Michael Undercover

I realized I needed to hide the other pill I'd gotten from the boss. I looked around and saw a ceramic lamp in the bedroom. There was some heavy paper on the bottom. I peeled that back and taped the pill bottle inside, after stuffing the bottle with cotton, so the pill wouldn't rattle. Then I glued the heavy paper back on the bottom to hide what I'd done.

I scanned the bedroom for any cameras or mikes planted for surveillance. I wouldn't put it past that bastard to snoop on me or even get off watching me nude or masturbating. I found nothing in the bedroom or bathroom and nothing in the kitchen. I did find one camera in the living room, and just made a mental note to be dressed any time I was in there. I knew If I pulled it, he'd find a sneakier way to plant it again.

I made a quick visit to a doctor that the boss had given me the name of. He did a quick check then put in a contraceptive implant so I wouldn't get pregnant. Shit was getting real. I was a woman and I would be fucking men, at least some. It still made me feel a little sick, but I tried to just put that behind me and focus on the job I had to do. He also put in an IUD, since he said the implant might not be effective for up to seven days.

I hit a department store near me and bought a couple pair of jeans and slacks, along with some tees and flats. I bought some more mundane bras and panties - not so lacy and with front snaps on the bras. I know I'll get the hang of hooking the other bras in back, but that makes it easier in the meantime. I went to the cosmetics area and bought a bunch of stuff and had the woman there give me a makeover and some tips on applying makeup better.

After some shopping I was beginning to feel comfortable in my skin and almost forgot I was a woman instead of a man. I stopped in a coffee shop to get a nice Espresso. There was a cute woman there, though a bit boyish, with short hair and boy jeans. I smiled at her and she walked over to me.

"Hey, honey. Mind if I join you?"

"I don't mind at all."

She smiled, and sat down beside me, then scooted her chair even closer. Damn, this girl moves fast.

"I haven't seen you in here before. Are you new to the neighborhood?"

"Just rented a flat a few blocks from here. I'm starting to explore the area."

"I'd love to be your tour guide. I'm Riley, by the way."

"Hi, Riley. I'm Michelle."

"So, you have any plans for the afternoon?"

"None. Why?"

"I thought maybe we could hang out, and even have some fun."

She gave me a smile, and I knew exactly what kind of fun she had in mind. Then again, that sounded pretty damned good to me.

"That sounds great. I need to drop some of this stuff off at my flat though."

"Great. We'll finish our coffee, then drop your stuff off at your flat and go from there."

Riley smiled, leaned forward, and gave me a quick kiss on the lips. We would go back to my place. Would we see much other than my bed though? Maybe not today. I don't want this to get in the way of my op, but it sure wouldn't hurt as a diversion.

After we finished our coffee, we walked to my place. I had my shopping bags in my left hand. Riley walked on my right side, with her left arm around my waist. Every now and then, she'd let her hand slip down over my ass, before moving it back to my waist. She was kind of slick, never pushing it enough to make me stop her or to attract the attention of passersby, but enough to let me know where she was coming from.

I unlocked my door and we went in, closed and locked it back, then Riley turned me around grabbed my face and gave me a passionate kiss. I kissed her back, and just let my packages drop to the floor. She kept kissing me as she brought one hand down to caress a boob while the other hand went right to my ass. I could feel my nipples getting harder as she began unbuttoning my top.

We were still standing near the door as she finished unbuttoning my top and slid it off my shoulders. She stroked both boobs, one with each hand before reaching behind me to snap my bra. I was really getting into it and began stroking her boobs through her top and bra. She moaned as she pulled my bra off, then stopped kissing me to drop down and take a nipple in her mouth.

I remembered the camera placed in the living room, and took her hand and led her into the bedroom. No reason to give an extended show to the boss. He could go find some porn sites if he wanted to get off.

We got in the bedroom and I pulled off her top and her bra. She resumed kissing, nibbling, and sucking on my nipples as she unzipped my skirt and let it fall to the floor. I unzipped her jeans and eased them down as we moved to the bed. My nipples were so hard, it felt like I could cut glass with them as she worked me over and I had a warmth rising through my body. She lifted on my hips and I lifted them off the bed as she slid my panties off.

"God. I love you femme types. These are so sexy."

She then buried her tongue in my cunt and licked like there was no tomorrow. She got her tongue farther in me than I thought a tongue could go, but I wasn't complaining. I could barely keep up as she switched from burying her tongue deep in me to licking my pussy, to sucking on my clit. I'd gone down on women many times, but Riley knew what she was doing. I wrapped my legs around her neck and pulled her close as she brought me to an orgasm that made me forget last night. I bucked my hips and fucked her face with my pussy as I came over and over.

I loosened my hold on her and she slid up beside me on the bed wiggling out of her boyshorts as she did. She kissed me and pulled me on top of her, stroking my ass and boobs as she did. I wasn't exactly just lying there, but was stroking her boobs and even snuck a hand down between her legs. She had more of a bush than I did, but I could feel the wetness from her pussy as I stroked her.

"Your turn, girl."

I kissed her and slid down to suck on her boobs. I had one nipple in my mouth and stroked the other one with my fingers. She moaned and stroked my head as I switched back and forth between the boobs sucking on one as I caressed the other. I kept at it until she moaned and rocked back and forth against me. I guess I couldn't be too bad at this, God knows I'd fucked enough women in my day, just never before as a woman.

As she settled down, I slid down between her legs. I know my tongue isn't as long as hers felt, so I eased a finger into her as I licked her clit. A little awkward, I had to be careful not to poke myself in the face as I fingered her. As she loosened up, I added a second finger, getting them as deep into her as I could manage. Before long, she came again. She drove her hips so much into my face, it almost felt like she was levitating off the bed.

We lay together in bed kissing and stroking each other for a long time, before we stopped, almost from exhaustion. I still didn't want to stay a woman, but was feeling that I could really get used to this. I wondered if somehow the boss arranged this, or whether I was just damned lucky. Either way, I figured I'd survive living as a woman, at least for a while.

"So, Michelle, what do you do for a living?"

"I've been bouncing between jobs, but I'm looking for something right now."

"I know a guy who'd hire you, but I'm hesitant."

"Why?"

"He is a major fucking letch. He'd be trying to get in your pants before the ink dried on the employment papers."

"I prefer women, but..."

"And I'm not sure I want to share you."

"Who is it?"

"A Russian guy, Boris Sokolov. He owns some payday advance shops, a couple of clubs, and some legal marijuana shops."

Here I am, wanting to get my foot in the door with Sokolov's operation and I luck into meeting a woman who knows him and can get me in. I guess there really is a God, and he seems to be on my side, I think. I need to play this a little cool though. I don't want to tip my hand by seeming too eager.

"I'm not sure what kind of a job my background would qualify me for. I've done retail sales, phone sales and shit."

"Girl, the way you look, Boris would hire you, then try to figure out what to have you do, when you weren't in bed with him."

"I don't think I like it if fucking a guy is a condition of employment. Besides, I like being with you. I don't want something to get in the way of that."

"It wouldn't be an all the time thing. Hell, he fucks me every now and then, but he also likes a threesome with two women. I've taken a few girlfriends and we've shared them."

Riley stroked my head and kissed me.

"You though - you're beautiful. He might just want to take you from me."

"We need to let him know up front that won't happen."

"Boris has money and power. Generally what he wants, he gets."

"I don't know if I like that."

I might not like it, but that's exactly what this op calls for. I need to get in Sokolov's operation, and if fucking him is what it takes, I guess I'll do it.

"Let's go out tonight. Boris has a club that caters to LGBT. If Boris is there, you can meet him. If he isn't then we just party, and maybe come back here after."

"I'd like us to come back here after, even if I do meet him."

"If you meet him, I expect it will be the two of us and him at his place."

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

We spent more time in bed having fun, before we showered to go out. Riley just wore what she'd had on earlier, but she wanted me to dress in the sexiest outfit I had. I was in a real short skirt, with a slit up the side and a low cut top. She put me in the laciest and skimpiest bra and panties, and wanted me in high heels. I'd practiced in the heels earlier so I didn't look like a total klutz, but was a little more ungainly than sexy in the heels. Boy did those heels make my ass move though.

The club was only about four blocks, so we walked. As I went along, I got more comfortable in the heels, but still wondered how women coped with this shit. At one point a couple of guys started catcalling. Riley replied to them.

"Fuck off, boys. She's taken."

The two guys came up to us and hovered over us. One of the two reached out and grabbed my ass. I kicked him in the groin, and leveled the bastard. His friend came at me and I took him out too. I might not have the muscle I had as Michael, but I still had all my fighting skills.

"Shit, girl. Remind me never to get you pissed off."

"They need to learn some respect."

One of them started to get up off the ground, and I kicked him in the face. Managed to break his nose and knock out a couple of teeth. He fell back down and stayed down.

We made it the rest of the way to the club with no problems. There was a burly woman at the door. She looked me over good, then turned to Riley, smiled and winked.

"Damn girl. Where'd you find her?"

"Just call me lucky."

The woman turned to me.

"Honey, you're welcome here anytime, with or without this dyke."

I smiled at her and she waved us in.

"Liz is tough looking, but really kind of sweet. I usually warn people that they don't want to mess with her though. After what happened on the way here, I might want to warn her not to mess with you."

"Sweet, femme, little old me?"

"Who takes out two big guys in thirty seconds flat."

"I thought it took at least forty five seconds, and if I hadn't caught them by surprise it would have taken at least a full minute or more."

We got drinks and Riley introduced me to a bunch of the women there, most of whom looked pretty damned interested in me. None of the men showed any interest, which was just fine with me. After a little while we got up to dance. We fast danced together and sort of with a group of women, so I was almost dancing with Riley and God knows how many other women.

A slow number came on, and Riley grabbed me to slow dance. She pulled me very close and had one hand all over my ass as we danced. I suppose I'm used to leading and doing the chasing, but I sort of enjoyed letting Riley take the lead. At the end of the number Riley gave me a long kiss. Another slow number started and one of the other women asked if she could cut in.

"Sorry. I think we need to sit down for a little while."

We smiled and walked back to where we'd been sitting and got another drink.

"I wouldn't have minded if you'd danced with her, Michelle."

"At least tonight, I'm a one-woman ... girl."

I almost said I was a one-woman man, but just barely caught myself. Riley kissed me and ran her hands all over my ass. I was nearing the point when I wanted to tell her we needed to leave and go back to my place. As I was trying to get the words together, Boris Sokolov walked into the place. Sokolov is in his forties, about six feet tall, maybe 210 pounds. He had a few extra pounds but was mostly muscle and bone. He had dark hair with a few strands of gray starting to appear. He carried himself like he knew he was in charge.

He walked through, looking at what was happening. He stopped to talk to the bar help and bouncers, then he spotted Riley and me. He stared hard at us, and then had a small, slightly wicked smile. He walked over to where we were, and as he approached, Riley saw him.

"Michelle, this is the man I told you about - the big boss, Boris Sokolov."

"I'm very pleased to meet you Mister Sokolov."

He had a broad smile as he replied.

"Please, call me Boris."

"Sir, Michelle here is looking for work, and I told her she should check with you."

"And what kind of work are you interested in doing, Michelle?"

"I have an associates degree in business, but I've mostly just done sales work - retail sales and telephone sales."

"I'm always looking for talented people, and I think you may have some talents that interest me. What do you think, Riley?"

"Michelle is very talented, and I think she's adaptable."

"Both very admirable. I have some things to check on, then let's talk about what I might have for you. In the meantime let me get you both fresh drinks."

Riley and I were sitting at the bar, and before Sokolov walked off, he turned and spoke in Russian to the bartender.

(In Russian) "Give them each a drink on me, but take the glass of the pretty bimbo and give it to Pyotr to check the fingerprints. She wants work, but I need to make sure who I'm dealing with."

Obviously Sokolov didn't know I spoke Russian. How would he, at this point? I would guess that Riley didn't speak Russian, or at least if she did, she hid her reaction well. The boss told me he had the electronic fingerprint files changed so the prints would NOT come up as Michael Thomas. If he screwed that up, I was dead. The bartender took our glasses, grabbing mine carefully so as not to smudge the prints, and gave us each a fresh drink.

Sokolov smiled at each of us, nodded and walked back to the office. Riley and I drank and danced for another hour or so before Sokolov came back out of the office and walked over to us. As he did he turned and spoke again to the bartender in Russian.

(In Russian) "She came up clean?"

(In Russian) "Just what she appears to be. Pyotr has a report for you on her."

With that, the bartender handed an envelope to Sokolov, which he put in an inside coat pocket.

"Ladies, this place is much too noisy to talk business. Let's go somewhere and see how Michelle here might fit into our organization."

With that, Sokolov gestured toward the door. Riley took my hand and we walked out, Sokolov immediately behind. The way cleared in front of us. Everyone cleared the way for Sokolov. Liz, at the door, opened it for Riley, Sokolov and me, nodding to Sokolov as he passed.

There was a big black limo right in front and a man opened the limo door. Sokolov gestured for Riley and I to get in so we sat in the limo, as did Sokolov, who sat right beside me. The driver got in and Sokolov spoke to him in Russian.

(In Russian) "Take us to my place. Stay close for a while. I don't know if I'll need you for anything else quite yet."

So what else did he think he might need that driver for? I wasn't really worried, but I couldn't take anything for granted either. Sokolov put his arm around me as we rode.

"So you and Riley are close? I guess that means you like girls."

"I do like girls, and I like Riley."

"Exclusively girls?"

"I'm willing to take a walk on the other side too - for the right person."

"I'm glad to hear that. I'd have thought it was such a waste otherwise."

"Some of the women think it's a waste if I take a tumble for a boy."

Sokolov laughed.

"No doubt. No doubt."

We arrived at a building and the driver jumped out and quickly came around to open the car door for Sokolov. He got out and held out his hand first to help me out of the limo, and then to help Riley. He waved us toward the door to the building where a doorman opened the door for us, with Sokolov following. We walked over to an elevator which Sokolov had to produce a key to open. His place was a little over halfway up the building. He was not so flashy as to go for the top floor, besides which, it becomes harder to isolate which floor he is on, just looking from outside.

He let us into a very posh place and gestured toward the bar and toward a sofa and told us to make ourselves at home. He in turn went into a room and closed the door behind him.

"He must really like you to bring you here already."

"He had me checked out."

"What? How? How do you know?"

At that point Sokolov came back out of the room and turned to me.

(In Russian) "So you speak Russian?"

(In Russian) "I learned it from my parents, growing up."

(In Russian) "Then you knew I was having you checked out?"

(In Russian) "I didn't think I had anything to fear."

Sokolov laughed, then spoke only English after that.

"Maybe I can really use your talents, and more of them than I first thought."

"Let me know how I can help you."

"Would you care to come in the bedroom, and perhaps enjoy the 'company' of your friend, then let me join the festivities?"

"I'm fine with that if Riley is."

"Sure. It was kind of what I expected."

"Then please, this way. And by the way, I sent my driver home for the night, but he'll take you both home in the morning."

"Then either you assumed we'd accept, or you figured we'd find our own way home if we didn't."

Sokolov laughed and opened the bedroom door for us. He had an ultra king size bed. It must have been twelve feet by ten feet. He was clearly ready to sleep three or more people in that bed. Then again, he was planning on doing a lot more than sleeping tonight.

Even though Riley and I had spent quite a while in bed earlier, I felt a bit shy. I guess she was a little more used to this. She took my hand and led me over to the bed. She kissed me and pulled me down on the bed with her. We took it a lot slower than we had earlier in the day. I think we were both in serious lust at that time. Now it wasn't just for us, it was also for our audience, Sokolov.

He took off his jacket and threw it across one chair, then sat in another chair close to the bed to watch as Riley and I made love. Last time, it was raw lustful fucking, but now it seemed to be sensual and slow, more about feeling something for each other than just raw physical pleasure.

She kissed me and stoked my body through my clothes, but was in no hurry to take them off me. I decided to ignore Sokolov and focus only on Riley, at least until Sokolov decided to join in. We kissed, caressed, and stroked each other as we slowly undressed each other. It was almost half an hour before we were completely naked and Riley pulled me down to eat her out.

I was licking her pussy and fingering her toward an orgasm, when I felt Sokolov lift up on my hips and Spread my knees. He came up behind me and as I Riley came, I felt Sokolov slip his dick in my pussy. It was only a mild shock. I knew something like this was going to happen. I continued to lick Riley as he slid his prick in and out of my cunt, fucking me doggy style. At first he held onto my hips, then he slid his hands forward so he could grab my boobs as he fucked me.