Deanne and Me

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Training for a 'new position'.
3.7k words
4.46
28.6k
3

Part 1 of the 4 part series

Updated 10/30/2022
Created 10/22/2009
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It was Friday, about two hours before my shift was to end. I glanced at the note that had just been placed on my desk. It was from the office manager of the call center I work in. 'Come see me when this call is done' is all it said.

Having no idea what bug might be up her ass, I wasn't looking forward to it but I did as requested. When I walked in her office, she was there with a lady younger than either of us. This woman was a knock-out! Long, thick, dark hair, soft brown eyes, full and tantalizing lips, and a body that screamed things to my anatomy that shouldn't have been being heard. "This is Deanne," said Sheila, my manager. "She's the new Corporate Director."

Deanne and I shook hands and smiled at each other but it was nothing more than the obligatory smiles that's so prevalent in these situations. I did notice however, that her hands were very soft and warm. I scanned quickly over her as she walked away to seat herself in a chair at the table in the middle of the room. Her flowing knee-length skirt was one of those that made you think you could see through it, but you actually couldn't. She had on a beige blouse that not only accentuated her dark hair and tanned skin, but flattered her ample bosom as well.

For those of you who know me, you'll not be surprised that I more closely examined her legs and ass - all of which easily achieved the "you can eat crackers in my bed" approval. The shape of her ass was nothing less than the one I had wet dreams from my whole life.

Not consciously realizing that Deanne had sat down and I was still staring at her shapely thighs that were now exposed to me, it was the voice of Sheila that snapped me back to the situation at hand. "Please have a seat. We have something to discuss with you."

Those words not only snapped me out of the trance I was in, but they sent a chill through me as well. Was I getting fired? Why introduce me to the new CM? What the hell is going on? My mind was now racing with countless but silent questions.

Seating myself at the same side of the table as Deanne was at, I took the opportunity to shoot another glance at her. My God! She was so sexy!! Good thing I was now seated or I would have been arrested for sexual misconduct due to the bulge in my pants! Those legs and thighs of hers were just begging me to pay some physical attention to them! I drew a quick mental picture of seeing her naked and I could easily envision me attacking her, sucking and enjoying those breasts, kissing those full lips, and pounding my cock into her seductive ass.

The meeting had been only going for a few minutes when Sheila looked at me and said, "you have been selected to go to Corporate for a month and have Deanne train you for a new position."

I immediately and uncontrollably grinned as I turned that statement into something purely sexual. I'd be more than happy to have Deanne train me for any position she wanted me in, and ultimately I knew this meant Deanne and I would be working closely together. That was fine with me but I had to wonder - is broken zipper replacements a tax write-off for job expense?

This woman would certainly be testing my professionalism as well as my self-control, but I had learned from the conversation that she was also on the Board of Directors so I figured it was in my best interest to not only learn everything she wanted to teach me, (still grinning here), but to make sure my hormones stayed under control.

The biggest shock was that I would be spending the next month in Hawaii and it would be paid for by the company! I'd be on the Island of Oahu! HOLY SHIT!!! Now, I admit that I don't know a whole lot about geography, but I knew that was where Pearl Harbor, Honolulu, the famous Waikiki beach, and, (a little bit of trivia here), the only palace on US soil - Iolani Palace, were all situated on that island.

I was still in shock the next week as I sat there beside Deanne on a jet, waiting to taxi out to start the flight. The flight was soon underway and it took little time for her and I to relax around each other. She was really easy to talk to and had a sense of humor that was close to my own.

She informed me that she was not of the 'all work' mentality and she expected me to enjoy the Island and all it's treasures. Not being one to resist an opportunity to investigate future opportunities, I asked if she was going to be my personal guide. Surprisingly, she said that she was planning on showing me a few places. My delight was impossible to hide as a big smile once again overtook my face.

Glancing down at her shapely legs that were escaping from under her thin, black skirt, I wondered if this lady ever wore slacks! I hoped she did or I could easily see myself being in in a hell of a lot of trouble around her. Even her voice, which had a slight accent to it, was seductive. The combination of her personality, her body, that magnificent long hair, and her voice were all so sensual that I spent most of the flight trying to nonchalantly hide the throbbing erection I had smuggled on board like a jewel thief with the Hope Diamond.

During the flight she informed me that there was a company paid rental car for me at the Honolulu International airport and I was to drive her to her house, then follow her to the hotel I'd be staying at. My smile and my erection both grew larger.

Several hours later the jet had landed and Deanne and I were driving to her house. I was following her verbal directions while trying to visually absorb all the beauty around me - both the geographic and feminine beauty.

When we got to her home she invited me in and I of course accepted. Her home was very beautifully landscaped as I sort of had expected, but it was absolutely stunning the way she had decorated it. There were minimal 'man-made' objects cluttering the beauty of the location and it was a paradise of it's own accord!!

She invited me to have a seat out on the lanai while she changed clothes, and upon stepping outside, I was in love with the area. She soon joined me, wearing just a halter top and short, flatteringly snug cut-offs. As soon as I saw her, my cock instantly throbbed in my jeans and I couldn't help staring. Her figure was the definition of sexual. Her long, slender legs blossomed into wonderfully shaped hips. Her waist plummeted seductively inward before gracefully widening to accommodate her large but obviously firm breasts. The graceful curve of her shoulders flowed magically under her long hair and emerged again to form a beautiful, erotically attractive face.

"You okay?" she asked as she walked toward me, affording me the opportunity to enjoy the gently alluring sway of her stride.

"Deanne," I sighed. "I think it would be best if I headed to the hotel," I answered as I looked into her soft, brown eyes. "Your home is absolutely wonderful, and I feel very comfortable around you," I said as I tried to gain control. "I'm perhaps a bit too comfortable around you," I added as I forced myself to look away from her.

"Please, call me Dee," she softly said as she sat down and crossed her legs. "Except of course for when we're at the office or around other coworkers," she added as she observed me staring at her tempting flesh. Oh-h-h-h!! Those legs!!!! There they were. Exposed and enticing from her feet to her hips. I savored every inch of her legs as I took trillions of mental photographs. She didn't seem surprised or upset at my behavior, which I was glad to see.

About an hour or so later, after a light snack, she said she'd drive to the "Princess Kaiulani", which is on Kaiulani Avenue, and I could follow her so I didn't get lost. It was around nine o'clock and we were soon heading to the hotel.

After going through the easy check-in at 'The Princess', the bell-hop accompanied us to my room. It was designated as a "Tower Ocean View Suite" and I almost fell over when I walked in. There was a king size bed, large sofa, and a huge glass top table with nicely padded armchairs facing it. I noticed the ocean view and almost passed out. To say it was breathtaking would be an understatement.

"Shit!" Dee exclaimed as she entered the room. "You'll never want to come to the office, and to be honest with you, I'm not sure I'm going to want to leave!" she said as we walked toward the patio after dismissing the hotel attendant. "You might be sleeping out in the car!" she said with a wonderful laughter in her voice.

My only response was a chuckle as we walked onto the balcony which was high above most surrounding buildings. Of course, being the gentleman that I am, I allowed her to step out first. It was purely accidental that I was staring at her ass when she unexpectedly turned around and said, "This is really..."

She stopped abruptly mid-sentence. I looked up at her and she was staring at me. I wasn't sure if she was pissed or appreciative. After what seemed like an hour, she finally spoke.

"This is at least the third time I've caught you staring at me from behind," she stated. I felt my face turning red. "Do you really like my ass that much?" she question me.

I know my face was going through the entire spectrum of reds as I looked at her. She was still staring at me but there was no smile on her face. She eventually began to walk toward me and I just stood there motionless, suffering temporary paralyses from fear. I didn't know if I had just written my pink slip or my invitation for sky-diving from the balcony without the benefit of a parachute.

She stepped up close to me and put her arms around my neck. "Remember," she whispered as she stretched to get her mouth beside my ear. "I'm your boss and I expect answers to my questions," she said as her fingers ran through my hair and her full, firm breasts pushed tightly against my chest. My arms instinctively wrapped around her as my hands landed firmly on her shapely and pleasantly firm buttocks. I pulled her tight against me. My erection was throbbing wildly in my pants, pounding it's Morse code of lustful desire through my jeans and her cut-offs. Our lips were only microns apart.

"Yes Ma'am, I like your ass," I whispered with a smile. Then our lips touched. It was like the movies - that first kiss. The softness of her lips, the feeling of her body pressed against me, her ass delighting my hands, all added to the pleasure I was feeling as her hands held my head firmly and her tongue gently slid into my equally anxious mouth. Our embrace lasted only seconds, but what a glorious few seconds it was. We were now standing there, both motionless and silent except for the soft panting from each of us, staring into each others eyes. "This shouldn't be happening," she whispered, but I noticed she didn't pull away at all. As my hands slid up over the bare skin of her lower back and to her soft shoulders, I kissed her again. "If you tell me to stop, I will," I whispered. My hands pulled her torso tighter against me.

"I am married, and I'm also your boss," she reminded me, not with anger or irritation but with a seductive sensual tone in her voice. I began to lift her halter top upward as I kissed her and said, "I know you're my boss. Are you telling me to stop?"

Our eyes were locked on each other and her halter was going higher and higher. She never tried to stop me but assisted me by lifting her arms. Within a few, long, anticipation filled seconds, her breasts were exposed to my appreciative eyes and hands. Cupping her breasts, one in each hand, I bent down and lightly kissed each of her already hard and erect nipples. Her body shuddered as my lips and tongue explored her previously hidden treasures. I felt her hands lifting my shirt and I obliged her by assisting her as she had me. After my shirt was off, it was amazing how quickly her cut-offs fell down! Don't know how that happened, but I was thrilled to learn she hadn't worn panties. Her shapely body was now fully exposed for me.

My cock was thrashing wildly with impatience in my pants as her hands slowly and cautiously unbuttoned and unzipped my jeans. She pushed them down and my aching erection was released. I gasped from exhilaration as her soft warm hand wrapped gently around my hot, rigid flesh. Her touch was phenomenal.

I slid my hands down the smooth, soft skin of her back and then over her ass. Squatting down in front of her my lips kissed a trail along her abdomen. Kiss by kiss, my mouth approached her pussy. My lips kissed her at the very top of her hair line and I felt her shaking as her legs parted ever so slightly. My fingers slid between her firm ass cheeks as my mouth descended the final inches and my tongue lashed out, licking over the soft, curly dark hair that covered her much desired pussy.

Gently but firmly turning her around and moving her backward toward the bed, she was soon on her back with my head buried in her sweet pussy. When I stole my first taste of her wine by licking inside her slit, she let out a gasp. My tongue then inched up the length of her smooth slit. Her hands pressed my head tightly against her and I released all my oral skills on her. Her pussy was amazing and with her legs squeezing my head, I licked wildly over her sensitive private area. She began squirming, moaning, gasping, and arching her back as I continued licking her slit.

When I sucked her clit into my mouth and flickered my tongue over the tip, she arched her back high and squeezed my head like a vise, letting out a long, deep, shuddering moan as I felt her succumb to the relentless teasing from my tongue and lips. "Oh Je-e-e-s-s-u-u-u-s-s!!!" she whimpered through clenched teeth as her orgasm was obviously growing to be quite intense. Her hands clenched my hair and was pulling it hard as my tongue licked up all the love potion I could.

My cock was throbbing wildly, banging it's head against the side of the mattress like a wild and crazed criminal trying to break out of a prison cell. As her orgasm slowly began to subside, I continued to lightly lick around her pussy and once in a while, slipped my tongue into her gloriously glazed clit. It was obvious to me that she didn't want me to stop, so I resumed my 'attack' and deployed my fingers to assist my mouth and tongue in giving her more sexual pleasure.

Gently parting her wet pussy lips with my fingers, I placed the tip of my tongue at the opening of her pussy. As I pressed my tongue flat against her pinkness, I slid it slowly - very, very slowly all the way up to her hard clit that was impatiently waiting for my tongue. Her hips lifted as if by levitation and I continued to do a series of slow, teasing licks up the length of her slit. My fingers slid into her hot tunnel and she released a gush of gratitude.

Stroking my fingers back and forth with the tips of my fingers rubbing upward and apparently hitting her 'G' spot, my tongue continued it's assignment and soon Dee was thrashing fiercely as her body released what seemed like gallons of cum to quench my burning thirst. Enthusiastically licking her pussy and sucking on her hard clit, my mouth and fingers took her repeatedly over the orgasmic falls of sexual pleasure.

She was asking me to stop, informing me that her body couldn't take another orgasm, but I didn't quite buy that so I coaxed one more orgasm from her. It was then that I was fairly certain she may be serious from the way she screamed and thrashed about as she peaked.

I moved my face away from her dripping pussy and slowly pulled my fingers out, licking her sweetness from each of them. "Oh shit!" she gasped as she tried to coax me to climb on top of her. "I've never cum like that!" she panted as I slowly positioned myself on top of her still quivering body that was glazed with a light, sexy film of sexual perspiration. My hard cock was beating against the cum and saliva saturated hair between her soft thighs as the heat and the wetness of her pussy enticed me even more. My desire for her body was expressed through the uncontrollable pulsations of my shaft.

I lifted my hips and my cock pressed itself securely between the heavenly wetness of those sweet lips that covered her pussy. This time, it was me that moaned with pleasure as her soft sensuality wrapped completely around my hot and attention craving rod.

"Baby, I'm sorry, but I can't let you cum in my pussy," Dee said with obvious disappointment on her voice. "Not tonight - but I'll explain later," she gasped quickly. "I just want you in me. Please promise you won't cum in me, but please, put it in me! I know it's unfair of me, but I want that cock in me so badly!" she gently pleaded in a frenzied babble as her hands ran over my ass, trying to pull my cock into her awaiting grandeur with the aide of her soft feet also pushing against my ass.

Even if I had wanted to refuse I couldn't have because she parted her legs a bit more and my marble-hard cock slid effortlessly into her tight, warm and saturated pussy. We gasped in unison as my length went deep inside of her. My cum filled sac was pressing tight against her ass and the tip of my cock was pressing into the roof of her vagina. "Oh my God! You're so thick!" she moaned softly in my ear. "God that feels so..." she started to say but stopped suddenly as I began to take long, slow strokes in and out of her pussy.

"OH! OH SHIT!" she exclaimed over and over again as I stroked my full length faster and faster in and out of her satin mitten that snugly held my cock. I knew I was stretching her lining to accommodate my width, and it felt as smooth and warm as I think dunking my cock in warm, melted butter would feel. The feeling was one of pure perfection.

I felt the unmistakable 'orgasm squeeze' from her pussy. Another flood of her nectar was released around my hardness while her fingernails dug into my back. Her body jolted and flinched as her pussy coated me with her hot syrup of happiness. I was trying desperately to maintain control a bit longer but I knew I was failing. My balls were aching, just waiting to unload the trainload of cum they had stored up and pressurized for dispersal. My cock was swelling thicker inside her smooth snugness.

"Oh Honey!" I moaned as I forced myself to quickly pull out of her. "I can't.... I can't hold off any more," I confessed with panic-stricken breaths. "I'm sorry but I..."

"Use my ass," she interrupted me with as she rolled over. "Fuck me in the ass if you want. I just want you to enjoy!", so I eagerly centered my engorged and oozing cock in the crack of her fabulous ass. When my mega-stimulated cock touched her soft skin, I knew it wouldn't take but a few seconds. The thick flame of my sexual fire buried itself deep between the gentle hills of heavenly flesh that was now underneath me. As I took my first few purely enchanting strokes, her soft, warm, pliable skin wrapped my cock in an embrace more wonderful than anything I've ever felt.

"Oh my God!" I softly screamed as my cock erupted. The pressure behind that first shot was strong enough to squirt it from between her ass cheeks almost to her shoulders! With each forward stroke another large sperm ball was fired and landed on her back until there were countless lakes of glittering sperm on her back. Then a river of sperm appeared, flowing from between her heavenly posterior like the magma that flows from volcano Kilauea. I had released so much cum onto her I was almost embarrassed, but Dee seemed to enjoy the fact that I had become so aroused and then was so satisfied by her.

I gently collapsed, totally drained by the pleasure from her wonderful body. We lay there, my soft cock merrily swimming in the pool of sperm it had created and I kissed her on the shoulder. She lifted her head and I kissed her neck. "I think we're going to be spending a lot of time together these next few weeks," she giggled as she nuzzled her head against me. Her soft, thick hair felt like strands of fine silk against my face.

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