The Family Pt. 01

"I... uh, I'm not sure," he began to reply.

"Oh, I know. You're not sure if you'll do this again. Blah blah blah. I've heard it before. I'm going to tell you what I have told everyone who has come before you: you'll be back and not for the reasons you're thinking."

"For now, let's get you into some panties and a bra and then we can work on your makeup," she added before he could respond.

She walked him over to a closet and pulled out some panties. She looked at him, opened a drawer and pulled out a pair of light pink, silk panties and handed them to him. He slid them on. The soft silk felt luxurious on his skin and he found himself getting unexpectedly aroused yet again.

Without even looking Savannah said, "Don't worry. Everyone gets hard the first time they put on these panties. You're not the first."

She opened another drawer and pulled out a matching bra. He awkwardly tried to put it on until she jumped in to assist him. She reached behind him and did the latches. Perfect fit. She then stuffed the bra with shapely pieces of rubber to make it look like he had breasts.

"The mirror is right over there," she said, pointing to the corner. She knew what he was about to ask before he could ask it.

Kerry walked over and looked at himself in the mirror. The silky smooth legs and body. The pink panties and bra. He didn't recognize himself. His hands began to rub up and down his body, feeling the fabric and the soft skin. His heart pounded frantically in his chest. He loved the feeling! He turned and looked at his ass in the mirror and smiled.

"I will say this, Mr. Bowen - you have an incredible ass. One of the best I've seen here," Savannah said in a matter-of-fact tone.

He smiled deeply at the compliment.

"Now, it's time for the makeup. This will take a little while since this is going to also serve as a tutorial for you. You can practice at home. I have a kit you can take home with you after tonight. You are always welcome to use my services here, but many of the girls decide they want to do it themselves after a while."

"How many girls are there?"

"Oh, I've lost count at this point. Several hundred? I don't know."

Kerry wanted to ask more questions, but Savannah's body language indicated that he'd probably get very few answers. He focused instead on the makeup tutorial he was about to receive.

For the next two hours, Savannah walked Kerry through the entire process. Starting with a facial cleanser and then a moisturizer, she moved on to a primer and color correction. She spent a good bit of time on applying a foundation and eye concealer. After adding contour and applying a bit of a rosy tone using highlighters, she moved on to the eyes.

She went through different eyeshadows and eyeliner, opting for soft shades so that Kerry's blue eyes would really pop. She thickened his already long eyelashes and moved on to the lips. She showed him how to use the lip liner and finally finished with a nice muted pink lipstick.

When the makeup was finally done, she went to the closet to find the perfect wig. She came back with two: one blonde, the other brunette. Kerry's hair was naturally dark, but he liked the idea of being a blonde.

"That one. Let's go blonde," he said, pointing at the curly blonde wig.

"Good choice."

Savannah showed him how to properly apply it. She put on a wig cap and applied glue to the front and waited for it to get tacky to the touch. She placed the wig on and used the makeup to blend it in naturally with his complexion.

"There. That looks perfect. Let me get Chloe so she can sign off on the work we've done," Savannah said as she walked out of the room.

Kerry couldn't take it anymore. He had not seen the final product yet. He stood up to walk to the mirror but before he got there the women came back in.

"Oh my. Savannah, you have outdone yourself. Of course, having someone so beautiful to work with never hurts," Chloe said brightly.

"Thank you," she replied proudly.

"So, have you chosen your name for the evening?"

Kerry had forgotten about that detail and felt caught off-guard.

"Um, I haven't. Do you have any ideas for me?"

"Let's see," Chloe started as she looked him over. After a brief pause she replied, "What about Madeline? Maddie for short?"

Something about the name felt... right. Kerry didn't know why, but he loved it.

"I like it. It feels... right somehow?"

"Ok, perfect. From now on you shall be known as Maddie. Savannah, get Maddie into a dress and bring her to my office. Thank you dear."

Chloe left the room quickly and Savannah went back to the closet and came back with a sparkling blue dress. She helped Maddie get into it and yet again, it was a perfect fit. She really did know what she was doing. She grabbed some matching pumps for her to try on.

Maddie slipped them on and awkwardly took a few steps, nearly falling over in the process.

"You'll get used to it. These aren't even that tall. You have an hour to walk around in them and practice. I suggest you use that time to do so," she said as she watched Maddie stumble around. She added, "So, are you ready to see the final product?"

"I think so," she replied.

Savannah walked her over to the mirror.

Maddie stood there in shock. What she saw in the full size mirror stunned her. Kerry was gone. In the reflection was a beautiful, sexy blonde woman. Her heart started pounding and her cock quickly stiffened and pushed out of the top of her panties. The outline of the erection showed clearly in the tight fabric of the dress.

"Yes, that's normal too. To be clear, that's going to happen a lot tonight. Don't be shy about it. Flaunt it. That's why you're here and doing this," Savannah said before adding, "And remember. You are Maddie now. You only respond to that name."

She grabbed Maddie's hand and twirled her around, looking over her entire body and face in the process.

"Oh Maddie. You are going to be the talk of the evening. You are simply luscious. Chloe has found yet another gem. Come with me."

The two of them walked out of the room and up the stairs to a large room on the second floor. Inside, Chloe sat at a desk with several boxes on it. There was a single chair in front of the desk that Chloe invited Maddie to sit in.

As she sat and the door behind them clicked closed, Chloe started, "Maddie, you look beautiful. Even more so than our algorithms predicted. The gentlemen tonight are going to be enthralled with you. However, they know the rules and as I mentioned before, there will be no physical contact. Should any of them break the rules, we will intervene immediately. Your comfort is my priority."

"Yes, ma'am."

"Your job is simple. Serve food and drinks as instructed. Should you choose to speak, you need to use as feminine a voice as you can. I'd like for you to try that now."

Maddie nervously raised the pitch of her voice and spoke softly, "How does this sound? Is it feminine enough?"

Chloe's expression soured slightly before she said, "That should be ok for now, but I think you could do much better with proper training and practice. For now, just minimize the speaking."

She continued, "You will receive your cash payment at the end of the night. In addition to the money, you will be gifted these boxes. Inside is an assortment of things. This box has an entire kit of makeup, the same ones Savannah used tonight. This box has an assortment of women's clothing and wigs. This box has various sex toys, anal plugs, lubricants and the like. This last box has a new laptop computer that is yours to keep. When you log in, you will find an application we've designed that will train you in applying makeup, training your voice and other odds and ends. This is all yours. Whether you choose to use it or not is up to you. I suspect you will."

Maddie didn't know how to respond, so she sat silently and smiled.

"Don't worry, dear, every girl is overwhelmed her first time here. It's normal. All of this will make far more sense in the coming weeks. Now, should you perform well this evening you will be invited back. These parties happen every weekend and the pay is the same each time. If we invite you back, you will be welcome to come as often or as little as you would like. Feel free to talk with the other girls working tonight, but remember your first priority is to take care of our guests. One last thing: you will see some of the girls tonight engaging in more... salacious behavior. As a reminder, you will not be doing that tonight and at no time will it be an expectation of you. These girls are doing so of their own free will. Now, do you have any questions?"

Her heart pounded as she contemplated all she heard. She thought to herself "just get through the night and get paid and get the hell out."

"Ah yes. Don't worry. Every girl thinks to themselves 'just get paid and get the hell out of here' their first time. That, dear, is also very normal. Just remember, I am here for you and if you need anything, you just find me and I will take care of you, ok?"

Maddie's head swam but she resolved herself that she could get through this evening.

"Yes ma'am."

With that, she was escorted out. She spent the next hour walking around to get used to the pumps. By the time Savannah arrived to retrieve her for the party, she felt comfortable enough in them to not look like a complete fool.

She was taken by a golf cart to the main house of the estate. It was an enormous mansion that seemed to have no end. The inside was expansive and awe inspiring. The ceilings seemed to touch the sky and the rounded stairs harkened back to movies about large, Southern estates. The walls glistened a perfect white; no imperfections could be found. Not a speck of dust or discoloration anywhere.

Savannah walked her into a massive ballroom with large, round tables spread around the room. Maddie looked around and saw many other girls just like her. She noticed several of them already sitting in the laps of some of the men at the tables. From what she could tell, there were at least 40 to 50 men at this event.

She looked to the right and saw a gorgeous girl in a white dress sitting in the lap of a handsome, middle-aged man. His hand was up her dress and clearly fondling her genitals. Her eyes were closed in pleasure. She looked to the left and saw another girl standing next to a man whose hand was feeling her ass as her large, erect cock pressed tightly against the front of her dress.

"Those are some of our more experienced girls. Don't worry. Everyone here knows you are off limits," Savannah said, knowing how nervous Maddie must be.

She escorted her to the bar in the corner of the room. It was being worked by several bartenders. Savannah introduced Maddie to one of the men.

"John, this is Maddie. As you can see, she is new and this is her first night with us."

"Nice to meet you, Maddie. Your job tonight is simple. You'll be taking various drinks to each of the tables as requested. Just come to me throughout the night and I'll hand you the drink and let you know the table number it goes to. That's it. Easy peasy."

She smiled and shook her head to acknowledge what he said.

"So, let's get started. Take this old fashioned to table 20. The gentleman in the white coat. Can't miss him."

Maddie grabbed the drink and took it to the table. She quietly handed the drink to the man, who looked up at her. His eyes opened wide and his mouth opened slightly.

"My god, you are absolutely gorgeous! Clinton, you have found another absolute beauty you devil," he yelled across the room. His deep Southern drawl was charming. He continued, "Please dear, do a turn-around for me so that I can see all of you."

She turned as requested. Half way through the turn the man shouted out, "Jesus christ that ass is perfection! My word, the gods crafted you by hand my dear. Simply delectable!"

The words drilled straight into her soul as she finished the turn-around. Her heart pounded and her cock hardened quickly in her panties. She shuffled a bit to let it spring out of the top of her panties. The man at the table smiled deeply as he watched her get hard right in front of him.

"Oh yes. The gods did craft you, alright. You, my dear, are simply perfect. Every inch of you. I do hope we'll see you back here in the future."

She smiled and returned to John at the bar. He looked at her, smiled and said, "Oh yes. The gentlemen here are going to adore you, Maddie. I have a feeling you'll be quite the hit. Take this cosmo to table 30, the gent with the beard."

As she walked towards table 30, she heard guest after guest commenting on her body as she passed them.

"Holy shit, her body is fucking perfect."

"Oh my god, I hope she comes back."

"Christ. How does Clinton find all of these gorgeous girls!"

"That... that is the perfect ass."

By the time she made it to table 30, her erection was rock hard. She felt like it was going to rip through the fabric of her dress.

She handed the drink to the man with the beard. He thanked her, took the glass but then reached up and grabbed her ass firmly. She gasped loudly and looked at him in shock.

"Oh god dammit, Gary. You're fucked now, you idiot," one of the men at the table sighed.

Within seconds, two extraordinarily large men showed up at the table and hoisted the bearded man from his seat. They were not gentle with him.

"Wait, wait. My mistake! I'm sorry, don't do this," he shouted as the men carried him away.

Chloe was there with them and said dryly as he was carried off, "Make sure he leaves the property immediately. He is not welcome back ever again. Use force if you must. Maddie, dear, are you ok?"

Maddie shook her head up and down. Chloe patted her back softly and whispered, "I'm sorry. That rarely ever happens. The last time was months ago. I assure you, it will not happen to you again, or I will murder them with my own two hands."

She was right. The party continued on and Maddie got into a bit of a groove. She enjoyed the eyes on her body. The comments. The compliments. The whistles. She felt electric as she glided through the room, grabbing the eyes of all the men there. Her rock hard cock stayed that way for nearly an hour straight as she bathed in the praise and adoration of the men around her.

After an hour or so, Chloe approached her and said, "Ok dear. You're doing wonderfully. All of the men here are asking me about you. Quite a few have asked that their drinks be delivered by you. Why don't you take a quick break, though. I don't want you to wear out before the night is over. Through those doors you'll find an area designated for the girls to grab a bite to eat or to get a drink. You'll find restrooms there as well. Take 10 to 20 minutes."

She welcomed the break and headed towards the doors. As she pushed them open, she saw a room at the end of the long hallway with a sign above it that said "Girls only."

What she saw in the hallway, however, truly caught her eye.

No more than 3 feet down the hall was a woman in a tight yellow dress, leaning with her back against the wall. She had an incredibly curvy figure with a large butt and very large breasts. At her feet was a man on his knees. He had her dress lifted up and he was giving her a blow job!

She paused and watched as his hands moved up and down her long shaft. He kissed the head as she cooed and moaned. He licked the shaft up and down, fondling her balls with his hand. The two of them didn't acknowledge or see Maddie as she walked by slowly. She stared at them the entire time.

Maddie was so turned on by what she just saw. She turned her head to continue down the hall but heard the feminine voice moan out, "Oh sweetie, I'm about to cum."

She turned and looked as the girl came all over the face of the man on the ground. Rope after rope of cum shot out as her body quivered in ecstasy. The man smiled as the cum splashed all over his face and into his open mouth. The girl leaned down and kissed him deeply when she finished. She then looked over at Maddie and smiled and winked. The man wiped his face with the handkerchief in his pocket and nonchalantly walked back into the ballroom. The girl in the yellow dress walked towards Maddie.

"Hi beautiful, I'm Marilyn. You are?"

"Oh, I'm Maddie."

"So, you're clearly new here. You are gorgeous, by the way. I hope you enjoyed the show," she said, smiling deeply.

Maddie blushed and Marilyn laughed in response.

"Come with me, honey. I'll give you the rundown."

Marilyn grabbed her hand and escorted her into the room at the end of the hall.

The room was large and had couches and chairs around all the walls. In the middle was a long table with drinks and snacks of all sorts. Marilyn grabbed a diet soda, cracked it open and took a long swig. Maddie grabbed a water bottle and opened it as she was escorted to an empty couch in the corner of the room.

"So, I'll be brief since we both need to get back to the floor soon. Yes, these tits are mine. Implants of course, but they're amazing. Completely paid for by the family. If you want something less permanent, they can order you some incredibly realistic breast forms custom matched to your skin tone. But that's for the future. Chloe will spell a lot of this out for you next time."

"I'm not sure," Maddie started to say before she was cut off.

"Oh honey, I can tell - you're coming back. Next week, in fact. I'd bet my new Porsche on it."

"I don't know if this is for me. I'm straight," Maddie began responding before Marilyn cut her off again.

"Sweetie, you are not straight. If you were, you would not be here right now. At minimum you are bi curious, but don't think too much about it. You'll figure out your sexuality soon enough. What a fun ride you have ahead of you!"

Maddie decided to sit quietly and listen. Deep down in her subconscious she knew what Marilyn said was accurate.

"Do you want to know the biggest lie they tell here? It's that we are here to serve. No, sweetie. We are not. We are here to be served. These men worship us. They desire us. They will spend ridiculous amounts of money to make us happy. We have all of the control. Our queen mother Chloe, has set us up for life. We are all goddesses here. You just don't realize it yet. Between this job and my Onlyfans, I am now making between 20 to 50 thousand per month. Believe me when I tell you that your life has been permanently changed. Don't try to process it all at once. Just trust me. You'll find out soon enough."

Maddie felt overwhelmed. Somehow she knew that she was just told the gut level truth and that others were seeing in her something she did not yet see. She finished her water bottle and got up to head back to the main ballroom. Marilyn stood with her.

"Oh, and sweetie, do enjoy the boxes they gave you tonight. Those are just the beginning. Especially the box of toys. I've been doing this for five years and I still use them to this day. Mmmmm mmmm."

Marilyn grabbed her hand and pulled her close. She gave her a soft, prolonged kiss on the lips and walked off towards the ballroom.

Maddie's head was swimming, but she vowed to push through it and finish the evening. Right now the priority was finishing the night and getting the cash. Any other considerations were for the future.

She made her way back to the ballroom and immediately started serving drinks again. The compliments and looks continued all night and her arousal never let up, even as she got into a groove. She even started playing it up more, winking and blowing kisses at the men in the room. Her earlier protestations and doubts had been put to bed. She was alive. Sexual electricity ripped through her body with each man she turned on.

She was the talk of the night. Every man in the room wanted her to come close. Nearly all of them would get up from their tables at some point to move closer to her. Several of them showered her with compliments and promises to take care of her if she'd come back. A few of the men told her she'd never have to work again.