Taxes and Torture

It was a dark and stormy night, and my asshole protested in delicious agony as my girlfriend railed me with her monstrously large black strap-on. Her pendulous breasts brushed against my back as she pushed herself against me, and I relished their softness against my skin. My cock throbbed with need as blood surged into my shaft and sweat poured down my back; she was really giving me a jolly good rogering tonight.

"Oh, yes! It hurts... it hurts so good!" I screamed, as she continued to thrust in and out of my screaming butthole.

"Wait, this is... you're into this?" my girlfriend asked breathlessly as she panted with exertion - she sounded a bit frustrated. I nodded as I shot her a weird look. She knew I liked this stuff, we had been together for... for... I couldn't really remember, actually.

My girlfriend put her hand up to her chin for a moment before she grinned. "I'll try this, then." She pulled her strap-on out of me with a little pop and cackled maniacally as her strap-on became hotter and hotter. I could feel a fierce and fiery heat emanating from it, and I marveled at how technologically-advanced the toy was; it almost felt like... magic. My heart began to race with anticipation at that point; I was definitely curious to find out how it would feel inside me, even though I knew I should probably be worried. I craned my neck to look back at my girlfriend, and I caught a glance through our window and saw a blood-red sky outside. My eyes widened, and it was at that exact moment that I remembered I was single. My stomach dropped as I realized that something was definitely wrong, but I didn't have time to think about it as... whoever this woman was thrusted into me one more, glorious time ramming her fiery rod into my already-sore ass. Its searing heat turned out to be deliciously pleasurable as it burned my butthole, and I was finally driven to ecstasy as my cock unloaded a cannonade of cum. I creamed all over her silken sheets and screamed triumphantly as my soul left my body and ascended to Heaven - or I guess it had actually descended to Hell? I knew I probably should have been concerned about that, but I couldn't think straight in my orgasmic haze.

"Goddammit, you are into it." She let out a frustrated sigh and frowned at me.

My cheeks turned crimson, but I didn't respond. My mystery lover shook her head, and my eyes widened as she started to... change. Her skin turned a deep, dark red color, and her eyes began to glow like burning coals. Her teeth grew needle-sharp, and horns sprouted from her head as I watched in stunned silence. She grew a tail with a little heart on at its end, and her fingernails became claws, which she slowly raked down my back. My skin tingled with a warm, dull pain that wasn't exactly unpleasant. I actually found myself smiling at her touch, and my cheeks blazed with heat. She let out a huff as she pulled her hands away from me and groaned.

"Yeah, this isn't working. Ugh, what am I supposed to do now?"

"W-what's wrong?"

"Well, you're not supposed to fucking like this; it's supposed to be a punishment, after all."

"A p-punishment?" I squeaked. "Why?"

You didn't pay your taxes, Steve. That sort of behavior gets you a one-way ticket to Hell, you know."

"So we are in Hell, then? W-who are you, really? I asked, as a shiver ran down my spine. Whoever she was, she not only my name, but also my darkest secret, one I had planned to take to my grave - and then again, maybe I had.

"I'm Lilith, your personal H-IRS torture succubus," she said, honestly sounding a little disinterested. "I'm, uh... supposed to be torturing you for your crimes... but you, er... seem to be enjoying it." I couldn't deny that; I was a huge masochist, and what most people would consider torturous was more like a dream cum true for me. I knew I wanted more of her titillating torture, so I tried my best to deny it. Unfortunately, I didn't do a very good job of it.

"Um, n-no. Nuh-uh!" I said, not-so-confidently, as my cheeks blazed hotter than her infernal strap-on, which was currently roiling on her black, lacy panties. "I'm, er, actually not enjoying it at all! It, er... it hurts!"

"It hurts 'so good?'" she asked, repeating my words in a slightly mocking tone. My cheeks grew hot at that, and she smirked at me. "I think I need to try a new tactic. Get... creative." I audibly gulped - I really didn't like the sound of that.

"W-what do you mean, 'creative'?"

"I'm supposed to be torturing you, after all. But, since you're into it, um... I guess it would be torturous for you to... not be tortured." she said, with a devilish grin. She let out a long, drawn-out sigh, and I felt her strap-on cool down in an instant. My dick was already spent, and yet I was still incredibly disappointed; I craved her spicy strap-on's horrific-yet-heavenly heat.

"Wh-what? No it's okay; you can torture me. I, uh, hate it! Uhhh, please, dooon't hurt me," I said quickly, desperately trying to sound scared. Lilith rolled her fiery eyes and frowned.

"Now you're just phoning it in. It's embarrassing," she said, with a bit of admonishment in her tone.

"Dammit, fine," I replied sheepishly, as my cheeks burned. "Um... so, what now?" Lilith just shrugged and let out another sigh.

"Hmmm. Well, I don't know, exactly. I've never had to torture a masochist before - people usually beg me to stop as soon as I break out my FlameFucker 5000. Um... we could go over all those discrepancies in your tax reports, or something? Um, do you have any ideas?" That FlameFucker 5000 in my ass again sounded like a good idea to me, but I knew that wasn't an option, so I decided to ask her a question about herself.

"Do you like your job?" I asked, with a shrug.

"M-me?" she stammered, as her cheeks turned a shade of red so deep it almost looked black; it was strange to see a demon blushing - it was kind of cute, actually. "Th-this isn't about me; this is about you."

"Well, why not? I'm curious," I said. I tried to move positions, but I realized I was chained to her bedpost. I wiggled my hands back and forth, reveling in that agonizingly sweet ache of steel scraping against my skin. Lilith rolled her eyes again before snapping her fingers, causing my restraints to disappear in an instant. I felt a little disappointed as I got up and turned around before sitting cross-legged in front of her. "Well, you are my personal torture demon, right? So, let's get personal."

"I... I don't want to. I'm boring; you don't want to know about me," she said, breaking eye contact with me as she looked away. She was quiet for a moment, but when she finally answered, her words were so soft I could barely hear them: "I... I hate it."

"Why?" I asked, as I frowned.

"Because... because..." Lilith said, and then something within her seemed to snap as she began to unload. "Because my job is awful! Our pay sucks, we get shit benefits, no breaks... not to mention management is absolutely hellish. I mean, I know we're demons, but still! Honestly, I'm kind of relieved that I don't have to torture you," she said, flashing a weak smile. "It gets so tiring, Steve, and I just... hate it.. Truth be told, I'm... kind of on thin ice with my boss."

"What? Why?" I asked, and Lilith let out another sigh.

"He says my job performance is... disappointing. I'm... just not that good at torturing people. I'm... trying my best, though! Honestly, I... I hate this job, but it's literally all I have Steve." She ran her hand across her extra appendage that was affixed to her panties and sighed. "You know, I thought this strap-on would help; it usually works wonders, even though I hate using it. Not even that worked, though! I just... don't know what to do." She shook her head and flashed a weak smile at me. "Ugh, listen to me spilling my guts over here. I'm supposed to be spilling your guts! I bet you'd like that, though, wouldn't you, Steve?" She chuckled despite herself, and soon she was laughing. It was more than kind of cute; it was honest-to-God, full-on cute. I smiled back at her before I spoke up.

"I-I guess I would, wouldn't I?" I asked, feeling my cheeks burn as I started to chuckle myself, and soon we were both laughing. We finally calmed down after a bit, and I spoke again. "I'm sorry your job sucks, but, uh... at least you're not dead, right?" She smirked ever-so-slightly at that.

"Well, I mean, technically speaking, I haven't been alive for a while, Steve. I've been doing this a long time. God...way too long. I haven't... felt... alive, in a long time." She let out a sigh and her mouth drooped into a defeated frown. Seeing her like that was more torturous than anything she could have cooked up on her own; it broke my heart to see her so sad.

"C-can't you just... quit, or something?" I asked. Lilith shook her head, and her gaze drooped down to her sheets. "You don't just quit in my line of work, Steve. Once you're in, you're in for good... unless..."

"U-unless?" I asked, confused. Lilith raised her head and met my gaze again, and her fiery eyes blazed with determination. "Steve, could do something for me?"

"Um, sure. What do you want me to do?" I asked.

Lilith grinned as she shot forward and kissed me, and my eyes widened for a moment before I leaned into it, and before I knew it, she plunged her long, pointed tongue into my mouth and wrapped her arms around me. She tasted like cinnamon with a hint of smoke, and it was divine and oh-so-sinful, all at once. We continued to kiss each other passionately, and her mouth was warm and wet as her tongue danced around my own. My dick twitched as she wrapped her lengthy tongue around mine; it felt so strange... yet so good.

Suddenly, she broke away from me and pulled back, and I frowned as each torturous second marched on. There was one thing on my mind; all I wanted was to feel her lips on mine... taste that smoky cinnamon flavor again; I could have kissed her all night, but each second away from her was agony, and not the fun kind.

"I-is this part of your torture, Lilith? Because it's... it's working," I said, with a frown. Lilith looked back at me, and there was a devilish, sharp-toothed smile on her face. She undid her strap on and casually tossed it aside.

"Oh, don't worry. A little torture will make this part much more satisfying." She shot me a wink and slipped off her panties and tossed those away too. The sight of her plump, red pussy was enough to make me drool, but Lilith had something else in mind; she turned around and grabbed her ass, seductively splaying out her crimson-colored cheeks for me. "What I want is for you to fuck my ass so hard I can't see straight... oh, and Steve? Call me Lily."

My cock stiffened at the request, and just like that I was ready for round two. I leaned over her and shoved my full length inside of her asshole, making sure to enter her slowly - I didn't want to hurt her, after all. She was so warm and tight, and she gasped a bit as I entered her.

"Oh, God, yes! That feels so fucking good, Steve! Fill me up! Give me all you've got!" I pulled my shaft out of her and thrust myself back in again, more forcefully this time. She moaned with delight, and her encouraging elicitation emboldened me to do it again, and again... and... you get it. I didn't hold back, but Lily clearly didn't mind.

Her body shivered with pleasure as I continued to repeatedly refill her with tight asshole, and her moaning only grew louder and more intense. Finally, she could take no more as she screamed, shoving her head into her sheets to stifle her cry; her body finally convulsed as her pussy squirted a stream of steaming demon cum across her silk sheets. It wasn't long before I came again, too, and I pulled myself out of her ass and leaned back, now completely spent. She got up and snuggled up against me, flashing me a satisfied sharp-toothed smile before she kissed me on the cheek.

"Thanks for that. It was... amazing; I liked it so much better than torturing you, even if you might have preferred that." I definitely didn't.

"Not at all! That was... so much better than anything else you've done tonight, Lili-er, Lily," I said, cheeks blazing as I smiled at her. "I can't wait to do that again." Lily stared at me for a second before her smile faded.

"Believe me, I feel the same way, Steve," she said, solemnly, as she frowned, and her gaze drooped downward. "But, um, we... won't be able to."

"Huh? Why?" I asked, confused. She was silent for a moment before she met my eyes again, and she looked absolutely heartbroken.

"I told you earlier, Steve. I can't quit my job, so the only option was for me to-" She was suddenly interrupted as a torrent of fire appeared, and a demon in a snazzy-looking suit stepped out of it.

"Lilith, get up," he said, and she complied without protest. "Your little... tete-a-tete, with him," he said, glaring at me, before he looked back at Lily, "was a blatant breach of company policy. Between that and your... unsatisfactory job performance lately, we have decided to void your contract with us. Do you understand what that means?" She nodded slowly.

"Termination," she said, and she shot me a sad look.

"W-wait! What do you mean, termination?" I asked. "What's going on, Lily?"

"You said you liked being tortured, so... This works out, doesn't it?"

"No. Fuck no, Lily! I... I just wanted you to shove your strap-on...in..." I said, before I let my thought trail off as my eyes drifted downward and eventually landed on it; they widened as an idea formed - a stupid, insane idea. I got up and picked it up, then tried to figure out how to turn it on. I remembered that Lily had cackled before it turned itself on, but... it couldn't be that simple, right? I hesitantly glanced down toward my weapon and let out my most devilish evil laugh. Scorching magical flames enveloped my hand as her toy lit on fire, and it was agony... wonderful agony.

"Wh-what are you doing?" her boss asked shakily, and I could have sworn he looked... scared. His reaction only served to strengthen my resolve; I wanted - no, I needed - to save Lily. She was my personal torture demon, after all, and no other torture demon would do.

"Steve, what are you doing? Just forget about me," she said. "They'll find you someone else."

"What if I want you?" I asked, as I jabbed my flaming dildo toward her boss.

"That's not how it works, Steve. It's the... end of the line for me. I'm sorry, but I... I thought you liked getting hurt."

"I do, but... not like this, Lily." I said, as tears welled up in my eyes. I grimaced and rushed toward who I could only assume was her boss, shoving my makeshift weapon toward him. I smiled with satisfaction as it his stupid suit on fire. He screamed and jumped around as his precious suit burned up, and I grabbed Lily's hand. My face was sweating, and I squinted my eyes at that wall of flame, which was luckily still burning - it was our one and only exit. "This is the way out, right? Let's go." Lily looked over at me, and all that fire in her eyes seemed to have dimmed - it looked like she had just... given up hope.

"Why are you doing all this for me?" she asked, shooting me a quizzical look. "I... don't understand. You barely know me."

"You wanted to quit, right? Then fucking quit. You don't have to do this, Lily; you deserve to be happy." She was quiet for a second, and looked over toward her boss, who was rolling around helplessly at that point. "Come with me. Please?" Her boss was still rolling around.

"Don't you fucking dare!" he screamed, as roaring flames licked his body. "I will hunt you both down endlessly if you take even one step through that portal!" I looked over at Lily and glanced at our exit. She smiled at me and nodded. "You owe me a new suit, you son of a—"

He hadn't finished his sentence when we both took a step forward to whatever it was that lied beyond.