A Pivotal Error Pt. 02

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Quinn wriggled again.

"If Auntie Willow wanted to fuck your face, she wouldn't need you to ask," Abi added.

"But maybe I like hearing it anyway," Willow giggled.

Abi reluctantly nodded her approval.

"Please Auntie Willow," he began, "I'm still so horny but nobody will even give me a ruined orgasm. Let me at least taste your delicious pussy one more time."

"Oh, I think our little girl just wants her cummies," said Willow as she flicked the head of his cock so that it listed to the left and then bobbed back up. "No more pussy for you tonight."

"And no more speaking either." Abi said before leaning in and whispering in his ear, "You did well though. Mommy is very proud of her good little girl," before fitting the gag in his mouth.

The young women chatted and drank wine for a while longer. Grace went upstairs to change and then sat back down in her chair, giving Quinn's wilting cock a few half-hearted pumps before reclining.

"So," Abi announced now that they were all present, "I thought to celebrate Quinn's first year in chastity, we could play a couple of games. The first game I'm going to need that double-ended dildo for," she said as she reached across the table while Quinn eyed her warily.

"So the game works like this," she explained as she removed Quinn's gag and forced one end of the dildo into his mouth. "I am going to ask a question to Quinn, and everyone has to write down their guess. You all received lipstick, you can use that to write your guess on whatever part of Quinn is closest to you. I know I'm scheduled to have Quinn all next weekend, but I'm going to give her up to serve the winner of the game."

"Oh my God," said Charlotte, "my room is such a mess, that would be amazing!"

"Oh I know," said Willow. "My dad is away this weekend though so we could really use someone to cook for us. Maybe you should lose on purpose for me Charlotte."

"Unlikely," Charlotte laughed.

"Okay, so our first question," Abi interrupted, "how many times did Quinn masturbate the day before she gave me her keys?"

"Oh, tough one, it's gotta be a lot right?" asked Grace.

"Unless she was already trying to be self-disciplined," said Willow.

"Hurry ladies, just a few more moments to write down your answers. Okay, Quinny, I want you to move your head up and down one time for every little cummy you made the day before you went into chastity."

Quinn nodded up and down, and the gigantic, flexible dildo bobbed with his mouth, bringing reams of laughter from the girls, who counted each one in unison until he reached five and then stopped.

"Oh my God Abi, she was like you are now!" Abi's mom joked.

"Looks like Grace is the only one with the right guess, so she takes the lead," said Abi. "Question number two: If Quinn couldn't have me as her keyholder, who would she pick as her second choice out of the women here?"

The girls recorded their guesses and then Quinn pointed the dildo at Willow, barely managing to avoid it slipping out of his mouth as he did.

"Too easy," Grace complained.

"Oh thanks Quinny," Willow said, massaging Quinn's testicles briefly in a show of gratitude.

"Question three: how many inches is little Quinn's cock when fully erect?" she then turned to instruct Quinn, "Quinn you can just sit still for this one."

"Oh this is tricky, I know she told me what it used to be but it's definitely shrunk quite a bit" said Willow as she reached out and began stroking him to his full length.

"Feel free to be extra precise so we can avoid any tied guesses," Abi instructed.

Once the girls finished she pulled a small measuring tape out of her bra and lined it up with the base of his cock. "4 and 1/4 inches," she announced.

"Oh not as small as I thought," said Charlotte.

"So Willow wins with a guess of 4.3, bringing her tied with Grace overall. Next question is, how many women has Quinn seen topless? And we'll let Quinn count it if she's at least seen both nipples."

The girls silently counted in their heads and then marked their answers on Quinn's increasingly colorful body.

"Go ahead Quinn."

Quinn bobbed his head, one, two, three times.

"Damn it, said Grace. "Okay so we know she's seen Willow," Grace said, "and I guess she might have had a good enough peak at Charlotte. Abi are you sure she hasn't cheated and seen you in the mirror or something?"

"No I think she's just counting her old mom," Abi said with a laugh. "We'll keep the answer though which means Willow and Charlotte both get points. Next question is a follow-up to an earlier question: If Quinn could pick the length of her penis, how many inches would she choose?"

"Oh my goodness, I have no idea," said Abi's mother. "Six? Just to be normal?"

"I was thinking one," said Grace, "just a tiny little microdick so she'd still have a clit for us to play with."

"What if she picks zero?" asked Charlotte.

"Well let's find out," said Abi. "Get your answers down ladies! Okay, Quinn so bob your head one time for each inch."

Quinn began bobbing and once more the girls counted in unison: "One. Two. Three. Four. Five. Six. Seven. Eight. Nine!"

Then Quinn finally stopped and the girls burst out laughing.

"Oh poor Quinny wants a big boy's dick," said Willow.

"More like a horse's dick," whispered Charlotte.

"One of us should put a big old strapon over Quinn's cage and let her pretend she's got a nine inch cock sometime," said Grace.

"Already have," said Charlotte. "Like the second weekend I got her I put this big realistic strapon around her waist. She begged me to stop because she said it was too much and she was going to come in her cage."

"That's so like Quinn," said Willow.

"Yeah I don't like letting her penetrate me, even with a strapon," said Abi. "I think it gives her too many ideas. But you girls are welcome to try it. I'm gonna do the next question now though. So, how many times has Quinn cried from a spanking given by any of us?"

"Poor little Quinny," said Willow.

"Don't act like she didn't cry after you spanked her," said Abi, eliciting some laughter.

"Quinn really does lick you differently after you spank her," Willow admitted. "She becomes much more tender."

The other girls agreed.

Once they were finished guessing Quinn bobbed his head three times, and despite his best efforts to do so in a dignified manner that might cause the girls to show some pity for him they could only laugh at the absurdity of the giant dildo lolling precariously in his mouth.

"Honestly girls, when cages first came into law most men I know cried more than three times in their first year from the spankings their wives had to give them," said Abi's mom, who generously refrained from calling the younger generation soft as she so often did at other times.

"Okay final question," announced Abi, happy to not encourage her mother to go on a historical tangent. "This one is worth two points to give the laggards a chance to catch up: How many women has Quinn kissed on the lips?"

The girls wrote their answers on the last unmarked skin of his body, with numbers ranging from one to six.

"Go ahead Quinny, give us the answer," said Abi.

Quinn remained absolutely still.

"Wait, does that mean she's never kissed a girl?" exclaimed Charlotte.

A silence fell over the group.

"Oh, not even little Janey boo?" Abi asked.

Quinn shook his head, and the silicone dildo with it. No.

"Holy shit, I thought she was just refusing to answer," said Grace, "I was about to slap her balls!"

"Is this the saddest thing we've found out tonight?" asked Willow.

"Yeah, it's pretty pitiful," agreed Charlotte.

There was silence for a moment before Abi spoke. "It is kind of sad. But at the same time, does anyone else think it's kind of hot? Like she's never kissed a girl but we've fucked her face dozens of times."

"Like we've taken her innocence?" Grace added.

"Yeah I know we all joke about her being our sex slave, or fuck toy or whatever, but she really is. We can do whatever we want to her and she just thanks us afterward," Willow said.

"I think if I had to put my finger on it, it's that I love taking things away from her," Abi mused. "I took her cock, and her orgasms and her dignity. I emasculated her. And now it turns out I took away her first kiss without ever realizing it. When she gave me her keys, she probably expected that first kiss was going to be with me. God that makes me feel like I need another round on Quinn's face just to cool down," Abi joked.

"Okay, let's find out the winner before you go and get too riled up," interrupted Charlotte.

"Fine," Abi conceded. "Willow guessed one on the last question, which was the closest, so she wins by a single point!"

"We should have made the game about ruining his cock instead of trivia if we wanted anyone but our resident librarian to win," Charlotte rolled her eyes as she spoke.

"Alright, now that we've announced our winner," Abi continued, "I want us to all go around the table and share one story, preferably a funny or embarrassing one, about our honored guest!"

"Oh, can I go first?" Grace raised her hand like she was in class.

"Yes Grace, go ahead."

"Alright. Three weeks ago everyone happened to be out of the house except Quinn who was staying in to keep up on cleaning. And I was going to a housewarming party and made it all the way there before I realized that I had forgotten my gift. So I had to go all the way back and it probably took me an hour. When I came in I didn't hear the vacuum going, or the dishwasher or anything so I peaked into Abi's room to see what Quinn was up to. She was applying Abi's makeup in the mirror, and was wearing one of Abi's bras stuffed with socks. And the funny thing was, when I saw her, she screamed and covered up her 'boobs' like she was some girl actually afraid of being seen. I cried laughing."

"Is that when you got the idea for her fake tits?" Charlotte asked.

"Yes exactly. She clearly wants them! Besides, I think it will drive her mad being able to wear them to bed, just groping her own boobs while her cock struggles in her cage. It's just delicious. Speaking of which, Charlotte, can you tell us the story of how you ruined her orgasm?"

"Well Abi already knows but I'll tell it fresh for the rest of you. This was like the third or fourth weekend that Abi let me borrow Quinn. At this point, we've already done all the fun games and my only priorities were for her to get me off and clean the house. So it's the Saturday morning, and I had kept her quite busy that night. I had her cage off the entire time though, she was just restrained from touching. Basically, she spent the night looking like how she looks now," Charlotte paused for a sip of wine.

"Anyway, she's busy doing dishes and I'm just leaning against the counter eating the breakfast that she made, wearing only a long t-shirt. Now I was already satisfied and at the stage of wanting her to lick my pussy just because I can make her. Not even wanting to cum, you know? Just wanting to feel good. So I pointed at the floor in front of me and she kneels down obediently and starts attending to me. And it feels nice, but I'm just scrolling through my phone at this point, mostly ignoring her. When it starts to feel a little better I lifted up the t-shirt and sort of start squeezing the one breast. Maybe pinching my nipple a bit. And then I rearranged my posture and when I did my leg just barely grazes her cock."

Here she imitated the slightest touch on Quinn's hard-on with her hand.

"And she lets out this big gasp, and she stops licking me so I look down and she's staring up at me with these sad eyes and she makes the most pitiful noise I've ever heard and then I see this stream of cum flowing out of her. Like she's pissing herself but it's definitely not pee. I guess because Abi always hides her boobs this was actually a big moment for little Quinny to make out a flash of tits. But at the same time I was acting like I couldn't care less. In fact I was pretty oblivious to how turned on she was. I guess she found it so degrading that it gave her a ruined orgasm."

"Oh, poor little Quinny," Willow said in her baby voice while Abi smirked.

"But the best part is that once she had recovered, she stared at the puddle on the floor, and I knew what she wanted. But I knew that she felt conflicted. Because it's one thing to have a woman pressure you to eat your cum, and another to ask her. So I just played stupid."

"What's wrong sweetie?" I asked. And she waited and waited and then finally said, "Do I need to clean it up? Do I need to eat it?" And I told her, "Oh no, that's fine, you can just mop it up." But she didn't move, she just kept staring at it. And finally I said, "Quinny, do you want to lick it up?" Then she looked up at me and nodded. "Oh Quinny, you nasty girl, eating cum is supposed to be a punishment. Wait, does it turn you on?" And she nodded again. "Well if you like it so much, I can't just reward you for having this accident. You're going to need to beg me. And then you're going to have to go upstairs and get my sister and my mother and bring them to watch." And she nodded again and I swear to God her cock still looked ready to explode.

So she brought my mom and sister down from upstairs and we all just stood there in the kitchen suppressing our giggles, and my mom of course makes Quinn beg and plead and her cock is just trembling at the thought of being denied. And my sister insists that Quinn eat her out before she have her treat, and so we watch Quinn doing it and the whole time we saw her glancing at this puddle on the floor from the corner of her eye. I have seen a man beg for release, and beg to taste pussy, but never beg to eat their own cum like little Quinn."

The girls howled with laughter at this one. Abi in particular enjoyed watching Quinn's cock act like a barometer, rising higher with each humiliating story.

"I've got another one to share about a puddle," Willow volunteered. "This was three months into chastity. I wanted to have some sexual experiences out in nature, so I took Quinn on a hike. We did our stuff but on the way back she started complaining about needing to pee. She asked if she could go in a bush, but I told her now that she's a girl she can't just pee on a tree, she needs to wait to use a toilet back home. Well she's crossing her legs on the car ride back and when we get out she's walking funny with her hands in her lap, but the thing is she can't pinch her dick to keep it in. She's just pressing on a hard tube so it does nothing. As soon as she got in the door she peed himself in the front entrance."

The girls laughed.

"Oh, it's not easy being in chastity is it, Quinny?" Grace consoled him.

"Abi, you're the only one left. What have you got?"

"Okay," Abi cleared her throat, "I think we can all agree that sometimes we feel guilty to a greater or lesser extent about how we use Quinn. And as we came up on the one year mark I was really thinking this through. For right now it's fine, I'm going to go to a local university, but I'll move out eventually and then what will happen to her? Like I don't think Quinn expected this," and she touched his apron, "when she offered for me to be her keyholder.

"So I wanted to give her a choice," she continued. "One night, about a month ago, I dressed in my sexiest lingerie and I opened the padlock on her cage and just left it hanging. She could remove the padlock if she wanted, or shut it again herself. And then I told her that she was free to do whatever she wanted with me, all night long. She could take off my clothes, she could fuck me, she could ask me to wake her up in the morning by sucking her cock. Whatever. But then the next day she would have to leave. We'd sign her up for a government program and she would become a ward of the state. She'd get unlocked once a month, which is maybe better than what she gets with me, and she'd be in charge of all her own decisions. Or she could close the lock."

Abi paused for effect.

"Of course, you already know how it turned out. She stood there shaking, and then started crying, and then closed her own padlock. And I'm very proud of her."

"And what did you do?" Abi's mom asked.

"I gently pushed her to her knees and had her perform her duty as my permanent slave." Abi said this with all seriousness. "She was never more eager to please than in that moment."

"Abi, I thought you said funny or embarrassing, why you gotta get all serious on us!" Charlotte complained.

"Oh, I think that's very sweet," Willow said.

"I think men are happiest when they're serving," Abi's mother spoke. "Serving and horny. We really have found the best way to coexist with them. I think Quinny here is actually living her best life," and she patted him on the thigh again. "She certainly chose it. Men can't control themselves. They need us to regulate their orgasms for them. Your father barely ever gets to cum anymore, but he's so much happier now that I make all the decisions for him."

"Mom, I hope you don't mind me asking, but when was the last time you let Dad have an orgasm?" Grace asked.

"No of course I don't mind. Umm, a full orgasm? I'm not really sure. You could ask him. I think it was before Christmas, maybe two or three months ago. I used to keep track when the laws first came into effect, but now I just sort of go by vibes. I'd say he's getting desperate enough that he's about due."

Grace's eyes glinted with mischief, "Well, we all know that Quinn loves the taste of semen, and it got me thinking... if Dad is due for release, and Quinn will be gone for a few days at Willow's house soon, shouldn't we let Dad make a mess now when our little French maid is here to clean it up?"

Quinn shook in his bonds and whimpered in protest, but his drooping cock spasmed and seemed to take on new life.

"Oh Quinny's had a big day," Willow sighed, "I'm not sure if we should push her that far. I don't think it's what she would actually want for her birthday."

Abi's mother allowed a sly grin to spread across her face, "I suppose it doesn't really matter what boys wants though, does it?"

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
AnonymousAnonymous4 months ago

Jane should kidnap him and own him for herself

AnonymousAnonymous4 months ago

Another absolutely amazing story! Since you asked I just wanted to share that i really love the world you have created. The background and world building is fantastic. I'm really looking forward to more stories based in this world. I am personally not into the sissification stuff, but MANY people are and i thought it worked well with the story. Anyway, looking forward to more of you work and hoping you don't keep us waiting too long!

JAFLoverJAFLover4 months ago

I would suggest having Abi loan Quinn to Jane. They run away and Jane takes possession of him and they start a new life of Jane owning him

AnonymousAnonymous4 months ago

I appreciate you sharing another story; this one was too cruel for my taste and I feel it was much meanier than your previous ones, but I respect your creativity.

I hope to read something of yours again, specially something less… brutal.

TiltingatWindmillsTiltingatWindmills5 months agoAuthor

I think this is the right place to conclude this short series. But if readers have suggestions for where to take Quinn's story next I would definitely consider them (or bring them on with new characters in a different place). Let me know what you liked in the comments and thanks for reading!

Share this Story

READ MORE OF THIS SERIES

Similar Stories

But I'm a Boy, Not a Cheerleader! Accidentally a cheerleader at the basketball party!in Transgender & Crossdressers
Bitched Out An ex con with a big cock makes me his bitch.in Transgender & Crossdressers
A New Job Finding a job in can be hard in this current job market.in Transgender & Crossdressers
White Girl Turns White Boy Sissy Ch. 01 White boy comes out to friend and she knows what he needs.in Transgender & Crossdressers
White Dom Turned Sissy for BBC Alpha white man learns his inferiority to BBC.in Transgender & Crossdressers
More Stories