Free Sex Advice
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!
Dr. Dick
Originally published June 2011