CHRISTINA'S SCHOOL FOR WAYWARD GIRLS

BY KENNA
kenna198401@aol.com

[ part 6 ]

Next week starts off pretty normal, considering that I’m a 14-year-old boy working in a girls’ school where corporal punishment and humiliating sex are the norm. But, Tuesday after work, Dad pulls me into his office at home. “Something’s come up,” he says to me. “Sierra’s parents are concerned about you working at the school. We’re going to have a conference tomorrow after school.”

“What’s up, dad?” I wonder. Am I going to lose my job? Is 14-year-old heaven a thing of the past?

“You don’t have to worry about anything. In fact, tomorrow at the conference you are to say nothing. Not a word. Nada. Got it?”

“Yes, dad.”

“Apparently Sierra mentioned to her parents that you are working there. I’ve handled cases similar to this before. I’ll handle this one. You can sit, watch, listen, and learn. Perhaps you’ll be headmaster someday and need to deal with a similar situation. But, this goes to the very core values of Christina’s School for Wayward Girls, so I’ll do all the talking.”

“OK,” I nod. “Do they know what goes on at the school?”

“Parents are officially told that corporal punishment is used. They are told that bare bottom spankings are used. They are not officially told that sex is used as discipline and character building, though most suspect it by the time the girl is a freshman. How much Mr. and Mrs. Terwillger suspect or know is unknown.”

He peers down his nose at me. “May I assume that Sierra helped you out at least once on Saturday?”

“Twice,” I say.

“Oh well,” he says. “We’ll set this straight tomorrow. Can’t have the Terwillgers thinking their little girl is a sex toy.”

“Yes, dad,” I agree, getting up to leave.

As I walk away, I swear he says, “Cutest nipples in seventh grade.” As I turn to look at him, he’s busy with something and acting like nothing was said. Maybe I misunderstood him or I’m hearing things.

The next afternoon when I show up at school, Mr. and Mrs. Terwilliger are in dad’s office. There are no girls waiting to see him. I knock and go right in. “Come in, William,” says dad.

“Billy,” says Mrs. Terwillger with a curt nod.

“Hello, William,” says Mr. Terwillger.

I sit down in the only free chair.

“Now,” says dad, “I understand you have some concerns about William’s employment at the school…”

Mr. Terwilliger takes the lead. “Yes, well, our daughter, Sierra, says that he is working here and as a teacher.”

“Nonsense,” says dad. “He’s the most junior staff member. He pushes a broom around the halls in the afternoons and on Saturday he assisted Mr. Crawford.”

“Well, given that corporal punishment is permitted and… the boy was present during her punishment on Saturday… I…understand it may have been…” he gets poked by his wife, “… umm, was delivered on her bare bottom…”

“Did William have sex with Sierra?” interrupts Mrs. Terwilliger.

“Let’s address these issues one at a time,” says dad. “First, William is an employee with the school who has signed a non-disclosure agreement just like you and Sierra have. To the best of my knowledge, William has honored that agreement. He has been closely supervised by teachers during any contact he has had with the students. So, his conduct is not in question.

“Second, you are fully aware that corporal punishment, delivered upon the bare bottom of the errant girl is a common practice at the school. You have signed statements that this is perfectly OK with you. You have signed statements that you acknowledge this is in violation of Iowa State law, but you believe that it is the parents’ prerogative to authorize such punishment.

“Third, is Michael aware that William is employed here?’

“Yes,” says Mr. Terwilliger. “Actually, I had her ask him if he knew that William was employed here.”

“OK, so third is that Sierra has violated the non-disclosure agreement with the school. It generally requires her to remain silent on school affairs and there is a specific clause that prevents her from releasing the names of school staff. Now, she is allowed to discuss those matters with you, her parents, because you have signed the statements as well. But, by telling Michael, she has violated the agreement.”

“He’s her brother,” says Mrs. Terwilliger.

“Her brother who has not signed the same agreements,” says dad. “Now that you and she have violated the agreement, there are two choices. The first is to expel her. It…” Both parents interrupt with a shocked gasp, “… would be a shame for her to have excelled for six and a half years at the school only to be cast out now. The title of Wayward Girl would never be bestowed upon her after all this hard work, so I think that is not what she wants. It is not what you want. It is not in her best interest.”

“No, of course not,” says Mr. Terwilliger. “Owww,” he adds as his wife pokes him. “Is that what you want?” he asks her indignantly.

She glares at him and then at dad. “No, of course not. What’s the other choice?”

“Well, before we discuss that, let’s visit the issue of William having sex with Sierra. Since he was under the supervision of Mr. Crawford on Saturday, such an accusation would mean that Mr. Crawford condoned the activity. Such an accusation would mean the end of Christina’s School for Wayward Girls. Such an accusation would be the same as expelling Sierra and 499 other girls. Now, I am quite shocked that you would bring such an accusation to such a hallowed institution that has stood for over 100 years. I you believe that is possible then I suggest you withdraw Sierra from the school of your own accord rather than slander this institution.”

The two parents look at each other. “What’s the other choice?” repeats Mrs. Terwilliger.

“I would expect that you know the other choice,” says dad. “We discuss it annually at the parents’ meeting. It is the contingency plan for violation of the non-disclosure agreement. You must tell the big lie.”

“The big lie,” they both murmur.

“Since this only involves your son… it does involve only your son, doesn’t it?”

“Yes, yes, of course,” says Mr. Terwilliger.

“You must talk to your son and deny any suspicions that he may have about the school. Sierra must participate. William sweeps the floor, but has no contact with the students. Deny corporal punishment. Deny bare bottom spankings. Deny most enthusiastically that Sierra had sex with William. Undo any potential damage to the school that has been done by this brief breach of protocol.”

“Is this really in her best interest?” asks Mrs. Terwilliger, addressing her question more to her husband than to dad.

But dad answers, “Of course it is. Look at all she’s accomplished. Do you think she’d have the same academic standards, the same goals, the same chance for success if she was at the local public school? In this entire country we only graduate 40 or 45 girls a year who can claim to be Wayward Girls. Give her another five and a half years and she’ll be one of them.”

“It really is what’s best for her,” says Mr. Terwilliger. “We did agree to the bare bottom spanking part. And, there’s nothing immoral going on here.”

Mrs. Terwilliger doesn’t look convinced, but she also doesn’t argue.

“And please don’t forewarn Sierra that she will be punished tomorrow for violating the non-disclosure agreement,” says dad.

“What?” says Mrs. Terwilliger.

“But, it was me that made her tell her brother,” says Mr. Terwilliger. “It’s my fault.”

“She wouldn’t have,” adds Mrs. Terwilliger. “She can’t be punished for following her father’s instructions.”

“Yes, I see your point,” says dad. “OK, then I will consider the matter closed.”

There is an exchange of pleasantries and then the Terwilligers are off. As the door closes, dad looks at me, “Well done, William, a fine job of keeping your mouth shut. Do you see how important it is to the parents that their daughter be a Wayward Girl? There is so much invested in their future that it provides incredible leverage. The school has never lost a girl yet and it won’t happen on my watch.”

“Impressive, Mr. Jackson,” I say.

I reach for the door handle to leave and dad says, “Besides, I’d hate to lose those puffies.” I don’t even bother to look back; I know he’s already acting like nothing was said.

Through the rest of the week, there’s a parade of bare bottoms, even Sierra’s is available for a spanking the next afternoon. From appearances, I’m guessing it’s a trumped up charge to test her resolve to be a Wayward Girl.

Saturday arrives and dad takes me to work an hour early. Mr. Crawford asked to see me early so he could show me a few things. He takes me down to a store room and shows me that there are all kinds of costumes, makeup, and interesting looking toys. We browse through them for a while, but it’s mostly so I can see what’s available. He’s already made up his mind on what we’re going to use today.

With a few minutes left before the girls arrive, he tells me that he’s asked for a couple of second graders today. When I mention that dad said he preferred seventh graders, Mr. Crawford replies, “I do indeed, but I figured that in the interest of training you properly I’d better show you a variety. Second graders are much different from seventh. And not just in their privates. Or perhaps in their most private of privates, their minds. You have to treat them much differently. Next week we’ll do juniors and the last week we’ll do fifth graders. After that, you’ll be on your own.”

I can hardly believe that last part. I think there ought to be a long, long waiting list to get this job, but somehow it’s been handed to me on a silver platter. Sure dad mentioned the importance of the non-disclosure thing and I’ve proven I can keep a secret, but turning me loose on a school full… or at least one girl every Saturday, just seems way too cool.

The second graders arrive and I meet Allison and Courtney. I’ve already seen the costumes that they’ll be wearing and they just are too hot for a couple of 7-year-olds. Mr. Crawford has pointed out that girls this age are less self-assured, less trained, and less compliant. Still, they are Wayward Girls, so some discipline is expected.

He has them step up onto the chair and then onto the desk while still wearing their school uniforms. “Second graders,” he says. “Second graders. Mere 7-year-olds. They haven’t the maturity in their cunts for full penetration, but don’t mind having the head of a cock rubbed up and down their slick little slits. They have no tits, but they do have nipples that will get hard and pointy. They have narrow hips and tight little asses. Round little buns just begging for a spanking. We’ll find out today if these two have mastered the art of cocksucking. We’ll find out if they know the meaning of humility. We’ll find out if they can suffer silently. We’ll find out if they are Wayward Girls. Are you Wayward Girls?”

“Yes, Mr. Crawford,” they both answer.

“I thought so,” he says. “Allison, you are a beautiful girl with that long brown hair and those pretty blue eyes. I’ll bet your parents want nothing but the best for you.”

“Yes, Mr. Crawford.”

“You’re pretty, too, Courtney,” I say. “Those big brown eyes are so sweet and I just love freckles.”

“Thank you, Master, Jackson.”

“Take off your panties and give them to me, Courtney,” I say.

She reaches under her short, tartan skirt and pulls down her white panties. She steps out of them and then hands them down to me. “Very good,” I say. “I like a little girl who follows instructions. You’re smart. Now, lift up your skirt and show me what’s under there.”

The little girl lifts up her skirt and shows me her slender thighs framing her fat, bare pussy. She holds it up for several seconds, waiting for my permission to put it down again. “Turn around and show me your ass,” I say. She turns, letting her skirt fall in front and lifting it up from behind.

“Take off your tie and blouse,” I command. She does as she is told, handing them to me as she removes them. “Good girl,” I praise her. “Now take off your T-shirt.” She skins it off over her head, standing now in just her short skirt. “That’s pretty sexy looking,” I tell her.

“Th-thank you, Master Jackson,” she says.

“Even sexier with that skirt off,” I say. “Give it to me.” She unzips the skirt and steps out of it. Now she’s completely on display, standing up on the desk. She looks a little nervous, glancing at me and then at Mr. Crawford.

“I hear you can tap dance,” I say. “I hear you’re a pretty good dancer.”

“Uh huh, yes, Master Jackson.”

“Pretend there’s some music and dance for me.”

There she is up on the desk, wearing just knee high and shoes, doing a little soft shoe dance for me. There’s no room for being shy when you’re a Wayward Girl. She performs for us like she does this every day. That’s what character building is all about.

“Take off your panties, Allison,” says Mr. Crawford.

“I don’t like to, Mr. Crawford,” says Allison.

“I didn’t ask if you liked to,” says Mr. Crawford. “I didn’t ask if you wanted to. I didn’t ask you to take them off. I told you to take them off. Now do it.” His voice stays calm and steady as he directs her.

Allison looks at her classmate, who has already set the example. “That’s right,” says Mr. Crawford. “Courtney is a good girl who follows orders like a Wayward Girl should. She’s already naked. Do you want her to show you up?” Allison fumbles at her skirt, but doesn’t reach for her panties. “Have you removed your panties at school before?” asks Mr. Crawford.

“Yes, but my teacher… she’s a lady.”

“Ahh, so you’ll show your pussy to a lady, but not to a man.”

“Yes, Mr. Crawford.”

“Well, character building is all about new experiences, Allison. So take them off and show me and Master Jackson your pussy. Do that or else he will hold you down for me while I take them off you myself.”

Allison eyes me and decides that the two of us could overpower her. She reaches under her skirt and lowers her panties, then hands them to Mr. Crawford. “Lift up your skirt.” She lifts it up, giving us a view of her pussy. “Now that’s not so hard, is it?”

“No, Mr. Crawford.”

“OK, now, pay attention to this. If I have to ask you to do something twice again, for the rest of the day, then I’m going to switch you five times. You do everything I ask the first time and there will be no spanking.”

“Yes, Mr. Crawford.”

“You want to be a good girl, don’t you?”

“Yes, Mr. Crawford.”

“You want to be a Wayward Girl, don’t you?”

“Yes, Mr. Crawford.”

“Fine, then take off your tie and your shirt.” She hurries to get her blouse off. “Now the undershirt.” She skins it off quickly. “Now, give me your skirt.” She drops her skirt to the desk and hands it to him. “Lay down on your back.” When she’s on her back, he says, “Spread your little cunnie lips open for me.” She reaches down and opens up her pussy, showing the tight tunnel between her thighs. He reaches out and puts his finger in that hole, only up to the first knuckle. “Very good girl,” he says.

“We’ve got some cute costumes for you,” I say. Mr. Crawford is letting me take the lead today although he has told me what to say. “Take off your shoes and socks, too. You’re going to start completely naked.”

The two girls strip off even their shoes and socks and then, “Here’s the first thing.” I hold out new stockings for Courtney. “Sit on the edge of the desk and let me dress you.” She sits down and I pull the leopard print stocking all the way up her legs. As I settle the second stocking in place, nestled against her plump pussy, I run a finger across her pussy lips. She squirms, but doesn’t complain.

I pause as Mr. Crawford does the same to Allison. Then, I present Courtney with long, leopard print gloves. They cover her arms, but leave her fingers exposed. After Allison is similarly gloved, I show Courtney the leopard print corset. I help her off the desk and then get her to step into it. I pull it up her body, seating it between her delectable little nipples and her precious little cunt. Then I tighten it, pulling in her waist to give her a little curve for her body. “You’re going to be kitty cats today,” I tell them.

As a topper, they get little kitty ears on their heads. Then, we paint whiskers on their cheeks with makeup. They are similarly clad, although Allison is wearing tiger stripes instead of leopard spots. They think they are pretty cute as they admire each other with giggles. Every little girl likes to play dress up. The difference with what we’re doing is that their private treasures aren’t hidden from view, but are accentuate by the sexy kitty costumes.

“Just one more thing,” I say, holding up a kitty tail for Courtney. Mr. Crawford has one for Allison, too. “Turn around and put your hands on the desk.” Courtney turns to present her ass to me. “Bend way over… farther… just like that.” The tail has a little cone at the end. The cone is about 3 inches long. It starts as a point and then flares out to about an inch and a half in diameter before dropping back to skinny again where the tail starts. I push the point of the cone against Courtney’s little pink asshole.

“Hunh?” says Courtney as I poke at her in an unfamiliar way. But the cone slides in and her tight little sphincter closes around it. It is firmly seated inside her. She reaches back to pull it out, but I catch her hands.

“No, it’s going to stay in there for a while,” I tell her.

Allison looks at Courtney and says, “It went up her butt.” She starts to turn around, but Mr. Crawford presses her tail into place. “Aaaahhh,” she gasps as her asshole spreads and then closes again. Her pert ass is violated and she can’t do anything about it.

“Now you’re kitty cats,” says Mr. Crawford. “You even have tails.”

The girls squirm around for a couple of minutes, but they understand the tails can’t come out until we say it’s OK. It’s kind of funny to watch them adjust to the feeling of a 3 inch dildo up their ass. When they have settled down a little, I sit down in a chair and pat my lap. “Hop in my lap, Courtney. I want to pet my kitty.”

When she sits in my lap, I start innocently enough by scratching her ears just like she was a cat. I scratch under her chin and rub her bare shoulders. Then, I rub her chest, feeling her tiny nipples. Her posture shifts slightly, telling me that she’s uncomfortable with my hands on her chest. “I love feeling up second graders,” I say, just to make her even more uncomfortable. “I like playing with your hard nipples. You don’t have titties, but you do have nice nipples.”

I glance over at Mr. Crawford to see that he’s got Allison squirming on his lap, too. But, I return my attention back to Courtney. “Such cute little nipples. I’ll bet you like having a boy play with your nipples like this.”

“Noooo,” she says softly.

“You should,” I say. “Such a pretty girl with such nice, hard nipples.” I turn her so she’s facing away from me, her legs straddling my legs, her butt pressing into my crotch. In that position, I can use both hands on her chest, cupping her nipples and squeezing them. “Tell me how much you like this.”

“No, I don’t.”

“You don’t have to like it,” I say. “But you have to tell me you like it.”

She digests that concept for a few seconds. “I like it,” she says simply.

“A lot?”

“Yes, Master Jackson, a lot.”

“Want me to stop?”

“Yes.”

“Say no, please don’t stop.”

“N-no, please don’t stop.”

“You like it when I pinch them and make them hard.”

There’s a moment of silence, then, “Yes, I like it a lot.”

Damn, I want to ask her if she wants to suck my cock, but like last week, I have to wait until 11. Instead, I have to shift her off my cock or else I’ll be in trouble with Mr. Crawford. I slide my hands down her body to rest just above the top of her stockings on the little bit of bare thigh that she’s showing. Then I start tracing little circles on her thigh with my fingers. As the circles get bigger, I get closer and closer to her bare pussy.

“You like it when I touch you here?” I ask.

“Yes,” she says. “I like it a lot.”

“Good girl. I’m going to touch your pussy. What do you think about that?”

“I think I’m going to like it,” she says.

So, I use one hand to caress her pussy, feeling her rubbery lips and the slit between them. She holds still, letting me have my way with her. I poke a finger in her up to the second knuckle. She’s tight and she jumps as I penetrate her even that little bit. “You like it when I put a finger in you?”

“Yes, Master Jackson,” she says. “I like it.” As she relaxes, I let my finger slide in and out, fucking her with my finger. She lays her head back on my shoulder and I wonder if she really does like this. My finger wanders up to find her clit and I rub that slowly. It takes a few minutes, but I can feel her getting wet. Then, she turns her head to look up at me. “I like it a lot,” she says softly.

I continue to tease her clit until she is panting and moaning softly. I know she’s getting aroused, but I’m not supposed to let her cum. Mr. Crawford notices as well. I haven’t been paying attention to him and Allison, but he’s got her little motor running, too. “That’s good,” he says. “Time to switch.”

The girls slide off our laps, looking a little confused that they were so close, yet now so far away from cumming. They wanted that dreamy feeling to continue.

“Time to be kitty cats,” says Mr. Crawford. “Kitty cats like to keep themselves clean. Show me how you can lick your hands and arms to keep them clean like a kitty.” They start licking their hands and arms. With a little coaching, they lick the back of their hands and then rub them against their faces.

“There’s places that a kitty can’t reach,” I say. “So, they let other kitties lick them there. I want to see my kitty clean Allison’s back with her tongue.” Both girls stop what they are doing and stare at me and then at Mr. Crawford. Allison turns away from Courtney, offering her back. Courtney leans forward and licks at Allison’s shoulder blade.

I watch for a few minutes, offering occasional praise at how good she is. She licks all over Allison’s back, at least the part that’s above the corset. Then I pull Allison’s hair away from her shoulders and point at Allison’s left shoulder. Courtney moves up there and then follows my finger around as I point at the back of the tiger’s neck and other shoulder. Still following my finger, she finds herself licking at Allison’s throat. The tiger lets out a soft coo as she appreciates the gentle lapping at her sensitive throat.

Without missing a beat, Courtney follows my unspoken instructions to lick Allison’s chest and nipples. Then I step away as Mr. Crawford gets Allison to repeat the same procedure on Courtney. It looks pretty hot to see the 7-year-old Allison being so tender with her classmate. It’s particularly exciting to watch her lick at Courtney’s nipples, hardening them as I had done with my fingers.

When Allison has made the complete circuit of all the bare skin above Courtney’s corset, I step back and the girls switch roles again. But, this time, Courtney is licking the bare skin below Allison’s corset. I start her at Allison’s left hip and she works around to her other hip, cleaning and licking every inch of Allison’s cute little ass in between. Then I move her around front. By now she’s getting into the kitty play and has probably had time to think about what’s coming up. She doesn’t hesitate at Allison’s pussy, but licks it thoroughly.

“Even more,” I say. “Lick in the slit. Find her clit. Lick it for her. I’ll tell you when to stop.” She parts Allison’s pussy lips with her tongue, tasting her classmate’s juices. She finds the hard little nub and soon has Allison moaning in pleasure. “Faster,” I tell her. “Harder. More.” She licks harder, encouraged by the pleasant sounds coming from Allison.

When Allison cums, they switch roles again. Allison is eager to get to Courtney’s pussy. She is flush with excitement from her own orgasm and wants to repay the favor. She tries to hurry, but Mr. Crawford makes sure she licks all of Courtney’s ass before getting around front.

After Courtney cums, we take the girls down to the dungeon. I find there is more than one room to the dungeon as Mr. Crawford takes me through a different door. Inside this room, the tie up points are not on the walls, but on the ceiling. We tie our girls to ropes hanging down and then pull them up into the air. We stop pulling them up when their feet are about a foot off the ground.

“You can use either room,” says Mr. Crawford. “This one allows you to stretch them more. I do love the view of a young girl’s body as it stretches from the ceiling.” He runs his hands down Allison’s taut body. He does it several times, caressing her strained muscles, her ribs, her smooth chest, and her firm ass. I take the hint and spend several minutes with Courtney. By now she’s used to my hands on her body. Perhaps she is even learning to like it.

Mr. Crawford picks up a wooden paddle and says, “Tough choice, Allison. Which do you want from me? My hands or this?” He swats her helpless bare ass firmly. She screams in shock and surprise.

There are plenty of paddles, so I start using one on Courtney’s ass. “Touch me, please,” she begs in between screams and sobs. “I like it when you touch me. Touch me anywhere.”

I attend to her nipples long enough for her to say, “I like it when you touch me there. It’s OK to touch me there. I like it whole, whole lot.” Then I resume spanking her. “Touch me in my privates,” she whines. “Put a finger inside me.”

She’ll do anything to stop the spanking now. As she gets frantic for my hands on her, I say, “Listen to you, Courtney. You’re such a slut. You want me to touch you. That means you can’t tell anyone that I touched you, here and here and here,” I let my hands touch her in all the places she knows are wrong. “You begged for my hands. What would people say about that?”

Courtney’s reply is simply heavy panting as her eyes wildly beg for my hands. She understands what I’m saying. I lean close to her and say, “This will just be our secret. It’s the secret of a Wayward Girl. It’s what makes you special.” She sighs with relief as I drop the paddle to the floor and caress her entire body.

It’s finally 11 o’clock as we return to the classroom. Her pussy may be too tight to use, but her ass has been exercises by the dildo for a couple of hours. I bend my little 7-year-old over and push my cock inside her ass. She grunts with pain and surprise, but doesn’t resist. I look down at my big cock, stretching her tight ass open, and I start to fuck her. It doesn’t take me long to fill her with my cum.

Mr. Crawford is even bigger than me and little Allison isn’t complaining about his cock up her ass. I wash off my cock and Courtney shows me that she’s pretty good at cocksucking.

After lunch and dodge ball, I get paired with a freshman. That’s a nice change for the end of the day and I fuck her good.

“Older girls are nice, too,” observed Mr. Crawford. “Next Saturday I’ve requested juniors so you can see how they do.”