Michael Undercover

Copyright 2017

NOTE - Since this story involves mob activities, there is violence and killing. If that bothers you, please do not read this story.

*****

I am or at least was a federal law enforcement officer. I was a damned good one too, if I must say so. I am Michael Thomas, the son of a French father and a Russian mother, but born in the USA. I grew up speaking English, French, Russian, German, and Italian, and learned how to speak them all with a native accent. That let me pass in a lot of different circles and allowed me to work undercover with all sorts of often unsavory people.

I became part of an elite unit focusing on various organized crime syndicates. I spent so much time undercover, at times I almost forgot who and what I was. That's easy to do. You have to live the life - you can't just pretend. As I said I was good - one of the best, but at times had to take a break from the undercover work, because I got too well known in the underground. That can be dangerous and even cost you your life.

One day, I got a text from the head of my unit, asking me to meet him at an address I didn't recognize. I know all our safe houses and secure meeting sites, and this was different.

"Michael, we need to crack Boris Sokolov's Russian mob."

"Boss, I've tried several times. That is one tight group. Even with my language skills I can't get anywhere near Sokolov. I almost got killed the last time I tried."

"I know. I think somehow they've managed to get a mole in our unit. They seem to know all our operatives. At best we get told to beat it, and a couple of our folks have disappeared."

"Including Dmitri, and his Russian was as good as mine - maybe better."

"He could do a couple of regional accents that you can't, but you're both damned good - or he was until he disappeared."

"Do you have any idea who the mole is?"

"There's four that I'm real suspicious of, and another four I'm not sure of. Hell, the only one I'm completely sure of is myself."

"I know that I'm not."

"But the mole would say that too. Michael, you I'm about 90% sure of, which is a hell of a lot better than most. And you have the Russian language skills necessary for what we need."

"How in hell do I get close to Sokolov and his crew when they know who I am and what I look like?"

"Obviously we would need to make you look very different from what you do now."

"Are you talking plastic surgery? That takes a while to heal from and leaves scars, besides it can only make just so much of a change."

"The only way we could really do it is with you as a woman."

"Are you shitting me? Even if I dress in drag, they'll sniff me out in two minutes flat."

"Not a man in drag, but a woman."

"You aren't doing a sex change on me. Besides that takes a lot of time to heal and leaves even more scars, and would not change me enough to fool them."

"There's an experimental medical research unit that we have ties to. They have a drug that can change a man to a woman, and changes enough other features to completely disguise you, including altering your voice."

"Look boss, I love my job, and I want to break open Sokolov's mob, but I don't want to spend the rest of my life as a woman to do that."

"Michael, they have another drug that can reverse that effect - change a woman into a man."

"Shit, boss. I don't know. If anything goes wrong..."

"Michael, you are the only person who can both do this, and who I can trust to do this. We will do our damnedest to make sure nothing goes wrong."

"Hell, even if nothing goes wrong, I know Sokolov and his crew. They use women like we use toilet paper."

"And there's a good chance he or one of his crew would use you that way before you could get close enough to learn anything."

"Fuck, boss. I don't know. I'm a guy. I like women. Do I really want to be Sokolov's sex toy?"

"You know it was Sokolov's mob that killed your brother."

"Yes, but..."

"Do you want to let him get away with that?"

He was right. I knew Sokolov's crew had killed my brother Joseph. I've been itching for a way - any way to pay him back for that. Could I do this way though?

"Question is, how far I'm willing to go to get even. I don't know if I can go that far."

"I won't order you to do that."

"I could always just quit if you did."

My boss sat back, and smiled. Then he put his hands behind his head.

"I need you to do this, but it has to be a 100% commitment on your part - heart, soul, and body."

"This is asking a hell of a lot."

"I've set up a false identity, with full background. No one has seen it but me. I have set something to replace your fingerprint files with some that will leave you untraceable."

"Clothes, money, bank account?"

"I have a selection of clothes here, and have a bank account and credit cards under a new identity. Once you change, I'll get photo IDs done immediately."

"If I agree and change."

"I have the drugs both to change you, and to change you back. You can do this. If anyone can do this, you can."

"If I do this I'm fucked - literally and figuratively."

"We'll get you an implant so you don't get pregnant."

I slumped in my seat, holding my head.

"I don't know if I can do this."

"I've done it myself - both ways. I wouldn't ask you to do something I wouldn't do myself. If I thought I could do this operation and that the mole would not fuck over the department. I wouldn't ask."

"I don't know how fucking reassuring that is."

"You can do this. And you can take down Sokolov once and for all."

"Shit. Give me the fucking drug before I change my mind."

My boss reached in his jacket pocket and pulled out a bottle with two pills in it. One was pink and the other was blue. I looked at them.

"Take the pink one now. I'm giving you a blue to change back when you feel you have to. Keep it somewhere safe."

"You bet your ass I'll keep it safe. I might do this, but I sure as shit don't want to be stuck this way."

I had a bottle of water, so I put the pink pill in my mouth, took a gulp of water and swallowed it.

"It'll take between five and fifteen minutes to take full effect. When it's done, Michael will be gone and you'll be Michelle."

"Michelle?"

"Michelle Popov. Daughter of two Russian immigrants who came to the US around the end of the Cold War."

It took a minute or two, but I went from feeling chills to feeling a tingling throughout my body. I could feel the bones in my face altering, and it didn't feel that good. My other bones and muscles seemed to change also. It was not genuinely painful - I've been tortured by people who know what they're doing. I know real pain, but it didn't feel comfortable. I could feel a drawing up in my groin, as my testicles and penis withdrew into my body. I could feel my chest expanding as my boobs grew, and the nipples became very sensitive.

I was almost hyperventilating as I sat there with my body morphing. My boss sat in his chair with his hands folded across his lap and a little half smile on his face. I could see and feel the hair on my arms thinning out and feel other hair on my face and legs going or thinning as the hair on my head began to grow. I am used to feeling in control of my body. I am proficient in hand to hand combat in many styles, including karate and MMA, but now my body was in control of me.

I had about fifteen minutes of rolling waves of aches and tingling before things began to settle down and I could breathe easily again.

"So, Michelle, how do you feel?"

"Wha... what?"

My voice was weird. I know we never really know what we sound like. You hear your recorded voice and it sounds nothing like what you think it does. My voice was now easily two octaves higher. I went from a warm baritone to a sultry alto.

"I can assure you, Sokolov and his people will never recognize you."

"What the fuck have I gotten myself into?"

"The kind of operation that can make your career."

"Or destroy it."

He got up and walked over to my chair and extended a hand to help me up. There was no way in hell I wanted his help, even if my legs were shaky. I ignored my hand and stood up, wobbling a bit as I did. He gestured in the direction of a mirror, so I walked to it to see how I looked.

I was shocked at what I saw. Before that pill, I had been 6'1" 185 pounds and fit, but not muscle bound. The face that my girlfriends told me was handsome and rakish was gone. I saw a woman with a very pretty face, about 5'9" and 135 pounds, and what appeared to be c-cup boobs and a nice ass. I looked in the mirror wanting to fuck the woman I saw there, though I knew it had to be me. I think my knees got a little wobbly again, before I regained control.

"Kind of a shock to look in the mirror isn't it?"

"That is me, isn't it?"

"It sure as hell is. You might as well get used to it. By the way, you can't take the second pill until 48 hours after the first one. We had some nasty results when that was tried."

"How? Who? What?"

"That was what happened to Dmitri. He freaked and took the second pill immediately and it killed him."

"Shit. You said there were some clothes?"

"Yeah, and I think I did a decent job of estimating your size. They're in your bedroom."

He gestured toward a door over to my right. I looked at it, then at him.

"My bedroom?"

"I had this flat leased for this operation. This place is yours until it's over. We may use it for a safe house after."

"I have stuff at my place..."

"And the other side will be watching it. If Michelle shows up at Michael's place, they will tie Michelle to Michael. After Dmitri died, you were the next obvious choice for this. They're still watching Dmitri's place and have been watching yours too. I had to work to shake them to meet you here."

"Yeah, I had to shake a tail too."

"Okay girl, get in there and put some proper clothes on."

"Girl?"

"Get used to it."

"Shit."

I turned and walked into the bedroom. It felt funny, and I realized that my hips had changed with the drug and it changed my stride, no matter how I tried otherwise. I might not be trying to shake my ass, but it moved a little more than it did before.

I got in the bedroom and nothing I was wearing fit quite right. I kicked off my shoes which were coming off anyhow. I took off my shirt, and my boobs popped out. I marveled a bit and wanted to touch them, but decided that could wait. My pants were too long and a bit tight in the seat, but loose in the waist. I unbuckled my belt opened my pants and let them drop to the floor, then kicked them off. I looked down where I'd normally have a bulge, and there was no bulge.

I pulled down my boxer briefs, and let them drop. I looked down at my bush. I ran my hand over it. As I got to my clit and my slit, I felt a tingling through my body and my pussy got wet faster than I'd have imagined. That would have to wait too. I saw a dresser in the room and walked over to it and opened drawers until I found panties and bras. Why the hell did it all have to be so frilly? I found the plainest of each that I could - bright pink, unfortunately. I would have to do some shopping.

I pulled on the panties, which went on pretty well. The bra seemed to fit decently, but I had to work a bit to get it fastened behind my back. I made a mental note to buy some front snap bras. I looked in the mirror, and in bra and panties, I looked too sexy for words. I wasn't sure just how well I was going to handle this.

I went to the closet and found several skirts, dresses, and tops. No jeans, no slacks, no tees that I could see. All the tops seemed to be cut almost down to my navel. I picked the longest skirt and most conservative top I could find. It was a little awkward first with the skirt, as it zipped and buttoned on the side, not in front the way my pants did. The top was just as bad, the buttons were all on the wrong side. I had a hellish time getting it buttoned up. In shoes, there were some high heels, and some mid heels, so I picked some mid heels that were fairly wide, to make it as easy as possible to walk.

I looked in the mirror again, saw a brush on the dresser, and brushed my hair quickly. I saw a bunch of makeup on the dresser, but decided I was not going to mess with that shit - not right now anyhow. I looked at myself, shook my head, took a deep breath, and walked out to where my boss was waiting.

"Not bad. You'll get the hang of this, and you can shop for a few more things."

"I'm glad you approve - I guess."

"You need to shave those legs though, girl."

I bristled as he called me 'girl', but looked down and my legs were hairy - not as much as when I was a guy, but still hairy.

"Makes me think your underarms and bush need shaved too. You have to work on your makeup as well. You have to be on it to catch the attention of Boris Sokolov."

"I really don't know if I can do this."

"Look, Michelle. You can't take the other pill for at least 48 hours anyhow. It's Friday night, and you have until Monday morning to get started. Sokolov has payday advance office two blocks away."

"Isn't there some other way?"

"Don't you think I'd do it if there were? We have a mole who keeps Sokolov aware of what we're doing. We can't get an operative in there without changing them beyond recognition. That's what we've done to you. Sokolov and his crew can look at Michelle Popov all day long and never think they're looking at Michael Thomas."

"I'm so fucked."

"Hang in until Sunday night. If you still think you can't do it, take the other pill. I'll send you to Nome to bust illegal whale blubber trading or something, and find someone else."

"You probably would too, you bastard."

"Look, I know this has been traumatic. Do you want me to stay, keep you company and try to comfort you for a while?"

I looked and there was a nasty little glint in his eye.

"Comfort me, my ass. You just want to get into my panties."

"Why Michelle. I only want to help you and want only the best for you."

"I think you've helped me enough for a while."

"All right, darling. I'll go then."

"And don't fucking call me darling."

"You better get used to it bitch. Sokolov and his crew will do a hell of a lot worse than calling you darling."

"Whatever. Just get out of here. My boss tells me I have to shave and put on makeup. And after this shit, I need some rest."

"Maybe diddle yourself a bit too."

"Fuck you. Get out of here."

My boss laughed, turned and walked to the door.

"There's an envelope there with your background. You're a pro, learn it, like you normally would. And there's a burner phone to call or text me, and my number is programmed in."

With that he turned opened the door, and left. I walked over and threw the deadbolt, though I'm sure he has a key for it. I turned out the lights in the living area, and went to the bedroom.

As it turned out, shaving my legs was pretty easy. A lot more area but no harder than shaving my face. It was trickier shaving my underarms. My face sticks out, the underarm kind of sinks in. I worked at it and got them both shaved without too many problems.

Shaving my bush - now that was interesting. I got some scissors and trimmed the hair as much as I could. As I was getting it ready to shave, I ran my hand over it and had more tingling and found I was very wet again. This was obviously going to be a problem and I'd put off attending to it earlier. I figured I might as well get a little fun out of this and get off, if only to make it easier to shave there.

I had taken off all my clothes to shave my various parts, so I went back into the bedroom and lay on the bed. I knew my boobs and pussy had been aching to be touched, well I was going to give them what they wanted. I caressed my boobs with my left hand and gasped. I had no idea my nipples and boobs were so sensitive.

I had one hand on each breast, caressing, tickling, tweaking, and tugging at the boobs and nipples. I found myself moaning and arching my back as I played with them. It felt better and better and I moaned and writhed in bed from the pleasure of it. It built up until I was hit with waves of pleasure rippling through my body. I lay there in bed moaning, writhing, and pumping my hips as I had my first orgasm as a woman.

I lay there trying to catch my breath and realized I had yet to even touch my pussy, which now seemed to want the attention more than ever. I half sat up against a pillow and moved my hands down between my legs. The first touch was electric and I moaned again. I spread my pussy lips slightly and ran a finger gently up the slit until I reached my clit. I wanted to work it over, but it was so sensitive, I had to take my time and build up.

With two fingers from one hand spreading my labia, I ran a finger from the other hand up my pussy, over and over, bottom to top. I dipped in slightly and finished each pass with a flick at the clit. Almost involuntarily, my hips began to move in rhythm to the stroking. The pleasure built and built until I plunged a finger deep in my pussy, while I played with my clit with the thumb and forefinger of the other hand.

I pumped first one and then two fingers in and out of my pussy as I played with my clit. My hips were bucking so much, the whole bed was shaking. I shrieked as I came and plunged both fingers as deep in my twat as I could get them. I lay there shaking and gasping for air as I had the best orgasm of my life.

I still wanted to change back to a guy, but damn that was great. I lay back and didn't bother with trying to shave or even put covers on, but just fell asleep naked on top of the bed.

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

I woke up the next morning, lying on my side with one hand cupped over a boob and the other hand cupped over my pussy. It took a few seconds to remember that the drug had changed me to a woman, and the things I was touching were me.

After my epic masturbation session last night, I woke up as sexually satisfied as I've been in a long time. I stumbled into the bathroom to pee, and remembered I wasn't going to be peeing while standing for a while. After I peed and wiped, I looked at the razor and shaving cream still sitting there and decided to go ahead and shave my pussy.

I left a strip about ½ inch wide and about 2 inches long above my pussy, and shaved the rest clean. I showered and figured I needed to get dressed and get started studying my back story. I've been in too many of these undercover ops, and know if I don't have my back story down rock solid, I may be dead - literally. The folks I'm infiltrating aren't playing hopscotch, they kill and maim with no second thoughts.

I was Michelle Popov, daughter of two Russian immigrants who came over around 1989. I was born here, but grew up speaking Russian at home, and English at school and with friends. I was an average student in high school - bright but under-achieving, and went to community college just long enough to get an Associates degree. I'd had a few minor run-ins with the law, mostly teenage escapades, underage drinking, shoplifting, streaking one time. I guess I was a bit of a wild child.

My parents had done well for themselves but they were both killed in an auto accident last year, leaving me with an inheritance of a couple hundred thou. That was enough to give me some security, but also little enough that I still had to work. I been a sales clerk, took a brief spin as an exotic dancer, and a lot of short unmemorable jobs.

Once I felt I had it down - I am a quick study - I brushed my hair, put on a little eye shadow and lipstick and a touch of base on my face and went out. I was in skirt and top, since the bastard didn't buy me any jeans or slacks. I had a small purse with credit cards, and as I was getting ready to leave, found a driver's license and passport with photos as I am now had been slid under the door. I added them to the stuff in my purse, really wishing I had a gun in there too, but that would have been out of character for Michelle.