Learning to Ride

Let me tell you a little story. 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. 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. 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!