Search Results: Cross Dressing

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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.

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Georgina

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

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

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.

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

A little bit of this, a little bit of that

Name: Jake
Gender: Male
Age: 16
Location: NM
Can u get more guys to tell about mutual masturbation stories? And how I can get my friends (both straight) to do it with me?

OK, I’ll ask my audience to send us stories about their mutual masturbation experiences.wanking

Hey guys, and guys and gals, here’s what I want you to do. Send me stories about your mutual masturbation experiences. You can post your stories in the comments section of this posting, or use the Got A Sex Question form in the sidebar to the right. If we get some good ones, I’ll put them up on my site.

As to asking your straight friends to jerk-off with you, well, that’s another issue all together. Most young men won’t even acknowledge that they pull their pud. Most ostensibly straight men wouldn’t consider choking the chicken in front of a gay guy, or even with a gay guy, because they think that’s…well gay. Maybe your friends are more open-minded about such things, but I won’t hold my breath.

However, if you think there is a chance they’d consider such a thing. Why not just come out and ask. “Hey guys, I’m hosting a circle jerk at my house on Wednesday afternoon after school. If you’re lookin for a good time all you have to do is show up, drop trou and spring a boner. We’ll all be handing our own meat, so it’s just for the ritual. Prizes for the biggest load and the guy who shoots the furthest.”

See, if ya make it a sport; they may cum.

Here’s a curious exchange I had with a fellow named Dennis.

Hi, thanks for taking the time to answer me. My new girlfriend is 49, sexually active, but has never given oral sex to a male. She was married 6 years to a man who had sex with her. He liked to dress in women’s heels and clothing but never asked his wife for oral sex. They had sex and he gave her oral. Could there be a reason why he didn’t ask for oral for himself? Could he have been cheating with men to get what the wife did not do?Submissive-Crossdressing

Thank you very much; I’m very concerned. Also my girlfriend has never jerked a man off including her husband. I’m concerned why is this? Dennis

Can’t see why you’re concerned at all, Dennis. Some men, your GF’s former husband for example, aren’t all that interested in getting a blowjob or even a hand job. He probably was a submissive and was way more interested crossdressing and pleasuring his wife than getting pleasured (blowjob or hand job) himself.

There’s no reason to think he cheated on his wife with other men either. He’s just a sub. Not a particularly difficult concept to grasp, right?

Then Dennis writes back to say: I’m concerned because I’m having trouble with her touching me and giving me oral sex. Is this normal? I’ve never encountered this. Thanks Dennis

Maybe, just maybe, she just doesn’t want to blow you. Maybe she doesn’t like the whole idea. Lots of women don’t like giving BJs. And you pestering her for something she’s not interested in doling out, is only gonna make matters worse.

Have you talked to her about it? If not, that’s the way to go.

I don’t think I have anything more to offer you besides the suggestion that you and your GF might want to consult a sex therapist. You might find that there are a lot of things that you and she need to understand about one another before you invest too much more into this relationship.

Good luck

Sex Play — Tips and Techniques

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, and the “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 “Sex Play.” It says it all, and it makes 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, sex play can be a meal in itself.

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 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!rose-flogger

In our hectic rush around world, 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.

Heart PadlockSex 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 sex play as “foreplay” we realize there is no such thing as spending too much time giving and getting pleasure. If 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.

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 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 there’s more about this in another tutorial — The Big Tease; How to Strip for Someone Special.Kama Sutra Body Souffle

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.

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.

GOK small coverCertain 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 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 younipple_clamps.jpg.

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. 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

More of The Erotic Mind of Kyle Henry — Podcast #383 — 07/22/13


Hey sex fans, welcome back.Kyle Henry directs FOURPLAY 01

The award winning filmmaker, Kyle Henry is back with us today for Part 2 of his appearance here on The Erotic Mind show. He is here to discuss his movie: FOURPLAY; Tales of Sexual Intimacy.

But wait, you didn’t miss Part 1 of our chat, did you? Well not to worry if ya did, because you can find it and all my podcasts in the Podcast Archive right here on my site. All ya gotta do is use the search function in the header; type in Podcast #382 and Voilà! But don’t forget the #sign when you do your search.

Kyle and I discuss:

  • The four stories of FOURPLAY; Tales of Sexual Intimacy;
  • Skokie, IL — unleashing the animal within;
  • Austin, TX — a conception story;
  • Tampa, FL — roll-on-the-floor funny T-room sex;
  • San Francisco, CA — a crossdressing sex worker and a quadriplegic man;
  • Sex and disability;
  • Directing sex scenes;
  • Erotica and porn;
  • What he looks for in the erotica art of others;
  • What the future holds.

Kyle invites you to visit him on his site HERE ! And be sure to like his film’s page on Facebook HERE !

(Click on the box art below to buy or stream Kyle’s movie.)

fourplayDVD

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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!

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