Q. I'm a straight woman in an open relationship with a straight man. I've always wanted to try receiving anal sex (and penetration with a strap-on), and I really enjoy masturbating with anal toys. However, no guy that I've been serious with, or been comfortable enough to have a casual fuckbuddy relationship with, is willing to try giving me anal penetration. My boyfriend once said he'd do anal if I really want to, but I can tell that it really bothers him, and he sometimes doesn't even like *discussing* the idea of anal sex. I'm more experienced than him, and in the past, I've introduced him to things that made him feel trepidatious-yet-intrigued, and he was always really glad afterwards. However, when it comes to discussing anal, he is definitely really, really grossed out by it.

I've considered posting a casual sex ad on craigslist, and I have a casual sex OKCupid account that's just a picture of my body, but I always feel really very uncomfortable setting up something with strangers. However, when I get to know people that I'm attracted to, somehow they tend to be people who have a strong aversion to anal sex.
I think this is something that I would really, really enjoy. What would you suggest?

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A. This is really two questions:

1. Can I get my dude to fuck me up the ass?
2. If not, should I find someone else to get my ass pounded?

Let's go with one at a time.

1. Trying to get your boyfriend to ass fuck you is going to be a bad idea. Everyone has some squick that is just something that is over the line for them. That squick is different for each person and your boyfriend has made it pretty clear that anal sex is his squick.

Getting someone to cross the line of their squick is, in general, a bad idea. In the same way that we all have fetishes and those fetishes should be respected we all have squicks and those squicks should be respected. And, just like fetishes, squicks often make no sense and are simply hard wired.

Beyond that, anal sex takes a lot of education and research to do right. If you do it wrong it can not only hurt, but also do damage. This means both parties have to be really motivated to learn about anal and how to do it correctly the first time. If your boyfriend is squicked by anal he's not going to have the dedication needed to sit down and read a lot and learn how to do it right. Which means, not only will you be pressuring someone you love into doing a sex act that really bothers them emotionally, you'll be making sure that your first anal experience is not only bad, but dangerous and ridiculously painful.

This assumes it would be even possible to have anal sex with him. If it's a really big squick he might lose his erection the second his dick gets near your bunghole.

So, yeah, stop trying to turn him into your poo pusher.

2. Now, as to whether or not you should try to get it up the ass from someone else.

You are in an open relationship, so absolutely you should go for it and I'll tell you how in a minute.

That said, first off, I want to provide some advice to women who are in this situation and not in an open relationship. (Mostly because when I first read this letter this morning I missed the words "open relationship" in the first sentence because I'm an idiot.)

Ask yourself how important it actually is for you to get anal. It's fairly obvious that I have no problem at all with infidelity. Hell, one of my favorite people in the world, Violet has not exactly been the most faithful woman in the world.

I am, however, against people who are dumb about being unfaithful. Don't do it unless it really matters to you. How do you know it really matters to you? It matters to you if you realize how much hard work goes into being unfaithful and still are willing to move ahead and do it.

When you do it, realize that it's a commitment. Get yourself a burner phone and hide it your box of Tampax (your boyfriend will NEVER look there.) Get a burner email account. Find a place to hide condoms. Use condoms. Tell a friend what you are doing and make sure they are willing to be your alibi should your boyfriend start asking questions. And, limit yourself to people who have been with unfaithful ladies before. Infidelity newbies will make mistakes like texting you when you are hanging out with your boyfriend and may get you caught. Or they may become more attached than you'd like and do things that sabotage your relationship.

If any of the above seems like too much work just to have anal sex, you don't want anal sex enough right now to cheat on your boyfriend to get it.

If, on the other hand, these seem like reasonable precautions then you are ready for anal sex and cheating and probably won't be a happy, fully satisfied woman until you do it, so here's what you do (which is also what you do if you have an open relationship).

Get yourself an account on Fetlife. Avoid Craigslist - which will be full of posers, liars and people who won't know how to give you what you want safely and sanely.

As I said before, for anal sex you really want to make sure the person who is buggering you knows what they are doing. You want them to be as experienced as possible, so that it feels good and not like a ring of fire.

But, you are also going to be with someone who is not your primary partner. You want someone who is going to be cool with you having a boyfriend. So, don't joint the Fetlife anal sex groups - join the Fetlife infidelity groups. That's where you'll find people who are used to fucking girls who have husbands and boyfriends and know what to do so they don't accidentally cause problems.

Once there, don't simply go for the first guy who is in your area and willing to fuck your ass. You said you don't feel comfortable with strangers, and that's a safe and sane attitude to have.

Instead, become active in the community and make friends. Eventually you'll find a guy who seems super interesting and super cute - who has expressed that he is experienced at anal. Get to know him. Spend a few weeks or even two or three months talking to him. Text him. Talk to him online on IM. Start a virtual relationship with him and figure out if you can trust him or not. This way he'll eventually not only not be a stranger, he'll be a non stranger who is into you and into anal. Which means, you'll feel good about letting him into your butt.

This method will take longer than simply putting up an anal ad on Craigslist, but will let you "end up" with a better experience with a guy you trust that won't impact your primary relationship.

And, after you've had some good times with him, find some way to let the Fetlife community know that he's not only good at helping women cheat but he's good in the back door, because, other women will also be looking for guys they can trust to bang their butt behind their boyfriends back and references are a good thing.

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If you want relationship advice from a drunk just use your burner email account and send the question to bcalendar@aim.com