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Crossdressing Fun

Friday
So my parents were away for the weekend and i was left with step sister (she will be called Sarah for all intensive purposes, she was 21 at the time). Sarah worked from 9 till 4 so this gave me a good window of oppotunity to go and play in her room. as soon as she had left i went straight into her room and took all my clothes off and started dressing myself in her clothes (i'm quite small for 16 so her clothes are actually a bit big for me). so first i put on a pair of panties, then a bra stuffed with socks to give a lil cleavage, so i can be more girly. then a short skirt that sarah wears to go out clubbing and a strappy top. so i get completly changed and then started to rumage through her room. looked on her computer and found some pictures of her in her bra and another picture of her topless. so i do begin to get really hard so i lie on her bed rubbing my crotch through her panties getting harder and harder, i need some relief and look what i can find to make it more interesting. i look in the top draw of her bedside table and find a vibrator. i turned it on and put in between my legs and pretended i was a girl doing it and i could feel i was going to climax soon. so i lifted my skirt and lowered my panties to my ankles. little did i know that my sister was walking up the stairs and i had left the door open. she knew that i came into her room to do this and she been wanting to get some proof so she had come prepared with a video camera just as i came she burst in filming me ****** ans try to cover myself while j i z z ing. it was so embarrassing.
but she gave me a choice i could either have the video posted on FB and shown to my parents or follow Sarahs rules for the weekend and the video would be deleted, so i took the obvious and accepted the punishment:

Must be dressed as sarah wants me to be dressed at any time.
I may not leave the house at all
I must ask to pee and sit like a girl
I am instructed to **** and will be filmed to ensure that i do not break my agreement and will be deleted at the end of my punishment weekend.
Sarah may spank me when and how she she likes
i must wear a collar at all times so that sarah can keep me under controll

Saturday
dressed in an even shorter skirt that showed half my bottom and my thong and i also wore a push-up bra and low cut t-shirt. i was spanked early in the morning till my bottom was very red and when sarah was tired. after my spanking sarah told me that i was to lie on her bed and wait for intruction so i did so. she come into the room holding a pair of handcuffs and told me to put my hands around the head-board where she then hand cuffed me. i was here all day she gave me water if a needed it and little food but i did not mind. later after it had become dark she came in and pulled down my skirt and panties and i instantley became hard and very embarrassed. she got the vibrator and rub me with it till i came and then told me that the punishment was over.

now everytime the parents are out she spanks me and toys with me
LilSimple LilSimple 18-21, M 4 Responses Oct 7, 2010

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Wonderful story and I can only imagine how embrrassed you were! Did this happen years ago or just recently? Do you still dress for your sister or for your own enjoyment now?

Sounds like you both enjoyed it :) Happy for you for having such a sweet and kinky stepsister!

I hope you thank Sarah for being so sweet to you. I had an old sister who would sometimes dress me up. Always a fun time.

Was that the last of your punishments?