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Claire’s Uptown Girls


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Claire’s Uptown Girls By Don Julian Winslow

You knew when she walked on by that there was something special about that girl. She had an unmistakable air ” stylish, elegant, with the classic looks of a thoroughbred, and the stride of a high fashion model. She was one of Claire’s Girls, one of those attractive, smartly-dressed young women who caused heads to turn as they strode in their heels down Park Avenue on their way to some discreet rendezvous. She had been carefully dressed and groomed and shaped to fulfill a very special role, to capture a look, to fit an image meticulously crafted by the sophisticated proprietress of the world’s most exclusive escort agency.

This sensuous narrative includes a series of vignettes, each one highlighting a different girl from the stable of New York’s finest escort agency. They represent a range of modern women: the brash, uninhibited young girl and the exciting sensually mature woman, the urban housewife, and the girl-next door, the businesswoman in her trim suit, the kinky dominatrix clad all in lather ” each with her unique provocative allure. We follow these young women though their sexual escapades, delving into sex in the city as they explore the outer fringe of the erotic.

Weight 0.99 lbs
Artist Credit

Cover Art Image Mayer George –

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It was just a few minutes after 1 pm when the cream-colored Rolls pulled up to the curb.  Wendy bent down expectantly, as the rear door opened and she found herself face to face with an attractive older white-haired man dressed in an expensive pinstriped suit.  His pale blue eyes looked her up and down, and then smiling his approval, he nodded, inviting her in with a beckoning gesture.

As the Rolls cautiously nosed out into the traffic, the gray-haired gentleman extended a soft well-manicured hand and, with quiet courtesy, introduced himself as Peter Hamilton.  Wendy let him take her hand as she responded with her name, or at least the one that Claire had given her, and the one she now answered to automatically.

“My, your hands are cold!”  he pronounced, eyebrows arching up to show his genuine concern.  He took her hand in both of his, holding it protectively. She let herself sink into the luxurious seat, prepared to enjoy being pampered.

Wendy couldn’t help being overawed by this wealthy man, so impeccably groomed, and well mannered, who had that air of good breeding — a man who moved with easy confidence from boardroom to country club.

She was starting to relax and feel more comfortable with him by the time they got to the Pierre, but when they entered the elegant lobby she felt her uneasiness return in a sudden rush.  Hamilton said nothing to assure her, but with his suave urbanity, merely offered her his arm, and she felt instantly better, grateful to slip a hand through his arm and have him pat it affectionately.  Just being at his side made her feel warm and secure.  To anyone in the lobby curious enough to pay notice to them, they would appear to be exactly what they seemed, a rather ordinary college girl being taken on a shopping trip to the big city by her doting father, or perhaps a charming rich uncle.  Beyond that they would be able to do no more than speculate   Wendy, still a bit overwhelmed by it all, was quite impressed by the luxurious suite that he ushered her into.  While she stood there gaping, he relieved her of her purse and hat, and stepped behind her to help her slip off her coat, his hands passing lightly over her shoulders.

Hamilton kept his eyes on the girl, drinking in that gracile figure as she bent over to peer out a window, eager to see the view.  To achieve that classic preppy look that Mr. Hamilton wanted, Wendy had selected a crisp powder blue blouse of oxford broadcloth, layered with a burgundy sweater of fine Marino wool, and topped with a well-tailored flannel jacket in traditional navy blue.  With that she wore a loose pleated skirt of wool plaid and a pair of deep burgundy tights.

Now, as he watched the young girl move, leaning down over the windowsill, he felt an indescribable twinge of longing, sharply evoking something from the past, something that he had buried long ago.

“Well, it’s certainly warm enough in here!  Perhaps you’d be more comfortable if you took off your jacket, and you won’t need that sweater.”  he suggested, taking off his own jacket.

Wendy turned back into the room, and paused to slip off of the navy blazer and fold it over a chair, before pulling off the sweater, smoothening down her mussed hair.  Hamilton had turned his back on her as he went to a glass fronted cabinet.  He now returned with a bottle of Champaign and two glasses. He pulled a small rounded chair to the center of the room.

“Take a seat,” he gestured grandly, pointing the champaign flutes to the easy chair, while he took a seat on the couch.  “Why don’t you kick off your shoes, and stay awhile?  I’d like you to tell me all about yourself.”

Wendy obediently reached down to slip off her favorite shoes, the soft suede pumps with the low stacked heels.  She settled back, letting the little skirt ride up as she crossed her attractive, nyloned legs.  She saw where his eyes went and smiled up at him with a little ‘thank you’ as he popped the cork, and poured the bubbly liquid into her glass….


“You know, you have such lovely legs, Wendy.  Why don’t you come over here and let me see them?” It was a softly spoken, courteous request.

She set her glass down and stood up, padding across the carpet to stand before him in shirtsleeves and skirt, looking down at him expectantly.

“Yes, splendid,” he beamed with rich approval in his voice. “Now, lift your skirt please,” he continued in a lowered voice, his blue eyes twinkling with amusement.

Wendy reached down to gather up two handfuls of the soft wool, hoisting the skirt up a few inches.

“Higher.”  He smiled encouragingly, looking up at her and giving her a wink.

The skirt inched upward uncovering the entire lengths of those thin supple legs encased in wine-colored opaque nylon.  Now, as she held her skirt at her waist, unveiling her tights-clad body from the hips down; she felt the first blush of sexual excitement.  Something stirred in her, to be showing herself to the silent man like this.

He had her stand like that for several minutes, saying not a word, not touching the girl, only admiring the splendid architecture of her loins: slender thighs forming the smoothly contoured arch; the narrow hips; those lovely legs, all encased in a shimmering deep purple.

“Turn around.”

Wendy turned, presenting her back to him, and finding herself face to face with her own reflection in a full-length mirror that graced the opposite wall.

“Now lean over a bit..that’s right, and pull your skirt up in back….Look in the mirror”.

Wendy widened her stance and bent forward from the hips, reaching behind her to hold up the short skirt.  She knew that there was really not much he could see through the opaque tights and yet the very thought of showing herself to him, her skirt hiked up over her jutting bottom…she found it to be incredibly erotic.  A delicious shiver of lewd naughtiness shot through him at the sight of the girl with the green eyes, bent over in wanton presentation.

For the longest time he kept her like that, her back to him, her skirt raised up, showing him her nyloned rump.  He was silent, but she could sense his presence, knowing his eyes were scrutinizing her slim legs and small tight butt; drinking in her nether regions, encased in those elasticized wine-colored tights.

“Beautiful,” he whispered in honest admiration, thrilling the girl to the core.

After several minutes he released her.  She was allowed to straighten up, to let the skirt fall into place, and turn around so that now she stood with hands at her side, just a few inches from his chair.  He reached for her, took her by the hand, brought that hand up to his lips and kissed it.   Now he held her hand in his as he looked up at her gave her a reassuring squeeze and a warm smile.

“Tell me Wendy, did Claire tell you why I wanted from you?”

She dropped her eyes, and nodded without a word.


“She said you’re into…spanking.”

“That’s right.  I just love spanking pretty girls.  I trust that’s okay?”

Wendy kept smiling as she silently nodded her head.

“Good!”  he pronounced.  “Now come here.”

With a gentle tug he drew her towards him.  Wendy let herself  be drawn to the fatherly man’s lap, Sitting on his lap, let herself be kissed on the cheek and then on the lips.  He held the kiss as one hand came up to hold her waist while the other found a stockinged leg .Curving around to fit the smoothened contour, his hand inched the loose skirt upward, uncovering her legs till the skirt was up around her waist.

Wendy, still a little tense, felt her reticence melt as she surrendered to this masterful man.  The man’s slow hand  caressing her thigh brought deliciously warm waves of pleasure, lulling her into a warm lethargy.  And when his hand tunneled under the rucked-up skirt, exploring between her legs to touch her there, just between the thighs, the young woman experienced a powerful surge of arousal that caused her to gasp and to breathe a long shivering moan into her lover’s  ear.

“Come my dear.  Over my lap you go. I want that pretty bottom of yours served up properly!”

Wendy, a little groggy with passion, moved to re-position herself the way he wanted her, laying limply  down across his lap, stretching out over his widespread thighs, head and shoulders hanging down inverted over one side, stockinged legs angling down the other till her toes dug into the thick carpet.  Once having assumed the classic spanking position, she closed her eyes and waited, tense and expectant.

Hamilton spread his legs a bit more, testing for the best balance, shifting her dead weight, relishing the feel of her solid hip pressed firmly against his lengthening cock.  Quite deliberately, he laid a cupped hand on that nicely rounded bottom, patting her affectionately through the soft wool of the skirt.  Wendy tensed up, then forced herself to relax.

Now she felt her skirt being raised in back, and her slack body shifted again so that as he worked the skirt up over her hips, exposing her lower body to his appreciative gaze. He admired the view: tapering legs sheathed in the slick wine-colored tights from hips to stockinged toes.

“Lovely,” he crooned, deeply impressed by the splendid sight he had unveiled, while he let his hand pass adoringly up and down the sinuous lines of a that slim youthful leg.  His hand continued its ride up the gradual backslope of a taut-muscled thigh to the more rounded prominence of a tempting rearcheek, over the crest of that little hillock then back down again, this time easing along the centerline to dip into the juncture between her legs, pressing there, exploring the soft folds of her hidden pussy through the layers of warm moist nylon.

Wendy couldn’t keep still, the electrifying thrill of that most intimate probing had her squirming uncontrollably in his lap, yet not a sound came from her inverted head.  Just when Wendy thought she could stand no more, the hand receded and began once more to slowly trace the sculpted contours of her loins, sliding along the tawny flanks, the slim, boyish hips, easing up and down those wonderful nylon-encased mounds in a slow lazy caress, and stirring dreamy warm feelings in the stretched-out girl who now hummed her contentment like a big cat.

Lulled into sensual lassitude, she could only smile to herself when she felt him fiddling with her underpants.  He hooked his fingers in the elastic waistband and ease down her tights, peeling the tightly-stretched nylon down and over her pantied behind.  Without being told, she obligingly raised her hips a few inches, eager to be helpful so he could more easily work the clinging tights down her thighs till they were left in place bunched up just above the hollows at the back of her knees.

Now Hamilton’s eyes drank in the delectable sight of Wendy’s tight-cheeked young bottom enticingly clad in a pair of silky blue panties, blue hip huggers that barely strained to contain her tightly-packed bum.  The legbands had ridden up so that two smiling bottomcheeks smiled back at Hamilton, peeking out saucily from below the overaching elastic legbands.  He sighed.


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