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Learning to ride

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Hey sex fans!

We’re all back from Spring Break. Did you miss us? We sure missed you. So ok, let’s get this ball rolling again with a timely question from one of my correspondents.

Name: Drew
Gender: Male
Age: 23
Location: Boise
I’m gay, I’m a virgin, and I think I may be afraid of sex. In all the porn I’ve seen, the bottom guy looks uncomfortable and in pain, why would I want that? I’ve only done anything sexual with one guy and I was so anxious that I couldn’t even get up. I liked the guy, he was hot, and I enjoyed all the fore-play type stuff, but I just couldn’t do anything else. Any advice on how to get over this?

First thing, don’t ever look to porn for your sex education; you will surely be misled. Second, that grimace that you report seeing on the bottom’s face as he is being penetrated, may be a grimace of pleasure not pain. I think you are projecting your own discomfort on the guys in the movies.

Let me tell you a little story. The other day I was walking in the park with Ginger the dog. Actually, I was trying to walk like a normal person, but she was pulling me along like a maniac. We were both, in our own way, enjoying some beautiful spring weather and the sights, sounds and smells nature in its glory. As we walked along we encountered a father and son who were seriously involved in what appeared to be the kid’s first lesson in riding a bicycle…without training wheels. Despite the father’s patient encouragement the kid couldn’t seem to get the hang of it. He would start out ok, but just as soon as his dad let go of the back of his seat the boy would wobble and eventually crash. There were plenty of tears, a skinned knee and the boy’s fear and anxiety was thick enough to cut with a knife. It was quite a scene.

The kid was convinced that he didn’t have what it took to ride on his own. His defeatism fueled itself and became a self-fulfilling prophecy. He finally gave up. Sat down on a bench, his bike in a tangle at his side, and refused his father’s pleading that he try again. In the kid’s mind the bike was the enemy another attempt would only hurt and humiliate, and so the lesson ended.

What the kid lacked was self-confidence, a sense of adventure and probably more importantly — balance. I wish I had had an opportunity to suggest to the boy and his dad, that they might try another ploy. I wanted to say, set the bike aside and work on that balance thing first. This would surely increase the boy’s confidence and it wouldn’t cost a blow to his ego or his knee. And it would be fun.

I would have suggested the dad start by helping the kid walk on 4” curb, balancing himself as he went. Then the dad could increase the challenge to include balancing on one foot, then the other. Once the kid discovered the power within him to accomplish these tasks, the bike could be reintroduced. The father would assist the boy in drawing upon his skill in balancing on the curb to master balancing on his bike.

The same will be true for you, Drew. Sex is nothing to be afraid of. Rather it is a skill that one learns. Some, obviously, take to it quicker than others, but everyone can learn a happy, healthy sexual expression that will build self-esteem and bring great pleasure.

I want you to start exploring and enjoying your bottom on your own. Like the kid in the park, you need to acquaint yourself with the powers that lie within you. He needed to find a sense of balance within himself; you need to find the Big Old Butt Pirate within yourself.

Most all of the discomfort in butt fucking is associated with your sphincter muscle trying to resist whatever it is being inserted in your ass. When this muscle resists to the point of spasm things can become very painful. So here’s what I want you to do.

  • First, before you start playing with your hole — relax. Just like the kid in the park would have needed to calm himself before attempting to balance on the curb. The same is true for you.
  • Take a relaxing shower, a warm bath, and/or try some deep breathing exercises to center yourself.
  • Have a ready supply of a water-based lube handy. Silicone-based lubes are swell for these exercises too. However, oil-based lubricants aren’t recommended for use with a condom.
  • Start with a little self-pleasuring. Stroke your dick with your lubed hand and get into your happy place.
  • Gradually slather some of that lube on to your balls and taint. With legs open wide find your hole and play with your rosebud. Gently massage the area around your asshole, but don’t side your fingers in just yet. Simply 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 your cock, you will find that your 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 you are comfortable with your fingertip inside, try pushing it in further and move it around a little. Try pushing it and pulling it out of your ass. Ya know, like finger-fucking yourself.
  • Find your prostate. It shouldn’t be hard to find if you’re all horned up. It will feel smooth and hard, like a flat stone.
  • Give that puppy a nice gentle massage. If you’re still stroking your wood, don’t be surprised if this prostate massage gets you to bust your nut. In fact, you will find that your prostate actually enlarges a bit and becomes more firm just as you are about to shoot.
  • As you jizz you will also notice that your sphincter muscle will tighten around your finger and pulsate with each squirt

Continue these self-pleasuring exercises until you are comfortable inserting a couple fingers in your ass. Then try a small vibrating dildo. In no time at all you will be ready to jump on your bike and ride…so to speak.

With these exercises behind you, no pun intended, the first time you actually fuck with a partner will be the incredible experience it is meant to be. If you encounter any discomfort you’ll know what to do — deep breathing to relax and priming your hole with a lubed finger or two.

  • First, attend to your personal hygiene. Make sure you’re clean inside. We don’t want any unsightly and embarrassing mishaps to mess up the big event.
  • Remember to take it slow. There’s no rushing pleasure. And you’ll be the one in charge of what goes in your ass, when and for how long.
  • Warm up with some foreplay, kissing, sucking, licking, rimming touching and massaging.
  • Have condoms and lots of lube near to hand.
  • While you’re warming up, start loosening up your ass with your lubed fingers, just like in your self-pleasuring exercises.
  • Once you’re comfortable offer your ass to your partner. Have him replace your fingers with his own. Try some swell finger-fucking first.
  • Once you’re relaxed and loose, lie on your side with your partner behind you. Have him slowly push his cock against your rosebud.
  • Try pushing out like you are trying to take a dump. This will help open up your sphincter for his entry.
  • As he enters you, have him stop so that you can breathe deeply. Give your ass the time it needs to adjust to the new sensations. If there’s pain or discomfort have your partner reverse course and go back to finger fucking before you proceed.
  • Make sure that your partner knows that if you ask him to stop; he will stop. Trust is very important in butt fucking.
  • As he fills you with his dick he will hit your prostate. This will send waves of pleasure through your body and signal your sphincter to open for even more.
  • You may find that you’ll even want to push your ass back to meet and engulf his cock.

By the time this happens you will happily discover that you are ridding your bike all by yourself. And you will be very happy.

Good luck

Twosies beats onesies, but nothing beats threes

Name: Therese
Gender: female
Age: 30
Location: Galveston
My husband and I are thinking about maybe trying a threesome. It’s been a big part of our fantasy life together for several years. We enjoy imagining ourselves with other people when we’re making love to each other. We probably would have acted on this before, but we know that having a fantasy is not as risky as trying the actual thing. What are your thoughts?

My thoughts? Well, going on the number of threesomes and group sex questions I’m getting from straight folks lately; I’d have to say that ya’ll are finally discovering what most gay folks have known for a long time — 3-ways and group sex can be way fun and a potent tonic for a flagging partnered sex life.

Threesomes and group sex are not all that tricky, especially when both partners in the primary relationship are up for the experimentation. And you guys sound like you’ve been priming the pump, so to speak, for some time now. Yeah it’s true, these things can blow up in your face, but that risk exists in just about everything we do. And I am of the mind that nothing ventured is nothing gained. But I also suggest you guys come up with a strategy on how to minimize the chances of being disappointed.

I’d begin by dialing down expectations. If 3-way sex has been part of your marital fantasy life for a while, I’d be willing to guess that these fantasy encounters are always fun and always successful, because they are the products of your imagination. If you go into a real 3-way with those kinds of expectations you could be disappointed. Reality doesn’t always live up to fantasy. The actual thing, as you suggest in your message to me, may not be as fantastic. But you’ll never know without trying. I always think it’s better to have low expectations and be pleasantly surprised when they are exceeded, than to be disappointed when high expectations aren’t met.

You guys need to decide on some ground rules well in advance of the possible encounter. Among the things you ought to consider are:

  • What will you look for in the additional partner.
  • Will it be another woman, another man?
  • Does it matter?
  • Who gets to choose the other partner?
  • Do either or both of you get to veto a perspective playmate?
  • Will the choice be spontaneous, or will you leave nothing to chance?
  • Will you interview for the position, or just put yourselves in harms way, so to speak and go with the flow.
  • Where will you look for these prospective partners?
  • Will you search online?
  • Where will the event take place? At your place, or somewhere neutral, like a hotel?
  • In terms of the sex itself, are there things that will be off bounds?

The more you know about all these things, the smoother the encounter will go.

Gay guys have it easier when it comes to 3-ways and group sex. First, they tend to have defined roles, like being primarily a top, or primarily a bottom. They are also gonna be playing with other gay or bi men. Things are not so easy for ostensibly straight folks, because including a third person will mean adding someone of the same sex as one of the partners. So straight folks have to ask themselves what will be the configuration of the play? Will it be just straight sex — all play directed toward someone of the other sex? Or will it include play directed toward someone of the same sex. Lot of straight guys get off on the idea of watching two chicks get it on, but would never contemplate mixing it up with another dude. So you see where you’ll have to be careful in choosing your playmate. If he or she has a different understanding of the group encounter, there will be problems.

That’s why I always suggest that before an encounter actually happens, it would be good for you to tell your perspective partner what your boundaries are. Also you’d be wise to discover what turns on your prospective playmate. Investing in this discovery process will save possible embarrassment later.

Once the 3-way encounter begins, there is an etiquette ya’ll ought to adhere to. First and foremost is don’t leave anyone out. If you sense there’s an inequity in the amount of play one partner is getting as opposed to another, then that’s a recipe for disaster. If someone seems to be losing interest during the sex play, then start paying that person a little more attention. Of course you guys might just set up a 3-way so one of you can watch the other play with someone else. Ya know, kind of cheering on from the sidelines, as it were. While that may not technically be a 3-way as most people understand it, this kind of set up is very common.

If your interest goes beyond a ménage à trois to, lets say a foursome or possibly a group, much of the same considerations as in a 3-way apply. But since you’re gonna be dealing with even more bodies, personalities and sexual proclivities, more caution is advised. And unless you’re a swinger, or can tap into your local swing set, these situations may be hard to find.

Good luck

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Quickies

Name: Vic
Gender:
Age: 37
Location: Hollywood
I think I have hemorrhoids can you tell me what to do and what kind of doctor I should see

You think you have hemorrhoids, but you don’t know for sure? Since you don’t include the symptoms you might be having, I really can’t help all that much.

What I can tell you is that hemorrhoids are abnormally swollen veins in your rectum and on your asshole. They’re like varicose veins you might see on a person’s legs only they’re in your butt. When bulging hemorrhoidal veins are irritated, they cause surrounding membranes to swell, burn, and itch. They can become pretty painful, and they can bleed too.

Hemorrhoids are caused by too much pressure in your rectum, forcing blood to stretch and bulge the walls of the veins, sometimes even rupturing them.

Frequent causes include:

  • Constant sitting
  • Straining with bowel movements (either from constipation or diarrhea)
  • Severe coughing
  • Heavy Lifting

What you can do to help:

  • Be sure your hole is clean after each bowel movement. Use a premoistened towelette, like baby wipes or Tucks for a thorough cleanup.
  • Avoid excessive rubbing and scratching.
  • Make sure the soap you use is scent and dye free.
  • Apply an ice pack to reduce swelling and follow this with a warm compress.
  • Take a sitz bath. Fill your bathtub with just enough warm water to cover your ass, add Epsom salts. Soak your sorry bum for about 15 minutes a couple times a day.

There are plenty of over-the-counter hemorrhoid treatments — ointments, creams, and suppositories. Give these a try, but if symptoms continue see a doctor. Any physician, including a general practitioner, will be able to diagnosis a case of hemorrhoids.

Name: Jon
Gender:
Age: 22
Location: LA
How can I make myself ejaculate harder and longer when doing masturbation?

Ever try “Edging”? This is a stop/start technique guaranteed to prolong the time it takes you to reach your climax. Grab your dick and begin to wank like usual. Only when you get near to cumming — stop stroking. After the urge to shoot subsides begin to slowly wank again. Every time you approach climax — stop the stroking. Repeat this whole ‘stop and start’ cycle for as many times as you would like. When ya finally shoot you’ll have a stronger orgasm and you’ll spew more spunk. Do an internet search for edging & masturbation, you’ll find a load of information posted by fellow edgers.

Another cool method is the “Squat ‘N Jerk”. Squat on the floor, and stretch your knees as far apart as possible. Lean against a wall if necessary. Feel the stretch in your feet, calves, thighs, taint and asshole. Begin your yank session. Try to keep your rod perpendicular to the ground as you stroke. Because of the tension in your fee, legs and butt, when you shoot you’ll be sure to get more bang for your buck. A variation on this technique is to squat on a dildo or a butt plug. ENJOY!

Name: Trev
Gender:
Age: 27
Location: Toronto
My boyfriend and I got into a fight last night and he punched me in the face. He lost his job about a month ago and since then he has been using drugs, mostly pot but sometimes speed too. When he gets depressed he gets angry and I have to stay out of his way. I’m worried about him but he won’t get help. He says he’s sorry about last night but it’s different when he is high. What can I do to help?

You could start by taking a long hard look at your own enabling behaviors. I can tell, even from this great distance, that you are a doormat. Remember, behind every abuser is an enabler. Behind every drunk and druggie there is an enabler. The fact that you are more concerned about your abusive BF welfare than your own safety tells me there is more to your unhealthy relationship than what you reveal here.

Many victims of abuse, and you are an abuse victim, Trev, believe the abuse is their fault. Regardless of how twisted your relationship may be, there is never sufficient cause for someone to punch his partner anywhere on his body, least of all in his face. Your BF has at least two major issues to deal with: a) his depression/anger/violence and b) his drug abuse. As you suggest these are related. You are neither well positioned nor well enough informed to assist him with either of his problems. In fact, as I say above, you are part of the problem.

You, on the other hand, have issues of your own that he can’t help you with, because he is part of your problem. Abusers often promise to change their behavior, and those empty promises often keep the victim from identifying the pattern of abuse in the relationship.

Anyone in a relationship that doesn’t have the emotional wherewithal to leave an abusive relationship needs help ASAP. Here’s a resource for you: The Gay Men’s Domestic Violence Project.

Good Luck

If it’s not one thing, it’s another…

Name: Malcolm
Gender: Male
Age: 40
Location: Johannesburg
I’m in love with this guy who is as sweet as the day is long. He’s everything I’ve ever wanted in a partner. What makes him so charming is he’s only recently come out as gay. Before this he was married. He is not jaded like so many other guys I meet. But there’s a problem. He’s real vanilla. I guess that’s the down side of coming out of a heterosexual marriage at the age of 35. He’s happy as a clam fucking me a couple times a week. He thinks anal sex is really adventurous and sexually daring. I on the other hand, am suffocating in the boredom. I know, now I sound really jaded, but I can’t help it. It’s just that there’s so much more to sex than what we are doing. I want to introduce him to some kinky shit, but I’m afraid that I will scare him off. What the fuck should I do?

I absolutely adore messages that start out: “I’m so in love. He/she is everything I ever wanted, blah, blah, blah!” Because I know that only a few words later the other shoe is gonna drop, and drop hard. “But there’s a problem, blah, blah, blah!”

Of course there’s a problem. There is always a problem…even with Mr. or Ms. Perfect, or maybe because your honey is so freakin perfect. Take it from me, sexual dissatisfaction will upset even the most tranquil and rosy apple cart and send everyone into a tizzy. Allow me to share with you something I wrote about this very issue about ten years ago. I think you will find the advice as fresh as the day it was written.

So you’ve met the person of your dreams only you haven’t got around to telling your new honey your dirty little secret. The sweet thing hasn’t a clue that you’re itchin’ for some big time bondage. Or that you’d sell your soul to be dominated like the scum that you are. Or you’re salivating over that dildo you have tucked away in the attic, the one that could be mistaken for a floor lamp. Or you’re craving to be spanked till your shameless ass glows in the dark. Or you want to hump his/her feet like a dog and gobble up his/her toe jam. Or you have this nasty little thing about spike heels, frilly knickers and jungle red lipstick.

Never fear, Dr. Dick has heard it all a million times before. Some sorry pervert’s got it bad for white bread. Dear Dr. Dick, Help! I’m in love with the sweetest guy/gal in the word, but our sex life is all vanilla all the time. I’m bored shitless! I know how to liven things up, you see I have this fetish (you fill in the blank) but I don’t know how to tell him/her about it and I’m afraid s/he’ll freak if s/he finds out. What’s a perv to do?

Introducing your partner to your personal world of kink is tricky; the whole little love match could blow up in your face. But a life of pretense and sexual boredom isn’t the way to go either. Why not just stand tall like the disgusting depraved creature you are and brazenly proclaim your fetish to little Mary Sunshine. After all, unless your boyfriend or gal-pal is as dumb as a post s/he’s already figured out that your mutual sex life limps. Besides, there’s nothing more satisfying than corrupting an innocent. Who knows, s/he may have secrets of his/her own.

Here’s what I suggest. Casually direct the conversation to the amazing variety of human sexual expression. You could reassure your sweetie that just because some things are unfamiliar don’t make them bad. Tell him/her that you’ve been waiting for your relationship to mature so that you could share the intricacies of your desires with him/her. This can be one of those precious bonding moments that Oprah’s always talkin’ about. This might be a good time to view that special video you picked up in the kink section of the local porn emporium. Invite her/him to explore your fantasy with you. Tell the little flower that your love for him/her demands that you share the fullness of your sexuality with her/him. Then pick one turn-on for the two of you to experiment with — lingerie, toys, dominance and submission, role-playing, whatever.

Decide on a safe-word, an out of context word your partner could use if the experiment is heading in an uncomfortable direction. For example, if the dildo is too big or the lipstick is too red, s/he could say “pickles.” The safe-word, when uttered in the scenario, will let you know that you need to change direction or slow down without completely destroying the built up sexual energy.

If this initiation process doesn’t work Dr. Dick suggests that you cut your losses and dump the white bread. Go out and find yourself a kindred spirit, someone you won’t have to apologize to for being creative in your sex play.

Good luck

Cushion for the pushin’

Hey sex fans,

Welcome to another installment of Product Review Friday.

Today we feature a product from a new company; at least they’re new to us. Join us in welcoming the good people at Little Deeper to our review effort.

I love bringing you news of small, independent adult product companies. And if they are green and healthful, as is the Little Deeper, than that’s a huge plus in my book.

But don’t take my word for it, lets check in with Dr Dick Review Crew members, Ken & Denise, for their thoughts

Little Deeper —— $89.95

Ken & Denise
Denise: “This is our first posting of the new year and we have a wonderful product to tell you about. The Little Deeper is a practical, easy to use and easy to store cushion that makes partnered sex more fun and less strenuous.”
Ken: “In other words, the Little Deeper is sex furniture. We’ve reviewed a couple of other such products in the past; you can find those reviews HERE!  In fact, Denise and I had the dubious honor of reviewing one of them. And all I can say is, that product was horrible.”
Denise: “Yeah, I remember how frustrated we both were. I even hesitated when Dr Dick invited us to review the Little Deeper. I was afraid that we’d be disappointed again. But I am so glad that Dr Dick persisted, because I am happy to report that the Little Deeper is amazing. We love the fun play on words too.”
Ken: “It just goes to show you that really good things can come from a good company, one who is interested in health and wellbeing, not just cranking out junk for profit.”
Denise: “So you may be asking yourself, what exactly is the Little Deeper. Well, it’s an ergonomically shaped, sturdy foam cushion covered in a removable plush red polyester cover. And it comes in it’s own very smart black zip-up carrying case.”
Ken: “Let me quote from their promotional materials, because I couldn’t express it better. ‘This simple, nifty device lifts and supports a woman’s hips, positioning them in the perfect position for lovemaking. Using the Little Deeper, you can leave behind the toil and effort that can sometimes be associated with enduring sessions of lovemaking, and now perform various positions with more ease and comfort. The cushion is anatomically designed to fit all body types and sizes, and can result in increased pleasure for both partners. As the woman’s hips are tiled at an ideal angle for penetration, a man can plunge into her body more deeply, which means he can simultaneously stimulate her G-spot and give himself limitless access to pleasure. Ultimately, using the Little Deeper cushion can result in more intense, more long-lasting and even more frequent orgasms during vaginal, anal and oral lovemaking.’”
Denise: “What the promotional materials do not tell you is that the handy-dandy Little Deeper works equally well when Ken is on the bottom and I’m pegging the bejesus out of him.”
Ken: “TOTALLY! When Denise straps it on, I know I’m in for the ride of my life. To tell the truth, I think she’s a better top than me.”
Denise: “See how sweet you are, honey? I suppose I understand why all the images on the Little Deeper website show traditional heterosexual coupling. But I think they do themselves a disservice by doing only that. The Little Deeper is for everyone — gay boys and lesbians will love it too. I also think this cushion would be great for older lovers and the bigger-build people among us too.”
Ken: “You’ll never have to struggle with ordinary bed pillows to prop up your partner’s pelvis for a roll in the hay. And the best part is, this simple device leaves your hands free to further pleasure your partner. And it works with a variety of positions.”
Denise: “I want to return to something I said at the very beginning of this review, because it bears repeating. The Little Deeper is easy to store. We’ve seen some of the other sex cushions that are available in stores and online; they’re huge and unwieldy. And unless you have a designated playroom, where in the world would you store something like that? The Little Deeper, in its nondescript carrying case, fits easily and discreetly in our bedroom closet.”
Full Review HERE!

ENJOY

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