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Hey, Woody!

I bought a couple of dildos to try loosening me up (one was about 7” and the other a thick one about 9”).  The results haven’t been so great for me.  I tried sitting on the dildos and then literally running out of the bathroom and jumping on my beau.

That works momentarily (he loves it!) but I’m still sore as hell for the next few days.  We had sex on Saturday and I thought I was having my period this morning.  My poor little butt cried murder!  A friend told me about something called Anal-Eze.  It’s a cream or something that is supposed to numb your muscles.  Do you recommend it?

—  Trying to hit bottom

Dear Trying:

Your letter is a prime example of Einstein’s theory that only two things are infinite–the universe and male stupidity.

Hopscotching across the house from dildos to d–ks?  I couldn’t make up this s–t if I tried. You’re doing everything wrong.

Topical anesthetics like Anal Eze or Orajel are the single worst things you can use to get to the bottom of your problem.  Or rather, the problem of being a bottom.

Why?  Because pain is a signal that something’s wrong.  If you mask the pain you’re going to end up doing something terrible, like tearing the lining of your rectum.  Or worse, getting the idea that your friends want to sit through a three-hour community theater production starring you.

Besides, the anesthetics won’t work.  They don’t penetrate far enough to relax the muscle.  It’s like using full sentences to seduce a party boy:  Good luck.

If you really want to try topical anesthetics you’ll need a prescription from a doctor because the over-the-counter crap doesn’t work. And if you do manage to get a prescription, I’d love to see your HMO’s reaction to the diagnosis.

If you want to bottom without any pain there’s a couple of things you need to know.   First, the anus has two sphincter muscles, the internal sphincter and external sphincter, which control your bowel movements.

Your internal sphincter is an involuntary muscle — which means you can’t control it. This is the sphincter that relaxes to let out gas and the stinky brown stuff. Your external sphincter is both a voluntary muscle and an involuntary one.

So here’s the thing:  No matter how much you want to get f–ked, your muscles will contract to keep the beast out.  Luckily, like any muscle, it can’t stay contracted for very long before it relaxes.

The trick is to trick your muscles into letting your trick in.  Here’s how:

1) Start with a very small dildo.  Buying a dildo the size of a normal penis is the biggest mistake people make.   Get a finger-sized dildo.

2) As the dildo becomes comfortable, gradually increase the size of the dildo until you can tolerate one that resembles the size of a normal penis.  “Gradually” means over the course of several weeks. This is the hardest rule to follow because men are pigs and we want what we want when we want it.  If you’re serious about getting f–ked without pain, you’re going to have to resign yourself to being patient and progressing slowly.