The Raffle Part 2 - anonymous Commission m/f

[whiteunicorn]

So it was that David, newly dressed in a school uniform complete with black trousers, blazer and tie, the latter with yellow diagonal stripes across it was lead along to another room off the dressing room, one that had all the hallmarks of a classroom. Which surely meant that Natalie was playing the part of a teacher, her outfit perfect for that role; namely a grey suit jacket and skirt combination over a tight white blouse completed by black high heels. That was all he has been able to guess about this scenario and the mystery of it had him quite excited.

‘Sit down David.’ Natalie ushered him into the classroom lined with a dozen desks, her head inclined towards the single chair at the front of the room. ‘As your form tutor it’s my responsibility to talk with you about this. I’m sure you know what I’m talking about.’

‘Actually, I don’t.’ David replied as he did as she asked. That was true, despite her confirming his theory about the school setting, he had no idea what this scene entailed.

‘Really.’ Natalie moved to stand before him with crossed arms, her voice as stern as her gaze. ‘Then let me remind you. For you’ve been a naughty boy. Playing all those pranks on your tutor. Surely you remember placing the bucket of red Gunge over the door to this very room so it fell on me as I walked in. You certainly had a good laugh as I stood there dripping in gunk. No? Or how about filling the teachers changing rooms in the gym with buckets and trip wires, waiting until I was in the shower and pulling the fire alarm, leaving me to trip each one as I dashed towards the exit. Or maybe you didn’t think I would notice you watching, drenched as I was in gallons of pink and white slime. Or did you forget the time you tricked me into the cafeteria with talk of a fight, only to find dozens of your cohorts waiting with pies and cakes and buckets of Gunge, all of which I’m sure you told them to throw at me. I’m sure that jogs your memory.’

It didn’t, how could it. David had never done those things but hearing Natalie’s descriptions he truly wished he had. Just imagining how she might look after falling foul of those pranks sent his cock twitching, the sudden temptation to stroke his length almost too great to resist. Almost. With a slow breath David controlled himself, even as he allowed himself a shy grin, having made a mental promise to enjoy himself with those thoughts when he got home.

Natalie must have taken his instinctive grin as a response given how her eyes narrowed a little.

‘I see you think that’s something to be proud of. Well..that doesn’t matter. Because the school has allowed me to take your punishment into my hands. So I’ve arranged a practical lesson for you, something the headmistress is very keen on as I’m sure you know. Now..stand up and don’t move until I get back.’

Trembling with barely contained excitement that had his legs shaking as he stood, David endured what was most likely the longest wait of his life as Natalie ducked in and out of the classroom, returning with buckets upon buckets, trolleys laden with pies and a covered basket, the cumbersome shape being the last item she struggled in with.

‘Oh no…school dinners. Not that. Please not that.’ David replied deadpan, his sudden off the cuff improv catching even him by surprise. Seemed the last scene and the shower they shared had eased his nerves.

‘Mock if you like.’ Natalie said coolly. ‘I don’t think you will be so cocky when I’m done with you. And you do seem…cocky.’ There was no missing the subtle meaning behind those words, even without the pointed glance Natalie shot towards his tented trousers, the loose material not hiding his erection in the slightest. ‘But we will get to that later. I’m sure you’d love to ‘burst’, wouldn’t you? Well..I’ll be doing the ‘bursting’ here.’

That made no sense to David, at least until Natalie whipped the cover off the basket, revealing the mass of balloons inside. Before he could question that, Natalie grabbed three of them, marched over to him and stuffed them under his blazer before fastening the buttons to trap them against his shirt. Instantly David’s breathing hitched up, the odd wobble of the balloons telling him they weren’t full of air but something much thicker. And messier.

‘I’m sure it wouldn’t take much to make you burst. Just one touch maybe. Like this.’ Natalie punctuated that with a slap against one of the balloons which exploded instantly to fling green Gunge across his chest. Barely had that started to seep through his shirt than Natalie did the same with the other too, red and blue joining the sticky mess that dripped down over his trousers.

‘No..don’t move.’ Natalie commanded even though he hadn’t. ‘I’m not done yet.’

So it was that Natalie, careful of the Gunge slicking his shirt, grabbed what turned out to be the last four balloons, tucking three of them under his blazer again. The last one she kept, raising it over his head before delivering a heavy smack against it. The pop rang in his ears seconds before the gloppy Gunge splattered onto his hair, dripping over his eyes and down his neck. The other three got the same treatment, the forceful smacks adding to the Gunge soaking his shirt and sticking it to his skin, a multicoloured stream working its way over his trousers.

‘Look what you have done to your uniform.’ Natalie half scolded, half teased, a little smile breaking her stern act. ‘Get that blazer off this minute, and your shirt too.’

‘Fine.’ David grinned, still playing the surly student as he peeled off the sticky cloth to stand before her in just his trousers. ‘Happy now?’

‘Oh no. You still need to learn your lesson.’ Natalie chided. ‘Lesson one..how it feels to be coated in pies. Let me give you a taster.’

David knew what was coming but that didn’t entirely prepare him for the pie smushed against his face with a wet splat, the cream stuck to him like a white mask. Or for the next two clapped around his head in the classic pie sandwich that clung to his hair which the first pie had left untouched.

‘There. You see.’ Natalie’s voice dripped with cool satisfaction. ‘Now, hold out your hand. It’s your turn. I want to see you humiliate yourself as you did me.’

A little disoriented David still managed to raise his hand to feel the heavy weight of a pie rested on his palm, the firm pastry sagging a little from the cream that filled it.

‘Now..push that into your face.’

Hesitantly, mostly because he was struggling to keep his balance, David raised the pie slowly to ease it against himself. Sadly too slowly, as his hesitation simply sent most of the filling tumbling to splat over his shoes, only a little cream added to the crust topped layer against his face.

‘No..no..no..terrible.’ Natalie chided even as a scrape of plastic on wood alerted his attention. Which did nothing to protect himself against the bucket of water splashed over his face, the forceful fling warning away the pie blocking his vision. ‘Here. Try that again.’

Trembling a little from the cool water, David hefted the fresh pie and drove it with all his might against his face. Despite himself he couldn’t stop screwing his eyes shut as the creamy filling plastered itself against his face, more than half of it flung against his hair.

‘Better.’ Natalie said firmly as David scraped the pie out of his eyes to see her collect two more pies. ‘And these..no..not there. On your chest. Go on.’

Gripped by the excitement of where this might be heading, David did just that, clapping the pair of pies against his chest, the cool cream flung over his nipples and down his stomach, his skin tingling everywhere it touched.

‘How does that feel? Humiliating?’ Natalie asked. ‘Because this is what you did to me, pelting my face and chest with pies as I begged you to stop. I bet it turned you on, pieing my boobs didn’t it? You even went so far as to pie me..somewhere else.’

David’s cock twitched again, both those words and the way Natalie stepped up behind him lanced straight to his libido. As was the way she hefted a pie into her right hand. ‘So…what if I pied you there? Slammed this pie into your crotch like the ones you flung at mine.’

David wasn’t given the time to respond as Natalie did just that and thrust the pie forward with a heavy splat as her hand massaged the cool cream into his crotch; the hasty pieing turned into a lingering grope, her hand curled to stroke his shaft a few times before her fingers rolled down over his balls.

‘Mmmm…you like being groped by your teacher hmm?’ Natalie whispered, not stopping her sensual caress as she grabbed another pie which she drove against his stomach with a heavy splat. With David’s moan being answer enough, Natalie switched to rub her palm over his head very slowly as her other hand rubbed a fresh pie and its creamy load all over his chest while her fingers tweaked his nipples.

It was David’s creamy load that occupied his attention though, the soft slow caress of his shaft building to a release he knew he couldn’t contain if she kept going. So it was with mixed relief and disappointment that he released a ragged gasp the second age stopped.

‘Such a naughty boy..getting turned on by the touch of your teacher who is punishing you.’ Natalie replied with a grin of pure wickedness. ‘I think I really need to punish you. Come here.’

Confused yet still excited, David followed Natalie as she sat down in the chair he had recently vacated as much as he followed the guiding hands that eased him on his stomach over her knees. ‘You know what happens to naughty boys..they get spanked.’

‘Spanked?’ David whispered as Natalie deftly undid his trousers and in one smooth movement tugged them and his boxers down. This sudden stripping made his cheeks glow with heat, but not as much as the slap of her hand against his bare flesh. It didn’t really hurt, just a quick stinging smack that faded to a warm glow even after his yelp of surprise faded only to build to another as Natalie drew her hand back again. Two became three, then four, then five; his cheeks growing warmer with each hit even as he began to anticipate the strike of her palm. Strikes that stopped as abruptly as they started, leaving his butt truly red and glowing.

‘Oh yes.’ Natalie replied belatedly. ‘But I’m not done yet. I think you need a little more. How does a pie spanking sound?’

Wonderful…amazing..exciting..too much? All those words bounced around his head without much of an answer being produced beyond a low moan which seemed to be enough of an answer for Natalie who wasted no time grabbing a pie.

At least, not with grabbing it. No doubt looking to draw out his expectation and excitement of that moment, Natalie left the pie balanced on her hand while David squirmed in her lap; his ass still glowing and his cock rock hard. Made only harder by the thought of what she was going to do to him next, by the simple thought of his on screen crush smashing that pie against his ass making him twitch.

Which was nothing to the twitch he felt when she actually did it, the pie literally smacked against him with a wet slap, the coolness of the cream soothing his inflamed cheeks a little even as it inflamed his cock even more. See, the hard swing Natalie delivered had flung the cream not just around his ass but down over his cock and balls as well, leaving his crotch more than dotted with the creamy whiteness.

SMACK.

David had missed Natalie’s grab of another pie and as such the next strike against his ass came as a total shock, the explosive strike chucking more cream down between his legs to add to the mounded mass clinging to his groin as more was also plastered against his cheeks.

SMACK.

David lurched forward from the force of the third, his cheeks burning as he could only imagine what he looked like, bent over the knee of his onscreen crush, his cock smeared with cream, to say nothing of his freshly spanked ass, the burning in which didn’t stop an amused chuckle slipping from his lips.

‘Is something funny?’ Natalie asked sternly.

David didn’t know how to answer that without breaking character. He would have liked too, to say how surreal it felt to have lived out one of his most private fantasies with the woman who had been the focal point of them. But he couldn’t find the words so he settled on a simple ‘no, miss.’

‘Good. Because I have lots more pies I could spank you with. But I’d rather save them. Now..get up. And sit down here. I may have spamked you enough but we aren’t done with your punishment. No..leave your clothes where they are.’

David shivered at that thought, his hands having dropped away from his trousers to leave them bunched around his ankles as he sat, his shirt and blazer that hung down over his waist doing nothing to hide his cream coated erection. An erection that Natalie was now eyeing purposefully.

‘Oh? Are you enjoying this?’ Natalie leaned over him, one hand on his bare thigh, the other so close to his cock as she mimicked that hand slowly jerking him off. ‘Does it really get you hard being punished and spanked by your teacher?’

‘Maybe it does.’ David said boldly. ‘Maybe you’d like to..do something about it?’

‘Oh?’ Natalie replied with a faux mocking tone that made David shiver with excitement. ‘Something like this? Hmmm? Something like your teacher jacking you off until you cum?’

‘S..something like that.’ David replied, that stutter having come as Natalie went further than teasing, her hand now performing the act she had mimed a few seconds ago, her hand tugging and stroking his cock.
‘I could..of course.’ Natalie whispered. ‘But..this is supposed to be a punishment. So I guess I should punish you more.’

‘I don’t see this as punishment.’ David gasped breathily, his cock twitching with the first pulses of his release. ‘Fuck, you are good at that.’

‘I know.’ Natalie smirked. ‘And I know it doesn’t. But what if I..stopped. Hmmm? Would that be..punishment?’

Just as Natalie breathed that last word, she did just that; her hand tugged off his shaft a second before David came, his rushing orgasm suddenly stopped in its tracks as his cock strained upwards in urgent need, his hips thrust after her retreating grip.

‘See..this is what I can do to naughty boys who find their teacher sooo sexy.’ Natalie whispered slowly. ‘I can take their desire, their naughty lusts and make them a hundred times stronger until they beg for release. If I wish. But..I think you are already too worked up. So I think we need to cool you down a bit.’

David was torn between liking and not liking the sound of that, the second proving the one that won out as Natalie moved back to the collection of pies and buckets to grab one of the latter. With a little bit of effort she hefted the smallish black bucket over to sit between his legs, allowing him to see the slushy and somewhat thick pink substance within.

‘Can you believe they had all this ice cream nearly melted in the cafeteria.’ Natalie whispered, her hand dipped lightly into the pink slush. ‘Luckily for them, I took it off their hands. And I think this is a much better use than throwing it away. Now..brace yourself..this is very cold.’

Cold was an understatement. Goosebumps raised all over David’s thighs simply as Natalie lifted the bucket towards his cock, the wave of chill surely a harbinger of what he was about to feel. Yet nothing could have prepared him for the feeling of the icy, slushy, half melted ice cream poured over his length and balls. He half trembled, half shivered with each litre of slush tipped against him, the bucket raised up and up, pouring the whole load over his cock. True, more of it was pooled beneath his feet than clung to him, but the cold effect lingered with icy tingles that hadn’t exactly curbed his desire.

‘Now..pull your boxers up.’ Natalie said firmly. ‘For I have a question for you. Do you know what I banana split is?’

Somehow David had the feeling it wasn’t the traditional dessert that she was thinking about, so he shook his head slowly. A denial that drew another smirk from Natalie.

‘Then I think I should show you.’

Heart pounding with excitement the ice cream hadn’t quelled, David followed Natalie as she stepped away to return, unsurprisingly, with a bunch of a particular yellow fruit in hand.

‘Bananas.’ Natalie said coyly. ‘Nice and soft and squidgy. The perfect base for a banana split. And I bet you can guess where these are going.’

David could indeed and wasn’t exactly surprised as Natalie quickly peeled two and tucked them into the sides of his boxers, against his hips. Or when she added two more at the front, the soft fruit nestled against his rapidly rehardened cock. What did come as a surprise was the fifth tucked neatly down the back of his boxers and snugly between the crack of his ass too, the already slightly mushed fruit making David squirm before Natalie grabbed and tugged his boxers up into a hard wedgie that drove the soft banana deep into his crack.

David couldn’t help but release a sudden moan of mixed pleasure and disgust as the soft banana was squashed against him, his erotic suffering only prolonged as Natalie fixed the wedgie in place with the help of a sticky cream pie that she plastered against his boxer covered ass.

Content that the squished mess wasn’t going anywhere, Natalie quickly moved to compound that feeling, her hands suddenly clapped against the bananas on his hips, adding to the mush in his boxers. And as if that wasn’t enough, Natalie slide her hands around to his cock.

David’s eyes went wide as he realised her intent, helpless to do anything but watch as Natalie carefully lined each of the last two bananas up against his shaft before pressing her hands together. Just like he was helpless to do anything but squirm as the mushy mess envolped his cock, her hands squeezing and mashing the soft mass against him, almost teasing him as she rocked his length from side to side, only stopping when he released a low moan of tormented pleasure.

‘Oops. Seems you are getting excited again. That’s okay though. Every banana split needs some ice cream.’

David froze at that, the mere thought of another coating of the icy pour bringing him out in goosebumps. Luckily…or unluckily…Natalie had something else in mind as she quickly brandished a tub of vanilla ice cream, this one closer to frozen than the bucket, and an ice cream scoop. One she put to good use, scooping out an elegant curled ball of ice cream which she neatly dropped into his boxers, right on top of his cock. More followed soon after, the heat of his body against the icy desert resulting in a trickle that grazed down over his balls, the cool caress making him squirm again.

‘There. So we have bananas and ice cream.’ Natalie said as she rose to admire her handiwork. ‘I guess now we need the cream.’

David guessed what that meant, his head suddenly raised in shock in perfect time to connect with the first pie that Natalie threw, his face taking it square on. Yet Natalie didn’t stop there. David had guessed she had kept more than just a few pies back, but nowhere near the storm of creamy filled treats that exploded against him from all sides. If it wasn’t one splashed against his chest, it was one dumped into his lap. Or slapped against his neck. Or rubbed over his hair, followed by a second along his shoulders. Then another slapped onto his stomach. Or two sandwiched around his head. Such was the near non stop pieing as soon all of him from his face to his shirt and blazer to his bare legs and groin were swamped under a heavy mass of pies, the cool cream seeping through his boxers a little by the time Natalie drove the last deep filled Pie against his face and smeared it down over his chest.

‘There. Don’t you look yummy.’ Natalie said with obvious mirth. ‘A perfect banana split. Well..no..actually.,something is missing. Ah yes.’

What Natalie meant, Dsvid had no ideas. Until his head was enveloped in something heavy and sticky that he couldn’t place, until the rich smell of toffee filled his nostrils. Unseen by him, Natalie had obviously hefted some container of toffee sauce which she was now pouring all over him, the sticky sweetness oozing over his shoulders to caress his front and back alike, to say nothing of slapping and slipping into his lap, running down his legs in heavy rivers even as it pooled around his groin.

‘Now we are done.’ Natalie said over a thump that was most likely her putting the bucket down. ‘Now..stand up. I want you to explain to me why you deserved this humiliation and how you look.’

Shakily, Dabid did just that, the final humiliation of this last shaming only heightening his desire and arousal again. ‘I..deserved this because..I played humiliating pranks on my teacher. I..pranked her and allowed her to be humiliated by messing her up. And allowing others to do the same. And..I..I.look like a banana split. I..feel like one too.’

‘Good boy.’ Natalie said firmly. ‘I think you’ve learned your lesson. But to make sure, I want you to pull up your trousers and walk home just as you are. That should help the lesson sink home. Right. Class dismissed.’

—————

Again it was and with much less hesitation on his part this time, David and Natalie returned for another quick shower. Not that David didn’t wish he could have lingered in it longer now the ice had been broken but he was too eager to move onto the final scene. One which he had the perfect idea for.

‘So..’ Natalie prompted as she sat with her robe tied at the waist yet slightly open to tease him with a glimpse of her cleavage. ‘Do you know what you want to try next? This is the last one I’m afraid, so I’d make it a good one. Some fantasy you’d really love to live out.’

‘Oh….I’ve got one.’ David replied coyly as he flicked to the scenario he had glimpsed earlier. ‘Ive always wanted to be on a messy Gameshow. And this one is perfect.’

If only Natalie knew how perfect. It might almost have been written just for him, his cock twitching with each twisted detail he read. Had she known, she might not have been as willing to go along with this bit there was no hesitation as she rose delicately.

‘Well then..we had better get changed. Unless I’m doing this naked.’

Actually, Natalie wasn’t as blasé about this as she seemed, pretty sure her chances of getting away clean weren’t great. After all, why leave it to chance when you could..arrange things…to ensure she got messy anyway. Still…she had been pretty ‘cruel’ to David time and it was only fair to give him revenge.

———–

Part 2 of my anonymous Commission where the fun is contuning in grand form. Things are certainly heating up in more ways than one. And the best is yet to come. If you guys like this checking out my Patreon will help you get into crafting something like this yourself with my Patreon Driven Stories.

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