An Executive Learns His Place

My phone dinged, an email from Tim, guy in our IT department. What the hell was he doing sending something to my personal address? How'd he even get it? I opened the message.

Luke,

I have an important matter to discuss with you that I don't think you'd want to talk about in the office. Meet me at the Motel 6 near the airport tonight at 7pm.

Tim

Who the fuck did the little shit think he was? I was senior VP of the company, married to the boss's daughter, and the boss was retiring in a few months. Everybody knew I'd be running the place soon. Hell, I pretty much already did. Took me a moment to even make sure I was picturing the right guy. Oh yeah, tallish dude, probably mid 20s, had one of those hipster beards. Always rode his bike to work.

I fired off a quick reply.

You got something to talk about, call my admin, tell her what it's about and make an appointment.

A minute later, my phone dinged. Tim again.

OK, if that's how you want to play it, but I don't know what your admin is going to think when I tell her that this is what it's about. Be at the Motel 6 at 7pm or I'll send that to her in the morning. Don't write back, just show up.

There was a link at the end of the message. I clicked on it. Shit, one of my favorite porn videos. This really hot shemale hooker in Amsterdam really working over a young couple. Where'd he get that? Thing is, the old man? The boss? He was the most up-tight, bible-thumping prude you'd ever want to meet. And if this link went to my admin, it was going to end up in front of him and I might end up having a conversation I'd really rather not.

OK, I'd go see the little shit. And then I'd figure out how to fire his ass. I am not someone you fuck with.

7pm. I knocked on the door of room 236 at the Motel 6. Tim answered. Damn hipster skinny jeans, tight t-shirt for some rock bank I'd never heard of. Had to admit he filled it out well, though. More muscular than I thought. Guess all that biking kept him in shape.

I pushed past him into the room and took the only chair. Figured I'd take control from the start.

"OK, I'm here. And you're real close to looking for a new job. So have your say and make it quick."

He smiled, sat down on the end of the bed.

"You know all about the boss's internet policies, I assume?"

I just nodded.

"The whole zero tolerance thing?"

Yeah, I knew. Years back when the internet was taking off and the old man had no clue what it was about, he happened to walk in on a manager who had the SI Swimsuit edition up on his screen. Boss went ape shit, wanting to know how "this pornography" could end up on his company computers. Never mind you could buy a copy from the newsstand in the lobby. IT guys explained to him, how the internet was just a medium, it could bring in anything, including stuff a lot worse than that. At first, he wanted no internet at all, but we were able to explain to him how that just wasn't an option for any business anymore, so then he set the policy. You get caught looking at anything inappropriate by even the broadest definition on the company network, you're fired. No warning, no second chances, done. First year or two, there were a couple firings every year, even a VP, but people got the message.

"Yeah, I know," I said. "So what?"

"So you should have been a little more careful with your porn habit," Tim said.

"Bullshit. I'm not stupid enough to look at anything at the office."

"Not the office, but sometimes when you're on the road and you sign into the VPN, you forget to sign off before you have your fun. And the VPN is the company net. So technically, you're looking at porn on company resources."

Had to think about that one for a second. Technically, I guess so. But I wasn't just anybody. I was his fucking son in law. And I pretty much ran the company now, had for years. Besides, his daughter knew I liked my porn, practically encouraged it. She'd never been that in to sex, her upbringing I guess, and as she got older, hardly wanted to put out at all. She figured the more time I spent beating off, the less I'd spend bothering her. It came to it, she'd talk to dear old dad.

"Nice try Tim, but fuck you. I think I can ride this out, and I'm pretty sure you can't. Better get your resume together"

I got up and started toward the door.

"If you're tastes weren't so exotic, I'd agree with you," he said. "But you sure do like movies of shemales fucking men in the ass. Old man might not fire you, ruin things for his daughter, but you really think he's gonna want to leave the company to somebody who likes that kind of thing?"

I stopped. Kid had a point there. And I did like the shemale stuff. I wasn't gay or anything, there was just something, I dunno, really kinky about it.

"So what's your play here?" I asked. "Money?"

He gave a short laugh. "Nah. Reason I'm even pulling this now is I just sold an app to the Google people. Lawyers are papering up the deal now, be done by the end of the week. Soon as they do, I'm gone. Gonna be richer than you."

Now I was confused. "So what do you want?"

"Just tired of seeing assholes like you get away with everything. I've seen how you treat people. You're a dick."

"So you're going to turn me in? Just wanted to make me sweat first?"

"Up to you," he said.

"I don't get it."

"You're a bad boy, Luke. What happens to bad boys?"

"What?" I said.

"They get spanked. Take off your belt and hand it to me. Then strip and bend over the end of the bed. I'm going to give you a good ass whipping. You take it like a man, and the boss never hears about your porn habit. You don't, I rat your ass out. I've got it all loaded up in an email ready to go - dates, the sites you were on, the videos you watched. All I've gotta do is hit send. So take your whipping like a man or I press the button." He was holding his phone up in his hand now.

"This is weird," I said.

"We've all got our kinks. Right now. If you don't strip, hand me the belt, and assume the position in the next 15 seconds, the message goes."

OK. Not much choice. Humiliating, but I could take it. Then I'd figure out how to get back at the punk. I pulled my belt off and handed it to him. Pulled the sweater over my head, stepped out of my loafers, opened my pants and let them drop, and took off my boxers. I walked to the end of the bed and bent over it.

"Keep yourself in decent shape for an old guy," he said. "Now, lay flat, stretch your arms all the way out in front of you, don't move and don't scream. This is going to hurt."

I did as he said. He waited a minute, then I heard a swish and felt the belt smack against my ass. Jesus, that hurt. Then again. And again. He altered the spots each time, so the pain was always fresh. Finally, after 10 strokes, he stopped.

I stood up and reached for my boxers, too humiliated to say anything. I'd taken my whipping and after this week I'd never have to see the little shit again. I just wanted to leave.

"Where do you think you're going?" he asked.

"I kept my end of the deal," I said.

"And I'm keeping mine." He fiddled with his phone a second, then said "Every trace of your porn browsing on the corporate net is gone."

"Then we're done here," I said.

"OK, if you don't want to talk about your habit of picking up hookers online when you're out of town on business."

I froze.

"You were smart enough not to do that on the corporate net, but you use the same passwords for everything. Makes you a pretty easy mark. I can match up your text messages to your travel dates and to the cash withdrawals from that account your wife doesn't know about. Got all that in an email, too."

Now I was frightened. I didn't know what to say.

"Cat got your tongue? Just as well, I don't want to listen to you anyway. Here's the deal. You're going to do what I say, exactly when I say it, or I'm going to ruin your life. I send this shit, the old man will fire you, your wife will leave you, you'll lose your ass in the divorce, your kids will hate you, and the odds of you getting a job at anywhere near your level will be shot to hell. Nod if you understand."

I nodded.

"Good. In the bathroom, there is a little outfit hanging on the back of the door. Put it on and get back out here. You've got five minutes."

I went into the bathroom. On the door was a black Merry Widow-type corset with garter straps, a pair of black stockings and a black g-string. I could only guess where this was leading, but I was without options. I pulled the stockings on, put on the corset and snapped the garters in place, then pulled the g-string up. Just stood there for a minute, looking in the mirror. I've never been a very hairy guy. It was a little too close to some of the shemale stuff I'd watched for comfort.

Tim called from outside the door. "30 seconds."

I opened the door and stepped into the hotel room.

"Aren't you a pretty little bitch?" He said. He was standing at the foot of the bed. "Come here."

I came and stood in front of him.

"On your knees."

I knelt.

"Now take off my jeans."

There was no point in pretending I had an option. I opened the button fly. The jeans were tight and it was hard to pull them down, but I did. He was going commando. And he was hung. Only semi-erect right now, but his cock was already longer and thicker than mine, and mine was 8 inches.

"Now beg me to suck my cock," he said.

"Please let me suck your cock," I said quietly.

He slapped me across the face, hard.

"I didn't say ask, I said beg."

"Let me suck your cock," I said louder. He raised his hand again. "PLEASE! Shove it in my mouth! Make me take it. Please! I'm begging!"

"Open your mouth as wide as you can," he said.

I did.

He took my head in both of his hands and thrust forward with his hips. His cock slid into my mouth, down my tongue, all the way to the back of my throat. He rocked back and forth a few times, his cock getting harder as he did. It had to be close to 10 inches and it was thick. My mouth was completely full of it. Then he pushed harder, the head of his cock hard against the back of my throat. I gagged.

"You're going to have to do better than that," he said, pushing harder. "Sink down a little, tilt your head back."

I did as he said, which gave him an angle. I felt his cock start to push into my throat, completely cutting off my air supply. I panicked, reached up and pushed against his thighs. He slapped me again.

"Keep your hands to yourself. Now take a deep breath, because you're going to take it all."

I gasped in some air, then he shoved his cock forward again. I tilted my head back, giving him the angle. He pushed harder and the massive member went all the way in, his balls flattened against my chin. I was gagging and couldn't breathe, but kept my hands down.

He rocked back, his cock coming halfway out and I gasped for air, then forward, ramming it back down my throat. I just submitted to his rhythm. I don't know how long this went on. It seemed like forever. Oddly, I felt my own cock stir a little in the pouch of the g-string. Tried not to think about that. Just the feel of the silk, I told myself.

Saliva and pre-cum ran down my chin and all over the front of the corset as he rammed his cock in and out of my mouth and deep into my throat. Finally, he pulled all the way out and reached behind him, taking a tube of KY Jelly and a condom from the dresser. He handed the condom to me.

"Put this on me."

I did, rolling it down his massive, erect cock.

"Now bend over the end of the bed again, spread your ass cheeks for me, and beg me to fuck you."

I knew better than to be half assed about it this time. I bent over the bed, reached behind me and pulled my ass open as wide as I could. My cock was pressed against the mattress and had gotten mostly erect now, sticking out of the top of the g-string.

I had to beg and tried to think of what to say, but suddenly the words just spilled out of me.

"Fuck me! Shove that cock up my ass! Make me your bitch! Rip me open with it!" My cock got harder, and it felt like I meant it. I didn't know what to think.

And then I stopped thinking, because I felt him spread some lube on my hole, grab my hips and press the end of his cock against my virgin sphincter. He pressed forward. It seemed like I would not yield, but then it started to slide in. I felt like I was splitting open, like he was tearing me apart. It stung and burned, but he kept pushing, further and further in. It seemed like there was no end to him, or to the pain, like I could feel him all the way into my stomach. Then he reached the end, his cock all the way into my bowels. He stopped there for a minute, then pulled back slowly, back in, back out. Each time, it hurt a little less. Finally, there was a hard, deep thrust that didn't hurt at all.

Then he started fucking me in earnest, as hard and as deep as he could, a slapping sound as his firm, muscled thighs smacked into the back of my legs at the end of each thrust.

I went limp, just sprawled flat against the bed, and surrendered to him. I could feel my own erect cock twitching against the mattress with each thrust. I could no longer tell myself the shemale videos were just kink. I wanted this.

I was actually disappointed when he stopped and pulled out.

"Back on your knees, princess."

I spun and sank to my knees, sitting back on my haunches so I would be in the right position to deep throat him. He stripped off the condom and started stroking it in my face.

"Guess what I want now?"

"Please give me your load! Nut in my mouth! Shove it all the way down my throat and pump it into my belly! Feed me your seed!"

He laughed. "I didn't even tell you to beg yet, bitch."

Then he stroked a little faster, gasped. I leaned forward, taking his cock into my mouth, angling my head back and forcing myself forward to give him access to my throat. I rocked back and forth, actually fucking him myself with my own face. I reached up and gently cupped his balls in my hands. I felt them tighten, felt his cock pulse. He grabbed my head, seating his cock as deep in my throat as it could go. I didn't care that I couldn't breathe. As his load pulsed into me, I stroked my own cock, spurting the biggest load I've ever made onto the carpet.

Finally, his cocked stopped pulsing, twitched a time or two and was still. He slowly withdrew it. Once it was clear of my lips, I took it in both hands and licked every spec from it before releasing it.

"Look at the mess you made," he said. He pushed my head down to the carpet. I didn't need his instructions. I eagerly licked my own cum from the filthy rug.

"Good bitch," he said. "I have such plans for you."