Undercover boobs

A luxury problem remains a problem. Even if it is one born out of luxury and privilege…it’s still a problem. That’s where Evan Bruckhall found himself currently. Many people would love to be in his situation, as the owner of a bar franchise with five different locations. He lived comfortably, and he had a good thing going. A caucasian, broad shouldered, tall, confident and slightly pervy man, he was pretty much set for life already at 29 with both money and women. His Franchise, Double Endrede was a slightly sexy bar, staffed by attractive women only. From one, to three, to five…to five.

The problem was that the growth had plateaued, and he didn’t quite know why.  He was making a profit, a nice one at that, but still things had not quite moved so that he was free to expand as he pleased. Many people would love to be in his position, but for Evan, it remained an issue. He had tried a few new things but so far nothing seemed to really pay off.

At first, he was stubborn enough to not ask for any help and just try new things that ended up making no change to the overall bottom line. With the stasis continuing, he was left with the one option he didn’t want. Ask his friends for help. Mind you, like him they were locally influential figures with quite some contacts and businesses of his own. But since his friends were in quite different fields for him, there was not much that they could do for him. Outside of, of course, for his friend Larry “Chairman” Chafford who worked as a TV producer who said he knew a contact that could help him, one of his colleagues named Mona Sullivan. 

The moment he got a picture of her he knew that he wanted to meet her. A sleek and hot looking red headed lady with a striking set of hazel eyes hidden behind a pair of sleek looking glasses and a snazzy, professional looking suit. For a second his thoughts strayed to the gutter but then recovered with ease. After all it was business first, pleasure second for him. 

But for a business meeting the two of them most definitely hit it off. It was peculiar to Evan how there seemed to be a connection and a bit of trust between them even though they’d only just met. They had been talking in a coffee shop, just getting to know each other for about twenty minutes when Evan turned to the reason for their meeting. 

“So, miss Sullivan, my friend Larry said you could potentially help me out with my business’s struggle to expand further.”

Mona smiled at him and played with her hair a bit.

“Well yes. Ever heard of Undercover Boss? I happen to produce a show with a similar concept to it called “The hidden manager”.  If you and your business were to participate in it you could solve your issue in two ways. The first is free advertising from your franchise being on the show being introduced to a public that might not know you. The second is that you can find out about common problems and difficulties that your staff face that seem to be invisible to you, the boss. We would disguise and set you up as a common employee from another branch coming here to be the center of a work documentary.

Evan motioned at himself with a bit of a sarcastic vibe. “I regularly visit my establishments, and I don’t think there’s any way you can cover up this with just a mustache.”

She had a bit of a smug, annoying yet knowing smile, as if she knew something he didn’t and she was about to pull a fast one on him. It had been subtly bothering ever since they had met but he easily managed to keep his poker face going for the time being. 

“Rest assured, our special effects team can go pretty far.”

Evan raised an eyebrow but made no further comment on it. For the first time in the conversation Evan deflated a little bit from his ever confident self to get a bit more sincere and frustrated. His posture changed, leaning forward a bit more.

“I feel like I’m bashing my head against a wall over and over. Whatever I’m trying, it doesn’t seem to go anywhere. If you really can make me blend in as one of the chefs I will give it a shot.”

Mona nodded. “We can demonstrate our techniques to you later. Say, tomorrow, two o clock at the Salvander Building downtown?”

“Sure.” 

“Before you head out, I just wanted to say that you are an incredibly sexy looking woman.”

Mona chuckled. “You aren’t really…”

Evan nodded. “Oh yeah. I am. Before you go disguising my body, how about you explore it first before you go ahead and try to disguise it.”

Mona paused for an awfully long time. Her red lips curled into a thin smile. 

“One time.”

“I doubt you’ll want to stop at just one, but we’ll see. I’ve got a SUV outside with blinded windows and noise isolation…and a very special back section.”

She motioned for the waiter to pay the bill so the two could leave.

———————–

The sex was amazing. Evan could tell that Nona wanted him from the moment she first laid her eyes on him. There was a real instant connection between them, and when that turned physical on the back seat it was just fantastic. He explored all of her, every hole and by the end she swallowed his load without issue. As she stepped out of the SUV she left with a smile, yet as she stepped to her car she was deep in thought, looking conflicted about what had happened. Evan didn’t get to see any of it, and he headed off curious to see what tomorrow’s meeting might bring…and even hoped for a round two with Mona perhaps if he got lucky. 

—————

Evan maneuvered through the busy floors of the local TV center called the Salevander building. After asking around he made his way to Mona’s office. After knocking on the door she let him in. The afternoon sun shone in her hair and made it look almost sparkling and super vibrant. Mentally, Evan ranked her a few points higher on his “hottest chicks I ever banged” list to be near the top.

“Good afternoon, Mona.”

“Evening, mister Bruckhall. Let’s keep it professional today, please.”

“Absolutely.” Evan kept his smile at seeing her again subdued for the moment. “Getting right down to it then, how can you really disguise me as to not be instantly picked out by my staff?”

“We have a thing for that actually.” She reached for a nearby suitcase and laid it open on her desk. Laying in there was an orange and white women’s outfit with the words Double Entendre on it.

“That’s a woman’s outfit, what is this a joke?”

“Look under it.”

He lifted it up to see the skin of a pale looking woman, completely empty on the inside. 

“What IS this?!?”

“That is a skinsuit. If you put this on, you will become this woman and become part of your own serving staff for a while.”

“That’s not a thing…that’s not possible”

“Allow me to demonstrate.” Mona leaned in to grab the suit, tugging at the hand that came ripped loose. “Put this over your own hand.” 

Curiously, he complied. He fitted the empty skin over his thick masculine left hand watching in complete astonishment as the skin wrapped around his hand compressing it down to a clean, sleek and very feminine hand.

“Oh my God…are you kidding me, that is not real.”

“If you put the entire suit on, you would become a perfect recreation of Evelyn Brenner, the newest server at Double Entendre’s Westhall street franchise that has a TV crew following her to show her getting used to the job. That’s what we’re going to tell the other staff members at least.”

“This technology is amazing, with this anyone could become a smoking hot chick. Anyone.”l Anyone…” His face fell, his eyes widening as he came to a realization that made everything click. The cheeky smile, the instant connection, he knew that person. Just…as someone else physically

He turned to Mona who had the biggest smug shit eating grin on her face.

“Chairman?”

 “Sup fucker.” She put both feet up on her desk, oozing with smugness.

“We had sex.”

“Didn’t plan on it but honestly, it was too funny to let it pass by. You were great by the way.”

“We had sex.” Evan stumbled through the sentence, still baffled.

“We’re both single men, so what’s the issue exactly?”

“I…eh…”

Mona groped her own chest in front of him. “Larry doesn’t show up at work any more, Mona is the one paying the bills because why wouldn’t I be as attractive as this at work? It certainly earns me positive attention, wouldn’t you agree?”

 “So wait, you have been secretly living as a woman for how long?”

“Not secretly….my colleagues know. And I’ve been doing this for a year now. When I’m home I’m Larry though…most of the time.”

“Okay.” Evan awkwardly sat there, still having one feminine hand while the rest of his body remained the same. “Okay…so…”

“Well the offer to participate in our programme is open.” Mona smiled at him warmly. “But its up to you to decide to go for it.”

Evan hesitated. “Me…as a girl?”

“If you can behave yourself during work…I’ll let you booty call Mona from time to time.”

And with that all doubt was gone in his mind.

“I’ll do it!”

“Excellent.” Mona motioned at the suit. “Now let me show you just how much fun it is to be a woman…and to always have breasts within reach!”

———————————————————————————————————-

Double Endendre was a cosy establishment by design. Lots of wooden decorations and brown and yellow tones, and of course lots of young attractive women in skimpy outfits serving the tables. The official blue and white outfit gave them little modesty…by design. 

Every morning opened with a team meeting at 10 AM. The employees and their manager had gathered up in a circle of chairs to go over the plan for the day. And today, and the next few days surely would be decidedly different. 

Ricky Wandermann was the man in charge, and you could see that from miles away. Tall, dominant, broad shouldered, muscular and handsome he easily demanded respect from everyone…even if he wasn’t one to give it out. The brown haired man with too much gel in his hair wore a slightly ill fitting suit, making him look more professional than he was.

Next to him sat Dani Dumonde, though everyone called her DD. Her brown hair was in a bob cut, with bright red cheeks and pretty blue eyes adding to a warm atmosphere. Almost always, there was a smile on her face. Though that wasn’t what people were looking at though, it was her massive E cup chest that seemed to draw all the attention. 

Up next was Paul Jackson, a lanky guy who worked the bar (and the fryers behind it). He had glasses on his face and a bit of an awkward look on his face. But his record was impeccable and his speed was on point. The least popular guy in the room, mostly in the shadows of the pretty girls serving.

Speaking of which, the final two members of the team made you think you had a case of double vision for a moment. Lana and Maggie Mocksberg were two identical twins, who took great joy in confusing people on who actually was who. Their red hair wrapped into a ponytail combined with them wearing the same thick rimmed glasses meaning there were no visible differences between the two.

That was the usual crew, but today there were three others present as well. Mona Sullivan, a local TV producer flanked by her cameraman Steve Stevins (a name he was commonly mocked for in his youth) and of course the new girl.

Evelyn Barkwood. Dressed in a sexy  outfit just like the rest, her modest chest covered in the logo of Double Endendre. What seemed to set her apart though was her plump, voluptuous ass, motherly hips and long legs. Her face was flawless, a little bit pale which contrasted strongly with her  long flowing dark hair.

“So, ladies…and Paul. Today is a bit of a different week than usual.” Ricky stood up and motioned at the camera. “Channel 6 is here to do a documentary called “Working Lives” focussing on normal chicks like y’all doing their jobs. Evelyn there.” He glanced at her ass just a bit too long. “Is their intern here to learn the ins and outs of working here. And that Miss Mona Sulivan, the producer. If there’s anything you need, let her know. Welcome to the team Evelyn.” The two of them shook hands.

“Allright, let’s get to preparing for our customers, we’re opening up in less then an hour. Dani, it’s your responsibility to help get her started and keep her going.”

“Understood.”

“Okidoki Boss!” Evelyn saluted him. He had spent all night thinking of how to play this character but in the end it was simple, a positive, upbeat dumb bimbo like all the rest of his employees. “I’ll really do my best to learn all I can.”

“Good.” Ricky got up and headed for his office in the back. “Get to it, ladies! Do what you’re good for!” Evelyn paused slightly thinking about how Ricky said that before disregarding it. Time to see how it really worked.

————————————————————

Steve followed her around, the camera rolling as Dani was being sincerely helpful in helping Evelyn get used to it. For the most part, Evelyn was starting to regret signing up, but for now he was sticking to it. Strangely enough, he had more of a struggle with the idea of working then the fact that he was a hot chick with a dump truck ass right now. But all the while, Dani was supportive and even a little bit motherly, helping her slowly get into the swing of things while Mona helped direct a few things. At times, both of them were split apart and they were asked opinions about the job and their colleagues to gather up info that could be stitched together on the cutting room floor later on. 

Outside of the working though, Evan was having a blast being just a dumb, brainless chick, greeting people and having herself be ogled at just how Evan would do himself to any women he personally ranked over 6 out of 10. Partly he took some time to talk to customers and get their feedback on the restaurant. It stung a little to hear that many people thought that the cosy environment Evan had setup for Double Endendre was seen as tacky by quite a number of them. Also complaints. 

Evan got a bit more serious now, having gotten used to the role he was playing he continued to smile at guys to entice them into giving up bits of info he could use later. Though at times Dani had to (gently) pull him away from a table because more things needed to be done in the moment. 

Speaking of Dani, Evan had to admit to himself that she was the one who seemed to keep things going. Now that he wasn’t just dropping by but in fact very much in the middle of things Ricky seemed to be much less hands on then he had expected of him. At times he did come out to direct them, but otherwise spent his day in the office. Evelyn was halfway through delivering a new order to a customer when she heard her name be called out by Ricky. Turning her head, she kept walking and smashed into Dani, spilling ketchup and french fries all over both of their shirts.

“Ay! LADIES! Get changed, and Dani, look where you’re going. Did you stuff your brain in your fat ass or something?” Ricky audibly chuckled, unaware of the camera filming him from across the room.

“Come on, Evelyn, let’s go.”

“I’m sorry, I didn’t mean to.” She began to try and clean up the mess on the floor.

“I know.” Dani nodded. “It will be fine, it’s your first day here. Come on lets get changed.”

With her leading the way they headed to the locker room. As Dani took off her shirt to reveal her bra underneath Evelyn noticeably paused to see a very fine pair of breasts in front of her. Evan glanced down, resisting the temptation to grope then.

“Oh, you swing that way? Like what you see there, Eve?” Dani teased her a little bit by tugging at her bra without revealing anything. 

“Thanks for the compliment, appreciate it. Nice hips by the way, do you hit the gym often?” 

She reached out to gently drag a finger across Evelyn’s thigh up to her ass. Evelyn for her part got extremely flustered, blushing hard as the feeling of having her ass touched in a loving way was far more erotic then he could have expected. Underneath the skin he could feel his erection suddenly kick in,creating a barely visible bulge just above her dripping vagina. In a bit of fear at being found out Evelyn turned around giving Dani full reach for her thick ass. With both hands she started to massage the two ass cheeks. It was simply heavenly to her and she was completely lost in pleasure. Only little squirms matched with heavy breathing escaped her lips.

And then there was the sudden slap on her ass that brought her back to reality. 

“Oh my God, girl, that was meant as a bit of a joke!” Dani laughed. 

“Eh, I..it was.” Evelyn stumbled, still thinking about just how pleasant that little bit of massage felt.

“Come on, lets get changed before Ricky barges in here.” Evelyn got up and swapped out her shirt. Five minutes after getting changed they were back in the game greeting and serving guests. 

——

Around sunset, Mona and Steve had enough. As a bit of a finisher for the day they decided to take up seats in the corner and eat something before they went. Evelyn was getting tired but there still were three hours of work to go. 

“So Evelyn, how was your first day?”

“Hard…but worth it. I guess. I did learn a lot about plenty of things.” 

“Good. Can I get another double twisty fries then?” The smug smile on her face increased by quite a lot even though no one else understood the connection between the two. Evelyn let out an annoyed grunt, only to turn around and have the boss staring at her.

“Ay, bitch, that is no way to treat customers, you’re coming with me.” Evelyn was flabbergasted, did she just get called a bitch in public? She wasn’t intimidated by Ricky at all but for the sake of things she followed him in a stunned silence.

—————————-

“Have a seat.” She did so,  glancing up at Ricky who seemed to tower over her. 

“Well, Evelyn, so far, it’s not looking too good. At all. You’re pretty sluggish, you already caused damage by smashing a plate, and altogether, I’m just not sure you’re really D.E. material at all. When the TV show is done, you’re not going to be sticking around unless you change things up.” He put his hand on her shoulder, rubbing it gently.

“But I can help you with that. Getting better, maybe a raise…”

For a confident man, he certainly was caught completely off guard, a dull “eh…” escaping her mouth. 

The message continued. “You’ve got a great ass, girl, but you need to kick it into gear. God, what a lovely dump truck.” Leaning down even more, sliding down to touch her ass with the other hand. Evelyn gasped, feeling slightly embarrassed at being aroused.

“You see, I’ve got connections in the company, I’ve charmed the braindead idiot in charge, and I can make your work a breeze….or difficult. But that…” He reached further down, beginning to rub her clitoris. “Is going to cost you. Don’t worry, I’ll help you out.”

Evelyn stuttered, suddenly worried Ricky may accidentally touch his burgeoning cock.

“I need to think about that.” She got up out of the chair but stopped when he called her name.

“I’m sure you’ll do the right thing, girl.” Ricky mocked her as she left. “I’l be watching you.”

——-

Mona and Steve had left already. Evan was determined to talk to Mona but right now he would just finish his shift. Dani could see the look on her face and wrapped an arm around her.

“You okay?”

“Fucking Ricky.” She silently fumed. Glancing back at his door she saw him standing there, dominantly glaring her down before closing the door behind him. “That…that was…”

“Yeah.” Dani gave her a quick hug. “We should just complete today and we can talk afterwards. We’re almost there.”

Evan had more than enough information for what’s holding him back. Not just working on the decor, but also squashing Ricky. It would have been easy to squish him with an instant firing but unfortunately the only reason why Evan did that was to appease his dad, an influential banker. If he were to fire him (and justifiably so) then he would end up possibly getting in his dad’s cross hairs which could make things very difficult for him. Much too difficult for the price of removing one bastard

Evan was so pissed that he even forgot to catch a glimpse in the changing room, preferring to get out of there and immediately call up Mona. With big steps and her ass swaying somewhat she entered the alleyway

The moment the other side picked up she raised her voice. “Larry. Dude.”

“It’s Mona, you know that right now.”

“Larry, Mona, Larry I don’t care, Ricky just fucking sexually harassed me.”

‘What?”

“Yeah, the moment you were out he went all fucking creep on me, saying how much he charmed the real me and how he could make working life hell for me if I didn’t fuck him.”

“What! Are you serious!?!” 

‘I know, fucking hell right, never should have given him the job as a favor to his father but I can’t fire him or invoke the fat cat’s wrath.”

“What if we set him up? I can definitely install some covert cameras.”

“Well, that still is a grey area, I’m not sure if setting him up is gonna work.”

“Need some help with that, Evan?” Evelyn flinched, staring back at Dani who glanced at him with a big, smug smile on her face.

“Fuck.”