UMD Stories


Kevin's Messy Lesson
Story by Deeppan9x
Posted 7/4/19     3167 views
Ever since Kevin's humiliation at the hands of his ex-girlfriend's mum and her sister, his life had taken a somewhat unexpected turn. It was there he'd discovered the thrill of being dominated by older women, especially when that domination involved him getting covered in cakes, pies, tarts, gunge and slime. Kevin had not actually dared go back to face them again but often thought of doing so.

So, he'd taken to writing down or drawing his fantasies of being pied or gunged by various older women. These included stars of films and TV but also women from real life such as his college tutor. And it was there that he'd come unstuck.

During yesterday's lesson with Miss Rafferty, Kevin spent most of his time doodling on a piece of paper and drew an image of his tutor, dressed only in lacy underwear, holding a pair of heaped cream pies. Unfortunately, in his rush to leave he'd left the drawing behind and only realised his mistake when he'd got a note from his tutor asking him to come see her the following day after class.

* * *

Kevin had a free period at the end of the day which he spent worrying about the upcoming meeting with his tutor. He tried to think positively and imagine it was about something else, but he just knew that Miss Rafferty had seen his drawing of her and he was in trouble. He just hoped that it didn't mean his expulsion, after all it was the first time he'd gotten in trouble.

Eventually the bell signalled the end of the day and students began filing out of classes and heading home. Kevin made his way to his tutor's usual classroom but when he got there, there was a note with his name on it pinned to the door. He pulled off the note and read it, it asked him to meet Miss Rafferty in the old cafeteria instead of the classroom but gave no reason why.

He hadn't been to the old cafeteria since he'd first visited the college along with his parents when he'd been deciding where to study. Luckily, he could remember where it was so made his way along the corridor and down the stairs to the ground floor. Finding the door to the cafeteria shut, he knocked and waited for a response.

"Come in" a female voice called out.

Kevin opened the door and walked in. He was somewhat surprised to discover the assistant principal Mrs Strickland in the cafeteria rather than his tutor. She was standing in the middle of the room which was bare except for a single plastic chair situated in the middle. This can't be good, Kevin thought to himself.

"Hello Kevin, please take a seat" Mrs Strickland said indicating the chair beside her.

Kevin walked over and sat down on the chair. He found himself facing a blank wall, with the assistant principle off to one side looking down at him with a stern expression showing on her face.

"I understand from Miss Rafferty that you've been having inappropriate thoughts about her and taken to drawing these down where anyone might see them" Mrs Strickland stated.

Kevin started to shake his head in a futile attempt to deny the truth when he heard footsteps approaching from behind. Miss Rafferty walked by and struck a pose in front of him. Kevin was astonished to see that she was dressed in only high heels and her underwear: black Basque, thong panties and a pair of stockings. As in his drawing, she was holding a pastry case heaped with what appeared to be fresh whipped cream in either hand.

Kevin couldn't quite believe what he was seeing. It was as if his all his fantasies were coming true and he couldn't help but twitch a little on the seat as he realised that he was starting to get an erection. Miss Rafferty gave him a knowing grin as she stepped right up to him and began to taunt him with one of the pies, waving it around near his face.

"Miss Raff..." Kevin began to say.

Without warning, his tutor smashed the pie right into Kevin's face. He was completed blinded by the pie but could clearly hear the laughter from his tutor and the assistant principal. He waited for them to say something, but it had all gone quiet, so he reached up and wiped the pie cream from his face until he could see again.

Miss Rafferty was still standing in front of him but was no longer holding any pies. She winked at Kevin before glancing over towards Mrs Strickland. Kevin did likewise saw that she was now holding a pie. Before Kevin could say or do anything, Mrs Strickland smashed the pie into his face and firmly ground it back and forth to ensure total facial coverage.

"Be careful not to get any cream on your suit" Miss Rafferty warned Mrs Strickland.

Mrs Strickland smiled at her colleague and took off her jacket. Then to Kevin's total surprise she continued stripping off, removing first her skirt to reveal black suspenders and stockings and then her blouse to reveal matching bra, garter belt and panties. Mrs Strickland might have a decade or more on Miss Rafferty, but it seemed she certainly kept herself in shape. Kevin was getting more than a little turned on by the assistant principal's display.

Meanwhile, whilst her student's attention was elsewhere Miss Rafferty had retrieved a trolley laden with a dozen pies from the interconnecting kitchen. She wheeled the trolley over towards Kevin and picked up two pies. She passed one of the pies to Mrs Strickland, and the pair of them simultaneously sandwiched Kevin's head with their pies. They each took another pie and one at a time hit Kevin in the face with them.

"It's a pity we can't spank naughty students any more" Mrs Strickland bemoaned.

"Oh, I think we can do better than that!" Miss Rafferty responded.

Miss Rafferty indicated for Kevin to stand up which he did. She then picked up a pie from the trolley and after a moment or two of teasing him with it, thrust it into his crotch. Mrs Strickland laughed at Kevin's obvious discomfort whilst Miss Rafferty picked up another pie from the trolley and offered it up to Mrs Strickland.

"Your turn" Miss Rafferty said.

Rather than immediately taking the pie and smashing it into Kevin's crotch, Mrs Strickland had an alternative approach. She undid his trousers before pulling them down, then pulled out the waistband of his underpants. Taking the pie from Miss Rafferty, she deposited it into Kevin's pants before reaching in and massaging the creamy filling over his cock and balls.

"Seems like someone is enjoying themselves" Mrs Strickland declared.

Mrs Strickland began to glide her hand up and down Kevin's erect member. Meanwhile, Miss Rafferty went back to the trolley and began to smash pie after pie into his face. Kevin just stood there, being humiliated and pleasured at the same time by these two beautiful, older sexy women and loving every moment of it.

As Kevin reached the point of climax, Miss Rafferty stopped pieing him and instead waited eagerly with the final two pies in hand. As he ejaculated, thanks in no small part to Mrs Strickland's intimate ministrations, Miss Rafferty used her pies like a pair of cymbals and smashed them against either side of the assistant principal's head much to her and Kevin's surprise.

* * *

The following day Miss Rafferty was having afternoon tea with her best friend and telling her all about the unusual disciplinary measures she'd taken with her student.

"I was so much fun, I need to do it again" Miss Rafferty said.

"I can certainly understand that" Julia replied.

The end.
Tagged male
Comments:
BlueGriffin:
7/4/19
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Hmm, nice lead to the next story. All four of them possibly having a fun time messing him....
cmfan777:
7/5/19
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I agree, with BlueGriffin. This is an excellent set up to a larger session, perhaps with all of the women. I wonder how Stacey would react to hearing about all of this.
Deeppan9:
7/5/19
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I certainly think the more the merrier...
Deeppan9:
7/5/19
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Mmm, I'd forgotten about Stacey.
cmfan777:
7/5/19
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If she hadn't cheated on Kevin, none of this would have happened. Perhaps either Kevin or the the newly Pie-enthused women should find some way to "thank" her?
Deeppan9:
7/5/19
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I wonder what form that "thanks" should take?
cmfan777:
7/5/19
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Hmm. It seemed Kerry was disappointed with Stacey. Perhaps some sort of comeuppance would be in order?
Deeppan9:
7/5/19
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Something pie-shaped for example?
cmfan777:
7/5/19
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One would infer that was a possibility, but I would not presume to know authorial intent. That notwithstanding, that's not a half-bad idea.
Oops:
10/19/22
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This is a very fine tale, with some excellent descriptions of the lingerie worn by each teacher ("...dressed in only high heels and her underwear: black Basque, thong panties and a pair of stockings...", "... black suspenders and stockings and... matching bra, garter belt and panties") in the context of femdom punishment WAMming. In particular I welcome Mrs Strickland's decision to undo Kevin's trousers and pull them down, then pull out the waistband of his underpants and throw a pie down them. Great narrative dynamic and look forward to more femdom punishments, please!
Deeppan9:
10/25/22
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Thanks for the feedback Oops and rest assured that more femdom stories are on their way
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