tagTranssexuals & CrossdressersFutanari Academy Ch. 11

Futanari Academy Ch. 11

byTheOrcKing©

First thing Monday morning, Bailey found himself sitting outside of the Vice Principal's office. He was ordered to report there by Pickwell who decided to let him stew over the weekend about his circumstances. To Bailey's surprise, Surbrina showed up and sat quietly on the bench beside him.

"It isn't my fault that you were the one that got caught." Surbrina sighed. "But all the same, it's fucked up that you were the only one caught, so I won't let you do this alone." She said, flashing him a nervous smile.

But Bailey just shrugged. "I got this. I really appreciate you coming to stick up for me, no one has ever done something that nice for me. But you should go. No sense in both of us getting in trouble over some bullshit school morality rule."

"It's fine." Surbina said, nervously tapping her foot.

"It is." Bailey said. "Now leave. I got this." He said with a confidence that Surbina had not heard from him before. She hesitated and then slowly stood, glancing back down at Bailey.

"Are you sure?" She asked.

"Positive. Get your cute little brown butt out of here." Bailey offered her a warm smile and Surbrina leaned down, quickly kissing him on the mouth.

"Good luck. Text me as soon as you are done."

Bailey nodded and let out a heavy sigh as he patiently waited in his seat. The weekend had been a blur since he left Lesbian Pimp Records, he felt light headed, but walked away from his night at the record store with a clarity he wasn't quite accustomed to.

"Mr. Hudson, they are ready for you." Said Ms. Pickwell's secretary from her desk, gesturing towards the door at the end of the hall.

Nodding his thanks, Bailey stood and headed down the hallway, pausing in front of the door with the big gold nameplate that read PICKWELL before he pulled open the door and stepped inside.

* * *

It was around three o'clock in the afternoon when Miss Angeli settled in at her desk in her office. She left the door open to catch some of the pleasant summer breeze floating in from outside as she stared at a stack of paperwork on her desk. She still felt hurt over what had happened between her and Bailey, she had no small measure of heartache over the ordeal and found it hard to push him from her mind. So much so that she just sat at her desk, staring listlessly at the work she had piled up.

"Don't suppose you have time for a coffee?" Came a voice from doorway, it was a voice that put Miss Angeli on edge and she immediately sat bolt upright, looking up in the doorway to see Ms. Pickwell.

"Ms. Pickwell, I was just..."

"Gazing off into space like a lovesick fawn?" Ms. Pickwell rolled her eyes. "You aren't the only one. Please don't make this more awkward for me than it already is, come. Have some coffee with me."

The pair headed quietly towards the senior cafe at the back of the school's cafeteria, it was a small coffee shop set up for and open to only the seniors of the academy in the morning, so now it was more or less empty, save for staff in the back of the house cleaning and cooking pastries for the next day.

Miss Angeli ordered a simple, sugary cappuccino and much to her surprise, the stern, reserved Pickwell ordered an iced frappuccino - whipped cream, caramel drizzle and all. She sat with her frosty drink, idly poking the mass of iced coffee and whipped cream with her straw as she sighed.

"I taught in the classroom for fifteen years before I became an administrator. I must say in that time, I never felt much of a connection with my students, they were all whiny, short-sighted, self-entitled little shits." Said Pickwell.

"Being young sometimes goes hand-in-hand with being stupid. It's part of growing up." Offered Miss Angeli.

"Ah. So I thought too, but after this morning, I am not so sure anymore."

Miss Angeli perked a brow. "This morning?"

"I had every intention of raking your little boy toy over the coals and breaking him. I would have broken him until he begged me on his belly like a little worm for every inch of my cock." Pickwell sighed, and then to Miss Angeli's surprise, the woman smiled, albeit slightly.

"What happened to Bailey?" She asked, her heart skipping a beat.

"Well, in summary. He told me I could go fuck myself."

Miss Angeli narrowed her eyes, mulling that over, before her beautiful face became scrunched up in outright confusion. "Hudson? Bailey Hudson?"

"The one and only." Pickwell confirmed, finally taking a sip of her drink. "My God, all this sugar and all these chemicals are revolting, but, soooo delicious." She said, taking another swig.

Miss Angeli moved a hand up to her forehead, and then moved her fingers back through her hair before shaking her head. "No, I don't think so. Bailey?"

"Oh it was him. I've overlooked him taking dicks in the men's room like some common streetwalker because he is young and needed to get it out of his system. But walking out of an adult bookstore all poppered up and wearing one of our school uniforms like this is the fucking mid-eighties is pushing the limits of what I'll tolerate."

"What happened to Bailey?" She asked again.

"Well, this morning he came to my office..."

* * *

Earlier...

When Bailey entered the room, he found himself confronted by not only Ms. Pickwell, but Ms. Roberts, and Nurse Joy who sat on either side of Pickwell across the conference table from Bailey.

"Have a seat Mr. Hudson." Pickwell said, cooly, gesturing for the empty chair on the opposite side of the table from them.

Bailey sat and braced himself, Pickwell went on the offensive almost immediately. "I hope you've enjoyed your time at our academy up until now Mr. Hudson." She said as she flipped through a folder that Bailey assumed was his student record as Miss Roberts stared daggers at him from across the table.

"Good grades, no incident of student discipline. A shame, you were a model student..." She taunted.

"Yup." Bailey said, unfazed.

"Well Mr. Hudson, I know all about your, shall we say, 'extra-curricular' activities and I must say it is very disappointing. Even after Miss Roberts intervened and attempted to reign you in, you just escalated your perverse habits."

"So what, you bring me into a board meeting with a random teacher and her kooky fuck-buddy nurse? Are you going to expel me, or did you really think I would get on my knees and let you all have a sword fight in my mouth in exchange for leniency?" Bailey asked, folding his arms over his chest.

"How DARE you?!" Miss Roberts growled, rising to her feet before Pickwell caught her by the arm, the pair locked eyes and Pickwell shot Miss Roberts a frightening look that almost shook Bailey's resolve. Almost.

"And you see Mr. Hudson, we simply can't allow this type of behavior go unchecked... A shame, I bet you could have your pick of colleges were it not for your lustful appetites."

"I don't know if it's because I am young or because I had a bad weekend, or hell, maybe I am just hopped up on the Wu-Tang, but I find myself with little patience for this bullshit. Get on with it, I have more important things on my plate."

"I have the power to end you Mr. Hudson, so I would suggest you change your tone."

"You going to throw me out of school?" Bailey asked.

"That particular option is becoming more appealing by the moment." Pickwell replied.

"Neat. Throw me out, I'll take my transcripts to another school and finish the semester there. You can stop me from earning credits at your school, you can't take away the ones I've already earned."

"Oh my power extends beyond this school, I can have you labeled as a nuisance and no one would touch you."

"Money has a lot more power. For example, do you know who can get into college? Anyone who can take out a fucking loan." With that Bailey sighed and stood.

"Mr. Hudson, we are NOT finished here!" Ms. Pickwell growled.

"I've spent the last 18 years of my life being badgered about how important going to school is and how important grades are and how important a private academy will look on my resumes and college applications. I realize now, all of that means fuck all nothing." Bailey stood and picked up his bag, slinging it over one shoulder, he paused at the door and turned to face them.

"I think, for the first time in my life I have found something that really is important, and if you pardon my french, I don't have time to sit here fucking around with you people. I have something to do." With that, Bailey flung open the door and walked out, throwing up a peace sign over his head before he rounded the corner and exited the office.

* * *

Now...

"Honestly, we were just going to scare him a little and pass his ass around like a joint for a couple of hours but..." Ms. Pickwell shrugged. "Don't get me wrong, I have half the mind the slap the taste out of his mouth for talking back to me, but I must say, to see a young person so determined. Well, I found it inspiring. I think if Mr. Hudson keeps his new-found resolve, he has a bright and promising future."

"What the hell has gotten into him..." Miss Angeli asked to no one in particular before she quickly shook her head.

"He can stay. But if he thinks he can speak to his teachers and the school administrators like that, he'll be out on his ass so fast his head will spin." Ms. Pickwell took a sip of her sweet, iced coffee and glanced over at the bewildered Ms. Angeli.

"As teachers we rarely hear a thank you. So for what it is worth, you did a good job. I only wish we had more pupils with his kind of resolve." Pickwell said before she rose and picked up her coffee. "Enjoy your coffee Miss Angeli."

* * *

It was a surreal and confusing day for Miss Angeli. She went back to her office and packed her things up before heading home, the weight of all she had just been told was heavy on her mind. She felt confused, and hurt. She was realizing now, that she wasn't mad at Bailey, but pushed him away out of fear for what might happen to him, but if he was able to overcome Pickwell so easily, she seriously misjudged him.

She pulled into her garage and then climbed out of her car, dragging her file box and purse with her, she headed into the house and paused immediately upon finding a massive puddle of rose petals on on the floor. The puddle of fragrant flower petals gave way to a trail that led it's way down the hallway and around the corner...

Miss Angeli felt her heart skip a beat, an excitement welling in her chest, but all the same, she silently set her belongings down, pulling out her phone and unlocking it before switching it to her left hand, she then headed towards the hallway, pausing to pull a chef's knife from her knife block before she head cautiously down the hall, the blade clutched at the ready. The petals created a trail from the garage door, down the hallway and into her bedroom which was illuminated by half a dozen vanilla scented candles spaced out on her dresser.

"What the fuck Bailey?" She asked, raising a brow as she entered the room.

On the bed was a massive pile of multi colored flower petals, the pile was so large, that Bailey was able to cover himself with it, cutely leaving only his face exposed where he was lying back on the bed.

"Yeah... I might have went a little overboard." Bailey said, bashfully.

"Yup."

* * *

"Pickwell told me about what happened." Miss Angeli said, sitting on the edge of the bed beside Bailey.

"I don't give a shit about that." Bailey sighed.

"You should! She's decided to let you stay, provided you don't pull any shit like that again."

"I'm not here to talk about school. Listen... I'm stupid. I got caught up in the moment and I didn't realize what I was doing was so stupid, or more importantly, that it would hurt you."

Miss Angeli sighed. "Bailey that isn't it, I was scared they would throw you out of school, that you would fuck up your life over a couple of loads in a goddamn bookstore! We've all been there, but I was just scared."

"I've just kind of went with the flow until now. I didn't know what I was doing, but after the last few days, I think it's all a lot clearer." With that, Bailey shifted so he was facing her, he stared into her vivid green eyes and felt a warmth swelling in his chest that confirmed his feelings.

"Veronica, I love you. And I am sorry I hurt you. I've never loved anyone before, but I know that I love you, and I am sorry for being a dick."

Veronica's mouth twitched as she tried to muster the words to reply to him, but instead she brought her hands up to cover her mouth, tears already welling in her eyes. "I love you too."

"Is... is that the good kind of crying or bad?" Bailey asked awkwardly, genuinely unsure.

"The good kind, dumbass!" She laughed. "Just kiss me you fucking idiot." She said, wiping tears from the corners of her eyes as she leaned close to him.

Their mouths met in a warm kiss as they fell back together onto the bed and into the sea of flower petals.

"My God!" Veronica said between, firm, urgent kisses. "Who's dick did you have to suck to get all these flowers?"

"It was actually two dicks." Was Bailey's reply as he quickly pulled at the buttons of Veronica's top, his lips brushing against hers as he pushed open her shirt, his hands dropping to squeeze her breasts through the red and black bra she was wearing.

"Shut up." Veronica snorted.

He fondled her for a moment or two before she forcefully used her weight to roll him onto his back as she straddled him. "You just lay there like a good boy for a bit." She said, jerking his belt free from his pants before tossing it on the floor.

With nimble fingers, she unbuttoned his jeans, pulling them down with his underwear in one single tug before she trailed kisses down his smooth, slender stomach, each kiss moving her lower until her mouth found his stiff, throbbing cock and engulfed it.

Bailey moaned loudly as Veronica aggressively sucked his cock, one hand squeezed and gently rubbed his hairless balls as the other moved lower, her thumb pressing against Bailey's warm hole as she firmly rubbed it, all while moving her head rapidly back and forth. She sucked him loud and sloppy, her warm saliva cascading down Bailey's shaft, the warm flesh of her cheeks squeezing his shaft in it's hot, velvety grip as she worked his balls.

She kept up that same level of intensity for several minutes before she pulled her head up, letting his wet cock spring from her mouth and slap against his stomach. She gripped it with one hand, gently tugging it as she lowered her mouth down to his balls, her finger sliding quickly in and out of his ass as her hot little tongue lashed out against his smooth sack.

"Your dick is as delicious as it is cute." She grinned, planting a warm kiss on his balls before she sunk lower, sliding her finger out of his ass and quickly replacing it with her tongue.

"Jesus!" Bailey gasped, squirming around on the bed and breathing hard as Veronica shoved her tongue deep inside of him, alternating between darting it back and forth and aggressively swirling it around, either of which made Bailey cry out in pleasure.

Veronica grinned as she tongue-fucked his delicious little hole, savoring the way he squirmed and moaned as she licked and lapped at him. Once he was wet enough she pulled back and stood up, leaving him panting there as she hiked up her skirt, bunching it around her hips as she pulled her skimpy panties to the side, letting her raging hard cock slip free. She immediately gripped it and slowly pumped it as she leaned forward and let a big, wet glob of spit roll off her tongue and onto the purple tip of her cock.

Bailey lifted his legs and spread them, holding them under the backs of his supple thighs as he relaxed and lifted his hips, offering up his warm, glistening hole to her as she lubed up her cock.

She climbed up onto the bed on her knees, not even bothering to kick off her spiked heels as she settled between his legs and gripped the shaft of her cock, using it to rub the fat, swollen tip up and down against his hole, teasing him as she smeared the last little bit of extra lube onto him.

He was more than ready to go and she knew it, so without further teasing, she pushed the head of her cock against his smooth, pink hole and pushed forward, hissing as she slid her cock right up his ass. She arched her back and began thrusting hard, driving her dick deep and hard into him as she leaned over him pressing her lips to his as she thrust into him, the pair moaning almost in unison.

Bailey wanted nothing more than to reach up and squeeze Veronica's large, soft breasts, but he kept his hands on his thighs, keeping himself spread so she could use him to her heart's content; he would just have to settle for having her bra-clad breasts brush up and down his bare chest as she fucked him.

Veronica broke their kiss, her hips were moving hard and fast as she fucked him deep, she was drowning in the pleasure his soft little body offered and she couldn't help but moan like a whore as Bailey squeezed his ass tightly around her cock, again and again. She would thrust deep, only have him clamp himself tightly around her, really milking her cock with his aggressive muscle control.

She dropped a hand down between them and gave his cock a playfully hard squeeze, pulling a moan from his lips before she gently twisted her hand around his shaft, pumping him up and down as she grinned, slowing her thrusts to match the speed of her hand stroking his cock. Bailey whined and moaned, wiggling his hips around as he simultaneously tried to thrust against her hand, and her diamond-hard prick.

Leaning forward again, she quickly planted a warm kiss on his lips, her breaths coming in hot hisses and moans of pleasure as she ground into him, her hand pumping his small cock even faster. "Tell me again." She hissed, her lips stealing another quick kiss from his lips.

"I love you!" Bailey moaned and Veronica felt a shudder of happiness, thrusting harder and faster into Bailey as she took the tip of his cock between her thumb and forefinger and aggressively rubbed it, causing Bailey to cry out as his sensitive cockhead was assault.

"Nnngh!" Bailey cried out as he came, his eyes rolling up into his head as he was fucked hard and deep, all the while as Veronica skillfully milked him for every drop, squeezing his sensitive cock and pumping it as he sprayed his creamy warm load all over his stomach.

"Again!" She said, releasing his cock as she planted her hands on either side of him, bracing herself as she really began to pound away, moaning loudly as she dropped her hips, thrusting with her full weight and grinding at the bottom of each movement.

Bailey could tell she was close, if the throbbing weren't a dead give away the swelling of her cock certainly was. "I love you!" Bailey called out again.

Veronica moaned in response as she bottomed out inside of him, her balls slapping loudly against his pert little butt as she buried her cock deep, letting out a cry of ecstasy as she came deep inside of him. She shuddered as several incredibly thick ropes of gooey, creamy cockmilk burst from her cock and filled the deepest part of his pink, warm little ass.

Spent, she collapsed on top of him, her head resting on his chest where she could clearly hear the pounding of his heart as he tightly wrapped his arms around her and kissed her on the top of the head.

"I love you too." She gasped, slowly closing her eyes.

* * *

Epilogue.

Six years later...

It was a hot August day at Westbrook Academy, marking the start of a new semester for all students, but for the senior class, it marked the end of their High School lives. The Academy had, years ago been a school for young men, but after the school went through a restructuring, it became a private, co-ed academy.

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byTheOrcKing© 20 comments/ 17788 views/ 29 favorites

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