My only child is 16 years old. He was curious about sex from a very young age and very open with me, so his interest in sexual matters gave me ample opportunity to talk with him about safety and consent. He went through a cross-dressing phase when he was small—mostly wanting to wear nail polish and try on mascara—and I felt like I navigated those waters pretty well, but his father made attempts to squelch those impulses. (He and I are divorced. He has since remarried and is less involved.) That's the background. I've always accepted that he is who he is and done my best to help guide and educate him. Then last year, I caught him trying to shoplift a pair of panties. I'm not the sort of mom who freaks out, but I made him put them back and talked to him about his actions. When I asked him why he stole them, he refused to tell me. I asked: "Did you want them to masturbate with? Did you want to wear them?" He said he wanted to try them on. I told him that if he wanted to explore, he needed to do that with a legal purchase and in the privacy of his own room. Today, I found a girl's bra in the laundry. He says he doesn't know whose it is or how it got there, but this isn't my first rodeo. What on earth do I do? If I send him to a therapist and this is about being trans or cross-dressing tendencies, I'm afraid that will shame him. However, this is now something of a criminal/ethical concern, and I want to nip that in the bud. He is in every way a wonderful human: kind, smart, funny, athletic, no drugs. Is this just the same kid who has always been curious about sex? Or are these warning signs of some sort of sexual deviance? Please help.
Mom In Sleepy South Carolina Lovingly Educates Offspring
Take a deep breath, MISSCLEO, 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, MISSCLEO, 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 misbehavior 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 Okay–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.