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Chapter 18
by
Nicegent42
What's next?
Chapter 17
A couple of days later, Calvin strolled over to the Downings household for a luncheon date with Ezme, consisting of a home-cooked meal and some Netflix ‘n’ chill. Ezme had already confirmed to Cal that their first date was the best night of her life, and that she was Ezme for good now, Zeek gone forever. Calvin was confused, odd thing popping up normally meant a prank, but their didn't seem to be any thing fake about how Ezme looked or what they did to him on their knees the truth seemed to be Zeek was actual coming out to his best his best friend, but Calvin knew he wasn't gay but Zeek didn't look like a boy any more and so long as that remained true he was happy to get sucked off, he always imagined…wished he would end up with Eliza but after that night he had been thinking about how and when he was going to bend Ezme over for a good fucking. A lunch date didn't sound like the right time for that but he always had hope.
Somewhat progressively not caring whether the nookie he got was cis or not, Calvin embraced Ezme’s truth and walked right into the trap as he hoped for a repeat of his first blowjob experience, or perhaps even something more. Maybe he could even convince Liz to join in on the fun; getting head from two sisters at the same time? Cal would die a happy man.
Before he ever arrived Ezekiel was rushing about in his kitchen, his waist cinched, bra straps digging into his shoulders under a white and blue tea dress all while his feet throbbed in a pair of high heels with thin ankle straps. With his all too feminine hands Zeek let out a long sigh before trying to wipe his flour covered hands off on the stupidly frilly waist apron. His sister, the bitch had been overly threatening to him about getting “his” dress dirty before the lunch date, one he was now cooking for despite being less than willing. “Liz, I got the chicken battered. What's next?” he yelled out knowing she wouldn't be far so she could make sure he followed the plan what they had in mind for the day differed from person, what Calvin had in mind though…
That was not what happened at all. The Pollo a la Diablo Ezme whipped up had the exact right amount of sleeping pills in to knock Calvin out cold. Zeek's mind had been fueled by **** Thea had repeated her performance with him and even if he didn't want to **** Cal he would have followed directions on how to cook just to make her happy. So he had minced around the kitchen, simple navy blue three inch pumps, a white and blue tea dress that hung down to his calves, a little apron, and of course the other womanly undergarments. If it had just been the dress and not the heels and bra it could have been comfortable, other than his own did hidden away and balls crammed up into his own body. From the early morning he spent time getting ready, trying and trying again to get the make up right and to have his hair looking just right Once asleep, Liz and Thea came out of hiding and the trio quickly got to work.
Zeek knew from experience that a single benadryl could make his friend... Ex friend to sleepy to function, so it was no real surprise to find Calvin face down in the food he had worked hard to prepare and hardly burnt it at all. That meant the plan was working and yet he found himself standing with his hands on his hips feeling annoyed that the meal he worked so hard on wasn't going to be finished.
Eliza leaned forward both her hands on the dinner table making sure the now passed out creep wasn't going to suffocate himself on the meal. ‘It would be a sad way to die drowning in mashed potatoes.’ she thought, highly amused. “Ezme you take his feet and we will get him upstairs for stage two, unless you would rather try to wake him up with a blow job.”Zeek didn't so much as respond his lipstick covered limp pressing into a line as he moved, one foot in front of the other to keep himself from stumbling in his current footwear to help the young man who was dead weight now.
Having seen his dick before, Ezekiel was the one to have to deal with undressing Cal, ridding him of body hair and re-dressing him in the outfit of their choosing, the entire ordeal was exhausting and he didn't understand how his Thea could get so much enjoyment from such an activity. Cal was still snoozing thanks to the aid of medication, but now he looked a bit different. Shaved smooth, dick tucked and taped, wearing panties that showed no sign of manhood, a corset, cinched tighter than most would wear it, stuffed bra, and a velvet green dress. One his sister said was a shame for her to lose even if it was for a good cause.
The dress was high necked almost like it wa a turtle neck, had three quarter sleeves, the skirt of it hung down low enough to cover the newly crossdressed boy’s knees so poking out from the dress were dark nylon covered legs an article of clothing Zeek had ruined a few pairs of before he was done with his part of things but to finish things off the girls added a little more. Like a second corset to be worn over top the dress, oddly it cinching much easier thanks to the first one doing its job to give the now feminized young man a more hourglass shape, on his neck they put on a simple black cloth choker,when that was all done Liz got to work. Shaving the **** boy's head and gluing a new human hair wig to his scalp. Just like with her brother Zeek’s money had been used to order Glamazon Premium next day delivery specifically for Cal, this wig was just as expensive as the last but looked dramatically different, this one was a brunette short bob cut with bangs.
Thea did makeup with help from her feminized assistant while Liz tackled nails and made sure her camcorder was positioned correctly for most of the makeover. When Cal awoke, he found himself handcuffed to a chair with three girls surrounding him and a god awful pain around his midsection that made him feel like he was being squeezed like advice while his feet were at an odd angle and cramped all three people around him looking at him smugly, a full body mirror beside them.
“Wakey-wakey, Catlyn”, Liz mocked in a low-pitched, song-like voice.
“Catlyn, who’s Catlyn? Wait, what’s going on?” Calvin slurred as he still didn't have all his faculties, arms pulling slightly on the cuffs finding them secure.
There was something, or more accurately many things off; his face felt heavy, there was a strange taste on his lips, a tickling around his neck, ears and shoulders, and the sensation of things gripping tightly to his body, weighing down his chest area in particular. Moving his feet, his shoes no longer felt sturdy or flat, like he was on his tiptoes. Slowly, his reflection came into focus.
Looking back at Cal was an eerily-familiar woman around the same age as him, sporting brunette hair, a bob haircut with her forehead covered from her bangs, a large bust and hips, trim waist, and a cute face albeit with heavy makeup.
“Here these might help you see Catlyn." Thea said, putting black rectangle shaped glasses on the face of their latest victim. The glasses just had regular glass in them but she thought they were cute, something a little office girl might wear.
The dark haired girl in the mirror handcuffed to the chair wore a form fitting forest green velvet dress with a corset over it the dress had partial sleeves allowing him to see her arms bound to the heavy wood chair, the dress went down to her knees where he could see shapely nylon covered legs he wished he could see more of. On her feet were heels that he imagined strode the line between work acceptable and making her ass look fuckable at least if his time working at his dad’s car store has taught him anything about how women dressed for work. The large hoop earrings told him she was looking more for attention than going to work.
“Ezmee, Eliza, what is going on, my head ... I feel so tired.”
When he spoke, so did the dark haired girl. He could see it in the reflection, her lips moving her lips and head in time with hil, and in that second it clicked, what she was wearing, why he was so uncomfortable and unable to get up from the chair.
“…Oh!” Cal said, pulling on his bindings once more. “You got me good, jokes over though.”
“Jokes over!?” zeeks voice came out in a shrill anger. “You made me suck your fucking dick. I should fuck your face see how you like it just because you are wearing a dress.
“Now, now May-May.” Thea didn't just touch the crossdressed boy still wearing the blue and white tea dress, she hugged him from behind and kissed his neck. She could feel his knees almost buckling from being kissed in such a tender spot. “We have set up a date for Catlyn and you are going with her to make sure she acts like the slut she is.”
“What!? Zeek responded while Cal looked on in confusion, his mind still recovering from whatever had been put in his food.
Eliza shook her head at her best friend giving her shitty brother too much positive attention as far as she was concerned.”A double date… I know how slutty you like to be, dear cousin. You can say no but then Catlyn here will be free to go, do you want that?” Shaking her head, Eliza walked out of her bedroom phone in hand still having things to set up.
Balling his hands into fists Zeek wanted to tell little miss perfect to go fuck herself, but her hold over him had only gotten stronger. “No, he needs to pay.” he practically growled, pulling free of his long-time crush, kissing her arm as he did, eyes narrowing at his ex-friend, a devilish smile on his face.
Ezekiel looked the person sitting in front of him over once more, this time actually trying to appreciate what had been created. He really couldn’t see Cal, the hair, and glasses doing a good enough job on their own to make it hard for him to tell without looking real hard. The dark haired girl struggling while cuffed her slim waist, nylon covered legs and heeled feet. His threat of fucking their mouth for **** feeling like a better option. “You know Catlyn, my good friend Calvin went to town o n me last night filling my mouth with his seed. It was disgusting. I wanted to throw up, but he seemed to enjoy it. He said I was a good cock sucker, are you a good cock sucker? He said rubbing himself through the dress and panties, the light material and his **** fantasy turning him on more and more.
“What!? Zeek, man, I don't know what is going on but just because your trans doesn’t mean I am. You don't need to feel ashamed for wanting my dick, weare friends… just closer than ever now.”
Blowing out a deep breath Zeek blew on the realistic but fake blonde hair out of his face that was hanging down in his face. “Trans? I, not trans, I have been blackmailed into this the entire time, I didn't want your dick or to ever know what cum tastes like.”
Scrunching up his eyebrows Calvin wasn’t sure what Ezmee…Zeek was saying it made so little sense. “I didn’t know, I swear… you have been flirting with me via texts and then the way you acted on the date. I mean come on you can’t pretend you weren’t having fun.”
Gritting his teeth, them outlined with his lipstick covered lips, Zeek stepped forward the heels on his feet clicking even as his body shook with rage. “Fuck you and yeah you know what I will! We are friends so it only seems fair that I get what you did.” Zeek continued to rub himself feeling himself starting to get hard. Once in front of the bound person he pulled up the dress and the panties down. He continued to rub himself now jerking off in Catlyn’s face.
“Ah… ah, come on, come on we can talk about this. No, no, no….. Please, please!”
The interaction was not what Theadora had expected at all and a large part of her knew she should end this but another had her sitting on the edge of the bed covering her mouth in shock as it unfolded.
“No? I think Yes!” Zeek said his anger burning him up inside as he grabbed the feminized figur in front of him by the back of the neck. They couldn’t be moved far but the shock of the **** action had the panicking figure open their mouth and that was all he needed to shove his cock between their pretty lips. He felt the warm wet mouth, the texture of their tongue as he slid his dick across it, then he heard a familiar sound as they started to gag. The last time it had been a sound coming out of him but now it was music to his ears. “Yeah bitch, take it! Take my cock!”
Calvin shook his entire body including his head as he tried to pull back to get the invader to his mouth, but he had no leverage despite the panic rising in him more and more whatever had been put in his food still left him drowsy.”Glug glug glug.” The sound came out of his mouth as saliva drilled down past the dick in his mouth as it was **** back and then forward again over and over again.’The fuck!’ He thought starting to feel like he was chocking as his face was fucked by thee person he had known since they were children and the worst part was they still looked fine as hell as it happened making it a truly surreal experience. Something slick started to trickle into his mouth it was watery but slightly thicker with a faint saltiness as precum started to leak from the cock in him
“Come on Caitlyn, you could at least put some effort in. My advice to you is the better job you do the quicker this goes oh and at least pretend to enjoy my cock, you can do this girl be a good little cock sucker.”
Getting up from the bed, Thea ran har hand up her Ezmee’s arm. “My pretty pretty girl, so angry.” she cooed gently, turning their face in her direction before leaning in for a slow sensual kiss.”Does thar feel good?” She asked, seeing their mouth practically hang open as they slowly nodded the rhythm picking up with eac nod as they groaned, not willing to stop thrusting their hips over and over again.
Thea gave her little May-May another kiss this time following it with another and another trailing them up the neck. “Your dates will pay but us girls pay them back in a different way. Didn't you like how I paid your efforts back?” she whispered
Zeek nodded loving his alone time with her even if she had an odd fetish.
“Then you are going to help Catlyn right? Do it for me, I promise to pay you back. May-May, I want to have you between my legs tonight but for that to happen you need to show Catlyn how to properly handle a thick piece of man meat. Knowing you will get a real prize, will you do that for me?”
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Locks for Love
Hair
Ezekiel is sick of hearing about how perfect his older sister is and plays a mean "prank on herby cutting her long hair, as punishment her has to learn how much effort goes into having long hair but soon as their father goes out of town thing get so uch more involved and worse for him.
Updated on Feb 12, 2026
by Nicegent42
Created on Dec 8, 2025
by Nicegent42
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