t see too much of him.  He eats my food and drinks my liquor and drives my car.  I pay for his cloths and gym membership.  He has yet to find a job.
I know I should just end it, but I love him and I would really miss the sex.  My friends ridicule me for thinking he loves me as much as I love him.  They tell me they know he sees other guys.  I’m so turned around I don’t know what to do.

Like my momma always used to say:  if it’s got wheels or a dick, you know you’re gonna have problems with it.  And I would add, if it’s got big wheels or a big dick you know you’re gonna have BIG problems with it.

Before we turn our attention to your no good boyfriend, let me make a few quick observations about you.  You’re a freakin’ mess, girlfriend! I mean really, you’ve broken all the cardinal rules about dating a hustler.  I know, I can hear you now…oh no Dr Dick, he’s not a hustler; he’s a good kid who’s just down on his luck and I’m just trying to help.  Bullshit!

Ya see, that’s the first cardinal rule of dating a hustler is never lose sight of the fact that he’s a hustler and you’re his john.  Don’t get me wrong; I have the deepest admiration for hustlers and their johns.  It’s just that this arrangement only works if everyone is clear about the ground rules.   And here are the ground rules — rich older gentleman connects with needy younger hunky stud for mutual benefit.  Rich older gentleman keeps needy younger hunky stud in room and board, booze, cloths, car, gym membership and the like; and needy younger hunky stud buggers rich older gentleman senseless with his big blond surfer-boy dick.  Get it?  Got it?  Good!

Second cardinal rule — what happens on vacation should stay on vacation.  Vacation sex, as wonderful and delicious as it may be, does not transplant very well to your non-vacation life.  You’re more likely to have success transplanting a delicate tropical orchid to your Milwaukee backyard than transplanting a vacation hustler fuck to your work-a-day world back home.

Third cardinal rule —don’t try to gloss a perfectly fine, fully functional and even an affectionate hustler/john relationship with talk of love.  It’s unnecessary, unseemly and untrue.  It’s lust, it’s limerence, it’s love sickness, whatever…it’s just not love.  Because LOVE don’t ever make you feel as bad as you’re feelin’.  Probably your friends would have less difficulty with your mooning over this guy if you were more honest about the nature of this relationship.  They wouldn’t be rubbing your face in the evidence that surfer-boy is pluggin’ other dudes.

Fourth cardinal rule — a size queen, like you Jack, should admit that you are enamored with the guy hose and how it fills you up plain and simple.  To pretend that you would string yourself out like this for a guy with tiny meat is just that — pretense.  Listen, there’s nothin’ wrong with bein’ a size queen, it’s the dishonesty I object to.

How is this young fella ever supposed to respect you when you don’t respect for yourself?  He probably had you pegged (no pun intended) back on the beach in the sunshine state. He knows you will tolerate his misbehavior, which of course gives him permission to do whatever he feels like doing whenever he feel like doing it.  And now he don’t even have to give up the occasional mercy fuck any more, even though that was surely part of the deal at the get go, right?

So the waif has yet to find a job after a year, huh?  Why is that not surprising?  But even a hustler needs his mad money, besides what is doled out to him by his long-suffering john.  I’d be willing to guess Mr. surfer dude is turning tricks to keep himself in weed and other essentials.

Thing is, this fellow probably would have treated you better if you would have just stuck to the hustler/john script.  Ya see, kids like this need structure.  He may have looked to you for this at one time, but when he realized that he had you cock-whipped, the teachable moment evaporated.  This lad is probably like most other boys with big dicks.  They learn early on that their cock gives them enormous power, because it is the object of desire for so many.  He soon discovered that you were no different than all the other men (and some women) in his life — only interested in owning a piece of his sizeable endowment.  And so he turned the tables on you.  You can hardly fault the guy.  You try to manipulate him with your money.  He outwits you and manipulates you with his johnson.

If you’re really serious about reining in the little monkey, you’d better come up with a clear, unambiguous message about what you will and will not tolerate.  And it better be something more than “I expect you to bone my scrawny middle-aged ass on occasion.” Because, until you do, he will roam wherever and whenever he wants.

There are many root causes for his behavior, just like there are many root causes for your behavior.  But since I’m talking to you, not him, I suggest that you get to the bottom of all of this by investing a good deal of time and energy with a competent sex-positive therapist. There’s one thing I can say for certain, if the status quo continues your resentment will boil over one day and there will be violence, the kind of violence that you may not think yourself capable of now.  But violence there will be; you can bank on it!

Is there enough goodwill between the two of you to resolve this unfortunate situation amicably?  Who knows!  If I had to guess, I’d say there was a slim to no chance for that.  If that’s the case, I advise you pack him up and put him on the next plane south.  And no more relationships for you, particularly with unemployed young men with massive schlongs, till you get your head screwed on tighter.

Good Luck ya’ll

Sex EDGE-U-cation with Voluptuous Lynn – Podcast #177 – 01/06/10

Hey sex fans,

We’re ready to rock and roll with a brand new year of podcasts in the Sex EDGE-U-cation series. As you know these programs take a look at the fascinating world of unconventional sexual expressions and lifestyles, fetish sex and kink.  We touch on topics both familiar and exotic.  And you can count on our investigations to be interesting, stimulating as well as very informative, because we chat with prominent educators, practitioners and advocates from all walks of life.

And to kick off this new year, I have something quite extraordinary for you.  Today, we feature the first woman of color to speak in this series. She is a sex worker.  She brings a refreshingly honest, unique and sassy voice to the ever-growing chorus of exceptional guests in this series. I am honored to welcome Voluptuous Lynn.

She describes herself as “An Ebony Cougar In Sin City,” but I think you will agree with me that she’s more akin to a tiger.  Her no nonsense approach to life, sexuality and sex work if truly refreshing, and she’s knock ‘em dead funny too. Oh, and you should know that today’s show is unusually long. Lynn and I got to shootin’ the shit and I completely lost track of time.

Lynn and I discuss:

  • Flying in the face of the culture’s notion of female beauty.
  • Leaving the vanilla world for sex work.
  • The life of this cam-girl and phone sex operator.
  • Being public about her work.
  • The impact of her sex work on her personal relationships.
  • Role playing with clients.
  • Advice for getting into sex work.
  • How she prepares herself, emotionally and physically for her job.

You can visit Lynn on her website HERE!

See a slideshow of Lynn at work and play.  Click on the thumbnails below.

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BE THERE OR BE SQUARE!

Check out The Lick-A-Dee-Split Connection. That’s Dr Dick’s toll free podcast voicemail HOTLINE. Don’t worry people; no one will personally answer the phone. Your message goes directly to voicemail.

Got a question or a comment? Wanna rant or rave? Or maybe you’d just like to talk dirty for a minute or two. Why not get it off your chest! Give Dr Dick a call at (866) 422-5680.

DON’T BE SHY, LET IT FLY!

Look for all my podcasts on iTunes.  You’ll find me in the podcast section, obviously. Just search for Dr Dick Sex Advice. And don’t forget to subscribe. I wouldn’t want you to miss even one episode.

Today’s Podcast is bought to you by:  Dr Dick’s Stockroom.

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Sophie Hirschfeld, Part 2 – Podcast #160 – 10/14/09

Hey sex fans,

We’re back with more mighty fine Sex EDGE-U-cation with my special guest, the etqet34aspxwatermarkedbeautiful, talented and oh so smart, Sophie Hirschfeld.  As we learned last week, she is a plus-sized model, stripper, camgirl, phone sex actress and writer.  And in this, Part 2, of our conversation, we continue our chat about her career as a sex worker, activist and educator.

You didn’t miss last week’s show did you?  Shame on you if you did!  But don’t get too down on yourself, because Part 1 of our chat is archived right there on my site.  Simply use my site’s search function to your right.  Type in Podcast #158 and presto!  But hey, don’t forget to use the #sign when you search.

Sophie and I discuss:

  • Sex work and her intimate relationships
  • Components of sex work that don’t involve sex.
  • Sex work, part of the service industry.
  • Fantasy and role-play.
  • Sex work, a double-edged sword — empowering yet demanding.
  • Current economic conditions add to sex worker rolls.
  • How some women justify their sex work.
  • Lesbian-for-pay cam chicks.
  • Her encounters with the pizza boy!
  • What the general public can learn from sex workers.

You’re also gonna want to visit Sophie at her fabulous website HERE!

BE THERE OR BE SQUARE!

Check out The Lick-A-Dee-Split Connection. That’s Dr Dick’s toll free podcast voicemail HOTLINE. Don’t worry people; no one will personally answer the phone. Your message goes directly to voicemail.

Got a question or a comment? Wanna rant or rave? Or maybe you’d just like to talk dirty for a minute or two. Why not get it off your chest! Give Dr Dick a call at (866) 422-5680.

DON’T BE SHY, LET IT FLY!

Look for all my podcasts on iTunes.  You’ll find me in the podcast section, obviously. Just search for Dr Dick Sex Advice. And don’t forget to subscribe. I wouldn’t want you to miss even one episode.

Today’s podcast is bought to you by: Dr Dick’s Stockroom.

drdicksstockroom.jpg

Sex EDGE-U-cation with Sophie Hirschfeld – Podcast #158 – 10/07/09

Hey sex fans,

I have something truly extraordinary in store for you.  As you know this Sex EDGE-U-cation podcast series takes a look at the world of fetish sex, kink and alternative lifestyles. We touch on topics both familiar and exotic.  And I chat with prominent smilewatermarkededucators, practitioners and advocates of unconventional sexual expressions and lifestyles from all over the world.

Well then, today, we add yet another unique voice to this growing chorus.  I have the distinct pleasure of introducing you to my special guest, the beautiful, talented and oh so smart, Sophie Hirschfeld.  She is a plus-sized model, a stripper, a camgirl, a phone sex actress and a writer.  But I think she’s best described as a philosopher of sex.  Oh, I should also mention that she is absolutely hilarious too.

We will be talking about her career as a sex worker, as an activist and as an educator.  You don’t want to miss a moment of this, sex fans!

Sophie and I discuss:

  • Where sex and science collide.
  • Magnus Hirschfeld and Sidonie-Gabrielle Colette.
  • Being an erotic entertainer.
  • Which is the oldest profession?
  • Getting into the sex industry.
  • Economic considerations of sex work.
  • Sex work on the front lines of sex education.
  • Her sex work and her intimate relationships.
  • The power of dirty words.

Be sure to visit Sophie at her fabulous website HERE!

BE THERE OR BE SQUARE!

Check out The Lick-A-Dee-Split Connection. That’s Dr Dick’s toll free podcast voicemail HOTLINE. Don’t worry people; no one will personally answer the phone. Your message goes directly to voicemail.

Got a question or a comment? Wanna rant or rave? Or maybe you’d just like to talk dirty for a minute or two. Why not get it off your chest! Give Dr Dick a call at (866) 422-5680.

DON’T BE SHY, LET IT FLY!

Look for all my podcasts on iTunes.  You’ll find me in the podcast section, obviously. Just search for Dr Dick Sex Advice. And don’t forget to subscribe. I wouldn’t want you to miss even one episode.

Today’s podcast is bought to you by:   Eden Fantasys.com.

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Wait, Wait, Don’t Tell Me…

Name: John
Gender:  Male
Age: 16
Location: San Diego
My dick is kinda small.  I want to add 3-5 inches.  How do I do that?

Jeez, this is just about my least favorite topic of all.  I keep promising myself that I won’t small_cock1respond to anymore “how do I grow my dick bigger?” questions.  And then along comes a young pup, like you John, and asks the question again.  Here’s a tip, everything I have to say about cock enlargement schemes I’ve already said.  If you want to know my thoughts about this wearisome topic scroll use my site’s search function in the sidebar to your right.  Search with key words like “cock shape”, “cock size” and “jelqing”.  Once you read through all columns and listen to the podcasts you will have all the information you seek.

Here’s a bit of an overview of what you’ll find.  First, you’re not even completely through puberty yet, John.  So if you could just chill out for a couple more years till your growing spurt is complete, you might find that nature itself will resolve your issue for you.  If, by chance, you find that by your 18th birthday your cock is no bigger than it currently is, then it’s time to make your peace with your piece.  Because basically that’s the dick you’re gonna have to work with for the rest of your life.

In other words, you have about as much chance of growing a bigger dick than what your genetics has determined for you as you do growing your feet bigger or adding inches to your height or changing the color of your skin.  It’s simply not gonna happen.  There is no true way of safely increasing either the width or the length of your johnson, short of a small_cock3surgical intervention. And I never recommend that.

Just like there are ways to give the illusion of bigger feet, darker or lighter skin or being taller than you really are, there are things you can do to create the illusion that you’re growin’ yourself a bigger dick.  But all the creams, the jelqing, the pumps, the weights the what-have-you, will only have a short-term effect if they have any effect at all.  In the end you will have spent a whole lot of money, wasted a lot of time, been consumed with a great deal of anxiety and possibly even injured yourself to wind up having what you’ve always had and not significantly more.

May I suggest that you practice accepting what genetics has determined for you in terms of cock size and everything else.  Because that will give you more time and energy to learn how to use what you have to its greatest benefit.  Luckily, our capacity to be a good, and even great, lover has nothing to do with the size of our cock.  Anyone who tries to tell you different is pullin’ your leg.

Name: Laurel
Gender: female
Age: 42
Location: San Francisco
My best friend, someone I truly love, has been really getting into S&M lately.  Some weeks ago she told me she now has a full-time slave.  She says it’s a lifestyle thing, but I still don’t get it.  The problem I have is that this isn’t a private thing between her and this guy. She parades it around and treats him like a slave 24 hours a day.  I find this really disturbing and it’s like she does this just to annoy me.  My husband and I are complete equals in every way.  I can’t get comfortable watching my friend humiliate and degrade someone like this.  My friend says I should just quit being so uptight.  Is this really just a question of me being closed-minded?  Or is there something radically wrong with someone wanting to humiliate and degrade someone else?

How did your best friend’s lifestyle choices, whatever they might be, suddenly become all about you?  If you really cared for this person as much as you say you do, or better yet, as much as you care for yourself and your delicate sensitivities you’d try to look beyond your superficial appreciation of what’s going on with your friend and her slave.

fem-domYou say your problem with your friend is that she doesn’t keep her perversion private; rather she and her man slave “parade around” 24hr a day.  What, you’d prefer she be a dilettante kinkster? Hell I give her credit for taking this thing seriously.  So many others compartmentalize their lives — this is me for my family and friends — this is me for playmates — and this over here is my secret me.

As to your friend, I doubt that she gives a flying fuck if her public antics annoy you.  In fact, that may very well be why she does it.  Let’s try and look at this as dispassionately as possible.  Your friend, by being so public with her kink, has entered the realm of political and sexual theater.  That is not in any way meant to diminish her commitment to her lifestyle.  On the contrary, only someone who is totally into this would have the fortitude to constantly poke a finger in the eye of polite society.  She has a message for you and us. And I suspect that it has something to do with the unfortunate sex-role stereotyping and stultifying gender conventions that plague our buttoned down society.  But best you get that directly from the horse’s mouth, so to speak.

I have no way of knowing why your friend does what she does, but she belongs to a very long and venerable tradition of flying in the face of the popular culture.  Sure she risks being cut off by you and ostracized by others.  And that has to hurt on some level even for those way out on the fringe.  Like all political theatrics she draws you into her world, albeit as an unwilling participant. Humiliating her slave in front of squeamish folks, like you, who don’t share her kink is asking for more than tolerance that’s for sure.  One could make the case that her behavior is foolhardy and counterproductive.  What’s for certain is she’s walking a fine line between performance art and alienation.  In the end, Laurel, you may find that it is you who will need to set the boundaries.slave

And I don’t think this is simply a question of you being too up tight.  But I fear that you are using a conventional mindset to try and decipher these very interesting goings on.  That’s simply not gonna work.  Like I said earlier, she’s being this public about what most people, including yourself, think should be private because she wants to make a statement.  I suspect your conventional mindset doesn’t know what to make of consensual power-play, which is precisely what this is.

You point out that you would never humiliate your husband like this.  No kidding?  Of course you and hubby aren’t engaged in consensual power-play, are you?  Because if you were, you’d understand your friend a whole lot better, even if you still disapproved of her public performances.

If you find your friend’s lifestyle so disturbing, you could simply ask her to chill the scene when you’re around.  She may or may not comply.  Another solution might be that you ask her for some alone time, just she and you, without her slave.  Hell, even a slave get a day off from time to time.  Again she may or may not comply.  If no arrangement can be made, then perhaps it’s time to part ways.  Hopefully you guys could do that with as little acrimony as possible.  There’s no need to burn bridges over this.  Who knows this might be a phase she’s going through…ya know trying to show everyone how edgy she is.  In time she might very well find that the fringe is not all that comfortable and decide to keep her kink more to herself.

Name: Jack
Gender:
Age: 52
Location: Milwaukee
I’ve been dating this guy for over a year.  He is the love of my life.  I love him so much, but he treats me like shit.  I met him on vacation in Florida.  He’s 26 a stunning, 6’3” 200lbs, blond surfer Adonis.  And excuse me for being so graphic; he has the biggest dick I’d ever seen.  The first time we had sex I saw stars.  He filled me up like no other person has.
When I got home we exchanged emails nearly every day and even had some hot phone sex a couple of times.  He was down on his luck, because he lost his barista job for coming to work stoned too many times.  I know I shouldn’t have, but I invited him to come live with me.  I flew him up, but I told him that this wouldn’t be a free ride, he’d have to stop smoking so much dope and get a job and he agreed.
The sex was fantastic for the first couple of months, but once he established himself as a star at the gym he found his own friends and now I don’t see too much of him.  He eats my food and drinks my liquor and drives my car.  I pay for his cloths and gym membership.  He has yet to find a job.
I know I should just end it, but I love him and I would really miss the sex.  My friends ridicule me for thinking he loves me as much as I love him.  They tell me they know he sees other guys.  I’m so turned around I don’t know what to do.

Like my momma always used to say:  if it’s got wheels or a dick, you know you’re gonna have problems with it.  And I would add, if it’s got big wheels or a big dick you know you’re gonna have BIG problems with it.

Before we turn our attention to your no good boyfriend, let me make a few quick hot guyobservations about you.  You’re a freakin’ mess, girlfriend! I mean really, you’ve broken all the cardinal rules about dating a hustler.  I know, I can hear you now…oh no dr dick, he’s not a hustler; he’s a good kid who’s just down on his luck and I’m just trying to help.  Bullshit!

Ya see, that’s the first cardinal rule of dating a hustler is never lose sight of the fact that he’s a hustler and you’re his john.  Don’t get me wrong; I have the deepest admiration for hustlers and their johns.  It’s just that this arrangement only works if everyone is clear about the ground rules.   And here are the ground rules — rich older gentleman connects with needy younger hunky stud for mutual benefit.  Rich older gentleman keeps needy younger hunky stud in room and board, booze, cloths, car, gym membership and the like; and needy younger hunky stud buggers rich older gentleman senseless with his big blond surfer-boy dick.  Get it?  Got it?  Good!

Second cardinal rule — what happens on vacation should stay on vacation.  Vacation sex, as wonderful and delicious as it may be, does not transplant very well to your non-vacation life.  You’re more likely to have success transplanting a delicate tropical orchid to your Milwaukee backyard than transplanting a vacation hustler fuck to your work-a-day world back home.

Third cardinal rule —don’t try to gloss a perfectly fine, fully functional and even an affectionate hustler/john relationship with talk of love.  It’s unnecessary, unseemly and untrue.  It’s lust, it’s limerence, it’s love sickness, whatever…it’s just not love.  Because LOVE don’t ever make you feel as bad as you’re feelin’.  Probably your friends would have less difficulty with your mooning over this guy if you were more honest about the nature of this relationship.  They wouldn’t be rubbing your face in the evidence that surfer-boy is pluggin’ other dudes.

Fourth cardinal rule — a size queen, like you Jack, should admit that you are enamored with the guy hose and how it fills you up plain and simple.  To pretend that you would string yourself out like this for a guy with tiny meat is just that — pretense.  Listen, there’s nothin’ wrong with bein’ a size queen, it’s the dishonesty I object to.

How is this young fella ever supposed to respect you when you don’t respect for yourself?  He probably had you pegged (no pun intended) back on the beach in the sunshine state. He knows you will tolerate his misbehavior, which of course gives him permission to do whatever he feels like doing whenever he feel like doing it.  And now he don’t even have to give up the occasional mercy fuck any more, even though that was surely part of the deal at the get go, right?

So the waif has yet to find a job after a year, huh?  Why is that not surprising?  But even a hustler needs his mad money, besides what is doled out to him by his long-suffering john.  I’d be willing to guess Mr. surfer dude is turning tricks to keep himself in weed and other essentials.

hot_guy2Thing is, this fellow probably would have treated you better if you would have just stuck to the hustler/john script.  Ya see, kids like this need structure.  He may have looked to you for this at one time, but when he realized that he had you cock-whipped, the teachable moment evaporated.  This lad is probably like most other boys with big dicks.  They learn early on that their cock gives them enormous power, because it is the object of desire for so many.  He soon discovered that you were no different than all the other men (and some women) in his life — only interested in owning a piece of his sizeable endowment.  And so he turned the tables on you.  You can hardly fault the guy.  You try to manipulate him with your money.  He outwits you and manipulates you with his dick.

If you’re really serious about reining in the little monkey, you’d better come up with a clear, unambiguous message about what you will and will not tolerate.  And it better be something more than “I expect you to bone my scrawny middle-aged ass on occasion.” Because, until you do, he will roam wherever and whenever he wants.

There are many root causes for his behavior, just like there are many root causes for your behavior.  But since I’m talking to you, not him, I suggest that you get to the bottom of all of this by investing a good deal of time and energy with a competent sex-positive therapist. There’s one thing I can say for certain, if the status quo continues your resentment will boil over one day and there will be violence, the kind of violence that you may not think yourself capable of now.  But violence there will be; you can bank on it!

Is there enough goodwill between the two of you to resolve this unfortunate situation amicably?  Who knows!  If I had to guess, I’d say there was a slim to no chance for that.  If that’s the case, I advise you pack him up and put him on the next plane south.  And no more relationships for you, particularly with unemployed young men with massive schlongs, till you get your head screwed on tighter.

Good Luck Ya’ll

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