"Val, please!" Angel gasped, bucking his hips in an attempt to get more friction against his straining cock. He'd had a cock ring on, preventing him from getting any relief until Val was satisfied. Although at first he wasn't complaining, having it on for almost an hour was starting to be borderline painful. "Boss, I-fuck, please- I need to cum!"
Valentino had pulled him aside after a meeting with some other big-shot pimps, and demanded that he take his frustration out on Angel's ass in some sleazy hotel a few blocks over. Pretty much all hotels had some types of sex equipment that just came with the rooms, which was par for the course, in hell.
"Those motherfuckers don't know who the hell they're messing with. All bark and no bite." He shoved Angel onto the bed and turned to look at the different toys in the drawers next to the bed. "Oh, this seems perfect," He purred, pulling out a shiny cockring. "Angel Baby, I haven't had that great a day, so make sure you do your best for me."
"Val, I wanna cum, please!" Angel whimpered, cock bobbing while Val continued to fuck him relentlessly. "Please, haven't I been good?"
Val slowed, and looked at him in disappointment. "Angie, I'm not even close to coming yet. You're really not even trying today, are you."
"No! No, I swear, I'm trying!"
Val rolled his eyes. "Fine. But don't you dare complain about the rest of today, after this kindness I granted you." He slid off the cock ring and roughly ground the heel of his palm against Angel's crotch, who keened and came with a shudder.
"Thanks Boss," he sighed, starting to sit up. "Now what?"
Valentino glared at him and shoved him down again, more violently than before. "I said I'd reward you, not that we were fucking done. Get on your stomach."
Angel nervously turned over, and Valentino quickly rammed back into him and pushed his head into the mattress. "W-wait! Boss, I just- I just need a second and then-"
Valentino growled and spanked him, hard. "Shut the fuck up, whore. What did I tell you about refusing me?"
"Good boy," Valentino whispered, running a hand up Angel's back. When he got to his head, he threaded his hand through Angel's hair and yanked, still thrusting into the pornstars ass. "Now just stay there, and do what you're fucking told."
Now, while Angel was a masochist, there's a notable difference between some nice waxplay or bondage, and hypersensitivity with no relief.
Angel bit his lip and grasped at the sheets, trying to ignore the borderline painful overstimulation he was experiencing. "Oh, Val," he moaned, trying to sound enticing. The faster Val came, the faster he would be done. "Harder, Daddy!"
Val chuckled and slammed into him. "Look at you, you little fucking slut. All bent over for Daddy, even though you just came."
Angel bit back a retort. It's not like he chose to be there for so long, its just Val takes a long fucking time to cum. "All for you, Val."
Valentino reached around and grasped Angel's member, running his fingers along the head. Angel bit his cheek to try and keep himself from coming again, but couldn't stop the shockwave that rippled through his body. "Oh, God," he choked out. "Val-"
"Angel, if you say what I think you're gonna say, believe me you are gonna have a way worse day than I did." Valentino's cock dragged along his prostate, and Angel nearly screamed.
"No, no, I'm sorry," he retreated. "Don't stop, Val." He squeezed his eyes shut and pushed his ass back onto Val's dick, despite the overwhelming sensitivity of his whole body. After a few more minutes of Val fucking him like a machine, grinding against his prostate with every thrust, he came again, covering his mouth to avoid screaming again.
Val slowed his thrusts before pulling out, and Angel almost sobbed with relief. "Did you-"
"No, I didn't fucking cum," Valentino snapped. "I don't think you're trying hard enough."
Angel hiccuped, moving to crawl towards Valentino, despite his trembling limbs. "No, Boss, I swear! Here, let me-"
"I'll tell you what you're gonna do." Val turned and thudded onto the bed next to him."If you're really trying, you'll have no problem riding me to prove it."
Angel looked at him, eyes wide. "But-"
"Angel, I swEAR TO GOD!" Val yelled, slapping Angel hard. "You're fuckin' useless! Get on top of me, of I'll beat the shit outta you."
Angel grit his teeth, cheek stinging, and nodded. "Yes, Boss." He gingerly moved on top of Val, before slipping the head of the pimp's cock into his aching hole. He cried out as the rod slid deeper inside, bumping against every ridge inside of him. As it pushed against his prostate again, he whined, and Val held up a hand.
"Stop." He commanded. "Stay right there, keep it pressed right against your g-spot. If you even think about moving, I swear I'll kill you."
A few stray tears slipped out of Angel's eyes as his shaky legs tried to support his odd position. Val started rocking into him gently, dick never losing contact with Angel's most sensitive spot. A few of Angel's hands shot out behind him, to try and stay balanced, and he nearly screeched as he was brought to climax again.
Val grinned menacingly and finally thrust up into him, pulling Angel down so we was pressed against Val's body. "God, Angel." He breathed into the spider's ear. "You're my favorite when you're like this, mascara running, barely able to breathe, and at my total mercy."
Valentino continued to fiercly thrust, as Angel gasped into his chest and squirmed, desperately trying to get away from the unwelcome intrusion. He was used to marathon sex, but usually there were at least a few tiny breaks for him to recover before being fucked again. Now there was virtually no pleasure left, just the pain of feeling like he was about to fucking implode or fall apart. "No," he whimpered.
"What did you just tell me?" Val asked thrusts slightly slowing and balls tightening.
Angel sobbed. "Stop, please! I-fuck, oh shit- I can't, it hurts!"
Val moaned throatily and sunk all the way into Angel, bucking as he flooded Angel's ass with cum. "Oh, that's the shit," he grunted, biting Angel's neck, who shrieked and went limp. "Fuck, that's sexy as hell." He stayed inside Angel until his cock was fully soft, and then slowly pulled out. He pushed Angel off of him, then scooted and slapped his shaft against Angel's cheek. "C'mon, Angel Baby, clean me up, will ya'?"
Angel licked all the way up the underside of Valentino's cock, grateful that he was done for now. He moved around Valentino's cock gently, knowing that he'd be punished if Val felt even a little bit of pain from the sensitivity. When he was done, he pulled back and swallowed, knowing that it would lessen any anger towards him.
"Yeah, baby." Val cooed. "That's why you're one of my favorites, you have absolutely no dignity." Angel looked down in shame, holding back tears. Val patted his cheek and turned, pulling on his pants. I'm having some friends over later, make sure you're all ready to serve them by 7. And don't worry, I'll give you some recovery time when they're here. None of them get to destroy you like I do." He strode out of the room, not even waiting for a response.
Angel stayed stock still for a few moments before finally letting out a shaky sigh. He rubbed at his eyes, wincing when his hands came away black. "Fuck, now I gotta reapply," he groaned to himself. He hurriedly dragged a makeup wipe from the nightstand around his eyes, curled up into the sheets, ignoring how disgusting he felt, and fell asleep.
About half an hour later, he pried his eyes open and gritted his teeth. He still had to clean himself up, and prepare himself for Val's little get together later. He stood, all of his hands braced against things as he walked so he wouldn't fall, and made his way to the shower. The water was lukewarm, and he softly cried as he washed himself, forcing himself to thoroughly clean his abused hole. As soon as he was done, he went back, balled up the sheets and threw them into the laundry chute before collapsing onto the bare mattress. He grabbed his phone, set an alarm for 5:30, and curled up as tightly as he could, arms pressed against his chest.
He dreamed of his life as a human, when he was alive. Back then, he could never show who he really was without being beaten up, or rejected, or laughed at. Even most of his family was cruel to him, choosing to see him as their own little lackey/punching bag instead of a son or brother. Now, in hell, he could freely express himself, but was it much better? He did enjoy porn, and sex, and drugs, but almost every day someone tried to take advantage of him, and sometimes he was forced to let them, or even to make them enjoy it. In both worlds, he was abused for who he was. Was one of them at least better? It didn't matter which. Or was he just destined to suffer? Waking up, he stretched and winced, cracking his knuckles. He stood and went to the bathroom, and began to reapply his makeup. He changed, made the bed again, and played on his phone until around 6:45. Then he stretched himself in preparation for Val's friends, and lay back on the bed to wait.
The door creaked open, and a group of about five or so tough-looking demons gathered into the room, followed by Val.
"Hey boys," Angel cooed, spreading his legs and trailing his fingers up his thighs. "Why don't you show this lonely lil' doll a good time?"