DEAR LADY A: My boyfriend, who is proudly versatile, is getting frustrated because I don’t ever “bottom” for him. I tried it a couple times when I was a teenager, and “it did nothing for me” is an understatement. Actually, it hurt and I hated it. But I love him and I want to please him. What can I do?

– Never A Butt Boy

DEAR BB: Never say “never”, darling! I’m so proud of you for not rejecting the idea of bottoming on the silly notion that you have to choose a side, either bottom or top, and stick to it for the rest of your life! You believe in versatility and that’s perhaps the hardest thing to learn. Logistically-speaking, anal is easy once you get the hang of it. I believe the key to your problem is that you stopped trying when you were just a clumsy kid, new to sex and probably not even close to properly prepared for the experience. Let’s rectify those rectum regrets right now, in four easy steps:

1) Once and for all, accept the simple fact that anal sex, when done correctly, does not necessarily hurt. It’s important for you to know this, both intellectually and emotionally. Trust my advice, trust him to try his best to keep you comfortable. And most of all, trust yourself. You can do this.

2) The three L’s: Lube; Loosen Up (literally); A Little More Lube (Seriously, you’re gonna use a lot!). Once you’re flush with lubricant, it’s time to play with yourself. Rub your anus with the lubed pad of your finger, until you get warmed up. This would be the perfect time to request a rim job from your beloved, by the way. You are, after all, doing this for him! Next, let your boyfriend suck or jerk you off a little while you insert one finger to test the reaction of your sphincter. Notice how it tenses up at first penetration, but after a moment, begins to relax. Practice this until you grow accustomed to the sensations of being hard and aroused while simultaneously relaxing the muscles in your ass with a finger inside.

3) Insert a smooth toy. Did you know they make butt plugs that massage your perineum and prostate at the same time? It’s enough to make a dirty queer girl wish she had one of those prostate thingys for just one night. You gay guys are so lucky!

4) The final step to the process, is to erase that last little bit of fear. You can do this by being a bottom in control. Lay your man on his back, and climb aboard. Make a game of keeping him patient, immobile and horny (handcuffs, perhaps?), then take as long as you want to slide yourself down onto his shaft and find just the right depth that’s comfortable for you. Next, experiment by rocking back and forth on him, any discomfort you’re feeling from his girth may very well be offset by the sensation of his cock rubbing up against your prostate. Once you’ve convinced yourself of your own power bottom status, feel free to “set him free” and let him pump away. I’m pretty sure you know what to do from there, you fierce, versatile boy!