Daddies of the Castle

by Adaline Raine

  Master Emerson sighed and rubbed his brow. “I apologize for her behavior and assure you that once I am through with her, she will express her remorse as well. She is supposed to be confined to her dorm room, and I will be speaking to the dorm master to see how she was able to leave undetected. Ordinarily, I would not betray another guest’s confidence, but I’m going to share with you, in hopes that you might understand her a bit more.

  “Cindy had a very benevolent Daddy, who brought her here often. He would leave her at the boarding school when he needed to take business trips, but just as often would come along and enjoy the festivities with her. Last fall, he fell ill, and he passed away at the beginning of this year. His estate takes very good care of Cindy financially, and he had purchased lifetime memberships for both of them, so Cindy comes here when she can, to try to take the edge off of her grief. The truth is, she is very lonely and without anyone corralling her, she’s fallen into some very bad habits. She will do almost anything to get attention, negative or positive. Since negative attention is easier to get, that is what she leans towards. She isn’t mean spirited, but like I said, her craving for negative attention has been winning out over her better nature.

  “We are in the process of assigning her a disciplinarian of sorts for her time here. Someone who can give her undivided attention and consistency.”

  Addi’s heart was breaking for the other girl. The thought of losing either of her parents caused her to cry deeply.

  Mommy held her tight as she wiped her own eyes. “That poor girl. Is there anything we can do?”

  “Yes—don’t give in to her. The last thing she needs is more people extending her grace because of their pity for her. It flows contrary to our desires, but what she really needs right now is rigidity. She needs to know that rules and expectations here at the Castle don’t change even though everything else in her world has crumbled.”

  Daddy nodded. “We can do that. Shall we leave, so the two of you can discuss her punishment?”

  Master Emerson shook his head. “Actually, if it wouldn’t inconvenience you, I think a little public humiliation would be good for her. Would you three be able to stay and witness her punishment?”

  Daddy and Mommy nodded. Addi looked uncertain, but slowly nodded as well. “If I have to. I don’t want to make her feel bad…”

  “Don’t worry, you’re not the one making her feel bad. She brought this on herself.”

  Master Emerson walked over, tapped Cindy on the shoulder, and took the headphones off. “I hear you’ve been teasing, spying, and showing disrespect to your elders, not to mention blatantly defying my orders for you to stay confined to your room today?”

  The time in the corner seemed to have subdued Cindy somewhat. “Yeah, but I didn’t mean to do all of that. I was just bored and wanted to take a walk, and then she was getting spanked and… I was just teasing.”

  “Well, your teasing and disrespect has led to hurt feelings, and your disobedience will not be taken lightly.”

  Cindy shifted from foot to foot.

  “Hands on your ankles. We will take care of your disobedience first.”

  Cindy moved to obey and then stopped. “After they leave, right?”

  “No. Right now. They aren’t going anywhere. I’ve invited them to witness your chastisement. Maybe being publicly disciplined will help you show more self-restraint in the future.”

  Cindy’s face flushed red but she obeyed, her white bottom vulnerably open and ready for her punishment.

  Master Emerson walked over to the wall and pulled down a long cane about the width of his pointer finger. He also opened a drawer of his desk and placed a solid oak paddle similar to a Ping-Pong paddle on top of the desk. “Cindy, you are going to count these out and say ‘I will not disobey’ as they land. Understood?”

  Cindy sniffed. “Yes, Master Emerson.”

  Master Emerson raised the cane up high in the air and brought it down hard on her bottom.

  Cindy screamed. “One, I will not disobey!”

  When he raised the cane again, Addi winced at the angry red welt on Cindy’s butt.

  Master Emerson brought it down again just as hard as the first time.

  “Two, I will not disobey!”

  When he was done, Cindy was sobbing, and there were six equally spaced deep red lines from the crown of her ass to the middle of her thighs.

  “Now, come over here…” He led Cindy to his chair, sat down, and pulled her over his knee. “This next part is for your rude and mean-spirited comments to Penny.”

  Barely giving Cindy a chance to process his words, he brought the paddle down on her left cheek, then her right, then the center. He never moved from the pattern; left, right, center. Left, right, center.

  Addi felt pangs of compassion for Cindy. She had been really mean, but Master Emerson was not holding back, and Cindy’s bottom was turning almost purple in the wake of his minstrations.

  Cindy wailed at the top of her lungs, and Addi got the feeling that it was more than the pain of the spanking causing Cindy’s immense grief. Addi hoped it was cathartic for her to get all of her feelings out. Maybe she wouldn’t be such a brat now.

  Master Emerson finished up the spanking with one last solid stroke to the center of Cindy’s bottom. He slid her panties up over her scorched butt and pulled her into a sitting position on his lap. Holding her legs with one arm and her head with his other, he cradled Cindy’s body and let her sob out her grief.

  Daddy and Mommy pulled Addi close to them while they all watched Master Emerson provide Cindy with tender aftercare. Addi felt so sad that Cindy wasn’t getting this sort of love on a regular basis. She vowed to be kind to her in class tomorrow, regardless of whether Cindy was bratty or sweet.

  After several moments, as Cindy’s crying turned to sniffles, Master Emerson stood her up and walked her over, her hand in his.

  “I think Cindy has something she would like to say to you three.” He gently prodded the now blotchy red-faced girl, one of her ribbons completely gone, and the other hanging at an odd angle.

  Swallowing and wiping her nose on the back of her free hand, Cindy spoke quietly, but earnestly. “I’m so sorry I made fun of you, Penny! I get spanked all the time—well, I used to. And it’s nothing to be ashamed of. I don’t even know why I was teasing. Can we still try to be friends?”

  Addi enveloped her in a tight hug. “Of course we can! And I forgive you. I’m sorry you hadta get such a big spanking! It looked awful.”

  Cindy squeezed her back. “It was, but it reminded me that my Daddy would never have put up with meanness like that.”

  She turned towards Addi’s Mommy and Daddy. “Mr. and Mrs. Cleaver, I’m awful sorry I was so rude and stuff. I wasn’t using my manners. Can you please forgive me, and can I still play with Addi?”

  Both of Addi’s parents pulled Cindy towards them and hugged her tightly.

  Daddy spoke first. “All is forgiven, Cindy. I know that sometimes Little girls forget, and have to be reminded that they are not in charge of their own lives. As far as we are concerned, your slate is clean.”

  “We’d love it if you’d come with Addi after school tomorrow. Perhaps we can go to the swimming pool. That is—if you’ve earned back your privileges?” Mommy glanced at Master Emerson.

  “We will have to discuss that with Cindy’s guardian for the week. She and I are going to meet him for dinner soon. That is a very kind invitation, though, and I will recommend that she be permitted—assuming her behavior is commensurate with such a treat.”

  Addi and Cindy clapped and squealed.

  “All right, little one. It’s time for us to head back to our room and freshen up for dinner. Cindy, we will hopefully see you tomorrow. Good luck with your meeting tonight.” Daddy kissed the top of Cindy’s head.

  Addi gave Cindy one last hug and followed her parents out the door.

  Addi sat on the bed and then squeaked. Three spankings in one day was a little much, even for her regular
ly disciplined derriere.

  “We have like an hour before dinner. What do you guys wanna do?” she asked, hoping she knew the answer, but not wanting to pressure them.

  “Well, that depends. Do you have a big girl mindset or a little girl one?” Mommy asked. “We could take a bubble bath or listen to Daddy read. Maybe play some cards. Or…” Natalie looked at her suggestively.

  “I want or !” Addi unbuckled her overalls, leaving them in a heap on the floor. Standing in only her shirt and socks with her braided pigtails, she definitely looked little girlish, but the feelings she was feeling were as far from that as possible. “I want a wild threesome with my favorite people on earth. I want to come hard, preferably more than once, and I want to feel your naked skin against mine.”

  She threw herself at Natalie, knocking her onto the bed. Natalie hissed slightly but ripped Addi’s shirt off with one hand while pulling her hair and kissing her hard with the other.

  “No bra, what a naughty minx you are today!” Natalie nibbled on the nape of Addi’s neck.

  Antonio joined them on the bed, having already removed all of his clothing.

  He carefully removed Natalie’s stockings and panties, then unzipped the back of her dress.

  She slid her arms out and Addi pulled Natalie’s slip off over the top of her head.

  Addi stopped and gasped. “What happened to you? You’re covered in bruises!”

  Natalie looked down and smiled. “Not bruises. Love marks.”

  Addi looked more closely and ran her fingers down Natalie’s breasts and stomach, then checked her back and ass.

  “I guess your slate really is clean. Glad I wasn’t around for this. I’d never have let him go so hard.” Addi knew she couldn’t actually have intervened, but was still relieved she hadn’t been around.

  Natalie nipped Addi’s breast. “I can leave some on you if it would make you feel better.”

  Addi giggled. “Whatever you want. Months without sex when you two have gotten me used to it daily was torture.”

  Natalie took her mouth dominantly while Antonio played with Addi’s nipples.

  “I seem to recall someone mentioning they wanted to come hard multiple times? If we want to make it to dinner on time, we should get started,” Antonio said with a rakish grin.

  While Natalie continued to kiss her deeply, Antonio brought his mouth down on Addi’s bare pussy. With all of the excitement of the day and the feeling of her lovers’ touch for the first time in so long, he barely had to touch her before Addi was writhing in pleasure.

  Once she had come down enough, she drunkenly muttered to Antonio, “Your turn now, Papi .” She only called him Papi during sex, but it always seemed to fit.

  This time, Natalie went down on Antonio while Addi played with his nipples and kissed him from belly button to mouth. When he signaled he was about to come, Addi took his mouth while Natalie finished him off.

  His orgasm was no less spectacular than Addi’s and Natalie kissed her immediately, so they could share the taste of his seed.

  Antonio instructed the ladies to lie on either side of him while he finger fucked them. They held hands, so when they orgasmed, they were able to do it in unison and feel as if they were doing it as one.

  Lying sweaty and satiated, the trio snuggled quietly for several minutes before Addi broke the silence. “Now that my sexual starvation has been met for the minute, my body is ready for food of an entirely more real kind. Think we can shower together without anyone trying to hump anyone else?”

  Everyone laughed, but they managed to get in and out of the bathroom without incident.

  Mommy brushed Addi’s hair and put it up in a high ponytail with a pink ribbon tied in a bow, and applauded over the adorable pink polka-dotted party dress Star had sent up for Addi to wear. Completing the ensemble with a pair of black Mary Janes, Addi felt like she was stepping straight out of Charlotte’s Web .

  Once Mommy and Daddy were dressed in their clothes—Daddy in a respectable suit, and Mommy in a more adult version of Addi’s dress, with gloves and a shawl—they were all more than ready for dinner.

  Roast beef, shrimp, and stuffed pork chops were available, along with every side you could dream of, and a full dessert bar, complete with someone to scoop as much ice cream for you as you wanted. Addi decided she was just moving into the Castle and living here for the rest of her life.

  Chapter 7

  “ A nd that concludes today’s lessons. I do have one final announcement. There is going to be a school dance Friday night. Wear whatever you feel comfortable in. The theme this week is butterfly garden. There will be dessert and an open non-alcoholic bar set up. We will be utilizing the rear gardens. Tonight’s homework is a paper on dominance and submission in the animal kingdom. See you all in the morning.”

  As Master Emerson finished his closing speech, Addi felt giddy with excitement and nerves. She hadn’t attended any of the dances when she’d actually attended high school. All the boys had been dumb, and it just hadn’t been her scene.

  “Hey Penny?” Damien caught her attention. “I was wondering if you’d like to accompany me to the dance. We can grab dinner together beforehand and walk over together.”

  Addi bit her lip and nodded. “I’d love that. Do you want me to meet in the dining room, or…”

  “I’ll pick you up at your room at 5:30, if that’s all right with you. Do I need to ask your parents for permission?”

  Addi blinked. “I have no idea. This has never come up.”

  Can I even go on a “date” when I’m in a relationship? Does this count as a date?

  “Why don’t I walk with you now and we can ask them together?”

  “Well, Cindy’s coming back with me and we’re having a play date. I mean, you can walk with us too, if you want. I don’t think Cindy will mind.”

  Cindy walked up behind them just then. “Mind what?”

  “Damien wants me to go to the dance with him, and he wants to ask my parents. Do you care if he walks with us back to my room?”

  “No, that’s cool.” Cindy said the right words, but she looked dejected.

  “Hey, it’s our special time. Damien can come over later or something.”

  “Yeah, I’m fine to wait.” Damien gave Cindy a genuine smile.

  “No, it’s not that. I just… I don’t have a date, and thought we could go together, Penny. But it’s fine. You two have fun.”

  Addi felt torn. She definitely didn’t want to hurt Cindy, but going as a couple with Damien also sounded really special.

  As she was debating what to do, Charlie, one of their classmates, came up. “Hey, Cindy! I hope I’m not too late. I wanted to ask if I can take you to the dance.”

  Before Cindy could answer, Brett piped up. “Not fair! I was literally about to ask her.”

  Addi giggled. “I don’t think you’re going to be wanting for an escort, Cindy. Are you okay meeting there with our respective dates?”

  Cindy nodded regally. “Now boys, no need to fight. You can both take me. There’s enough Cindy to go around.” She kissed each of them on the cheek. “I have plans right now, but let’s talk tomorrow about when y’all are going to pick me up.”

  Charlie and Brett seemed agreeable to the deal, so Addi, Cindy, and Damien walked up to her room.

  “Gimme one sec to make sure they are presentable,” Addi teased when they got to her room.

  She slid inside and was glad she had thought to check first as the couple was lying naked on the bed, feeding each other chocolate.

  “Did you two forget about our play date with Cindy? Also, Damien’s here. He wants to ask your permission to escort me to a school dance on Friday. I said yes, but then I wasn’t sure how you two would feel. Is it okay for me to go on a date when I’m already taken? It’s not like I wanna run off and marry him or something.”

  Mommy glanced at the clock and sat up. “Sorry! We must have lost track of time. We’ll be ready in two minutes. As for a dance…”


  Daddy sat up and pulled Addi into his lap. “I don’t see why it would be a problem, but your face looks guilty. Do you feel badly about liking the attention?”

  Addi nodded.

  “I think, since you’re playing the role of a schoolgirl, a schoolgirl crush makes perfect sense. I’m fine treating this like Pops sending his daughter off to the sock hop, if you want that experience.”

  Mommy nodded as she pulled a sundress over her head. “Me too. There will, of course, be a curfew and I expect ladylike behavior from you, little girl, but I don’t have any jealousies, if that’s what you’re worried about. You’re ours and that isn’t going to change, but if you want to explore and experience different things one on one with a boy your own age, I have no issues with that.”

  Addi beamed and kissed Daddy’s cheek. “Thanks, guys! I’ll go let them in. Daddy, put some pants on!”

  She stepped outside again. “They are almost presentable. Cindy, I forgot to ask, did you bring your swimsuit? I’m dying to try the slide!”

  Cindy grinned. “Yup, Star set me up this morning. Oh! I didn’t tell you yet, my new guardian is named Uncle James. He’s so nice!”

  Addi grinned. “I’m so happy you have someone, even if it’s just for the week.”

  Daddy opened the door. “Hey, kiddos, how was school?”

  “It was great, Mr. Cleaver. I didn’t even cause a drop of trouble.” Cindy curtsied.

  Damien stuck his hand out. “Damien Grey, sir. I don’t mean to interrupt your afternoon. I just wanted to ask you and Mrs. Cleaver if I could take Penny to dinner and the dance on Friday.”

  Daddy gave Damien a serious look as he shook his hand firmly. “That should be fine, but I expect you to treat her with the utmost respect, remember that her Little isn’t even in high school yet, and have her back here by midnight.”

  “And I expect ample opportunity to take pictures!” Mommy shouted as she stuck her head around the door.

  Damien nodded solemnly. “Yes sir, yes ma’am. I’ll treat her like a princess, nothing untoward, no turning into pumpkins, and lots of pictures. All of that, I can do!”