The Tailor Ch. 01 - Amanda Fits Her Client

The elevator announced the floor: "Floor 60. Executive suites. Wilson, Thompson, and Farewell."

Amanda Cole arrived for her appointment with Bill Wilson as scheduled. Dragging her leather sample case behind her, Ms. Cole took pride in being punctual. She arrived at Bill Wilson's administrative assistant's desk precisely at 11:30 am.

Bill Wilson shared the top floor of the 60 story office tower with his two senior partners. It was a luxurious space, but it was a suitable acknowledgement for the success of the firm. The floor provided for a gym, several meeting rooms and each partner, had a corner suite. Bill was the senior partner - he had the best view.

"Good morning Shelly. I have an appointment with Mr. Wilson at 11:30. I'm Ms. Cole, Amanda Cole. I'm his tailor. I'm actually replacing Tony.

One of the great perks Bill enjoyed was custom suit shopping in the office. He generally hated shopping; the quarterly tailor visits kept Bill looking sharp.

"Of course. Mr. Wilson is expecting you." She directed him to her boss's inner sanctum.

Amanda strode into Bill Wilson's spatial office with purpose, her black Stessy stiletto heels accentuating her lengthy athletic gams.

Shelly eyed Amanda's perfect beauty with envy, not that she was any slouch herself. Just turned 30, Yale Law, Shelly had been trying to hook her boss for the past six months. To no avail. And now this hussy was barging in, she thought.

Amanda was dressed in an impeccably tailored three-button blazer dress that accentuated her slim figure perfectly. The hem was cut just below mid-thigh and almost dangerously revealed her stocking tops with each stride.

Bill caught himself staring as she strode up to him, then composed himself.

"Mr. Wilson delighted to meet you," she extended her hand in a firm handshake.

"Likewise, but I was expecting Tony?"

"He's down, sadly. Covid. He's OK and recovering. He suggested me as the perfect match to service you. I'm double vaxed, by the way, and we have cleared you, so everything should be fine. Let's get started, shall we?"

"Hold on a sec," Bill said, raising his hand.

Amanda raised her hand to cut him off. "I've anticipated your objection. Let me settle this. I'm a woman. This is 2021, Mr.Wilson. I am a professional tailor. Actually, I'm a Master Tailor. I've apprenticed at the finest Saville Row establishments in London. I've also studied with the finest couturiers in Milan, Hong Kong, New York and New Delhi. I've trained under the top masters in this business. Bill. May I call you Bill? Let me assure you; you are in the finest of hands.

Bill nodded. OK. Already he was under her spell.

"So, let's begin." Amanda crouched on her haunches, spreading her knees to access her sample case and removed the fabric swatches. Inadvertently, or perhaps on purpose, she flashed Bill a lingering glimpse of her stocking welt, pale thighs and her sheer white lace panties.

She noticed his gaze.

"So Bill," as she clapped her knees and case shut, "what do you think about this season's samples," she directed his eyes to the swatches with a wry smile.

Bill was flustered.

"OK, Bill. I saw you peak. It's an occupational hazard. I don't mind. Did you notice the stockings?"

"... they're Falke, Lunelle 8 Peacock," Bill said.

"Oh my, I'm impressed. So you are a fan?! Here let me show you," and she swept up the hem of her dress. Bill got another fantastic glimpse of her feather-styled stocking tops, her pale thighs and lace panties. His cock was now swollen, though not erect, and it was all his mind could do to use willpower to control his arousal.

"Don't you just adore the peacock feather welt? They make me feel so sexy. Especially when someone catches a glimpse."

Just as suddenly, she dropped her hem and closed her legs, "So what would you like to see first stripes or solids?"

"Errr Solids," Bill stammered.

"Great."

Their conversation revolved around colours, styles and patterns. Bill was entirely under her spell, mesmerized by her perfectly manicured nails, the swell of her breast in her fitted suit dress, the red of her lips. Her voice. Her scent. What was that scent, he wondered? She was way better than Tony, he concluded.

"Amanda? If I may, what is that perfume you are wearing?"

"Of course, it is Eau de Amour. It's a secret blend - very potent. It is actually formulated as an arousal enhancer. So if one is caught up in its vapours, it enhances both their arousal and their partner's arousal. All righty then, Bill, so let's get the measurements done. I need you to strip now."

"Pardon!? I didn't have to strip when Tony took my measurements last visit."

"I know, but we have a new digital measurement algorithm and a new device that will improve and enhance the suit's fit. It's amazing. Now strip. Please."

Bill hesitated. It might have been her perfume, beauty, or the glimpse of her panties earlier, but his cock was filling, and his objection was quickly diminishing. Resistance was indeed futile.

"Relax, Bill. It's just down to your boxers. Don't worry; I'll preserve your modesty. You won't be the first man I've seen in their underpants," she smiled.

Bill shed his shirt. He hesitated at his pants, mentally checking if his underwear was clean; satisfied, he dropped them.

"Good job, Bill. Now. Our new fitting utility actually requires close contact device-to-skin measurements. I will be scribing various arches and lines across your body, front and back. No need to be embarrassed; I've seen and measured all shapes and sizes. And no sucking it in, mister. OK? These measurements need to be precise. Seriously, this suit fitting will be like none you have had before, and it will be the best suit you have ever had. Ready?"

"Ready," Bill responded.

Amanda further described the process to distract him, "So the way this works is I have two thimble type devices that I track along the key meridians of your body. It might tickle, but it is exact. OK?

"OK."

"Great. We start with the neck and work our way down. Top to tail, as they say. Just relax and please breathe."

Amanda placed her thumbs gently on the front of Bill's neck and then drew them around his neck to the back. Bill felt her firm breasts press against his shoulders. Were those her nipples, he thought? No, they must be her dress buttons.

Amanda measured on, gently tracing the critical measurements of his arms and shoulders.

"OK, Now, arms out." She again pressed close to him and traced the measurement of his chest.

Bill could now feel the early sensations of his now rising erection as her thumbs traced across his nipples. Amanda moved to his front and bent down to capture his waist measurement, giving Bill a perfect glimpse down her dress. Bill had sufficient time to see her Sarrieri balconette bra. One of Bill's hobbies was women's lingerie. Amanda looked up and smirked.

"So just a few more measurements. Are you OK? Breathe Bill," She smiled at him and dropped to her knees and traced the outline of each foot. Then she worked her way up his legs measuring the girth and length of his calves and thighs.

Her soft, delicate touches strained his willpower as he struggled to contain his erection.

"Just a few more measurements. Waist, hips and inseam. You OK? Need a break?" Bill shook his head, "I'm good."

Now her head was perfectly aligned with his straining groin. Her breasts brushed against his thighs as she traced her thumb measuring device first around his waist. Then she moved to scribe over his buttocks to capture his hips measurement.

Bill lost control. His cock sprang through the fly of his boxers, just grazing her lips.

"Fuck! I'm so, so sorry. So embarrassed." Bill moved to cover his cock and stuff it back into his boxers. As If.

"Bill. Bill," Amanda grabbed hold of his hips as his now engorged cock oozed precum stood fully erect before her. She bit her lip and licked her lip. Fuck, she thought, it's gorgeous. Be professional. Breathe."Bill. Look at me!"

Bill looked down, but his cock blocked the view. Amanda took hold of it and shifted her perfect green eyes; simultaneously, she delicately smeared the precum over his cock head.

"Bill, Nothing to worry about. OK? Breathe. I've seen tons of penises (not so lovely as this, she thought). I'm a professional tailor. We deal with stuff like this all the time. OK?

Bill nodded, "I'm just so embarrassed.

"Aw, Bill. Trust me on this; you have nothing to be embarrassed about." She tried to keep her glee in check.

"There now. Relax. We're almost done."

"That wasn't so hard, right?" she said, chuckling to herself. She settled again on her haunches, her knees spread wide and presented Bill with yet another perfect view of her exquisitely lace panty-covered quim.

Looking up at him with her perfect green eyes. She smiled.

"Nothing left now but to gauge your drop."

"Drop?" Bill asked hesitantly.

She giggled. "Yes. Have you not heard that before? It's crucial. Most men have, shall we say, a natural position for their scrotums. It's never dead centre. It's either left or right and also not a problem for average men. "Unfortunately, you are not average," she said as she delicately stroked Bill's cock and gently caressed his scrotum with her nails. She smiled. So we'll have to deal with this erection.

"Can, can, we just skip this," Bill strained to resist

"Not advisable. Our new suits are particularly well-fitting. If we don't get the drop right, you end up; how can I put it. Well, frankly, you'll end up nutting yourself by crossing your legs or getting into and out of a car. Not a pose you want in a tough negotiation. Also, getting the drop right might actually enhance your negotiations with members of the other sex. Trust me, Bill, this is nothing I've not seen before. And as I mentioned, I'm a professional tailor. We are trained on how to efficiently deal with clients in this predicament to minimize their embarrassment when situations like this arise. So to speak. So shall we take care of this bad boy?" She licked her lips in anticipation.

Bill nodded. OK

Amanda stood up. "If you don't mind, I need to take off this dress. It's gotten hot in here, and also, I really don't what the risk of staining it." There were only five buttons, and the dress puddled at her feet before she finished explaining, and Bill could process the permission. She turned and picked it up and placed it on the couch arm, giving Bill a perfect view of her firm ass as she bent over.

Turning again, she presented Bill with one of the most magnificent sights he had ever enjoyed. The balconette bra was enhanced by a matching sheer lace embroidered bikini brief that perfectly framed her waist and mons. The lace gusset moulded delightfully against her quim's lips, enhancing her smooth slit.

Closing on Bill, Amanda reached into his briefs, looking him intently in the eye. She took his cock delicately in her hand and began to gently stroke it softly. "Relax, Bill," Amanda breathed into his throat, kissing his neck. Then, slowly dropping to her knees, she kissed along his body, maintaining eye contact. Licking her lips, she then kissed his stiff shaft and flicked her tongue around his corona to tease him. "How's that feel?" Next, Amanda moved to his balls and gently tongued them as she continued to lightly stroke his cock. She loved how he felt.

"You're loving this, aren't you, Bill?"

"Yes. Fuck. Please don't stop." he stammered. Bill's mind was mush.

Amanda reached between her legs and slid her panties aside. She might as well enjoy the experience, she thought and started fingering her pussy, sliding up and down the slickness of her moist slit but not entering. Her pace matched her sucking on Bill's member, and her moans of pleasure reverberated pleasantly on his cock, "Oh yes, Bill...."

She took it into her mouth and began to suck him in and out, allowing her tongue to continue to swirl around his cock as she took it deep into her throat. Then, she increased the pressure and intensity of her head bob; Bill grabbed hold of her head and began fucking her face gently.

Suddenly Amanda pulled back, releasing his cock. Standing up abruptly, she removed her bra and peeled off her panties, tossing them both carelessly aside. Bill was a bit confused. Maintaining a grip on his cock, she guided him to the couch and pushed him back.

"I need more, Bill, OK? OK? I want to fuck you, I need to fuck!" she said, dripping saliva and precum down her chin.

She didn't wait for an answer and kissed him passionately on the lips and guided Bill's fuck stick into her now sopping fuck hole. She slid balls deep in one stroke and moaned into Bill's mouth as the pleasure ripped through her cunt.

Amanda started with a slow sensual rocking action from a squat. She touched her forehead to his, looking intently into his eyes. "Suck my tits Bill."

Bill did as requested. She guided his head.

"Harder!" Amanda pressed his head onto her breast. 'Suck it! Bite it! Not so hard. There. There!. Like that. Fuck. Fuck. "

Amanda slammed down on him fiercely. Amanda knew it was coming. A perfect cum tsunami.

She now straddled Bill's cock, knees on the couch. He was plunging up into her as she thrust down on him. His hot ragged breath on one side of her neck, hers' on his other. Her juices were squelching as they flowed down Bill's balls and down his ass crack. "Don't come in me, OK? Hold off," she breathed into his ear.

Bill nodded, but Amanda knew he wasn't going to last. Men never kept their promises in this realm. She was closer, and without warning, she erupted in a powerful orgasm that shook her body; her mouth opened, gasping for breath in a fuck grimace and then she literally popped off Bill's cock and slid down his body, squirting girl cum everywhere.

Taking his cock in her mouth again, she tasted the creamy sweetness of her own pussy juice mixed up with Bill's precum. Amanda had been around enough men that she could tell when they were going to come. Bill suddenly went rigid and pushed her head down on his cock. Moments later, he erupted with a groan and body spasm. Thick gobs of sperm pulsed into her mouth. Amanda swallowed every drop.

They both embraced in a sweaty pleasure hug, laughing and giggling sheer joy. Pleasure hormones rippled in every muscle and sinew.

"Hmmm. Well, that was fun," Amanda said as she slipped up their mutually drenched bodies until she was greeted by Bill's face, who had the biggest grin. They both glistened from their efforts. She kissed him again passionately and deeply. Finally, Bill got to taste himself on her tongue. He might have objected in a previous life, but now he was beyond minding.

A beep sounded, and Amanda bounded to her feet.

"Time's up, Bill. Your Shelly will be back soon, and she'll be pissed if we are presenting like this."

"Like what?"

"Like we've been shagging all morning!"

Amanda tossed him a pack of wet wipes that she pulled from her magic bag, "Tidy up, mister and get dressed.

She'd snapped on her bra and mopped herself up, and was now searching for her panties.

"Bill, did you see where my knickers landed?"

Bill was just buckling his pants and tucking himself in.

"No, sorry."

"Bill, they're $200 knickers."

Bill was gobsmacked. "Seriously??"

"Seriously. No worries. I'll add it to the fitting invoice."

The lock on the office suite was released just as both Bill and Amanda had sorted themselves.

Shelly entered the suite. "Sorry, boss, I just remembered we had a meeting. I'm early."

Immediately, she'd sensed the lingering odour of sex when she entered. Surveying the office, the out-of-place furniture, she knew that tom fuckery had indeed occurred, and she was ticked. Glaring at Amanda, how dare she, she thought. Then she spied the panties tucked between the couch cushions. She discretely palmed them and slipped them into her pocket.

Bill had recovered enough to ask, "Hold on a sec Shelly. Amanda, fitting service? What's that about?"

"Well, Bill. This technology does not come cheap, and I'm sure you found the experience fulfilling. And the service is available any time, should you need to remain current. She winked.

"Fine," said Bill.

"It's been my pleasure to service you Mr. Wilson. There's a coupon for the first fitting service on the web. We should have your suits ready in a few weeks" I'll be in touch." Amanda clapped her case closed and moved to the door.

""Oh Amanda, a moment, please," Shelly said as she caught her out of Bill's office.

She closed on Amanda grasping her arm firmly, and in a low voice, she asked, "Did you fuck him?"

"I beg your pardon?"

Shelly pulled Amanda closer: "You fucked him. Didn't you? I can smell it on you despite your perfume. Your lipstick is smeared, and you aren't wearing panties. By the way, what is that perfume?"

Amanda was surprised; how did she know about the panties?

Shelly released her grip on Amanda. "Sorry. I'm just so frustrated. I've been trying to fuck him for months. Next time, please include me," she smiled, "Here, you might be missing these," she said as she discretely passed Amanda's sodden panties. "Fuck, but I actually might need a towel to dry my hand - was that all you?"

They both giggled, and now both felt their pussies moistening

"Shelly. Why don't you set something up? Soon."