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"Cassie!" Daniel called. He finished tieing his shoes and stood up.

"Yes?" I answered. I entered the room and walked over to Daniel. I was relieved he would be gone for a few days. I needed some alone time.

"Well I'm all ready to go. I'll call you when I get to my parents place. Oh and remember, Gerald should be calling you about dropping off my paycheque." He leaned forward and kissed me goodbye.

"I can't wait to finally meet your boss. You have been working for him way too long for my to have not met him yet." I smiled inwardly remembering the badboy stories Daniel had told me. "Have fun. Don't forget to call me. I'll see you in a few days."

"Love you," Daniel smiled. He grabbed his bags and headed for the door.

"I love you too. Bye!" I blew him a kiss and closed the door behind him. "Time to relax." I plopped myself on the couch and turned on the tv. I had strict plans to watch tv, drink two bottles of wine and stumble to bed at 3 a.m. Although there was the matter of Gerald. It's Friday night, I thought, He's probably busy with his kids or something.

I slipped into some thin fabric shorts and a tube top. It was just too hot for underwear. I popped the cork on the first bottle of wine. I thought about using a glass but eventually decided the bottle was easier. No dishes to wash afterward.

I had just polished off the first 1.5 litre bottle when a firm knock on the door made me jump. No one ever knocked on our door especially not at 9:30 in the evening. Without a second thought to my attire, I jumped up off the couch and headed for the door. I stumbled, realizing I had probably downed the wine a little too fast.

I unlatched the door and pulled it open to see a tall man, about 6"2, in his mid forties. He had blond shaggy hair and bright blue eyes. He had a bit of a beer belly, but he looked solid and strong.

"Hello?" I asked, tentatively. I saw as his eyes widen. They flashed down my body and back up to my face. The electricity between us was instant.

"Hello. I'm Gerald," he reached out his hand. I shook it. It was warm and rough.

"Oh, Gerald! It is so nice to finally meet you. Would you like to come in a minute?" I offered before I could think twice.

"Um, okay. Maybe just a minute then." Gerald stepped into our apartment. His large stature made our living room seem smaller than it really was. I locked the door out of habit.

"Would you like a drink?" I sang as I skipped into the kitchen. I was feeling quite light headed by this point. I pulled out two wine glasses and popped open the second bottle of wine. I carried our glasses out, balancing the bottle under my arm. "Here," I passed Gerald a glass.

"Oh, Thank you but I don't really drink," Gerald tried to hand back the glass.

"Please join me? I feel a little pathetic drinking alone. Besides, you can afford to stay a few minutes, can't you?" I was tipsy and feeling lonely. I didn't want to sit in silence anymore.

"Okay, I suppose one glass couldn't hurt," I saw him glimpse at my crotch as I sat down opposite him. I had forgotten I wasn't wearing any panties and had spread my legs a little to wide when I sat down. This little glimpse suddenly made me horny beyond belief. From what Daniel had told me Gerald and his wife never had sex. Gerald was developing a habit of digging for details about our sex life. This thought added to the gathering wetness in my shorts.

I sat with my one leg pulled against my chest as innocent as I possibly could, pretending I didn't know what was peeping out of my shorts. I saw his gaze rest momentarily between my legs. He licked his bottom lip but quickly recovered returning his eyes to my face. I smiled at him.

"It's so nice to finally meet you!" I repeated, my cheeks beginning to flush. Gerald smiled.

"Yes, I believe you mentioned that. It is very nice to meet you as well. Daniel has told me a lot about you." Gerald smiled, almost naughtily.

"So what brings you by?" I asked, sipping my wine. I knew damn well why he was there, but now I desperately wanted him to stay.

"Oh Daniel didn't tell you? I have his paycheck. I thought you would be expecting me," He blushed as he scanned my body once again. Obviously he thought I had dressed this way on purpose. "Apparently not." My face went completely hot.

"Oh my goodness!" I squealed, pretending to be shocked and embarrassed. I looked down at myself. "I didn't realize I was so inappropriately dressed. It's just so hot up here. But if I am making you feel uncomfortable I can throw on a sweater," I stood and went for the laundry hamper. I bent right over with my bum partially facing Gerald. I could feel my thin shorts ride up and pull tight between my bum cheeks.

"Um, well, I think you're dressed fine. I mean, you are right, it is hot up here." He was having trouble controlling his voice. Good, I thought, I was turning him on. But what 40 something year old wouldn't be turned on by a tipsy, half naked 20 year old.

"Good," I sighed, "I can hardly stand what I am wearing now little lone more clothing. The heat doesn't agree with me." I picked up my glass and emptied it in two gulps. I smiled at Gerald. I couldn't help notice the growing bulge in his jeans. He abruptly stood, his eyes locked on my bottom.

"Well, now that you've got the cheque I had best be going." He cleared his throat twice and turned toward to door. I tried to move forward to walk him to the door but I stumbled over the laundry basket knocking it over. I fell forward toward Gerald. He turned just in time to catch me before I hit the floor. He had one hand around my waist and the other dangerously close to my breast. His hands felt wonderful on my body. I giggled and let out a little squeal, clinging to him.

"Oopsies," I giggled more, arching my back to look up at him. "Good thing you were here to catch me." I ran a hand up his arm and lightly down his chest. He was wonderfully sexy. His manly scent swarmed my head. He continued to clutch me to him. He looked almost breathless as he stared down at my partially exposed body. He allowed his hand to graze across the material covering my pussy as he helped me stand back up. It caused me to shiver with excitement. I had never been so turned on by an older man.

"Maybe I should help you to the bedroom and then I should probably get going," Gerald kept one hand on my hip and the other pressed lightly against the small of my back. He guided me down the hall to the bedroom. He flicked on the light and closed the curtains. "Well, Cassie, it was lovely meeting you..." Before he could continue I reached a hand up and touched my fingers to his lips.

"Please, Gerald, don't leave me. Daniel always leaves me alone. Please, Gerald, I don't want to be alone." I slowly drew my hips closer to his body until we were almost touching.

I looked up and met with his boyish grin. That was the only confirmation he needed. He moved his body forward to close the gap between us. He slowly ran his strong hands through my long curly hair. I moaned deeply as this was my most favorite way to be fondled. He slipped a hand to the back of my neck, bending my head back. He carefully licked his lips then lowered his mouth to mine. Our lips met and our kiss immediately grew with passion. His tongue carefully explored my mouth taking my breath away. His hands slipped down my back. His thumbs caught the waistband of my shorts pulling them over my bum and allowing them to fall to the floor. He cupped my firm bottom moaning into my mouth.

I was desperate to get his clothes off. I had never seen a real man naked, not in person anyway. I tugged at his belt, struggling to undo it. He pulled away from me slightly, confidently smiling down at me. He swiftly undid his belt and removed his pants. Immediately his cock sprang up through the thin material of his boxers. His cock looked enormous compared to Daniels. Gerald removed his shirt revealing his broad hairy chest. My hands shot to his chest. I had never thought of a hairy chest being sexy before but seeing Gerald's almost made me lose my composure. I ran my hands over his chest just grazing his nipples. I trailed the hair down his stomach to his boxers. I carefully lifted the waist band of his boxers and slid them down to his knees. His thick cock sprang out to meet me. I gently took it in my hands. I softly ran my fingers up and down his length, completely entranced by his thick thighs and hairy balls. I looked up into Gerald's face. His eyes were filled with lust and his mouth was half open. I could tell he hadn't had his penis held so tenderly in a very long time. I wanted to please him. I wanted to make up for his wife not satisfying him in years.

I stuck out my tongue and slowly swirled it around his fat mushroom cap. I could taste his sticky precum. I slowly worked my way down his shaft, licking the entirety of it. When It was good and wet I returned to his tip. I opened my mouth and quickly thrust his entire length down my throat. I felt it slam into the back of my throat. I quickly withdrew and slammed my face down again. Gerald threw back his head and let out a loud gasp. Immediately he was thrusting back, forcing his dick further down my throat. I could tell he was starving for this moment. I continued to suck, lick, and stroke his cock. I could feel it pulsing against my tongue.

Gerald suddenly pulled his dick from my eager mouth. He bent forward and picked me up by my bottom. I was surprised at how he effortlessly lifted me up to him holding me tight. I wrapped my legs around his waist wanting to be as close to him as possible. With one hand he roughly pulled my tube top over my head and threw it on the floor. He stared at my perky 34C breasts. His boyish grin took over his face making me want him all the more. He grabbed a fistful of my hair and kissed me deeply. He forced his tongue down my throat urgently probing. His breath quickened considerably as his kiss turned almost violent. I gasped for breath.

Without warning, Gerald threw me backward onto the bed. I let my legs flop open finally giving Gerald a perfect view of my glistening pussy. He bit his bottom lip and lunged toward me. He buried his face in my pussy inhaling as deeply as he could. He lapped up the pool of juices that was gathering at my hole. He flattened his tongue and licked from the bottom on my slit to the top. The feeling was incredible. He stopped at my clit sucking and slurping the little bud. I moaned deeply, He held my hips down to keep me from bucking. He returned to my hole shoving his tongue in as far as it would go. He rubbed his entire face around my pussy drenching him in my juices. He constantly sniffed deeply as he worked which made me feel incredibly dirty. He couldn't get enough of the smell of my wet cunt.

"You smell so good. I had forgotten what young pussy smelt like," Gerald managed to say between slurps. I didn't realize my scent was so attractive. I had spend most of my life being embarrassed by my strong feminine odor.

Gerald roughly flipped me over. He pulled my bum up into the air. I automatically spread my legs to allow him better access. He spread my ass cheeks as far as they would go. It pulled painfully on my asshole. I could hear him almost panting now. He brought his face very close to my ass. I could feel his hot breath on my tight little hole. No one had ever been this close to my asshole before. I felt his nose graze my hole. He breathed in deeply through his nose. He was sniffing my ass! For some reason this made me almost collapse with pleasure. I had never been so violated before. It made me feel disgustingly dirty and I liked it. He sniffed deeply once more before circling my asshole with his tongue. I was shocked at the feeling. Gerald lapped at my hole allowing his spit to run down to my pussy,

"Ahhhuhhh" I cried out. I was ready to cum and we had barely started. "Please," I whispered, "my pussy..." I trailed off unable to finish my sentence.

"What's that?" Gerald asked, "What about your pussy?"

"Please...please.." Was all I could manage. He flipped me onto my back and pushed my legs up so that my knees were resting on my shoulders. He lowered himself to me guiding his cock into my now dripping pussy, His cock filled me, stretching me to my limit. I heard him let out a low growl when the last of his dick was swallowed by my pussy. He slowly rocked back and forth. He growled each time his cock was fully submerged in me. He began to pick up speed slamming into me harder with each stroke. Our faces were only inches apart. He grinned as he searched my face, watching my eyes roll back with pleasure.I had never been fucking with such force and care at the same time. He made sure each stroke was as enjoyable for me as it was for him.

I felt the pressure of an orgasm building fast. I knew I wouldn't be able to hold back for very long. "Gerald, I'm going to..." His lips slammed into mine. He devoured my mouth with deep passion. I could taste myself on his lips. Then I came. Hard. I screamed and bucked wildly from the power of it. Gerald held my by my hair, thrusting with all his might. I clawed at his back and shoulders, almost unable to handle the waves of pleasure. Gerald slammed into my one last time. He held me tight, continuing to push as hard as he could. I could feel his cock spasm and twitch. I felt a hot liquid inside me.

Gerald collapsed on top on me, gasping for air. I was helplessly weak.

"That was amazing," I managed to whisper. My voice was hoarse. Gerald chuckled and propped himself up on one arm. He carefully stroked my face, wiping away hair and sweat.

"I knew hiring Daniel would prove to be the best decision I ever made. You, my dear, are amazing." Gerald grinned. He cupped my face in his hand and tenderly kissed my puffy lips. Slowly he rose from the bed and began collecting his clothes. He stared down at me while he dressed. "It seems, my dear, I have stayed a little longer than I should have. My wife will be wondering what happened to me." My heart sank. I wished for him to stay. He held my gaze as he dressed. I stood, not wanting to look as pathetic as I felt.

"Well, it was a pleasure to say the least," I giggled. A half hearten attempt to disguise my disappointment at his departure. He caught my hand and roughly pulled me to him. He grasped a fist full of my hair and kissed me deeply. My heart skipped and fell into my stomach. He withdrew and smiled that boyish grin of his.

"I didn't say I wouldn't be back tomorrow." He winked and turned down the hall. I followed him to the door, painfully aware that I was still completely naked. At the door Gerald turned and swiftly grabbed me by the bottom. "Oh and don't you dare shower while I'm gone." He kissed me deeply once more and then he was gone. The door slowly closed behind him allowing anyone who was in the hallway to see me standing naked in my door. I could hardly wait for the following day.

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Unexpected MorningWhen looked upon her eyes shined as if to radiate the passion for life which lay within. Eva stood in the cool morning air, her flesh tingling after the cold water of the lake. Every morning she took delight in the peace this sheltered lake gave her before the day really began. It made her feel centered and had the effect of purifying her of any worries she might have of what the day held in store. But as she stood there naked letting the suns spring rays dance on her body she...

3 years ago
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Unexpected night of fun

It was a warm spring evening and the smell of the rains from that afternoon was still in the air. With the windows of my truck rolled down as I drove, I could smell the sweet smell of the spring plants mixed in with the wet stone smell coming up from the streets. I enjoyed the refreshing air. I had been home alone, bored, and decided to seek some excitement. I had no idea what awesome experiences were in store for me this night. In my head I had been going back and forth about where to go. A...

3 years ago
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Unexpected Experiences

I had been house sitting for the last week while friends were away. A beautiful home that had a gorgeous pool and hot tub that I had been dying to use. Unfortunately terrible weather had prevented it until today.  Today was perfect for a lazy day lounging by the pool and I intended to make the most of it. I slipped into my bikini, grabbed all the essentials for the day and made my way to a banana lounge where I could read, doze and work on my tan for as long as I wished. By mid-morning I'd...

Straight Sex
2 years ago
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Unexpected date

“Just a minute,” I yelled. Rolling out of bed I picked up some random clothes that where laying around, not bothering to check exactly what I was putting on and not caring at this time in the morning. Whoever was knocking had better have a good reason for waking me up early on the weekend. There's no way I'd be able to fall back asleep either. My German Shepherd was barking, it's tail wagging, no doubt happy I was starting the day early. I walked to my front door, running my hand through my...

4 years ago
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Unexpected Morning

Unexpected MorningWhen looked upon her eyes shined as if to radiate the passion for life which lay within. Eva stood in the cool morning air, her flesh tingling after the cold water of the lake. Every morning she took delight in the peace this sheltered lake gave her before the day really began. It made her feel centered and had the effect of purifying her of any worries she might have of what the day held in store. But as she stood there naked letting the suns spring rays dance on her body...

2 years ago
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Unexpected Encounter In A Park

Hi guys, I’m Varun(name changed) from Bangalore. I’m a bisexual strongly attracted to men who are older than me. Possibilities do exist. So if you wanna know more about me and my experiences, get in touch with me. So this story is about an unexpected encounter that happened to me last year. I was 19 years old then. I was always fascinated to see new dicks and gave a fetish for underwears. Also, I like exploring sex in public places. This story outsets when I wanted to inquisitively experience...

Gay Male
4 years ago
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Unexpected Morning

Unexpected MorningWhen looked upon her eyes shined as if to radiate the passion for life which lay within. Eva stood in the cool morning air, her flesh tingling after the cold water of the lake. Every morning she took delight in the peace this sheltered lake gave her before the day really began. It made her feel centered and had the effect of purifying her of any worries she might have of what the day held in store. But as she stood there naked letting the suns spring rays dance on her body...

3 years ago
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UNEXPECTED TURN

When Jake first realised he was attracted to his mother, he had no idea that his lust would take such an unexpected turn, leading him down roads he never would have imagined in his wildest dreams. Jake was eighteen, and had just finished high school when he started planning to seduce his beautiful, 42 year old mother. Just the thought of sucking on Lucy's big, delicious breasts was enough to make Jake's uncut 7-inch cock stand up straight and start oozing with pre-cum. Following the advice of...

2 years ago
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Unexpected Restroom Sex 8211 Part 3 8211 The Restroom Again

This story is the continuation of the previous story. As I told before having sex with one girl led to a snowball effect. It’s really surprising to see that there have been so many women around me; whom I thought didn’t even care about boys or made people feel that they were confined to themselves; were not like that. It was the case of Janani Priya that taught me a lesson. We are all deluded about people. We just can’t find who is what. Ok enough philosophy for today. Ill introduce myself...

3 years ago
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Unexpected Turn 8211 Event Of A Lifetime

Hey all this is Raj, 23 from Bangalore. This is story of mine having sex with an unexpected person and how it turned out to be one of the best ever had. The story begins when I completed my boards exam and waiting for the results. During that time my family decided to go on a vacation to Andaman and Nicobar islands but I stayed back with a lot of stubbornness as was not interested to roam around so being the only son my parents weren’t so confident on letting me stay home alone so they asked my...

Incest
3 years ago
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Unexpected Sex With Neha

Hi guys this is a story when I was I had a huge crush on a girl called Neha. We were good friends but she always used me in her studies to get her work done. I helped her thinking that she respected me and we were good friends but that was not to be… After knowing each other for two years we were supposed to go for a college trip to Manali for a couple of weeks. My friends always told me that she was a bad girl and stay away from her but I never listened. I wanted to propose her but I never...

3 years ago
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Unexpected Move From Asha

This happened a four months ago. We have one manufacturing at Nagpur. As I am the head for India and as part of employee engagement we used to have our family day function at each location. I had requested my assistant Asha to go to Nagpur and help the team a week before so that we have 100% participation from employees and their family. While discussing this I got a call from Nagpur factory that employee involvement is not at all there and that he is confused. Local HR is busy with day to day...

4 years ago
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Unexpected Experience With Sanjay Uncle 8211 Part 2

Hi! All friends, I am back with another interesting episode of my unexpected. but exciting and real encounter. Your valuable comments are welcome. After that exciting evening in his house, we became very intimate and one  day, he planned for a long night-session of sexecitement, as his mother would return only after one more week, but I discarded it as impracticable and left it at that.  The following Sunday, Sanjay anna(uncle) lunched with us and with my parents’ permission, both of us went to...

Gay Male
2 years ago
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Unexpected Encounter With Sanjay Uncle 8211 Part 1

Hello friends, hope you liked my earlier story with my master. Here is another one for you to read and offer your valuable comments and encouragement With the summer camp and the feverish activities associated with it coming to a close, and sir’s absence for nearly three weeks( on domestic reasons), I felt miserable, like a fish out of water. The fantastic taste of that unbelievable and unexpected sweet forbidden pleasure with sir (My master love-locked me -3) was haunting and making me...

Gay Male
3 years ago
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Unexpected Outcome

Unexpected Outcome At the ripe young age of 25, I had everything going for me. I could get all the dates I wanted and with almost any of the town's hottest- looking ladies, too. I had college degree and a good, well-paying job, a nice car and a decent apartment. Then, one day, my world came crashing down around me and everyone else too, for that matter. No one knew it at the time for the only news available at this point was that the Earth was going to have a near-miss experience...

3 years ago
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Unexpected Outing Part 1

"Unexpected Outing" Part 1. John returns home in female clothes following an accident. Fiction by Johnny Cumlately. John's earliest recollection of cross dressing when he was about 12. He would surreptitiously "borrow" his mother's underwear. She was even then years behind the times and wore pink satin knickers with elastic at waist and thighs. She also wore corsets with miles of lacing. John, now 35, had been happily married to Mary for about ten years. They lived in a pleasant...

2 years ago
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Unexpected Mommy revised Parts 4 and 5

Unexpected Mommy - Part 4 by Trish5160 Mrs. Stone could not believe the erotic display on her couch this evening.? She instinctively knew Alix was participating in sexual intercourse even though it was just a dream for him.? She knew by his movements.? Voluntarily he had parted his own legs wide, his moans, the thrashing of his head from side to side, the heavy breathing.? All signs of a female in heat.? All signs of a female being taken. There was...

3 years ago
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Unexpected Outcome

Unexpected outcome. At the ripe young age of 25, I had everything going for me. I could get all the dates I wanted and with almost any of the town's hottest- looking ladies, too. I had college degree and a good, well-paying job, a nice car and a decent apartment. Then, one day, my world came crashing down around me and everyone else too, for that matter. No one knew it at the time for the only news available at this point was that the Earth was going to have a near- miss...

2 years ago
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Unexpected Meeting Coming Home

Unexpected Meeting - Coming home by strangefun WARNING: This story contains graphic depiction of depraved sexual acts, sisification, sexual abuse, humiliation and torture. Read at your own discretion! From the author: This is a continuation of the "unexpected meeting" story, and for all the sissies, I recommend reading it wearing your favorite sissy outfit and, of course, a chastity device, so you can feel the same confinement and sexual frustration I felt when writing...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Unexpected Opportunity Unexpected Bonus Pt 2

I stood naked in front of my full length mirror. I absently stroked my shaven pussy as I thought about my evening with Gerald. It had been two weeks since we had our unexpected encounter. I constantly thought about seeing him again. He hadn’t come back the following day and I was beginning to think he was regretting what he had done. I didn’t completely blame him, I mean he did have a wife and kids. I’d better get dressed, I thought. I was meeting the girls downtown at our favorite bar. I...

Mature
3 years ago
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Unexpected circumstances

Unexpected circumstances.I don’t really know why I did it. I still don’t. Boredom I guess. I hadn’t used the Hotmail account I’d set up years earlier for as long as I could remember. Fully expecting it to have been closed, I navigated to the website and typed in my username and what I thought was the password I’d selected at the time of creating the account. To my surprise, the account hadn’t been closed, just suspended due to inactivity. As I watched the list of e-mails populate on the screen,...

3 years ago
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Unexpected Weekend Chapter 3 Final

"So what did you end up buying for dinner tonight, Mr Chef?" Alice said excitedly "I got us a couple of steaks and thought maybe a nice steak dinner with all of the trimmings, chunky steak cut chips, mushroom, tomato, onion rings and peppercorn sauce" He replied "Oohh very nice, getting the real VIP treatment here" she said with glee "Well only the best for my guests" he said "I wanted to make you something nice and if I can be rather blunt, something that I won't have to slave...

1 year ago
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Unexpected Gifts

"You sure you don't need me, Sir? I don't mind sticking around." "No, Don. Go on, enjoy a few days off before we get swamped." "All right, then. Thanks." Don left his boss, who was in remarkably good spirits considering how close Christmas was and how busy they would get in a week. However, he decided, if the boss said take some time, Don wasn't one to argue. He knew he'd be working his ass off soon enough, so he'd get while the getting was good. After speaking to the boss, he...

3 years ago
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Receptionist Bonus

Sitting through the hearing was worse than she would ever have imagined. Dr. Roxanne Tremblay sat before the disciplinary committee of the hospital for the first time in her career. They couldn't do it, Roxanne tried to assure herself. They couldn't play the video in front of the whole committee. Her hands were trembling as she watched the chairman of the committee toying with the remote control to the TV. He was only waiting for one committee member to return from lunch. "Sorry I'm...

3 years ago
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Unexpected Wedding Night

I was plowing through the snow towards the cabin in front of me. Unexpectedly being stuck in this snow storm with temperatures dropping fast, that place was my only hope of some protection from the cold.On my way back home from a neighboring city, I ignored the weather warning partly because I couldn’t afford to stay in a hotel And partly because I just wanted to be home. But halfway through the long forest road, disaster struck, my front wheels locked up in a corner and my car went straight...

Interracial
4 years ago
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Unexpected Stranger From novella entitled ESCAPE

Chapter One It was Friday night around ten o’clock, Lauren guessed. She wasn’t really sure, because the only thing that had her complete attention at that moment were dark brown handsome eyes boring into hers with such intensity that she couldn’t look away. She was mesmerized. The night had started out innocently enough. She and her girlfriend had come to MacAllister’s bar to celebrate her girlfriend’s birthday. The next thing she knew, her friend on the barstool to her right was laughing with...

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