Hey Woody!

As an underpaid psychoanalyst, I thought you might be able to help us.  After a month’s breakup last year due to infidelity on my part over a need to get some butt, my lover and I decided to give it another go.  I told him I’d agree to a monogamous relationship if he’d learn to, er, uhm, take it like a man.  I expressed my need to be the top occasionally and that I was not willing to live out the rest of my life without f–king someone every now and again. I feel our acts of love should be a free exchange of roles (top some; bottom some).  He said he’d be willing to work with me on learning the pleasures of receiving.  I was elated because I really love this guy. 

So I moved back in and agreed to monogamy.  It has been almost a year and I still haven’t gotten any.  We talk about it some, to which he replies “Later,” and I occasionally ease my finger up his a-se when we make love, but he is adamant about not going any further.  He says he just doesn’t get the pleasure I do out of being penetrated.  Hmmm.  Frustration is setting in and my eye is wandering.  Frankly, I’m afraid I might end up cheating on him again.  Maybe I was a bit foolish thinking he would change.  And, maybe I’m a bit foolish even bringing this up as a point of contention in an otherwise perfect relationship.  For the sake of love, do I just give up my need to top? 

— Need Anal Penetration

Dear Need Anal:

Your desire for reciprocity is understandable; your tactics are not.  Basically, you’re engaging in sexual blackmail (“If you don’t give me what I want I’ll get it from someone who will”).

Try this instead:  Acknowledge that he’ll be trying for your sake, not his, and that it means the world to you. It’s a lot harder to say no to a loving request than an angry demand.

Great lovers do things for each other in bed simply because the other one wants to.  They may not necessarily like the act but they get pleasure out of their partner’s pleasure and that’s the aim here—not just for you to get what you want, but for him to experience how much it excites you.  Remember, love means never having to say “I’m sorry, I won’t do that.”

Here’s what you need to do:

  • Offer a “no pain” contract. Lovers may owe each other the gift of their bodies but not if it causes physical pain.  Just as he is obliged to do things he might not like you are obliged to do things that won’t hurt.
  • Let your tongue do the talking. A soft, warm, moist tongue will help him experience the anal area as a source of pleasure.  You can’t hurt anybody with a tongue.
  • Let your fingers do the walking. Circle his perineum and sphincter with a well-lubricated finger in the gentlest way possible.  Do this for several sessions without actually entering him.  When he gets used to it then enter s-l-o-w-l-y while bl-wing or manually stimulating his penis (you want to associate erections with the anal area).
  • Let the toys do the tilling. Graduate to a small, then average dildo. When he’s ready, get a toy about your size.  By the time you enter him with the real stick he’ll have no problems.
  • Let him do the talking. Ask him to do a running commentary so you know what’s too hard, too much, too fast, too whatever, etc.  Don’t make the mistake of thinking that what feels good to you is going to feel good to him.
  • Let yourself do the moaning. Moan, grunt, smile and sigh.  Remember, this is about him getting pleasure out of your pleasure, so show it.

Check out Woody’s latest book, How To Top Like A Stud: A Penetrating Guide to Gay Sex. LINK: