Punishing Heather Ch. 02

Punishing Heather, Ch. 02

This is a pretty short chapter, meant to get the plot moving along after some time away from this story. Like Ch. 01, there is some non-con/reluctance content. If that isn't your thing, please enjoy some of my other stories.

"You're a mess, Heather," said Lauren with a sneer. "You look even worse than usual."

"Fuck you," Heather responded. Lauren just smiled and reached into her bag.

"I don't know what they've done to you already, but I can promise that you won't enjoy what I've got planned for you. It's payback time, cunt. Stand up." Saying this, Lauren took out the most enormous strapon dildo I have ever seen. It had to have been a foot long, and monstrously thick. Heather's mouth gaped open in shock at seeing it. Now she was standing, being held in place by Ken and Josh.

"See this? I bought this a few months ago but have never had a chance to use it. I always tell Hailey that I'll punish her with it when she misbehaves, but she's just the most obedient little slave that I never have a reason to."

Hailey smiled lovingly at Lauren

"Thank you, mistress."

"Fuck you too, slut." Heather directed this at Hailey, who looked innocently taken aback. Hailey looked to Lauren, whose face had quickly changed from smugly superior to enraged. Lauren delivered three hard slaps to Heather's face. These weren't sexual or erotic slaps, but truly violent blows intended to hurt. Heather tried to avoid them but was being held firmly in place. She sobbed as Lauren addressed her.

"Do. Not. EVER. Talk to her like that. I swear to God I will fucking end you. Hailey is my property, and I do not tolerate dumb, worthless cunts like you mistreating her. Tell me you understand."

"I... I understand..." said Heather, sniffling.

"Tell me you're a dumb, worthless cunt." Another slap, though less forceful than before.

"I'm... a dumb..."

"Worthless." Another slap.

".. worthless... cunt."

"Good. And so you never forget, I'm going to fuck your asshole with this. It's going to wreck you, and you will deserve it. Guys, bend her over."

"Hold on, I have an idea," I interjected. "All of us want to fuck her ass, but it'll be best if she's still tight. How about we all use her first and you use that as the grand finale?"

"Fair enough. You're lucky, bitch. They're going to work you over first before I use this monster on you."

Heather was now bent over the desk with Ken and Josh holding her arms. She was pinned, with no hope of escape.

Lauren grabbed two handfuls of Heather's ass and jiggled them around.

"Look at this fat ass, boys. The only attractive part of this slut's body, if you ask me. Unless you like those fat cow tits of hers. I can't believe you guys have fantasized about fucking this ugly whore." She gave Heather a few spanks and then reached between her legs to play with her pussy.

"Oh my God, your pussy is soaked, Heather. You're fucking disgusting, leaking all of this cum from your little skank hole. I can't believe what a dirty slut you are."

Heather didn't respond, but just took the verbal barrage in silence. She clearly wanted to cry, but held back.

"Well, get started. I want to see this slut getting her asshole ripped open. But she's going to do something for me too." Lauren unzipped and removed her pants and hopped up on the desk, sitting with her open legs facing toward Heather. Ken and Josh moved Heather so that her face was aligned with Lauren's pussy, and Lauren quickly grabbed her by the hair and forced her down.

"Someone get a cock in her ass so this bitch can moan into my pussy." Lauren made eye contact with me as she said it, and I took up position behind her. I lubed up my hard cock and pressed the head against my boss' asshole. Heather squealed indignantly at how she was being treated and tried to struggle away, but it was clearly a hopeless endeavor.

"Please... please... don't do this to me, please... I'm sorry, sorry for everything!"

"Good start... but if I don't fuck your ass now, how will you really learn your lesson? Just take your punishment like a good girl. You might even enjoy it. You said yourself that you're the anal queen. Or was that just bluffing?"

I pushed into her, my cock head breaking through the ring of her asshole and causing her to scream. It was the desperate, hopeless scream of one who knows that resistance is useless.

"Please... too big... please, please slow, go slow... oh my God, oh my God it hurts!"

"I know it does, Heather. I know." I ignored her protests and pressed deeper.

"Get in there and eat my pussy," Lauren interjected. "Focus on me and you won't notice how much he's hurting you. You'll get used to it."

Heather must have started right into her task, because Lauren began moaning almost immediately. Heather quieted down too, only letting out the occasional grunt as I pushed deep into her and began thrusting.

"How do you like that pussy? Are you sorry for laughing at me for being a lesbian all those times? Sorry for teasing me? Huh? I can't fucking hear you!"

"Ugh, yes! I'm sorry Lauren! I'm sorry!"

"Louder!" Lauren slapped Heather's face roughly several times. "Tell me you like pussy!"

"I like pussy!" Heather yelled when Lauren allowed her back up.

"That's right you like pussy, especially mine. Have some more."

I drilled Heather's ass for another minute as she was forced to pleasure Lauren. Ken and Josh both had massive erections as they held her in place. John stood off to the side enjoying the whole scene, stroking himself lightly. Hailey stared lovingly at Lauren as the domme in the pair used another woman for gratification. It was a scene of true sexual perversion.

When I pulled out, Heather managed to let out a sigh of relief, but her reprieve didn't last long as John quickly filled the void. He gripped her hips and began thrusting hard into her immediately, not giving her any time to adjust. John had mentioned wanting to assfuck Heather before, when we had begun to plan this whole thing out, so I was happy to see him getting what he'd always wanted. Heather, on the other hand, was struggling with it.

John was fucking her mercilessly, like the only thing he wanted in the world was to inflict retribution on her tight hole. He slapped her ass hard as he used her, causing her to yelp in pain and surprise each time.

"Keep doing that," Lauren encouraged him, "every time you hit her, her tongue goes crazy on my clit. I'm going to cum, she's going to make me fucking cum. Use her fucking ass."

John needed no instructions to use our boss' backdoor, and his thrusts kept up their hard pounding for a few more minutes until he lost all control and shot his load deep inside her. When he pulled out, his cock was still hard, but he stepped aside to allow someone else a go.

"Someone get the fuck back in there, she's about to make me cum. Don't give her ass a break." Lauren was taking control of the situation, issuing orders like she was the real boss here.

"I'm next," declared Josh as he motioned for me to take his place at Heather's side. We traded places, and he lined up his huge dick with Heather's asshole. His cock was menacingly large - an absolute monster. Somehow it seemed to have gotten even bigger since this whole process began. While this swap was going down, Lauren had a short but seemingly intense orgasm as she rubbed her clit.

"Please... no... too big..." Heather protested as she felt his strong hands on her, spreading her ass to prepare for his cock. Josh applied a large amount of lube to both Heather and to his cock.

"We'll see. You've gotta try black dick in your ass once. I thought you were the anal queen, huh? Can't be a queen until you take a real king up that ass."

"I'm sorry, please don't punish my poor little asshole anymore. Please don't shove your big black dick into me. I promise I'll be good from now on."

"Hold on," Lauren interjected, pulling Heather's hair and looking deep into her eyes. "This bitch is fucking enjoying it. I can see it in her eyes. Sneaky bitch thinks that she can act like she doesn't want it. This could be a lot more fun for everyone if you stop the games and admit you love what's happening."

"I... "

"Say it. Say that you're a dirty whore who likes getting gangfucked. And tell me you want that big black dick up your ass."

A brief look of resignation washed over Heather's before she answered. Through a big smile, she admitted it.

"I love to be gangfucked. I love to be treated like the whore I am. And I want that big black dick up my fucking slutty ass."

"You heard the bitch, Josh."

Without saying a word, Josh took what he wanted and shoved himself into her already well-fucked asshole. He wasn't as rough with her as the rest of us had been, but he didn't have to be; his gargantuan piece of meat was punishment enough.

"How do you like that big black cock up your ass, Heather? Tell me how much you love it." Josh was clearly enjoying himself.

"Oh, God... I... fucking... love it... so big, so fucking hard, so deep up my fucking ass. Drilling me so hard and deep."

"Maybe I can get you addicted. You'll be black cock only from now on, huh? Can't wait for you to tell Travis the news."

Heather couldn't respond to Josh's taunts about her boyfriend because her face was once again buried in Lauren's pussy. However, it was clear she was enjoying the experience from the moans of pleasure coming from her.

"Cumming... make me cum, slut, that's right," Lauren said as she gripped Heather's head with both hands, before going almost completely silent. Her body was wracked with a strong orgasm as she kept Heather firmly in place. Meanwhile, Josh kept sawing his massive cock in and out of our boss' well-used asshole. By this point, Heather seemed almost not to notice. Soon, Josh was cumming as well, grunting as he shot his load up her back passage.

He remained at almost full size once he pulled out, making the rest of just a little bit jealous. There was a strange lull in the office as everyone processed what had just happened. Heather was panting with exertion, but seemed to have accepted the fact that she was enjoying herself. She stood, now that she was no longer being held down, and scanned the room with a lustful smile.

"I hope you all enjoyed that."

"I think you did too, slut." Lauren grabbed Heather by the hair once more as she said this, getting right in her face. "I think you want to be treated like that every day."

"Maybe it's what I need." Heather pressed her lips forward as if about to kiss Lauren, but Lauren pulled back laughing.

"Ha.... you think I want to kiss you? A filthy cum slut like you? No, these lips are for Hailey. You really are a stupid bitch, huh?"

"Guess so," said Heather with a smirk.

"So what now?" I interjected. "You didn't get to use your big toy on her."

"I've changed my mind," Lauren answered. "I want to save that for later. Tonight, actually. Heather, be at my place at 7:00 PM. Hailey and I have plans for you. Tyler... you're invited too. But right now, Heather needs to call corporate and tell them that the store won't be open today due to a suspected gas leak in the shopping complex. Isn't that right?"

"Yes ma'am," said Heather, taking the hint.

"And then you need to go home. Rest and recover, because tonight is going to be a lot more work for you."