I'm 26 years old and I came out of the closet last year, ready to be myself by any means necessary. For the past 10 years or so, I've hidden my sexuality by having relationships with females, but never having sex with them — I couldn't take the charade that far. So now that I'm fully entrenched in the "life," I'm ready to take on guys. But honestly, I'm scared. The only sex I've ever had has been with my hand, and I can't really imagine anal sex. My friends tell me to get a dildo and practice with that, but I'm afraid I won't do it right and end up hurting myself. They have offered to help me put it in or put theirs in, but still I'm scared of the initial penetration. I know I'm not officially gay until I do this, but aaarrggghhhh. Am I just being a pussy?
No, Fraid, you're not being a pussy, because pussies actually like having penises in them. Believe me, I asked mine. But your apprehension is normal, and being gay doesn't prepare you to have something shoved between your biscuits. Why? Because you have two sets of muscles down there — one that makes sure you don't accidentally spray dookie cookies three to four times a day, and another that closes automatically when something pushes against it. So it's only natural that just the thought of something going in makes your butt muscles clench in horror. After all, your bootay isn't used to receiving gifts. In your 26 years, it has been a giver — to diapers, toilets, and maybe even alleys. So in order for it to become more comfortable participating in sexual fun and games, you need to train it. The key is relaxation — something that a little liquor, lube, or the other l-word — love — can buy you. But before you try any of those, I suggest a finger. Not just any finger, your finger. The next time you shower, breathe deeply and gently stick a digit into your bunghole. After a few tries, you can move onto a buttplug or a dildo made especially for anal contact (others might get lost up yonder), or even a real, live penis. But before you do any of this, you might want to give yourself an enema with clean tap water so your chute is sparkling-clean. You're out of the closet now — people know where to find you; we don't need you to leave a trail of buttcrumbs like some kind of fuckin' Hansel and Gretel.