Teachers Bet

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An angry bet with huge implications.
4.9k words
4.14
167.6k
101

Part 1 of the 2 part series

Updated 06/07/2023
Created 01/09/2015
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TheDarkCloud
TheDarkCloud
4,496 Followers

Holly shut out the inane chatter of her colleagues and the pounding music in the bar and raised her glass of vodka lemonade and took another large gulp, drained it and slapped it on the counter and motioned for the barmaid to give her another. It would be her sixth and she knew it was more than she should drink and much quicker than she should but she didn't much care. As she waited on her drink she glanced round and her eyes met with PE teacher Joe Price he raised his glass of beer in mock salute and Holly felt sick, she grimaced in return and hurriedly returned to her freshly served glass and angrily started on it.

Holly Will was a pretty, buxom, blonde, 33 year old drama teacher at St. Cameron's School in Oxbridge. The reason for her antagonism toward Mr. Price involved another teacher who wasn't there that night on the teacher's night out and in all likelihood wouldn't be back at school. Ken Brook was a gay English teacher and had made a great friendship with Holly in their three years together at the school (they even started on the same day). But from the off Ken had butted heads with Mr. Price and so had started a fairly deep seated feud.

Holly was sure that Price was just an old bigot that hated homosexuals , and she was right but he seemed to take a particular dislike towards Ken and tried to make his life hell at all times. In part it was also because Ken was so close to Holly because there was nothing the old letch like better than leering at pretty young blonde women. Things built and escalated until a series of claims from boys (all over 18) on the senior soccer team that Price ran seemed to incriminate Mr. Brook as making inappropriate advances towards them. When he was caught entering the changing rooms when they were naked his number was up.

Of course it had all been at set up. Mr Price seemed to engender a zealous following from the boys in his team so that they would seemingly do anything he told them. And he told them to ingratiate themselves to Mr. Brook, become his friend and then they set him up to be in the changing rooms at the wrong time. So now it seemed certain he would lose his job and that bastard Price was grinning at Holly like the cat that got the cream. She hated it and she hated him.

A couple of vodkas later and half the rest of the teachers had gone home or were thinking of it when Joe Price sidled up beside Miss Will at the bar and hissed in her ear.

"Don't look so happy Miss Will, what's wrong? Your little playmate ready for the chop?"

"Fuck off you old fuck!" she hissed back under her breath.

He just laughed and drank some more beer before leaning in and retorting.

"Damn you look sexy when you're angry, I'd just love to fuck you while you were wild like that, be a hell of a ride."

"Drop dead you old pervert, under no circumstances I can think of would you get near this."

"That so? You know Miss Will you look so pretty when you're angry and I'm guessing you want some kind of revenge on me for what I did to that faggot friend of yours, well if you're brave enough I got a proposition for you. Interested?"

Maybe it was the drink, maybe not but Holly was interested and listened in horror and interest in equal measure to the proposition Mr. Price put to her and she, in the end agreed to it. Next day when she had sobered up she considered backing out but she was sure she would win it and the reward for that was just too good plus she was a competitive person and didn't like to back down from anything, in that regard she was very like Mr. Price himself.

*

During a long, angry, drunken exchange that, by the time they were finished, saw the bar empty of all of their colleagues, this was the deal they came to. Fittingly it centred on Price's Senior soccer team, if they could lift the inter county championship then Miss Will would come into the dressing room after and offer her sexual services to both the coach and the boys on the team for the night. If they were to fail to win the championship then Mr. Price would submit to visit Mr. Brook and apologise to him while naked, on his knees and sucking his cock while Holly filmed the event and the film would be shown to the team after.

As an add on if the team failed to win Mr. Price would agree to get his full head of hair shaved bald and also his trademark bushy moustache shaved off, to Holly's surprise Price demanded the same forfeit from her, that after his team had lifted the trophy and she had serviced his boys she would get her head shaved bald too -- a terrible shame given how alluring her long, blonde hair was.

Despite these fantastical stakes they both agreed and both felt they would win. The coach was confident in his motivational abilities and also knew he had a good group of lads this year. Miss Will knew that St. Cameron's school had not won this competition in decades and indeed, last year had finished third bottom out of the eighteen schools that entered it. And, as alluded to earlier, both participants in the bet were, in their own ways, fierce competitors that never backed down, so while others would have flinched the next day at the enormity of what they were betting both Holly and Joe instead woke up determined that they would win the wager and were already looking forward to humiliating the other hugely.

Still though, neither fully trusted the other to honour the bet if they lost so they came up with a back up try to ensure that they did. Both wrote letters of resignation from their jobs addressed to the Headmaster and left the letters with Mrs Cotton, a science teacher they both knew and trusted to be discreet. Even at that she didn't know the nature of the bet only that if in May both of them came to her and asked her to post their letter that she would. This in effect allowed either Miss Will or Mr. Price to forfeit the bet but in actuality lose their job and in the current climate both knew that they could not afford to lose their job. Both were not worried about this though as they were both equally certain they would win and that if they lost they would honour what they had claimed.

*

The team won the first six games of the season much to Holly's dismay. After each game Mr. Price seemed to find her and give her a knowing smirk. Indeed after that sixth victory which confirmed them top of the league he went further, after a class he entered as the kids left her drama class and with her sitting at her desk writing he sneaked up behind her and leaned down to whisper in her ear one word.

"Bukkake!"

She nearly shit herself in fright and jumped up half in anger half in fright and confronted him.

"What was that! What do you mean?"

"I said, Miss Will, Bukkake. If you don't know what it means then look it up on the internet, though not on the school computers. Though judging by the look on your pretty little face I guess you've come across the word before. How interesting, guess I was right you are a dirty bitch, aren't you? Well goodbye for now."

Holly stood and glared at the asshole as he exited her room and hurried after him to shut the door and sit down again to catch her breath. The worst thing was he was right. She did know what a Bukkake was, she had seen videos and pictures on adult sites that showed a single woman getting ejaculated on multiple time by many men and she had masturbated and dreamed about that fantasy before. She was experienced sexually and had had several partners (though she was happily single at that time) and she had done a lot of pretty dirty, kinky stuff. How else would she have taken on this damned bet? But still she was not prepared to lose it. All afternoon during class though she could not shake the image of her on her knees in the boys changing rooms, her face and body absolutely covered in semen and her gagging and begging for more...

*

Things had changed a month or so later though after the team lost two games then drew their next one and dropped to third in their league. This time it was Holly that paid Joe a visit as he sat in the changing rooms after a class. She strutted in and dropped a magazine open in front of him, it was a gay porn mag she had been given by a hugely supportive Ken and the picture on the page was that of a bald older man on his knees submissively sucking the cock of a standing younger man.

"Like what you see old man? That'll be you come May, sucking away at Ken's dick and being his fucking bitch!"

Mr Price just glared at her then snarled.

"You're the fucking bitch around here! Now go on get out of here and take that faggot shit with you!"

Holly turned the page and showed him the next shot in the hardcore photoshoot where the older guy was licking the younger guys arsehole.

"Yeah, and that'll be you too Price, wait until your team see you as a cocksucking asslicker, be a real eye opener for them and their hero, won't it?!"

Holly scuttled out as a shoe was thrown after her and she had to nip into the loos on the next floor to quickly frig herself at the thought of their revenge on him.

*

But around Christmas time the team won a couple of back to back fixtures to go back into first place and this time it was Price's turn to goad, it was turning into a twisted game for the two of them. Waiting until the end of the day he stepped into her class, strode over to her and dropped a neatly wrapped Christmas present on her desk. Holly looked up surprised (though with the team top again she had expected him to put in an appearance).

"What's this Mr. Price?"

"Early Christmas present for you Miss Will. Why don't you go ahead and open it."

She paused but curiosity got the better of her and she undid the red bow and ripped open the paper to pull out the sluttiest looking air of red bra and panties imaginable. The bra was a peep hole one, designed to show nipple, the panties had no gusset and opened easily for access. Holly held them up with a look of disgust.

"You can wear them in May when we lift the trophy Miss Will, I'll be looking forward to it. In fact I'm already imagining you in them."

And with that he stuck his right hand down the front of his shorts and clearly started to fondle himself while looking straight at her. She didn't react just looked pityingly at him before sneering.

"I bet you've got the smallest dick imaginable you old fuck."

"Yeah? Well you're going find out soon enough slut" was his exit line.

*

After Christmas results were variable to the extent that Holly was visiting Mr Price again with only four games to go and the team in third place. She was wearing a light Summer dress and stepped up to Joe and held out her hand holding her phone and pressed a video message. The screen came to life with the image of Ken Brook naked and leaning back on his sofa masturbating (he had officially been released from his job just two weeks prior after months on suspension), Ken peered into the camera and played with his large, stiff dick and spoke to Mr Price as he played with himself.

"Well you old prick, getting nervous? You should be? I'm gonna choke you with this thing, I'm gonna ram it so far down your throat, you're going to cry and beg me to stop but won't and by the time I'm done you are going to crave the taste of my cock."

The video went blank and Holly set it down then reached under her dress and neatly took off her bra and panties under her dress and handed them to Mr. Price, they were the slutty ones he had given her at Christmas.

"Better hang onto these, asshole because you are going to be wearing them when you visit Ken. Red is the team's colour isn't it?"

*

And that proved to be the end of their mutual goading as things got busy towards the end of the school year and things got awfully tight in the soccer league. So tight, in fact, that the outcome of their bet and the school's attempt to win the league for the first time in forever would come down to the last match of the season with them in second place and two points behind the team in first place, who they were playing at home on that last day.

Holly couldn't help but attend with pretty much the whole of the rest of the school and she felt she was probably the only one of them praying for a defeat. The prospect of losing was horrible but at that she had a wetness in her panties at that prospect and would be lying to herself if she didn't admit to a few fantasies about what would happen were she to lose this bet. But no, on the whole seeing Price either humiliated in a homosexual situation or agree to hand in his notice was much the more preferable option the pretty blonde thought. Still..

In the end it came down to almost the last kick of the game, with the game tied at one all and nearly at the end the home team earned a late corner, they threw everyone up and when it was swung in the tallest of the boys rose like a salmon leaping and slammed a powerful header home sending the home crowd into hysterical celebration, especially as the referee called a halt to the game mere seconds later. As everyone around went wild Holly just sat stunned in place as she contemplated what she was going to have to do (and she would do it , she was no welcher on bets plus she just could not afford to not have a job). Amongst the delirium on the pitch, even as he was mobbed by excitable players Mr. Price scanned the crowd and seemed to lock eyes with Miss Will and she knew what he was thinking right then.

Holly made all the right noises to the kids and other teachers but she just wanted to escape, she had sent Ken a heartbroken text and was trying to flee when Joe cornered her and handed her a plastic bag, she knew it had that damned lingerie in it.

"Tomorrow morning at the changing rooms here at 8am, me and the boys will be waiting, and wear those Miss Will!"

She paused and fought back tears of frustration.

"Unless you want to go with me to Mrs Cotton and ask her to send your envelope, either way is good for me."

She bit her lip and stammered.

"No, 8am, I'll be there."

*

It would be no great surprise to learn that Holly spent a restless, fitful night during which she achieved very little sleep. Before going to bed she had spoken with Ken who was crushed that his opportunity to humiliate the man who had made his life hell was gone and did not seem overly sympathetic to what Holly faced. They hung up not on the best of terms.

Then she must have changed her minds a hundred times about going through with it or agreeing for her resignation to be handed in. She imagined her life with no job and no money coming in and couldn't see how she could cope with that scenario. Yet there was a part of her that was aroused by the situation, excited at what she was going to be made to do in the morning with all those horny young men. But it wasn't the team that really bothered her, it was Mr. Price. She had spent the year going back and forth with him, trading insults and threats, she hated him more than anyone she had ever known and tomorrow she would effectively be submitting to him. She did not think he would be pleasant about it. And yet she finally did find a little sleep imagining him doing all manner of unmentionable things to her and even she could not deny her pussy was soaking wet at the thought.

So with a confusion of thoughts and feelings infusing her Holly drove to the school that Saturday. The place was deserted except for a variety of cars in the car park at the PE block outside the changing rooms. She recognised Joe Price's car and several belonging to senior boys (again they were all well over 18 years of age, so at least Holly didn't have to worry about anything untoward in that direction). She got out of her car and locked it and was disconcerted to find her hand shaking as she put the keys into her designer handbag. She smoothed down the hem of the yellow summer dress she was wearing and steeled herself before walking on her matching yellow high heels over to the changing room door.

A smell of manliness assailed Holly's sense the moment she opened the door. A musky, sweaty, deodorant laced stench that overcame her and seemed to weaken her resolve as she passed through the inner swing doors and was faced with 15 men all in just their shorts waiting on her (and yes Price stood amongst them in just his shorts).

There was a cheer at the entrance of Miss Will. Of course there was, she was the hottest teacher in the school by a mile, many of the males in that dressing room had grown up having wet dreams about the busty, blonde drama teacher and now they were about to live them out.

"Well, well. So you showed up Miss Will. I'm impressed, I had you down as a quitter, thought you'd back out of our little bet."

Holly fixed the gloating Price with the harshest stare she could muster, before muttering "no."

Then from the boys themselves came a chant.

"Get your tits out for the lads! Get your tits out for the la-ads!"

It was a laddish, humiliating refrain, made all the worse because she knew them all and because she was about to do what they were singing about. She did hope it would die down, but when it didn't and they kept on singing she sighed and reached down and pulled her yellow dress up and over her head and stood before them in all the glory of the red slutty peep hole bra and crotchless knickers the Coach had goaded her with. At least it stopped them singing as most were struck speechless at the sight of her, some had doubted Coach Price that this would happen but there she was, stripping off.

Holly felt like a cheap slut taking off her dress on demand like that, standing there in these tacky under garments as they wolf whistled and ogled her. Her cheeks went red with shame but actually she also secretly enjoyed the reaction her little strip had engendered in the males, who didn't want to be lusted after? And judging by the stiff ridges emerging in their shorts she was certainly arousing something in them!

"See, I knew those would suit you Miss Will. Really shows what a slut you really are. Still as good as you look in them I want to see you out of them, strip them off!"

Price's words were tinged with real dislike for the pretty teacher. She paused a moment but in the end caved and undid her bra and dropped it then stepped out of her panties and defiantly kicked them at him as she stood bare naked before them. Showing lighting reflexes Price caught her discarded panties and held them up to his nose and loudly inhaled them.

"Just as I thought bitch, you are wet as fuck for this. No, don't bother denying it I can smell it here, the thought of sucking and fucking all these dicks has got you wetter than the Thames in flood!"

She just stood there and burned with shame. The thing was he was right and it killed her that he knew it for certain now. He dropped his shorts to reveal a thick, stiff cock and walked confidently up to her. He smirked at her and it really hit home how she had lost. The whole year's goading and sniping between them had led to this moment. He placed his hands on her shoulders and slowly but firmly pressed down to push her to her knees before him. When she was on her knees he grabbed his cock and slapped her cheeks with it several times and when she opened her red lips to complain he shoved it right in.

If Holly had thought she could control things while dishing out blow jobs that morning she was quickly proven wrong. Price fucked her mouth like it was a cunt, pounding in fast and hard, his balls slapping noisily on her chin as he did so. He grabbed her hair and held on tight meaning she couldn't withdraw and for a few minutes just treated her like a piece of shit cheap whore until he grunted, pulled his dick from her gasping lips and sprayed a thick load of cum all over her surprised face. As is slowly dropped from her nose and lips he stood back and announced.

"Right boys, she's all yours, treat her like all sluts deserve to be treated."

TheDarkCloud
TheDarkCloud
4,496 Followers
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