Tug of War 19

When Saturday finally arrived, Susan once again woke up her stepson before sunrise. "Come on, Susan" Timothy complained, covering his head with a blanket. "Let me sleep a little more. I don't have to go to the school today!"

"I know, sleepyhead. But we have a busy day ahead. A woman's work never ends, you know. So wake and shine now!"

The boy reluctantly got up and went to the bathroom. After a quick shower, he returned to his room and gasped when he saw what was on his bed. "You're not really expecting me to wear this, are you?" he asked in horror, pointing to a light pink piece of clothing. 

"Do not even think about starting it again, young lady! Don’t you remember what we talked about two days ago?"

"I remember, of course, but... I can't wear a bra!"

"Why not? Every girl wears a bra."

"I'm not a girl, Susan!"

The woman sighed, annoyed. "Look, Timmy, if you're going to keep acting this way, why don't you simply give up on this game and go to that military academy like your father wants so badly?"

"W-what?"

"I've told you a million times... You won't defeat him unless you really strive for it. You have to believe that you want to be a girl. Instead of that, you're making a big fuss about such a silly thing like wearing a plain training bra."

"I'm sorry, Susan" the boy said, looking down at his polished feet. "You're right, I guess, but... I'll look silly wearing a bra!" he claimed, convinced it was a good excuse. "It's not like I have something to fill the cups, right?"

"Oh, sweetie, you truly still have a lot to learn!" the woman said, gazing at him with something that resembled pity. "Do you honestly think that all young ladies can naturally fill their bra cups?"

"Umm... Yes?" Timothy said, feeling stupid and embarrassed since he was making his inexperience with girls even more evident. 

"You're mistaken! A lot of girls your age need some help in this regard, since their bodies take a little longer to develop. That's why there are bra pads inserts" she said, showing the boy two small pieces of silicone. Timothy stared at those things wide-eyed. It was obvious that Susan was really committed to making their little scheme a success. She seemed to always have everything planned ahead… 

"So, are you going to a good girl and try on your bra now, pretty please?"

"Fine, Susan!" Timothy finally gave in, knowing it was useless to keep resisting. He first put on the pair of briefs matching panties, remembering to tuck his private parts between his legs. Then, he grabbed the bra and slipped his arms into the straps, but he had no idea how he was supposed to fasten it at his back. 

Susan then came to his aid. "Since this is a new thing for you, it’ll be easier if you fasten it in front, and then turn it around. Let me show you". And so she did, while Timothy stood there, once again feeling like a perfect sissy. "See? This is how you’re supposed to do it. Now I'll take your bra off again so you can put it on yourself." 

It took three attempts until the woman was finally satisfied with the boy's efforts. Then, she helped him adjust the straps, and inserted the pads into the cups. They weren't that big. Susan told him his breasts were just a-cup size… for now. But even so, Timothy felt it was very weird having that extra volume on his chest.

"You'll get used to it, honey" the woman assured him when she noticed his discomfort. "In a few days you won't even realize that you are wearing a bra, but at the same time you won't be able to live without the support it provide to your girls" she playfully added. "Do you want to see how you look?"

"Umm... Yeah, why not..." 

"Alright, but first let's fix your hair and makeup."

When Timothy was allowed to stand in front of the mirror, it was another shocking experience for him. With the inserts on, it really seemed like he had boobs – small ones, true, but still boobs! The illusion was disturbingly perfect. This, added to his styled hair, make-up, painted nails and hairless body, made him look even more like a girl. 

He took a deep breath, trying to calm down. This was only a temporary situation… He just needed to be resolute and brave and pretty soon it would be over. However, he had no idea how brave he would need to be that morning because Susan still had many surprises planned for him…