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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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…Because I Said So!

Once again, I have the pleasure of introducing all you perverts and pervettes to some very appealing playthings. Thanks to my inquisitive correspondents and the treasure trove that is Dr Dick’s Stockroom, I’m able to bring you another installment of my ever so popular, SEX TOY AWARENESS feature.

Name: Oliver
Gender: male
Age: 32
Location: Atlanta
I want to try a butt plug or at least I think I do. I have a friend who swears by his. The other day he took me to the store to pick up some groceries. All the while he was acting all weird and giggly and stuff. I knew something was up, because the Safeway is just not that festive. He told me later that he was wearing his butt plug while we were shopping. Are these things really that much fun?

Well ya know fun is in the eye (or in this case…the bum) of the beholder. I know a couple of guys (and even one gal) who wear their plugs for hours on end. A plug of modest size can offer loads of stimulation for an extended period of time. And, like your friend, only the wearer will know the source of his/her shit eatin’ grin. My one female friend says she wears hers when she irons. She told me that ironing used to be a chore she dreaded. Now the drudgery has turned to delight, thanks to her prodigious plug. She also reminds me to tell you that plugs are not only for assholes. She has another set of plugs just for her pussy. What a creative lass!

c933.jpgOliver, let me introduce you to your new best friend for life — the Tulip Anal Plug (C933). This gracefully designed butt plug features a rounded tip for effortless penetration. The yielding tulip shape fans out to a wide, 11⁄2 maximum diameter, then slims to a narrow column, making for an effective fit. This toy is meticulously manufactured by hand in the USA using the finest materials available. And that’s really important considering where you’re gonna shove this puppy.

The Tulip Anal Plug is made from 100% Ultra-Premium Platinum Silicone (read: first class stuff). Hypoallergenic, phthalate free, perfectly odorless, this toy is great for people with sensitive skin or for those who want a more environmentally friendly play option. This plug is boilable, bleachable and dishwasher safe. Isn’t it a comfort to know that this nontoxic, waterproof playmate can be so easily sterilized? And last but not least, the wide base provides improved manipulation and a helpful safeguard too.

Name: Patti
Gender: female
Age: 38
Location: Washington DC
My best friends are getting married. They’re going to Canada to get hitched, because my friends are lesbians, and…well you know how we are here in the states about that. Anyhow, I’m looking for an unusual bridal gift…for two brides!

Yeah, I do know how we are here in the states! Maybe Canada will annex us one day.

c212.jpgWhat lesbian bride wouldn’t want one of these delightful toys? The Njoy Fun Wand (C212) is more than a sex toy. It has as many applications as a Swiss Army knife. (And you know how them lesbians love their Swiss Army knives! They never leave home without it.)

The lucky brides will be able to insert one end for amazing g-spot orgasms, or use the beaded end for anal ecstasy. Your friends will be able to practice their Kegel exercises with this thing too. In no time they will have vaginal muscles of steel. And when the dreaded lesbian bed death occurs, as you know it will, the Njoy Fun Wand can be used to apply pressure to knots in their back and shoulder muscles.

Since it is handcrafted from the highest-grade stainless steel, the Njoy Fun Wand will last a lifetime. It’s the gift that keeps on giving. It’s easy to clean with mild soap and water. Measures approximately 8″ in length, with the widest section measuring 1″ in diameter.

It has a hefty weight to it, and it will hold temperature — warm or cold — just in case your friends have a little kink to them.

j420.jpgName: Ward Clever
Gender: male
Age: 40
Location: Suburban, USA
My wife, June, has been passing around the beaver, if you know what I mean. This has got to stop. That beaver belongs to me. What do you suggest I do to teach her a lesson?

Dear Ward, I know how trying it can be when the little woman wanders. What’s a husband to do? I think it’s time to trap Beaver Cleaver, if you know what I mean. And I think you do. Here’s what you’ll need to get the job done. Deluxe Female Chastity Belt, Pink Leather (J420), a top quality piece of pink leather BDSM fetish gear. So feminine, yet so sturdy!

This deluxe locking chastity belt has a waist belt, and a second belt going between the legs flaring out in an hourglass shape around the crotch area, giving more coverage in front and in back, while narrowing between the legs to conform to pelvic anatomy. Ward, my friend, not only will this little number trap June’s beaver, it will keep her bunghole from wandering too!

This leather harness is a full-fledged chastity belt. Both belts are adjustable and lockable. The whole belt requires four locks (not included). Remember, beavers are wily creatures; so security is a must if you want to get the job done right.

Name: Cameron
Gender: male
Age: 24
Location: Winnipeg
Doc, I’m fed up spending so much money on disposable douches. Is there anything out there that is safe and reusable?

b004.jpgYou’re in luck, darlin’! The Shur Shot (B004) is a douche/enema nozzle that is outfitted for use as a shower attachment.

The nozzle is 6″ (15cm) long. It’s attached to a metal hose almost 6 feet (1.7 meters) long. On the other end of the hose is a valve, which you screw on to your shower spigot. Then both your showerhead and the 6-foot hose attach to the valve. In one position, the valve will direct the water flow to the Shur Shot, and in the other position the water goes to your showerhead. Isn’t that brilliant engineering?

Here’s a tip, when you buy a product like this, be sure you buy quality. I do not recommend the cheaper plastic models you sometimes see around. If you buy the Shur Shot you can be confident that blasted thing will last. You will also have the proper length of hose, which is like totally important for reaching those hard to get at spots.

Name: Bette
Gender: female
Age: 45
Location: Redding, CA
One of the medications I take every day has a very unfortunate side effect. It causes acute vaginal dryness and that, as you know, can make intercourse painful. I’ve tried several lubes, but they only seem to help on the surface and I need deeper lubrication. Is there anything you can suggest?

c123.jpgYou betcha! I have just the thing for you. Holy cow, check out the Lube Shooter (C123). This package comes with 3 disposable lube shooters that put lube where you want it, deep in your pussy! No more wasted lube! No more messy sheets. Just a comfortable fuck!

Simply remove the plunger, pour the lube into the shooter. Replace the plunger and depress until the lube begins to ooze. Insert the lube shooter into your pussy and slowly depress the lever. How fun is that? This handy device is perfect for lubing up one’s ass for some deep slippery butt fuckin’ too. But probably you perverts figured that out already, huh?

Good luck Ya’ll

Liberating The B.O.B. Within

So ya finally decided to become a B.O.B. (Big Old Bottom)? Tired of missing out on all that ass-play everyone’s talkin’ about? Been secretly trippin’ on the exploits of your favorite porn stars? (“Jeez, would ya get a load of that. His hole looks like the Victory Arch in Paris, for god sake.”) And now want a piece of the action for yourself? But wait, there’s a wrinkle, you’re a virgin or worse yet, there’s been an “Exit Only” sign on yourgallerygay_20061125_085924.jpg poop chute for so long that the mere thought of someone diddlin’ your ass hole makes you blanch and swoon.

Dear Dr. Dick, Help! I want to be a bottom; at least I think I do. My boyfriend’s been begging for my booty big time, (my girlfriend just got herself a strap-on, YIKES!) but I’m just too tight down there and he’s really big (and she thinks turn-about is fair play). Our play time always end the same way, frustration for him (her) and a pain in the ass for me. How do those porno guys and gals do it?

fucking_men.jpgFirst off, darling, “porno guys,” as you so lovingly refer to them, are professionals (yeah, huh!). And Dr. Dick suggests that a novice butt pirate like you not try that fancy stuff at home before you know the basics.

So listen up, bottom wannabes, pleasurable buggering depends upon on three simple, but important things: 1) The will, 2) Being relaxed and 3) A considerate partner.

First. You gotta really want to get fucked. This may sound elementary, but it’s not. Some of my clients secretly confess that they don’t anyone near their precious tushie, and no amount of pleading and whimpering on the part of their long-suffering partner(s) is gonna change that. For some getting it up the ass is associated with11.jpg domination not pleasure. Manly men don’t bottom for nobody. (Oh sure Mary, me thinks you doth protest too much.) Others have religious reservations. (If god wanted me to get fucked he would have given me a vagina.) Still others have aesthetic concerns. (Oh no, that’s way too icky and messy.) I can assure you that these boys ain’t never gonna be a bottom no how.

Second. Let’s just say your dyin’ to get fucked, but you’re so intimidated by your top’s one-eyed monster that your quivering asshole is like totally shut down. Chill out! Why not begin your sex play with your partner giving you a relaxing sensual back rub. After awhile he could move on to a little butt play (and I do me play). The object here is pleasure not penetration. Have him tease your asshole with his finger. A tongue works nicely too. (This is called rimming, but you probably already knew that, because you’re not a complete idiot, huh?) A gentle circular motion works best. Have him use his hands to spread your ass cheeks, this will give your top better access to your rosebud and give you a double dose of pleasure. After a while, a lubricated finger can be inserted for a bit of a prostate massage, which is ohhh sooo delicious. When you’re ready to kick it up a notch, have your partner try inserting two fingers or a small dildo. Rhythmic deep breathing will help keep you relaxed. And when you’re all loosened up and ready to become like one of them “porno guys or gals,” you can him plug in the real thing. No more meat substitutes for you. Experiment with different positions. Try sittin’ down on that big old thang, or do it doggie style. Getting laid while on your side with your man comin’ at ya from behind gives you a bit more control over the depth of his thrusting. And of course, there’s also the traditional missionary position; you 12.jpgon your back, legs spread eagle and your pumps pointing to the stars.

Third. Having a big dick doesn’t automatically make a guy a good top. A considerate partner, big dong or not, will happily join you in exploring your asshole. He will concentrate on pleasing you first, because he knows that an investment in your anal pleasure today will reap a harvest of mutual pleasure tomorrow. (Coming soon! Dr. Dick’s tutorial for tops. Don’t miss it.)

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