Caught Red Handed Pt. 03

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Marc loses his anal virginity.
3k words
4.67
52k
105

Part 3 of the 4 part series

Updated 06/09/2023
Created 02/19/2020
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You guys have voted, here are the results. A story where readers get to vote on what happens next. You guys picked the plot and you guys decided on what will happen. All characters engaged in sex are of the age of 18 or older.

*****

Walking into school, I feel a bit nervous. What if Jude knew I was under the desk sucking Principal Davis's dick? Rumors would spread like wildfire and everyone would think I'm gay or something. "Mr. Weeks. Principal Davis would like to see you," Mrs. Stanton says, Principal Davis's secretary. She's a very attractive red-headed woman with knockers slightly smaller than soccer balls. Does she have a dick too? Does every woman have a dick? Of course not. Now I'm just being stupid.

I follow her into the front office. "Have a seat, she's currently busy with a new student."

I sit and wait. What is she going to make me do now, suck her cock again? Will I ever get out of this? Is this how the rest of my time at school is going to be spent? On my knees sucking my principal's cock? What if she wants more? What if she wants to...

A chill goes down my spine as my entire body shakes at the thought. I'm pulled out of my own head as the door to her office opens up and a tall gorgeous blonde girl walks out with a kid I know... what's his name? Riley, I think? Principal Davis follows them out. "I'm glad you chose our school, Ms. Cummings. Your education is of our utmost importance. Mr. Owen is certainly one of our brightest students and I'm glad you two are already close. He will be able to show you around."

"Thank you very much," Ms. Cummings says, biting her lip. I've never seen eyes like hers before, they're purple. Probably contacts.

"Come on," Riley says. "Let me show you to your locker."

She follows him out of the Principal's office.

"Mr. Weeks, just the person I was hoping to see. But unfortunately, I have a meeting. I would like to see you after school. It may take up a large chunk of time, so don't make any plans."

"Uh... Yes, Principal Davis," I swallow down my nerves as she gives me such a wicked smile and a sly wink.

"Now be off. I wouldn't want to make you late for your first class," she says.

I scurry off out of there as quick as I can. My mind filling up with all sorts of lewdness. I don't even think I can imagine what she has in store for me after class. I feel trapped. Not able to say no without reaping such severe consequences. And yet... Part of me is almost excited. The feel of her thick cock as it slid across my tongue was unlike anything I've ever dreamed of. Just thinking about that strong musky scent makes my mouth water. The way she asserts control and the touch of her hands through my hair as she pushes that cock between my lips. I nearly jump out of my pants as a hand lands on my shoulder. "Woah. Relax, man, it's just me. You were off in space or something," Anthony says.

"I... I was just thinking about our history quiz... That's all, " I mutter.

"Sure... Okay." Anthony laughs. "Dude, you know you're pitching a tent right now, right?"

I look down at the horror of my dick trying to break through the prison of my jeans. I quickly grab my books and hold them in front of my crotch.

"Anyway... I guess that tranny girl... Mackenzie, the one who is somehow dating the new starting quarterback, god only knows how that happened. I guess she's throwing a party on Saturday," he says.

"I don't think they like being called that," I say.

"Who cares. She, he... whatever pronoun they refer to themselves as is still a biological boy. You can't argue with science," Anthony says.

I let out a sigh. "I take it you're not planning on going?" I ask.

"Are you kidding me? I doubt anyone's going. No one wants to be seen with a tranny," he says.

"Dude, don't call her that," I spit out.

"What's gotten into you?" he asks.

"Nothing," I say. I certainly don't want to give Principal Davis any more ammunition to use against me. "Is Noah going?"

"Who cares. We can't be seen with him. It'll ruin our chances at ever being popular," he says.

"Why do you care so much about being popular?" I ask.

"And you don't care about what everyone else thinks about you? If we get popular, we can finally get laid. Maybe I can get a chance with Lauren Day," he says.

I let out a sigh and roll my eyes. "Whatever."

As we sit through class, my thoughts are only one subject, Principal Davis and her big fat cock. What if she wants to... What if she wants to put it up my butthole? I'm not ready for that. I don't think I'll ever be ready for that. And yet, why can't I stop thinking about it?

"Marcus, would you care to answer?" Ms. Whitney asks.

"Uh..." I look up at the board at her equation. Great, integrals. I'm not good at those. "I umm. I don't know. I'm sorry."

"Maybe if you paid closer attention to the lecture, you'd be better equipped to tackle such an equation," she says. Does she have a cock too?

At lunch, I meet up with Anthony at our table. We both watch in silence as Noah, dressed in a plaid skirt and white blouse walks by us along with the four girls he hangs out with now. He glances our way, but his eyes quickly run away. "He really does look like a girl," I mutter. A hot one at that.

"What is going through his head to just dress up like that?" Anthony asks. "Does he honestly not care what other people think of him?"

"Is that such a bad thing?" I ask.

"When it causes you to dress up and pretend to be a girl, yeah," Anthony says.

"I don't know, maybe we're being too hard on him," I say.

"Are you honestly siding with him?" he asks.

I sigh. "I don't understand why you're so against it."

"Because it's not right," he says.

I cross my arms. "Whatever."

If he really thinks that, what would he think of me if he ever found out I was sucking Principal Davis's dick?

The rest of school went by so slowly as I watched the clock click down until I have to meet with Principal Davis. My mind's filled with thoughts on what she will do to me. My stomach feels as if I swallowed a jar full of ants and they're crawling all over the inside of it. My hands are all clammy. My heart's racing like I'm about to take an exam that will decide whether I'm going to pass or fail.

As the final bell rings, my tummy tightens and sweat starts to drip from my brow. I feel like I'm stuck in slow-mo as all the rest of the students rush out eager to get out of school for the day while I make my way to meet my fate.

"Yo, Marc, are we going to tackle Chillshore tonight?" Anthony asks as he meets up with me as I make my way to my locker. "I still need the shield that drops in the battle."

"I... I don't know. I have to meet with Principal Davis... Besides, I'm pretty sure Aratheon is going to be down for maintenance."

"Really? What for?" he asks.

"Nothing! Just extracurricular activity stuff," I spit out.

"Okay, well text me when you get done," he says.

"Yeah... I'll talk to you later," I say, grabbing my bag. I feel like a prisoner on death row, walking to meet my end by lethal injection.

As I walk into the Principal's office, Ms. Stanton has me take a seat. The room feels like it's getting smaller and smaller as my heart beats faster and faster. I think I'm having a panic attack.

My skin feels so cold. Like I'm standing out in the middle of a blizzard, and yet I'm sweating. Suddenly the Principal's door opens up and Stan Read walks out. He glares at me before he leaves. "Mr. Weeks. Come on in," Principal Davis says as she stands at the door. "Jill you can take off. Once I finish with Mr. Weeks, I'll need to head over to the board and finish up there."

The red-headed office secretary nods with a knowing smile. "Have a good night, Principal Davis. Go easy on him," she says as she packs up her things.

My body moves on its own accord as if compelled to do so. She closes the door behind me and I hear the click of the lock as she lowers the shades. My heart's racing 7000 RPMs. "I suspect you understand why I am having you stay after."

I gulp down and barely manage to nod. She gives me a wicked smile. "Good."

"You're still a virgin aren't you?" she asks, raising an eyebrow.

Once again, I find my head nodding.

Her smile grows deeper and more devious. "Just as I hoped for."

"Now... Get undressed," she says. "I want to see that lovely body of yours."

I gulp down another swallow of nerves as I look up into those narrow dark eyes of hers. "Come on now, I don't have all evening."

I set my bag down and reluctantly take off my clothes, pulling my shirt over my head and then dropping my pants. She never takes her eyes off me as she bites her bottom lip. After I strip completely naked, feeling more vulnerable than I ever have, she circles me like a lioness with her prey. "That ass is perfect," she purrs.

"I can tell you're more than a bit nervous. That's okay. Since this is your first time, I will go easy on you. But don't expect it in the future," she says as she unbuttons her blouse, revealing that dark olive skin underneath. "This is, after all, discipline for your bad behavior."

She pulls off her blouse, and then undoes her bra, revealing two large melons with quarter size nipples. "But, if you are my good little boy, I might be willing to reward you."

"Now why don't you unzip my skirt," she says, turning her back to me. I take in a deep breath and slowly tug the zipper down on her skirt. She smiles and then wiggles her hips as she slides the fabric down, revealing a butt so perfect, it has me mesmerized. "Like what you see?"

I thoughtlessly nod as my jaw hangs wide open. She laughs as she turns around. "I'll admit, you're definitely one of the cutest boys I've disciplined. I always thought you were such a good boy before the other night. But if I'm being honest, I can't say I'm not happy about this turn of events. I haven't had a sub in such a long time and you're so perfect for the role."

She dips her fingers below the waistband of her lacy panties and slowly pulls them down and tosses them on the desk. Her cock springs out like a rat trap being triggered. Her dick is so big. I can't possibly imagine fitting up my ass. My butt hurts just thinking about it. "It's going to hurt, isn't it?"

"Just a little at first," she says. "But don't worry, I've taken many anal v cards. Since you've been so compliant, I'll ease the pain. It'll only hurt for a little bit, then you'll be begging me for more."

She places her hand against my chest and pushes me up against her desk. Then she spins me around and bends me over, making my heart practically jump up into my throat. I can feel her hands spread my asscheeks apart before she buries her face in my crack. Her tongue slides up and down before it runs a lap around my tiny butthole, sending a chill through my body. I grab ahold of her desk as she pushes her tongue inside me. Her hands squeeze and knead my butt as she gives my asshole a good tongue bath. It actually feels really good. I don't think I have felt this good before. It's warm and wet. It sends tingles through my body.

She gropes my ass and gives it a slap, leaving a hot sting as the sharp pain echoes through my nerve endings. She then stands up and walks around the desk. She pulls out a bottle of what I can't assume is lube from her desk. She drenches her big stiff cock in it before making her way back behind me. I tense up as I feel the cold liquid splash down the crack of my ass. Her finger runs up between my cheeks, then in one swell push, I go stiff as her finger plunges inside my butt. I can hear her laugh as she twists her finger inside me. "Relax."

As soon as I take in a deep breath, a second finger squeezes inside of me. She grabs my asscheek, digging her nails in my skin. Before I can fill my lungs, another finger plunges inside of me. She pushes them in and out of my ass. I can feel it stretching to accommodate them. To my relief, she pulls them out. I let out a sigh before my eyes go wide as I feel something a lot thicker slide up the crack of my ass.

I grip her desk as the tip of her dick meets my tight little pucker. My teeth sink into my bottom lip as the head of her cock presses into the entrance of my backdoor. With a loud pop, her dick sinks inside of me. I gasp out as I collapse on her desk. It definitely hurts. And it's not comfortable at all. I feel really full.

"Breathe," She says as her hands spread my ass cheeks apart. "The worst part is over."

I fill my lungs with air and let it all out slowly. It feels so weird. I can't believe I'm doing this. What would people think if they saw Principal Davis plowing me up the ass? Slowly, she pushes more of her dick inside me as a groan escapes my lips. She pulls out just a little, before pushing another inch inside me. As my groans get louder. She stuffs her panties in my mouth. "Shhh. Be silent, slut."

Her hand crawls up my back and grabs ahold of my hair. Another loud slap sets my ass ablaze with stinging pain. Suddenly, her dick slams all the way inside me, making my eyes go wide as tears roll down my cheeks. "Listen very closely, Marcus. You are my bitch boy from now on. I'm going to fuck this ass every day and you're going to take it like a good little slut. Understand?"

I mumble out a yes as she pulls out and slams back into me. Her hips smack against my ass. "What's that? I didn't hear you?"

"Yesh!"

She pushes my head against the desk and starts to pound my ass. Her hard thrust echo through my body as a hot flame ignites inside me. Like a firecracker going off, an explosion of pleasure erupts inside me. My own cock, hard as a rock as she slams inside me. I moan out uncontrollably. She laughs. "I knew you were such a dirty slut. Now, you're my slut. I'm going to breed you like the whore you are."

The sound of her hips slapping against my ass echoes throughout the room. "Take my fucking dick," she moans. My ass is burning with pleasure as she saws at it with her big fat dick. She grips my hips as she takes my anal virginity. I'm lost in the sensation as I burn inside. I feel the weight of her as she leans down on top of her, pressing her breast up against my back. "I'm going to have so much fun with you, my little whore. I can't wait to bring you home to my dungeon."

I moan out a muffled jumble of words through her panties stuffed in my mouth. She pulls them out. "I want to hear you say it. I want to hear you submit to me. Say it. Say you're my bitch."

"Yes, Principal Davis. I... uuurggghh." She thrusts hard into my ass, causing an earthquake to shake through me. "I'm your... I'm your bitch!"

"That's a good boy," she says. She pulls my hair as she slaps my ass and really starts to hammer away at my tush. I vision blurs as my eyes roll into the back of my head. The feeling so intense, I black out drowning in all the pleasure. My own cock erupts over her desk as my ass clamps down on her dick. "Fuck, I'm going to cum."

She hilts herself inside of my ass. Suddenly a hot stream of her steamy juice fills me up to the rim. I feel as if I melted like a stick of butter in a microwave. She still continues to thrust inside of me until she empties her balls in my ass. Finally, she pulls out with an audible pop.

She grabs my hair and slides my face down her desk. "Lick up your mess."

I stick out my tongue and clean up the cum my little cock shot out which signifies the last of my independence. I'm completely and utterly her bitch. "Now, get cleaned up, get your stuff and get out. I've got shit to do."

I hope you enjoyed, please feel free to leave your feedback in the comment section below and give it an honest rating. Please check out my profile for more!

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22 Comments
AnonymousAnonymous4 months ago

No justice in here, just bullying by someone supposedly against bullying.

jrrtolkien420jrrtolkien420over 1 year ago

I have dreamed of being a slut for a beautiful TG lady.

BetaDickSlaveBetaDickSlaveover 1 year ago

Love it, this is definitely my kinda dominant fun :))

88girfriend88girfriendover 1 year ago

I agree with some of the comments I have seen here. Would love the see Noah in the story more. Otherwise good read.

AnonymousAnonymousover 1 year ago

This is my favorite story so far on literotica.

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