I am a women in her 40's. A male friend of mine, who I have been having a sexual relationship with for many years, is dying of cancer. On his bucket list, he has requested for two threesomes—one with both me and another man, one with me and another woman.

I haven't found a girl yet but I have found the perfect guy. I had a sexual relationship with him in the past. Both men have always treated me with respect and kindness and both are clean of disease. They are both open to exploring and experiencing being with a man for the first time and all that it will entail; kissing, mutual oral sex, and trying to both be tops and bottoms for anal. Neither one of them has met the other but based on my recommendation and an exchange of photos, both are good to go. I've been doing my best to prepare them. I really would like for them to enjoy themselves and get the fullness of whatever they are seeking out of their first same-sex encounters. For our rendezvous, I've told them both to practice ahead of time with a dildo, to make sure they evacuate, to be clean shaven both on the face and in the privates, and to be slow and gentle at first when going in from behind—and, of course, to bring lube.

Do you have anything to add? Any suggestions?

A Wish Not Covered By The Make-A-Wish Foundation

One suggestion.

Don't plan on having just one MMF threesome, AWNCBTMAWF, plan on having two or more MMF threesomes—assuming there's mutual interest after the first one, of course, and assuming your friend's health is good enough to be making plans for the next few months.

Here's why you should frame this MMF threesome as the first of a possible set or a possible series: so long as this threesome is hyped as a one-time, one-off, one-shot deal, both of your male friends—your dying friend and the friend you've tapped—are gonna go in feeling like they've gotta cram every last gay thing into this one threesome. Dude-on-dude kissing, two dudes giving and receiving blowjobs, dudes taking turn topping each other and bottoming for each other: that's an awful lot of man-on-man action for one night. Not only are you placing a lot of pressure on both men to perform, AWNCBTMAWF, you're not leaving much time for you, your needs, or your lady bits/butt/mouth.

You don't want your dying friend to feel rushed or pressured to do everything—what if ass isn't in buttfucking gear on the big night?—or to leave feeling like his first MMF threesome was a failure because he didn't tag every gay base or fill every manhole. Even if a second or third MMF threesome doesn't happen—if there isn't time or mutual interest—the one that does will feel easier, breezier, and more successful if both guys are free to enjoy what comes without having to worry about what doesn't.

And just for the record...

People with sexually transmitted infections aren't unclean. They have an infection—some treatable, some not, some a big deal, some not. And remember: "expose" does not necessarily/always equal "contract." You can have safe/safer sex with someone who has a sexually-transmitted infection and risk exposure (your partner might be shedding the herpes virus, your HIV+ partner's condom might break) or even wind up being exposed (your partner was shedding the herpes virus, your HIV+ partner's condom did break) without actually contracting the particular sexually transmitted infection you were exposed to.

Your friend with cancer may have a compromised immune system, though, and a herpes outbreak—a first one—could be very aggressive and very unpleasant. So do your best to be stay safe. But keep the risks and rewards in perspective. For example, I can't imagine your friend who's dying of cancer is too concerned about contracting HIV just now.

Good luck!