Chuck Bass, of the long-gone masterful TV drama Gossip Girl, is an ethical mess of a character. He’s a rapist, for one thing, and arguably emotionally abusive. He’s a cutthroat businessman who sometimes makes cruel decisions to keep his bottom line afloat, he’s rude to his parents and step-parents, and he usually doesn’t even treat his closest friends with consideration or love.
None of this is excusable. But sexual fantasy exists beyond the plane of ethics. So, admittedly, Chuck Bass is one of my favorite fictional characters to fantasize about, read fanfic about, and make sexual speculations about. Here are some of my headcanons for what’s lurking in Chuck’s sex toy collection…
Like Christian Grey, Chuck Bass has a “playroom,” though he would never be so churlish as to call it that: it’s his boudoir. It’s kitted out with a Liberator Esse chaise, which he uses in a wide variety of imaginative ways. However, despite his Grey-esque proclivities, he thinks Fifty Shades of Grey is pathetic trash, an opiate of the suburban kink-curious masses. The day he catches you reading it is the day you discover what it feels like to get repeatedly and aggressively spanked with a trade paperback.
He keeps an Njoy Eleven displayed elegantly on a sideboard in his bedroom, atop a charcoal-grey velvet Throe. When you’ve been very, very good, he has you fetch both for him, and he makes you squirt with deft, almost businesslike precision. Afterwards, he leaves both items outside his bedroom door for the maid to wash. She does this quickly and without asking questions.
He’s obsessed with gold-plated bedroom accoutrements, because he’s always got scads of cash burning a hole in his silk-lined pockets. He keeps a gold Eroscillator near the bed for use on beautiful visitors. Occasionally he mentions an interest in forced orgasm play – sometimes it’s a threat, sometimes a promise. One day he actually follows through, blindfolding you, then tying you to a rococo chair and the Eroscillator to you with black silk rope. He turns it to the top setting and sits back in his leather recliner with his fingers steepled, watching with quiet mirth as you squirm and scream.
He owns a gold-plated Lelo Earl prostate massager (he would never be so crass as to call it a “butt plug”). It was a celebratory gift he bought for himself when an important merger went through. You’ve come to know that when he wears the accompanying gold cufflinks out to dinner with you, it means he’s feeling libidinous. But he never lets you fuck him. You never dare to ask.
