pov

Clad in a skintight, black latex dress, and tall, 4 inch platform black heels, Jessica was a stunning figure as she looked down at her two slaves, on their knees. “Up” she said to Hailey.



“Yes Mistress Jessica.”



Hailey stood, naked, save for the black collar around her neck.



“Now” Jessica said, looking at the other slave, “it’s time for a little fun with my new slaveboy. Stand, and do not move except when moved.”



Adam stood, his plain clothing standing out amongst the scantily clad girls. Nodding to Hailey, Jessica commanded:



“Remove his clothes.”



Giggling naughtily, the seasoned slave began to run her hands up and down Adam’s body, teasing each part as she slowly removed his clothing. His conditioning was barely holding up–any less talented a hypnotist then Jessica, and he would have broke down into a whimpering mass of lust and frustration. Instead, he merely whimpered and moaned quietly as Hailey removed the last items of his clothing, his naked body appropriate considering the scenery, and his 8″ cock hard as a rock.



“Hand on your cock slave.”



“Yes Mistress Jessica.”



His hand flew to his dick, and his mind rolled in pleasure as they met–it took everything he (well, his deeply controlled mind) had not to begin stroking.



“As I give the following commands, you will pleasure yourself, and this pleasure will wash away any fears or resistances you may have. You will have no choice but to enjoy it.”



“Yes Mistress Jessica.”



“You are going to stand there calmly as Hailey slides long, black, silk gloves onto your arms, and long, black, silk stockings onto your legs. The feeling of the silk on your skin will drive you insane—every time you think about it, the feeling will only get better. As Hailey puts the heels on your feet, you will begin to realize what a sissy slut you are. You will think and act like a girly little pussyboy. Is that clear?”



Adam’s mind was on fire. She was making him…into a girl. He should be furious. Embarrassed. Scared. But he only felt pleasure. The pleasure in his cock and the pleasure in his mind–perhaps the pleasure deep down in his subconscious that he always wanted to deny was there–manipulated his mind and controlled his actions. He gave the only possible response.



“Yes Mistress Jessica.”



With that, Jessica took the gloves and stockings off of a nearby table, heels clacking across the floor and hips swinging as she walked. Handing them to Hailey, she commanded:



“Put them on him.”



“Yes Mistress Jessica!” the trained slave said excitedly, her secret obsession with crossdressers from a life long past bleeding through. Walking to him, she grabbed him firmly by the wrist, and began to roll the glove up his arm…



His body was on fire. The silk felt like heaven and hell all at once. The soft, cold, teasing touch of the fabric on his skin sent ripples across his body that screamed in pleasure. He couldn’t avoid loving it. He couldn’t avoid wanting it. He couldn’t avoid the wonderful feeling of these feminine cloths wrapping his body….



She reached his legs, rolling up the stockings to slide them on. She was enjoying this. She was so thankful Mistress Jessica let her think enough to enjoy things. Mistress Jessica was always so good to her. She’d never want to go back to the before times, when they were simply platonic friends, never knowing what they could become…



He couldn’t bear it. And now she was going to get the heels! He wanted them. He wanted to be Mistress Jessica’s little pussyboy. He wanted all of it. The silk enchanted his skin and his mind equally–all he could feel or think was the pleasure of having these girly pieces of clothing touching his body. The heels! Hailey was sliding them on now. The four inch stiletto propped the ball of his foot up high off the ground. It was an amazingly awkward feeling, and only made it more embarrassing, and therefore more pleasurable, for him. Or was it her…? He…she…wasn’t really sure…



She loved it. So much. The sight of him dressed all in feminine accessories, the black cloth and leather against his tanned skin. It lit her pussy aflame. There was something so attractive about a hot male trussed up as a woman like this. She just wanted to have him. He giggled… she moaned…



She loved her heels! Giggling and smile, she leaned inward and outward awkwardly, sighing from the thought of her legs held up in the air like a slut by these amazing shoes. She looked at Hailey. Hailey was a hot girl. Very hot. Wait, girls didn’t like other girls? Or, only good girls like other girls. She’s a good girl right? She’s a girl, right? Ah, doesn’t matter. Anyway, who was that over there…



With that, he locked eyes with Mistress Jessica, freezing and staring intently, girlish smile frozen on his face. Jessica stared back, a naughty and pleased grin on her occupying her own.



“Hello my little sissy. How do you like your clothing?”



Giggling, he responded:



“I love it soooo much Mistress Jessica! It’s naughty and slutty and it feels so good!”



He giggled again, his high pitched tone octaves above the submissive, obedient responses he had uttered earlier.



“Good little sissy. Hailey, you look a bit bothered. Let it out, whatever it is. Now.”



With that, Hailey collapsed to the ground, hand flying to her pussy and fucking herself silly. She struggled to keep her eyes open. Why did she love seeing this so much? She just had to have him… her… whatever… she wanted it so bad.



“That’s well enough of that slave” Jessica said, grinning. “Do you want our little sissy here?”



She stopped immediately, staring at Jessica like a pet to its owner.



“Yes Mistress Jessica!”



“Then take her” Jessica snapped—to which Hailey bounded over and threw her tiny little frame onto the sissyboy. She wrapped her arms around his shoulders, and legs around his waist, combining the feeling of his skin and the silk as she prepared for the best feeling of all…



Oh! Suddenly the hot girl was up on her! What was her name… what was her name… Hailey! The sissy stared hungrily at Hailey, in her mind dripping at the thought of taking the sexy female slave. Little did she know, she was about to have her…



FUCK YES. It felt SO good! Hailey let out a howling moan as she plunged her pussy onto the sissyboy’s cock!



“Oh yes! Fuck me you little girl! Fuck me, fuck me, fuck me!”



She flew up and down his cock, feeling the silk rub against her skin, reminding her that the long, thick cock she was fucking was attached to a hot male wearing hot female clothing. She couldn’t stand it. She just couldn’t stand it! The pleasure was so GOOD…



Oooooh! This felt AMAZING! She LOVED fucking Hailey! She struggled to maintain her balance, stood up on the towering heels, and the awkward struggle only made the experience more pleasurable—she was such a dirty, slutty girl! Slutty girls fucked, and they fucked in big, tall heels! She giggled uncontrollably. It was so dirty and slutty and fun and felt so GOOD! She didn’t get exactly how Hailey was doing it—how did rubbing two pussies together feel so amazing?—but it didn’t matter. Giggling, she begged “Please fuck me…”



MORE! All Hailey could think was MORE! She screamed in pleasure, just as the giggle reached her ear—it was so SEXY! She loved hearing the dirty pussyboy giggle, and grabbed him (her?) tighter. His (her?) cock was so big inside her, it was amazing. She just wanted to slam herself down on it over and over and over…



“Cum” said Jessica, in a manner that was somehow both matter-of-fact and mischievous.



“OH! OH! OH! OH!” She could feel herself releasing, lifting, exploding! She had never known pleasure like this in her life! She was giggling and moaning uncontrollably! Good little sluts get pleasure! Good little girls get to cum…



“YES! YES! OH YES!” Hailey howled, her cries of pleasure only drowned out by the feelings in her body. She was trained to cum on command, and it never lost its potency, but this time was so much BETTER! Her pussy pulsed in waves of indescribable pleasure that spread throughout her body and orchestrated her limbs—they clawed and grabbed at the giggling sissy, pushing Hailey down harder on the pussyboy’s exploding cock. She could feel it fill her pussy with cum, and it drove her so wild she could barely stay conscious!



“Fill me you dirty, giggling slut!” she screamed, pumping his cock with practically inhuman speed, before collapsing onto the ground in a twitching mass of pleasure, lust, and brainwashing. The cum leaked out of her pussy, and she lay there limp, nothing moving but her amply sized chest—her mind was blank except for the instinctive ability to remain alive. She had been fucked empty. And she loved it…



He had no idea what was going on. Everything felt so good. Everything was amazing and pleasurable. Everything made him want to giggle. The silk on his skin and the cum on his cock fought to tell his brain what gender he was. But it didn’t matter. Everything felt too good for it to matter. He collapsed, cock pulsing and mouth smiling…



Mistress Jessica surveyed her work. Hailey lie on her back, eyes glazed over and pussy oozing with cum. Adam lie on his side, a dumb, slutty smile on his face, and cum covering his long, black stockings. She removed the dildo from her pussy, sliding it out from under her dress, and turned off the vibration. That was good. But now someone had to clean up. And it certainly wasn’t going to be her. Hailey and Adam couldn’t do it—they weren’t even conscious, and were due for conditioning anyway. “Well then” she thought.



“Zoey! Lexi! Get in here slaves!”

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