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The Amateur Escort

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Lynn is a 42 year old widow. She meets Alex one night at a bar of a 5 stars hotels where she usually meets male escort. She confused him for one and from a misunderstanding, Alex lives is going to derail. Lynn has very special needs that need to be attended to, very frequently.

Chapter 4: The Waiter

The summons came not via the new, sterile phone, but through a thick, cream-colored envelope delivered by a concierge to his apartment. Inside, a single cardstock sheet with an embossed hotel crest. "Wednesday. 8pm. Imperial Orchid. Wear the navy suit."

No further instruction. The echo of ‘practise’ hung in the air of his cluttered flat, a ghost of jasmine and exert ion.

At 7:59pm, Alex stood before the door of their usual room. He adjusted the cuffs of the navy suit, another flawless, silent command from her. He knocked, once.

“Enter.” Her voice, unmistakable.

He pushed the door open. The expected scene of a dining room evaporated. The suite was in its usual setting while he had expected a dinning table to be set. "Come over there" her voice echoed from there room, where the bed stood, stripped of its usual linens and dressed instead with a stark, waterproof white sheet. It was a clinical altar. Upon it, Lynn reclined against a mountain of silk pillows. She was completely naked.

The sight stole the air from his lungs. The suit and time had him expecting a semi formal function he would have to attend with her. He understood that the suit will soon be useless. Her expression was one of serene, imperial composure.

“Close the bedroom door,” she said. “They’ll bring the food shortly.”

He did, leaning against the solid wood for a moment, his heart a frantic drum against his ribs.

"Get changed, we re not going to ruin that suit now that you look decent" she pointed to a small bag with her chin. Inside a male string. He looked at her, pleading.

"I don't want your... thing messing with my food". Alex obeyed. She looked at him as he changed, enjoying the view.

A soft knock announced the arrival of the food in the living room. Two attendants had wheeled in a trolley laden with dishes under silver cloches, a bottle of Krug in an ice stand, and two crystal flutes. They left as silently as they came.

"Go bring the food in". Alex went back to the living room where he found the trolley and wheeled back inside the room.

“Bring the oyster,” Lynn directed, nodding toward the trolley. “And the champagne.”

He moved stiffly, the absurdity of the scene wrapping around him like a fog. He popped the cork, poured, and brought a flute to her. She didn’t take it.

“You will feed me,” she stated. “Start with the champagne.”

He knelt on the edge of the waterproof sheet, the material crinkling under his knee. He brought the flute to her lips. She took a small sip, her eyes holding his. “Now. An oyster. No sauce.”

He fetched a shell, the cold, briny mollusk gleaming within. He held it to her mouth. She parted her lips, tipped her head back, and let him slide it in. She swallowed, her throat working. A droplet of liquor escaped the corner of her mouth and traced a path down her jaw.

“Clean it,” she whispered.

He bent and licked the salty bead from her skin. His tongue touched the faint, roughened texture of a scar. He was trembling.

“Now,” she said, her voice low. “Your mouth is idle while I eat. Correct this.”

A current of understanding, dark and electric, jolted through him. This was the ‘practice’, refined. He set the champagne flute on the side table. With one hand, he selected a slice of ruby-like tuna sashimi. With the other, he reached between her legs.

She was already wet. The heat of her was a shock. He touched her, searching for her clit, finding it swollen beneath his fingertips even as he raised the fish to her lips. She ate the sashimi, her eyes fluttering closed as he began to circle that tight, needy knot with a steady, insistent pressure.

“More strucutre,” she breathed around the food. “Your aim is familiar yet unsustanined focus. Prevalence and passion lacking in the application of fingering dialectic must escalate.” He understood the gist, her words were orientational bullshit masking a raw need for more"fuck me". In reality an authorization for finger penetration. So he did. He slid two fingers deep inside her, curling them instantly to find that same spongy ridge he’d memorized on the proxy. She gasped, her back arching off the bed, a low moan vibrating against his fingers.

“Champagne,” she demanded, her composure cracking.

He brought the glass to her lips, then focused back to his duty.

"You too" she said. She grabbed the bottle, poured a splash directly into the hollow of her navel. The pale liquid pooled in the delicate dip. He bent his head and drank it from her skin, his tongue lapping the cool, bubbling wine from her stomach. The act was profoundly more intimate than anything before.

"More" She asked. He understood the assignment. He moved lower, his mouth replacing his fingers, his tongue licking a broad, wet path through her folds. She slowly pourred champagne between her breast until it flowed into his mouth. She tasted of salt and musk and now, faintly, of champagne. He delved inside.

“The oyster,” she gasped, her hands fisting in his hair, not guiding, just holding on. “Put it on me.”

He obeyed, his mind singular. He took a chilled oyster from its shell and placed it on the swell of her pubic bone, just above where his mouth worked. He ate it from her body, his tongue flicking the cool, slick flesh into his mouth before returning to her clit, sucking hard.

“Again,” she panted.

He placed a slice of fatty toro on the bruise just below her ribcage. He ate it, his teeth grazing the discolored skin, before burying his face between her legs again. He fucked her with his tongue, driving it in and out, then sealed his mouth over her clit, applying a rhythmic suction that made her cry out. The room filled with the wet sounds of his mouth on her cunt, her ragged breaths, the crinkle of the sheet beneath her.

“Now. Inside. Fingers. Now,” she commanded, a ragged edge of desperation in her tone.

He pushed three fingers into her, his palm grinding against her as he worked them in a relentless, curling rhythm. His thumb pressed down on her clit. He felt her inner muscles begin to flutter, a frantic, tightening pulse around his fingers. With his other hand, he drizzled champagne directly over her clit.

She came with a shattered scream, her body bowing off the bed, her cunt clamping and convulsing around his invading fingers. He kept moving them, working her through the violent waves, drinking in the combined taste of her arousal and the expensive wine. Her heels dug into the small of his back, holding him there as she shuddered.

When the last tremors subsided, she pushed his head away weakly. She was panting, slick with sweat and champagne, her painted cruelty replaced by a spent, open vulnerability. For a few seconds, she just looked at him, her chest rising and falling rapidly.

Then, like a sheet of ice reforming over a turbulent pool, her mask slid back into place. She gestured vaguely toward the trolley. “Clean this. Then clean me. A hot cloth. Then you may use the shower in the adjoining room before you go.”

He was dismissed. The instrument was to be wiped down and stored.

He gathered the dishes in a numb haze, his fingers sticky, the scent of sex and seafood clinging to him. He fetched a steaming cloth from the bathroom and returned to the bed. She lay still, allowing him to wipe the champagne and oil from her stomach, her thighs. She didn’t flinch.

As he turned to leave, she spoke, her voice quiet, aimed at the canopy above. “The proxy. Did she scream?”

Alex stopped, his hand on the door handle. The memory of the woman’s cries, her choked affirmations, echoed. “Yes. Twice.”

A long pause. “Louder than me?”

He understood. This was the real evaluation. Not of his technique, but of her own effect. “No,” he said, truthfully. “Hers was controlled. Yours is… raw.”

He left without waiting for a response. Under the scalding hotel shower, he scrubbed at the smells, but they seemed baked into his skin. There was two enveloppes when he was done. The bedroom door wad closed. He took a cab home.

It had been a week and he was exhausted. His palms ached from practicing kneading techniques on a foam dummy his tutor provided. The ghost of jasmine seemed embedded in his sinuses, a permanent filter over his world.

Friday arrived with a stark, grey dawn. His new phone chimed at precisely noon. "Imperial Orchid. 4pm". No other words. He knew the ritual by now: the silent ride up, the soft click of the lock, the hushed expanse of the suite awaiting its purpose.

The room was prepared. The massage table stood central, draped in fresh linen. A cart holding bottles of oil and neatly folded towels awaited his professional touch. Lynn stood at the window, already undressed beneath a white terrycloth robe. She did not turn.

“Begin,” she said, her voice flat.

He washed his hands meticulously at the suite’s wet bar, the scent of antiseptic lemon soap overwhelming. He approached the table as she let the robe fall. Her back was a map of old, faint silvery lines. He poured oil, warming it between his palms.

His hands made contact with her skin. He worked in silence for twenty minutes, his fingers finding the cables of tension in her shoulders, the rigid plate of her lower back. The only sounds were the soft slip of oil and her measured breathing. He felt a dangerous, unprofessional urge to speak, to puncture the sterile quiet.

“How was your week?” he asked, the words too loud in the quiet room.

Her muscles flinched beneath his palms. She raised an eyebrow, tilted her head just enough to catch his reflection in the dark window glass. Her surprise was a cold, visible thing.

“Nothing said we can’t talk,” he followed up, his thumbs pressing into the knots along her scapula.

“I would rather not, though,” she stated, closing her eyes again, a clear dismissal.

He swallowed the rebuttal, focusing on the topography of her body. He worked lower, his touch firm and clinical. When his hands glided over the swell of her buttocks, he felt no responsive softening, no hint of yielding. He followed his training, his protocol. He applied strategic pressure to her glutes, his fingers venturing to the sensitive inner planes of her thighs. Nothing. She remained a statue of tense marble. The perfunctory, technical part of the massage concluded. The silence rang in his ears.

“Turn over, please,” he said.

She did. Her face was a mask of indifference. He began on her front, starting at her feet, moving up her calves, her thighs, avoiding the core of her. When his hands finally brushed the soft skin of her lower abdomen, he felt only a coiled vigilance. He moved to her breasts, kneading the soft flesh with a deliberately sensual, circling motion. Her breathing stayed even. He lowered his head, taking a nipple into his mouth, suckling gently, then with more insistence. He slid a hand between her legs.

She was dry. Unresponsive. He worked his fingers, trying to find a rhythm, a pressure she would accept. After ten minutes of futile effort, she let out a sharp, exasperated sigh.

“Stop.” She pushed his hand away. A flush of frustration colored her neck. “Just stop. You can’t make me come. Not today.”

She sat up, swinging her legs off the table. She snatched her robe, wrapping it around herself with a sharp, angry motion. “Get dressed. We’re going downstairs for a drink.”

The hotel bar was a cavern of low light and deeper shadows. They took a secluded booth. She ordered a neat whisky. He asked for a beer. The silence between them was a live wire.

“You’re allowed one question,” she said finally, not looking at him, tracing the rim of her glass. “About this. About us. Choose it carefully. But first listen very closely. This won't be said twice.”

She took a sip of whisky and went "You would have noticed that I'm older than you. I have had experiences, many, which led to me knowing exactly what I need and when. That's why I have the protocols, the methods, the routine. You don't improvise. Now I have invested a bit in you already and you have fared well so far. But you seem to need a bit more ... connection, so go ahead".

He studied her profile, the sharp line of her jaw, the weariness beneath the impeccable makeup. He thought of the proxy’s screams, the raw sound of Lynn’s own climax, the devastating quiet of her body today. The question formed, dangerous and essential.

“Why did you dismantle your late husband empire?”

Lynn’s fingers stilled on the glass. A complex, unreadable series of emotions flickered behind her eyes—amusement, pain, assessment. She took a long drink.

“You did your research,” she said, her voice a low whisper. “It wasn't his for starters. If anything it was mine. I sold it so that everything that he was, died with him". She finished her glass. "Now drink up. We’re going back.”

The room felt colder upon their return. The table waited, a silent accusation of his failure. He felt her frustration emanating like heat. “Continue,” she commanded, lying back down, her eyes fixed on the ceiling.

His hands felt clumsy now, weighted with failure. He tried again, every technique he’d learned or instinctively known. She remained a closed system. After another agonizing ten minutes, she gripped his wrist, halting him.

“Enough.” She sat up, walked to a sleek leather case on the dresser, and placed it on the bed beside him. She opened the lid. Inside, nestled in black foam, was an array of vibrators—sleek wands, ominous g-spot hooks, thick, realistic silicone.

“Pick one,” she said, her voice devoid of inflection.

He looked from the box to her face. This was a demotion. A revocation of his supposed skill. His throat tightened. He selected a medium-sized wand, black, unassuming. He turned it on. A low hum filled the room.

He guided the buzzing head to her clit. Within seconds, a tremor ran through her. Her eyes slammed shut. He pressed it firm against her, watching her hips make a minute, involuntary lift. He didn’t need skill now, just persistence. He held the wand in place, the vibrations thrumming through his own fingers. In under three minutes, her body stiffened. A sharp, choked gasp escaped her, more relief than pleasure, as the orgasm was wrung from her by the machine.

When the shudders passed, she pushed the wand away. She stood on unsteady legs, walked to her purse, and pulled out a white envelope. She tossed it onto the rumpled massage table.

“We’re done.”

He dressed in silence. He picked up the envelope. It was thin, lighter than air. Half the usual stack of crisp bills lay inside. The message was unequivocal. Payment for service rendered. The service had been inadequate. He pocketed it, the paper feeling like a lead weight against his thigh.

He left without a word. The elevator descended, mirroring the hollowed-out feeling in his gut. The proxy had screamed. Lynn had screamed. Tonight, only the machine had hummed, and he had been merely its holder. The silent phone in his pocket felt less like a tool and more like a shackle. He had gotten his one answer, and it had only deepened the maze.

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