Deep Undercover Ch. 01

"Lovely. Such a lovely sight, Lydia. I could admire you all night."

The man stood up and walked away. Lydia tried to follow his feet, but he stepped out of her limited field of vision. She considered running, but she knew there was nowhere to go. Fleeing, she decided, was the worst thing she could do.

The man returned a minute later. He poured a liquid all over her crotch. She couldn't see what it was, but the odor of it somewhat resembled olive oil. The man stood over her with his feet on either side of her hips. He bent at the knees, lowering his still-erect cock to her crotch. He slid his cock up and down her slit and all along the crack of her ass. When his cock was as slick as her crotch, he placed the tip against her asshole and pushed.

"Not there! That's the wrong hole!"

The man said nothing. Instead, he continued to burrow. Dana's hands reflexively shot back and pushed against the man's torso. Two men grabbed her wrists and pushed them up and into the center of her back. Pain shot through her shoulders. She considered kicking her legs, but she realized that her arms would be dislocated or broken before her legs found a target. She was immobilized.

"Please," she protested. "Not there. You're too big."

Dana knew from experience that the man's cock was too big. Once, after a night of drinking, she tried to take Levan's cock in her ass. He couldn't even get the head past her sphincter. It was the first and only time she had ever attempted anal sex. Until now.

"Stop!" Dana sobbed. "I don't like it in my ass!"

The man continued pushing. Pain shot through her torso, starting in her rectum and ending in her stomach. A different kind of pain rippled through her shoulders.

"Just relax, Lydia. This doesn't have to be painful."

Dana knew she was helpless. Resistance was only going to get her hurt or killed. One way or another, he was going to get in her ass. The only question was how much damage she suffered before he was through. Fighting is pointless.

"OK. OK. Just give me a second."

The man relented. He didn't back up, but he stopped moving forward.

Dana took several deep breaths.

"Tell these men to let go of my arms."

The two men looked up at him. He nodded and they let go of her wrists.

Dana took several more deep breaths and willed herself to relax.

"OK," she said.

A burning pain tore through her guts as the man resumed pushing. Despite the pain, Dana resisted the urge to squeeze. She felt her sphincter yielding as the fat head pushed its way into her rectum.

"Unnnnnnnnngh! Oh god, that hurts!" Dana cried.

Dana felt as though she were being ripped in two. Her ass was on fire while a stabbing, nauseating sensation was shredding her bowels. She tried to breathe, but the pain was shutting down her bodily functions. Just as she was about to pass out, she felt a spike followed by a sudden lessening. The man stopped pushing.

"The worst is over," he said. "The head is in."

Dana felt like she had been penetrated by a jagged metal crown encrusted with jewels. Her ass was still burning, but the searing pain in her gut was gone. Her ability to breathe returned. She took several deep breaths and then braced for the next wave.

The man resumed pushing. His cock penetrated her ass inch by inch. When it was halfway in, he pulled back and poured more oil on his shaft. He set the oil down and pushed again.

A fresh wave of hurt washed over Dana, but it was less intense. As inch after inch of thick cock filled her ass, Dana became accustomed to it. After several minutes of slow penetration interrupted by brief withdrawals, Dana felt his balls slapping against her pussy lips. The man paused.

"Are you alright?"

"I'm ... coping," she answered.

The man started pumping in and out of her tight little butthole.

"Go slow," she pleaded

The man grabbed her hips and pushed, slowly at first. He thrust his cock in and out, pumping faster as every minute elapsed.

"Gentle. This is my first time."

Dana reached between her legs and flicked her clit. The fire in her ass never went away, but she thought if she could rub herself to an orgasm then that sensation might overwhelm the pain. In any event, the sooner the man came the sooner her ordeal would come to an end.

"Easy. Easy. Ahhh--not so hard."

The man thrust into her at a steady pace, his fat cock stretching her asshole over and over. Dana reached a point where the nausea went away and the burning became manageable. I think ... I think ... I can ... endure this ... if it doesn't get any ... worse.

"Like that," she urged. "Just like that."

The man was slamming into her butt with controlled but forceful thrusts. Dana felt like her asshole was shredded into confetti. Despite her best efforts, she was no closer to an orgasm than when she started. She doubted that she would ever be able to shit again. Her fingers stopped flicking her clit as she contemplated the rest of her life with a colostomy bag.

"Mmmmmm! Mmmmmmmm! Mmmmm! Ungh!" The man grunted. "Here ... cums! Ungh!"

Dana felt a different kind of warmth in her bowels. The man's pace slowed and his grip on her hips lessened. A second later his cock slid out of her ass, followed by a stream of semen.

Overwhelmed by all the Tequila, marijuana, sex and pain, Dana collapsed on the floor.

* * * *

Espinoza and Harris stood at the end of the dock taking turns looking through the binoculars. It was after 3:00 a.m. They had just exited their boat and were waiting for the Sea-Ray to arrive. Harris heard the distant engines before he saw the boat's lights. The two men retreated to the parking lot and waited for the passengers to disembark.

Nineteen girls got off the boat. Dana was not one of them.

The chef followed several minutes later. Harris and Espinoza were waiting for him at his truck.

"Where's Dana?" Harris shouted.

"I don't' know," Chef answered. "She didn't get off the boat."

"What the fuck do you mean she's still on the boat?"

"She went upstairs and never came back down."

"Chef, you're pissing me off." Espinoza pulled his gun and pressed it against Chef's forehead. "Tell me where the fuck she is."

"Look, all I know is that around 11:00 a drunk prostitute stumbled into the galley and told me she was replacing Lydia. I never saw your girl again."

"Did you look for her?"

"Hell no. They had armed guards at the stairs. I wasn't allowed to roam around that boat."

"Why did she have to go upstairs? She should have been able to plant the bug on the main level. What was Crespo doing upstairs?"

"Crespo wasn't there. It wasn't his boat."

"Whose boat was it?"

"Las Casas'."

"Las Casas? I thought Crespo was hosting the party."

"That's what Renee told me. I don't know when the plan changed."

"Get the fuck out of here, Chef. And don't say a word about this to anyone."

Chef got in his van and sped off.

"Well, what are you waiting for?" Harris said to Espinoza. "Call this in. We've got to get the Feds to go after them."

"We can't call anyone."

"What do you mean?"

"We don't have any support. This operation was never approved."

"What? You've got to be fucking kidding me. You said Hendricks approved it."

"I lied."

Harris slammed his fist into Espinoza's stomach. Espinoza doubled over, but Harris hit him in the face with an upper cut. Espinoza fell to the ground, unconscious.

"Dana!" Harris shouted into the early morning sky. "Dana!"

To be continued ...

* * * *

I want to thank my beta reader, Etaski, and my editor, Linda62953, for their assistance on this story.