Watching Punishment

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Dean groaned but picked up the pace. Still balanced on one hand, he grasped her by the hair and held her still while he rammed his cock down her throat. Her body bucked on the bed, thrashing and pitching as he thrust into her throat but her hands remained resolutely knotted in the bedspread. Dean lifted his eyes from the body he was violating and sought Diana. She was weeping openly. When she met his gaze, her hands twinkled in the cuffs, making them rattle. She twisted her clothed body this way and that way but never broke the connection of her eyes to his. She was panting, her tongue constantly licked her lips.

Dean felt the first hint of an orgasm and not wanting to loose it into Lola's mouth, perhaps "not wanting" was an overstatement, preferring to pump cum into her cunt, he pulled out of her mouth. Lola lay on the bed, her head hinged off the edge, grunting and gasping. Dean helped her to sit up and shuffle forward so she could lay back and not have her head dangling. She lay, her blouse a ruin, her tits bared but wearing the bra above them, across her chest, her skirt still tight on her thighs and ass.

"Oh fuck me, Deano, you know how to punish a girl!" Lola finally regained her voice. "God, you can use me any old day you like, daddy O." She laughed, not the giggled but a woman's chuckled. "That's what I'll call you, Daddy Orgasm!"

Dean grunted. He moved around to the other side of the bed, grasped the woman by the knees and slid her across it to the edge. He felt up the sides of her tight pinstriped black skirt for a zipper. He found two, one on each side. He released each and the tautness of the skirt dissipated. She lifted her lower legs, the obvious invitation to strip the skirt down them but Dean stopped to remove her black velvet half boots. He held first one leg by the calf and removed the shoe. Lola lay still, still recovering her breath.

When her feet were bare, he shifted the skirt down her bare legs and off. She wore only a pair of black bikinis that were clearly wet, the plume showing her arousal covered most of the visible cloth. Lola was very, very wet. Dean tucked his fingers under the woman's panties and peeled them off of her body. He crawled over her and stripped off the bra and the shredded blouse. She lay quiescent under him, licking her lush lips and watching him with glistening anticipation. He bent down and licked and sucked her nipples, back and forth, kissing around the arch of her smoky breast and bitting her a little each time he moved away from a spot.

Finally, he left her, gratified to see that glazed, aroused look in her eyes. He glanced at Diana. Her eyes flicked from the nude woman to him, back and forth as though she couldn't control their movement. Dean focused on Di, waiting for her eyes to fix and stay with his but before that happened, Lola spoke.

"Belt." She whispered, her voice barely a groan, barely a grunt. "Skin. Please!"

He turned back to her. The belt lay lank beside her head.

He turned her, moving her body as though she had no will and indeed she gave him little help. He twisted her around so she lay lengthwise on the bed. He crawled up her body, pushed her legs wide and mounted her. She tensed then, clinched down on him with legs and cunt. Her back arched and she orgasmed, so she said.

"Coming!" She groaned. "God, oh god, coming!"

Dean ground down into her, their pubic bones crunched together. Lola bucked under him again. He pulled out of her scorching pleasure. That stopped Lola's bucking climax, which surprised him. She writhed a little on the bed. He used her knees to twist her over onto her face and picked up the belt. Standing beside the bed, looking across it at Di, he regarded the naked black woman.

"Count, Lola." He said and brought the belt down on her ass. It snapped like a cracking tree limb. She screamed.

"One. Oh god, Master, one!"

He looked over at Di on the bed, arms pulled wide, legs akimbo. Her skirt covered her but she kept jerking one leg as though trying to move it. She hung from the cuffs, her hands no longer holding onto their chains. She dangled.

"Count, Diana." Dean said, his voice even.

"What?"

Dean struck Lola's bare ass, hard. The belt snapped on her flesh, making it quiver. She didn't move a muscle but cried out immediately.

"Two, Master!"

"No. Not two, Lola, not until Diana counts for us, with you." Dean struck her again. Lola cried out again.

"One Master!"

"How many will she get, Diana?"

"What?" Di lifted her head, her eyes from the naked woman to look at Dean.

Dean struck Lola again. Di's lips clamped shut.

"One, Master, oh god, one!" Lola cried out again.

"Disrespect me again and we could be here all night and poor Lola won't sit right for a week!" Dean said, speaking as though he were discussing the weather. He tossed the belt on the bed beside Lola. Her hand moved to it but she didn't grasp it. She caressed it, her fingers tracing the edge of the leather. Dean saw that, the tenderness in the motion. Lola seemed to feel his eyes on her skin, turned her head his direction and twisted to look up at him, her breasts puddling under her. Di saw, she couldn't see Lola's eyes but she felt it, the exchange between them. She shivered.

Dean walked over to the little mini bar and found a couple jiggers of scotch and poured both into a tumbler. He tasted it, set down the glass and picked up the ice bucket. He found a hotel robe, donned it and looked at the two women. Di was hanging, not looking at him. Lola lay on the bed, naked, not moving at all. She seemed to be soaking in the moment, the stillness, the anticipation. He walked out the door and down to the ice machine, filled the bucket and walked back. He was only a few steps away from the door when he had that awful realization that he'd not picked up the key card on the way out. He shrugged. Small mistakes do not make small men. Small ambition may, though.

He knocked on the door. Waited. Knocked again.

When it opened, he was hard again because there was only one way the door opened. Lola stood at the door, naked, her great tits waved at him. Dean raised his eyes from those alluring breasts and found her eyes. They were glassy, glistening. Her lips were full, moist and she kept licking them with her thick, pink tongue.

"Forget something, Master?" She said, her voice ripe with amusement.

"You're my key...and my key hole." Dean muttered, suddenly amused with himself.

He pushed past the nude woman, going to the little bar he sat the ice down. Di was watching him. He put ice in his drink and turned around. Lola stood at the foot of what had been her bed. He gestured at Lola with the drink in his hand.

"Come here, Lola." He said softly.

She moved with celerity, making her breasts waggle and jig. She didn't stand before him, she opened his robe and pressed her voluptuous body against his. Her skin was not cool but dry, smooth and silken. She put her hand on his hard cock and held him before looking up at him. Dean put the glass to her lips and tipped it up. She sipped some of it and choked a little then gained control and swallowed the fiery liquid.

Dean took another drink and set the glass down, now frigid in his hand. He pushed Lola away and shrugged off his robe. She made to get to her knees but he grasped her by the arm and turned her to the foot of Diana's bed. Lola understood immediately, she bent over, spreading her feet a little, and planted her hands on the bed. She arched her back and her pussy made a soft little noise, like when a spoon is stuck into a large pot of jam. Diana stared down her body at them, widening her legs a little but her crotch remained covered by her skirt.

He moved behind her, fingered her pussy until she opened to him and then entered her. His cock penetrated the hot, wet slurry of her body, jolting him with the fabulous feel of her pussy. Lola groaned softly but otherwise didn't move. Her body clamped down on him and she massaged his cock with her expressive cunt.

"How many times shall I strike her, Diana? You decide. This is your punishment."

"Fifty!" Lola chortled. "I love the belt! Badger will love it if I am bruised to hell and gone next week!" She laughed, a throaty purr in her throat. "He loves when I groan in pain and he has to comfort me and like that!"

Dean slapped her ass, a playful swipe that nonetheless cracked in the humming silence of the room. She moaned.

"Shut up, Lola. I wasn't talking to you."

"Everyone is talking to me, Master." She giggled again but when Dean ground his cock around inside her, she stopped and hummed to herself. Dean took hold of her hips and intensified their joining. They were joined, her lush ass crumpled between them pressing at him, enveloping his senses, commanding his attention. He wanted to move, to hammer her, to fuck her, to slam her flat onto the bed. He didn't. He remained still, but inside, she gnawed at him, shifting her cunt around his cock, pulling at him as though to drag him deeper.

"Di, I asked you a question." Dean said, raising his eyes from the woman mounted on his cock to the one cuffed to the headboard of the bed. She looked confused and terrified at once. He understood. "You may answer my questions, but just that. No commentary, no begging, not yet anyway. Answer me, woman." His voice sounded like the hum of a motor, low and steady but with a resonate grumble to it.

"Twenty, sir." Di whispered.

"No."

"Twenty-five, sir?"

Dean nodded.

"That's a good girl, Di. You finally got it right." He hunched against Lola, rocking her forward. She groaned from the feel of his cock touching her, moving around inside her molten cunt. She squelched then and Dean felt her verdant body bubble between them. He pulled free of Lola, regretfully, albeit, and peered between her legs. A line of clear liquid streamed down one thigh, ending just above the lined back of her dark knee.

He tapped Lola gently on the small of her back.

"On the bed, dear." He said softly. When she made to stand, his hand restrained her and she realized she wasn't returning to her own bed. She put a knee on the end of Di's bed and let it take her weight. She hesitated when she neared Di's foot. Di watched her movement with a sort of dazed fascination.

"I've always wanted to, Master." Lola whispered.

"What? Wanted to do what?" Dean asked. He knew. Badger had told him about Lola's midnight confessions but he'd dismissed them but now they came back to him but this time from Lola's own lips.

"I want to eat your girl." Lola spoke slowly, as though trying unfamiliar words, like it was a new language for her and she was unsteady in it. "Master." She added belatedly and then turned her head as though to look at him but didn't twist all the way around.

"She doesn't like that idea." Dean whispered.

Now Lola did twist to look at him, her smooth, brown body rippled as she stressed it to look back at Dean. She posed in mid-crawl, one knee on the bed the other still stuck to the floor.

"Do you care?" She asked, her eyes flashing with challenge. "Master?" She added, late again.

Dean moved his gaze to Diana and found her gaping at him. He offered her the slightest of smiles and then put a hand on Lola's ass and gave her a little shove. She finished mounting the bed, stopping to pose now on all fours, just about touching Diana's feet. Her breath surely puffed onto Di's legs.

"She'd love it when I finished with her!" Lola mumbled. Dean smacked her lightly on the ass.

"Di, open your legs. Lola, lay down between them, as close to her crotch as possible without touching her." Dean went to the other bed and picked up the belt. "Count." He said, "both of you." He brought the belt down onto Lola's stout ass with casual force. It barely made a sound.

"You can do better than that." Lola whispered. "Master." She added, still late, again.

"One." Diana said, her voice croaking.

"One what? Di?" Dean struck Lola again.

"Two, Master." Diana hissed her eyes fixed on the woman between her legs like it was a huge viper.

"No, Di. Count properly!" Dean struck Lola again. This time she jerked and the belt cracked on her ass, making it move and jiggle before she tensed, drawing up her muscles in response to the driving sensations assaulting her.

"One, Master! One!" Diana cried out then, suddenly weeping, her voice gurgled with it. Tears appeared in her eyes again and one burst free and ran down her cheek. "Oh Lola, I'm sorry!"

"Shut up, bitch, don't distract him." Lola snarled. "One, Master." She added, her voice suddenly bow string taut.

Dean stuck her again and again, and again. Each time, Di numbered it with her streaking voice and Lola groaned then echoed the count. Dean laid the belt to the black woman until they got to thirteen using regular timing, hesitating just enough for their voices to wriggle in and announce the count. To that point, the steady, regular, even distribution moved from the tops of her thighs in the shadow of her butt, to the small of her back. He stopped.

Lola was panting but oddly, Diana was panting harder, louder, constantly licking her lips, sucking air between her teeth. She sounded like an orchestral interlude in an atonal opera. The room felt small, close. Dean waited. Neither woman moved. He was hard, so hard he felt like the skin on his cock was too small, constraining him.

He struck Lola flush across the arch of her ass. Hard.

She jerked and screamed, not a word but that inchoate screech that is supposed to gain God's attention and hold it.

"Fourteen, Master. Oh god, Master!" Diana's voice crackled, almost harmonizing with the belt.

"Fourteen! Master!" Lola agreed.

Dean waited. And waited. And waited.

His cock began to wilt, so he'd waited a beat too long. He struck again. Lola screamed this time.

"Fifteen, Master." Di gasped, all volume drained away from her tone leaving just the husk of the words as though she was being turned inside out by their departure from her lips.

"Fifteen, Master Dean!" Lola's voice went all throaty, gravelly and rough. Dean struck her again and then again and again.

"Sixteen, seventeen, eighteen!" Diana rasped then gasped. "Master. Master. Master!" She rattled.

"Sixteen, seventeen, eighteen." Lola said but her voice was languid, soft.

Dean hit her again, the hardest yet. Lola's scream was loud and long. She spoke first though.

"Nineteen, Master Dean. My god, my god, my god!"

"Nineteen, Master Dean." Diana echoed, her voice going small and dainty.

Dean struck Lola again. This time, finally, her ass moved. The whole time, she'd laid between Diana's spread legs not moving a muscle, like a hare hiding from the fox, her arms folded under her chest, elbows against her sides.

"Twenty, Master." Lola said her voice finally tightening.

"Twenty, Master." Diana agreed.

Dean counted to ten and struck her again. Both woman responded, almost together, no longer seeming to acknowledge each other, mingling their voices together into a lurid chorus. He struck Lola again and her ass rose and dropped but then repeated the motion, haltingly like an engine struggling to ignite and run on its own. In just that way, Lola's ass began to move, up and down, humping nothing but an idea.

Dean struck her again.

"Oh god, Twenty-three, Master, my sweet, sweet Master!" Lola's voice broke.

"Twenty-three!" Diana's voice had turned papery, brittle, like she was scrapping the words out of her ribcage with the jaw bone of a jackass.

Dean struck Lola's ass again, the hardest yet. Lola howled but she continued to hump nothing. She wriggled her ass once and her pussy squelched, sounding loud in the room.

"Twenty-four!" Lola gasped. "Master, master, master, twenty-four!"

"Twenty-four." Diana's voice was quiet, almost non-existent, making no more sound than a hummingbird's wings, whirring with her attention. "Oh my loving Master."

"Oh Christ's chairs!" Lola whispered. "Oh my god, my god, Sir, I am so turned on. I have never been this wet. I'm a puddle waiting for you to dip into me. My god, you can belt me anytime, Deano!" She giggled harshly, not as before, but cackling almost. "Master Deano, I mean."

Dean didn't move. He regarded Diana with a steady gaze, not moving until finally she lifted her stare from the naked woman laying between her spread legs to Dean's eyes.

"Tell me when, Kitten." Dean whispered.

She goggled, Diana did. Her eyes grew wide again and nearly round.

Dean didn't move, not a muscle, not the belt which this time unlike every time before, he left laying on Lola's tortured ass. He didn't move his eyes from Di's eyes either. He held her gaze until she blinked furiously and looked away, at the windows, the ceiling the bar, all around her as though tracking a sparrow trapped in the room, and doomed.

Dean waited.

"Oh my god." Lola lifted her head. She struggled to her elbows. With one hand she moved the flap of Diana's skirt from between her legs, exposing the white skin of her inner thighs and the burgundy thong. Lola took a finger and moved the swatch of fabric covering Di's pussy aside.

Dean did not shift focus. He felt Lola look back at him. Diana still wasn't meeting his gaze.

"She doesn't like that." Dean said, heard the hoarse quality of his voice, cleared his throat and repeated himself, word for word. "She doesn't like that."

Lola turned back to Diana's pussy and suddenly ran her tongue up the rippling folds of it. Diana flinched and cringed away.

"Twenty-five! Master!" Diana cried out, locking her eyes on the woman between her legs.

Dean cracked the belt onto Lola's ass, so hard she both jerked and yelped. He tossed the belt aside but froze.

"Twenty-five, Master Dean." Lola mumbled.

"Twenty-five, Master...Dean." Diana echoed.

Dean pushed Lola's legs wide and knelt in the space between them. He grasped her by the hips and lifted. Lola crooked her knees under her body and let him set her down on them, as though she were a folding table, built for his convenience. He moved behind her. She wriggled her ass. It was hot to the touch and she groaned as his hands gripped her, pulling her ass cheeks apart in preparation for entering her.

"Tell me to fuck her, Kitten." Dean whispered.

"Fuck me, for fuck's sake! What are you asking her for! It's my cunt! Uh, Master." Lola growled. She felt his cock bobbing against her ass and tried to fit herself onto it to no avail. She needed his help. She keened a little in her throat.

Dean waited.

Diana's eyes finally found and halted on Dean's. She blinked a few times but didn't look away. She licked her lips then nodded once. When Dean didn't respond, she pulled her eyes away from his and focused on the black woman on all fours between her legs.

"Yes, fuck her, Master." Diana whispered softly.

"What, Di? I didn't hear you."

"Yes, Master, fuck her. Fuck Lola."

"Is that a command, Di?" Dean asked archly. That brought her eyes back to his.

"Oh god!" She gasped. Her arms rattled the cuffs and she shifted back, pulling herself up on the bed. "Please, Master, please fuck her. Fuck Lola."

Dean didn't move, still.

"You want to watch, Di? You want to glut your eyes on the sight of me thrusting my hard cock in this cunt?"

"Of course she does, for fuck's sake!" Lola snarled.

"Oh god, yes!" Diana gasped. She bent her knees, leaving Lola unframed on the bed. "I do. Fuck her, like you'd fuck me if..." Her eyes widened. "I'm not supposed to be talking!"

Dean positioned his cock at Lola's entrance and thrust into her. Her body welcomed him, a slick desire that let him slide deep into her. Lola dropped her head onto her forearms, shivering. Her ass was hot against Dean's body as he docked with the bent black woman, her ebony body accepted him with compliments and wet agreement that this was her purpose in life, to be beaten and penetrated.