The following morning Jeff walked down stairs to find his parents in the kitchen waiting for him. His Dad was sitting at the table, while his Mom...
Jeff had to do a double take upon seeing His Mom. He knew that in terms of women, that she was always on the more attractive side, but after what he did to women, he could tell that she wasn't just attractive anymore. She was hot. Awkwardly hot for Jeff, since she was his Mom.
He tried looking away from her, but she scoffed this and rolled her eyes. His Mom, being the already somewhat tall, dark brown haired beauty was leaning against the counter with her arms folded below her notably larger boobs. She had been a bit larger than average before, but now she had to be at least an H cup. Add them to her still attractively slender figure and then with her ass being lifted up by her new footwear, a pair of black leather, knee high ballet boots that she wore overtop her skinny jeans, and Jeff was finding it hard to look at her.
"Jeff, I just don't understand why you are like this. Do you dislike me? What have I done to deserve this kind of treatment from you?" Asked his Mom, clearly annoyed by something he did, but he wasn't quite sure what that was exactly.
He looked to his Dad for help, but he just sighed and shook his head. "Jeff, I think you have been disrespectful to your Mother for long enough. If you can't even do that, then I fear for how you act with other women, and girls your age. If you can't even stand to look at or even address them directly, then we have a serious problem, and the both of us have agreed that as your parents, it will be best to start taking steps to correct this disrespectful behavior of yours immediately."
Jeff was absolutely confused out of his mind. What did he do? How was he being disrespectful? He had a lot of questions, but no room to ask them, as his Mom immediately followed up his Dad with her part.
"Jeff, we have decided that until you are able to properly interact with girls and women, we will be gradually turning you into one. It's not a conventional method, but this will allow you to have a more empathetic understanding on what it feels like to be ignored and avoided when you spend so much effort to look good for the people you love."
"Wait a minute, what? But I wasn't-" tried to explain Jeff but his Mom held up a hand. "Jeff, we have been watching you for a while now. And it's clear that you are actively avoiding looking at me, even when I am speaking to you. You are even doing it right now as we speak."
"But I'm not trying to be disrespectful towards you" exclaimed Jeff forcing himself to look at his Mom, but then started feeling awkwardly attracted to her, and instinctively looked away.
"You say that, and yet you still are not looking at me" pointed out his Mom.
Jeff knew it was not going to get any better if he didn't say something. So with a deep breath, he forced himself to look her in the eyes and came out with it. "I don't mean to be disrespectful. It's just that you're.... too hot... and it makes me... feel weirdly aroused, since... you're my Mom, and all."
The deafening silence after his confession was the loudest noise Jeff had ever heard. "Jeff, that's disgusting. I'm your Mother! And I don't condone incest. I'm happy to hear that it isn't that you don't hate me, but this is an absolutely worse situation. It's decided, you will be slowly feminized until you are fully adjusted to living as a girl and no longer find me attractive in that kind of way. This will be a long process, but both your Father and I agree that this is for the best, and will not be accepting any arguments or complaints from you. If you try to resist, then we promise you that we will take more drastic measures to ensure that you are complying with this. So don't try and test us and just accept what we say without question."
Jeff was speechless. He was completely in disbelief at the current situation, and was secretly incredibly aroused as well. His deepest kink was going to be played out in real life, in a completely serious manner and not something he can just get out of with a safeword. It was an incredible mixed feeling of excitement and nervousness.
In Jeff's silence, his Father spoke up. "For starters, we are going to begin by having you wear these full time." His Mom then walked over to the closer with a naturally seductive sway to her step as she glided across the floor, clearly a master at walking on tiptoe. She bent at the waist, causing her ass to stick up into the air as she pulled out a shoe box. She then straightened back up and placed the box on the table in front of Jeff.
Jeff gulped and opened the box, revealing a pair of stilletto platform lace up ankle boots that had the same appearance as his current pair of sneakers. These shoes were slightly modified however, as while they did have the laces to tie, there was also a hidden band around the ankle that came together in the front with a matching hole on each end. The box also had a pair of small key locks, each in the shape of a small heart. And it didn't take a genius to guess what they implied.
Jeff looked up at his Mom, too distracted by the shoes to be bothered with her appearance. She nodded and explained. "We don't ever want to see you again without these on unless we give you explicit permission to take them off. When you need to clean yourself, I will remove them for you. But the second you are done, I will put them back on your feet. You also will sleep wearing them, just like how all every other girl does. And when you become more proficient in walking in these, then I will change them out for a taller pair. This will keep going until you are just like me and are living exclusively on tiptoe 24/7, even when cleaning yourself. Now put them on."
Jeff hesitated to move, so his Mom rolled her eyes and forced him into a chair while she put them on for him, tightly tying up the laces before she secured them shut with the locks. To anyone who didn't know, the shoes wouldn't look to be locked onto his feet, as the heart locks just looked like some kind of decoration. And the keyhole was hidden on the backside too, so unless he or his parents told someone, they would never know.
Jeff tried his best to stand up while concealing his erection, but this wasn't easy to do. Hiding his boner was simple, but keeping his balance whike taking steps was not. He could feel how they lifted his ass and caused his back to arch, pushing his chest up and out a bit as well. His Mom then went into a whole detailed explanation on how to walk in heels, from taking slow, careful steps, to power walking, jogging, and even sprinting. Then she went into taking tiny steps, how to move his hips, and then a bunch of concepts and mannerisms that she expected him to have fully learned and implimented as soon as possible.
They then had an awkward breakfast when Jeff was still sorting out his feelings on whether he should be feeling more mad or more elated by the current development as he secretly enjoyed the feeling of his platforms and heels bouncing into each other and the metal foot rest beneath his bar stool.