Tug of War 32

"This is not working, Susan" Timothy complained once again, desolate. "We need to do something about it."

It was late afternoon on Friday, which meant that another week was coming to an end, and Timothy hadn't yet defeated his father. This situation was driving him crazy. As if the fact that he had to dress and act like a girl all the time while he was at home wasn't enough, that charade was also causing complications for him at school. 

The boy had never been as bullied as now, which definitely was having a big impact on him. He felt like crying with worrying frequency, not to mention how helpless he felt before his tormentors. He was sure he would be even more screwed if it weren't for Martin, his friend, who had already saved his ass a few times now. 

However, even his friendship had gotten shaken recently, as Timothy painfully recalled… 

Everything had happened earlier that day, when Martin approached Timothy before their first class. "Hey, Tim" he said, looking embarrassed, which was completely out of character for him. "Can we talk for a minute?" 

"Sure, man!" Timothy replied. "Before anything else, though, I'd like to... well... I'd like to thank you for what you did yesterday, you know… at the basketball practice. I owe you one, man."

"What?" Martin asked, looking confused for a moment. "Ah, yeah, the basketball practice! Don’t worry about that, man" he waved his hand, as if he wanted to dismiss something unimportant. "I just gave Adam what he deserved."

"Yeah, right, but thanks, anyway! So, what do you what to talk about?"

"Well..." Martin started, scratching the back of his head. "Listen, Tim, is there something you want to tell me?" 

"I don't understand, man. It was you who said you wanted to talk to me."

"I know, but what I mean is... You've been changing, Tim. Even I can see that. Your hair, your nails, your skin... Everything!"

"W-what are you trying to imply here?" Timothy asked, the fear growing inside him.

"I'm not trying to imply anything. I just want to say that whatever is going on, you can count on me. Really, no matter what. You know that, right?"

In other circumstances, being able to think straight, Timothy would probably have appreciated hearing such words. At that moment, though, he was once again overcome by his emotions and wounded ego. "So, what you are saying is that this is okay for you if I become a sissy?" he snapped, angry. 

"A sissy?! Are you crazy, man? I'd never call you that!" 

"Oh, really? You talk about my hair, nails, skin, and I am the crazy one here? Now what? Are you going to say that I am overacting like some hysterical faggot?"

"Calm down, man!" Martin said, holding his friend tightly by the shoulders. "It’s me, okay? We've been friends since kindergarten! I’d never say that you are acting or that you look like a sissy. In fact, you look… you look…"  

"I look what, man? And why are you staring at me like that? You know what? Get lost, Martin! I don't know if you came here to mock me or if you went crazy for good, but get out of my way… Now!"

Remembering that incident one more time, Timothy now was sure he had screwed everything. Martin was just trying to support him, after all. It was just that it hurt so much to hear from his best friend how much he was changing… And 'changing', in this case, meant that he was looking less and less like a guy.  

"We definitely need to try something new, Susan" he insisted, as he painted his nails. "I can't keep living like this." 

"Sweetie..." Susan softly said, stroking the boy's hair. "I know this situation is hard for you, but you need..." 

"Stop it! I don't to hear again that I need to be patient! I want to beat my father as soon as possible… even better if I can do that tonight!"

"Well, sweetie, if you're in such a hurry, you know very well what I think you should do." 

"No, not that!" Timothy shook his head, annoyed. 

"In this case" Susan sighed. "There is little I can do other than say that you need to be patient one more time. But you know you're being foolishly stubborn, right? You've been wearing panties and bras, dresses, high heels... What's the matter of wearing the pretty nightie I gave you?" 

Timothy had heard his stepmother repeating that all week long, but in each of those occasions he had flatly refused to even try that damned nightwear. "The matter is that you don’t expect me to simply wear that thing, right?" he said, grinding his teeth. "You expect me to wear that thing in front of my father!"

"Well, isn't that the whole point? Unless you're planning to just have some fun, what's the use of wearing it away from his father's eyes?" 

"But this is too much, Susan! Don’t you understand? If my father sees me wearing underwear... female underwear... I don't think I'll ever recover from this trauma!"

"Don’t be such a drama queen, Tiffany! This is just clothing. I assure you that you'll be perfectly fine. Your father, on the other hand, I'm not so sure about him... Perhaps he's the one who will actually get traumatized… so traumatized that he'll do anything for you to stop dressing like a girl. Just think about it. A man like your father saying his only son wearing such a beautiful and feminine garment… So, what you say? Do you want to be beat him tonight or not?" 

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About an hour later, Timothy was standing in the living room wearing the white satin nightie that ended just below his crotch and had a low-cut neckline. He thought he couldn’t feel more exposed than that, and cursed himself for always doing what his stepmother suggested to him to do. 

"Wait, Susan. How can I wear a bra with this nightie?" he had asked a little earlier, while he was getting dressed, hardly believing he was discussing such matters. "It will look all wrong!"

"Good point, young lady" Susan said, smiling proudly. "It seems you're on the way to becoming a women's fashion expect, aren't you? You won’t need a bra tonight, though. This nightie has a build-in bra, so you can settle your inserts in this. I'll show you how." 

To complete the outfit, Susan gave him another pair of white stockings, 2-inch mule heels with faux fluffy fur, and a new pair of white bikini panties. "Those are lace panties!" he protested, holding the delicate piece with his fingertips in horror.

"That's right, sweetie. The thing is that you can't wear cotton panties with this nightwear. That would be a crime, as you know very well! I just praised you fashion sense, remember? Use it again. Now be a good girl and get dressed. Oh, and don't forget to tuck your little stuff between your legs, as usual."

Once Timothy was ready, he finally went downstairs and couldn't help it but felt pleasurable chills all the way because of the nightie. Man, it feels as good as the stockings, he thought, angry at himself. He knew he was a guy and shouldn't be enjoying wearing women's clothing that much, but it would be a lot easier if he didn’t get so thrilled whenever he was while wearing soft materials. 

At the living room, Timothy and Susan didn't have to wait long until the other family member arrived. When Richard entered the house, the first thing he was his son – wearing lingerie and posing like a real model as Susan kept saying how stunning he looked. 

"I think it's time for me to have a little talk with my beloved daughter" he said, advancing toward the boy. "Or should I say my beloved niece? Why do you look so surprised, Tiffany? Yes, I just met Mrs. Bennett, and she told me some very interesting stories about you…"