He laughed as he stood in front of the mirror and then preceeded to select and play his sister's records. You stay there while your sister and I call her friend and tell her that she can't now be her bridesmaid " his mother said. The two women left the room to Sam's room to empty his wardrobe of all male clothes and replace them with a few skirts and dresses. For me it started in my early teens. I discovered masturbation (wow what a joy!) and womens legs became of particular fascination to me. God they looked so smooth and sexy, how I longed to touch them, to see if they felt as soft as I imagined.

We'd love to see your stories posted here, think you have a story to tell or have written stories posted elsewhere. Aunt Marilyn, showed me around and where everything was. Then we left, to go for fish and chips, to eat at Tally’s. On return, aunt took a shower, and offered me to take one after her, which I did, to freshen up.After an hour or so, he decided he'd had enough. He turned off the record player, put the records away and reached round to unzip the dress. He tried to calm down by sitting on the bed and as soon as he was calm again, he tried the zip. But it was not budging at all. So I put everything away, except when I came to the underwear, there was a problem. Mom had accidentally left one of Jody’s panties in my pile. Jody is my elder sister who is just 2 years older than me. I held her panty in my hands, feeling the silky material. I was a typical 10th grade boy, so as you can imagine, my mind raced at the thought that I was holding panties in my hand.

Feeling very mischievous, he wondered what it was like to wear such a garment. Without hesitation he laughed to himself as he took it off the hanger, unzipped the dress and stepped into it. Carefully he pulled his arms into the sleeves but his shirt made it very difficult. He removed his shirt making it easier for his arms to go through the sleeves. Then he reached round and zipped up the dress as far as he could. It was about 3 inches away from fully zipped and he noticed the pull that the dress had around his waist and chest. Sam, on the other hand, was unemployed, as he had only left school a few months ago and as yet, was still to find a job. After a great meal and sex we laid in bed together where I secretly wondered what surprise my wife had in store.

The Surprising Moment Of My Crossdressing Life.

For the next couple of days, everything was quite normal. My sister rarely bothered me and I was pretty much over the things that happened before. After being pissed at my buddy for the next hour or so for telling her, I told him he might as well tell her I’d be willing to try it again, but I wanted to completely dress not just wear a bra in front of her for a minute. I figured that would deter her. Well, I was wrong. She gladly accepted and the next weekend I was there in her room for my first real crossdressing moment. I went from calm and cool to nervous as all hell when I realized she was REALLY into it. Make-up was out. Clothes on the bed. And many of her bras lying out for me. I literally stopped at the door of her room. My buddy laughed, pushed me in, and said he’d be watching TV. He only wanted to see “the final product”.