The Family Pt. 02

The sunlight slowly crawled into bed with Kerry. It was warm and comforting as its gentle lips softly whispered that it was time to wake up. Kerry's eyes opened slowly. As the fog began to lift, the vivid memories of the night before trickled into his mind. His naked, smooth body tingled all over as he thought about the men who stared at his feminized body the night before. The cat calls. The compliments. The slack-jawed stares. His cock quickly stiffened as he re-lived those moments.

His fingers lightly brushed over his rock hard cock and up and down his smooth body. He laid there enjoying the gentle sensation as the memories of the night before replayed with intense clarity.

Kerry had never thought much about his sexuality before now. His life had been too chaotic to think about anything other than survival. He wasn't entirely sure what last night meant for him. Was he gay? Bisexual? Could he be trans? He wasn't sure, but he did sense that this new path was one he wanted to head down. Those answers would undoubtedly come in time.

On top of it all, the name Maddie had already wedged itself into his identity. In just one night, he had gone from a financially struggling, single guy who could barely pay his bills to an exotic woman desired by men - and with plenty of cash in hand. That new identity felt ... perfect. Just the thought of being called Maddie by those men was making him incredibly horny.

He decided he was done with normalcy for now. He called his boss and quit his job and spent the morning laying in bed, wearing only a pair of pink panties that were included with the various gifts from the night before. He went through some of the videos on the laptop, including a few focused on the various sex toys he had been gifted. The thought of some playful experimentation was intensely arousing.

While perusing through the various videos, the phone rang. It was Chloe.

"Hi Chloe!"

"Oh my, good morning, Maddie. You have a good bit of energy this morning. How is my beautiful new girl doing after her first event?"

Maddie came alive and responded, "I'm amazing! I cannot wait for Saturday to get here. I'm going through the gifts and videos and I have so many things I want to try this week. Thank you so much for having me and for the gifts and for ... well, everything."

"Sweetie, I also cannot wait to see you here again. We have many things to discuss, so please come early on Saturday so that we can chat before the evening gets started, ok?"

'Yes, ma'am. I will be there," Maddie replied.

"Excellent. Have a good week and call me if you need anything at all."

With that, Maddie's day officially started. After going through more of the videos, she decided to spend some time working on her own makeup application. The videos were extensive so she had to take the laptop and set it next to the mirror in the bathroom while she practiced. She now understood why women had makeup tables!

As expected, the first several attempts yielded some interesting and hilarious results. After a couple of hours of practicing she decided to set it aside for now. She felt confident she'd get better over time. Her mind, however, was focused on other things.

She opened the box with the fancy calligraphy label that read "Toys." Her eyes opened wide as she saw the large assortment of butt plugs, vibrators, dildos and a large box at the bottom that had the brand name "Hismith" adorning it. She emptied the box, already knowing what most of the items were, having watched the instructional videos earlier.

Her eyes locked onto one particular toy, though. She opened one of the simple black boxes at the bottom of the treasure chest and inside was the most realistic dildo she had ever seen. It was long and thick and the skin and veins looked and felt real. Even the scrotum and balls were convincingly real! The card in the box conveyed that it was a "Real Cock 2."

As she held it in her hands her mouth began to water. Her fingers instinctively caressed the tip as she stroked the shaft softly. She lifted the realistic dildo towards her lips and her tongue stuck out and licked over the soft head. Her mouth made an "O" shape as the dildo entered her mouth. She instinctively kept her teeth away as her lips suctioned onto the shaft as her tongue worked over the convincing flesh.

Maddie's cock was rock hard and began to leak precum into her panties. She moaned as she moved the realistic cock in and out of her mouth. She had never done anything like this before, but this felt right. It felt ... perfect.

As she took the toy out of her mouth, she realized she now had an urge to try the real thing. She was stunned at this sudden realization, but her stiff, throbbing cock was proof that this desire was real and profound.

Her attention now shifted to the butt plugs, the other dildos and the mysterious Hismith device. She opened the box and unzipped the enclosed carrying case to see what mystery was inside. The tubular object was too big to be used as a dildo itself. A quick perusal through the small instruction manual made everything clear: it was a sex machine! With a suction cup that could hold to any surface, this device would do all of the thrusting for you.

She knew she wasn't quite ready for this device, but the idea of it intrigued her. She wasn't even sure if anal was something she would enjoy. The thought of it was a little intimidating, so she decided to take her time in figuring all of this out.

Maddie spent the week exploring her femininity and awakened sexuality. She loved the feeling of the butt plugs inside of her during the day. She had also taken to fingering herself in the shower, something she found she enjoyed a lot. She also kept her body shaved and smooth and wore only women's clothing all week. On the rare occasions she went out, she did revert to boy clothes. When she'd get home, she would tear them off as they no longer felt comfortable to her.

When she received phone calls during the week asking for Kerry, she winced at hearing that name. As the week progressed, her old life seemed like a distant memory. This new identity was all that mattered.

By the time Saturday rolled around, she was ready. She woke up energetic and eager to dive deeper into this awakening. She made her way to the estate early to spend some time with Chloe.

*****The Rings*****

Chloe's eyes got big when Madeline walked into her office. Her jaw slacked just a little bit in disbelief as she said, "My goodness, Madeline. It seems someone has made some progress on getting themselves comfortable with makeup and ... well, all of it! You look stunning!"

Blushing hard, Maddie responded, "Thank you. I spent all week going through the gifts and videos you gave me. I've even begun the voice training, though I think it will still take some getting used to."

"Well, dear, it's far better than last week but that's not saying much," Chloe responded with a wry smile and a gentle laugh. "Come here, let me take a good look at you."

Chloe held her hand and spun her around, looking up and down every inch of her body.

"My, my. You are already getting the hang of this. I had a feeling you'd be a natural and you have not disappointed! So, dear, let's sit down and talk more about what we do here and what is now available to you."

The two of them sat and Chloe began, "As you've now seen, the events we hold weekly are ... unique. We attract a certain clientele that pay us well to present them with the most beautiful crossdressers, femboys and trans women. How you identify doesn't matter much to us. You are presenting an alluring feminine energy that they find highly desirable. That said, you undoubtedly saw some of the extracurricular activities that took place."

Maddie smiled approvingly and Chloe took notice, adding, "I can see that you found that aspect intriguing! Well my dear, here's the reality: you are not required to do anything you are not comfortable with. If you want to maintain a hands-off approach for your entire time here, you are welcome to do so. However, if you want to open yourself up to additional experiences, we have a system that signals to our clients your level of participation. Along with opening yourself up more, there is a subjective financial incentive paid directly by our clients, but do not let that dictate your decision. Please, please only engage with what you are fully comfortable with."

"I understand," Maddie replied.

Chloe turned around briefly to grab a fancy, mahogany box which she put on the table in front of Maddie. She opened it and revealed a set of rings with various colored stones.

"These rings indicate what you're willing to engage in to our clientele. No ring indicates hands off, as you've already seen. The yellow ring is the first step. With this ring on, the men can feel you up, including stroking your cock and grabbing your ass. No penetration is allowed, however. Many of our girls never move past this ring and that is perfectly fine. The green ring indicates your willingness to engage in and receive oral satisfaction, all the way to completion."

Maddie's body began to warm and her cock started to harden as Chloe spoke. She tried not to let on, but her employer saw right through it.

"I can see that the idea intrigues you! As I noted, do not feel any pressure whatsoever to wear any of these rings. And if anyone does pressure you, let me know immediately and they will be dealt with. The next step is the blue ring. This ring indicates that you are open to anal penetration to completion, with protection of course. To be clear, all of our clientele are regularly tested to be disease free, but we recommend protection and engaging in anal sex without protection is technically against our policies. The purple ring indicates that you're willing to be the dominant figure in anal penetration, same caveats apply as with blue. Finally, the red ring is an indication that you are open to all sexual exploration and the discussion of specific kinks. Now, do you have any questions for me?"

"So, if I decide to wear the yellow ring tonight, can the men start touching me and stroking my cock at any time during the evening?"

Chloe responded, "Yes, dear. Now, if you find that you're getting more attention than you care to get or if they wear you out, you can take the ring off. Most of the men are respectful of the fact that everyone has physical limitations. For many of them, simply caressing your ass or feeling you up is all they want. A few of them do like to get our girls off, but that is not the norm."

"If they do, do I have to clean up after myself?"

Chloe laughed and replied, "No, sweetie. There are others working tonight who will take care of that."

Maddie adjusted herself in her seat. Chloe asked, "Are you thinking of wearing a ring tonight?"

Maddie smiled and excitedly responded, "Oh yes. I want to wear the yellow one to start."

"You're already getting excited, aren't you dear," Chloe asked seductively with a single eyebrow raised.

Maddie blushed and responded, "Yes. I don't know why, but the thought of it is so exciting."

"Well dear, no pressure, but I would bet you'll want to try out the other rings in the near future. Though, if you think you're ready for blue, purple or red, please see me first. I prefer to personally ensure my girls are truly prepared for what's ahead of them," Chloe added in the same seductive tone.

The two of them stood up and Chloe noticed the bulge poorly hidden behind Maddie's dress. She walked around the desk and stood next to her, putting her hand under the skirt and softly grabbing the bare, hard cock underneath.

Maddie gasped and her stiff, smooth girl cock twitched with delight. Chloe's hand gently caressed the swollen head and moved up and down the shaft. Her face was next to Maddie. Their breaths intermingled. Maddie could feel the precum begin leaking out of her. Chloe's finger lopped it all up.

She lifted the finger to Maddie's lips and as she pressed the precum to her lips, her own lips moved forward to share in the taste. The short, soft kiss was sweet and wet. That moment lasted two lifetimes for Maddie, though. She had never been more aroused than in that moment.

Chloe took a step back and simply said, "Oh Maddie. You are going to absolutely love it here my girl. And I am going to absolutely love having you here. Go on, now. Get ready for tonight. Come see me after the evening is done. I have more to share with you."

With that, Chloe stepped back behind the desk and Maddie made her way out with the box of rings in her hands. While she knew she'd only be starting with the yellow ring tonight, the promise of the other colors made her heart pound with excitement.

*****Yellow*****

After spending a good bit of time with Savannah to get ready for the evening, Maddie rushed to the main building to be there at the start. She was wearing a yellow dress, with a skirt that was intentionally short in the front, the bottom just above knee high. Her natural curves were emphasized by this dress, including her perfectly round bubble butt.

As soon as she walked into the main hall, she demanded the attention of every man there. She quickly made her way to John at the bar to see what orders she could take. He handed her an old-fashioned and pointed to the gentleman that ordered it. As soon as she started walking, she heard the men talking around her.

"She's already wearing a ring! I cannot wait to see how this goes."

"I will absolutely be checking her out tonight."

"One week and she's already into it. She may be the perfect woman!"

Maddie's heart raced and as she reached the destination table, her girl cock was already growing. The man at the table was in his early forties but was quite handsome with a salt and pepper beard and a strong, broad physique. He looked Maddie up and down and reached over to pull her close.

Maddie smiled as his hand cupped her ass and squeezed.

"Such an incredible ass, dear, " he said with a southern drawl.

He sat Maddie down on his lap and his free hand quickly moved under her dress and pulled her skimpy, yellow panties to the side. Her smooth, hairless cock began to quickly stiffen as his hand gently fondled the flesh. Maddie's eyes closed as he began to slowly stroke her hardening flesh.

She was just one drink in and was already getting a hand job!

After a moment, the man stopped and gently placed her panties back into place. Maddie stood up and asked him, "I'm sorry. Did I do something wrong?"

"Oh no, sweetheart. You are perfect. I'm just making sure you last the evening. You and I will have many moments together down the road. I can see it. You keep doing what you need to and I will be admiring you from afar."

Maddie took a breath and smiled and walked back to the bar. John greeted her and asked, "So, yellow tonight, huh? For a lot of the men, it's their favorite color. You gonna be ok?"

Maddie smiled and confidently responded, "Oh, I absolutely will. I'm going to be fantastic!"

John laughed and handed her another drink for a table on the opposite side of the room. She took it gleefully and quickly made her way across the room. Along the way, several of the men briefly stopped her to feel her up, which she gladly obliged.

By the time she reached the table at the end of the room, her erection was stiff and lifting her skirt up comically. As she approached the table, a man in all black signaled the drink was for him.

He was younger with short cut blonde hair and a striking physical presence. Maddie handed him the drink and he had her sit on his lap. This time, there would be no teasing. He immediately started stroking her rock hard girl cock and whispering into her ear.

"Do you like the way daddy is stroking your stiff clitty?"

She moaned approvingly as his hands moved gently but firmly up and down her shaft.

"Yes, daddy. Stroke my girl cock," she moaned.

His fingers gently caressed the swollen head, sending jolts of pleasure up her spine. Her nipples got intensely hard and sensitive. Her heartbeat was racing as this handsome bear of a man stroked her flesh softly.

"Daddy wants you to cum for me. Are you ready to cum for Daddy?"

"Oh yes, daddy. Mmmmmm, I'm ready," she cooed.

She was ready. Her body couldn't take it. She clinched up as the waves of pleasure surged through her. She suddenly shot her cum violently into the air. Rope after rope of her thick, white cum shot out, with some landing on her dress and some on the table. She collapsed into the arms of the man, who let go of her cock, and brought some of the cum on his fingers up to her lips. Without hesitation, she licked it all up.

"Good girl. Good, good girl," he said.

The euphoria was intense. She had never experienced anything like that before. When she opened her eyes, she could see the other men at the table staring at her and smiling. Several nodded approvingly. Before she could even stand up, a girl in a skimpy maid outfit had come over to clean up.

She stood up, turned around and said "Thank you daddy," before making her way back to John.

"That was quite the show, Madeline! Are you sure you're ready to take another drink? You can take a break if you'd like," he said as she approached.

"Actually, I think I might do that. I'm going to head to the back for 5 minutes. I'll be back shortly," she responded.

As she made her way to the back area for a break, she saw a familiar face.

"Hi gorgeous! I'm so happy to see you back," Marilyn said as she approached and hugged Maddie.

"I'm glad I'm back. I think I'm really going to like it here," she responded.

"Oh sweetie. I just watched the show you gave. Those men are into you. The way you just melted into the arms of that man and the way your body moved when you came - you had them hypnotized. Hell, I couldn't look away! But I need you to excuse me. I'm wanted in room five."

The two of them walked into the hallway and as Marilyn approached one of the doors to the side room, she turned back to Maddie and said, "Do you want to join me? You can just watch. Maybe get some ideas. I think he'd like it, actually."

Without thinking, Maddie quickly replied, "Sure!"

As they walked into the room, a slightly older man was sitting on the edge of the bed, already completely undressed. He was in good shape and when the ladies walked in, he spread his legs and said, "I did as you asked my queen. I'm cleanly shaved and completely clean."

Marilyn walked up to him, pushed him hard in the chest so that he was laying on the bed. She gently examined his cock, which was now rapidly growing. After a few seconds, a thick, long cock was under her control.

"Someone is excited about our little adventure. I brought a friend. I hope you don't mind," she said.

"Not at all. She's gorgeous my queen, but she's wearing yellow so I'm guessing she's just going to watch?"

"Yes, for now."

Marilyn pulled the front of her dress up and flung out her thick, hard cock. She took her rigid flesh and pressed it up against the cock of the man on the bed. She slowly started stroking them together.

Maddie watched intently, as the gorgeous, feminine figure took control. Her heart was pounding fiercely inside of her chest.

"Maddie, dear, would you mind unzipping my dress?"

She walked behind Marilyn and pulled the zipper down. Marily stepped back and let the long, blue dress drop to the ground. Her long, hard cock was curved upward and the tip glistened as precum had begun to leak out of her. Her skimpy white bra barely held in her large, round breasts.

"Would you also mind getting my bra, sweetie?"

Maddie unclipped it in the back and Marilyn's large, round breasts bounced forward and out.

Marilyn moved closely to the man and asked him, "You're absolutely sure you're clean?"

"Yes, my queen. I'm positive."