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

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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

Beaver Trap

Everyone here at DDSA.com is about to head out for our annual end of summer holiday. But before we do, there’s this little ditty.

Name: Ward Clever
Gender: male
Age: 40
Location: Suburban, USA
My wife, June, has been passing around the beaver, if you know what I mean. This has got to stop. That beaver belongs to me. What do you suggest I do to teach her a lesson?

Dear Ward, I hear ya!  I know how troubling it can be when the little woman wanders. What’s a husband to do?Deluxe Female Chastity Belt-1

I think it’s time to trap that Beaver Cleaver, if you know what I mean. And I think you do.

Here’s what you’ll need to get the job done. The Pink Deluxe Female Chastity Belt, a top quality piece of pink leather BDSM fetish gear. So feminine, yet so sturdy!

This deluxe locking chastity belt has a waist belt, and a second belt going between the legs flaring out in an hourglass shape around the crotch area, giving more coverage in front and in back, while narrowing between the legs to conform to pelvic anatomy. How thoughtful!

Deluxe Female Chastity Belt_2Ward, my friend, not only will this little number trap June’s beaver, it will keep her bunghole from wandering too!Large Heart Padlock

This leather harness is a full-fledged chastity belt, don’t cha know. Both of the adjustable belts are lockable. The whole belt requires four locks (not included). Remember, beavers are wily creatures so security is a must if you want to get the job done right.

And while you’re at it, pick up four of these Large Heart Padlocks. You’ll want to properly secure the chastity belt and what better way to do that then with a little something that says, “I Love You?”

See, being a thoughtful loving husband is as easy as pie.

Good Luck

I like to watch…

Name: Jim
Gender: Male
Age: 67
Location: Jacksonville, FL
My question…I like to watch my girlfriend have sex with other men. This particular time she had sex, she told the guy she was going to give him or leave her “love mark” on him and she proceeded to bite his inner thigh. She and he laughed afterwards. Should I be concerned that that she may have feelings for this guy (a total stranger) we found on the internet. Also should she be caressing, fondling, and massaging him, and deep kissing him? She said she was angry with me because I questioned why she went so far. I have been bothered by this but she says there was nothing but acting on her part. Please get me out of my misery.

You’re a cuckold, Jim! Enjoy the torment you pervert! And thanks for presenting me this opportunity to tell everyone in our audience about this delightful fetish.a171827_xlf

So I suppose ya’ll know that the traditional definition of a cuckold is a married man whose wife cheats on him behind his back. However, there is such a thing as a cuckold fetishist. In fact, this is one of the most popular and fastest growing fetishes around these days. The cuckold fetishist not only knows about his wife’s dalliances, but also often enjoys the humiliation of being forced to watch. Witness poor Jim here.

In this fetish the woman is dominant and she takes on additional partners, while the male takes on (or is forced into) the submissive role. Hot, hot, hot, right? You betcha! The wife enjoys multiple partners, but the husband is made to remain sexually exclusive with her alone. This fetish can take on all kinds of permutations. Check out Dr Dick’s How To Video Library for a load of videos on this very topic. Look for the VOD tab in the header above. All you have to do is search for CUCKOLD. http://theater.aebn.net/dispatcher/fts?userQuery=CUCKOLDs&theaterId=42740&genreId=101&targetSearchMode=basic&isSearchCriteriaReset=true&searchType=movie&locale=en

a118951_xlfWhat makes a guy enjoy being cuckold? Sometimes this is part of a sexual fantasy, one of being humiliated. The guy may also just get off on watching his wife fuck other guys. I even know some guys who love this because they like watching another guy or other guys have sex. Others like being “forced” to service the other guy. You can see where this would be a freakin’ paradise for a bi or closeted gay guy, huh?

The wife and her other partners, on the other hand, no doubt get off on the scenario too. This is one way for a woman to enjoy multiple partners while controlling the sexual outlet of her husband. It’s kinda like forced chastity; another very popular fetish these days, don’t cha know. The cuckold fetish is also a common kink for the guy who is more absorbed with his wife’s pleasure than his own. I know, it’s hard to believe; but there are guys like that out there. Our friend, Jim, here is probably one of them.

Good Luck

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Nothing beats threes

David
My wife and I have wanted to add a third person to our relationship. Would you have any advice for us on how we could do this? Is this something that you could assist us with? We are in our mid forties and wanting to do this with someone we can trust.
Please help.

Hey David, try using the search feature in the header. Type in 3-way and/or swinger. You’ll find a wealth of information (both written and audio) on the topic you raise.

Here’s a taste of what you will find:3way-78516707835_xlarge

Trying new things can be really fun especially when your playing with people you like and are turned on by. I’d suggest you keep the event light and breezy. Too many people try to script a 3-way to within an inch of its life, and that can ruin the whole damn thing. At the same time, just hooking up for quick shag can be a little too impersonal.

There is another way. I suggest that you, your wife and the potential partner start your encounter by getting a bite to eat together. A little food and a couple cocktails can be a great start to the adventure. No doubt all three of you will be a little nervous, so make this part of the outing sexy and flirtatious. Each of you could practice your seduction skills on each other. In doing so, you will soon discover the sexual hierarchy…and there always is one in these kinds of encounters. If there are any ground rules for the encounter, this is the time to mention them. You and your wife should have discussed this ahead of time. The more you discover about your potential partner in this non-sexual, but seductive environment the more prepared ya’ll will be for how the rest of the evening will play itself out.

If it were I, I’d want to get a sense of how experienced the other person is at having a 3-way. Other important questions; are either you or your wife bisexual? Is the person you are inviting to join you bisexual? If the answer to either of these questions is yes, you can be assured that the dynamic of the 3-way will be fundamentally different than if none or only one of you is bi.

Be sure to inquire about the sexual fantasies of your prospective partner and share some of your own. In most situations, all the partners in a ménage are equal. Make sure that your potential play partner knows what turns each of you on. You’d be wise to know in advance what turns him/her on as well. That will make the event go a whole lot smoother.

There are some fine videos in my How To Video Library on the topic. Look for the Video Library tab in the header, then search for 3-way or swinger.

Here’s another tip: I’ve done several podcasts with seasoned swingers. All these conversations are part of the Sex EDGE-U-cation show, don’t cha know. This series of interviews takes a look at the world of fetish sex, kink and alternative lifestyles. We touch on topics both familiar and exotic. And I chat with prominent educators, practitioners and advocates of unconventional sexual expressions and lifestyles from all over the world. Here’s a fine example: The founder of Life On The Swingset, Cooper Beckett and his ever so lovely podcast co-host, Ginger. All these conversations about consensual non-monogamy are fun and informative. Don’t miss miss them!

Good luck

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