Sex Advice With An Edge — Podcast #57 — 03/31/08

[Look for the podcast play button below.]

Hey sex fans,

I’m back with a whopper of a show for you today. We return to our usual question and answer format this week, because I have a hot load of stimulating questions from all over the freakin’ place. And I, of course, respond with an equal number of feisty, friendly and oh so enlightening responses! Hey, it’s what I do.

Wooly Jumper is all wet and can’t figure out why!
Jordan is too big for his GF! Or so he wants me to believe.
Ste and Mat’s lace curtains are malfunctioning.
Dylan seems to be edging way too much.

BE THERE, OR BE SQUARE!

Today’s Podcast is bought to you by: Dr Dick’s How To Video Library.

Podcast: Play in new window | Download

March 28, 2008June 17, 2026

Guilty Pleasures

Name: Anonymous
Gender:
Age: 22
Location: Phoenix
Dear Dr. Dick, I’m a pretty good looking guy, with a pretty average penis size, with a pretty average ego and confidence level. I am unable to make a first move. Whenever the situation rises, I become nervous as a little girl and the only thing I can think of is the awkwardness of rejection. Its really starting to throw me off balance when I cant get the physical attention I need, you know? It’s starting to make me think I’m gay also, which is totally fucking with my head. Help me out dock, what’s going on?

Well, anonymous, the fact that you couldn’t even bring yourself to include your first name on this anonymous submission form, or even think up a plausible substitute marks you as a world-class wimp. And hey, here’s a tip, stop comparing your total lack of cojones to being a girl or being gay. You are neither — a girl don’t need no balls and gay men have ‘em. You, on the other hand, need to grow yourself a pair, pal

So you’re 22, a pretty good-looking guy (or so you report) with an average sized dick (although I don’t see what that has to do with anything), and yet you still are stumped on how to connect with a chick. Holy cow, did you miss junior high?

Is there anything about you that a woman might find interesting? Are you intelligent, witty, fun to be with, a good conversationalist, sensitive, kind, a good cook, romantic…are you rich? Listen chum, you’re gonna need more to recommend you than bein’ pretty good lookin’ and a modestly sized peanut.

“I can’t get the physical attention I need…” I’m gonna go way out on a limb here and guess you mean you can’t get laid, right? Maybe you oughta work on your presentation. I mean, what self-respecting woman is gonna want to put out for someone as desperate as you.

Start by getting off the pity-pot and learn to handle rejection. Don’t take it personal, rejection is just part of being a grownup. Also, jettison the notion that women are put on this earth simply to satisfy men’s physical needs. That’s so freakin’ Neanderthal.

Put your pride aside and start connecting with women as friends, not as potential fuck meat. , Sex flows from intimacy for most women. If you take the time to get to know a woman first, without that lean and hungry sex-starved look that I just know you have, you’ll find that, unless you are a totally dorky klutz, even you may get laid sooner or later.

Name: Carol
Gender: Female
Age: 28
Location: Montreal
I like oral sex, but my new BF doesn’t know what he’s doing down there. He’s really sweet and I like him a lot. Unfortunately, he thinks he’s like this really great lover when actually he sucks…and not in a good way. I know he reads your column, he was the one that turned me on to your site, so could you give him some pointers on how to orally pleasure a woman. He doesn’t listen to me.

Instead of me, who has no pussy, pontificating on the joys of muff diving, I turned to my #1 friend of the lesbitarian persuasion, Joy. Not only does she have her very own chuff, she sure as shootin’ knows her way around other gravy boats as well. I shared your message with her and asked for her advice. I figure, if you wanna learn how to do something right, ya talk to a pro. Simply put, no one sucks cock as good as a queer; no one gobbles clam like a dyke. Enough said!

Joy’s first comment was…and I quote. “What’s this chick doin’ with a dude? If she wants good head, she should bed a dyke. Once you go lezzie, you never go back.” Ahhh, Joy is such a…joy!

Ok, so giving a chick some head is about the most perfect sexual thing you can do for a woman. It makes her feel special. What woman doesn’t groove on knowin’ her partner finds her finger-lickin’ good? And maybe that’s a real good place to start this tutorial. If you don’t like the taste or smell of pussy juice, give up on the idea that you’ll be a fabulous lover. However, if you want to give this whole muff diving thing a try, but you don’t know if you can handle your partner smell, or she’s unsure about you bein down there, because she thinks she might smell, you guys could start off by showering or bathing together.

Many women prefer oral to intercourse, because it has the potential to give her an exceptional orgasm. And for all those gals out there who need loads of direct clitoral work to get off, mouth to clit stimulation is one of the easiest, most enjoyable ways to get make that happen.

Joy says that the biggest mistake a guy can make with a pussy is divin’ in without knowing his way around. And like I always say, ladies, it is absolutely up to you to introduce your partner to your particular beaver. Remember, just because he may have been with other women, that don’t make him an expert on your parts. Get it? Got it? GOOD!

The novice cunt lapper will do well to approach this amazing piece of human anatomy very gently…at first. If the woman you’re eatin’ wants it more vigorous, she will ask for it. So relax and enjoy! If all this licking and sucking isn’t a turn on for you, it won’t be much of a pleasure for her, either. So, if you’re heart is not in it; I say don’t even bother.

Don’t make the mistake that Carol’s boyfriend makes. Listen to the feedback you’re gettin on the job you’re doin’. If you’re not gettin’ feedback, ask for it. Just don’t talk with your mouth full. Once you hit on something that works with the gal you’re with, stick with it for a while. Unless of course you’re trying to drive her wild with some tongue teasing.

Joy insists that a soft tongue and a relaxed jaw works best. And believe me, she knows of what she speaks. She always starts out licking her pal from vaginal entrance up to her clit. She follows the outer edges of her pal’s pussy along both sides —slowly at first, then more rapidly. Sometimes she’ll even throw in a little raspberries — you know, the mouth vibration you make when you force breath through lightly closed lips. Joy swears by this technique, don’t cha know! Sounds like so much fun I kinda wish I had me a cooch.

Don’t be caught with idle hands while you’re eating out-at-the-Y. Gently press her two outer vaginal lips together then run your tongue between the inner and outer labia one side at a time. Try poking your tongue into her vagina. The majority of nerve endings in a typical woman’s vagina are around the opening and within the first couple of inches inside. Target them with a darting tongue motion. Insert a hardened tongue into her hole. Try moving your tongue in and out, as well as in circles around the inside of her opening.

Spread her outer vaginal lips with your fingers. With your tongue pointed, gently flick your tongue around her clit. Feel free to roam around in there, but keep coming back to her clit, because it’s the most sensitive area…just like your dick head, you dickhead!

Some women find the direct approach too intense. If this is the case with your woman, blow a stream of warm breath over and around the clit. This lighter breathy touch might just do the trick. Again, be sure to ask for feedback and then do precisely what she says.

Once your partner is good and hot and juicy wet, Joy suggests you kick things up a notch. Spread her lips, expose her clit and give it a quick little suck. If this hits the spot, you might want to lightly pull back her clitoral hood and repeat the quick sucking motion. Joy assures me that this feels incredible, and it’s just the thing to do if you feel like tormenting your partner. Now take her exposed clit into your mouth and gently suck on it, simultaneously flicking your tongue over and around it. This, combined with fingering her vag, will usually produce an intense orgasm.

Keep your tongue and hands busy flicking and massaging, poking and prodding lapping and kneading. In other words, find out what she likes and how she likes it and let her have it just that way.

Finally, Joy suggests you surprise the little woman by having a mint or an ice chip in your mouth while you go down on her. These can create a very intense tingling sensation and will enhance your performance immeasurably.

Name: Jake
Gender: male
Age: 23
Location: Omaha
I’m 23, and I’ve been dating a 30-year-old chick for nearly a year now. I come from a very conservative Christian upbringing and I love that she is more experienced than me. My girlfriend likes to tie me up. I’m a college gymnast so I have very defined muscles. They are a huge turn on for my girlfriend, which I guess explains why she likes to see me struggle against the rope. I get real turned on too when I’m tied up. Sometimes she teases my penis and testicles with a feather or a piece of leather, which drives me wild. I’m worried though, because I think this is gonna warp me somehow. Do you think this is perverted? Why is it so much fun?

Ahhh yeah Jake, I do think it’s perverted. I think your girlfriend is a big fat pervert and I think you’re still a little tiny pervert, but well on your way to being a big fat pervert, just like your girlfriend.

And why is this bondage thing so much fun? It’s such a blast because it’s perverted, nasty and forbidden, silly! One can only guess what your fundamentalist Christian mom and dad would think about their star athlete son trussed up like a thanksgiving turkey while a considerably older dominatrix punishes his family jewels. I fear this apple has fallen a great distance from the tree, right Jake? I absolutely love it!

Bondage is fun for you because you have to relinquish all your male privilege — Christian, preppy frat boy control — to this unlikely kinky lady friend of yours. And what’s even better, you let her have her way with you. I have a feeling you’re not telling us everything about what she does to you when you’re all tied up. I’d be willing to guess there is a lot more perversion here than meets the eye. Not that that’s a bad thing, necessarily. I think it can be very therapeutic as well as amazingly hot to be completely helpless and in the control of another.

For a dominatrix, like your girlfriend, there is, as you say, the visual aspect to bondage. I think she’d agree, there’s nothing sexier then young masculine, muscular male flesh wrapped in ropes while having his cock and balls available for discipline. It’s the ultimate form of objectification. And, I might add, that you guys are turning all of society’s conventions — particularly the sacred “male as top” rule — on their head. YOU GO!

This has got to turn your crank, on some base psychological level too. I would so love to know how you and your girlfriend met. How she introduced you to the perv lifestyle. And more importantly, how you came to submit so unequivocally. That’s the real story here.

Jake, you are on the cutting edge. And I think you have some sense as to how radical your play really is, don’t you? I think it’s the radical nature of your play that gives you pause, right? It’s not the actual bondage, discipline and possible humiliation that concerns you as much as you feel like you are losing your moral moorings. Nothing about what you are currently experiencing at the hand of this woman has any connection to the life you were brought up in. That has to be a bit of a jolt, which makes it all the more enticing. And there is virtually no turning back, is there? Once you’ve tasted the sweetness of surrender, vanilla will never again be enough.

Trust me, none of this makes you a bad person. On the contrary, if you embrace and integrate all this new information about yourself and live your life with authenticity and integrity, it will make you exemplary.

I do have one fear, however. I fear that one-day you will begin to second guess this harmless submissive eroticism and cave to the dictates of the popular culture. The worst case scenario would be for you to continue to enjoy your BDSM lifestyle on Saturday nights, then rush off to church on Sunday morning to join the choir of sanctimonious hypocrites who do one thing in private, but publicly endorse and promote a sex-negative message of repression and denial. That, my friend, would be criminal…and a real perversion.

Good luck ya’ll

February 29, 2008June 17, 2026

I’ll Bite…

Name: Bob
Gender:
Age: 22
Location: NJ
I have been having a ton of rough sex with my boyfriend and the last time we did it he complained that I ripped something up there and that it burns whenever I try to slide in. He also says it burns sometime when he does #2 and he finds blood also! What can we do to get him better and prevent this from happing again?

Oh Bob? Are you completely brain dead? Tell me that you and your BF have been doing so many drugs that you’ve both fried your brains to the point that neither one of you can put two and two together. Please tell me that, because that is the only explanation for either or both of you not attending to your abused BF’s butt hole before now. You simply can’t be that friggin’ ignorant! Where there’s pain and blood, there is BIG trouble. Your BF needs to see a doctor immediately. If an infection sets in, he could lose his bowls. And he’ll have to shit in a bag for the rest of his life.

Listen up, you monkeys! If you’re gonna be doin’ a lot of rough sex, especially were delicate innards are concerned, you gotta know that it’s only a matter of time till you cause some serious harm. And I know for certain that rough sex inside someone’s asshole is simply impossible unless the bottom is wigged out on some mind and body altering substance. This is absolutely and always unadvisable!

If you have some death wish, fine…proceed. But if you are serious about wanting to know how to prevent this from happening again, that’s easy too. First, quit the fuckin’ drugs…at least while you’re fuckin’ each other senseless. Second, rough sex is fine to a point. But if the rough sex involves abusing someone’s rectum or colon, then you’re goin way too far.

Name: Thomas
Gender: male
Age: 18
Location: Dublin
I just want to know how you start and ask a girl to have sex.

Well, that sure is to the point, Thomas! I suppose the answer to that query will depend on the young woman in question. Do you have a particular girl in mind? Or is this a generic “how to” question?

I’m of the mind that the direct approach works best, just so long as you’re not gonna be a dick about it. That being said, if the chick is a mate of yours and you fancy her, you’ll need to take a different approach to finessing a fuck than if you want to shag a relative stranger.

So, before I go much further with my advice on how to bag a bird, I think we’d better take a good look at you first. Is there anything about you that would make you attractive to a young lass? I mean if you’re not overly geeky and have a bit of charm about you, your task is gonna be considerably easier than if you are some uncouth Neanderthal who just wants to dip his wick in some fine pussy.

If you’re not sure what kind of guy you are, ask a woman friend for her honest feedback. If she tells you she’d bump you in a pinch — you may have something going for you. If she tells you that she’d rather let her cooch die a slow lonely death than fuck the likes of you — you definitely have your work cut out for you.

Regardless of what group you fall into — the “possibly fuckable”, or the “not fucking ever;” you can always improve your image among the ladies. Look to how you present yourself; make sure you are groomed, clean and odor-free. Dress to impress. That doesn’t mean fancy or fussy. Just make sure it looks like you gave your cloths a thought before you dressed yourself. Make yourself interesting; have a point of view. But share it sparingly. If you can’t be clever and witty, then keep your mouth shut for the most part. Women love the strong silent type. And they rarely know if the silence is stoic or stupid till it’s way too late.

And if you really want to get laid never approach any woman like she’s a piece of meat. If you think women are put on this earth simply to satisfy a man’s needs, stick to pullin’ your own pud. And here’s a tip: I always suggest that a guy squeeze one off before he goes on a date. This will take the edge off his sexual tension and his blue balls won’t be so friggin’ obvious to the lass he’s tryin’ to woo. There’s nothing more unattractive to most women than a desperate fuck. Besides, if you don’t jerk off first, you’ll have way too short a fuse and you’ll be finished before she even begins. Get it? Got it? Good!

If you’re not already friends with the chick you lookin’ to bone, take the time to become her friend. This will involve some effort. If you’re not in it for the long haul, then skip it and find yourself a pro who will get you off for a few quid.

If the woman in mind is already a friend, and she trusts you because you’ve been nice to her, you’re half way there. She’ll be more inclined to say yes to your direct request.

Keep in mind that women are different from men, especially where sex is concerned. Few women are as casual about sex as are most men. So if she says no don’t take it personally. She may just be shy, or not ready, or not sure. It’s your job to draw her out, be patient while you do so. And most of all reassure her that you have her best interest at heart.

If she is uncomfortable with you, ask her why. You may learn some very interesting things about yourself that you need to work on. Maybe she just wants you to take your time and finesse her into giving up the bump.

If she has her wits about her, she’ll be concerned about the whole pregnancy thing. This is much more serious concern for a girl then for a boy. If you’re not well versed on several methods of contraception, you’re not ready to have sex. Sexually transmitted infections ought to be a concern for you both. Don’t be a fuck-up; always use a condom.

If you’ve got a hardon, it’s not the right time to be pestering a chick for sex. Talk about having sex at another time when the need is not so urgent. If you pressure her to service your wood, you’re going about this at the wrong time and in the wrong way. If she senses that all you want is to satisfy your loathsome self, she’ll have you pegged as the asshole you are.

Remember that there are lots of different ways to have sex, so she might welcome one type while rejecting another. Maybe she’d be up for a hand job or blowjob, just no full-on fucking. Whatever the case may be, you’d be well advised to get her off a couple of times before you look to your own satisfaction. Whatever you do, respect her boundaries and let her know that you won’t pressure her to do anything she doesn’t want to do.

In the end, there no standard way to ask for sex, but if you treat the woman with respect, honesty, and patience, you can be sure that whatever words you use they’ll be more welcomed than if you’re a jerk.

Name: Sita
Gender: female
Age: 19
Location: Delhi
Hi!
I came to know u through the net. I am from India and I am 19 years old. I am married for the past one year and I have a problem. Myself and my husband had sexual relationship which meant only breaking of the hymen but whenever he tries to insert it I cry out of pain and stop him from it. I really do not know how to overcome this problem. Kindly help me please.

The two most likely reasons for this painful fucking are: 1) you’re not aroused enough before the fucking begins, or 2) you have a physical condition that might make fucking painful, even if you are aroused.

I’d be willing to bet that, in your case, Sita, the first reason is the more likely cause of your discomfort. This is often the case with young people having their first go at sex. One can hardly fault them, both women and men in our culture, as well as the women and men in yours, are not particularly informed about their own sexual response cycle, much less the sexual response cycle of their partners.

Young women new to sex, may not have time to come to full arousal before their man starts trying to shove it in. A woman, particularly one who is new to fucking, must come to full arousal before her partner attempts penetration. A man, on the other hand, needs only to have a stiff dick. And if the young men in your country are anything like the young men here in the good old US of A, they pretty much a hardon 24 hours a day. This obviously makes them ready and eager for the old in and out long before their female partners are ready and eager for the same. If your husband is guilty of this, and I’d bet my last rupee that he is, your body will resist him, even if you want to make a go of it.

I’d also be willing to bet that your culture, like ours, doesn’t value a woman’s sexuality or pleasure as much as it values a man’s sexuality and pleasure. If that’s the case, you’re gonna have to struggle against those cultural forces to gain your rightful place as an equal sex partner in your marriage.

Start by being well informed about your own sexual response cycle. If you don’t know what turns your crank, don’t expect your hubby to know what to do. My first question to you is: are you orgasmic? If not, there’s a whole lot of remedial sex learning for you to do on your own. If you resist doing this, for whatever reason — women are not supposed to do that, blah, blah, blah —you can say good by to ever enjoying sex with your man.

Once you figure out how your body work, it’s gonna be your responsibility to instruct your husband on the subtleties and points of interest of your particular pussy. Touch is very important to most women: often a woman will want to be touched and caressed all over, not just on the sexually charged points of her body like her tits and clit. Take your husband on a little touch tour of your body. Literally, take him by the hand and touch yourself with his fingers. Show him the kind of touch you like in the places you like to be touched. Take your time with this. I can guarantee he’s not gonna get it the first time out.

With your help he’s gonna be able to see your arousal build. He should be encouraged to use his lips and mouth as well as his hands. Make your man work for his bone, darling. If you let him just pounce on you like a sack of rice, that’s how he’s gonna respond to you. If you want him to behave like a lover rather than a conqueror, then you’re gonna have to demand that of him.

If you’re not fully aroused, your pussy will be dry. Use a lubricant to make yourself slippery and to facilitate penetration. If you can’t get commercial lube, cooking oil, body lotion or saliva is better than nothing at all.

If you follow these simple steps, Sita, you will have greater success with your fucking. You will experience great pleasure for yourself and be a fount of pleasure for your husband. In the end, it is you who must take the lead in this. Know your own body, so you can teach your husband about it. Then insist that he respect and use that information.

Name: Tench
Gender:
Age: 27
Location: San Francisco
Dear Dr. Dick: I read your response to someone having trouble making gay friends. You said casual sex tends to be the norm for making friends in the gay community. I actually agree, but I wish that weren’t the only answer. My boyfriend and I have been happily together for over a year and a half. We lost a lot of “friends” because we are in a monogamous relationship. It seems they were friends to the extent they had a chance of sleeping with (or dating) either one of us. So now we have significantly less friends, which tends to happen I suppose when a couple takes the time to grow together and bond. But now we want to re-emerge to the social scene, go out more often and have fun. We don’t want to make friends vis a vis threesomes or on open relationship. Are you saying we’re doomed to never have gay friends again unless we put out? Honestly, that’s how it often seems in SF, and frankly, it’s not acceptable. I’d rather just be with my boyfriend. Thanks!

What an interesting predicament you present. Would you mind if we examined things a bit closer? You’re tellin’ me you guys used to have friends before you got together in the sexually exclusive relationship you’re currently enjoying, right? Then these former friends…and I think it’s pretty safe to assume these were mostly single friends…began to drop away when they realized they no longer could compete for either of your affections, right?

Well, do ya blame ‘em, darlin’? I sure don’t. I mean why would any self-respecting single gay man stick around? Just to enjoy your little nesting experience from afar? Gee, no thanks!

If these former friends were also suitors to either you or your current husband, why would you want them to hang in there? You are making such a big deal out of the exclusivity of your nest, wouldn’t these others just be unwelcome 3rd wheels, as it were? I believe these other, not so exclusively encumbered as you, gay men would be much better served by taking their leave of you and your current husband and trying to find their own nesting situation. On top of the sexual tension that would continue if they did stick around, they’d also not be positioning themselves very well to find their own mate. Would you not agree?

So, ok I hope we cleared up that part. Now you say that you and your current husband are through with the first stage of nesting, the really exclusive part. And you now want to increase your circle of friends. Ok, that’s not a particularly tall order to fill! You’d probably do well to look to other couples for these new friendships, right? I mean, what would you old married guys have in common with single queer men…other than your youthfulness?

Good luck ya’ll

February 18, 2008May 15, 2026

Sex Advice With An Edge — Podcast #51 — 02/18/08

[Look for the podcast play button below.]

Hey sex fans,

We have a sweet load of very interesting questions from the sexually worrisome. I, of course, respond with an equal number of clever, resourceful and oh so informative responses! Hey, it’s what I do.

Leticia wants to get out from under her BF!
Chris wants to know if a guy can pop without shootin’.

And…

Another Handy Dandy Sex Toy Advisory: Plug Your Hole In Three Easy Steps.

BE THERE, OR BE SQUARE!

Podcast: Play in new window | Download

January 28, 2008May 15, 2026

Sex Advice With An Edge — Podcast #48 — 01/28/08

[Look for the podcast play button below.]

Hey sex fans,

I have a load of very fascinating questions from the sexually worrisome; and they’re all men this week. What’s up with that? I, of course, respond with an equal number of captivating, witty and oh so informative responses! Hey, it’s what I do.

DJ wants to know if it’s ok for he and the hubby to bone one of his patients.
Brett thinks his wife is closet bisexual. But he’s just bein’ a guy.
James is new at this whole blowjob thing!
Ricardo is playing birth control Russian Roulette.
Sean and Mel are clueless butt pirates! They should get to know one another.

BE THERE, OR BE SQUARE!

Today’s podcast is once again bought to you by: DR DICK’S HOW TO VIDEO LIBRARY.

Podcast: Play in new window | Download

January 25, 2008June 14, 2026

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.

If 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.

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.

There 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.

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.

Ok, 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.

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.

Once 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

January 21, 2008May 15, 2026

Sex Advice With An Edge — Podcast #47 — 01/21/08

[Look for the podcast play button below.]

Hey sex fans,

I have a nice load of provocative questions from the sexually worrisome. And I respond with an equal number of astounding, amiable and oh so informative responses! Hey, it’s what I do.

Amy’s vibrator don’t work no how!
Dan is dating a woman with a blockage. But what kind of blockage?
Jon’s meds eliminates his spooge output. Pity that!
LD’s partner died, but he wants to get back in the swing of things.

FINALLY, ANOTHER SEXUAL ENRICHMENT TUTORIAL

The Big Tease; How to Strip for Someone Special

BE THERE, OR BE SQUARE!

Podcast: Play in new window | Download

January 14, 2008May 15, 2026

Sex Advice With An Edge — Podcast #46 — 01/14/08

[Look for the podcast play button below.]

Hey sex fans,

I have a might big load of thought-provoking questions from the sexually worrisome. And I respond with an equal number of dazzling, charming and oh so informative responses! Hey, it’s what I do.

Seattle Guy has way too many questions, some of which are the wrong ones.
Dan and Rebecca wanna cum together.
Erin, Joy and Gene get quickies.
James has been fucked up for 25 years…or more.
S’s BF is hung like a horse! What could be the matter with that?
Alx has a thing for her older brother!

BE THERE, OR BE SQUARE!

Podcast: Play in new window | Download

January 11, 2008June 14, 2026

Loose Change

Name: Tia
Gender: Female
Age: 19
I have a problem. I’m still a virgin, but my bf thinks I’m not. It’s really my fault he thinks this, cuz I told him I was all experienced and everything. We’ve been going together for about 8 months already and I really want my first time to be with him, but how am I going to act all experienced when I don’t know what I’m doing.
HELP ME PLEASE!!!

That sure enough is a pickle you got yourself into darlin’. You’ve got some ‘splanin’ to do Lucy!

Funny, because I’m more likely to hear from young women who are not virgins, but who want to know how they can fool a new partner into thinking they are. I guess we can chalk up all this deception and confusion to the powerful associations every culture imposes on virginity…female virginity, that is.

Like most things sexual there is a huge double standard between the cultural and individual importance of virginity for women as opposed to men. Cultural expectations about virginity are also tied to age as well as gender. For example, our society expects its 16-year-old girls to be virgins. To be otherwise, at that tender age, would be a scandal in most communities. (Jamie Lynn Spears comes immediately to mind.) But a 35 year old woman who is still a virgin is considered an old maid — or worse, a dyke.

Of course, things are more fluid when it comes to boys and men. On the one hand, a 16year old boy who is not a virgin may raise some eyebrows in some communities. But many others in those same communities would praise him for being a stud. On the other hand, a 35 year old man who is still a virgin is the butt of jokes — or worse, a queer. In fact, he’s also more of a disgrace to his gender than an old maid is to hers. Funny how that works, huh?

I hasten to add that there is a lot to argue with in terms of these arbitrary cultural norms, and I encourage ya’ll to argue away. God knows I do! And you don’t have to buy into them either. God knows I don’t! But till things change, these norms are the norms, like it or lump it.

I’d love to know why you felt the need to deceive your BF in the first place? Do the people you hang with, prize sexual experience over sexual innocence for a young woman of 19? And what are the expectations of your group regarding a 19 year old guy? I’ll bet the expectation is that he not be a virgin. Right?

Well you can see why a lot of people, not just you Tia, find this whole thing just too damned complicated. And rather than add to the confusion or the deception, I encourage you to come clean with the BF about your cherry.

Here’s why I think this is the best policy. First, if the BF is sexually experienced, it will be very difficult for you to hide the fact that you’re not. Besides, like you said in your message to me. “I really want my first time to be with him.” Why not just come out and tell him that, sweetheart? No man is gonna turn that down…ever. Simply put, that is the most sexually charged and treasured sentence in any language.

Begin the big talk with your man like this. “Baby, I got something real special to tell you. You know how I’ve been sayin that I’ve been with other guys and everything? Well that was just my way of keeping all the other guys from pestering me for my junk. Baby, the truth is that I haven’t had sex before now. And the best part of this is I’ve decided that I really want my first time to be with you. My cherry belongs to you, baby”

Like I said, Tia, no man is gonna turn that down. The BF will be so flattered you won’t have to pretend to be something you’re not. Clearing the air like this will also allow you to relax when the magic moment finally happens. And relaxation is the key to enjoying yourself. And you should enjoy yourself.

Name: Mikel
Gender: Male
Age: 25
Location: Seattle
My problem is: I have a fixation on cut dicks, so when I’m having sex with uncut people, I can’t enjoy it. I feel it’s dirty!!! Should I ask my partners their “shape” before having sex? Wouldn’t I sound like a whore?

What a curious concern you have. I mean, not the cut/uncut thing…that I understand. Lots of people have a preference for either natural or snipped meat, so I’m cool with that. Sometimes the preference is even culturally induced. Ok, fine! I also know that some guys prefer what they don’t have. Lots of clipped men like uncut cock, and lots of natural men prefer their partners to be cut. Some people make a big to-do about foreskin, as you suggest, because they think it’s unsightly and/or unclean. Personally, I think that’s complete baloney, but hey, to each his own. Right?

I also know that most people who have a strong cut/uncut preference want to know in advance if their perspective partner’s dick is to their liking. And obviously, the only way to find that out is to ask outright. Ok, so far so good.

What I don’t understand about your question is that you think it might be whorish to be up-front and ask a guy about the condition of his trouser snake. Like, WHY? Either you don’t understand the meaning of the word “whore,” or you’re too self-conscious about taking responsibility for your personal tastes in tonsil ticklers . Either way it makes no sense.

Think about it this way, say you don’t ask and you discover, to your great dismay, that the guy you’re about to bone has some fine lace curtains. And you get all turned off and this screws up the screwing. You feel bad, he feels bad, and you look like a jerk. Wouldn’t it have been better to save yourself and your unlucky partner the embarrassment of shutting down a fuck by taking responsibility for your predilection before cloths come flying off? Heck, I don’t know about you, but I’d prefer to be thought of as a whore than a complete asshole.

Dr Dick has a hard and fast rule when it comes to sex. If you can’t bring yourself to ask for what you want, then you deserve what you get.

Name: William
Gender:
Age: 30
Location: UK
Hi There
I am new to this scene, and I have very little experience in anal sex and I am seeking your help and advice. I am a top but I have a problem keeping my dick hard or staying hard during anal sex. I find it harder to fuck an ass compared to fucking a pussy. Here is the problem: Once I get my dick hard, put on a condom and start fucking, my dick sometimes goes soft on me. Is that normal? How can I keep my dick hard long enough in the ass to enjoy the fuck? Sometimes even when my dick is hard, I find it hard to penetrate an ass. I use lube, so what am I doing wrong? People in gay porn can fuck and fuck like there is no tomorrow. I want to enjoy anal sex too!! Any advice? Please let me know if there is anything I can do to improve in this area?

Boy, you’re in luck, William! Last week I published my long-awaited: Finessing That Ass Fuck — A Tutorial For a Top. Check it out! It’ll answer a lot of the questions you have about butt fucking.

But before you take off to read that, I’d like to address one of the specific issues you raise, about keeping your dick hard while fucking. You are right to point out that fucking an ass (male or female) is different from fucking a pussy. But regardless of what hole you’re invading, a nice hard stiffy is essential.

Do you know what a cockring is, William? If not, I suggest you acquaint yourself with these amazing low-tech wonders. Here’s what you should do. Turn your attention to the Dr Dick’s Stockroom banner at the top of this page. Click through that link and go to the Sex Toys for Men section. Look for Erection Help there you will see the link to cockrings. Prepare yourself to be sorely amazed at the variety and functionality of these little devils.

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

I recommend the flexible and/or adjustable cockrings. These are generally made of stretchable rubber or leather. For the more daring there are the metal variety. These may look pretty, but they can be a bitch to put on and to take off. Here’s how ya put a rigid one on.

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

As you can see, putting one of these little buggers on before you have a raging hardon is gonna be easier. To take the cock ring off, simply reverse these steps, pushing your flaccid cock back through the ring first, followed by each of your balls and finally your ball sack.

It’s absolutely essential that you not wear an inflexible (metal) 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 johnson.

Remember people, play smart with all your toys!

NEXT, ANOTHER SEXUAL ENRICHMENT TUTORIAL

Beginning Sex Play — Tips and Techniques

The most frequent questions I get are from your average dick and jane, (or dick and dick, or jane and jane) who want to spice up their sex life. Inevitably they describe the kind of sex they’re currently having. And almost universally the description makes this grown man cry. Jeez, the boredom. How do they stand it? It’s a wonder any of them are having any sex at all.

What is it with the humdrum, run of the mill, we’ve always done it that way mentality? Are ya’ll afraid that if you add a little something new to your sex chore. from time to time, that the sky will fall? Holy cow!

Today’s tutorial is another attempt to motivate you to get off your butts and make something interesting happen in the sex department. We’ll begin with what was once called foreplay.

First off, I hate the word “foreplay” because it suggests that all these really great sex activities are only a lead up to a single — “more important” activity — fucking. It also implies that ya’ll can dispense with the one in order to hurry up and get to the other. And that, my friends, is always a huge mistake.

From now on I want us to banish “foreplay” from our vocabulary. Instead let’s start using “Beginning Sex Play”. It says it all. It says it’s at the beginning, but there’s no suggestion that anything in particular must follow.

I’m of the mind that we’d all be better served if we thought of sex play as a continuum of pleasure and pleasuring — with a beginning, middle and an end. If you ask me, our sex play ought mirror our sexual response cycles — arousal, plateau, orgasm and resolution. That way we’re less likely to overburden one particular activity at the expense of all the others. Get it? Got it? Good!

Experienced sex fans agree; the best sexual encounters include an extended period of sensual play at the beginning of most sex play. This brings increased pleasure to both partners, and will make whatever else that might follow more satisfying. Just remember, beginning sex play can be a meal in itself.

Beginning sex play brings spice to the encounter because it gets our motors started. Even all you major sex athletes out there who are perpetually primed for sex will benefit from some hearty beginning sex play. It will help cool your jets and make the encounter last longer than a firecracker. And I know that you know what I mean!

In our hectic rush around world, beginning sex play is particularly important. It helps us transition from the daily cares and woes to the realm of sensual pleasures. The workaholics among us need more time to become fully aroused. Their minds are still filled with the junk of the day, and not yet ready to give or receive pleasure. And pleasuring and being pleasured takes a big attitude shift from that of the rest of the day. In fact, if you’re gonna approach sex and pleasuring with the same mindset you have on the job or with the kids, give it up now and be done with it. You’ll only walk away from the encounter disappointed.

Beginning sex play primes us for maximum pleasure. Men will have the time we need to come to full erection and women will have the time they need to properly lubricate. By the way, this is called the arousal stage in our sexual response cycle. But you probably know that already, right?

When we stop thinking of beginning sex play as “foreplay” we realize there is no such thing as spending too much time giving and getting pleasure. If beginning sex play evolves into full-on fucking — SWELL. Both partners will be fully aroused and fucking will flow naturally and effortlessly from the pleasure enjoyed at the beginning of sex play.

Beginning sex play can include everything from chocolate and whipped cream to whips and chains. But let’s not get too far ahead of our selves. Let’s start at the beginning of beginning sex play. Most people miss out on the pleasure of undressing with and for their partners. Stripping out of, or being helped out of our daily wear and into something sexy or nothing at all can be very arousing. It’s also a visual signal that we’re shifting out of our work-a-day world and entering the realm of sensuality. Stripping is an art form, ya know. We could all learn a lesson or two from the folks who do this for a living, but more about this in a later tutorial.

Creating the right sex environment is important too. Make sure the room is warm. Proper lighting and music will surely add to the mood. Scents are also important. More and more people are incorporating erotica into their sex play — reading a sexy story together or enjoying some hot porn will make the encounter memorable.

Most women complain that their partners don’t kiss long enough and rush the kissing to get at their pussy. Guys, what the fuck? You want pussy? Use your mouth to maximum advantage kiss and nibble all over everything. Literally devour your partner with your mouth. Believe me, if you do this right, by the time you get to her pussy she’s gonna want to give it up big time.

Beginning sex play is the perfect time for setting the mood for all that might follow. It’s a time for sharing fantasies, role-playing, dirty talk or some full body massage. Always have some nice lotion available then use your hands, forearms, feet and elbows to knead your partner’s muscles and naughty bits.

Certain areas on the body are more hot-wired than others. It’s your job to find each and every one your partner has. As you massage vary your strokes and touch to stimulate your partner. Roll your fingertips across his or her nipples and behind his or her ears as you kiss him and tease her with your tongue.

If you’re doin things right, your partner will be moaning with pleasure. If she or he starts getting impatient it’s time to bring out the restraints. There’s nothing like some hot erotic bondage to punctuate your beginning sex play.

While your darling is subdued and possibly blindfolded, crank things up a notch. Add different sensations and stimuli, a warm chocolate sauce followed by ice cream. A fur mitt followed by a Loofah. Introduce some sex toys — a vibrator, tit clamps, or an anal stimulator.

Don’t forget to check in with your partner from time to time. Ask for some feedback and direction. Do you like this? Or do you like this better? Never presume to know what your partner likes simply because he or she liked it before, this is a recipe for boredom and the dreaded bed death. If words fail you, SHOW your partner what you want. Then encourage your partner to do the same to you.

Beginning sex play is not about pressing the right buttons in the right order. It is about understanding what makes your partner tick and supplying and applying those things to their greatest sensual advantage. There are many ways to give your partner extreme pleasure, and it all begins in your brain. Beginning sex play is as much of an art form as it is a necessity.

Finally, the basic premise behind all of this is that a great lover is one that gives pleasure because it is its own reward, not a means to getting something else.

Good luck ya’ll

January 7, 2008May 15, 2026

Sex Advice With An Edge — Podcast #45 — 01/07/08

[Look for the podcast play button below.]

Hey sex fans,

Today is my first podcast of the New Year. I have a really delectable show for you today. We have a great big load of stimulating questions from the sexually worrisome. And I respond with an equal number of stunning, appealing and oh so informative responses! Hey, it’s what I do.

Ashley wants to squirt for her BF.
Young Troy keeps bangin’ away, but he oughta try a different approach.
Ralph has a bone to pick with the red hankie crowd.
Jayrol wants a wife, kids and a white picket fence. But wait, there’s a rub!

BE THERE, OR BE SQUARE!

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