My Naughty Secretary

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Shy young secretary comes out of her shell.
2.8k words
4.53
142.1k
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Part 1 of the 2 part series

Updated 06/07/2023
Created 02/27/2016
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DASTONE
DASTONE
510 Followers

The year since I met Samantha has been the most exciting time of my life since my cousin had taught me how to properly please a girl and gave me the confidence to do so before unleashing me on the unsuspecting girls of my High School (let me know if you ever want to hear THAT story).

I was drawn to her quiet and shy demeanor, her genuine kindness and joy at being with people, her quick smile and contagious laugh, and of course her beautiful and innocent appearance. The first few times I tried to talk to her she was almost too shy to respond, but after weeks of running into each other at the corner coffee shop I was finally able to get her name and that she worked as a secretary in the office building across from mine.

Though she was about 10 years my junior, eventually she agreed to a date, and then another. When I succeeded in getting her back to my place after a romantic dinner I found that while she was almost as innocent as she appeared, her appetite for sex nearly matched my own. Her shyness, combined with years of thinking she wasn't sexy enough or pretty enough, had held her sexuality back. But each encounter in my bed seemed to whet her appetite even more.

I watched as her confidence grew, in herself and in her sexuality. Her hair changed, her makeup changed, subtly replacing the young and naïve innocent teenager with a sultry and enticing young woman who made heads turn no matter where she went. The clothes changed too, unflattering outfits and boring shoes turning into sexy and revealing skirts and blouses matched with heels that showed off her long smooth legs and firm round bottom.

My sweet little kitten and transformed into a sex-crazed tigress and I loved every minute of it. How could I not when she spent every chance she could get either stroking or sucking on my all too willing shaft? I felt like I was in some kind of porno every day. Even the sluttiest girls I fucked in high school didn't crave sex like Samantha did. Even as I write this it sounds too far-fetched to be true, but I swear it's like my cock and cum had become some kind of life sustaining ambrosia to this girl.

I laugh when I think of how she used to be too nervous to hold my hand or show any affection in public, always looking around or blushing if anyone saw me kiss her. Soon she was the one seeking affection no matter where we were, looping her arms around my neck and kissing me as if no one was around. I quickly realized that an audience actually excited her. The first time I fucked her in public, even though no one could actually see us, I found her wetter than I had ever experienced and she came so hard I thought she had blacked out.

We were out at dinner and she had spent the entire meal turning me on so thoroughly I thought I might rip straight through my jeans. I had picked her up from work so she was still dressed in her tight charcoal skirt that almost reached her knees and a white blouse that showed a generous amount of her large firm breasts, especially after she unfastened another button or two. As we drove to the restaurant she talked excitedly about her day and gossiped about how she had caught one of the other secretaries leaving the CEOs office with something white still dripping from the corner of her mouth.

"Seriously though babe, she's such a slut!" she said "She only does it because she wants Debbie's job when she leaves next month." I remembered from previous conversations that Debbie was going to have a baby soon and had decided to retire early to be a stay at home mom. Not that she'd be hurting, according to Samantha her husband was some rich banker so she didn't really need to work anyway.

"Weren't you going to apply for that one too?" I asked her with a smile, my hand resting comfortably on her thigh.

"Well yeah," she said as she looked at her makeup in the visor mirror. "But I'm sure not going to crawl underneath Scott's stomach to find and suck his dirty cock to get it." I laughed as she closed the mirror and scooted closer to me. Leaning close she whispered seductively, "Especially when I already have access to this perfect cock, and all the yummy cum I can drink." She slid her hand up my thigh as she spoke and softly stroked my rapidly swelling shaft through my jeans.

I kind of lost my train of thought around then and had to focus on keeping us on the road. She smirked at me and just kept talking about the goings on in her office, her hand never ceasing its soft and slow movement in my lap. By the time we parked in front of the restaurant I was pretty sure my cock would never be soft again.

Her lips closed around my earlobe as I put the car in park and she purred softly before I pulled away and stepped from the car, willing my cock to subside a little so I didn't make a scene when we walked inside. As I opened her door she swung her legs out, purposely flashing me the tops of her thigh high stockings and garter straps leading up her pale smooth legs. Given my near obsession with thigh highs and sexy lingerie she had pretty much ensured that I would indeed be drawing a few stares when we entered the restaurant.

A self-satisfied smile graced her face as we walked inside and I laughed at myself for not realizing that anyone who looked in our direction would be too busy staring at her to even realize what that long thick bulge traveling down my right thigh actually was. We were quickly shown to a table and sat across from each other. I noticed the young hostess staring down Samantha's blouse when she handed her a menu and gave her a smirk. She quickly left the area with a pink blush creeping up her cheeks.

Looking across the table I caught Samantha subtly undoing another button on her shirt with the result that the edge of her black lace bra was now peeking out at me. Apparently she had noticed the girl's lingering gaze as well. When the waiter came by she was absently trailing a long red fingernail up and down the swell of her right breast, pretending to read the menu. He fought the urge to stare as he took our order before hurrying away while adjusting his pants under the apron he wore.

Dinner continued like that, Samantha teasing me and pretty much everyone else who bothered to look over. As we were waiting for the check I suddenly felt something sliding up my leg. Looking down I saw her stocking clad foot slid between my legs, her toes brushing over the bulge in my pants. Looking up I caught her hungry gaze on mine.

"I'm ready for my dessert, Daddy." She whispered, loud enough for me to hear and for the couple nearby to wonder if they had heard correctly.

I managed to stifle a growl of arousal as the waiter handed me the check and I in turn handed him my card. She had started calling me Daddy lately when she was feeling especially playful or kinky. We hadn't talked much about D/s stuff at that point in our relationship, but she quickly learned just how much I loved when she called me that. A haze of arousal settled over me and I don't really remember signing the check or leaving the restaurant. All I could think about was shoving my cock into the naughty little minx across from me.

We were in the car a block away from the restaurant by the time she succeeded in getting my cock out of my pants and into her mouth. She sucked and stroked desperately, her need matching the consuming arousal that burned in my chest. Turning onto a side street I parked on the side of the road. We were in front of a small office building that was obviously closed for the day. The street was well lit but empty of cars and pedestrians.

I exited the car, my cock still sticking out of my pants, throbbing in need. Hurrying around the car I opened her door and yanked her out by the arm. "If you're going to act like a little slut all night then that's exactly how you'll be treated," I growled as I spun her around against the car. The buttons of her blouse pinged off the car as the thin white fabric came away in my hand.

A gasp turned into a moan as I yanked her bra down and firmly kneaded her big perfect tits. "ohhhh Daddy! Wait someone might..." Her words were cut off as I turned her face and captured her mouth with my own. My bare cock was leaking precum all over the back of her skirt as I ground against her, pinning her against the car. My hand a fist in her hair as she broke away from the kiss and gasped for air. "FUCK ME DADDY!!" She cried, her words echoing off the buildings.

Moving her down the car I bent her over the hood and yanked up her skirt. Her panties barely covered her glistening slit and were obviously soaked with her arousal. Yanking them to the side I buried myself to the hilt inside her. A scream pierced the sky as my thick shaft forced her sheath to spread around it. "Yes Daddy... Fuck yes... fucking give it to me... fuck!!"

She came on my cock twice before I finally buried myself inside her and filled her pussy with a load of thick cream. I collapsed over her on the hood sucking in deep breaths of air. Looking over at her I thought she had passed out but then she stirred and gasped loudly, whimpering as she breathed. We straightened our clothes and returned to my home where we fucked again, sharing a long deep climax before falling asleep together.

Even now that remains as one of the most incredible experiences of my life. Since then she has moved in with me and we have continued discussions about DD/lg and other kinks. Her natural submissiveness has become increasingly obvious and she has taken to calling me Daddy almost full time, even outside of the bedroom. She has become quite the exhibitionist as well, often finding a way to tease me in public where someone else can see and be aroused by it as well. Those days are always followed by nights of fierce and sweaty sex until she cums at least twice on my thick shaft before swallowing my cum.

"Daddy's cum should never go to waste." She stated after a particularly exuberant session. Turning she laid down on the bed, her perfect ass showing off a bright pink handprint.

Smiling I collapsed next to her and she curled against my chest. "I don't think any of my cum has touched the ground since the first time you tasted it you thirsty little slut." I said and gently caressed her back.

Kissing my chest she looked up at me and winked. "Daddy's yummy cream needs a place to go after all," she giggled. "It's too good to waste and Daddy deserves to have it all swallowed." Her love of drinking my cum always surprised me but she usually preferred it in her mouth to anywhere else. Without another word she drifted off to sleep, a happy smile on her face.

The next day I reluctantly left for the office, kissing her cheek and quietly leaving her sleeping form on the bed. Usually she insisted on a good morning suck or fuck before I left but after last night I guess I couldn't blame her for sleeping in. She didn't have to be at work until later anyway. She hadn't gotten the position we had talked about months before, but did end up getting a new and better position anyway.

I was an hour into a two hour meeting when my phone pinged. The first picture showed her in a steamy bathroom with a towel wrapped around her lithe frame. The next couple showed the towel dropping away revealing her delicious treasures. The last displayed her fully nude, head thrown back and fingers buried in her smoothly shaven pussy. Along with the picture was a short message. "Remember not to show anyone Daddy!"

I shook my head and put the phone away, trying to bring my thoughts away from my swiftly rising cock and back on the meeting. This was a somewhat new development for her, sending naughty pictures to me at work. The shy girl who used to nervously glance away from me at the coffee shop was gone, she would never dream of sending something like that. In her place was the girl I loved, a girl strong and confident in herself and her sexuality, always seeking new adventures and experiences.

After a long morning of meetings and frustration I returned to my office for a lunch break. Calling to my secretary I asked her to order me a pastrami on rye from the corner deli and to go get it for me. Closing my office door I turned off the light and collapsed in my chair, leaning back and closing my eyes.

"What the..." I exclaimed suddenly, jerking upright as I felt something sliding up my legs. Looking down I saw a naked Samantha grinning up at me like a cat about to eat the proverbial canary.

"Hiya Daddy," she grinned innocently. "I didn't get my breakfast this morning so I figured I'd come have it for lunch. I'm sure you won't mind." Her hands deftly opened my pants and fished inside for my cock. Purring softly she pulled it out and wrapped her lips around the tip.

"Sam wait, I can't do this right now," I started to say, even as my shaft swelled in her expert fingers and mouth. She just smirked and kept on sucking and stroking. "Oh I see," I said as I gave into the growing pleasure. "You don't even care if someone comes in. In fact, I think you'd like that wouldn't you little slut? You want someone to catch you, to see you with Daddy's big cock in your mouth?"

Her moans met my ears as she sucked harder, her hand disappearing between her legs. Seeing my phone on my desk I smirked and grabbed it. Turning on the video recorder I pointed down at the brunette head bobbing in my lap. "I think you want everyone to see you like this. A filthy slut on her knees desperate for her Daddy's cum." Looking up with a whimper Samantha saw the phone and her eyes flew wide.

"That's right little whore," I said with a grin. "I'm going to record you swallowing my cum, and then who knows who I might show it to?" Samantha let out a moan and her eyes rolled back into her head and she quivered fiercely through a powerful climax. Her sucking stopped while she came, but then she resumed with a vengeance, somehow even more desperate to receive a load of my cum.

I could feel it building when a knock sounded on my door and Cynthia entered the office with my sandwich. Coughing I sat up and pushed my chair towards my desk, hoping she hadn't seen Samantha's head in my lap. "Here's your lunch boss," she said as she set it on my desk. She turned to leave before stopping and giving me a questioning look. "Although I don't know if it smells as good as the other snack you already have in here." She smiled and winked before heading to the door and closing it behind her.

Turning back I found Samantha's bright eyes looking up at me, a hungry look in her eyes as she deep-throated my cock. Moments later my balls tightened and my cock convulsed, shooting ropes of cum into her waiting mouth. She sucked and sucked until she had every drop before lifting her head and swallowing with a moan of satisfaction.

"Thank you Daddy," she said as she crawled from under my desk. "I needed that. I have to get to work but I'll see you at home tonight." Swiftly she dressed and headed for the door to my office. I saw her give my secretary a wide grin and then she was gone. A moment later Cynthia was back in my office wearing a smirk.

"You might have to show me that video sometime boss. I bet it was pretty hot."

DASTONE
DASTONE
510 Followers
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