A Pivotal Error Pt. 02

Author's note: This story contains themes of femdom, humiliation and feminization. It's the finale of a two-part series taking place in a world of enforced male chastity.

"Does it feel good to be out? It's been a few weeks now."

"It feels so good Mommy," Quinn groaned.

"I'm glad to see your little tool still works. Sometimes I worry about it stuck in there for days on end."

Quinn was sitting on Abi's lap, naked but for his stockings and garters and uncaged for the first time in so long. His hair had finally grown enough for braided pigtails and he had two red bows holding them in place.

Abi wore a gray plaid skirt, a cute blouse, and a clean white headband in her blonde hair. In short, she was dressed like a cultured young woman, and the imbalance between her refined clothing and Quinn's nakedness only reinforced the power dynamic between them.

She was using this opportunity to run her hands over Quinn's body. His smooth legs, his soft, flat tummy, his hardened nipples. But of course she wasn't touching him where he wanted. Not there. It seemed like never there.

"So I noticed you borrowing my makeup."

Quinn froze.

"Do you like dressing up like a girl now? Should I push you to go further? I could make you wear only girls' clothes outside of the house."

"I noticed, Mommy cums harder when I dress like a girl," Quinn strategically answered only the first question.

"It's true. I'm glad you noticed. So you do it all for me?"

"Well I... I make my panties wet when I see myself in the mirror."

"Oh such a naughty girl." She stroked his hair and he blushed as a tingle passed down his spine.

"It's true that I like you better as a girl. I think boys are mostly gross, don't you agree?"

"Yes mommy."

"Why do you think boys gross?"

"We have ugly, veiny cocks between our legs, and we're hairy, and all we want to do is spurt our juices everywhere."

"But you're not hairy are you? You barely had any hair to start with and we've shaved everything that's left. And you have a nice sissy cock, all locked up and tucked away. Now you just leak like a polite little girl. Maybe one that's a bit too horny for her own good, but that's how I like to keep you. So you like being a girl for me?"

"Yes Mommy."

"If that's true I'd really like you to try harder. I don't want to catch you without makeup on in the house anymore. When I wake up in the morning I want the cute cheeks I see between my legs to be rosy with blush. I want you to be so convincing that if a stranger comes in they would never for a second suspect that you're a boy."

"Of course, Mommy."

"Tell me my sweet, are you happy to have me as your keyholder?"

"Yes Mommy."

"There isn't anything you would change?" Her hands circled ever closer to his groin, just barely making contact with his testicles.

He gasped.

"No, I'm very happy."

"I'm not going to ask you again for a long time, my pet. Be honest."

She stopped moving her hands to let him know that the fun was over until he answered.

"Sometimes Mommy likes to humiliate me."

"Yes dear, it makes me very wet."

"But sometimes it hurts."

"You mean it hurts your feelings?"

He nodded.

"I've noticed. You cry sometimes. But when I remind you about what we did later on you always get very tight in your cage, don't you?"

"Yes," he admitted.

"Let's make a deal then. If you say no to my offer, I will try and be kinder... less embarrassing. Does that sound good?"

He nodded again.

"Here is my deal. On my phone I have a few videos I've compiled together. There's the video of the first time you went down on me, wearing your mother's dress, with your precum dripping from your little cock. It goes all the way till I finished spanking you with that hairbrush. Then there's a video of you acting as a naked footstool at one of our parties. And the video of you in that ballerina outfit. My deal is this: for every female contact that you send those videos, I will play with your cock for ten seconds. But if you don't want any future humiliations, then you should start now by showing me that you care more about your dignity than you do about having someone play with the toy between your legs. If you show me that then I promise to be more respectful in the future. What do you think?"

She set the phone down in front of him and began rubbing her hands over his inner thighs.

Quinn thrashed around on her lap, needing her touch so badly.

"You can't make up your mind? It's too bad, I would very much like to feel that hard cock pulsing between my fingers," she leaned in and licked his ear as she spoke, causing him to tremble helplessly.

"What should I do my pet?"

She waited for an answer while his breathing deepened.

"Send it" he finally whispered.

Abi smiled. "Send it to who my sweet? Just Willow? Willow and Charlotte? That wouldn't give you very long. I have lots of women in my phone though. Women who may have noticed you wearing some eyeliner, or seen the panty line under your jeans. They might suspect something but this would be a real shock to them. Could you imagine, dozens of your female classmates getting this video. Showing each other? Laughing."

Quinn continued wriggling on her lap, but Abi's hand came no closer to his cock than before.

"Your mom is on my phone you know? I could send it to everyone. That would be a good long play session for you. You might even cum if I'm not careful."

Finally she wrapped her fingers around his cock. He took in a quick breath and froze, waiting for her to continue.

"Tell me. Tell me who to send it to so I can stroke your little toy."

"Everyone. Send it to everyone." His voice was a hoarse whisper.

"What a good girl. I think you made the right choice. No one will ever look at you the same again. As it should be."

***

"Abi, can you stay behind for a few minutes to talk?" Ms. Jones asked casually.

Charlotte and Willow gave Abi a puzzled look as they packed their bags and headed to their next class.

When the rest of the class had filed out Abi walked over to Ms. Jones.

"Did you want help with these two?" Abi asked indicating the two male volunteers who remained tied to their tables.

"Oh no, you can leave them. I sometimes ask the girls who have these two as volunteers to leave them tied up at the end of the class."

Abi gave her a quizzical look.

"What I wanted to say, Abi, is that I've heard about the boy you're keyholding for, Quinn?"

Abi nodded, unsure of where this was going.

"He seems like a nice boy - I've even seen him walking obsequiously beside you, wearing his little collar."

"I don't mistreat him you know, I'm not sure what other girls are saying," Abi began but Ms. Jones cut her off.

"What I was going to say is that I'm proud of you. From what I've seen from you in class, you never looked very interested in chastity. Your grades in other courses are excellent, and in mine they're mediocre. But some girls do better in the real world than they do in a classroom, and I think you're a natural keyholder."

"Oh," Abi was caught off guard. "Thanks I guess."

"I can tell that you probably don't have a normal relationship with Quinn. As in you're not dating or whatever. And I wanted you to know that it's fine for you to chart your own path. Some people wonder why I'm still single, but the truth is, I take what I need from men, and I don't give anything back. So I don't need a partner. Do you know why I have these boys tied up even though school is over?"

"You're going to make them lick you?"

"Abi, I wouldn't have chosen the two boys with the biggest cocks in the class if I was going to have them lick me. I'm going to use them like human dildos."

Just then the phone rang.

"One second," Ms. Jones said.

Abi strained to hear the conversation on the other end of the phone. It sounded urgent, but Ms. Jones only appeared annoyed.

"Shit," Ms. Jones cursed as soon as she hung up the phone. "Abi, I have to leave. It's not quite an emergency, but I don't have time to untie these miscreants before I leave," she gestured at the intricate knots that held down the two bodies in front of them. "Can you do me a favor and take care of them for me?"

Abi nodded.

"Or," Ms. Jones smiled deviously, "You can have them take care of you before you let them go."

And with that Ms. Jones turned and left the room.

Abi considered the situation. The two male classmates were blindfolded, gagged, and wearing headsets that were blasting white noise. She could do whatever she wanted with them, then when she was finished, untie just a single hand, and leave while they struggled to release themselves. They would have no idea who had used them. Most likely, they would assume that whatever happened was at the hands of Ms. Jones.

Of course, she could make them lick her, but why not take it a step further. Both of the boys did have impressive packages, even now that they were almost limp. She admired the larger one, picking it up and letting it fall, watching it twitch in response and come half to life. It was already bigger than Quinn was when he was erect.

What better time to try than now?

Thinking things through she brought out her phone and typed out a message to Quinn.

Come to Room 129. Close your eyes and then knock before entering

Quinn would already be on his way home, so he wouldn't arrive for another five minutes.

Decisively Abi went over to the boy with the slightly smaller, more manageable dick, and began massaging it back to life. He was incredibly responsive and soon she was stroking a rock hard shaft.

She pulled her panties down and found to her surprise that they were already wet. Then she climbed on the boy, hiking up her skirt around her waist before pausing briefly.

"Here goes nothing," she said to the room.

As she pushed the boy's penis inside her she mentally compared the experience to playing with her dildo. It was warmer, slightly larger and more textured. There was something indescribably sexy about having a responsive being underneath her like this. The boy gasped as soon as the head of his cock felt her wetness. She watched the muscles on his hip and legs contract as he tried to push upwards against the ropes.

"Fuck this is hot," she whispered to herself.

She gradually acclimated to his cock, pushing herself down until she felt him press against her cervix. Then leaving him there she simply rocked her hips back and forth, savoring the fullness and allowing her hands to wander over her body.

Even though she was barely moving she saw the boys face change rapidly and felt his body spasm beneath her.

"Fuck, you came already," she said to the presently mute and deaf body beneath her.

Just then she heard a knock at the door and smiled to herself.

"Come in quickly," she ordered. "And eyes closed!"

Quinn cautiously entered the room with his eyelid firmly sealed, feeling his way forward by the sound of Abi's voice.

"Good... to your left... watch for the table".

When he finally arrived at her desk she dismounted, plugging her hole with two fingers.

She wanted to keep Quinn in the dark for as long as possible. She guided his face down between her legs,

"Stick your tongue out," she said as she aimed him right at a white rivulet running down her thigh.

He licked, expecting to taste her pussy juices, and then looked puzzled when he didn't.

"I want you to just plant your open mouth on my pussy" she instructed, smiling because he hadn't figured it out yet.

Carefully he moved up until he felt the familiar contours of her vulva. She removed her fingers just in time for his lips to seal around her and then she held him in place as she felt a glob of cum roll out of her.

Quinn recoiled, perhaps he had figured out the taste, or just found the change in consistency unexpected but she held him in place.

"Be a good girl and swallow the meal Mommy has saved for you."

She watched as Quinn relaxed and then the muscles on his neck contracted, as if he was a patient, reluctantly swallowing a large pill.

Abi had often looked on as Willow and Charlotte forced boys to eat their own mess in chastity class. She had seen their eyes wide in fear, and watched them struggle to keep their mouths shut as she herself had sometimes helped by holding their nostrils closed until they finally yielded. She remembered asking once how it had tasted, and the boy describing his own juices as thick, salty, and gross. She wondered how it tasted to Quinn.

"Good girl. You can open your eyes now."

Quinn's eyes went wide, and he looked left to right, perhaps discerning the boys still tied on either side of him while his mouth remained clamped on Abi's labia.

"Do you like your dinner?" Abi asked.

Quinn nodded unconvincingly.

"Good. Then I'll work on getting you another one right away!" she grinned and guided him by the hand over to the other table.

She circled the table first, running her hands over the boy's flesh and the ropes that tied him down. She wrapped her fingers around his testicles and squeezed so that the skin went taught and his veins popped into focus.

"I think it's so hot that at this very moment his balls are full of cum, and in a few minutes that very same cum will be inside your tummy," she said as she placed her other hand on Quinn's stomach.

Quinn swallowed as if foreshadowing what was to come.

She climbed carefully up on the second boy. Grabbing a bottle of lubricant next to him she squirted his half-mast member and began stroking it to its full length. She'd need all the help she could get fitting this one inside her.

"He's so big Quinny. He's the biggest in the school. We've measured them all you know."

She looked down at the boy's rigid pole, satisfied that it was as large as it would get.

"Why don't you kneel there, next to my legs and I'll call you when you're needed."

Quinn knelt where she pointed.

Abi held the young man's tool in place and prepared to impale herself on it.

"Quinny, I've got to admit, I'm a little nervous. Can you hold my hand."

He reached out a shaky hand that met with hers.

"Thank you Quinny."

With her other hand holding the cock in place, she parted the lips of her soaking pussy with his head and then allowed her weight to bear her down.

"Fuck," she cried out as she took the first few inches.

She pulled back up before repeating the process, going slightly deeper. Three times she did this before she finally slid all the way down, feeling her insides rearrange to accommodate the phallic intruder.

"Oh my God I feel so full," she cried out.

As she slowly grew accustomed to the girth inside her she sped up her pace and while she rode the young man's obscenely large member she toyed with Quinn mercilessly.

"Do you wish this was your cock that I'm riding."

"Yes" he mumbled.

"Why do you think I don't use you like I'm using him? I could fuck you every night if I wanted to."

"Because my cock isn't like his."

"No it's not. What's different about it Quinny?"

"Mine is much smaller."

"Tell me I deserve a big cock."

"You deserve a big cock," he whined.

"Fuck, I'm coming," she called out as she squeezed Quinn's hand with a vice-like grip.

"Oh my God, I rarely cum from just penetration. That felt so good." she gasped. "And he's still hard. Stand up Quinny, I want you to play with my clit as I fuck him again."

Quinn positioned himself slightly behind and to the side of her so he could reach his hand down to her crotch. She was a sodden mess, but her clit was so engorged that it was easy to find. He rubbed it in time with the movement of her hips and she ground them against her captive.

The second orgasm was easy to coax out of her and when she finished, panting, Quinn thought she would be done, but she only murmured, "Again."

The ropes on the young man had loosened slightly, just enough for him to move his hips a few inches, and so this time Abi leaned back and allowed her human dildo to fuck her.

Abi unbuttoned her blouse and let it slip to the ground. Then leaning back she rested her elbows on the boy's legs and opened a large space between them. She relished the feeling of Quinn's eyes on her body. Fucking her shackled classmates hadn't been as fulfilling as she thought it would be until Quinn's adoring eyes were there to give the act consequence.

She quickly grew tired of this position and straightened out. "Undress. I want to hold your balls while I fuck him," she ordered.

Quinn quickly stripped down so that his only covering was the small, pink chastity device. Abi would normally refuse to touch him when he was so drenched in his own precum, but she seemed less concerned than normal and reached out to fondle his testicles.

"Do they hurt?"

"Yes Mommy."

"They must be so full for me. They're overflowing onto my hand," she stuck her fingers in his mouth as she continued to grind on the cock buried deep inside of her.

"Fuck I want to cum one more time before he finally finishes inside me," she slowed her rhythm to a slow grind as she spoke. "But I need your help to get off now Quinny. I want you to kneel again like a good girl."

"She reached behind her back and began unclasping her bra," Quinn could feel his pulse beating in his temples.

"Now look down now at your cock. Not just a little, try to touch your neck with your chin."

Quinn adopted the severe posture so that he could no longer make eye contact with Abi.

"Alright, now I'm going to take off my bra and drape it on your cage and you will keep your eyes looking straight down."

Quinn heard her undo her clasp and then saw the bra descend on his cock. The fabric between the two cups was right on the base of his cock, where his skin bulged before the cage prevented his blood from flowing in. He knew now that all he had to do was look up and he would see Abi in all her glory.

"I know this will be tough for you Quinny, but I want you to keep your eyes down. If you look up I promise I won't punish you at all. But i want to know that Mommy can trust you to obey me. So don't disappoint me sweety."

Quinn started shaking, staring at the bra as it dangled from his imprisoned cock.

Abi did her best to put on an aural show for him. Breathing raggedly, she renewed her attack on the boy beneath her, fucking him so that the sound of their skin slapping together filled the room. She kept waiting for Quinn to look up, but his head remained tilted down. She ran her fingers through his hair but he did nothing more than shiver.

"Oh you're such an obedient girl, listening to Mommy fuck but not watching her. It must be unbearable for you," Abi teased him between breaths. "Look at that long strand of precum hanging off your tip, it's almost as long as my bra. Fuck Quinny I wish you could see my boobs right now. How they lift every time I rise up and then come down every time I skewer myself on him. Tell me you want me to cum again."

"I want you to cum on his cock, Mommy."

Abi loved when he embellished her dirty talk like that. She felt so sexy, fucking this boy while Quinn knelt on the ground, denying himself the pleasure of staring at her not from coercion or fear but because he was enamored with her. She wanted to stretch her power further, to push him to his limits.

"Would you give up your touchy time if it let Mommy have a third orgasm?" she asked.

"Please, Mommy, it's been so long."

"You wouldn't do that for me baby?"

Abi had lost count but it had been almost three weeks since his last release from the cage, and she had promised him a teasing session that very night.

"Please Mommy, I can't take it."

She could see his flesh filling up every nook and cranny of his cage, searching for some escape.

"Oh Quinny, I'm getting close, please say it," she pouted. "You know it will turn me on so much to hear you deny yourself."