On Principal

"Put your hands up!" The officer called out making Chip drop the system he was holding knowing he was screwed. As the officer did the routine of putting the cuffs on him and explaining the charges along with reading his rights he felt slightly defeated as they knew he was the one responsible for all the theft of this particular game system adding up to nearly sixty thousand dollars making it a felony.

4 months later

"Chip to the principal's office, Chip to the principal's office!" Came over the intercom making him sigh as tomorrow was his final trial date in which he knew he would be found guilty. Though he had a feeling this was to tell him he was being fully expelled, granted he didn't think it would take this long but Principal Celestia was somewhat understanding and gave him the benefit of the doubt.

He got up from his desk grabbed his stuff and started to make his way towards her office, though he wondered what she would say. As he checked in with the secretary he felt at ease for some reason, but he just figured it was because he had accepted he was screwed the day he was arrested. Not to mention Celestia never gave off an intimidating aura, more of a mother scolding her child vibe.

"Chip, you can go in now," The secretary said making him nod before getting up to go into her office.

Opening the door he was a bit surprised to see Celestia passed out on her desk making his eyes go wide. He had heard she hadn't slept in a few days but to see her so exhausted she would be asleep while working was a surprise. Closing the door behind him he went over shaking her and other various other things to wake her to no avail.

"Geez, she is really out..." Chip said as he looked at her as she was now in a new position.

She was now leaning back in her chair letting him get a good view of her decently exposed cleavage. Some thoughts were starting to stir within him as it seemed she wasn't waking up and seeing she was still breathing. He bit his lower lip as these thoughts only grew the longer he stared.

"I'm already going away for years, might as well do something more fun..." He told himself as he stepped back up to her.

He hesitantly reached out with one of his hands to grab her one of breasts, gently groping her to see if she would respond to it. Getting a little more confident he reached with his other hand and moved it into her shirt grabbing her bare boob with that hand. Her skin was so silky smooth, though he couldn't believe he was doing this.

As he continued though he could feel his dick harden more and more, granted he would have been turned on by her anyway. This was every Canterlot Hgh guy's dream to get to do this to either of the sisters, though he wondered how far he could get. He removed his hands before turning her chair away from her desk and stared at her for a moment while moving a hand down his own pants to stroke his member a few times.

Though he quickly stopped as he stepped closer to her again and slowly started to undress her starting with her overshirt which came off easily. He then started working on her normal shirt which was much more difficult but she didn't seem to stir, and once off revealed her blue bra. Seeing her this undressed he couldn't help but whistle a bit as she was very beautiful.

"Hopefully we have the time, and you don't wake up before I'm finished," Chip said as he undid her bra clasp letting her good-sized breast free. After he got the bra fully off he once again started to fondle her boobs again, this time even popping one of her pink nipples into his mouth and began to suck and nibble at it.

Though he froze a bit when he heard her give a little moan and he remained frozen with one breast in one of his hands while the other popped into his mouth he relaxed once he realized she was still asleep. It did make him want to go much further and by being very careful he managed to put her on her stomach on her desk without waking her. He quickly admired her ass before quickly grabbing it.

"Hmm, she really is a heavy sleeper I guess," Chip said as he squeezed her ass. Quickly pulling his hand away he started to work her pants off which was easier with her position as he pulled her pants down he also grabbed her panties as well.

This left her fully exposed making him bite his lower lip as he pulled down his own pants to reveal his fully hardened member. Kicking off his pants as he stepped forward grabbing her ass again before sliding that hand between her legs and slightly rubbing her slit to see her reaction. After seeing that she didn't react he put more pressure behind his finger going a little deeper but not fully penetrating her.

He could see her tense as he continued to tease her and give a little moan but this time he didn't stop as he kept a close eye on her. Though at this point he didn't care if she did wake up cause he was going to do this no matter what. After a little more teasing and getting her a bit wet he pushed his finger in her getting a slightly louder moan than before.

But once again he wasn't stopping and added another finger which as he moved them in and out she finally started to seem to stir from her sleep. This is what made him stop but he had a smile as she turned onto her back his fingers were still inside of her, and as she twisted to get onto her back she let out a moan. Though she wasn't fully awake it gave him the opportunity to withdraw his fingers and stood up spreading her legs and lining his dick up to her entrance.

"Hmm... w-what..." Celestia murmured as her eyes fully opened and after a few seconds she focused on him.

"Good, now I'll be able to freely hear you without worry," Chip said as she gave him a slightly confused look before she looked down to see her exposed body and he lined up at her entrance her eyes going wide.

"W-wait... Gaahhh!" She screamed out as he forced his way into the pure white woman in front of him. He kept looking at her as he let out a loud moan himself. Seeing her breast jiggle from the thrust, her hands grabbing the edge of her desk as her face contorted in a mix of pain and pleasure.

He did not wait as he pulled back leaving only his tip in her before thrusting back into her making her grunt as he managed to get most of his member in on that second time. Though he did stop for a second relishing the feeling of being inside of her making him realize that his tip was already kissing her womb with you still having a bit more left to get inside. Looking at her he saw her looking at him with her beautiful eyes that had formed some tears in the corner.

"I-I..." Celestia tried to speak but was cut off by a forceful kiss from his as he once again pulled back with the goal to get his entire length inside of her.

"You better be ready, 'cause I'm going to get it fully inside of you," He said after breaking the kiss before once again slamming back into her making her scream out as his tip slammed past the entrance to her womb and into the back.

Though he had already locked the door to make sure they were disturbed for a minute, his head was swimming with pleasure. He did not care as he started to thrust in and out of her making her give a mixture of moans of pleasure and grunts of pain. Not long after he felt her wrap her arms around him and digging her nails into his back.

"S-stop..." Celestia begged as he continued though as he looked into her eyes they told him she was starting to enjoy it, though with her nails digging into his back it wouldn't have been that hard to figure it out.

"I'm so c-close a-already..." He said making her eyes go wide as she could tell he wasn't lying making her whimper a bit.

"N-not...AHHH!" Celestia moaned out as her head snapped back as he hilted completely inside of her to unload.

"Yeess!" He moaned out as he shot rope after rope inside of the woman he could feel her break his skin as her grip tightened on his back. Though her grip loosened as her arms dropped limply onto her desk allowing him to pull out.

As he pulled out and immediately fell into her chair he looked at her breathing heavily as cum leaked out of her which made him wonder if she had also come from that. The idea made him smile, though that smile faded as she shakily managed to prop herself up looking at him with tears falling. Though her tears weren't why he stopped smiling, he wanted more lurching forward he once again locked lips with her making her fall back as it seemed she didn't have the energy to fight back.

"Hmmph!" Celesta moaned out as he slid his fingers down to her slit again and now that it was completely soaked made it easier for them to enter her.

He broke the kiss and removed his hand from between her legs he forced her to turn onto her belly, which again she didn't offer much resistance to. A smile formed as he knew she wasn't thinking about what this position would allow him to do, but he only added to that by sliding his rehardened member across her sensitive entrance. Though he did plunge back in just so he could feel the pleasure of her velvety tunnel making both of them moan out.

Withdrawing fully, he then lined up to her ass hole making her look at him with complete fear it seemed as he smiled at her. Before she had the chance to object he forced as much as he could into her tight tunnel making her scream out in utter pain. This made him toss his head back in complete pleasure from the way her ass was massaging him as if to try to push him out.

At this point though he could hear people outside of the door trying to get it open to see what was going on. He knew he didn't have much time but he also knew he didn't need much time. Quickly pulling out of her tight tunnel leaving just the tip in again he slammed back into her and forced the rest of his dick into her.

"GGaahh! I-it hurts!" Celestia managed to stammer out with full-blown tears streaming down her face. Though something clicked, while her voice was laced with pain it seemed she was enjoying it as well making him wonder if she enjoyed the pain.

It all didn't matter as he just wanted to make the most of this before they were interrupted as he started to thrust in and out. He was on top of the world as he was fulfilling one of his fantasies of having sex with the hottest woman in the entire school. Not long though he felt himself start to get close again.

"A-almost done!" He shouted out as Celestia only responded in pained moans as he hilted inside of her unloading into her ass and making her snap up where he could feel her squirt onto his legs. Though he managed to pull out of her ass while he was still unloading squirting some cum onto her ass before shoving his member into her convulsing pussy to finish up.

As they both came down he instantly fell unconscious onto the ground as he fell and his member pulled out of her with a loud pop. Celestia seemed to have lost consciousness for a moment which she quickly regained as the door swung open to reveal Luna. They seem to share a moment before Luna shut the door.

"Nothing is wrong, she was just having a nightmare," Celestia heard Luna say from outside.

"Gee, gonna be sore for two weeks," Celestia said as she rubbed her ass, though she frowned as cum leaked from her pussy. "Damm it, forgot about birth control."

She looked at the unconscious Chip, she really hadn't expected him to be so bold as to rape her while she was asleep. Though, she wouldn't necessarily call it rape since she had wanted to fuck him anyway before he was sent to prison, though her exhaustion had taken hold. Looking at him though, he was still very much hard.

"After fucking me in my both holes, you're still hard. This is why I like younger men," Celestia said to herself as she knelt down grabbing ahold of his dick giving it a little kiss at the tip giving a little smile. "Guess it's my turn."

She quickly inserted his member into her mouth humming making him moan and his eyes shooting wide open as he gave her a confused look as she bobbed up and down. He let out moan after moan as she swirled her tongue and as he looked he could see she was leaving behind pink lipstick. All of it was confusing but he grabbed the hair on the back of her head forcing her to stop as once again he moaned out cumming inside of her mouth.

"Good, now that we've had our fun let's talk about what's gonna happen next," Celestia said as he let go of her letting her swallow the cum still in her mouth as his member started to go limp finally. The way she said that made him shiver a bit as he did wonder what she meant.