Chapter 21

Soon after leaving the store Liam found himself not able to hold his tongue any longer. As he replayed the events that just transpired over in his head. Miss Megan had known them, and she had instructed him to flirt with the boy. She had intended for him to be asked out all along. It felt like she was playing a strategy game to maneuver him into place, while the only thing he could focus on was not flipping the board and receiving some punishment. He wished he didn’t feel so weak, if it wasn’t for the vitamin shot, she gave him he was sure he would feel just as tired. Multiple days feeling like this… he had to be fighting something off, but without proper rest it would probably linger. He hoped she caught whatever he had, and her symptoms were much worse.

“Look, I have done everything you have told me to do, but there is zero chance I’m going to go on a date with a boy!” Liam said firmly as he stomped his heeled foot.

Pressing her lips together Megan locked her blue eyes with the feminized young man’s own blue eyes. The threat of prison, the threat of punishments all only seemed to hold sway over Liam for a short time without needing a refresher. They did seem to work longer and longer, but still his will seemed to always come back. Without a word Megan pinched one of his newly pierced ears, pulling as she walked closer to the rail that separated the second floor they were on from the fall to the first story.

Liam found himself almost stumbling in his heels as he was pulled painfully with the tall blonde woman. She pressed him to the metal and glass railing, so that if wasn’t there he would plummet to the first floor of the mall. “I don’t know what has gotten into you missy. You know better than to talk to an adult that way, the only place you get to be in charge is if I set you up to babysit some toddlers and only then if there is no actual adult around. You will be going on a date with the nice boy, you will smile at him, laugh at his jokes. If he wants to hold your hand, then you will hold his hand. If he kisses you, you will kiss him back.”

She watched Liam’s girly face shift between anger, disgust and fear. “If he wasn’t seventeen I would tell you to give him a nice blow job as a thank you and tell him how yummy his cum was. So thank your lucky stars you wont have to do that, but I swear Leah if by the time that date is over if you don’t have his number in your phone with at least a few flirty texts to him we are going to stop at a brothel. I will lie and tell the madam you are eighteen and looking to taste your first cock. Or maybe we will stop at a sex store to buy two of those pison machines that you attach a dildo to. I can tie you up and have one setup for your ass and the other your mouth. If you wont behave like I tell you to that could be a good way for you to spend the rest of the summer and much cheaper than buying you a wardrobe.”

When she stopped talking Megan leaned a little closer as she narrowed her eyes. “Now tell me, should I treat you like Leah the sweet boy crazy teen girl, or the alternatives?” She wasn’t even sure if the brothel would do anything without ID proving Leah was eighteen, something she did not have or if the device she was talking about was available to just purchase like that, but she didn’t think Liam would know either.

“You wouldn’t!?” Liam felt like his voice was failing him as his overactive imagination showed him what she was talking about in vivid detail.

“Oh I would, and then after you were fucked all summer from the front and behind you would have one chance to convince me not to turn you over to the police. Do you think you could say anything to convince me not to turn you over after I gave you chance after chance to get out of going to prison for what you did?”

“But I didn’t…” Liam trailed off, he had already tried telling her what happened, but she didn’t believe him. “Nooo…” He drew out the word feeling sullen.

“Then what will you do?” Megan said, her voice a soft whisper that even Liam could hardly hear as close as they were together.

Earlier he had thought playing the part would get him some leeway, but he had ruined that because he couldn’t hold in his anger. “Go dress shopping with you Miss Megan and then go on the lunch date with the cute boy?”

“Good, now take out your book and mark down two strikes, but because I think the two of you will make such a cute couple I will tell you what. If you can convince him to come to church with us on Sunday you can have that reduced back down to one strike.”

“Church?”

“Have we not talked about this Leah?” Megan asked, honestly not sure if she had brought up the subject or not. “I have started attending service again and as a good Christian girl you will be going as well. Now come along, we have so many outfits for you to try on.”

The two didn’t just go into one department store, they went from one and then to another. The mall had five major department stores and she had promised him to hit everyone. “Don’t worry Leah, we will hit all the department stores today so you can see the different outfits. Maybe this weekend we can come back so we can do some more shopping, I bet you would just love that.”

Trying on the feminine clothes was not his idea of a good time, his only saving grace was it was early on a weekday so there were few people around to his embarrassment. With each outfit he tried on he found Miss Megan opening one of the shoe boxes and telling him to try on this pair, or that with the outfit. She had handed him a pair of four inch heeled ankle boots, that were light brown leather, with a dark brown for the heel and toe and a leather strap going across the ankle to look like it held it on, while it really just had a zipper on the inside of the foot. It was to go with an outfit that consisted of a long sleeved black blouse with a keyhole opening to see just a hint of breast. A light brown leather pleated skirt, paired with a black thin belt. After he had it all on she opened up a pair of black pantyhose, telling him to try them on with the outfit.

With the package open he knew at least they would be purchased. Holding them he made a sour face, the flirty leather skirt was so short that it made him wonder how girls could stand it, let alone when they wore a mini skirt. He had always loved seeing their long legs in short skirts, but never wanted to see his own that way. The only good thing about the girly clothes were the soft cotton panties and even that he would never admit out loud.

That outfit had been moved to the yes pile, that seemed to be getting much more clothes than the no or maybe. The next thing he wore that Miss Megan gushed over and he did too to stay in character was one he would have a hard time describing to anyone. It was a dress that had a black skirt that went almost to his knees, made to look like it wrapped around and buttoned on his left front side and where it split at the bottom you could see white and black horizontal stripes that matched the top part of the dress. The only thing that broke up the stripes was the solid black collar that had matching buttons to the skirt portion. With it Miss Megan had handed him to wear the white and black pinup looking heels Jeremy had picked out for him.

“This outfit is a must, you look beautiful in it Leah, in fact I think Jeremy might like to see you in it for your date today. What do you think?”

“I think I would love this outfit even if he hated it, but I really hope he thinks I’m as beautiful in it as you say Miss Megan.” The dress was tight enough to really highlight his pushup bra enhanced chest. If it wasn’t him looking this way, or him feeling the sway of his chest along with the skirt brushing across his legs he would have liked the sight.

“Oh, I’m sure he will, but we will have to get you a slip to go under the dress. Not like we weren’t going to get you some slips and half slips before we were done.” She laughed, and so did Liam though he wasn’t sure why she was laughing.

In another store he tried on a white bag dress with a tight jean jacket. At first Liam thought the jacket already had it’s sleeves rolled up, but upon closer inspection it was just made to look that way and when he put it on he realized it only came down to mid back, along with that it was too thin to offer much protection or warmth. It was less a jacket and more a fashion accessory.

When they were all done the pair started to make their way to the car to drop off their goods. At his point both of them had to carry the bags and even then both were fully loaded up. Liam was trying to prepare himself to be hanging around the teen boy when his tormentor stopped, looking in a small shop, at it’s window display. “Come inside Leah, I think you will look just amazing in that.” Glancing in the window display was a navy blue dress that came down to below the display's knees. It had a tied bow at the left hip and the navy fabric stopped just above where its breasts were, with a sheer fabric continuing up to its neck. Allowing a hint of the dummy's breasts to be shown, while still allowing for modesty. Then atop its head was a little circle flat hat with a bow on it. The outfit looked ridiculous to Leah, but instead of voicing his actual opinion and earning the woman’s wrath once more he smiled broadly to show off his braces as he followed her in, acting as if he was full of mirth as he giggled. “That looks just so pretty Miss Megan!”

When he put it on the dress ended up coming just a little above his knees instead of below them like the dress up dummy and just so lucky for him in one of the shoe boxes was a pair of navy shoes, that had a five inch stiletto heel. When the store attendant put the little hat on his head he looked in the mirror after letting Miss Megan take some photos, much like every outfit he tried on. To him it looked like the girl in the mirror was about to go to the Kentucky derby. At this point he had learned his opinion didn’t really matter for what would be purchased and what would not, but the happier he acted and more he pretended to like an outfit the less strict and commanding Miss Megan was.

“This dress is lovely, Miss Megan I just love it! Do you think I could get it? I don’t know where I would wear it, but it is just so pretty.”

“If you love it that much Leah I don’t know how I can say no to you, though I see a similar dress with lighter colors I think you would love just as much. It would be perfect for a garden party, how about we get both?”

The price of just one of the dresses was just over two hundred dollars after taxes. The cost of todays shopping was extravagant and he knew for a fact his brother didn’t have the money to cover the cost of the day. Miss Megan was spending her own money, left and right just to dress him up like some Barbie doll, she had to be because there was just no way Chuck’s credit card was going to cover all this.

Loading bag after bag into the back of the SUV, Liam shook his head slightly at how much they had gotten. “Thank you for today's shopping trip Miss Megan, I had just so much fun with you!” Liam did his best to sound like today was the best day of his life.

“Aww, you are welcome Leah, but I know a girl like you can never be really done with shopping. So after your date we have the last two department stores to hit still, and at least one more shop. Can’t have you without a bikini for the summer can we?”

“That would be horrible.” He said truthfully at the idea of getting a bikini.

“Don’t worry dear, we will get you a few. Do you think Jeremy would like to come and see you try them on?”

“Eeep!” Liam squeaked, feeling his face turn red at the idea of putting on something so girly and intimate let alone in front of a teen boy.

“That might be a little much for your first date, we don’t want Christine thinking you are trying to seduce him.”