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 and I felt like I navigated those waters pretty well. 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 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. Is this just the same kid who has always been curious about sex? Or are these warning signs of some sort of sexual deviance?
— Mom In Sleepy South Carolina Lovingly Educates Offspring
Take a deep breath, MISSCLEO, or take two.
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. He knows you've always accepted him for who he is, 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, 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.
My hunch is you don't have a sex offender on your hands or a kid drifting into organized crime. 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 this is something he needs to discuss with you at all.
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. 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. 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 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
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, "sixteen 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, PARENT, 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. 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.