Come on, we all knew he wouldn't.

Before he could collapse into comfort on the couch, Deedee came back into the living room from the hallway. In her hands she held a pair of basic white platform heels. “Set your purse on the counter and follow me.” Her tone made it clear that not doing exactly as she said would cause a problem. So with a resigned look Trent stepped up to the counter and gently placed the expensive purse there. Following his father out to the garage, Trent saw Deedee standing before a metal folding chair. In front of the folding chair sat the heels he had seen her carrying only a moment ago.

“What are we doing here?” In response to Trent’s question, Deedee simply reached up and pressed the open button that was attached to the wall. The garage door silently slid open to reveal the driveway, Deedee’s car, and of course the street and neighborhood beyond.

“We aren’t doing anything. You are going to practice walking. Now sit.” Trent slowly made his way over to the chair and sat down, still unused to wearing a skirt in any way, he sat much as he would have before. A sigh was all the response that action got from Deedee as she kneeled down in front of Tiffany. Reaching down, she gently pulled the expensive designer heels off of his feet. Not wanting to give his feet time to swell up, she swiftly placed the much more padded heels on her son’s feet. These were still a tall heel, but with the two inch platform, the six inch heel only caused a four inch arch instead of the much taller arch she had been forcing him on in the Louboutins. “Apparently we will be learning how to sit as well.” Standing up fully, Deedee made her way to a shelf and placed the heels there.

“So here is how this is going to work. You are going to walk from that chair, straight down to the edge of the driveway and back. Each time, you will stop, sit in the chair, cross your legs like the woman you are, then uncross them and stand back up. Each time I see you do this correctly, you will be rewarded. After five rewards, you will be allowed to stop for the day.” Reaching down, Deedee took Tiffany’s hand in hers and pulled him up to a standing position. Pulling him out of her way, Deedee turned so her back was to the chair. “I will demonstrate. Now, pay attention.”

Looking directly into Tiffany’s eyes she winked once before setting off down the path she had proscribed. Each step of Deedee’s was meant to command attention. As she moved down the driveway her ass swayed from side to side, each step was on a perfect straight line as she moved. Her elbows stuck close to her sides, but she let her arms sway naturally below the elbow. Deedee’s back was ramrod straight, her shoulders were pulled back which emphasized her large bosom and her heart shaped ass. Each step let the unrestrained parts of her body jiggle in the most pleasant manner that Trent had ever seen. The sound itself even felt sensual, the click clacking of the heels on the hard surface. It was all so perfect as she moved. When she turned around to walk back towards him, he saw that her gaze was locked in front of her. She didn’t look side to side, at him, or at the ground. Instead she kept looking forward. Between her braless breasts and ass bouncing around, Trent didn’t take much information in from the walk. He did manage to notice that she did it all with a radiant smile.

Approaching the chair, Deedee turned and softly sat back into the chair. Her back stayed straight as she sat, her shoulders and chin maintained their positions as well. Looking up at Tiffany, Deedee leaned slightly to one side and slipped her boot covered leg up over her other knee. Uncrossing was just as feminine. Standing up, Deedee quickly moved out of the way and pointed to the chair. “Your turn.”

Trent gulped as he realized that he had absorbed almost none of that. Why did his father have to be so goddamn sexy? He could feel his cage restraining him again as he stepped in front of the chair. The heels on his feet felt more comfortable than the ones from earlier, but his calves and thighs were already starting to burn from just having stood around in them for a few moments. He was a bit worried about how far this was about to push him. So with as deep a breath as he could take, he started his walk down the driveway.

Deedee’s eyebrows rose as she watched her son walk down the cement. She was amazed that it actually wasn’t nearly as bad as she had expected. Her own first day in heels had been like an elephant on a toothpick. Here Tiffany was, her round ass already naturally swaying and jiggling. She wondered if he moved like that naturally and if she had just never noticed because she wasn’t staring at her son’s ass before. Just as he was about to turn around she realized that she needed to control her gaze. Letting the resting bitch face that she had been practicing all day fall into place, her eyes tracked him as he moved back to the chair.

Watching him sit on the other hand was a travesty. He didn’t smooth his skirt, his knees split, and his ass banged down into the chair. Deedee shook her head sadly as she watched him cross his legs. Inwardly she was surprised he had that kind of flexibility already. His ability to stand up was actually better. So by the time he looked to her to see her reaction, she was able to continue with a neutral expression. “You failed. First, you didn’t walk the line correctly. Second, you didn’t sway your hips enough. Third, you didn’t smile. Fourth, you kept looking at the ground in front of you. Fix those then we will see how else to adjust your walk. As for your ability to sit down.” Her grimace warned him just how bad this was. She had picked apart his walk in more than four ways, all with a neutral face. Now she had a look of disgust and disappointment on her, he could only imagine how bad it was. “I just showed you how to sit down not 30 minutes ago. A chair is a chair. Whether it is in a car or not Tiffany. And for god sake, don’t bang your ass into the chair like it is your boyfriend’s cock! Sit down gently.”

Trent’s eyes widened at her exclamation. His boyfriend’s cock? Wasn’t Deedee his girlfriend now? Why would he ever have a boyfriend? Then the next thought hit him, his girlfriend had a cock. Suddenly he was picturing himself sitting down onto Deedee’s lap. Fear broke out in him and he replied in the only way that had seemed to be effective today. “Like, I’m sorry.”

“You are sorry, what?” Her question confused Trent as he stood there fidgeting in his outfit. Perhaps the only good thing he had realized about all of this so far is that having long nails was like having a built-in fidget toy.

The only thing he could think was that she was demanding some sort of honorific now that she was acting like some kind of deranged barbie drill sergeant. “Ma’am?”

“Good enough for now. Perhaps in the future you will do well enough that I will consider allowing you to call me something else. But for now, when we are in private you will refer to me as Ma’am. Now, do it again and fix the things I told you to.” The next half hour was a grueling process as Trent began to walk up and down the driveway. With each step he became more and more aware of all the things different with his body that had escaped his attention previously. His ears began to hurt from the constant swaying and bouncing of his long dangling clip on earrings. Each step was like a small earthquake in his corset as his breasts bounced inside there, the fake flesh jiggling enough to concern him what it would be like when they weren’t compressed down in such a tight garment. He even noticed that his ass was jiggling. During that entire time, he never once managed to get a perfect rotation. Each attempt was better, but somehow he kept managing to screw something up.

“Fuck it. Keep practicing.” Deedee’s tone carried hints of exasperation and frustration as she collected the heels he had worn earlier and stalked into the house. As the door to the house from the garage slammed closed, Trent inwardly rejoiced. Sitting down on the chair he relaxed as much as he could. The corset kept his back so straight, and all the sitting down on the metal chair was making his ass hurt. Oddly enough, it was just more comfortable when he rotated his hips in the chair and crossed his legs at the knee. He didn’t want it to be, but the pain of the constant walking was starting to get to him.

Trent spent the next five minutes trying to think of a way out of the situation he was in. He tried to think of ways to delete the images, he tried to think of ways to get new clothes. All of it was impossible without his phone. What was he going to do, run to the neighbors and say ‘Hi, my dad turned me into a sissy, please help’. Not for the first time today, he sat there feeling like he was about to break down. Trent was so deep in thought of escape that he never heard the door open.

Deedee’s heels clicking on the pavement wasn’t even enough to let him know she was there as he sat buried in his own misery. “And what are you practicing right now Tiffany?” Deedee’s stern voice shocked him straight up out of the chair. Smoothing his skirt out behind him in a subconscious gesture, he turned to look at her.

“I like, umm, I just sat down Ma’am” The way that he had to move his face to affect the inflection of his valley girl accent made him feel even more girly. There was something that required him to move his head to get the right sounds. It was odd that he was able to just let himself fall into it so easily, but each word seemed to come with its own expression. “And like, my feet hurt so bad.” Deedee’s raised eyebrow reminded him to add on the honorific. “Ma’am.”

“Bit late on that one darling. But that is alright. You will learn. Now, I have a training aid here. Stand up, and walk around to the back of the chair.” Keeping herself out of his line of sight, Deedee followed along. “There you go, hands on the chair. Bend at the hips. Good girl. Now, spread your feet a bit. Good, right there.”

Trent’s nerves began to get the better of him. This was the classic porn or spanking pose. He knew it well from hours upon hours of porn viewing. “Please don’t spank me Ma'am. Like I’m trying! I swear.” He could feel the tops of his stockings and the bottom of his ass exposed as he stood there bent over. Slowly, he felt his skirt slip even farther up till his hips were entirely uncovered. Turning his head he tried to see what she was up to.

“Face forward.” The words cut off his movement and **** him to stare down the driveway. A sudden realization that anyone walking by or driving by would be able to see what was going on here caused a whine to slip from his throat. Deedee wanted to laugh at the feminine sound coming from her son, but she knew it was about to be much worse. Reaching her hands up, she slowly hooked one finger through the back of the thong that was currently riding up Tiffany’s ass. Slipping it out to the side, she took the lubed up plug she had prepared inside out from behind her back where she had hidden it. “If you so much as move one step, try to stop me in any way, or tell me to stop, then I blanket every contact you have with images of you sucking a cock. Am I clear sissy?”

Trent’s eyes closed as his face sagged; he just knew she was about to spank him. Chewing on his lip he managed to **** out the agreement she wanted. “Yes Ma’am.” Chewing on his bottom lip he stood there and did everything possible to calm his nerves down. He could feel her hand on his big bouncy cheeks as she spread them. He only had a moment to think that she didn’t need to do that to spank him before he felt the cold metal and lube covered object brush up against his hole. “Oh god, fuck.” The Tiffany voice had fled, this fear was pure Trent.

Suddenly, it got worse. “Hey Deedee, long time no see!” At the bottom of the driveway stood Jessica, their gorgeous next door neighbor. The beautiful blonde was in her mid 30’s but still looked like she was in her 20’s. Trent had spent many nights laying in bed and stroking his three inch cock to thoughts of her. Almost as if she realized what was going on, Jessica paused at the edge of the drive. “Uh, do you need me to come back later? I wanted to ask if Trent was moving back in. If so I could use his help around my house.” Trent had done everything he could to spend extra time around the beautiful woman when he had lived there, hauling boxes, painting, anything really.

“No no, come on up babes! I’m just helping my cute little girlfriend Tiffany here with her garter strap. You know how it is when the back ones come undone. Such a pain.” Deedee’s voice carried past Tiffany as she slowly started to worm the plug into his ass. Her next words were whispered softly for just Tiffany to hear. “You might want to fix your voice and control your facial expressions baby, I’d hate to have to tell Jessica there that her favorite little toy is now just a Barbie doll. Flat crotch and all.”

“Oh my god, I know. I had one come off last weekend at a party. It took me forever to fix.” Jessica looked amazing as she walked up the drive. She looked like she was headed to another party now, clad in a little black dress and some black hidden platform heels. “So, I thought I saw him yesterday when I was on my run, but by the time I got a chance to come by, no one answered the door. I thought I heard the TV though, and your car was at work. So I just figured I’d stop by and see. Wouldn’t want someone breaking into your house or something.” Her heels clicked along the pavement as she strode up into the garage.

In an effort to ignore the feeling of his ass being pushed open by the metal plug in his father’s hands. Trent focused on her walk. What did she do differently than Deedee? Instead of watching her boobs bounce around in the tight and low cut top, he focused on her foot placement, the way her elbows seemed locked in at her sides. In his own mind he tried to rationalize it as staring at a hot older woman. Still, this wasn’t the lustful gaze of a 19 year old, it was the appraising gaze of a woman, even if he didn’t realize it.

“No, he was here.” Deedee rolled her eyes. “He came home and well, let’s just say he reacted badly to the new me.” Deedee no longer had to yell to be heard as Jessica had walked up into the garage fully now. The neighbor kept her distance so as not to infringe on Tiffany’s space while her skirt was hiked up, but she was still much closer than Trent would have preferred. Slowly Deedee worked the plug into Tiffany’s tight virgin asshole.

“Really?” The disappointment in her voice and on her face wasn’t surprising. Jessica had long been a supporter of the LGBTQ community. “I thought better of him. He always used to be so supportive whenever we would talk about the community.”

Trent’s face was a mask as he did everything he could not to cry out in pain as the plug slowly worked its way into his rectum. Doing everything he could to take his mind off the pain and the invasion of his ass, he thought back to the discussions that they had had. Of course he had supported her feelings about the community. Jessica was hot, in fact she was so hot the only thing that could possibly have been hotter was her and another girl. She had even told him about the time she flirted with her boss Rachel at work. As the plug slid home finally, Trent tried to blame the memory of Jessica flirting with another hot business woman for the feelings that hit when the item in his ass finally settled. What he couldn’t explain was the moan that slipped out of his clenched teeth.

Jessica’s eyebrows raised as she took in the scene and the sound coming out of Tiffany before she continued on. “That sucks though hun. I know we talked a bunch about what it would be like with him coming home and how you kept wanting to put off. I’ll bet a surprise like that wasn’t the best way.” Leaning her hip against a set of cabinets in the garage Jessica lounged comfortably, her arms crossed under her breasts, pushing them up even more. “Finally got that garter strap settled huh?” Her gaze said that she believed that about as much as she had believed that Trent just wanted to be helpful each time he came over while she was wearing a bikini.