Goodbye Brother, Hello Sis-sy Pt.2 (Patreon)

Chapter 2

While Stephanie finished off her day working in the store Shayla and Jenny had a wonderful day out. It didn’t take too long for them to get a message that they had been added to a chat group with the two of them and Linda. Although it was Stephanie who would do the heavy lifting she wasn’t in the group.

That evening upon coming home Stephanie wasn’t given her usual duties. Her stepmother had given her the nights off for the coming week while she worked on reeling in the next sissy for CC’s. Getting of home duties wasn’t something Stephanie was particularly happy about though. She preferred chores to seducing a guy and her stepmother had made it very clear that she shouldn’t slack, or she would be sorry. With full information about what Stephanie did in her room and what she did on her phone there was no one she could trick her stepmother by not doing as demanded and spending most of her night relaxing.

Stephanie felt awfully nervous about what she was about to do, failure wasn’t an option and so she had to make absolutely sure not to mess this up and show too much. Stripping out of her blouse and skirt down to Lingerie It consisted of a white lace bra with a small black satin box between the cups. White in order not to show through her white blouse. A similar thing went on with the white stain waist chinch she was wearing. It laced up in the back with black satin ribbons and had four white garters running down her legs underneath her black lace thong with its white sating bow sitting at the front, holding up her sheer black seamed stockings which ended in a pair of skyscraper black stiletto heels. 

It wasn’t the extremely sissy lingerie like sold in the store as her stepmother insisted on matching down to the lingerie, claiming it formed a bond with her sissy stepdaughter. It was perfect for what she was about to do as going too sissy would probably give things away. She just hoped her extremely girly room wouldn’t ruin things. She had to try a while to find the best possible angle for the picture she wanted to take but eventually she got it, sitting back up and cringing as she was about to send it to this guy she didn’t even know.

About ten minutes later Shayla and Jenny got a message both at the same time. They were just having a nice dinner out at a gourmet burger restaurant, but both instantly dropped what they were doing to check their phones. They both erupted in a giggle fit as they saw what Linda had sent them.

Her message was a simple one. “I think our future sissy is biting.” It read, but the screenshot was simply priceless. A sexy photo of Stephanie laid out over her pink satin sheets in her lingerie looking over her shoulder seductively was the first thing that caught their eyes. They both had to admit that the sissy looked amazing, her waist was surprisingly slender and her bottom surprisingly full. If either had to pick a guy to crush on it was definitely sissy Stephanie.

“Hey Jake I just got back from work. I wanted to thank you once more for the amazing evening at the club yesterday and I was wondering whether you’d like to carry on where we left off. Xoxoxo Stephanie <3” the accompanying message read.

From the time stamps they could see Jenny’s brother hadn’t hesitated to reply at all. Unlike what they were expecting though he didn’t point out the fact Stephanie obviously had the wrong number. He clearly wanted to score more pics. “Hey babe, can I say you look spectacular in that set. I’d definitely love to finish what we started. You’ve made me rock hard once more. Why don’t you send me any more of those juicy pictures so I can keep this hardon going until I can see you.” He had sent. 

It was a little disturbing to Shayla and Jenny the way he texted to what he thought was a woman, but then again he would soon regret that. The bastard, trying to get more pics out of a girl who obviously had the wrong number. The only reason it was funny was because Ken clearly had no idea Stephanie wasn’t a real girl and that he unknowingly was opening himself up to the trap.

What followed was a quick back and forth where Stephanie sent another sexy picture followed by a request from Ken and another pic answering that request. It went on for a while until Ken was starting to tell Stephanie to strip for him. A reply stayed out for a while after that. “Well, why can’t I get a pic of you first? I want to see you again so very badly. <3” Came Stephanie’s reply, baiting Ken out to reveal his identity.

It worked like a charm. In no time Stephanie received a text message back in the form of a selfie Ken had taken. “Sorry babe, I don’t know who that Jake is, but I’m sure he’s hitting himself over the head by now. Must have mistyped a number or something. Thank you for the pictures thought they were hot.” Read the accompanying text. Obviously Ken had no shame over the huge dick move he just pulled. He was completely aware of the fact that he probably would get no more reply though, but it was fun as long as it lasted. 

Much to his surprise he got a new message in his inbox soon after. A pic of Stephanie biting her lip seductively, one strap of her bra teasingly lowered. “His loss, you look pretty hot yourself though tiger, what’s your name? where are you from? I hope you weren’t joking about that hardon you talked about. Can I see it please. I’d love to see what you’re packing, please I’m so horny. Xxx” Stephanie sent accompanying her picture. She felt rather disturbed about the fact that she was actually reeling this guy in, but she had to or her stepmother wouldn’t be happy.

Ken was very surprised to receive a message back after revealing he wasn’t who this Stephanie thought he was, but upon reading her message he couldn’t help but smirk. He didn’t know why, but he must be riding a wave of good Karma or something. One thing was for sure. He wasn’t going to let this opportunity slip away from him. He wasn’t going to be as stupid as that guy who probably mistyped his number and let this chick slide. 

Fuelled by arousal and his hormones Ken let all caution slide, the saying that if something seemed too good to be true it probably was, didn’t even cross his mind. This chick was hot and very eager as well it seemed. He was more than happy to send her some pics back if it meant getting even more and even sexier pics from her. Meeting her would be even better, but since she had the wrong number he knew the chances of that actually being possible were slim to non-existent. She probably lived too far.

Stephanie’s previous pics had indeed made his cock hard, the full 5 inches of it.  Without hesitation Ken pushed down his sweatpants and boxers, rolled his gaming chair back and snapped a pic of his cock which he promptly sent Stephanie’s way with the following message. “Here you are babe, all hard for you, I’m Ken from Fibaro city. Now why don’t you show me your tits?” He sent back expecting to trade his low effort dick pic for some more of this girl’s sexy pics.

When Jenny and Shayla got a new message ping Jenny refused to open it. “Oh god, if his dick is in there I don’t want to see it. Can you check please and if so can you just delete that message from my chat and phone.” Jenny said with a shudder making a gagging noise.

Shayla just opened the pic not all that bothered, sure she didn’t want to see any dicks either, but knowing how much trouble Ken was getting himself into she couldn’t help but be morbidly fascinated to see it all. Opening the next screenshot she instantly started laughing. “Oh god Jenny, your brother’s cock is pathetic, I can’t imagine any girl will mourn that thing getting locked away. Hell his pic is as low effort as they come even. The least he could do to make up for his pathetic size is to try and make an impressive pic.” Shayla laughed as she deleted the screenshot from her girlfriend’s phone.

“Ew, Shayla, shut it I don’t want to know. I can’t believe that asshat thinks any girl actually wants to see something like that.” Jenny cried out disgusted.

“It’s deleted, don’t worry about it. Check this though, this is the part of the screenshot I think you will want to see. Don’t worry, I cropped the nasty bits out and sent you the cropped version.” Shayla laughed.

Underneath where the dick pic and Ken’s message had been there was a picture of Stephanie without a bra. Without the push-up effect she barely had an A cup, but she did have large swollen nipples which looked very inviting to play with. Her message read. “Oh my god really? That’s where I live. Heavens be blessed I was fearing I would need to find someone else to give it to me good when you told me you weren’t Jake, but that cock looks so delicious and you live so close by that I really really hope we can set up a date. Oh god I’m already having a hard time deciding what hole I want that beast of yours in first. XXX” 

Ken couldn’t believe his luck, this was only getting better and better. Heaven’s be blessed indeed. While this chicks breasts were nothing to write home about, her eagerness more than made up for it. Besides there was no way in hell he was going to pass up the opportunity to get such a sexy slut as a fuck buddy for this summer. Hell her booty was sublime and if he fucked her from behind he wouldn’t even see her lack of breasts. This was starting to look like he would have the summer of his life. He had never scored this easily.

“Mmm I’m ready whenever you’re ready babe. I’m in vacation so really whenever you have time I can make time for you. Be careful though I’m a feisty one 😉. Why don’t you show me your pussy? I’d love to see what I’ll fuck.” Ken sent back horny past thinking straight.

“Easy tiger, while I could send a pic you’ll have to do with what I already sent you. I want there to be some surprises still. Why don’t we meet Wednesday morning? I have a day off of work so we have all the time in the world to have some fun. By the way do you have a place? Oh and do you have some outfit requests? I love to dress up for a date. I hope you’re a little kinky cause I love that. XXX” Stephanie sent back distracting from the fact that she wouldn’t sent any more pics. If only Ken knew that there was a real surprise in her panties.

Since his sister and her stupid girlfriend were never home Ken saw no problem with this Stephanie chick coming over. “Oh I love kinky. Just put on something sexy babe. If I see what you have on now I’m sure you will have no problems finding something to wear. In any case I’m looking forward to Wednesday. I’ll ping you my location in a bit so you don’t have to search. By the way more pictures are always welcome.” Ken sent back.

“Great, Wednesday it is, then you can see it all in person. I can’t wait to have some fun with that delicious cock of yours. XXX” Stephanie sent back surprised how easy this had been. She had expected to need all the time she got to clear this job but it looked like she would have this guy in a cage before the time she got to seduce him was even over. She was sure her stepmother would be pleased, especially since she had picked the day that Marcy would be in the store so she wouldn’t have to run it on her own. Stephanie really hoped she would get a reward for her efforts.

Linda was very pleased with her sissy stepson indeed. He had done an excellent job all be it on a very easy prey it seemed. Still Stephanie had done great, Shayla and Jenny had loved it as well which was all she could have hoped for. It looked like yet another client was in the pocket. The girls had already let her know they were so looking forward to Wednesday.

Chapter 3

What remained of his Monday and nearly all of Tuesday Ken hadn’t been able to put Stephanie out of his head. He ended up masturbating to her pictures multiple times, unable to wait until Wednesday. Finally Wednesday did arrive however and he woke up to a message from Stephanie telling him she would arrive in about an hour.

Getting out of bed Ken took a quick shower, put on a pair of fresh boxer shorts and did a quick sweep of his room to get most of the trash out of the way. He checked himself out in the mirror with a wink, confident that he would own this sex date. Ken hadn’t the greatest figure, but he had more than enough self-confidence.

A few minutes later the doorbell went. As fast as the wind Ken threw on a bathrobe and rushed downstairs, ready to wow this hot and eager chick. When he opened up the door however his jaw dropped. This chick looked great, even better in real-life.

For the occasion she was dressed completely out of the ordinary for her. Instead of her usual frills or bright colours she looked way tougher than usual. For today Linda had decided that her sissy stepson could play the Domme for a change. It was just as much to mock her as it was to make things easier for her. After all she had hinted at being kinky and Linda figured if Stephanie could tie Ken up then there was no way this could fail.

It had been embarrassing for Stephanie to actually have to learn how to act dominant again. With her girlfriends before she had fallen under Linda’s control she had always been dominant, but now Linda had had her rehearse almost all of last night. It just felt so weird and unnatural. Even now she could barely contain her nerves. She didn’t have a dominant bone left in her, but Linda had warned her that she better put up a really good act then or improvise. Failure would not be tolerated.

Stephanie had definitely dressed the part. Her shoulder length red bob cut went perfectly with her dark smoky eyes and the fire engine red lipstick. She wore a long black coat reaching till under her knees, black leather ankle boots and sheer black stockings all that peaked out from under it.

Stepping inside she quickly dropped her coat and as a result Ken’s jaw dropped even further. Underneath the coat Stephanie was wearing a black leather under bust corset, pushing her small breasts up to make them look bigger. It didn’t cover her nipples though which were covered by two crosses of black tape. From the coreset a pair of garter straps held up her sheer black stockings. The only other thing she wore was a pair of black leather panties that luckily managed to keep her cage pressed back between her legs.

While Ken liked what he saw and while Stephanie was definitely dressed the part, he still didn’t really see her as imposing at all. She looked nervous and fidgety if anything. Since she couldn’t even seem to act as if she were dominant there was no other choice than to improvise for Stephanie.

When she spoke up it became even harder to take her serious. She had a pretty bad lisp. “Hey, look I’m sorry, but I am a little nervous about this all. I thought if I dressed the part I could keep my nerves under control, but oh well. It has always been a dream of me to tie someone up and treat their cock as my toy, so could we please try that? I would love that. I promise I’ll give you the best time ever and you can do whatever you want with me afterwards.” Stephanie rambled, pleading came so much more natural for her.

“Oh uhm yeah sure, we can do that babe. I’m all yours. Just don’t spank me.” Ken joked as he gave her a wink. She spoke funny, but he guessed he couldn’t really blame her after he saw that ball in her tongue. All he could think about after seeing that was how great it would feel on his cock.

“Great, you’re the best. You won’t regret this I promise.” Stephanie squealed as she gave him a quick excited hug and a kiss on the lips. It felt gross kissing a guy, even after all this time, but she was so happy that she had managed to convince him despite literally everything going wrong. She had to get him in that cage before he noticed her cock otherwise it was game over. The pressure was immense. Luckily Ken couldn’t know that he would soon regret this sorely.

“Let’s go up to my room and you can tie me up, then my cock is all yours to play with babe.” Ken just said, unable to wait to get his rocks off. He didn’t know what to expect, but the thought of laying back while this chick did all the work, even with being tied up sounded pretty great to him. Getting dominated wasn’t really his jam, but this chick was clearly all about the cock so why not indulge a little fantasy of hers?

Nerves raging through her entire body knowing what she was about to do Stephanie followed Ken up to his room. Once there she nearly tore his bathrobe and boxers off, the five inches of cock instantly poking out. She gave it a quick peck, keeping his arousal going as she knew that was the only reason Ken was so easy to handle.

“Now just let me put this on you stud, then lay down on the bed and relax. Let me do the rest and enjoy.” Stephanie said pushing up against him, letting his cock rest against her corset as she proceeded to tie a black satin scarf around his head to blindfold him. Ken just smirked letting her do her thing as he lay down on his bed.

Wasting no more time Stephanie quickly pulled out four pairs of pink leather cuffs. Tying him down was her first and most important job. After that there was no threat of this failing and no rush anymore. In rapid succession she cuffed both his wrists and ankles to his bed posts. She then put up her phone on Ken’s desk, getting a good angle to record like her stepmother had demanded.

“Mmm, where are you babe, my cock is feeling lonely.” Ken moaned as Stephanie didn’t immediately pounce him after she had cuffed him to his bed. Stephanie remained silent though. She just went to her bag and pulled out an ice pack which was just cool enough to do its job. Wasting no more time she pressed it against Ken’s cock who shivered from the cold touch to his most sensitive area.

“What are you doing babe? Is this some weird foreplay you wanted to try out? It feels strange.” Ken said, when an answer stayed out for a while and the cold was growing uncomfortable to the point where he could no longer maintain an erection he carried on his questioning. “Babe, I don’t like this thing you’re doing. You know cold and cocks don’t go that well together right?” He asked a little worried.

Stephanie still didn’t reply, she just kept the icepack in place until Ken’s cock would shrivel up any further. Ken was getting restless now though. “What the hell is going on, what are you doing, This is no fun, you promised me a good time.” He complained, starting to fight the cuffs who could more than handle his struggles.

Completely ignoring his protests Stephanie carried out the main part of her order and selected the tightest cage that would fit. In a swift trained motion she locked it in place on his cock, sealing his fate. Even though she pitied him his fate now was out of her control as well. The padlock with the CC’s logo had sealed the hot pink ring behind his balls and the hot pink cage part together. She had no key meaning he was trapped. She had trapped him. While she didn’t wish this on anyone she was saving her own ass here.

If anything Ken would have it worse than her, at least his cage was worse. It was a special model, the ring behind his balls thicker, housing a shocking mechanism that could be activated with the press of a button. Anyone with control over that button would be able to control him.

“What the fuck did you just do? What did you do to my cock? Answer me you fucking bitch, I can feel you did something down there.” Ken said his struggle growing fiercer. He could feel that he was in trouble, that this was not normal in the slightest.

A few moments later it appeared like some clarity would finally come his way. His cock wasn’t cold anymore, but it was in something awfully uncomfortably tight as it tried to grow back to his normal soft size. At least this Stephanie started untying his blindfold though so he would soon see what she had done.

Instead of clarity he got the shock of a lifetime though as he got his vision back. Stephanie was sitting over top of him, a knee on both sides of his head. A cock in a hot pink cage dangled right over his face. She was pumping a big pink dildo in and out of her ass rapidly, moaning as she did so. “I’m sorry, but I had to do this.” Stephanie moaned as she continued pumping away.

“Who are you, you fucking freak? You’ve been a fucking guy this whole time? Get that nasty thing out of my face and release me right this fucking instant! You fucking faggot. I will beat you to a fucking pulp.” Ken screamed, angry out of his mind as Stephanie kept pumping that dildo in and out. She felt terrible for doing this, but her stepmother had insisted she’d do this if she could do so safely.

Ken was so pissed and so busy trying to struggle away from underneath Stephanie that his worries about what was happening down at his cock fell to the background. “I’mmm Sorry, I have to mmm.” Stephanie moaned in her lisp as after about a minute more of fucking her ass with that dildo she came, shooting a load of warm watery cum all over Ken’s face.

Blushing underneath her makeup she quickly got off the bed, put her dildo and scarf back in her bag, threw her panties back on and approached a still screaming Ken. “I don’t have the key to that thing, but I have the key to your cuffs. If you want out at that thing you have to come see me at my job in the CC’s boutique.” Stephanie said apologetically as she dropped the key in his right hand and rushed out of the room with her phone, putting on her coat and rushing out of the house, making sure she would be far away by the time Ken managed to free himself.

“Come back here you fucking bitch, I’m no where near done with you!” Ken screamed behind her to no avail as he struggled to unlock his cuff one handed. It took a while, but after he had managed to get his right hand free his left hand and feet quickly followed. He was disgusted with the goo this fucking freak had left behind on his face. it had a faint cum scent, but it was clearer and not as strong smelling. Nevertheless he had seen up close where it came from.

On his way down to unlock his feet he finally paid attention to what this girl, guy or whatever had done to his cock. He was horrified to see it locked in a cage that looked just like the one which had dangled over his face moments earlier. Worse even was that it looked so small, smaller than his cock got when flaccid which was probably why it was so uncomfortably tight. The hot pink and the heart shaped padlock with its two engraved C’s looked so terribly girly. One thing was certain he had to get this thing off of him and soon at that.

First things first though Ken thought as he jumped up and rushed to the bathroom to wash that nasty load of cum off his face. Even after scrubbing his face with soap three times he could still swear he could feel and smell it. It was so gross.

When he was certain his face wouldn’t get any cleaner he looked down to his cock again. Taking another ample amount of soap he lathered it on all around the cage, the ring and his balls. Trying with all his might he attempted to slide the cage off, but he had to stop as it became clear he would rip off his cock or pop his own balls before the cage would be going anywhere without the key.

What was it this bitch had said? The key was at the CC’s store where she worked. The same store that got its name engraved on that padlock? There had to be something seriously wrong with that bitch, she had to be seriously stupid to think it was a good idea to let him know where she worked. Oh he was going to beat the key out of the bitch.

While Ken was in the shower Stephanie had managed to make her way back to the CC’s boutique where she was instantly greeted and praised her stepmother who’s smile grew wide upon seeing the video she had made. It was just perfect. Oh that guy was so pissed. She bet it wouldn’t be long until he would arrive here. His threats were pretty serious though so Linda took her shock button close by. She’d probably need it. In any case it was better to be safe than sorry.

Smiling broadly she sent the video Shayla and Jenny’s way. They were just having lunch downtown and immediately erupted in loud laughter. “Oh my god, look at that she even came on his face. Your brother is so fucking mad, this shit’s hilarious.” Shayla cried out once she got her laughter under enough control to even manage to talk.

“Hahaha the look on his face when he saw that caged cock dangling above him while Stephanie fucked her own ass with a dildo, that must have hurt his ego, that she preferred a dildo over his cock. His slurs are intolerable though. I think one of the first things we’ll have to do is punishing him and making him apologise to Stephanie.” Jenny smirked. God she wanted to see her brother punished so much for all he did to her, Shayla and now poor Stephanie. Although given his situation his reaction towards Stephanie was understandable.

Ken couldn’t know it, but while he was pissed, fresh out of the shower, trying to ignore the discomfort of this small cage while searching online for this CC’s shop, planning to get this stupid cage off no matter what he had to do. His sister, Shayla and Linda were planning to trap him completely. Jenny and Shayla moved to the area around the CC’s boutique, ready to ‘catch’ Ken once Linda had him dressed up.

Disgusted Ken scrolled through the webpage of this CC’s boutique. The whole store seemed catered to freaks like this Stephanie. In fact she was introduced on the site as the sissy stepson of the owner Linda, a tall imposing woman who made his cock throb painfully, trying to grow hard in the small cage. The remainder of the site was filled with all kind of sissy tips and tricks, along with pictures of some sissy with long curly black hair. One who looked a little less frail than Stephanie or the interim employee Marcy who worked there on Wednesdays. The black-haired sissy was dressed in various outfits with clickable images leading to the outfits in the CC’s online store.

There was no way anyone actually wanted to wear anything like that was all Ken could think. Something he became even more certain off when he saw the insane prices of these outfits. Finally he did find what he was looking for though, an address. Not knowing what to expect he took his baseball bat with him, just to be sure. That Stephanie bitch would give him the key or be very sorry, or rather that and be very sorry.

Throwing on his clothes, a simple jeans and t-shirt combo, Ken walked out to his car. It was a simple second hand one, but it got him from place to place, that and it was his. His sister had often bugged him to use it since he sat home all day anyways and his behaviour is what forced her and Shayla out. He had always refused though, laughingly saying they could use it if Shayla gave him a blowjob.

On his way into the city, all Ken could think off was how he would get that Key back and make Stephanie pay dearly for what she did to him. His anger hadn’t quieted down a single bit. If anything, he was even more pissed now, the more he thought about it the angrier he got.