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Chapter 36
by
thosearemysecret
Where is he taking her?
The County Fair
It was county fair time and that meant most of the students in Kyle's class could be found there at night. Kyle wanted the first date to be very public so everyone could see that he had, in his opinion, scored with the hottest girl in school.
"We're going to the county fair," he sent in a text. "I'll pick you up at 6 p.m."
Tanya loved that she'd get to see Kyle but she hated the idea of going to the county fair for exactly the same reason Kyle was excited to bring her. Everyone would see her with him. In spite of her crush and desire to be around him, she was still harboring some of her natural hangups. She tries to type a different suggestion but instead sees the words "Great! Can't wait."
Kyle followed up with "don't dress too fancy or sexy." He didn't want to write that but Maggie was very clear that he had to behave and treat this like it was any other first date. He should go with her, treat her like a gentleman would treat a lady, make out some, and bring her home. Kyle was worried that if she dressed too sexy he'd be tempted to break Maggie's rule.
Plus, Kyle was determined to use as little influence as possible. He plans to try and woo Tanya for real, so if whatever is going on with her wears off she'll still like him. "In fact," he adds to his text, "we're going to the county fair so maybe go farm hand look. Just wear overalls, cowboy boots, and a hat."
Kyle smiles as he sends off the message. He was proud of himself. "Cowgirl" wasn't a look he was particularly into, so he was sure it would reduce his interest in sexy times with Tanya.
Meanwhile, Tanya receives the texts telling her to not dress sexy or fancy followed moments later with new instructions of "just overalls, boots and a hat." The latter overwrites the former in her mind. Tanya frowns reading the message. She doesn't have any of those items in her wardrobe so it means she'll need to go shopping.
It took a while for Tanya to find a store that sold the three items she'd need. However, on the outskirts of the town where it turns rural, there was a Farm and Feed that also sold clothing. When Tanya came out of the changing room wearing "just overalls" and nothing underneath the clerk's eyes practically popped out of her head. Tanya's breasts were on full display with the overall straps barely providing any cover.
"This doesn't seem right," Tanya says to the clerk who is standing in front of her trying to find the words to reply. "I don't mind showing off my body but I probably need something not quite as revealing for going to the county fair but it has to be just overalls, boots, and a hat."
"Oh!" the clerk exclaims finally finding her words. "Um, why don't you go back into the changing room. If you're committed to that....uh....look...I think you really want some night out, going line dancing overalls...not...not those...I'll bring you something."
Tanya does what the clerk says and waits a few minutes until the clerk hands a pair of overalls over the door.
"Come on out when you're dressed," the clerk says and holds her breath.

Tanya comes out and the look is slightly better. The front flap comes up higher but too much shifting in one direction or the other is practically an accident waiting to happen. "Are you sure you want only overalls?" the concerned clerk asks. "Typically a person would wear at the least a tube top underneath."
That seems like an absolutely practical idea to Tanya and phrased any differently she likely would have taken the clerk up on the suggestion. However, Kyle's command stands. "This is exactly what I want."
"Well," the clerk shakes her head "although risky that look really works on you."
Tanya grins at the compliment while looking in the mirror. There's a lot of skin showing but she hears her brother's voice whispering in her head "you like showing off your body." A week ago she never would have even considered wearing something like this but now...she loves how much it shows.
"Mind if I wear it out?" Tanya asks putting her shoes and other clothes in a bag.
"Sure, I guess," the clerk replies and rings up Tanya.
Tanya confidently exits the store in the boots, overalls, and hat. She can feel the mostly male shoppers at the Farm and Feed store ogling her as she leaves. Her heart thumps in her chest at all of the attention. She knows her bare feet in the boots are going to be an issue later, but right now she doesn't mind. This is what she wanted to wear and all of the attention was delicious.
Tanya arrives home to an empty house. She has about an hour before Kyle was scheduled to pick her up, so she does her makeup and fashions the hair sticking our from under the cowboy hat. As she looks in the mirror she can't help but think it's a ridiculous look but at least she'll be noticed. The doorbell rings promptly at 6 p.m.
Kyle expected to see Tanya grumpily dressed in unsexy overalls when she opened the door. He didn't expect her to be dressed in only overalls without a top. His eyes drift over her body and pause briefly on the side boob sticking out from behind the overall front flap. His eyes go down and he admires how tight the pants part of the overalls are. He practically drools staring at her. "H-Hi. Holy....Tanya you're so...incredible. Are you really going out like that?"
"Of course," she replies with a small as she closes the door behind her and gives Kyle a big hug. She's so excited to be going out with her crush. "This is what you wanted t me to wear, isn't it?"
It takes a moment for Kyle to respond. He isn't used to such close affection from Tanya. He breathes in the smell of her shampoo and just holds her for a moment. He could tell her to go inside and change but justifies not doing so by his goal to control her as little as possible during the date. "Of course, Tanya, you look perfect," he whispers in her ear as he forces himself to pull away. "Be a gentleman," he thinks to himself. He escorts Tanya to his car and they head off to the County Fair.
They're both very quiet on the car ride. Kyle because he's terrified of saying anything that could influence Tanya. Tanya because she's anxious about being with Kyle and the fact that she's going to get to show herself off in this new outfit. He parks, but as they get out of the car Kyle has a moment of worry about Tanya's very revealing outfit. Although he appreciates the eye candy he worries that it might be too much for a county fair.
Does he give her his jacket to cover up or stick with the revealing look?
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"Yes"
A girl cannot refuse any request made of her
Updated on Mar 20, 2026
by madmaniac
Created on Mar 20, 2006
by madmaniac
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