The Family Pt. 01

Kerry had some tough decisions to make. His roommate John had left him in a lurch. They had just renewed their one year lease for their two bedroom apartment when John lost his job and decided to move back into his parents house. That wasn't an option for Kerry. His foster parents kicked him out of their house 2 years ago - the minute he turned 18. He spent months sleeping in his car or on the couch of some random friend. It was a little over a year ago when he was able to convince John to split rent with him for this current place.

Money was tight, but the bills were paid and he didn't have to miss any meals. The job at the local hardware store paid well enough, but not enough for him to afford the entire apartment on his own. He had just enough money saved to make it one month but he would be in trouble after that. His love life was a dud as well, so there was no girlfriend or boyfriend to turn to.

He considered finding a second job, but working another 20 hours per week would probably still leave him short each month and burned out to boot. Of the few friends he had, none were in a place to help split rent with him. After talking with the apartment manager, the best he could offer was to help Kerry find someone else to take the lease off his hands. Even worse, all the single bedroom apartments were taken, so that would have to be an option of last resort.

Kerry was nervous about the situation, but he had learned to fend for himself while in the foster care system. His real parents abandoned him when he was just 5 and his years bouncing between foster homes had taught him that he could only rely on himself. He was kicking himself now for even wanting to share an apartment, but it made so much sense financially and John had been one of his few close friends. To his credit, John felt terrible about it and offered to ask his parents if Kerry could live with them for a bit, but it wasn't an option in his mind.

After two weeks with no news from the apartment manager and the rent coming due pretty soon, Kerry knew he had to take action. He went to various sites online to try and find work but very few places in the area were hiring for part timers. He tried to find jobs that paid more than the hardware store, but he wasn't qualified enough to nab one of them.

As each day passed, his desperation grew. He had called an endless number of companies and had interviewed twice, but nothing was working out. By the end of the week, Kerry had gotten nowhere and he was running out of companies to call.

When he woke up on Saturday, he jumped on his iPad and started the search again. While looking for jobs he came across a nondescript posting that he nearly scrolled past.

"Special dinner servers needed for elite and particular clientele. One evening for 5k. Call for interview. "

He looked at the small ad and thought it had to be a scam of some sort. One evening for 5 thousand? That was insane.

Yet, he couldn't stop thinking about it. His curiosity had taken over. He punched the number listed on the ad into his phone and placed the call.

"You've reached the voicemail of Chloe Felder. If you're calling about the need for dinner servers, leave your name, number, age, sex, height and weight after the beep. If you don't hear back from me within 2 days, we're not interested. *beeeeeeep*"

"Uh, hi. My name is Kerry and my number is 555-1948 and I'm twenty years old, male, five foot five and I weigh one hundred twenty five pounds. I'm really interested in finding out more about this opportunity. Thanks."

As soon as he ended the call, he had immediate regrets. Why did he give out all that information without hesitation?

He shook it off and continued to spend his day looking for a new job or a part time job that he could potentially take on. After a few hours of dead-end phone calls, his phone rang from an unidentified number. He normally sent those straight to voicemail, but something told him to pick this one up.

"Hello?"

"Hi, is this Kerry I'm speaking with," the feminine voice with a sophisticated British accent asked.

"Yeah, who's this?"

"Kerry, my name is Chloe Felder. You called me earlier about our need for dinner servers. Are you still interested?"

"Yes, I am. Is it really five thousand for one evening of work?"

"Yes, but very few people are hired for this and the gentleman who hosts these dinners is very particular about who works his events. I'm going to text you a link after our call ends. If you go to that link, it will let you securely upload recent photos of yourself. I need a photo that shows your freshly shaved face up close and one that shows your body, preferably in a swimsuit or underwear. If you're not comfortable doing this, then this work is not for you. Should I see that you haven't uploaded pictures within the next two hours, I will assume that means you are not interested and you will not hear from me again. If you are, and you upload the pictures as requested, I will contact you again to let you know if we are interested or not. Have a nice day. *click*"

With that, the call abruptly ended.

Kerry was perplexed, but before he could think about it any further his phone buzzed, indicating that he had received a text. There was an abbreviated link, just as she said. With his curiosity piqued, he logged into his iPad, pulled up the browser and went to the site. All that came up was a blank page with two buttons that said "Picture 1" and "Picture 2".

Kerry decided to go shower and shave before uploading pictures. Once done, he came back into the room and took a close up of his face and another of himself wearing nothing but his boxer briefs. He uploaded the pictures to the site and waited by his phone.

No more than 10 minutes had passed when his phone rang.

"Hello?"

"Kerry, this is Chloe. My client thinks you are a suitable candidate. The next step is for an in-person interview with me. I can meet you tomorrow at 8AM. I will text you the address of a local coffee shop in the city and we will meet there. Do not be late. *click*"

This lady did not mince words. She was direct and to the point.

His heart was pounding in his chest. This was incredibly mysterious, yet he wanted to find out more. Plus, what was the harm of meeting a woman in a coffee shop? He didn't know if he would take this job, but he definitely wanted to learn more about it. He decided to at least meet with Chloe the next morning and make his decision once he knew more.

---The Interview---

The next morning, Kerry woke up early and made sure to drive to the coffee shop with plenty of time to spare. At 7:50, he walked inside and sat in a chair in the back corner. He was the only patron inside. Five minutes later, he saw a silver Mercedes Benz pull up next to his run-down car. A woman with an hourglass figure stepped out of the car and made her way inside.

She looked at Kerry and gave a knowing smile. She walked up to the counter, placed an order and walked over to him. He stood up to greet her.

"Hi, Kerry. I am Chloe. Please, have a seat."

She was drop-dead gorgeous. She was easily several inches taller than him with large, round breasts and a perfect bubble butt. Her figure was on full display because of her tight blue dress that cut off just above the knees. She had long, curly black hair and her eyes were a crystalline green that seemingly shimmered in the light. Her lips were colored ruby red and the soft features of her face made her seem both gorgeous and approachable.

"I take it you had no problem finding this place."

"I did not. I don't live too far from here," he replied.

One of the women working behind the counter approached with two cups. She handed one to each of them.

"Thank you, dear. Now lock up," Chloe responded.

Suddenly, all of the workers exited the store with the last one locking the door behind her. The building was suddenly empty except for the two of them.

Kerry felt nervous but did his best not to react.

"Oh, don't worry. This conversation requires absolute privacy. My client owns this coffee shop and many others like it. This is to ensure our talk is completely private and uninterrupted," she said.

Kerry stayed quiet, waiting for her to continue.

"This dinner party has some very particular requirements that you may or may not be comfortable with. What I'm about to describe to you must remain a secret. You may not share it with anyone you know. Anyone at all. You will be asked to sign a non-disclosure agreement. In exchange for signing this, you will receive one thousand dollars today in cash. Whether or not you decide not to take the position, the money is yours. But should you break the agreement, my client is prepared to... well, let's just say that you should not think about breaking the NDA. Is all of this clear to you?"

"Yes," he replied softly.

Kerry could really use that cash even if he didn't take the job. He couldn't believe that he would walk out of here with a thousand in cash for just showing up!

Chloe pulled papers out of her bag and put them on the table. She then signaled to one of the workers to come inside.

"Read through this agreement then sign here, initial here and date here," she said.

The NDA wasn't long, but it was blunt. It made clear that discussing the arrangement with anyone or even just writing about it would make Kerry subject to a lawsuit for breach of contract and punitive damages in excess of one hundred thousand dollars!

Kerry hesitated for a moment but decided that keeping a secret was more than worth it for the cash he would receive. He signed and dated the document. Chloe signed and dated it as well and the employee that had come back inside stamped it, signed the paper as well and went to the back room. When she returned, she handed a copy of the document to Kerry and walked back outside.

"Ok, so now that all of that is done, here is your cash. This is yours to take, no matter what decision you make today. As for the dinner, here are the requirements. You will be required to dress and present yourself as a woman. You will wear a wig unless your hair is a suitable length, which yours is not. You will be required to wear makeup and your entire body is to be freshly shaved and smooth all over. And yes, that means every nook and cranny. You will adopt a feminine name of your choosing, but one that I will approve of ahead of time. You will work at a private dinner for my client and his guests. You will serve them food and drinks throughout the evening. The event will take place next Saturday between 8PM and 1AM. You are not expected to speak, but if you do, we ask that you use as feminine a voice as you can muster."

Kerry was stunned. He stared at Chloe as he processed all that she said.

"Do you have any questions so far?"

"Ummmm, no," he sheepishly replied.

"Then I will continue. You are not engaging in prostitution. You will not be required to have sex or perform any sex acts during the event. You will remain fully clothed at all times. If any of the men propositions you or touches you inappropriately, you are to notify me immediately and they will be dealt with poste haste. Should you need assistance with the attire, makeup or body preparation then you should come to the event location four hours early. My team will assist you with any and all of this. This is mandatory for your first time working with us and optional should you join us again in the future. Now, do you have any questions?"

"So, basically, I'm going to dress up as a woman and serve food and drinks for the evening?"

"That is basically correct."

"And there's no sex or sexual contact required of me?"

"Absolutely none."

"And I will be paid the additional four thousand that night?"

"No, you will be paid five thousand at the end of the night. In cash. The one thousand today is in exchange for signing the NDA."

"And what if I don't want to do it again? What if I do it this once and decide that is enough for me?"

"That's completely fine. The NDA, as you read, is a lifetime agreement. So long as you do not write or talk about the event or anyone involved with it, you can walk away as if nothing ever happened," she replied.

"When do you need to know if I want to do this?"

"You have exactly 24 hours to think about it and make your decision. I will text you tomorrow morning asking for your response. If you decide to join us, I will send you directions on Friday evening. Again, you will need to be at the facility at 4PM on Saturday since this is your first time. Do you have any other questions?"

"No. I'm good," he responded.

Chloe stood up and walked out of the coffee shop. The workers shuffled back in and began working again as if nothing had happened. Kerry looked around with a mental haze, unable to fully process what had just happened.

He eventually left the store, wandered home and tried to stay busy for the rest of the day. He couldn't stop thinking about the offer and the financial relief he would get for just an evening of dressing like a woman. It seemed like a small sacrifice for more money than he'd make in 3 months of work.

As the night wore on, he thought of how many times he had struck out this week looking for work or a simple job upgrade. He thought of the looming rent and other bills that had to be paid. While the thousand he received today was going to help for the short term, earning an additional five thousand could set him up for months and buy him the time he needed to figure things out.

He sat on the couch, thinking deeply as the TV mindlessly buzzed away in the background. He began to imagine what it would be like to dress like a woman. He imagined men sitting around, checking out his body as he glided across the room, handing them drinks and food. Kerry suddenly found himself getting unexpectedly aroused as he thought more about it.

His heart was pounding as he imagined the men checking out his ass as he walked by. The thought of one of those men grabbing his waist and feeling him up made his heart race. His cock was now rock hard as he daydreamed about what it might be like.

Kerry quickly opened his eyes in shock. He shook his head violently as if to shake something off of himself.

"What the fuck was that," he muttered to himself.

He got up, grabbed a bite to eat and eventually settled into bed for the evening. In just a few short hours he'd have to make up his mind.

---The First Time---

Like clockwork, Kerry's phone buzzed at exactly 8AM the next morning.

"What's your answer, Kerry? Will you be working with us Saturday?"

He quickly typed in his response and hit send: "Yes."

"Ok. Directions to follow Friday evening."

With that, he breathed a sigh of relief. He could get through one evening of dressing like a woman in exchange for financial stability. For now, though, he had to worry about getting to work and going through the normal grind. He got dressed and went to work as he had done for the past couple of years.

The rest of the week was as boring and normal as every other week. Work, come home and eat, play games or watch television and go to sleep. Rinse and repeat. Each day disappeared into the next until Friday had finally arrived.

By the time Kerry got home Friday evening, he had all but forgotten that he was going to get a text that night. When his phone buzzed and he looked at it, his heart leapt as he was quickly reminded of what he had in store for the weekend. The text from Chloe had directions on how to get to the facility followed by the message, "4PM. Do not be late."

Oh shit. This was really happening! Kerry's mind raced at the thought of what awaited him in under 24 hours. He was nervous but excited. He quickly convinced himself that the money was what he was excited about, but deep down he knew there was more to it. He pushed those thoughts down and focused on the financial windfall he'd be able to celebrate on Sunday.

"Just get through tomorrow night," he thought out loud.

Thankfully, the long day at work made getting to sleep a foregone conclusion.

Kerry went through some of his normal chores on Saturday before hopping into his car at 3PM to make the drive to the facility. When he made the last turn, he saw an enormous, gated estate. He pulled up to the intercom at the gate at 3:45. Before he could reach out to buzz it, a voice came through the speaker.

"Good, you are early. When the gate opens, take the third road on the right. Drive to the end of that road, take a left and go to the house at the very end of the road."

The giant, black gates began to slowly move inward. He drove as instructed and found himself at the designated house after a few minutes. Chloe was waiting at the door.

"Kerry, I'm glad you're early. This is Savannah. She will be assisting you tonight. Please follow her to your private quarters where you will get ready for the evening," she said.

Behind her was a pretty girl with long, blonde hair wearing khakis and a button up white shirt. She smiled and started walking into the house. Kerry followed behind her.

At the end of the hallway she opened the door and invited him in.

"Mr. Bowen, the bathroom is through that door. Please go ahead and take a shower. Use the soap that is on the shelf. It is a new bar. Use it to scrub yourself from head to toe. When you are done, let me know and I will come in to help you shave. Please do not be shy. I have seen it all before," Savannah robotically instructed him.

He smiled, nodded and proceeded to undress and take a shower. The soap smelled of lilacs and berries and made his skin feel cool and incredibly smooth. He scrubbed from head to toe as instructed and took his time enjoying the hot water rain down on him in the extraordinarily large shower. He cut off the water, wrapped himself in a towel and called for Savannah.

She stepped in, smiled and said, "Lose the towel."

He shyly tossed it aside. She looked him over and said, "Oh good. You're not particularly hairy. This shouldn't take too long."

She grabbed a razor and some cream and dislodged the shaving head from the wall and turned the water back on. She immediately began applying cream to his legs and started shaving. He could tell that she had done this before as she quickly shaved off the hairs, rinsing the blade periodically with the shower head.

She moved him around in the shower like a doll, shaving every inch of his legs. She turned him around and nonchalantly cupped his balls and began applying cream all over his genitals. He quickly became aroused and embarrassingly said, "I am so sorry."

"It's normal. Don't worry about it," she replied dryly.

She proceeded to shave his balls and shaft. She turned him around and muttered, "Wonderful. You have no body hair. This makes my job easier. Lift your arms, please."

He lifted them and she applied the cream and quickly shaved under his arms. In under 10 minutes she had managed to shave his entire body from the neck down. She reached over and squirted lotion into both of her hands and began applying it all over his body. She rubbed it in gently but quickly. The fragrance was strong and feminine. Kerry found himself fixated on it.

"Your face appears to be freshly shaved. I think we can avoid that for today," she said as she looked him over.

"Ummm, is there a reason I have to be shaved from head to toe?"

"You won't act feminine if you don't feel feminine. Shaving like this helps you get into the right mindset," she replied before adding, "Oh, and if you decide to join us again, we could begin working on laser hair removal. We have our own equipment on premises. Or, if you'd prefer, we could do waxing instead. Also, your hair is already somewhat grown out. I bet you could grow it out to an acceptable length in 8 or 9 months with the right diet," she said in an analytical voice.