Zack is the 34 year old wild, unconventional and attractive protagonist of the story. He is tall, has expressive dark eyes and colors his hair blue. As the Creative Head and co-owner of leading ad agency Impressions, Zack has many admirers. His life has its share of schemers with his brother Ben and girlfriend Tania desiring his feminization to meet their own selfish ends. By making a laughing stock of Zack, Ben wants to amass all his popularity. By feminizing him, Tania wants to satisfy her deepest fantasies.

On Tania’s suggestion, Zack dresses as “Zina” to be able to write the perfect ad copy to endorse women’s cosmetics, dresses and lingerie. Slowly and steadily, Tania and Ben trick Zack into completely becoming Zina— with silky long hair, breasts and a pussy. Though Zina is loyal to Tania, she finds that she is powerfully attracted to her client, Daniel Garfield.

A Slippery Slope in an Ad Agency

Chapter 1 – Adman in a Dress

Zack walked in into the smooth glossy interiors of family-owned Impressions Advertising Agency. It was huge and super-successful. Impressions even owned an independent company that handled the array of clients it received and catered to their advertising needs.

As he walked into the room Zack drew admiring glances from his staff on his blue streaked hair, eyebrow-piercings and the tattoo of a Scorpio (his sun sign) on his upper arm visible through the sleeveless denim shirt. His spunk, wit and style also attracted many followers. Zack’s eccentric style of dressing went with his role as the Creative Director of Impressions. Zack was tall, wiry and at the peak of his prime at 34. Many ladies coveted him, but he was loyal to his long time girlfriend, Tania.

Ben, Zack’s 36 years old brother, walked into his cubicle, peeked in and requested to have a word with him. He was as different from Zack as chalk from cheese. Unlike Zack, Ben was pale, ash blonde and lacking in personality. He doubled up as the Accounts Executive and Communications Executive of Impressions Ad Agency, but none of the employees paid him the slightest attention. Even though Ben had equal stakes in the company as Zack, he was never treated as the boss. The younger brother was indisputably the popular one: both professionally and socially. This was the cause of some jealousy in Ben. The fact that he had silently been in love with Zack’s girlfriend Tania was the cause of resentment as well. However, Ben never displayed any of his inner emotions. His manner was bland and matter-of-fact, and expression inscrutable. Nobody suspected that beneath the solid, placid exterior lay a creature simmering with passion.

“Bro” Ben presently said in his flat voice “the biggest client ever contacted us today. He wants us to endorse his line of beauty products for women, that is if we bag the deal”

“And who is the biggest client?” Zack asked curiously.

“Daniel Garfield, of Minerva Products” replied Ben

“No Kidding”! said Zack enthusiastically “he’s one top dog! I bet he has a HUGE budget!”

“That he does” agreed Ben “but don’t cheer this soon. We’ve not hooked Garfield yet. You will have to create an impressive enough ad campaign to do that. Otherwise, he’ll go to Vistas, our rival ad agency.

“I’ll never let that happen” swore Zack “we can’t let that slimy Damon win. I’ll create such a swell hard copy that will blow Garfield away”.

“Well, good luck” said Ben drily “here’s the creative brief’.

Zack went into his cubicle and skimmed through the creative brief written by his brother. It briefly stated the background of the famous Minerva Products, contained a lot of other information, a note about the target audience and the budget. Zack couldn’t help noticing that the budget for the ad of Minerva Beauty Products was a whopping 4 crores’.

“Wow” Zack breathed “that’s’ quite a sum!”. Even though Impressions was a very successful ad agency, it had never got a client with such a big budget before!

“A client with a big budget would mean profits for Impressions and greater pay for the employees; I must clinch this”, he thought his jaw set in determination. Zack sat down to write the catchiest, most persuasive ad copy. He would, later on, create the most appealing website for marketing purposes. Zack was an ace at both words and design.

Tried as they did, the words wouldn’t flow. “Funny” thought Zack “a creative block has never happened to me before”. He attributed his inability to write to the stress created by the big budget assigned to the project and fierce competition from Vistas. He thought of contacting his creative team to brainstorm ideas, but Zack saw that all the cubicles were empty.

It was but obvious why. No one worked on a new year’s eve, especially in the urban metropolitan city of Bangalore. Zack remembered that he had a date with Tania later in the evening. He looked at his watch. Zack had two more hours to go before he was supposed to pick his girlfriend up. For now, he was to work–alone.

Zack wrote many a copy and crumpled the sheets up in frustration. What was wrong with him? Had all his creative juices dried up? It seemed like he had lost his ability to think, leave alone write. Zack crumpled into a dejected mess on the floor and put his head down on his folded knees.

He heard the door knob turn and the door open with energy. “Zack?” breathed a familiar husky sexy voice “what’s up, honey?” Zack raised his defeated face to his girlfriend Tania. She looked stunning in a red gown that complemented her tall, slender figure. Her size eight feet were encased in nude sandals and dark red hair pulled back in a chignon. Tania was more than just a pretty face. She owned the successful Rainbow TV channel that offered ad space to Zack’s agency at a subscribed rate because he was her boyfriend.

Apart from her black handbag, Tania was carrying two rather massive polythene bags with her.

‘Oh! Sorry, darling’ said Zack remembering “I forgot to pick you up. A gorgeous woman like you doesn’t deserve a hopeless boyfriend like me”.

“Hush” Tania shushed Zack putting a lithe finger on his well-formed lips “I can see you’re in a bad place. Tell me exactly what the matter is”.

Zack told her.

“What does Minerva Beauty Products cover exactly? asked Tania

‘Hmmm… the usual thing’ replied Zack “lipsticks, mascaras, eye shadow and stuff, you know.’

Tania listened intently. She had always had a secret kink: to feminize her sexy boyfriend. Even though she didn’t desire to be a man, Tania often dreamed of being the dominant in the relationship and treating the feminized version of Zack as her whore. As Zack spoke, an idea struck Tania. A naughty, wicked idea. She made full use of the opportunity presented to her to her advantage.

‘You know, Zack’ she said in a slow deliberate voice ‘the reason you’re not able to write a good copy is because you aren’t thinking like a woman—after all, they are the target audience of your ad”.

“So, you write it for me” said Zack

“Come on, Zack’ laughed Tania “I am a businesswoman, not a creative!”.

“Well, then I am dead meat today” said Zack holding his head in his hands.

“Not necessarily” Tania smirked and bit her lower lip. Her green eyes twinkled mischievously.

“What do you mean?” Zack blinked.

“You could be a woman for tonight” said Tania “for as long as it takes you to write a good, persuasive copy”

“Ha! You’re joking right?” laughed Zack.

“Never been more serious in my life” said Tania “suppose you’re writing about a car, you’ve got to test drive it first. If you’re writing about a particular candy, you’ve got to taste it. The same applies to beauty products!”

“Damn! I am not doing it!” said Zack.

“Think about it” said Tania “Minerva Products is BIG. If you don’t grab Garfield, Vistas will!”

The thought of the huge hairy Damon getting the ad contract was too much for Zack to bear. “Guess, it wouldn’t hurt to give it a try” he said grudgingly.

“That’s a good sport!” said Tania approvingly. Desire and excitement stirred somewhere down below. Tania’s most erotic fantasy was finally going to come true. But wait… she should never let Zack suspect. He would think she was a pervert. Tania reminded herself to play it cool and act very business-like about the entire affair.

“Okay, where do we start?” asked Zack hesitantly.

“Well, I got an extra dress along” Tania said nonchalantly pulling out a slinky short blue number from one of the polythene carry bags “Just in case I dropped wine or something on the one I am wearing ….. Why don’t you try it on ?”

“In here?” asked Zack looking aghast.

“In the restroom, silly” Tania laughed

“Gents or ladies?” asked Zack dubiously.

‘Why ladies of course” said Tania peremptorily leading Zack across the corridor to the ladies bathroom. He squirmed uneasily as Tania got him to take off his jeans and Bob Marley t-shirt and had him put the flimsy little dress on. Zack did’nt have too much hair on the arms and legs, so the dress didn’t look as grotesque as it would on any other grown male, but Zack’s well-toned biceps, muscular calves and, of course, his flat chest were a giveaway of fact that he was a man dressed in drag.

Zack self-consciously looked at his bony knees and bare arms and nervously said

“You don’t think this is too skimpy, do you?”

“Of course not” said Tania with energy “I think it is perfectly delicate and feminine”.

“God, my feet look so weird in these sneakers!” Zack exclaimed.

“Abracadabra!” said Tania pulling out a pair of transluscent blue slippers from her bag.

“You almost make me feel like Cinderella” grumbled Zack trying them on. Surprisingly, they were the perfect fit .

“Hey!” Zack said getting slightly suspicious now “it’s almost as if you shopped these for me!”

“Of course not, honey” said Tania deceptively “You and I are the same shoe size”.

“Are we?” Zack raiased a skeptical eyebrow, as Tania asked with barely concealed excitement:

“Okay, now where are the Minerva beauty products? You surely have samples”

“They are in Ben’s cabin–in the first draw”

“I’ll get them” Tania who was familiar with the layout of Impressions rushed to Ben’s office and got the kit that contained Minerva beauty products. Trying to steady a hand that was quivering with the excitement of a fantasy supressed for years, Tania bedaubed foundation on her boyfriend’s smooth skin, lined his dark eyes with kohl, curled the lashes with mascara and painted his lips a frosty pink. With each stroke of her the make-up brush,Tania’s pulse quickened. Zack was ACTUALLY metamorphosing into “Zina”, the lover she had dreamt about over and over again!

Zack confused her excitement for dizziness. He thought a fanting spell was coming over Tania. “Honey, are you okay?” he asked concerned “shall I get you a gin and tonic?”

“Of course, I am okay” said Tania steadying herself and giving Zack a bright artificial smile. “Now excuse me, I’ve got to change”. She disappeared into one of the toilets with the other bag she had brought with her and emerged a few minutes later wearing a neatlytailored black two-piece suit and a tie with blue and white stripes. Zack noticed that she had put on a pair of men’s black loafers.

“Where has that come from?” asked Zack zapped.

“Oh, I first brought you an extra pair of clothes as well” Tania fabricated “in case you spilt whiskey or something on the ones you’re wearing”. Before Zack could react, Tania grabbed him by the arm and said:

“ Let’s hit the pub and welcome 2016, baby!’.

“Are we going like this?” asked Zack incredulously.

“It would be fun” Tania coaxed.

“It would be ridiculous” Zack corrected.

“Come on, baby” Tania cajoled “we’ve been a dull conventional couple for SO LONG! Don’t you want some zing… some chutzpah in our love life?

“I am content the way we are” replied Zack.

“Don’t be such a bore, Zack”, Tania said “for a creative, you are pretty dull”. She pursued her month in a pout. “Dull” Tania had just called him. Dull. The word could sound a death knell to their relationship. Zack realized it was evident that Tania felt their relationship was beginning to stagnate. If she continued to feel that way, there may be a chance that she would leave him. And Zack could never envisage the prospect of losing a smart and beautiful girlfriend like Tania. He loved her to distraction.

‘Okay babe’ he said grinning reluctantly ‘I guess I’ll oblige this eve’.

‘That’s my chick..I mean, dude!’ said Tania hugging him exuberantly ‘thank you, darling’.

‘Hey, but what about my creative copy??’ said Zack remembering.

“You can complete it after dropping me home” said Tania leading Zack down the corridor towards the exit. A few accountants and employees from the media buying department had decided to spend New Year’s Eve working away. Creatives, whose dates had stood them up, had also decided to return to office and finish up pending work. They were completely unprepared from the sight that confronted them; that of their favorite boss in a revealing blue dress and makeup being lead down the corridor by his suited-booted girlfriend. They stopped whatever they were doing and gaped at the couple. One saucy executive called Sally gave Zack a flighty look and remarked:

‘Seems like you’re getting in touch with the woman in you Zack’

Emboldened by Sally, timid Dean said: ‘So you let the lady wear the pants?’

‘Ha ha!’ Zack simpered actually distressed at all the attention that he was getting “Tania and I decided to swap genders for the night!”

There was some embarrassed tittering from the subordinates.

“Whatever floats you boat, boss” a malicious voice reached Zack as he stepped outside the office building and moved towards the parking lot “whatever floats your kinky boat!”

Click here to read the rest of the story!

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