Oct 20 2016




Talking about anal sex is weird. At first.

But here goes.

First times are really special . Your first kiss, your first REAL kiss, the first time you got fingered in the backseat of your parent’s Subaru. These are moments that you look fondly back on for the rest of your life. But for some reason the first time you attempt anal sex is often the last time and it’s scarred in your memory as painful and embarrassing.

I’m not an anal sex expert – but I am a rare being (according to online forums) since I’ve never had a bad anal sex experience. I’ve had hilarious experiences, “meh” experiences and eventually incredibly deep/erotic/intimate experiences but there are some concrete lessons I’ve learned along the way.

1. It’s Not Me It’s You

I don’t usually badmouth men, but the backasswards expectations of guys is the #1 reason anal sex doesn’t work. Expectations for women is that they are supposed to “know what to do” and that men show up for the occasion.  Women I’ve talked to have read books on the subject, practiced and prepared themselves mentally and emotionally for this. But, it’s men who are in the driver seat, and they disproportionately have the power to make it a good or bad experience. So read up!

2. Be a Boyscout

Actually is your boyfriend in the room? Could you go get him?

Hey dude – yes, I’m talking to you. Show up to the gunfight with a mother-fucking gun. Be prepared. Not just with a toolkit of lubes and toys and towels (although yes! to all those things). Be prepared to do more work. Foreplay is the biggest part of anal sex. A woman should be HIGHLY aroused. I’m talking best-sex-of-her-life aroused, so she can be in a good place for anal. This is your moment to completely be in charge, which is where the eroticism and excitement for most people comes from. So be ready for a long evening of gentle, passionate, understanding and take-charge sex that eventually will blow your mind.

3. I’m sorry – did you say something?

LADIES – If you need more foreplay (or more lube) to get comfortable. Ask.

4. Turn Back Around

What are you doing? I mentioned anal sex and you immediately turn around? No – turn back around. Rookie move.

The #1 mistake women make their first time is they get all “porny” and position themselves on all fours. This is THE most difficult and painful angle for a woman. Especially if you  feel nervous – you’re completely vulnerable, staring at a wall instead of your lovers face. This is the worst.

My suggestion is a missionary position with your hips lifted with pillows. My personal favorite is spoon style, you really get a chance to connect your entire bodies and there’s more cooperative give and take of speed and depth. For well-endowed partners – these positions are far more comfortable and your body naturally moves in a direction that reduces friction and increases awesomeness.

5. Use Your Words

I am a lady. And you can be too. But in order to communicate what you want (and don’t want) you need to get used to saying poop and butt and anal.

So you best get over your giggles and learn to express yourself.

A word about poop: Your body is a magnificent machine and runs on a schedule regardless of whether you decide to have anal sex. And there’s no shame in having a beautifully functioning digestive system. So if you don’t need to #2 in the next 15 minutes, you’re good to go! If you feel a little nervous about the timing, say “not tonight babe.” There should be an unspoken agreement that the subject is then closed. He doesn’t need the details.


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