Dress for the job you want (+1 Alpha)

“A job interview actually. But I’ll leave the questions about style to you, you’re a *experienced tailoress* after all.”, he taunts back, hoping she had a professional argument with one or two older tailors in the past.

“Ah, you got me there. I guess we’re both more mature than we look”, John thinks this is the first real smile he gets from her.

Ms. Bianchi takes measuring tape from her belt and motions for him to step on the stool in front of a tall mirror. As he stands there, his eyes (involuntarily) land on the black haired woman’s proud set of breasts. A plan on how he might finance his business clothes forms. And he thanks god he isn’t stuck with an old man as his outfitter…

“Can you even take my measurements in these baggy clothes? Give me a second, I’ll make this easier for you”, without further ado he disrobes his upper half. John isn’t as jacked as he might like, but he has a solid build, broad shoulder and ,even though it isn’t a six-pack, a flat belly.

The expert seems to agree with that conclusion. This is probably far from regular practice, especially with them being man and woman, she lets it happen. And throws him an appreciative glance.

“So, you want a tight modern fit, hmm? Very well, I’ll be sure to be extra diligent with my measurements…”

“Take all the measurements you need...” John offers with a slight flex of his chest muscles.

Ms. Bianchi smirks, going to work immediately, wrapping her measuring tape around John’s belly and cinching it tightly around his back. “Breathe as you would normally…” she instructs, reaching around and placing her hand against John’s bare stomach to control the depth of his breathing.

“A 34 Waist…” the seamstress mutters to herself, pulling out scrap of paper and hastily scribbling the number down. “Now lift your arms above your head…” she commands him.

“Like this?” John chuckles, raising his toned arms in the air slightly. The tailor nods, stepping closer to John as she begins to measure his broad chest, her hands smoothing out the tape across his pecs and drawing an involuntary giggle from the back of John’s throat as she grazes one of his nipples.

“Ticklish, Mr. Williams?” Ms. Bianchi asks, quirking her eyebrow in amusement.

“Perhaps,” John says, doing his best to hide his impending smile.

The next few minutes proceed much the same with the seamstress measuring John’s upper body, taking repeated measurements of his chest and arms, occasionally cracking a smile at the results she finds like she was sizing up a piece of steak for dinner.

“That should be enough for the top.” the lady finally announces. “Now let’s do the bottom half…”

Grinning wickedly, John begins to slowly rub himself through his jeans. Hopefully he interpreted their playful banter right. Ms. Bianchi sinks lower on his body, halting at groin level. Her face, directed straight forward, is undecipherable from Johns position.

“Do you have any idea how many customers try to impress me with their *measurement* down there? There’s a reason this would usually be done by a man. You’re lucky you’re cute, or else I-… I’d…”, her voice started challengingly, but quickly lost it’s fire. Ironically John had gained that fire. His rubbing and her talking so close to his cock, have literally breathed life into it. And more confidence into John.

“I would never want you to feel uncomfortable, Ms. Bianchi. I’m not trying to make a move here, but I think you see my predicament. My pants could never be a decent fit, if we didn’t include this”, he withdraws his hand and now unveils what the Italian lady must have seen already, going by her stutter. His cock now strained down his trousers leg and feels like it’s even bigger than back at home.

“I-If you put it like that Mr. Williams, I beg your pardon. This is something I sho- I mean every good tailor- should pay special attention to. We wouldn’t want you to tear apart a perfectly good set of pants just because I didn’t think of that third leg of yours”, now she looks up at him again and that playfulness has returned to her voice. Along with a certain seductiveness.

She finishes up her measuring, doing her due diligence, but her eyes regularly return to Johns still confined dick. As soon as she’s done, she builds up her courage and addresses him again.

“Now I’ve done all the lengths I need, except the literal *elephant* in the room. The hmm current obstruction makes it a hard- I mean tough- to take a precise length like this. Would it be alright with you if I took a closer look? For the fitting?”, at the end the only addresses Johns *lower head* instead of his face.

“Oh, be my guest Ms.-“

“Donatella. Or Dona if you like. A man and his tailor should have a close connection, wouldn’t you agree, Sir?”

“Yes, I see us having a long and intimate business relationship in the future”, he smirks down.

Eager for more, the young tailoress reaches down and fumbles with his pants buttons and zipper. And as his pants and boxers hit the floor in one fluid motion, so does Donas jaw. Freed from his imprisonment, Johns cock rises, hitting his still exposed belly. Still in awe Dona raises the tape close to the pulsing member and goes scarlet red as she internally reads the number.

“A-Almost nine inches in length and two and a half in diameter. Sir, you might not be my richest customer, but I’d bet the family business that you’re the biggest. I think I’d profit greatly from you as a repeat customer. Would there be any way to persuaded you to turn your back on other establishments?”, her hands stay on Johns cock, even though the tape has subtly disappeared.

“I’m sure a beaty like you would be able to persuade me *into* a lot of things. But right now, we might indeed make this a business transaction. You see, I’m in a bit of a bind financially. And I see, you’re in need of something else I possess. How about you lend me a suit with the needed *room for growth* and in exchange I’ll lend you the jawbreaker down here?”, John twitches the cock that Dona has unconsciously started caressing.

Blushing profusely, Donatella shifts in her half-kneeling state and then leans over, even as John grabs at her dark, wavy hair with his hand, taking hold of it and guiding her head down to his crotch. He rubs his cock all over her face insistently. She has sucked a mans penis before, sure, but she has certainly never done it for a customer before. Let alone a customer that blatantly told her, he wouldn’t pay a single dime in her store.

But right now, all she can think about is putting that cock between her lips. That’s exactly what she does, sucking the first few inches into her mouth and bobbing her head up and down on Johns cock. With the faces she’s making, it’s obvious how pleased she’s with Johns part of the bargain. To her it’s delicious, better-tasting than she ever expected. The well-off professional can’t get enough of it and before long she’s happily trying to deep-throat his entire prick down her throat, with Johns help of course. Their combined effort get them so far down, her throat shows a visible imprint of his cock. She gags and chokes on his dick, as quietly as she can manage in the hopefully still empty shop.

The thrill of this stunning woman worshipping his cock in exchange for giving him a no-doubt criminally expensive suit, drives John wild. This is like a win-win situation, the only difference, that now it’s a double-win for him and a sore jaw for her. Her technique is excellent, but his hefty meat is still taking a toll on her. Being the nice guy John is, he decides to not hold back for much longer.

“You’re the only employee in right now, aren’t you? I don’t want to keep you busy forever. How about I give you that safety deposit for the suit right now?”

She nods as best as possible with so much cock buried inside her gullet. John grabs her head assuringly with both hands. They hold eye contact while he helps her get all the way down.

As soon as her bottom lip kisses his balls, he unloads inside her. Spurt after spurt shoots into her stomach. Her eyes roll back into her scull and her face takes on a blissed out expression. The cum hits too far back for her tongue to catch its taste, but the hot sticky feeling that coats her throat, her quim can’t help but quiver.

“Thkth fur huur bithneth~”, Dona utters incomprehensibly through her mouths intruder.

“A pleasure doing business with you”, John pets her head, “But you really shouldn’t leave a mess like this.”

He withdraws his cock all the way and yes, his lower half is a mess. She left slobber and rests of overflown cum on his thighs and little specks down on his shoes. The once proud professional blushes like a school girl about to address her crush.

With meeting his eyes, she really does lick his thighs clean. After the first lick she lets out a badly suppressed moan. God, he tastes as delicious as he looks~, she closes her eyes and shudder. As she’s done with his thighs, savoring every lick, her eyes shamefully travel to the puddle between her young customers feet.

“Oh, I’m a new customer and it’s just the two of us. Feel free to show respect in whatever form you think fits, I could be persuaded to become a repeat customer”, he gives her a devilish smirk.

Dona goes all the way down and if she feels defeated for a “customer” (that would cost her money…) to demean her like that, it passes in a moment. Because as soon as her tongue starts tracing over his shoes, she realizes this is just right.

What started as her giving in to a ludicrous impulse triggered by this strangers massive tool, turned out to be one of the hottest moments of her life. What would that thing do to me if he would actually come near my pussy~, her licking turns even more enthusiastic. In no time his shoes are flawless again. Still an old pair of sneakers, but spotless none the less.

They disentangle, Donatella scurries out her eyes trained on the ground, as opposed to her head-held-high attitude of earlier, and John undresses completely. When she returns a while later, her arms hold a stack of clothes. She avoids his gaze, places the stack on a bench and retreats to the store, mumbling something about giving him privacy to redress.

She sure hasn’t skimped out on the suit. His new three-piecer is as high classed as he could have imagined. It isn’t a perfect fit, of course she couldn’t tailor a new suit for him in a couple of minutes, but she sure found one that fits him meticulously. After John has put on his new clothes, he balls up the old ones and puts them in a bag Dona kindly handed him alongside the suit.

When John walks out of the stall and back to the reception at the front of the store, the shop is far livelier than earlier. John can make out two store employees talking with potential customers and an older couple browsing the ties by themselves. When he reaches the reception, Donatella Bianchi looks at him like they meet for the first time.

“Sir, don’t mind my humble opinion, but that look suits you exquisitely. You look just dashing”, she tells him almost coyly.

“And I have only you to thank for that. A true professional.”

“If you are so s-satisfied with our service, may I interest you in our premium customer experience? For so esteemed customers, we offer sort of a newsletter. You leave your credentials with me and we’ll keep you updated on all future offers that would fit your individual needs. If you ask me, we can even wave the usual entrée fee for it. The deposit you left here today will more than cover it”, she gives him a subtle smile, her tongue escaping the edge of her mouth teasingly for a mere second. She pushes an empty piece of paper closer to him. There might be a premium service here, but this is clearly personal.

“Yes, I would love to keep in touch”, he writes down his contact information and hands it back to her, “You’ve really gone above and beyond today, Dona.”

“You’re too kind, Sir. As an artist at heart, working with such a ~unique~ commodity can be a real eye-opener. I hope we can accomplish even more the next time we meet.”

“You and me both”, he hands her the bag with his old clothes, “I shouldn’t drag these along, would you do me the favor and take care of them for me?”

“Of course!”, she grabs the bag and stores the clothes beneath her desk. “And Sir? I wish you good luck with the interview. I have no doubts you’re the perfect fit for the position.”

Their eyes meet a final time and they share a thinly veiled inside joke, her employees and the customers around them none the wiser. John leaves the store for his interview, looking more dashing than ever.