Originally published June 16, 2005:

I can't ask my doctor about this one, and hope you and your specialists can help. I am a crossdresser currently going through feminization training with an internet Mistress. We are about to embark on a simulation of my getting my period. This will require that I use tampons for several days. I know of toxic shock syndrome (TSS) and the requirement to change tampons frequently, but are the risks greater for anal use of tampons?

I want to be sexually smart and not harm myself. Please help.

Pre-Menstrual Sissy

My response after the jump...

First, a medical opinion: "A search of the medical literature turns up nothing to guide us," says Dr. Barak Gaster, Savage Love's long-suffering medical go-to guy. While there are no cases of death from men putting tampons up their butts, Dr. Gaster nevertheless thinks it's a bad idea. "I'd still be worried about constipation from excessively dry stool or the tampon getting lost up there," he says. "So, even though there's not much risk of infection, I'd still recommend he wear pads instead."

Now, a sex-advice columnist's opinion: Isn't inflicting a little discomfort the whole reason your Mistress is ordering you to shove tampons up your ass? If you get constipated, take some Ex-Lax; if you lose one up there, you'll just have to ask a doc to dig it out for you. The relatively small risk of constipation or a humiliating visit to a proctologist's office shouldn't keep you from following your Mistress's orders, PMS. Do it, sissy.