Five Dates

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

"What's on the poster, Matt?"

"You'll see."

"If it's a picture of me, I swear to God, I'm out of this car the second it stops."

Matt's eyes flared up, and he put a small bag in Dalia's lap. "I don't like your tone, slut. Look in the bag."

Dalia unzipped the little pouch to find a fat dildo and a butt plug with some lube. She opened her mouth, but Matt held his hand up and the words died on her tongue. "One more word from you, and I'll send you back. Rich will get a package in the morning, and all of this will be over. Is that what you want?" She shook her head hard, her hands clenched around the little pouch. "You want to keep being my fuck toy?"

Dalia flinched at his words, but she nodded and blushed when her pussy clenched at his humiliating words. She eyed the fat dildo, it wasn't too long, but it would stuff her full to the brim. What would it be like to walk through a crowded bar like that, juices dripping down her thighs, getting closer and closer to cumming?

Matt's voice startled Dalia from her fantasy. "How much longer before we get there?"

The cabby answered. "A few minutes maybe."

"Thanks."

Dalia got the message, she was on the clock. She cast a quick glance at the driver, grabbed the dildo and slipped it between her legs. Her lips were wet enough to take the monster, but she had to push hard to get all of it in. A moan slipped from her throat as the toy did its job. The driver winked at her when their eyes met in the rearview, and Dalia's hand froze as a wave of embarrassment made her pussy squeeze down on the toy. She blushed scarlet and shied away from his knowing eyes.

Dalia grabbed the plug and squeezed lube on the bulbous head. A flash of shame made her stomach clench when the tube spluttered. She didn't dare look up again, certain the driver was looking back to see her humiliate herself even further. She lifted off her seat and pulled the back of her skirt up.

The driver said, "Is everything all right, Miss?"

Matt muffled a laugh, and Dalia boiled with frustration at her predicament. It was his fault she was half-standing in the back of a cab with her tiny asshole hovering over a fat butt plug, chatting with their driver. "I'm fine, thanks. Just readjusting something."

"Do whatever you want, but please stay seated. Safety policy."

Dalia could've died of shame. This complete stranger thought this was her idea of fun, that she was some kind of slut who got off on this. The plug stretched Dalia's ass as she carefully lowered herself on it. She took deep breaths and squeezed her eyes shut to fight the burning pain until she'd stretched her asshole wide enough to take the toy. She thumped in her seat, the rest of the plug filling her ass in a flash, bumping into the fat dildo. Dalia moaned as pleasure spread through her body. So full.

Dalia still lay panting with her eyes closed when the car rolled to a stop and Matt got out. Dalia hurried after him, readjusting her skirt as she went. Every step she took twisted the toys stuffing her holes, and she couldn't keep up with Matt's fast pace. "Stop, Matt."

He looked back at her flushed face with a grin curling the corner of his mouth. "What's wrong?"

"You know what's wrong."

"You're such a horny little slut, Dalia."

"I'm not! This is your fault."

"My fault? I didn't even touch you." He started walking again. "Come on, it's only a five minute walk."

"Why do we even have to walk? We took a cab. Why not give him the right address?"

Matt winked at her and said, "Where's the fun in that?"

Wonderful. Frustrated, Dalia pushed herself to put one foot in front of the other. And repeat. Again and again, faster. Still Matt gained on Dalia. If she didn't speed up, he'd leave her behind, panting, on the edge of cumming. Every step stirred her body up even further, the sweet burn in her ass, the constant pressure pushing against her sensitive pussy. It trapped her in her own little world, so much so that she bumped into Matt's back when he stopped.

He grabbed Dalia by the waist to stop her from falling over and pointed at the bar sign with the cardboard tube. "We're here."

"Andrews? Never heard of it."

"Nina liked it here. It's cozy, and the people are great. She loved to perform here."

"Nina? What did she perform?"

"Obedience, slut. For her that meant sexual servitude." He pushed the door open and went inside, leaving Dalia behind on the sidewalk. She was tonight's entertainment. Just a few steps inside those doors, and he'd show her off as his fuck slut again. Dalia laughed to herself, her body was burning up not even half an hour after he'd picked her up. She was his fuck slut. What other choice did she have?

Dalia pushed the door open, and a pleasant buzz greeted her inside the bar. What had she expected? Some poor girl dangling from a Saint Andrew's Cross, with a machine pumping plastic cocks in and out of her holes? Maybe a blond slut with big fat tits, and a real cock choking her. Dalia swallowed and pushed down her thoughts. She was just distracted.

Matt waved her over, a beer and a glass of deep burgundy wine on the table. "You knew I like red?"

"Bordeaux or anything else French."

Dalia smiled and took the glass. "You remembered."

"Yeah, kind of stuck in my mind."

Dalia took a sip and let the rich taste roll over her tongue. "It's good." She gestured towards the room and said, "So this is it?"

"Disappointed?"

"You said it was kinky."

Matt laughed and said, "Most of the time, this is what you get. People get together for a drink and a good time. But once a month, they put up a show in the back."

"Like what?"

"All kinds of things. I've seen floggings here, and I suspended Nina once, along with a few other slaves. She loved that one, made some friends. They had a glory hole a couple months back, and last month it was maid night. I would've loved to see you serving people with your tits out."

"What are you making me do?"

Matt leaned in close, his warm breath brushed past her ear. "We're playing pool. If I win, I'll fuck you on the pool table and all of these people..." He kissed her neck and then whispered, "they'll see you cum like a slut."

Dalia sat frozen, her body trembling. "And if I win?"

"I take you home, and our date is over."

"Just like that?"

"Just like that. Isn't that what you want? I mean, it's not like you get off on being my fuck toy, do you?" He chuckled when her answer stuck in her throat. "And of course you're not soaking wet just thinking about it." Matt reached between Dalia's legs and slipped his hand inside her panties. She whined when he rolled her clit between his fingers. "But maybe I'm wrong."

Matt's hand disappeared, and he wiped the tips of his fingers on Dalia's top lip. The smell of her own arousal filled her nose, and Dalia moaned as her pussy clenched around the fat toy. Matt took a sip from his beer and winked at someone sitting at another table. Dalia swiveled her head only to find a table loaded with people waving at her.

She slumped back in her seat and drank her wine in the hope it would calm her down at least enough to stop blushing, but it did nothing. Wherever she looked, she got a knowing little smile and a greedy stare. They all knew, and they were looking forward to seeing her lose her dignity. No, not in a million years. She had to win, no matter what. She had to.

A murmur went through the room when Matt got up from his seat and offered Dalia his hand. He led her through the maze of tables at his leisure, showing off his slut. A good part of the patrons followed them into the back room where a pool table and a corkboard stood set up. They filed in and stood at the edges of the room as Matt slipped his poster from the tube and pinned it to the corkboard.

1.Bra

2.

3.Sweater

4.

5.Panties

6.

7.Stockings

8.

9.Heels

10.

11.Tank top

12.

13.Skirt

14.

15.Pussy plug

16.

17.Butt plug

18.

19.You lose

20.

Dalia read the list, and the full weight of Matt's control over her fell on her shoulders. He'd known she'd obey him and dress as he'd told her to. Her skirt barely covered her ass, and her top wasn't something she could wear without a sweater to cover up. Her tits would spill out. Matt wanted to tease his audience with tantalizing glimpses as he slowly undressed her. Worst of all, he'd been confident her holes would be stuffed by now.

Matt cleared his throat, and the murmur in the room died down. "The rules for tonight are simple: to win the game, one of us needs to pot ball one through ten in order. My slut has an added rule: whenever I pot a ball, she loses the piece of clothing that matches the number on the ball. All of you can help her get naked. Don't hold back on the teasing either, she loves it."

A knowing chuckle ran through the small crowd, and Dalia's skin prickled with all those hungry eyes on her. She swallowed and said, "Matt, you sure this is a good idea?"

"Don't worry, everyone knows the house rules. Hands and mouths are fine, keep all the rest to yourself."

That wasn't much of a reassurance, and Dalia edged further from the people closest to her. Her heart beat in her throat. Why did this turn her on so much? Matt nudged her, and she hopped forward until she bumped into the pool table. He pushed a cue in her hand and said, "You can start, slut."

"I'm no good at pool, Matt."

"That's fine, we'll still make it exciting." He put his hand between her shoulders and pushed her forward until she was level with the table. His hand slipped down her back and disappeared under her skirt. He tapped the plug in her ass and said, "Just stand like this and put your hand on the table so you've got something to put your cue on. Then you pull back..." True to his word, Matt pulled the plug back, and Dalia struggled to focus on the white ball. "And once you're comfortable, you tap it hard."

Dalia groaned when he slammed the plug back in its place, and her cue hit the ball with a hollow thunk. She got up and glared at Matt, "That's not fair."

"Then why didn't you stop me? My turn."

Still angry, Dalia watched Matt as he leaned down on the table, focused and relaxed. His cue struck the white cleanly and seconds later the thunk of the number one ball hitting the pocket sounded. Dalia's stomach clenched as an excited murmur rose from the crowd. Matt lined up again and everyone in the room held a collective breath, but he missed his follow up. He stood up and shrugged in apology. "Too bad. Any volunteers want to help my slut with her bra?"

"Me!" Two small hands dragged Dalia down onto a chair. A petite woman with short brown hair and beautiful hazel eyes made herself comfortable on Dalia's lap. Her eyes twinkled above her little button nose as she leaned forward and pressed a feather light kiss on Dalia's full lips. Shocked, Dalia opened her mouth and let herself be lost in a slow kiss. Her lips tingled when the girl pulled back and said "Get her arms up."

Dalia's arms were pulled up, and the sexy little minx on her lap reached around her back and unclipped her bra with practiced ease. She reached down Dalia's sweater and yanked her bra up in one go. "You guys take care of the rest."

The girl's little hands slipped under Dalia's sweater and found her rock hard nipples. She pinched them with her sharp nails and kissed Dalia hard when she moaned. Dalia pushed her hips up as the girl twisted her nipples harder and harder, pulling her tits away from her body, until she hopped off Dalia's lap and left her panting, her body aching for more.

She was a slender little beauty. Toned legs, an amazing ass that ran up to a tiny waist and a set of perky breasts. "That should do it, I'm Lara by the way." She squeezed Dalia's tits through her sweater. "Better get going, slut, I don't want to annoy your master when he's being so generous."

Dalia sat stunned for a second. It was happening again. People accepted she was Matt's fuck toy, like it was obvious. She pushed off the chair and grabbed her cue. Matt edged nearer to her, but she flashed a look at him. "Don't."

He smiled wide and said, "Good luck."

"I don't need any."

Matt raised his hands and took a step back to give Dalia space. She took a deep breath and aimed at her own number one ball, the cue slid between her fingers, and she pushed forward. A clean hit. She smiled when it ricocheted and dropped another ball down the pocket. "There."

"That one's mine."

"What?"

"Take a look, which one's missing?"

Shocked, Dalia scanned the table, and she grimaced. "Your number seven."

Matt glanced at the corkboard and grinned. He waved the sleek brunette over and said, "Lara was it?"

"Yep."

"I'm Matt. Could you take care of her skirt?"

"Sure, can I take my time?"

"Whatever you want, she'll love it."

The two grinned at each other before Lara turned towards Dalia, hands on her hips. She nodded towards the pool table. "Stand like you're about to be fucked."

Dalia hesitated, this girl wasn't Matt. She didn't have to do anything she said. Dalia glanced over at the chair in the corner and swallowed as her nipples throbbed, begging to be hurt more. What would happen if she gave in and let this beautiful young woman loose on her? She didn't know.

Lara closed the distance between them and pushed Dalia's head down until her forehead pressed against the cold wood bordering the pool table. Dalia had hesitated too long and now her decision had been made for her. "You heard your master, slut, I expect you to obey me. Now put your hands on the table and don't you dare move them."

Startled, Dalia obeyed and put her hands on the edge of the pool table. "Matt, can you tell me if she moves her hands?"

"Of course."

Matt's boots appeared in the bit of floor Dalia could see, and her heart sank. With Matt involved, she had no choice, anything this girl wanted was as good as a command now. She whined when Lara yanked her skirt down, and the flimsy piece of protection slipped down to her ankles. The brunette ran her nails over Dalia's bountiful ass, waking up the skin. "Are you ready, slut?"

Dalia moaned as Lara wedged her panties tight in the crack of her ass, pushing the toys deeper inside her holes. Her pussy and ass squeezed hard when Lara's little hand slapped down on her round cheek. "Answer me."

"Yes! I'm ready."

"Tell me, why am I spanking your ass?"

"I don't know."

"Because you're a slut. Say it!"

"I'm a slut."

Lara's hand slapped down hard on her cheek. "Louder."

"I'm a slut!"

Another slap. "Again."

"I'm a slut!"

Lara worked up a rhythm, forcing Dalia to spill out her degradation as she got her ass reddened. Lara stopped when Matt spoke up. "She moved her hands."

"The little slut." The little brunette gestured for Matt to take her place as she reached between Dalia's legs. Dalia's breathing stocked when Lara's nimble little fingers closed around her clit, poised to make her squirm. "Matt, punish her ass hard. And you, slut, you're going to cum for me."

Dalia squeezed her eyes shut and pressed her forehead harder against the pool table. She didn't want to cum, not like this, not in front of so many people. She groaned when Matt's strong hand struck her burning ass hard. Her body shocked forward, pushing her into Lara's fingers. So close.

"Beg for it, slut."

"Please."

"Not good enough."

"Please!"

"Saying it louder doesn't make it better."

Matt didn't slow down, and every blow jostled the fat toys stretching Dalia's holes. Her legs trembled, she couldn't fall down on her knees. Not now. "Please make this slut cum!"

"Better. I want more."

"Please let this fuck toy cum! Please! I need it! I need to cum!"

"Why?"

"Because I'm a slut!" Tears rolled down Dalia's cheeks as the humiliating words tumbled from her mouth. She repeated them over and over, until finally a monster orgasm erupted in the pit of her belly, sending juices streaming down her legs. Dalia's body shook with the intensity of the pleasure, and she fell to her knees with her head hung down in shame. She'd done it again. Another humiliating orgasm she'd never wipe from her memories.

Matt and Lara stood next to each other, looking down on Dalia. Matt nudged Lara and said, "Nice."

"Thanks, she's just so responsive. Thank you for letting me play with her."

"No problem, she loves it just as much as you do. Stay close, the game's not over."

Lara grinned up at Matt and said, "I know." She grabbed a fistful of Dalia's hair and pulled her to her feet. "Can't wait for you to lose again, slut."

Dalia blushed as Lara kissed her cheek and smoothed her hair back like she was a little girl, and not a grown woman at least a decade older than her. This girl, she was just like Matt, pushing her to places she didn't want to go.

But there was no option for Dalia to stay within her safe zone. Matt potted one ball after the other, and she lost every scrap of clothing she had, except for her tank top. Her tits jiggled freely in the excuse for a top, and her hands itched to cover up the toys poking from her holes, but Lara watched Dalia like a hawk with a cue in her hand, ready to cane her ass whenever she dared to hide her shameful state.

Tears sprang into Dalia's eyes when ball six dropped. Lara smiled at Dalia as she hooked the straps of her top and edged it down, revealing more and more of her fat tits. She yanked it back up when she'd cleared Dalia's tits so the stretchy fabric pushed up Dalia's big melons. "There, that looks great."

She reached between Dalia's legs and swiped her little hand along Dalia's overflowing pussy. Her hand came back up, shiny with Dalia's juices, and Lara sucked her fingers dry, her hazel eyes never leaving Dalia's. "You're dripping, does this make you horny?"

Dalia wanted to shake her head so bad, but Matt loomed behind Lara. Her stomach twisted as she did, but she nodded. Lara smiled and pressed a kiss on both of Dalia's nipples. "Good girl."

She ran her little hands down Dalia's arms and grabbed both her wrists in a soft but firm grip. One push told Dalia to cross them behind her back. She obeyed, and Lara walked around her. "Go where I lead you, slut."

"Okay."

Dalia walked forward when Lara pushed, but her steps faltered when she got closer and closer to the crowd. Lara spanked her ass when she stopped. "Keep going."

"Please don't."

"Keep going or you'll regret it."

It was hard, but Dalia forced herself to step forward again. One more step, and she was in reach of the greedy hands reaching for her tits. A little closer, and the toy in her slit wasn't safe either. She counted the seconds as all those hands touched her, soft and hard, teasing, pinching. Her mind swam as the hands overwhelmed her. The only anchor she had was the small hand locking her wrist in place.

One quick pull, and Dalia stumbled back, away from the horny crowd, only to hobble a few steps further so everything could start again. Dalia didn't know how many people had played with her tits and pussy by the time they finished the tour, but her body was set to explode. She needed a surer touch to get her off, all the frantic hands on her body had done was set her on fire.

"Your turn, slut."

Dalia stared at the cue in her hand and blinked. "What?"

"The game, it's your turn."

Dalia nodded and randomly made a shot. She couldn't care less. What she wanted was release. Her pussy throbbed around the toy stretching it open, and she looked on from faraway as Matt potted another ball. A small hand pushed down on her shoulder. "Get down on your back." Dalia obeyed, hazy with arousal. "Now spread your legs wide and keep them that way."

"Okay."

"That's a good slut. Very good."

The small brunette appeared between Dalia's legs, smirking down at her. "Now fuck your pussy. Cum for me."

1...45678...10