The Prescot Chronicles Ch. 02: A Mentor Seduced

He opens his email and taps out a message, thinking about his words carefully, as you never know who is looking over your shoulder when an email pings into your inbox.

"Ms. Davidson, I just wanted to reach out to you to say thank you for attending my presentation this past Friday. I tried to contact you earlier but lost your contact information. Thankfully, I still have the pen you shared with me after I presented. I found your participation in my session to be very stimulating and wanted to let you know that I've been giving considerable thought about the points you raised in our discussion afterwards. I would love to carry on that conversation, if that works for you.

Sincerely,

John Prescot"

Reading his message over for typos, he clicks send and sighs. He was pretty sure this wasn't a good idea, but it was still better than being unhappy.

With nothing else to do, John shuts down his laptop and goes about tidying up his desk. He picks up a stack of atlases his students had been using that day and takes them into the back room to put away on the shelves. As he is reshelving the books, Lily opens the door from her classroom and walks in.

"Hey John!"

"Oh, hi Lily, how was your first day?" He smiles, remembering how excited he had been after his first full day of actual teaching. Admittedly more than a few years ago now.

"It was great, thank you so much for sharing those lesson plans with me, they were so easy to follow."

John shrugs, "No problem, why reinvent the wheel? Once you feel comfortable with the course curriculum, feel free to ignore them and chart your own path."

Lily, now leaning against the shelf where John has kneeled to finish putting away the atlases, looks down and says, "Thanks, I appreciate the vote of confidence."

John looks over and notices he is eye level with the hem of Lily's skirt, her nylon covered legs just a foot away from his face. He looks up slowly, taking in the elegant form before him of the tight skirt hugging her legs just so, and the curve of her breasts outlined clearly in her striped shirt. At this angle, John can make out a slight pucker between buttons and the lacey black bra revealed beneath.

Looking up at Lily's face, who is looking around the room and thankfully hasn't noticed John looking her over, John says, "You were always one of the smartest students to come through these halls Lily, you will do amazing things, I have no doubt."

Looking back to John, still kneeling on the floor, Lily smiles, blushing slightly. She gently reaches out with her right hand, cupping the side of John's face, "Oh John, you're too kind." He smiles, feeling her fingertips trace over his jawbone as she pulls her hand away, "You were always my favorite teacher, in fact you're the reason I wanted to become a teacher in the first place." She stands up from her leaning position and steps towards the center of the room. "But I have to ask," she pauses, "what's up with the clothes here??"

John stands turning towards the opposite wall, where he has left a pair of pants and shirt hanging beside a sport coat. "Ah, my emergency clothes," he chuckles, "That is one of the most important things in this room, and something I doubt that they would have mentioned in your college courses. Having a change of clothes is crucial when you spill coffee on yourself mid-morning, as I found out several years ago."

"Oh?" Lily raises an eyebrow, "This sounds like an entertaining story..."

"They never tell you in teachers' college, coffee cups without a lid are the enemy. Especially when you have to cross a hallway during class change. Someone bumped into my arm, and I had a large double-double all down the front of me. Thankfully it wasn't very hot. But what a mess." He laughs at the memory of standing in front of his class wearing his coffee.

Lily joins in laughing, "I can only imagine!"

Nodding, John adds, "Surprisingly it's difficult to be taken seriously when it looks like you've pissed yourself." He motions to the set of clothes, "So ever since I've kept emergency clothes here."

Lily looks back at John, glancing down to his crotch, no doubt picturing the image of a coffee drenched John, "You're lucky it wasn't hot... you might have burned something important. Think of how disappointed your wife would have been." She giggles, biting her lip slightly as she turns her attention back to the stack of papers she had set down on the table initially.

Without thinking, John says under his breath, "Not like she'd notice..." Standing and reaching up to the top shelf John pulls down a set of maps he plans on using the next few days, "Well you look like you have your hands full with those papers, I'll leave you to it. If I don't see you before you leave, have a great night, Lily."

She looks up, smiling and replies, "Night John." She watches him leave, stack of maps in hand, and thinks about how he had responded to her comment. Watching his rear end as he exits Lily thinks back, she had always had a huge crush on John when she had been in his classes, and while he was an amazing teacher, the fact that she (and many of the girls in the school) thought he was hot in that dignified teacher/professor/older man way certainly made it easy to take as many classes from him as she could.

He has always been so nice. He welcomed authentic debate in his classes and encouraged his students to challenge the history as written in their outdated texts. Further, and lending to his sex appeal in her mind, was that John Prescot was genuinely charismatic and caring. A genuinely nice person who wanted nothing but the best for those around him. It made her sad, thinking that this amazing person might not be truly happy. He deserved so much better. Could she do something about that? Would he even be receptive, she wonders? She was pretty sure he had been checking her out as they had been talking.

Like all the boys in the hallway and her classes that day, Lily seemed to know when they were looking her body over. She loved knowing she had that effect on them, even as she pretended that she didn't notice. It was like when she had 'accidentally' dropped her book earlier in the day and had bent over to pick it up just as her 5^th period class was coming in. It made her so wet feeling all of those eyes examining her ass with her skirt stretched tightly over it. Lily smiles, feeling the delicious tingle start once more in her loins, squeezing her thighs to enhance the sensation.

John Prescot would be hers. She firmly cups her left breast, squeezing and feeling the hardening nipple pressing against her fingers. She stifles a moan as she gives the sensitive nub a squeeze, relishing the mixture of pleasure and hint of pain as she does so. Smiling to herself, she feels her panties becoming increasingly wet as she imagines what she is going to do with, no, do TO John Prescot.

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The Pursuit

Over the next few days John and Lily spend their free periods in the morning going over the curriculum for her courses, John produces pre-made lesson plans for her to use, while Lily starts to make little alterations to them that better suit how she plans on delivering them.

Towards the end of Lily's second week working with John, they have settled into a routine of spending most morning preps together. This Friday morning is no different, as the duo sits together working at the table in the back room. Lily leans forward ostensibly to examine this sheet or that page, relishing the opportunity to press one of her breasts against John. The first few times she does this John thinks it must be an accident, just a matter of happenstance, but as she does it for the third time that Friday morning, the end of their first week working together, John can't help but feel the firm protrusion of what is most certainly her engorged nipple pressing against his upper arm.

In a moment of boldness, John turns towards Lily and reaches across the table to grab a highlighter pressing his arm up against the breast she is pressing against him. He notes that she doesn't pull away but seems to bite her lip at the sensation.

'Interesting...' he thinks to himself, 'very interesting indeed.'

For good or worse, the period comes to an end before he has a chance to explore this newfound discovery any further. Gathering their materials up quickly, John stands, a noticeable bulge present in his pants. He stands as Lily continues to lean into him, feeling her breast press against his arm and, as he turns, the bulge in his pants.

Feeling the sudden pressure of Lily's breast rubbing against his rapidly stiffening cock, John lets out a small moan. He looks down at Lily, blushing, before turning quickly and moving to the door back to his classroom.

Lily smiles to herself as she watches John flee, her nipple aching at the thought that it had just been rubbing against his swollen cock. She reaches up and gives her nipple a quick squeeze before gathering her own materials and heading to her classroom.

As lunchtime arrives, John bumps into Lily down in the teachers' lounge, she smiles at him as she sits down across the table with her yoga themed lunch bag.

"Hi John, thanks again for all your help this morning. I really appreciated all of the points you made," she says, a wicked grin crossing her face. Looking down as she unpacks her lunch she asks, "How was the rest of your morning? I hope it wasn't too hard."

John almost spits out his coffee as she asks her question, "Er...um...no. It...it was just fine. Thank you." Blushing three shades of red as he examines his sandwich with far too much intensity.

Barely able to conceal her amusement, Lily adds, "Well that's a relief, although if things get too hard, let me know and perhaps I can help you out." She lets the last phrase dangle in the air between them, watching his face for a reaction.

She is not disappointed, as John looks up from his food and meets her gaze with a look of surprise mixed with just a touch of lust. "Thank you...I'll keep that in mind," John manages to reply.

From under the table John suddenly feels a nylon hosed calf press against his leg, slowly rubbing up and down. Lowering her voice slightly, Lily says, "I really hope that you do John...no matter how hard, I'm sure I could help handle it."

"I appreciate that Lily, I really do." He packs his container back into its bag and pushes back from the table. Lily notices a knowing bulge quickly growing in his pants as he stands. "I'm afraid I have to run, got a few kids coming in for extra help."

With that, John quickly retreats from the staffroom but instead of heading to his classroom, he heads into one of the staff washrooms upstairs on the third floor, locking the door behind him. Thankful that the staff washrooms were actual private rooms and not a series of stalls, John quickly undoes his belt, unbuttons, and unzips his pants and reaches down to rub his painfully hard cock.

He had thought that Lily was just being bubbly all week, but what had happened today made him realize that perhaps she had other plans in mind. Closing his eyes as he pulls down his boxers, taking his cock fully in his right hand he slowly gives his shaft several long deliberate strokes. Stifling a moan as his cock throbs in his hand, he recalls the feeling of Lily's perky breasts pressing against him. Her own arousal is evident in the hard as rock nipples straining against her shirt against his arm, or earlier this morning, his cock.

He continues to stroke his cock, picturing in his mind Lily's naked breasts and wishing he could feel her bare nipple rubbing against his cockhead, his precum smearing over it and covering her areola in the glistening fluid. What would it feel like, to press his cock between her tits, he wondered? Emily had never been interested in letting John tit fuck her, would Lily? As he strokes himself, he pictures Lily on her knees, blouse wide open and his cock enveloped between her two firm 34Cs, just enough to squeeze together and make a nice fuckable passage. She looks him in the eyes, as his cock pressed between her tits, before lowering her head to lick his cockhead whenever he thrusts up. Moaning as he feels her tongue flick across the tiny opening of his cock now leaking generous amounts of precum for her to lap up.

"God Lily, that feels so good," he says to her in his fantasy. Letting out another gentle moan, "I've always wondered just how your tits would feel to fuck them." He feels his cock throb, his balls already starting to tighten as he races towards climax.

"It feels so good John, your cock fits perfectly between my tits," comes her sultry reply. "We don't have much time, will you cum on my tits for me?" she pleads.

Hearing Lily say that is all the encouragement he needs, with a grunt and one last pump, Johns' cock erupts shooting cum all over Lily's lightly freckled breasts, chest and chin.

"Fuck yes, John, cum for me. Mmmm, yes daddy, cover my tits," Lily moans, taking a dollop of his cum and licking it off her finger.

Opening his eyes, his fantasy fading as his cock throbs and shoots one last spurt, making a plop sound in the open toilet bowl. He takes a handful of facial tissue and wipes the excess cum off of his cock, disposing it into the toilet as well before flushing and fixing up his clothing.

John exits the bathroom, taking a quick look around thankful to see that the hallway was still empty, before heading back to his classroom. Sighing in a feeling of post-orgasmic bliss, even if it was self-induced. Would the real Lily let him fuck her tits like that, he wondered, as he returned to his class.

10 minutes earlier...

Lily watches John quickly pack his things and hurry from the lunchroom. As soon as he is out of sight, she grabs her own things and follows. Based on the size of the bulge in his pants as he stood, Lily guesses that John is in dire need of release and decides to follow him. As he enters the first private bathroom, she quickly rushes into the second one very carefully to shut the door as silently as possible. She hears John undoing his pants through the shared air vent, and quickly the sounds of him masturbating float to her ears. Lifting her skirt Lily starts rubbing her pussy just feet from where John is stroking his cock. Biting her lip tightly as she dips her hand beneath her soaked panties, she drives a pair of fingers into her aching pussy.

Fingering herself while John is next door stroking his cock, Lily smiles knowingly when she hears John say her name. Her pussy squeezes her fingers at the thought that he was picturing them fucking. In a moment of boldness, she answers him, hoping that the response is part of his fantasy.

"It feels so good John, your cock fits perfectly between my tits," she purrs. "We don't have much time, will you cum on my tits for me?" she pleads.

As she fingers herself hard and fast, she can hear him moaning as he approaches his orgasm. She moans for him, "Fuck yes, John, cum for me." Panting, she adds, "Mmmm, yes daddy, cover my tits..." when she hears him grunt several times. She smiles to herself, wishing she had just taken his load across her chest. The thought sets off her own climax, her pussy squeezing her fingers tightly, spasming their own contractions while her hand is covered in her juices.

Taking a moment to come down from her orgasm, Lily straightens her dress as she hears John vacating the room next door. Listening as his footsteps fade down the hallway, Lily opens the door to the second bathroom, licking the last of her juices from her fingers as she heads back to class for the afternoon.

After school, John packs and leaves quickly. Waving sheepishly to Lily as he passes her room, he stops for a moment, "I'm afraid I have to get home right away. Have yourself a great weekend."

Lily steps out of her room as she says, "That's too bad, I was hoping we could grab a drink, I owe you so much for all the help these past few weeks." She gives him a hug, pressing her breasts tightly against John's arms, making it a point to nestle his arm between them. Giving him a kiss on the cheek she adds, "I am in your debt, John."

Blushing slightly, John replies, "Think nothing of it, just glad to help." After a moment to pause he adds, "I'm very happy you've joined our staff, and that we get to work together."

Lily beams up at John, "Me too, I'm so happy that I get to work with you." She asks, "Are you sure you don't have time for a quick drink?"

John nods, "I'm afraid so, Emily is out of town again, and I have to get Zach to his hockey practice."

Nodding, her disappointment evident. "Alright, well maybe another time. Have a great weekend," she says leaning up to give him one more kiss on the cheek.

Smiling, John turns and heads out, blushing and feeling the warm wet spot Lily had kissed as he departs.

Monday comes around far too quickly, the weekend a blur of chores and running errands. John's dreams are filled with an erotic mixture of Charlotte and Lily, the resemblance between them was uncanny. If he didn't know any better he could easily have mistaken Lily for the Charlotte he had been with 20 years ago.

Standing in the shower, the water running off him, John pants as he strokes his cock. Picturing Charlotte sitting on the edge of her hotel bed, legs splayed open and fingers frantically pumping in and out of her soaked pussy. She moans, opening her eyes and looking directly at John, biting her lower lip as she drives her fingers deeper. Panting as she pumps her fingers deeper, she calls out "Fuck yes, oh god yes..."

John continues stroking his cock, grasping it firmly as he strokes himself. Precum drips from his head as he reaches down and gently cups his balls, feeling them tensing as he begins his inevitable climb to orgasm.

In his mind, Charlotte licks the fingers of her free hand before reaching down and begins to flick her engorged clit. Instantly her moaning transforms into high pitch squeals as her body shudders, sending her over the edge. Her pussy clamps down and starts quivering around her fingers, her juices squirting out around her buried digits.

Watching Charlotte cum, squirting around her fingers, recalling how delicious her juices taste is more than enough to send John over the edge. With a grunt and a moan, he pumps several thick ropes of cum against the shower wall and down the drain. As he comes down from his post orgasmic flood of endorphins, John finishes washing up and turns off the water. Reaching out of the shower enclosure he pulls his towel from the rack and dries off.

Lily clearly has her sights set on him; she had made that much clear on Friday. Thinking as he dresses, John frowns. How was he going to deal with her advances? Did he even want to? It was one thing for him to hook up with Charlotte, who he has since admitted to her and himself that he was still in love. But Lily wasn't Charlotte, no matter their physical similarities. Straightening his tie mirror, John looks himself in the eyes. No, it just wouldn't be right for him to pursue Lily. He would just have to find a way to let her down gently.

Monday morning flies by, John buried himself in a pile of essays during his free period, effectively ignoring Lily who had tried to flirt with him but had backed off when she noticed the pile of work before him. Mid-morning the staff was reminded of their monthly meeting after school that day, poking his head into Lily's class in between second and third period he asks, "Did you see the message about the staff meeting?"

"No, I'm afraid I haven't checked my email yet."

"Last Monday of the month is always a staff meeting, right after school down in the library."

"Awesome, thanks for letting me know, not that I had plans after school today anyways," she chuckles but John can see a hint of sadness in her eyes as she turns.