The Seduction of Ms Caster

As I walked into the home room for morning registration I saw my best friend Noah already sitting at our table, lazily scrolling through his phone, his expression vacant through tiredness. Normally I would be much the same, but today was different. Smiling coyly to myself I pulled out my seat, placed my chin on my fisted hand and my elbow on the table, giving him the smuggest look I could manage.

"Pay up." I remarked, causing him to look up from his phone.

"Whuzzat?"

"I finished the bet last night."

"Bullshit." He looked worried now, though not yet convinced. I slid my own phone onto the table with the screen unlocked, a chat open.

Me: last night was intense. round 2 soon?

Lindsay: That could definitely be arranged ;)

"Fake. There's no way that's her." Noah protested.

"Oh yeah?" I asked incredulously, snapping my phone back up and rapidly working my thumbs. "Watch this."

Noah turned just as I hit send and watched Lindsay Turner pull her own phone from the pocket of her khaki cargo pants, blushing as she read the message, her own thumbs soon moving quickly. My phone buzzed and I read the message with pride, replied, then once it had buzzed again slid the open phone back onto the desk.

Me: at lunch? I'll drive us to the beach and show you a private spot

Lindsay: Don't tempt me! I don't have a change of clothes. :(

Me: good, skinny dipping's more fun

Lindsay: Oh god! I'm already getting wet!

"Jeez... okay, that's impressive. I was genuinely convinced she liked girls."

"Clearly not." I confidently remarked.

And what reason did I have not to be confident? Our year was small, just seventeen of us left, and though we had all passed the most awkward stages of puberty, not all had waltzed through quite as spectacularly as I had. Whilst Noah stood at 5'10" and was built somewhere between lean and skinny, I was closer to 6'2", and at my last weigh in I was 194 lbs of muscle. I had been a member of both the under 18's basketball and rugby teams before I aged out of their bracket six months ago, and now only play recreationally until I leave for college. But that's still a couple of months away, so for now my physique serves no purpose other than appearing pleasing to the eye. Honestly, the down time has been nice, and let me focus on other things. Like the bet.

Of the seventeen of us left there are eight girls and nine boys. Up until the end of last year I had been dating Georgina Pearson, but she got drunk at the Halloween party and got fingered by some college guy. We had a very loud, very public argument where I punched said college guy, but more than his nose was broken that night. Ever since then,

Georgie

has been somewhat of a social pariah, whilst I have been afforded great sympathy. That is where the idea of the bet started.

Noah had never been lucky with the girls, even with me as his wingman, whereas I've always been treated more favourably. The first day back after October break - one week after the party, and one week since anyone other than Noah had seen me - Brittany, Becca, and Lucy all made a move to let me know they would be happy to supply a shoulder to cry on. Lucy was persistent about it, in fact.

"Jesus Christ, Caelan," Noah had uttered. "I can't get one of them to look at me, and yet every girl in class wants to fuck you."

"I mean, you're not wrong. Can you blame them?" I smarmily replied. The attention was nice, and I wasn't in the best of head spaces, so I enjoyed the confidence boost.

"Asshole. I bet you really think you could, huh?"

"Could what?"

"Fuck every girl in class."

"I mean, discounting Georgina for obvious reasons, I bet I

could

..."

"Oh you

bet

you could? Bet what?"

"I'm not making a bet about this." I faltered, not liking where this was going.

"Oh, so you don't think you could do it? Ain't the hot shit you claim?" He goaded.

I narrowed my eyes and a thin smile formed on the side of my lips. "Okay, you're on. I bet by the end of the school year I'll have banged every girl in class."

"A hundred?"

"Deal." We shook on it, right as registration began being called.

That was five months ago, and now I had done it, with eight weeks of class to spare. I started with Rifa Mitri, knowing that due to her culture she would never go for it if I was seen as a player. We went on three dates before we had a fairly eventful week of daily sex, though that culminated in both of us deciding we were too different to take things seriously.

Lucy Morgan came next, and was by far the easiest to win over. A ride home from school was all it took for her to offer me a friendly blowjob, and who was I to refuse? We hooked up at least ten times since then, and each time was memorable. She is

wild

.

Brittany Macleod, Laura Devlin, Becca Wilkinson, Aimee Corrance, and Candace Parsons came over the next few months. From December to March I spent so much time in their company that I nearly forgot what my mother looked like. But that left just one. Seducing Lindsay had been different. She was shy, bookish, and a tomboy - not my usual type. Most assumed she was gay, but as it turns out she's just odd. She had only been part of the class since the beginning of the year, and as such hadn't really made any friends. In order to win her over, I bought a copy of the book she was reading and sped through it. An in-depth conversation about the strength of Hazel Grace Lancaster was all it took for a friendship to bloom, and a further two weeks of spending time together sealed the deal. As it turned out, not only was she not a lesbian, but she wasn't a virgin either, having experiences with two people before me. And that leads us to now, and my winning of the bet.

Or so I thought.

"Doesn't count." Noah protested, obviously not looking to fork out £100 that he likely didn't ever expect to lose.

"Explain?"

"Last time I checked there's another girl in the class." He retorted, glancing to the front of the room and nodding in the direction of Ms Caster, our class head.

"Fuck right off, we agreed girls in the class, not teachers." I argued, annoyed at the very notion he'd consider this a part of the bet. Whilst I had definitely enjoyed my recreational activities this year, I wouldn't have done them if not to prove the point.

"Ms Caster, can I ask a question?" Noah raised his hand, a look in his eyes that I didn't like.

"Yes, Noah?" The ever cheery Ms Caster asked.

"For the purposes of counts and such, are you considered part of the class?"

"Well, technically yes," Ms Caster offered. "My name is on the attendance sheet, and in the event of, say a fire alarm or an evacuation, my name would also appear as the head of the class."

"Thank you

very much

." Noah drew out every word, a smug smile of his own now across his face, though mine was nowhere to be seen.

"There's no way you expect me to," I stopped in the corridor, looking around to see that no one was close enough to hear. "Seduce Ms Caster."

"She's divorced, ain't that old. Hell, she's actually kinda cute. In her own way." Noah laughed, his observations not inaccurate but entirely irrelevant.

"Bro, I can't believe you'd stoop this low for a hundred quid." I tutted my disapproval.

"Buy me lunch for a week and we can call it quits." He offered, slapping my shoulder.

"Nope. A bet's a bet. And after this, I need to teach you a lesson. I'm taking your money." I defiantly replied. Noah stopped moving, then laughed harder than I had ever seen as I continued walking on to class.

#

For the last two years I've worked part time at the local golf club and leisure centre. It's a very exclusive affair, with annual memberships costing upwards of a thousand pounds. Tony, the manager, was my dad's best friend, and I've long believed he only gave me a job out of pity when my dad passed. But it's worked out well, I work as the lifeguard as well as the odd job guy, and the pay is far better than anything else I'm qualified to do. Plus it means I get plenty of opportunities to look at rich women in their bathing suits. I unironically love my job.

Each year we host a company raffle to raise money for a member chosen charity, with prize winners being picked out of a tombola. Last year I was chosen to pull the tickets, with the only stipulation being that none of my family entered. Tony hasn't asked me yet, but I'm going to make sure I can host it again this year.

As I entered the Golden Orchard Golf Club - thirty minutes early, no less - I approached Tony with my usual can-do attitude. As always he greeted me with a warm smile, the evidence that he still holds me in high regards even years after my dad's passing.

"Hey kiddo. You're early. Too much free time?"

"Hah, something like that. I was actually gonna ask if I could host the charity gala again this year?"

Tony eyed me curiously before shaking his head lightly. "Sure. You did fine last year."

"Cool. Can I try to sell tickets at school?"

"Ah, there it is. None of the kids in your class are allowed to win."

"Tony! They aren't kids, we're all eighteen now. But no, I was just going to ask the teachers."

"Ah. Well that's fine. You're a good lad, Caelan."

"Thanks, Tony."

#

"And the winner of the grand prize, a one year platinum membership to the club is..." I moved my hand into the tombola, then let the small named ticket I had stowed away earlier slip into my palm. "Molly Caster!"

Cheering and clapping rang out, and I stepped down off the small stage to hand the card which would give Ms Caster access to the resort. She smiled excitedly as the small metal coloured card was handed over.

"This will work until your named card is made up. I look forward to seeing you there, Molly." I said as I handed it over, kissing her cheek. I had started the practice last year with the elderly Mrs Henderson, who had won a wine and cheese selection, then again when Mrs Connor tapped her finger to her own cheek after she won a fruit basket, though I suspect she enjoyed the kiss more than her prize. The smooch I planted on Ms Caster lasted longer, though, and after my lips had left her face I noticed it had turned a noticeable shade redder.

"Thank you, Caelan. I look forward to trying it out."

#

The gala had been held on a Tuesday, so it was three days before my next shift. Still, on Friday at school I had mentioned it to Ms Caster, telling her she should come down to relax. The air was warm, the pool was large, and the membership had started from Wednesday morning. She had already let two days go by without making the most of her prize.

"I have papers to mark." She protested.

"There's plenty of space for that. I can reserve a table and parasol for you, you can sit in the shade with a cocktail, it could make the process a little more relaxing." She eyed me almost harshly. "Okay, okay, a mocktail." I relented, my hands raised in a faux-defensive manner.

"It would be nice..." She trailed off.

"I'll see you there, Ms." I warmly told her, my smile evident, then turned to leave for work.

My shift began at five, so when she hadn't arrived by six-fifteen I assumed she wouldn't be coming, but then she appeared. She was wearing a modest black one piece with golden clips, a blue sarong loosely tied around her waist, a pair of sunglasses obscuring more than half of her face, and a book bag under her arm. Her figure wasn't the same strive for perfection that the girls in class aimed for, she had a few extra pounds around her waist, her thighs were thick, and her usually well hidden breasts were larger than I had ever thought. I almost didn't recognise her. Noah's offhand comment struck me then.

Kinda cute in her own way

. He didn't know how right he was. She waved to me and I came down from my guard's chair to greet her properly for the first time. Her smile was warm and true, and I couldn't help but smile back.

"Glad you could make it, Ms Caster. You look great."

"Thank you, Caelan. It really is luxurious here, I feel so out of place." She commented as she looked around, seeing people reclining in the evening sun with drinks in their hands, people swimming laps in the lengths pool and splashing playfully in the leisure side. Her eyes widened as she caught sight of one guest with her top untied, her bare back soaking up the sun's rays. I saw her looking and my smile turned into a grin.

"There's very little dress code. No lower half nudity in the open areas, but tanning your top half is permitted. If you want to follow me I'll fetch you that parasol and table I offered you."

"Thank you, Caelan." She almost gulped. She looked mildly uncomfortable, but also intrigued.

"Here we are," I outstretched my hand and showed her to her seat. It was less than a metre out of direct sunlight, but had adequate shade for grading papers. As she sat I leaned down and looked her in her eyes.

Huh, they're green. Never noticed before

. "Give me a moment and I'll call Mickey over to get you a drink. If you need anything else, just give me a shout."

After a further forty minutes I decided to have a swim of my own. It was seven now, so the sun was no longer at its hottest, but it was still warm enough to enjoy a dip in the water. I pulled my tank top off and jumped in, completing five laps before resting at the side of the pool and glancing over to Ms Caster.

"Sun's not going to be out much longer. You should swim while you can." I called over.

"Oh... maybe next time." She tentatively called back, her reluctance obvious.

"There's only three of us here, Ms Caster, you're letting the pool go to waste."

"I... Okay, you win. Give me two minutes."

We swam together for fifteen minutes, me slowing my usual pace to keep beside her. As we took breaths at the side of the pool we chatted, and more than once I caught her trying not to look at my physique. In fairness, I was looking at her, too.

Whilst the obligatory 'who's the best looking teacher?' conversations had definitely taken place in school, I had never truly considered Molly Caster to be a particularly sexual being. Now I could see how foolish I was. Her auburn hair had matted to her face, somehow slimming it whilst accentuating her well symmetrical features. Even without a dash of makeup her lips were full, her eyes were wide - though slightly bloodshot from the water - and her skin was clear. At school her hair was usually resigned to a ponytail, though it had some considerable length, and now it clung to her neck and shoulders, trailing down over her chest. Her nipples stood ever so slightly erect through the material, and I felt myself begin to harden.

"Ahem... Race you to the other end." I blurted out after staring a little too long at her chest, my imagination running wild. We took off, and I let her take the lead, happily trailing behind her as we made the lap.

"You let me win." She scolded as I resurfaced.

"Have to keep you coming back." I joked, then winked at her as I wiped my face. She smiled, then pulled herself out of the pull.

I watched on as every inch of the fabric clung to her body, fitting her form more intimately than any clothing normally should. She hooked her thumbs into her suit at the rear and I saw the slightest glimpse of her bum, and at that point my semi-erect member became full.

"I'm done swimming for the night, but I don't have a towel. Would you mind grabbing me one?" She asked inquisitively. I looked at her face and knew I had been caught admiring her.

"Sure, just... give me a minute." I meekly replied.

She looked at me, confused at first, then it must have clicked, because her face reddened and she shyly nodded as she went back to her table. Once I had calmed down I got out of the water and grabbed the towel.

"How was your visit, Ms Caster?"

"More enjoyable than I expected. I haven't swam in so long, I forgot how nice it felt."

"Glad to hear it. So... you'll be back?"

"Yes Caelan, I believe I will be."

#

Over the next four weeks I was at the club most nights, just to work out if Ms Caster would be there. When she wasn't I went home early, but when she was there we spent more time together than she had expected. Despite my ulterior motives, much to both our surprise, we became friends. We made a game of our swims, her being unable to best my speed, but a general knowledge question from each of us at the end of the race evening the odds in her favour. She was a fountain of knowledge on top of being a very attractive woman, and I soon realised that beyond finding her conventionally attractive, I had a crush on her.

"Who was the first Prime Minister?" She asked as she floated there, looking smug as she always did when one of her questions stumped me.

"No... I know this." I protested, raising my finger to halt her gloating. "Walpole...?" I asked, almost scared of her coming response.

"You wouldn't have known that if not for my exemplary teaching." She offered, trying to grasp victory any way she could.

"Uh, you've never taught me history, Ms."

"Irrelevant. I lead a fine example." She laughed. In response I splashed her, water gently cascading over her face. She gasped, her expression shocked, but a devious smile soon formed on her lips. Before I knew what had happened she had dunked my head under the water, then splashed me as soon as my head resurfaced. We both laughed, then I dove under once more, grabbing her foot and tickling it, her legs flailing wildly before I took off for the other side of the pool.

"That's it, now you're in trouble, Mister!" She called out as she sped after me, another wave hitting me as I raised my arms in surrender.

"I yield! Have mercy!" I dramatically pleaded.

"No mercy for ticklers!" She responded, her hands once again landing on my head and pushing me beneath the surface.

The previous time this had happened I had fallen back, but this time I did the opposite, moving in her direction, causing her to push my face into her body, narrowly missing her breasts but making contact with her tummy right down to her crotch. I felt her stiffen as I steadied myself by placing my hands on her thighs, resurfacing to see her wide eyed expression.

"I..." She went to speak before a stream of water escaped my mouth, arcing through the air and making contact from her chin to her chest.

"No mercy for dunkers!" I responded, raising my hands to her waist as I lunged forward, taking her under with me.

Our bodies pressed together for mere moments, but the excitement surged through me as I felt her form against mine. She grabbed on and we both came up, our arms around each other as we took a breath. After the water left our eyes we looked at one another for several seconds before one of her hands found my chest and she slowly pushed herself off of me.

"I should go." She nearly whispered, the words barely coming.

"No, you stay, technically I am working." I replied, wading towards the edge of the empty pool and pulling myself out, standing still for a moment at the edge, doing nothing to hide the tent in my shorts. Ms Casters lips slightly parted as she stared for longer than I expected, only turning away once the noise of a door closing brought her back to reality.

"Enjoy the rest of your night, Ms." I called as she floated there, her face awash with emotion.

#

"You should just give me my money now, Cael. You know it ain't gonna happen." Noah's voice came down my headset as we gamed together.

"Shut up and concentrate. We have bugs southwest and I plan on keeping these rare samples." I demanded, eradicating the enemies on my screen.

"Mate, can't even admit to yourself that you bit off more than you can chew?" He taunted as I watched him get swarmed less than 100 metres from the extraction point. "Oh shit, res me!"