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Chapter 9

Is Kylie ready?

Of course not.

"I..." Kylie's dark tan skin started to turn red. "I'm not sure." Show lowered her head, embarrassed.

Jill sat up. "Come here darling." she ordered her daughter and Kylie listened, shuffling up toward her mother and giving her a big hug. "It's alright." Jill brushed a stray strand of curly hair out of her daughter's face. "It's okay to be nervous."

Kylie took a deep breath and felt comfort as her mother's hand caressed her cheek. She closed her eyes and felt the calm wash over her as her mom's fingertips worked their way down her neck. It felt nice.

But her nervousness returned as she felt her mom's hand start to caress the top of her chest then push down under her t-shirt and cup her small left breast. Here eyes flung open. She wanted to be the type of woman her mom wanted her to be, but this felt wrong. This was wrong. Even as Kylie felt her nipple harden under her mother's palm, she knew something wasn't right.

"Shhhh" Jill stayed comforting. "There's one thing I've learned darling. And that's that life is about pleasure. It doesn't matter where that pleasure comes from or how society looks down on it. What only matters is that you get it as much as you can. We're going to prepare you for tomorrow, okay?"

Kylie nodded, letting out a barely audible, "okay," not knowing what came next, but not expecting her mom to slip her hand back out of her shirt and grab her cell phone. Kylie looked on confused as Jill dialed a number and started to talk.

"Hi Frank, it's Jill... I'm sorry, I know it's late... I need some help... at the store.... great! see you in twenty minutes." And Jill hung up the phone giving her daughter a smile.

Kylie returned it with a perplexed look.

"I've been with a lot of men," Jill explained, "And I've made a lot of friends. Not just people to fuck, but real friends.... and friends help you when you need it."

Kylie didn't understand.

"Put on your shoes." Jill added. "We're going shopping."


Twenty minutes later, as promised, Jill and Kylie pulled up to a small little clothing boutique in a nice part of town called "Lips." Nothing seemed odd about it, other than being almost 1:30 in the morning.

Jill smiled at her daughter, "If we want you to feel confident and sexy tomorrow, we have to make you look sexy."

And Kylie thought she started to understand. But it still seemed like an odd thing to be doing in the middle of the night. The door to "Lips" opened and a gentle-looking man with gray hair and a welcoming face peered out at them.

"Come in." He grinned, hugging Jill and then politely shaking Kylie's hand "It's a pleasure to meet you Miss Kylie. I'm glad I could help." So far Kylie felt confused and weirded-out but also oddly comfortable. Her mom was being nice and this man was being very kind.

When Jill walked her over to the lingerie section and Kylie started to fill a kind of dread build in her gut, the nice man sensed it and excused himself. It made Kylie feel better.

"Let start with this one." Jill turned toward Kylie holding up a skimpy piece of underwear.

Kylie winced. She'd worn nice underwear before, but never with the intent of showing her body off to dozens of men. This was very new for her. "That's like practically see-through." She said.

Jill took a look at it, "I thought it was all see through." And smiled.

And mother and daughter shopped for a good hour, Jill always suggesting something revealing, Kylie resisting, until they found an outfit they could agree on.

Kylie stared at herself in a mirror, sporting a short, tight, white dress with a low-neckline and a pair of white over-the-knee lace socks. She could tell that her mother was happy with it.

"It's perfect. It's white, which says that you're pure." Jill said eagerly.

Kylie stared at herself in the mirror closely. She could see her dark nipples through the fabric. "You can see my breasts in it." She said.

"Which says that you're not going to be pure for long." Jill smiled again.

And Kylie couldn't help but smile back. She was finally feeling a little comfortable. She stripped off the dress, put her normal clothes back on and headed with her mom to the register where the kind man was waiting for them.

"Good choice" he said when he saw the dress, taking another look up and down at Kylie. Kylie smiled at it. She'd have been embarrassed by it just an hour earlier. Now she felt flattered. "Will you be paying now?" The man asked.

"Of course." Jill answered, pulling her shirt off over her head.

Kylie froze. "Wait!" She shouted. Her mother and the kind man turned toward her. "What's going on?" she demanded.

"Oh darling. I haven't paid Frank in cash for years. I haven't paid for much in cash for years."

Kylie grimaced. "I guess I'll wait in the car." as she started backing away.

"Absolutely not!" Jill snapped as she slid down her jeans, revealing a shapely ass for her age, clad in a pair of cotton panties. "We said we're preparing you for tomorrow and this is part of that. Don't worry, we won't spoil you. Isn't that right?"

"That's right." the kind man responded. "We'll be very gentle. Now come over here and pull down your Mommy's panties."

Kylie resisted.

"I don't think you understand how this works, hon." Jill explained. "Frank tells us what to do and we do it." Jill stood facing her daughter.

Slowly, Kylie walked over, taking a good look at her mother and Frank. Two friendly faces. This was happening. She knelt down in front of her mom, slipped her fingers into the sides of the cotton panties and pulled them down, staring at her mother's bald snatch.

Now what?

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