Mistakes were made

Deedee’s comments continued as she led him back back into the closet that was quickly becoming the center of Trent’s world. “I’m sure you know what the first three mistakes were. We will have to see if you paid enough attention to understand what the fourth could have been.”

Stepping into the room a few feet behind Deedee, Trent watched her with a questioning look as she stepped over to what had been the closet of his old bedroom. Not wanting to keep her waiting, he spouted the first thing that came to mind. “The first mistake was like totally ignoring what you told me to do.”

Deedee’s tepid response to his version of the story was evident on the look in her face as she slid the closet doors open and pulled out a tall white wooden barstool. Turning, she moved it to the center of the room and placed it directly in front of the mirror. “Try again. What was it that I told you to do that you refused to do?”

Trent had been hoping to avoid having to say exactly what it had been. He didn’t want to think about the plug ever again, but she was going to **** it out of him. “Like, I totally didn’t put the plug inside me like you told me to.” His mind worked feverishly to try and find a phrasing that would retain any of his masculinity. Saying the words out loud only seemed to make them more real.

Unfortunately Deedee had other expectations. “Close, but no. Repeat after me Tiffany dear. I didn’t shove my plug up my sissy ass like I was told.” Pointing at a spot near the stool, Deedee motioned for Tiffany to move closer to the stool. Deedee’s actions and tone were completely dispassionate as he had ever seen them. To Trent’s eyes it was almost like she was following a script that had been laid before her.

Stepping up to the stool, Trent actually found it easier to simply use her words. Yes, they were more embarrassing and certainly if anyone other than Deedee ever heard him say them he would die of embarrassment. However, just repeating the line that Deedee prepared for him was simple recitation. It still stung as his practiced valley girl voice spoke the humiliating line. “Like I didn’t shove my plug up my sissy ass like I was told.”

Moving around behind Tiffany, Deedee pushed on his back lightly. Understanding of what was going on suddenly blossomed in Trent’s mind as he could tell the stool was at the perfect height that if he bent down and placed his palms flat on it, he would be at a near ninety degree angle. Taking a deep breath, he bent over at the waist, his hips jutting out behind him. The skirt he wore was barely long enough to keep any of his modesty while standing straight up and down, bent over in any way his ass was almost completely exposed. Spreading his feet apart to shoulder width, he was able to comfortably hold his body in the position he knew she wanted him in.

“Good girl.” Shame riddled Trent’s mind as the praise sent a flush of happiness through him. While a part of that could have been elation at finally getting it correct, he still hated that being called a girl made him feel good in any way. Deedee’s hand reached out to pat his bare ass affectionately before she continued. “Now, what was your second mistake?” Stepping away from him, she moved to a set of drawers and slid them open. Out of the drawers Deedee retrieved the plug he had worn the previous day as well as the bottle of lube that had been with it.

He had known from the moment she had led him into this room what was about to happen. If he was honest with himself, he had known from the moment he refused to put it in that morning that he knew it was going to happen. Still, the sight of the bright shiny plug sent a sliver of fear into his chest. “Like, my second was showing the girls in the store my cage. I should have been more careful.”

“I’m going to accept that one, even if you could do better. We haven’t spent a lot of time on the fact that you should call your little caged toy a clit. But since you specified your cage, and accepted responsibility for it, I will accept that.” Reaching back into the drawer, Deedee pulled out a slightly larger plug than the one that already sat on the desk. “So, you are one for two. Let’s see if you can get any more right.” Pulling out a third even larger plug, Deedee set it next to the other two.

Trent’s mind tried to connect the dots and his fear made it easy for him to assume that mistakes would result in the plug’s size being upgraded. Not even wanting the smallest of those inside of him, he certainly wanted to do everything in his power to avoid any larger ones. A small part of his mind did question just how many of the toys she had. “Like, my third mistake was like not cleaning you like I should have just now. I like, should have been a,” Trent’s voice went silent as he had been about to call himself a bad girl. Desperately not wanting that label, he tried to find a better way to say it. “I like, should have been better. I’m totally sorry Deedee.”

Hearing him invoke her name like that reminded her of her instructions from the day before. Toying with forcing him to call her Ma’am before had been something she had taken from what Miss Jameson had done with her. The feeling of it had never truly gelled for Deedee, discarding the idea felt like the correct choice for them. It was yet another thing that she would be doing differently than had been done between her and Miss Jameson. “Shakier, but still acceptable. Now, what was the mistake that you think you may have made today?”

Trent was elated at having managed to state what she wanted correctly. So far it had been more about how he had admitted to each mistake more than knowing what each mistake had been. The only problem now is that he didn’t know what else he may have done incorrectly. Deedee smiled as she took in his form while he concentrated on trying to figure out what the nature of his mistake could have been. Seeing him there legs straight, bent over at the waist, tiny skirt riding up high and showing off his big round bouncy asscheeks, his hands palm flat on the stool as he chewed his lip. It was visions like this that drove that voice that she was doing something wrong deeper and deeper with each passing minute.

“While you think on that, I’m going to get you ready for some of your punishments. Do not move.” Reaching behind her, Deedee gathered up a red scrunchy from her makeup table. As she sauntered towards him, Trent had a difficult time not noticing the tented skirt that bounced around as her hips swayed side to side.

Walking to his side, Deedee carefully gathered up Trent’s long flowing blonde hair into her hands. “Let’s make sure this doesn’t get in the way shall we?” Using the scrunchy she pulled the gathered locks into a high tight ponytail that stuck out from the back of his head at an angle.

The entire time that Deedee was playing with his hair, Trent wracked his brain to try and find another mistake he made. Was it something to do with Brittany? He had followed all of Jessica’s orders. Was it having to ask for money for the outfit? That didn’t seem right. His mind discarded every option it ran across as he watched Deedee stride back to the place where she had laid out the plugs and lube.

“Well Tiffany my dear. Time’s up. Did you figure it out?”

Trent closed his eyes and did the only thing he could think of. He hated the thought of begging like this, but throwing himself at her mercy seemed like his only recourse. “Like, I’m clearly too much of a blonde to like, know this stuff. Could you tell me Deedee?”

“I will make you a deal Tiffany. You have a choice. Either, you can be punished for not knowing what you did wrong.” As she said those words she reached in and pulled out an even larger plug. Trent goggled at the size of it, not even sure that the toy could fit inside of anyone, let alone him. “Or, you can promise to make it up to me, since I have to tell you what you did wrong.”

The breath that flowed in and out of Trent became ragged as he realized just how bad she had him over a barrel, almost literally. Looking over at the plugs, Trent knew that they would be painful and would likely be something he had to endure for hours. His other option was to give Deedee even more leverage over him. To give her a blank check. Still, his eyes locked onto the bulbous end of the largest plug and he shivered in fear. “Can you like, tell me please?”

Deedee nodded happily as she put the largest plug back into the drawer. “Of course I can baby. I’m glad you trust me enough to know that I am always here to guide you.” Moving back over to Trent, her fingertips slowly drew lazy circles on his skin as she slowly walked around him. “Tell me Tiffany honey. Where are the clothes you left the house in?”

Sudden realization shot through him as he winced. Of course that was a clear mistake. Jessica had been in such a hurry to leave, and he had been so worried about not flashing the movers that he had left the bag of clothes sitting on the floorboards of the car. “Like, that’s not my fault!” The petulant response erupted from him. “Jessica totally drove off too fast!”

Deedee tsked quietly as she headed over and collected a pair of items from the table. “So you refuse to take credit for your actions? Instead, you blame the woman who took you shopping as a favor to me.” Sighing loudly, she stepped behind him. As she moved, his eyes shot up to see which of the plugs she had removed. Tension fell out of his body as he realized that she selected the second smallest of the solid metal anal toys.

Feeling her walk around behind him brought most of that tension back into him. Breathing out through his painted plump lips, he closed his eyes in anticipation and tried to prepare himself for the invasion that was to come. Even as prepared as he thought he was, the feeling of the cold lube dripping onto his exposed ass nearly made him jump out of his locked on high heels.

Deedee stifled a giggle as she saw his reaction to the feeling of the cold lube dribbling down the crack of his bountiful ass. It had taken a fairly substantial portion of her willpower not to lean forward and try to lube up Tiffany’s ass with her own tongue. The thought of having any part of herself inside of the puckered hole in front of her was enticing, yet she knew he wasn’t anywhere near ready for that. For multiple reasons.

Taking a good portion of the lube into her hand, Deedee applied it generously to the plug. Trent was almost vibrating with fear in front of her as she teasingly ran the tip of the plug up and down the crack of his ass. Placing the tip right against his hole, she began to push it into him gently. “Open up for me Tiffany baby. The more you relax and open up for me, the less it will hurt. I promise baby.”

Trent’s initial reaction was to clench his body tightly and try to repel the invader. Somehow there was a huge difference between today and the previous day when she had first inserted something inside of him. Listening to Deedee’s words helped him control his body's reaction. His breath caught as the bulb continued to press inside of him. With each millimeter he could feel himself stretching around the plug. At first it was easy to keep himself open and accepting of the feeling, then as it continued to stretch him out, Trent was **** to spend more and more willpower to keep from trying to **** the invader out of him. Just as he was about to give up and scream out in pain, the plug slipped all the way in.

The sudden relief of the plug seating itself correctly, combined with the buttons on the inside of his body that it pressed as it settled into him caused a low moan to escape from him. His breath caught as he felt his dick inside of his cage begin to swell with the feelings that were building inside of him. Taking a few long deep breaths he finally managed to get himself under control. Finally opening his eyes, he stared forward and saw Deedee standing in front of him. The tent in her dress was inches away from his face.

“Now dear, perhaps we talk about what you owe me.”