I’m a 50-year-old cis straight female writing with a question about my son. He’s 19 and in college. I’m a single mom and we are very close. When he was eight, I found him on my laptop looking at videos of “strong women” wrestling with men. Since then, that’s all he looks at online and fantasizes about. There is a particular woman he follows. For a fee, you can wrestle with her. She engages in other acts as well (BDSM), but according to my son, sex is not permitted. He says her website is very clear about this. He assures me she’s legit and has only positive online reviews. I asked to look at her website, but he was reluctant to show me due to embarrassment. I didn’t push it. Then for his upcoming birthday he asked if I would split the cost of a session with this woman: $600!...

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I’m a 50-year-old cis straight female writing with a question about my son. He’s 19 and in college. I’m a single mom and we are very close. When he was eight, I found him on my laptop looking at videos of “strong women” wrestling with men. Since then, that’s all he looks at online and fantasizes about. There is a particular woman he follows. For a fee, you can wrestle with her. She engages in other acts as well (BDSM), but according to my son, sex is not permitted. He says her website is very clear about this. He assures me she’s legit and has only positive online reviews. I asked to look at her website, but he was reluctant to show me due to embarrassment. I didn’t push it. Then for his upcoming birthday he asked if I would split the cost of a session with this woman: $600! My first concern is for his safety. Maybe I listen to too many true crime podcasts, but I’m worried that something bad will happen to him and I’ll never see him again. I know that many people visit sex workers and live to tell the tale. And now, as I sit here writing this, I realize that it’s sex workers who are the more vulnerable ones. So, maybe his safety is a non-issue. Still, I’m his mom and I worry. My other concern is that engaging with this woman may mess him up sexually. He hasn’t had any prior sexual experiences and I’m worried that if this woman is his first experience, it will make ordinary, real-life pedestrian sex uninteresting for him in the future.

I have no one to talk with about this which is why I’m reaching out to you. I’ve always maintained an open and non-judgmental relationship with my son, but I’m really struggling with this. He already has an appointment and I’m super ambivalent about this and need your reassurance.

They Grow Up So Fast

“I’ve always been kinky,” journalist and author Jillian Keenan wrote in her 2016 memoir Sex With Shakespeare. “My fetish appeared early, long before I knew anything about kink or the diversity of sexual lifestyles. As a child, I pored over any book that mentioned spanking, paddling, or thrashing. Tom Sawyer and The Whipping Boy went through many early reads, as did, believe it or not, key entries in the Oxford English Dictionary…. I looked up the definitions for spank, paddle, thrash, and whip so often that, after a few years, my dictionary automatically fell open to those pages.”

Keenan’s memoir tracks her two lifelong obsessions: the plays of William Shakespeare (way kinkier than your high school English teacher ever let on) and her love of spanking, obsessions that have intersected and informed each other in surprising ways throughout her life.

Reading Sex With Shakespeare might give you some comfort...


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