Tug of War 10

It was still dark when Timothy heard someone calling his name. "Wake up, sweetie" the voice insisted. "We're already late." 

The boy opened his eyes feeling disoriented. "Umm... Susan... What is going on?"

"You have to get up, Timmy."

"What time is it?"

"Ten past five." 

"But school starts at eight! Why are you waking me up so early?" 

"Don't you remember? You agreed to help me with household chores, sleepyhead. So you need to get up now right now. We have no time to waste." 

Still grumbling, Timothy got up and went to the shower. When he returned, Susan handled him some clothes he had never seen before – a short gray top with kitten print, lilac jean shorts with frills at the tips, and a pair of pink slippers. 

"I bought you some new clothes yesterday" the woman said, responding to the boy's inquisitive look. "Just for you to wear at home, of course. You'll see that your father will get really mad when he sees you in them. Now hurry up and get dressed!"

Reluctantly, Timothy did as she asked. He couldn't believe he was wearing women's clothes! He soon noticed that they were very tight, especially the shorts, which compressed his thighs and butt almost like a second skin. "I think you got the wrong size, Susan" he said. "These clothes are too tight and short. Look."

"Don't be silly, Timmy. Those pieces are supposed to be exactly like that. You’ll get used to it. Trust me, sweetie, you look so freaking adorable! However, I see a problem here..."

"W-what problem?"

"Your underwear. This isn't meant to be worn with this kind of clothing, so I can see it through the shorts. Gosh, I knew I should have got you some new underwear, too! I'll do it later, but for now we'll need to improvise. Wait here a minute."

When Susan returned, she was carrying a white piece of clothing. "Try this on. I think it'll fit better."

Timothy looked at the underwear in his hands with apprehension. It wasn't much different from one of his briefs, but still it felt a little softer and more delicate. "That's a pair of panties, isn't it?"

"I guess one could say so..." Susan smiled. "But honestly, darling, this is not like I'm giving you a pair of lace red thongs, right? This is just some bland, cotton underwear. You won't feel any difference."

"B-but whose is it?"

"It’s technically mine, but I've never wore it. This isn't exactly my style, if you don't mind discussing underwear preferences with me... You have no idea how amazing it feels to wear some silk, elegant lingerie set... Would you like to try that, sweetie? I bet you would love it as much as I do… Oh, don't look so mad, silly. I'm just teasing you. Now, are you going to put on that underwear or not?" 

"I don't know Susan..."

"Remember that I'm not here to make you feel uncomfortable, darling. If you think this is too much, that’s totally fine. You can always give up on this little game and..."

"No! I... I'll put it on, Susan" Timothy said, hardly believing is own words. "I'm already wearing women's clothes, so what’s the big deal, r-right? I was being silly. I'll do this in the bathroom."

"Oh, while you are in there, you should try tucking your stuff between your legs, sweetie..."

"W-what?!" Timothy cried out, shocked.

"Your crotch will look way better this way, Timmy... Those shorts were not designed to accommodate an extra volume on the front, if you know what I mean..."

When Timothy returned from what was a very traumatic experience, he sat down so his stepmother could style his hair. He couldn’t deny that it always was very nice and relaxing, despite the nuisance he kept feeling between his legs. Susan combed his hair meticulously, once again putting it in high ponytail. 

When she was done, she allowed Timothy to see his complete look in a mirror. "What you think, honey?"

"I... I don't know what to say, Susan" said the poor boy, stunned. As much as he tried to avoid thinking about it, the only word that could define his appearance now was sissy.

"I know this is hard, but remember that you are supposed to love all this, okay? That's the only way to trick your father."

She then took the boy downstairs, where there was another not so nice surprise waiting for him…

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Hey, guys! Tomorrow I'm going to post "MILF"! :-)