Category Archives: Transvestite

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

A Little Sex History

Happy Gay Pride Month!

It’s time, once again, to post my annual pride posting.

In my lifetime I’ve witnessed a most remarkable change in societal attitudes toward those of us on the sexual fringe. One only needs to go back 50 years in time. I was 13 years old then and  I knew I was queer.  When I looked out on the world around me this is what I saw. Homosexuality was deemed a mental disorder by the nation’s psychiatric authorities, and gay sex was a crime in every state but Illinois. Federal workers could be fired merely for being gay.

Today, gays serve openly in the military, work as TV news anchors and federal judges, win elections as big-city mayors and members of Congress. Popular TV shows have gay protagonists.

And now the gay-rights movement may be on the cusp of momentous legal breakthroughs. Later this month, a Supreme Court ruling could lead to legalization of same-sex marriage in California, and there’s a good chance the court will require the federal government to recognize same-sex marriages in all U.S. jurisdictions where they are legal — as of now, 12 states and Washington, D.C.

The transition over five decades has been far from smooth — replete with bitter protests, anti-gay violence, backlashes that inflicted many political setbacks. Unlike the civil rights movement and the women’s liberation movement, the campaign for gay rights unfolded without household-name leaders.

And yet, I sense that soon, if it hasn’t begun already, we will experience a backlash in the dominant culture. I don’t relish the idea, but I’d be remiss if I didn’t mention it. And when it comes, as I think it will, it won’t smart nearly as much if we know our history. And we should also remember the immortal words of Martin Luther King, Jr. “The moral arc of the universe bends at the elbow of justice.”

In honor of gay pride month, a little sex history lesson — The Stonewall Riots

The confrontations between demonstrators and police at The Stonewall Inn, a mafia owned bar in Greenwich Village NYC over the weekend of June 27-29, 1969 are usually cited as the beginning of the modern Lesbian/Gay liberation Movement. What might have been just another routine police raid onstonewall.jpg a bar patronized by homosexuals became the pivotal event that sparked the entire modern gay rights movement.

The Stonewall riots are now the stuff of myth. Many of the most commonly held beliefs are probably untrue. But here’s what we know for sure.

  • In 1969, it was illegal to operate any business catering to homosexuals in New York City — as it still is today in many places in the world. The standard procedure was for New York City’s finest to raid these establishments on a regular basis. They’d arrest a few of the most obvious ‘types’ harass the others and shake down the owners for money, then they’d let the bar open as usual by the next day.
  • Myth has it that the majority of the patrons at the Stonewall Inn were black and Hispanic drag queens. Actually, most of the patrons were probably young, college-age white guys lookin for a thrill and an evening out of the closet, along with the usual cadre of drag queens and hustlers. It was reasonably safe to socialize at the Stonewall Inn for them, because when it was raided the drag queens and bull-dykes were far more likely to be arrested then they were.
  • After midnight June 27-28, 1969, the New York Tactical Police Force called a raid on The Stonewall Inn at 55 Christopher Street in NYC. Many of the patrons who escaped the raid stood around to witness the police herding the “usual suspects” into the waiting paddywagons. There had recently been several scuffles where similar groups of people resisted arrest in both Los Angeles and New York.
  • Stonewall was unique because it was the first time gay people, as a group, realized that what threatened drag queens and bull-dykes threatened them all.
  • Many of the onlookers who took on the police that night weren’t even homosexual. Greenwich Village was home to many left-leaning young people who had cut their political teeth in the civil rights, anti-war and women’s lib movements.
  • As people tied to stop the arrests, the mêlée erupted. The police barricaded themselves inside the bar. The crowd outside attempted to burn it down. Eventually, police reinforcements arrived to disperse the crowd. But this just shattered the protesters into smaller groups that continued to mill around the streets of the village.
  • A larger crowd assembled outside the Stonewall the following night. This time young gay men and women came to protest the raids that were commonplace in the city. They held hands, kissed and formed a mock chorus line singing; “We are the Stonewall Girls/We wear our hair in curls/We have no underwear/We show our pubic hair.” Don’t ‘cha just love it?
  • Police successfully dispersed this group without incident. But the print media picked up the story. Articles appeared in the NY Post, Daily News and The Village Voice. Theses helped galvanize the community to rally and fight back.
  • Within a few days, representatives of the Mattachine Society and the Daughters of Bilitis (two of the country’s first homophile rights groups) organized the city’s first ever “Gay Power” rally in Washington Square. Some give hundred protesters showed up; many of them gay and lesbians.

stonewall02.jpgThe riots led to calls for homosexual liberation. Fliers appeared with the message: “Do you think homosexuals are revolting? You bet your sweet ass we are!” And the rest, boys and girls, is as they say is history.

During the first year after Stonewall, a whole new generation of organizations emerged, many identifying themselves for the first time as “Gay.” This not only denoted sexual orientation, but a radical way to self-identify with a growing sense of open political activism. Older, more staid homophile groups soon began to make way for the more militant groups like the Gay Liberation Front.

The vast majority of these new activists were under thirty; dr dick’s generation, don’t cha know. We were new to political organizing and didn’t know that this was as ground-breaking as it was. Many groups formed on colleges campuses and in big cities around the world.

By the following summer, 1970, groups in at least eight American cities staged simultaneous events commemorating the Stonewall riots on the last Sunday in June. The events varied from a highly political march of three to five thousand in New York to a parade with floats for 1200 in Los Angeles. Seven thousand showed up in San Francisco.

Back To School Q&A Show — Podcast #296 — 09/05/11

Hey sex fans, welcome back!

Happy Labor Day! I really loved having the last several weeks off from podcasting. As much as I love doing the podcasts they are loads of very hard work and a breather, from time to time is just what the doctor ordered. But now I’m back, all refreshed from the hiatus, and ready to address the concerns of the sexually worrisome who have been contacted me with their questions and concerns.

And I am delighted to welcome back my most excellent summer intern, Monique, again this week for her last show with us before she returns to the ivy-covered walls of academia. As you probably discovered last time she joined me, in Podcast 293, Monique is smart as a whip and has a remarkable talent for sex advice.

This week we hear from

  • Mystery Woman is involved in a very dangerous relationship.
  • Jerry is a crossdresser and he treats his wife like shit.
  • Worried has a “GF” but she won’t kiss him on the lips.
  • JGrant hasn’t been using protection while fucking around.
  • Laura is afraid she’ll fart at an inopportune time.

 

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: Hot Plus Size Lingerie.

Plus Size Lingerie

A Sizzlin Firecracker Of A Q&A Show — Podcast #216 — 07/05/10

Hey sex fans,

I know it’s a holiday weekend here in Americanskiville, and I know I should be hanging out at the pool or barbeque instead of slingin’ my tits over this hot microphone, but I can’t help it. I gotta catch up on all the questions that have been piling up since our last Q&A session back in May. And there’s a shit-load of ‘em don’t cha know.

We hear from:

  • Mike says it takes him too long to get off.
  • Tomas is terrified he might be gay.
  • Astrit has questions about anal douching.
  • Connor has a overly sensitive dickhead.
  • Sharon is very suspicious about FSD, or female sexual dysfunction.
  • Glenda loves giving her husband blowjobs, but he doesn’t cum that way.
  • Angelo is a crossdresser and his wife pegs him in the ass.
  • Bill doesn’t like the advice I give some women.
  • Paul might be a teensy bit queer.
  • Josh has a BF that doesn’t like his foreskin.

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

I wanna take a moment to remind you to check out another great website in the Dr Dick family of sites. It’s my new PRODUCT REVIEW site — drdicksextoyreviews.com

That’s right, sex fans, now it’s so easy to see what hot and what’s not in the world of adult products. I review of all kinds of adult related goodies — sex toys for sure, but also condoms, lubes, herbal products, fetish gear as well as educational and enrichment videos. DON’T MISS A SINGLE ONE!

Look for the drdicksextoyreviews.com. You’ll be so glad you did.

Today’s Podcast is bought to you by: DR DICK’S — HOW TO VIDEO LIBRARY.

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