I've read your column since I was 13. It has made me laugh, gag, cry, question, and gain understanding countless times. Normally I'm one to answer my own questions and learn things the hard way. But today I'm at a bit of al loss. My wife and I are trying to develop some safe sex guidelines for ourselves and we're having trouble finding the line where risk supersedes pleasure. But let me back up a hair first.

We've been together seven years and married for five. We have a strong and amazingly successful relationship. It's so great for two reasons. One, we are very compatible in our attitudes, sexual desires/fetishes, and in our parenting (we have two young children). This is really just luck, our first 6 months we were just fuck buddies… until we realized how well it was working. And two, COMMUNICATION. Honest and open communication is the basis for any successful relationship open, monogamish, monogamous and everything in between. In short, we're happy and successful.

A few years back we wound up instigating a an orgy after a wedding reception—and we LOVED it. Our already fantastic and kinky sex life has been even more amazing ever since then. Through trial and error along with some experimenting we've settled into a hot and sexy relationship with a couple of friends who are also both bisexual and share a number of our kinks (which were a bit too intense for most others we've brought into our bed). We've managed a pretty wonderful balance between our sex life, both with each other and in groups, and our number one priority, which is being fabulous parents. We are out to the world about being "poly" because we think it's important for the world to know it can work well. We are very happy.

So, what on earth could our question be then?

Well, we are having a hard time finding the line where our desire to be safe from disease trumps our desire for pleasure. This is something we need to set in stone when we are not in the middle of a fuck session because in the moment we are both likely to say, "Put your cock in me bare and slap me harder."

So far we've gotten it down well enough that we've decided if a dick is going in a hole it needs a condom. Oral sex is less risky (that's true right?) and we don't want to bother with condoms or (gag) dental dams for sucking, licking, and fingering. Our uncertainty comes in the grey area between the two.

What is the risk if three of us are lined up and being penetrated in turn by the fourth person? Do we need to change condoms between each penetration? What is the etiquette here? How likely are we to pass an STI from one person's hole to another person's hole by not changing condoms when we switch holes? What about the toys? Washing the toys between each person they're inserted in seems a bit interruptive. How risky, as compared to unprotected sex, is sharing a toy? Are there any risk factors we are not taking into consideration here which we should be?

Thank you for all your replies to everyone who's written you in the past. These have been instrumental in my growth, both as sexual person and as a parent. This is shameless flattery in hopes you post/reply to my letter.

Perhaps Orgasms Less Likely Yet?

My response after the jump...