Michael Undercover

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I managed to overhear something about a big operation that was going down in a couple of days. I tipped off my boss, and since that was something that I presumably didn't know, it was safer to bust that op. My boss said he thought he was getting closer to the mole from his end and would let me know something in a few days.

The op got busted up by my true organization, but I got no response to any of my messages to my boss. I found myself back at Sokolov's place, and after some perfunctory fucking, we got dressed and several of his men showed up. One of them was real nervous and it was the guy I overheard.

"I know there has been a leak around here, so I've been testing all of you. You've each been told about something that none of the others knew. Only one of those things got to the feds."

"Boris, I swear to God. I didn't tell anyone. I don't know how they found out. It had to be someone else."

"Mikhail, you were the only one I told. Anyone else who knew had to find out from you."

Mikhail got down on his knees, begging for his life and swearing he had nothing to do with the tip. Pavel and Nikolai dragged Mikhail from the room.

"Make sure he can't ever be found, and there's no tie back to us."

"Michelle, I know you loved Riley. Are you sure you don't want to go be with her?"

"Do you want me to go? Do you think I should go?"

"That's your choice. You're a good soldier. I'd hate to lose you, but it is family."

About that time, the door opened and James, who had been number two at the investigative unit walked in. He kind of sneered at me, then turned to Sokolov.

"I couldn't stop Smith from breaking up that operation, but he had an unfortunate accident during it and was killed. These things happen, you know. Died in the line of duty and all. Now I'm the director, so we can make sure there are no more problems."

"And all his records and files on me?"

"Anything of substance was wiped out. He had collected a lot of data on your organization. It wasn't just one operation, he had found out more than I even knew about your business and people. There may have been a bigger leak than just Mikhail."

"Any idea who and how?"

"We had one operative, Michael Thomas, Russian mother, fluent Russian speaker and an experienced undercover agent. I am still working out how he could have gotten access, but he has been out on assignment for a few months. It has to be him."

"We have to neutralize him."

"His only connection back was to Smith, and he's dead. Thomas can collect whatever he wants. I'm in charge now and nothing will come of it, but I'll do what I can to neutralize him anyhow."

"Good. Now we can act with a lot more freedom."

"I can give your little girlfriend a ride since I'm leaving anyhow."

"Thanks... but I can find a way home."

"Not a problem to take you, besides I like to get familiar with folks moving up in Boris's operation."

"Go ahead. He's on our side, even if he is a fed."

I didn't want to spend any time with James. He already figured out that Michael had infiltrated the organization. I didn't want him to tie Michelle to Michael. Sokolov patted me on the ass, and I reluctantly left with James. He had a car downstairs and he opened the car door for me.

"You can just drop me at..."

"I know where you live. I can take you all the way there."

We got there and he insisted on walking me up to my flat. I told him I was perfectly safe, but didn't want to make too big a deal of it. I opened my door and he said we needed to talk and insisted on coming in. As we walked in, I could see that someone had been there. It was a professional, they searched the place leaving things almost perfect, but folks like me leave little signs that tell us.

"Well, Michelle, or should I call you Michael?"

"What do you mean?"

"One of the things I found when I took over the department was a secret medical research operation and drugs that could change a person's sex, without any operations. Then I figured out that Michael had to have become a woman, otherwise we'd have found him out by now."

"That's absurd."

"About the time Michael went undercover, Michelle joined Sokolov's organization. Both about the same age and similar coloring. And Michelle has fearsome fighting skill - just like Michael. Too many coincidences - beyond which Michael's double maternal great grandfather was named Popov. You were damned slick, and seducing Boris's niece to get an entry was clever as hell."

"I didn't know she was his niece, and she seduced me."

"Well then lucky, I guess. As you can tell, I searched the place. You've kept it squeaky clean, except for one little bottle that held one pill that could change Michelle back to Michael. Don't bother looking - it's not there any longer."

"Why didn't you just rat me out to Sokolov?"

"Because you can be more useful to me staying in his operation. And I suspect you still want to change back to Michael, and you can only do that if I provide the means. And I'll only do that as long as you're useful to me in various ways."

"So you want me to pass information back to you?"

"Among other things."

"What else?"

"You've been fucking Sokolov, you can fuck me too. You make a nice looking woman, and I want to make use of that."

"Are you serious?"

"In your bedroom, and take off your clothes."

"Don't do this."

"Would you rather I tell Boris that you are the stooge? Would you rather spend the rest of your life running from his men than fucking me occasionally?"

"I'd rather not do either."

"In the bedroom and naked, now."

I needed to buy time to find some alternatives, but that wasn't going to happen tonight. Yes, I could try to kill him. I might succeed, or he might kill me. Either way, Sokolov knew James was giving me a lift. If he turned up dead the evening he gave me a lift, he'll figure I had something to do with it.

I turned and walked toward the bedroom. James followed me in and closed the door, not that privacy exactly mattered. I took off my top and my slacks, and he gestured for me to keep going. I took off my bra and looked at him, and he just stared back at me. I slid my panties down and stepped out of them and kicked off my shoes. He gestured toward the bed and I lay down there, and glanced to the side, where I could see that indeed he'd moved the lamp where I'd hidden the pill.

James took off his clothes and climbed on the bed. I could feel as his prick rubbed against my pussy lips. I knew he was teasing me - not teasing because I wanted it, but because I didn't and he was going to show his control over things. He rubbed the tip of his dick up and down my slit a few times before easing the head about an inch inside me.

"I'm not going to ask you to beg for it. We both know you'd be lying. We both know you'd rather cut it off than have me stick it in you."

With that, he slowly slid he dick in until he was all the way in, balls deep. I was used to having Sokolov fuck me, so it wasn't anything shocking or unusual. It was just that James was such a sleezeball, and essentially he was forcing me to fuck him. I just thought of it as whoring myself out for my own survival.

He wasn't as big as Sokolov, not that it mattered. But he decided to fuck me slowly, to draw it out. It wasn't to lengthen my pleasure, he figured I was miserable, and he wanted the misery to last as long as he could. He slowly pounded away at my pussy, looking me straight in the eyes the whole time. I looked right back at him. I had nothing to be embarrassed about.

He kept at it until he began to speed up and stiffen his body, then he stuck it as deep into me as he could get and moaned as he came deep in my cunt. He was sort of out of it for a few seconds, then regained his composure, looked me in the eye again, with his dick slowly starting to soften inside me.

"So how was it? How did you like having me fuck you?"

"You're just another dick - nothing more."

He looked mad as hell, and oddly I could feel him getting harder again. He got off me though and told me to get on my hands and knees, which I did. He got behind me and stuck his prick in my ass. It was not as hard as it had been, but still hard enough to give it a go. He was still wet from being in my pussy, so it was not too uncomfortable.

"You probably don't care much about your cunt. It doesn't even seem real, but your ass - now fucking a guy in the ass, that is real."

"I'm not a guy now though, but thanks for your consideration."

He started slamming his dick as hard into my ass as he could. He wanted some pain, but mostly humiliation. So far I wasn't giving him much satisfaction, apart from orgasms. He pulled my hips tight and shot a load deep in my ass. As the throbbing in his dick eased, he pulled out of me and let go. I moved forward and half rolled onto my side.

"I'd tell you to clean it off, but you'd probably try to bite it off."

I just smiled at him, as he got off the bed and started putting his clothes on. I sat up on the bed, still naked, not bothering to try to hide anything from him. If he wants me to be his whore, that's exactly what I'll be - no feeling - not pleasure, pain, pride, or shame. I'll do this until I can find a way to end it and end him.

"You'll see me again - before too long."

With that, he turned and walked out. I went to the front door after he exited and made sure it was as locked as I could get it. I went back in the bedroom and checked and sure enough the bottle and pill were gone from the base of the lamp. He didn't even bother to try to glue the paper base back. Just made it clearer.

* * * * * * * * * * * * * * * * * *

I continued working for Sokolov. I was no longer interested in taking him down. I wanted to take James down or better yet take him out. My other challenge was finding more of the drug that could change me back to a man. I know there was a research program. I had to figure out which one and who to contact to try to get what I needed.

I managed to get in my former unit's computer system. James had shut down my regular password, but I had long ago set up a backdoor, with my old boss's help. It took some digging but I identified the research unit that produced the drug that changed me. I also identified three of the senior people there. Two of them were married, but the third was divorced.

Bob, the divorced guy hung out at a couple of different clubs, but seemed to strike out a lot with women. That gave me a chance to use my female assets to get his cooperation. James in the meantime kept visiting and fucking me. Once he realized he could not humiliate me through sex, he simply used me as a way to get off. Sokolov still had me come to his place for sex once every week or two. For him, I was becoming more of an asset in his organization than just a sex toy.

I had to tread carefully, but there were a couple of other Russian mobs in town. James had come down harder on them, while letting Sokolov slide, which allowed Boris to expand his territory. I knew that the other mobs were resentful, but they weren't going to strike directly at the man. There were a few border areas where the mobs had a no-man's-land, and Sokolov had me occasionally be an emissary to the others. I let it slip that the reason the feds were targeting them was James, and also let it slip where he could be found.

James had a girlfriend, in addition to his wife, and besides fucking me. James emerges from a building and walks toward his car. Two men come out of the shadows with guns, and approach him. One man waves his gun at James. James looks like he is reaching for his wallet, but pulls out a gun. One robber shoots James, only wounding him. James shoots and kills the robber. The other robber, manages to disarm James, who stands there defiant. From the shadows, I emerge. James sees me and sneers.

"I should have known you'd be behind this, Thomas."

"Michelle Thomas is dead. You killed her. I'm Michelle Popov."

"So you're throwing in your lot with murderers and thieves."

"The mob has killers and thieves, but at least they don't hide behind a mask of morality."

I picked up James's gun and pointed it at him. I am wearing gloves.

"They don't shoot down an unarmed man in the street and call it justified. They don't let a child dies for lack of food, a veteran die for lack of shelter, a mother die for lack of medical care, and say it's because they were lazy takers."

"You've bought into all kinds of bullshit."

"No, I took off my blinders and I'm looking at the world as it is, and it's run by too many crooked politicians and crooked businessmen."

I got closer to James who backed up slightly and looked around. I pointed the gun straight at James chest.

"You won't get away with this."

"If you die in a robbery gone bad, what's to tie me to it?"

James began to look scared and slowly backed down an alleyway away from me, and I followed him.

"Can't we find some other way out?"

"No. I can't trust you, and you made this inevitable. If you'd just let me leave town and be with Riley, you and Boris could have gone on for some time."

James dove to one side and pulled out a gun from another holster, and aimed it at me. He shot and hit me in the chest, but I was wearing a Kevlar vest. When James fired, the other mobster with me also fired killing James immediately.

I found out that James had spread word at my old unit that I'd gone undercover and then switched sides. That was kind of true, but I only switched sides because James took away my alternatives. I was quickly becoming one of Sokolov's best mid-level people and was making a lot of money doing it. I didn't care about the money and stashed most of it, managing to become pretty rich doing so. In truth, I realized that Sokolov was not much worse than some of the dirty, double-dealing politicians and businessmen we had around the town. Boris was at least sharing the wealth with the people making him wealthy.

The situation with the mobs stabilized. Boris gave up a little of the territory he'd gained, but also kept some of it and they had a détente between them. Every now and then Riley and I would manage to get together, either her visiting me, or me visiting her. I still missed her, even more badly since I was free from my old job of trying to take down her uncle.

It took me several weeks to get where I could approach the researcher named Bob. He was a pretty easy mark, being divorced and not having much luck with women. I started slow to gain his trust, first just talking to him a few times at one club, then having a drink or two together, and then having dinner with him. His ex-wife was getting a lot of his pay as alimony, so I ended up springing for dinner, and I pumped him for information about his work.

He was something of a braggart, and to hear him talk, most of the advances at that lab were due to his work. I figured that was bullshit, but I didn't so much need his brain as his ability to get some of that drug. With enough booze in him, he talked about the drug, but said they'd been told by James to destroy all stocks of it. Even in death James was trying to play a step ahead of me. He said that it was possible some of the drug had escaped that destruction.

"You know, Bob, I have some lesbian and transgender friends who would love to get their hands on those drugs. Most of them are desperate to change genders, and if this drug could do it, they'd want it."

"I think I can get my hands on some. Which type do you want?"

"How about a few of each type?"

"That's tough, and if I get caught taking it I'll be fired and lose not just my job but my entire career."

"If I offered ten thousand dollars a dose, what could you get?"

"Cash? No way to track it back?"

"You've got it."

"I'd need at least twenty thousand per dose."

"That's tough. Most of them don't have that kind of money."

"That's it - take it or leave it, and I need some non-monetary compensation too."

"What kind of compensation?"

"I'm divorced and horny. I want sex."

"I suppose I can find you someone."

"I'm not dealing with some vague someone - I'm dealing with you - and I want you in my bed."

God, like I really needed one more horny man who wanted to fuck me. But it probably was no surprise he wanted more than just cash. At this point, wasn't it worth fucking another guy if it would get me what I wanted?

"How long would it take to get the drugs?"

"Maybe a week or two, but if I'm going to do this for you, I want you to come to my place tonight."

This shit is getting old. Does everything I need have to be bought with my pussy? But I went back to his place. I suppose the nice thing was he could only really get it up once. After he was done, I told him I had to work tomorrow and had to get home. I told him that I'd get him twenty thousand in advance for the first dose of the blue version.

Two days later, he said he hadn't managed to get any of the blue version yet, but he still gladly took the money and insisted I fuck him again. I did, but told him I wanted results if I was giving him money and sex. He said to check back with him in a couple more days and that he thought he could have extra, so he wanted more money then too. Another forty thousand. I was getting suspicious as hell.

A few days later, I had the forty thousand, and he said he'd found some of the drug but with the security they had at the lab he was having trouble getting it out. Of course he got sex and money before he told me that.

"Look. I want results. You're now cut off until I get some results."

"I'll get it, but I need another three days. Come back then with sixty thousand more and I'll have three of each type of drug."

"You sure as shit better."

Three days later I showed up at his place with sixty thousand dollars. He let me in and then pulled a gun on me.

"Look bitch. I want the money and I want your cunt. Hand over the money and strip."

He was a medical researcher, not a trained fighter. I had the gun out of his hand in about two seconds. I held the gun to the bottom of his jaw, so a bullet would go right up through his brain, assuming there was one in there.

"You rotten son of a bitch. You never intended to get me the drug. You were just going to fuck me and take my money and give me nothing. I should just kill you right now."

"I... I can't get the drug. But there's another man who can. I'll introduce you. He'll get you what you want."

"Why should I trust you after you've fucked me over?"

"I'm telling the truth. Please don't kill me."

"Call him. Tell him what we need. Have him bring it here."

"Why do you even care about this?"

"I'll tell you later. Just get him here."

Bob called the other guy, who was still at the lab, and said he could get the drug. Bob told him that it was critical, but that he could get sixty thousand for three of each pill. We sat and waited for an hour until there was a knock at the door. I opened it to find another middle aged male researcher standing there. He came in and saw Bob who was still pale from fear.

"This woman wants those pills. I've gotten money and sex from her, but couldn't get her the stuff."

"I was told there would be sixty thousand for me if I got it."

"Here's sixty thousand, you count it while I check the pills."

I handed him the cash and he handed me the pill bottle. I opened it and looked at the pills, which looked like what I'd taken before but I no longer trusted anyone. I walked over to Bob who sat nervously in his chair.

"Well if he got sex, I think I should too." The other man said.

At that, I did one strong hit to the head and knocked Bob's out. The new man's eyes about bugged out of his head.

"This man cheated me, that's what he gets for it. Tell you what, you'll get sex, if you don't double cross me."

"I... wouldn't do that."