Working Late

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A chance encounter at school and a night of pure passion.
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Holister
Holister
38 Followers

CHAPTER ONE

The last person at school again, grading middle school science papers and writing reports that only a few parents will actually read. The last hour of daylight outside was giving way to a warm spring evening, and the sound of wind through the trees outside takes your attention away just long enough for your mind to wander to thoughts of coffee.

Lifting your cup from the stack of papers, you retrieve your keys from the top drawer where they spend much of their time next to a small collection of rubber bands and confiscated knickknacks. You stand. You stretch. You're only in your late thirties, but sitting down for two long hours has made your back feel like what you imagine a seventy year old feels like.

The divorce that allowed you to move into this small town and away from the city, was the same thing that allows you to work late without remorse. Other faculty members now long home, either happily entertaining families, or disdainfully avoiding them while maintaining the facade of a happy family.

Sara would be somewhere stuck in traffic on her way home to Dale. Thanks to the combination of time, distance and a few sessions of late nights with mates, your thoughts of her are less and less vivid, and less and less frequent. In fact, sometimes you almost wish that they are happy together.

Mostly, right now, you just wish you were doing something more interesting than writing reports.

Walking around a school campus after everyone has left for the day is a surreal experience. The sounds of kids laughing and shouting define the atmosphere so much that without them, you notice the damp smells and bareness or the concrete constructions. The same damp smells seem to dominate your own memories of school and the nights you left late after drama rehearsals or detentions. Not a bad smell, not unclean, just damp and industrial.

That's what this place was at the moment. Industrial. An arrangement of concrete awaiting a purpose. No sound except for the shallow echo of your own footsteps heading towards the teacher's staffroom.

Three years here now. Most nights you're the last to leave. The principal's left, administration staff all bundled out the door at the end of the day. You know the stillness of this place, the sounds it makes, the shadows that are left by emergency lighting in darker corridors.

You know these sounds, but what you hear now is different.

The sound of wind past the doors at the end of the corridor eventually gives way to a soft rustling.

As you move closer, the light underneath the door becomes more obvious. A solid line of white light spilling out announcing that you're not alone here tonight. The sounds continue and you hear the unmistakable sound of the toilet stall door opening. When you look up you realise that you're standing pensive at the door to the senior girl's locker room.

No one should be here, and certainly no students should be left in the building.

The noise is unmistakable though, now footsteps, clumsy heals on the hard tiles, then spray of water in the sink. You have to knock. The only other alternative is to stand looking like a pervert lurking outside the girl's toilet.

You wrap your knuckle against the door. It's halfway between a forceful rhythm and a gentle tap, but it's enough to announce your presence. After the third wrap of your knuckle against the timber, silence. She, whoever is in there, is still.

"I'm coming in" you command in a matter of fact tone, loud enough to pierce through the heavy door. Perhaps too loud you think as it echoes down the hall.

You gently push on the door, the light spilling out as your eyes adjust to the bright white of an otherwise pristine white girls locker room. The only thing blocking the white is a tall girl, standing awkwardly perched on stiletto heels, in a short black dress and pale blue tube top.

From her expression, she's as shocked to see you as you are to see her. There is something familiar about her, but you can't place her. There are a lot of students at the school though, and you don't know every single one.

"It's far too late to be in here miss," you say in the falling tone of a practiced teacher's voice. "The building has been locked up for ages. What are you doing here?"

Silence. Your question lands, but it's met with silence.

She stands there, still awkward and looking just a little scared. You look around, and everything seems to be in appropriate repair so you assume that she hasn't been vandalising the place.

"Well come on then," you say. "We can't stay here all night."

You hold the door open and stand out of the way, dipping your head as if to gesture to her to walk through. She does, leaving the sounds of her heels clipping as she walks like she's only new to such high heels.

The smell of perfume gently draws your focus to her neck as she walks past and, for the first time, you acknowledge that she has a fantastic boyish beauty to her.

You still can't shake the feeling that she is familiar to you though.

"Down the hall, to the left." You say gently as she walks ahead. "We'll call someone to pick you up from my classroom."

CHAPTER TWO

She made a beeline for a particular seat in the classroom, third row back, second in from the left.

This was a very strange spot to pick in an empty classroom. It was almost as if this was her regular seat. But she was definitely not one of your current students. She must be a senior. She looked 18 at least, but still with the shyness of a middle schooler. She turned her toes in, and crossed her arms to pull a sweater over her undeveloped chest. She definitely lacked the confidence of many of the angst-ridden teens that usually populate that area of the hallway.

As you sit, and place your coffee cup back on the desk, you let out a quiet sigh as you realise you didn't even get to the staffroom for your coffee.

You collect your thoughts and look over at her.

This is the first time you've been able to see her. Even as she tries to shrink into her chair, all you see is her awkward and innocent beauty fighting to shine though her obvious fear and regret.

You've never been good with teenage girls, they are as the book would suggest, from Venus, half a galaxy away from your Mars.

"Do you have your phone?" you ask genuinely.

For the first time you hear her speak. It is a quiet, breathy and shy whisper of a voice. The type of voice that would have disappeared in anything but the silence of a classroom with no students.

"Nope!"

"Do you know your parent's number, or should I look it up for you?" Now you have something of a more direct tone in your voice, you're not sure why or where it came from, but there it was, commanding action.

"Please don't call them," louder now, but still in a forced whisper.

She has sat forward and is looking at you with big, wet eyes, and it was then that your mind made the connection. The tone and intonation coming from that exact chair only a couple of years ago.

"Henry?" you ask, now mirroring the shy whisper she had used previously.

"Y...yes Mr. Fenaughty. Oh my god! Please! Do not call home."

"Wow!" You sit back in your chair, amazed, shocked and confused.

She is still looking at you, big eyes now coming to tears that will soon make mascara run. Like her awkward walk in high heels, she sits in a manner of someone not used to the role of a girl. Your eyes cannot help to wander down her body, past her folded arms still tugging at the sweater to cover her shame. To her short dress now slightly stretched between legs slightly apart revealing just the hint of light coloured cotton and lace panties.

She brings them back together, and you blush, wondering if she noticed.

"Don't call me Henry please. Not when I'm dressed like this." There were still tears in her voice.

"What should I call you then?" You ask with sincerity, now looking back into her deep eyes.

"Amy. I like the name Amy."

"Well, Amy, I'm guessing that you parents don't know about this side of your life."

"No. Mr Fenaughty." She was starting to speak more clearly as she relaxed a little.

"I'm not really sure what to do in this situation, Amy."

You stand up, and walk around the desk to approach her slowly. As she follows you with her eyes she seems to relax slightly more and loosen her grip on her sweater.

"I can't say that I've ever been in a situation like this. Normally, if someone is on school property after hours, we just make sure they get home, pretend that it's a bigger deal than it is, and move on from it the next day."

You let your honesty sit with her and watch another piece of tension leave her shoulders.

"Why were you getting changed here?"

The pause was almost long enough that you thought of another question to break the silence, but then she answers.

"I was getting ready for a date." There was a tone of remorse to her voice now. "I couldn't get ready at home, so I waited for everyone to go, and...I guess I didn't expect you to still be here."

You want to cheer her up now. "Well, you do look very pretty for your date."

She smiles. She smiles for the first time. Again you're taken back to a disaffected boy sitting in your class, perfectly average and almost trying to shrink out of sight. You think for a moment.

"You know, I don't think I've ever seen you smile." Your tone switches from teacher, to something approaching fatherly. "You should do that more often."

"Do you really think I look pretty?" She says.

"I really do."

There was a moment of silence as you look at her, noticing the way that her brushed hair sits delicately against the side of her face and runs down to just above her collar. The length aloud by the school for boys, but long enough that with care, looks equally feminine.

She looks away and down a little. Shy and coy, she is embarrassed and fiddling in her seat. As you continue to look at her, you notice the small features that might give things away, the awkward way she sits with her legs slightly apart, the shoulders forward and her feet, in their heels struggling for purchase on the floor.

Her chest offers little, but that is not uncommon of the many of her peers. If you're being honest, you never been one for big breasts anyway.

You catch yourself, shamed for a moment as thoughts race through you head. 'This is a student', you remind yourself.

"So, where is your date then?" You offer, strapping back into the flow of the stilted conversation.

"I was going to meet him at his house. I don't really want to be recognised, so he was going to drive me out of town for dinner." Amy's voice was somewhere between sorrow and guilt. "I'm a little scared though. I've never done anything like this before."

"What do you mean? Gone out on a date?"

"Well I've gone out with a couple of the girls from here before, so I guess I've been on a date...but..." she trails off, leaving you to fill the void.

"You mean you've never been on a date as a girl before."

"Yeah...and...well, he's a little bit older than me too."

"How did you meet him?"

At this point Amy had relaxed again and some of the tension had left her body. "We met online. We've been swapping messages for a couple of weeks."

"Does he know that you're...um..."

"Yeah. He knows."

Silence again. Another moment where you both regroup you collective thoughts.

You break the silence, as seems to have become your role. "I really don't think this sound like a good idea. A stranger driving you out of town for your first date. I think that you know it's not a good idea. I think that's why you're scared."

"Ahah." She says quietly, but resolved almost like she's been told off in class.

"Come on then, let me get you home."

CHAPTER THREE

It wasn't until you were half way to her house when she blurted it out.

"Shit! I can't walk through the door like this."

It was dusk, and the street was clear. All the cars tucked into the driveways and garages. Lights turning on and dinners being prepared. Your own microwave meal would have to wait.

At this point however, dinner was far from your mind as you turn to look at Amy. A look of panic in her eye. In the dim light now, the endearing panic seemed to firm up her posture and she arched her shoulders back heaving forward in her top. If she had breasts they would be stretched against the thin fabric right now, but all this pose demonstrated was that she truly was flat chested.

Her lips however quivered with perfect glistening lipstick. Bright red, just one shade darker than anything that would paint her as a slut. She had obviously practiced her makeup skills well. Her eyes were as white and her lips were full and red.

You stop the car. "What should we do?"

"I have to get changed back into my normal clothes. I don't want my parents to see me like this.

She didn't skip a beat. The seatbelt retracted and she removed her shall. She unzipped bag between her legs, leaning forward to retrieve her more familiar boy clothes. It was at this point in the fury and struggle of managing her bag and clothes in the confined space of the passenger seat of your car that you eyes drifted down her body.

Over the sparse chest conceited by a tight thin fabric, noting her two tiny but erect nipples defining where her breasts should be and the slight embossing of what you assume must be a training bra. Still drifting down the bare, perfectly smooth and flat exposure of her midriff. Over the top of a mini skirt and then into the realisation that with her legs spread to access the bag, the skirt has lifted and seating perfectly in light coloured lace panties is a bulge that announces a perfectly proportioned cock.

You are now helpless at you feel pressure building in your own underwear. Your eyes are transfixed. Your mind undressing it and wondering if it is all as smooth as the thighs beneath the panties. How long have you been staring? Has she noticed? It might have only been a second, but you want for this fleeting moment to be your forever.

She was looking around. Darting her eyes out and between each window.

"Is there somewhere I can get changed?"

You raise your eyes up from her gorgeous mound to meet her eyes. If she had noticed at all, she was more taken by panic at this point, and didn't show any sign of anything else. Pail, slight trembling and eyes white and wide again, looking at you for help.

"I...I..." is all you could get out before she launched out a suggestion.

"Is your house anywhere near here?" Her words hung in the air for a moment, and you are left feeling a sense of urgency, fear, guilt and pure sexual frustration all at once. Your remember the feeling from when you were about her age...the feeling of your first time.

Although you are sure that she is not feeling the same rush of sexual thoughts about you, you cannot help but wonder where this is going to go.

"My apartment is about 5 minutes away." You offer while trying to play down your enthusiasm.

"Can we go there please?" Her eyes white and begging again.

CHAPTER FOUR

She walks ahead of you up the stairs towards your apartment door. You find yourself trailing a little, trying to catch another glimpse up her short skirt before the night is over. All you see is the tiny triangle of her panties creeping slightly over one cheek, but not quite into the crack. It was at this point you notice their pattern. Very faint love hearts, and rainbows, the palest light blue, so pale that you want to be next to it to admire them.

You reach the front door, and retrieve your keys. Putting them into the door, you look at her as if this will be the end. She looks back at you with a smile. She has calmed down a lot now.

You open the door and flick the lights on.

She steps in first, and you close the door behind you.

"Nice place Mr. Fenaughty." She offers in something of an adult tone which doesn't seem to fit her frame.

"Thanks." You pause for a moment, and then throw caution to the wind just a little, "It's been a difficult night, would you like a drink?"

"Is that what you ask all the girls you bring here?" She responds without answering. "If it's okay, I need to use the little girls room" there was hint of play and irony in her tone which did exactly what she wanted and lightened the mood.

"Sure. It's just through there."

Your one bedroom apartment really isn't designed for entertaining.

Your arm still hangs in the air as she follows the gesture you're making through the bedroom and into the ensuite.

She closes the door, leaving it ajar just a crack, and the quiet sounds of her pee hitting the ceramic of the toilet bowl join the clicking sounds as you throw ice into a glass. You make your drink leaving an extra empty glass on the counter, not wanting to be presumptuous. After you first sip you meander around your own small living area, passing time like an anxious stranger in your own home.

It was an awkward amount of time though, too long for her to pee, and your curiosity blended with your nerves and concern. You start to think about what she might be doing; what she might have found.

When you go into the bedroom, she is sitting on the end of your bed. Legs just apart, comfortable and curious at the same time. She is holding the thing that you really did not want her to find and you remember that you must have left it out on the nightstand last night.

"Has this been inside of you Mr. Fenaughty?"

There was no other word for it. She looked cheeky. Her eyes looking up at you playfully, never breaking from your own. It was only in your peripheral sight now that you could see her fondling and twirling the toy that had been in your arsehole last night.

A black, vibrating plug still had the dried remanence of stale lubricant. She was not afraid of it. If fact, she seemed to a have perfectly switched the power dynamic, taking charge and letting you know that she now shared your dirty little secret.

"I want in inside me now Mr Fenaughty."

Something happened to you in that moment, you lost a piece of you. That last remaining pice that was holding you back. Now, as you watched her slide back a little in the bed, lift her skirts and slide down her panties. You weren't her former teacher, you were her man, and you wanted to taste her.

Her panties still around one ankle she rocked back and presented the smoothest little arsehole you had ever seen. You put your drink down and step in towards her, taking the toy from her hand and immediately and without hesitation runing your tongue around her pert hole leaving a train of saliva as you go.

You look up and she is still craining her neck to look into your eyes, the cheeky look starting to give way to ecstasy. You push one finger into her and she breaks her gaze, letting her neck relax and she lets out a moan that combines pain and pleasure. The muscles around your finger suggest that this is a completely new experience for her.

You take your time, and she relishes each and every moment.

After her tight arsehole loosens a little you gently slide out from her watching as her rings close immediately leaving no trace save for the gloss of your saliva. Your are preparing her now. You know that there is no way she will take the plug immediately, but she is ready - hungry even - for two fingers.

You lick your fingers, noting the taste of her on the one that had just probed her tight, virgin arse. As you push with a deliberate, gentle but unrelenting force, she squeals in her slightly husky boy tone. She squirms, but not so that she wants to be free. You keep pushing and probing and her tight hole gives way for you.

Above her hole her cock has remained rock hard, standing at a mast of at least seven inches, smooth and delicious. With two fingers now firmly inside her, you take her cock inside your mouth and close you lips around the cut head before sliding down half way.

Holister
Holister
38 Followers
12