Help! My Boyfriend Wants Anal More Than a Republican Congressman

Dear Allie,

My boyfriend of about six months really wants to have anal sex with me. It's all he talks about. I want to make him happy, but I'm scared that it's going to hurt too bad, plus I'm concerned about the cleanliness stuff.

If I go through with it, what do I need to know? Are there any tips that will make it easier. Any advice would be appreciated!

Thanks,

Scared of Anal

Suck it, Ann Landers! Is anyone asking you how to successfully have tushie sex? 

Nope, I didn't think so.

Sure, this blog will ensure that I never get hired as anything other than a latte-maker or one of Nevada's legal hookers, but who cares, I'm doing the work of angels. 

Now, let's get this girl so comfortable with anal that she will be bent over like Roberto Arango at a Bachmann after-party.

Alright, SOA, there's a few things I want to ask before I give my tips on anal. First, do you want to do this or are you just doing it to appease your pain-in-the-ass boyfriend? If it's the latter, then I want you to think about actually going through with it. I think most sex acts, especially those we aren't initially comfortable with, should be done because of some personal desire to do it.

But for sake of giving advice, I'm going to assume that deep down you want to GET IT IN. So here's my advice for an anal-newbie.

1. RELAX. Seriously! Breathe. Don't tense up. And it might even help if you have a more traditional form of sex beforehand so your body is already in Go-Mode.
2. Lube. Water-based if you are using condoms and maybe something oil-based (because of the lasting factor) if you guys are condom-less. Remember to be safe. Tests done, etc.
3. Speed. Go slow until your comfortable and make sure you pass this morsel of advice on to your seemingly eager boyfriend. 
4. Call the shots. Come to the agreement that if you begin to feel overwhelmed you can stop the act. This veto power might make you feel in control enough to get through any inhibitions.
5. Cleanliness. A little gross I know, but try to have some type of movement before you partake in the act. If you're still feeling self-conscious, buy an enema and call it a day.

Other than that, it's up to you, SOA. You are the only person who knows your body and what you are comfortable with. Hopefully this helps! 

Now. Go. Perform an act that will make your father wake up in a cold sweat with a desire to buy a gun.

XOXO,

 Allie

P.S. If after reading this you think, "Hmm... is that a ingrown hair or herpes?" Write me at notreallyabarista@gmail.com or on Twitter @AllieOopsie. You will remain anonymous!