Goodbye Brother Hello Sis-sy Pt.1 (Patreon)

Intro

Shayla and Jenny had been a remarkable couple form the get go. They were the first openly lesbian couple in their rather conservative school. Not only that, but they were also the first openly interracial couple in their school. It surely got them a lot of sideway glances, but neither of the girls really cared. The school was really strict about their anti-bullying program so no one could actually really do more than look at them strangely. 

They loved each other and that’s what mattered to the girls. Besides they also had a lot of support from friends who admired how they didn’t seem to care about the social standards and for the bravery of coming out. Society might have become a lot more liberal already, but even now things like this remained relatively taboo in reality.

Most of those friends played on the girl’s hockey team, just like Shayla and Jenny did. As a team it was important to stick together, a team was like family. So just like family their fellow team members vowed to support the girls no matter what. Of course there was also some teasing involved, but all in good fun. If anything, the relationship of the girls had strengthened them as a team.

While both girls came from a rather similar upper middle class background their home situations were completely different. Jenny grew up with a brother who was 20, two years older than her and Shayla. Her parents were almost never home, they were either working late or on business trips. Her brother was living in a dorm near his college building.

As a result Jenny was often home alone without supervision at all. After all she had just finished her senior year at high school, so she was too old to need a babysitter. It served as the perfect place for her and Shayla to hang out, which they did pretty much every day after school. At least until they would share a place at college where they were going after their long summer break.

Shayla was from an adoptive family. Her parents were very supportive of her relationship. They had always supported her in every way they could. It was her happiness that came first for them and so they made no problem out her staying over at Jenny’s so often. They were proud of their daughter to be as brave as she was.

Although Shayla had long thinly braided hair and Jenny preferred a short pixie cut with curls on top It was Shayla who was the most masculine in her dressing. She never really wore skirts or dresses, preferring leggings or tight jeans instead. 

Jenny was More of a girly girl in a strange way. She nearly always wore skirts or dresses, often paired with pantyhose or over the knee socks. She even wore quite a lot of pinks, nearly always having a pink accent somewhere in her outfit. Yet at the same time she looked though as well. Her short hairdo combined with her preference for Dr. Martens boots compared to Shalya’s sneakers and the way that she often wore at least one leather piece as well made her look quite though despite the skirts and dresses.

Both girls were in excellent shape thanks to their frequent hockey practices and matches. They each had a strong arms and legs with a flat stomach. Jenny was about 5’7” tall while Shayla was 5’10” tall, just like Jenny’s brother Ken.

Where Shayla had jet black hair, dark brown eyes and a mocha skin, Jenny had steely blue eyes, nearly grey, light blonde hair and a rather pale complexion. They surely were opposites when it came to that part of their appearance.

The girls had been looking forward to their summer break for a long time. Without school to attend they could just hang with each other all day long, doing fun stuff, going out with their friends,… It truly seemed like it was going to be perfect. A perfect break before they would move in together at college where they both had earned a full sports scholarship. 

Now that their break had started, they realised there had been one oversight. Their own private place at Jenny’s house while her parents were at work was no longer private. Her brother Ken had moved back home for the summer and he was being a big pain in the ass towards both girls.

Shayla had only rarely seen the guy, but upon seeing him it was instantly clear that he was Jenny’s brother. At 5’10” he was taller than Jenny, about the same Height as Shayla. He did have the same blue eyes and the same blond hair as his sister though. Even their hairstyle was somewhat the same. Ken like a lot of guys these days had his hair shaven up on the sides and longer on top. Not quite as long on top as Jenny’s though and without the curls.

It was also clear that Jenny was the more athletic of the two. Ken didn’t really look like a whimp or anything. He just looked average not skinny, not fat, not tone or muscular. It wasn’t surprising either. Ken just liked gaming and partying with his buddies at his frat house. He hadn’t worked out a day in his life and he had no intention of changing that.

When it came to his sister’s relationship, he was a real asshole however. He was somewhat racist and believed both girls should try a man before they decided they were so called lesbians. Aside from the often-crude remarks Ken completely blew it when he started trying to hit on Shayla in the rudest ways possible. Since his sister wouldn’t listen to him he had taken it on himself to fuck some sense into her girlfriend and prove to both girls they were better off with a guy.

His way of hitting on Shayla was sickening though. It made both girls so angry. His latest remark about how he had “some milk for her chocolate” as he had called it really was the straw that broke the camels back. It was extremely rude and just disgusting. Especially with how he had grabbed his crotch while looking straight at Shayla when he said it.

Both girls had wanted to beat him up badly, but they were smart enough to know if they did that, they would be the ones in trouble. Even if Ken really deserved it. From that incident on the girls no longer went to Jenny’s place. Instead they hooked up at a nearby bus stop and ventured into the city from there. It wasn’t what they had imagined their summer to be like but it would have to do for now.

It was on one of those bus rides they met a sissy, they had caught him, or her, or whatever a couple of times outside that strange boutique called CC’s and from their conversations, rather one-way conversations for sure, an idea to get back to Ken had started to form.

Chapter 1

Another day, another rendezvous at the bus stop had arrived. This time however both girls were very excited. From their conversations with the bus sissy they had figured out that the owner of that boutique knew what she was doing, and they hoped a conversation with her could lead to a plan to deal with their problem. With how embarrassed the sissy on the bus had looked it sure seemed like it would be fun.

Filled with excitement the girls got off at the bus stop right outside of that ridiculous store they had passed by so many times. Just walking towards the store sent the girls into a fit of giggles, looking at the outrageous outfits the shop mannequins were dressed in. “Oh my fucking god Jenny can you already Imagine your brother in that cheerleading uniform?” Shayla said pointing to one of the mannequins.

It made Jenny smirk. All of the outfits in the store front looked like a style you might find in every day life, but they were all rather sexualised. Despite everything being shorter and tighter than what you would ever encounter in a normal situation the outfits weren’t really suited for a sexshop either. They all looked sexy, but the mainly pastel colour schemes and the ruffles and frills that seemed to be slapped onto every possible part of the outfit made them look cute in a way as well. It was a strange combination that looked nothing like any self-respecting person would wear.

Yet apparently there were people who wore stuff like this, that much had been proven by that sissy on the bus. That encounter had also showed the store had lingerie just like their outfits. “That would certainly be delicious, maybe he could cheer at our games and become our new team mascot. After all the regular cheerleaders always fell too good for the girls hockey team, even if we ranked the highest out of all of our school’s sport teams. They chose to support the football and basketball team over us.” Jenny replied with a smirk imagining that very scenario.

“Besides it would serve him right, he hasn’t missed a single game of his college football team and he isn’t even that into sports. Hell I can tell from his snap stories that all he’s interested in is the parties afterwards and perving on the cheerleaders during the game. It would be poetic justice for sure. Let’s not get ahead of ourselves though. There’s no way he would even touch a plain pair of cotton panties unless if he managed to steal them out of a girl he perves on’s hamper.” Jenny said, a certain hint of disgust in her voice.

“I know, I know, Still it’s funny as hell just imagining him in something like that. You’re right though we should not get ahead of ourselves, let’s see what that store owner has to say first. Still if it ever comes this far I certainly want to see him in that outfit.” Shayla explained with a smile, pushing open the door and heading inside.

They were greeted by the delicious sight of a gorgeous slender figure wearing very high black patent leather heels, a pair of sheer black seamed stockings with the tops left bare by the awfully short black skirt that hugged her cute bottom perfectly. Her white blouse seemed to be made of a shimmering satin and the big black bow tied underneath her neatly cut red bob cut looked kind of off. It looked slightly ridiculous, but not as much as a lot of the outfits in the store. Well they guessed you had to promote your wares, right?

Both Shayla and Jenny liked what they saw. They were quite open in their relationship, feeling secure enough with one another that they didn’t shy away from spotting girls together. They had often talked and fantasised about involving another girl just to spice things up. It had been a fun fantasy to discus, but there was no way they were going to come out with that knowing how their current relationship was only barely accepted.

“Uhm Miss, excuse me, but are you the owner of this store? We know one of your customers and we were wondering if we could discus a certain situation we’re having.” Shayla spoke up, dragging the pretty girl’s attention towards them.

She looked quite young to own a store already, only slightly older than they were if they had to guess. There also was something slightly off about her that the girls just couldn’t put their finger on. She had a very pretty face, and despite a rather flat chest she was an overall pretty girl. The front of the blouse looked even more ridiculous than the back did though. The ruffles lining the row of buttons, the high collar and ruffled cuffs just weren’t things you would expect on a normal blouse.

Their wonder only grew bigger when the girl spoke to them with a bad silly lip, looking rather embarrassed. “No, I juth work here. My mommy ownth thith thore. I’ll go get her for you.” She said before walking off, leaving both girls standing there perplexed, throwing questioning glances at each other as she walked away in a ridiculous swishy manner. 

A few moments later the young redhead returned following behind a tall curvy redhaired woman that looked rather imposing. She wore an outfit similar to the young girl, but hers looked pure business and classy rather than frilly and slutty.

“Hello girls, I’m Linda and I want to welcome you to CC’s. My sissy stepson here told me you needed help with a certain situation. So please go ahead, elaborate, what do you need help with.” Linda asked in a friendly tone loving the completely dumbfounded look on Jenny and Shayla’s faces. 

It was a look she knew all to well, the same look she got from everyone once they realised Stephanie was actually a guy, or well a sissy. The time when she had been a guy was long gone. Getting those looks always made her proud. It told her she had done a perfect job sissifying Stephanie. 

“No way that actually is, or rather was a guy, there is just no way.” Shayla exclaimed while Stephanie blushed bright red.

“Well Stephanie here was Stephen about a year ago, but as you girls can see calling her a guy now would be a grave offense to any real guy around. No Stephanie here is just a big sissy, why don’t you follow me to my office, and you can see for yourself. Back there we can also discuss your situation in more detail.” Linda said with a smirk, somethings never got old. Like rubbing in just how big of a sissy Stephanie had become.

Quietly still too shocked by disbelief the girls followed along to the big office in the very back of the store. “Have a seat girls, and by all means have a look around.” Linda said proudly as she pointed to the framed pictures on the wall highlighting every big moment in Stephanie’s sissification from lean muscular jock to slender frail sissy, carrying a highly embarrassed look in each picture.

“Oh my god I can’t believe it, she actually was a guy at some point, a real macho as well from the looks of it.” Jenny said comparing the blushing Stephanie who had entered behind them with a picture from a shoot Stephen had taken in his full football gear striking a though confident pose for a team promotional campaign. It was the only picture of Stephen without an embarrassed look on his face. The only picture of who he had been. Linda just liked keeping it around to show off how big the contrast had become.

Despite the well documented photo journey on the wall both girls still carried a look of sheer disbelief on their faces. “Stephanie, why don’t you show these girls that their eyes aren’t deceiving them?” Linda suggested to her mortified stepson. Even after all this time she still couldn’t get used to the humiliation of being shown off to new people. 

She did know better than to even hesitate when her stepmom told her something though so she quickly raised her short skirt in a graceful way, grabbing the edges between her thumb and index finger before lowering her panties showing off the small pink chastity cage tightly locked around her cock.

“Look that is the same thing that sissy on the bus was wearing. I guess we’re certainly in the right place, if I hadn’t seen it with my own eyes, I never would have believed it.” Shayla exclaimed obviously still in awe.

“A sissy on the bus? You must mean Marcy, our first new sissy to the CC’s family since I opened this store. Is that why you girls are here?” Linda asked dragging the attention back to herself and the original topic as the girls both took a seat on the comfortable leather chairs in front of the desk.

“I guess we must be talking about the same person. I mean how many guys, uhm I mean sissies take the bus in full lingerie? Hell I don’t even know any girls who wear such elaborate matching sets, especially not on a normal day.” Jenny said still sounding impressed. 

“Oh you’d be surprised given a little let’s say persuasion I could bring out the sissy in pretty much any guy.” Linda smirked hinting that she wasn’t afraid of using more questionable means to achieve her goals even if it was against the guys will. 

The hint didn’t escape the girl’s attention at all as their smiles grew bigger. “We’ve definitely come to the right place. You see we have a problem back at home that needs to be dealt with. My girlfriends’ brother is back home from college and he’s a big nuisance. He constantly harasses us over being lesbians and he’s a big racist as well. We kind of planned to spend a nice summer practically living together pretty much on our own since her parents are gone so often, but now staying at the house has become pretty much unbearable.” Shayla explained. 

“It’s so bad that we literally have to head out into the city if we want to spend some time together and well on one of those trips we met that sissy. We were just poking some fun at him just because it looked kind of cute how nervous he looked and when he showed us that chastity cage, or rather when we discovered it we pretty much thought it might be a solution to my brother problem. Especially if we could get him into panties after we saw how easy to manipulate that sissy on the bus was.” Jenny carried on.

“I can most definitely help you girls with that particular problem. All I really need is to know how far you girls want to take this which can range anywhere from wearing panties to a level equal like my Stephanie. As well as your permission and a little side info.” Linda said with a confident smile already looking forward to sissifying yet another victim.

Both girls gave each other a big smile before answering in unison. “Oh we definitely want to take this as far as possible and you certainly have our permission to do whatever you deem necessary to get his sorry ass in panties.”

“Just as I hoped. Well then I basically have two options. You can either wrestle him into that cage, or seduce him into it or whatever fits you most. Point is when you get him in a cage which I would gladly give along, you can use his arousal against him to get him to agree to more and more. This would take time and effort with a chance it wouldn’t succeed since neither of you has any real leverage over him or any kind of relationship you can exploit to trick him into it. I bet Shayla would be the best bet to achieve that, but if she had a sudden change of heart I bet it would arouse suspicion.” Linda explained.

“There is another option however. One to kickstart his feminisation in a big way which should give you girls plenty of control from the start. It’s also a method that would require nothing at all from you. I’ll take care of it. All you girls will have to do is be at home when I tell you to be there.” Linda explained with a smirk, already guessing which option the girls would choose.

“We’d be foolish not to go for that second option right? Please do enlighten us though, how do you plan to accomplish that? I know my brother and there is no way he would come here on his own, let alone agree to being put in lingerie.” Jenny said somewhat sceptical.

“Well I’d have my Stephanie seduce him and trick him into a cage. Of course it’ll need to be a special cage capable to administer a shock so she can get out safely. I imagine your brother could get aggressive and unlike the two of you there is no way Stephanie can defend herself. My sissy stepson can definitely use some more exercise in seducing guys as well so it would be a win win.” Linda explained making Stephanie shudder, she was still attracted to women only and having to flirt with guys was the worst. She knew she would do it though, she just couldn’t say no to any of her stepmother’s demands.

“Once she has him locked up, she’ll tell that she doesn’t have the key, but that he can come retrieve it at her job, giving him this address. Once he enters here I’ll make sure he doesn’t leave without a full set of lingerie on him before sending him home where ideally you girls will be waiting to catch him in his lingerie and gather some blackmail material. That should keep him nice and docile.” Linda said with a big smile.

During the entirety of her explanation she had only seen the girl’s smiles grow. It was obvious that they were looking forward to seeing her plan in motion. Even more obvious once they both exclaimed. “We can’t wait to do this!” In union.

“Great, consider it done then. All I need from you is your brothers phone number, your phone number, your home address and the promise you will keep on coming here. I can help with everything from clothes to salon visits and training. Let’s just say the sissification process is kind of a hobby of mine. So I would love to be involved and preferably involved rather intensely.” Linda said with a big smile.

Stephanie was the only one not excited about all this. She knew she would be expected to do everything from seducing the brother, to getting him in that cage and eventually getting him here. If anything failed it would be her ass on the line.

The girls looked excited about it, but there was also a hint of worry when Jenny spoke up. “Look Linda we would love to come here for everything, especially seeing how Stephanie looks, I mean damn if I hadn’t had such an amazing girlfriend, I would have probably hit on her in a club. The only problem is that seeing some of the prices of your clothes I’m afraid we can’t even afford to buy a full outfit, let alone pay for all the work that goes into the set up. As much as I would like to see my brother as a sissy, I’m afraid we just don’t have the resources to make it happen.” She said somewhat disappointed.

“Oh but that’s no problem at all. In fact this won’t cost you girl’s a cent. I can think of plenty of alternative ways to get paid. In fact depending on how much you’ll be able to miss your brother and the kind of things you agree for him to do, you might even earn some money off of him. Consider money you would make off of him as a repayment for the expenses you had to make to get away from the house and of course for everything you had to put up with.” Linda said with a big smile easing the girls into feeling justified into what they were about to agree to.

“Could you give some examples of those alternative ways to finance this?” Shayla asked more curious than sceptical. 

“Well first of all Marcy, the sissy you girls know from the bus works here every Wednesday to earn back some outfits she wanted but couldn’t pay for. I could also use models to make a catalogue and advertisements. A door to door maid service is also an idea. Not only does the sissy get the job done, it’s also entertaining to watch them mince around.” Linda started off.

“Of course there are also less conventional jobs, but ones that earn way more. There are a lot of people, especially men who love dating sissies for various reasons depending on what they want to do on those dates there is a lot of money to be earned there. Of course if you don’t want things to get so physical you can also make a website for the sissy with some naughty videos.” Linda informed hinting at sex work without actually using the term.

“I think those dates sound wonderful, and I think he should at least have one every week. That is once he is fully trained of course. We couldn’t accept money unless the date was satisfactory, and I have a feeling that’d require some specific skills.” Jenny said with a smirk, obviously aware of what kind of dates Linda meant.

Shayla wasn’t being so subtle, however. She just said out loud what everyone was thinking. “Oh absolutely, once he is trained he should have frequent dates. With all his rants about how men are so much better than women and how we should try a guy instead, I think it’s only fair to hook him up with a guy. I mean he’s the one who claims we should try a dick every time we react irritated or angry. Cause of course we aren’t angry about his misogynistic shit but because we’ve never been properly laid.” Shayla said getting visibly angry just think about all the things Jenny’s brother had said to them.

“Yes, I also think his first date should be with a black guy, even hell it shouldn’t even be a paid date. Just as long as he gets some chocolate for his milk-y white bottom.” Jenny added viciously, obviously still enraged over the insanely rude way in which her brother had hit on Shayla.

“From what I just heard I think that’s a great idea. After all it sounds like your brother really believes that a dick fixes all problems, so getting a regular lay should be the best thing to ever happen to him right?” Linda chimed in as they all had a giggle.

“So when do you think we could kick this off? I mean I guess it will take a long time to get to the point we just discussed.” Jenny asked getting back to more present matters.

“Well not necessarily. The special cage I plan to use for your brother is one I haven’t tested myself yet, but I believe it can be a very effective training tool. With it you should be able to train him into doing everything you wish in no time. At least I’m hopeful that will be the case, but trust me when I say that once you get them locked up they’ll give in sooner or later. Men are just such horny creatures.” Linda confidently said with a smirk.

“Of course it will take a little time to get that cage on and to get him to come here. Let’s say till the end of the week. I’ll give my Stephanie till Friday to seduce him, put that cage on and make him come here to get the key. When he leaves it’ll be in full lingerie and I will send you girls a text to let you know he’s coming.” Linda said with a big smile. 

The smile instantly got reciprocated by both girls as Jenny took out a note and started writing down their phone numbers along with the one for Ken, she also wrote down their address as requested. “That sounds awesome. Here is the information you asked for. God I’m looking forward to this so much.” She said, her eyes gleaming.

“Great, then I guess the next time I see you girls will be with the sissy in tow visiting my store. I’ll have Stephanie send you screenshots of the entire conversation. If you see any points in which my sissy stepson could improve then be sure to let her know. I’m pretty certain she’d love to perfect her seduction game.” Linda replied with a smile. Stephanie just meekly stood by. She wasn’t thrilled at to get this task but of course she wouldn’t say so, definitely not with her stepmother nearby.

“Oh gladly and don’t worry, my brother is a very easy target. I can’t imagine he’s hard to seduce at all. Any attention from a girl, or someone as pretty as you is probably enough to get him going. If you wanted to meet up with him he’d probably move heaven and earth just to arrange that meeting.” Jenny giggled.

“Yeah, just be sure not to let him find out you have a cock, then you should be fine. He’s a big bigot on top of a racist. If he finds out then meeting with him would be pretty much impossible, no matter how hot he thought you were at first. Anyways, good luck and thank you for the help, I’m looking forward to seeing the results when he comes back from here already.” Shayla said with a big smirk.

“Those are very good tips to get this set up started. I guess this is goodbye for now then. You can expect to get many screenshots to keep yourself entertained though.” Linda said as they all said their goodbyes with the girls heading further into the city, looking to enjoy their day. Soon they might be able to enjoy their time back at home again though, in the meantime they simply couldn’t wait to see how easily Ken would be drawn in by Stephanie.

Back at CC’s Linda was giving her sissy stepson some instructions on how to get this set up. “Alright Stephanie, the scenario we’ll go with is you sending that guy a spicy selfie, with something along the lines of having enjoyed the adventure last night after the club a lot, and hoping to set up a repeat soon. You can go with the whole having gotten the wrong number narrative, something like that guy from last night not knowing what he’ll miss.” Linda explained the start of the conversation.

“From there on out it’s all in your hands, I want you to make the conversation juicy and entertaining for our clients to read. Your sole aim is to get him as eager to meet as possible. There is no need to worry about the date just yet. I’ll give you specific instructions when the time is there. For now just make his head as crazy for you as possible.” Linda concluded her instructions.

Stephanie dipped into a deep curtesy, her way of nodding her head. It wasn’t like any other answer was allowed anyways. She didn’t look forward to this task at all however. The thought of sending sexy pictures to a guy was rather disturbing as was getting him to lust over her, but since she would have not only her Stepmother but these girls watching as well she knew she better do a very good job, anything less and her stepmother would be very displeased which was something to be avoided at all costs.