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Rendezvous in Chicago - Chapter 3

"Erootic affair continues as business conference continues"

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The next morning, Jill rose very early, utilized the fitness center, showered, primped, dressed and was out the door before Dave even stirred in the bed. She joined some colleagues, she knew only from trade publications, for breakfast, having introduced herself in the lobby.

Soon she was off to a general session of the conference and then moving between breakout sessions for the remainder of the day. It proved to be a valuable experience both in terms of establishing contacts and adding to her already substantial bank of knowledge, that she would be able to utilize in her position. Her industry was changing rapidly and, as always, Jill Miller pursued the leading edge developments with a thirst to be at the top of her game.

Meanwhile, while not sleeping in as if on vacation, Dave arose at 7:00 AM and was amazed to find the suite in a perfect state of housekeeping, but no Jill. It soon registered what an awesome suite mate he had; Jill had not only attended to take care of all of her personal needs, but also managed to do a quick cleanup of the previous night's hastily discarded clothing, even neatly hanging up his clothes. He actually wondered if housekeeping's services would even be required. 'What an amazing woman this is, this Jill Miller. Quite impressive,' he thought.

Dave went for an early morning swim, completing a good forty five minute workout of laps. He returned to the suite, attended to his personal needs, showered, dressed and grabbed a light breakfast before his first 9:30 appointment. He had arranged to meet with a number of his more substantial clients in the city center, while he knew Jill would be attending her conference during the days they were together. Not one to blow off a week, no matter how enjoyable his “roommate” might prove to be, he had prepared his own itinerary to take advantage of his time in the city.

Additionally, Dave made one more stop on his way to the suite, stopping by an adult toy store.

At four bells the final breakout session ended for the day. A number of the conference participants were headed to the lounge for socializing over a pre-dinner, pre-evening, and/or pre-evening hook up. Making her excuses Jill bolted for the elevator hoping to find her lover back in the suite. At 4:07 the door to the suite swung open.

Dave's jaw dropped as he was mesmerized by his lover whom he had not seen today. Jill was so fucking classy, dressed in a charcoal pinstripe business suit that hit her just above the knee, with a three inch slit on her left thigh. With each step the flash a her thigh had her leg loving roommate out of his desk chair and into her embrace. He rushed at her with such force that he backed her uptight against the door.

He gathered her wrists in his left hand and stretched them above her head thrusting her chest out involuntarily and into the grasp of his right hand. Her ivory laced blouse was soon unbuttoned and her supportive but sheer bra unclasped. In one swift motion the blouse, the bra and the jacket to her suit were all stripped from her, baring her beautiful voluptuous breasts. He planted his mouth on Jill's, and the two engaged in a tongue dueling kiss that robbed them both from normal breathing. They were locked in a tongue tango that bordered on each trying to devour the other.

Dave's right hand moved down to unzip her skirt away. He lowered her thong down her lovely thighs, over her knees, then her muscular calves and her thin ankles. Jill cooperatively stepped free from this last protection from her womanhood.

While still holding her wrists high above her head, Dave took a step back and lusted over the vision before him. Her make up was perfect, classy but not slutty. Her high cheek bones enhanced the sparkle of her translucent icy blue eyes. Her soft auburn hair was so rich and shiny, so healthy in appearance. His nostrils filled with the hot, spicy scent of her Emporio by Armani perfume and then his eyes drifted lower. He took in her heaving voluptuous tits with their lovely areola and hard nipples. Drifting lower still, the slight puff of her soft tummy and her landing strip leading to her already moistening pussy presented such an erotic sight. Finally he reached his special treat, Jill's sheer black thigh highs and black three inch pumps with their noticeable red soles.

What an absolutely wondrous sight! His face showed his obvious appreciation of her dazzling attractiveness to him. Her physical beauty was so obvious. But Dave knew far more about this woman than her physical attributes. He knew her as an intelligent, driven and successful woman. She willingly would enjoy baseball and football games, give him a good poker game rivalry and had an earthy tone that could easily flow from a person in control to a lusty lover in a heartbeat. And, the most attractive feature of his lover was that she was so aroused by his attentive and loving pursuit of his prize: her!

This brief scene took only seconds to play out, but time felt like it stood still.

Jill waited and and while she loved his obvious appreciation of her physique, she longed for Dave to take her, just ravage her!

As if she mentally transmitted her desires, Dave stepped back into her, again roughly pushing her against the door and in one exceptionally fast motion, released his diamond cutter hard cock from its confines and in an instant was pressed against her tummy. Jill could feel his cock throbbing, causing her already aroused pussy to flow with moisturizing lubricant. She craved to be taken, hard and insistent and this was not lost on Dave as he positioned his dick at her maidenhead and thrust up into her love channel. He wasn't gentle. He was in control and she loved his focused and forceful intrusion into her life giving cunt. He rapidly thrust in and out of her steamy center, while she humped her pelvis on his cock like a cheap whore. They were both soon enraptured in the throes of their ecstasy, coupling like two animals in the wild.

They were all too soon on the brink of their mutual climaxes but savored their coinciding release knowing the night was young and the week was only beginning. Dave finally thrust into Jill's sex to the hilt, his balls slapping against her extended pussy lips and he spewed his baby batter deep within her womb. Jill was overcome with her orgasmic release and her pussy pulsed and contracted around his manhood with her pleasure radiating from her center throughout her writhing body, reaching all of her extremities, her knees buckling as her lover pressed her firmly into the unmovable wall. She was totally vanquished, her body was like a puppet in the complete control of her lover, having totally surrendered to his conquest.

Dave released Jill's wrists and she lowered her arms to encircle his neck pressing her luscious breasts with their firm peaks burning into his chest, as she wrapped her legs around his torso and locked her ankles under his cute butt. With ragged breathing, Dave secured Jill's heaving body against the door until he was able to re-gain a somewhat normal breathing pattern. Stroking the undersides of her strong thighs and up the tight cheeks of her sumptuous ass, he then carried his lover into the bedroom and gently laid them both down on the bed while never breaking the most salacious kiss; two lovers unwilling to break their carnal bond.

“Relax here, darling, while I prepare the next station on our journey to explore the pleasures of your body.”

“Mm … that sounds so erotic. After that welcome do you think I will be able to hold up while you play out your plan of ecstasy?”

“Jill, the next step is meant to give you a short reprieve to re-rejuvenate your batteries … and mine,” he chuckled.

So while Jill relaxed briefly into slumber-land, Dave went into the adjoining bathroom and made his preparations. Soon thereafter he re-entered the bedroom and tenderly kissed his lover first on her lips, then her eyelids, then nibbles the length of the sides of her neck, following in quick succession his tongue tasting her soft skin and dipping into her ear, whispering, “Ready to continue beautiful?”

“Mmm … show me the way my sexy, handsome prince.” Dave took her hands and led her into the bathroom now dimly lit from the glow of a dozen candles. The room was engulfed in the vanilla scent given off from the candles and the vanilla oils in the hot bath he had prepared for his lovely lady. As he helped her remove her stockings and heels, his nostrils were filled with scent of their recent lovemaking being emitted from her womanly core, displayed just at his eye level. He resisted his temptation for further sexual antics and helped her into the bath, lowering her body into this pool of rejuvenating elixir.

“Let me wash your back and then I'll leave you to relax and recharge for a while.”

“You do know this is spoiling me, don't you?”

“Jill, I want to spoil you and make this experience one that will never be erased from your memory. Now just relax sweet lady. You need to unwind.” Dave then went into the living room, with perfect timing as there was a light rap on the door.

“Room service.”

Dave again quickly donned a robe, gathered the strewn about articles of clothing, throwing them hastily into the bedroom and retrieve a twenty from his cash to tip the worker. He opened the door and a very professionally dressed middle-aged man entered the suite pushing a cart that held all the makings for Jill's favorite drink.

“Good evening sir, I'm William and I'll set up over here. It will take me about five minutes to prepare your first couple of drinks. Do you need to watch me in case the lady would like an additional cocktail?”

“Thank you, William. I'm Dave, and although I know how to prepare this drink, it certainly couldn't hurt to gain any tips from a professional.”

“Thank you, sir.” William went about mixing two of the beautiful concoctions under Dave's watchful eye. Dave did take note of a number things that William did to enhance the presentation of this pretty cocktail. “Thank you again, William. That was very interesting and quite helpful.”

The drink cart was left as Dave escorted William to the door while slipping the twenty into his hand.

About five minutes later, Jill emerged from the bath. Not bothering with a robe, Dave admiringly took in the fully exhibited body of his lover. He took her hand and instructed her, “Now, honey, close your eyes. No peeking,” he chided her. He led her into the living room and introduced into her manicured hand her favorite drink. “You can open now.”

Jill's eyes opened as she expressed her surprise after her first taste, “Oh, Dave, white chocolate raspberry martini? Are you serious? You think of everything.”

She leaned forward and kissed him, while he could not resist fondling her sumptuous breast.

“Come, let's sit on the couch while you tell me all about your day. Who of interest did you meet? Who gave interesting presentations? Did you glean any new ideas to help you day to day?”

So the conversation carried on comfortably through the next hour with both Dave and Jill totally naked and absent of any inhibitions, as they enjoyed a drink and talked about each of their experiences of the day.

“Jill, while I was out today, I bought you a little something that I would like to see you wear this evening when we go out to dinner,” as he handed her a small thin gift wrapped box.

Her eyes were gleaming in anticipation of what might be inside. “Oh, you shouldn't have bought me anything. I don't have anything for you.”

Smiling an almost lecherous smile, he said, “That's okay. I didn't expect anything. But if you use this tonight, you will actually be giving me a very special gift indeed. Are you going to open it?”

Jill unwrapped the box and removed the lid. Peeling back the tissue paper she looked somewhat puzzled, questioning what she was looking at.

Dave interjected, “It's called a silver finger, clit g-string! If you could wear it tonight, I'm quite sure that dinner could be most interesting.”

“And you would rather I wear this than nothing at all under my dress.”

“Well let's just say that it should be a most stimulating evening.

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And with it nearing 7:00, we should probably think about getting ready to make our 8:30 dinner reservations.”

With that, they moved to the bedroom and Dave showered while Jill did a touch up on her hair and applied fresh make up, including a small amount of Emporio perfume behind each ear and behind each knee, knowing full well the manner in which her lover adored her long toned legs. Before the night was over, he would be giving them a little extra attention.

To compliment her soft mandarin colored cocktail dress, she inserted her dainty toes into dark tan thigh high stockings, feeling luxurious as she pulled them delicately up over her thin ankles, then her exquisitely sexy calves before clinging to her beautifully strong thighs, that she knew would be useful before the night was over. Smoothing each stocking, she loved the sexy feeling they always created in her brain, already so aroused with excitement of what pleasures she knew would come tonight.

Next, she took a deep breathe as she looked at her lover's gift, reaching for it with trembling fingers.
She felt the arousal of her clitoris as she wondered what affects this handy little toy might impart during the course of dinner. Could she really wear such an article throughout the entire dinner? Would she be experiencing wave after wave of pleasure coursing throughout her body continuously? Would she even be able to eat or actually carry on a coherent conversation? What if she met someone from the conference - could she appear to be her normal confident and professional self, or would she be a blathering air head?

So, with trepidation and excitement, slid the “garment” up her sexy legs and positioned the toy in place, with the finger tight against her little man in the boat. She immediately felt a small amount of pleasure and thought, “Hmm, not bad. This will be fine," and smiled, realizing her gift would not render such a level of arousal that she would appear out of control. Little did she realize the full effects …

She slipped her stocking clad feet into each of her black and cream strap back open toed heels. Then she stood to cross the room to slip into her dress. As she took those few steps, she was unexpectedly jolted with pleasure from her little device. Her knees felt weak and she felt slightly light headed and so stood still to regain some semblance of normalcy. The waves of pleasure subsided to a manageable level. 'Wow, can I really wear this thing all evening?' she questioned.

Jill slipped into her dress that had a plunging neckline to just below her ample breasts, providing the display of an ample exposure of the sides of each of her beautiful tits, a very sexy exhibition of cleavage and the full skirt resting about 4 inches above her knees. She ambled into the living room area, becoming a little more comfortable with her little toy. She was happy to find that she still had about half of her martini left as she took a seat to relax and await Dave. About ten minutes later Dave exited the bedroom, looking so sexy in his tan suit, with a crisp white shirt and a colorful tie, all of which would compliment his dreamsicle date and enhance his normally tanned skin tone, with his full head of rich salt and pepper hair.

Jill arose from her chair as he entered the room, and they both stopped dead in their tracks perhaps six feet separating them, with each drinking in the attractiveness of the other. Both could not wait to have people see them as a couple; an attractive and sexy couple, with the adoration of each other so apparent in their eyes. They were happy and in love, and it showed.

By the time they made it to the elevator from their suite, Jill's new toy was really doing a number on her. “You know, if I can endure the treatment from your toy that long, when we return from dinner, we are going to live out a fantasy of mine.”

“Oh, and what exactly is that? What is your fantasy? And what do you mean if you can endure it that long?”

Dreamily gazing into his eyes, with her arm around his neck, her full voluptuous rack firmly pressing against her man, while the elevator made its decent from the top floor, in a husky whisper, leaning into his right ear, Jill said, “You fucking bastard, you have me as horny as a two-bit whore with this little device working on me. You will just have to wait and see the effects of your toy and patiently await my fantasy, which will remain my secret until then.”

Dave was hard as a teenager, with his lover in such intimate contact and with her words delivered in such a sultry manner. His excited state had him briefly consider skipping dinner altogether. He knew better, of course, and he decided to enjoy the sexual interplay with his delicious roommate. He realized that after a few hours of teasing and stimulation, Jill would be on the edge all night and begging for him to take her - to take total control of her and fuck her hard.

He so loved arousing her in such a salacious manner, after months of explicit chatting online, he loved keeping her in this state of excitement. He had dreamt about an evening like this for so long and to extend the full pleasures of the long tease, rather than rushing into unrestrained and uninhibited hot sex, just wasn't the option he wanted just yet. He was going to enjoy this evening all evening and reap the sexual favors as his reward when they returned from dinner, even though he thought Jill might just ravish him any second.

His mind was racing with the options and scenarios, but he was jolted back to reality when the elevator came to a quick stop and the doors parted revealing the hotel's main lobby. Slightly red-faced, the two lovers stepped apart and, holding hands, emerged out the doors and into the beautiful summer evening. Checking his watch and enjoying the cool breeze off of Lake Michigan providing a respite from the heat of the day, he suggested that they walk the four blocks to the restaurant, knowing that her state of arousal from the stimulation of her toy would have her juices being produced like a leaky faucet and running down her thighs into her stocking tops. Jill objected and sternly advised Dave that a cab would be a requirement, not an optional request. So they took the first cab in the cue; damn if she didn't flash the valet again. Well it saved on tips as the young man stood there with his mouth agape, not even thinking about the normal automatic gratuity.

They arrived at the restaurant with a half hour to spare, requested and received preferred early seating. With the help of a Franklin to the mater de, they were escorted to a wonderfully secluded corner booth, providing the lovers with some modicum of privacy. Only the head waiter and his two hand-picked young assistants were allowed near the table. Difficult enough to control, the two young men were falling all over themselves, making any excuse to service the table until Dave requested from the head waiter that they be allowed some fairly private time without further interruption. “Please sir, just serve the food with attentive, but not overwhelming service.” The two young men were instructed to attend to this table only upon instruction from the head waiter.

With Jill feeling frisky from the continual, if not always intense stimulation from the g-string, she provided the young men with ample displays of leg and boob to keep the lads at least semi-erect. There were whispers and chuckles each time they returned to the kitchen, as the entire wait staff was fully aware of the MILF's occasional flash of her charms.

Dave awkwardly consumed his entree and beverages with only his left hand while rarely removing his right hand from between Jill's stocking clad thighs, with the frequent dips passed the skimpy undergarment and into her drooling quim. Jill barely touched her dinner, her mind overwhelmed in her continuous state of sexual excitement. She must have mentioned to Dave a half dozen times that she thought the room temperature was too warm and that she really wasn't hungry.

"Perhaps we could return to the room soon?" she inquired.

Following a leisurely hour and half culinary experience, Dave took her hand and said, “Do you think we should return to our accommodations, or would you care to linger over an after dinner cocktail?”

“You bastard,” she hissed, “You know I have been on the edge all night! Now get my sweet ass back to our room and slide that pole of a cock in this pussy, before I take a knife and cut the damn thing off, so I can stuff it in my cunt myself!”

Dave calmly offerred, “Oh? Are you in a hurry?” with a sly grin exposing his knowing torture of this delicious damsel, who was definitely in distress.

On her shaky legs, Jill led him from the restaurant, into a waiting cab and attacked the man with her tongue plunging into his mouth. She barely gave him the opportunity to tell the cabby their destination.

As soon as the livery screeched to a halt and Dave handed the driver the first bills he could fish from his pocket, a ten and a twenty for a twelve dollar fare, she once again manhandled Dave pushing him into the glass wall elevator car. The car was unoccupied, but it really didn't matter as she reached beneath her dress and hastily removed the g-string, dislodged Dave's fully erect cock, pulling his dick to her cunt entrance, raising her hem and on her tip toes, she demanded, “Now Mister, my fantasy! Shove that prick up my cunt until I scream with my release.”

With the dexterity of a ballerina, she hit the button to bring the elevator to a halt as the overheated pair humped and fucked like two wild animals, right there in plain view of anyone who might look up at the car stopped between the fourth and fifth floors and rocking from the mating of its occupants. So aroused were they that it couldn't have taken more than a half dozen ravaging strokes before his cum was blasting into her steamy pussy and Jill screamed the release of her orgasmic delight!

The emergency buzzer and bells suddenly began screaming also, calling attention to the halted unit. The couple blushingly acknowledged their embarrassed sighting of the small crowd gathered below gawking and applauding their carnal performance. They dislodged the emergency car hold, as Dave dislodged his still leaking cock from her oozing pussy. Jill thought, 'What the hell, give 'em a real show,' as she lowered herself to her knees and took Dave’s cock in her mouth, cleaning their ejaculate, and then wiped her mouth with the back of her hand and waved to their impromptu audience as the car then zoomed to the top floor.

Giggling and guffawing their way down the hall to their suite, the couple could barely contain their admiration for each other. They were having fun and truly enjoying their love affair. Both realizing the night was still young and their lovemaking would continue into the wee hours of the morning, as they attempted and failed miserably to satiate their lustful desires.

As the same elevator car opened on the first floor for the next occupants, a razor thin man in his late seventies followed his ever complaining old bitty of a wife who tipped the scales at close to three hundred pounds to take sole possession of the lift. The air was filled with the scent of the recent carnal activity. His wife protested, “What the hell is that damned smell. This hotel has to have the worst housekeeping staff of any we have ever run across!”

The older gentleman spotted the hastily discarded silver fingered clit g-string in the corner on the floor. Bending to retrieve the toy, memories from decades gone by rushed to his head as his nostrils filled with the succulent aroma of Jill's juices.

“Now what the hell is that you picked up off this filthy floor?” his wife questioned. But she was paying scant attention to him as she rummaged through her purse for her already used hanky to cover her nose.

The old man slipped the toy into his jacket pocket without comment … just a knowing lecherous smirk.

Published 
Written by oz99
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