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Caught! (SalesGirlAnna x megajosh19)

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SalesGirlAnna

Star
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.
 
Joshua Master was a shy young 19 year old man who lived with his parents. he stood at 5'6" with dirty blonde hair that went down to his mid back and shockingly bright blue eyes. Josh had a strange love for his neighbor Ms.Stewart but not just for her but, also her clothes. So much so that he would sneak into her house while she was at work and admire them. The last thing he ever expected was for her to come home early from work.

"I.....I can explain just give me a minute please you see i love the way your clothes look and i wanted to see how they looked on me so i was going to hold them up to the mirror."
 
Annabelle listened... "I see... I see..." She thought for a moment... "So, you want to be a cross dresser..." Then she remembers that Joshua'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..."I won't tell your Parents... but if you really want to be a cross dresser I want you to come back here tomorrow after he leaves for the airport... You are going to be spending the summer with me as my niece..."
 
"Alright Ma'am i will be here after my parentes leave tomorrow."

Josh then went home and wasted the rest of the day. the next morning dressed in a plain white T-shirt and a pair of slacks Josh wished his paernts a safe trip and waited till he saw them turn the corner, he then proceded to lock his house up and put the key in his pocket.

"Ok all ready to go now I just need to go next door"

Josh walked to to Annabelle's front dor and reached for the doorbell but froze wondering if this is a good idea or not before steeling himself and pushing the doorbell sealing his fate for the summer.
 
Annabelle smiled when she opened the door and saw Sean standing there, "Come in Josh... Come in..." once the door was closed, "So Josh... Have you given any thought on what you would like for a girl's name?"
 
Josh stood there blinking not expecting a question like that.
"No Ma'am i haven't thought of one i never really think this would be happening. Sorry about that it is still new to me to have someone know my secret."
He stood there waiting to be scolded lik a child thinking Annabelle was mad at him.
 
"That's all right," Said Annabelle, "I'll just have to come up with a name for you... What do you think of Lilly? Come with me..." Annabelle then guided Lilly upstairs to her bedroom. "OK, Lilly... Today you are going to live every girls dream day... I'm going to take you to the salon to get your hair done then we are going to go shopping for some new clothes for you... But, you can't wear what you are wearing now... So, I need you to take off all your clothes and we'll see how well you fit in my clothes..." Annabelle then started looking through her dresser for some underwear for Lilly to wear...
 
Josh now named Lilly blushed a little at the name and how feminine it sounded. He then heard about his hair needing to be done, while Annabelle was looking for underware he decided to voice his opinion. "No offense Ms. Stewart but what is wrong with my hair?" He waited for her to answer as he also wanted to know what she was picking out.
 
Annabelle turned... "Well, it's not really cut in a woman's style it need's to be trimmed and styled." Annabelle handed Lilly a blue satin and lace bra with matching bikini cut panties. "See how these fit while I get you some clothes..."
 
Lillly stared at the bra and panties wondering how he was going to fit in the bra with a lack of breasts but figured Annabelle might have something planned. He then started to strip his clothing when Annabelle wasn't looking and after slid the blue bikini cut panties up his legs they were a bit big around the hips but otherwise fit like a glove. Lilly then tried to get the bra on but had some trouble. "Ms.Stewart i need a bit of help" he asked while his face was quite red for needing to ask.
 
Annabelle came out of the closet with a purple top, a black pleated skirt, and a pair of black Mary Jane Flats. She smiled as she looked at Lilly... "First loosen the straps..." Annabelle did this and handed the bra back to her, "Now put it on backwards then hook it together turn the bra around so the cups are in front, put your arms in the strap loops and then adjust the straps." Once Lilly did that, Annabelle asked, "So... How does everything fit?"
 
Lilly stood their in the matching bra and panties feeling both awkward and complete. She then took the pleated skirt and purple top from Annnabelle and started to put them on they seamed to fit okay but the top was loose in the chest area but, that as only because she had no breasts actually being male. Lilly then looked at herself in the mirror and went wide eyed at the tomboyish looking girl staring back.
"Wel-well they fit okay although the bra feels a bit loo-loose since i don't have breasts." Lilly replied with a stutter she long thought she had gotten rid of.
 
Annabelle reached into her drawer and took out a couple of breast pads and put them into Lilly's bra... "How's that?"
 
Annabelle smiled, "You look wonderful... Lilly... Alright, if you are ready let's get going..." Annabelle smiled as she started to make her way out of the bedroom door.
 
"If you like..." Said Annabelle as she got into the car. A short time later they arrived at the hair salon. Emily the woman who owned the salon walked up to them, "Hey, Annabelle... What Can I do for you today?"

"Well, my niece Lilly just came into town and well as you can she she needs a new hair style"

Emily looked over at Lilly and smiled, "Sure... Come with me..." Emily took her hand, "So dear what kind of look were you going for?"
 
Lilly blushed as the woman took her hand and led her to a chair. "Well i was thinking of getting it styled however you saw fit but, first i was thinking of dyeing it a golden blonde color for something a little new if it would be much trouble?" Lilly asked a bit shyly.

For the next hour Lilly's hair was dyed the color she asked and her hair layered and trimed but the length kept her hair had more volume and bounce, she had a couple long bamgs framing her face and her forehead was not hidden, and it was now a beautiful golden sunshine blonde color. "Well Aunt Annabelle how does it look I like it at least?" Lilly asked Annabelle while twirling a bit of her hair around a finger.
 
Annabelle smiled, "You look great, Lilly... Great job as usual Emily..." Annabelle paid Emily and she and Lilly headed to the mall. "Now, time to get you a proper wardrobe. Where should we start? Clothes, underwear or shoes?"
 
Annabelle nodded, "I agree. Sounds like a plan..." Soon they reached their first stop, Victoria's Secret..."This is wear I get all my lingerie...." Then the two headed inside. "Get what ever you think you need. But, no thongs..." Annabelle whispered into Lilly's ear. "They won't keep your cock down."
 
Lilly blushed a deep scalet when Annabelle whispered in her ear. "O-Ok Au-Aunt Ann-Annabelle." she stutered out. Lilly then went around picking out nighties panties and some stokings and went to try them on. She found that hey fit like a glove and changed into her skirt and top. "Ok Ma'am I am finished. They then procceded to check out and go to the next store.
 
Annabelle smiled as Lilly went around picking out items. Annabelle could tell that Lilly was truly happy. After Annabelle paid for Lilly's purcheses they headed to the shoe store and the sales man said, "Hello, ladies... what can I do for you?"

Annabelle smiled, "My niece here needs some shoes..."

"OK..." said the salesman, "Follow me..." He took Lilly by the hand and guided her over to some chairs.

The salesman sat down in front Lilly and said "Now, what were you looking for, Miss?"

Annabelle sat down next to Lilly and said, "We are going to need several pairs of shoes. My niece lost everything in a fire and we need to replace her stuff."

The salesman nodded, "OK... We just need to get a size here..." The salesman took Lilly's left foot. Removed the shoe placed her foot into the measuring device "Size 8... I'll be right back."

The salesman then headed to the back room.
 
Lilly fidgeted in her chair as she waited for the salesman to come back. Lilly was nervous that she would fall in a pair of heels and her secret would be uncovered.
When the salesmen came back he was holding 3 different boxes each containing a different sizes of heels a 2" that she tried on and walked in easily, a 3" that went as easily as the 2" heel and last was a 5" which she had trouble with at first but after a bit of practice she was walking in them fine.
After she picked out several pairs of heels she was brought some tennis shoes which she got 3 different pairs of. In total she had gotten 16 pairs of shoes, 6 2" heels, 5 3" heels' 2 5" heels and the three tennis shoes. "Thank you so much sir." Lilly said as Annabelle paid for the shoes.
 
Annabelle smiled as she watched Lilly. Lilly had everyone fooled even Annabelle was believing that Lilly was really a girl. Once Annabelle paid, they took what they had bought so far to the car. Then they went to the clothing store. Annabelle smiled, "Knock yourself out, Lilly..."
 
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