Pegging The Boss

Pegging the Boss
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File Size: 132 KB
Print Length: 25 pages
Fortmat: ePub
Features: Flowing text
Language: English

Price(USD): $0.95


Traffic was a bitch on I-95, and I knew I’d be late. Some dark-haired asshole who looked like an FBI-type in a Beemer and Oakley mirror sunglasses tried to cut me off when I was three cars away from the tollbooth as I eased off the turnpike onto the interstate. Came within an inch of my bumper. White hot rage shot through me, along with a flushed, hyper-alert sense. No way. I sat in this fucking line for 20 minutes and now Mr. Entitlement USA thinks he can cut me off?


He waved and shrugged, like he was oh-so-innocently asking for a small favor. I shook my head slowly, glad I was wearing sunglasses, too, because the red-hot death ray would have shot out my eyes and burned him to a gristled little crisp.

He smirked and shot forward, tapping my bumper. Fuck you, buddy. My car is crappier than yours and I am insured. You hit me, you’re slumming.

I eased up and turned the wheel slightly to the left. No way I was hitting him. Ever vigilant, I made it so that in this game of chicken, I would win. Move an inch, take an inch. Like sex, I was doing to get what I wanted.

Right now.

He backed off and I moved forward, victorious. BAM! Take that. Someone with less determination than me right behind me let him in. I looked in my rearview mirror and realized he was flipping me off.

So I shot him the bird back. Fuuuuuuuuck you, dude.

And then he proceeded to follow me. Fine. Whatever. We were trapped in gridlock for the cloverleaf onto I-95, so I pulled out my makeup case. I always ran out the door a few minutes late, so I’d learned to prioritize. Powder, blush, mascara, lipstick. Done. I’m sure in a few years I’ll need a hell of a lot more makeup, but at 21 the worst I need is a little undereye concealer if I party all night and come into work a little hung over.

Not true today, though. I got what I needed last night. My boyfriend, Darren, finally put out. That man has a tongue that could lick the moon if he really tried. Damn. Too bad he has to drink a six pack before he’s willing to go down. My clit appreciated the effort, and it was a nice change from our boring, vanilla sex. I mean, missionary position is nice once in a while – what woman doesn’t like to have a broad man’s back to grab onto and scratch when she’s screaming and coming like a freight train with a full load – but every single time?

If I climbed on top of him and rode his pole he practically yawned. Getting that tongue to flick my pussy took a ton of alcohol. And when I suggested using a strap-on last night, that had, apparently, been the last straw for poor old Darren. His baby blue eyes had bugged out of his head.

“Lindsey, you’re nuts!” I’d never seen a person actually spring out of bed, but Darren managed it, naked and loopy from the beer. We hadn’t even had intercourse yet; he’d finally gone down on me and I’d been moaning with pleasure just a few seconds ago.

“No – it’s just a thought. I figured we could be adventurous.”

“By shoving a plastic dick up my ass?” Now he was scrambling into his jeans. He yelped – catching some pubes in his zipper as he rushed. I bit my lip to stop myself from laughing.

Ah, damn, I wasn’t going to get his cock in me now, was I? “Well,” I crooned, climbing across the bed on all fours, letting my breasts dangle and rub against the sheets, sending tendrils of lust down to my increasingly-wet pussy, “everyone has fantasies, you know? I just thought I’d – ”

“No fucking way, Lindsey. I’m done. It’s bad enough you want me to – ” he waved vaguely at my crotch – “put my mouth on, on that. But now you want to be the man and fuck me with a dildo you wear around your waist? You need to see a shrink.”

Now I was pissed. “If anyone needs a shrink, Darren, it’s you. If you have to liquor up in order to, well, lick her up, then you might be gay. Go find a nice bar with men and explore a little. Have a nice life.” I’d been screaming the words as he walked down my apartment hallway and slammed the door just as I said the word “life.”


And that had been my night. The end of a weird 6 weeks with Darren.

So no undereye concealer today. I’d gotten off and ended a relationship. Today was about being reborn, cleansing myself, and just breathing. It was Friday and I had decided at the last minute, before running out the door, that I would go on a little trip, alone, to my parent’s cabin in Vermont. Packed up some good erotic romance novels, my sex toy collection, and some Junior Mints, all neatly crammed into my laptop bag. Sitting in a cabin, watching porn and reading some good, raunchy shape-shifter crap was my idea of a cleanse.

This asshole in the Beemer kept following me as I pulled off the interstate and went down the back roads to the office.

And then pulled into my parking lot at work.

He parked in a spot right by the main door. The spot that said “Reserved for the Vice President of Marketing.”

I was the new marketing assistant.

Oh, shit.

The asshole in the Beemer was my boss. Mark.

All I was trying to do was get to work on time. The damn turnpike is always crowded, but there’s always someone at the front of the line who will let me in. A $50,000 contract at work was at stake; if I was late and lost the client, I’d lose my job. I drove up past the 40 or so cars in line and figured I’d edge in. And then I saw Lindsay, the new marketing assistant, in her little red compact car. Damn. It’s like the universe read my mind. Just this morning the alarm clock had woken me out of a hot dream, with Lindsay the leading lady. She was only six years younger than me, and that auburn hair drove me wild. Were the silky curls leading to her womanhood auburn, too? Could my tongue blaze a trail through that blazing hair? My cock pushed against the zipper of my pants and I shifted in my seat.

Surely she’d let me in – she knew how important this client meeting was. I eased my dad’s Beemer into place and tried to get ahead of her.

No dice. So I stared at her, hoping she’d recognize me. When she finally looked at me, her cool gaze turned me on even more. Rich hair the color of copper pipes, with painted lips so full they could take on my erect cock – and more. Her pert nose rested perfectly under a pair of sunglasses, skin the color of new milk. And I could see a hint of breast in her cleavage under the suit jacket she wore, unbuttoned and hanging under her seat belt. And beneath the steering wheel I knew those long, lean legs were pushing pedals, while my hand wanted to reach down, slide up her calf, over her thigh, and stroke her off.

My hand actually reached for my own damn thigh and nearly unzipped my pants and stroked off right then and there. Instead, I clamped down on my own steering wheel and smiled at her, then shrugged.

She shook her head “no.” Ah, come on! I shot her a nasty look and beeped my horn, a friendly tap. She turned away and grabbed her steering wheel.

So it was going to be like that, huh?

Winning games of “chicken” was my specialty. I tightened up and pushed forward, inches at a time, trying to get her to let me in. She fought back, though, and I tapped her with the BMW’s bumper. My parents would kill me if I cracked it, though. I’d have to let Lindsay win.


This time.

She got through and I flipped her off reflexively, not even thinking about it, but she saw me and returned the bird. A flash of anger and arousal filled me like a balloon at a helium tank. Could she piss me off even more?

Could I want to fuck her even more?

We’d settle this at the office. Maybe it was time for a performance review for Ms. Lindsay. A very detailed, intimate performance review. And as long as we took care of things after hours, it would be fine.

Wait – no. Down, boy. You’re a VP now. Twenty-seven years old and a fucking VP. No piece of ass, no matter how intelligent and hot, would derail that.

Or would it? My cock itched to sink into her. To claim her. To show her, exactly, who was the boss.

Mark parked his car and I pulled into a spot way, far across the parking lot, as far as I could get from him. Oh, shit! I just got into a road rage contest with my hot boss!

And I’d won. An evil grin stretched over my face. He was new, like me, and eager to prove himself. Like me. I had decided before I graduated with my bachelor’s degree that I would never sleep my way to the top. Mark had made that very, very hard these past few months. He looked like a young version of David Duchovny, tall and lean, calm and together, with a droll manner and laughing eyes that were intelligent and – under the surface – passionate. Maybe even kinky.

If he had half the kink I hoped was there, then I’d quit my job just to fuck him. Whoa! Where was that coming from? I wasn’t about to lose my career over some hot guy. No, no, no.

What the hell was I doing, fantasizing in the parking lot like this? My boss had just tried to cut me off on the turnpike and I had played a game of “chicken” with him. And won. And we’d flipped each other off.

I might lose my job even if I didn’t fuck him.

A heavy sadness overwhelmed me, tinged with anxiety. Walking into the building was hard. “Hi, Lindsay!” shouted Lou, the old security guard who manned the front desk. I waved back and pulled out a cheerful smile. Lou beckoned me with one finger. “Watch out,” he whispered conspiratorially. “Mark just blazed through here, and he seems pissed.”

“Oh, yeah? Thanks for the tip, Lou,” I said, walking slowly toward the elevator. The four-story ride felt like a walk to Death Row. I got off the elevator and scurried to my office, hoping no one would talk to me. Once I was safe behind my own closed door I booted up my laptop and tried to bury myself in email.


That worked for about 45 minutes.

And then Mark barged right in to my office, scaring me. I jumped up and my jacket slid off my shoulders, falling around my elbows. Shrugging my arms worked, but it also made me heft my breasts, which Mark zeroed in on immediately.

Subtlety wasn’t his strong point. He’d been eyeing me for months, since we both started.

“So what the hell was that on the turnpike, Lindsay?” he growled, pacing back and forth in front of my desk. He was wearing an expensive Brooks Brothers suit, a pinpoint white oxford, and a tie that probably cost more than a week of my salary. Dark brown hair cut perfectly to frame his strong jaw. Chocolate eyes that begged me to turn them dark and impassioned.

But he wasn’t winning this one. “I could ask you the same thing! Cutting me off like that. I’d been in line for 20 minutes. Just because you drive a BMW doesn’t mean you get to cut like that.”

“The McClintock campaign was this morning. You made me miss the beginning of the meeting. A $50,000 contract.” He looked at me like I was the stupidest thing on the planet.

Ah, fuck. I’d forgotten about that. “How was I supposed to know who you were? I didn’t realize it was you until you pulled into your parking space, Mark.” Now my arousal was turning to irritation. If he was just going to bully me, then forget it. My sex toys, Junior Mints, and YouPorn were all I needed.

He walked around the desk and reached toward me, his hand firm against my right forearm. “I tried, but you were in your own world.” He smiled with his eyes, but his mouth was set in a strong, angry line. The mixed signals were confusing.

“I can’t read minds, you know?” I shrugged, willing away the surge of lust that his touch brought out in me. My eyes lingered on his belt buckle, looking down, down to find the upright bulge I wanted to ride. A pool of warmth filled my panties, which I wanted him to remove.

With his teeth.

“You can’t?” His voice was like warm velvet. “I thought you could. That’s why we hired you. For your – ” his eyes traveled down my body, then back up, his face flushing and eyes darkening with desire. “– mind.” His hand began caressing the inside of my elbow, brushing lightly against my breast. I inhaled and nearly moaned.

“Lindsay, I think you can read minds.” He pulled away and sat up on my desk, legs spread toward me.

“What am I thinking right now?” Maddeningly, his face showed virtually no expression. His eyes and body, though, burned for me.

My clit wanted so much more than it had gotten from Darren last night. To think I’d been satisfied – no, convinced myself I’d been satisfied – by Darren’s pathetic tongue, when this man was standing in front of me, wearing a neon invitation that screamed “Fuck Me Right Now”? Hah.

“I think you want me to fuck you.”

He grinned. “I think you have that backwards.”

A thought hit me. If we were going to do this, let’s do it all the way. Reaching into my laptop case, I fumbled to find my target. Got it.

Clutching my new strap-on, I slowly pulled it out and into view. “No. I don’t have it backwards at all. I think – ” I said, stepping between his legs and running the tip up his thigh, “–I want to fuck you.”


Now, this was the point where I either got fired or I got laid. Well, Mark got laid. Someone was going to get fucked either way.

This was not how I expected my quick meeting with Lindsay would go. When I marched into her office, having managed to save the McClintock campaign and signing the new contract, I thought I’d chew her out and, maybe, convince her to go out for drinks after work. Angry? Yes. Frustrated? Sure. Victorious? Yep.

Being asked to be ass fucked by a strap on? That was not what I’d expected. At all. This was new territory. Virgin territory, you might say. I’d had a pinkie finger here and there shoved in me by an enterprising girlfriend, but no one had every suggested pegging. So now my direct report wanted to turn me into a bottom?

Who was the boss here?

I arched my eyebrows and stared into her green eyes. She blinked twice, coquettish and pretending to be guileless, but the promise of freaky fetish sex was too incongruous. Who was this woman?

And where had she been all this time.

She stroked the strap-on’s head against my shaft, slowly following my dick from base to top, applying slightly more pressure as she hit my mushroom cap. I grabbed her and pulled her face to me, kissing her and parting those lush lips with my tongue. An eager mouth met mine as we immediately became Human Resources’ worst nightmare. Thankfully she was such an underling in the company that she’d been given a crappy office with no windows. As if reading my mind – hey, maybe she really could! She pulled away, went to the door, and locked it.

Then she turned around and began a slow strip tease. Panties first, which she brought to her face and sniffed, then threw at my head. They bounced to the ground but I didn’t retrieve them, instead mesmerized by the show. She scooched out of her skirt, revealing a heart-shaped ass and hips meant to be clutched from behind, perfect handlebars for rear entry.

Next, her shirt, which she threw off with more haste. Then her bra. Now she was naked and she came back to me, breasts as soft and supple as I’d imagined them while jerking off at home, Or in my office next door. She hadn’t known, so it had never hurt to think about fucking her. I stopped for a moment – or had she?

And then she reached forward and with one swift move unbuttoned and unzipped me.

Ah – she read my mind. I slid off the desk and slipped out my clothes. Now we were both naked.

“The staff meeting!” she suddenly squealed. The clock read 8:56 a.m.

“I’m the boss,” I murmured as I drew the length of her to me, pressing every possible square inch of our bodies together. “If I don’t show up, they won’t care.” She relaxed into me and her hands roamed my back while I lowered myself, licking a trail between her breasts, tongue finally reaching that blazing crotch, ready to tongue her into a frenzy. With gentle hands I parted her legs and flicked once or twice just enough to make her shudder.

Then I stood and lifted her on the desk. “I need a more ergonomic office environment, Ms. Jennings,” I said as I went down on her, the scent a musk mixed with lavender, her curls hiding a bright red nub and a slick hole that was ready to be filled. She filled her hands with my hair, pushing me rhythmically into her clit, tongue tracing careful circles and linear lines designed to provoke her, but not take her to orgasm yet. I slid a hand up to find her nipple and pinched, then entered her with two fingers, one hooked up to find her G spot.


Her breath hitched with a pattern I knew. Soon she was writhing and screaming through gritted teeth, shoving my face into her clit, grinding into me as I struggled to follow her, tongue using a steady pressure to keep her going as wave after wave made her juicy and soaked.

She eased down from her orgasmic wave and then sat up, hazy and unfocused, yet oddly determined.

“Your turn,” she said, and I stood there waiting for her mouth.

Instead, she reached into her laptop bag and brought out a bottle of lube. Then she reached for the strap on, slid it up into her wet pussy, and closed her eyes. A long sigh and a sudden tightening of her abs showed me a slow, simple orgasm I didn’t know women could achieve. And then she withdrew the strap-on’s dildo and clinched it around her hips.

“You weren’t kidding?” I asked.

She feigned innocence. “Whatever made you think I was?” Then a laugh that sent shivers through my dick and into my ass filled the room.

She shot me a questioning look. “You in?”

I hesitated, then smiled. “No, but apparently you will be in a few seconds.”

And that’s all it took. She guided me onto the desk, in the same position she’d been in a minutes ago. This was new – missionary with the man on…bottom.

She took the lube and stroked the dildo carefully, loading it up, blending it with her juices. Then, using the same hand, she slid one finger in my asshole, pouring more lube over my hole with the other hand. I was soaked, and so was her desk blotter. She grabbed a small footstool and stood on it, trying to find the right height and angle. And then – pressure and pleasure. Withdrawal. In – out. She’d go in a half inch, then my muscles pushed the dildo out. In – out. Her hips bucked, slowly, like mind did during sex with a woman, except hers were less practiced, more awkward My hot, red, tight cock was screaming for attention but I didn’t care, fascinating and aroused by the attention my ass was getting.


And then – pain. Exploding, blinding pain that filled me and completed me. Pleasure and climax all at once, the friction that withdrew the sensation to nothing. Then the filling and friction. And now – oh, oh oh! A perfect pressure point inside that made me writhe, grabbing anything I could reach, squeezing the life out of it as the agony and the ecstasy blended.

And then it was gone.

Back again.

Gone. She pumped in and out, with more practiced strokes, her hands preoccupied with balance. I reached for my cock and nearly came with one light touch.

Then she did it for me, solely with the strap-on, as something shifted and now a pleasure vortex in me turned my entire world into one pinpoint of orgasm, shattering everything in the room. I grunted and groaned; she put a hand over my mouth. I bit her palm and she used her other hand to touch herself, head thrown back, my mouth biting her and her other hand bringing her wave after wave of climax as we rode the ocean together, surfing through this tsunami of lust.

And then the phone rang.

I fumbled to answer it, heart pounding, cock twitching, head reeling. “Mark Warham.”

“Mark, I think you forgot about the staff meeting,” my secretary said.

“Oh.” I stared at Lindsay, who was grinning triumphantly at me. “Yeah. Be there in a minute.” I hung up. We both started getting dressed. My orgasm left me with a jizz covered belly; Lindsay kindly handed me a box of tissues and I laughed. She kept sneaking glances at me and smiling.


Fully dressed, we looked at each other. “Do I look OK?” we asked in unison.

Laughing, we both answered, “You’re fine.”

“So, how was that?” she asked.

“I feel drained but full, all at once,” I answered, suddenly a bit self-conscious. “Is that normal?”

She flinched and looked unsure of herself. “How would I know? I’ve never done that before.” She slid the strap-on into her laptop bag, along with the bottle of lube.

“So why did you…?” I let the words hang in the silence.

After a full minute passed, she looked at me and said, “It’s like playing a game of ‘chicken.’ Whoever backs down first, wins. I figured I’d throw it out there and see if you, uh, backed down.” An evil grin filled her face again, making her glow.

“Then we’re 1-1 for today,” I replied, pulling her to me for a kiss.

“That depends,” she said between kisses, “on how you interpret the game.”