Just a note on your advice to Pre-Menstrual Sissy, the man whose Mistress ordered him to put tampons in his ass: There are reasons why he should be careful, aside from constipation and it "getting lost." Primarily, the rectum is not self-lubricating, unlike the vagina, and a dry tampon in a dry rectum can cause adhesion problems. If he sticks it up there, he could easily have the upper cotton layers bonded inside his ass. This is less than comfortable, and can cause infections. I would suggest that he lubricate the tampon with Vaseline or a similar substance before insertion.
Tampon Play Troubles
Here's some extra advice for Pre-Menstrual Sissy, and also info that your menstruating readers might be interested in. Traditional tampons or pads have rayon in them. Your body can absorb the rayon from the tampons. Often this causes cramps and discomfort, since your body really is not made to be absorbing rayon. Sissy might want to go to a natural food store or co-op and get unbleached cotton tampons. Sissy could also tie something to the end of the tampon string to keep it from getting lost in his rectum. Maybe Mistress can think of something extra humiliating?
As a physician and a submissive crossdresser, I thought you would like my perspective on rectal tampons. First, I agree with you completely that PMS should do as he's told! Secondly, I follow some common-sense guidelines for all inserted objects. Nothing sharp or breakable. Clean it. Lubricate it. Remove it. Clean it again (or discard it). I remove tampons after a few hours. First-timers should figure out how a tampon works before actually inserting it, and experiment with different positions (lying on your side or back, on all fours) for insertion. And, most importantly, don't forget to leave the little string hanging out!
Tampons Allow Men Periods Of Naughtiness
Thanks for sharing, TPT, BH, and TAMPON--nothing alleviates the nausea of a hangover like the mental images your letters conjured up.