Brianna Clarke Undercover

Ch 1. The Husband

As a private detective Brianna Clarke adopted numerous roles and disguises. This evening she was the dominatrix Mistress Leila. Her sub was Colin Patterson, an overweight middle-aged blackmailer. It was their second session together. There wouldn't be a third.

Brianna, a gorgeous twenty-eight-year-old brunette, wore BDSM black leather. A skin-tight, strapless, plunging V-neckline minidress with matching elbow-length gloves that left her fingers exposed. Thigh-high boots with pointed toes and thirteen-centimetre spiked heels.

Around her waist was a pegging harness with a twenty-centimetre textured strap-on dildo.

Colin was naked and bent over at the foot of his luxurious fourposter bed. His arms outstretched; wrists tied ceremoniously to the bedposts with silk scarves. A good tug and he'd be free. But he too was roleplaying, and he'd paid Brianna handsomely for her to dominate and humiliate him.

After two hours he was near the point of exhaustion.

"How naughty have you been?" she asked.

"Very bad Mistress Leila." His voice just audible.

She pumped her hips driving the plastic silicone device deeper into his ass.

"Do you need more punishment?"

"Yes, Mistress Leila," he said weakly.

While continuing to thrust the dildo into his rectum she reached around his fat stomach and squeezed his balls.

"AAAAH," he screamed. Tears rolled down his cheeks.

"What did you say worm?"

"Please Mistress Leila. I can't take much more."

She let go his testicles and began to gently stroke his cock with tender but firm fingers.

He purred in delight.

After a few minutes of an intense hand-job he was ready to explode. Then she stopped.

This was the fourth time she'd brought him to the edge and paused. How many more ruined orgasms could he endure?

"Please Mistress Leila. Let me come."

"You haven't earned that right wuss."

She undid the leather strap that held the pegging harness to her body and took a step back leaving the dildo buried in his ass.

"I'm going for a drink," she said. "While I'm away I want you to think of all the punishments you deserve."

During their first encounter she'd surreptitiously checked out his lavish home. As a result, she knew where to go. She exited the bedroom and raced to his study where she quickly found the incriminating file. She unzipped her right boot, wrapped the file folder around her calf, and then re-zipped.

After she poured two fingers of Glenfiddich into a tumbler and added three drops of distilled water, she returned to the bedroom.

He was still prone at the foot of the king-sized bed with the dildo fully engorged in his ass, the straps hanging down along the backs of his thighs.

What a pitiful sight she thought. But let's focus on the assignment. All she had to do now was exit without his realizing she'd stolen the information that compromised her client.

She swallowed the Scotch in one gulp, tossed the empty glass aside and then yanked out the dildo dropping it on the floor. His ass let out a noise that sounded like a fart.

"Lie spreadeagled on your back weasel," she demanded.

As he stood up the silk scarf restraints immediately came undone. He awkwardly climbed onto the bed. After hours of punishment his entire body ached. He lay on his back and slowly spread out his arms and legs.

Using additional silk scarves, she fastened his wrists and ankles to the posts of the bed.

She looked down at him. Prone, open, vulnerable, and paid to be abused. What a loser.

Earlier that evening she'd added 2.5-centimetre acrylic stiletto extensions to her fingernails. She slowly scraped them down his stomach leaving deep red lines but not breaking the skin. He moaned in pleasurable agony. She did it again with the fingernails of her other hand.

"Oh yah," he muttered.

She paused at his genitals.

He squirmed in anticipation of what she might do.

She dug her nails into his balls.

"AAAAAAAH," he yelled in anguish.

Wrapping her fingers around his cock she stoked up and down the length of his shaft. Minute after minute. Another enjoyable hand-job. Occasionally she added a twisting motion.

"OOOOOOO," he cooed ecstatically.

She inserted the sharp end of her index fingernail into the opening of his circumcised dick.

He shrieked in agony and almost pulled loose from the silk scarf restraints.

Bending over so that he could admire her cleavage, she softly licked the top of his cock. Precum oozed out.

"OH YES."

She slapped his balls, and he yelped in pain.

How much more could he tolerate? Excruciating torment mixed with erotic delight.

He was panting as though he'd run a marathon.

"Did you think of some sexual punishments I can inflict on you?"

"Yes, Mistress Leila." His voice a mere whisper.

The masochist says beat me. The sadist says no.

"Your torture," she said, "is to think of even worse abuses until I return. It may be in five minutes. It may be five days. But I'll be back to bash your balls and it'll be unexpected, humiliating, painful, and debasing."

He exhaled in contentment.

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Ch 2. The Wife

Brianna was putting on her trench coat in the opulent foyer of the Patterson's home when the front door opened. A good-looking middle-aged woman entered pulling an expensive pink roller suitcase.

"Who are you?" the woman asked.

"A business associate of Mr. Patterson," Brianna lied. "And you?"

"His wife."

She wore a form-fitting, uber expensive, pale green designer outfit that complemented her red hair.

"I've met all his associates," she said. "But I've never met you."

She eyed the beautiful Brianna. Stunning. Self-assured. Confident. Beige trench coat. Leather stiletto boots with cockroach killer pointy toes.

"You look more like a working girl."

Should she protest? Bolt for the door? If she fled, they might suspect that she came with an ulterior motive, such as theft.

She'd have to brazen it out.

"Where is he?"

Brianna nodded towards the bedroom.

"Come with me," the other woman said leaving her suitcase in the foyer.

They entered the bedroom and were surprised to see Colin in his pyjamas sitting in bed under the covers reading a novel. The scarves, strap-on harness, and dildo were nowhere in sight.

"Tasha," he said lowering his book. "What a surprise. I wasn't expecting you until tomorrow evening."

"Evidently. And you needed pussy?"

"I'm not a hooker," Brianna said. "I'm Mistress Leila, a dominatrix."

She removed her coat and let it fall to the floor showing Tasha her black leather outfit. Never stop roleplaying was Brianna's motto.

"How marvellous," Tasha exclaimed. "We're all into fifty shades."

Tasha slipped out of her bodycon dress. She wore cherry red bondage lingerie that complimented the colour of her hair. An excruciatingly tight lace-up corset with matching garter belt and stockings. Sexy lace trimmed panties. Stylish stilettos.

She eyed her husband. "Why didn't you wait for me, darling?" To Brianna she asked, "How much did he pay you?"

Brianna answered and added "I'm worth it."

"Was she?" Tasha asked Colin.

"Oh, fuck yes."

Tasha walked over to the dresser, picked up Colin's wallet, peeled out a wad of bills that she handed to Brianna.

"Are you ready for round two?"

Never step out of character. "Yes," she said tucking the money into the top of her left boot.

"Did you cause him pain?"

"A lot."

"How cruel were you?"

"Very."

"How many times did he come?"

"I didn't let him."

"Excellent. Did you tie him up?"

"With silk scarves."

"Rope's better." Turning to Colin she said, "Get in position."

He obediently removed his PJs and sat on a pillow at the top of the bed with his legs in lotus position and his arms outstretched. Because of his size he looked like a welcoming Buddha.

Tasha opened the bottom dresser drawer and removed four rope coils that she used to secure his right arm and left ankle to one bedpost and his left arm and right ankle to the other bedpost. The restraints were all the right length.

She put a ball gag in his mouth.

"His torture is to watch us." Tasha said.

Did Brianna have a choice after she admitted that she was a dominatrix?

"Are you the sub?" Brianna asked.

"We'll alternate."

Brianna sashayed over to Tasha. Putting her arms around Tasha's neck she gave her a passionate kiss. For over a minute they explored one another's mouths with their tongues. As they did so, Tasha unzipped the back of Brianna's leather minidress while Brianna undid the laces of Tasha's corset.

They parted lips and stepped back. The dress and corset fell to the floor. Neither woman wore a bra. Without saying a word, each removed her underwear.

Tasha was about to take off her garter when Brianna said no.

"I'll stay in my boots and gloves," she said. "And you keep on your garter, hosiery, and heels. I'll be kinkier for him."

They looked at Colin whose eyes lit up. He nodded in approval. He had a fetish for naked women in fuck-me shoes. The beautiful buff Brianna in boots. His nude wife in stilettos. His cock became rock hard just looking at them.

Tasha's body was firm and toned, the result of hours at the gym preventing middle age from taking its toll. Brianna had the figure of a runway fashion model. Tasha's boobs were larger than Brianna's with large dark areolas. She was a natural redhead with a muff of long curly red hair whereas Brianna's was a neatly trimmed brown landing strip.

They kissed again. Brianna's right hand fondled Tasha's left breast. Unexpectedly, Tasha viciously jabbed two fingers into Brianna's pussy. In response, Brianna pinched Tasha's nipple with her overly long fingernails. They each groaned in pain into the other's mouth. Sadism and masochism.

They fell onto the king-sized bed and positioned themselves close to Colin so that he could see and hear everything. They fondled, caressed, and explored one another's bodies with their fingers and lips and tongues, varying between inflicting pleasure or pain. Joy or suffering. Being the dominate or the submissive.

Colin squirmed. It was an erotic sight. Passionate girl on girl action. Would he come by watching them cavort on the bed?

Sometimes they'd include him, stroking or sucking on his dick. Occasionally they slapped his balls. It was unclear whether he bellowed in joy or agony into his ball gag.

Tasha retrieved two twenty-centimetre dildos from the dresser's bottom drawer. One was the silicone sex toy that Brianna had used to peg Coilin's ass. The other was a ten-speed vibrator. For the next fifteen minutes they used them to arouse one another and Colin's cock.

Brianna positioned herself so that her legs were wide apart. Her hands were over her head massaging Colin's balls. Tasha's face was in her pussy, sucking her clit. The high-speed vibrator whirled in Brianna's ass. She was in erotic heaven.

After what seemed like never-ending moments of sensual pleasure, Brianna cried "Oh, fuck yes" as she came and squirted in Tasha's face.

She lay panting, sprawled on the bed covered in sweat like a damp rag, and not wanting to move. She just wanted to be. The ten-speed continued to gyrate in her ass.

"That was so great," she said, "but I need a moment."

"Not happening bitch."

Tasha, now the dominatrix, moved to the top of the bed placing her cunt in Brianna's face and her head in Colin's crotch. Cunnilingus and fellatio.

"Eat me," she demanded.

With her face buried in Tasha's snatch Brianna inhaled the other woman's odor. Separating her overly abundant pubic hair, she kissed her vulva, sucked on her clit, fingered her anus.

Tasha stroked and sucked Colin's dick. But she won't let him come. For agonizing minutes, he moaned into his ball gag. Drool dribbled from the corners of his mouth down his chin.

Brianna transferred the ten-speed from her ass to her cunt. Then she picked up the tapered silicone dildo and inserted it into Tasha's pussy. Tasha purred contentedly.

She continued to stimulate Tasha with her lips and tongue while rotating the sex toy deep inside the other woman's vagina.

"AAAAAAAH," Tasha screamed as she orgasmed.

"FUCKKKKKK," Brianna cried as the vibrator in her love box that was still set on high cascaded her over the edge.

Afterwards the women lay on the bed exhausted, sweating, and panting.

"I need a drink," Tasha said. "You?'

"Thanks."

Tasha stripped off her garter belt, nylons, and shoes. Strolling naked out of the bedroom and into Colin's study she poured generous amounts of Scotch into two tumblers and returned handing one to Brianna. They clinked glasses and chug their booze.

Brianna hadn't removed her boots.

"What about him?" she asked.

Colin was in agony. For thirty minutes he'd watched two hot women repeatedly bring one another to ecstasy, while he sat bound to the bedposts. During that time, they'd cruelly taken him to the point of an orgasm and then stopped. Over and over again. He couldn't take much more. He wanted to scream. To lash out. To come.

"Let's take him out of his misery," Tasha said. "Slowly."

They alternated sucking his cock. First one woman for ten seconds. A pause for ten seconds. Then the other woman for ten seconds, followed by another pause.

It was excruciating. He'd be at the edge and then they'd rest, only to be brought to the tipping point again and then stopping. When not giving a blowjob, they'd laugh gleefully at his plight.

They were cruel and sadistic. Evil and vile. And he relished it.

Eventually he came.

It was a satisfyingly large load that Tasha transferred to Brianna through a kiss and that she snowballed to Colin through another kiss after she removed the ball gag. Then she forced his jaw shut so that he'd swallow all of his own cum mixed with the saliva of the two women.

"You earned your keep," Tasha said to Brianna as she untied Colin.

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Ch 3. The Son

Brianna quickly dressed and exited the bedroom leaving the naked Tasha and exhausted Colin cuddling on the bed.

She was halfway to the front door when it opened and a handsome young man the size of a giant entered. He was massive, almost two metres in height and over a hundred kilos in weight.

He glanced down at the pink roller suitcase in the foyer and then at Brianna in her beige trench coat and black leather boots.

"Huh?" he grunted.

All she wanted to do was leave the Patterson residence with the information she'd stolen from Colin's study. But he blocked her exit route and was far too large for her to get around.

"Who are you?" he asked.

Twenty-two different responses raced through her mind before she heard an unexpected announcement.

"She's you graduation present, Arthur."

Brianna shot a look over her left shoulder. Tasha, wrapped in a plush white terry robe, stood outside the master bedroom door.

How far did roleplaying go? Would she have to comply?

She examined Arthur. A lustful grin graced his face.

What had she gotten herself into? To steal a file for her client, she'd pretended to be a dominatrix. She'd pegged the husband, followed by lesbian sex with the wife. Would she now have to service the son?

"Be gentle," Tasha said. "He's still a boy."

She returned to her bedroom closing the door softly behind her.

Brianna sighed. It looked like she had no choice.

"Where to big boy?"

He picked her up in his arms as though she was a paper doll. Carrying her to his room he said that he was twenty and had just graduated from university with a degree in philosophy.

"But everyone thinks I'm a jock because I'm so big."

He put her down and sat on his bed.

"I appreciate Mom's offer and I'd love to have sex with you. But I can't."

Normally this would be good news. But he said it with such disappointment and sincerity that she asked why.

"I've only dated four other girls. They were all my age. Each time, when the relationship started to get serious and we thought about sex, they baulked as soon as they saw it. Said it was too big. That I'd split them in two."

"What did you do?"

"I jerked off on their boobs."

Brianna was intrigued. How large was it?

"Show me."

Arthur stripped and stood naked in front of her. He was all muscle with a ripped body. His limbs like tree trunks. His torso like steel.

"I work out for two hours every day," he said.

He was normally proportioned for a giant except for his colossal dick. It was larger and thicker than anything Brianna had ever seen. It looked like a truncheon.

"See what I mean," he said meekly. "Women don't want anything this size inside them."

She understood why eighteen-year-olds with limited sexual experience might be reticent. But Brianna considered herself a woman of the world.

"It doesn't intimidate me. Lie on the bed Arthur."

She took off her trench coat. He drank in her BDSM outfit. His penis become more erect.

She'd manipulated Tasha by keeping her boots on when they had sex. But this was different. As Arthur's graduation present, she'd have to be completely naked.

She sat on the chair by his desk and carefully removed her boots hiding both the money and purloined file from his sight. She slipped off her dress and thong underwear.

She poised before him nude with arms akimbo. His huge fully erect cock throbbed in anticipation.

Climbing on the bed she lay down beside him and kissed his full lips. He put his arms around her. She massaged his six-pack abs and then took hold of his mammoth cock. It was so large her fingertips couldn't touch one another. He grabbed hold of her ass cheeks.

"Arthur, I'm going to lick your cock to get you lubricated and then I'm going to mount you cowgirl style. We'll go at my pace. Understand?"

"Uh, yup."

"Afterwards you'll be able to brag that you actually fucked a woman."

"Giddyap."

She licked his testicles. He squirmed. Had no one ever done that to him before?

She took one of his jumbo balls into her mouth. He wiggled as his cock danced in delight.

"Oh yah."

She massaged his perineum with her long fingernail. He gasped. Obviously, this was another first for him.

"Don't stop," he said.

Beginning at his scrotum she licked up the side of his dick and then kissed the top of his circumcised penis before she slowly took the huge bulbous head into her mouth. It was like sucking on the top of a baseball bat.

With her right hand she pumped his shaft while she took more and more of his cock into her mouth. It was humungous. Larger than trying to swallow an unpeeled banana.

Controlling the gag reflex she let it enter her throat.

"Holy fuck," he called out.

She could only take half its length. She'd choke otherwise.

While continuing to pump his shaft with her hand she slowly removed her mouth from his cock.

She gasped for air. He was panting.

"No one's ever done that to me before," he said.

Now was the time for him to experience real sex.

Even though he was twice her size in width, she positioned herself with her legs widely extended on either side of his hips spreading her cunt to the max. Holding her vulva open with her fingers she slowly lowered herself onto his enormous piece of meat. She took her time rocking down his shaft taking more and more into her. After thirty seconds he was fully engaged in her.

A mighty throbbing gargantuan male muscle was stimulating pussy places that no cock had ever touched before.

"Oh my god," he said.

"Fuck yes," she responded.

She pumped up and down on him. He responded with gusto.

"Suck on my boobs."

His abs muscles were so strong that it was no effort for him to raise his chest so he could lick and nibble on her nipples.

As he stimulated her breasts she rode up and down on his cock with increased enthusiasm and energy. It was heavenly having him so deep inside her. Her cunt was expanded to its limit. But she didn't care if he split her apart. It was pure ecstasy having him fuck her pussy and suck on her tits.