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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

Between a rock and a hard place

Name: Adam
Gender:
Age: 34
Location: UK
I have been attracted to male children for years. Having been arrested for viewing child porn I realize that I need to pursue a celibate lifestyle. I realize that celibacy is a demanding lifestyle. What advice would you offer me?

You present a particularly touchy issue for our culture, Adam. But before I respond, I’d like to help you with some of your vocabulary. You say you need to pursue a celibate lifestyle. I think you mean to say you need to pursue a sexually abstinent lifestyle. The two concepts — celibacy and sexual abstinence — mean different things. Unfortunately, way too many people use these terms interchangeably. This is not a good thing and only serves to muddy the waters further.

Celibacy has a very specific meaning. Let me whip out my trusty, handy dandy Funk & Wagnalls dictionary. Celibacy: the state of being unmarried. Some people infer, especially those of a strict religious bent, that celibacy also connotes sexual abstinence. Ya see, religious people are of the mind that there is no legitimate sexual expression outside the confines of heterosexual marriage. Legitimate or not, unmarried people have always been and always will be sexual, so making that unfortunate connection between celibacy and abstinence ill advised.

The only thing we ought to be able to say for sure when someone identifies him/herself as celibate is that he/she is not married. To assume a celibate person, even one who has taken a vow of celibacy, is sexually abstinent is quite a dangerous stretch indeed. Need I point out the very unfortunate sex abuse scandals that continues to plague the Roman Catholic Church?

In the same way, if someone identifies him/herself as sexually abstinent, the only thing we ought to be able to say for sure is that he/she is not engaging in any type of sexual expression. It would be false to assume that a sexually abstinent person is not married, because there are a lot of married people who are indeed sexually abstinent.

In your case, Adam, I believe you are telling me that you are both not married (celibate), and because of your particular sexual predilection — young boys — you must also be sexually abstinent. If I’ve got this right…and it is very important that I not misinterpret your words…then I think there are options you may not have considered.

I firmly believe that we learn all our sexual expression. I hasten to add that sexual orientation and sexual expression are not one in the same thing, just like celibacy and abstinence are one and the same thing.

Everything we eroticize, in your case boys, is learned behavior. You learned to eroticize boys at some point in your life; you can now learn to eroticize a more appropriate group of people. This isn’t a particularly easy thing to accomplish, but it’s not impossible either. Again, I am not saying that you can reprogram your orientation, but I am saying that you can learn to redirect your erotic attentions elsewhere.

Anytime any one of us discovers that the object of our desires is someone inappropriate, we need to adjust our eroticism immediately. This is the better part of being a sexually responsible person. In our culture, pedophilia is just one such inappropriate eroticism, but there are many other taboos. A father for his daughter, a mother for her son, a boss for a subordinate, a man for his neighbor’s wife, a teacher for her student, a counselor for his/her client, a congressman for his page…are you getting the picture? I hope so. And the list goes on and on.

I believe learning to readjust your eroticism to a more appropriate outlet is a much better option than trying to live a sexually abstinent lifestyle. The reason I believe this is that having a more appropriate outlet will at least help you channel your pent up sexuality. If you have no outlet, or limit yourself to masturbation, you will most likely intensify your longings and further fixate on the inappropriate object of your current desires.

Like anyone trying to wean him/herself off a bad habit, the task ahead of you Adam, will be challenging. But it will also be enriching and life-affirming. I hasten to add that you ought not try to do this on your own. Work with a sex-positive therapist.

You’re a relatively young man with many years ahead of you. These years can be filled with happy, healthy and appropriate sexual expression. Make it happen.

Good luck

Pride Goeth Before The Fall

Name: Jen
Gender: female
Age: 59
Location: North Dakota

I’m a widow and I am so sad. The fellow I’m going with, I really love him, but I can’t have an orgasm with him. I was able to have an orgasm with my husband who is passed away. And I can when I am playing with a toy by myself.

He has such pride and I don’t want to hurt his feelings, because it would take me about a half hour of foreplay to get there.

Thank you for your message, Jen. Your concern about your man and his inability to rock your world is, sadly, a very familiar complaint. I hear it from women all the time.pride

You say that your man is prideful and that you don’t want to hurt his feelings. But are you really willing to sacrifice your sexual wellbeing on that altar? I hope not. Even prideful men can learn something about pleasuring the woman they are with.

Let’s just say that this guy your dating knew how to pleasure all the women he has ever been with previous to you. That pedigree doesn’t make him an expert on pleasuring every other women he will meet, and that includes you.

Allow me to share with you the exchange I had with another woman in your situation. Perhaps my advice to her will be helpful to you. This is from…

Name: Zoe
Gender: female
Age: 25
Location: Boise
I learned how to masturbate when I was 12. From that first time I’ve loved how it makes me feel. No matter how good my lovers are; they never come close to the pleasure I feel when I’m touching myself. I like the intimacy I have with my boyfriend, but he’s not very good in the sack. I’ve been trying to get him to watch me masturbate, or we could masturbate together, so that he’d know how to touch me and make the bells ring. Unfortunately, he’s really straight-laced and he thinks my suggestion is perverted. He resists every time I bring it up. Sometimes after we have sex, I wait for him to fall asleep then get myself off. Is this selfish?

selfish-man

You betcha it’s selfish, selfish as all get-out. Not you, Zoe, but the bonehead you’re fuckin’. This is a classic, “you can lead the horse to water, but you can’t make him drink” sorta deal. Only here we have a “you can lead the horse’s ass to the mysteries of pussy, but you can’t make him appreciate them.”

I gotta ask, what makes a sexually enlightened chick like you hook up with and stay with bozo like him? Do you actually think that he’s gonna magically come around one fine day and let you lead him to nirvana? I think not. You know why I think this? It’s because you’ve created a monster — an “all I need to worry about is me gettin’ off in my girlfriend’s snatch” kinda monster. And that’s one scary kinda monster.

I am of the mind that it’s fruitless to try to get an obstinate partner, like your guy to do something he doesn’t want to do. The nagging alone will harden his resolve to resist. This does not mean you’ll never get your way. It just means that you have to go about this in a completely different way than, “oh honey, won’t you please cum and watch me jill-off? In the numbskull’s defense, he may be missing the point completely. He may not understand why you want him to watch you pleasure yourself. So if your agenda is to get him to be a better lover, that’s how you’re gonna have to approach the big lug.

First off, he needs to be told, in no uncertain terms, that he’s not the Hercules in the boudoir he thinks he is. This is gonna sting his ego like crazy and it might very well be the end of him and you altogether. But I assure you, risking this is much better than maintaining the status quo. Because, with each passing fuck, he will be more convinced then the fuck before that he’s da man.im_da_man

Once you burst his bubble, you’ll need to immediately inflate a new one for and with him. Us men folk can’t live very long with out our illusions. Begin this inflation process by taking some responsibility for this predicament. Own up to keeping him in the dark about his lack of sexual prowess. Then tell him that there’s a very easy and fun fix for the problem. Maybe if he understands that you want to jill-off for him as a tutorial, he’d be more compliant.

I’d be willing to guess that if you made this presentation more of a game or a role-play scenario then a seminar he’d be more receptive. Why not try something like this. Introduce a blindfold into your sex play. Have him strip down to his jock for you, then blindfold him. It’s gonna be his job to get you off without using the magic wand he has stuck in his jock. The blindfold will necessitate that he use his hands (and mouth) to find and pleasure you. While you tease his dick inside his jock guide his hands to your pussy. He’ll no doubt be fumbling around at first, so you’ll have to encourage him with some dirty talk, or actually use his hand to jill yourself off. Just remember keep it fun and playful and keep his dick safely tucked away.

You can see how this little exercise could be educational for him without being emasculating. Once he figures out that there’s more to sex than the old in and out, he might actually cum around, so to speak. Similarly, you might, on another occasion, submit to the blindfold yourself and have him use your hand to jack himself off. In time, you be able to do away with the blindfold altogether. But then, you might want to introduce restraints of some sort. While he’s buck naked and restrained put on a hot and horny show for him. Tease him with your self-pleasuring, but don’t let him touch you. Maybe rub yourself with his stiff cock. Since he’ll be unable to resist, it will be like masturbating with his pecker. Doesn’t that sound like a load of fun for all concerned?

Good luck

The Great Porn War

Name: Jennifer
Gender: Female
Age: 23
I am 23 years old and I like lesbian and gay porn. It’s been my favorite since I discovered it a few years ago. But my boyfriend hates the thought of people of the same gender having sex. I don’t like hetero porn, and that’s all he uses. Is there any way I can get him to enjoy my kind of erotica?

porn.jpgYour boyfriend a dreadful drag, huh? What’s he afraid of, do you suppose? Ya think he’s afraid he’ll pop wood while he’s watchin’ gay porn with his girlfriend. That’ll surly to shake his masculinity to its foundation. I mean, it’s one thing for him to get a boner when he’s checking out the queer stuff by himself — and you know he does! It’s another thing all together for him to get hard watching two dudes fuck while he’s with you. It’s clear to me that your BF has issues, darling. And I think you know that too.

Now I’m not suggesting that he has to like everything you like, or that you have to like everything he likes. A couple can have a really healthy relationship despite differences in the kind of smut each prefers. But matters of taste aside, I think a smart chick, like you, knows that porn is as much a political statement as it is a sexual statement.

Here’s what I mean. Most straight porn features male identified sex — exclusively. That’s probably why you, and 90% of your sister women, don’t like it. The producers of most of the stuff in this genre create it with a predominately straight male audience in mind. And you can pretty much count on it exploiting women in the process. Gay porn does not exploit women, for obvious reasons and lesbian porn is the most radical of all. It is unabashed female identified sex. No female exploitation there. Of course, I’m talkin’ about real lesbian porn, not the caca that simulates girl-on-girl sex that gluts the “straight” porn marketplace.

Most straight males get off on hot girl-on-girl action in straight porn, because the performance represents male identified sex. In fact, one of my good gal pals in the porn business often says that girl-on-girl sex in straight smut is about as far away from authentic female sexuality as gay porn, which has no women in it. i just can't

I’m gonna go out on a limb here, Jen and guess that you’re a little too radical for Mr. Whitebread. But if you think that he’s worth the effort involved in loosening him up, start by reassuring him that there will always be a place in your heart for his johnson even when you’re enjoying a sweet lesbo fantasy. If you really want to enjoy yourself with your guy while you enjoy your dyke porn, give him permission to do a voice over for the movie you’re watching together. Tell him you want him to pretend he’s a porn star and he’s gonna appear in the next scene with the two chicks you’re watching. Watch the lezzie scene together and then have him tell you what’s gonna happen in the next scene when he catches the two naughty vixens. Perhaps you could suggest that he roll play that with you after the movie. Ya see, Jen, you’re gonna have to trick the monkey into watching what you want, cuz he ain’t gonna open his mind all by his-own-self.

Deprogramming him of his homophobia may be a bit more challenging, but there are ways. You could start by telling him that everyone knows that no one sucks a guy’s dick like another guy. And so you want to pick up a few pointers from the pros before you go down on him again. When the big cock-sucking scene begins start grabbing at his package. We all know he’s gonna be hard as a rock. Those repressed types are so damned predictable. Now if at all possible start blowin’ him with the same vigor as the dudes in the movie. Blowjobs are the great equalizer. Mr. Whitebread will be enjoying himself so much he’ll hardly have time to reflect on how radical he’s becoming.

lesbian pronIn the end, I don’t think you should compromise and watch hetero porn unless he’s willing to compromise too. Of course you both could watch your chosen porn privately, but where’s the fun in that. Or you could just trade-off one scene of his for one scene of yours. Or compromise with some hot bisexual porn. There’s not a whole lot of really good bi porn out there, but there is some. Just be discriminating. Life is just too short for bad smut.

You could try dueling porn. Two screens, two TVs or a TV and a computer screen, each playing a different type of porn. Or you could really throw caution to the wind and have a full-blown fuck-O-rama — multiple screens with multiple images all going at once. It’s so easy to do these days with the proliferation of computers tablets, phones even, and online porn. And just about every household has at least two TVs and two computers lying around. So knock yourself out, girl!

It’s clear to me, Jen, that you’re gonna have to take the lead in this. You being the more enlightened one. I believe that your arousal will arouse him. And if your fire doesn’t ignite his, simply throw the bum out!

Good luck Ya’ll

Wonderful World of Butt Plugs!

Cassandra
I’m really curious how you actually overcome the fascination of wanting anal sex? What do you do and what does it take?

Ahhh, your pullin my leg, right? Cassandra, darling, I don’t get it. You have a fascination with wanting some hot backdoor action; is that correct? Am I supposed to gather from this rather round about way of putting things that you have yet to explore ass fucking? That’s what it sounds like to me.

i'm wearing my butt plugIf I’m correct in this assumption, the sure-fire way of overcoming this or any fascination of wanting this or anything else is to indulge yourself the very thing you’ve been wanting. This is not rocket science.

Once you have a taste of what you’ve desired, you’ll no longer need to overcome a fascination. If by chance, you’re actually wondering if you want to enjoy your butthole or not and you want to discover this on your own without the pressure of having a partner present; then I suggest you do a little experimentation on your own.

Allow me to introduce you to the Wonderful World of Butt Plugs! Not sure what a butt plug is or why you would want one? Or maybe you sure enough know a butt plug from a hole in your head, but you just don’t know how to go about choosing the right one for you. Well, never fear, because Dr Dick is here with another one of his Handy Dandy Sex Toy Advisories: Plug Your Hole In Three Easy Steps. And you can thank all my inquisitive correspondents and the treasure trove that is Dr Dick’s Stockroom for the heads up on these puppies.

A butt plug is an anal stimulation device that allows you to enjoy sustained anal pleasure (and prostate stimulation for the men folk) without the worry of having your toy fall out, or worse, disappear up your chute.

Let’s look at a typical butt plug to get a feel for how it works. Unlike most dildos and other anal toys, a butt plug is shorter and has a unique shape. The insertable part is often a tapered cone shape, designed for easy insertion and that all-filled-up feeling while it’s in place.

The plug tapers more dramatically near the base into a notch. This allows your sphincter muscle to close down on the plug keeping it firmly in place. Finally the wide base keeps it from slipping inside your bum.

Pretty gal-darn clever, huh?

But why would I want a plug in my ass? You might query. That, my friend, is a question only a rank amateur would ask. Unfamiliar with the joys of butt play, are ya? Well, here’s the 411 on anal pleasuring. Your bum is chock full of nerve ending that, when stimulated, induce intense pleasure. And a butt plug can be worn for hours at a time for a sustained dose of devilish delight.

Once you decide to give a plug a try, you’ll have loads of options to choose from. There is a slue of different sizes, shapes colors and textures. They come in several different materials. And some even vibrate. How fun is that?

Let’s look at all these options in turn.

— Start with SIZE.
If you’re new to the whole anal thing, I recommend you try something small. You’ll want an insertable length of less then 4” and a diameter of 2.5”. Feeling a bit more daring? Want to increase the insertable length and/or diameter? Knock yourself out, my friend. There are dozens of sizes available.

— Next choose a Material.
Got the dimensions you want, but not sure about what kind of material you want plugging your hole? I know that may sound funny, but it actually does matter what you insert where the sun don’t shine!

Say, Dr Dick, how do I know what material is best for me? Excellent question! See, you’re becoming a well-informed consumer already. Let me detail some of the finer points for you.

Latex — the granddaddy of sex toy material.
PLUSSES —
Inexpensive
Soft and flexible
Use with both water-based and oil-based lubes.

MINUSES —
Porous, thus less hygienic
Difficult to clean
May contain phthalates
Distinct rubbery odor

Jelly —advancements in chemistry transformed ordinary latex into even softer and more pliable jellies.
PLUSSES —
Inexpensive
Super-soft and flexible
Appealing translucent jelly-like appearance
Use with both water-based and oil-based lubes.
Comes in a variety of colors

MINUSES —
Porous, thus less hygienic
Difficult to clean
Probably contain phthalates
Distinct rubbery odor

Silicone — a non-latex product that come in two varieties — firm and soft.
PLUSSES —
Durable and long lasting
Easy to maintain
Hypoallergenic
Waterproof
You can sterilize silicone toys by boiling themc552.jpg
They’re bleachable
Dishwasher safe
More realistic feel
Retains body heat
Comes in a variety of colors
Less of an odor

MINUSES —
More expensive
Use only water-based lubes

Stainless Steel —it is smooth, hard and a thing of beauty.c991.jpg
PLUSSES —
Super-durable and long lasting
Nonporous
Easy to maintain
Hypoallergenic
Waterproof
You can sterilize Stainless Steel toys by boiling them
Bleachable
Dishwasher safe
Much heftier weight
No unpleasant odor
Can be warmed or chilled
Use with both water-based and oil-based lubes.

MINUSES —
More expensive
Hard and inflexible

Pyrex Glass — a hard dense glass that will not shatter or splinter. A work of art.
PLUSSES —
Super-durable, long lasting
Nonporous
Easy to maintain
Hypoallergenic
Waterproof
You can sterilize Pyrex toys by boiling them
Bleachable
Dishwasher safe
Hefty weight
No unpleasant odor
Can be warmed or chilled
Use with both water-based and oil-based lubes.

MINUSES —
More expensive
Hard and inflexible

New Supersoft — a new material that’s has the closest feel to real-life skin. It can be both soft and rigid.
PLUSSES —
Less expensive
Great texture

MINUSES —
Very porous
Less hygienic
Always use with a condom
Use only both water-based lubes.
Difficult to cleanb667.jpg
Distinct rubbery odor

Rubber — An old standard!
PLUSSES —
Inexpensive
Durable, very long lasting
Waterproof
Use with both water-based and oil-based lubes.
Comes in a vast array of colors
MINUSES —
Very porous, less hygienic
Difficult to clean
Distinct rubbery odor

— Next choose Special Features.
Once you’ve decided on the material you want, you can customize your butt plug with special features like:

  • Bendable
  • Inflatable
  • Multi speed vibrating
  • Suction cup

— Next choose Texture.
Latex, silicone and rubber butt plugs come in an array of textures. Which one of these buggers will tickles your fancy?

  • Bulgedtunnel plug1
  • Noduled
  • Nubbed
  • Ribbed
  • Smooth
  • Studded
  • Swirled
  • Veined
  • Velvety

Good luck.

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