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Goodbye Brother, Hello Sis-sy Pt.3
🕑 Added 2021-01-02 10:13:35 +0000 UTCChapter 4
A short drive later Ken made it to the CC’s boutique. Getting out of his car he headed straight for the entrance, baseball bat in hand as he slammed open the door. Knowing something like this could happen Linda had waited at the counter by the entrance instead of in her office where she usually was. Marcy was cleaning somewhere safe in the back of the store while Stephanie had gotten permission to relax in the employee’s lounge to get over the nervousness of what she had done.
What mattered was that both sissies currently in the store were safe. Linda knew neither of them would be able to stand up for themselves. Hell she doubted they would even be able to handle the situation with the shock button in hand. While she loved humiliating her sissies she would let no actual harm come to them and since they obviously couldn’t protect themselves that was Linda’s job. A job she happily did as it rubbed in how much they needed a stronger person to care for them.
“Can I help you with something young man?” Linda simply asked in a calm tone raising an eyebrow as she approach him, clearly not at all threatened by the bat he was holding. Ken while not very short wasn’t all that tall for a guy either he was just average yet Linda towered over him easily, especially in her tall heels. Both her figure and outfit radiated sex appeal. She was Ken’s wet dream, but he was angry enough not to be thinking with his cock this once.
“I’m here to have a serious talk with your sissy stepson or whatever, that bitch of a Stephanie. So tell me where the fuck she is right fucking now!” Ken screamed as he pointed his bat at Linda who still was anything but impressed.
Calm as ever she simply pushed the bat down. “I’m afraid that won’t be possible. I won’t have some wannabe tough guy like you get near my Stephanie, especially not when you’re obviously planning to hurt her. Now put that bat away right fucking now and tell me what you’re here for.” Linda said, her tone calm yet ice cold.
“I fucking told you what I’m here for you fucking bitch. I’m here to see that freak of yours now bring me to her or bring her here it’s the same to me. She did something horrible to me and she’s going to make it right right now. Well what are you waiting for? Do you want me to smash in this glass door of yours?” Ken asked threatingly pointing his bat at the door.
“Oh now I remember, you’re that wimp my Stephanie went to see this morning right? The one with the pin dick who thought himself to be some kind of big shot right? The asshole that tricked my Stephanie into sending pictures even though she clearly had the wrong number? Yeah I told her to put a cage on you, obviously you were just a sissy in the closet, besides no one is going to miss such a pathetic cock.” Linda smirked catching Ken completely off guard.
Shocked he just looked up at Linda. She was behind all of this? She told that sissy to lock him up? The insults about his cock only made it worse. Who did this fucking woman think she was messing with? He was no fucking sissy. Losing his shit right then and there he started swinging his bat at Linda. “She fucking loved my cock liar.” Ken screamed as if trying to justify himself.
Linda still didn’t budge. She simply pressed the shock button she had kept at hand and just like that Ken collapsed on the floor before her, curling up in a ball as a searing pain took hold of him, hitting him straight in his balls, cock and pelvis. It was worse than a kick in the nuts, worse than anything he had ever felt, and it lasted very long, until Linda was happy and released the button.
Putting the front of her heel on his hand holding the bat she pressed down till it hurt. “Let go of that stupid toy sissy. Of course my Stephanie like your cock, she likes literally every cock, but then again yours is just an overgrown clit, locked up as it should be. Deep down you long to serve cock as well, real cocks that is. You’re just too much of a sissy to admit it, but don’t worry I’ll show you your destiny.” Linda spoked down on him, driving up the pressure on his hand until he released the bat.
Squatting down she picked it up and put it in the umbrella holder as if it didn’t worry her one bit. “Now kiss both of my shoes and apologise for assaulting me you fucking sissy.” Linda smirked down to the pained Ken.
“You’re crazy you fucking bitch, never. You will fucking pay for this, you and that freak of yours.” Ken screamed up at her, still in pain. All it got him was another harsh shock to his most sensitive parts, making him ball up on the floor yet again.
“I can do this all day long sissy, now if you want me to stop shocking your cock, be a good sissy and do as your told. It will be so much easier for the both of us.” When she saw Ken was about to speak up again she just pressed the button before he could get out a word. Still he hadn’t learned his lesson. He tried two more times after that, but each time was met with another shock.
Ken obviously was stubborn, not that Linda minded much. She liked making him squeal. Eventually he did get it trough his thick skull however that he wasn’t going to win this battle. Unable to take any more of those shocks Ken eventually gave in. Reaching forward with his head he planted a kiss on the toes of both Linda’s heels, cringing as he could pick up a slight foot odour. “I’m sorry for assaulting you.” Ken eventually mumbled, not at all happy about doing this, but the couldn’t take another shock, he was scared that this crazy woman would actually fry his balls.
“Louder sissy, I can’t fucking hear you or do you need another shock? Also you can address me as Miss Linda. Now do it all again.” Linda sternly instructed. Afraid of yet another shock Ken Kissed Linda’s shoes again.
“I’m sorry for assaulting you Miss Linda.” Ken meekly replied, hating every bit of it, but he had to safe his precious balls. At this rate this crazy bitch would render him infertile. He had to comply, at least until he got that key and got out of this stupid overly tight cage.
“Much better, now get up and strip completely naked, all down to your new accessory. I know you’re standing in front of a glass door, but frankly I don’t care. The sooner you carry out my order the sooner I’ll take you a little further back so you aren’t as exposed to the whole wide world anymore.” Linda smirked.
Ken couldn’t believe this was happening. This Linda bitch couldn’t be serious now could she? Her threating look and the way she held her finger at the ready on the shock button told him she was in fact very serious. He couldn’t do that, he had to put a stop to this he thought as he got up. Linda just moved her finger closer to the shock button as he looked as if he was about to protest.
It ended up being enough of a threat to stop him and making him stoop down to take off his shoes and socks under Linda’s watchful eye. Next he stripped out of his t-shirt. Then his pants came down, but when it came to his boxers he couldn’t bring himself to go further anymore. Pleadingly he looked up at Linda. She just responded by moving her finger onto the button, ready to press it down at any given moment.
Going pale out of fear of getting shocked again Ken quickly lowered his boxers revealing the hot pink metal cage locked around his cock. As soon as he had his hands free he used them to cover the cage up though, embarrassed as he stood with his naked bottom towards the street.
Linda just smirked, another key to her ever-growing collection of locked up sissies. With a brisk movement she slapped away his hands, grabbing a tight hold of his balls as she used them to pull him deeper into the store. Not more than a couple of feet though as she soon stopped at a small bench standing at the end of a rack filled with all different kinds of brightly coloured and elaborately designed shoes.
Without a single warning Linda sat down and pulled Ken over her nylon covered legs, letting his caged cock settle in between her thighs. “Now let’s teach you a real lesson. You are not to talk back or disobey your superiors. You are not to threaten anyone ever again and you shouldn’t disrespect your fellow sissies calling them such derogatory names.” Linda said sternly as she started raining down blows on his bare bottom.
This crazy woman was clearly stronger than she looked, easily able to keep him down and her hits hurt like a bitch. More than his bottom however his ego was hurting something fierce. His day had started so wonderful with the promise of amazing sex with a hot chick, but it had all quickly gone down hill from there.
The sex had never happened, instead he was locked up in a way too small cage which apparently could shock him. On top of that it looked ridiculously girly. Only to be humiliated by this hot looking woman called Linda. His anger had quickly turned into fear and embarrassment as he now lay across her lap getting spanked like a child or some sissy like she claimed he was. She might have taken him a bit deeper into the store, but he was still awfully close and visible through the door.
Just when he thought things couldn’t get any worse a bus pulled up right in front of the door. Luckily only two people got off, but his face instantly went pale when he recognised them clearly as his sister and her girlfriend. To his never-ending shame their eyes crossed and there was a clear moment of recognition. Immediately he cast his head down hoping he had been wrong and they hadn’t recognised him. Their relationship wasn’t the best after all. He couldn’t know this had all been a set up and that his sister and her girlfriend had been the ones asking for it.
With his eyes cast down to the floor, trying to hide himself as well as he possibly could on Linda’s lap, a surge of panic coursed through him when the bells rung announcing the door had opened. “What the hell Ken, is that you? Is that really you?” He heard his sisters voice as footsteps rapidly approached and Linda stopped her spanking, keeping her hand on his now slightly reddened and warm bottom.
Since they had indeed spotted him Ken looked up with a bright red face to see both Jenny and Shayla smirking down on him. Maybe they could help him though, they had to right? “Help, this crazy woman has put a shocking device on me and is keeping me captive here. You have to run to the cops or something.” He exclaimed in panic, hoping they would help them for family’s sake cause the way this Linda woman treated him was insane.
“Silence sissy! Hello girls, do you recognise this sissy here? I was just teaching him a well-deserved lesson.” Linda said casually keeping him pinned down on her lap.
“Yes we do, it’s thanks to this asshole that we have to move in the city each day so I can definitely imagine him being a douche at other places as well. What is going on here though? Jenny just recognised her brother when the bus pulled up.” Shayla asked feigning ignorance, acting like this was in fact the first time they saw Linda or came here. They had Ken right where they wanted, but it would be easier to use catching him here against him instead of letting him know how he had been set up.
“This sissy here tricked my poor Stephanie into sending him all kinds of dirty pictures. She obviously had the wrong number and yet he acted like he was the guy she intended to send to. When she asked a pic in return he finally revealed himself by sending a dick pic. I saw the pic and it was simply pathetic, but Stephanie just can’t contain herself when she sees a cock, no matter the size.” Linda started her explanation.
“I insisted she deserved better and that she’d lock up his cock to teach him a lesson. One for extorting pictures out of people, and two for sending dick pics. I made her make it obvious on where he could then find her so I could have a strong word with him. Instead of being ashamed over his actions however he threatened to beat up my Stephanie, my store and then me with a baseball bat and I couldn’t let that happen as I’m sure you girls understand. It was obvious to me that he was just a repressed sissy, the size of his clit and his erratic behaviour strongly pointing in that direction. I just so happen to know exactly how to deal with sissies.” Linda carried on twisting the situation a little with her so called expertise. All she needed was to create a good foundation for the girls to build on.
“Trust me, I have encounter more than enough cases just like your brother, all repressed sissies deep inside. They turn out aggressive, assholes and bigots. All just so they can cling to some sick ideal they have of manliness, so they can cover their deepest desire, because they’re afraid and embarrassed to show their true sissy selves to the world.” Linda continued her explanation, trapping Ken with her words, if he’d want to argue with his sister and Shayla now they could always refer back about how it was logical that he would claim he didn’t want to be a sissy and how it was falling back into old bad habits.
“The best way I have found to deal with this is to force that inner sissy out, which is exactly what I planned to do with your brother. Of course now that you girls are here I will respect what you think should happen to him as he has wronged you as well. I heavily suggest my approach though. You’ll need to be stern as sissies like him will do anything they can to deny their true nature, but if you keep it up you’ll find that they are so much easier to have around that they become much better persons.” Linda finished looking at the girls expectantly while keeping a stunned Ken pressed over her lap.
“I am no fucking sissy, and you need to let me go right fucking now. What the hell Jenny, you’re just as crazy as this bitch here, why haven’t you called the cops yet?” Ken cried out shocked at what Linda had been saying and just as shocked at how his sister and her stupid girlfriend had just stood there and listened without trying to rescue him.
Jenny’s face instantly darkened, she had been pissed at her brother over how he had bullied her and most of all Shayla out of the house, she was pissed over how he treated a girl in a phone conversation and it had actually been shocking to her that he had come here with a baseball bat. “I don’t know who you are, but you have a point. It seems like you haven’t spanked him hard enough just yet though.” Jenny said coldly looking down at her brother.
“What the acutalmmmmph!” Ken exclaimed shocked, but he was quickly muffled by Shayla’s hand pressing against his mouth, preventing him from ranting and cursing any further.
“Didn’t you hear your sister you fucking sissy? Shut up! And Miss, I’m pleased to meet you, I’m Shayla, this is my girlfriend Jenny, and she is right this pathetic excuse of a man hasn’t been spanked hard enough just yet.” Shayla said, speaking down viciously to Ken while her tone became a lot friendlier as she spoke to Linda. This whole set up was working awesome. She felt so empowered. Finally this bastard was in his rightful place, humiliated and punished. Oh she was enjoying this so much.
“I am Linda by the way and I believe you girls are right, he really hasn’t been spanked enough just yet if he starts using such foul language.” Linda said casually as she started raining down another ten blows to Ken’s already sore red bottom. He had to do his best not scream and show just how badly this was hurting. They were already calling him a sissy and the last thing he wanted was to prove them right by acting like one.
“Hmmm, it looks like the sissy is trying to act though. Let’s see if we can change that. A first step to making him come to terms with his true self is making him let go of his reservations.” Linda explained making Ken wonder what she meant. It quickly became clear as she started spanking him again, raining down blow after blow without relenting. Each one hurt more than the last and eventually Ken couldn’t hold back from sobbing anymore. Tears rolled down his cheeks as she stared sobbing loudly, only then Linda relented.
Ken felt miserable, his ass was on fire, and he believed he wasn’t going to be able to sit for about a week. On top of that Linda had gotten her wish, she had gotten him to sob like some kind of sissy, as if getting spanked over her lap hadn’t been embarrassing enough just yet. Adding insult to injury his sister decided that now was the time to further beat down on his pride. She hated her brother for all the pain he had caused her and Shayla and she couldn’t wait to see him in panties. “Look at you, how pathetic. Linda is right, you’re nothing but a great big sissy, crying over a wittle spanking.” She mocked him, enjoying how his face soon matched his bottom.
Defeated Ken just groaned as he tried getting his sobbing under control. There was nothing he could say to sooth his ego which had received a harsh hit. He had indeed cried like a sissy and that in front of his sister and her girlfriend. Making matters even worse Shayla pulled her hand away only to use it to snap a picture of his teary eyed red face and his red bottom. She loved the sight, definitely one to remember.
“So girl’s I believe I have spanked him hard enough by now, but what about you? From what I heard he’s been awful to you as well would you each like a turn spanking him next? Or should I just continue and actually try to help this poor excuse of a person by forcing his inner sissy, his deepest desire out?” Linda casually asked as Ken could only listen to it in horror. More spankings? He didn’t know if he could take that, especially not after only just getting his sobbing under control. Then again he didn’t like the alternative either, but worst of all, the choice wasn’t even his.
“Well first of all thank you for the offer Linda and while I’m sure this sissy here won’t say it I’d also like to thank you for trying to help him despite everything. I guess we’ll have to see if you are right and if this will actually make him more sufferable. In any case I suggest we get on with your initial plan we’re sure you’re busy and we wouldn’t want to take up too much of your time. You can count on it that he’ll get punished by us when we get home though.” Jenny said wanting to see her brother all dressed as a sissy so very badly.
“As you wish Ken get off my lap right now. Girls please follow along. I have the perfect outfit in mind seeing what a huge cry baby he is.” Linda said with a smirk as Ken was more than happy to get off her lap, but if he thought he was getting away he was sorely mistaken, with ease Linda quickly grabbed onto his wrist not about to let go any time soon as she herself got up, leading him down an aisle between the rows upon rows of over the top girly clothes and accessories. It looked like a nightmare to Ken who tried covering up his chastity cage as best as he could while shamefully being led by his hand.
Shayla and Jenny were having a blast as they walked behind him, giggling non-stop. Seeing Ken walk at Linda’s hand, his bottom beet red made him look so juvenile and like such a huge joke. He really looked like a pathetic sissy even without an outfit to match. One thing was for sure, he didn’t look like Jenny’s older brother at all.
Things only got better as they arrived at the stage in the back of the store, made into a corner at the back they guessed this was their final destination. Both girl’s instantly started giggling while Ken looked increasingly worried. “Girl’s why don’t you have a seat and get comfortable? I’ll take sissy behind the curtain. I would have just put him in an outfit and kicked him out, but well since the two of you are here I might as well go for the full experience. Now that there is an audience I bet the sissy will love modelling.” Linda explained as she drug Ken up the stage behind the curtain. Shayla and Jenny didn’t need to be told twice as they eagerly took a seat.
Once behind the curtain Linda shouted loudly from behind the curtain to be heard throughout the store. “Marcy! Come here a moment will you? I have a job for you!” She might have Ken under control but she wanted to safe Stephanie from another confrontation, besides by now Marcy had worked here long enough to know her way around the store and the products.
Initially Marcy had been grateful to be allowed to work in the back of the store, especially when that angry guy had marched in. As she heard his threats she had honestly been scared. What if he hit Linda over the head and she was next in line. There was no way she could defend herself she had never been the strongest, and she had only grown weaker much to her dismay.
It was honestly a relief when she heard Linda overpower this guy. Relief that soon went into more nervousness when she recognised the voices of these girls who had teased her on the bus all that time ago. Apparently this was the brother they had been talking about back then. How did they manage to get him to come here? It was awfully convenient, too convenient not to be a scheme.
Whatever it was it didn’t matter she had a job to do no matter how nervous she was to get in the sight of these teasing girls. Mincing like she had been taught she took a slight detour to walk down the row closest to the side of the stage hoping to avoid the girls who were sitting in front of it. It was a bit of an idle hope however as her heels were rather loud, something that drug the attention the moment she stepped into view.
“Oh my god Marcy is that you?!” Shayla exclaimed being the first to notice her as the girls giggled in union. Marcy had still been wearing lingerie under her guys clothes when they last saw her so seeing her with her hair, makeup and fully dressed as a sissy maid made a huge difference. Ignoring the shout out Marcy minced onto the stage behind the curtain and curtsied for Linda awaiting her orders, glad to be out of sight again.
“Marcy! Is that anyway to greet our guests?! When you get off stage I want you to give them a proper greeting. You can fetch everything right after that and then go back to entertaining our guests when I am getting this sissy here dressed. Now for what I want you to fetch.” Linda said then proceeded to whisper the outfit she had in mind in the sissy maid’s ear, not wanting to spoil the surprise.
Embarrassed beyond believe Marcy minced of the stage walking out front right before the two girls where she dipped into a deep curtesy. “Good morning ladies, I’m sorry for being so rude and not greeting you earlier. I hope you have a pleasant shopping experience here. If you don’t mind I’ll go now for a few minutes since I have an outfit to fetch.” Marcy said trying to appease Linda’s disapproval from earlier.
“Oh my god, Marcy, you look amazing, you have changed so much since we last saw you. That dress really suits you, pink obviously is your colour.” Shayla laughed as she eyed Marcy up good with a certain lustful amusement in her eyes as she imagined Ken in a similar outfit.
Jenny gave him a once over as well, but she seemed to be in more of a hurry. “You look great Marcy, but you can go now, we can catch up after you delivered that outfit. I can’t wait to see my asshole of a brother in whatever it is Linda has in mind.” She said urging him away.
Fearing that she was being watched by Linda Marcy dipped into another curtesy before mincing deeper into the store to fetch the outfit Linda had whispered into her ear. Her retreat was followed by the giggling and gossiping from Jenny and Shayla behind her back. It was unnerving, at least she wasn’t the one on display here. The moment this Ken who really seemed like an asshole who deserved it to her was on display she could quietly retreat.
While Marcy was searching for every piece of Ken’s soon to be outfit, Linda was sternly watching over the naked caged soon to be sissy who looked absolutely mortified. Every giggle and chattering he heard coming from his sister and her girlfriend at the other side of the curtain was making matters worse, especially since he couldn’t hear a word they were saying. It was clear by their refusal to help earlier that they hated his guts so thinking about how they would soon be in charge of him was absolutely mortifying.
It took a while, but eventually Marcy returned to the stage with a ruffled mass of pink clothes. Both Shayla and Jenny looked at Marcy closely, hoping to sneak a peak of what Ken would soon be wearing. Apart from his outfit looking frilly and pink they couldn’t make out much though, not that they minded, those two things were pretty great on their own as they looked forward to how he would be looking even more now.
While the girls looked excited, Ken looked absolutely mortified catching a glimpse of his soon to be outfit. He was about to run away, but one quick look from Linda, daring him to do so made him stop and hang his head in shame instead. The outfit looked like an absolute pink nightmare, but he couldn’t run, not like this. Besides he was rather certain that Linda would catch him rather quickly, especially with Jenny and Shayla’s help and her look told him he was in for an even harder spanking then.
As dire as his situation was looking Ken realised that he didn’t have much of a choice other than to go along with this, maybe if he just let this bitch of a Linda have her satisfaction of teaching him a lesson, and Jenny and Shayla the fun of seeing him humiliated, it would all just go back to normal. He had a sinking feeling that it was an idle hope, but it was all the hope he had.
“Thank you very much Marcy, why don’t you go and entertain our guests while I get this sissy here ready to show off?” Linda asked with a bright smirk, this was going to be such fun, putting a sissy in his first outfit was always the best, especially a reluctant one like Ken. Marcy dipped into another curtesy before walking off the stage leaving Linda and Ken alone.
Instantly Linda directed her attention to Ken who was looking more mortified than ever. “It looks like we’re alone now Ken. Pity you have all that body hair, but don’t worry, I think we’ll be able to conceal it and have you look like a half decent sissy. Once I’m done with you your look will suit the real you so much better.” Linda said as she started by sliding a very pink and slippery pair of satin panties up his legs.
While Linda was helping Ken in his entire new outfit Marcy was back in front of Jenny and Shayla, to entertain them during the wait. “Hello girls, would you like me to go and get you a drink?” Marcy asked dipping in a deep curtesy. A drink was just an excuse to be away from them as long as possible though. He only had to stall until Ken was ready, then all attention would go to him, that much she was sure off.
“I don’t know about you Shayla, but I’m not really thirsty. I don’t need anything but let’s say a twirl for starters.” Jenny smirked having a blast as she looked at the embarrassed oh so pretty Marcy.
“Well Jenny, I’m hella thirsty, thirsty to see that sissy ass. If you give us a twirl you can stop right with your back to us and flip up that skirt, I’m curious to have a closer look at the panties you’re wearing, considering your outfit they just have to be very cute.” Shayla said as both girls erupted in laughter.
Mortified Marcy carried out the demands, hoping for once that Linda would hurry up. Jenny and Shayla were having a blast making Marcy show off her panties, back and front, they even went as far as to cope a feel of her bottom and inspect her cage very closely. Eventually after about 20 minutes the announcement Marcy had been waiting for came. “Are you ready girls? In a few moments the curtains will open and I will reveal to you Sissy Ken.” Linda announced over the speaker as the lights dimmed and a spot was placed right on the curtain. Instantly both girls turned their attention to the stage, allowing Marcy to subtly move away.
