Curiosity Killed the Cat, but Satisfaction Brought It Back

“…Yes.” Amy bites out. Now it’s a combination of curiosity and lust that keeps her here. This is fucked, and it has to be a joke, but it’s a hot, fucked joke.

Dr. Wynn smiles, reaches into her desk drawer and pulls out a fucking horse dildo and a bottle of lube. She slams the dildo on her desk so it suctions down, then douses it in a generous amount of lube.

“Shirley, ride.” Dr. Wynn orders.

“Yes ma’am!” Shirley says brightly.

She climbs up on the desk, giving Amy a clear view up her short, plaid, “fuck me” skirt to see the bright red panties beneath. She then reaches under her skirt and drops those panties, revealing a round, puckered asshole with a metal piercing poking out around the rim, and pair of small, feminine testicles hanging under a flat, metal chastity cage. The transwoman or sissy or femboy or whatever she is spreads her cheeks, gaping her asshole and pressing it down on the flared head of the dildo, slipping it inside her with a lecherous squelch. She squats, still wearing her stiletto heels, and begins to rock up and down on the toy, making a symphony of lewd noises.

“Now, Shirley,” Dr. Wynn says in a clinical tone, “Tell Miss Dean how your real self feels about this.”

“My real self hates it miss!” She says, brightly, letting out another soft moan as she does so. “Part of the conditioning makes sure he feels everything just like it’s the first time, and he was a very transphobic, homophobic man. He’s screaming in my head right now, begging me to stop.” She says, with a giggle. “You would think he would know by now that will never happen, but his conditioning prevents it.”

She lets out another, erotic gasp as the toy slips deeper into her asshole. “He has to fake like he likes it and pretend to be Shirley, his fake self, who’s really nothing more than an extra layer to his humiliation. For example, I can tell you all about how I’m planning to go offer blowjobs to some local street thugs I saw on the way into work today.”

She presses further down onto the toy, giving a lewd squeal as she does so, before continuing, panting. “He’s known all day I’m planning to do this, but he can’t stop it, because it’s really him planning to do it, and even though I’ve done stuff like that a thousand times by now, each time is just as bad as the first.”

She picks up the pace, moaning and whimpering more frequently. “His life is a living hell, and the best part is, it’s all his fault! His wife tolerated him abusing her, but when he made her have a threesome she realized she was bisexual, and that lead to her falling in love with a woman, contacting Purity Medical Group, and condemning him to spend the rest of his life as Dr. Wynn’s slutty sissy fuckdoll.” She lets out a particularly loud moan as she hilts the toy in her butt, before looking up at Amy with a board, slutty grin. “Isn’t that great?”

It could be fake. It could be. But every part of it feels so perfectly wrong. The way each moan interrupts her soliloquy just enough to accentuate the sexual element, while the cheery, bimbofied quality of her is in such stark contrast to her word, and her eyes are so vapid and empty Amy can almost see the anguish in them, but not enough to be certain it isn’t her imagination.

“Finish, Shirley, then clean my desk.” Dr. Wynn says. “Come, we’ll talk in the foyer while she concludes her ride.” She adds to Amy while Shirley picks up the tempo to a fever pitch.

“That was horrifying.” Amy says, as they step through the doorway.

“But hot, because by his own admission, the victim deserved it.” Dr. Wynn points out with a smile. “We don’t use that demonstration for just everyone. We were reasonably certain you’d appreciate it more than you found it unsettling.”

And, Amy has to admit, she’s not wrong. For all that it was horrifying, it’s much harder for her to wrap her emotions around a theoretical wife-beater’s torment than it is a hot transgirl moaning like a bitch while riding a dildo. Her brain says this is a bad, horrible place and she should run, but her pussy says she could think of a few ways to add to Shirley’s punishment that would be pretty fun.

“We’re not monsters.” Dr. Wynn continues, “Shirley’s case is one of most **** **** modifications, and even then, we ordinarily ensure the subject is perfectly happy in their new state. Only in the case of truly deserving victims, like the man Shirley was, do we leave a subject in a condition they truly hate. Shirley actually attempted to **** her ex-wife before we got her, so it was decided she deserves something suitably unpleasant to reinforce the magnitude of her misdeeds.”

Amy hesitates a long moment before saying: “What…hypothetically, what would you do for my husband? Nothing like that, right?”

Dr. Wynn looks aghast at the notion. “Oh, no, nothing like that. We need to review your psychological profile, as well as gather some information about him to be sure, as finding something that both satisfies you and leaves his base personality unaltered can be a particular matter, but I suspect you’d be most pleased with our Vixen package.”