Turn Around

by Jennifer White

  

Sandra was upset. The company she had worked at for over 20 years had gone out of business, and now she was unemployed. She had been searching for comparable jobs, but there was nothing to be had. Faced with mounting bill, and getting near the end of her unemployment, she decided that she needed to get *any* job, even if it wasn't the ideal one.

The new bar down the street had a sign in the window that they were hiring waitresses. She hadn't ever been there, but she heard that the young crowd loved to go there, and party all night long. That sounded like a good chance to earn good tips; if they drank a lot, they'd run up the bill.

So Sandra swallowed her pride, and went in to apply. She needed a job. She arrived in the early afternoon, before the place had opened up. She asked for an application, and filled it in.

When she was done, she handed it to the manager, who read it over.

"Hello, I'm Sean" he said.

"Sandra. Nice to meet you Sean."

"You're a bit over-qualified for this job. You really don't want to do this, do you?" he said.

"Well, since they closed down Antonio & McKenzie's, I haven't been able to find a job. And I've got bills piling up, so I need to get out there and do something. I did some waitressing back in college, so I know I can do very well at this. And I have been in the customer service department for 15 years, so I know how to work with people. I also..."

Sean cut her off rudely.

"Yes, but this is a waitressing job. I don't think you would be very interested in it."

She thought it was strange how he seemed to be so discouraging about her applying for the job. Why was he being so negative about her?

"I understand that it is a waitressing job. That is what I am applying for."

Sean gave her a funny look.

"Let me show you something" he said. He got up, went out of the room, and returned a few minutes later with one of the waitresses. She looked to be about 23 years old, and as pretty as a model.

But what was really shocking was the uniform she wore. It was quite skimpy, more like a swimsuit with a ruffle around the waist that looked like a micro-mini skirt. The legs were cut very high up to the hips. In the front of the legs, it was cut high as well, then came down over the crotch with a narrow strip. One thought filled Sandra's head when she saw this: bikini wax.

She hadn't been waxed in years. She was 45 years old now, and she felt very sensitive about her looks. She felt that she was past her prime. So certain things like keeping her pubic hair perfectly groomed had fallen off her beauty ritual.

She looked lower at the girl's six inch heels. And the deep V in the top, showing off her boobs. She had marvelous cleavage, enough to make Sandra feel jealous.

But how could you be expected to wait tables in that getup? Is that why Sean was trying to discourage her? Because she didn't look like this pretty young girl?

"You wear that outfit?" she asked the girl.

"Yes honey. We get very good tips."

"I bet you do" she said.

"This is our standard outfit. All waitresses here wear it" said Sean.

He paused, waiting for Sandra to excuse herself, and leave. But she was angry inside! He was trying to get her to quit, because she was too old. How dare he try to keep her from working there, just because of her age? That would be lawsuit material, so he didn't just say it outright. But it was implied.

Well, she would show him.

"Fine. I could wear that. When can I start?"

Sean gave her a blank look.

"You need help you say. I don't see anyone else here applying for the job. And I accept the terms. So when do I start?"

"I'm sorry Sandra, you're very nice, but you're not qualified" said Sean.

"How so? I have waited tables before. I am very qualified."

Sean looked at the young girl, then back at Sandra. His patience was wearing thin.

"Look" he said, "the customers who come here are mostly young men, 21 to 25. They expect certain things in a waitress. If we don't keep up the proper image, they will go elsewhere. I'm sorry Sandra, but we can't hire you."

"Why? Because I'm not in my 20s, and I don't have huge fake boobs?"

"You said that, not me" said Sean defensively.

Sandra turned and walked out the door, as Sean smiled smugly. He thought he had defused the situation, and now he could get back to work.

* * *

 

The next day however, Sandra showed up at the office, but this time accompanied by another woman. Her lawyer.

"This is Janet Hertz, Attorney at Law" said Sandra. "She is representing me in this matter."

"What matter?" said Sean, innocently.

"The lawsuit I will file, for age discrimination."

"Hold on a minute! What discrimination? You decided that you don't want the job, so how is that my fault?"

"Don't play games sir" said Janet. "I have been apprised of the entire situation. You are in deep trouble. We will file with the state and federal authorities. You will be faced with hundreds of thousands of dollars of legal fees to fight this off, even if you manage to win in court. And if you lose, the settlement will be enough to ensure that you lose the club."

"I can afford it" he said, but inside he was getting very upset now.

"I think not. I did some research on you sir, and I knew that you are in debt up to your eyeballs. You are hoping that you can turn a profit, so you can pay back your creditors, before they get upset that you haven't been paying them. I think the Bartelli brothers will be most upset, won't they? And they don't just collect interest. They break kneecaps."

Sean was so upset at this invasion of his privacy! How had she found out about his secret backers? They would *kill* him if they found out that a lawyer knew they were the silent partners in the business. His rage boiled over, and he exploded.

"Then you can see why I can't hire her!" he yelled. "She's too old, and she'll scare away my customers! I need someone young and pretty! She'll put me out of business!"

 

There was a deafening silence as Sean realized what he had just said. He was in trouble now. He had just said something in front of a lawyer, that would nail him to the wall in court. He was going to lose everything now.

"I.....I...." he started to say, but there was no way to repair the damage.

"My client is willing to let the matter drop, if you are willing to sign a settlement with her" said Janet.

"How much?" asked Sean.

"Your pride" replied Janet, handing over a document. It was three pages long, and spelled out in minute detail what would be expected of Sean, if Sandra was to let the matter go.

The women turned to each other and smiled. They had him, and there was nothing he could do but to sign and date the paper, binding him to a set of promises.

 

"My work here is done" said Janet, who put the papers into her briefcase, and turned to leave.

"Thank you" said Sandra.

"Glad to help you" replied Janet. "You'll make an excellent club manager."

* * *

 

The first term of the settlement was that Janet was hired immediately as the club manager. That meant that she didn't have to dress up in the skimpy uniform. Instead, she worked in her office, making sure all of the operations ran smoothly. That took away power from Sean, who had been the manager as well as the owner.

But that was fine, because the second term of the deal would keep Sean so busy that he wouldn't have time to manage the club anyway.

"Do I really have to do this?" he said, looking at his copy of the signed document. The first part was bad, but the second would be worse.

"Yes, you do. Now go get everyone, and introduce me" she said.

 

Fifteen minutes later, all the club employees were gathered together around the bar. Sean walked in with Sandra, and stood in front of everyone who was assigned to come in early. The second shift would meet her later.

"It is my pleasure to introduce our new club manager, Sandra Washington" he said, applauding. Everyone joined in. "From now on, she is in charge. I would like everyone to introduce themselves when they get a chance, so she gets to know all of you."

 

The employees all came over and greeted her. The waitress who she had met yesterday remembered her.

"Hi, I'm Heather" she said.

"Nice to meet you properly Heather. I'm sure I'll enjoy working with you."

"Me too. I'm so glad we have a woman for a manager now. Sean just didn't understand certain things."

"Well don't worry Heather, there will be some changes around here. Sean is going to come to understand what it is you girls go through every night. In fact, I'd like your help in teaching him that lesson. Here is a shopping list. I'd like you to change into your street clothes, go out, and get these things for me."

Heather looked over the list. As she did so, her face lit up. She looked up to Sandra.

"Does this mean...I mean, are you going to..."

"Yes Heather. Sean is going to be in for a tough night. We have lots of work to do, so you had better get going."

Heather giggled as she headed out the door. This was going to be fun.

* * *

 

When Sean returned in the afternoon, Heather and Sandra were waiting for him.

"How did it go?" asked Sandra.

Sean just glared at her. He of course had been totally embarrassed to go out to a spa and get a bikini wax. And it hurt! They just ripped the hairs out by the roots. Ouch! He had never thought of the pain that he might have forced the girls to go through. Sandra had also made him shower, and shave off all his body hair. He felt like a freak.

"We have done some shopping for you" said Sandra. "Its time to begin your transformation."

Heather rubbed her hands together in anticipation. She couldn't wait, after seeing the items she had on the shopping list. Sandra was all smiles too. Only Sean was upset. He knew what was coming, but he couldn't do anything about it.

These two were about to turn him into a woman.

"First, you need to strip naked" said Sandra.

Sean looked reluctant.

"Don't worry honey, I've seen naked men before. And soon you'll be a girl, so you need not feel embarrassed to be naked in front of us."

Sean undressed, but stood behind the desk so he would have something to him a little. He could see the girls staring at the neatly trimmed tiny rectangle of pubic hair above his crotch.

"First of all" said Heather, "we need to hide that *thing* you have."

She pulled an item out of the shopping bag that made Sean gasp. It was flesh colored, and looked somewhat like a pair of shorts. But in the crotch was something scary: a fake pussy.

"Put this on" ordered Sandra.

Sean was glad to have something to cover up his nakedness, but skin tight shorts with a latex rubber pussy was not what he had in mind. He couldn't take his eyes off the mirror, where he saw an image of himself staring back, but with a woman's genitals between his legs.

"A real woman doesn't like to go around naked, so you'll want to be putting on panties right away" said Heather, handing him a pair of black thong panties.

Sean put them on, and stared at how they laid flat across the front of his crotch. There was no bulge, like he normally had in his briefs. It made him feel scared, weak, and he trembled.

"Now for up top" said Sandra. Heather pulled out two very large fake breasts. She walked over to him, and held them up for size.

"Looks good" said Sandra.

Heather took a few drops of the special glue that came with them, and put on the left breast.

"Hold this in place" she told him. "You don't want to have them uneven, do you?"

Sean held the breast in place, while she glued and attached the second one. It was very cold at first, but it started to gradually rise up to body temperature.

"Now hold this one too" she said. "You need to keep them from moving for about a minute."

Sean saw himself in the mirror, and he looked like a woman who was shy about letting someone see her breasts, and was holding her hands over them. Between that and the panties over his smooth crotch, he really felt torn up inside now. The weakness that the fake pussy made him feel was amplified by the sight of himself with tits.

"Okay, let them go!" said Sandra, looking up from her watch.

Sean let his hands go. He expected *them* to fall off. But they stayed in place, and actually jiggled a little bit from losing their support, just like a real woman.

"Bra" said Sandra.

Heather pulled out a white lacy bra. It was the kind that helped lift and separate the breasts, creating move cleavage. She put it on Sean, who stared at the image of himself wearing a bra. It left the top of the breasts exposed. Looking down he saw lace and cleavage. It made him feel a tingle in his groin, but with the tight fitting pants, there was no room for him to grow hard. And even if he had been able to get hard, the latex rubber in the crotch would have hidden his bulge anyway.

"Very good!" cooed Heather. "You'll make a very sexy waitress."

"Yes Allison, I think you'll do just fine" said Sandra.

"Allison?" said Sean.

"Yes. That's your name, now that you're a girl. Allison."

 

On the inside, Sean was already feeling upset over what they were doing to him, and the fact that he had to go along with it. As they feminized him, he felt weaker, which was very hard to take for a powerful man used to ordering women around. He viewed women as somehow inferior, but now he was starting to look like one himself.

Yet somehow, now that they were calling him by a girl's name, it made him feel even ten times weaker. This was terrible. It was getting worse and worse.

"Put these on" said Heather, handing him a pair of ecru pantyhose. He put them on, with Heather providing some directions to make sure he didn't cause a run.

"Nice legs babe" said Heather.

"Yeah Allison, you have very nice legs. The other girls will be jealous."

Sean hated how his legs looked long and sexy, like a girl's. It was another blow to his diminished manhood. But what came next, was even worse: the uniform.

"Put it on Allison" said Heather. "You get to wear the same thing that all the other waitresses do."

Sean's hand was trembling. The skimpy uniform that the girls wore? How could he put it on? He didn't even know how to put it on. It was sort of like a woman's one-piece swimsuit. He just looked at it.

"It won't bite" said Heather, who showed him how to step into it.

"Look at yourself in the mirror Allison" said Sandra. "You're a sexy *waitress* now."

Sean felt ridiculous in the skimpy outfit with the ruffle around the hips, the high cut legs, the plunging neckline showing off his new boobs. How could the women wear these things? He felt almost naked. He felt exposed and vulnerable. He felt cold.

"Have a seat Allison" sand Sandra. "We have a lot of work to do."

They made Sean sit with his back to the mirror on the wall, so he couldn't see himself as they went to work. Heather put a long blond wig on him, while Sandra put long fake nails on his hands, shaped them with a nail file, and painted them a bright red, followed by a glossy topcoat.

Now Heather started applying makeup to his face. Sean didn't know what all the powders and creams were called, but they seemed scary to him. She kept putting on more and more, then splashed him all over with perfume.

Sandra put large hoop clip-on earrings on his earlobes, which felt uncomfortable from the pressure. She also put a necklace on him, which dangled down low, almost to his breasts.

"That will help keep men's eyes on your boobs" said Heather. "And that's good, because you want to show off your bod if you want to get good tips from those horny young men."

The thought of being ogled by young men made Sean extremely uncomfortable. He squirmed in his chair.

"Look, she's very eager to get out there" said Heather.

"First she needs her shoes" said Sandra.

Heather had also purchased a pair of black stilettos, in Sean's shoe size. She put them on him, and he was now complete.

"Come look at yourself in the mirror Allison" said Sandra.

Heather helped 'Allison' stand up. Sean was very wobbly, walking in heels for the first time. He had his arm around her, as she guided him to the mirror. Sean looked up, and saw himself.

Long blond hair cascaded down the back of his head, and over his shoulders. His face was covered with heavy makeup. His eyes! His lips! They didn't look like his. They looked like they belonged on a sexy girl.

He looked down at his big breasts, and shivered. They seemed real. Moving down, he saw the sexy high cut of the legs, with the flat little strip of material covering his crotch. His legs looked long and sexy, with his calves looking exciting in the dangerous looking heels.

He looked like a sexy woman, and he felt very turned on. He felt the pressure in his crotch as his manhood tried to get hard. But there was no room because of the tightness. And the fact that his feminized appearance was a turn-on, was very scary. He looked good enough to turn himself on. Oh no!

"Lets practice walking Allison" said Heather.

 

Sandra got to work doing her duty as a manager, as Heather trained 'Allison' on how to walk in heels, how to carry a drink tray, how to write up orders, and the other little things he'd need to know as a waitress.

"Heather, you had better go get changed" said Sandra.

"Okay boss. What should I do with Allison here?"

"Take her with you, and introduce her to the other girls."

"Come on Allison, it's time to introduce you to everyone" she said. "You'll be working section 5 tonight, so I'll show you your tables too..."

* * *

 

It was getting late, and the crowd was building. The club was getting more and more busy, with the small line starting to form outside. All of the waitresses were very busy serving customers. Especially 'Allison', who was new to the job of waitressing, and seemed to take three times as long to do everything as the other girls.

"Come on honey, pull your wait" said Heather. "You're falling behind."

"But this is *hard*!" said Sean.

"Allison, even a woman can do this job. Our old manager Sean used to say that all you had to do was walk around and flash your tits. How hard can that be? Now get to work!"

 

Sean's feet were aching, and his legs too. Not used to standing on his toes for so long, he was starting to get a cramp in his leg. Not to mention the great embarrassment he felt being in public, in this getup. The way the drunken guys looked at him, and at his tits! He felt so uncomfortable. He tried to bury himself in the work to make the time fly by. But it dragged on, and he was almost on the verge of tears.

Sandra walked around the club, making sure everything was running smoothly. She noticed that one of the beer taps at the bar was sputtering a little, a sure sign that the keg was running low. She called downstairs to get a replacement ready, so there would be no interruption of service.

"Thanks Sandra" said Janie, the bartender. "Sean never helped out with stuff like that, so I'd get all backed up while getting a new keg ready."

She was efficient, mixing drinks as she talked. Sandra nodded. Women were good at multitasking, which was a critical skill for a bartender. She would remember Janie's efficiency when it came time for performance reviews.

"Excuse me Miss, are you a manager?" asked a man at a table behind her.

"Yes sir, how may I help you?" she replied.

"Well, I've been here quite a while, and I haven't even seen a waitress yet. I'm getting impatient."

"I'm sorry sir. I'll got get Allison. She has this section."

A minute later, Sandra dragged 'Allison' over to the table.

"Allison, these people have been waiting here for 15 minutes, and you haven't even taken their order yet! This is unacceptable. I want you to take their orders right now, and buy them a round on the house. Don't ever slack off like that again! Now get to work!"

The men smiled smugly. The stupid waitress was getting chewed out in front of them, and they were getting a free round. Sandra had turned a group of dissatisfied customers into happy ones. She had done a superb management job. Only Sean suffered, getting chewed out by a woman, in front of others. As if wearing his skimpy outfit wasn't bad enough. Now he really was on the verge of tears.

* * *

 

At the end of the night, Sean was ready to collapse.

"How do you do it?" he asked Heather. "My feet are killing me, my legs hurt, I feel cold, I feel like I've had every guy looking at my tits all night...I can't do this job!"

"There, there Allison" said Heather. "You'll get used to it."

"What do you mean 'used to it'? This is just for tonight, isn't it?"

"Tell *her* Sandra" said Heather, grinning from ear to ear.

"That's right Allison" said Sandra. "Look at the agreement you signed."

"I thought it said that I had to be a waitress for one night, so that I would understand what the girls had to go through."

"Yes and no" said Sandra. "Yes, you had to do it for one night, but no, there was some fine print. It said that if you did not perform at a satisfactory level, then the clause in appendix A kicks in. Clearly you were not satisfactory tonight. I had 14 complaints from customers, and 13 of them were about *you*. If you were a full time waitress, I would fire you right now."

Sean looked at her, knowing that she was right.

"Appendix A states that in the event that you are unable to properly fulfill the requirements as stated in the main portion of the before mentioned agreement, then you are to adhere to the following additional requirements: 1) You shall perform your waitress duties for a period of one month. 2) You shall remain in character full time during that period. 3) At the end of the aforementioned one month period, you shall be rerated, according to the criteria previously state, and Appendix A shall apply."

"In other words" said Heather, "you have to be a girl for a whole month now. And at the end of the month, you'll be rated. If you are a good girl, we'll let you go back to being Sean again. If not, then you're going to be Allison for another month. Then another. Then another. Until you get it right."

Sean could no longer hold back the tears. They started to flow freely now. This was hard for one night. How could he do this for a *month*?

"Don't cry Allison. Your mascara will run."

"You had better buy her some waterproof mascara next time" said Sandra. "She's a girl who likes to cry, being so emotional and all."

"Is there any other way to get out of this?" asked Sean. "I can't go around being a girl for a whole month."

"I'm glad you asked" said Sandra. "I happen to have a document right here."

She handed over a pile of papers stapled together.

"It's all legal mumbo-jumbo, but it boils down to one thing: you can sign the club over to me as the full owner, and I will release you from your servitude. Or you can keep the bar, and be a girl. Your choice.

The night was so terrible, that Sean could not envision himself going through it again. With a trembling hand, he signed the papers, giving Sandra full control of the bar.

 

Just at that moment, the door burst open. In walked three large dangerous looking men in suits and ties. The Bartelli brothers.

"Where is Sean?" asked Vinnie, the eldest and leader of the brothers.

"He's not here. I am Sandra, the new manager and *owner*. How can I help you?"

"That little slimy worm. If I get my hands on him, I'll kill him!" said Vinnie.

"Why, what's the matter?"

"He owes me money. You can tell him that I'm putting a hit out on him! He is dead meat. He can run, but he can't hide. We'll track him down, anywhere he goes to. You can tell him that!"

"I sure will" said Sandra. "But don't worry, now that I'm the owner, I will make sure that your loan is repaid by the end of the year."

"Thank you. But tell that slimebucket Sean that he is dead."

"I will. Goodnight gentlemen" said Sandra.

The brothers turned and left.

 

"Well Allison, it looks like you had better not return to being Sean any time soon. Not if you want to live, that is."

Now Sean really started to cry. He had just signed the club over to Sandra, so he had no money and no job. And now he was under threat from his life, and Heather was right. The only chance he had to avoid being hunted down by the Bartelli brothers, was to stay undercover, as Allison.

"What am I going to do?" he sobbed.

"You can work here, as a waitress" said Sandra.

He looked up at her, his eyes full of tears. She was right. It was his only option. He was stuck being a waitress now.

* * *

 

Once Sandra took full control of the club, she started making several small changes. First, the uniforms of the waitresses were changed, allowing them to wear more comfortable shoes, and something less revealing. It was still sexy, with a short black skirt, but it at least covered them up enough to be comfortable.

She also started making the club more woman-friendly. Instead of being a place where young men came to ogle pretty waitresses, bit by bit it became a place where women hung out too.

In fact, after six months, there were often more women than men in the crowd. Sandra hired sexy young men to wait tables too, and had them wear something to show off their bodies as well, with tight pants that left very little to the imagination.

The club raked in the money, and she was able to pay off the Bartelli brothers months early, something they very much appreciated. Even Allison had become a wonderful waitress, getting one of the largest tips every night. Everything ran as smooth as silk, and everyone was happy, with the possible exception of Allison, who was still getting used to being a woman full time. Allison had taken Heather's advice, and was starting on female hormones, to help make things easier. One day soon, she would be a real woman.

* * *

 

"I think it's so funny!" said Vinnie Bartelli.

"What a crack-up!" said Sandra.

"I mean, Sean in that get-up like one of your waitresses? How did you ever get him into that?"

"Oh, I just kind of used some legal blackmail, and made him think that it was in his best interest."

They all laughed, as they downed a drink.

"Listen Vin, I want to thank you again. Your threat was what made Sean stay as a woman full time. You were really convincing. I almost thought that you meant it."

"No problem dear. Anything for my family. Even if you are a distant cousin, you're still one of us."

"I hated to have to use you, but I think we're all happy from the deal."

"Yes. We got our money back, with interest, and early. You get a club of your own. And that worm Sean has been turned into a girl. A very happy ending!"

"I'll drink to that!" said Sandra, raising another glass.

  

  

  

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