Deedee's Date

Trent’s eyes popped open as he heard the woman’s voice for the first time in years. “Deedee, I want you to get ready and meet me at Vintano’s Wine bar. I need you for a date.” The crisp voice had a self assured tone to it. It was easy to tell that this woman was used to giving orders and having them followed.

“Miss Jameson, I, I understand.” Trent’s eyes locked onto Deedee’s. The look of fear on his father’s face was something he hadn’t seen since the morning when he had walked in and seen her dressed up for the first time. Deedee licked her plump lips as she tried to think of what to say. “But…”

Chloe’s voice cut through whatever Deedee had been about to say like a serrated knife. “But what? Surely the little project I gave you the weekend off could use some instruction. I’ll tell you what, bring her along and I’ll watch over her while you entertain our guest.”

Even without being in the same room as the woman, Deedee’s eyes hit the floor as she realized that she had clearly overstepped by speaking out against the order. “Of course Miss Jameson. What time would you like us there?”

“The reservation is set for one. Wear that purple dress, and those new Jimmy Choo heels. We are going for more of a sophisticated woman, not the slut look you normally prefer. Feel free to dress your toy up however you want, but make sure she has all the appropriate accessories.” With that last demand the line cut out as the person on the other end hung up.

Deedee’s eyes squeezed shut in embarrassment and frustration. She had wanted to keep Tiffany and Chloe apart for as long as possible. Hearing herself as she whimpered and groveled to Miss Jameson while she knew that Tiffany was standing in front of her dampened any part of happiness that the morning had created. She could feel the frustration at Chloe grow as well. She had trusted the woman when Chloe had told her she would have the weekend to spend with Tiffany. She knew she would have known better.

Handing the phone back to Trent, Deedee turned back to her shower. Her voice was soft as it trailed over her shoulder. “Go back to your television. I’m going to take a long shower then we can start getting ready. I’ll need to coach you on how to interact with Miss Jameson. Otherwise we will both be in trouble.” The sound of the hot shower cut off any further words as Deedee dove under the stream and let it envelop her completely.

Trent’s eyes were locked on Deedee’s back as he stood there frozen in the bathroom. The sudden change in his parent was something he didn’t think he would ever grow used to. The confident and vibrant milf that had been his workout coach for the morning had been replaced in the space of moments by a simpering sycophant with just the sound of a woman’s voice. He wondered briefly if that was the type of person Deedee wanted him to be.

After a moment of staring at Deedee in surprise, Trent flicked his gaze down to just catch the screen on the phone going dark. A deep breath was the only sign of frustration he allowed himself as he saw a chance at his freedom disappear. A small bit of hope blossomed there though, it was clear that Deedee hadn’t thought that him having access to the phone was anything to be concerned with. That meant that there was always the chance he could gain access and delete the videos and images she had shown him.

Stepping back into the bedroom, Trent tried to access the phone only to realize that Deedee had it locked via her facial image. Shrugging he collapsed onto the bed and tossed the useless phone to the side as he flicked on the television and tried to lose himself in some random show.

Back in the bathroom, Deedee went about her typical Sunday shower. She had been amazed to learn what an everything shower was when she started her feminine journey. Her ex wife had never cared as much about her appearance as Deedee did. There was a brief moment where she thought to correct herself and blame her desire to look good on Miss Jameson’s teachings, but that thought quickly fell apart. Deedee liked looking good. She liked being stared at and admired by people. She loved the way she felt when she stood in front of a mirror. It had nothing to do with Chloe Jameson, other than the fact that Miss Jameson had **** her to learn it about herself.

Shaking her head, the long wet tresses flopped around her head as she shoved those thoughts from her mind. Deedee instead turned her thoughts to the potential date that she could be seeing today. Even though she had been distracted for most of Thursday, she would have remembered if there had been a business meeting for Miss Jameson this weekend. She also couldn’t think of any potential meetings that she would have been requested to join that were coming up either. It seemed to her that this meeting was likely something that Miss Jameson cooked up to benefit herself or in an effort to exert control over Tiffany.

That last thought of Chloe having any control over Tiffany sent a shiver of anger through Deedee. She knew just how hypocritical it was, but there was no way she was going to allow another person to treat her child like she was being treated now. She could feel the anger at that thought settling in the back of her mind like a steel pole that slid against her spine. Chloe may have control over her, but Deedee would not let the woman get her hooks into Tiffany.

Stepping out of the long and involved shower, Deedee dried herself off and began to apply lotion to her smooth and lithe body. Trent looked over as he heard the shower cut off and couldn’t help but stare as Deedee began the sensual process of slathering herself in moisturizer. The way her long nailed hands rubbed along her long legs, taut stomach, large ass, and even her large breasts kept his attention locked onto her. Deedee caught the attention out of the corner of her eye and decided to enjoy the attention instead of pushing any training with Tiffany.

Once that process was complete, she slipped into a silky robe and headed over to lay in her bed as well. Laying back with her head against the pillow she allowed herself to zone out to the sound of the television. Trent laid there uncomfortably for the next few hours. He wanted to ask questions about what was going to happen or what the correct accessories were, but at the same time he was afraid of what the answers might be. Indecision kept him quiet while Deedee simply lay there quietly.

After a few hours of quietly watching random television shows, Deedee sighed and sat up. “Turn it off dear. We need to start getting ready.” Deedee spent the next hour and a half getting both of their makeup and hair done just right. Once again, she seemed completely focused on the task, not saying anything to Trent outside of the instructions to make her job easier. Trent’s look was done before Deedee completed her own. The soft nude lip and smoky eye look set off his eyes perfectly, while Deedee gathered his hair up in a messy bun to show off his slender and elegant neck. For herself, Deedee built up a more dramatic night time look that featured dark smokey eyes and equally dark lips. Her own hair hung free in long natural looking waves.

Trent froze when he saw Deedee open up a drawer and pull out the plug he had been wearing the previous day, as well as a second slightly larger one. Turning to him, she asked him a question for the first time since before the phone call. “Do you need help or can you handle it yourself?” It was odd that he would think of a request for him to shove an anal plug in himself as caring, but there was a softness to Deedee’s request that showed she wasn’t out to harm him.

“Like, I guess I can handle it.” Trent didn’t want to wear the horrific plug, but he didn’t see a way around it. Certainly, he had no desire for the feelings from the last few times Deedee had inserted it into him. At Deedee’s nod, she placed a bottle of oil based lube on the counter and went about the process of lubing up and inserting her own plug. Trent watched as Deedee swiftly slipped her anal toy in, only starting as she turned towards him with a raised eyebrow. Shaking himself, he tried to copy her actions.

The process took longer as he tried to find the right way to shove it inside of himself. His mind fought with his body as he knew he needed to insert it, but there was a bit of a block. Watching him struggle with the insertion, Deedee stepped up and spoke softly. “Just relax baby. This is perfectly normal. Lots of people use toys like this. Just open yourself up and slowly work it in.” Taking a deep breath, Trent followed her instructions. While it certainly wasn’t easy, he finally got the bulbous end to slip into place. A shudder and bite of his lipstick covered bottom lip was the only reaction he allowed himself to the pleasurable feelings emanating from inside of himself.

Moving into the closet, Deedee began to lay out both of their outfits. For Tiffany, she selected a white lacy thong and matching halter neck bralette. Over that went a short yet elegant white skater dress that left his back open. As she gave Tiffany time to slip into those, Deedee began her own longer and more involved process. The black strapless corset pulled in her shape even more than normal. Pulling a pair of black lace top stockings up, she hooked them to the garters before the black matching thong slid into place. Deedee’s dress was a purple off the shoulder midi pencil dress that hugged her snatched figure tightly and showed off all of the hard work she had put into her body.

Trent was surprised at the height of the heels that Deedee then clasped around her ankles. The 100mm black ankle strap heels were the lowest he had seen her wear. While she picked out a pair of white 120mm So Kates for him to slip into. A pair of clutch purses, white for him and black for her completed their outfits. The pair of perfectly dressed feminine creatures strutted from the house to Deedee’s car with more than enough time to arrive at the restaurant.

A few minutes into the drive, Deedee realized that she had been zoned out for most of the preparation process. Turning, she looked over at Tiffany and saw him fidgeting nervously. Deedee realized that she had failed to prepare him for what was about to happen. Unsure of how to even start describing what was about to happen, she took a deep breath. Watching the scenery pass by she realized she had less and less time the longer she put it off. “Tiffany dear, this is going to be a strange afternoon. I’m sorry you have to see this, but it was bound to happen sooner or later.”

Trent looked over at Deedee questioningly. “Like, what was bound to happen? I don’t understand this. Why does she get to just call you up and tell you who to date?”

Deedee sighed. “You aren’t the only one being **** to do things they don’t choose to, honey. Miss Jameson does this every once in a while. Either for a client, friend, or sometimes just for fun. I will be escorting a man, or even a group of men.” Swallowing, she turned to watch his face as he took in the news that she would be prostituting herself at the orders of another person.

Trent was stunned. He had known all along that Deedee was under Miss Jameson’s control, but it was a different story to see that control exercised with so little effort. A different thought came up in Trent’s mind, but he was able to keep himself from blurting out the obvious question. Deedee saw multiple expressions flash across Tiffany’s face as she watched while they stopped at a red light. Finally, Tiffany spoke up. “Like, why am I here?”

Deedee nodded and pulled the car across the intersection after the light turned green. “You are here because Miss Jameson wants to test me. She will either try to use you to gain more control over me, or simply try to gain control over you. I will do everything I can to stop either from happening.”

Trent went quiet as he contemplated the mess that the pair of them seemed to be in. He desperately wanted to ask Deedee how what was being done to her was any different than what she was doing to him, but he could tell that now was the wrong time to dive into that messy question. Deedee’s eyes glanced over to Tiffany’s face periodically as she drove the rest of the way in silence. There was more she wanted to say, but she still wasn’t sure how to explain it all to him. Or even if he cared to hear it.

Pulling into the parking lot of the wine bar made the questions in both of their minds moot. Stepping out of the car, Deedee waited for Tiffany to join her. Taking a deep breath, Deedee fixed a bright smile onto her face and looked down at the younger blonde. “Always smile. Only address Miss Jameson as Miss Jameson. If she gives you an order, try to follow it. And most importantly, don’t get involved if you can help it. The less parts you play, the less involved you will be.”

Turning, she held out her hand for Tiffany. The pair’s long nailed fingers slipped together and with a quick squeeze of Tiffany’s hand, Deedee led them into the restaurant.