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Tommy Boy

I hadn’t meant to corrupt him ­ it just sort of…happened.

As with most tales, this one begins at the beginning, all flowery prose and propriety, introducing first myself, and then the character that we’ll call “Tommy Boy,” for the sake of his anonymity.

My name is Kayla North.

I am a Canadian woman thirty years of age, as of last month, and hopefully the wiser for it. I am of above-average intelligence, and average humor, and hold a degree in Computer Science from the University of Manitoba. My education is the one thing that I’ve not yet had the opportunity to apply to the ‘real’ world, for reasons I’ll disclose shortly.

I am five foot nine, one hundred and forty pounds, the last time I checked. I have dark green eyes and long hair that is naturally quite curly: I dye it burgundy every two months. I use my Shapes Co-Ed Fitness Center membership on a daily basis, and as a result, am in immaculate shape. I am a bisexual by nature, and dominant partner by choice. I haven’t had a steady boyfriend or girlfriend for the better part of three years: I prefer it that way.

I am a firm believer that the benefits of casual sex outweigh the disadvantages of such a lifestyle…

I am the Owner-Operator of the Boulevard Motor Hotel located at sixteen hundred Queen Avenue, in Winnipeg, Manitoba, Canada. I won the place in a poker game with the previous owner, Bill Gilroy, who had recently won the 6-49 lottery and was feeling as generous with his wagers as he was feeling rathe…amorous that night. Which meant very generous, and very amorous. He was after a piece of my ass, and didn’t seem to mind that all that I, university student, could afford to wager against his bar was my piece-of-shit Honda Accord, a striptease, and a blow job.

Suffice to say, I did not lose, but won the bar instead (and Bill Gilroy is now retired in the Bahamas somewhere, likely still chasing after university-aged pussy). So, long story short, I’ve been operating the Boulevard for the better part of nine years now. The place turns a good profit, and I love the ambiance and the people ­ from the circuit strippers to the DJ to my bartenders to my waiting staff ­ I wouldn’t give them up for the world. I can’t imagine leaving the Boulevard to pursue a career in computer science, especially since my education is now all but obsolete. I’ve never worked in the industry, so I’d likely be so far behind the times…

I’m a Pascal, COBOL, C and C++ programmer in a Java and HTML world.

Suffice to say, it would not be worth my while to pursue computer science. And besides, I’m happy with my Boulevard. At times, I’m ecstatic with my ownership! And I have so many reasons why…

Perhaps I’ll tell you a little bit about the Boulevard or “Bully” as we like to call it, before I introduce Tommy Boy, my former flavor of the week…

The Boulevard Motor Hotel consists of three parts: a thirty-six seat licensed restaurant called Amanda’s, a fourteen-room hotel on the second floor, and the ‘Bully’ beverage room itself, which seats a hundred and twenty, and has standing room, and Video Lottery Terminals (VLTs) for plenty more. The Bully also has a cordoned-off eighteen-by-eighteen foot dance floor, attached to the DJ booth, with two removable ceiling- to-floor poles for the strippers’ shows. The tables are all round, with four chairs a piece, and sturdy despite the many bar brawls that have occurred here over the years. There’s an L-shaped bar where two bartenders are normally stationed, with a third bartender on Whisky Wednesdays and Fun Fridays, our busiest nights of the week.

Our motto here at the Bully is “cheap booze and wild entertainment.” The strippers work from Thursday thru Saturday (inclusive) with six shows a day, and we usually have a live band or new DJ every Wednesday night. Monday nights are our football nights, when we have the game on the big screen (in season). Tuesday nights are Ladies’ Nights, we try to get the male strippers in for a show twice a year; even more often if we can book them ­ they’re harder than hell to book, unless you know the people involved personally (but then, that’s another story).

Though I’m a non-smoker by choice, the Bully is not; we have an awesome air-exchange system that clears out most of the smoke, making the atmosphere a pleasant one for all concerned. On the dance floor, the music is blaring, enough to make one senseless, but in the tables along the walls, the noise is low enough for one to carry on a decent conversation, without having to scream your replies over the newest Top 40. There you go – that’s the Bully, my favorite part of the establishment, and by far, the most profitable end of my business…

Now the story I’m about to tell you is one that occurred the summer I turned twenty-five. I was younger then, and as ambitious as always, both in and out of the bedroom. This is the tale of Tommy Boy, who I will introduce to you now.

Tommy Boy walked into my bar like he owned the place, which sort of irked me, this being the first moment I had ever seen him here. He walked like the pompous sort of jackass who has a big dick and likes to get laid a lot…the kind of pompous jackass who thinks himself above reproach, and above women in general. The kind of guy that really irritates me, really pisses me off.

The kind of guy who needs to be taken down a notch… or two.

I was bartending that Thursday night, since Theryl was going to be a few minutes late, due to car trouble. She was one of my favorites, while under my employ ­ a very dedicated and hard worker, that girl. Theryl made one hell of a margarita, let me tell you… I lost her a few years ago, when she decided to take up Nursing. She comes in here once in a while with her new husband, so it’s nice to see her familiar face, even if she doesn’t work here anymore. I never burn my bridges, old lovers being the only exception.

Tommy Boy would come to be one such exception…

He was blond haired and well built, easily six feet in height, with broad shoulders and a real fly-popper of a package. He had a perpetual hard on, as he would for the duration of the short time I knew him. As he approached my bar, I could tell that his blue eyes were fixed on my breasts, acknowledging my tits before he acknowledged my face. Irritating, in short. He made a point of staring at them, as though he had never seen a C cup before…

It was then, from his first glance, that I decided to break him, however I could.

“Hi,” I greeted him anxiously, with the slightest bit of mischief in my smile. “Haven’t seen you in here before.”

“It’s my first time in here, actually.” He replied with a lazy drawl, his baby blue eyes stealing away from mine to glance again at the plunging V-neck of my shimmering gold shirt. So he liked my boobs. A lot. Not that I can blame him: they’re a very nice set, perky with youth, but rounded with maturity. Two perfect handfuls…

Anyway, he seemed easy enough. I would soon learn just how easy he was…

“What are you having?” I asked the brazen boy, guessing his age to be at least twenty.

“I don’t know ­ what time are you off?” He smiled at me then, and I saw a predator in his grin. He obviously thought himself so… smooth. In truth, his youthfully naive overconfidence was really quite amusing.

This was going to be too easy…

“As soon as Theryl gets here.” It was just my luck that she was behind me at the time, logging into the Squirrel point-of-sale system. “And there she is.”

“Sorry I’m late,” said Theryl, with a toss of her wildly curly red hair. She flashed me a smile, and winked one of her cat-like green eyes. She had overheard some of the conversation, and knew her boss well, for the go-getter I admittedly was (and still am).

“You already apologized on the phone,” I told her. “Thanks for calling in. This is-?”

I left the question open for the young man to answer. “Tommy. Tommy Boy.” He said quickly, catching my drift.

“Tommy Boy.” I told Theryl, returning her wink. “And I’m Kayla, she’s Theryl, and now that we’re all acquainted, I believe we were heading upstairs to my favorite room, isn’t that right, Tommy?”

“Hell yes,” the young man replied eagerly, and prepared to follow. I hiked my black latex skirt up an inch or two higher for his benefit, and left the confines of the bar. Tommy Boy met me at the door, and as soon as we stepped across the threshold, I was upon him, kissing him madly, deeply, with much vigor.

He had a lazy tongue, and was pretty much a lousy kisser all around. His hands were on my ass, squeezing the buttocks firmly, but not as firmly as I would have liked… These two things only irritated me further, and were inspiration enough for me to turn the kiss into a harsh one, one that left him gasping for breath as I pushed him up against the front desk of the hotel portion of the Boulevard. Nancee, who was at the desk, ignored my aggressive manner, being used to my appearances at the front desk with my various flavors of the week.

Leaving the young man breathing heavily at my side, I smiled at Nancee with my kiss-swollen lips. The keycard to my office was presented to me immediately. “The keycard to room two-oh-nine, please,” I added, as an afterthought. To my knowledge, it was vacant.

“Certainly,” she replied, and was quick to hand it over.

We ascended the steps quickly, with Tommy Boy bringing up my rear, peeking as much as he possibly could at the athletically firm young ass that wore crotch-less panties beneath the latex miniskirt that clung to me like a second skin. As I was opening the door to the second floor, he approached me from behind and pressed his pelvis into my ass. I could feel the beginnings of Tommy Boy’s hardness there, and was immediately brought to feelings of excitement… The poor boy had no idea of what I had in store for him.

This was going to be fun…

The walk down the hall was a short one; I inserted the keycard in the slot provided in door two-oh-nine, and opened it wide, allowing a grinning Tommy Boy to step through the doorway into pitch black darkness. I closed the door behind me, and felt him approach.

“Take your clothes off.” I instructed him flatly, as his hands felt for me in the dark.

“You show me yours, I’ll show you mine,” he said, trying to be suave. He felt for my breasts, so I crossed my arms.

“Take your clothes off, or this ends now.” I growled, keeping perfectly still.

For a long moment, he was quiet. His hands fell away from my breasts. I could tell that he was wondering at my cool tone, and was maybe beginning to suspect that things were going to be done my way, or not at all…

“Fine,” he relented, and I heard the zipper of his jeans slide down. “I’ll take my clothes off.”

My clit twitched in response. I was going to give him a night that would be memorable for the both of us, but one that he would never be able to forget… and I promised him this. “You’ll never forget what I’m going to do to you tonight.”

“Is that a threat?” He asked, and froze where he stood.

“No, dear ­ that’s merely a promise.” He seemed satisfied with my answer, because the next thing I knew, my eyes adjusted to the dim light offered by the closed drapes, and I could see his leopard- print G-string: a G-string that was tent polling with his beautiful erection. His jeans hit the floor with a soft thud, and a small grin broke out on my face.

He took a step towards me. “Look, Kayla ­”

I put a finger to his lips, silencing him. “Now your shirt.” Begrudgingly, he complied. “And your G-string. But leave your socks on.”

“Leave my socks on?” He asked, confused.

“It’s kinkier that way,” was my brisk explanation. I was losing what little remained of my patience…

“Leave my socks on?” He repeated.

“Look, Tommy Boy, do you want to fuck or not?”

That silenced him. His reply was the sound of his shirt sliding over his head, and then hitting the floor near his jeans. He was beautiful, in the dimness, with a broad, muscular chest, and flat stomach that tapered down into lean hips, long legs, and strong-looking thighs. He removed his G-string next (the choice of underwear amused me ­ few guys walk around in G-strings…), and was completely nude to my eyes, save but for his black socks and the small gold cross on the thin gold chain that hung from his neck.

Brazen, I observed his eight inches of manhood: his penis was attractive enough, pointing up along the thin line of light-colored hair that ran from his groin to his navel. His erection was thick, and ribbed slightly in places; he had no foreskin, but a very nice head, shaped quite like a mushroom. A single drop of pre-cum glistened in the near dark; all in all, his was a very nice package.

Again, he approached me…

“Go lay face down on the bed.” I told him, cutting off the squawk that had sounded in his throat ­ he had been about to talk.

“But-”

“Now.”

“Lady, you sure drive a hard bargain…”

He really had no idea… no idea of what his big mouth had landed his small ass in. In silence, I picked up his clothing, and watched him climb unto the bed, white ass in the air. “Face down.” I reminded him, and watched him comply. “Now wait for me here ­ I’ll be right back. I have to slip into something more… comfortable.”

I stepped back into the hallway with his clothing in my hands, and rushed to my office: room two-oh-six. Slipping the keycard into the door, I threw his clothing on the bed in the corner, and grabbed my ‘bag of tricks’ from beneath my broad desk. The duffel bag contained all that I would need… I quickly stripped off my gold shirt, and adjusted my black merry widow.

Locking my office door behind me, I returned to room two-oh-nine and heard Tommy Boy’s sigh of relief.

“There you are ­ but where are my clothes.”

“I moved them. Don’t worry ­ they’re in a safe place.” I closed the door behind me, and he was bathed again in darkness.

“Could you turn the light on while you’re there?” He asked meekly.

“I prefer ‘doing it’ in the dark.” I told him, and approached the bed. He began to roll over, to face me, but I stopped him. “Face down!”

“All right, all right.”

“And be quiet. I prefer my men strong but silent.” He didn’t reply. “Good boy.” I unzipped my bag of tricks, and felt for the pocket that contained my police-issue handcuffs. The key was where I had left it, at the bottom of the pocket. A smile on my lips, I withdrew the handcuffs as quietly as I could. “Roll unto your back.”

“What?”

“Be quiet! Roll unto your back.” Begrudgingly, he did as I instructed. “Now your hands – put out your hands, and close your eyes.” He obliged me, but very slowly. He seemed to have lost trust in me. He flinched as the cold metal of the cuffs touched his bare skin, and he was jerking away, but it was too late ­ I had already fastened both cuffs by the time he completely realized what I was doing. “Roll unto your back ­ you need to be punished.”

“Handcuffs ­ you like it rough, baby ­ don’t you?” He laughed triumphantly, but had nothing to be triumphant about.

“Be quiet.” I slapped his white ass then, as hard as I could. The noise of the slap echoed off the walls, rather loud. My hand stung, but I knew his ass stung even more.

“What did you do that for?” he shrieked, angrily.

“Because you won’t shut up!” I snapped, and slapped him again.

He groaned aloud this time, his surprise replaced by fear. “Quit that!”

“What, you don’t like it rough?” I seethed, and withdrew the softer of my whips from my bag of tricks, the one with the rubber handle, and the tassel-like end. I drew it along his back, over his slender white ass, and spanked him once. “C’mon, be a man. Take it like a man, you wimp!”

“I think there’s been a mistake…”

“Did I not tell you to shut up?” I raged, spanking him again with the flat of my hand.

His body jerked and a grimace of pain crossed his handsome face. “Sorry.”

“You bet you are!” I ranted, and spanked him again. My hand was stinging, but I was excited now ­ my pussy throbbed as I mounted his still form, and massaged his abused buttocks with my hands. With my right hand, I touched myself, found the wetness of my excitement there, and smiled.

Tommy Boy most certainly had not been expecting this…

“Now roll back unto your back.” I ordered, in cool, harsh tones. I didn’t move a muscle to help him, but was rather pleased by his efforts to obey me. I thought that he would have lost some of his erection, from the shock of my actions, but surprisingly, he was ramrod- straight and hard to the touch. For a fleeting moment, I held his cock in my hand, enjoying the feel of his throbbing self there… and then I let him go. He would be in me soon enough… and I was ready for him. In so many ways… “Good. Now I’m going to fuck you, and you are going to like it.”

Without further ado, I withdrew a single condom from my bag of tricks, and tore it open. Hastily, I squeezed out the air in the tip, and rolled it down the length of his long, lovely shaft. He used his muscles to make his cock stand straighter, higher for me, and I smiled. This was going to be fun… I knew very well the kind of pleasure a woman could get from an erection like his, and looked forward to taking some of that pleasure for myself.

Handcuffed hands before him, he lay at rest, waiting for my next move. I raked my eyes and hands over his body, from his large, awkward-looking feet to his knobby knees, to his protected penis, to his flat stomach, to his sculpted chest, to his wary grin. He was warm to the touch and tense with desire… He didn’t know what to expect next, clearly.

I hiked my skirt up to my flat stomach, and dropped the whip that I had used earlier. I fingered my hairless slit in full view of his eyes, blue eyes that grew wide as I played with the stainless steel piercing there. My Isabella piercing, the one that went through my clitoral hood… It was for his pleasure that I licked my finger, and inserted it deep into my crevice, and then drew it out to tease that single barbaric piercing.

I watched him swallow with anticipation, and smiled down at him. I threw my right leg up over the bed, over him, and moved myself into a riding-style position. I was straddling him, with his thick cock between my legs, my throbbing pussy only an inch or two away from that eager rod of his… Tossing my hair over my shoulder, I leaned forward, until I was above him, took his cock in my right hand, and guided him to my moist slit. I slid him over my labia, teasing myself; teasing each lip, teasing him. I guided him back towards my happy little hole, and decided then to let him in…

First, only an inch of him.

Then, two inches… three… and then in one smooth, slick motion, I took his entire nine inches into me, and gasped at how good it felt, to have that big, hard cock inside of me. I was throbbing around him, he was throbbing inside of me, and it was then that I felt the first tremor of what was promising to be the beginning of a truly mind blowing orgasm. I knew my body well… Knew how it would respond to him…and reveled in that knowledge.

With him inside of me, I bore down on him, until he could enter me no further. I squeezed him with my kegel muscles, and heard his gasp of surprise.

“What the fuck was that?” He asked, clearly impressed with the strength of the muscles in my vagina.

“My kegels.” I replied, “Now shut up, and let me fuck you.”

Still squeezing him, I slid my pelvis forward, ever slowly, and then back, even slower, enjoying how he filled me so completely, enjoying the feeling of having him deep inside me. It was heaven, pure heaven…

The animal in me wanted a little bit of Hell, a little bit of sin. Mine was a molten, angry hunger…an itch that needed to be scratched the only way I knew how.

And so, I grabbed his shoulders, and ripped my pelvis forward, and then back, and felt him stiffen in response. I was going to ride him hard, and ride him quick, until either he came, or I did ­ I was now beyond caring. Like a madwoman I rode him, I rode him with hatred of his cocky nature, I rode him with a newfound lust for life. I rode him with anger, and with appreciation, with angst, and with growing satisfaction…

His erection remained hard and true within me, caressing my inner walls with such sweet and savage intimacy, I soon felt a need to cry out, and did. As the stirrings of my orgasm ripped through me, I cried out “Bastard, you fucking bastard,” and slapped his chest with renewed passion. He answered my cries with one of his own, and it was then that I came, with all the force of a hurricane, I arrived at my final destination, and felt a foreign spasm within me, the spasm that was his own release…

As my mind slowly collected itself from the brink of madness, my body shuddered again: aftershocks from my orgasm…Rejecting him in my ecstatic mind, I climbed off of him, and pulled my skirt back down. I was finished with him, for the most part.

I went to the coffee pot on the table in the corner, on wobbly legs, and smiled into the Coffee Mate. “I’m going to make some coffee. Would you like some, Tommy?”

“Uhm…sure.” he said unsteadily. I heard the bed creak beneath him, as he moved into a sitting position. “Can you…uh…un-cuff me now? I have to get rid of the rubber.”

“Right.” With a sigh, I turned around, and walked to the bag of tricks that rested near the bed. Withdrawing the handcuff key, I released him: one hand, and then the other. He rubbed his wrists, and looked up at me with boyish innocence.

“You know, no one’s ever treated me like that…and I really…I don’t know. I mean, it was weird, but I kind of liked it.” He looked up at me with his big blue eyes. “Can we do it again?”

I had meant to break him. I hadn’t expected him to like it…

Like I said, I didn’t mean to corrupt him – it just sort of …happened.

The End


This entry was posted on Friday, May 2nd, 2014 at 6:17 pm and is filed under Anal, BDSM, Sex Stories. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.

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