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Sylvia O’Stayformore, Part 2 – Podcast #151 – 09/09/09

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Hey sex fans,

We’re back with the toast of the Emerald City, Sylvia O’Stayformore and more of her naughtySylviacharming Sex EDGE-U-cation.  There’s nothing like the wisdom of a drag queen to put all this sex, sexuality and gender stuff into perspective, don’t cha know.

Did you somehow miss Part 1 of this enjoyable conversation?  Well, all ya have to do is use the search function in the sidebar to your right.  Type in Podcast #150 and PRESTO!  You’ll find last week’s show.  But when you do your search, don’t forget to include the # sign.

Sylvia and I discuss:

  • Becoming Sylvia and her signature look.
  • Crossdressing; compulsion or recreation.
  • The difference between a drag queen and a female impersonator.
  • If there is a hormonal or genetic component to crossdressing.
  • The skill involved in being a drag queen.

Be sure to visit Sylvia on her MySpace page HERE.  She’s on Facebook too, HERE.

Due to the popularity of last week’s show and the inclusion of the Jizz4U LIVE video archive, I’ve decided to added a new one this week.  Today’s archive features Sylvia and her special guest, Miss Indigo Blue.  Be sure to check it out.  And yes, there will be another naked man.  Hey, it’s what we did!

You’ll find the video HERE!

See a slideshow of the fabulous Sylvia O’Stayformore at work and play.

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: Eden Fantasys.com.

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Sex EDGE-U-cation with Sylvia O’Stayformore – Podcast #150 – 09/02/09

Hey sex fans,

This week we gonna get some pretty delightful Sex EDGE-U-cation.   This is, of course, the podcast series that looks at the world of fetish sex, kink and alternative sexual lifestyles.  My guests have included prominent educators, practitioners and advocates of unconventional sexual expressions and lifestyles from all over the world.  And today I am proud to add another category to that list today — Entertainers.DSCN7819

Yes siree, buckaroos, my guest is the one and only Sylvia O’Stayformore.  She is the toast of the Emerald City, don’t cha know.  She is my friend, a brilliant drag performer and a laugh riot on stage and off.  She has tickled my fancy on several occasions, if ya know what I mean.

And guess what?  I even had the good fortune to co-host a live sex show with Sylvia a couple years ago.  As a special treat, I’ve added that video to this posting; scroll down to find it.  Be sure to check it out, cuz it has a naked man in it; and happily he ain’t me.

Sylvia and I discuss:

  • Her humble beginnings.
  • Crossdressing vs. transvestism.
  • Crossdressing and drag.
  • Her own personal journey and her activism.
  • Women drag queens?  Who knew!
  • Reasons why people crossdress, and the challenges.
  • The sexual charge of gender specific clothing.
  • Getting hit on as Sylvia.
  • Common myths of crossdressing.
  • Advice for parents of crossdressing kids.

Be sure to visit Sylvia on her MySpace page HERE.  She’s on Facebook too, HERE.

See a slideshow of the fabulous Sylvia O’Stayformore at work and play.

Click on the thumbnails below.

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Folks:  I had to post the video archive separately.  Having it included in this posting screws up the works, don’t cha know.  You’ll now find it HERE

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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Debra Christina Darling, Part 2 – Podcast #137 – 07/08/09

Hey sex fans,

We back with Part 2 of my fascinating discussion with the amazing Debra Christina Darling.  Debra self-identifies as a straight drag queen, don’t cha know.  So you can be certain she’ll be dishing out a EC Cruise 004heft dose of attitude with her point of view.

Debra is here as is part of my Sex EDGE-U-cation podcast series, where we look at the world of fetish sex, kink and alternative sexual lifestyles.  We chat with prominent educators, practitioners and advocates of unconventional sexual expressions and lifestyles from all over the world.

If you some how missed Part 1 of this uninhibited conversation, look for Podcast #135 on my Podcast Page.  You’ll find a tab for that page at the top of DDSA.com.  Or you can use my site’s search function.  Simply type in Podcast #135 and presto!  But don’t forget the # sign.

Debra and I discuss:

  • Why we fetishize women’s clothing.
  • Where one finds women’s clothing to fit a male’s body.
  • How she came to be Debra.
  • Drag Queens we’ve known and loved.
  • Therapeutic crossdressing.
  • Coming out as a crossdresser to family and friends.
  • Support services for crossdressers and transexual folks.

Check out some of these resources: TransSpace, Tri-Ess, A Crossdressers Secret Garden and Cross Dressers Anonymous.

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 HOW TO VIDEO LIBRARY

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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.

[nggallery id=30]

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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