Tag Archives: Q&a

What A Drag


Here’s something unusual. Just last month we heard from Roxie, a crossdresser at a crossroads. Today, another crossdresser. That’s what’s so unusual, two in one month. Maybe it’s something in the stars. Anyway, our fabulous friend here has a bit of the ennui.

Name: Mariah
Gender: Male
Age: 23
Location: Brewster NY
I have been doing a lot of crossdressing secretly and I have no idea how to stop. Its been going on for quite a number of years and I am not sure exactly what I should do. I enjoy a lot of other things that I won’t mention. I guess my question is how long does it take to get over this?

Mariah darling, I’m confused. You’ve been secretly crossdressing for a number of years and now you want to stop? Why? Sounds to me like you’re still into it. A lot!

crossdressingAnd then you tantalize me with; “I enjoy a lot of other things that I won’t mention.” What’s up with that?

So ok, you’re a kinky little transvestite; is that such a big deal? Crossdressing is a relatively innocuous fetish, as far as fetishes go. And if you’ve been doing it for years, albeit secretly, I’d guess you have your fetish under control. It doesn’t sound like it’s messin’ with or spillin’ over into the rest of your life. So again, my question is, why stop?

If you’re just bored with it, which doesn’t sound like the case; why not simply pack up your frilly knickers and dancer heels and drop them off at the Goodwill? If you don’t have women’s clothing around the house, you won’t be able to crossdress. So that part is relatively simple.



However, getting over a fetish is not so easy as ridding yourself of your frocks. There’s probably a psychological and an erotic hook in your crossdressing, as there is for most folks who do drag. After all, this is what makes the whole exercise a turn on and so much fun. You can learn to wean yourself off this activity, if you really, really want to. But again my question is: why?

If you feel your crossdressing is screwin’, up your life, or contaminating your relationships; well, that’s another thing. But you don’t say that. Maybe you just need some assistance in understanding what’s going on with you and some support from others like you. And that, my dear Mariah, is very easy to come by. First, let me direct you to a couple of brilliant podcast interviews I’ve done with two amazing crossdressers — first, Debra Christina Darling. (You’ll find Part 1 of that conversation HERE and Part 2 HERE!)   Then there’s the toast of the Emerald City, Sylvia O’Stayformore. (You’ll find Part 1 of that conversation HERE and Part 2 HERE!).  Or just use the the search function in the sidebar to your right, type in either of those names, and PRESTO! Faster than you can say Lane Bryant, you be taken to their podcast postings.

These interviews are chock full of information about crossdressing; the dos and don’t as well as the whys. I’ve also supplied a short list of online resources for crossdressers, drag queens, and transgender folk.

Good luck

What’s a mother to do?

What we have here is an exchange I had with a woman and while I don’t know anything about her, not even her name, I can make some inferences. If I had to guess, she’s in her 40’s. She’s married and has kids.

You must talk to a lot of women in your practice and hear from a lot of women through your advice site. What would you say are the main sexual concerns of women over the age of 40?

Research shows that approximately 40% of women experience sexual problems. But a 2008 study out of Harvard suggests that only a few — 12% — are concerned enough with these issues to do anything about them. I find that not only surprising, but shocking! That suggests to me that sexual wellbeing is not a high priority for a good number of women.  What a bummer!sexual-Frustration

Low libido, diminished arousal, difficulties with orgasm, pain with sex or body image concerns all play a part. A lot of this is directly connected with having an ineffectual partner. I mean, I’d give up sex too if I was consistently frustrated and unfulfilled. But what about masturbation? Are sexually frustrated women seeing to their own needs through self-pleasuring? I don’t see any hard data, you should pardon the pun, on that topic.

We hear a lot about the horny dad and the tired mom, but what do you do if the “roles” are reversed – and dad is tired and mom is horny?

Curiously enough, I hear from way more men these days, who are exhausted, depressed or overweight and who have little or no libido, than I hear from women with the same problems. Sign of the times? You betcha!

But don’t sink to the lowest common denominator. Here’s one of my most popular tutorials, Sex Play — Tips and Techniques.

How can parents find common “ground” when it comes to when they might have sex (as in day of the week or time of day)? Does it always involve compromise? Can our internal clocks ever synch up?

Synching up schedules my not always be the solution. If we wait for that to happen, we could die waiting. The answer might be finding a middle ground. “I may not be up for full on fucking at the moment, but I’ll give you a fantastic hand-job.” Or “I can’t seem to get it up right now, but hand me your vibrator and I’ll send you to heaven!” I’m a huge proponent of mutual masturbation.

Another suggestion might be something like The MoodSign. We reviewed this very clever gismo awhile back. In fact, it was among our Best Products List for 2013. Check it out and see if something like this would help.

If parents are interested in kinking it up, what are some simple, not too scary ways to introduce it into the relationship?

Keep it safe and consensual. Always have a safeword. I developed a workshop called; The Gospel of Kink. I’ve also conveniently packaged this workshop into a workbook with the same title. You can find the book HERE!

GOK small cover

Both the workshop and book are designed to help people, like you, develop the skills they need to effectively communicate with one another and improve their problem solving skills. The workshop and book, as the title suggests, are specifically geared toward folks in kinky, BDSM, and alt-culture relationships, but even vanilla couples will find what I present very helpful.

Bondage games are always fun. And you don’t need anything beyond what you already have in your closets — silk scarves, belts, shoe strings, etc.

Nipple clamps, playing with sensations like ice cubes and hot wax, hair pulling, making use of blindfolds and gags

Discipline/Spanking is always fun too — a ruler, a hairbrush, a wooden spoon, a belt, rubber bands. See my tutorial: Spank Me, Daddy.

Role play is always a delight. Don’t forget about phone sex.

There are tons of instructional videos at Dr Dick’s How To Video Library.

I always suggest that couples read erotica aloud to each other. That never fails to get one’s motor purring.

I’d also love to talk with you about the taboo of sex, particularly with the parenting set, and how parents, moms, and dads, can work to break stereotypes without feeling like a sexual “deviant.”

Really? What would be so wrong about being a deviant?

Good luck

Selfish So ‘n So

Name: Andrew
Gender: Male
Age: 34
Location: Texas
I’m selfish. I don’t feel like having sex with anyone, not even my boyfriend. I can masturbate all I want and get off just fine but I prefer to do it alone. My boyfriend is frustrated and wants me to go to therapy, but I’m extremely uncomfortable with the idea. I’ve had selfish times like this before, but this one has been the longest (almost 2 years). Usually they’d last a few months at most and seem to have happened independent of whether I’m doing great or depressed. I’m also fairly certain that this isn’t to do with my current relationship. The reason is that past selfish times have happened whether or not I’ve been seeing someone. When I get this way, even guys who are perfectly my type (like my boyfriend) can try all they want to get into my pants (literally and figuratively) and will not be successful. When I’m like this I notice that I barely think about sex unless a dirty picture, movie or text is in front of me, and I’m only trying to get away when a hot guy is trying to get in my pants. I’m usually good at finding out what’s going on in my head, then solving an issue but this one has me stumped.

So you’re tellin’ me you’ve been withholding sex from your long-suffering BF for nearly 2 years? That’s not being selfish, my friend; that’s torture. Your refusal to see a therapist about this, because you are “extremely uncomfortable with the idea,” also tells me that your issues are deep seeded and you’d rather keep these things hidden and stifle your relationship then get them out in the open and resolved.

love music

I’m sorry, Andrew, but I have virtually no patience for folks like you. If you were single and you wanted to live your life like this; that would be fine. But you’ve involved your sexually messed up self with another human who has needs that are just as important as yours. And that, sir, ain’t right.

I have one real simple premise that I live by. And it is, each of us has a right to a happy, healthy, integrated sex life. If there is something that is getting in the way of achieving that, whatever it might be, it is a problem that needs to be addressed immediately.

As far as relationships go, I am of the mind that we ought, first and foremost, work to honor our commitments of mutual support. Are there ways that these two moral principles — a right to a healthy sex life and one’s relationship commitments — can coexist when one’s relationship excludes the possibility of happy sexual expression? Yes, I believe there are. And many couples achieve that balance, because they have an overriding love and concern for one anther.

Now the facts — not all loving relationship, including many marriages, have a sexual component. Many, for one reason or another, simply don’t. In fact, most long-term relationships are not sexual in nature. However, a partner in loving relationship who is unable to provide sexual satisfaction to his/her partner should give that partner permission to find sexual fulfillment outside the relationship. I hasten to add that these are often very difficult negotiations to hammer out. But to do less than try to make these accommodations is, I believe, a form of sexual abuse.

If your partner is trying to negotiate a satisfactory solution to your problem and you are opposed to even discussing the issue or seeking the professional help you desperately need you will destroy a perfectly good and viable relationship. And that is unconscionable in my book.

I am not suggesting that you deny your sexual issues just to appease or pacify your partner. Nor do I condone simply letting your selfishness become the path of the least resistance. These options will only create a divide between you and your partner that will not be able to be bridged.

If you ever hope to escape the corner you’ve painted yourself into, you’ll have to buck up and be honest with your partner and commit to getting the help you need.

Good Luck

A cock in a frock with his marriage nearly on the rocks

Name: Roxy
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.

transvestiteFolks, Roxie here is identifying himself 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, or better still, crossdresser. Which is literally the practice of crossdressing; wearing the clothing of another sex. Which as we all know, or should know, must not to be confused with a TS, which means transsexual, or better still, transgender. (Here’s a tip:  the terms transsexual and transvestite are outmoded because they are heavily pathologized, as medically or psychologically abnormal.) A transgender person is someone who self-identifies as a gender other than the one she/he was assigned at birth. I hope we’re all down with that now.

Now back to you, Roxy. It seems to me that you’re really overreaching here. Desires are wonderful 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 relationship. Seems to me your long-suffering wife’s feelings deserves more than the casual consideration you seem to 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, contemplating fucking this up by skipping out on her just so you can get all gussied up so you can find a dude to pound the bejesus out of you to satisfy the girly side of your psyche.TV01

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 men 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 the 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 while she’ll get a great show. Now that’s devotion. And while this is not for everyone, it sure as hell works for them.

RHPSWill your little woman go for something like this, Roxy? Who knows! 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

He Can’t Cum!

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. Does he have erections? Does he masturbate? Is he on any medications? These are the first questions I’d ask him. Since he isn’t here and neither are you, I’m gonna make a stab in the dark.cover up

If I had to guess, I’d say your man is suffering from a real bad case of performance anxiety. He doesn’t need a medical doctor; he needs to learn to relax and be in the moment. If this is an arousal phase issue then that should help. If it’s and orgasmic phase issue, relaxing and enjoying the pleasure will also help.

Here’s how performance anxiety 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 can think 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. And this can interrupt either the arousal phase or orgasmic phase of our sexual response cycle.

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 sounds to me like performance anxiety is putting a damper on his sexual arousal and thus short-circuiting the rest of his sexual response cycle, including orgasm.

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 psycho-sexual 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.

Good luck

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