A Take a deep breath, or take two—take however many you need until you’re back in touch with your inner mom, the one who doesn’t freak out. Your son may be a cross-dresser or he may be trans or he may find bras and panties titillating because women wear them and he wants to sleep with women (not be one). (Lots of gay boys are titillated by jockstraps—but a closeted gay boy can collect ’em all without freaking out his mom.) We can’t know whether your son is a cross-dresser, trans, or merely titillated, but he’s clearly exploring and wants to do so privately. So while he could go to his mom and ask for a pair of panties and let her know exactly how he intends to use them, he doesn’t want to ask his mom for a pair of panties or share his uses for them with his mom. He knows you’ve always accepted him for who he is (but a reminder never hurts), so if this is about his gender identity, well, you’ll have to trust that he’ll share that with you when he’s ready. But if this is about a kink, he may never share that info with you, because why on earth would he? Kinks are for sharing with lovers, not mothers.
Give your son some space, including the space to make his own mistakes. As teenage misbehaviour goes, swiping a single pair of panties isn’t exactly a crime spree. If you suspect he snuck into the girls’ locker room and made off with a bra (there has to be an easier way for a guy to get his hands on a bra!), you’ll want to address that with him—not the “Why do you want a bra?” part, but the risk of getting caught, suspended, expelled, or worse. There are too many prosecutors out there looking for excuses to slap the “sex offender” label on teenagers—especially in the Bible Belt.
My hunch is you don’t have a sex offender on your hands or a kid drifting into organized crime. You have a slightly pervy teenage boy who’s curious about sex and who may, like millions of other men, have a thing for women’s undergarments. You should emphasize the Not OK–ness of shoplifting panties from stores or stealing bras from classmates (or the siblings of friends or laundromats or thrift stores) and the possible consequences should he get caught—theft charges, suspension/expulsion, losing friends, coming into the sights of a sex-negative prosecutor. (Seriously: A man like Harvey Weinstein gets away with assaulting women for decades, but prosecutors across the country are throwing the book at teenagers who got caught sharing pics they took of themselves with their BFs/GFs/NBFs.) But otherwise, I’m going to advise you to back the fuck off. Your son knows you love him, he knows he can talk to you about anything, and he’ll confide in you if and when he’s ready—if, again, this is something he needs to discuss with you at all.
Q My father passed away suddenly. I had a very idyllic childhood and was close to my father and my mother (who is also deceased). Upon sorting through my father’s stuff after his death, I stumbled upon his erotica collection. If it were just a stack of Playboys, I would have thought nothing of it—that’s just men being men. However, his collection contained material that was quite disturbing to me, including photos depicting violent sexual acts and fictional erotica books and magazines with themes of incest. Additionally, there were letters from people with whom he was obviously having extramarital affairs, including during the time that I was a child and believed that we were a “normal” family. Since discovering this, it has been hard for me to come to terms with it and think of my father in the way that I used to. I can barely stand to look at a photograph of him. I consider myself to be a sex-positive person, and I realize that even parents are entitled to be kinky, but I simply can’t get over this. Any suggestions for how to deal with what I’m feeling and how to try to get past it? —Parent’s Arousal Really Ended Nice Thoughts
A Sex-positive, huh? Could’ve fooled me. Your dad was a kinky motherfucker—you know that now—and if you’ve been reading Savage Love for a while, you’ll know that lots of people are kinky and, distressingly, lots of people out there “enjoy” incest porn. “Of the top hundred searches by men on Pornhub,” Seth Stephens-Davidowitz writes in his book Everybody Lies: Big Data, New Data, and What the Internet Can Tell Us About Who We Really Are, “16 are looking for incest-themed videos.” And it’s not just men: “Nine of the top hundred searches on Pornhub by women are for incest-themed videos.” That’s cold comfort, I realize, and it doesn’t make it any less squicky, but your dad’s tastes weren’t as freakish as you thought and/or hoped.
As for his affairs, your happy childhood, and your suddenly conflicted feelings…Your mother isn’t with us, so you can’t ask her what her arrangement was with your father. But it’s unlikely you would have had such an idyllic childhood if your parents’ marriage was contentious and your mom was miserable about your dad’s cheating and his kinks. It seems likely that your mom didn’t have a problem with your dad’s sexual interests or she tolerated them or—and I hope you’re sitting down—she was an active and happy participant. (Kinky women weren’t invented in a lab in San Francisco in 2008.) If your mom didn’t have a problem with your dad’s kinks (which she had to have known about) or his affairs (which she might not have known about), I don’t see why they should be a problem for you.