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Abby’s Adventure

Category: Anal Sex
13.09.2019
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She sat sullenly outside his office, kicking at the leg of the chair with the heel of her black loafer. She knew this was it. She was going to get expelled for sure, and there wasn’t a damn thing she could do about it. She silently cursed her rotten luck. Just then the door opened.

“He’ll see you now,” the voice said She looked up and saw the short, middle aged woman with soft gray hair smiling sympathetically at her and stood up to face her fate.

Taking a deep breath, she walked slowly into the office and closed the door behind her. She knew the routine. This was the fourth time this semester she’d been sent here to face him, and she was very frightened of her fate. He was not an easy man to sweet talk, especially when the punishment was deserved.

The first time was for back talking the sister who taught English class. That had gotten her a stern lecture. A couple weeks later, she’d been caught with a pack of cigarettes in the girls bathroom. She lied and said they weren’t hers, claiming that she’d found them on the floor and was merely going to throw them away. She got detention for 3 days for that. They couldn’t prove they had been hers, so she weaseled her way clear from a more severe punishment.

The last time, she’d been caught cheating on a midterm exam. For that, she’d felt the sting of the dean’s hand across her backside. It was 2 days before she could sit comfortably at school. That time, she also got grounded by her parents for 2 weeks. She was also informed that next time she’d be expelled. Her father also gave her an ultimatum. Either behave in school or the next time, he was going to spank her. 18 or no, she was still his child and it was his right to discipline her how he saw fit.

Well, here she now was. Facing Dean Gregory Thomas and his stern justice. He looked up from his paperwork and scowled. “I’m not happy with your behavior, Abby. Sister Margaret has told me some disturbing things. What do you have to say for yourself?”

Abby gulped. This was it. There was no way of explaining the soda bottle of alcohol she’d been carrying around with her. She had only wanted to try getting through a day without getting caught. She thought that nobody would notice that she was drinking in school. She wasn’t drunk, after all. It was just her luck though, that Sister Margaret walked around the corner into her spilling it as she was taking a drink and recognized the odor. She’d been busted.

Abby only shook her head slowly, knowing anything she said would make it worse. She knew she’d be expelled, and she’d get spanked and grounded and lose her car when her parents found out. Dean Thomas stood up and walked to the window. He cleared his throat and then began.

“Abby, I haven’t spoken to your parents yet. This is a very serious offense. It’s also the fourth time this semester that you’ve been sent to see me. You know that the extent of this act could get you expelled for the rest of the year, in which case, your tuition would be forfeit and you would have to attend the entire of next year to graduate. I doubt your father will be happy over that. He swore last time you’d get a rather severe punishment should you misbehave again.”

Abby looked at her shoes and said softly, “Yes, Sir. He said he’d spank me.”

Dean Thomas turned to face her. “Abby,” he stated, “we both know he’ll do more than spank you. You can bet that you’ll find yourself grounded for the rest of the school year and probably all of the next, plus losing all privellages. You may be 18, but that will mean nothing. You will have no choice but to live there in order to finish the school year. You also have your college education to look at. He doesn’t have to help you there either.”

Abby nodded again. She knew he was right. She just didn’t know what to do about it.

“I’m prepared to forget this little incident ever happened, Abby, but it will cost you.”

She looked up, astounded, not fully comprehending what he was telling her. He chuckled at her expression. “What are you talking about, Sir?” she asked quietly.

“Abby, right now, you don’t have much to bargain with. I can make or break the rest of your life right now. I want you to think about that. How much is too much to save your ass?”

This shocked Abby even more. Dean Thomas never talked like that to the kids in the school. Not even when he was fuming and raging at them. Abby took a deep breath and asked, “What do I have to do?”

He smiled. “First of all, you are going to get your pretty ass spanked. I don’t mean like the last time either. Last time, you were covered by your skirt and underpants. This time, you will not be protected by anything. Your bare skin will feel the sting of my hand.”

Abby paled, knowing she was in for it. It had hurt the last time and she’d at least had the protection of her clothes. The man knew how to swing his arm and make a girl squirm. She also knew, though, that her father would do the same if he found out. She agreed.

Dean Thomas smiled again. “Good. That’s a very good girl, Abby. There’s also one other thing. You will accept anything that I do to you without protest. If at any time, you want me to stop, I will. But then I will immediately ring your parents and tell them of your little stunt with alcohol and let them deal with you from there.”

Once again, Abby nodded her head, knowing he was right. He reached down and held out his hand, taking hers and helping her up. “Please remove your skirt, Abby.”

She unzipped her short tartan skirt, stepping out of it, standing before him in her white blouse, panties, white knee socks and black loafers. She folded it neatly and placed it on the chair she just vacated. “Now the panties,” he said softly.

Abby shivered with embarrassment and fear. She knew this was going to hurt. She also knew that once she did that, she would be exposed. She was a student, but also a young woman and he was a 30 year old man, very attractive and very intimidating all at once. She slipped her feet from her loafers and slowly slipped her panties down her hips, depositing them on her skirt and nudging her shoes under her chair with her stocking feet.

She shyly cupped her sex with her hands, shielding her mound from his gaze. She flushed, hoping he hadn’t noticed that she was shaved. Her boyfriend Alex liked her bare, so she felt the urge to comply. Besides, it made it easier when she explored her own body at night.

“Please bend over the table there, Abby. Reach across and grab the other side and don’t let go. I want you also to spread your feet apart, about shoulder width. That’s a good girl.”

Abby did as she was bid, knowing she had little choice. She shivered as she felt his eyes on her. She clenched her eyes shut tight and prepared for the blows to fall.

Behind her, Dean Thomas stared with utter appreciation at the young woman spread out before him. The creamy skin of her ass and thighs was causing an erection that threatened to bust his zipper. And the little minx was shaved, her sweet young pussy a pretty shade of pink that begged to be licked. He gritted his teeth and crossed to stand beside her. He rested a hand on her waist and took a breath before speaking. “Abby, I’m going to spank you now. Please stay in this position. I don’t want to have to hold you down anymore than this. I would hate to have to restrain you for this.”

She nodded, her eyes scrunched tightly shut, waiting for the first blow to fall. She started as she felt his warm hand come to rest on her bottom for a moment before he pulled it back and delivered the first blow. She clenched her teeth and sucked in a breath, shocked at how much it had hurt. A bright red handprint rested on her rump, staining it. Dean Thomas shivered in anticipation. This somehow was turning him on even more, seeing the handprint resting there on her left cheek. He quickly followed with another to her left, making her jump once again.

He pressed down a bit harder on the small of her back with his hand, making sure she stayed bent across the table. He rained blow after blow across her bottom, turning it pale pink to bright to red. Somewhere along the line Abby’s cries of pains had turned into soft moans. He snapped into reality and realized something was different. Looking down at her bottom, he saw moisture trickling down her thighs. He gaped as he realized this girl was turned on by the punishment he was dealing out to her. The shocking thing was, he was turned on by delivering it.

He stopped, his hand still resting on her bottom, feeling the heat of it rising into his palm. He slid his hand down between her legs and cupped her sex. Abby cried out, shuddering in pleasure as his fingers sought her dripping pussy. He sank his fingers into her sweet wet walls, feeling her warm walls contract and draw him in deeper. He brought his other hand under her and around in front of her, seeking her clit. He found it, that throbbing little nub, and rolled it with his thumb while he sank his fingers in again and again into her burning sex.

Abby groaned. “Ahhhh, Dean Thomas. Yes, that feels so good!”

Dean Thomas gritted his teeth and hissed, “Call me Greg, Abby. Right now, I’ve got my fingers in your cunt and I’m about to fuck you. I’m just Greg right now.”

“Yes, Greg, yes! Ah, God, that feels so good!” Abby gasped.

She shuddered then, crying out as she came and soaking his hand in her sweet juices. Pulling his fingers out of her still-pulsing vagina. he reached for his zipper, managing to clumsily undo his pants in an amazingly short amount of time, freeing his aching, straining cock from its confines. With his other hand still stroking her clit, he sank his full length into her, groaning as she enveloped him in her velvet walls. He pulled back, and then plunged in again, giving her his full length.

He fucked her slowly, thoroughly, taking his time and keeping her young body thrumming with pleasure. He paused once, pulling his cock out almost all the way, and slid his thumb deep into her, feeling her juices flowing freely. Removing it, he brought it to her anus, circling it slowly. He teased the sensitive membranes, while keeping her in a constant state of near orgasm with his cock and fingers.

He slowly sank his thumb into her ass, nothing her gasp. “Relax, Abby. Just breathe. Go with it, sweetness.” He felt her ring open almost immediately, and eased his thumb in a little deeper. He groaned and clenched his teeth, fighting the waves of pleasure that threatened to overtake him. Not yet. He wasn’t ready yet.

He slip his cock from her pussy and put the head of it against her asshole. He groaned loudly, “Breathe, Abby, just breathe. I swear I’ll go slow, just breathe!” He pushed himself slowly but firmly against her, the head of his cock popping in before he halted his movement. He felt her tense and heard her cry out. Greg rubbed her clit again and stroked the soft skin of her back. He reveled in the imagery of it. Her Hair a mass of red tangles against the table, the bright red skin of her bottom from the spanking he’d given her a few minutes ago, his cock in her ass. It was all more than he could take. He began to move into her, slowly at first, giving her time to adjust.

Abby moan loudly, shivering with the sensations flooding her young body. Greg’s cock was stretching her ass, filling her, while his fingers were now moving in and out of her aching pussy. His thumb rolled on her clit, sending shockwaves of pleasure crashing through every nerve of her body. “Oh Greg, I’m gonna cum again!”

Her body tensed and she shuddered through her orgasm. Greg cried out as she came hard, her pussy drenching his hand and clamping around his fingers, while her ass gripped his cock tightly. He roared, thrust into her a few more times before he joined her in the vortex of orgasm. His body jerked a few times, then he collapsed on her, pinning her to the table with his weight.

Slowly, his head cleared and he regained his senses. Realizing he still had his cock in Abby’s ass, he slowly disengaged himself from her, easing out and off of her. Reaching out a now gentle hand, he caressed the flaming flesh of her bottom, his handprints still clearly visible on her pale skin. “Your parents will never find out about your little lapse in judgment, Abby. Nothing will be noted in your permanent record. I think you’ll do just fine for the rest of the year.”

Abby smiled softly as she stood up. She walked slowly across the room and retrieved her skirt and panties. Slipping them on, she stepped into her loafers once again. She turned to face him with a naughty glint in her eye.

“Dean Thomas, something tells me I’ll do fine in my studies, but I also have a feeling the Sisters will need to send me here a bit more often because of my behavior.”

Greg’s jaw dropped, and Abby laughed as she turned and walked out the door. Her face bore a look of complete satisfaction as she began scheming what to do next to get sent to his office. This would definitely be a very good year.

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