A Pivotal Error Pt. 01

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.

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, hmmm fuck" 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, Oh God." 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.

Boys are so sensitive, 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?"

What could this be? 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..."

That explains a lot. 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.

This might not be so bad, 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 one 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?"