Degrading, punishments, overstim
"When I told you that you wouldn't come for three weeks, did you think I was joking?"
"Uhh... Umn.. No, ma'am..."
"Then why, do tell slut, did you come only two days in?"
"I- I- I- I... I'm so sorry! I'll never do it again! Mistress, I promise!"
"I didn't ask you to apologize, H/N. I asked you why you came before I said you could."
"Fuck, Y/N..." he whimpered practically petrified to speak. "I was really horny and- an- it... It didn't help that I thought about you f- fuh- fucking me..." he squeaked.
"Well isn't that cute?" Your hushed and tender tone almost made him feel off the hook. "Baby, I'm still going to punish you."
"N-no miss, ple-"
"Hush!" You were still pissed. "Shut up. Don't make a sound." The both of you stayed in silence, adrenaline and fear pumping through H/N's veins while you started to think of ways to punish your slut.
"H/N."
"Yes, ma'am?"
"Since you love coming sooo much, why don't you do it over, and over, and over again?"
He whimpers, visibly sweating with tears starting to form in his eyes. "W-won't that hurt?.."
"Of course it'll hurt. Itll feel good at first but eventually your pain will completely overpower the pleasure. You'll be begging me to let you stop but will I allow it?"
"N-no?"
"That's right! See how you can be a clever little where sometimes?"
"Mhm..."
"Turn your camera on and aim it at your pathetic excuse of a cock."
"Yes ma'am." You watch your screen as he does what he's been ordered. His 6 1/2 inch cock hard, twitching, and already dripping precum takes up the majority of the monitor.
"That's it, good slut." You say in a honeyed tone to which his dick trembles in response. "Go on, start."
He starts playing with his tip, little whimpers already escaping his pathetic little mouth. "Your whimpers are so adorable, whore~" Those words make him let out another, then another, and as he stops playing with his tip and starts to jerk off, those whimpers turn into loud moans of pure ecstasy.
"A-ah!~ I'm - I'm sooo closeeee~"
"Come baby."
The moment you order it, he does so and stops touching himself. Watching his still brow makes you raise an eyebrow and with just the right amount of sass you say, "Did I tell you you could stop?"
He being so whimpers again, barely being able to form words. "Uhnn nn-nno ma'am..."
"Then keep going, worthless mutt."
He does as ordered and continues to jerk off, his moans louder than they were before since his sensitivity is heightened. "Fuhh- Fuckk~" His tries to hold in his moans, trying only to let out whimpers yet he's still loud as fuck. "Hnghh- ah! Ah! Mn! Hah!" He squeaks like a scared little puppy.
"Such a cutie~"
This goes on for half an hour but, to H/N it feels like days. Days of torture. "M-mistress please let me stop, please pl- please let me fuh- fuh- hahn!~ let it stop!~"
"And why would I do that?"
"It hurttsss..."
"I know baby, I know. That's the point."
"Ughh please... I've orgasmed six times alreadyyy~ Please- I don't even rh- thu- think I have any cum leftt..."
"One more time. Then, you can stop"
"Thank you, thank you so so so much mistress. You're so fucking kind..." In just a few moments he orgasms again, only a teeny droplet of cum leaks from his now aching dick.
"Thats it, good mutt."
"Th th thanks for letting me stop... I'm so glad its o-over.."
"Oh no baby, your punishments just started..."
An: Y/N is so evil omg...
5 min break/aftercare: you two just talked about cute little romantic things like holding hands, maybe cuddling, etc.
