Chapter 6

The next day, they received the schedule for their second film, and reality set back in. But with each day that passed, their confidence grew. Madeline’s scenes with Cody grew more intense, and she found that she enjoyed the thrill of performing. Timmy and Holly’s contributions were invaluable, their creativity and dedication earning them respect within the company.

Their relationship with Marcus grew more professional, their interactions peppered with a hint of familiarity. He had become a mentor of sorts, guiding them through the shark-infested waters of the adult entertainment industry. Madeline found herself drawn to his experience and authority, seeking his advice on how to navigate their new lives. Despite his initial skepticism, he had come to respect their unconventional bond, recognizing the fierce loyalty and love that fueled their success.

The siblings continued to support Madeline in her scenes, their roles evolving as they grew more comfortable with the explicit nature of their work. Timmy’s camera skills had improved dramatically, capturing the raw emotion and passion that set their content apart from the rest. Holly’s flair for set design and styling had become a signature of their brand, creating a sophisticated yet steamy atmosphere that left viewers craving more.

The day they received the schedule for the third film, Madeline felt a peculiar mix of excitement and trepidation. Anal was a new frontier for her, a challenge she hadn’t anticipated when she first agreed to this venture. She took a deep breath and read the script, her eyes widening at the explicit content. It was more intense than she had imagined, but she knew that pushing boundaries was part of their appeal.

Holly, ever the meticulous planner, immediately sprang into action. She studied the script with a focus that made Madeline’s head spin. “Okay, Mom,” she said, her eyes gleaming with determination, “we need to prep you for this. It’s going to be a big scene, and we want it to be perfect.”

Timmy, his own excitement palpable, offered his services. “I’ll help,” he said, his voice a little too eager. “I know I don’t have Cody’s size, but I can get you ready.” Madeline couldn’t help but feel a warmth spread through her at her son’s willingness to help, his small cock already tenting his pants.

Holly nodded thoughtfully. “It’s a good idea, Mom. We need to make sure you’re comfortable with it, especially if you’re going to do it on camera.” Madeline felt a thrill at the thought of Timmy being the one to prep her, a twisted sort of role reversal that she found incredibly erotic.

Timmy’s eyes widened with excitement as he stepped forward, his smaller cock bobbing in anticipation. “I can help you get used to it,” he said, his voice filled with both eagerness and concern. “It’ll make it easier for you when the time comes.” Madeline felt a rush of love for her son, for his willingness to do whatever it took to ensure her success.

Holly watched the exchange with a knowing smile, her eyes dark with desire. “It’s a big step, but we’re all in this together,” she said, her voice soothing. “And if anyone’s going to take your virginity in that way, it should be someone who loves you.”

Madeline took a deep breath, her heart racing. “Okay,” she murmured, looking at Timmy. “If it’s what you want, I trust you.” Timmy’s face flushed with excitement, his hands shaking slightly as he took his mother’s hand. “Thank you,” he whispered, his voice hoarse.

They retreated to Madeline’s bedroom, the room that had become a stage for their most intimate moments. Holly pulled out a bottle of lube and a set of anal plugs from the drawer, her movements efficient and professional. Madeline lay down on the bed, her legs spread open, her heart thumping in her chest. Timmy’s gaze was filled with love and concern as he knelt between her legs.

“Spread them for me, Timmy,” Holly instructed, her voice low and steady. Timmy’s cheeks flushed, but he did as he was told, his hands gently gripping Madeline’s plump ass cheeks and pulling them apart. Madeline felt a flutter of nerves as she watched her children, their expressions a mix of excitement and trepidation.

Holly coated her fingers in the cool, slippery lube before bringing them to Madeline’s anus. She traced light circles around the tight entrance, watching her mother’s face for any signs of discomfort. Madeline took a deep breath, her body tensing slightly as the coolness met her skin. Holly’s touch was gentle, almost tender, as she worked to relax the muscles, her eyes never leaving Madeline’s.

“Spread them wider, Timmy,” Holly murmured, her voice filled with a seductive confidence. Timmy’s grip tightened, his own excitement palpable as he followed his sister’s instructions. Madeline’s pussy was already wet from their earlier encounter, and she felt a strange sense of anticipation building as Holly’s lubed finger hovered above her.

With a gentle push, Holly’s finger slid into Madeline’s ass, her eyes locked onto Madeline’s face to gauge her reaction. Madeline’s eyes widened with the sensation, the slight burn quickly giving way to a surprising fullness. Timmy watched, his own cock now fully erect, as his sister worked the plug into their mother. His hand reached for his own cock, stroking it lightly as he took in the intimate scene before him.