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Posted 20 hours ago

Sissy Caught: First Time Feminization, Crossdressing (A New Woman (Transgender Women and Feminized Men Romance Stories))

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I don't know if she ever told anyone, but I never heard anything about it from anyone. I was scared to death for months afterwards. I would see Jan from time to time and she would wink at me, giving me a knowing smile, but she never brought it up again. It was one of the most intense experiences of my life... The first time was while I was still living at my parents house and I actually got caught. They were out of town on business (they owned a small electronics company) and my sister was at work. Well she does look great. You wouldn’t be able to tell unless he makes little mistakes; like SHE did earlier by saying you’re her sister.” Thank Donna. I just love wearing scarves & bandanas in my hair along with my aprons. I just think the look is so sexy!

I eliminated most of the replies and narrowed it down to two that seemed promising. One of the ‘finalists’ was only available that night, which was not possible, so now I was down to one. I was hoping this would pan out. I’d hate to miss out on this opportunity. I only had a few days. So this last prospect sounded really serious. He just needed 20 minutes notice to get there, and promised he would show up. Believe it when I see it, but nonetheless, I was pumped, excited, nervous, scared… all the normal emotions I always feel when arranging a meet up with a complete stranger.Yes Nicola. Take the clothes off and lay down on the bed. If your going to do this, we’re going to make you do it right, Dawn where is the glue?” But I couldn’t stop visualizing about all the cute lingerie and clothes that my girlfriend had after that moment. I wanted to try on everything. And it started again, I would sneak into my girlfriend’s closet and wear her outfits whenever I had a chance. It went on for a month and then I decided to get myself a nice hair wig and a pair of heels. I didn’t wanted to buy more things because I knew it would be a problem to hide them from my girlfriend. I returned the clothes to my mom and she said if I wanted to talk about it. I said I was sorry and just wanted to know how it felt to wear a dress. She agreed to not tell dad and after that moment I made sure to never get caught like that. My mom didn’t asked me about it again and I think I feel more comfortable like that. It took me quite some time to get up the nerve to head out. What if someone drove by? What if my sister came home unexpectedly? So many what if's!

Yes I was, we all know someone has been trying on your sisters and mothers clothes for quite a while now. It was just a matter of time before we caught you at it .” I must have taken like thousand of photos and videos of me going around the house. I was too scared to go out in public but I did step out in the balcony at night fully dressed from head to toe. It was an exhilarating feeling. I dressed everyday for the whole week my wife was away and when it was time for her to return. I just got rid of all the stuffs that I brought and promised to never dress up again. I walk over to the large full-length mirror in my sister’s bedroom, and immediately jump away and hide.Borrowed one, silly boy. There's plenty lying around in her room. Just go grab one of those." She smiled again and James felt a nauseous feeling grow into his stomach.

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