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The Girl Next Door (SalesGirlAnna x Alexander May)

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SalesGirlAnna

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Joined
Jun 14, 2011
Annabelle Stewart walked into her home after a long day at work. She was an executive vice president in charge of sales of a clothing company. She pulled her long red hair out of its bun and started to head up the stairs of her suburban home. She was wearing a blue blazer, a matching skirt that goes a bit past her knees, a white blouse, white stockings, 2" black Mary Jane pumps, pearl necklace and earrings. She was 33 years old 5' 7" 110 lbs. 34b.

She opened the door to her bedroom and saw the boy next door, going through her dresser drawers. His parents were good friends of hers and they each had keys to the others home. "WHAT THE HELL ARE YOU DOING IN MY HOUSE?!" She screamed.
 
Jace Stark didn't usually do this sort of thing, and the only reason he'd done it today was because of a stupid bet with one of his friends. He'd assumed it would be easy, in and out. After all, his parents had keys to her house. He'd seen her a few times and he knew she wasn't supposed to be home yet. Usually she got home about half an hour later, he never would've guessed that she'd actually catch him. He was wearing the same thing he'd worn to school, a plain black shirt and a pair of jeans. His eyes were a light shade of blue, and his hair golden blonde. He'd always taken care of his body and he was about 5'5 weighing in about 130 lbs at 16 years old.

He turned around too quickly, some of her clothes still in his hands. "I-uh-I'm-uhh...I'm here to-." He came up with nothing at the same time that he realized he was stil holding her bra and a piece of langerie, and hid it behind his back as if she hadn't already seen him holding the items of clothing.
 
"Your hear to what?!" Annabelle marched over to him and grabbed her clothes out of his hands... "Tell me why I shouldn't call your parents... No forget your parents... Tell me why I shouldn't call the police..." She crossed her arms across her chest and waited for an answer.
 
His eyes widened at the suggestion at her calling his parents, and then at the police he started shaking his head, clasping his hands togeter. "No no no! Please! I'll do anything you want just please don't call my parents or the cops!!! Please! If my parents get another excuse they'll send me off to military school, and if I get involved with the cops my chances of a good scholarship are ruined!" He could see his whole future burning to a crisp, and all because of some stupid bet.
 
Annabelle smiled. I knew that Jace's parents were leaving the next day and would be gone for most of the summer. They would be in Europe for business and pleasure..."OK... Come back tomorrow after your parents head to the airport and we'll discuss your punishment..."
 
"O-ok..." He was both worried and relieved. Why would she just let him go like that? It seemed odd...it didn't stop him from heading home, and going about his normal schedule.
 
The next morning she was in her kitchen reading the paper and drinking coffee. She was wearing a simple blue blouse, blue slacks, and black ballet flats. She heard the car next door pull out of the driveway and she sat there patiently waiting for him to return.
 
When he'd woken up for the morning, he'd put a smile on his face and promised his parents he'd be good, and tried to stall them a few times, fearful of what Anna would do. When the time had come that he'd run out of things to stall them and they left, he went over to her house and stood before the door staring for a minute or so before he sighed and knocked on it lightly.
 
Annabelle walked to the door, opened it and gave Jace a big smile, "Jace! Glad you could make it come in..." She open the door for him. She took him into the living room, "Have a seat..." she pointed to the couch and she took a seat in the chair next to the couch. "I've been giving some thought to your punishment, Jace, and I've come up with the perfect punishment... While your parents are gone, you will live here... as my niece..."
 
He didn't like the way she smiled or greeted him. Glad he could make it indeed...as if he had a choice. When she told him to take a seat, he did, and listened to what she had to say, frowning slightly. "Wait....your niece? Doesn't niece mean that I...." He trailed off as he realized what she was getting at.
 
Annabelle smiled, "That's right... you will be living here and dressing like a girl... You wanted my clothes so badly yesterday... I figured that you must be a cross dresser and I figured I'd help you live out your fantasy..."
 
He was at a loss for words...as well as options. He could either do it....or go to jail. Neither seemed ideal to him but he knew which was better. "I....And........." He could think of nothing to say, and decided to simply say nothing and look to her unsure of what to do know. "Umm...and I...what do....when?"
 
Annabelle wasn't sure what he was trying to ask her... "Yes... well... We need to come up with a new name for you..." Annabelle thought for a moment... "I've got it... Jade... For this summer you will be my niece, Jade... OK, Jade... First things first... We have to get you some clothes so lets head upstairs and see how well you fit into my clothes..."
 
Annabelle took Jade by the hand and escorted her up the stairs to her bedroom. Once they were inside Annabelle started to look through her drawers. "OK, Jade... Strip... Get those silly boy clothes off... You won't be wearing them anytime soon..."
 
He did as she asked, taking off his shoes and socks followed by his shirt and then by his pants. He took them off and dropped them all at his feet for lack of better place to put them.
 
Annabelle took out a bra and panties set. They were purple satin and lace... She turned and saw he still had his underwear on... "Come on, Jade... Get that boy underwear off..." Annabelle then held the bra and panties out to for him to put on. "Try those on for starters..."
 
He took those off as well before he took the set from her, putting on the panties first and then the bra. They were a tight fit but they fit none the less. As he put them on, he told himself he was doing it because she was making him, even though it was arousing him quite a bit to dress this way.
 
Annabelle watched as he put the bra and panties on. She made sure he tucked his penis between his legs to keep the bulge from showing... "Hmm... Looks like we need to go up a size..." Annabelle reached into her drawer and put a couple of foam bra inserts into the bra. Annabelle went into her closet and came back with a pink top, a black pleated skirt, and a pair of black Mary Jane Flats. "Put these on and we'll see out they fit..."
 
He frowned as he glanced at them, but he moved to put them on as well. He managed to get them on, but they were a tight fit as well. The only exception was the flats. They fit almost perfectly.
 
Annabelle watched as she dressed, "OK... So we know we are going to have to go up a size or two on the clothes... But the shoes fit you well..." Then Annabelle then guided Jade over to her vanity... "Have you had any experience with putting on makeup?"
 
He frowned as he looked at all the different types of makeup, jewelry, and other assorted baubles Anna owned. "No....as a matter of fact I don't have any experience with it."
 
"OK..." Said Annabelle, "Make sure you pay close attention, because soon you'll have to do this all by yourself."

She explained to Jade how to apply make up and all of the do's and don'ts after several minutes Annabelle was done... "And that's that. Have a look in the mirror..."
 
He looked at himself in the mirror, just looking. Given a little while, he'd be the perfect girl in these clothes and makeup. The only reason he didn't was because his hair was to short. He'd probably have to wear a wig until his hair grew out naturaly. With the rate his hair grew, that'd probably be in a week.
 
"You are in luck... I have a blond wig that I used for a Halloween costume last year.." Annabelle walked into the closet and came back with a blond shoulder length wig She placed it on her head and styled it a little... "Very nice... Take a look..." She turned Jade to face the mirror.
 
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