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Ace In The Hole

Name: Kevin
Gender: Male
Age: 22
Location: Toronto
I’m just out of college and have a ton of bills and no real job prospects at the moment. A friend suggested I do some escorting to make ends meet. Guys tell me that I’m hot and I like sex, but I don’t know if I could pull it off. Suggestions?

You betcha I have suggestions…a lot of ‘em, don’t ‘cha know.

Being hot and liking sex are great assets if you decide to turn pro, but you’ll need way more than that. Being a sex worker is not like having sex for love or even having recreational sex. You will be exchanging sex for money and that makes it a business proposition. Therefore you’d be wise to approach this with as much forethought as you would any other career move. It is, after all, the world’s oldest profession.

abs.jpgIf you do decide to set up shop, so to speak, you’ll need the capacity to have sex with a much wider range of people than if you were looking for a date. And probably just as important, when there’s an exchange of money, the john becomes your customer. And you know what they say about the customer always being right. The truth of the matter is that all pro sex is client directed. It’s not about you even when it looks like it’s all about you.

So let’s say you’re a really great fuck, fun to be with too. You’ll also need the emotional distance and psychological resilience to cope with the intimacy issues this line of work creates. This is precisely the point where most fledgling sex workers flounder. They either give too much or not enough. Some actually resent their clients for renting them. I know, this is totally absurd, but it happens all the time. This lack of clarity will cause you to have trouble establishing healthy boundaries between you and your john.

Regardless if you are a cheap street hustler turning tricks to support a drug habit or an expensive rent-boy who is servicing the rich and famous, the pitfalls are the same. A lot of sex workers are self-destructive or have huge unresolved sex issues that they try to compensate for by making people pay them for what they usually give away.

If you still think this is a line of work for you, Kevin, be aware that your mind and body are your greatest business assets. Take care of them. Nurture them. Keep them clean, fit and toned. Hygiene, both physical and mental, is a must. Body awareness, not the narcissistic type, and safe-sex practices are your frontline defense against STIs (sexually transmitted infections). Make it your business to be tested for HIV and the other common STIs on a regular (every 3-6 months) basis.

Stay clean and sober while on the job. More sex workers get busted for drugs rather than hustling. Know how to handle a drugged out client. You’ll probably see a lot of those. Know that they can take forever to get off, and can sometimes be paranoid and dangerous.

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Speaking of getting busted; you know this line of work is against the law, don’t you. That of course doesn’t stop lots of people from plying their trade. But the successful ones will have their wits about them, particularly in terms of how they market themselves. Never suggest, in any forum — written or spoken, that you are offering sexual favors for money.

Be fiscally responsibility. Plan for the lean times…and there are always lean times. You’ll probably be a hot property at first; ya know the whole “new meat” phenomenon. Don’t let this go to your head. Count on there being cuter, younger, hotter competitors getting off the bus tomorrow. Try to cultivate a number of regular clients. Have a thought to how and where you will market yourself. And I fully encourage you not to do this full-time, at least not at first. If you find it difficult to meet your financial goals, you’ll be tempted to do more and more risky things just to make ends meet.

Sex work is often more about being psychologically present than a sexual performance. Your clients will often be more lonely and isolated then they are horny. Treat them with respect. Improve your mind. Make yourself interesting. Stay abreast on current affairs and the popular culture. Develop other skills like massage and bodywork.

You should have at least one trusted friend who knows your whereabouts at all times, or who has access to your appointment book. Protect yourself: use a pager or cell phone and never make a date with anyone who won’t share his/her phone number with you. Always make a call back before you head out. Keep an appointment book, in code if you must.

Carry a travel bag or backpack with you to all your “dates”. This should contain the basics: condoms, lube, massage oil, handi-wipes, toys, etc. But you should also have an extra shirt and mace (or other protective equipment). Keep all your belongings — clothing, phone, watch, and wallet — together and near your bag. Know where that bag is at all times and be ready to pick up and leave if there’s trouble.

I also suggest that you connect with other sex workers in your area. There is strength in numbers. Other rent-boys will provide you with essential information about troublesome clients and help you get the lay of the land, so to speak.

Finally, here’s a few of great resource for all sex workers — The Sex Workers Outreach Project, BAYSWAN, AIM and St James Infirmary.

Name: Clare
Gender: Female
Age: 40
Location: St Louis
My best friend can’t bring herself to sever her ties with her ex-boyfriend. Even though their last attempted reunion ended in a very violent fight. My friend has this weird nostalgia for the relationship she had with her ex at the beginning. Back then, before he started drinking and drugging, they did have a couple of good years, but that was a long time ago. I’m very concerned for my friend. She’s often depressed and she is pulling away from her friends. I think she is seriously considering getting back with her no-good, two-timing ex. I know that my role as a friend is to love and support her, but her ex is not to be trusted. I fear as much for her safety as for her heart. What’s a friend to do?

So many things are going on here, Clare. It’s hard to know where to begin. Your friend can’t sever her ties with her ex because she doesn’t want to. Even if she wanted to end it once and for all, it’s not an easy thing to do.

Anyone who has been there will tell ya that quitin’ a bad relationship is as difficult as quitin’ booze or dope…maybe even harder. Most folks in poisonous relationships can’t extricate themselves because they are part of the toxicity. Bad relationships, like the good ones, are completely dependent on the participation of both individuals in the couple. Each one feeds off the other and each one’s bad behaviors rewards and facilitates the pathologies of the other.

domistic_violence02.jpgThere is no such thing as a good, psychologically healthy person in a bad relationship. There may be one in the couple that is less culpable, or less abusive, or less self-destructive, but there is never one that is without blame.

Like all junkies, your friend is hooked. Her depression and withdrawal are outward signs of the pathology. Nothing is gonna change this for her until she acknowledges that she is caught in a downward spiral. Domestic violence — and we ought to label the nature of your friend’s relationship for what it is — will escalate. It always does. Will your friend get out in time? There’s no guarantee. Is there anything you can do? Well that, Clare, is a more difficult question to answer. If you do too much you are at risk of supporting her habit. Or worse, you could be co-opted into the pathological dynamic of the relationship.

The best you can do is to tell your friend how you feel about her predicament. Speak your mind in no uncertain terms. If you decide to confront your friend with an intervention, I suggest that you have some well-considered resources to hand her while you are doing so. For example, you could do some legwork and find a some local domestic violence resources — a hot line, a shelter, counseling referrals and the like. Once you make this intervention and it’s over; drop it. Drop it for good. This is the hardest thing a friend has to do, but constantly badgering someone in your friend’s condition is counterproductive. If you can’t stand to witness the self-destruction, take your leave of the friendship and hope for the best.

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However you play this, don’t hold your breath for a happy ending. They happen sometime, of course, but real life is so not like the movies.

Name: Dena
Gender: Female
Age: 32
Location: NYC
I love my cunt. In fact you could say I have a cunt fetish. I love to stuff my cunt with really big toys. My current BF introduced me to fist fucking and I love it. I guess what I want to know is can this be dangerous?

I love it, a chick who refers to her pussy as a cunt! You go, girl!

But what’s this…you’re just now gettin’ around to askin’ if fisting is dangerous? Not before, but after you’ve had a fist in your cunt? Well, so much for being proactive. I’d be willing to guess that you probably already have some data on the advisability of this form of extreme sex play. You clearly have enough information to declare that you LOVE IT.

hanball2.jpgOk, for everyone in my audience who hasn’t heard of fisting (both those with a cunt and those who are cunt-less), let’s start at the beginning. I trust you know what fingering is, right? Whether it’s fingerin’ a pussy or an asshole, it’s loads of fun to diddle someone’s innards. We already know that fingerin’ a dude’s hole will stimulate his prostate, which even non-gay men are finding to be way fun. And fingering a pussy will stimulate a woman’s G-spot. Ok sex fans; take that fingerin’ concept and multiply that by 5. That’s right, fisting is inserting a whole hand/fist into cunt or asshole.

For all you folks who haven’t fainted away, yes, it is anatomically possible, and yes, it CAN be EXTREMELY pleasurable. I hasten to add that gettin’ a whole fist inside a pussy is somewhat easier than gettin’ a fist in an asshole. But for folks like you, Dena, those who are into massive penetration, nothing is a bigger turn-on. Fisting aficionados say that handballing is the most intimate and complete way to touch another human being. This kind of extreme penetration has to be worked up to slowly and gently.

To your question if this practice is harmful…well not if ya do it right. First off, the fisting top does NOT make a fist and ram it home. Trust and communication between partners is as essential as is tons of lube. Some folks swear by Crisco, others the legendary J-Lube — a handy-dandy concentrate for veterinarian use. They believe this product stand apart from the rest because it’s more slippery and gooey. You can find J-Lube in Dr Dick’s Stockroom. See the My Stockroom tab right there at the top of this page. How freakin’ convenient is that?

The fisting top must, of course, respect his/her partner’s limits and pain threshold. Safe fisting is happy fisting. And to that end, keep the following concerns in mind.handball1.jpg

First of all, the fisting top must cut and file all his/her nails until every finger is as smooth as it could possibly be. Your fingers will be in some very delicate places — places that may not have pain receptors. You’ll want to insure that you minimize all chance of causing injury.

Make sure your partner is relaxed, comfortable and turned on. When a woman is aroused, her pussy lubricates, relaxes, expands and lengthens; all of which are very important for accommodating a fist, don’t ‘cha know.

Even the wettest cunt in the world will need lots and lots of lube during fisting. There’s no such thing as too much lube, so prepare for a big fat mess. Lube your hand, the back of your hand, between your fingers. Keep applying lube as you go. Push the lube into the pussy (or asshole) with your fingers. Remember if you’re using latex gloves, oil-based lubes will dissolve latex.

Start with one or two fingers and work your way up to three and then four. Most people need some time to further relax their muscles, and some may require several stretching sessions, over weeks or even months, before they can actually accommodate a whole hand.

Tops, be sensitive to your bottom’s feelings. You are trying to finesse part of her body to open and to admit part of your body deeply inside her. If you take your time, the energy exchange between you and she will move you both into an altered state. Communication and relaxation is key.

handball_self.jpgOnce you’ve reached a five-finger insertion, you’re almost there. But it’s at this precise point that the handballing top needs to be the most attentive. Your partner’s pussy is being stretched to its near limit. Your partner is going to be riding a wave of pain/pleasure. If you find her cunt has reached its limit for the time being, respect that and pull out slowly. But if your partner wants more, then slip your knuckles inside. Be sure to fold your thumb under your fingers, so that your hand will form a duckbill wedge shape. This will allow you to gradually stretch your partner open as you press on. Apply steady but slow pressure.

Your partner should tell you when to push and when to back off. Careless fisting can cause muscle and tissue injuries. If the top goes too fast or too hard there’s gonna be more than discomfort, there will sure enough be injury. Listen to the owner of the pussy; she will let you know the difference between hurts so good and hurts really bad.

Your knuckles are the widest part of the hand and the most difficult part to get past the opening of the cunt. If there’s gonna be resistance to the insertion of the fist, it’ll probably be at this point. Wait until your partner is ready before making the big push. She may be able to help by bearing down (like if she were birthin’ a baby, or taking a big dump). Once your knuckles slip past the ring of muscles around the vaginal entrance, the pressure will ease off. Now you can gently roll your duckbill shaped hand into a fist.

At this point, the owner of the pussy or asshole may want a gentle pumping movement with your hand. Fisting can produce extremely intense sensations; so ask her what feels good to her.

When the session is done, make your hand into the duckbill wedge shape once again, and gently slide it out slowly.

Good luck ya’ll

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How To Get A Chick’s Phone Number

ASK THE EXPERTS!

ATTENTION SHOPPERS!

So many people are writing in for information about sex toys — What are they? Where can I get ‘em? How do I work one of these? Can you suggest a good one? Do these things really work? — that I’ve decided to inaugurate a new feature here on Dr Dick Sex Advice SEX TOY AWARENESS. Just like another popular feature — The Sexual Enhancement Tutorials — the STA will be chock-full of swell information while being downright entertaining.

Here’s what I’m gonna do. Thanks to Dr Dick’s Stockroom I have the wherewithal to SHOW & TELL you everything you need to know to make an intelligent decision about buying a quality sex toy. And you can shop at Dr Dick’s Stockroom with confidence. We carry the best quality and widest variety of sex toys for adventurous men and women. The service is prompt, convenient and responsive. We never share information about our customers with anyone, and all orders are shipped in discrete packaging. What more could one ask?

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So, sex fans, I hope you will find my SEX TOY AWARENESS postings helpful (and entertaining) and that you will enjoy shopping at my store.

Name: Tadd
Gender: Male
Age: 31
Location: Arizona
In one of your podcasts you told some guy about a strap on kit he could buy for his GF. Could you repeat that? I’ve been trying to find one.

I think you are referring to my 04/09/07 podcast. I responded to Karol from Poland inquiry about a strap-on kit. I said: “As to your question about a strap-on and what a guy should know about buying one for his female partner. That’s another really goodb664.jpg question. I suspect the overriding concern for the amateur butt pirate is to get his gal a comfortable harness that can accommodate a couple different sized dildos. May I turn you attention to the Dr dick’s Stockroom banner on the left hand side of www.drdicksexadvice.com. Click through there and search for the Bend Over Beginner Harness Kit (B664). The good people at JT’s have painstakingly put together everything you need for your first pegging!”

  • Is there someone in your life who is curious about strapping it on, but doesn’t know quite where to begin? Well, we have the perfect starter kit! Everything a beginning sensuous player would need to strap it on is included in this package (except their favorite water-soluble lubricant – sold separately).
  • This strap-on harness is low-riding with a fuzzy, deep purple velvet front and highly adjustable nylon straps. The kit has 2 color coordinated, shimmery purple dildos. These hypoallergenic silicone dildos are shaped and sized appropriately for those just beginning anal play adventures. The smaller is approximately 4″ long and 3⁄4″ wide, while the larger one is 5″ long and 11⁄4″ wide.
  • A powerful variable-speed mini-vibe sits in a secret pocket behind the dildo to give the wearer an extra jolt of fun. The straps are adjustable, fitting up to 50″ hips. The 11⁄2″ O-ring can be exchanged for play with other sized dildos (sold separately). Washable, smart, and sexy. Bottom line – this is one hot strap-on package!

Good luck

Name: Jordan
Age: 19
Location: Michigan
What is a cockring and how does it work?

Holy cow, Jordan, where to begin. Every man should know about cockrings. Cockrings, in one form or another, have been around for as long as there have been cocks…and that’s a pretty long time, don’t ‘cha know! They are low-tech, but extremely effective means of getting it up and keeping it hard.

Cock rings can create larger, harder erections. Since blood flow enters your dick through arteries deep inside your dick, and leaves it through the veins on the outside of your tool, wearing a cock ring can help to keep more blood inside your dick shaft. And as all you rocket scientists know blood is what causes erections in the first place. Some men claim that wearing a cock ring intensifies their orgasm.

I recommend the flexible and/or adjustable cockrings. These are generally made of

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stretchable rubber or leather. Let’s take a look as some now. First, the Neoprene Cock Ring (B642).

  • This light yet durable cock ring is made of neoprene – an oil-resistant substitute for natural rubber. Neoprene displays outstanding physical toughness and resistance to damage caused by flexing and twisting. It is an extremely versatile synthetic rubber with 70 years of proven performance in a broad industry spectrum.

Next, we have these festive little numbers, Gummy Cock Rings (B170)

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  • Fruity-colored cockrings with multiple soft knobs. When unstretched, it fits snugly around a pinky finger. When stretched, it can expand to a surprising diameter. Once removed, the ring will slowly contract to its original size. One size fits all.

For the more butch among us we have this handsome devil — Leather Cock Ring w/ Pyramid Studs (A413)

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  • This ring comes with pyramid-stud hardware for that extra-macho look. It measures 9/16″ and sports three snaps to adjust the size for a snug fit.

For the more daring there are the metal variety. They may look pretty, but they’re a bitch to put on and to take off. Here’s how ya do it.

1. Pull your ball sack through the ring first.
2. Follow this by popping each of your balls through the ring one at a time.
3. Now bend your cock down and pull it through the ring.

Let’s take a look at some of these. First, the standard Aluminum Cock Ring (A888)a888.jpg

  • This style of Cock Ring is a significant improvement over the standard steel O-ring. Since it is made of aluminum, it is very lightweight and perfectly smooth, as no connector seam is necessary.
  • Sizing hint: Measure the circumference of (the distance around) the erect penis at the place where you want the ring to go. Divide by 3.1 and you have a ballpark number for the diameter of a snug-fitting ring.

b352.jpgThen there’s “cockring as fashion statement” — Teardrop Cock Rings (B352)

  • The Teardrop Cock Ring is worn around the cock and balls, but what makes this cock ring different is that it gently massages the perineum (the spot between the balls and anus) and other erogenous zones. It is made out of anodized aluminum, which is lighter and smoother than its chrome-plated counterparts, and preferable for people who have nickel allergies.

It’s absolutely essential that you not wear this kind of ring for longer than a couple hours. Make sure you don’t buy one that is too small either. If your dick is turning an angry red or worse, purple, or it is cold to the touch, you’re in trouble. Take that ring off immediately. If you don’t you will risk serious injury to your precious dick.

Good luck.

Name: Betty
Age: 22
Location: Fremont CA
I think my roommate is a lesbian. She hasn’t come right out and said so and I don’t know how to ask. Her birthday is coming up and I thought I would get her a sexy toy or something to let her know that it’s ok to talk to me about sex and stuff. Do you think I should get her a dildo? What kind of dildos do lesbians like?

Jeez Betty, how the fuck should I know what lesbians like? I’m pretty well versed on most things sexual, but even I am at a loss when it comes to the mind of a lesbian. I just put in a call to my favorite lesbiaterian, the magnificent Diana, for the 411 on toys for dykes and dyke wannabees.

b367.jpgIf you don’t want to be too provocative in your gift giving, Diana suggests you start out with a — I Rub My Duckie Vibe (B367)

  • These floating, waterproof little guys sit by your bath, jacuzzi, or bed with nothing more than those big innocent blue eyes to give away their real purpose in life!
  • Squeeze their backs and watch your smile grow as they seduce you and massage your tensions away. Waterproof On-Off Switch. Strong but quiet motor. Requires two AA batteries (included).

If you really want to pitch your friend an unambiguous message, Diana suggests a — b193.jpg

Vibratex Rabbit Habit (B193)

  • This vibrator does everything! It has three functions. The shaft gyrates and is bendable with a wire inside to keep its angle. Mid-way down, there’s a capsule of pea-sized pearls that rotate around the shaft for an undulating/ripple effect. And the bunny vibrates for clitoral stimulation.

If this doesn’t do the trick, Betty, nothing will.

Good luck

Name: Gary
Age: 58
Location: Tampa
I’m a widower; my wife of 29 years died a little over a year ago. I’m just now getting back into the swing of thing. The sex I had with my wife was very conventional now I want to try something different. I want to go to a dominatrix. I’ve always had a fantasy about a woman owning and punishing my privates. It’s a big turn on. Is there anything I should know about this?

I love it; another kinkster in the making. Coming out as a perv is better done late than b702.jpgnever, in my opinion. My first suggestion is that you find a better term for your privates than “privates”. You sound like your mommy. I suggest cock and balls, it pretty much says it all very succinctly.

Have you done your homework in terms of finding the right dominatrix? I suppose you have at least a couple in mind, right? Might I suggest that when you make contact with one or another of these professional women that you be very specific about what you want and how you want it.

Here’s a tip…a good submissive, or sub — that’s you, Gary, will want to bring his dominatrix, or dom a little gift to start things off on the right foot. May I suggest this little number: A Male Chastity Kit (B702).

  • It represents the latest design in modern male chastity. The natural flow of lines in this model represents the penis and conforms to the body. The slim, smooth lines permit this device to be worn easily under clothing. It is slightly vented with curving lines and custom openings for comfort and hygiene. The material, a highly durable transparent polycarbonate, is functional and appealing, and its strength exceeds that of acrylic and many other plastic blends.

Good luck

A Rose By Any Other Name

We’re all back from spring break. The Dr Dick Review Crew is all rested and relaxed. Sadly, I can’t say the same thing about me. oh well, no rest for the wicked.

Doc:

I enjoy your podcast, the frankness and open vocabulary is exactly what I like. No need in beating around the bush, just get to the point. Wish more people would live by that philosophy.

Ok. I am a 45 YO, gay male, very experienced sexually, some say whore… LOL! I enjoy a lot of fetishes; the unusual has always been very attractive to me. The more bizarre the more I will probably like it.

Until I was about 40 I was a DOM top. I started experimenting with the group party world and enjoyed it greatly. Became an experienced fisting top with some formal training, I guess you could call it an apprentice who graduated, or so I thought. Then a few of the FF bottoms suggested I was missing something. Because I didn’t have any experience as a FF bottom I couldn’t realize the true feelings and emotions involved with fisting. I was encouraged to experience fisting as a bottom.

This was a HUGE ordeal for me. The mental change alone was like, wow. The first time I crawled into a sling and had my whole ass on display, legs spread like a woman at her gynecologist…man was I uncomfortable. This was 5 years ago. Now I can hop into a sling and take a fist-fuck fairly easy. I now understand the advice given to me: I finally understand what fisting is all about.

Now my issues.

I have changed. My whole personality has been altered. Changing from a Dominate Top to fisting bottom has created issues with my head and overall sexuality. These changes are now affecting my sex life. I guess I need some help figuring things out.

Thanks,
Jimmy

Thank you, Jimmy, for your message and your kind words about my podcasts.

We really get boxed in with all our self-identification we do, huh? I mean I know why we categorize ourselves and others as gay or straight, top or bottom, sub or Dom. It helps us understand ourselves and communicate in a kind of shorthand with others. But there is a downside to this, as you suggest.sex sling

I believe that human sexual response is a whole lot more fluid than we give it credit for. But this fluidity is often stifled when we overly compartmentalize ourselves or others. Not to mention the fallacy of the binary system — being one thing or the other.  It just ain’t so and you are the perfect case in point.

I’m always talking about how the best tops are those who, on occasion, bottom. The best submissives are those who, on occasion, dominate. Besides the wider range of experience this provides us, we also grow in emotional maturity encompassing both our yin and yang.

Also the words we use to describe ourselves have, over time, become heavily laden with unintended cultural connotations. Top/bottom, sub/Dom are classic examples of this. That’s why I believe that we ought, from time to time, reinvent the language we use to talk about ourselves. In this case, I prefer terms like: giver/receiver over top/bottom. A change in vocabulary can certainly cut through a lot of the cultural nonsense and it can open the door to a more fluid sexual expression; as I believe it ought to be.nekkidbookclub

I hasten to add that at lot of hard-core pervs disagree with me on this. And that’s perfectly fine with me. It’s just that, if our language detracts from our experience, or hems us in, rather than facilitates it, and frees us up, something’s out of whack.

You will pardon the shameless self-promotion, but I’d like to call your attention to my latest book, The Gospel of Kink. It’s a communication and relationship building workshop in workbook form. It centers on the skills us kinksters need to communicate with others, and initiate, build, and maintain the relationships that will serve us well. Learn how to ask for what you want and get what you ask for from the people best situated to fulfill your desires. The book covers a lot of the territory that you raise in your question.

Stay in touch and let me know how this sits with you.

Good luck

Spring Break, Bitches!

We’ll all be on Spring Break till Monday 04/14/14.

 

…of course my break won’t begin till after my Backdoor Basics Workshop on Thursday, 04/03/14.  I hope you join me for tons of fun and loads of adult products to giveaway.

 

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