tagTranssexuals & CrossdressersThe Principals' Choice

The Principals' Choice



He couldn't stop his hand from scribbling the last of his thought onto the paper, a few moments of silence before he looked up through his blonde bangs and focused his eyes on the teacher who had called his name.

"The principal wants to speak with you." The dark haired female set the phone on her desk against the receiver, hanging up the phone in a relaxed manner. She didn't mind losing her student for a while; his grades were more than acceptable.

"Alright..." The teen stood, releasing his pencil onto the desk, making sure that it didn't tumble onto the ground. He strode past the watching eyes of his classmates, as the class all wondered and gossiped about the boy. They came up with the most obtuse theories to why he was being pulled out of class.

The boy put his hands into his dark jean pockets, feeling the wallet that resided in his pants. He rubbed the leather, as he stepped into the hallway. His drivers' license was the only piece of plastic that inhabited it, but it gave him a sense of comfort.

He wondered what it could be. It didn't take long for the boy to theorize why he was being called to the office. His spine shivered, as he pondered if she really would take the risk of meeting with him during the school day, with her secretary right outside of the door. Hopefully she wasn't looking for the full package deal, and would be happy with an appetizer instead. He could care less if she lost her job; it was his own reputation he was worried about. The boy had enough to deal with already.

As his feet echoed off of the tile floor of the school hallways, he thought back to his first encounter with his superior.

The ticking gave the room an uneasy feeling.

"Alexander, what is it exactly you need?"

The red haired female looked away from her computer monitor, adjusting her gaze into the eyes of the boy in front of her. He was sitting laxly in the chair, on the other side of her wooden desk. She adjusted the tight bun her hair was tied into, and surveyed the body of the student. He was a blonde, shorter for his age, not even six feet. But he was in shape, not athletically fit but admirably thin. The boy was wearing a green shirt, that read "Science > Religion" in bold, white letters. It was questionable, but not against school policy. She was very interested in this student.

"Well..." He started, his eyes avoiding her gaze, showing his lack of confidence, a trait of someone who enjoys taking the backseat in most social environments. She sat back in her chair, her dress coat wrinkling slightly as she did so. Her chest pressed against her white cotton shirt, that she wore under her business suit. "I'm eighteen now, I've almost graduated, and I wasn't..." He paused, unnaturally. "Sure that I'd be eligible for the scholarships I was hoping for."

She moved her body forward, almost hunching over the keyboard, quickly opening her student portal, looking up his grades for the school year. Her green eyes darted across the screen, as her fingers worked with a purpose. The principal scanned his grades. 'One hundred, A, A, one hundred, satisfactory, pass, pass. What is this kid worried about? The worst grade he has would make most parents blind with joy.' She pinned her pupils back onto the boy.

"So, I was wondering if there was any way that I could make sure that I can get them, without a doubt." He shifted in his seat.

"Hmm..." She rested her hands on the arms of her chair, surveying the situation. "I see. Well, what I can do is write you a letter of recommendation to the state, and they might have something for you." The freckled face of the confident female stared down this nervous boy, from her chair. Her black heels slowly tapped against the carpet, invisible to the boy, as there was a wooden panel blocking visibility to what was under her desk.

"No, what I mean is, are there any after-school things I can do, like a club or extra-curriculum project?" He gestured with his hands, having difficulty forming the words as he went along.

'He's a smart boy, but he is more socially awkward than my ex-husband.' It reeked from the student, like he had just had a giant tube stuck up his ass. 'Oh, shit; wrong thing to think about.' She shifted in her seat, wheeling herself forward, putting her legs under her desk. "Honestly, Alexander, it's almost the end of the year. Clubs and extra projects aren't really... practical. I doubt I have a teacher available for something like that."

The blonde haired boy's eyes dropped, his eyebrows followed, his face forming slowly to show a disappointed expression. It made her skin crawl, her fingers curled and she had to pin them on her wooden desk before she scratched her own palms. Her self-control for not pouncing on this student was admirable. She cleared her throat, getting a serious, superior and commanding expression on her face, her green pupils as fierce as possible. "There's no reason crying over it. I'm sure you'll figure it out on your own." She was close to bursting a gasket.

"There has to be something..." His face slowly curled differently, a hopeful look in his eyes. "Is there anything I can do? Do you have anything that needs done? Any jobs I can do for you? I need everything I can get."

She closed her eyes, taking a deep breath and thought about dead kittens for a little while, and the blood rushing through her head slowly receded, deflating her hormones. "There is one scholarship." It was one she had already planned to give to this particular boy, for his academic prowess. "The 'Principals' choice' award."

"What do I have to do to get it?" He shifted in his chair, moving closer to her desk, literally standing on the edge of his seat, waiting.

She opened her green eyes, staring into the blonde students' expression. "Well, kiss my ass of course." Then she smirked.

He snapped out of the memory, coming back to his surroundings, as the office around him materialized.


The teen stared at the females' angelic shaped face, slowly blinking.

"Yes, I'm here to see Ms. Evans." He removed his hands from his pockets.

"Right. She's waiting for you." The secretary pointed to the office, where he walked, opened and stepped into.

His eyes met with the principal in the slightly dark room, the blinds closed and lights dimmed. Alex closed the door before anything was said, but once it was, he turned to the red haired female.

"Mmm, I missed you Alex." She licked her lips, a light pink lipstick covering her juicy lips. The shadows cascaded over her figure, as she sat in her chair, a foot or so away from her desk.

"Uh-huh." The blonde replied, moving his tongue around his mouth, making his tongue salivate.

"Show some affection. It won't hurt you." She smirked, her fingers slowly moving to her chin, as she laid back in her chair.

"Can we get this over with? I'm missing class." He walked away from the door, stepping to the chair on the other side of her desk.

Since she began regularly visiting her boy, he had gained confidence, some at least. It seemed their meetings were helping him in more than one way. The red haired principal was encouraged by this fact. "Oh, eager to leave already? That's not very nice, Alex. I love your company." She remained still in her position.

"I don't want to get caught." He said, flatly, placing his hands on the back of the chair in front of him.

"Oh, don't worry about that, babe. Come here." She beckoned her hands, waiting for her student to come around the desk.

Alex swallowed, walking slowly around the desk, watching as her arms stretched out to meet him. Her hands wrapped around his hips, pulling him closer. The well-dressed female planted her fingers on his clothed ass.

"Mm." Her eyes raked up and down his body, her lower regions coming back to activity.

"We don't have time for that." He looked down at the superior, hoping she wouldn't push for such an activity.

The female got a devilish look in her eyes, and spoke in a demeaning tone. "I'll decide what we do, slut."

His body shivered, as his eyes looked into her lap, seeing a noticeable arousal.

She turned her chair toward him, her body facing him. "Get to work, then, if you don't want me to pound you."

Alex avoided her eyes, keeping his gaze on her legs. She was wearing slacks today. The blonde boy placed his hands on her knees, sitting down on his shins. He was level with her lap, as his hands slowly moved up her thighs, and undid the button on her pants. The boy snuck a look up at the principal, and she was smirking with anticipation.

He unzipped her, and tugged the pants down to her knees, where they fell down the rest of the way. Her groin was bulging at the seams, barely contained in the black laced panties. Her own hands came down and pulled the underwear off, lifting her ass up as they moved down to her mid-thigh. The blonde teen watched as her manhood spilled out of the tight clothe. It throbbed to full light; her sac slowly expanded to its bigger than average size. He watched as it leaked a dribble of pre, in its full glory. He remembered the smacks he had received when he grazed it in the past with his inexperienced teeth.

"Remember, Alex, that if you get cum on my clothes, I'm gonna fuck you." She meant that literally.

The teen could tell what expression she had on her face, without even giving it a glance. It was the same look she always wore, one of sadistic satisfaction. The creases of her lips were turned up, her green pupils dilated, her cheeks tightened. Alex slowly leaned his head closer; the smell of her feminine body wash covered his senses. It smelt like a unicorns' sweat. He noticed her mound of pubic hair; it was something she never trimmed. Alex had plenty of memories of the hair tickling his lips.

Alex opened his mouth, a line of saliva slipping through his boyish lips. His eyes were pinned on Ms. Evans' throbbing shaft. His tongue slowly migrated out of his mouth, and he moved his head into position. The boy dragged his wet, pink tongue across the side of her crown, and moved his hand to her base, keeping the thick member in place. He licked down her left side, then up the bottom, coating the length in wetness, giving him just a mild taste of her girl dick.

"Oh, Alex, you've gotten so much better at this." One of her hands ran through his blonde hair for just a moment.

He felt urged to continue, he didn't have all the time in the world. The boy swirled his tongue around her crown once more, working up one more side of her shaft before positioning his mouth at her tip.

Alex drifted his tongue just above her head, letting his saliva drip down and cover her burning hot organ. He placed his pink muscle against the back of her tip, as his lips encircled her. Gently, he moved down, swallowing just a few inches in his tight mouth. Both of his hands shifted to her lap, placing themselves against her curves. The boy lowered his head down as far as it could reach, just a couple inches away from swallowing her base. Her cock throbbed wildly, her heat burning the saliva that coated it away. His tongue watered, bathing the covered length in warm liquid.

"Mmm.." She groaned, both of her hands on the arms of her chair, tightening their grip on the leather. Her knuckles whitened, her lips parted slightly to reveal her teeth grating each other gently.

The teen lifted his neck, his lips abandoning the member inch by inch, until they revealed her crown. He stopped, encircling her sensitive tip once more, before diving back down. Her shaft filled his mouth, as his lips massaged every centimeter of her flesh. The boys' tongue worked magic, shifting constantly, trying to amplify the feeling wherever possible.

His speed increased; his mouth working from her head to as far as he could reach, a few stray hairs tickling his nose. The boy did not allow this to distract him, closing his eyes as he raked his lips up and down her woman cock. His tongue continued to work, swirling from side to side.

The boys' speed doubled, drastically shifting his body into a better position. He eagerly sucked her off, pumping his head with a swift pace. Her tip slipped into his throat, as he repressed his urge to gag. Alex felt her hand move into his thick hair, for now just twisting her fingers in the smooth blonde locks. He pressed on, extending his neck, feeling her thick member press against his mouth, throbbing with excitement. Adrenaline pressed into his veins, once he opened his eyes, and heard a knock on the door. He moved to take his head away from her groin, only to feel the principals' entire body shift. She now faced her desk, and quickly pushed the boy with her legs into the small cubby under her wooden desk.

"Don't stop now; it's only a minor inconvenience." She whispered, before looking to her door and announcing, "Come in!"

The door opened, Alex didn't know what woman it was, but he could feel the heels of the principal press against him. She was quite serious that she didn't want him to stop.

He began slowly, his hands now at his sides. Alex didn't have much of any room under the desk; it sat in front of him, throbbing slowly. Its size was slightly reduced, because of its position. It was only an inch from his face, from where he sat on his knees. He could hear another woman speak, but couldn't make out the words, as they were slightly hushed.

The boy began by shoving his lips to as low as they could reach. Her hips tightened, as he dragged his mouth to her tip and down again. He noticed drags in her speech when he dived down on her.

"If she wants tooo- that's her choo-ice." Her hands fiddled with documents on her desk. "Well, I'm in the middle of w-rriting some docu-uments. Can you co-ome back laterr?"

He continued his wet assault on her shaft, until he heard the door of the office close.

"There..." She shifted in her seat, lifting her hips away from his lips, breaking contact with her member.

The woman slowly pulled her seat away from her desk, and pulled the boy by his hair after her. "Ooow.." He stated, for a moment unsure of what she was doing.

"I'm gonna make your jaw ache, boy." She smirked wildly.

She stood out of her chair, sending it back a foot or so, and pulled the blonde teen to her groin. She stared down at the boy, as he opened his mouth, "That's a good slut." The well-dressed principal put one hand on the back of his head, and the other on his chin, holding his head in place quite effectively. Ms. Evans positioned her tip to his lips, and thrusted herself into his throat. Her base was kissed by his lips, his nose buried in her pubic hair.

The woman could hear him struggle with his gag reflex, and began pistoning herself into her cute boy-toys' throat. Her hips bucked, his plump lips sucking her off. She face-fucked the blonde boy, feeling her arousal build. "Oooh, yes." She groaned out, as the wet sounds of his mouth accepting her cock filled the room. He stared up at her expression emptily, as her girl dick raped his mouth.

There was little time before she took the speed to the extreme, slapping her thighs against his cheeks, swiftly bringing herself to a prolonged orgasm. She moaned, as her tip shot out her seed, burying it in his throat. Rope after rope of her cum filled his mouth, which he attempted to swallow. It dribbled down his chin in a few streams. She continued pumping her emptying cock into his throat, until she removed it from his mouth, and managed to get a few shots on his face, coating his cheeks and mouth. He breathed heavily on her cock, eager to get oxygen in his lungs. The blonde teen stared up at his principal.

"Mm, that was so good, I think I'll have seconds."

The green eyed predator smiled.

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