Academy Pt. 03

Abbi could sense Mr. Cleveland behind her, his eyes roving across her back, bottom, legs, and feet.

Oh, please, please, please fuck me! Abbi mentally shouted. Fuck me, fuck me, fuck me!

Instead, she took a deep breath and awaited the arrival of his hands. It wasn't long before they were there, soft yet firm, warm, and insistent.

"Would you like me to use oil, Miss Abbi?"

"Ooh, that would be so nice, yes."

"It dries up really clean and won't ruin your uniform."

"I trust you sir," Abbi allowed.

He started with her shoulders, down her arms, and up her neck. The combination of his strong hands and the lavender massage oil made her unclench internally for the first time that day.

"You don't have much tension, young miss. That's good," he determined. "In fact, you are quite supple, if you don't mind me saying so."

"I don't sir," she replied, face smooshed into the headrest. "Mind, I mean. You say the nicest things to me."

He started to work down her sides and back, stopping just short of her bra, as if it were a line he didn't yet want to cross.

"I'm going to unhook your bra now."

"Yes, sir." Abbi had never felt so relaxed and horny at the same time. Bliss.

He fumbled a couple of tries back there, hands too slick with oil to get the job done right.

"Here," Abbi insisted. "Let me get that for you." She reached back and undid the clasp, then decided just to go for it. "Could you put this on the bed?"

Abbi leaned back and twisted around to give him a peek, her nipples hard little pink pebbles.

Mr. Cleveland's sharp intake of breath told her that the small gesture had hit home as intended. Their hands touched when she handed him the bra, a tiny spark.

"I'm sorry," he began.

Abbi leaned back onto the chair, burying her face once again.

"What for, sir?"

"I accidentally saw something I shouldn't have."

This shy teacher routine was just too fucking cute.

"You should be more careful then, sir."

"I will, young miss, I promise."

He returned to the task at hand, his hands doing great work up and down her bare back. When he started working on her sides, his fingertips would graze her boobs ever so slightly, sending more shivers and waves of goosebumps.

There was a new line that he got ever closer to, but strategically shied away from. The waistband of her briefs was the new battlefront and she ached for him to just pull them down, tear them off. There was nothing in the way, and simply putting her feet back on the floor would relieve them from her completely.

My panties, take them off, please! Abbi thought. Panties!

"How am I doing, Miss Abbi? How are you feeling?"

This is it! This is your chance! She thought. But no. How can I make it his idea? I kinda want to put up a fight, make it weird.

"I feel so relaxed and safe, sir. I could almost fall asleep right here."

"There's one more spot I should really take care of before we finish up, if you'll allow me."

My pussy! My ass! Take care of my private parts by fucking them!

"I don't know, sir. You mean my bottom, right?"

"Yes. I mean no, it's actually your lower back."

"I don't know, Mr. Cleveland. You'll have to pull them down, right? My panties?"

This is all so silly and oh so fucking hot, Abbi mused.

"Yes, young miss," Mr. Cleveland pleaded. "I will need to pull your panties down, but I promise not to do anything that would, I mean, anything dishonorable."

"I trust you, sir. I guess you can pull my panties down, if you just work on the spot you said."

A long moment passed, or so it seemed for them both before he hooked two fingers into the waistband and gave them a pull. They immediately slid back up and he was forced to pull them down again, more forcefully this time.

Abbi felt so vulnerable and exposed with her whole naked butt just hanging out there in the air.

"Oh, my goodness," Mr. Cleveland confessed. "Oh, my gosh."

Say something sweet about my ass, I dare you.

"These handprints are from Nurse Polk, right?"

"Yes, sir."

"Unmistakable," he stated. "I'm so sorry this happened to you, sweetheart."

"It's ok now, Mr. Cleveland, really."

"No, such a perfect little bottom shouldn't be so badly marked, no matter how much you may have deserved it."

"It's ok, Ms. Ford said I took my punishment like a real big girl."

"I'm sure you did, dear," he swooned. "I can, I have, um, sorry."

"Yes, sir?"

"I have a special lotion that can ease any pain that's left there and even make the marks go away faster, if you'll allow me."

"I don't know, Mr. Cleveland. Are you supposed to be touching little girl's bottoms?"

"I really shouldn't, but I just feel so bad for you."

"If it makes you feel better, you can use the special lotion. You have my permission. Just don't..." Abbi paused, wondering if she was taking this too far.

Don't stick your finger in my butthole, she almost said. Wait, no, would that be so bad?

"Don't?"

"No, sir, forget it. It's ok."

The lotion Mr. Cleveland applied was like a fresh, cool breeze, and his hands were nimble as he worked it carefully into her skin.

"Nurse Polk put her finger and a thermometer in my bottom hole," Abbi blurted out.

Mr. Cleveland stopped his motion, cupping her pert, curvy little cheeks.

"Did she?" he asked, shocked.

Abbi had turned her embarrassing habit of talking and sharing too much and turned it into a sexy weapon. She promised herself to do this more often in the future. Fun!

"Yes," Abbi breathed. She craned her neck around and flashed him her best doe-eyes.

"I'm so sorry that happened, but I'm sure Nurse Polk had a perfectly good reason to."

"It made me feel all weird and slippery inside."

"Did it?"

Abbi could feel the waves of arousal radiating from this man.

"Yes. I thought it would hurt too, but it just made me feel wrong inside. Like, it felt kinda good, but I shouldn't be, you know, liking it."

Abbi put her face back in the donut again, the shame as near to real as it could get.

"Well, you're safe now, Miss Abbi," Mr. Cleveland choked out. "I'll make it all better back here."

He returned to massaging her alabaster peach, more forcefully this time, plainly determined to make good on his promise. As sneaky as his side-boob contacts were, he was, by stark contrast, careless with his fingers as they brushed by her private parts. The cooling lotion did nothing to quench the fire that he had started down there.

"Um, Mr. Cleveland?"

"Yes, Miss Abbi?" he answered, slowly separating and compressing, separating and compressing her butt cheeks while working the lotion in.

"I think that weird feeling is starting to happen again."

"Is that so? Maybe I should stop." He didn't though. This guy is smooth.

"Maybe. Is it normal to feel, like, squirmy and warm and butterflies deep in your tummy while getting a massage?"

"Those sound like very adult feelings, Miss Abbi. I don't know if you should be telling me about them."

He started to move up her back and shoulders, away from the runaway nuclear reaction he'd started in her nethers.

"Am I in trouble for feeling weird? I feel like I'm in trouble again."

"No sweetheart, you're not in trouble."

"Oh, good."

He withdrew his hands, stepping back. His body heat faded away into the background, leaving her shivering in extremis.

"I know how to make the squirmy feeling go away," he said, voice shaking. He came closer and whispered warm breath in her ear. "If you let me, I'm really good at making good little girls feel calm and safe from the squirmy feelings."

"How?" was all Abbi could manage.

"It would feel just as weird at first, maybe weirder, than what Nurse Polk did to your bottom."

"How?" she begged again. "Why?"

"The squirmy feeling could be made all better if you let me massage the inside of your vagina."

"You want to rub the inside of my flower?"

"Oh, yes, young miss."

"I heard when a man and woman love each other, he can ask the woman to kiss his thing before rubbing it inside her flower."

"Did you now?"

"Yes, and the man will kiss the woman's boobies, and squeeze her butt, and they get naked and roll around and stuff."

"Do you understand what you are talking about?"

"S-E-X." Abbi spelled out. "Like what we were looking at on the homework."

"That's right, Miss Abbi. You can say the word, you aren't going to get into trouble."

"Sex," she blurted out. "Do you want to rub the inside of my privates with your thing?"

She heard Mr. Cleveland move around to the side of the chair, hiding the sight of her blooming flower, puckered butthole, and sweet cheeks as too great a temptation.

"More than anything, young miss." He finally answered.

All she could think about was getting that dick inside her, so Abbi leaned back again to get a good look at him, get a better read on how to proceed.

"Is that cuz you love me, sir?"

"Oh, no, sweetheart," he said, crestfallen. "We can't, Miss Abbi."

"What? S-E-X? Or be in love?"

"Both, I'm afraid."

She stood up to approach him, panties finally falling to the floor. He held is hands up, warning her to stay away.

"Can't we just pretend for now?" She didn't understand how pretending would seal the deal, but it seemed like an innocent enough thing to ask to keep the game going.

Mr. Cleveland just shook his head.

Abbi stepped closer, looking up at him with the puppy-est of puppy-dog eyes.

"We can't Miss Abbi, it's forbidden."

Abbi resorted to hugging him tight and pleading, muffled against his chest. He didn't hug back at first, but his breath hitched when she grabbed hold and she could feel his pulse through the erect cock that was pressed against her belly.

"Pleeeeease?"

He drew one arm across her shoulders and another cradling her head, reassuring.

"I think I have an idea, something that can help you with the squirmy feelings."

"You do?" Abbi looked up, real tears pooling in her big blue eyes. All her emotions had gone into overdrive, and the sensation of embracing, her naked, him clothed, had nearly pushed her over the edge.

"Yes, sweetie, but you have to trust me."

"Of course, I trust you sir."

"What I have in mind might be a little scary at first."

"I won't be afraid if you say I'll be ok."

"You'll have to get back on the massage chair."

"I'm not done hugging you yet." She moved her tummy against his raging hard-on, feeling it shift under his trousers. "What is this, Mr. Cleveland?"

"That's my penis, young miss."

"Is it like this all the time?"

"No, dear, it only gets erect like this at special times."

"Is it um E, Er, um, E-wrecked because you love me?"

He looked down at her, wistful.

"It's ok Mr. Cleveland. You don't have to say it out loud." Abbi snuggled against his chest, holding on for a few more moments before he put his plan into action. "When it's wrecked, does your thing make you feel as weird inside as my flower does?"

"It doesn't feel weird to me, it just feels exciting and happy."

"Is that cuz you're a grown-up?"

He nodded.

"I'd like to make you happy, Mr. Cleveland. I give you permission to touch me with your thing even if it is against the rules."

He shook his head, but Abbi liked where this was going anyway.

"Ok, it's time to go back on the chair, Miss Abbi."

As bittersweet the end of the hug was for her, the growing anticipation of getting penetrated by this man was overwhelming.

Mr. Cleveland took her hand and led her the couple of steps back to the chair. She knelt on the leg supports and settled in once again, the pads still warm from before.

"Please be as still as you can, ok?"

"Ok sir," she answered, a thrill running through her whole body.

Mr. Cleveland knelt beside her and twisted a lever at the base of the chair. To Abbi's surprise, the pad supporting her torso raised while the arm and leg supports moved up and apart, leaving her supported by the chair in a doggy-style position.

Aw, yeah, she thought. It's fucking ON!

"I'm going to make sure you can't fall off the chair while I'm, uh...If any of the straps feel too tight, please let me know, ok?"

He threaded a nylon strap through a hole in one of the arm supports, closing the Velcro snugly over her wrist. He did it again closer to her elbow.

He wordlessly did the same on her other arm. She wanted to watch, but the new angle of the chair and its headrest made it difficult. She did her best to imagine what was happening, picturing it in her mind from afar.

"Have you ever been restrained like this before, Miss Abbi?"

"No sir," she squeaked. "Is this the scary part?"

"Are you scared?"

"A little, but it's ok."

He moved to her side, drawing a strap across her upper back and another just above her hips.

"What happens if I want to get off the chair, sir?"

"You know your safeword, right?" His voice sounded different, his tone calling for a short timeout.

"Yes sir."

"Ok, then," he sighed, proceeding to strap down her legs at the top of her calves and at the ankles right where her feet hung off in space.

Then there was nothing for another beat that felt just a little too long. Admiring his work?

"Is everything ok, sir?"

"Forgive me, Miss Abbi, I can't help but look at you now."

"Does it make you happy to see me like this?"

"Oh yes."

"Then, I'm happy too."

Abbi listened as he moved over into the corner where the rolling red metal box was. There was a couple of metallic snaps and other noises as he took the cover off of whatever it was, then the sound of him rolling it into position behind her.

"I'm starting to get scared again, Mr. Cleveland."

"I'm right here, dear. It's going to be fine. Is your vagina all slippery and wet?"

"I think so. It feels really hot down there. Do you need to check?"

"You do need to be properly lubricated," he stated, sliding his hand over her ass, down to her special place. His probing fingers found her sopping pussy. "Very good, sweetheart. All nice and wet."

Abbi sighed as his fingers lingered around her engorged lips.

"So, let's talk about what's about to happen."

He came around and knelt in front of her, looking dead-serious. She could only imagine how silly her face looked, squished into the donut.

"You shouldn't look back there, ok? It might scare you too much."

"What is it?"

"I'll explain, but I don't want you to look. If you want, I can put a strap here to keep your head down."

"I won't look, I promise." This was her first experience with hard bondage, and they were now far outside her comfort zone. Hearing her head might be restrained was so scary it hurt to think about.

"I believe you, princess," he confessed. "I have a special tool back there that's going to make you feel all better. It has a penis that will move around inside your vagina for as long as it takes to give you the most special feeling ever. Do you know what I'm talking about?"

"Sometimes I rub myself all over and play special games with my flower and it feels like an earthquake in my whole body. Is that what you are talking about?"

"Yes. It has a special name, that feeling. It's called an 'orgasm' and the machine will be using the penis it has to give you one. Once you have the orgasm, the squirmy feeling in your tummy should go away for a while. How does that sound, sweetheart?"

"It sounds so nice, Mr. Cleveland. Can't you just use your pe-pe-peanut to give me a gazzum? Wouldn't that make you feel better too?"

"I can't dear." That seemed to be his final word on the subject.

Abbi shifted around to test the bindings. He did his job well; they were tight enough to create a whirlwind of fear and reassurance. Her online Daddy told her often that real-life play sessions would feel this way, and to do her best to embrace both feelings, along with the physical sensations to get the most fulfillment.

She thought for a moment about how he looked on Skype the last time they played, back a few months ago now. He looked proud.

If he could only see me now, she thought.

Mr. Cleveland was still crouching in front of her, seeming to wait for some kind of sign from her, looking more excited than proud.

"Are you ready now, Miss Abbi?"

"Is it going to hurt?"

"It might be uncomfortable at first. The penis I put on there isn't very big, and I have lotion to make it easier for you to take."

"I want the peanut to be as big as yours."

"It's about the same, I think."

Abbi thought of ways she could talk him into doing a visual comparison for her, but the longer she dragged this out, the hornier she got, so she settled on:

"Ok, Mr. Cleveland. I think I'm ready. I'm really scared now, but you aren't leaving while the thing is inside my flower, right?"

"No, sweetheart, I'll be right here."

He stood up and disappeared behind her again.

"Just to be safe, I'm going to make the penis extra slippery for you, so it shouldn't feel bad when it first goes in."

Hearing him apply lube to the dong stoked the already raging fire inside her. There were other noises which she assumed were the steps he was taking to get the fucking machine started.

A Fucking Machine! Abbi squealed a little with the thought.

"Is everything ok, Miss Abbi?"

"Is it inside me yet?"

"No, almost there. You will know when it's happening."

Abbi had only seen a couple of videos featuring a fucking machine. Her favorite genre lately being age-play DD/lg porn (her Daddy gave her the link to the first one she ever watched, and oh boy!), the idea of being reamed out by something from the darker side of PornTube only confused her grasp of the situation.

"Ok, the tip of the penis is touching your flower now. Can you feel it?"

"Cold!" she gasped.

"Sorry dear, the lube and your body should warm it up quickly enough. I'm going to push it in a little now."

The sensation was enticing, to say the least. Her toys were all either of the realistic, fleshy type, or the firmer vibrating type. This felt too big and solid for her.

"Eww, it feels so weird!" she complained, but her heart was not quite into it. She felt like it was the right thing to say anyway.

"It's not all the way in yet. Can you be a big brave girl for this next part?"

Just fuck me already! This was even more maddening than when her Daddy would tease and torment her with orgasm denial when they played online.

"Aww," she whined. "Yes, sir."

Mr. Cleveland pushed the cock in a bit too far, nudging up against her cervix.

"Oof!" Only her gynecologist had ever plumbed so deep.

"Sorry! The machine needs to figure out how deep it can safely go, ok?"

The only answer she could offer was a moan as the machine started to move, tenuously at first. It was kind of nice despite the feeling that it was close to splitting her in two. Usually, her IRL boyfriends would pound on her for a couple of minutes, blow their load into the condom, and collapse next to her, leaving Abbi to take handle her own business after they had fallen asleep. Crazy that a machine was fucking her with more control and care than the last man who said he loved her.

"How does that feel, young miss?"

Mr. Cleveland's voice snapped her back into the moment.

"Ohh, it feels so wrong, sir. Are you sure this will make me feel better?"

"Um-hmm," he reassured. "I'm going to give you the thing that controls it in a minute. Can you hold on for me a little longer?"

"Yes sir," Abbi moaned.

The machine stared to pick up speed, pistoning into her, filling her too full on the inward stroke, leaving too empty a void on the outward.

"I'm going to experiment with a couple of settings, then I'll give you the remote, ok?"

"Unnnngggffff," was all that came out. Abbi closed her eyes and turned her whole attention inward, all her energy being pulled into the moment, the dildo steely and insistent.