Detective in Red Lipstick

"Do you enjoy sucking them?"

She politely smiled. "Any real woman does. You could say I'm a proud cocksucker, but I'm here for business on behalf of Mr. Santino."

"Do you want to join the party? Do you want to be initiated? I can make it happen because I'm in charge of the initiations."

"What happens after?"

"Then, you're free to taste whatever you'd like on this island. No charge. Consider it a perk of your service to us."

"That's a sweet offer," Elisa said, showing obvious interest. "Why are you doing this for me?"

Mindy took steps forwards and their faces had become so close that they could feel each other's breath.

"I realized, I've never had an Asian here before," Mindy said, almost like an epiphany. "Most of my women are European, American, or Latinas. I've had some Arabs before. Perhaps it's time I expand my palate."

Whatever would happen, it would be sexual. There was no doubt about it. Time was of the essence and this was her window of opportunity. She needed to get her eyes on the full activities of this island to report back to her superiors. Raiding an island could only be possible for extreme circumstances. She needed more proof.

Hopefully, if she was lucky, Mindy would just eat her pussy. Maybe the other way around. Elisa had played with other women in college, so it wouldn't be the end of the world.

"Only if you promise to be gentle," Elisa said, batting her eyelashes.

A lustful expression appeared on Mindy's face. "Follow me. I'll be as gentle as I can. And I'll make this quick."

Locking arms, they went inside one of the nearby bungalows. At first glance, the room looked ordinary and cozy. Upon closer look, there were sex toys on the tables and erotic paintings on the wall.

"Please, on your knees," Mindy said like a sweetheart.

Elisa followed instructions and got down on her knees. Luckily the floor had a carpet. She looked at a professionally made painting on a wall, which featured a woman on the table with her legs up, with men lining up for a turn.

Her vision was suddenly obscured when Mindy wrapped the scarf around her eyes. It was being tied around the detective's eyes and she had become blindfolded.

"Don't move a muscle," Mindy said in a playful way. "Be right back."

Suddenly she was left alone with the door open. Would anyone outside see her? What would they think? Minutes had passed. The wait was excruciating. Did they know she was a cop? Did Santino tip them off? Would they interrogate her? Would they kill her? If they did, no one would know.

Her heart pounded while she remained on her knees. Part of her wanted to make a run for it. But she was experienced in dangerous situations and knew how to keep calm. Her instincts told her to remain in place.

Footsteps returned and she heard the chatter of male voices:

"What a fuckable looking sex kitten."

"Cute Asian babe. Should be fun."

The footsteps came closer and Elisa knew that she was surrounded. There was a ruffling sound in front of her.

"Open your mouth, doll," Mindy said.

Elisa complied and parted her lips. If the barrel of a gun had been placed in her mouth, at this point, she wouldn't have been surprised. Instead, she felt the soft skin of a man's erect penis. It was a welcomed relief.

"Close your lips," Mindy ordered. "Suck on it."

It was Elisa's first foray into blindfolded sexual acts, and with strangers of all people. She did her best to suck under the circumstance. Normally she'd dive right in. For this, she didn't know how to act being blindfolded and watched. She didn't know if she should use her hands or not, but she did. She stroked the man as she sucked, picking up her pace.

When the man moaned, Elisa felt a pulsing sensation in her pussy and she sucked even harder. Yes, she was on the job as an undercover detective. But the thrill of sucking someone off, an unknown, while the madam observed was strangely intoxicating. It felt horrible, too. She worked her hand, tongue, and lips around the stranger's dick. It pained her to do this. But it felt so good. Was this man a security guard or someone rich and powerful? Maybe it was a staff member. She sucked it the same, regardless.

"Move over," a different guy said. "Let's see how much those skinny lips and small mouth can fit."

Another? Elisa shuddered at the thought of taking another cock. One was a clear violation of her ethics. For any undercover assignment, she had always been pressured for sex and she was always able to find a way out of it. But two cocks? It was gratuitous. She was wet.

The other man pushed his way into her mouth and Elisa found herself sucking on two men at the same time. Her mouth was stuffed and her cheeks bulged on both sides. Unsure of what else to do, she used her hands to hold each shaft. She wanted this to be over with so she could do her job on the island.

Deep down, this was a fantasy that many women have. She was one of them, though she never dreamt of doing anything with people like this, whoever 'they' were. As she sucked, she prayed that these men wouldn't recognize her someday. If these men were connected and this case went big, surely they'd dig into her file, wouldn't they?

It was a strange feeling knowing these anonymous men could someday realize that they had been sucked off by the lead investigator on this case. But then again, they could never tell anyone either. The truth was, Elisa knew these men wouldn't be arrested. Only the person who made the blackmail tape was the target.

"You have the best mouth," a man said in a low moan.

Mindy added, "She's a real cocksucker. Look at her go."

While trying to make these guys cum as fast as possible, Elisa felt a pair of soft, feminine hands on her hair. Mindy was caressing her head, helping her bob back and forth.

If these people knew that Elisa was a cop, they didn't show it. Or maybe they just wanted to enjoy as much as they could before bringing this to an end?

"Suck it like a lollipop," Mindy said in an excited voice. "You have two in your mouth. Go on, make a popping sound with your mouth, for each dick."

Elisa winced with shame. She held each cock tightly and pulled them out of her mouth. For each cock, she gave a hard suck and pulled it out to make a popping sound. Both men seemed to love it as they laughed softly to themselves.

She knew Mindy loved it too, receiving a kiss from her to the side of the cheek.

"My lollipop can squirt," a man said. "The way you suck my lollipop is making me real excited. Finish the job. I want to see what you look like with my juices in your mouth."

"Same here," the other man said, throbbing into Elisa's hand. "You work it like a pro."

Mindy rubbed Elisa's hair. "You heard the men. Suck it like a lollipop some more. You're so good at it. I knew you'd be."

Clenching her eyes shut behind the blindfold, Elisa stroked the men harder and faster. Her arms were skinny but strong. Her fingers were thin and feminine. She spent a lot of time in the gym, staying in fighting shape for her job in case she'd ever need to defend herself from an attacker. Instead, she was now using her strong arms and tight grip for something else...

"Open your mouth," Mindy said gleefully. "Your red lipstick makes your face so pretty. Now it's a target for the lollipops. Gentlemen, you know where to finish."

Hearing those words excited the men, because Elisa felt them throb so hard in her hands. She stroked them, pointing their cocks to her own mouth. Then she opened her lips wider. She felt the two cocks being guided by a helping hand, presumably Mindy, to make sure that the cum hit its intended target.

The first spurt came from the left side and it hit the inside of her cheek. The guy on the right shot directly onto her tongue. They coated her mouth and she tried not to flinch. To flinch or to close her mouth would show weakness, and she was terrified that she'd fail her initiation and this was all for nothing.

She gulped down what she could while keeping her mouth open. She nearly gagged on it. Her mouth was filled with cum and her taste buds were overwhelmed by their distinct flavor.

"Good girl," Mindy said. "Now it's time to be initiated. Then you'll be one of us."

Elisa was horrified. That wasn't the initiation?

She felt her shoulders being pushed down by Mindy's hands. The detective was now on her hands and knees, still blindfolded.

The back of her dress was lifted. A sharp object was used to cut her panties away. Was this the part where they'd hurt her and reveal that they knew she was a cop all along? That Santino had told on her?

Instead, she felt a lubricated finger press against her small anus. It made her flinch, naturally, but she did her best to remain still. She resigned herself to the fate that she'd be sodomized in some way, as the finger dug even deeper to coat her rectum.

"Time for me to take this ass," Mindy said with lust. "Women can have cocks too, you know."

The finger pulled out and Elisa felt the distinct feeling of a strap-on dildo being pressed against her anus. It was definitely going up her ass. The only question she had was, how big was it?

She knew she'd get very little mercy. She felt Mindy's hands clench onto her shoulders to hold on. With a gentle push, Elisa felt her asshole being stretched as the dildo went deeper. Another push and it went even deeper. She gasped and some of the cum dripped from her mouth, running down her chin, onto the floor.

"Now beg me for it," Mindy said confidently. "I need to know you're the right material for our island. I just need to hear it. I love hearing women beg."

Swallowing her pride, she had already come this far.

"Ughh... fuck it..." Elisa whispered. "Fuck it... take it...please..."

The shame of saying those words was nothing compared to the pressure she felt in her bottom. She was certain the men were still watching this, enjoying the sight of her being sodomized. And she was positive that Mindy had so much pleasure dominating her like this.

She was being fucked. The thrusts came faster and faster. In between, she felt Mindy pulling on her silky black hair, her cultural pride and joy, which was now being used for sexual purposes.

It became agonizing as it went on, as the dildo went all the way in. She was being fucked so hard that Mindy's crotch was slapping into her flesh. She had been spanked a few times with an open palm, too. With some of the deeper thrusts, she even felt the hardness of Mindy's abs against her butt, whenever Mindy bent over.

In a moment of weakness, the detective confessed between moans, "My ass will never be the same again..."

But that pain turned to pleasure when Mindy reached below and fingered her clit. Having her clit rubbed was Elisa's favorite stimulation for an orgasm, and within moments, she was on the verge of screaming.

She could only imagine what the two men were thinking, watching this unholy lesbian coupling. She was certain the men were still there because she hadn't heard them leave; why would they? Elisa envisioned the sight to be something crude; an ultra-fit madam ass fucking an uptight Asian woman who was blindfolded with a cum filled mouth.

She wasn't sure which was more embarrassing, the cocksucking, the sodomy, or that she started to scream and cry like a small puppy. In the bedroom, she was known for being loud and making a twisted face when she came. This was the first time she came from having anything up her ass. The orgasm was memorable and she was dripping from her pussy.

"There, was that so bad?" Mindy asked, grinding to a halt while giving the undercover agent pats on her wet pussy. "I'd say you've passed our test."

The dildo pulled out, leaving a gaping feeling in Elisa's asshole. Her entire body flinched when Mindy slapped her ass powerfully and the sound echoed in the room.

Mindy added, while caressing the detective's hair, "And remember, nothing you see on this island should ever be repeated to anyone else, except for people already in the circle. If not, there will be consequences. Severe consequences, do you understand?"

"Yes, I understand."

With a mouthful of cum and a sore asshole, Elisa had done all she needed to do in order to conduct a full reconnaissance of orgy island.

When the blindfold was pulled, Elisa looked upwards at the two men she had just sucked off. Her jaw dropped, letting some of the wayward cum drip onto her chest.

It was true. It was all true, she thought.

***

The robe was partially open, leaving bare the center of her body, as she had just finished a shower. She lounged around her apartment while coffee was brewing.

Elisa watched the news unfold on cable news. Rothstein had been transferred to a protective unit after a fellow inmate had made an attempt on his life. Twitter was ablaze with speculation about who was behind this. Pundits were in a frenzy. Deep down, she wondered how long Rothstein could survive. In the world of the powerful, anyone could be gotten to.

With her robe still open, she sat down for coffee and breakfast. The tv was still on, playing the news in the background. Her laptop was open and she checked her email.

She opened a message with the subject: Red lipstick

I hope one day I'll get to experience those gorgeous lips of yours while you're wearing that red lipstick. I think about your mouth often. You have a sexy face.

In the meantime, I'll always have this memory. I have one copy. You have the other copy. I destroyed the original copy before the Feds raided the island.

Our secret, forever

x

Clicking the attached file, a video played on her laptop It was the first time Elisa had ever watched a video of herself in a sexual situation. The hidden camera video was approximately 34 minutes long, which meant that her entire interaction on the island had been recorded.

She watched herself sucking cock while blindfolded. She forwarded the video to see herself sucking two cocks. Another forward, she watched herself being fucked by Mindy, who had a sparkling look on her face. It was like something out of a hardcore porn, rather than a major criminal investigation. But her reluctance -- and eventually giving in -- made the whole thing much more arousing than any professionally produced video. This was raw. This was real.

Taking a sip of coffee, she remained emotionless. Her eyes shifted back to the tv, seeing a video loop of Rothstein in handcuffs as the pundits kept up their speculations. Her eyes shifted back to the island fuckfest on her computer.

Her fingertip was on the laptop pad, ready to delete the video and email. If this video had been anyone else (and not her) she would have done the right thing and submitted this video as evidence to the police department. But this was her. This was Elisa at her worst. Or maybe her best?

She pulled her finger away, and instead she ate breakfast while the video played until the end. Deleting the video? Not today. Maybe not tomorrow. Maybe never.

When she finished breakfast, she closed her laptop and changed her clothes. It was time to head back to the police department.

The End

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