Private Detective: Tina Boyde

"I don't do this for free," she said.

"Too bad. This is the initiation."

"Then I'm leaving."

"Are you a fucking cop?" he asked coldly.

"I'm a working woman here for business."

He gestured to his cock. "The business is right here."

Tina hesitated while she looked at Redmond's growing cock. She reluctantly dropped down to her knees and immediately grabbed the cock with both hands. The cock made her fingers look skinny in comparison. She stroked it fast. Then she bent down to take the cock inside of her mouth. She sucked as fast as she could. The faster she sucked and bobbed her head, the more he moaned.

"Oh fuck," he groaned. "You're one hot bitch."

She ignored the compliment and continued the oral techniques she had learned from spending time with countless female prostitutes. It wasn't long until she felt Redmond's impending orgasm. She knew she had no choice but to swallow. And she did. She jerked his cock and swallowed every shot of cum.

When it was over, she stood up and wiped her mouth with the back of her hand.

"Damn bitch," he groaned. "You're the real deal. There ain't no way a cop could suck cock like that."

"Believe me now? Or should we use a lie detector and truth serum?"

He put his wet cock back inside his pants. "You passed the test. Now let me show you something."

Redmond stood up and finished fixing his pants. He led Tina out of the office and down the hall. They walked up a flight of stairs and there was a hall filled with different rooms.

"What's this?" she asked.

"This is where the real action happens. I could use a bitch like you for some of my clients. Yeah, you'll be a big hit with the fellas."

"What kind of money are we talking?"

"Depends," he replied. "If we've got a party going on, you'll get a thousand bucks minimum, straight from my pocket. Clients pay extra money on top of that. We've got plenty of people coming here with deep pockets. With a mouth like yours, you should be rolling in dough."

"Deep pockets huh? That's exactly what I want. I'm not interested in working regular johns. I'm here to make real money."

He slowly nodded. "Yeah, alright. We may have something coming up soon. There's a party with some friends of mine. Deep pockets. They love having fun. They always enjoy sampling the new products."

"I'll be there."

"Sure. Alright. First I'll need to get one of my girls to train you on how everything works. You know, the etiquette. That's very important around here. I run a respectable joint."

"I can see that," she replied. "The sooner I learn the ropes, the better. I want to be ready for that party as soon as possible."

He smiled, "Damn bitch, I like your attitude. Either you love to fuck, or you're flat broke."

"I'm just trying to make a living like everyone else."

"Nothing wrong with that."

They exchanged contact information. Tina gave him an email account which was specifically created for the undercover operation. Before she was allowed to leave, Redmond was insistent upon receiving another oral encounter.

Part 3 of 3: Becoming the Bondage Woman

Grace was a tall statuesque woman. She was dressed in a leather corset and leather boots. Her hair was tied in a ponytail. She had just finished a private session with a client.

"So you're the new girl," Grace said.

"That's me," Tina replied.

The two women exchanged pleasantries and shared their history. Grace explained her past as a high-end escort. Tina gave a concocted story about how she was a stripper in various cities.

Grace gave a brief tour of the bondage rooms. The rooms were nice. They were fancy, classy, and well lit. There were sex toys and devices which Tina had no clue about.

"Have you ever fucked a man in the ass?" Grace asked bluntly, with a smile.

Tina smiled back. "No, I haven't."

"Shame. Have you ever fucked a woman in the ass?"

"I don't have a cock."

Grace opened a drawer and picked up a strap-on dildo.

"Now you do."

"Is that what the clients here want?" Tina asked.

Grace nodded. "You'd be surprised how many rich guys want to get pegged by beautiful women."

"Pegged?"

"Fucked in the ass."

"Oh, well I look forward to obliging those requests," Tina said with a slight grin.

Grace smiled, "It's really easy. Just lube it up and give it a go. Work your way in gently. Then have fun. Would you like me to give you a demonstration?"

"I can figure it out, thanks."

"That's too bad. You have a lovely body."

"Thanks," Tina replied. "What else do the gentlemen here want? I definitely wouldn't mind sticking some of those larger dildos up their asses. Or maybe even giving them a few smacks with a paddle."

"Depends on the guy," Grace said suggestively. "Sometimes you'll see a guy who's obviously a rich and powerful man, but he wants to get fucked in the ass or slapped around. Sometimes you'll see a guy who's unassuming but he just wants to treat a woman like absolute shit."

"Is that hard to deal with?"

"It's part of the job. You adapt to everything. Give the clients what they pay for."

Tina slightly nodded. "Do you like working here? You can be honest with me. I won't tell anyone."

"Honestly, I'd do this for free. On your first day, you'll find out why. But enough about me. You still have plenty to learn."

Tina was dumbstruck that any respectable woman would provide those services for free. Grace winked, then continued with the tour.

***

The next day. Tina was in Astrid's downtown office. It had been a while since they last saw each other. Both of them were dressed in business casual outfits while they had coffee.

"There's a big event this weekend," Tina explained. "I'll be at the bondage club along with Redmond's inner circle and other associates. I'll try to identify his crew, then later I'll conduct further investigations on them. It shouldn't be long before I get the dirt you need. Maybe several weeks. Maybe a few months."

"That's exactly what I was hoping to hear. I knew I hired the right lady."

"You get what you pay for."

"Speaking of which, you've managed to earn Redmond's trust. He usually doesn't trust many people."

"I have my ways," Tina replied.

"Did he initiate you?" Astrid suggestively asked.

"That's not important."

"But I want to know. Did you suck him off?"

Tina gave a faint shrug. "Yes."

"Did you like it?"

"I didn't come here to talk about that. Let's stick to business."

Astrid smiled, "Fine. Thank you for personally coming here and giving me an update. I really appreciate it. When this is all over, you'll get your money. Who knows, maybe I'll hire you again someday."

"You should keep your nose clean after this. You're beautiful, rich, and you have everything going your way."

"Thanks for the advice," Astrid sarcastically replied.

"Is there anything else I should know about? What should I expect at the bondage club?"

"It depends on who you're paired with. I'm sure you'll have fun. I did."

"You sound like you miss going there."

"Not really," Astrid replied. "I've already found another bondage club to indulge my pleasures."

"Try to stay out of trouble. Let me know if you have any useful information which could help me later."

"Leaving already?"

Tina nodded. "Yes, unless there's anything else you want to discuss?"

"You know, you've never asked me about the video that Redmond is using to blackmail me with. Aren't you a little curious?"

"Why would I be curious? I already know what sex looks like."

"Not like this. Care to have a look?" Astrid asked.

"Sure."

Astrid walked over to the large flat screen television in her office and prepared to play a video. The video started. It was a hidden camera placed in a bedroom. Astrid was completely naked on screen. A large middle-aged man came on screen and Astrid got down on her knees and performed oral sex.

The rest of the video showed Astrid being bound and gagged on the bed, then being ravished in a rough manner.

Tina's eyes were transfixed on the screen. She had never seen sex done so roughly.

"Exciting, isn't it?" Astrid whispered in the investigator's ear.

"Do you actually enjoy that?"

"It's not for everyone. But yeah, I love it once and a while. It's something to indulge in."

Tina's eyes remained glued to the screen. "It looks disgusting."

"Well, if you find yourself in that position at the party, just think of all the money you'll be making later. Focus on the money. Maybe it'll help ease the pain."

A sinking feeling grew in Tina's stomach. It made her sick thinking she might actually be in the same position as Astrid in the video-- bound, gagged, and ravished.

She immediately left the office without saying a word, wondering if she was making the biggest mistake of her life.

***

The bondage club looked much different at night. It was lively and exotic. As a former Vice detective, Tina was amazed that law enforcement had never heard of this place before.

She changed her clothes in the private back room alongside the other women. She wore a sexy tight fitting corset. Black boots to match. Her hair was tied in a ponytail. Her biggest fear was that a criminal she had previously arrested would recognize her, but Tina's heavy make-up and colored hair took care of that.

There was a bar and lounge area where a group of well-dressed men were relaxing with drinks. Scantily clad women were everywhere, flirting as much as possible.

Tina surveyed the rooms. The men surveyed her back. It was slightly uncomfortable having her body being gawked at, but she had experienced that feeling several times before during past undercover assignments.

She immediately recognized a few low-level figures who had been known to law enforcement in the past. They were now Tina's leads in the investigation.

A man tapped Tina's shoulder from behind. She turned to see a thin male in his early 30's, with a fairly meek appearance. She wondered how someone like that could be involved with such bad people.

"Are you new here, miss?" the man asked with a high-pitched voice.

"It's my first official day."

"I'm Steve."

"Tina."

"Pleasure to meet you."

"Likewise," she nodded. "What can I do for you, Steve?"

"I think you know. Upstairs, in the room?"

Tina gave a sexy nod. "Are you a top or bottom? Let me guess, you strike me as a bottom."

"Sometimes," he nodded back.

"And tonight?"

He looked around to make sure no one heard. "I want to be a bottom tonight. Yours."

"Follow me."

Tina led the man up the stairs to the bondage room she was assigned. She did her best to act cool. She remembered everything Grace had taught her. It was a nerve-wracking feeling. She had never done anything so sexually deviant before, and it scared her, and excited her at the same time.

She closed the door once they got inside. They made small talk to relax.

"Shall we get to business now?" she asked, trying to sound sexy.

"Yes, please."

"Pull down your pants and underwear. Bend over the table."

Steve nervously unbuckled his belt and let his pants fall to the floor, along with his underwear. His penis was small and flaccid. Tina wondered how the man could ever please a woman with that thing. He turned around and bent over.

She opened the drawer and wore the strap-on. She took no pity on the man since he was involved with criminals, so she used the giant 9 inch dildo. She showed some mercy by applying plenty of lube on it.

"Reach back and spread yourself," she said.

He obliged.

Tina positioned herself behind him and pressed the tip of the sex toy against the man's anus. She gave a little push and entered his body. It amused her that Steve whimpered like a little girl. She slowly pushed deeper and deeper.

"Fuck, how big is that thing?" he gasped.

"Keep your mouth shut until I address you. Is that clear?"

"Yes mistress."

It made her pussy wet being called a 'mistress.' It was a newfound feeling of sexual power over a man. It was especially arousing knowing that she was pegging a criminal associate.

While the dildo was half-way inside, she bent down and put her lips against his ear.

"So, do you work for Redmond?" she asked, pushing deeper.

"Yes," he whimpered.

"What do you do for him? I'm curious?"

She pushed a little deeper.

"I... I can't tell you that."

"Come on, Steve, I'm curious. I love bad boys."

"It's a secret," he moaned.

She pushed deeper. "This thing is 9 inches. I can do this all night long."

"Alright, alright, alright! Just don't hurt me."

"Do you move products for Redmond?"

She pushed harder, allowing most of the dildo to be shoved inside of his delicate ass.

"Ahh!!! Alright! Yes!"

"Bad boy! I think you need to be punished. Don't you agree?"

"Yes ma'am! Please punish me! I've been very bad!"

Tina gave a hard push which shoved the entire 9 inch dildo up the man's ass. He cried and whimpered. She began to fuck him with a few thrusts. Just as she was beginning to have fun, the man reached down to jerk off, and he grunted loudly while shooting several massive strands of cum onto the floor.

When it was done, he laid face down onto the table, breathing heavily.

"What a sensitive prostate you have," she teased. "That's too bad. I was starting to have fun."

She yanked the dildo out of his ass, leaving a gaping hole. Then she gave his bottom a soft pat.

"Put some ice on that," she said.

***

Tina returned to the party. Her eyes scanned the room. She noticed a few more criminals who were known to law enforcement. Her photographic memory hadn't let her down.

Before she could get a full survey of the room, Redmond approached her, accompanied by another large burly man. Tina instantly recognized the man as the person who had sex with Astrid on the video.

"You're doing one hell of a job," Redmond told her. "Not bad for your first time. All the guys here want to fuck you, in case you haven't noticed."

"I've noticed."

"I'd like you to meet Cutter," he said, gesturing to his friend. "He's been asking about you all night. He loves breaking in the new girls."

Tina shook the man's hand. "Pleasure to meet you."

"You too, lady," Cutter grinned.

"I'll leave you two alone," Redmond said. "Enjoy yourselves."

Redmond returned to the party, and Tina was left awkwardly with the large man.

"The boss has been telling me a lot of good things about you," Cutter grunted.

"I'm sure he has. Look, I don't mean to be rude, but I'm sure there are plenty of other ladies here who would be better suited for your needs."

"What's the matter? I ain't good enough for you?"

"I'm not feeling well," Tina replied.

"I got a pocket full of cash and a giant cock in my pants. Ain't that gonna make you feel better?"

"You're a real class act."

"This is a whore house. What do you expect, lady?"

"How about a man with some sense of decency?"

He grabbed her by the arm. "Get the fuck upstairs, lady."

Tina reluctantly obliged the man and led him upstairs to her assigned room. All she could think about was how Cutter ravished Astrid sexually and secretly recorded it so that Astrid could be blackmailed. Tina wondered how a beautiful and wealthy young woman could ever agree to have sex with a scumbag like Cutter.

Once they reached the room, Tina closed the door. She was seriously considering striking him unconscious and making her escape.

"Feel like being a bottom tonight?" Tina asked.

Cutter unleashed a powerful laugh. "You some sort of comedian? I ain't no fucking bottom."

"Then what do you prefer?"

"How bout you take off that sexy corset. I've been waiting all night to see those tits."

Tina rolled her eyes. She briefly thought about grabbing a sex toy and bashing the large man over the head with it. But the odds of putting him out were slim. Cutter's head looked like it was made of stone. The only realistic option was to do what he wanted. No one would ever know besides Cutter and Redmond.

She untied the corset and worked to remove it. It wasn't hard. Before long, the corset was open and she removed it from her body. She stood completely naked before the man, wearing only a pair of leather black boots.

"Not bad," he nodded. "Those tits are a little small, but I like the overall package."

"What now?"

"Come here baby."

Tina reluctantly approached the man. He took a step forward and they were face to face. He reached in his pocket and grabbed two pairs of cuffs. Tina briefly wondered if Cutter knew she was a former detective, and the thought terrified her.

"What are you going to do with those?" she asked, hiding her fear.

"What do you think? We're going to have some fun tonight, you sexy slut."

Cutter grabbed each of her wrists and cuffed them. He led her to the side of the room and cuffed both of her hands to the wall. She simply allowed it. In all her years on the police force, she had never been in a tense sexual situation like the one she faced with Cutter.

His massive hands roamed and fondled her body. Tina closed her eyes. The man's hands were large and strong. Nothing was gentle about it. Both of her breasts were groped hard, and her delicate small nipples were pinched to the point where they badly hurt, but she didn't make a sound. Cutter's hands moved down her body and grabbed both of her toned ass cheeks. Then his hands rubbed between her legs and pussy.

"We're going to have some fun tonight," he said.

The hands stopped touching her and he moved away. Tina was facing the wall, cuffed, so she couldn't see what Cutter was doing.

Suddenly, a powerful pain ripped through her bottom end. She had just been struck by a flog. It caught her completely by surprise. It made her scream.

"What the fuck are you doing?!" she yelled.

"You're in a bondage club, lady. Redmond told me what a slut you are. So you should be used to this."

Another hit from the flog came. Then other. The flogging came in an intense series of blows which made Tina's ass burn with pain. She made groaning sounds, but she didn't want to give Cutter the pleasure of hearing her scream any further. After ten more hard flogs, the strikes ended.

Cutter got down on his knees and buried his face between Tina's ass and pussy. His mouth opened wide and he slobbered everywhere.

"You taste good," he said during a brief break. "They don't make pussy like this anymore."

Cutter's mouth continued sucking and slobbering. It felt surprisingly good to Tina. It was a much needed relief from the painful flogging. She arched her back slightly and pushed her rear towards his face, giving him better access. Surprisingly, Cutter began to lick Tina's asshole, which was something she had never felt before.

"That feels nice," she admitted in a moment of weakness.

Cutter stopped. "This rimjob ain't for your pleasure, lady. It's for mine."

He stuck his tongue inside and then pulled out, giving several more licks around the ring of Tina's asshole. Then he stopped and walked away.

Tina wondered what other surprises were in store for her. But then she remembered the video of Cutter with Astrid. Whatever Cutter was planning, it wasn't going to be very nice.

A cold object was suddenly pressed against her anus. It felt like a small lubricated dildo, and it was forcefully shoved inside of her ass. She clenched her teeth as the sex toy was pushed in her rectum.

"Like that?" he asked with a sadistic tone.

"You're a real fucking jerk."

"I'm paying good money for this. I'll act however I want."

Cutter stood behind Tina and adjusted her hips. He used his strong hands to place Tina's hips exactly in the right spot. The sex toy was still hanging out of Tina's asshole.

He pressed the tip of his erection against Tina's wet pussy. Then he gave a hard push and penetrated her hole. He grabbed Tina by the shoulders and pushed himself all the way inside with a forceful movement, making her gasp out loud.