by Orestes

Copyright© 2010 by Orestes

Sex Story: Tamara Ross is eager to make a difference. She begs her superiors at the FBI for an undercover assignment. The opportunity comes, but is she willing to go far enough to make the sting work?

Caution: This Sex Story contains strong sexual content, including Ma/Fa   BDSM   Humiliation   Oral Sex   Anal Sex   Bestiality   Exhibitionism   .

"I don't give a fuck who she's with, I'm checking her for a wire."

Tamara's head was clouded with the hazy euphoria of heroin, but even in this state, her body tensed at Tony's words. It was hard to know how to react. Nobody can teach you this sort of thing. If she complained too much, they'd think she was wearing a wire, no matter what they found. If she didn't protest at all, it would seem even more suspicious. She settled on a middle course.

"Hey, Rabbi, you gonna let this guy talk about me that way?"

The older man smiled.

"Take it easy, Tamara. He's just got to be careful, on account of all the shit that's going down. If Tony wants you searched, that's the way it's gotta be."

That was settled. If Rabbi said that they could search her, she'd have to live with it. She had to do what he said around here.

"So what do you want to see?" Tamara asked Tony.

One of his friends answered instead. " I'd settle for a good look at her tits, " the man said, leering openly. He was a middle-eastern man, probably Iranian. Rabbi nodded for Tamara to comply.

This was the scene that Tamara had been waiting for. If it meant that he had to show her tits to these guys, she was willing. It was the first time that Joe 'Rabbi' Rubini had let her stick around while the boys were over. The fact that Tony was suspicious of her wasn't unusual. His reputation pegged him as borderline neurotic about security. She was amazed that he wasn't demanding she leave.

"All right, " said Tamara, beginning to unbutton her blouse.

Tamara Ross couldn't help but mentally review the events that had brought her here. She had to remind herself why she was doing all of this.

"You can't get in ... going undercover into a criminal organization is a job for a man. " Tamara's supervisor had been adamant.

"Look, you said yourself, these guys are suspicious of any new guys.

They've all watched 'Donnie Brasco' enough times to be paranoid about any wise-guys they don't know. I think we should come at it from a whole new angle."

"These guys have no respect for women, " Cecil argued. " It's a man's business. They would never allow you to participate in anything. I'd be surprised if they let you hang around while they discuss anything important. Besides, how the hell would you get in?"

That was her opening. She had this planned out.

"I happened to go to school with Josh Rubini. We even dated for a while, so I got to know the family."

Josh had been killed in the crossfire of a recent mafia slaying. Tamara could see the wheels spinning in Cecil's head. Perfect.

"It wouldn't be out of place for me to show up at the funeral. His father, Joe the Rabbi, still does some of the books for the family. If I can get in with him, I'm sure I can get some important information."

Cecil was still shaking his head.

"And how are you going to get close to this guy?"

"Maybe I can be of some comfort to the old man, if you catch my meaning. Don't worry, intelligence says that the old guy is impotent. He just likes to have women around to keep up appearances."

"I'm still not sold on the idea."

Tamara wanted this badly. This is the kind of assignment she had been itching for ever since she trained as an agent. Instead, she'd been stuck will low-level crap. Window dressing, really. She would say anything to get a decent assignment.

"Look, Cecil, I'll be careful. I'll check in every week. First sign of trouble, and I'm out of there."

Of course, they both knew that her assurances were false. Every successful undercover agent had given her the same story. The supervisors want to hear you say that you'll be careful to cover their own asses, but once you're in, it's the results they're after. After you're undercover, it's a whole new game.

You'd say anything and do anything to stay under. The stories she'd heard were both exciting and horrific. For most of the agents, it meant participating in the criminal activities of the organization they were trying to infiltrate. Violence, drugs, weapons ... whatever. For her, well, she didn't know. Whatever it took to stay under. That was the name of the game.

So this is where she found herself, a month later. Pretending to be some drugged up whore, and pulling off her blouse for Tony and his Iranian friends. Rabbi often had her undress for him privately. He might be impotent, but he still seemed to enjoy Tamara's naked body. For that reason, she'd given up early on trying to wear a recording device. Of course, she would never put anything about it in her reports to Cecil. That would only open her up for ridicule by the guys at the bureau.

Another thing that didn't go into the reports was the drug use. Early on, Joe and his immediate family seemed suspicious of Tamara's motives. Why would a pretty young girl want to stay in a relationship with an impotent old man? It was becoming a problem. After she began to accept his gifts of drugs and money, everyone seemed much more comfortable about her motives.

Actually, it made a pretty good cover. When Rabbi thought that Tamara was doped up, he was a lot less cautious about what he said in front of her. She could listen in on his end of phone conversations, and pick out anything useful. Usually, she could dispose of the drugs in private, but every once in a while, Joe insisted that she shoot up in front of him.

That's the way it had been just before Tony and his friends arrived.

"Hey, your girl has a nice set, Rabbi, " Tony said, admiring her now exposed breasts.

Tamara blushed. It was one thing to be naked in front of the old guy, but it was humiliating for the agent to strip off her clothes in front of the other three men. She was actually thankful for the way that the heroin was numbing her anxiety. She always kept herself in shape for the physical elements of the job, and she could see that the men were enjoying looking at her tight body.

"Let's see the rest of her, " the second Iranian man suggested.

Rabbi nodded again. He was enjoying the show as much as the others.

Tamara unhooked her belt, and allowed her pants to glide down her legs to the floor. One of the Iranians whistled as her shapely legs were revealed. With the pants around her ankles, she was left wearing only her panties. She hoped that it was enough to convince them.

"I don't know, Rabbi, " declared Tony to the elder man. The big Italian was making a game of this now, seeing how far Rabbi would let him go. "I've seen cops hide wires in the smallest of places. Maybe we should see under those panties."

Tamara looked to Joe Rubini, but he wasn't giving any sympathy to his girl. Without further delay, she pulled her panties down to her knees.

"Turn around, " ordered Tony.

"Bend forward, " added Reza.

If the guys at the bureau could see her now, she'd never hear the end of it. She bent forward to give the mobsters a view of her ass. She tried to hold back the tears of shame. She'd have to be tougher than that if she wanted to stay undercover. A lot tougher.

"Bring your hands back, and spread your cheeks for us. Open up your legs a bit. Give us a real good view."

She followed his commands. Slowly, Tamara pulled her ass cheeks apart to give Tony and the boys a good view of her tight hole. Bent forward like this, now with her ankles apart, she was sure they had an unobstructed view of her pussy too. She had heard stories from other agents about when they were forced to strip, but she knew it was nothing like this. She could feel the men's eyes roaming all over her lewdly exposed body.

As shameful as the position was, and as much as the whistles and lewd comments about her body hurt her pride, she had to stay in character. As far as Tony and the other guys were concerned, she was just some stupid slut, who would do most anything to keep herself supplied with drugs. She had to keep that illusion intact.

"You've done good for yourself Rabbi," Tony declared. "I ain't seen an ass as sweet as that since high school."

Rabbi seemed pleased that the younger mobster was admiring his woman. Despite his years of service, he was quickly falling behind the younger man in status. Tamara's heart began to pound uncontrollably as she listened to the men talk further.

"What's mine is yours Tony. Any time you're visiting, Tamara will be available as part of my hospitality to you."

"Are you sure?"

"I'm an old man, Tony. I can't do the things that a pretty young woman like Tamara should have done to her. I'm sure she'll be happy to do whatever you want, as long as you give her a little treat afterwards."

Tamara couldn't believe what she was hearing. Not only was she showing these creeps her body, but now Rabbi was giving Tony permission to use her in exchange for drugs. The idea revolted her, but she couldn't think of a reason to protest the arrangement. After all, that was the premise of her relationship with Rabbi in the first place. To protest it now would draw suspicion.

"You're a kind man, Rabbi. Maybe she could give me a blow job while we talk about business."


Tony and his two Iranian friends took seat at the table. Tamara had no idea what to do next. She wasn't sure they would let her walk away now, even if she wanted to. Besides, that would end the whole assignment. A month of letting Joe the Rabbi paw her naked body would be for nothing.

Do anything to stay under cover, she reminded herself. Reluctantly, she dropped to her knees, and crawled under the table.

Okay, I can do this, she told herself silently. At least he doesn't want to fuck me. Yet.

Tony unbuckled his belt, and dropped his pants. His big Italian cock was already hard. He was seated across from Rabbi, with the two Iranians on the other sides of the small table. She crawled up between his legs and began to tentatively lick the underside of his prick.

"Oh, she has a frisky little tongue, " he told his friends.

Like the character that Tamara was playing, she felt like a complete slut. She had only just met Tony in the last fifteen minutes, and she was already under the table, flicking her tongue up and down his hard shaft.

A strange sense of arousal was buzzing through her body. She tried to convince herself that it was just the role that she was playing, or the effects of the injected drugs. Yeah, the drugs. That must be it.

"Your cock is making her wet, " said Rabbi. " I told you that she wouldn't mind."

The old man had his hand under the table, and was fingering Tamara's exposed pussy from behind. She tried to fight the sensations, but Rabbi was skilled with his fingers, and was playing her perfectly.

Better get this over with, she told herself. With an aptitude that surprised even her, she wrapped her mouth around the big tool. When it reached the back of her mouth, she took a deep breath, and then allowed his flesh to penetrate her throat.

"Oh, she's good. I don't think I've ever had a girl take me that deep."

Great, Tamara mused to herself. There's a skill that she could brag about to the other agents. She could see the scene in her head ... a group of FBI agents bragging about their mastery of mafia etiquette, or marksmanship, or perhaps their ability to speak Italian. What would she have to say? ' Well, Tony Carusso thinks I'm a great cock-sucker. '

Tamara breathed rapidly through her nose. Rabbi's fingers explored her wet pussy from behind, and to her ultimate shame, her body was betraying her. She couldn't control the sensations of pleasure building within her. She could only hope to bring Tony off before ... before ... no, she didn't even want to think about it.

"That's right, bitch. Keep those lips tight for me. " Tony was really getting into it. One of his big hands came down and grabbed a handful of her dark hair.

It was a race now. She desperately wanted to get the big Italian off before her own body came too close to climax. She tried to clear her head of all thoughts, and concentrate on his cock. She tried not to think about the fact that she was naked beneath the table, with her panties around her ankles. She tried not to think about the two Iranian men, who had pushed their chairs back, and were watching her suck cock. She tried not to think about the humiliation.

Especially not the humiliation of being fingered from behind by the impotent old Rabbi, and the way she was pushing her ass back lewdly to greet his fingers now. Where was her pride?

Tony's cock was throbbing in her throat. She could still bring him off before her body did the unthinkable. She could feel her breasts jerking and swinging beneath her as she bounced her head up and down with desperation.

"Mmmm ... mmm " she groaned around his base of his prick, trying to coax him to orgasm.

"Oh, man, she's begging for it..."

Tony was so damned close. The big head of his cock was swelling in her throat. Her jaws ached from the effort. Just a little more, she told herself. He can't hold on long.

Just then, her orgasm ambushed her. It came on so quickly, and so violently, that she completely released Tony's cock from her mouth with a loud slurp.

"Oh my god ... oh my god ... oh my god..." she squealed over and over as the climax overtook her body and senses. Her hand was still firmly planted around the base of Tony's cock, and as an afterthought, she continued to jerk his saliva covered prick.

He rewarded her with a warm stream of cum across her cheek. He was cumming on her face, and enjoying it thoroughly.

"Oh, yeah. Let me cum on your face, bitch. That's a good little slut. Take it all."

His indecent words only heightened her continuing orgasm. Her whole body shook uncontrollably as she buried her face in the lap of the big Italian, and let him spill his cum across her lips, nose and chin.

By the time Joe stopped fingering her pussy, one side of Tamara's face was completely covered in Tony's thick sperm. Fighting back revulsion again, she forced herself to lick the remaining cum from the tip and shaft of the mobster's cock. While she continued to clean Tony's cock, the conversation above the table turned to business. Tamara strained to hear every word.

When all was said and done, Tamara was actually able to collect some good information for her report. Cecil was overjoyed. She had some collected some contact names, and some dates of Iranian drug shipments. It wasn't anything earth shattering, but it was enough for Cecil to enthusiastically recommend that Tamara stay undercover.

"That is, if you're still sure you can handle this, " he gave her an escape hatch.

"I can handle it. " said Tamara, with more confidence than she felt. " Don't worry about me, sir."

She went away from her meeting with Cecil with mixed feelings. Yes, she wanted to stay undercover. This was an important investigation, and it would be a real feather in her cap if she could help to bring down the Lombardi crime family. This was her first step in earning herself a place amongst the most respected undercover agents in the bureau.

On the other hand, she dreaded going back to Joe Rubini. How many sex acts would she have to perform to maintain her cover? How far would Joe let it go? She wasn't eager to find out the answers to these questions.

The internal argument raged while she drove towards Rabbi's urban home, above a kosher bakery. No, she didn't want to submit to the advances of his friends. But she couldn't help but think about how sweet it would be to put these guys behind bars. Especially that pig Tony Carusso. Once they were in prison, her time with Joe Rubini would be a distant memory. It would all be worth it in the end.

She hoped.

The smoke was so thick in Rabbi's apartment that the mobsters didn't even bother to draw the shades. A couple of the early arrivals for this evening's meeting had come directly from an afternoon baseball game, and were well on their way to drunkenness. They settled in, lighted up some cigars, and ordered some Chinese food.

Throughout the early evening, the room filled, until there were more than a dozen men in the upstairs apartment. No sign of Tony Carusso. That was a relief to Tamara. She didn't want to do a repeat performance for the big Italian. So far, the other guys had left her alone. Sure, there was the odd slap on her butt, or lewd comment, but it was nothing that compared to the previous meeting. Mostly, Tamara was expected to fetch drinks for the guys, and act perky. Rabbi seemed pleased by her manner with his guests.

She could definitely handle this. She was even getting some decent information from the bits and pieces of conversations she could listen in on while passing.

One the whole, the evening was progressing quite well for Tamara. Until Tony arrived.

"Hey Tony ... ya beautiful son of a bitch ... how's it going?" One of the men announced Tony's arrival as he walked through the door. Tamara's heart sank at the mention of his name. One by one, each of the mobsters rose to greet the rising young star of the Lombardi crime family.

At first, Tamara thought that she might be able to avoid him, while he socialized with his associates, but as soon as he saw her, he waved her over with a gesture of his hand.

"Tamara, come over here. I brought a little something for you."

Hesitantly, she approached him.

"This stuff is going to knock your socks off, " he said, pressing a small package of heroin into her hand.

"Mmm ... thanks Tony. I'll bet it's delicious, " Tamara responded, and gave him a kiss on the cheek. " I'll save it for later."

"No. I want to see your face when you shoot this stuff. It's dynamite."

God, he was putting her on the spot in front of all of these guys. There was no way she wanted to shoot up now. It wasn't only the drugs that she wanted to avoid. She knew what the exchange was. Drugs for sex. He couldn't expect her to have sex with him right now, could he?

"Maybe we could find someplace more private..."

"No. I'm sure my friends won't mind."

She had no more excuses. With only minor hesitation, she rolled up her sleeve and prepared to shoot the drugs into her bloodstream.

"Ohhh ... fuck..." she said, as she felt the heroin begin to tease her brain. Tony wasn't kidding, this stuff was really potent. It hit her fast, and her head spun with chemical pleasure.

Now for the other part of the exchange. Tony pulled her with him to the sofa. He sat back, and began to unbuckle his belt. He was definitely showing off for the guys now.

"How about hopping on for a ride?"

' I don't know what I'm going to do, ' Tamara wrote in her private journal. The reports that she prepared for Cecil were so full of lies that it felt strange to put her actual thoughts to paper. ' I know I'm losing my objectivity. Sometimes you'll see a gambler who just can't walk away from a game. He's lost so much, that he feels like he just has to win sometime. He knows he should walk away, but he just can't -- I feel like that gambler right now. '

' Every time I think about the things I've done to maintain my cover, I feel sick to my stomach. I think about the first time I straddled Tony Carusso's lap, in front of all those guys, and worked his cock into myself. I remember how my head was spinning from the drugs. God, I'm so ashamed of the way I bounced up and down in his lap, with all the guys watching. The way I faked pleasure while he sat underneath me, and reached his big hands up my blouse. '

' So I should walk away, right? That's what I'd tell the gambler, before he placed that final bet. I should walk away before I lose myself. Several times a week, Rabbi brings over his friends. Each time, I give a little bit more of my pride away. Each time, my body craves the heroin just a little bit more. How long before I can't turn back? Before I become an addict? '

' I talked to Nick Anderson at the bureau the other day. He's one of the best there is. I had to ask him a question:

"When do you know if you're in too deep? When to bail out?"

"You don't, " he confided in me, in a quiet corner of the cafeteria.

"Jesus, Tamara, don't breath a word of this to anyone ... but I once killed a man while undercover. I was just playing my character, and sometimes it's hard to draw the line. If I hadn't have killed him, one of the other guys would've. But it got me in deeper. Deep enough, eventually, that I was able to bring a lot of guys down. But that's the thing, Tam. When you're in, you've got to do what it takes. Whatever it takes."

' It was like he was reading my mind. The only thing I think about when I close my eyes at night is bringing these guys down. That will be my redemption. My salvation. If I walk away now, I don't know how I'll live with myself ... with the things I've had to do for these pigs. If I walk away, the bitter taste of Tony Carusso will be on my lips forever. '

' So I stay there. Playing the part of a drugged up whore. Sucking ... fucking ... shooting up. But I listen. Even when they think I'm too fucked up to remember what they say. I listen for names, and dates, and locations. For dollar amounts and drug shipments. I can't wait for the day that I can put Tony and his boys in prison. That will make it all worthwhile. '

' It's ironic. As much as I detest Tony, he's my best link to the more powerful members of the family. He invited me to a meeting with his boss tonight. Rabbi warned me against it. "You don't know how insane these guys are, " he told me. " Stay here, and I'll take good care of you." Is he afraid to lose me to Tony? '

' How could I possibly stay with him? This life is killing me. Each day, I crave the drugs more. The longer I stay with Rabbi, the worse it will get. I need this chance. I need an opportunity to end this thing. It's so close I can taste it. '

' Whatever the outcome ... I think that this is my final bet. I'll walk away from the table after this. '

Tamara could feel her excitement growing. Tony's driver was bringing them to the house of a prominent member of the Lombardi crime family. Even Tony seemed nervous about the meeting. Tamara knew why he was bringing her with him. She was like an offering to a more powerful member of the family. If he was pleased by her, it would improve Tony's status in the organization.

He rested his hand between her legs, and felt up and down her inner thigh absently. She was accustomed to his wandering hands. He liked to have her sit on his lap over at Rabbi's place. Like a pet, that he stroked and fondled while he spoke. At these times, she almost welcomed his gentle touch.

"You're sure you wanna go through with this?" He asked her.

How touching. It was the first time Tony had shown any concern at all for her. Something in his tone even made her consider her decision for a moment.

"Yeah. No problem. As long as there's plenty of the sweet stuff, I'm game."

She knew what card to play with these guys. As long as Tony only saw her as a junkie, her cover was safe.

The car stopped at their destination, a large house nestled amongst ancient conifers. The leaves were turning, and glowed yellow and red in the evening sun.

Inside, security was tight. Despite Tony's increasing power within the family, the guards searched him for weapons. Tamara was searched too, but only briefly. With the tight clothing that she was wearing, it would have been difficult to conceal a weapon.

In the living room, six men were already seated. One of them rose to meet Tony at the door. The other men listened quietly.

"I'm glad you could make it, Tony. I'll introduce you to everyone in a minute."

He gave an appraising glance to Tamara.

"You brought a girl?"

Tony seemed much less assertive in the presence of this man.

"Uh, yeah, Len. I heard that Paul likes a girl who's willing to please. She's definitely willing."

"Is she okay?"

"Oh yeah, me and the boys have been partying with her for a couple of weeks at Rabbi's place. She's an old family friend of his. Don't worry, she's so wasted most of the time, she don't know if she's coming or going. But the things she'll do for a couple of points, well, it definitely makes her worth having around."

"A pretty little thing too. I'll bet that Paully is gonna like her a lot."

Tamara had heard of Paul Lombardi. He was very near the top of the family. She felt a chill go through her body. For the first time since going undercover, she considered what would happen if she was discovered as an agent. This was a guy who routinely ordered people killed. Somehow, that made the whole thing more real.

Len brought Tony around the room and introduced him to the other guests. The names were all familiar to Tamara from her briefings at the bureau office: Simon the Angel. Fuzz Malone. Tido Barone. The list read as a virtual who's who of the Lombardi family.

Tony seemed as nervous as she was. By the time Paul Lombardi finally came into the room, Tamara's mouth was dry, and she was itching for something to take the edge off. That part of her cover was becoming less of an act each day. She craved the sweet kiss of heroin to calm her growing anxiety. It was going to be hell beating the habit when she finally pulled out.

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