WIMP!

Trent Richards met a woman in a bar near a hotel to find her drinking a Manhattan in a booth.  The woman’s called Monique, a thirty-something blonde with a curvy figure and big breasts.  What struck Trent was she was wearing a dark trench coat and sunglasses, even in the dimly lit bar.  There was a manila envelope under a black-gloved hand.  He knows she’s the woman he was supposed to meet because a heart-shaped diamond-crusted clasp was on her lapel.

“Monique?” Trent asked with a slight smile, and the woman nodded, gesturing for him to sit.  “I don’t have much time, so if you could reach the point quickly, I’d appreciate it.”

“How’s Lilly?” Monique asked in a cool, sultry voice.

Trent gasped.  “How do you know my wife?”

“I don’t,” Monique said with a shrug.  “I know of her.”

“What’s this all about?” Trent asked with a frown.

She sneered and slid the envelope to him.  The man stared at it, then back at the mysterious blonde-haired woman.  She casually took another sip of her drink.  Trent sighed, took the envelope in his hands, then pulled out a clutch of papers.  His eyes widened as he flicked through them, and his face turned pale.  His head snapped up, and he blinked at her with his mouth agape.

“Where did you get these?” Trent asked, a tremble now visible in his hands.

“A hacker friend of mine,” she said.   “Interesting, don’t you think?”

“These documents have nothing to do with me,” Trent said, putting them down.

“Oh?” the woman chuckled.  “Then you won’t mind if I send them to your CEO.  When he gets the police to trace those embezzled funds to the Swiss bank account numbers, the fact those accounts are in your name will raise a few eyebrows.  And get you arrested.”

Trent sighed.  He eyed the woman and saw a steely resolve in her face.  She was playing hardball.  “So you’ve brought me here for blackmail?” he asked.

She smiled.  “Yes, and so much more,” she said coldly.

“More?”

“I want a cut of the money you’re stealing, and—I want you.”

“Me?  What the fuck are you talking about?” Trent said, slamming his hand on the table.

“I need a new sub,” she said.  “And men like you make the best playthings.”

“A new sub?  You’re fucking crazy, lady,” Trent said with a sneer.

“I’m a dominatrix, Trent,” Monique said.

“What, like a prostitute?”

Monique smirked and shook her head.  “No, I don’t do it for money.  I do it for fun.  I have an opening for a new submissive, and men like you make the best subs because you have too much to lose if you don’t obey my every command.”

He shook his head.  “What are you talking about?”

Monique raised her hand, and a waiter appeared and put a glass of scotch before Trent.   “Take a drink and calm down,” she said calmly.   “The way forward is clear.  First, you’ll pay me ten thousand a week into the bank account on the slip of paper in the envelope.”  Trent fell back, took the scotch, and drank it.   “For that, I won’t send those documents to your boss and the police.”

“What else?” Trent asked, glancing around.

“You’ll be my new sub and obey my every kinky order,” she said coldly.

“Sub?  Sub?  I’m a married man, lady.  I can’t be doing kinky shit with my blackmailer.”

She lowered her hand, and then her sunglasses and Monique’s icy blue eyes peered at him.   “Then I guess you’re going to jail for the felony of embezzlement.  How will your sweet wife cope knowing her husband is a criminal and liar?  What will happen to your so-called marriage then?”

A well of anger from deep in his stomach threatened to explode as Trent stared intensely at Monique.  His fists clenched, and sweat broke out on his forehead.  Then he gazed at the documents on the table and finally understood that this woman had him by the balls.  He would have to do what she said or lose everything, even be her submissive in some kinky sex play.  His shoulders sagged, and the anger left him.  He bowed his head, shaking it.

“I think you now understand that I own you, Trent.  Body, mind, and bank accounts,” Monique said smugly.  “From now on, you only talk when I ask you a question.  Is that clear?”  Trent nodded, his face red.  “Good,” she said.  “Now, I have a room booked at the hotel next door.  I want to examine my new property properly.  Come on, time to start your new life.”

Monique stood and moved toward the exit.  Trent sat for a moment and glanced at the papers in his hands.  He knew he had no choice but to follow the mysterious woman.

*****

She turned to Trent in the lift, grabbed his balls through his trousers, and squeezed them hard.  When Trent didn’t react, she laughed loudly.

“I knew what you were when I saw you,” she said coldly.  “You’re a wimp and need to be put in your place.”

“I—”

“Shush, you only speak when I say so.  I’ll forgive you this time since you’re new to this,” she said.   “But further unwanted outbursts will see you punished.”

Trent nodded.  ‘What’s the deal with this woman?’ he wondered.  ‘I need to find a way to get out of this.’

When they got to the room, she sat in a chair and told Trent to get her a drink from the bar fridge.  Trent took a small bottle of vodka, poured it into a glass, and handed it to the woman.  He then went to sit, and she held out her hand.

“Did I give you permission to sit?” she asked coldly.

He shook his head and stood to wait for her to say something.  Monique remained silent for about five minutes, sipping her drink and eyeing Trent up and down.

“Take off your clothes,” she said.  “I wanna see what I’m working with here.”  Trent went to speak, and again, she held her palm to stop him.   “I could just have those naughty documents showing how you’re extorting hundreds of thousands of dollars from your employer sent to the police.”

Trent swallowed hard, as he didn’t want that.  ‘I’m trapped, for now,’ he thought.  Eventually, the man stood in front of her in his white briefs, and again, he remained silent for a while. Monique checked him out.

“How old are you?” she asked.

“Ah, forty-three,” he said.

“That’s forty-three, Mistress,” she corrected him.

He cleared his throat and said, “Forty-three, Mistress.”

She nodded.   “You’re pretty fit for your age.   Do you work out?”

“Yes, Mistress.”

“Good, I hate fat middle-aged men.  Turn around, spread your legs, and bend to touch your toes.”

After Trent assumed the position, he waited several long minutes.  He found it hard to stay in that position.  Monique suddenly slaps his ass hard, and the shaking man jumps.

“OK, Wimp, stand and face me.”  After he did, she said, “Open your mouth.”  Monique grabbed his chin hard and stared into his mouth like a doctor.  “Hmmm, good teeth, I like that.”  She rubbed a hand through his black, slightly graying hair.  “Nice hair.  I hate baldies as much as I hate fatties.”  Trent was blinking rapidly as she continued her examination of the goods.   “OK, let’s see it,” she said, pointing to his briefs and the floor.

Trent lowered his underpants, stepped out of them, and stood before her naked.  He hadn’t been naked in front of another woman apart from his wife for twenty years and felt body-aware as the woman stared.  Then Monique started laughing, and Trent blushed a deep red.

“I’ve seen some small dicks in my time, but that’s the smallest by far,” Monique smirked.

Trent’s chin wavered, yet nothing came out.

“Hmm, I bet your wife doesn’t bother with it anymore?  Does she?”

“Um, no, Mistress,” he said with a shaky voice, almost a squeak.  “We haven’t had sex for a very long time.”

Monique laughed coldly.  “No wonder.  There’s no way your babydick could ever please a woman,” she said and laughed again.  “I’m surprised she even married you.  Why did she marry you, Wimp?”

“Ah, that’s kind of personal, Mistress.”

“Get one thing straight, Wimp,” Monique snapped.  “You will share with me every part of your pathetic existence.  Is that clear?”

“Yes, mistress.”

“Go on then.  Why did Lilly marry—that,” she said, pointing to his small dick.

“Ah, she’s a Christian, so no sex before marriage, Mistress,” he said.  “She didn’t see my penis until the wedding night.”

Monique burst out laughing, slapping her knee.  “You fooled her,” she said between cackles.  “Made her think she was buying a Porsche when you were nothing but…but…a Mini.”

“It’s average, mistress,” Trent shouted, but the woman’s laughter made him blush.

Monique continued to laugh.  “How did you ever think that was average?” she asked, then sat clutching her stomach as the laughing gave her a stitch.  “Surely, you saw the other guys in the changerooms in high school.  You must have seen how much bigger they all were than you.  So much bigger.  That looks more like a large clit than a penis,” she shouted and laughed.  When she regained her breath, she shouted, “Your head just sits on those t-tiny balls like some kind of acorn.”  Trent dropped his head and whimpered.  “I’ve seen toddlers with bigger junk than that, Wimp,” she shouted through her laughter.

The man’s body sagged, his shoulders curled over his chest.  He stood there, taking Monique’s laughter and comments, not saying a word or moving.  A sudden weakness in his legs made Trent shaky, and he felt like a piece of meat on display.

“Do you want to see what a real cock looks like?” Monique asked suddenly.

“What?” Trent said, his head snapping up.

The sexy blonde slapped his face for not correctly addressing her.  Trent flinched.

“Know your place, Wimp,” she said coldly.  “Now, ask me nicely.”

Trent frowned, knowing she wanted him to ask her to show him a real cock, yet he wondered whose it might be.  “Can I please see a real cock, Mistress,” Trent asked softly.

“Why do you wanna see a real cock?” Monique asked with a raised eyebrow.

“Um—”

She suddenly slapped his face hard again.

He shook his head at the pain.  “Because I don’t have one, Mistress,” he tried.

She nodded.  “No, you don’t have a man’s cock.  Yours is more like a baby’s little doodle.”

Monique laughed, suddenly removing her sunglasses and throwing them into the chair.  The woman undid the belt on her trench coat and the button and peeled it off.  Trent gasped.  Beneath the trench coat, Monique wore nothing but black lingerie.  She had a camisole with a push-up bra showing her sexy cleavage, her nipples visible beneath the dark lacy material.  The woman also had a suspender belt attached to some black thigh-high stockings and a pair of black silk panties.

Trent stared at her panties to find a bulge in front that shouldn’t be there.  ‘I’m not the only one with a secret,’ he thought.  Monique put her hand on his shoulder, pushing Trent to his knees.  It wasn’t hard, as his legs felt like jelly.

“What are you waiting for, Wimp?” she barked coldly.

Not needing encouragement, Trent lowered her panties, and a large uncut cock sprang out at him.  His eyes bulged, and he gasped.  Then the man sighed because it was not a real cock.  It was a strap-on dildo.  Trent stared at the dildo wide-eyed when Monique slapped him on the head.  Trent took the cock in his hand and started touching and stroking it.  The rubbery flesh felt hard and big.  The humiliated man couldn’t help but see the difference between the dildo and his small dick.

Monique laughed.  “I bet you thought I had a cock for a moment, eh, Wimp?”

“Yes, Mistress,” he said, rubbing the fake cock.

“This dildo is special, though.  Do you know why?”

“No, Mistress.”

“It’s the very dildo your wife, Lilly, uses to fuck herself with when you’re not home,” Monique said with a smirk.

Trent stared at her beautiful face and cringed at her smirk.  “What—err—Mistress,” he muttered.

“Smell it and taste it,” Monique said.  “Go on, your wife used it this morning.  Stuffed the whole thing up her cunt and came on it.”

First, he smelled his fingers, then the dildo itself.  There was a definite smell to it.  He could taste a fishy/pissy flavor when he licked the head.  Monique took his head in her hands and forced the head into his mouth.

“This is what Lilly has replaced you with,” Monique said hotly.  “She cums hard on this fake cock daily and yet, won’t even touch your pathetic babydick.  Taste her cunt on it—taste her cum.”

The dildo felt so thick, and Trent had trouble taking it in his mouth and gagged.

“Be careful, Wimp.  Real cocks can choke you, not babydicks like yours, though,” Monique taunted.  “Imagine Lilly wishing she had a real man while she fucked herself daily with this dildo.  What a loser you are, Wimp.  Lilly doesn’t want you.  She wants this big cock.  You’ve been replaced, Wimp.  She’s cuckolding you to a toy.  Mmmm, you take to sucking cock quickly.  Small dick wimps usually do.”

Trent tried taking more of the dildo down his throat, gagging as it filled his mouth.

“I’ll have to train you to be the cocksucker you were born to be,” she said, laughing.  “Don’t worry, soon you’ll be deep-throating cock like a veteran prostitute.”

Trent couldn’t believe there was any way he could take something this big all in his mouth, and the prospect of being a cocksucker made him feel sick.  The taste of his wife’s pussy was washing away, and he swallowed the rehydrated juices eagerly.  ‘Lilly really is fucking herself with this thing,’ he thought.  ‘How the fuck did Monique get it when Lilly just used it this morning?  Oh my God, any wonder Lilly doesn’t fuck me anymore.  I can’t compete with this.’

“Stand, Wimp,” Monique ordered.  When Trent did, she squeezed his dick and balls hard, making him squirm.  “Does that feel good?”

“No, Mistress.”

“Good, because it doesn’t matter whether you like it or not, do you understand?”

“Yes, Mistress.  I only want to make you happy, Mistress.”

Trent felt dizzy.  He had never had submissive thoughts before, but the man felt sexually aroused even though his body felt broken.

“Do you want to be my sub?” Monique asked.

“Ah, I thought I didn’t have a choice, Mistress.”

“No, you don’t, but I like to know how my subs feel.”

He sighed.  “Then, no, I don’t wanna be your sub, Mistress,” he said with a flushed face.

She nodded.  “Good, but what you want doesn’t interest me,” Monique said with a pinched mouth and cold eyes.  “I own you now, and you’ll do whatever I say, no questions.”

His body sags.  “Yes, Mistress.”

“What about your wife?”

“What do you mean, Mistress?”

“Maybe she’d like something better than a dildo and a babydick husband?” Monique asked.  “I know I would.”

“I-I don’t know, Mistress,” he muttered.

“Describe her to me.”

“Um, well, she’s attractive, forty, five feet six, and slim,” he said.  She has brown hair and green eyes and is clean, Mistress.”

“Her bra size?”

“Thirty-Two C, I believe, Mistress.”

“What does her pussy look like,” Monique asked with a smirk.  “Or don’t you remember?”

Trent swallowed hard.  “Um, she has chubby outer lips with dangling inner ones with just enough trimmed pubic hair, and her clit is pretty large, the hood, in particular, Mistress.”

The blonde femdom smirked.  “Bigger than your pathetic dick, I’m guessing?” she asked.

“No, Mistress.”

“Do you have any photos of her?”

“In my phone,” he said.  “Not naked ones, though, Mistress.”

“Next time,” she said.  “I want you to take a video of her fucking herself with this dildo.  I wanna see it.”

“Please, Mistress, leave Lilly out of this,” he said.  “She hasn’t done anything.”

“Oh?  The problem is your clueless about what she does,” Monique said coldly.  “So it’s time you found out.  It’s time you learn just how much Lilly despises you.”

Trent shook his head, his breathing hard, and his body trembled.  ‘Lilly,’ he thought.  ‘My Lilly, she’s a good woman—a Godly woman who respects our marriage.’  While Trent was processing these thoughts, Monique removed the strap-on and threw it on the floor.

“Lay down face up on the carpet, Wimp,” Monique shouted.  Trent did so willingly.  Monique told Trent all small dick wimps have to eat pussy, but they could never fuck one.  “Pussy is for real cocks, or big fake cocks, but not babydicks,” she teased.

The room suddenly seemed warmer as he watched Monique kick off her shoes.

“Are you gonna have sex with me, Mistress?” Trent asked.

She rolled her eyes.  “What did I just tell you, idiot.  Pussy is not for babydicks.  I wouldn’t even feel your useless dick inside me.  Where’s the fun in that?  Can you make me cum with your mouth, Wimp?”

“Yes, Mistress.”

She stood over him with a foot on either side of his head.  Again, with arms akimbo, she stared down at him.  “What do you see, Wimp?”

“Your pussy, Mistress.”

His point of view was extreme.  Monique towered over him, and at the center of his vision was shaved pussy with fat lips.  Her scent was strong, musky, slightly piquant, and captivating.  As Monique dropped to her knees over his head, it became larger and larger in his sight, and then it swallowed him whole.

“Eat my cunt, Wimp.”

“Yes, Mistress,” he mumbled under her, and his tongue darted out and tasted her fresh pussy.

Trent’s mouth closed over one pussy lip, kissing and licking tenderly before doing the same to the other.  She waited to see what the man would do next, feeling his tongue ran a furrow until it reached the bottom of her pussy.  Trent gave a suggestive lick toward her ass before he swept incredibly slowly up her slit until he suckled her clit like a newborn.  Monique settled back, making herself comfortable, as Trent repeated the sweeping maneuver several times.  Just when he thought she couldn’t take the teasing any longer, his tongue slid inside her cunt.

Monique gasped and then moaned because Trent had a long tongue.  Her body ground into his face, filling his sensations with the taste and smell of her womanhood.  Her legs clasped his head tight, making breathing more difficult.  A hand went behind her back and grabbed Trent’s hair, pulling his head into her pussy to aid the work of pleasuring her.

Over the next quarter of an hour, Trent stayed well away from her clit, with the occasional swipe to edge her along.  Instead, he concentrated on filling her cunt with his tongue and tasting her as much as possible.  Monique found herself remembering past subs.  None of them had shown the attention to detail her new Wimp was giving her.  The blonde dominatrix became more and more aroused.

“Are you enjoying it?” Monique asked.

“Yes, Mistress.”

“I’m enjoying it, too.  You’re a natural pussy eater.  Does Lilly let you eat her pussy?”

“No, Mistress.”

“She’s missing out, the stupid bitch.”

Monique suddenly gasped loudly, her body rocking on his face.  Her pussy clamped on his tongue, then, as it let go, a gush of lady cum dribbled into his mouth.  It tasted so good. Trent nearly came, too.

“Oh—Oh—good—Wimp,” she moaned.

Trent kept going, as this wasn’t over until Monique said so.  She wasn’t letting the man get much air, just enough to keep him working.  The blonde blackmailer fell into a steady rhythm humping his face, making her body respond fully to the incredible sensations his licking tongue gave her.  The feelings grew again, getting stronger and stronger until she had to hunch over Trent due to her second orgasm.

Trent’s face was slick with Monique’s juices now.  His head hurt, and he felt he’d never regain his breath.  Monique’s pussy quivered on his face as she enjoyed the little aftershocks from her orgasm.  Pulling his head by the hair, she jammed his face into her crotch again.

“Eat me, Wimp—Eat me,” she urged.

Trent felt broken.  As he began to tongue her pussy again, he sensed she knew how emasculated he was.  Not only was she blackmailing him for money, but also the woman planned to use him for God knew what.  Trent’s manhood, whatever it may have been, was now gone.  Monique gloried in triumph over him, rubbing his face in her pussy and ass, making him pleasure her.  Her clit began pulsating with need again as a third orgasm built.  The woman pushed her pussy into his face with force.  Trent wondered if he still had a face.  Maybe all that was left was an imprint of Monique’s pussy.

Smothered in pussy again, Trent fought desperately to please her.  He needed to breathe so badly, though.  Monique used his nose as a dick to hump, mashing it against her clit repeatedly as she humped his face.  Trent felt as if he was about to die.  The man’s sure death was coming, barely even aware she was approaching her third and biggest climax on his face.  With his brain starved of oxygen, he saw flashes of light.  Monique screamed in bliss as a powerful orgasm rippled through her body in endless waves of ecstasy.

Thankfully, she fell off Trent onto the floor next to him.  Trent gasped for breath, sucking air down as if a drowning man.  All he could taste and smell was Monique’s pussy.  Trent’s face and hair were slick with her cum and wetness.  The blonde woman lay beside the man, basking in her pleasure, rubbing her clit, bringing her to another climax.  Then she scooped up her creamy cum and stuck her fingers in Trent’s mouth.

“Suck it, Wimp,” she moaned.

Trent did, experiencing Monique’s taste with renewed freshness.  They lay there for about ten minutes, catching their breath.  In all this time, Trent’s boner never went down.  After she regained some composure, Monique noticed his boner and flicked it a few times, making it wobble.  Trent nearly came.

“Is that as big as it gets?” Monique asked and snorted.

Trent felt a pain in his chest as he gazes at his fully erect, dripping dick.  “Yes, Mistress,” he muttered.

“Have you ever measured it?”

“Yes, Mistress.”

“Well, how big is it?  It looks fucking tiny,”

Trent swallowed hard.  “Three-and-a-quarter-inches, Mistress.”

“Oh my God,” Monique shouted, “that’s fucking hilarious!”

Then she burst into laughter, the kind where you lose control and have to drag in breaths.  Monique’s face turned red like Trent’s, but for different reasons.  Trent’s dick softened some as he fought the desire to flee.  He had never felt so degraded in his life.

After the blonde settled a little, she demanded, “Jerk it off, Wimp.”

It took Trent a while to get it hard again after the abuse, but the man jerked it off as best he could.  Monique watched him with a big smirk.  Trent didn’t know how, but after a few minutes, he ejaculated with a shudder and a grunt.  However, all he ejaculated was one small globule of watery semen.  Tears welled in the broken man’s lifeless eyes.  Trent felt so small and insignificant his bottom lip started to tremble.

“Fuck, even your cum is pathetic,” Monique said and laughed again.  “I guess those tiny balls don’t make much jizz, eh?”

“Sorry, Mistress,” he mumbled.

“We’re gonna have a lot of fun together, you and I,” she said.

“Yes, Mistress.”

“Well, I’m gonna have fun, but you might not,” she said and chuckled.  “Are you ready for it?”

“No, Mistress.”

“Good, now take that dildo back home before Lilly misses it.”  She laughed.  “She won’t miss your babydick, but she’ll miss that big plastic one badly.  She keeps it under her clothes in that bureau, bottom right drawer.”

Monique got to her feet, put her panties back on, and then the trench coat to hide her lingerie.  The woman put her silk gloves and shoes on and then grabbed her bag, placing her sunglasses in it.

“OK, I’m going, Wimp,” she announces.

“Yes, Mistress.”

“You’ll set up a new email address and buy another phone just for speaking to me,” she said.  “My phone number is in the envelope, so text me all the details when it’s done.”

“Yes, Mistress.”

“I expect your first payment in the bank account by tomorrow night and every week after that.  And don’t forget, I want a video of Lilly using that dildo by the end of the week.  You’ll catch her doing it if you sneak in the house at about ten.  Every day like clockwork, she shoves that big toy up her cunt until she cums.”

He nodded, and Monique left without even saying goodbye.

Trent sat on the bed long, thinking about what had happened.  His face was still covered in Monique’s pussy juices.  Thoughts were racing through his head, varying from total guilt and shame to excitement and pleasure.  He had a shower, dressed, and left.  When Trent was going through the lobby, a man grabbed his arm.

“Excuse me, the lady said you were paying for the room,” he said, pointing to the reception desk.

“Did she?  OK, I guess I am.”

*****

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