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Don't Wait Up

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James had always been fascinated with his sister and desperately wanted to know what it was like to be a woman. His sister was older than he was and had a very active social life. She was your typical, up for anything, party girl. Out all night, every night, and still finding the tie and energy to hold down a decent job during the day. As a result, James was able to indulge his little cross dressing fetish on a regular bases. He was forever trying on her club outfits and dresses and loved walking around the house (when his mother was too preoccupied to notice) in any one of his sisters pairs of heels. Thankfully their house was mostly carpeted, bar the front entry way.


One day James found he had some time to sneak into his sisters room and have a little fun. It was about an hour before Abbie was due home from work, and she already had tonight's outfit ready and presented nicely on her bed. He'd have to do his usual and take careful note of where everything was so that when she put it on later, she didn't realise that James had already worn it. He was a little disappointed when he saw it was a simple pair of cut off jean shorts and a blue jacket. He assumed that since just his favourite, tiny little blue thong was there and the matching bra was missing, that his sister was likely wearing it right then. Oh well, he thought. At least he'd get to try most of it on. 


That's when a little silver sparkle caught his eye. At the front of his sisters wardrobe was a pair of silver, strappy heels. Simple, with a few straps. James wondered how they could ever stay on someones feet as there wasn't much too them. They must be new as he was in his sisters closet often and had never seen them before. The were placed as if they were the shoes she planned to wear tonight, which seemed strange as his sister usually wore a pair of blue stilettos that matched the jacket he was now holding in his hands. Well, she did like to mix things up sometimes. Both with ehr wardrobe and her various boyfriends. 


James shrugged it off and stripped out of his pj's and started getting dressed in the outfit his sister thought she'd be wearing later. The little blue thong was the item that fit the best, in that they didn't fall down. His genitals were small enough that the triangle at the front covered most of them and he did like the way it kinda tickled between his butt cheeks. He put on the jacket next, again disappointed that there was no top or bra under it, but resigned int he fact that he didn't want to go digging through his sisters drawer or hamper for something suitable. Then he pulled the cut off shorts up and held them in place. "Oooh! Look at me! My names Abbie and I think I'm so pretty and perfect. All the boys want to touch my boobies."; James said. That's when the little silver sparkle caught his eye again.


Holding the shorts in place, he walked on his tipee toes over to the silver shoes and slid his feet into them. As he was trying to figure out how he could keep them on his feet and walk around, the shoes suddenly started moving. Two straps emerged near the top and quickly wrapped themselves around James' legs, holding the shoes in place. Then they slowly wound themselves further and further up his legs, disappearing into the shorts. James froze and felt a strange warm sensation start to radiate out from his groin. He didn't know what was happening, but little red spots appeared down by his feet. James panicked, thinking maybe he had cut himself and was bleeding, but he immediately noticed that it was his toes, or rather his freshly painted toe nails. At the same time, his feet were growing to fit the shoes perfectly. He also noticed that his legs were getting longer and all of the little peach fuzz disappeared off them. At the same time, something on his chest felt awful sensitive. A little disarming at first, but nice. When he looked he noticed two perky breasts rubbing their erect nipples against the inside of his sister's jacket. When he reached for them, he noticed his hands were now long and slender, identical to his sister's with ehr trademark long pointed nails, painted to match his toes. 


"Holy moley!" James said, but was shocked to hear his sisters voice come out of his lips. He ran over to his sisters mirror and looked at a perfect copy of his sister looking back. He sat down at her make up table and just stared. A million thoughts ran through his mind. What happened? How could he fix this? What would his sister say? What would his mother say? It took him a few minutes to realise that as he sat there thinking, he had been expertly doing his sisters face up with her make up. He couldn't believe how perfectly he had done. That's when he decided to go the extra mile. 


James grabbed his sisters blue purse, somehow knew exactly what to put in it and reslising that his ID (or rather his sisters ID) would be needed before leaving the house. He hoped that his sister would see the fun in this and let him go out, even if for just a little while. Knowing she was almost home, he quietly snuck down the stairs. Not paying attention to how easily he was able to do it in his ridiculous heels. His mother was still n the basement, washing and folding the laundry, so all he had to do was sit and wait by the front door for his sister to get home. As he heard her car pull up, he realised he hadn't gone searching for a bra so still didn't have one. His mind told him, of course not as the perfect one would be walking through the door any second. He could only imagine what his sister would say when he asked to borrow that too, although, considering what he had already 'borrowed', it seemed like such a small thing.


As the doorknob turned, James started to feel a bit nervous. His sister walked in with her head down, turned and closed the door, then turned around and looked up. 


"WHAT THE F..", was all she was able to get out before there was a large flash of light. It took a few seconds, but when James was able to see again, he was shocked. Standing in front of him was a perfect copy of James, with his sisters close mainly all on the floor around his double. The new James stood speechless, and that's when the old James realised how much easier this was going to be. He sauntered over to his old body, pulled his sisters top up over his old head and quickly snatched the lacy blue bra off his little boy body. "Better go put your pj's back on before mom sees you standing here nude or you'll be in trouble JAMES." Abbie didn't know what to do, so she raced upstairs to see if she could figure this out. "You'll find them in MY room JAMES" the old James giggled as he reached down to pick up his sisters discarded purse (and ID) and car keys. 


"What's going on guys?", James and Abbie's mother called up from downstairs.


"Oh nothing mom. Just helping my little brother out a bit.", James called as he slipped the jacket off, hooked on the bra, and then put the jacket back on. "I'm heading out with the girls mom. See you later!", James said as he scooped up what were now his discarded clothes and headed out the door.


"I won't wait up then dear. Just be safe!", his mother said.


As James was pulling out of the driveway, he looked up to his room to his sister, dressed in his discarded pj's, looking out the window crying. James simply smiled and waved as he pulled away. 

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MrBannanaMan's avatar
is she ticklish?