I love teasing guys and playing hard to get. OK, it's a cruel, but I can't help it. I was born a natural flirt, with big green eyes, a tight little body, and luscious brown locks. In high school, I was always known as "that girl." It's a compliment, even though it doesn't sound like one. I never worried about being tossed into the trashcan as a freshmen, or getting soup dumped over my head. I'm a flirt, but guys and girls can't help but like me no matter what. But I learned my lesson eventually...here's my story:
I had turned 19 recently, and was on the verge of adulthood. All my life, I had been babied by my parents - I was the first in my class to get an iPhone, sport Doc Martens, and sip Martinis without looking like an amateur. I'll admit it, I was spoiled.
But at 19, my parents were tired of my uppity act. I was smart but lazy, so I never fulfilled my father's dream of attending Harvard University. Honestly, I didn't care. Harvard was overrated anyway; filled with snobby nerds who had nothing better to do than bury their noses in ancient English books.
So my parents decided on a compromise for me: I had to work my at my dad's law firm as a secretary. I sulked and pouted for weeks. To me, work was something unheard of. I was used to getting a monthly allowance from my parents and spending it all before the 30 days were over. However, my father put his foot down and told me I was going to be secretary to a Mr. Brad Pickers.
So the following Monday, I was up at 5 am. I dug through my wardrobe, trying to find a sexy yet appropriate outfit. I knew my usual tight pencil skirts were out of question, since my father was driving me to work and wouldn’t approve. At last I dug out a crumpled white blouse; it smelled of rotten food and had a long orange stain on the left sleeve. Damn! I threw the blouse into my hamper and continued rummaging through my clothes.
A knock on the door startled me and I whipped around quickly. “What?” I snarled at my mother, who was standing at the doorway with a pink bathrobe wrapped snugly around her petite frame. Her pretty face gloated at me, “Not so fun waking up early, right honey?”
“OK, seriously Mom. I don’t have time for this,” I grumbled under my breath. My mom was so annoying. She knew how to push my buttons and she was pushing them well! I sighed and continued searching for a damn blouse.
“Need a blouse?” she asked sweetly. I rolled my eyes; my mom had a million blouses so borrowing one wouldn’t hurt. She probably wouldn’t even notice if I stole her blouses. “Yeah sure. Mine are dirty,” I said.
She laughed, “And when do you wear blouses Miss Prissy? Isn’t your usual attire a miniskirt and leather boots?” I turned, ready to give her a piece of my mind but she was gone; to get a blouse I hoped. I sat on my plush recliner and began applying makeup. It was crucial for me to look good, because this Mr. Brad guy could be one hottie with a body. And if that was the case…I wouldn’t mind playing some hard to get. I was applying my mascara when my mom came in with a lovely silk blouse. “Here honey, don’t ruin this okay?”
I paused, my hand in midair. Why was my mom being so nice? I knew this silk blouse was one of her favorites, so I didn’t understand why she wanted me to wear it. “Uh Mom, this is your favorite blouse. Why are you giving it to me?”
She smiled and smoothed back my hair, “I want my baby to be the prettiest girl at work today. Perhaps you’ll even meet a nice lawyer. You know, you’re old enough to start looking for a husband. I don’t want you marrying a hooligan.” I laughed and wrinkled my nose, “Mom, I had no intention of marrying a hooligan. I did it to annoy you and Dad.”
She began braiding my hair, “Honey, you might not know it, but your dad and I love you very much. We think you’re a talented young lady who has lots of potential. But you need to step up your act, okay? Now have fun. Bye sweetheart.” With that, she unbraided my hair, blew me a kiss, and left the room. I sighed, time to go to work.
4 hours later, I was sitting at my desk, fantasizing about Brad. He was the hottest guy I had ever met. I was so unprepared to meet him; I thought about giving my dad a lecture for not warning me about Brad. I always had the upper hand with guys, and when my dad introduced me to Brad, I wasn’t the one holding the cards; it was Brad. He was immaculate – 6’0, lean and muscular, with sharp grey eyes, and a thousand watt grin.
From the moment I met him, I knew he had me hooked. Fortunately Brad was only 25, so there wasn’t much of an age difference. He wasn’t married and his previous girlfriends all looked like runway models. However there was one thing that was different about Brad – he wasn’t cocky. I know good looking guys are typically arrogant and that’s a major turn off for me. However Brad was intelligent and witty which was more of a turn on for me. So here I was, sitting at my desk and drooling about my boss who was less than 50 feet away from me.
The door opened and I looked up from my computer. Brad stood there, and everything else vanished. “So Leah, your dad’s got you working for him eh?” I blushed and chided myself, “Yeah it’s a great way to earn some cash.” He flashed me that brilliant grin and looked at my computer. Uh oh. I was browsing through lingerie. “Ah…I can explain. I was just um taking a break,” I muttered. “Leah, I’d prefer you keep your mind on the task at hand.” And with that, he turned and strode down the hallway.
I groaned and buried my head in my hands. This was fucking great. He probably thought I was browsing through lingerie for him. All of a sudden, a devious thought formed in my head. I was here to play hard to get, not be some mousy submissive secretary. I checked my appearance in my hand mirror and straightened my collar. Time for the game to begin.
The next day, I put together a semi-sexy outfit. I borrowed a satiny red blouse from my mother and pulled on a short grey pencil skirt. I wore black lace push up bra which accentuated my C-cup breasts nicely; and pulled on a little black thong. I could feel my juices leaking out at the thought of Brad and contemplated masturbating to him. I imagined Brad would have a nice thick dick, one which I could suck, lick, and kiss and never get tired of. I imagined waking up to him in the morning, watching his chest rise and fall with each snore, and making coffee for him before 6. Ah yes, sleeping next to Brad would certainly keep me on my toes.
As soon as my dad parked his silver Mercedes in the designated spot, I grabbed my purse and dashed to the elevator. I wanted to bang Brad in the elevator, have him moan out my name while his gunky white cum splattered on the immaculate brass. I sighed, and hurried to my desk. Today was going to be fun. My plan was to make Brad some nice coffee, chat him up during lunch, and wait for whatever happened.
I hurried to the coffee room and grabbed a handful of glazed doughnuts (his favorite). Then I poured a cup of cappuccino and carefully walked down the hallway with his breakfast. I could feel the eyes of the other men ogling me and a feeling of disgust rolled over my body. I loved to show off, but I didn’t like it when lecherous old men ogled my ass, breasts, and pussy. But still, that didn’t stop me from showing off and I swayed my hips from side to side, knowing I was probably to going to cause some heart attacks and boners.
Brad was already at his desk, looking over some files. “Hey, you’re here early,” I told him as I set down the coffee and doughnuts. He surveyed my outfit and flashed me a grin, “Well aren’t you a sexy little vixen today Leah,” he said saucily. I gasped and my hands rose to cover my chest. Brad stood up and shut the door, locking it behind him. “I know what you’re doing Leah. I already knew when I saw you looking over those lingerie catalogs. Do you think I’m that stupid? I’ve been working for your father ever since I graduated from Stanford! Do you know how many girls have played hard to get with me? Well let me tell you something, I know your tricks. So don’t play hard to get; because you’ll be the one regretting it in the end. Now get out.”
I stared at him in awe; this guy knew what I was doing! He wasn’t dumb and knew what I was getting at all along. I glared at him on my way out and slammed the door behind me. I wasn’t stupid and I knew I was going to do anything
to get him to notice me.
The next day, I notched up my game. I wore a long pea coat which was perfectly suitable since the weather turned stormy and windy. Underneath I wore a lacy red push up bra, see through lace camisole, the shortest skirt I owned, and 5 inch fuck me stilettos. Today Brad wouldn’t be the one in power I thought wickedly, I would be the one. I decided against underwear because I wanted Brad to see my freshly shaved pussy lips and the wet juice that clung to them. I wanted him to fuck me with my skirt and stilettos on. The thought of him bending me over his desk and slapping my ass turned me on so much that I let out a moan.
As soon as I entered the building, I made a beeline for the coffee room. I picked up his doughnuts again and made another cup of coffee hurriedly. I rushed down the hallway, paying no attention to the old guys who were ogling my tan bare legs and luscious brown locks. I opened Brad’s door and he was sitting there as usual – reading portfolios and typing away.
I slammed the door and locked it, grinning at him while I did so. “Hey Brad,” I said saucily and set the cup of coffee and doughnuts before him. Then I dropped my purse, and started unbuttoning my coat slowly, never averting my eyes from his. His mouth dropped open when I shed the coat and his face turned a shade of pink. “You like?” I whispered and walked toward him, swaying my hips and never averting my gaze. I settled on the edge of his desk and gently tapped his growing cock with my foot. “So what’s wrong honey? Cat got your tongue?” I smirked and peeled off my camisole, feeling prouder than ever for sitting in front of my boss with only a bra, skirt, and heels.
During this entire ordeal, Brad did not utter one word. He sat motionless while I unhooked my bra and dropped it on the ground. I grabbed my breasts gently pinched my nipples, moaning as I did so. I spread my legs and brought a hand down to my wet pussy, lightly feeling the dampness. I giggled in pure delight as I realized I was leaving a stain on his mahogany desk. “So what do you think?" I asked huskily, my hormones already in sex overload.
Suddenly Brad grabbed my waist and picked me up; settling my back against the wall and wrapping my toned legs around his lean frame. He stared intensely into my green eyes with his grey ones and started fingering me slowly. I moaned and squealed, pressing him closer to me. He made me put one foot on the ground and held my other leg up; so it was easier for him to finger me. A second finger slid easily into my sopping pussy and he smashed his mouth against mine. His other hand started playing with my clit; we settled into a rhythm and I couldn’t help but let out squeals of delight from time to time.
“Unnnh!! Oh yeah Brad! Come on! Finger my pussy!”
He grunted with exertion and shoved a third finger in. I let out a moan of pain and delight, wrapping my solo leg around his waist tighter. He whispered in my ear “That’s the sexiest sound I’ve ever heard,” and then with that he stopped.
I glared at him and found his hand; trying to force his fingers into my pussy again. “Why’d you stop?? I was going to cum!!!” I hissed indignantly. He grinned at me wickedly and stepped away from my sweat soaked body, “That’s why I told you not to play hard to get with me,” he whispered. He stepped away and re-buttoned his shirt, smoothing his hair and wiping his hands with Kleenex. He bent over and grabbed my camisole, bra, purse, and pea coat, setting them on his desk. “You better tidy yourself and get out,” he told me before sitting down and resuming his typing.
I gasped and felt the humiliation wash over me. I couldn’t believe he was so cruel! He didn’t even let me orgasm I fumed silently. I yanked on my camisole and quickly buttoned my pea coat, then snatched my purse. “This isn’t over,” I told him before heading out.
Later that night at home, I knew it wasn’t over. He had humiliated me today and he knew he had power over me. Now I had to step it up a notch and play the upper hand. I was not letting Brad get away with this. I was going to do whatever it took.
The next morning I was up at 7 am, pulling on my jogging attire. I had to maintain a good figure in order to snag Brad and the only way to do that was by running 6 miles. I didn’t bother with a shirt since the morning sun was nice and warm. Besides, I needed to tan and figured it wouldn’t hurt if I caused some morning wood for early male joggers. Before heading out, I examined myself in the mirror. My spotless complexion went nicely went with my pouty pink lips and thick hair. My stomach was toned and I looked hot in a pair of tight black spandex, a hot pink sports bra, and Nike running shoes.
I headed out the door and did some stretches. To my delight, a few male runners were already in the park and when they passed by me, I saw the rise of a tent in their shorts. I grinned to myself and started running, pacing myself so I could run 6 miles in around 50 minutes or less. As I was on my fourth mile, I got a pleasant surprise. I saw Brad, his back turned to me, stretching and preparing to run as well. I grinned and jogged up to him.
He turned when I was a few feet away and I saw a look of lust fall over his face. “What the fuck Leah. What are you doing?”
I smiled at him impishly and sat next to him. Fuck my run I thought, four miles was enough anyway. “I was running. I need to keep in shape you know,” I replied off-handedly, arching my back and pushing my breasts out while I did so. He stared my breasts, not knowing how to respond. I leaned closer and wrapped my small hand around his growing erection. “Hmmm what is this? A present for me?”
“OK, that’s enough,” he growled and got up, pulling me up as well. He pushed me ahead of him, leading us deeper into the park. “Where are we going?” I asked, unperturbed. I wasn’t afraid of Brad, and I wanted him to know that. Thoughts of him banging me on a park bench got me hot and horny and I stopped abruptly, only to have him slam against me. Taking advantage of the situation, I rubbed my round ass against his erection and ran my hands over my body. “Come on Brad. Take me right here, right now in the park. I’m already horny and wet. You can slide easily into my pussy,” I told him, my pussy getting wetter by the moment.
“You bitch. I fucking told you not to mess with me! Well you’re going to get your penance,” he growled into my ear. He pushed me into the bathroom and locked the stall door. My back was shoved against the cold cement wall and he pulled down my spandex, revealing my shaved pussy. I wasn’t wearing any underwear and he smiled at the sight. He pushed my spandex down to my ankles and pushed my sports bra up; revealing my firm C-cup breasts and perky nipples.
Brad knelt down and started lapping at my pussy, his nose rubbing against my clit. “OMG!!” I shouted out, he really knew how to bring me to an orgasm. He leaned back and shoved two fingers into my hole; never averting his gaze from mine while he did so. “Ahh, ahh, ahh,” I moaned, pinching my nipples while I did so. His fingers were magic; then without warning, he stood up, yanked down his running shorts and shoved his cock in me. I let out a scream of pleasure and pain, as my pussy was getting accustomed to his large dick. “Look at me,” he hissed, and smashed his mouth against mine.
I moaned and he began bouncing me up and down on his dick, occasionally tweaking my nipples and sucking my neck.
“Ahhh!! Yessss!!! Yesss!!” I shouted, not caring who would stop by and listen. He continued thrusting into me, hard and deep, growling and moaning as he did so. I kept moaning in pleasure, my hands gripping his lean butt and running over his muscular torso. "That's right!! Fuck meeeee!!" I squealed, as he plunged in harder and faster.
Suddenly I felt his hot cum splashing inside of my walls. He let out a loud grunt and held me against his body tightly, releasing everything he had. Without warning he pulled out and yanked back his running shorts. He ran his hands through his messy hair and hurriedly washed his hands in the sink. He smirked at me before leaving, "See ya."
I gasped, my eyes brimming with tears of humiliation. He certainly knew how to push my buttons! He was right, playing hard to get with him wasn't getting me anywhere. I dropped to my knees on the cold cement and started sobbing. The fury and horniness of the past week was getting to me and I was deeply exhausted. I attempted to wipe away the cum but made a bigger mess so I pulled up my spandex and pulled down my running bra. I re-did my hair and washed my face and hands slowly, relishing the feel of cold water against my sweaty skin. As I sadly trudged home, I realized I had to come clean and tell him my feelings on Monday.
On Monday morning, I sat at my desk, feeling more dejected and lonelier than ever. I was wearing an appropriate outfit for once; a buttoned up white blouse, black slacks, and 3 inch heels with minimal makeup and a plain braid. I absentmindedly read some portfolios and awaited Brad's arrival.
At 7:30 on the dot, he came appeared at the end of the hallway and started walking toward my desk. He passed by without a smirk or word and shut the door behind him. I sighed, smoothed my blouse, and got up to give him the dreaded talk.
I hesitantly opened the door and peered in. He was typing on the computer, paying no attention to me. I opened the door wider, and stepped in "We need to talk Brad," I murmured. He glanced up and I saw weariness in his eyes as he surveyed my outfit. "Very well. Shut the door," he instructed. I obeyed and closed it, inching my way toward his desk. "Sit," he commanded and gestured toward a small chair. I nodded and sat, feeling as vulnerable as a kitten. "What are you here for?" he asked.
I sighed, and wrung my hands. "Brad, you've probably noticed my outfit. Well this outfit is telling you that I'm giving up on my hard to get game. You're right, you won this game. I was no match against you. So I'm here to tell you I lost." I looked up at him sadly. He stood up and knelt next to me, caressing my hands softly while he looked into my green eyes. He seemed sad.
"Leah, baby I didn't want to do that with you. I was enthralled with you on day one, and I really wish you didn't play that game with me. I'm older than you and I'm very experienced in the ways of women. I minored in psychology in college so I know these tricks. I was turned on, but I didn't want you to win, so that's why I went through great lengths to make sure you'd lose. Do you understand now? I'm sorry for humiliating you, but I have feelings for you Leah...and I want you know now."
I glanced at him, my eyes brimming with tears. I threw my arms around his neck and sobbed into his suit, "I have feelings for you too."
He smiled warmly and pulled away, gently stroking my face. "Let's go out Leah. And maybe we can teach each other a thing or two."
And that's how I learned my lesson.
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