Total Woman Mentors 02

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Evelyn and Mr. Rubin
4.2k words
4.33
10.2k
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Part 2 of the 6 part series

Updated 10/27/2022
Created 03/25/2013
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Evelyn had discretely taken position at the base of the stage steps during her father's just concluded warm-up session. She now mounted the stage. Striding to the fishbowl, she dipped in and quickly retrieved a numbered disk, holding it high overhead for all to see.

"Number 6." she announced with a jolly air.

A cheer came from Lounge No. 6 as the father-daughter couple disentwined and the happy man rose to his feet. He caressed his daughter's cheek and whispered 'see you later, honey'.

Applause accompanied Mr. Rubin as he marched to the steps and mounted the stage. Evelyn met him near stage right and took his hands to draw him close for a hasty whispered one-on-one.

"Hello, sir, pleased to make your acquaintance...and undoubtedly much more soon to come. For now, we must give them a little tease before we depart. Let's keep it simple; just strip me naked piece by piece. Sound okay?"

"Sure thing, little lady!"

Evelyn led Mr. Rubin to center stage and stood in front of him facing the stage front. The auditorium was obscured by the glare of the spotlight. Mr. Rubin stared into the shadowy auditorium over top of Evelyn's dark pinned up coiffure. He was easily a head taller than the curvy female even though her feet were elevated on stiletto heels. Between hairdo and heels, Evelyn wore a navy bare shouldered evening gown with tight abdominal sheaf above which, for now, triangular panels hid the promising mounds on her chest.

Waggling her hips to call for attention, Evelyn reached behind her neck and fiddled with the neck strap clasp. She feigned difficulty with the catch and looked back timidly at Mr. Rubin. He took over and after a moment held the separated twin tops above her shoulders. Evelyn smiled at the auditorium and shimmied her hidden shoulders and tits as the signal for Mr. Rubin to let go. The panels floated down and revealed Evelyn's bare breasts to the audience. A gasp of admiration filled the stage. Evelyn acknowledged the compliment with another shimmy. She took Mr. Rubin's hands and placed them on her boobs. She showed him how to cup, bounce, squeeze and fondle the fleshy globes in the style she thought the audience would favor. Mr. Rubin willingly obliged her wishes. The audience voiced their appreciation.

Encouraged, Evelyn let Mr. Rubin keep working as she reached behind her back and unclasped the gown's waist band catches. The puckered abdominal sheathe opened outward and Evelyn folded the fabric down over her hips. She pushed down and the dress fell to the floor. She stood topless in thong panties, thigh banding stay up hose and her heels. Mr. Rubin never missed a beat in his fondling of Evelyn's breasts.

Taking his hands in hers, Evelyn turned Mr. Rubin sideways to the audience and whispered for him to squat down. Evelyn stood hand on hips, her boobs mounted high and forward on her chest in profile to the audience. Mr. Rubin looked up as she rested her heel on his horizontal thigh. Mr. Rubin worked the buckles and straps and removed her fashionable footwear, setting it aside. He returned to graze his hands lovingly over her nylon clad toes and ankles. Evelyn switched feet and Mr. Rubin repeated the procedure with equal care. When finished, Evelyn winked and whispered 'the hose'.

Mr. Rubin smoothed his hands over Evelyn's shins and calves. He brushed his palms past her knees and finger walked to the top band of the nylon stockings. He admired the cameltoe displayed in the tight thong and looked forward to exploring there later in private. His fingers poked between the stocking band and the creamy warmth of her inner thighs. He imagined that soft flesh clamping his outer thighs. Before that fantasy could be realized, he must complete his duties here on stage and retire to a private setting.

Mr. Rubin rolled the stocking band over and his palms turned it down Evelyn's thigh. The nylon moved willingly as his hands smoothed it towards her foot. He pulled the last of it off her toes. Evelyn switched feet.

Mr. Rubin caressed this leg in turn and he was bolder with the finger walking above her knee. His digits pressed on the panty covered cameltoe. It was soft and warm. Evelyn let the fondle pass without complaint. The second stocking rolled down and joined its twin in the pile of clothes.

Evelyn in bare feet offered her hands to help Mr. Rubin to his feet. She loosed her hair pins and the dark tresses fell over her shoulders front and back, partially concealing her tits. She strode stage left, waving a cupped hand 'goodbye' to the audience as she led Mr. Rubin offstage. Pausing out of sight, they watched Mr. Rubin's daughter, Suzy, climb the short stage steps and pick a disk from the fishbowl.

Suzy waved the medallion over her head as she called out "No. 5!"

The cheer from Recliner 5 was followed by a tuxedoed gentleman bounding to the steps. At the top, Suzy met him for a quick coordination conference and then she led him to center stage.

Evelyn gently pulled Mr. Rubin away further back stage and led him out into the corridor.

"Suzy will be fine, Mr. Rubin. She and the rest of us are very capable of taking care of ourselves...and others. Let's go to your guest suite and I'll demonstrate how capable I am of taking care of you."

The naked but for thong panties student led the way to Mr. Rubin's guest suite. He watched her ass cheeks move adorably on her sashaying hips. She paused at his door as he swiped his keycard. He bade her enter and followed. Checking that the door was securely locked, he turned. Evelyn was standing full on with her hands on hips, watching attentively for his opening wishes for her.

"Well...I guess first thing I should do is get undressed. Can you help me with that?"

"Of course, sir."

Evelyn approached Mr. Rubin and waited as he removed his tuxedo jacket. She hung it on a clothes stand and returned.

"You are very tall, Mr. Rubin. Maybe you should sit so I can reach you better."

Rubin sat on a cushioned Ottoman. Evelyn undid his bowtie and unbuttoned his shirt. She stooped and leaned in to attend to his left shoe and sock. Her breasts dangled forward on her chest and Rubin's hand cupped one. He bounced it a bit, hefting the weigh, admiring its fluid resiliency. He rolled the nipple as she attended his other shoe and sock. He released it as she kneeled up and pulled his shirt tail out of his pants. She worked the cufflinks.

Standing up, she walked behind Mr. Rubin and skimmed his shirt off. She arranged all of the newly removed garments neatly on the clothes stand.

Evelyn knelt again before Mr. Rubin, unbuckled his belt and unzipped his fly. He helped her by lifting his butt when she pulled his pants and briefs over his hips and down his legs. He sat on the Ottoman naked as Evelyn attended his wardrobe. She took off her numbered choker and set it safely aside. There was no need for it now. She would put it back on tomorrow before the next partner re-shuffle. Evelyn returned and kneeled between his spread knees, resting her butt on her heels.

"Mr. Rubin, let's share some thoughts about your likes and dislikes. You didn't hesitate to manhandle my tits and you were very good at it, too. Right now, I'm in the perfect position for a seated blowjob. Or we can have penetration sex in any number of coitus positions. We have all night so you will have plenty of time to instruct me in different ways. Got any favorites you want to start with?"

"Well, Evelyn...you've got marvelous big fun-bags and I haven't had a good tit-fuck in a while. I want to ride you missionary style and feel your soft warm thighs clamping and caressing my legs. I want to pump wads of spunk deep in your cunt. But you're right. You are in a perfect position to give me a seated blowjob. So let's start with that and move along from there."

Evelyn smiled up at a Mr. Rubin who had certainly found his groove. She kneeled upright and shuffled forward, rubbing her soft hands inside his hairy thighs. She caressed higher until one palm cradled his balls while the other wrapped his semi-stiff shaft. She stroked it.

Evelyn licked her lips with anticipation as she examined Mr. Rubin's cock. It was stiff and long enough to fill her hand. Evelyn slid a finger pad along the main vein and lightly stimulated the lesser veins elsewhere on the shaft. She leaned in and kissed the tip with her wetted lips. She caressed the crown with her flat tongue and slurped his knob past her cherry colored lips. Her head swiveled to maneuver her tongue all around the circumference.

Evelyn's hair hung forward and partially obscured Rubin's view. He flipped the offending strands behind her back. Evelyn kept going without hesitation. From past experience, she was aware of and prepared to handle the upcoming sequence of events. As she worked her oral labors, the hair falls fell forward again. This time Mr. Rubin gathered them in his fist and clenched them in a tight bun behind her scalp. Evelyn began taking deeper breaths in preparation for Mr. Rubin's inevitable next moves.

Mr. Rubin suddenly realized that the hand holding her hair was, in fact, holding the handle of Evelyn's head. His zeal overtook him. He jammed Evelyn's head down and forced more of his cock into her mouth. Evelyn breathed deep and held it. Mr. Rubin pressed down further and pushed his knob past her tonsils and into her throat. He held her there momentarily and pulled her up again.

Mr. Rubin watched as Evelyn took a deep breath. Awareness set in. Of course, she had respiratory limits; but what were they? He pressed her down again until his cock slid into her throat. He held her there for a five count and pulled her up. That seemed okay. After she caught a few deep breaths, he pushed her all the way down again and held for a count of eight before pulling up. Again, that seemed workable. Down again and a ten count. He felt some resistance before he reached a full ten. They must be nearing her limit. He waited for her to catch a few full breaths then proceeded.

He pushed down smoothly and counted. At ten, there was a shudder. At twelve there was a definite rebuff. He released her hair and she pulled back halfway for air, and then lapped up and off his erection. She looked serenely in his face as she breathed deeply.

Evelyn was not dismayed. Her TWA coach-tutors had been generous with their energies, demonstrating that the aroused male was naturally macho and inquisitive. Harsh behavior was customary when the male explored his boundaries in a sexual relationship. She habitually got forceful treatment from a virile male. That was expected and she had been taught to receive and manage it.

"That was really good, Evelyn. Can you do that without me forcing you?"

Evelyn giggled. "Of course I can. Lay back and relax while I show you that and more."

"No, let's save that for later. My balls feel really full and I'm primed for a monster cum-shoot. I want to watch it explode all over your face. Let's move on to the tit-fuck. Lay back and relax while I use you that way."

Evelyn laid back. Mr. Rubin climbed off the Ottoman and crept up her torso. He rested his hairy ass cheeks on her toned belly as he twitched her nipples. Evelyn's breasts reposed on her chest in torus-shaped ovals. Mr. Rubin patted the outer budges setting liquid ripples oscillating through the masses. Evelyn wretched her head up to watch his exploration of her tits' resiliency. She looked uncomfortable.

Mr. Rubin grabbed a throw-pillow from the nearby bed. Taking the familiar hair handle hold, he jerked Evelyn's head up and jammed the cushion underneath. Her bolstered head was now situated to watch the action and provide open access to her succulent lips.

Mr. Rubin's erection stood tall. He played lovingly with Evelyn's fun-bags that would momentarily engulf his rigid rod. Evelyn waited patiently as he fondled her masses to the warmth that would add coziness to their impending pleasure. Their shared glazed expressions told of their readiness to go on.

"Sir, may I lend a helping hand to get things moving?"

"Yes, I'd like that.

Mr. Rubin placed Evelyn's hands on her tit sides and pushed his cock down into her spongy vale. She compressed them to completely enclose his manhood. He felt the warmth created by his previous kneading of her boobs. He gripped her nipple nubs and shook them, feeling the tremors massage his stretched cock skin. The sensations were heavenly. Evelyn's spittle still coated his rod and provided the lubrication. They began.

With every stroke, Mr. Rubin's solid cock rubbed the entire length of Evelyn's boob tunnel. When his engorged knob was presented at the top, she kissed and licked the slit; prompting little nerve flickers down the shaft to his balls. She stretched her neck to suckle his knob each time he chose to linger topside.

Evelyn gave her full devotion to amplifying Mr. Rubin's pleasure. His repeated moans and groans filled the room. Their varied intensity and dwell time expressed his satisfaction with her stimulation efforts. Evelyn sensed Mr. Rubin's mounting passion was reaching a peak. She got ready for her cum shower.

Mr. Rubin finally cried out and held himself steady high on her chest. The first massive shot hit her lips and splattered up her nostrils. Evelyn pushed her head back as far as the cushion would allow. The second shot spewed across her cheeks and forehead, spilling onto her splayed hair. The third one splattered the opposite cheek and spilled into her ear. The fourth rope only made it to her chin and dribbled into the hollow of her throat. Mr. Rubin pulled back and deposited his remaining load in the confines between Evelyn's tits. As he held his rod there, he again vibrated her boobs by the nipples and reveled in the resulting trickle of tremors.

Mr. Rubin's balls had delivered their built-up cum load that now coated Evelyn's upper body. The milky puddles were slithering down the gentle slopes of Evelyn's sperm speckled face. Mr. Rubin used his fingers to catch the sticky flows and deposit them on Evelyn's cum-stung lips. She lapped up each serving as he took care to find all the wayward strands for her consumption.

They rested in-place as Mr. Rubin lost his erection. Evelyn waggled her tits between her palms before paroling Mr. Rubin's dick from its enchanting prison.

Mr. Rubin crawled and stumbled to the bed and lay back content but fatigued. He lazed in a twilight afterglow of pleasure. Evelyn used the in-suite bath to wash the sticky residue from her hair and renew her cum tarnished face and nipple makeup. Refreshed, she joined Mr. Rubin in the bed and they dozed.

Mr. Rubin awoke and quietly surveyed the slumbering creature in his bed. Evelyn was truly a delight to behold. He saw that she retained her panties. He remembered admiring the smoothness of her soft inner thighs during the stage show and his stated desire to feel them caress his own outer thighs. The time had come to partake of Evelyn's nether regions now that he had heartily reveled in her upper facilities.

Mr. Rubin gently brushed his finger over the prominent cameltoe hidden under the silky thong. It was soft and yielding. He knew it would make an impeccable shroud for his embedded cock. Evelyn stirred at his touch and looked into his eyes. He held her sleepy gaze as he plucked at the ties of her thong. She lifted her butt as he gracefully slip the fabric off her ass and tossed it away.

Mr. Rubin pushed her knees wider and kissed the smoothness of Evelyn's upper inner thighs. He smelled the faint musk emerging from her juicy vulva. His oral caresses climbed higher. Evelyn lifted and spread her knees further facilitating Mr. Rubin's quest. He nuzzled her protective skin folds aside, burrowing in to lap the sheltered pink flesh. He smelled her musk and tasted its salty oils.

Evelyn's hands caressed the back of Mr. Rubin's head. He heard her moans. She was rendering up volumes of fragrant emollient. His chin, lips and cheeks were slippery with her genital dew. Mr. Rubin backed out and kneeled up between Evelyn's spread thighs. During his face time in her grotto, Mr. Rubin's erection had returned. Evelyn smiled as she regarded the sturdy rod with its super-sized knob that had recently packed her throat. She knew it would be a tight fit in her cunt even after it got past her entrance. She was thankful for the added lubrication that Mr. Rubin had caused.

Mr. Rubin leaned in and planted his arms on the mattress, framing Evelyn's luscious form beneath him. He ducked down and kissed her open mouth, smearing her essence about her face, sharing with her the smell and taste of his new favorite flavor.

Raising and locking her in his gaze, Mr. Rubin slowly lowered his hips. Evelyn levered his shaft with thumb and finger and aligned his cock to a proper angle. The knob touched her engorged lower lips and pressed for entrance. When half the knob was enclosed by her pink lips, Mr. Rubin was confronted with Evelyn's unintentional resistance. Her tight vaginal ring needed time and effort to stretch open before absorbing the insistent swollen crown. Mr. Rubin was willing to provide the effort but unwilling to permit the time. He pressed firmly and his cock nudged a fraction of an inch deeper. He pressed harder still and got all but the rim of the corona inside.

Mr. Rubin held Evelyn's gaze as he took a deep breath and lurched his hips down. That worked as his top two-inches popped into the warm tunnel. He paused. Evelyn merely rolled her hips higher acceding to the assault on her cunt. She was trying to streamline the orifice widening to come. Mr. Rubin punched his stout erection all the way down Evelyn's slippery vagina, feeling every fleshy fold scrape his knob. His tip found her cervix just before he was fully seated and compressed it to make more room for full burial. Mr. Rubin jogged little strokes to test his freedom of movement within Evelyn's close-fitting body.

Evelyn clamped her soft smooth thighs over Mr. Rubin's hairy legs and crossed her feet behind his back. He enjoyed the fine caresses of her clamping thighs. He pumped his cock in gradually longer strokes. The cycling jostled her breasts in the familiar ripples and he grinned at the motion. Evelyn noted his interest and waggled her shoulders for a better boob swaying show. Mr. Rubin stole intermittent nips and pecks on her grinning lips and then her oscillating nipples as he enjoyed the sensual presentation.

Mr. Rubin and Evelyn both felt the tremors when his cock knob pounded hard on her cervix. He wanted more of that feeling. He ran his biceps beneath her knees and folded her legs higher for deeper penetration. Braced in a pushup-plank position, he hinged his hips in a cacophony of thrusts, hammering her cervix even harder. The resulting sensations were intense and thrilling. Evelyn's cunt was well-stretched by the oversized intruder; she loved it.

Evelyn felt blessed that luck had paired her with Mr. Rubin. She knew she would reminisce with fondness about their time together. It was already a highlight of her numerous TWA memories and this congenial liaison was scheduled to continue throughout the night. By dawn, she hoped to be sexually drained and passionately fulfilled.

Evelyn's musings were interrupted by emergent sounds filling the room. She heard Mr. Rubin making moans, groans and grunts interlaced with deep and shallow breaths. Evelyn realized her own unwitting vocalizations were rivaling his for consideration. She was ready for a satiating conclusion to this activity.

The orgasmic sparks usually started in his toes but this time Mr. Rubin felt them skittle first across his cock head. He thrilled as they streamed outward to his extremities and flowed back more intensely. As the electric waves coalesced again in his groin, his back snapped into a reverse arch. He slammed his cock deep inside Evelyn and froze, roaring his triumph of erotic conquest. Torrents of his cum flooded her womb. The ejaculatory pulses set off Evelyn and she also wailed in ecstasy. He felt her spasms undulate along his shaft and that kept him perched on his sensory high so much longer. When her vibrations ceased and his body muscles finally surrendered their tension, he collapsed on her welcoming body and recovered with deep cleansing breaths.

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