Hi there,
 
I always want to have anal sex with my girlfriend who is 19 (23 years younger than me). I have followed some instructions and tried a few times but have not made it. The problem is that I just can't get in there, though I used lube and she has not resisted. Any advice about that? Furthermore, I am much keen to kiss and lick her anus but she thinks I am weird. Is the act normal?
 
Thanks,
Bummed Out

Dear B.O.,

You sound like a very polite man, so we'll do our best to ignore the mild ickiness we're feeling about advising a 42-year-old man on popping his girlfriend's backdoor cherry. But just to put our minds at ease, will you please pinkie-promise us that she wants this as much as you do? Because "she has not resisted" isn't quite doing it for us.

Anyway. Onto the anal action. We don't have the space here to get into all of the ins and outs of going in the butt--it would take an entire book to answer all your questions in full. But here are ten things we think are most relevant to your particular case...

1. You say you've used lube, but you should know that the rule of anal is "too much lube is nearly enough." A little dab won't cut it. Also, your lube could be too thin for the job--try a thick, water-based lube like Maximus.

2. If your girlfriend is nervous about taking the Hershey Highway, then she could be tensing up back there without even realizing it (they don't call it "being anal" for nothing). Make sure she is super relaxed by treating her to an extra dose of foreplay. You might even want to give her an orgasm first.

3. Your penis shouldn't be the first thing you go in with. Start with a well-lubed pinkie (yep, that one you just promised us with). Move up to a larger finger, and then maybe try a small butt plug or mini dildo.

4. Once you're ready to graduate to your own penis, you'll still use your fingers to warm up the area first. Plus you can use your fingers to feel whether the, er, rosebud is tense or relaxed.

5. Did we mention lube?

6. Ask your girlfriend to help guide you in with her hands. She can also move her body toward you, rather than you thrusting toward her. Being more in control like this should help her relax.

7. That thing we said about thrusting? Don't do it. Ever. This is a time for gentle, slow, small movements.

8. There are more ways to do anal than just doggie style. Some people find it easier--both physically and psychologically--if the receiver is lying on their back with their legs up.

9. There's nothing weird about rimming. Sure, it's not the meat 'n' potatoes of sex for most couples, but part of its appeal is how taboo it is, right? Maybe she's calling you "weird" to hide her own discomfort with the act, in which case you could try a little ass-kissing next time you're in the shower together.

10. If your girlfriend is interested, have her explore your backdoor with a finger (or more). If you've both been on both ends of the equation, then you'll have a better sense of what to do...and what not to do. Plus it's just nice and symmetrical. (And don't complain, dude: you're 42 and you've got a 19-year-old girlfriend who's open to a little Greek love. Life is pretty good, no?)

Back to you,

Em & Lo