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Ace stared at the collection of paddles and whips on the bed and not for the first time regretted having such as overly organised boyfriend. Sure, it was great when he needed to pack for something or revise, however sometimes it led to embarrassing moments such as these where his boyfriend starts collecting paddles, floggers and whips to try out together.
“I have them sorted by shape, size and from how likely you’ll be able to walk properly the next morning.” informed Riddle, attempted to break the silence that had occurred when he had first showed the collection of spanking equipment to his boyfriend.
Ace wanted to scream at the innocent look in the shorter teens eyes but he kept his cool and tried to now show the panic on his face
“D-don’t you think this is a little excessive, housewarden?” laughed Ace nervously, as he tried to not make it obvious that he was rubbing his thighs. “I-i mean will we even get through half of these?” he asked, trying his hardest not to feel aroused as he scanned through the items on the bed. ‘Think about the headmaster in that ugly shirt, ugly shirt, ugly shirt!’
“Of course not!” reassured Riddle, putting a comforting hand on Ace’s shoulder. “I just want to make sure that we have a safe, communicative environment, both inside and outside the bedroom! I don’t want to use the collar on you and I think this is the most effective way to both punish and please you.” he splayed his hand out on the bed and picked up a small paddle and then leaned in close to Ace’ ear. “After all, I thought you would be happy by this. You always get so wet whenever we discuss punishment like this.”
Ace gasped at the lewd words and immediately sprang away from his housewarden before grabbing a pillow and burying his face in it.
“Don’t tease!” Ace whined, affronted by the sounds of Riddle’s chuckle at his situation. Riddle rubbed his hands on Ace's leg and tried to stifle his laughter.
“I won't.” reassured Riddle, still trying to stifle his mirth. At Ace’s pout he took another deep breath and gave Ace a gentle smile. “We don’t have to do anything right not, don’t worry.” he reassured, bringing the redhead closer to him to place a kiss on his forehead. “I just wanted to go over a few things so that when we do, do this, we don’t end up crossing any lines or boundaries.”
Ace pouted, cheeks still red, however he understood where his housewarden was coming from. It would be super embarrassing on his end if he couldn’t handle getting spanked by one of the paddles or flogs and he would rather not start crying because of that.
‘You’ll still be crying none the less from squirt-’ came the voice inside his head and Ace mentally batted it away, hoping that his face didn’t flush darker or hint at what he was thinking.
“Sure, housewarden!” Ace flopped back, trying to give off an air of bravado, but failing due to the way he had curled up ever so slightly. “What do we need to discuss about you s-spanking me.”
Turns out, there was a lot to discuss. For almost 2 hours they had sat, side by side, inspecting the paddles and flogs and noting which ones they should start with. Well, Riddle was inspecting them whilst Ace was hiding his face and squeezing his thighs to try and stave away his arousal.
They also settle on a small flogger, no bigger than Riddle’s hand and a simple wooden paddle. Ace bit his lip as he watched Riddle pick them both off and ha to drive away all his thoughts when he thought about what Riddle could do to him, then and there.
Then they had talked about when they would use them. They had agreed it would be an alternative to the collar if he broke a queen of hearts rule. Ace was tempted to joke that he would break the rules all the time now but that would be admitting to the near puddle that was going on in his pants right now and there was no way he would admit to something that embarrassing, no matter how eager his boyfriend was to please him.
Riddle had initially suggested doing the number of spanks by the number of the rule that was quickly rules out by one of his pillows making direct impact with his face.
(“Are you insane!” demanded Ace, taking another pillow to Wack his boyfriend with it. “There are over 800 rules! Do you want me to die!?”)
They had agreed on a set number of 20, which changed depending on the number of offences and what the offence was.
Strangely enough, there was a certain...twinkle to Riddle’s eyes when he had suggested the number and whilst as tempted as Ace was to confront that, he also realized that this was a horny twinkle and usually when Riddle had a horny twinkle, he tended to make good on it, so Ace let it go for now.
(Stupid)
They had wrapped the conversation up by discussing what could be said during the play and what was forbidden. For example, Ace refused to count any of the spanks, and Riddle wanted to reaffirm the punishment. They had compromised by Ace declaring why he was getting spanked before and after the spanking session and thanking Riddle for it, before and after.
They had then had an intense make out session which led to Riddle discovering just how wet Ace was and eating him out to the point of tears and then bringing him a cherry pie to satiate his pouting boyfriend.
“I’m just happy that you’re excited about this.” Riddle told him, this time avoiding the violent pillow attack with a teasing smile. “I just want you to be happy.” Ace had the shoveled a forkful of pie into the other mouth and made himself home on the shorted lap, demanding that Riddle stop being so sappy about spanking him.
Riddle indulgently smiled and opened his mouth for another piece of pie.
The time to use the paddle and flogger came sooner than either of them had really excepted, even with Ace’s nature to act out and break the rules.
It had happened during an unbirthday party and Ace had broken the stupidest rule there was. He took a bite from the cakes before Riddle did.
Now, normally he wouldn’t make such a rookie mistake, but sue him! He’s been twitchy ever since the talk with Riddle and he might have forgotten that he was supposed to wait until after Riddle to start eating the desserts.
Immediately, the table got quiet and everyone's eyes became glued on Ace and Riddle, who were sat facing one another and opposite sides of the table. The other students were whispering to each other about what was going on, some even snickering, waiting for Ace to be collared.
Deuce was shaking next to Ace, flashing him a look that clearly said ‘YOU IDIOT!’ whilst Trey and Cater both winced, waiting for the shoe to drop and for Riddle to start screaming.
However, Riddle surprised everyone there, including his boyfriend.
“Ace, why don’t you see me after the unbirthday party, in my room? You seem stressed and I can dol out some appropriate punishment then. For now, enjoy your cake.” He reassured before taking a bite of his own cake. Noticing the quiet he looked around and noticed all the gaping faces. Coughing slightly, he turned to Trey and innocently asked “Aren’t you hungry, Trey?” he asked the incredulous man.
The bespectacled junior blinked for a moment before nodding and letting out a hesitant and chuckle and slowly everyone else started eating, with conversations spewing left and right, many about what just happened. Or more accurately what didn’t happen.
From the corner of his eyes, he can see Deuce and Ace shive each other slightly as Deuce attempted to wheedle information out of his rival/friend whilst Ace tried to continue eat the desserts in front of him.
Riddle internally chuckled as he willed himself to relax and try not to think about what will happen soon.
Riddle couldn’t help but feel nervous as he waited for Ace to enter his room. He had the flogger and the paddle laid out next to him and his bed was made to perfections. There were extra sheets in the bedside drawer and he had prepared the bath with what could need. Now, it was waiting and hoping that his boyfriend didn’t get overwhelmed and back out.
Too soon, he heard the door knock with what Ace dubbed their “Nighttime frisk” knock and he took a deep breath before allowing Ace in.
“Come in.” he called out as he prepared himself for tonight.
Ace shook silently in front of the door to Riddle room and contemplated just running away and dealing with the consequences later, after all, what’s the worst that can happen?
‘A lot, stupid.’ his mind insulted as he thought about the long list of punishments that can be given to him if he doesn’t attend this punishment session.
Finally, he took a deep breath and released it slowly.
He’s most likely overreacting. Yeah, he’s overreacting! Maybe housewarden Riddle just wanted to check on him and make sure everything was okay! What was else was going to happen, hahaha?
With newfound confidence he lifted his hand and knocked on the door.
“Come in.” came his boyfriend steady voice and he prepared himself for the punishment.
Next time, he was never going to listen to his inner voice, instead he was going to simply make his way back to the kitchen, gorge himself on cake, and then go to sleep. That would be 100x better than his current position!
Why?
Because currently he was as naked as the day he was born, over the knee off his still very much clothed boyfriend whilst the older held paddle in one hand steadied his ass with another.
He squirmed, in some pathetic attempt at trying to escape, but a firm hand on his hair kept him silent.
Quite frankly he did do this to himself. Why he thought it was a smart idea to strip when he was going to face a punishment, he had no idea. He firmly blamed the fact that Riddle hadn’t touched him since the paddle talk on why his libido spoke over his common sense.
“Now, I think that 10 each will help cement the lesson properly.” Informed Riddle about the punishment was going to be doled out.
At such a lower number Ace couldn’t help but cheer slightly. He had only broken one rule so it won’t hurt as much!
Stupid.
“Now, before we start, safe words first.” Riddle checked over to make sure that his boyfriend would be okay.
“Green is Go, yellow is slow down and red is stop!” Ace answered, invigorated again due to his belief that his punishment was going to be minor.
“Good boy.” Riddle praised and gently stroked the hair that he had in a rough grip. “Now, explain why I'm doing this and how thankful you are that I'm correcting your behavior.”
“I’m getting punishment because I ate a tart before you! Thank you for punishing me housewarden Riddle~.”
‘Cheeky little brat.’ Thought Riddle fondly before the punishment began.
Ace takes it back; the punishment is not easy whatsoever. He had, naively, assumed that since the housewarden didn’t look like he had much strength that he would breeze past the spanking.
He did not.
And now he was sniffling as Riddle gently patted his flank.
At first it hadn’t been so bad. The spanks have stung the first few times; however, Riddle had also managed to gain his footing and the spanks had been harsh, each one echoing, one after the other.
However, not matter how much Ace sobbed, no matter how much he squirmed, no matter how much his ass was going to bruise tomorrow, there was no denying the wetness between his legs.
Ace whimpered as he tried to figure out his surroundings properly, still a little dazed from the way Riddle had spanked him and desperately needing to cum. However, he also remembered that he was supposed to thank Riddle for spanking him so he attempted to make his mouth work.
“T-thank you for the- AHHH!” wailed Ace as he felt a rippling effect on his cunt. Riddle has struck his pussy with the flogger.
It turns out whilst he had been reassuring Ace with one hand, the other had gone to the flogger to continue his punishment.
Riddle struck his cunt again, this time angling it so that the flogger hit his cunt as much as possible. Ace tried to squirm, newfound vigor to attempt to lessen the pain from the blows.
However, no matter how much he moved, all it led was to Riddle bringing down the flogger harder than before. He brought it down once again so that it aimed on Ace’s lips and then on the hole.
Finally, Riddle brought it down and the flogger managed to reach everywhere, The clit, the lips and the hole. And that seemed to be all Ace needed before he squirted all over Riddle’s hand and the flogger. The younger, sobbing at the humiliation, didn't seem to notice when Riddle’s fingers had been tracing the outer lips.
Riddle gently rubbed the youngers clit, amused at the heat radiating of it and he couldn’t help but smirk when he heard Ace squeal as he pinched his clit.
Suddenly, Ace gasped as he felt something penetrate his cunt. However, due to being far too exhausted he couldn’t see what Riddle was fucking him with, the only thing he could sense was the ridges from the object and riddle gently rubbing his back.
He could feel the objects ridges overstimulate his pussy. He let out a little wail when he felt the tip of the object nudge his g-spot, not used to the strange bumps or the object in him.
“There, there, just one more, for me.” Riddle gently told him and Ace knew it wasn’t a request.
They didn’t really have to wait long either. The combination of Ace’s sex still stinging from the spanking earlier, and the way the object in his pussy was pressing against his g-spot, combined with his current overstimulation allowed Ace to squirt again.
It also made him black out.
Riddle blinked as he stared at his boyfriend's unconscious figure before he gently laid his boyfriend down on the bed, legs spread. Riddle bit his lip, looking around as if afraid that someone will walk in on him before he gently lowered his head towards his boyfriend's pussy and started placing small little kisses on the clit.
Ace’s poor thighs had begun twitching erratically as Riddle started enthusiastically leaving slobbering, wet kisses all over his cunt, reaching everywhere he could manage, still not waking Ace up. Eventually, he let the poor thing rest after he had made Ace squirt for him again.
He gently carried his boyfriend to the bathroom. (Doing all those upper body exercises with Jack were paying off!”
“Please forgive me!” and Riddle could have sounded actually apologetic if he also didn’t have that smirk on his face.
“No!” pouted Ace childishly, wrapping himself with the blanket like a burrito. “To f-fuck me with the flogger! Where is your shame!” snapped the younger, glaring at his housewarden when it seemed the other had let out a laugh.
“You squirted!” Riddle immediately realized that was the wrong thing to day, but before he could take it back, Ace began pelting him with his pillows.
“Pervert!” accused Ace, crossing his arms and turning away from his boyfriend before looking down as a blush overtook his face. “But I didn’t exactly...exactly hate it, okay!”
Riddle only allowed himself a fond smile before finally joining his boyfriend on his bed and wrapping his arms around him and peppering his face with little kisses much to Ace’s resignation. Just as Ace started to untense, Riddle leaned in close and whispered “Next time, I can fuck you with both the paddle and floggers handle.”
It was so worth the loud screech and consequential pillow attack he received form his boyfriend.