Caught by Kyle Ch. 01

Alright, longest disclaimer ever, but READ THIS, because I won't be responsible if you read something in the story that disturbs you.

First of all, this is not a romantic story with feelings of love and mutual respect. The main character is not a nice guy, he's not a woman trapped in a man's body, and there is no love and tenderness. This story is just smut with more dialogue and plot than your average stroke story.

Two, there is gay sex in this, which most of you have undoubtedly already figured out, but you'd be surprised at some of the oblivious individuals out there.

And lastly, there is mention of STDs in this story. I don't have enough imagination to write a story where that risk isn't present. If the mere mention of VDs is enough to make your pole wilt, then backclick right now.

Disclaimer over. Thank you to debby69 and verbinator for providing male perspective.

***

"And the winner for most sales this quarter is..." Bryan paused dramatically.

"We all know it's Mike! Quit milkin' it, Bryan!"

Everyone chuckled.

Bryan grinned. "Well, yeah. It's Mike. And thank God it is, otherwise we might have to go outside and see if the sky was falling!"

I grinned as I stepped up to accept the top sales bonus. "Thanks," I said to Bryan before turning to the crowd of employees gathered in the upstairs lunchroom. "I'll try and set the bar a little lower next quarter, 'kay guys?"

Most people grinned, a few rolled their eyes, and a couple muttered under their breath. I smiled in satisfaction. Fuck, yes. This was what I was all about: beating the competition. I could not give a shit less if they liked me or not.

At thirty-four, I was the star broker at the firm - the large firm, I might add - the highest paid broker there, the only one who never had to work a graveyard shift if I didn't want to, with a boss who loved me more than he loved his own children. Outside of work, I had a beautiful Jewish wife who my mom loved, a newborn baby boy, a big house, a hot car, and a hot shiksa girlfriend. My life was every man's dream.

"All right, in other news: this is Kyle Adams," Bryan gestured to a built blond guy in a powersuit standing at his side. The beefcake nodded and gave a casual four and a half finger wave. He had those nice, all-American kind of good looks. Probably didn't have two intelligent thoughts to rub together, but that kind of wholesome, attractive face tended to close the easy deals, at least.

I smirked as I caught my slutty receptionist and Joanne from accounting checking him out and whispering. And not just the easy business deals...

"We figured we may as well introduce him to everybody at the meeting. He was the prize of his last company, and we had to work real hard to steal him, so everybody be good to him."

Everyone chuckled. Or rather, the men chuckled. The women tittered. Looked like the beefcake was gonna be getting some office pussy.

Bryan started going on about some company safety meetings - blah, blah, blah - and the expectations for the upcoming quarter and annum. Frankly, if it wasn't directly about me, I didn't particularly care. Some might call that vain; I call it honest. People just pretend to give a shit about others and all this tedious shit they really couldn't give a fuck about. Why bother? Be honest with yourself, if with no one else, that was my motto.

The meeting was called to a close – finally - and I started to head back to my office.

"Hey, Mike! Hang on a sec, I wanna talk to you and Kyle here in my office," Bryan called out.

The door clicked shut behind us, and Kyle and I settled into plush chairs beside each other.

"You guys didn't really get a chance to actually meet out there. Mike Feldman, Kyle Adams."

I shook his hand, noticing with a flicker of annoyance that his hand dwarfed mine.

"Feldman? That Jewish?"

I rolled my eyes as I turned back to face Bryan. "Does it sound Hispanic to you?"

Bryan frowned at me, but I heard a chuckle from the annoying schmuck beside me.

"All right, let's get to business." Bryan shuffled some papers, looking, to my mind, like someone who was just trying very hard to look business-like. "I want you two on the same team."

"Thought Kyle here was one of the best?" I asked drolly. "If he is, then I don't think we need a babysitting period for him. And I'm really busy, Bryan."

"It's not for training." Bryan's gaze flicked away. "He'll be leading your team with you."

I stilled. "I beg your pardon?" I turned to find the pretty-boy smiling angelically at me.

Fucking chucklehead! He had the vapid, beatific grin of an all-American jock, but I could see the wry amusement in his eyes. God, I wanted to knock his teeth out.

Bryan's thumbs were twiddling: always a dead giveaway that he was nervous. "Mike, I told you I wanted you to start going after some really big accounts. Don't misunderstand this: you're good, but you'll need help. You'd probably land the big fish on your own, but you definitely will with Kyle here."

I opened my mouth to argue, but Bryan met my eyes; he wasn't going to back down. The fucking traitor. I put on my game face, pouring every ounce of charm into my friendly smile. "Well, when you put it that way...Welcome aboard, Kyle."

That amused gleam still glinted in his eye as he shook my proffered hand. "Thanks, Mike."

The way he said my name grated along my every nerve ending. I didn't even notice I was grinding my teeth. He not only looked like a jock, he spoke like one, too. A baseball player. That's what he reminded me of. A big, star baseball player, talking to some balding, insignificant sports commentator.

"Well, I better get back to work," I said, sidling toward the door.

"Great, you can take Kyle with you and show him the lay of the land."

I forcibly stopped myself from grinding my teeth into dust. "Yeah, great. Let's go." I didn't even check behind me to see if he was following as I strode out the door.

***

The day had been total shit. I hadn't even gotten a short reprieve before having to deal with the dickhead. He'd been over my shoulder all day. I'd tried to give him shit to familiarize himself with, and either he wasn't really going over them or he was a fucking speedreader or something, because he'd be right back in my office two seconds later, looking for something to do, asking me what I was doing, acting like he understood complicated things with only the half-assed explanations I'd give him. The worst part was that I was scared he was just that good.

All day long, I had to bite my tongue until I damn near chewed it off, and he knew. Every time I got annoyed with him, he could tell, and he was amused. Fucking bastard.

There was no way I was going home tonight. Nor was I going to see Tamara; she was starting to get a little too clingy lately anyways, so I'd probably have to start thinking about replacing her soon. Amazing how your outlook on life can change in just a few hours...

I unlocked the dingy door to my even dingier apartment in the indescribably dingy building on the other side of town from my real home. I had it kept relatively clean, but there was only so much you could do with an apartment in a craphole like this. On the other hand, the landlord took cash and didn't ask questions, so it suited my purposes.

I took a beer out of the fridge and cracked it open, taking long swallows on my way to the bedroom. I stopped in front of the mirror, grimacing at what I saw. Oh, I was good-looking, but in a generic, non-rugged, skinny kind of way. That had seemed good enough until the beefcake walked in today.

He was an Adonis, the bastard. Blond hair that bordered on too long, but managed to stay just shy of it. I ran a hand over my closely trimmed head. His broad, muscled shoulders clearly dwarfed mine, even hidden underneath his expensive suit. And his hazel green eyes made my brown ones look absolutely plain and unremarkable. I really, really didn't like this guy.

I finished my beer in gulps, then strode over to the closet and flung open the doors. Not twenty minutes later, I was more beautiful than the beefcake could ever be.

My long brown hair was shiny and lustrous, offsetting my honey-colored contacts perfectly. My breasts, showcased in a tight, V-necked cashmere sweater, were just shy of large; big enough to tantalize boob men, small enough not to repulse the teeny-titty lovers. My long, stockinged legs were mouthwatering from my tiny denim skirt right down to my four-inch heels.

Mike might not be prettier than Mr. Kyle Adams, but Tiana sure as hell was.

I slung my purse over my shoulder and went out looking for a date.

***

The hot, sun-soaked air of Los Angeles hit my face as soon as I stepped out of the airport. Baltimore was nice, but I'd always loved sunny places. I was here because Martin, the owner of Real Investments, wanted the business of his old college buddy Ted Wallace. Supposedly the old guy was unbelievably loaded, moving back to Baltimore at some point, and considering giving his friend his business, but just needed an extra push. I was the company closer, so here I was, ready to spend a couple of hours doing the song and dance for Martin's buddy then the rest of my three days enjoying some LA sights and sunshine.

"Lot warmer than Baltimore, isn't it?"

If only I was here alone...

I frowned at Kyle, as he came up next to me, beefy arms and shoulders stretching his white T-shirt, making me feel scrawny and ridiculous in my black wifebeater.

"So whaddya wanna do after we land this, man? It doesn't sound like this guy needs more than a little push, so we'll have tonight and the weekend to kill."

Was this guy just completely without a clue? I glanced at him and saw the amusement there. No, he definitely knew I didn't like him. The last couple of weeks I'd cooperated with him, but I'd made no effort – besides not openly telling him to fuck off - to hide my disdain for him. He just didn't seem to care. Every time I was short, he'd get that amused look on his face that just made me want to punch him.

"I don't know what you're planning on doing, but I'm gonna go visit some friends," I snapped.

If one interpreted visiting friends as picking up men while dressed as a woman, I wasn't technically lying.

"Oh. Well, I guess I'll try and find myself some action tonight. Some beautiful ladies out here," Kyle said, grinning at a tan and shapely twenty-something year old as she smiled at him on her way by.

I was not standing around all weekend while women made bedroom eyes at this asshole. "Let's get going. Sooner we get this done, sooner we can each go about our respective plans," I said testily.

"Whatever you say, man."

***

Ted Wallace didn't get rich by being a fool; he was old and fat, but one of the sharpest motherfuckers I've ever met. He asked some tough questions and pushed for the kind of special treatment that would get most people laughed out of my office. Not him, though. He knew how much we wanted him, and he was making sure that he got as much as he could from us.

Galling as it is to admit, Kyle was smooth as butter. Answering some questions just that much better than I would have, and slapping down some of Wallace's more ridiculous demands while managing to be totally inoffensive.

Not that I was sitting there useless. I'd picked up the ball when Kyle had dropped it a couple of times, stepping in smoothly and mixing just the right amounts of truth and bullshit.

In short: we nailed it. Ted wanted a very large and very diverse portfolio that would yield a lot of profit in the next ten years, which meant lots and lots of money; Ted Wallace had dropped figures that had literally given me a bit of an erection.

Now we were back at our hotel, with Kyle for some reason lounging on my bed as if we were best girlfriends on a sleepover. He'd brought over celebratory beer so of course I hadn't turned him down, but now the beer was gone. And he was still here.

I glanced at the clock. "Right, well, I gotta get going right away."

He grinned wryly, and I gritted my teeth, wondering what the fuck he always found so amusing about my brush-offs.

"All right, Mike. I'm gonna go check out that bar across the street."

"Yeah, have fun, man," I said, rolling my eyes as he finally left.

I showered, and took extra time with my clothes, hair, and makeup. I chose a gold lamé halter top, and a black leather mini. I chose my curly wig tonight, and pinned it up, leaving some tendrils to curl around my face and the nape of my neck. My makeup bordered on slutty, but I had a line I never crossed with it; I wasn't interested in looking like a drag queen. To complete the picture, I slipped on my black knee-high boots with the stiletto heels. My olive-tinted skin seemed extra radiant today.

I couldn't keep from smiling as I looked at myself in the mirror; I was such a hot bitch.

Swinging my little gold handbag and my hips, I decided to take the stairs: I was wearing a silky thong that felt magical as it rubbed against my freshly shaved sac.

I'd researched the red light districts of LA before coming, so I smoothly told the cab driver to drop me off at a store on a street that was marked as a walk for transvestite hoes.

Some crossdressers have a big thing about being viewed as people with thoughts and emotions and many other sappy things; not me. I had no interest in being respected and loved for who I was. I loved being used by perverted men who just had a kink for fucking men in skirts. That was it. The money was small change to me - laughable, really. I just liked being used like the little hoe that I was.

I smirked at a couple of hideous trannies as I passed by them, my lips twitching as they glared at me; no hoe liked new meat on her block, but it was especially understandable for these ugly bitches to be pissed off with me: I was hot and wearing nice, if slutty, clothes, whereas they looked like Courtney Love on steroids. Ew.

It wasn't even two minutes before I was picked up by my first date. Toyota Camry, clean, carseat in the back. I smiled invitingly at the driver as I slid into the passenger seat. He was a business-casual type just this side of being plain. Good-looking, in an innocuous kind of way.

"Hi, honey. You mind if I see what you're packing?" I reached over and grabbed his package, not waiting for an answer.

'Hmmm. Average all over.' I quickly dubbed him Mr. Average in my mind, giggling at my own little joke as he reached into my lap and nervously squeezed my cock - already semi-swollen with arousal - in return, completing the universal hoe-john procedure for proving that neither one of you is a cop. After he removed his hand, I absently stroked my cock underneath my skirt.

Unlike some crossdressers, I can never get so into the whole being a girl thing that my dick becomes a pussy or a clit to me - a dick is a dick, and women don't have balls. But it's really not a sad thing for me; I think of it like being a woman, but with male genitals, which somehow seems obscene and extra nasty. Much hotter than these teary-eyed trannies who are 'women trapped in men's bodies.' Jesus. With that much estrogen, no fucking kidding you're a woman trapped in a man's body. No way would any doctor be coming near my dick with a scalpel. No, sir.

"You know where to go, honey?"

He nodded, his eyes now fixed to the road as he pulled out.

"This your first time?"

He shook his head. "Second." His voice was barely audible.

"Well, what do you wanna bet I'm better than the first? All my boys tell me they've never had a girl as good as me."

He smiled weakly.

I frowned. Cute as the inexperienced were, they were never much fun for talking to.

We finally pulled into an empty school parking lot hidden from the view of the road. I grinned. His last trick must've shown him this place.

"It's eighty for a fuck, forty for head, that okay?"

He nodded.

"What say we get in the back seat?"

He nodded again.

I didn't get out and use the door, instead climbing between the seats, wiggling my ass seductively as I passed him. I felt a hand brush my thigh, then quickly pull away.

I easily unbuckled and moved the carseat, wondering if Mr. Average was pondering how I knew how to take a carseat out so quickly. I set it on the floor and sat back, turning to face him. I spread my legs and ran my fingers over my panties in invitation. He climbed into the back slowly, and half-rested back against the front seat divider/armrest.

I mentally sighed; I really hated the ones who couldn't take any of the control. But I pasted a smile on my lips. "Come here, baby."

I tugged him to me, and he surprised me by pressing his mouth to mine, moving his lips against mine until they opened, then thrusting his tongue inside. His tongue was warm, and tasted good, like coffee. I slid my palm down his belly and massaged his cock. It was rock hard, jumping at my touch through the material of his pants.

His hand slid up underneath my short skirt, and he brushed his fingertips across the ridge of my dick. I broke away from his lips to ask what he wanted tonight, but moaned instead when he palmed my balls and trailed his hot mouth down my neck. It took me a moment to catch my breath.

"Do you want to fuck me, baby?" I moaned, growing increasingly excited at the thought of stuffing his cock inside me, average or not.

He tore his lips away from my neck for only a second, "Yes." He twisted and pressed me down to lie along the backseat, licking down to my cleavage as he did so.

I hooked my leg around his and rubbed my foot along his calf, arching up against him as he tongued everything that wasn't covered by my top and rubbed his cock against mine. I felt a wet drop form at my little slit, dampening my silky panties. Suddenly he pushed my leg down, grabbed my thong by the sides and slid it down. I nearly came when he leaned down and gave my rapidly distending cock a tonguing kiss.

"Please fuck me!" I pleaded, unable to believe this completely average guy had me so excited.

I thought I saw him give a crooked smile, but he quickly flipped me over onto my stomach. I rose up onto my knees and thrust my ass back at him. I jerked so hard I banged my head into the door when instead of the push of a cock or even fingers against my rosebud I felt that hot, eager tongue. My cries were caught in my throat as he stroked and probed my tight anus.

"Do you have a condom on you?" I gasped.

"Yes." I could feel his warm breath against my rosebud. I shuddered.

"Put it the fuck on and get inside me NOW!"

I felt him smile.

I heard the crinkling and tearing of foil behind me. I stayed in my position - a bitch ready to be mounted - clutching the edge of the seat in anticipation. The smooth, latex-clad head pushing at my tight opening nearly made me cum right there. The lubricated condom and my saliva-slicked ass made for easy entry, and I groaned as he pushed past my tight sphincter. I never let myself get too loose - if I started getting a little on the loose side I'd take a break for a few weeks - so my ass wrapped around him like a glove as he slid in.

He grunted quietly behind me as he began working his cock in and out, lightly holding my hips.

"Feel good, baby?" I moaned teasingly, rocking backward and clenching my ass around him.

"Yes," he said breathlessly.

His cock was pushing on my swollen prostate gland, harder and harder as he got increasingly less shy. His hands were gripping my hips tightly now, and his hips slapped against my ass as he pounded into me. My cock was practically streaming pre-cum as I took the onslaught on my G-spot. I jerked as a hand wrapped around my cock, using a finger to smear the fluid leaking copiously from the slit, then beginning to jerk me.