Room Service - Madeleine Delivers

Author's Note. Hi all. Returning to Literotica after too long a pause. I appreciate any and all critical feedback - positive and not so. Many thanks to Allegra for their sustaining inspiration. Hope you enjoy!

*****

The Mulberry negotiations were dragging. Jack was pissed. His client was a jerk, and his opponent's client was a fool, and they deserved each other. They should settle and move on. Instead, they each pressed on in their petty little war. As a senior partner at Aubrey & Maturin, with over 30 years of practice, he knew this should have been easier. This negotiation was business, and in the end, the only losers would be their shareholders. The winners, of course: The lawyers.

Early in the process, Jack realized this was going to be a war of attrition. Each day exhausted him, so rather than commute an hour each way from home, draining him further, Jack elected to rent a suite at Two King East in downtown Toronto. Two King was a small boutique hotel, tucked into the middle of a condo development, it offered discrete and top-notch service to executives who needed a quiet getaway. In keeping with the low key presence except for a bar, there were none of the usual hotel amenities such as restaurants, gyms, or pools. In fact, Jack couldn't remember ever seeing the chambermaid carts that typically jam hotel halls.

Slim, very attractive women staffed the front desk. Their uniform was sharp and professional; a black sleeveless wrap dress with surplice neck. The length rose to mid-thigh. Stockings and black heels completed the standard outfit . Managers wore tailored jackets. All wore deep red lipstick with either short hair and hair up. As attractive as they were, they were all very business. All guests and visitors had to be cleared by them on arrival. If you weren't announced, you could not get access to the guests.

The bar was one of the stops at the end of a weary day. Jack had struck up a relationship with the regular bartender, Ms. Madeleine. Jack's favourite drink was a double Dalwhinnie Scotch. Early in his visit, Madeleine took some delight in pointing out to Jack, "Oh, a double D, like me." Ms. Swann may have been the only chink or might that be the kink in the hotel's iron clad ultimate discretion directive: Staff must not be too familiar with the guests.

She had his double Dalwhinnie poured and waited for him at his usual time. Jack usually ordered a dozen oysters and flirted with the beautiful twenty-something.

On this particular day, Jack arrived at the hotel much later than usual. He bypassed his usual stop at the bar and made his way directly to his room.

The elevator whisked him directly to his floor. There were just four suites per elevator lobby which assured guests a fair amount of discretion and privacy. There were no peepholes on the door, a strict no knock policy: discreet buttons, if needed, activated chimes within the suite to announce visitors. Actually, residents would have already known who was coming as they would have cleared them at the reception desk. The elevators went directly to guests floor. Of course, staff could use their pass keys to access all levels if needed. All of this was actively monitored by security; all security tapes were deleted on a 24-hour cycle.

He was pretty sure he had the floor to himself, but then again, the hotel was so quiet there was no way to know for sure. The suite had become Jack's sanctuary. It contained a decent sized living room offering generous lake and city views in two directions, a large TV, a proper desk for working. A small kitchen with stove and fridge was available should he feel like whipping something up himself, There was a generous bedroom equipped with a king-sized bed and a full bathroom, both with fantastic city views. Some evenings after assaulting a homemade dinner, Jack just loved to plant a genuinely girly bath bomb in a full tub with candles and a very large whisky and take in the night time view. The bathtub would comfortably accommodate two, which caused Jack a bit of frustration. He hadn't had time for a relationship for quite a while.

Jack had just stepped out of the shower when the door chime sounded. Jack wasn't expecting anyone, so he ignored it. Next, he heard the door opening. "Room Service!" a young woman's voice called out cheerily.

"WTF! I didn't order room service," thought Jack. He quickly donned one of the suites' plush bathrobes and prepared to confront the intruder.

"Hello, Mr. Aubrey, sorry to barge in on you," Madeleine had advanced her cart past the threshold, giving Jack a disturbingly awesome view of how short her skirt was as it rose on her thin, stocking clad, thighs. " Ms. Thomas said I should deliver up this Valued Guest care package as soon as you'd finished in the shower. Your favourite I believe; a dozen oysters and an extra large Double D - double Dalwhinnie. Just like me!" She turned and presented her chest smiling brilliantly and handed him the drink. Indeed, though it was becoming an old joke; it was not one he was going to grow tired of soon.

Wait a minute, he thought.

"Care package? How would you know? How would you know I just finished in the shower?"

"Oh. Sorry, Mr. Aubrey. Shit. Sorry. I blurted that out."

Jack smiled and chuckled, "Ok. No worries, but tell me."

"OK. Please let me assure you we do not spy on our guests. I know how disturbing it might be revealing our subtle monitoring. Please keep it secret. It's for the guest's benefit. The hotel prides itself on anticipating every guest need so to do that..."

Setting the cart aside, Madeleine moved toward him. She looked deeply, sincerely into his eyes, Jack became aware of her scent. Her green eyes fixed on his.

"So they monitor each suite's key occupancy sensors regarding internet usage, heating, cooling, water pressure, stuff like that. As it was explained to me, they have a log-thingamajig.

"Algorithm?"

"Sure. Anyway, when you didn't stop by at the bar as usual and since the desk attendant said you looked pretty bummed, the Duty Manager thought you might need a pick-me-up. The Guest Monitoring System helped us get the timing right. In this case, we pretty much knew when your shower ended so we'd arrive just in time with some interesting treats, which based on prior orders we knew you'd like. And of course, I knew you'd be interested in a double D. By the way; I brought the bottle," she whispered, "just in case."

"So you spy on your guests."

"No. Not at all!"

"Are there cameras?" Jack was becoming a little more agitated. Evidence of his late night self-amusement sessions could be devastating.

"Absolutely not! Mr. Aubrey, I'm probably saying too much but, yes we do know how many people are in the suite. It's for security - Heat sensors, motion sensors and such, but there are no cameras. And all files are deleted on a 24-hour cycle.

Madeleine moved to the table and placed the tray of fresh oysters down.

"Let me fix the bed for you," She moved to the bedroom and began to pull the covers down. As she reached for the pillows, she placed one knee on the bed to get better leverage on the sheets, and her dress hiked high enough that Jack caught a clear view of her delightful pussy just visible beneath the fabric of her sheer briefs.

Madeleine glanced back, "These plush beds are too high for tiny girls like me. It's hard to protect one's modesty, but I know you weren't looking." She giggled.

As if! Jack couldn't resist watching her as she moved about the rooms. She had a tiny waist that spanned out over well-proportioned hips.

When she turned to him; Jack noticed her bright green eyes, her gentle curves, her full soft lips and clear, smooth skin again. She was glowing.

"So can I assist you with anything else Mr. Aubrey?" her voice was velvety soft with a subtle indiscernible accent. Jack gazed at her for a few moments then shook his head to release him from her spell. He his hand through his still damp hair, "um. Yes eh no. That will be all, thanks," he mumbled.

Madeleine smiled mischievously and sauntered towards him, her hips now moving more seductively. She reached up and released her hair shaking out the soft curls. She pressed against him, running her fingertips along the lapels of his bathrobe. Jack became aware of her floral perfume; his cock stiffened further. So far he had managed to control it with his hand in the robe's pocket.

She leaned in and pressed her pouting lips to his and moaned. "Are you sure there isn't something else ...em...I could help you with?"

Jack's cock surged to full attention, and he lost his grip. His swollen member parted the opening on his robe, and it slapped hard against Madeleine's thigh.

"Oopsie," Madeleine squealed delightfully. "OH, my! It seems I've caused a bit of stress there. Let me take care of it for you." Without waiting for Jack to answer, she leaned in again, her soft lips again on Jacks'; her tongue soon inside his mouth. At the same time, her warm hand had taken charge of Jacks' rock hard manhood. Jack moaned into her mouth.

"Hmm, yes Mr. Aubrey, I think I know exactly what you need."

Jack protested feebly. " Madeleine, I don't think this is appropriate."

"Sure it is Jack."

"I'm mmmmarried.

"Of course you are. Relax. I won't say a word"

Madeleine dropped to her knees, kissing his abdomen in a few places; her eyes locked on his until she was eye level with Jack's cock. She paused briefly and gathered her hair in a hair band. Satisfied, she took hold of the base, and her other hand cupped his ball sack.

"You have a very nice cock, Mr. Aubrey," she kissed the tip gently, "Hmmm. I just love the scent of a freshly washed cock."

Without pause, Madeleine went about the slow sensual worship of Jack's manhood. Jack loved the sensation as her hot mouth enveloped his swollen glans as she applied firm suction.

"Oh My God. You keep that up, and I'm gonna explode."

Madeleine moaned in appreciation of the compliment, taking all of Jack in her mouth, pressing her nose against his groin and moaning seductively. Slowly pulling back, her lips tight on Jack swollen shaft, her tongue taunted every millimetre, ignited every nerve. Jack's eyes rolled in ecstasy. Reaching the tip, she pulled sloppily away, giggling at his reaction. She flicked her tongue on his purple glans, slapping the corona gently, "And no Jack. You cum when I say so."

Grabbing his cock firmly and looking him directly, "So Jack, do you want me to be your dirty little cum slut? Do you want to fill my dirty mouth with a big load of your hot jizz?" She giggled and then again drove her mouth hard on Jack's cock causing his balls to tingle, and his toes curl.

"Fuck me!!" Jack moaned.

"Yes I will, but first we play."

And so it went. Slowly Madeleine worked him in and out of her soft full lips, taking him deep into her throat, gagging, coughing up mucus and his precum. All the while, her free hand delicately massaged his ball sack.

Jesus fucking Christ thought Jack, in less than a minute she'd gone from innocent maid to smouldering porn star. Jack was quickly losing what little control he had as Madeleine enveloped him in her maelstrom of pleasure. He grabbed her head, partly as an effort to hang on but also as much to guide this gorgeous little wenches fierce tempo as she slurped and bobbed her head on his jewels drenching his groin in a frothy mix of saliva and Jack's precum. Pressure mounted on Jack's end.

"Enough! Enough! Please!" He pushed her away suddenly forcing her to release his cock and bent down plunging his tongue into her mouth.

"Fuck my life. I'm sorry, I couldn't last much longer, and I want to experience all of you. My turn to torment you..." Standing her up, he smiled devilishly and started to kiss his way down her neck, her shoulders and the base of her throat.

"Hold on Jack. First, let me slip into something more comfortable." She pulled away to give him the full show. The wrap dress' three buttons were popped in addition to the hidden modesty button. Madeleine slowly peeled off the shoulders, and the dress dropped to the floor revealing Madeleine in all her splendour. Her pert full breasts were braless; her erect nipples were obviously begging for attention. She sported an interesting ouroboros tattoo about her navel, and the dark spot on the sheer full briefs betrayed how invested she was in our encounter.

"Come, let's get comfortable," she peeled his robe off, grabbed his cock and guided him to the bedroom. They fell into a warm, sensual embrace, giggling, sloppily mashing and biting lips and tongues while caressing each other's bodies.

"My turn now," Jack said breaking the kiss."

"Please, Sir, have your way with me."

Jack began his journey down her body. He playfully pulled, sucked each of her delightful breasts and gently biting each nipple and then soothing them with his tongue. As he applied attention, Madeleine squealed and moaned in appreciation.

When Jack's hand cupped her panty soaked mound he elicited a squeal of appreciation, "Fuck Jack, I thought you would never get there!

"Jesus, Madeleine, your panties are soaked."

"Of course! You've been teasing me for days. Now let's get them off!" She kicked her legs up and rolled the sheer briefs, up and off. "Want a taste," she giggled and offered the sodden garment to Jack, "I know this is one of your interests you filthy pervert." She giggled.

Fuck, Jack thought they are tracking my web traffic. No matter. Jack took the delicate garment and weighed it in his palm. It was saturated. He brought it to his nose and sniffed deeply. "I think we'll need a taste test of the source to be sure. Spread them wide for me, please, you dirty girl."

Madeleine giggled again and smiled appreciatively as she spread her thighs, "Dive in, good Sir."

Jack dropped his mouth on her sodden quim beginning his detailed exploration. Her mound was shaved bare, silken smooth. Jack paused and inhaled; she smelled fresh and tasted delightful. He kissed her labia gently, and she purred in response.

His further ministrations were slow and deliberate. It had been quite a while actually since he'd been with a woman so young and beautiful and he wanted to be sure to savour every moment.

He used his finger to open her lips and gently toyed with her opening. Madeleine responded appreciatively to his attention. She was oozing so much juice as she felt it drip down her ass. She thought Jack seemed to instinctively know her every sensitive spot and how to trigger it. Her breath came in short excited gasps in response to his touch.

She spread her thighs further, giving him greater access to her cunt. Jack paused and reached up to grab a pillow to place under her hips.

He resumed kissing her and tonguing her, slowly, stroking her passion. His tongue slid up and down her slit, then deep as his tongue plunged it into her hole. He slurped her juices, savouring the taste. Her clit was hard, and he moved his lips to engulf it and flick it with his tongue; bringing her closer to the edge.

"Fuck...Jack...I'm gonna cum all over you... if-if you keep this shit up," she breathed.

"Bring it! Give it to me! Drown me!"

Her pussy juice was sweet and thick as syrup, and it flowed freely. Jack continued his enthusiastic assault on her cunt. Madeleine's breath shortened, her right hand guided Jack's head, pressing him gently but firmly in his efforts. Her passion rose on each breath. Her entire core was aching to cum.

"That's it, Jack, there, there. Suck my clit, please! Please," she squealed as she squirmed beneath him, Jack added a finger to his assault, playfully probing her opening. Slowly driving deeper in light strokes. "Two fingers, please Sir," Madeleine begged in short breaths "Two will make me come. Please make me cum!"

Always willing to oblige, Jack abandoned his oral assault and kissed his way back up her body, and resumed his worship of her nipples which elicited increasing signs of pleasure. Making his way further up they soon begin to mash lips and tongues together in a fierce and sloppy tango.

Meanwhile, he deployed finger number two and directed his attention to the roof of Madeleine's tight molten cunt. Her legs spread wide, her knees up. She moaned and whined as Jacks' finger squelched in an out of her.

Her hand atop Jack's wrist guided his tempo and ensured his rhythm. Jack broke their sloppy kiss and gazed at her; she had the fuck grimace, the look of wanton ardour, pure animal lust her eyes begged him to finish her.

"Please oh please! Jack I'm so close..." Her hips were rising and falling with the thrusts of his fingers."

Suddenly, she took hold of his fat cock with one hand, "Fuck me now! Fuck me! Please. I need your cock in my cunt now!"

Without waiting for a response, Madeleine straddled Jacks hips, With a firm grip of his rock hard cock, she guided it to her dripping fuck hole and slid down balls deep, letting out a deep moan as her pussy adjusted to the girth of Jack's cock. Her eyes rolled back. Jack grabbed her breasts kneading, pinching her nipples between his thumb and forefingers.

"Harder," she growled as she ground down on his cock.

She bent down and kissed him hard biting his lips. Her breathing, now fierce. She stared directly into his eyes. Jack returned the gaze, grabbed her hips and now raised her up and down on his cock, pulling her up and down on its full length while thrusting up into her at the same time.

"Fuck yes! That's it, Jack. Fuck my cunt! Fuck my cunt! Blast that load inside me!"

Jack let her take charge, content to watch her gorgeous tits bounce up and down, and the sight of his glistening cock disappear in an out of her dripping fuck hole. She was fucking him now as a woman possessed. Her head tossed back, her eyes closed, one hand pulling hard on her left nipple taught while her right strummed her clit madly. Jack continued to pump into her as hard as he could, lifting her then bringing her crashing down his thick cock.

"Oh yes! Oh yes! Ohhhhhhhh yes! Oh God, I'm Cumming!" she squealed as her whole body began to shudder and twitch. Jack could feel the sudden warmth of her girl cum smother his cock and drip down his ass crack, soaking the sheets. Her pussy pulsed against his cock causing it to erupt as Jack cried out in ecstasy and pumping what felt like a gallon of cum into her.

Madeleine collapsed onto Jack's chest. He released her hips. Their heart rates slowed. Their breathing recovered.

"Fuck me, Madeleine. That was awesome! I don't remember when I was so thoroughly fucked. Ever."

"Mr. Aubrey. You were indeed pretty awesome too." Somehow she had recovered faster, she leaned in and kissed him deeply, then bounded off the bed and headed to the other room. She returned with the platter of oysters and the bottle of Dalwhinnie, smiling brightly.

"So let's have some oysters and a Double D and then let's fuck again. OK? I'm actually under orders to ensure complete customer satisfaction. So are you thirsty for more?"