TITLE    : A Pivotal Error Pt. 01
STORYID  : a-pivotal-error-pt-01
SUMMARY  : Things go downhill when he disobeys his keyholder.
AUTHOR   : TiltingatWindmills@lit
DATE     : 2023-12-07
CATEGORY : non-consent-stories
FLAGS    : h
TAGS     : |femdom|cunnilingus|facesitting|petticoating|sissification|chastity|tease and denial|denial|humiliation|feminization|


<i>This story contains elements of femdom, humiliation, and feminization. It's part of a world that starts with Election Night Denial, but it should stand on it's own.</i>

Charlotte, Abigail, and Willow stood around the lab bench, chatting aimlessly as they secured their naked, male subject with ropes.

"Abi, would you mind tying a quick double-column, legs to ankle? What's his name struggled a lot the last time and I just want everything nice and tight."

"I think 'what's his name' is Tim." Abi chimed in.

"Umm, pretty sure it's Adam."

The anonymous male tried to speak but only managed to drool through his rope gag.

"Too late to find out now," said Charlotte as she finished an immobilizing gag tie. At that point, the sheer quantity of rope gave the impression that their victim had been battened down by overly zealous pirates.

"Girls, it's nice to see you employing some of the lessons we learned earlier in the semester, but the purpose of this class isn't tying knots. Can you get onto your goal please?"

"Sorry Ms. Jones."

"So what's the class record for this again?" Abi asked as she poured a healthy dollop of lubricant on the boy's already erect penis and began stroking with a feather light touch.

"Four consecutive ruined orgasms," Ms. Jones said in passing.

"I think that's manageable," Abi looked at the other girls for confirmation. "Worth trying for a few bonus marks anyway. I wonder how long it's been since Adam came?"

The boy, who was not named Adam, groaned as she briefly clenched the base of his shaft and then let go, watching to see if anything would happen.

"I'd guess a few days, he'd probably have made a mess already if it was any longer. Here let me take over." Charlotte began making tiny circles on his frenulum with her finger. "So I have this theory that the key to timing a ruined orgasm is actually what you say to him. You can't know what's going on inside his head, so you have to put something there to push him over the edge. He doesn't even have to believe what you're telling him. Here watch this." And she leaned in to whisper in his ear as she kept one finger moving on the underside of his shaft.

"Listen my pet, in a few seconds I'm going to move my finger really fast and then I'm going to stop. I know that right now the thing you love most in the world is my finger on your cock. And even though I'm going to be so cruel and take that away from you, I want you to cum for me. I want you to cum because ruined orgasms turn me on. And tonight when I go home I want to touch myself while I think about your little spurting cock. Can you help me then? Help to get me off?"

The boy's head was almost fully immobilized but he managed a nod anyway.

"Good, I'm stroking pretty fast now" she said as she picked up her pace. "Are you thinking about me touching myself? Picturing me in my bed tonight, with my hands under my panties, whispering your name while I finger fuck myself? Yes? Does that feel good? Can you hear me moaning, <i>hmmm fuck</i>" she intoned even closer to his ear. "Can you hear the wet sounds my pussy makes as I rub furiously with my fingers?" She put two of her fingers in her mouth as she said this and then smeared her saliva across her cheek, "I want you to picture me coming, my round, open mouth, my panting, <i>Oh God</i>." And then Charlotte stopped suddenly. The girls watched the cock as it bobbed up once, twice, and then three times. Charlotte leaned in even closer, "Cum for me like a good little boy."

Another second passed and then finally a slow white ooze poured out of his tortured head.

"See! Easy as can be." Charlotte waited until the boy's cock stopped twitching and then scooped up his semen and used it as more lubricant.

"Ugh can you not do that? It's so gross." Abi complained.

"Really, we're almost halfway through this course on chastity and you're still grossed out by boy juice," Willow defended Charlotte as she took her turn with the subject.

"Well there's a reason we put them all in cages isn't there? So we don't have to deal with stuff like that," Abi replied.

"I'm pretty sure the original intention behind enforced chastity was to create a subservient class."

"Hi, I'm Willow and I took Anthropology last semester!" Charlotte crossed her eyes and pushed an invisible pair of glasses up her nose. The other girls laughed.

"Well I don't care if it was about reducing crime or creating a new gendered power structure, a nice thing about chastity is that you can make a man clean up his own mess if you want and never have to touch it," Abi maintained.

"You need to let loose a little Abi," Charlotte said. "Willow is a shy, stuck up nerd, but even she doesn't mind getting a little jizz on her hands."

"Doesn't it turn you on at all, playing with dicks every time we have keyholding class?" Willow asked.

"Well first of all, we don't play with dicks every class. There are the classes on ropework, the classes on legal theory, the classes on female sexuality..."

"Okay, okay" Willow interrupted. "But when we have guys volunteering - don't you touch yourself when you get home?"

"Nope. Never. Like in general even."

"Wait, how have we not covered this before?" Willow released the boy's cock and it sprung free to slap against the skin of his abdomen where it remained unattended.

"There's not much to it. Like things arouse me but I don't like touching myself. I guess I don't like messes, or the smell that lingers on your fingers. Maybe it's just some relic of prudishness from my grandma, I don't know."

"Okay but you've had an orgasm before obviously" Charlotte clarified as she picked up the pulsing cock in front of them and began rubbing it again.

"I don't think I have," Abi replied.

"Mother Mary, what the hell? Where were you the day Ms. Jones gave us all vibrators and had us use them in class?"

"Stayed home."

"Okay. Well if you don't like the smell or the mess why don't you just make a guy go down on you and tell him to clean it all up after. There's plenty of dudes who would love to do it."

"Sorry I'm not Charlotte Fleming, hottest girl in the school."

Charlotte tossed her straight brown hair over her shoulder and put on a pouty pose while Abi giggled.

"Come on Abi," Willow gave her a raised eyebrow. "Lots of boys think you're cute. You have that sweet, girl next door vibe going on. Guys love that. And they really love blondes. Hell, I barely put on makeup or anything and I've got three numbers in my phone of guys I can text any time I'm horny."

"Oh fuck that was close" Charlotte removed her hand just as she sensed an oncoming orgasm and was rewarded when a tiny drop of cream emerged from the struggling dick in front of her.

"First of all," Abi ignored Charlotte's interruption and continued, "You have huge tits, Willow. Second, even Charlotte has to trade off something, like letting them lick her boobs or whatever. And third, I guess I'm a little nervous to have guys see me naked down there. I'm worried they'd talk and say things." Suddenly she remembered that there was a man at their very table. "And you, Adam, don't you breathe a word of this conversation or I'll squish these distended little balls worse than you'd ever imagine," and she slapped his testicles before continuing where Charlotte left off.

"Okay, I think you're too worried about how much guys talk." Charlotte leaned forward, propping her elbows on the boy's chest as she spoke. "There are rules about not speaking badly of your keyholder. I know they're hard to enforce but guys are generally terrified to break them. And I think most of them are too humiliated to discuss chastity stuff with one another anyway. You're overreacting."

"That's exactly it though. When I become a keyholder for the first time, then I think I'll feel comfortable enough to experiment a little more. I can have him go down on me and it will be completely on my terms. In the meantime, I'm happy putting my sex drive to work getting me good grades."

"I will grant you that I'm also frustrated with not being a keyholder yet." Willow said. "The mothers at this school are way too reluctant to give up their keys until you've finished the courses. And there's not much point in dating if you can't get a guy's key. Plus, ever since that article came out claiming the health benefits of frequent orgasms for men, mothers around here have become way too lenient and the guys are just not desperate enough. But if I had my own toy to place with, I'd keep him locked up for weeks and it would be so much better."

"Yeah, you've got me there too." Charlotte admitted. "I get super horny when I'm on my period and none of the guys around here are desperate enough to go down on me then. But if I was a keyholder he wouldn't have a choice..."

"Oh damn it!" This time it was Abi's turn to interrupt. She had already released her hand, but it was a second too late. The nameless boy had already begun shooting his load.

"So much for the class record," Charlotte complained as she leaned back to narrowly dodge the first spray.

***

Abi left the girls to clean up and headed to her next class.

She attended a co-ed finishing school that had become mandatory in their state three years ago. It was one to two-year program for high-school graduates where female students took courses on leadership, finances, and keyholding, while male students took courses on household management, culinary arts and massage therapy. And there were some co-ed college level courses, including chemistry, which Abi was headed to next.

"Oh, hi Abi!" It was Quinn, her chemistry seatmate.

"Hi Quinn, you ready for today's lab?"

"Yes ma'am!" he replied. "Are you okay with our normal split -- you manage the glassware while I take notes and wash up?"

"Yes it really does work the best. Your writing is so pretty and I'm just too clumsy around the sink!"

Abi felt a little bad about Quinn not developing his lab skills, but realistically he would never use them, whereas Abi might actually have a career in science.

The instructions were on the board when they walked in so they went straight to work. Throughout the lab Abi felt like Quinn was a little distracted. Once she caught him checking out her ass, though he looked away immediately, and then he was awkward for the rest of the lab.

<i>Boys are so sensitive,</i> she thought.

At the end of the class she was preparing to say goodbye when Quinn interrupted,

"Hey Abi, is it alright if I talk to you about something? Something kind of private?"

<i>What could this be?</i> Abi thought.

Abi didn't really have any guy friends, Quinn would be the closest. Maybe he felt the same. Perhaps he was having girl trouble and wanted her advice. Or did he want to ask her out?

"Of course," she replied with a smile, still pondering to herself what it could be.

If he was asking her out, she would obviously say no. Quinn was cute. Not just in the sense that he had a cute face, but also that he had a slender build, and was maybe an inch or two shorter than she was. She had to admit she did like looking at his face. It's not like she got lost in his eyes, but she found them striking enough to know that they were blue. Certainly from time to time he could be rather charming. But she had two preferences in a partner, manly men (a dying breed to be sure) and women. Quinn was too much in between.

As Abi interrogated her feelings towards him, Quinn pointed them towards a quiet hallway and then fidgeted as they walked in silence together.

"So, what is it?" Abi finally asked.

"I turned eighteen yesterday..."

<i>That explains a lot.</i> Quinn was going into enforced chastity for the first time. She had never really noticed that he wasn't a volunteer in any of her keyholding classes, but it made sense now.

"Happy birthday! But uh, everyone else has been eighteen forever? Most of our class is about to turn nineteen, if they aren't already."

"Yeah, I skipped a grade a while ago."

"I see." Abi waited for him to continue.

"So the thing is, I asked my mom if I could choose a keyholder other than her, and she said yes. Well she said she didn't care. Basically I can choose whoever I want. She even gave me the paperwork and the key," Quinn pulled both out of his backpack.

"Quinn are you crazy? You're eighteen now -- men aren't allowed to carry their own keys in public! You could let yourself out any time you want!"

"Well that's the thing. I was hoping you'd agree to be my keyholder."

Abi was caught completely off guard. She paused and stuttered and then finally felt the need to be decisive and say something.

"Here give me the key then, and I'll think about it. Come to my house tonight at eight and we can talk. Okay?"

Quinn smiled and nodded.

***

Abi waited in her room for Quinn to come up the stairs. She had already given her mom instructions to send him up. She wanted to do this right.

When he walked in she was disappointed to see him wearing the same clothes from earlier that day. He clearly wasn't treating this with the respect it deserved. Meanwhile she had put on a black lace dress with long sleeves and done her hair in an up-do.

At least he was suitably impressed by her.

"Oh wow, Abi, you look, amazing."

"Thanks Quinn. Why don't you come in." She was the very image of a sophisticated host. Wearing only jeans and a t-shirt, he suddenly felt like she was ten years his senior.

She sat in the only chair in the room. At first he stood awkwardly, trying to decide if it was too forward to sit on the edge of her bed, until she finally gestured for him to sit on the carpet at her feet.

"So I've given some thought to your offer. And I've decided to accept."

It had taken her only a couple hours of consideration. She couldn't think of a downside. At the very least she would get a part-time domestic servant, and if she was being honest, the thought of finally experimenting sexually made her sort of giddy. Willow and Charlotte had been more persuasive than she would have liked to admit.

Quinn smiled broadly and only then noticed that she was already wearing the key he had given her on a bracelet.

"I've signed the paperwork here. I just made a few amendments to the list of services you're expected to provide. Nothing major -- mostly stuff about cleaning frequency and so on."

Quinn breathed a sigh of relief. He had been steeling himself for rejection.

"While we talk a little bit about your roles and responsibilities, maybe you could start by massaging my feet."

"Right, of course." Quinn fumbled to take off her socks but muscle memory soon took over.

<i>This might not be so bad</i>, Abi thought to herself as Quinn began kneading the balls of her feet.

"So, most guys spend a little time in training before their 18th birthday to get used to things. I assume you did a few practice days or weeks in the device?" Abi asked.

"No, I kind of kept putting it off."

"Oh. Did you at least try out some periods of umm, self-denial?"

"No, well yes. I tried. They just weren't very successful."

"How many days? Be honest with me, you know how important it is to not conceal anything from your keyholder."

"One."

"You did <i>one</i> day without masturbating? That's it?"

Quinn averted his eyes and nodded.

"Yesterday?"

"No, a few days ago."

"Okay, and how often do you masturbate in a normal day?"

"Maybe three or four times. Sometimes more."

Abi suspected that five might be more of the norm.

"Well you may be in for a rough first month. Why don't you stand and I'll have a look at your cage, and make sure everything is fitting right."

Quinn stood up and began taking off his clothes. Unlike many of the boys in her program, she had never seen him without his clothes on. He had never attended those classes.

Quinn's furtive movements were somewhat endearing. Abi had been in dozens of rooms where all the men were naked, and all the women were clothed. It was too commonplace to be shocking. Even her father, her cousins, and a few teachers had been without clothes at one event or another. But she was unprepared for what she felt now.

Her room, the carpet, the muted lamplight, her childhood possessions -- it all made for an extremely intimate setting. It reminded her of a historical story she had read about a couple in an arranged marriage who were undressing for the first time in front of each other.

And there was nobody else here telling them how to do things. Abi alone was in charge. She had told him to sit on the ground at her feet and he did. She had told him to massage her, and he did. She had made him tell her about his private sexual habits, and she had not reciprocated in the least. And now, Quinn was undressing before her because she had told him to.

Her breath caught in her chest with this confluence of emotions.

When Quinn dropped his pants she was a little surprised by what she saw. He was less muscular than most men, and almost completely hairless. Maybe a light, dusty fuzz on his legs that you didn't notice unless it caught the light. And then of course, like any man, the same impotent genitals, trapped in a transparent device. She didn't find him attractive as a man, but the thought that without his cock he looked very nearly like a woman intrigued her.

"Did it hurt last night when you woke up?" she asked softly.

He nodded.

"Men can get up to five erections per night. The pain can be especially bad if your cage doesn't fit right and pulls your testicles away from your body. Can you come closer?"

He took a step towards her so that only inches separated their legs. She reached out and gently cupped his testicles.

"Your base ring is a little too big." She had a keyholder kit from class, and took a fabric measuring tape out of it and used it with a practiced hand. "I'll go to the shop and buy you a new one."

"I thought it actually felt too tight."

"Trust me, this will be better. Anyway we don't want you to be tempted to escape. I should add that even if you do, you won't be able to get back in on your own, so I would figure it out."

"Of course, I would never."

"I think you'll be surprised at the things you would be willing to do once you've gone a week in chastity."

He didn't respond.

"I'll see if I can spot any chafing or if I need to unlock it to inspect you."

Abi turned the device over in her hand carefully and Quinn suppressed a groan.

Just then there was a knock at the door and it quickly opened.

A young woman came partway through the door before stopping. "Oh sorry, I forgot you had a guest over!"

The woman, who looked like a younger, more petite version of Abi, smirked and then closed the door slowly.

Quinn was mortified.

"Sorry, that was my sister, Grace, just snooping. She probably did it on purpose. Next time I'll have you lock the door."

Abi returned to inspecting the cage and its contents as if nothing had happened, though she took note of how embarrassed Quinn looked. Probably he did know Grace, she thought, they would have been in the same year until he had moved up a level.

"Your skin looks fine," she continued, "but I'll let you out for a few minutes just because you might need a break. It would be better if you had eased into this gently you know?"

She took the key on her bracelet and unlocked him, opening up the device faster than he could have done himself. She left the base ring on and waited for his body to react but nothing happened.

"You must be really nervous, huh?"

She took his flaccid member by the hand and pumped it a few times, stopping when he moaned.

"I don't want to go too far. I've seen guys shoot off before they even get hard and I'm not one to allow accidents."

She waited for him to reach his full length and then spoke, "Everything looks to be in working order. There are some ice cubes in a bowl over there, can you bring them for me?"
<hr pg="2" />"Already?" he responded. "I thought..."

She shot him a death glare and he immediately scampered off and brought back the ice.

"I will not allow you to speak back to me, Quinn. I want you to get back on your knees, and kiss my feet, and thank me for putting your cock back in its little cage."

He quickly knelt to the floor. Holding up her foot reverentially he repeated, "I'm sorry for speaking just now. Thank you for locking my cock up in its cage."

"Little cage," she corrected him.

"Little cage."

He began kissing the instep of her foot. Slowly and softly. He seemed naturally sensual. He lifted her second foot, and she gave it to him, accepting kisses there.

She watched for the telltale sign of twitching in his cage and was gratified when she saw it.

Eventually he kissed her toes one by one, and then put one in his mouth to suck on.

She let out a quiet moan.

Emboldened, he worked his way back up her foot, kissing her ankle and then the very lowest point on her calf.

"Did I invite you to kiss my legs, Quinn?"

"No, I'm sorry."

"That's enough then. I think it's time for you to go. I'd like to start a routine with you, Quinn. Each time you leave my presence I want you to thank me for being your keyholder. But don't always say the same thing. Try and be creative to show some genuine gratitude."

"Right. Thank you for helping me to control my orgasms."

"Not bad. But to be clear, I'm not helping <i>you</i> to control <i>your orgasms</i>. <i>I</i> am controlling your orgasms."

Quinn gulped and nodded and let himself out.

When he left, Abi allowed herself to slouch a bit in the chair and realized that she was wet.

Ever so tentatively she slipped a finger under her panties. She was <i>quite</i> wet.

She massaged her flesh just around her outer lips and moaned involuntarily. Instinctually she slipped her middle finger inside herself, finding that it plunged in more readily than she expected.

A second moan.

She thought back to Quinn kneeling on the ground before her. His angelic face looking up at her, following her orders. If she had told him to kiss her legs he would have done it. She suspected that she could have told him anything. She could have made him pleasure her. She was in fact <i>going</i> to make him pleasure her. She knew this now.

Her other hand pulled her dress and bra down and she lightly let her fingers circle her nipple. Then she tweaked it slightly. It was already erect and sensitive.

Her hips were moving against her will now and a pressure was building inside her. A warmth and a tingling that was escalating faster than she expected.

She withdrew her slick middle finger and used it to apply pressure to her clit, imagining that it was Quinn's tongue. Gradually the tingling began to spread and came on in powerful waves and she cried out loud enough for her sister in the next room to hear. It was a seismic experience, and one that shifted the plate tectonics of her thinking.

When it was over, she lay there, slouched on the chair for long enough that her tailbone hurt before she finally got herself up. Her legs felt like jelly and she barely made it to the bed.

No wonder Quinn did this five times a day.

What a thing she was taking away from him. And what a thing she had just gained.

***

"So, when you finally become a keyholder, what are you going to do with your first toy?" Willow asked Charlotte and Abi.

Abi still hadn't told the girls about what had happened.

"God, I think I'll probably go nuts for the first week or so. Just make him do the nastiest sex stuff for me." Charlotte responded as she clicked the handcuffs shut on their new subject.

Today's session was on punishment devices; chastity cages meant for short term discipline. Charlotte was inspecting one with small studs on the inside. "God this must hurt" she whispered.

"Can you make sure his headphone music is turned up before we start?" Abi asked.

Charlotte obliged by turning up the volume up on the subject's headset.

"What about you Willow, what are you going to do?"

"Definitely he's going to have a sore jaw. At least at first. I hear a lot of women slow down with that after a few months and then start to appreciate teasing him a bit more. How about you Abi?"

"Oh you know me, I'm mostly excited about having him rewrite my sloppy chemistry notes for me and things like that."

"Of course, Abi the abstinent," Willow joked.

"Actually guys, I did want to tell you something. You know Quinn, he's my lab partner in chemistry? He asked me to be his keyholder... and I said yes."

"Shit no way! Does that mean -- has he gone down on you? Have you had an orgasm?"

"No and yes. I actually touched myself thinking about it. It was amazing. I did it three times last night and then had to stop myself because my fingers were getting sore."

"Oh my god this is such good news. And we finally have a friend with a man to boss around. So when are you going to make him do it?"

"Girls," Miss Jones interrupted. "Can you please get to your task?"

"Right. Sorry" Charlotte said as she began applying ice to the ignored erection in front of her. "Willow, can you pass that micro cage, the one that's almost flat. I want to see if we can squeeze it in there."

Once Ms. Jones was out of earshot Abi responded.

"I want him to be a bit hornier first. He's only been in chastity for a few days. I was thinking this weekend. But I gotta say my imagination has sort of been running wild. I think the part that gets me off is the power, and I'm worried I'm going to push his limits too far too fast."

"No such thing girl," Charlotte responded. "Guys are crazy about sex. Look, at this idiot" she gestured to the restrained male body in front of her. "He volunteered for our class because he thought he might get a ruined orgasm and instead we're putting his dick in a thimble." She said this as she actively pushed his still puffed-up member into the absurdly small cage.

"Yeah I mean you signed the contract right?" Willow asked. "That means his reproductive system is technically your property. As long as you don't permanently damage him I think it's fine."

"Okay that puts me at ease. I gotta say though this is harder than expected. I'm not sure if all guys are like this when they start out but Quinn is really stubborn."

"Didn't you say his mom kind of ignores him? She definitely doesn't care too much if she gave his key away to whoever he wants. Maybe he's just used to being independent."

"Yeah I guess so."

"Got it!" Charlotte had managed to click the lock shut on the micro cage.

"How can it get that small?" Willow asked peering at the cage.

"I think it pushes most of the penis back inside the body. That's why his balls are pushed out like little balloons," Abi moved them around as she looked for evidence of the now hidden penis.

"Thank God I'm a woman," was all Charlotte had to say.

***

Two nights later Abi received a message from Quinn.

<i>I think I'm having a medical emergency</i>

She called him immediately.

"What's happening?"

"I've got this really bad pain in my testicles. I'm worried they're losing circulation or something."

"Is it a sharp pain?"

"No, more like a dull ache, from the inside."

"And what color are they?"

"Like regular color? Maybe a little more red than the rest of my skin."

"Have you injured them at all?"

"I don't think so."

"Quinn, you just have blue balls. You've been aroused without any outlet and you're having some swelling. It's fine. You'll get over it. Put some ice on them."

"But they would feel better if I had an orgasm, right?"

"Don't even try that on me. The answer is yes, but I'm not letting you out."

"Abi come on, it's been almost a week. When are you going to let me cum?"

"Whatever day it was just moved one week later. Now that you're legally a man you need a woman's permission to ejaculate, and I'm not giving it. If you want a release you could at least come beg me in person. Anyway, I don't believe you're suffering that badly yet. I've certainly gone longer."

"It's driving me crazy though. All I can think about is sex."

"Oh is that so?" Abi's tone changed. "Why don't we work on some honest communication. If I believe what I hear, then maybe I'll let you out a little sooner." As she said this she put her phone on speaker and lied down on the bed, pulling her shorts down to her knees.

"What do you want me to be honest about?"

"What sort of fantasies are you entertaining?"

There was a long pause.

"Well, do you want out a little earlier or not?"

"Okay. I'm thinking about you. Who else? I chose you as my keyholder because I think you're smart and walk to the beat of your own drum, but also because I think you're really sexy. And now this sexy girl is asking me how often I masturbate and not allowing me to touch my own dick."

"And that turns you on?"

"Yeah I guess so. It also means I have to think about you all the time. I have to sit down to pee and I think about you. I can't sleep on my stomach because the cage is too bulky so I think about you. And then thinking about you makes me horny. And I want to get hard but I can't and that reminds me of you too."

Abi slowly began circling the entrance to her pussy as Quinn spoke.

"So it sounds like you would do almost anything to cum right now."

"Yes, anything."

"If I made you humiliate yourself in front of my friends, you would do it?"

Another pause.

"Yes."

Abi bit her lip and began pleasuring herself in earnest.

"So if the only way you got to cum was if you had to hump a pillow on the floor while me and Willow and Charlotte watched, you would do it?"

Another long pause and then a quiet, "yes".

"If I said you can cum but you have to do it by jacking off in your mom's panties, would you?"

"Yes."

"God that's hot. Okay, tell me more about what it's like. From your perspective, being controlled like this by a girl in your class. Give me lots of details."

She quietly hit mute on the phone and then moaned as she clenched her hand between her thighs.

"It's crazy. Like one day you're just a girl in my class. We work together on the same assignments, we both have to deal with parents and grades and applying for part time jobs. And then the next day you have so much power over me. You become like a goddess overnight."

Abi could not have scripted a better conversation to touch herself to. Quinn continued, "And meanwhile I wake up every day with an aborted erection and aching balls. Sometimes I try to grab myself but there's nothing there. I roll over and grind against the bed but I can't feel anything. And when I walk I hear this quiet clicking noise from the lock as it hits the cage and it reminds me of you too. I think about your body. The way your long, sandy hair falls in ropes over your shoulders. The swell of your breasts inside that black dress you wore. How I want to rip it off and touch you everywhere. But I know that even if you told me I could do whatever I want there'd be nothing I'd be able to do. It would only make the frustration worse."

Abi was getting so close, she could feel that impossible pressure building and she just needed to let it burst. She was panting now and grateful that she had muted the phone.

"It's so hot knowing that it's all out of my control," he continued. "Knowing that you could keep me in there for weeks and I couldn't do anything about it. I already have to stop myself from begging you to let me cum. I know you wouldn't like it but I need it so badly. I can't focus on my studies, all I think about is your body and my cock. Please Abi, if you could just let me out for five minutes. You wouldn't even have to touch me. Just let me have an erection for five minutes and then put me back in my little cage."

When he called it his little cage she finally came.

"Abi. Abi are you there? Abi?"

"Yes, sorry, that was good."

"You sound out of breath, are you walking uphill or something? I thought you were home?"

"I'm fine. And you'll be fine too. But I've gotta go. Come to my house tomorrow night. I'll give you your new cage. Okay?"

She hung up before he could respond and basked in the afterglow of her orgasm.

***

This time when Quinn arrived, he showed up in a suit, bearing flowers.

"Better," said Abi when she greeted him at the door before taking him upstairs.

Once again Abi took her place in the chair and ordered Quinn to undress. Then she showed him his new cage.

"It's pink," he said.

"Yeah, do you like it?"

"Umm, yeah, thanks for getting it."

"I got you something else as well." She pointed to her bed.

"Sheer panties... are these for you?" he asked as he picked them up.

"No, they're for you silly. To match your new pink cage. You probably noticed how heavy the cage feels, this will offer you more support than men's underwear. Plus, I think they'll look good on you."

He flinched a little but managed to control himself. "Thanks. It's very kind of you."

"I know. Anyway, let's get that old one off."

He stepped closer and she unlocked him. This time he sprang to attention with no touching needed on her part.

"How does that feel?"

"So good, oh my god. Thank you Abi."

"Remember, you're no longer allowed to touch your cock. Ever. If you do it's right back in the cage."

He nodded.

She admired his phallus. So much like himself. Smooth, well-shaped, and so very different from the angry, vascular meat sticks she handled in class.

"So, do you want me to touch it?"

"God yes, please Abi, you know I'd do anything."

"Beg me then."

"Abi, please play with my cock. I've been so good this week. It's been so long since I came. Please touch me even just for a bit."

"You said on the phone you would settle for just having an erection again." She moved her hands across his stomach and legs, egging him on. "Why should I play with your little cock?"

"Oh Abi, please, can't you see how hard I am? How crazy you're driving me?"

His cock twitched as if to prove his point.

"Fine, just a little then."

She dragged the flat of her fingernail from the base of his cock up to the tip and inserted it ever so slowly into the hole of his cock. Then back down again, this time running the line between his two testicles as he shivered at her touch.

"Oh, looks like someone is drooling. Very impolite." She motioned to a small drop of precum accumulating on the tip of his cock. She made a small ring with two fingers and ran it up and down his shaft, careful not to get too close to the liquid.

"How about I hold this here and you can move how you like?" she offered him the small circle she had made with her hand.

Quinn nodded yes and began thrusting into her hand, but she kept her grip so loose he could barely feel it.

"Are you getting close?"

"Oh my god yes, please just a little more."

"Wow, it only took a week to turn you into a premature ejaculator." Abi squeezed her hand tight so that he suddenly shook with pleasure. "Or maybe you already were?" And then she released her hand.

Quinn continued bucking his hips into the air but there was no pressure and he moaned in exasperation.

"Oh god, no!" he whined.

His cock pulsed like it was trying to pump semen out from an empty reservoir and only a single white, ruined drop emerged from the tip.

"What did you do to me?" he cried out.

"That was a ruined orgasm. You didn't like it?"

"It felt... so empty!"

"Are you still horny?"

He nodded vigorously.

"You should try to start liking them, because they're the only kind of orgasm that I'm going to give to you. Now lick up that little drop of cum quickly because it's time to put your little man back in his new home."

"Do I have to?" Quinn looked with disgust at his own ejaculate.

"Quinn, you're making me angry. Please follow orders quickly or I'll have to punish you" Abi said quickly.

Quinn looked aghast. He was still trying to process this idea of her not letting him have a full orgasm, and now he had to eat his own cum and then go back in the cage already.

Quickly he put the white drop on his index finger, dabbed it on his tongue and swallowed like he was downing a pill.

Abi smiled to herself. It was standard practice for the early days of chastity to make men consume their own emissions, and Abi was going by the book for now. Besides, she regarded semen with more disgust than Quinn did, and had no intention of cleaning up for him.

As soon as he finished, Abi wasted no time stuffing his appendage into the small, pink device.

When she heard the click of the lock, she felt a power that she had never experienced before. He was truly hers. Her toy.

She looked up at him waiting and although she could tell that he was fighting his own instincts he still managed to say, "Thank you for playing with my cock."

"Technically it's my cock now, but you can call it yours if it makes you feel better. Leave the panties off for now. I want to have a clear view of my toy for what comes next."

She once again put her foot in his lap. When she nodded he began kissing.

"This time you can kiss my legs."

He went faster this time, any patience eroded by his lust. She could see him stealing glances up her skirt and she didn't even mind. He would see more soon enough. She parted her legs for him and his kisses climbed up past her knee. She was breathing heavily when she finally decided to tell him.

"I want you to lick my pussy."

And just then, he stopped kissing her.

"I... I'm not ready," he blurted out.

She almost thought she had misheard him. "You're not ready?"

"I'm so sorry. It's just, I've always had a thing about this, a sort of hang up. I'm sorry this is so embarrassing."

"You think it's embarrassing for you?!" She could not contain her anger.

"I want to, I really do, it's just I think it's like an acquired taste or something and I need to..."

"Wait, so you stand there and expect me to play with your cock, but then when I ask you to return the favor you back out? Talking about how you'd do anything to cum, but won't even have oral sex with a beautiful girl. Stand up right now."

She was furiously running through options in her mind. She could bend him over the bed and spank him until he was raw. She could grab him by the balls and force him to do what she wanted. But she wasn't aroused anymore, just angry.

"Put on your panties. Go ahead. A real man doesn't need to be forced to pleasure his keyholder. You're not a real man, so you won't be wearing men's underwear. And leave the suit there. You're going home in what you're wearing now."

It wasn't until then that he realized how bad of a mistake he had made.

"My laundry is in the closet. You can take it with you. I'll expect it washed and dried and back tomorrow morning. And you'll need to stop by my sister's room and ask her for her clothes too because you're going to be washing them as well."

When he stepped out with the hamper in his arms she slammed the door, leaving him alone, and mostly naked, in the hallway.

***

"I am absolutely enraged." Abi explained. "I feel humiliated. Like there's something wrong with my body, and he hasn't even seen it." The girls were in the changing room after volleyball practice. Almost everyone else had trickled out already.

"There's nothing wrong with your body," Willow comforted her. "You look like a goddamn model. And I got a pretty good view of what you have going on down there when you and I got tipsy that one night. I think you've actually got a really gorgeous pussy. It's just bad luck that you have this insecurity and the one guy you wanted for your first time is the one guy that doesn't like eating girls out."

"I don't get it, I would have just tied him up and ridden his face," Charlotte said as she reached behind herself to try and get her strapless bra back on.
<hr pg="3" />"That's not the point, he should want to please me!" Abi explained.

"You're right, you're right," Charlotte agreed. "I just think that if you had mounted his face he might have started to like it a little. You can lean back, play with his balls, and suddenly he's willing to do it the next time."

"Well regardless, the moment has passed, and I think we should help plan the next move," said Willow.

"I want to make him eat so much pussy he drowns," Abi was holding nothing back.

"So like, your own pussy or are you saying you'll need help?" Charlotte said with a smirk.

"I'm not the jealous type, if you want to borrow him you can have it him."

"Noted," said Charlotte.

"Seriously though. I am going to turn him into my mindless sex slave. I want him at my beck and call and desperate to bring me pleasure."

"I like the sounds of that."

"Okay but how are you going to do it?" Willow asked. "This moment calls for some clear-headed thinking. I think he's got some Mommy issues that might be worth exploring, but we can also go a more blunt route and try tearing down his pride."

"Or just keep making him hornier," Charlotte whispered under her breath.

"I like Option 2, Willow," Abi ignored Charlotte. "He deserves to be humiliated anyway. Any ideas?"

"Well, you're off to a good start, I just think you need to dream bigger."

***

She ignored his messages for the next day and he found himself alone in the chemistry classroom. A week passed with no invitation to visit her home except once to do her laundry. When he came she had seven pairs of panties laid out for him and a note telling him to drop his old underwear off at her house as he would no longer be needing them.

He was still inescapably horny. He tried to volunteer for the keyholder classes (the school kept backup copies of everyone's key) but they said they were already full until the end of the year.

Abi did return to chemistry, and the next time he saw her he was stunned. She had started wearing more makeup, pink and gold eyeshadow, and although she was in one of her old blouses, there were not nearly as many buttons fastened as the last time she had worn it. He wasn't the only one who noticed, and he became jealous of the other guys who stared at her. Had she already asked them to do the thing that he had refused?

Another week passed and finally he received a message telling him to come to a coffee shop later that evening.

When he sat down across from her, he was almost wild with desire. But before he could speak, she interrupted him.

"I want you to know that I'm not angry anymore," she started.

He felt a wave of relief sweep over him.

"I signed up as your keyholder and that means training you. And you need a lot of training. So I've given some thought as to how to best do that. First, this is for you." She passed a collar across the table. It was pink leather with a small, steel hoop. He knew that keyholders sometimes made their men wear these when they had done something terrible. It seemed he was now in that camp.

"I want it on you 24/7. I'll let you know when I think you've earned removing it, but I don't see that happening any time soon."

"Second, I know you said that eating pussy is an acquired taste, so I think you need to spend more time acquiring it." She shimmied beneath the table and then reaching downwards pulled up the pair of panties she had been wearing. "Put these in your mouth."

He did. He could smell her on them. Taste her. He wondered if she had touched herself in them.

"I want you to leave them there, all night long. You can use duct tape if you need to, I don't care. And I want you to understand that this is a gift, not a punishment."

He nodded.

"Third, I've brought you some clothing." She passed him a large shopping bag. He peered inside. There were white jeans, thin stockings made of lace and cotton, a few short skirts, and panties of multiple colors and fabrics.

"It's not laundry. They're things I want you to wear. I think you've had too much independence and need to be reminded that someone else makes your decisions now. The skirts and dresses are for when you're home. Either visiting me or in your own house. If you're not naked in those two places then that's what you'll be wearing. In public you can wear the jeans, but make sure you keep the stockings on underneath. As for the panties, those are your underwear now. You can throw out whatever you've used until this point if you haven't already. Why don't you go to the bathroom now and try on an outfit."

Quinn stepped into the bathroom, and stared at himself in the mirror. How did he get here?

He rummaged through the clothing. The panties were mostly lace, or satin. There were only two cotton pairs that seemed more for everyday use. He thought he should probably start there, but part of him was drawn towards the smoothness of a white satin. He slipped it over his legs and shivered as he did. The way they clung to his hips and concealed his cage gave him an illicit thrill.

He shook himself out of his temporary trance and forced on a pair of jeans, scolding himself for whatever he had felt a moment ago.

When he returned Abi could see that he walked funny in the jeans, they were a little tight, as she had hoped.

He pointed to his mouth, asking permission to remove the panties. She nodded, "only for a moment."

"Maybe a size larger..." he began saying but she cut him off.

"No, they're perfect. I like how I can see the bulge of your cage. It's a stretch fabric so the tight fit is the point."

"Yes, Abi."

"Good. Just so you know, Charlotte and Willow helped me pick these out. So they know what's going on. And I've told a couple of other girls I trust, but they know to keep it to themselves. I want you to be self-conscious. I want you to walk around the halls noticing the way girls look at you, and I want you to be guessing which ones know that you're wearing women's lingerie under your clothes."

"Yes Abi. Thank you for buying me new clothes."

"You're welcome. Although there's a receipt in the bag. You can bring me cash with the next load of laundry. And starting tomorrow I'd like you to start stopping by my house in the mornings to make breakfast."

"Yes, Abi."

"And you can help my father with cleaning the kitchen and tidying up. Do you have any questions?"

"No. That's fine. But I did just want to say... I'm sorry for being a brat."

"I accept your apology. We had a difficult start Quinn, and you've got some more growing pains to go through. But I think it won't be long before you're very happy that you picked me as your keyholder. Now put the panties back in your mouth, you're done talking for the night."

***

At home that evening he tried on multiple pairs of his new panties. He told himself he was just needing to test which ones were more comfortable in his cage. But when he tried on a pair of stockings he could no longer lie to himself - he found it unbearably erotic. He had chosen a simple white pair. But their softness, and the stretch of them as they glided over his legs - it was intoxicating. Looking in the mirror from the waist down, wearing a short, pleated skirt and the white stockings, there was no way to know he was a man. Even when he pulled up the skirt so he could see the bulge from his pink cage beneath the translucent panties it was easy to forget how he had once looked.

At school he blushed furiously when he ran into Charlotte or Willow. They seemed to act normal, except maybe for the smallest of smiles, or a quick glance at his legs. Before he left school he would meet with Abi, who would take off her panties from beneath her skirt and pass them to him to put in his mouth. They were always soaked.

Although he found his petticoating treatment too humiliating to be sexual while he lived it out during the day, at night while he lied in bed, feeling the shifting silk of his underwear, and tasting Abi in his mouth, he dreamed of the next day, imagining how some woman he had never even suspected might approach him in the hallway and whisper the simple words, "I know."

That weekend was the first time his mom was actually in the house at the same time as him. He briefly considered disobeying Abi's orders to always wear female clothing around the house. Instead he delayed going to the kitchen for breakfast, slowly working up the nerve to face his mother. Finally, he climbed down the stairs in his skirt and stockings.

His mom laughed of course, and he quickly let her know it was only because he was being punished.

"Sure honey, I'm sure it's completely out of your control," she said with a smirk.

Keyholders disciplined their toys, his mother obviously knew this. But when she had her friends over for cocktails later that night she was less forgiving.

She made jokes at his expense, and her friends insisted he remove his panties and pull the skirt up high enough that they could see the pink of his cage under his skirt while he served them.

That was the first night that he began to experience leaking from his device in earnest. Quinn wanted to believe it was just the time spent in his cage, a full month now, but the constant drip forced him to reckon with the idea that perhaps he was turned on by humiliation. Something he had never even considered before.

He wiped his precum away once and didn't notice it was back until one of his mom's friends pointed out the strand dangling from the small slot at the front of his cage. Even though he discreetly tried to wipe up, within ten minutes it would be back. It was actually his mom who spotted him cleaning it and told him to leave it alone. She didn't approve of men wiping themselves like that in public. He tried to not look at it, but the women started keeping track of how long it was growing. Laughing about how his strand of precum was now stuck to his leg and forming a ridiculous loop that swung as he walked. He asked to be excused three times until finally his mom told him that when he wasn't busy serving he should stand in the corner with his hands behind his back, waiting to be called on. So he stood there, oozing precum while the ladies drank and chatted and ogled him.

That night in bed he put serious effort into removing the device for the first time. Perhaps if he hadn't been so swollen with arousal he could have gotten it off, but he stopped when he felt that he was sure to injure himself.

The next day in school he discovered to his horror that the front of his pants had a wet stain. His panties were barely visible through the thin, dampened fabric, but the pink of his cage was unmistakable.

He did his best to cover himself with a textbook until he tracked down Abi and showed her.

She pulled him silently into an empty classroom and told him to stand with his hands behind his back.

"Don't move," she instructed.

Then she sat up on a desk and reached her hand inside her skirt. He realized she was going to masturbate in front of him.

"Does my little boy want to tell me what's wrong?" she asked with relish.

Quinn understood that she was getting off to his suffering, and that his role was to help her, but in a very real way he also just wanted to explain the problem and understand if there was something wrong with him.

"Last night my mom made me serve her friends cocktails. And I wore the skirt you gave me. And her friends were making fun of me and then I started leaking. I guess I just have too much cum and it's flowing out now? Abi, seriously can you help me? Is something wrong?"

"All boys dribble out of their cage when they've been in chastity for too long." She spoke in a matter of fact tone at first but then switched to a playful one. "I kind of like the fact that it makes you like a girl. Now when you're aroused you don't have an erection, you just cream your panties."

Quinn groaned as his cock began expanding to fill his cage uncomfortably.

She savored his frustration as she continued. "So what's the problem then? Do you not like the clothing I've bought for you?"

"I like it."

He could hear her fingers rubbing against her slippery flesh. It was the first time she had ever touched herself in front of him.

"How does it make you feel to be on display like this?" She gestured at his crotch.

"Weak. Humiliated. Powerless." He answered.

"Do you like the fact that I'm touching myself because you're suffering. Does it turn you on to be dominated like this?"

"Yes," he admitted quietly.

"When you look in the mirror, when you're wearing your little pink cage and your stockings - do you look like a boy or a girl?"

"I look like a girl."

"But you like the way girls look, don't you? You like their smooth skin, their cute clothes?"

"Yes."

"Does it turn you on then? Looking at yourself in the clothes that I make you wear?"

"Yes," the word sent a spasm through him as he admitted it.

"It sounds like you should be thanking me then."

"Thank you."

"Thank you for what?"

"Thank you for putting my cock in a little cage, and dressing me like a girl, and denying me until I leak all over myself."

"Fuck I'm getting close."

"Abi, please," Quinn hesitated because he knew he was on uncertain terrain. "Please let me taste your pussy. I'm sorry for before but I'm ready now."

"Fuck. Say it again."

"Please let me taste you just once. I, want it. I need it," He inched closer to her.

She shook her head. "No, you don't get to lick me yet. But you can kneel here and suck on my finger while I cum. Would you like that?"

He nodded quickly.

She pulled out the finger that had been buried in her pussy and offered it to him. He took it inside his mouth. It tasted like all the nights he had rolled around in sexual torment. It tasted like insufferable pleasure. And he was starting to like the taste.

"I think your wet patch is growing." She mused between breaths. "You must really like watching me cum while you drip in your cage?"

He nodded.

"Beg to watch me cum then."

She removed her finger from his mouth long enough for him to speak.

"Please let me watch you cum. I want to see you enjoy all the pleasure that you won't allow me to have. Please cum in front of me Mommy."

At the word 'Mommy', Abi bent forward and began convulsing. Quinn was in awe of her. The pink flush on her cheeks, her parted lips, the sweat on the curled hair of her temples. The way she was wracked with so much pleasure that she looked as if she was in pain. He wanted nothing more than to be the one that made her feel that way.

He watched her first orgasm subside only for a second to take its place. She shook under its force. When her body finally steadied, she was panting.

She held out her fingers and Quinn licked them clean one by one.

"Good boy," she whispered between gasps. "From now on, no matter who is around, I want you to call me that. Because it's true. I'm your Mommy now."

***

During the next two weeks Quinn became a fixture around Abi's home. He showed up early in the morning to make breakfast for the household and he came after school to do chores and cook. Abi's sister Grace would often join him in the kitchen, reaching under his skirt to grope his ass while their mother laughed, and their father made himself scarce.

Grace loved to dawdle beside him while he worked in the mornings. She would wear shorts and a tank top and say how her clothing felt so masculine whenever he came over.

Grace and Abi both loved it when Quinn called her "Mommy" in front of them. Abi would demand it just to make Grace laugh, and then Grace would tease him about it later.

"Is our new servant girl going to go upstairs now and ask if she can lick her Mommy's pussy?"

Quinn reacted by simply by blushing.

One morning Grace came down the stairs carrying a gift box and presented it to Quinn. He undid the ribbon warily and found a French maid costume inside.

"Umm, thanks, Grace. That's very thoughtful of you."

"I thought our little servant girl should get a proper uniform. Why don't you try it on?"

"Maybe I should ask Abi first?" Quinn tried to delay.

"She's still in the shower. And you're not done cooking. Just be quick and put it on for me."

Quinn slowly unbuttoned his blouse and dropped his skirt, not daring to make eye contact. Grace bit her lip as she looked on. Quinn tried to preserve some modesty by rushing to get the maid uniform on, only to find that he couldn't get the skirt to cover much lower than the very tip of his pink cage.

"It's just what I was hoping for. Why don't you run along upstairs and show Abi."

Quinn walked up the stairs with Grace trailing, cognizant that she could see anything she wanted to from beneath his skirt.

When he knocked on the door Abi almost fell over laughing.

"It's perfect. It's perfect! You'll have to wear this for me every morning! Mom, come look at Quinn you're going to love this!"

On a more typical day, when he finished cooking, Quinn would bring Abi her eggs and toast and help her pick out her outfit for the day.

Abi treated him during those moments as just another female friend, even though she knew that the sight of her in her underwear as she held up different sets of clothes wreaked havoc on Quinn's sex-addled brain. And so she acted oblivious as he ogled her breasts, studiously noting to herself which style or color of bra seemed to distract him the most.

While she loved the attention he paid to her body, she also appreciated the strange trust that was growing between them. Different from when they were lab partners of course, or even friends. Sort of the respect that a doting servant might have for his mistress.

One Saturday morning she was lying on her stomach on the bed, still in her underwear, when Quinn walked in. She was reading a book, some novel he had picked up for her. He looked longingly at the shallow valley running down the center of her lower back. Abi's hair was still wet, and there were gray spots on her white panties from the droplets that she had missed toweling off.

He set the serving tray on her bedside table and used the moments of her distraction to admire her body.

"Mommy?"

"Yes?"

"You look so sexy today."

She turned another page without looking up. "Oh, you like my ass, do you?"

Now that he had to refer to her as 'Mommy' it felt out of place saying complicated sentences. The very word seemed to force him into a dumb, submissive tone.

"Yes, Mommy."

"Is that so? Does that mean then if I offered to let you lick it, you would accept?"

She stopped reading but didn't look up from her book, pretending to barely register his response. Her words hung in the air while a fan droned in the background.

"Yes, I would. Yes please."

"Go ahead then," she said nonchalantly.

Carefully he got up on the bed, straddled her legs and leaned forward. He kissed the curving skin of her ass right where her panties ended. Then he shifted to the other side and licked her skin there.

"When I said lick my ass, I didn't mean my cheeks."

The words came out of her without thinking. She barely knew why she said it. She had never wanted a man to lick her there. In truth she thought it was disgusting. But apparently some malicious part of her still wanted to punish him. To dominate him. If it was disgusting, then Quinn ought to do it for her.

He trembled above her. He had turned down a similar offer once and regretted it ever since. He couldn't make the same mistake again and they both knew it.

He gingerly stretched her panties to the side and licked her cautiously. Then he forced himself to do it again, but deeper. And again. Deeper.

At first Abi was nervous. Would he hate this? Would he hate her for it? She didn't like to admit it, but when she had rejected him before it had hurt her pride and now she was taking a bigger risk. But as he continued, she found herself forgetting what was happening and just enjoying the novel sensation.
<hr pg="4" />It tickled. It felt vulnerable. It felt good. She moaned. Loudly.

"Fuck."

Encouraged by her reaction, Quinn began licking more intently.

Abi could feel his cool saliva running down into her pussy. She slipped her hand under herself and began humping it, pushing her ass up into Quinn's face and then back down against the heel of her palm.

Quinn was at first too shy to touch her anywhere else with his hands. But he took a risk and began rubbing her legs. When she didn't protest, he moved up to her ass, groping her as he devoured her with his tongue.

"Fuck, I can't believe you're eating my asshole. You're being such a good boy for Mommy. Now I know you'll do whatever I say."

Quinn moaned helplessly. She felt him rub his cage against her legs. It was wet with his precum.

"No cummies for little boys. Only Mommy gets to cum. I'm going to have enough orgasms for both of us." She grunted the words out as she continued grinding against her own hand. "Are you going to help Mommy cum? Are you going to help me like a good little boy?"

Quinn was too busy to respond. He felt like an animal, no longer in control of itself, thrashing in his cage and hungry only for one thing: the pussy that was inches away and still denied to him.

"Fuck, Mommy's cumming. Don't stop. Don't stop."

For the first time, Abi squirted as she came. Quinn heard it but didn't know what was going on, and Abi was too preoccupied to notice anything other than the fact that it felt extra good and extra wet.

Eventually she rolled over and looked at Quinn, who couldn't bear to look back in her eyes.

She knew she had almost broken him. She stood to go back to the shower.

After she returned and Quinn had changed her bedsheet, she handed him something.

"What is this?" he said, holding up the thin cotton pad.

"It's pantyliner. For your leaking. I think you've earned it."

Experimentally he slipped it into his panties, feeling confused by the mixture of embarrassment and warmth towards Abi for thinking of him.

***

The girls sat around the lab bench while their latest victim struggled in his bonds. Today's class was on tease and denial. The goal was to always have at least one hand touching the man's genitals at all times, but to not give a single orgasm during the 45-minute class.

"So it sounds like you've turned him into the perfect toy?" Willow asked Abi.

"Yeah, he does whatever you want, he's a good cook, you can humiliate him and he doesn't get grouchy," Charlotte created a mental list, "Is he good at pleasing you?"

"I still haven't let him," Abi said as she traced circular patterns around the tip of the volunteer's engorged, purple head.

"Here, let me tie him up, he's gonna need some help to make it to the end of class." Willow leaned forward, intentionally smothering the boy's face with her voluminous breasts, and tightened a shoestring around the base of his shaft. The girls watched as his rod became even harder and darker, the veins popping like some alien horror.

"So when are you going to have us over to your place? I thought when you became a keyholder we'd all get to have a little fun." Charlotte punctuated her remark by rapidly pumping the throbbing demon five times and then slapping his balls twice - a move which she referred to as a 'testicular reset'.

"Soon! I promise," Abi responded.

"Just after you've fucked his face yourself first, huh?"

***

On the day that Abi invited herself over to Quinn's home, it had been two months since Quinn went into chastity, and two weeks since the last time he had been released for an inspection. As was often the case, his mother was out late.

Quinn made dinner and cleaned up while Abi went into the bathroom and reapplied her makeup.

She re-emerged looking absolutely stunning. She wore a tight, dark blue dress that barely contained her cleavage and clung to her flat stomach and legs while pearl earrings and dusky eyeshadow made her the image of twilight personified.

She took Quinn by the hand and guided him upstairs. She had been to his room before, as a sort of inspection, but this time she walked right past his door and instead opened his mother's.

"I'm not supposed to go in there," Quinn said as he watched her open it.

"Quinn, who is your Mommy now?"

"You are."

"Good. Come with me then."

She sat him down on the stool in front of his mother's vanity and pulled up an armchair which his mother kept in the corner.

"I want you to know that I'm not planning on doing this all the time." She said as she grabbed his mother's makeup kit off the table. "Maybe on special days like this one. It's just that I've already forbidden you from touching yourself. Or having an orgasm. I've emasculated you so much, I can't resist taking it one step further. Now stay still for me."

She found it somewhat difficult to apply makeup to someone else, but by the time she was finished she was reasonably happy. It wasn't excessive, just enough to make his eyes pop and his cheeks blush. Then she rummaged through his mom's closet until she found a short summer dress and put it on him. He easily passed for a flat-chested girl with a pixie-cut. A cute one at that.

"Now I'm going to take you out of your cage. But I don't trust you not to touch yourself, so we're going to use these," and she brought out a pair of velcro cuffs on thin gold chains. She passed the chains through the loop on the front of his collar so that his hands were restricted from moving any lower than his chest.

When she was finished, she finally unlocked him.

Setting the cage down on his mother's vanity, she watched as his erection rose gradually before her. She noticed the chains go taught as the instinct to touch himself caused him to pull against his collar, and she smiled inwardly. She pulled his baby blue panties down and behind his smooth testicles so that they supported them and pushed them out lewdly.

When he was as hard as she could expect, she reached for a thin red ribbon sitting amongst his mother's hairclips and tied a bow around his penis so that it throbbed and grew dark for her.

Then she sat at the edge of the bed and indicated that he should sit on his own feet just in front of her. Carefully, so not as to give too much stimulation, she lifted the skirt of his dress and dropped it above his erection. Looking down at him she smiled at her handiwork: a cute dewy-eyed girl stared up at her, hands restrained, with a helplessly throbbing hard-on.

She found a reflection of the scene in his mother's full-length mirror and paused to pick up her phone and record a video. It didn't even occur to Quinn to object.

"I don't want you to speak anymore tonight, do you understand?"

Quinn nodded.

"Tonight, I'm not going to ask you for anything, I'm just going to take what I want. After tonight I will continue doing the same. You are going to become so used to licking me that I will merely have to lower my eyes in the direction of my pussy, and you will kneel and service me. I am going to fuck your face so often that it will become second nature to you. And still, I expect you to always be eager for more. I want you to be more desperate to give me my next orgasm than I am to take it. Even when we're with my family or friends, or out in public, I want you on the constant verge of begging me for another taste of my pussy. And if you're not, then I will keep you locked up until you are."

She pulled her skirt up higher so he could see her black, lace panties.

"I'm about to show you my pussy for the first time. My pussy is your new master. Everyday when you wake up in the morning, I want you throbbing and aching because you spent all night dreaming about how to please it."

Quinn was trembling on the ground beneath her as she spoke.

"Boys are never good at licking pussy their first time. But if you fail to please me as I want, I will punish you. And I will keep punishing you until you get it right."

She glanced down and saw that Quinn's cock had already leaked to the point of forming a small puddle on the hardwood.

She smiled again.

"Go ahead then. Worship my pussy."

When Abi pulled her underwear to the side Quinn gasped. The glowing pink of her skin, the flower of her youth, the gleam of the wetness on it in the dim lamplight - it overwhelmed him.

Quinn leaned in immediately and she had to stop him.

"Start slowly." She said it as a warning, as if he was already close to failure.

Chastened, he held himself back, kissing her calves, her knee, her thigh. Sucking on her leg so that he left a trail of little red marks on the way to her innermost place.

Then finally he allowed himself to lick from the bottom of her slit to the top. But the taste activated something primal in him, something she had trained, and he plunged his tongue as deep into her as he could. He sucked her labia and clit into his mouth and moaned in his own pleasure.

She grabbed him by his hair and stopped him. "Slowly." She paused for emphasis. "I want you to make gentle circles starting here. So I can barely feel them. You can increase the pressure later when you hear me start to really moan. Good that's it. Open your mouth and put your whole lips on my pussy, I shouldn't even see your tongue working. Better."

Now that he was finally bringing her some semblance of pleasure, she took a minute to savor the sight of it. His feminine face, with his naturally long eyelashes, now accentuated and darkened, his striking blue puppy-dog eyes looking up at her, searching for her approval with his mouth latched on to her flesh.

"Good girl," she said. It was the first time she had ever said that, and Quinn felt his head spinning.

"You're making Mommy very happy," she cooed as she squeezed Quinn's face together between her thighs.

Quinn watched her breasts heaving in her dress and would have reached out to hold them if his wrists were not cuffed to his own neck.

"I'm so glad that I own your little cock. I love how hard it is for me," she looked at the side mirror as she spoke. "I don't think I've ever seen a cock that hard in my life. I know you can't see it, but it's dripping so much I almost thought you had an orgasm. I am going to own that cute little piece of meat forever. I'm going to keep it safe in its little cage where it belongs. And I will only ever let it out on special occasions. But never to orgasm. I'm keeping all that cum in your balls. If you want to let some out, you'll just have to keep leaking in your panties."

She watched his cock jolting in the mirror.

"You must be practically frantic hoping that I'll touch it. Maybe even just by accident. But I won't. After all, the only reason your cock exists is to make you so horny that you'll do whatever I say."

Quinn moaned into her pussy.

"Hmm it vibrates when you moan. I like that. Fuck, that's nice too. Keep going like that. Faster, yes. Oh God." She began squeezing her legs rhythmically as her orgasm approached. Quinn was lost in the feeling of having his head trapped between her soft thighs and though he struggled to breathe he continued as best as he could.

Abi cried out, gripping the sheets with her hands and pulling them toward her and she collapsed backwards onto the bed as she climaxed. Quinn kept licking until she pushed him to the side with her thigh. Then he crawled up beside her, hoping that she might be willing to cuddle, or if he was lucky, perhaps touch his aching member. But he had misunderstood completely. She was not happy with his performance.

"I need you to get up now and go to your mother's vanity," she said to him, her business-like tone returning as she rose, upset that he had interrupted her. "Remember, no speaking. Good, now bend over and put your face against the wood and stay there.

She took another minute to collect herself, enjoying the slowly receding emotions and sensations from the first time someone had gone down on her.

At last she spoke. "What you did tonight was to try and give yourself pleasure with my pussy. You were aiming to satisfy your need for sex and so you failed your new master." She got up and walked toward him as she talked. "You have two punishments. The second punishment will happen later tonight. When your mother comes home, you will still be wearing exactly what you have on now and you will explain to her why there is a puddle on the floor and why there is a stain on the sheets," and she pointed to the wet mark that she had made herself.

"And the other punishment you will take now." And she picked a hairbrush off the vanity.

***

Three weeks passed since that night, and things had mostly gone according to plan for Abi. It was then that she finally relented and sent Quinn over to Willow's house, bearing a small envelope.

When he knocked at the door that evening, he didn't know who to expect and was surprised to recognize Willow standing there. Her shoulder-length brown hair was curled in long tresses and she wore a short skirt and tight cardigan. With her large glasses she looked every bit the part of a sexy librarian. Quinn had always admired her smarts, and seeing how attractive she looked this night he couldn't help but wonder how life might be different if he had asked her to be his keyholder instead.

"I like your outfit," she said to him. "Very cute."

"Thank you," he replied self-consciously, tugging a little at the hem of the polka-dot dress that Abi had chosen for him.

"I hesitate to ask, but your lips look so full and shiny -- are you wearing lip gloss?"

"Yes," he said again, bashfully.

"Well it's subtle. The eyeliner too. The dress... not so much. Why don't you come in."

"I brought wine," Quinn said as he handed her a bottle from a bag.

"Oh thank you, let me pour us a glass."

Willow returned with her family crystalware and then ushered him into her living room. The house was quiet. Willow sat on a sofa and gestured next to her. Quinn sat with his knees together and his hands in his lap.

When she offered him the wine Quinn took a sip and felt the burn behind his ears. He wasn't used to drinking.

"So what did Abi tell you about tonight?" Willow asked.

"She said that I am to follow your orders and she sent me an envelope," he produced it as he spoke, and she took it from him.

"That's all?"

"Yes."

"Abi tasked me with a rather difficult conversation," Willow began. "She suspected that I might be the more appropriate messenger for this, and I tend to agree."

Quinn nodded and gulped down more wine.

"Quinn, how would you regard Abi? What position does she have towards you?"

"She is my keyholder."

"Right. But a mother can be a keyholder. So can a wife. What is Abi?"

"Well she was my friend. We've never really talked about it but she doesn't spend time with other boys," he looked at his skirt and then looked away as he said this, "so I guess we're kind of like girlfriend and boyfriend."

"That's a pretty natural way to interpret things." Willow agreed. "Most of our classmates who are keyholders for someone outside of their family are keyholders for their boyfriends. They date a boy for a year or two and then maybe a mother will give them her boy's keys. You and Abi go to the same school, you asked her to be your keyholder, just as many guys might ask a girl to be their girlfriend, so you could say that she is your girlfriend, even if you haven't officially phrased it that way."

"Yeah, plus we umm... well we have sex."

"You go down on her all the time, right?"

"Exactly."

"But we should maybe think this through more. I'm worried that you've gotten caught up in a bit of a fantasy. I know this isn't easy to hear but let me ask you some questions. Does she ever let you cum?"

"No, not exactly."

"What do you mean, not exactly. Oh, I can see you tensing up. You don't have to be shy around me, I've seen it all. We women are used to talking about this kind of thing even if you're not. Did she give you a ruined orgasm?"

"Yes."

"How many times?"

"Just once."

"Does she like to tease your cock? Does she play with it every few days?"

"No not really. Sometimes she lets it out of its cage. But she'll mostly just look at it. She'll tease me with what she says, like she'll say, 'Isn't it too bad that there's no one who will touch your poor lonely cock' but then she'll put it back."

"Okay and when you go down on her, does she take off her top? Does she let you suck on her breasts?"

"No, I've never seen them actually. Except in a bra."

"Wouldn't you like to see them? Wouldn't you like to touch them? Most guys love boobs."

"Yes, but she's never offered. And I'm too afraid to ask I guess."

"Surely she knows you want to see them? Don't you think she sees you staring at them?"

"I guess so. I'm sure she has her reasons."

"Do you think that's normal girlfriend behavior?"

"I guess not."

"And your outfit. You didn't dress like this before, did you? She chooses what you wear now?"

"Yes."

"Do you know why she dresses you up like a girl?"

Quinn paused.

"I think she likes forcing me to embarrass myself. But I also know she's more turned on by women, so she makes me look like one."

"What makes you think that? Be honest, this is important."

"Well there's a few things." Quinn took a deep breath. "For instance, one time, she let me out of my cage. And before I could get hard, she used medical tape to tuck my cock between my legs. She had me in full makeup that time and dressed me up like a ballerina. She tied my wrists behind my back and then tied them to the door and she let me try and hump a chair, which was just out of reach. Then she masturbated while watching me. She came four times. I've never heard her scream that loud."

Willow's eyes were wide, she hadn't heard that story.

"Alright, so you think she likes watching a girl try to masturbate more than a boy. You mentioned you perform oral sex - how often do you do that?"

"Everyday. More than once a day."

"Is it true that she makes you get up early so that the first thing she feels in the morning is your tongue on her pussy?"

"Yes, that's how I wake her up."

"Okay. Let's think of other models for relationships in your life. Does your mom have a boyfriend? Do you know what their relationship is like?"

"She has men over, but only ever one night at a time."

"I guess you don't know what they do then."

"Actually... I watch. She always stays in the family room with them. There's a corner at the top of the stairs where I can see them."

Willow realized this was maybe the most shameful thing he had told her yet.

"And what do they do?"

"She makes them put on a strap-on harness, and then she lets them fuck her."

Willow knew she shouldn't ask, but she couldn't help herself. "And when you watch this, do you get wet... in your panties?"

"Yes."

Willow stifled a gasp and decided to move on quickly, "Well regardless of how you feel about that, it is definitely one way that lovers act. When a woman doesn't have a man's key she might make him wear a toy. Is that something you do with Abi?"

"No."

"So thinking about how girlfriends and boyfriends normally behave, yes girlfriends often order their boyfriends around, but they also do nice things for them right? Pleasure them sometimes and so on. And then thinking about how you and Abi behave, would you say that you are closer to being her boyfriend, or closer to being her sex slave?"

Quinn was speechless.

"Because looking from the outside. I think you're actually closer to being her sex slave. A couple of nights ago when we all went for dinner, I heard you whisper to her when you thought you were being quiet. You were pleading with her, 'Mommy can I please, <i>please</i> taste your pussy.' You had already eaten her out at least once that day, and you couldn't even stop yourself from begging for more, in public."
<hr pg="5" />Quinn blushed furiously. "I'm sorry, I can't help it. I need it. I can't go ten minutes without thinking about it."

"Yes, because she's trained you. Listen, it's not just that I think you're her sex slave. It's what Abi believes as well. And that's important because Abi wants to use you in the way that you'd use a slave, and not a boyfriend."

She picked up the envelope.

"Do you know what's in here Quinn?"

"No." His tone was dejected.

She ripped open the envelope. "It's your key," she said holding it up. "Abi gave me this key because she is letting me borrow you. I'm going to use you. I'm going to ride your face, and make you pleasure me all night long. And because I'm not Abi and I don't have a weird aversion to bodily fluids, I'm going to torture your weeping cock until you beg me to stop. And, Quinn, it won't end tonight. Because Charlotte wants to use you too and so she's going to have her turn. And Grace wants to use you, and Abi doesn't mind sharing with her sister because she doesn't think of you as a boyfriend. And if some other woman asks Abi I think she'd lend you to them as well."

She paused to let him think but saw he was becoming too upset.

"Shh, shh, come here." And Willow grabbed him gently by the head drawing him down to her lap facing up. "I think this will make you feel better."

She unbuttoned her cardigan and pulled her immense breasts out of her bra for him. When she offered him her dark, puffy nipple, he latched on immediately.

"There's a good little girl. Now let me do something nice for you." Willow pulled his dress up, exposing his cage, and then slowly unlocked him while he suckled.

His cock gradually began to grow, and with two delicate fingers she encouraged it to its full size.

"Look at you. Absolutely soaking wet. I know part of you is quite sad to have this dream of dating Abi crushed. But I think most of you is nervously excited to have confirmation of what you always suspected. You're a little servant girl now and all you need to focus on is pleasing our pussies."

Willow anticipated that this might be a bit too much for Quinn to handle and withdrew her touch from his partial erection just in time to avoid a full orgasm. "Shhhh, stay still, don't thrash about, just relax. Let it ease out of you," she coached him and waited patiently as his muscles untensed and a slow trickle of cum spilled out of him. She caught it in the palm of her hand.

"Good, that's how good boys take their ruined orgasms. No messy spurting, just a nice steady stream. Here," she said as she spread the glaze on her nipple. "Clean that up for me."

Quinn obeyed, consoling himself on her teat.

"Now Abi wouldn't be very happy if she found out about your little accident, but I think you're still plenty horny and I'm sure that a few hours of teasing will have your balls completely refilled before you leave in the morning. This will be our little secret, okay?" She said as he continued swirling his tongue around her areola and she gently toyed with his still swollen balls.

"Do you like the taste?"

He seemed to be in another world but eventually responded with a nod.

"That's good. Let me feed you some more," and she grabbed the base of his cock, squeezing more cum out like toothpaste and then applying it to her nipple. "I have a theory that when men are in chastity they spend so much time thinking about their precious semen swirling around in their balls that when it's finally out they are far more inclined to like the taste." She weighed his testicles in her hand as if measuring the volume of liquid inside.

"It's sort of too bad you know," she continued musing. "I'm pretty sure that the natural progression of things was for you to become Abi's boyfriend. But she never forgave you for refusing to eat her out. That was your pivotal error. Or your good fortune. Who knows? Perhaps you'll like being a sex slave better than a boyfriend."

What would have been a shattering revelation only a few weeks ago now barely registered. Quinn didn't even look like he heard it. He was so far into a submissive state of mind that his brain was little more than warm goo, incapable of focusing on anything other than the taste of his own ejaculate on Willow's warm breasts.

Quinn continued until he could no longer detect the bitter, salty remains of his own seed at which point he began to recover from the disappointment of his almost-orgasm.

"Momm-" he began saying.

"You can call me Auntie."

"Auntie Willow, I'm sorry that I came without your permission. I tried to stop myself."

"That's okay dear."

"And auntie?" Quinn stared up at her with his big, pleading eyes.

"Yes," she responded, suddenly full of motherly concern.

"Can I please lick your pussy now?" his cock twitched and drooled as he asked, and Willow smiled at the endearing sight.

"Of course, dearie."

