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

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