Existential crises are hard to sum up.

The rest of the meal had proceeded in silence as Trent wallowed in his situation. Placing a crisp hundred dollar bill down at the table, Deedee pulled Tiffany back onto his cursed and painful high heels. Seeing her table clearing out, Krysta stepped up to begin clearing it all off. When she saw the fairly large tip that Deedee had left, she turned to the girls. Her eyes took in the pair of stunning women in front of her and she spoke up. “Oh my god, you two are so cute together. I love your shoes! I always wanted a pair of Louies but well, you know how it is.”

Deedee’s smirk wasn’t just directed at the way she knew the compliment would make Tiffany feel, but also in the way it allowed her to continue to twist the dagger in his masculinity. “She begged and begged. And it had to be the pink ones of course, couldn’t be any of the other colors, no it had to match her favorite dress.” Rolling her eyes dramatically, Deedee giggled and locked arms with Tiffany, pulling her along before Trent could defend himself, they stepped carefully from the building.

With the excitement of the past few hours still affecting her, as well the dose of viagra from Ashley. Deedee kept her black leather hobo bag in front of her to hide any untoward bulges. As Deedee helped Tiffany across the parking lot, she decided to try and continue to train her new woman. “Tiffany dear, women don’t carry their purses like that. You are gripping it tighter than you did my cock earlier.” Trent’s instant reaction to the open admission of the sexual **** from earlier was to whip his head around in an attempt to make sure they were alone. Upon seeing they were still alone, Trent shook his head back and forth in resignation. The simple action caused his long blonde tresses to move across his neck and shoulders in a way that still felt alien to him. “That is an expensive purse you have there. I let you borrow it so you could match your shoes. But if you don’t treat it well, then I won’t feel comfortable lending you one next time.”

As the exhilaration and fear of the possibility of being heard slid away, Trent found the wherewithal to roll his eyes at Deedee’s antics once again. “Like why would I want a purse anyways? I don’t have a wallet or, like any money, remember?”

“Of course baby, and if that is your choice, fine. But you aren’t going to be wearing anything with real pockets in it for the foreseeable future, and a woman needs to keep certain items close. I would rather carry a purse than look pretty ridiculous walking around with a tampon, makeup, and a condom in my hands, wouldn’t you?” Everything had a purpose it seemed. Apparently that purpose was embarrassing Trent at every opportunity. Trent’s mind managed to somehow skip over the tampon and get stuck on the condom. What would he need a condom for, no woman was going to sleep with him with his dick all locked up.

Getting back to the car, Deedee stepped up and opened the door for her date. “Getting into a car is different than before sweetie. You can’t just jump in. Unless of course you want to flash those cute panties at a boy. Now, before you sit, reach back with your hand and smooth your skirt down. Then I want you to sit back onto the seat carefully. Once you are fully seated, then you swing your legs in together. Remember, a lady’s knees should only part when her partner wants something.” The lascivious grin on Deedee’s face showed that that demand would be coming sooner rather than later.

Trent tried to follow the instructions that had been laid out to him. “No no, not like that hun. Stand up, do it again.” And so came his first deportment lesson. Over and over again his father made him stand up and sit down, getting in and out of the car repeatedly. Trent could see people pointing at the two of them as he kept trying to get used to Deedee’s exacting opinion of a perfect feminine action. The tall stiletto heels on his feet did not make the process any easier. Standing up took an amazing amount of effort on his quads, and the angle of the arch kept his calves tightened so much that by the third try they were starting to burn. All in all it took him more than twenty tries to finally get it right.

Finally allowed to sit in the car, Trent sighed and tried to relax for the drive home. Leaning back against the seat, he was resting his eyes for a moment before his attention was grabbed by the feeling of a hand once again intruding on his thighs. “Hunny, I said a lady keeps her knees together didn’t I?” Looking down Trent realized that in his attempt to get comfortable, he had allowed his knees to split apart. If he had been in public, every man would have been able to see up his skirt and catch sight of his bright white panties.. “Now, I told you at lunch that there would be benefits to doing as you are told. There will also be consequences of not doing as you are told. For example, if you want to sit with your legs open like that, I can find my shortest skirt for you. Then we can go sit at the park across from your college’s football practice facility. Without any panties of course, because only a girl who doesn’t wear panties wants to sit like such a slut and let boys see exactly what kind of girl they are.”

The threat was delivered so nonchalantly that it took Trent a moment to realize just how bad that would go for him. Over the years Trent had started to suffer from small man’s complex. Only without the looks, size, or skill to enforce his will on others he had settled on using his father’s money. Many of the kids on the team were there on scholarships, so Trent had used every opportunity to embarrass them and make himself feel like a bigger man. If even one of those neanderthals figured out who he was, it would mean more than just an embarrassment. “I..I’ll like, I’ll be good.” It was the only words he could think to say that might mollify the woman whose talons were now resting between his thighs and toying with the tops of his stockings.

“Good girl.” The rest of the trip consisted of Trent squirming in the seat in an effort to not reveal just how turned on he was by the gorgeous milf that sat next to him as she played with his inner thighs gently. For her part, Deedee largely ignored Tiffany. She knew that her new toy needed time to settle into the situation. She had barraged her little wifey with so many new concepts and conditions over the last few hours that she decided to give him a break until they got home.

Arriving at the house, Deedee opened her door and stepped out of the car. Following suit, Trent froze as his father’s feminized voice struck through the air. “Tell me what mistake you just made.” Freezing in place, Trent wracked his brain to see what he could have possibly done wrong. He had stood up exactly as she had told him, he knew it.

Unable to figure it out, he finally spoke up. “I like, don’t know.” Shaking her head sadly Deedee made her way over to the side of the car that he stood on. She opened the door and pointed at the seat. Without hesitation, Trent slipped back into the car. Lifting his heels he demurely positioned himself correctly and looked back up at her. “See, I did it just like you showed me.” Going to stand up again and prove his point, he stopped when she began to slowly close the door.

“You stood up fine dear. But remember, this isn’t about doing one little thing right, it is about doing all the things correctly. I need you to learn that every action needs to be thought about before you make it. Every time you are about to do something I want you to stop and think. ‘Is this what a woman would do?’ Now, with that in mind, what did you do wrong?” Deedee sat there waiting to see if her trainee would pick up the concept quickly enough.

Trent’s mind ran through a thousand possibilities as he tried to figure out what the hell he might have done incorrectly. Each thought came up empty. It was such a simple thing, he wasn’t sure how he could have made a mistake. Deedee sighed as she stood there thinking that Derek had taught Trent this long ago. Of course it hadn’t been from the woman’s side of things but from the man’s. Finally, Deedee could tell that Tiffany had given up. “A woman doesn’t open her own door. She waits for a man to open it for her.” The simple statement came from Deedee and as he heard it, Trent’s eyes dropped to the floor. Of course it was that simple, and that embarrassing. Sitting there waiting for a man to open his door? It was insane.

Deciding to fight back finally, Trent spoke up. He made sure to speak with as deep a valley accent as possible as he addressed her. “Like totally, that makes sense, for sure. Like the problem is, a man did open in. Just cause you dress me like this doesn’t mean I’m going to turn into some sissy like you. I mean, like shouldn’t you have waited for me to open your door then?” The defiance felt good to Trent as he sat there looking up at her. He could see she wanted to be upset at him, wanted to do something terrible, but technically he hadn’t broken any of her rules yet.

It took a moment before Deedee responded. “Cute thought. Really, I commend you for finally growing a spine of some sort. Bad choice, but still a cute attempt.” Deedee’s own deep breath expanded her chest and pressed her large breasts out. Letting the deep breath out she opened the door and stepped back. “You know what isn’t ladylike? Talking back. Now, let’s go inside. It is time for you to start your training for the day.” Turning from the car Deedee stepped along the walkway to the front door and opened it up. Not even caring to look and see if Tiffany followed, she slipped into the house and left the door open.

The warmth at finally having stood up to his father in any real capacity was slowly fading from Trent as he sat there. Slowly replacing the feeling of success was the fear of the reprisal that he knew was about to occur. One thing that Deedee and Derek both had in common was that they never really exploded. Sure Derek had yelled, but it was always controlled, pointed. He yelled for effect instead of anger. It was clear that Deedee had retained that icy anger. Stepping out of the car, he stood up exactly as he had been shown, without even really thinking about it even though Deedee wasn’t there anymore. Softly closing the car door he began to walk inside. After having been off his feet for almost half an hour on the car ride home, the walk from the car to the front door was unpleasant to say the least. With each step he forgot more and more of the instructions that had been given to him. Stepping inside, he closed the front door and began to walk to the couch.