Hell, Yeah: Shaun's Story Ch. 1

Story Info
The boss tells all.
4.1k words
4.77
86.9k
25
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
firstkiss
firstkiss
3,009 Followers

[To the men in my life: Jerry, who doesn't even know he inspired me to write this when he asked to hear Shaun's story; harddaysknight, for the advice, wisdom, and support only a fellow writer can give; Dan, for his uniquely male point-of-view and the glimpse at his boxer shorts; S.H. for inspiring the character of Shaun in the first place; and C. for speaking every day in Shaun's voice and making me feel as beautiful and loved as my heroines are.]

I feel a little guilty about it now, but the first thing I noticed about her was her breasts; they were great, the best pair I've ever seen on a real-live woman anyway. The doormen and the guys in the kitchen were betting they were fake but Jackie didn't seem the type; besides they had this way of bouncing under her t-shirt when she walked which was 100% genuine.

Getting to know her was easy, since we worked together a lot and she liked to talk. Frankly I was a little surprised that Mac hired her in the first place; generally the women he hired were hot and stupid. Jackie was cute and smarter than every other woman in the place. She was also hilarious to work with, and gave it back as good as she got it. You couldn't put anything past her and she took the teasing and joking like she was one of the guys.

In less than a month it seemed like she'd been working at Mac's forever; the customers loved her, Mac thought she hung the moon, and the place just ran better when she was behind the bar. I don't think the other girls thought much of her, possibly because they had nothing in common, but Jackie didn't put much score in the "skinny bitches" (her phrase, not mine) anyway.

She was tough and spunky and could swear like a sailor; and I wanted her from the first second I saw her. But life has a way of complicating things, no matter how much you wished it otherwise; she had a boyfriend. He was a fucking idiot and a slacker, but Jackie seemed attached to him so I didn't push the issue. She didn't talk about him much anyway, which suited me just fine; it was easier to pretend he didn't exist that way.

I dated too, the usual string of pretty girls without much between the ears. When you're a bartender it's easy enough to come by the willing ones, and although my low standards sometimes made me feel guilty I wasn't stupid enough to say no. If Jackie thought anything of my girlfriends she said nothing, which was weird because we could talk about everything else.

She had this way of flirting which seemed natural and fun; the customers responded to it and so did I. I'm not sure she was even aware she was doing it, but she had this way of making you feel at ease, like you were the smartest, funniest guy in the room. She tried to explain the niceties of hockey to me; I tried to enlighten her on football. We could talk all night about every subject under the sun or sit in silence and drink a half-dozen beers and be perfectly happy either way.

I could watch her work all night, loved the way she bent over to grab a beer from the cooler, loved the subtle curves of her body beneath her baggy golf shirt. As time went by I found myself just waiting for those opportunities when she'd brush past me; and hoped like a desperate teenager that she'd touch my arm or let me touch hers. She had this way of looking over her shoulder at you and smiling which made me hard every time. Each night we worked together was torture, but I wouldn't have given those shifts up for anything.

The first time I knew I was really in trouble was the night I spent an entire shift trying to figure out if her hair was brown or red and if her eyes were blue or grey; I was thirty-two years old and feeling like a fucking ass for wanting a woman I'd never have; she had me wrapped in knots and she didn't even know it. We worked together as friends for more than four years before my opportunity came.

The night she told me she'd dumped her slacker boyfriend I know I wore a shit-eating grin the entire shift; I tried to be supportive and sympathetic and all that crap that girls think they need, but she saw through it easily and didn't seem to care; her sense of humour carried her through.

"Fuck him," Jackie laughed, popping the cap off another bottle of beer. It was her fifth one of the night, a few more than she usually had after work, but she held her liquor better than any other woman I knew so I wasn't worried. "He's an asshole."

"Yeah," I muttered in agreement, watching out of the corner of my eye as she stripped off her work uniform to reveal the tank top underneath. It was such an unconsciously sexy gesture that I was hard instantly.

"I'm not thinking about him ever again," she sighed, tossing her wavy brown hair over one petite shoulder; her hair looked so soft I just itched to touch it. "I'm a strong, independent woman; I don't need a boyfriend." She giggled semi-drunkenly into her beer.

I chuckled, raising my beer in a silent toast; Jackie smiled her sexy little grin in return and we both went back to watching sports highlights in the darkened bar. It was our nightly post-work ritual and we'd been doing it for four years but all of a sudden it felt different to me. She was right there, sitting beside me, completely unaware of how fucking cute she was and how much I wanted her; if I was a braver guy I'd have reached for her right then and there, but I was scared she'd turn me away. After all, she didn't treat me any differently than any other guy she knew and at the time I had no idea what she really thought of me.

The truth was Jackie did need a boyfriend; she deserved a man who would treat her well and live to make her happy. I wanted to please her, to take her home and show her how much I wanted her, how possible it was for her to be satisfied. I knew the sex would be amazing between us, and I ached to show her just how good we could be together. But common sense got the best of me and I sat silently and watched the light of the television flicker off her face as she got drunk in celebration of being single.

And so I started seeing Lisa, mostly because she was pretty hot and she'd been easy to get; she flirted openly with me one night while I was working and I took her home. If Jackie noticed she didn't say anything; we'd always been strangely silent in regards to our relationships outside of work and every time I fucked Lisa I felt a little guilty because I was wishing she was someone else.

There were a lot of things I could never tell Lisa, it was almost like she didn't care that I had friends, a job, or plans for the future; and at times I suspected she was using me just like I was using her. It was no surprise to either of us that we broke up and I can't say I missed her when she was gone.

But I had a hard time telling Jackie and I didn't know why. Maybe because we'd never really talked about my seeing Lisa; maybe because I didn't want her to think I was a shitty boyfriend; maybe I just didn't know what to say.

I felt like I was stuck in a purgatory of my own making, waiting for things to happen in my career; waiting for the girl of my dreams to notice me; waiting for the fucking balls to do something about it all.

And then the opportunity came and I still can't believe that it happened.

It was the Sunday of the NFL division finals and I'd left the office to help Jackie bartend; not that she needed the help, she'd bounced around behind the bar with her unique blend of cheerfully sarcastic excitement all night long; her mood was so contagious that by halftime I'd forgotten the bitchy, post-breakup-bull-shit phone call from Lisa earlier in the evening.

So I teased and flirted and Jackie gave it right back, unaware of the effect her sexy little laugh had on me. The shift flew by even though I kept finding myself distracted by the smallest things: the little curl which had escaped her ponytail to rest against the back of her neck; how good she smelled when I got close enough to breathe her in; hell, even the way she wrapped her hand around a bottle of beer had me thinking the wrong things.

So when the night was over and we were having our post-shift beer I told Jackie about breaking up with Lisa and she seemed genuinely concerned, and when I put my arm casually around her and she didn't shy away I was so pleased I couldn't keep the grin off my face. All I could think about was kissing her and how warm her bare shoulder was against my arm.

How we got on the topic of oral sex I'll never know, but Jackie slipped it into the conversation so easily it made my head spin and my dick hard. I choked on my beer while she laughed and cleaned up after me. We'd always avoided topics like that and when we went back to watching sports highlights she was strangely quiet. Usually she pestered me with questions and comments and I couldn't help but wonder what was going on in her pretty little head. It was just as well that she didn't know what was going on in mine.

"What is this?" Jackie asked after a long stretch of silence; she kept her eyes glued to the T.V. screen.

I tore my gaze from the Bulls/Pistons highlights to glance over at her and tried to sound cool. "What is what?"

"This. Whatever this is, you know, between us. What is it?"

My heart stopped; the little voice in my head was screaming at me to make my move. I tightened my arm around Jackie, swivelling her barstool so we faced each other again, knees bumping. I wound my other arm wound around her too, caressing the length of her bare arm and watching as her beautiful blue eyes grew wide.

"I don't know," I admitted, hoping I sounded more confident than I felt; I had no clue what I would say or do if she turned away. "Want to find out?"

A sexy smile bloomed slowly across her face, and I found myself wondering why I'd ever thought her cute; Jackie wasn't just cute, she was fucking gorgeous.

"Hell, yeah," she whispered and then she kissed me. Later we would argue as to who kissed who first; I'd never admit that it was her, but to be honest it was and the fact that she wanted me back made me dizzy.

Every bone in my body jolted with shock as our lips met, and when her tongue found mine it took a moment for my brain to register what was happening; my cock, however, was right on board.

So I did what was I'd been dying to do for four years: I kissed her back. All the while hoping it wouldn't be the last time because she was amazing. Her mouth was scalding hot, her tongue insistent; she met every move I made with one of her own and made the sexiest little noises I've ever heard. It's possible I forgot to breathe.

I tightened my grip around her narrow waist and deepened our kiss. I couldn't keep my hands off her; I wanted to touch her everywhere. Her curves were amazing beneath her white tank top and I was hard just from knowing they were mine to touch, at least for the moment. Jackie dug her hands into my hair and moaned sexily, holding on to me as if she were afraid of falling off.

I wanted desperately to move the proceedings to somewhere more comfortable. It was way too warm in the bar and Jackie was practically sitting on my lap. Let me be the first to say that there isn't enough room on one barstool for two people, especially when one of those people is getting bigger every second. No girl has ever had me as worked up as Jackie did and I wondered what else she was capable of; I was aching to find out how far she was going to let me go.

"Fuck." I panted, breaking the kiss with a gasp. "If I'd known you kissed like that, I'd have done it long ago." I couldn't help but grin like an idiot while Jackie laughed and traced the edge of my jaw with a soft finger; my cock jumped inside my jeans. "We can't do this here," I smiled, leaning forward to drop a path of kisses along the length of her neck; I'd wanted to kiss that spot for four years and was well rewarded for my patience when Jackie arched against me, purring deep in her throat.

"The office?" she gasped raggedly.

I was so excited I wasn't sure I could stand but I helped her off her barstool and lead the way through the doors into the back hallway and then into the office I shared with Mac; there was a sofa in there which was the ugliest thing known to man, but it was damn comfortable. I'd never fucked a girl on it, but I sure as hell was going to try.

I sat down on the sofa and pulled Jackie down to straddle me; for a moment there was a nervous look in her eyes and I was afraid she'd bolt, but she started kissing me again and I forgot all about being scared that we might be messing up a great friendship with a moment of passion as what little blood left in my brain shot straight from my head to my cock.

Jackie had her hands in my hair again as I traced the sexy curve of her hips and waist, trying to get up the courage to touch her breasts; when I finally brushed against them Jackie moaned encouragement. Chuckling, I ran the pad of my thumb across her nipples, in awe as the contact made her arch her back.

"You like that?" I laughed, gasping as I broke our kiss. Jackie nodded wordlessly. "I want to see them. Take your shirt off."

She shifted her position on top of me, pulling the white tank top off with an enthusiastic yank. There was a minute when I couldn't do anything but stare at her breasts; my first impression all those years ago had been right, they were fucking amazing. She was wearing some sexy, lacy white bra that was so completely unexpected I almost forgot what to do; nervously I ran my hands over the white lace; her nipples hardened even more at my touch.

"You should not hide these beneath those damn golf shirts." I murmured as I lowered my head to run a line of kisses across her chest. "I'm voting for a change of uniform."

Jackie shook her head and said nothing, but her eyes were wide and there was a small smile at the edge of her mouth which I longed to kiss, except that I was temporarily distracted by her breasts. "The little t-shirts didn't fit," she gasped as I licked her right nipple through the lace of her bra. "I tried, too tight."

"I would have loved to see that." I couldn't help but laugh even though the mental image of Jackie trying to wiggle her amazing breasts into one of the waitress's little t-shirts was sexy as hell. I wasn't sure if she'd appreciate the joke however, so I just stuck to doing what I was doing and kept licking her hard nipple, all the while wondering how much harder it was going to get.

"I bet," she teased, running her hands across my shoulders as I sucked at one breast while flicking the nipple of the other with my thumb. "You perv."

I bit gently at her hardened nipple and laughed; half at her teasing me and half in disbelief at the situation. My cock was rock hard inside my jeans and Jackie knew it; she wiggled her hips against me and I groaned. I clutched her ass and pulled her closer, trying to keep her from wiggling too much and spoiling all the fun before it had hardly begun.

I started kissing her again, partly because I couldn't resist the bottom curve of her lip and partly because I was dying to distract her enough to undo her bra. It's the oldest trick in the book, but it works, and the look on her face when her bare breasts hit the cold air told me she hadn't seen it coming. Then I just leaned back against the couch and stared; I couldn't help it, she was glorious. Grinning broadly, I palmed the generous weight of her breasts with my hands.

"Damn," I murmured shakily, unable to hide the hitch in my voice. "I've been fantasizing about these for four years. They're even better than I thought they would be."

"You fantasize about me?" Jackie asked, grinding above me. The pressure in my boxers was starting to become uncomfortable, but I couldn't have stopped her if I wanted to; I'd dreamt about the moment for too long to let a little discomfort get in the way.

"Hell, yeah." I ran my hands around to her spine and down to cup her ass, kneading her through her jeans.

"What about the Skinny Bitches?" Jackie asked with a cute, little pout. "Do you fantasize about them?"

I straight out growled at her; how could she not see how amazing she was? Even when pressed against evidence as obvious as my hard-on did she really have no idea what she did to me? "I don't want the fucking Skinny Bitches." I ran my hands possessively over her ass, the curve between her hips and waist, the heavy roundness of her breasts. "I want you. I've always wanted you." I grabbed the back of her neck and kissed her hard, unsure of how else to prove my point.

I don't remember getting naked I only remember that we must have, because suddenly we were back on the couch with her straddling me and nothing in between us; it was the most amazing feeling in the world. Jackie was hot and soft and smelled so fucking good that I could have died right then and been a happy guy. Her body was everything I'd fantasized it would be; curvy and smooth, with sexy little sprinkles of freckles that I'm sure she hated but which I was starting to love; I wanted to trace out each path with my tongue to find out where it led.

I dipped my hand between her legs, feeling for the slick heat of her; she was wetter than I ever would have thought and I could have come right then and there, but she beat me to it.

"Shit," I laughed, shaking my head in disbelief as she arched her back and moaned with pleasure. "That didn't take much!" I ran my fingers further, dipping into the warmth of her pussy; she was so hot my knees were shaking. It was a good thing we were sitting down.

"Sorry," she apologized, leaning in closer to kiss me. "It's been a while."

"I just hope we haven't finished before we've begun," I laughed, feeling her muscles contract around my fingers. My head was reeling; when I'd woken up that morning I never would have guessed that before bedtime I'd have my fingers buried inside her. Dear God how I wanted to bury more than that.

"Hell, no. I can have a few more." Jackie smiled brightly and there was a daring glint in her eyes which I liked.

"Really? Lucky girl. How many?"

She shook her head. "I don't know. I've never kept track. I usually lose count after six or seven."

Laughing, I bent to briefly take a nipple in my mouth. I removed my sopping fingers, rubbing my hard cock against her. "That sounds like a challenge." Some day I was going to see how many I could give her; at the moment however, one more would have been enough. I could feel myself grinning like a fucking idiot, but everything was so unbelievably perfect that I couldn't stop.

"Please," Jackie moaned as she ground herself wetly against my cock. I didn't want to wait another second; I didn't think I could have if I tried.

"Gladly," I growled before putting my hands around her narrow waist and lifting her enough to fit myself inside. Even though I'd done it a million times, with a dozen different girls, Jackie just felt different; it was the best feeling in the world and hearing her scream as I filled her almost made me come on the spot. "Shit," I said through gritted teeth, trying to hold on long enough for us both to enjoy it. "You're so fucking tight. This isn't going to take long."

"No worries," Jackie gasped as we easily found our rhythm. "You'll owe me."

"I want to see you come again first." I ran my hands up to her breasts, letting her set the rhythm, so fucking pleased when she got it just right. She felt so good around me and looked so good riding above me that I couldn't have spoken if I tried; I wanted to remember every second in case it never happened again.

As much as I wanted her to come again, I was starting to get worried that I'd finish before she did; but once more Jackie didn't disappoint. She cried out as she came a second time, the hot walls of her rippling around my cock, driving all thought of my holding back from my head; I felt myself explode with a growl, vaguely aware of Jackie through the fog as she slowed her movements above me. My ears were ringing from the combination of her cries and my own orgasm; it was the best I could ever remember feeling.

firstkiss
firstkiss
3,009 Followers
12