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Sex EDGE-U-cation with Debra Christina Darling – Podcast #135 – 07/01/09

Hey sex fans,

Debra & Karen

And now for something completely different.  Ya’ll know how through this Sex EDGE-U-cation podcast series, we’ve been looking at the world of fetish sex, kink and alternative sexual lifestyles, right?  And how we’ve been chatting with prominent educators, practitioners and advocates of unconventional sexual expressions and lifestyles from all over the world, right?

Well then, today we take another walk on the wild side.  I bring you Part 1 of my conversation with a true original.  My guest is the one and only Debra Christina Darling

Debra self-identifies as a straight drag queen.  That’s right you heard me; he’s a straight man who crossdresses, and has done so for most of his life.  But what’s so special about that?  Lots of straight men crossdress.  This is true!  But few are as “out there” and as willing to challenge some of the popular notions of sex and gender held by both those inside, and outside, the crossdressing community.  I can assure you sex fans, Debra has balls and the attitude to match; thus the drag queen designation, don’t cha know.

You won’t want to miss a minute of this exceptional discussion!

Debra and I discuss:

  • Crossdressing vs. transvestism.
  • Her own personal journey and her activism.
  • Famous crossdressers in history.
  • Reasons why people crossdress, and the challenges.
  • The sexual charge of gender specific clothing.
  • Common myths of crossdressing.
  • Advice for parents of crossdressing kids.
  • Male crossdressing / female crossdressing, the double standard.

Debra shares with us several crossdressing resources and invites you to check them out.  The Esprit Conference, Karen Williams’ site, The Emerald City and The Ingersoll Center.

See a slideshow of current and historical crossdressers.

Click on the thumbnails below.

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BE THERE OR BE SQUARE!

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

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

DON’T BE SHY, LET IT FLY!

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

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

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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.

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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?

cock-buffet.jpgI 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 issex_toys_dj212901.jpg 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 Eden Fantasys 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 sex_toys_gef90178bs.jpgkeep 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.

  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.

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.

do-not-disturb.jpgFrom 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 yousex_toys_rd9613.jpg 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.

sex_toys_ki0001.jpgBeginning 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 sexysex_toys_ks0092.jpg 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 sex_toys_055337396x.jpgto 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 differentsex_toys_ss34047.jpg
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.

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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

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Watch Your Language, Mister!

Before we get started today, I’d like to take a minute to explain something to ya’ll. You will notice just to the right of this posting there is a section called CATEGORIES. If you scroll down from there you will notice that there are loads of topics— well over a hundred — that I’ve written about and/or included in one of my podcasts. Next to the topic you will notice a little number. That reflects the number of postings that include that particular topic. Isn’t that fucking brilliant?

So if you’re looking for information about something, I encourage you to check there first, before you send me a question. You may find that I’ve already covered your concern at length.

The CATEGORIES section is also a great resource for those looking to investigate new and interesting aspects of human sexuality.

Name: Martin
Gender: Male
Age: 50
Location: ?
Thanks in advance for your assistance, Dr. Dick.
Here’s my dilemma; I’m so in love with my partner, he’s actually the man of my dreams. We met much later in life, he being 45 and I’m 50.
I was married before w/children, out now as a gay man and all is well with my children’s relationship.
My partner has always known he was gay, has had numerable relationships and was a sexual addict. He has wanted me to understand his past in relationship to his level of happiness now, stating that he was a bottom slut only because he was never truly in love or satisfied.
He wants me to believe that “I”m the one” that has changed his life-long addiction to strange dick up his ass.
I can’t seem to get past his past slut behavior, and oftentimes get so pissed off because he wants me to meet and develop friendships with many of these past fucks (primarily because they were military buddies also).
Why can’t I accept his slutty past and stop the suspicions?
Why do I get so upset just knowing that he was a total bottom slut??
How can I get him to understand that I have no desire to know any more about his sexual past and just focus on creating our lives???
Thanks.

Martin, Martin, Martin! How you do go on, honey. Take a look at your language, why don’t ‘cha? Could you possibly be more pejorative when speaking of the sexual experience of someone who has lived a different lifestyle than you? I doubt it. Look at how many times you use the word “slut” to describe the man you say you love. How can you tell me you love someone you have so little regard for or understanding of?

Your man wants you to understand his past, but you don’t take it at face value. You69201_7_122_1143lo.jpg belittle his experience, possibly because it doesn’t match your own very limited, sexually exclusive, predominately heterosexual lifestyle.

Listen, lots of gay men (and some straight men) have loads of sex for all kinds of reasons. Sometimes just for the fun of it…or, as your man suggests, just to be a big ‘ol bottom slut. There’s absolutely nothing wrong with that. A guy can be happily sexual without loving each and every one of his partners. And the sex can be really great too. Just like a guy can have very unsatisfying sex with somebody he loves deeply. None of these things are necessarily dependent on the other. Don’t make such a tangle of it all, Martin. Sex, love, intimacy are all very different things.

I also want to reinforce my belief that there’s no such thing as a sex addict. Compulsive behavior? Sure! Out of control behavior? You betcha! Self-denigrating behavior? Absolutely! Sexual addiction? No way!

Try for just a minute to extricate yourself from your sex-negative mindset by exchanging the notion of eating when you talk about your friend’s sexual exploits. Would you have the same revulsion if your guy said he had shared food with lots of other guys? Some of it was fast food that didn’t satisfy very much. Sometimes he ate just because he wanted to, not because he was hungry. And now he wants you and he, as a couple, to be friends with some of the men he ate with. Sounds perfectly reasonable to me!

Your man is trying to open you up to seeing life and sex as most openly gay men do. This is fundamentally different from how some formerly closeted men see life and sex. If you let him, he just might help heal you of your sex-negativity.

Finally, jealousy is one of the worst human emotions. It is a kind of hatred, you know. Sometimes it’s hatred of another, but it is always self-hatred. We’d have no reason to be jealous if we had enough self-confidence. You say you love this man, but I challenge you on that. It’s clear to me that you have a much greater love of your provincial notions about sex then you have for this guy.

Here’s a tip, Martin — jettison the unhealthy attitudes about sexual expression and give your guy a chance to be himself, not what you want him to be, or what you think he should be. You’d be well served by working with a sex-positive therapist to help you get over this. Do it now, because if you hesitate you will surely ruin the very relationship you claim to treasure.

Name: Pete
Gender: Male
Age: 60
Location: New England
What is sounding the penis and why is it called that?

Sounding is a kind of urethra play. It’s called that because the it involves sounds, a kind of dilator. Why not mozie on over to Dr Dick’s Stockroom and check out the Sounds & Dilators section. You’ll get an eyeful!

Urethra play freaks out lots of folks. Most of us equate having something inserted into our urethra…for any reason…with a root canal by a sadistic dentist. Not something purposely done for the sheer enjoyment of it.a974.jpg

I’m always curious about how folks come to odd fetishes like urethra play. One of my correspondents back in July, Georgia, wrote that her urethra play began when she was a child. She asked her mother where babies came from. Her mother said it’s where peepee comes out. Georgia looked down there and saw this teeny-tiny hole. She knew having a baby was difficult and painful and thought, no wonder! So she decided she’d better try and make the opening bigger. And so it began.

Once a guy told me his fetish started when he was playing doctor with his older cousin. His cousin inserted a twig into his urethra, mimicking how he thought a doctor would take a patient’s temperature. This guy said that the moment was so sexually charged, even as boy of no more than 5, that his piss hole became an object of fascination and pleasure from that day onward. When I knew him, he was able to insert the bristle end of a toothbrush into his urethra. That bit of unsolicited information just about made me swoon into a faint back then. Even now, retelling that story gives me the willies.

So ok, this isn’t for me, but I am told by those in the know that because the urethra is such a sensitive organ, stretching it can provide exquisite sexual pleasure.

Practitioners of this unique kink often start out young, like Georgia and the other guy. Maybe it’s just a function of one’s natural curiosity about his/her body, when one day he/she discovers their urethra. They toy with it, stretch it and find pleasure. Once that happens, of course, it becomes like most pursuits of pleasure. It becomes a fascination, then a full-blown kink.

If a little accidental stretching is pleasurable, they wonder, what about intentional stretching with one kind of gadget or another — Q- tips, thermometers or a ballpoint pen? Once these kids are old enough to do some research, they discover an array of medical implements available to them; like latex or plastic tubing, catheters and urethral sounds and dilators. Well, you can see how this could just grow and grow…pretty much like any fetish. Pleasure is curious that way, spurring us on to higher and higher heights.

But like all pleasure related things, practitioners ought to have their wits about them when they play with their pee hole. I think it’s ill advised to be stretching your urethra with just any old thing lying around. One’s bladder and urethra are sterile areas and one ought only use sterile equipment and procedures while inserting anything in there. And one ought to take one’s time with this sort of play. Incremental stretching is advised. The use of mind altering, or body desensitizing drugs is not recommended, for obvious reasons. Like I always say, safe and sane play is happy play.

And here’s something you should know — the male urethra is approx. 10 to 13 inches long and has a “J-shaped” curve to it. The female urethra is much shorter, only approx. 2 1/2 to 3 inches long, and there is no curve. Therefore, a woman can stretch her urethra much easier and to a greater extent than a man can. You will find that these gender differences also makes for gender specific toys.

Name: Alice
Gender: Female
Age: 19
Location: Minnesota
My new boyfriend is really frustrated and doesn’t want to have sex anymore because he can’t come. He says he’s had this problem for a while and hasn’t come with any girl for over a year. I see how upset he is and I know he still wants to sleep with me but says it hurts when he gets excited and nothing happens. Is there something I can do? I tell him to see a doctor but I don’t think he will. thanks a lot!

Wow, that’s a bummer Alice. Unfortunately, you don’t supply me with enough information for me to make an educated guess about what might be up with him. So I’m gonna make a stab in the dark.

If I had to guess, I’d say the lad is suffering from a real bad case of performancetom03a.jpg anxiety. He doesn’t need a medical doctor; he needs to relax.

Here’s how this nasty thing works. Say a fella has a less than satisfying sexual experience for one reason or another. Before he know it, he replaying the incident over and over in his head, till that’s all he thinks about. The proverbial molehill becomes a mountain. He brings his anxiety to his next sexual encounter. His hyper-consciousness primes him for more disappointment. And he’s ready to interpret all disappointment as a failure.

Well, you can see where I’m going with this, huh? His fears become self-fulfilling. Before he knows it, he begins to avoid sex. His relationships suffer. He develops a full-blown sexual dysfunction. And his self-esteem takes a nosedive. His preoccupation with his problem makes it less likely that he’ll be fully present during sex with his partner, which pretty much fucks up his sexual responsiveness and any hope for spontaneity.

It looks to me like performance anxiety is putting a damper on his sexual arousal and short-circuiting his sexual response cycle.

This is nothing to fool around with, especially for someone at his tender age. When I see this sort of thing in my private practice, I always begin the therapeutic intervention by calling a moratorium on fucking of any kind. This immediately takes a great deal of the pressure off the couple. From there we begin to rebuild the partnered psychosexual response one step at a time. We begin with sensate focus training, stress reduction and relaxation exercises. I have the greatest confidence in this method. It succeeds over 90% of the time.

Name: Roxy
Gender:
Age: 37
Location: SF Bay Area
Dear Dr. Dick, I am slowly but inexorably marching to my wits end over my current dilemma. I’m a part time TV married to a wonderful girl who I find very satisfying emotionally, mentally and physically. So what’s the problem, you’re asking? The problem is that before we got married I had several sexual encounters with men (yes, with me dressed and made up as a girl). Some of which were quite thrilling, and now I find that I am yearning to get all dressed up and find a male partner who will satisfy the girl side of my psyche sexually. I don’t want to cheat on my wife (with whom I’ve talked about marital fidelity…if I cheated and she found out, her line is that our sex life would be over), but I feel the compulsion to act getting stronger all the time… what should I do? Sincerely, Distraught in downtown

Before I respond to you, Roxy, I want to make sure my audience knows what we’re talking about.

Folks, Roxie here is identifying as a part-time TV. That, of course, has nothing to do with the box in your living room on which you watch The Brady Bunch reruns. TV in this context means transvestite. Which is literally the practice of cross-dressing, wearing the clothing of the other sex. Which as we all know, or should know must not be confused with a TS. And I don’t mean the poet, but a transexual. A transexual is a person that self-identifies as the gender other than the one he/she was assigned at birth. I hope we’re all down with that now.

It appears to me, Roxy, that you’re really overreaching here. Desires are wonderful2070257205_55f002f39a.jpg things. We just better know the difference between a desire and reality. I encourage you to think twice about realizing this particular desire of yours if it means upending your marriage. Seems to me your long-suffering wife’s feelings deserves more than the casual consideration you afford them.

Most TVs I know would give their left falsie for a partner as understanding and accommodating as your wife. And look at you, considering fucking this up by skipping out on her. Just so you can get all gussied up and find a dude to pound the bejesus out of you to satisfy the girly side of your psyche.

I never advocate the cheating option. But I know how compelling sexual fantasies can be. On the other hand, maybe some kind of additional accommodation could be made with your wife. Maybe she’d be up for a 3-way.

I know this marvelously kinky woman, Abby, who pimps out her beautiful straight boyfriend to totally hot gay gays they meet at the best gay nightclubs. She does this just so she can watch the straight BF get pounded. I hasten to add that the beautiful straight BF is a willing participant in this unusual ménage. Curiously enough, he’d never think of doing this on his own. For him, the turn on is not the part where other guys fuck him, although that is pleasurable. It’s pleasing and being dominated by his kinky girlfriend that turns his crank. So when Abby snaps her finger, you know for certain that Ty will soon be buggered senseless. Now that’s devotion. And while this is not for everyone, it sure as hell works for them.

Will your little woman go for something like this, Roxy? Got me! One thing for sure, you’ll never know unless you ask. Here’s a tip. To sell this whole ménage thing to the wifie, I encourage you to play up how HOT it will be for her. How much fun she’ll have watching and possibly even directing her pansy-ass husband take it up the bung-hole. How it’s gonna blow her mind, and shake up your traditional sex roles and really spice things up in the boudoir. With a sales pitch like that she might just give it a whirl.

I don’t envy your dilemma, Roxy, but I think something interesting could come of this just as long as you’re upfront about it with your wife. If ya don’t, you’ll soon be a cock in a frock with his marriage on the rocks.

Good luck ya’ll

 

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If It’s Not One Thing, It’s Another!

Name: Julie
Gender:
Age: 26
Location: 41425
I am a virgin. I am also just asking How do I keep my first time from hurting? Some Say Lubrications in exess, but I am very small.

Yep, lots of lube is important — first time and every time. 05_10_12.jpg

But there is so much more you can do to prepare yourself for your first fuck. Begin by knowing your body and your sexual response cycle. Is it safe to assume, even though you are a virgin to full-on fucking, that you are familiar with masturbation? If not, darling, that’s where you should start. If you enjoy pleasuring your body to orgasm, you will likely know the kind of stimulation you need to achieve full arousal. This is precisely the information you will want to pass on to your partner before the fuck-fest begins as well as throughout the event.

The more you know about your body and the mysteries of your particular sexual response cycle the smoother things will go for you and your partner. Nowadays there is absolutely no need for anyone to come to their first partnered sexual encounter uninformed about sex in general and his or her sexuality in particular.

Most women experience pain during fucking (for the first time or anytime) because of one of three basic reasons: 1) She is inexperienced, 2) Her partner is inexperienced or unversed about mutual pleasuring, 3) She is not fully aroused. Right away you can see how a familiarity with your body in general and your pussy in particular will short-circuit at least two of the three basic reasons right away. And while you can’t account for the sexual prowess of your partner, you will be able to direct him/her on how to touch and make love to you. And that, my dear, takes care of the third basic reason.

One other thing, a lot of women don’t relax during sex…thus discomfort…because they worry about becoming pregnant. If you’re not well versed on all methods of contraception and actually practicing one of them, you’re not ready to have sex. And one other thing, sexually transmitted infections ought to be a concern for both you and your partner. Don’t be a fuck-up; your partner ought always use a condom.

Name: Dave
Gender:
Age: 20
Location: Sydney
The other day I had to stop myself pissing mid-flow.. and god it hurt like fuck… felt like my ass was being tugged, from within. why does this happen? and can there be any damage from doing this at all?

Jeez, ya got me, pup! Was this some kind of muscle spasm? The muscles in your pelvic region, specifically your pubococcygeus muscle (or PC muscle), are responsible for stopping the flow of pee. Could you have injured or strained these muscles in some way? Has this happened before? One thing for sure, if this continues; have a doctor take a look right away.

Name: Drew
Gender:
Age: 22
Location: Idaho
Is there any way that I can increase my quality of orgasm? I’ve been having shitty orgasms for the last year, so shitty that they really shouldn’t be called orgasms. I’m on antidepressants (Effexor XR), and I fear that is a factor. I’m also having trouble keeping an erection, it never really gets fully hard and then kinda fades in and out over the course of masturbation or oral sex. Any ideas?

I think you put your finger on the problem right there. Antidepressants can sure enough fuck up a person’s sexual response cycle — interfering with both erections and orgasms. c917.jpg

Short of going off your meds, which I don’t advise…at least not without consulting your physician first…there are a few things you could try. I advise all my clients who are struggling with this same issue to use a cockring. It helps them get and keep a harder hardon. And of course, the more firm your rod, the more likely you will have a “quality” orgasm. I also encourage other clients on antidepressants to use a vibrator during their sex play…alone or with a partner(s). There are several different kinds — wands, dildos, eggs, bullets and plugs. Check out Dr Dick’s Stockroom for every imaginable kind. Of special interest for you might be The Rude Boy (C917)

Name: Jennifer
Gender:
Age: 42
Location: AZ
No joke, I am writing for my best friend who is a 41 year gay man and a virgin. He has never had any type of intercourse and has had brief foreplay with only a few. He can get erect when masterbating but not with a partner. He has tried to “wing it” and pick up men only to be “punched in the gut” again and again and again. He does not pick up anyone anymore because he considers it “false advertising”. He is super cute, very funny and works in the entertainment industry. He is so lonely and very depressed and completely against any type of medication. He wants to share his life with someone so bad. He says that no one has his problem and medical doctors say that the plumbing is fine. He seems to think that because he was able to masturbate at 8yrs old without a true erection that this ruined him. All my research points to performance anxiety and ED which he completely denies. He tried Viagra and that did not even work. Please share your best advice…I really want to help him. Thank you!!

My best advice? Okey dokey, here goes!

This boy needs a sex-positive therapist big time and right away. He is a freakin’ ball of sexual neurosis, for cryin’ out loud. However, the likelihood of your best friend actually seeking the help he so severely needs is nil. Especially since he can’t even cop to performance anxiety and ED issues with you.

And you know what, Jennifer? You may actually be enabling this dude’s dysfunction by allowing him kvetch about his love life…or lack there of. Lay down the law, darling. Tell this miserable wretch he needs to get professional help ASAP. If he refuses, cut him off from your shoulder to cry on. If he can’t grow a pair of cohunes and address his issues like a man, then you oughta grow a pair for him till he get a life. And that’s my best goddamn advice. So there!

Name: Rachel
Gender:
Age: 32
Location: Houston
I have the pleasure of dating (for the first time) a man who is uncircumcised (his foreskin completely covers his head. I love giving oral sex, but I’m a little intimidated. Lots of info on “cercumcised blow jobs” … not so much on Mr. natural. How do I blow his mind!

Doll, havin’ a natural man don’t make suckin’ his cock any different than suckin the cut variety. Except that you have a whole lot more delicious willie to play with. Let’s start with the basics. There’s no one best way to make oral love to a boner. No two cocksuckers will do it exactly the same way. But all have one thing in common, and that’s the desire to satisfy. Technique and position take a back seat to simply craving a cock in your mouth. We’re not talkin’ rocket science, girlfriend, it’s just a pecker and a mouth doin’ what comes natural.

vein.jpgBegin by taking a good look at the object of your desire. A big stiff woody with lace curtains is a wonder to behold. And even those little willies can be cute as hell. Visually explore the whole enchilada. Feel it’s shape, its thickness and texture. Sick a finger under his hood and trace his dick head. Nibble on his foreskin. Pull on it and stretch it out. He’ll be sure to let you know if you are doing too much.

Use your tongue to trace a line from his dick head down the underside of his shaft to his balls. Draw back his foreskin and slop your tongue all around his corona. As you do, watch your man’s eyes roll back in his head in ecstasy.

Let his cock slide inside your mouth. Let your lips slide over the head and down the shaft a little, but, for god’s sake, watch out for your teeth! Slide your mouth down farther and open wider. Feel the stretch in your jaws. When his dick gets close to your throat, you may begin to gag. This is a normal reflex that you will, in time, be able to control. Ask for some feedback on your efforts. Just don’t talk with your mouth full.

There are lots of other things you can do with your mouth. Lick his dick, suck on it and flick your tongue rapidly across the top of his dick. Or you can simply move your mouth up and down his joystick drawing his foreskin back and forth with your hand as you go.

Dive into his crotch, lick his inner thighs, lower belly, and slobber all over his nuts. Keep your mouth wet, a thick wad of saliva will add to the pleasure and eliminate irritation. Don’t be afraid to be sloppy. Increase your speed or slow it down. Fondle and cup his balls in your hand.

As your man is about to spew, he will become more excited and may start some pelvic thrusting. If he does and you start to gag, use your hand to guide his dick in and out of your mouth. Remember that you’re the one in charge here. Encircle your lips firmly around his cock and over your teeth. Keep the other parts of your mouth as relaxed as possible (actual “sucking” is unnecessary at this point). Keeping a regular rhythm is nice, but don’t let it get boring. If you vary your position and your stroke you won’t get fatigued.

Name: Bruce
Gender: male
Age: 19
Location: UK
What’s a PA? I sometimes see this abbreviation in online personals but I can’t figure it out. thanks

Well, Bruce, PA could mean a whole lot of things. It could be an abbreviation for Pennsylvania, public address system, personal assistant, parental advisory, pussy addict …hell, even Port Arthur, Texas.

pierced.jpgBut if I had to guess, you are referring to PA as in Prince Albert.

A PA is probably the most common male genital piercing. It enters the urethra and exits immediately behind the glans on the underside of the cock.

The Prince Albert Piercing, also known as a “Dressing Ring”, was apparently designed to strap the penis tightly against one’s leg to minimize the bulge caused by one’s rod when wearing the very tight trousers, which were fashionable during the Victorian era. We sure have a different ethinc about that today, huh?

As the rumor has it, Prince Albert, queen Victoria’s hubby, wore one of these little numbers to hold back his foreskin so he would keep his johnson sweet-smelling so as not to offend the Queen. What a fuckin’ gentleman!

Good luck ya’ll

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