Or at least, we get there by the end.

Standing there in what used to be his childhood bedroom, and was now a closet that would rival any popstar or supermodel, Trent was conflicted with how to push forward. All he wanted was for this to be over, but there seemed to be no path towards that. Every moment was another indignation, another spike into his ego designed to make him question who he was. He stood there, staring at himself in the mirror and trying to decide if this type of life was any better than the threats that Deedee was holding over him.

Turning those thoughts over in his mind, he kept coming back to the moments where Deedee continued to love bomb him. Those moments only seemed to appear when he had found a way to please her. Even with all of the other negative things she levied against him, he couldn’t deny that those moments felt good. He wanted to say that he hadn’t felt pride at finally managing to meet her standards, but he knew that wasn’t the case. As scary as that was, the worst parts that seemed to lodge in his mind was the feeling of their makeout session. He knew that the enjoyment he had felt during those moments was wrong, but that didn’t change the way his body responded. Nor did it change the tingling that he could still remember across his whole body.

With **** left but to follow his father, Trent stepped out of the bedroom carefully. Deedee had been right to caution him about the new shoes. Walking in mules was nothing like a pair of heels that held onto his feet. Taking even smaller steps, he did manage to figure out the proper way to mince into the bedroom. Once he entered, Deedee once again took control of the situation. In moments he was in her bathroom with makeup wipes removing the work of the girls at the salon. He thought he should have been happy to finally get it off of his face, but once he saw himself in the mirror, something felt off. After they had both taken their makeup off, Deedee spoke up. “Your nightie is right there on the counter. You can change here in the bathroom if you want. Oh, and don’t forget to take your little step aid out and clean it. Unless you want to keep it in, of course.”

Without looking to see if Tiffany would follow instructions, Deedee slipped into her bedroom. Pulling off the robe, she also shed herself of the panties that contained her sizable bulge. Naked now except for her own heels, Deedee selected her own night clothes. The champagne colored silk shorts with the black lace edges fit her ass perfectly, and the drawstring would allow her to keep her dick from flopping about during the night. The matching top was made of skin tight black lace and had a cute little black bow that nestled between her breasts. Stepping up to the bed, she began to pull down the covers and slipped into the expensive cotton sheets.

Meanwhile, Trent stood staring at the rose pink satin and lace nighty that had been left for him. Deciding that those could wait a moment, he moved to tackle the plug that was still up inside of him. Pulling his white thong panties down, he was **** to lean forward over the counter to be able to comfortably reach back. Reaching back, he was suddenly aware that this would not be as straightforward as he had hoped. Using one hand to separate his cheeks, the other reached back to try and grab the plug, only for his nails to interfere. Not used to the extensions, he was having a difficult time finding a way to secure a grip on the plug without stabbing himself.

After several aborted attempts, he gave up and stood up straight. There was no way he wanted to call Deedee in to help, but leaving the plug in overnight was an even worse idea. Finally, he spoke up. “Like, can you come help me please? I like, I can’t get this thingy out of me.” He hoped that the overly stereotypical language would endear him towards her in the moment.

Deedee’s voice drifted into the bathroom from the bed and he just sighed as he registered what she was saying. “Interesting, I would think a capable person would be able to do that. Tell me though, what is in it for me? Why should I come help you?” Deedee could feel just how petty her answer was and knew that Miss Jameson would not approve, but the pain in her heart at his refusal of her advance was making it hard to act as lovingly as she had all day.

Gritting his teeth, he knew this was just her way for driving the spike farther in. It was bad enough that he wanted nothing more than to get it out, now he had to negotiate with the person who had put it there in the first place. Wracking his mind for a reason, he once again realized that he still didn’t truly understand her goals in this. The only thing he could think of to offer were things that she was already forcing him to do. Deciding to give one of those a try, he spoke up. “Like, what if I promise to act like the perfect girlfriend for you tomorrow babes?” Inwardly, Trent cursed as he made the offer. It was the last thing he wanted, but it was also the easiest thing he could think of. Tomorrow was Saturday. A typical Saturday with his girlfriend usually meant just chilling on the couch and watching netflix.

The response he got was the sound of Deedee’s mules slapping against the bottoms of her feet as she stepped into the bathroom. Having realized that she would need to help him no matter his answer, she had already been on her way. Closing his eyes so as not to have to watch the scene he knew was about to unfold, Trent bent over slightly at the waist. Deedee stopped for a moment to see Tiffany standing there, white panties down around his knees, his ass pushed out towards her like a prize. It was astounding what could happen in so short a time.

Stepping up behind him, Deedee’s hands settled on his hips lightly. Even without the corset, she was astounded at how round his ass and hips really were. Slipping one hand up along his spine, she decided to draw this out and see how far she could take it. “Bend over more, I need you to arch your back and really give me access to you.” Her hand on his upper back pressed gently to see if she could get him to bend over in front of her like this.

Suddenly unsure if he had made the right decision, Trent could find no way forward but to follow her instructions. Slowly, he bent over and presented his ass to her. His legs were straight as he placed his hands on the counter for balance. With his eyes squeezed shut, he tried to disassociate himself from the encounter. Then, with a jolt his eyes opened as he felt a hand slap against his derriere. As his head popped up he arched his back even more and opened his eyes to see Deedee standing behind him. Surprisingly, her expression was neutral as he felt one hand reach down and spread his cheeks.

Then he could feel it, her fingers pressing against and moving the plug that sat in his ass. He hated how the tingle that ran up and down his legs made him feel. The feeling of the cage around his dick tightening and restraining him from growing made him feel like he was being pushed to the edge of a cliff, but unable to ever jump off. Gritting his teeth, he searched over his shoulder to see Deedee there, dispassionately wiggling the toy back and forth to loosen the grip that his sphincter had on it. Even with all the conflicting emotions and feelings that were lighting his brain up like a bug zapper, he could tell that something was off with his father.

Then it was done. The plug slipped from him without making a sound, of course a sound did come from Trent. The short moan was cut off as soon as he realized he was making it. Wordlessly, Deedee stepped from behind him and set the plug into the sink. “Wash this carefully. Soap and water, make sure to get all the soap off it, then leave it to dry.” It was odd to Trent not to hear some sort of term of endearment out of Deedee. Seeing that there was a new set of panties to match the nightie he was supposed to put on, Trent slipped the white pair off completely and tossed it into a nearby laundry basket. Not sure how to approach the situation, he simply moved forwards with his instructions.

Finally getting to see the object that had been inside of him for over an hour, Trent was amazed at how small it looked. Inside of him it had felt large and invasive. Sitting in the sink as he waited for the water to warm up, it looked like a tiny little thing. Standing there in just his heels, Trent dutifully cleaned the plug. Once that was sitting by and drying off, he stepped over and began to put on the outfit Deedee had set aside for him to sleep in. The rose colored panties slipped over his hairless legs comfortably, but the nightie took some getting used to as he slipped it down over his large breasts. Finally letting feeling it settle, he realized that it would not even cover the entirety of his panties. Sighing dramatically, he stepped in the bedroom.

Seeing Deedee laying on her side and facing away from him made Trent pause as he tried to think about where he would sleep. “Like, I guess I’ll go take the couch.” A grimace appeared on Trent’s face as he realized that he had not even consciously tried to make the accent appear. His heels slapped against his feet as he began to head towards the living room.

“No, you will not.” Again, Deedee’s voice sounded off. The softness and teasing quality to her tone was missing. “You will sleep in my bed with me, like a proper girlfriend. Isn’t that what you promised Tiffany?” Without turning over to look at her son, Deedee lay there and stared off into blank space.

“Like, yeah.” The accent was **** this time, his voice thick with emotion as he realized what this could possibly mean. She had been teasing him all day with her body, and now she was forcing him to sleep next to her. Stepping out of his heels, he slipped into the soft bed quietly. The room was quiet as Deedee reached up and turned out the lights plunging the room into darkness.

“Good night baby.” The whisper from Deedee slipped from her lips so quietly that Trent didn’t manage to understand what she was saying, so he laid there quietly. Trying to find a comfortable position with the new weight attached to his chest and a small plastic cage wrapped around his dick, it took far too long for the both of them to fall asleep.