Miss Stepsister Pt. 03

This short story takes place in the same world as many of my other short stories; a world where CFE (Chastity for Everyone) is a company that has normalized control games/dynamics and chastity. CFE has released all sorts of fun app-controlled toys to make these sorts of fantasies a reality. The disclaimers for this particular story can be found in part one but know that all of these characters are 18+ and completely fictional.

This is the final part of this story, and I apologize for how long it's taken me to write. Here's a little recap if you've forgotten what happened in the first two parts:

Part 1

Oliver accidentally gave his stepsister control of his chastity device anonymously on the CFE dating app. She gave him the option to back out when he learned the truth, but his fantasies got the better of him and he transferred permanent control of his app-controlled chastity to her. There is no key, his version of the app no longer has the permissions to open his own chastity, and she has all the power.

Part 2

The next day, Khloe (Oliver's stepsister) makes Oliver take on a treasure hunt that forces him into some slightly humiliating situations and forces him to confront just how helpless he has become. In this process, he is outed as a submissive locked in chastity to his neighbor and stepmother; twenty-four hours of unremovable time is added to his chastity lockup; and he is told by Khloe that he will be completing the final challenge of the treasure hunt-a short survey of his kinks-before the night is through or else she'll be telling Carly-One of Khloe's friends that Oliver failed to hook up with at their parents wedding-all about their current situation... Oh, and he's got no choice but to come to Carly's house tonight, so Oliver has no idea how that's going work... but his desperation is growing by the second.

Enjoy part 3!

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CHAPTER NINE

Oliver pulled up in front of Carly's townhouse at seven. As soon as he did, Khloe rushed out the front door to meet him.

"So glad you could make it, subby stepbrother." Khloe said as Oliver got out of the car. "Put these on." She handed him a black spandex hood, handcuffs, and a collar.

"You can't be serious."

Khloe tapped a button on her phone and Oliver's chastity gave him a shock. "You know better than that... but while we're on the subject, you will address me as Mistress instead of Miss Stepsister in front of Khloe to keep our little arrangement a secret. Carly knows that my new sub is coming over but she doesn't know who it is. So, if you don't want to wear the hood, that's up to you. The collar and cuffs are going on, though."

"You said you wouldn't tell her, Miss Stepsister!"

"I said I wouldn't tell her about our arrangement. I won't tell her it's you under the hood unless you specifically ask me to. Your anonymity is completely in your hands."

Oliver couldn't believe this was happening. He looked around to see if anyone was watching. The street seemed to be empty. He put the collar around his neck and latched it closed. The hood went on next. It didn't have eye holes but the spandex allowed for limited vision. The only hole in the hood was on his mouth. He locked the handcuffs around one of his wrists but before he could lock the other, Khloe corrected him.

"Behind the back, subby stepbrother."

Oliver sighed. He was already in this deep, what difference did it make? "Yes, Miss Stepsister." He clicked locked the other cuff on securing his hands behind his back.

Khloe clicked a leash onto his collar and led him towards the house. She carefully helped him up the stairs and through the front door.

"Oh my god, you were serious?" Carly shouted. "Who is he?"

"Carly, this is subby. Subby, this is Carly. You can address her as Miss." Khloe tugged on Oliver's leash when he didn't say anything. "Well..."

"Hi, Miss." Oliver said. His cheeks were burning under the mask. Would she know his voice? Would she recognize his mouth?

"I can't believe you brought some submissive dude over for movie night." Carly said.

"You were asking how things were going on the CFE app and if you should try it... and this is how it's going."

"So... he likes this?" Carly asked.

Khloe pulled out her phone. "Let's have a look and see." She opened the CFE app and went into a menu Oliver didn't have access to. "This meter shows how turned on he is." It was like a volume meter on an old stereo with a needle that pivoted from left to right. It was deep into the right-hand side sitting in a section labeled desperate.

"How does it know?" Carly asked.

"Because his little cock is locked in a smart chastity device that can measure how hard he's trying to get, his heartbeat, and all sorts of other things," Khloe said, "If he wasn't locked up, he'd be rock hard right now."

"I can't believe guys just lock up for you willingly."

"Some do. Subby actually made a little mistake with me, but as you can see, he's enjoying that mistake quite a bit. Why don't we get more comfortable and you can ask him all the questions you want. It'll be fun, right subby?"

"Yes, Mistress."

"Good boy. I'll get us some drinks. Carly, take him to the living room." Khloe handed the leash over to Carly.

"I... okay," Carly said as Khloe left for the kitchen. "Are you really okay?" Carly asked Oliver when Khloe was out of earshot.

"Yes, Miss." Oliver said. He didn't know what else to say. There was nothing he could do and Khloe hadn't been wrong. He would never have admitted it normally, but this was turning him on like crazy.

When Khloe got to the living room with an open bottle of red wine and two glasses, Carly and Oliver were just standing in the middle of the room, neither really sure what to do.

"This won't do..." Carly said. "Pour us some wine, I'll fix him up." She handed the wine to Carly and pulled a chair over to the corner of the room where a potted plant was hanging from a hook in the ceiling. Khloe took the plant down, pulled Oliver over, and looped the leash into the hook. "That's better, don't you think subby?"

The leash wasn't tight enough to choke him, but Oliver could only move a step out into the room before it was. With his hands handcuffed behind him, there was nothing he could do about it, either. "Yes, Mistress."

"Oh my god, I kinda want one," Carly said.

"I told you."

"And he really likes this?" Carly asked again.

"Do you genuinely like being treated this way, subby? Does it turn you on? As humiliated as you are, are all of your fantasies coming true?

"Yes, Mistress."

"There you have it. Should we find out what really turns him on?"

"What do you mean?" Carly asked.

"There are challenges on the app that I can make him complete. He's been running around on a treasure hunt for me all day and his next challenge is answering a survey. The sensors in his chastity effectively work as a lie detector and if he doesn't tell the truth, he'll get a little shock. If he fails to answer, it'll add time to his chastity lockup that not even I can remove."

"How long is he locked right now?"

Khloe checked the app. "Seventeen hours that I can't touch and then as long as I want after that. One of his challenges today had an option where people could add a day to his lockup and someone did."

"I'm making an account." Carly said.

"Yeah?"

"Yes! I want a boyfriend with a lie detector locked to his cock! You know how easy that relationship would be?!"

Khloe laughed and opened up the treasure hunt page on her CFE app. "Lucky for subby, the app has some AI integrations now that recognize voices and intent, so we don't even need him to log into his app in order to start the survey." She selected the survey and turned on the audible voice recognition feature. Her phone read the third challenge of the treasure hunt aloud. It was exactly the same as Oliver had read earlier in the day:

Challenge #3 - Take the Test

Little subbies have been known to lie about the things that turn them on. Challenge three aims to correct this. If you choose to take the test, you will be given a set of questions. Your CFE device will use its sensors to measure how you react and change your fetishes on the CFE app accordingly. These settings cannot be changed back by you for three months, which means it will alter your dating profile, change future challenges in treasure hunts, and potentially even open new features for yourself and keyholder within your chastity app.

If you have a keyholder, this challenge must be completed by them asking you the questions aloud. If you do not have a keyholder, you may take the survey online.

For those that finish this challenge, you win the treasure hunt and the prize will be delivered by currier within the hour. For those who opt out of completing this challenge, you will not receive another challenge for 48 hours. For those who start the challenge and stop halfway through, you will forfeit the treasure hunt and add five irremovable days to your lock up after the treasure hunt's deadline. Choose wisely little one... and good luck!

Khloe hit begin and her phone asked for verbal confirmation from both parties. "I consent to begin the survey, do you subby?" Khloe said.

"Yes, Mistress."

The set of questions popped up and Khloe showed her screen to Carly, who started to giggle. "Alright subby, there are five mandatory questions and then it gives me the option to ask as many of my own questions as I want. If you lie twice, you fail the challenge. Do you understand?"

"Yes, Mistress." Oliver's cock was straining in his cage. The nervousness and vulnerability combined with having no real choice in the matter was driving him wild... and even if Khloe wanted to, she couldn't take his chastity off until tomorrow.

"Question number one." Khloe said. "Would it turn you on if your Mistress decided to keep you locked in chastity permanently, only letting you out while you were securely restrained, and only releasing you from those restraints once you were locked back up in chastity, ensuring that the only person in the world who will have access to your cock, including yourself, is your Mistress from this point forward."

Oliver had already been turned on but the idea had him straining even harder. The question scared him... but completely losing access to his own cock did turn him on and that was the question. "Yes, Mistress."

"Oh, look at this." Khloe said as a notification popped up on her phone. "Do you want to tell subby about the new option I have in my CFE app?"

Carly read the notification aloud. "You may now enable chastity guard. This is a feature that ensures your sub's chastity device cannot be unlocked unless he is secured in CFE restraints and vice versa. This ensures your sub will always be restrained and under your control while this setting is enabled."

"Isn't that a fun little addition, subby?" Khloe said.

"Yes, Mistress," Oliver said. He was very thankful that Khloe and Carly couldn't see his face right now. His cheeks were burning red with shame at the effect this was having on him.

"Question two." Khloe said. "Would it turn you on if your mistress forced you to wear women's clothing in private and panties under your normal clothes while out in public."

This wasn't something Oliver would have thought turned him on but in the back of his mind, the humiliation of being forced to wear women's clothes tickled something deep inside. He was already so turned on though, there was no way it could tell something he didn't even really know for sure himself... right? "No, Mistress."

The phone made a buzzer sound similar to when contestants give a wrong answer on a gameshow. Khloe smiled. "Tisk tisk, subby. That's the only lie you get and it just changed your dating profile name to little sissy as a punishment.

"He wants to wear panties?" Carly asked, grinning from ear to ear.

"Oh, I think it's more than that," Khloe said. "He wants me to put him in heels and pantyhose and maybe a little skirt because it'd be humiliating and that turns little subby on.

"Seriously?" Carly asked.

A notification popped up on Khloe's screen that said, Sub is too turned on for their CFE device to accurately detect their answers. Please allow them to cool down. You will receive a notification when your sub is ready to continue the survey.

"Seems like it!" Khloe said. They both laughed. "Let's go come up with some of our own questions in the kitchen and let subby cool a bit."

"Oh, I like that idea," Carly said.

The two women left the room and Oliver was left standing in the corner contemplating just how much his life had changed over the past two days.

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CHAPTER TEN

When Khloe and Carly came back, Oliver had calmed down a little. It had taken fifteen minutes before Khloe's phone had chimed notifying her that the survey could continue; that standing in the corner all alone had served to calm Oliver's cock enough to carry on.

"How's subby doing?" Khloe asked. "Feeling a little better now?"

"Yes, Mistress." Oliver said. His cock was already stiffening back up just from the two women entering the room while he was so helpless.

Khloe watched the meter rising on her phone. "We better get through these quick before he needs a break again." The two women giggled and sat back down on the couch with their wine glasses in hand.

"We've got a bet going on if the next one will turn you on or not." Carly said. "Khloe thinks yes, but I'm not so sure."

"Only one way to find out," Khloe said. "Question three. Would it turn you on if your Mistress forced you to suck another man's cock?"

Oliver didn't think it would but he didn't want to rush his answer. Genuinely, he had no desire to suck another guy's cock. At least... he didn't think he did. His cock was even getting softer at the thought... right? "No, Mistress." Oliver said. There was no buzzer.

"I told you!" Carly said.

"Yeah, yeah... question four. Would it turn you on to be forced to watch your Mistress get fucked by another man while you were locked in chastity?"

Oliver could feel things shift the other way and there was no way around it. "Yes, Mistress."

"Okay, that I don't get," Carly said.

"Well," Khloe said. "It's too much for him to be forced into pleasing a guy but the humiliation of having to watch a real man fuck me while he's helpless still turns him on. It's a fine line, but that's why we do things like this. Now we know one of his limits. Isn't that right, subby?"

"Yes, Mistress"

"Good boy. Question five, the final mandatory question, would it turn you on for your mistress to restrain you, put on a strap on, force you to suck it, and then take you in the ass with it?"

"Yes Mistress," Oliver said. There was no point denying it. He could feel what the question was doing to him already.

"That's hot," Carly said.

"Right?" Khloe said. The app shifted to a screen that listed the questions, Oliver's answers, and whether or not he had been telling the truth. A message popped up saying they had entered the free question round and could ask as many questions as they liked or end the survey at any point. "Carly's got our extra questions and these count for the treasure hunt so I don't want to hear any buzzers that make you lose." Khloe said. She got up and walked towards Oliver. "Understand, subby?"

"Yes Mistress."

"Good boy." Khloe said.

"Alright, fist question," Carly said. "Would it turn you on if your mistress stripped off your clothes right now?"

Oliver didn't want to answer... but what choice did he have? "Yes, Miss."

Khloe revealed a pair of scissors that she had been hiding and moved in closer.

"What are you doing, Mistress?" Oliver asked genuinely concerned.

"I'll buy you a new shirt," Khloe said, and without hesitation, she cut his shirt off, dropped the scissors, unbuckled his pants, and pulled Oliver's jeans and underwear down in one motion. In five seconds, Oliver went from fully clothes to only wearing his chastity device, hood, handcuffs, and collar.

"Would it turn you on if I got a closer look at your chastity?" Carly asked.

Oliver's mind was melting. Everything was happening so fast. "I..." He hesitated. "Yes, Miss." He knew the answer but it was hard to wrap his head around how quickly his situation was changing.

Carly got up and knelt down in front of Oliver. She looked at his chastity, poked it with a finger, played with his balls a little, and then went back to the couch.

"What do you think?" Khloe asked.

"I love it." Carly said. "He's got a nice body, too."

"Right? Keep going."

Carly looked back to her phone and the list of questions they had come up with. "Do I turn you on?"

Oliver had never felt so helpless. There was no point in fighting anymore, though. "Yes, Miss."

Khloe sat back down on the couch with Carly and sipped her wine.

"Would it turn you on if you were my submissive?" Carly asked.

"Yes, Miss."

"Would it turn you on if Khloe sold me control of your chastity?"

That one took Oliver by surprise. Could they do that? Was that even an option on CFE? The idea that Khloe could just sell him like a piece of property was... well it was hard to deny the effect it was having on his cock. "Yes, Miss."

A notification popped up on both Khloe and Carly's phones. Carly had set up a CFE account while they were in the kitchen and the AI recognized the question along with Oliver's answer and it opened up an option for Khloe to pass control of Oliver's chastity to Carly.

"Would it turn you on to know that your answer acts as consent and we now have that option?" Carly asked.

"Yes, Miss."

"Would it turn you on for me to come over there and remove your hood... and if I like what I see, Khloe is going to do it?"

Oliver didn't know how he felt about this one. "Can I ask for clarity... in private?"

"Yes, subby, Khloe said. "Can you give us a second?" She said to Carly.

"Of course," Carly said, and she left the room so they could talk.

"Do you not want me?" Oliver asked.

"Oh, subby. This was fun but I think we both knew it wouldn't last. Not with our parents together. Not with us both staying at home in the summers for the next few years. You didn't know it was me when you locked up and you never would have if you did."

"Yeah but... it's different now." Oliver said.

"I know." Khloe lifted his hood up over his mouth and kissed Oliver long and slow. She gently bit his lip when she pulled back and put a hand on his locked cock. "I'm glad I got to know the real you, and I'm glad you got to know the real me. Carly's going to Western after the summer too, though. You'll be at the same university, you can actually date in public, and now that she's got a little taste of control she wants more. It's perfect. Plus, she really did like you when you met at our parents wedding. She just wasn't looking for a one-night wedding fuck. I don't know for sure, but I think she's going to be pretty happy when she pulls your hood off... if this is something you want." Khloe pulled his hood back down over his mouth.

"I guess I just... we didn't really..."

"I know. It's better this way though, and you know it."

"Yes, Mistress," Oliver said. He knew she was right. The stepsibling taboo had added a layer to his humiliation... but he had set out to find a dominant woman he could build something real with. As incredible as Khloe was... there was no long-term way it could work. It was impossible not to be a little disappointed, though.

"Good boy. Now I'm going to sell you to the hot girl who rejected you not that long ago and there's nothing you can do about it aside from accepting your fate as her new submissive, sissy, slut."

"Yes, Mistress." Oliver was straining in his cage at the thought.

"Carly!" Khloe shouted.

Carly came back in. "Are we ready to proceed?"

"Yes, Miss." Oliver said.

Carly walked up to Oliver, licked her lips, and then slipped his mask off. "Holy shit... You locked your stepbrother up in chastity?!"

"Well... he locked himself up and gave me control, but yeah."

"You dirty little stepbrother slut!" Carly said. She was grinning so wide it almost hurt.

Oliver's cheeks were burning again and now they could all see it.

"And that is why it couldn't last." Khloe said. "So, do you still want him?"

"Yes I do." Carly said. She grabbed Oliver's caged cock and just held it in her hand. "I want him and I want complete control over him. Do you want that, Oliver?"

"Yes, Miss." Oliver said. His cheeks were on fire.

Khloe pulled up the app and hit the button to finish the survey. It congratulated her and Oliver for his completion of the treasure hunt. Khloe quickly found the new menu she had for transferring control of Oliver's chastity. She selected Carly's profile, listed the details of the price her and Carly had agreed upon, and hit accept.

Carly's phone chimed. She pulled it out in front of Oliver and showed him the notification, then turned away so he wouldn't see how much she had spent on him. Carly tapped the button to accept and took complete control over Oliver's chastity. She still couldn't open it for about sixteen hours because of the guaranteed lock time Oliver had gotten during challenge number two, but she had no intentions of unlocking him any time soon anyway.

"Alright you two love birds," Khloe said. "I'm going to go satisfy some growing urges and let you two get a bit more acquainted." She finished her wine and started walking towards the door.

"Thanks, Khloe." Carly said. She didn't take her eyes off of Oliver as she spoke. "Seriously... this is not how I thought the night would go, but thank you..."

"I'm glad it worked out." Khloe said. It was bittersweet but she was quite happy with how things had worked out. She was already messaging one of the other guys that had given her temporary control of their chastity just to message her. "Have fun!"

The door closed and Carly licked her lips. "Seriously though, does this turn you on as much as it's turning me on?"

"Yes, Miss." Oliver said.

"I think I'd prefer Miss Carly when it's just the two of us."

"Yes, Miss Carly." There was a lot rolling through Oliver's head but it was impossible to ignore the effect everything that had just happened was having on him.

Carly had a few new notifications in the CFE app. She plopped down on the couch and grabbed her wine. "I think I'm going to enjoy this," she said. "Shall we see what these notifications are?"

"Yes, Miss Carly."

"Let's see, the first one says that I've now got a lie detector switch I can turn on with you and there are a couple options. I can make it so that if you lie to me at any time, you get shocked. I can also make it so that if you ever lie to anyone you get shocked... Hmmm, let's stick with the first one for now." Carly toggled the first option on. "Does the idea that you can't lie to me turn you on, Oliver?"

"Yes, Miss Carly," Oliver said. There was no shock.

"Good boy. Let's see here. The next one is choosing your prize from the treasure hunt. It says it will get couriered to your location from the closest CFE warehouse. Three options here and... I think I'm going to pick... the CFE high heels that lock around your ankles." The phone dinged in response. "Are you excited to try on your prize, you little sissy?"

"Yes, Miss Carly," Oliver said.

"Good. The last notification says that there will be a new challenge to replace the treasure hunt next week and there are bonus prizes for those who do multiple challenges in a row. That's fun! We'll have to make sure you keep at it so we can collect more toys. Is that what you want, Oliver?"

"Yes, Miss Carly." Oliver felt the shock in his chastity. It wasn't a big shock, but it was enough to make him yelp in surprise.

"Oh, looks like that wasn't quite the truth. I'll ask again before we start the next challenge and if you're up for it, maybe I'll add in some rewards of my own for following through. Does that sound good?"

"Yes, Miss Carly." There was no shock, and Oliver sighed in relief.

Carly grinned. She jumped up, pulled a chair over to the corner so she could stand on it and pull down the leash from the hook in the ceiling. Holding the loop, she guided Oliver over to the couch and had him kneel in front of her. "Normally I don't move quite so fast with guys but there is something about knowing I can do what I want with you that makes me want to see what you can do." Carly pulled her jeans and panties down and sat in front of Oliver showing him her shaved pussy. "Do you like what you see, Oliver?"

"Yes, Miss Carly."

"Good. Use your mouth until your prize is delivered and let's see if you can make me cum."

"Yes, Miss Carly." Oliver said. It was a little awkward with his hands cuffed behind him, but Oliver leaned forward trying to find his balance. Before he could, Carly grabbed the hair on the back of his head and pulled him into her. Carly was dripping with desire and Oliver went to work lapping up every drop.

"Do you want to know what Khloe's price for selling you was?" Carly asked.

Oliver looked up and met her eyes. He nodded without moving his mouth away from her pussy.

"The price was that when you're within fifty feet of her, she gets control of your chastity's ability to shock you."

Oliver just looked up at Carly with big doe eyes.

"She can't unlock you; she can't control anything else with your chastity... but when you're with her you will still have to do what she says or risk getting shocked. Do you understand?"

Oliver nodded again as best he could.

"Mmmmmm, good boy. You're going to be eating pussy every night from now on. Mine or hers. Your job is to learn how to please a woman without that little cock of yours because clearly you need the practise."

Oliver doubled his efforts. He slid his tongue inside of Carly as deep as he could get it and he licked up until he found her clit. He swirled his tongue in circles around it, hoping to please her.

"That's cute. Don't worry, you'll learn" Carly said, "and you won't be getting out of that chastity until you do." She grabbed his hair harder and held his head just where she wanted him. "Slower. Don't be afraid to suck on my clit with those perfect little lips... There you go. Mmmmm, I should have done this years ago."

THE END