Search Results: Self Esteem

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And they’re off…

Name: Dan and Rebecca
Gender: Couple
Age: 25, 20
Location:
We are a happy but frustrated couple looking for advice. I’m a 25
year old male, and my lovely girlfriend is 20.

I have no problem bringing her to orgasm and pleasing her, but since we’ve been seeing each other I have not been able to cum once. In the past it was always difficult for me to cum during sex, my first time (age 18) my then gf and I went for about three hours before we just gave up. Usually I would have to jerk myself off afterwards but now I can’t even do that.

However if I am alone with porn I am easily able to masturbate and can get off a few times a day. How is it that I can jerk off to pictures that mean nothing to me, but can’t cum for the woman I love the most?

I’ve spoken with a doctor and he said medically there is nothing wrong with my penis. What do you suggest we do? We are really getting frustrated and just want to be able to please each other.

Simply put, there’s a difference between the psycho-sexual response we have when we are alone and the one we experience with a partner. Your doctor is right, there’s probably nothing wrong with your unit. It’s all in your head…or your mind, to be more exact. And I’m not being flippant.

If I had to guess, I’d say you have a real bad case of performance anxiety, pup. Here’s how this nasty thing works. Say I have a less than satisfying sexual experience for one reason or another. Before I know it, I’m replaying the incident over and over in my mind’s eye till that’s all I can think about. The proverbial molehill has become a mountain, don’t ‘cha know. I then bring my anxiety to my next encounter. My hyper self-consciousness primes me for more disappointment. And I’m all prepared to interpret the disappointment as a failure. Well, you can see where I’m going with this, huh? My fears become self-fulfilling and I find I’m beginning to avoid partnered sex and my relationship flounders, I develop a full-blown sexual dysfunction and my self-esteem takes a nosedive. My preoccupation with my problem makes it less likely that I’ll be fully present during sex with my partner, which pretty much scuttles my sexual responsiveness and any hope for spontaneity.

It looks to me like performance anxiety is putting a damper on your sexual arousal and short-circuiting your sexual response cycle, Dan. Get thee to a sex-positive therapist ASAP, darling! Believe me, this is nothing to fool around with, especially for someone at your tender age.

When I see this sort of thing in my private practice, I always begin the therapeutic intervention by calling a moratorium on fucking of any kind. This immediately takes a great deal of the pressure off the couple. From there we begin to rebuild the partnered psycho-sexual response one step at a time. We begin with sensate focus training, stress reduction and relaxation exercises. I have the greatest confidence in this method; it succeeds over 90% of the time.

Good luck

Hey dr dick! What’s that toll-free podcast voicemail telephone number? Why, it’s: (866) 422-5680. DON’T BE SHY, LET IT FLY!

Name: Gene
Gender:  Male
Age: 45
Location: Orlando
I am a homosexual, and I have a “friend” who has been incarcerated for five years. The relationship while he was out with me was excellent. I have asked him numerous of times is he having sex with the homo’s in jail and he responds by saying no. I think otherwise, and he wants to come back to me upon his release. My question is “should I wait for him”?

Gene, Gene, Gene, there are so many things wrong with this picture, I hardly know where to start. Your man’s in the big house for 5 years, and you expect him to keep it in his pants for the duration…just for you? Like WHY? Hey, he’s in the clink, darling, not in a monastery. Oh wait; even monks in a monastery don’t keep it in their habit nowadays! At any rate, it may not be up to him if he has sex or not…if you catch my drift. He might be someone’s bitch right now, he’s just not telling you about it.

Should you wait for him? You mean, all alone by yourself with no one to comfort you while your guy is doin’ his time? This sounds like the script for a real bad 1950’s prison movie. You could play the role of the long-suffering girlfriend pining away while her good-for-nothing man pays his debt to society.

Honey, you need to get out more.

Good luck

Name: Erin
Gender: female
Age: 32
Location: AL
Is it wrong for a married woman to want to masturbate when alone?

Gee, let me see. Is it wrong for a woman to feed herself when she is alone?

Erin, what could possibly be wrong with wanting to pleasure yourself when you are alone? As we all know, many women only get off through masturbation. Hell nowadays, liberated women folk everywhere are comfortable enough with their sexuality to jill-off even with their partner. So no, I don’t think there’s anything wrong with self-pleasuring…alone or with a partner.

Besides, there’s no better way to get to know your body and your sexual response cycle. Once you acquainted yourself with how your body works, you’ll have a whole lot more information about how you tic that you’ll be able to share with your partner when the time comes. It’s a win/win situation for ya’ll.

Name: Joy
Gender:  female
Age: 21
Location: California
I have been dating this guy for almost 3 year and also live with him. I love the way he makes love to me and i love dick, but sometimes i just want to make out with girls… does this make me a lesbian at all?

Hardly, not even a little bit lesbian! Ya see, it takes more than suckin’ face with another chick to make a gal a lesbiterian. You’re gonna need to get yourself a she-mullet, some plaid shirts and a vibrator that you can kick-start. Now that’ll make ya dyke for damn sure. Sheesh!

Hey dr dick! What’s that toll-free podcast voicemail telephone number? Why, it’s: (866) 422-5680. DON’T BE SHY, LET IT FLY!

Learning to ride

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

The Heartbreak of Male Performance Anxiety

I get a dozen or so messages a month on this topic. I’ve written about it in numerous postings and spoken about it in several podcasts, but still the email comes.

One of the real bugaboos for anyone, regardless of gender, is living up to our own expectations of sexual performance. So many things can get in the way, literally and figuratively, of fully enjoying ourselves and/or pleasuring our partners.

The arousal stage of our sexual response cycle is particularly vulnerable to a disruption. And when there’s trouble there, there’s no hiding it. A limp dick or a dry pussy can put the kibosh on all festivities that we may have hoped would follow.

However, performance anxiety can strike any of us, regardless of age, and at just about any point in our sexual response cycle. This is a particularly galling when it seems to come out of the blue. And regaining our composure can be more far more difficult than we imagine.

Today we will be focusing on male performance anxiety.  I’ll address female performance anxiety at a later date.

Here’s Bob, he’s 26:
Doc, this has never happened before. But I couldn’t get it up tonight, and this chick was H.O.T. Now I’m not gay at all, but I haven’t had sex in about 3 years because I was locked up…so I masturbated pretty regularly, about 3 or 4 times a week. But I can’t figure out why I was soft… the only thing I can think of is I ate clams tonight and I’ve never had them before. Could it be that or should I get checked out?

It weren’t the clams, darlin’! And I don’t think you need to get “checked out” either…at least not right away. If you could back away from the situation a bit and stop freaking out, I think you’d discover the source of your problem all on your own.

Here’s the thing—while you were out of commission there in the slammer, you relied, as you say, on jerking off. Okay, cool. We all do what we gotta do. Now the first time you try to score after your release…you go soft. This tells me you have a mild case of performance anxiety. We all get that from time to time.

There’s probably nothing wrong with you or your johnson. You just got the jitters first time you tried to get you some after being away, that’s all.

The anticipation of boning this H.O.T. chick—fueled by some predictable self-consciousness; what with just getting out of the big house and all—pulled the plug on your wood. No surprise there, right?

What I don’t want to see happen is for you to replay the incident over and over in your mind’s eye til that’s all you can think about. If you do, this proverbial molehill will become a mountain. You’ll then bring all this anxiety to your next encounter, setting yourself up for even more disappointment. You can see how this shit can snowball? If you interpret every less than satisfying encounter as a failure, your fears will become self-fulfilling. You’ll begin to avoid partnered sex and you’ll develop a full-blown sexual dysfunction. And your self-esteem will take a nosedive, too.

If you’re preoccupied with your performance, it’s less likely that you’ll be fully present during sex with a partner. This pretty much fucks up your sexual responsiveness and any hope for spontaneity. Why not just relax into the whole sex thing and not try to prove your manhood with your pecker?

Then there’s Steve with a slightly different take on this meddlesome problem:

My partner and I have been together for just over 3 years now in a monogamous relationship. I am the top and he the bottom. Our problem is not premature ejaculation on his part, but his inability to have an orgasm at all. No matter what I try and even if he masturbates, sometimes it is impossible to get him to cum. Is this a medical issue? Have you ever heard of this?

Delayed ejaculation is the difficulty one has ejaculating even with a firm erection and sufficient sexual arousal and stimulation. This problem is not uncommon. For most men, delayed ejaculation occurs during partnered sex more frequently than while masturbating. In fact, 85% of men with delayed ejaculation can usually cum by jacking off. However, in partnered sex, the guy may be unable to ejaculate at all, or only after prolonged partnered stimulation. This problem can be very frustrating and cause distress for both partners involved, as you already know.

What causes delayed ejaculation? Well, it could be a number of things. It could be something as simple as performance anxiety, or inadequate stimulation, or there could be neurological damage.

I don’t want to be too reductionist here, but most of us experts believe that the majority of instances of delayed ejaculation aren’t physical in nature, but rather are the product of psychological concerns. Simply put, there’s a difference between the psychosexual response we have when we are alone and the one we experience with a partner. There’s probably nothing wrong with your partner’s unit. It’s all in his head…or his mind, to be more exact. If I had to guess, I’d say he’s got a real bad case of performance anxiety.

When I see this sort of thing in my private practice, I always begin the therapeutic intervention by calling a moratorium on fucking of any kind. This immediately takes the pressure off the couple. From there we begin to rebuild the partnered psychosexual response one step at a time. We begin with sensate focus training (Sensate Focus is a series of specific exercises for couples that encourage each partner to take turns paying increased attention to their own sensations. More about these helpful exercises in the weeks to come.), stress reduction and relaxation exercises. These applications are designed to reduce performance pressure and instead focus on pleasure. The idea is to get them to stay in the moment; absorb the pleasure present without worrying about what is “supposed” to happen.

Finally we address as frankly and openly as possible any fears or anxieties that they may have—as individuals or as a couple. I have the greatest confidence in this method; it succeeds over 90% of the time.

Ok, let’s recap shall we?

Overcoming sexual performance anxiety is dependent on five simple things.

  • First, a guy needs to be attuned to his sexual response cycle — arousal, plateau, orgasmic and resolution phases. He should know what kind of stimulation he needs at each phase to fully enjoy himself and satisfy his partner.
  • Second, the more worried a guy is about a performance issue, the more likely that problem will present itself. A bad experience in the past can often set the stage for its recurrence.
  • Third, don’t be afraid to talk this over with your partner. Withdrawing from your partner or shying away from sex altogether will only increase the likelihood that the problem will persist.
  • Forth, be proactive! Fearing the loss of your sexual prowess or feeling sorry for yourself is counterproductive. Confront the challenge head on. Employ sensate focus training stress reduction techniques and relaxation exercises to help you push past this temporarily impasse and regain your self-confidence.
  • Fifth, free yourself from the mindset that your dick is the center of the universe. Your manhood or your capacity to be a great lover does not reside in your genitals. Expand your sexual repertoire. Remember, pleasure centers abound in your body as well as your partner’s.

Good luck!

Come Out, Come Out Wherever You Are

Just in time for National Coming Out Day, which just so happens to be today, October 11th, we have this from Craig:

Doc,
I’m 19, and I’ve decided that I’m gay. But I don’t know how to tell anyone. I’m afraid that I’ll lose my friends and family. I come from a very religious family, and they’ll never understand. I don’t want to hurt them, but I want to be honest about who I am. Just wondering if you could help me.

Coming out is never easy—or almost never—but having to do so to bigoted people makes things worse. There are many different aspects to the coming out process. It means both owning and valuing who you are, and sharing that information with others. You’ve apparently laid the groundwork by self-identifying as gay. Unfortunately, coming out also means learning to deal with the hostility many people have toward us sexual minorities.

Owning your sexual identity and integrating it into your overall sense of self is the first step in what I believe is a lifelong process. Your sexual preferences are just a small part of who you are. It is indeed an important part, but it’s not necessarily the defining element that some would make it out to be. In this instance, LGBT folks are not all that different from everyone else who is awakening to his/her sexuality. We can take some comfort from the fact that we are not alone. So many other segments of the population are marginalized and discounted because of their race, gender, age, religion, ethnic origin, you name it. Let’s face it, pup, our culture doesn’t do real well with diversity.

And ya know what else? There are a whole lot of us who are marginalized and who are discriminated against, who then turn right around and discriminate against and marginalize others. This just breaks my heart! Hopefully you’ll avoid the temptation to do this yourself.

Being different in our society is a double-edged sword. Obviously, it’s a challenge to the status quo, but it also frees us up to tread a less traveled path. To compensate for the difficulties of being a minority, we get to define ourselves in ways that are unavailable to the dominant culture.

I don’t suppose any of us is ever entirely really free of our own internalized homophobia, any more than other marginalized minorities can rid themselves of their internalized self-doubt. No one can completely escape the prejudices and biases that surround them, but most of us make our way, regardless. That’s why coming out is so important. It empowers us. It increases our self-esteem. Honesty increases personal integrity. And when we stop hiding or denying this important aspect of ourselves, we have greater freedom of self-expression, and we become more available for happy, healthy and honest relationships.

So, how much do you know about LGBT history? Knowing that you belong to a big and vibrant community with a long and illustrious history will enhance your queer identity. You’ll find positive role models in every era of human history, and in every human endeavor—and affirmative role models will help you achieve a positive sense of self. (However, you’re gonna have to do some digging. The dominant culture suppresses queer history, which often leaves those who are just coming out feeling isolated, alone and unsure. Fear of rejection from the dominant culture is greatest for those who don’t know they belong to something bigger and stronger than themselves.)

Knowing your gay history will also give you ammunition to refute those around you who will try to label you as sick or sinful. Loads of LGBT folk have enriched civilization through science, religion, music, politics, art, theater, sports and literature, to name just a few. Long before you and I showed up on the scene they were paving the way for the freedoms and tolerance we currently enjoy in this country.

If you’re not already involved in your local gay community, it’s high time you got hooked up. Practice your coming out skills with other LGBT people. Coming out to those who are most likely to be supportive will make this phase easier. And in doing so, you’ll be creating a natural support system of friends who will be your gay “family.” You will also find helpful resources, including support groups, crisis lines, gay-friendly churches and synagogues, social outlets and political and cultural activities and organizations.

Once you’ve honed your coming out skills with the queer community, you’ll be ready to move on to straight folks. This will probably be a mixed bag. Some won’t give a hoot. Others may have a lot of hoot to give. The best advice I can give you is the same advice I received from my gay elders when I was coming out at about your age: Make your coming out a celebration.

Listen, if you carry your hat in your hand, shuffle your feet and look all dejected when you make your announcement, your audience will have little choice but to receive the information as bad or troubling news. However, if you stand up, look the person in the eye, and tell her or him that you have some wonderful news to share with them, you will be giving them a running start on receiving the information as good news. Besides, a positive presentation will help short-circuit some of the initial shock or confusion they may experience.

Expect that most straight folks—particularly those of a religious bent—will need some time to get used to the idea of you being queer. And as you suggest, it is quite possible that some family members or friends may reject you initially. But it’s not the end of the world, and lots of people, even some religious folks, come around in their own sweet time.

Coming out to others will be a more positive experience if you’re comfortable in your own skin. Hopefully you’re not overly dependent on others for your sense of self—a tall order for someone of your tender age and background. But remember, thousands of people, young and old from every corner of the world, are making their first tentative steps out of the closet right this minute. You are not alone.

How well you do fare may ultimately hinge on controlling, as much as possible, the time and place you come out. If you “out” yourself as opposed to being “outted” by someone else, you’re more likely to succeed. Being able to judge the receptiveness of your audience is also important. The best time for you might not necessarily be the best time for the person you’re about to tell. (F’rinstance, grandpa’s funeral may not be the ideal time to announce to your family that you’re a big fat flamer.)

While some friends and family may have figured you’re queer long before you have, give everyone the time and space he or she needs to work through the news. Be prepared for some negative reactions. (Having some supportive friends available to talk things through afterward, or retreat to, will help.) If you do your best to bring the news in a life affirming way and your audience still rejects you, that’s not your fault; nor does that make them right. You have the right to be who you are. You have the right to be out, proud and open about all the aspects of your life, including your sexuality. Never let people unable to accept that, even if they are family, diminish your self-worth.

Coming out may be difficult, but it’s also very rewarding. Coming out affirms your dignity, as well as underscores the dignity of other queer folk. Finally, never take for granted the freedom and tolerance the dominant culture begrudgingly gives us. It’s only through vigilance and political action that we secure our rightful place in society.

Good luck.

Overcoming a Fear of Sex: A Step-By-Step Process

All phobias can be overcome with some effort. The same is true for conquering a fear of sex. Here, I walk a young gay man through his trepidation with anal sex. We take simple, easy to accomplish steps to build confidence and dispel his apprehensions.

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 it up. I liked the guy, he was hot, and I enjoyed all the foreplay type stuff, but I just couldn’t do anything else. Any advice on how to get over this?
Drew

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

Let me tell you a little story. Recently I was strolling in the park with my dog. We were each, in our own way, enjoying the sights, sounds and smells of nature in its glory. As we walked along, we encountered a father and son who were deeply involved in what appeared to be the boy’s first lesson in riding a bicycle—sans training wheels. Despite the father’s patient encouragement, the kid couldn’t seem to get the hang of it. He’d start out okay, but just as soon as his dad let go of the bike, it would begin to wobble and the boy would eventually crash. There were plenty of tears, a skinned knee, and the boy’s fear and anxiety were thick enough to cut with a knife.

The boy was convinced that he couldn’t ride on his own. His defeatism became a self-fulfilling prophecy. He finally gave up, sat down on a bench, his bike in a tangle at his feet, and refused his father’s pleading to give it another try. In his 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’d had the opportunity to suggest to the boy and his dad that they 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’d have suggested the dad start by helping the kid walk on 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 repertoire 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; you need to find the Big Old Butt Pirate within.

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

  • Before you start playing with your hole—relax. 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, this type of lube isn’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, find your hole and play with your rosebud. Gently massage the area around your asshole, but don’t slide your fingers in just yet. Simply get used to the sensations 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. You know, like finger-fucking yourself.
  • Locate 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 it a nice gentle massage. If you’re still stroking your wood, don’t be surprised if this prostate massage gets you to ejaculate. 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’ll notice that your sphincter muscle will tighten around your finger and pulsate with each squirt.

Continue these self-pleasuring exercises until you’re 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. This will help you avoid an unsightly and embarrassing mishap that might mess up the big event.
  • Remember to take it slow. There’s no rushing pleasure. Remember, 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 plenty of lube near at hand.
  • While you’re warming up, start loosening up your ass with your lubed fingers, just as you did 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 finger-fucking first.
  • After 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 essential.
  • 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 riding your bike all by yourself.

Good luck!

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