Category Archives: Ass Play

What does is all mean?


Name: Jane
Gender: Female
Age: 23
Location: Vancouver. BC
When my boyfriend and I have sex, there’s a 50/50 chance that he will put his penis between my butt cheeks and hump me that way until he cums. (It’s just intense rubbing, no anal penetration). Even though I don’t feel like I’m getting any pleasure from it, my vagina gets wet, and if he touches me down there and feels that I’m wet, it turns him on even more. What’s going on here?
He’s very affectionate and he tells me he loves by my body. He says he’s totally straight, but this whole anal thing confuses me. If he’s not gay or bi-sexual, why is it that it takes him 20+ minutes to cum during vaginal sex, but only 5 – 7 minutes to cum during anal?

Ok, Jane, to start with, your BF isn’t doing anal. Believe me, darling, you’d know if he were. Anal sex, by definition, means anal penetration. There’s a name for what your freaky boyfriend is doing — rubbing his cock in your crack, but not penetrating you. It’s a form of frottage, or sexual stimulation by rubbing. This is the sexual practice of choice for most lesbians, most commonly referred to as pussy-bumpin’. Hey, maybe your BF is a lesbian!analsex joke

Second, your pussy may be getting wet because your boyfriend’s pre-cum and spooge is dripping down your crack, past your “taint” and all over your fine cooch. It ain’t you producing the wetness, which explains why you’re not aroused. I hope that clears up the mystery juice for ya.

Third, loads of exclusively straight men are into anal. Most are into butt fucking their women, but some are into being fucked BY their women. We call this practice pegging — a woman straps on a mighty fine dildo and drives her man insane with a buggering he’ll not soon forget. So you see, fucking is not just for cunts anymore!

Forth, perhaps, just maybe, your vagina isn’t as tight as your what your man is experiencing between your ass cheeks. Maybe, just perhaps, that’s why it takes him less time to bust a nut that-a-way than in a more traditional form of fucking. Also maybe, he’s more turned on with the allure of the forbidden, taboo backdoor action. I guess the only way you’ll know is to ask your BF straight-up, as it were, so to speak.

So let’s review then, shall we? Now that we know for certain that an interest in cornholing a sweet ass is not just a gay thing. You can relax about your BF bein’ queer for wanting to hump your bum. For some guys this is their favorite kind of sex. They love to bust a nut by rubbing their dicks between a chick’s tits, thighs, buns, or feet. It’s anyone’s guess why these dudes prefer this to getting off in, on or around a pussy, but whatever it is, it’s completely harmless.Anal sex

Here’s a tip, Jane. Relax into this with the ‘ol BF, why don’t ya? Once you stop worrying about his sexual orientation because of his fascination with your be-hind, you may actually enjoy the special attention he’s paying your boot-ty.

And hey, if your BF’s freak with your ass crack isn’t gettin’ you off, you don’t have to just lie there and take it, ya know. While he’s grinding away back there, you could be spending some quality time with little miss clit with say a swell vibrator. Soon you’ll be enjoying things as much as he.

Good luck

Wonderful World of Butt Plugs!

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.
Soft and flexible
Use with both water-based and oil-based lubes.

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.
Super-soft and flexible
Appealing translucent jelly-like appearance
Use with both water-based and oil-based lubes.
Comes in a variety of colors

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.
Durable and long lasting
Easy to maintain
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

More expensive
Use only water-based lubes

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

More expensive
Hard and inflexible

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

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.
Less expensive
Great texture

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!
Durable, very long lasting
Use with both water-based and oil-based lubes.
Comes in a vast array of colors
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.

What a pain in the ass!

Name: Dan
Age: 55
Gender: Male
Location: Illinois
My wife and I have enjoyed anal sex (giving and receiving to each other) for years, but now I have a problem I need help with. I had a hemorrhoidectomy surgery 3 months ago and we waited 3 months to start up again. Now using the same strap-on as we have been using it was very uncomfortable. The strap-on is only 1-1/2 “thick and I tried again by my self but it did not matter how much lube I used it still hurt. Then I started bleeding. It seems that when the hemorrhoidectomy surgery was done it made my rectum smaller. The question I have is; is there away to stretch the rectum back to the pre-surgery size or do I have to buy smaller toys (the 1-1/2” is the smallest we own right now)? I appreciate any help you can give.

Sorry to hear about the pain in your ass, Dan. I know that recuperating from invasive surgery like that isn’t fun.

ass-painHere’s the thing; I believe that you’re gonna need way more than 3 months to heal completely from the hemorrhoidectomy. I know, bummer, huh? If I had to guess, your down (pardon the pun) time will be more like 6 months to a year.

At 3 months, your ass is, no doubt, healed enough for comfortable bowel movements. But butt fucking is quite another thing. And I don’t think it’s simply an issue of stretching your rectum or the amount of lube you use. Internal healing isn’t like external healing. Plus, there’s the fact that every one of your bowel movements is stressing your rectum making the healing process more lengthy. I encourage patience.

That’s not to say that you still can’t enjoy your hole. External simulation on your rosebud will feel real nice. Digital stimulation, just inside your hole, might also be possible. Just don’t over do it or you will find the healing process will take even longer.

I have a question. Are you able to stimulate your prostate without pain? Or do you experience pain with any insertion to any depth?

Since you’re not here to fill me in on the gory details, I’ll try to respond to my own questions. If you are able to stimulate your prostate without difficulty, I recommend that you keep your anal wanderings to that depth. If, on the other hand, you can’t even go that deep without discomfort, then I suggest you stick to external stimulation for the time being.pain-in-the-ass

I already suggested butthole massage, but don’t forget your perineum, or taint, if you will. I suggest that you find a good strong vibrator, perhaps one that has a pointed (phallic) shape to it. You’re gonna want some fine pin-point accuracy for this stimulation. Move back and forth between your hole, over your taint, to your balls. Stimulate the whole shebang down there. I think you will find that pressing the vibe into your perineum will shiver your prostate in the most delectable way. Done correctly you will discover that your whole pelvis will light up.

[Anyone out there who is afraid of anal insertion, but wants to experience some of the fabled pleasures associated with being a butt pirate, will want to give this external vibration thing a try. Who knows, one day you might wind up slipping the phallic shaped vibe in your ass for real and discover that your insertion fears were unfounded.]

Dan, give your ass at least 3 more months to heal. At that time try doing some very careful and tentative insertions to see how things feel down there. If there is even the slightest pain [internal pain as opposed to sphincter discomfort] stop what you are doing. Don’t try and force the issue. Like I said, this could take a year to heal properly.

Keep me posted on your progress.

Good luck

Bottom Wannabe

Name: Bottom Wannabe
Gender: Male
Age: 29
Location: Ocala, FL
Dr. Dick, First of all, I love your site! It’s informative, fun, and funny! My question is related to how to be a better bottom- I’ve read all your forums on this and my question is related to enemas. To be blunt and short, I bought a gay enema water syringe/bulb, squirt water up my ass a few times to clean it out. Sometimes I’m a totally clean bottom and other times, after a good fuck, there is shit that comes out on the guy! :-( It devastates me when this happens, and more often than not it happens. I’ve quit having anal sex and just stick to oral sex. I love getting a dick up my ass, but I’m too embarrassed. What am I doing wrong? What can I do differently? I put probably a quart of water at a time in my ass before squeezing it out. The problem exists if I have sex right away or if I wait a couple of hours.

If you are douching properly before the butt fucking there shouldn’t be much seepage if any. Maybe you’re not taking care of business correctly. Or you’re using the wrong kind of douche. (Check out the Ergo Speed Douche, it gets excellent reviews.) Or maybe you need to douche twice. Or maybe you’re being fucked too hard. I know that a vigorous fucking will introduce a lot of air into the bottom’s rectum expanding it and making for that “OMG, I gotta take a dump” Ergo Speed Douchefeeling.

It appears that your bowels are working perfectly well, so you do not want to mess with that any more than what you are already doing. My guess is that it would be a whole lot easier to alter your mindset about poop than to alter anything else in this equation.

You know the saying; “Shit happens”? Well then, now you know the true meaning of that phrase. Just about anyone who is on the receiving end of a vigorous fuck is gonna have a little seepage. If ya can’t stand that, if it offends your delicate sensitivities, your bottom wannabe days will be numbered.

Here’s my suggestion: do the best you can with the prep work and then enjoy the fuck fest. Have a trick towel handy at your bedside to discreetly mop up any shit that happens. It’s not the end of the world. And remember what I always say: There can be some unexpected side effects to rootin’ around in someone’s hole, regardless how fastidious the bottom is about his hygiene. Just ask porn stars.  But, in the end, they are just side effects; so make your peace with that and don’t give a shit. It’s no big deal; you’re just being human.

Good luck

Tricks Of The Trade — Part 1

A friend of mine, who is writing a book about male sexuality for women, asked me if I could be her go-to-guy for a bunch of questions she had about pleasuring a man which she wants to include in her book. I think it is only fair that you, my loyal audience, should get this information before anyone else does.

What would, in your esteemed opinion, be your five hot tips for giving a great hand job?

First, there are 10, not 5. Hand jobs are too important for just 5.

Most men love a good old-fashioned hand job. Here’s the deal with a lot of us folks who own a dick. We first become acquainted with the pleasure our cock can offer through handling ourselves. And when it comes right down to it, there is rarely a mouth, pussy or ass that can compete with the variety of stroke and firmness of grip that a hand can provide. Simply stated, the humble hand job is the ideal way to pleasure your man. Just remember, even though jerkin off your guy isn’t particularly exotic, as far as sex acts go, it never has to be boring for you or him.busy masturbating

1) I am of the mind that a brilliant wank begins with a first class lube. Many guys swear by silicone-based lubes for this purpose, but a hand job connoisseur will probably have his very own favorite. Start off with just enough lube to make things slick, you don’t want to over do it. Get a feel for his johnson and what you have to work with. Skillfully draw back the skin of his rod toward the root of his dick till it is taut. This is much easier to do on uncut men, but even most cut men will have some skin left for move.

2) Tell your dude how much you like his meat. A hand job is a perfect time to marvel at the work of art before you. Feel free to uooh and ahhh a lot. Your man will get off on you admiring his unit. For, as we all know, a hard man is good to find. Can you wrap your fingers around the base of his unit and get a good grip there? If not, you’ll want to consider a cockring for this purpose. if you use a cockring, you’ll free up both your hands for what’s to come.

3) Now that you got yourself a really nice boner goin’, get between his legs. Take his cock between the palms of your hands, interlock your fingers and guide your hands up and down his shaft. Your thumbs should be on the underside of his dick, so that on each stroke up and down, you hit his frenulum with the pads of your thumb. Now with his cock still between your palms, rub your hands together, like if you were warming them. This will provide a great new sensation for your guy.

cock,schlong, dong4) Hold his cock in one hand and with the well-lubed palm of your other hand, slowly move it in nice lazy circles all over his dickhead. This is a particularly delicate procedure, especially if your man is uncut. His dickhead will be super sensitive, now that he is fully aroused. And don’t forget, if you are using a cockring, his pecker will be even more engorged than usual, making it hypersensitive. Be sure to ask for feedback on this move. If he finds this too uncomfortable, move on to something more pleasurable. Here’s a tip: us men being who we are will, no doubt, already be giving you directions on what to do and how to do it down there. So all you have to do is follow his lead. Remember, he knows his way around his joint better than anyone.

5) Don’t forget to service his nuts. Since a guy’s jewels are less sensitive to touch than his dickhead, you can manhandle them a lot more. Squeeze and tug and even gently slap those babies to your heart’s delight. While you are doing that, and with his dick flat against his belly, shimmy the heel of your hand up and down the underside of his cock. You see how you are incorporating different sensations and movements all at the same time? Keep this up and your man will be putty in your hands, no pun intended.

6) Interlace your fingers and make a tight passageway through the palms of your hands. Pump up and down his shaft this way. As you get to the top of his cock close the passageway even tighter. Then make him squeeze his way in as you slide back down to the bottom. Then with one hand rapidly following the other in only a downward stroke, make like a perpetual penetration tunnel. This will make his eyes roll back in his head in ecstasy.titty fuck01

(This might be a good time to incorporate other parts of your body besides your hands. Most men get off on a titty –fuck. Cozy his cock between your boobs and have him hump away. You can also use your feet in the same fashion. Lots of guys can really get off fuckin’ a chick’s (or dude’s) feet.)

7) Now, back to the hand job. Rhythmically stroke only his rod. Watch as his dickhead swells and turns red or even purple. Once it’s bright red, use your fingertips on the tip of his dick like you are turning a doorknob, first to the right, then to the left. Lightly at first, but slowly increase the pressure till he begs you to stop. Now you got him right where you want him.

8) Here’s where things can get really interesting. When he’s least expecting it, move one of your hands down past his nuts and taint. You know what a taint is, don’t cha? That’s the patch of skin between his balls and his asshole. It got its name from taint ass and taint balls, ya get it? Anyhow, once past his taint you’ll find his rosebud. With a well-lubed finger massage his pucker. If this is virgin territory for your man, he’s in for the thrill of his life. Continue to stroke both his cock and asshole. Don’t be afraid to try and push your fingertip past his sphincter. If he lets you inside, you will have access to his prostate. But even if he doesn’t, massaging the outside of his hole will bring him very close to an explosive conclusion.

9) If you’re ready to finish him off, so to speak, pick up the pace of your stroke. He will be breathing heavily now and he’ll look down over his chest at the miracle happening between his legs. Tell him to throw his legs in the air and spread them as far apart as possible. This will add considerably to the muscle tension that you’ve already built up. And a thunderous orgasm is all about muscle tension.

Now bring this puppy home. Lick his balls, finger his hole and beat his meat. Insist that he keeps his feet in he air and his legs splayed. Momentarily, he will begin to quake with building mini-orgasms. He will no doubt try to buck himself to conclusion, but don’t let him. For the moment you’re in charge down here, not him. Tease him one last time as he nears ejaculation. When he’s almost there, suddenly stop what you’re doing. This will, of course, drive him crazy. And don’t resume your stroking till he begs for it.

It will probably only take a few more strokes before he gives up the spunk. Keep your face, or at least your eyes, out of the way, because when he finally blows it will be explosive. If you’ve toyed with him for any length of time, you will have built up quite a load and it will shoot in spurts till he is empty.

10) His cock will be hypersensitive after he cums, so be gentle.



1. “Male G-Spot” clarification — we’ve heard the prostate referred to as the “male G-spot,” but we’ve also heard the frenulum given the same name. Which is it? Or is this term not appropriate for either one?cake & sodomy

Male G-Spot more appropriately denotes the prostate, definitely not the frenulum. However, let’s be grown up about this and skip the unnecessary comparison between the G-Spot and anything in the male anatomy. Because that’s like saying a clit is a female penis. If we must use shorthand for the prostate, try P-Spot.

2. How should a woman go about finding and petting the prostate?

  • First, trim your fingernails and file them smooth. And before you start playing with a man’s hole have him relax.
  • Take a relaxing shower, a warm bath, and/or try some deep breathing exercises will help him do that.
    Have a ready supply of a water-based lube handy. Silicone-based lubes are swell for these exercises too. However, this type of lube isn’t recommended for use with a condom.
  • Start with a nice hand job. Stroke his dick with your lubed hand to get him into his happy place.
  • Gradually slather some of that lube on to his balls and taint. While his legs are open find his hole and play with his rosebud. Gently massage the area around his asshole, but don’t side your fingers in just yet. Simply let him get used to the feelings of playing at the opening of your ass.
  • Let your play include the tip of your finger entering your ass.
    If you do this while you’re stroking his cock, you will find that his hole will actually open and invite your finger. That’s the great thing about pleasuring one part of your body while learning to pleasure another.
  • Once he’s comfortable with your fingertip inside, try pushing it in further and move it around a little. Try pushing it and pulling it out of his ass. Ya know, like finger-fucking your man.
  • About an inch or so inside your man’s ass, move your finger in an upward motion along the wall of his rectum. You’ll discover a round bulb of tissue the size of a walnut — this is his prostate.
  • It shouldn’t be hard to find, particularly if your man is all horned up. It will feel smooth and hard, like a flat stone.
  • Give that puppy a nice gentle massage with your fingertip. If you’re still stroking his wood, don’t be surprised if this prostate massage gets him off. In fact, you will find that his prostate actually enlarges a bit and becomes more firm just as he is about to shoot.
  • As he cums you will also notice that his sphincter muscle will tighten around your finger and pulsate with each squirt.

3. What’s the best position to put the guy in to do this?

body as art5821Your man should be on his back, while you face him between his open legs. This gives you access to cock, balls and asshole.

4. Should a girl be worried about hurting her lover while playing with his prostate?

If you go slow and are gentle, there’s nothing to be concerned with. Don’t forget to ask for feedback. And if you want to know what he is feeling, finger your hole first.

5. In your experience as a sex therapist, do you find that straight men are wary of letting their female partners explore anal play?

Oh yeah, big time! Straight guy have it in their head that ass play is gay. I always respond that would be true if only the gays had prostates.

6. If so, how would you advise a woman to address or overcome any homophobic paranoia her partner might have in regards to anal play?

This is a very delicate issue. The best a woman can do is invite him to experience the new sensations. Anything more than that can backfire. If she is too insistent, or tries to shame him into it, the guy’s fears will quickly become a phobia.

7. In your experience, is male vulnerability a factor in anal play, and if so, is there anything a woman should do or say to psychologically care for her lover?

Oh yeah! Like I said above, ass play is often associated with gay sex. The best thing a woman can do is watch some hot butt sex porn with her man, where the dude is on the receiving end of things. These are called pegging vids. Then there are How To Videos like TRISTAN TAORMINO’S EXPERT GUIDE TO ANAL PLEASURE FOR MEN.  Check out Dr Dick’s How To Video Library for loads more titles.

Look for PART 2 of this series on Friday, October 10th.

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