The Sexual Misadventures of Flash Sentry

by SubBasementQ

Rating: mature
Tags: Flash Sentry, Anthology, Main 7 (EqG), Principal Celestia, Vice-Principal Luna, Porn, Fetish, Comedy, Non-consensual, Equestria Girls, Sex
Length: 3269

An anthology of Flash Sentry's ridiculous sexual exploits.

An anthology of the various (but unconnected) sexual misadventures of Canterlot High's second favorite hapless dork. No situation is too ridiculous, and only a few fetishes off-limits.

So join Flash as he finds himself in a variety of silly sexy situations that shouldn't be taken too seriously, won't you?

All characters depicted are, of course, 18+ years of age.

Cover Image by Excelsio36.

Published 2021-11-20 19:00:01 UTC
Last updated 2021-11-20 19:00:01 UTC

The Pilot Program

There were many things Flash Sentry expected to happen when he was called to Principal Celestia's office; a conversation about his grades, his imminent graduation from high school in a few months, his future college plans. She took an interest in things like that with her students.

He was not expecting Vice-Principal Luna to be there. Flash had never been a discipline problem in all his years at Canterlot High, so he never really interacted much with her.

And he most definitely was not expecting both of them to tower over him and start taking off his clothes. At the moment, Luna was standing behind him, tugging off his hoodie, while Celestia stood in front of him, reaching for his belt.

“W-wait, what?” Flash said, as his brain tried to comprehend both what has happening and what he had just been told.

“I said, we've decided it would be better if you attended school in the nude for the rest of the year, Flash,” Celestia said matter-of-factly as she undid his belt buckle. “It's a new program we're wanting to test.” She yanked the belt swiftly out of the loops of his jeans with a “ziiiiip” sound as leather brushed denim.

“A program where I have to be naked?” Flash asked, his face turning red. Luna finished removing his jacket and began pulling his shirt over his head.

“Yes,” said the vice-principal, as she raised Flash's arms so she could remove his shirt. “We've found a recent study which suggests prolonged public nudity can help reduce shyness and increase confidence. We've decided to try it out with a test case... and we chose you.”

“But, I'm not shy!” Flash protested. He turned to look back at Celestia and gulped as the administrator dropped to her knees in front of him and began undoing the front of his pants. “Uh... s-seriously. I don't have a problem talking to people.”

“And yet,” countered Celestia, as she popped open the button of Flash's pants and began to slowly pull down the zipper. She looked up at him with a sultry look in her eyes. “We've noticed how you haven't dated anyone ever since Princess Twilight stopped visiting.”

Flash let out a yelp as Luna wrapped her arms around him from behind and rested her head on his shoulder. “Yes, and that's not good for your well-being. You've been pulling away from your friends, your classmates, even your teachers have noticed you don't participate in class much these days.”

Flash swallowed, acutely aware for the weight of Luna's head on his shoulder, her breasts pressing into his back, Celestia's hands as she gently lifted each of his feet to take off his shoes, then placed them on his waist, her fingers tucked into the waistband of his jeans.

He also felt his penis beginning to harden and he blushed even deeper. Ohgodohgodohgod...

Celestia gave him a knowing smile. “Look how red your face is, Flash. That's not the look of a young man confident in himself. Why, most men in your position would be thrilled to have two experienced women undressing him and would have a huge grin on their faces at least. You're definitely the ideal candidate.”

Celestia began taking Flash's pants down. Flash raised his hands to stop her, but Luna grabbed his wrists.

“Ah-ah,” Luna chided gently. “This is happening, Flash, and there's no getting out of it. So be a good boy, and let Principal Celestia take off your pants.”

The two sisters exchanged a knowing look and Celestia tugged Flash's jeans down to his ankles. Flash swallowed again as Celestia encouraged him to lift his feet one at a time so she could remove them completely. He was really wishing he had worn a pair of boxers today instead of white jockey shorts. Celestia got to her feet, noting the bulge in the front of Flash's shorts. Her lips curled up in an amused smile.

“This is for your own good, Flash. You'll see. Everyone will see what a handsome virile young man you are,” she said, putting a hand on one of his shoulders and guiding him closer to the desk. She turned him so his back was to it. Luna walked around to the other side, pushing Celestia's office char away so she had room to stand behind it.

“And when graduation comes, you'll be able to stand proud and tall when you collect your diploma,” Celestia continued. “And it will all be thanks to this program. Canterlot High thanks you for your willingness to participate.”

“But I--” Flash was interrupted when Celestia gave him a gentle push so he was sitting on the desk. Luna put her hands on his shoulders again and gently tugged him back, resting his head on her chest. She crossed her arms over his chest, holding him gently, but firmly, in place.

Flash stared, confused, terrified, and aroused as Celestia reached out and slid her fingers into the waistband of his underwear. His panicked brain raced as he tried to figure a way out of this, finally latching onto something that might work.

“My mom!” he cried. Celestia frowned and made a quizzical noise. Flash nodded rapidly.

“I don't think my mom would approve of me doing this!” he said, practically shouting. “I mean, she... she, uh, she--”

“Has already given her permission,” Celestia said.

Flash blinked. “What?”

“Well, you didn't think we wouldn't talk to her first before setting all this up, did you?” said Luna with a small laugh. “That would be unethical!”

“Indeed,” said Celestia. “We explained what the program hoped to accomplish and she gave her enthusiastic consent. She's had the same concerns we've had about your social withdrawl, so she feels this will help you as well. Now, let's have those undies off, shall we?”

Before Flash could say anything more, Celestia whipped off his underwear, leaving him clad only in his socks on the top of the desk. His face went bright red as his erect penis slapped onto his abdomen.

“Oh my!” said Luna in mock surprise. “Sister, dear, it appears this has been a bit too much for him. Look at how... turgid he is.”

Celstia made tsk-ing sounds with her tongue. “Now, Flash, what sort of impudence is this? We can't send you back to class with an erection. It's very rude.”

“Uhhh... sorry?” Flash said, unsure of anything else to say, then let out a yelp as the principal reached out and cupped his testicles in her hand. She gently squeezed, causing Flash to let out a moan.

“My my my,” Celestia sighed. “It appears all of this has been a bit too much for you. I suppose there's nothing for it.” She looked up at Luna. “We're going to have to drain him before we can move forward.”

“Drain?” Flash asked. The two administrators ignored the question.

“I agree, sister,” said Luna. “It really is the only way.”

“Right,” said Celestia, looking back down at Flash. She gently squeezed him again. “Now, you are going to be a good boy and let us drain you, aren't you, Flash? We simply cannot let you out into the halls like this.”

“I... I guess?” Flash answered. “I mean... um... you could just give me my clothes back?”

Celestia smiled and shook her head. “Now, Flash, don't be difficult. You've been selected for the program and we're going to ensure you do your duty. But first... Luna?”

Luna leaned over and Flash yelped as she grabbed his ankles and pulled, leaving Flash flat on his back on the top of the desk. Luna spread his legs wide, leaving him fully exposed. Celestia walked around the desk, opened a drawer, and extracted a tube of lubricant and a latex glove. She pulled the glove on as she returned back to the front of the desk.

Flash looked up at her with trepidation. “What are you doing?”

Celestia gave him a smile that was meant to be reassuring, but seemed, to Flash, to have a dangerous edge to it. “In order to completely drain those naughty testicles of yours, I'm going to massage your prostate.”

She applied some of the lubricant to the fingers of her gloved hand. She stepped between Flash's splayed legs. “This will help you ejaculate aaaaaaall of that semen you have backed up and then we can send you back to class without the distraction of this...”

Celestia reached out with her ungloved hand and gently patted Flash's now fully-hardened penis, causing him to inhale sharply. “... and you can get on with your day!”

Celestia slipped her lube covered fingers between Flash's buttocks and up against his anus. Flash sucked in a breath as the cold lube came in contact with him. Celestia gave him another smile.

“Just relax. I'm going to slide my fingers inside you now.”

“Inside?!” Flash yelped. He tried to get up but Luna yanked on his legs again, and Celestia pushed on his chest, forcing him back down.

“Now, Flash, you've been such a good boy so far,” Celestia said, a cold note entering her voice. “Don't cause a fuss now. Yes, I have to go inside you to reach your prostate, but it's going to feel soooo good, don't worry.”

“Yes,” Luna agreed. “You don't want to wind up in detention, do you?”

“Detention?” Flash asked, looking up at the vice-principal.

Now it was Luna's turn to smile. “Yes. Which means more time spent naked on school grounds... and possibly a spanking as well. Now, you don't want that, do you?”

Flash swallowed. “N-no.”

“Good. Now, relax and let Principal Celestia milk you. You'll feel much better afterward.”

Celestia didn't wait for Flash to respond. She took advantages of his distraction and pushed her first two fingers inside him, causing the boy to cry out in surprise.

“There we are,” Celestia cooed. “That wasn't so bad, was it?”

“Aaaaagghh,” Flash replied as he felt the older woman's fingers slide deep into his rectum. A squirming sensation that quickly turned to a sharp tingling sensation of pleasure as her fingertips came in touch with the firm round bulge of his prostate.

“There it is,” smiled Celestia. She picked up the tube of lubricant and flicked the cap open with her thumb. She upended it over Flash's groin and drizzled more lube onto his penis. Flash let out another hiss of air between his teeth as the cool goo came in contact with his hot skin.

Celestia put the tube back down and then reached down and gently took Flash's penis in her other hand. “And now we can begin.”

She began to stroke him, smearing the lube along his rigid shaft. Flash's head went back and he let out a moan as the pleasure began to overwhelm his brain. The two sisters smiled at each other, and Celestia redoubled her efforts, not only stroking Flash, but she began pumping her fingers in and out of his ass, pressing her fingers into the button inside him.

Flash's own discomfort was quickly overwhelmed by the sensations of pleasure coursing through him. Every prod of Celestia's fingers sent an overwhelming surge of pleasure to his penis, which itself was being ruthlessly stimulated by Celestia's incessant stroking. He found himself letting out gasps and moans as the two administrators smiled down at him, pleased with the emotions they were eliciting from the boy.

“There we go,” Celestia said, increasing the speed of her strokes. “Just relax, Flash. Let it all out. Don't hold back. It's for the best.”

“Yes,” Luna agreed. “It will all be so much better when you've had everything milked out of you. Be a good boy and give us what we want.”

Celestia curled her fingers inside Flash's ass and began rapidly brushing the tips back and forth across Flash's prostate. The feeling of pressure in his penis increased and Flash cried out. Luna quickly slapped a hand across his mouth.

“Shhhh... you don't want to get too loud,” she whispered into his ear. “Why, someone could come in here to investigate and what would they think? Oh, my! What if someone sees you being milked so thoroughly by your principal and your vice-principal? It will be all over the school! No, no, you're going to be a good boy and be quiet, aren't you?”

Flash moaned into her hand again, causing the two sisters to exchange another mischievous smile.

“Well, I suppose it IS a bit overwhelming,” Celestia said, jabbing her fingers hard into Flash's prostate, letting out another loud muted moan. “We'd better finish this up.”

She redoubled her efforts and looked down at Flash, who met her eyes. “Now, come along, Flash. I want a nice big ejaculation from you. I want you to pump out as much as you can. It's important.”

Flash began thrashing on the desk, causing Luna to lean over him to hold him in place, her breasts pressing into his face. Flash let out a surprised muffled “Oof!” as Luna's chest nearly smothered him.

Celestia used her thumb to tease the sensitive spots directly under the head of his cock. Flash's back arched sharply, before crashing back onto the desk.

“Oh, GOOD boy!” Celestia cheered. She resumed stroking. “Such a good boy. Now, give me your semen, Flash. Give it all to me. Keep being a good boy and let me have it. Let it aaaaaaall out. Empty your testicles. Right now!”

Flash screamed into Luna's chest as he went over the edge and his penis began spewing semen into the air, causing it to slop down his shaft, onto Celestia's hand, and onto his abdomen.

“Therrrrre it is! Good boy! Such a good boy! Look at all of that!” Celestia cheered, not ceasing her stroking of Flash's cock and prostate, wringing more moans from the delirious teen. “Keep going. I want every single drop.”

To Flash, the torment seemed to go on forever as Celestia manipulated his penis and kept punping her fingers in and out of him. His hips bucked as his body tried to escape the stimulation. In actuality, it was only a few more seconds before Celestia finally let go of his cock and let him relax. Luna stood back upright. Flash lay on the desk, breathing heavily as he came to his senses, letting out a sharp yelp as Celestia yanked her fingers from his anus.

“Good boy,” Celestia said, shucking off the glove. “Just lie there and catch your breath, Flash. I'll be with you in a moment.”

She pulled a handkerchief out of her jacket pocket, then looked at Luna. “Could you get that thing we talked about earlier, please, Luna? I think we're going to need it.”

Luna nodded and left the office. Celestia turned her attention back to Flash. She smiled as his peins began to deflate and she used the handkerchief to begin cleaning him up.

“There, that wasn't so bad, was it?” she asked as she wiped up the residue of Flash's orgasm. Flash only let out another moan. Celestia smiled.

“There, there, just relax. We just have one more thing to do before we let you go back to class.”

She finished cleaning her student up and tossed the handkerchief in the wastebasket as Luna came back into the office, carrying a small bag. Celestia took it from her and turned to Flash.

Flash himself was finally starting to regain his senses. He took a deep breath and squeezed his eyes shut, trying to clear his head. He felt lightheaded and dizzy. He took a few deep breaths, then his eyes popped open as he felt something hard and cold being clasped around his genitals.

He propped himself up on his elbows and then upright and stared at the bright pink plastic... thing that his penis had been slid into and cupped around his balls. There was a hole at the end of the protrusion that sheathed his cock.

“What the hell?!” he said, looking up at the obviously amused sisters.

“Well, we need to make sure you don't get another erection while you're in class,” Celestia explained. “This little chastity device will make sure that doesn't happen.”

“And you don't need to worry about needing to use the restroom,” Luna added. “That's what the hole at the end is for.”

“But, why?” Flash asked, getting off the desk. He frowned at the odd sensation of the plastic chastity cage containing his junk. “Why do I have to do this?”

“Because you're the best candidate!” Celestia replied. “If you show that you can overcome your shyness, it will inspire many other students to break out of their shells!”

“That's not what I --”

But he was interrupted as Celestia continued. “Now, this what we're going to do. Every day before school, you will report to my office where Luna and I will milk you and get you locked into your cage – “

“My cage?” Flash asked, but Celestia kept going, ignoring his outburst. As he stared at Celestia, Luna came over and gently pushed him into the chair in front of the desk, then began putting his shoes on his feet.

“ – and leave your clothes here,” Celestia continued. “Then, at the end of the day, you'll come back here and one of us will unlock you and let you have your clothes back so you can go home. Understand?”

“No,” Flash answered, standing up. Luna also got to her feet and rejoined her sister. “I don't understand. This whole thing is just weird and – “

He was interrupted again as the bell signaling the next class change. Celestia grinned and put and arm around Flash's bare shoulders, gently pushing him towards her office door.

“Oh, I'm sure there'll be a period of adjustment, but after a few days, everyone will get used to it. And don't worry about your teachers. The faculty has been fully informed so don't worry about getting into trouble. If anyone gives you any grief, let me know and I'll have a word with them.”

“Now,” said Luna, hading Flash his backpack. “Off to class and we'll see you after school!”

Celestia opened the door. “Have a good day!”

Flash blinked as Celestia ushered him toward the open door. “Wait! Hang on! I – YIPE!”

The “YIPE!” was because Luna had given him a short, but not hard, slap on the ass, which caused him to jump through the door and out into the crowded hallway. Celestia closed the door behind him and smiled as the students outside, and Flash himself, let out shrieks of surprise at the presence of a naked boy in their midst.

“Well,” said Luna. “This should be interesting.”

“Oh, you just like the idea of making him cum every morning and locking up his cock afterwards, you sadist,” Celestia smirked.

“Well, that is a side benefit,” Luna admitted. She snapped her fingers. “Oh, damn! His mother wanted pictures of him in the cage!”

“We'll take some when he comes back for his clothes,” said Celestia.

Luna nodded. “Well, I guess we should get back to work. I'll be back after school.”

“Have a good day, Lu!”

After Luna left the office, Celestia began gathering up Flash's clothes, folding them up and placing them in a drawer of her desk. She sat down and turned her computer back on.

“Such a lovely day,” she murmured, idly remembering the look on Flash's face as he orgasmed all over her hand. She shook her head and got back to work.