Earn 'em baby!

Deedee couldn’t keep the smile off of her face, the interaction with Jessica had gone perfectly. Every little piece of it had been a slap in the face of Trent’s remaining masculinity. Their heels clicked along in a staccato rhythm as the pair of them made the short trip back into the garage, Deedee pulled Tiffany along with her by the hand in order to make sure he didn’t try anything stupid, like running away.

“You know Tiffany baby, you are going to need to learn to speak to men. You can’t keep acting like a mute. Sooner or later some big strong man is going to take your silence as acceptance and you are going to be even more sore than your little tushy is right now.” Deedee’s free hand crept down to Trent’s skirt clad behind and rubbed it gently, her fingertips just brushing against the newly installed plug.

Swallowing to give himself a chance to get into the right mindset to speak again, Trent took a half step forward in an attempt to stop the fondling of his ass by his own feminized father. “Like, I just, I don’t know if I can do this Ma’am.” It was the first time that the honorific had been applied to a sentence correctly and it brought a nod of acknowledgement from Deedee.

“Tell me hunny, what don’t you think you can do?” Deedee’s fingers slipped from Tiffany’s as she allowed him to step out of her range. Turning to lean against the shelf that Jessica had previously occupied, she motioned for him to sit down again.

Trent’s eyes flashed with annoyance at the way that his father was handling all of this. He was following the god damned rules and it just kept getting worse somehow. It didn’t help that while he had hated every moment of dealing with Jessica, just having her around while the plug had been seated in his ass had pressed buttons in his body and mind that he didn’t know existed. If he hadn’t been caged at the time, his skirt would likely have been showing just how much all of this was turning him on. Deciding to stand in a vain attempt at defiance, he shifted a hip to the side to try and find a more comfortable way to stand in the painful heels. “All of it! Look I…” The outburst bubbled up out of his throat in Trent’s voice only for him to realize his mistake half way through. “Like I, I’m sorry ok? I know I like, said a bunch of terrible things. And like I fully get what you went through for me. So like, please can this just stop now? I like, I get it.”

The smile on Deedee’s face slipped away slowly as the hissy fit of her son turned girlfriend began to gather steam. It was clear that Trent was apologizing for Deedee’s feelings, not for his actions. “I’m glad you are sorry, although I think you are more sorry that you are being punished than anything else. As for quote unquote, fully getting it?” The finger quotes in the air that accompanied that statement were full of derision as she continued on. “You really don’t. You think that a few hours of embarrassment, some casual flirting, and a bit of foot pain are all I went through? Do you truly think that the few hours you have been doing this somehow equates to the year of horrors that I endured?”

Trent froze as he felt the anger begin to radiate off of Deedee. It seemed like every time he tried to fix this, it only made the problem worse. Back when it had been Trent and Derek, a simple apology and an offer to do some chores would have been all it would take to mollify the parent. Not that he ever fulfilled the offer to do any chores around the house. Ever since his mother had left, Derek had walked on eggshells to keep his son happy. Something in the last year had changed that. With all of those thoughts running through his mind, Trent couldn’t find a way to move forward. Reaching up, he swept an errant strand of hair back behind his ear as he stood there.

Standing there silently, it became apparent that Deedee was waiting for an answer. Instead of continuing. Sadly, Trent had no answer. Seeing no other recourse, he decided to try and appease her by completing this assigned task. Stepping over to the chair and lining up in front of it, he began his walk down the driveway again. His focus on it was laser sharp as he stepped slowly and carefully. Each sway of his hips and each foot placement was calculated to be exactly as he had been trained. The turn at the bottom of the driveway was so well executed that the skirt around his hips flared out, the light material floating in the air as he made his way back up. Making sure to plaster the fake smile across his lips, he stared straight ahead and almost ignored the hot milf in the leather skirt that had her eyes glued to his body. Reaching the chair, Trent turned and gracefully sat down, his hands slipping behind his to gracefully pull his skirt in as she landed lightly on the seat. Even with the light touch as he sat, he could feel the plug inside of him move around. Slipping one leg over the other, Trent casually crossed his hands over his knee. Taking a moment to pose there, he stood back up slowly. Again his hands smoothed out his skirt as he stood tall. His gaze fell on Deedee as he waited for approval.

“Again.” The single word was the only response that Trent received. This pattern followed itself for the next three attempts. Each attempt pushed Trent’s anxiety up through the roof, to the point that when he stood and waited for the order from Deedee after his third attempt, his hands were shaking at his sides with nervousness. The cold detachment that she had been giving him ever since his failed attempt to apologize was causing a whiplash effect. One moment Deedee was fawning over him, the next it was like there was not a single thing he could do correctly. His inability to predict the mood swings was beginning to fray his nerves.

“Good.” Reaching up, Deedee’s long nailed finger pressed the button for the garage door. As the large metal door slid closed, Trent stood frozen and unsure what to do next. His eyes locked onto Deedee as she pushed herself off the shelf. The silence stretched between them for what felt like an eternity as her gaze traveled up and down his body. Trent began to search his mind for anything that could break the tension. Finally, Deedee spoke again. “Inside.”

With that simple proclamation, Deedee stepped into the house. Not once looking back to see if Tiffany followed her, she walked through the house and into her closet. Unsure of exactly what was happening, Trent had **** but to follow along. While perhaps not as perfectly as it had over the last few trips up and down the drive, Trent’s body was becoming more and more used to the movements that the tall heels required of him. An outside observer would have had trouble finding any difference in the way the two individuals walked, although perhaps the second one had a bit of extra sway to their step.

Stepping into what used to be his old bedroom, Trent let his gaze take in the room. For the first time he realized just how much of a wardrobe Deedee had truly built up. The wall of heels was the least of it. Each other wall was covered in a rack of clothes that contained any manner of sexy outfits. “It is amazing to me that we can both wear the same sizes, as long as you are corseted of course. Or if it is stretchy enough.” The playful tone in Deedee’s voice was yet another mood swing. Turning to look at her, Trent saw Deedee sitting at a vanity. Reaching down, she began to unzip the tall over the knee boots she had been wearing all day.

After pulling them off, Deedee deposited them along the wall before selecting a pair of white mules. Slipping into those, the four inch heels brought her roughly to the same height as her son. “You have been a good girl for a bit now, and I owe you your rewards. But I think we both could use some relaxation first, don’t you? Turn around, and I’ll get your zipper.”

Given the opportunity to get out of the clothes he was currently trapped in, Trent turned around as swiftly as he heeled feet would let him. The zipper whispered into the quiet room as Deedee pulled it down. Trent could feel the breath of the woman behind him as she released him from the dress. Slipping her hands in, she slowly pushed the dress off of his shoulders, allowing it to fall down to catch on his corset slimmed waist and expansive hips. Trent stood still, unsure of how to help, or even if he should. The feelings of her hands on his bare skin sent small jolts of pleasure through him.

Looking down, the white corset came into his view for the first time that day. The heavily boned white garment closed in the front with golden tabs. Behind him, the cord lacing held the back completely closed. Realizing just how large the breasts on his chest were, he wasn’t able to tell where his flesh ended and the fake breasts began. Turning his gaze away from the prosthesis, he was greeted by something incredible. Deedee had paid attention to Chloe’s methods as she had been feminized. One of those was to never skip a chance for the target to be able to feel beautiful or feminine. With that in mind, she had positioned Trent so he faced into the mirror she used as she dressed each day. The antique stand mirror showed Trent a half dressed woman in a corset and heels, as a pair of long nailed hands came from behind her to rest on her hips. Of course, that wasn’t actually a woman, it was him.

Trent’s eyes locked onto his reflection and he lost himself in it. Deedee was able to reach down and guide his feet out of the dress so that she could place it along with all her other garments for laundry. Meanwhile Trent studied the form he saw. His eyes shifted along his form as he hoped to find something that would show the masculine man he had been earlier in the day. Shifting to get comfortable in the high heels, again he cocked one hip to the side. The very feminine pose emphasized his new, and already existing, curves even more. “Tell me what you see Tiffany.” Deedee’s voice was softer as she moved up behind him, completely hidden from view.

Trent’s breath was shaky as he tried to find a way to salvage his pride. The gorgeous creature before him would give his girlfriend a run for her money in a beauty competition. Not only that, but she was garbed in some of the most feminine garments in creation. Swallowing audibly, Trent opened and closed his mouth, trying to find the words to say something that wouldn’t make him sound like a bubbly bimbo while he spoke in the way that had been demanded of him. “Like, I guess, like, I see a man who is being made to dress like a girl.” It was the closest he could find to the truth, that also happened to feel true to him.

“If by making you do this, you mean forcing you to follow through with something for once in your life? Then yes, that would be a fair statement.” And there it was, the bitterness was back. His eyes locked with hers as her head sprouted over his shoulder in the mirror. The look on Deedee’s face once again showed that he had missed the mark when asked to do another thing. “I don’t understand you Tiffany. One moment you are doing things perfectly, and the next you go and fuck it up by letting your ego get in the way.” He could see her working a thought around in her mind, as if deciding how to handle a difficult situation.

“Perhaps I have been going about this the wrong way.” Stepping around in front of Trent, Deedee filled his vision. With the change in heels and their height equalized, Trent stared into Deedee’s blue, almost gray eyes. Reaching out, she took control of both of his wrists, sliding them up till they rested on her shoulders. Sliding her hands down along his bare skin sent tiny jolts of pleasure to Trent’s brain. Each jolt was accompanied by the panicked thought that this was wrong, and not just because of the way he was dressed. Settling her hands down on his hips, Deedee pulled the feminine pair together. Without a choice in the matter, Trent’s body molded against the stunning older woman in front of him. Hundreds of tiny feelings began as her body rubbed against his in ways he had not felt before.

“This is wrong.” Trent’s words were completely without filter as they slipped out of his pink lips. Deedee’s grin never faltered as her hands slipped past his hips to settle on his ass, her long nails drawing short lines in the soft skin. Leaning forward, Deedee stifled any further protests by pressing her lips against his. Unlike this kiss before, this makeout session started much more tenderly. Each brush of the lips was soft. At first Trent tried to stop it, to pull away. But his fathers greater strength held them together. Later recollection of this event would show that perhaps he was not trying to escape as hard as he could have.

Slowly, he began to reciprocate Deedee’s advances. Falling back into patterns that he had established as a man, Trent tried to take control of the kiss. Each time he did, he was rebuffed. Deedee would pull away just enough to create space before speaking. “Softer baby.” Slowly, he began to take a more submissive role in the process. Each time he became more submissive, he was rewarded with greater fervor. The two stood there kissing each other for what felt like eons, although only a few moments had actually passed. Finally, Deedee broke the kiss and stepped back, giving Tiffany’s ass one final grope. “Perhaps you respond better to the carrot than the stick.”

Trent stood there in a fugue state as he tried his best to rationalize what had just happened. He told himself that he was only going along with this to appease Deedee. He only did it to try and find a way back to his masculinity. Yet still, in the back of his mind another voice yelled. It screamed and hollered that he had enjoyed it. Worse yet, it wasn’t just the kiss he had enjoyed, it was all of the feelings. Swallowing, Trent shoved that thought deep inside himself and spoke up again. “Like, can I please get changed now?” While his face had displayed the war of emotion inside of himself a moment ago, the look he showed to Deedee now was one that conveyed a complete lack of emotion.

Deedee was not prepared for the hurt that sprung up inside of her at the look on Tiffany’s face. The past year had trained her that using her sexuality as a weapon was the best tool in her arsenal. Typically she was able to achieve anything she wanted if she could leverage her sexuality towards her goals. Not only that, but for the briefest moment she had opened herself up to the person in front of her. She had allowed herself to feel the sort of feelings that she had buried years ago when her wife left. Now, they were being trampled on.

Sudden anger flared in Deedee, before it could boil over she shoved those feelings back into the dark hole where they belonged. Trent could see the war within his father’s face as well after his question. Slowly, the sexual tension from the makeout session between the two drained out of the room. Moving back around behind her son, Deedee began to undo the lacing on his corset. “The first rule you will follow while in this house is that you are Tiffany at all times.” Slowly the corset loosened up a bit more. Before moving to loosen it enough for removal, Deedee quickly reached around and undid each of the garter straps holding up his stockings.

“Second, you will wear high heels while within my house. The only time you may have them off is while sleeping, or while in the shower. No heel will be below three inches. Not that I have any in my collection that are below four.” Trent shook his head as he thought about being trapped in the oppressive and painful shoes. He did not understand why Deedee was so obsessed with them, but resolved himself to get out of them as soon as possible. Distracted by his thoughts, Trent was suddenly aware that the corset was loose enough that Deedee could reach around to the front and undo it. As the halves opened up, Trent felt the weight of his unsupported breasts for the first time. Almost without thought his hands slipped up to support the breasts that now extended from his smooth chest.

The sudden flush of feeling was more than a little surprising as his palms rubbed up against the erect nipples of the fake breasts on his chest. Unable to suppress his reaction, Trent’s sudden intake of breath let Deedee know exactly what had just occurred. “I was wondering when you would get there.” Setting the corset down, she continued on. “Those are very expensive tits you have there hunny bunny. Not quite as much as mine, but closer than you would think.” Giggling at her own joke, Deedee stepped away from the half naked man as he cupped his large breasts.

“They have a sensor attached to the nipple, it feeds into a little computer, which moves a little motor around to manipulate your nipple. Think of it like a rumble controller for your tits.” Picking up a pair of mules that matched her own, but in a soft pink she stepped back over to him. Crouching down on her heels, Deedee set the shoes next to Trent and began to undo the ankle straps holding his current shoes in place. “They are fully waterproof. And the makeup Sara used to blend them into your skin should last a few weeks. We can get it touched up when we go to the salon for our nails in two weeks. So don’t worry, you won’t be without them for a long time.”

Trent tried not to let the frustration show as he listened to Deedee describing just how much effort had gone into making him into a woman. Realizing that the buckles were fully undone, Trent stepped out of the white platforms and stood flat footed for the first time since waking up that morning. Sadly, it didn’t take Deedee long to slide the stockings down off his legs and motion for him to step up into the mules. “These are harder to walk in hunny, so be careful. Maybe walk a little slower, instead of a big sway, try a bit of a mince instead.” Stepping into the new heels, Trent stood there clothed only in his panties and new heels.

Taking the time to put away the pieces of clothing she had removed from her son. Deedee left him to stand in the middle of the room mostly naked. Taking pity on him as he stood there, she eventually tossed a soft silk robe to him. His long nailed hand snagged it out of the air, although the gesture almost cost him his balance as the aforementioned mules were indeed more treacherous to even stand in, let alone walk. Slipping the robe on, Trent could only sigh as he realized that the bottom edge of it would barely come to his upper thighs.

With Trent mostly taken care of Deedee herself began to strip off that day’s outfit and don a robe of her own. Unable to help himself, Trent’s eyes locked onto Deedee’s black lace boyshort panties and the large bulge that they contained. Still upset at herself for allowing Tiffany the chance to hurt her again, Deedee stepped out of the room as she belted the robe around herself leaving Trent to stand alone in the room that used to be his bedroom.