After my parents got divorced when I was ten, I was living with my Dad. He was bisexual and had a boyfriend that stayed with us. On some weekends I would stay at his boyfriends parents house with his sister, she was my age. We would share a bed and we both would only wear t-shirts and underwear to sleep in. I liked the panties she always wore and one time after she was asleep I got up and got into her dresser and got a pair of her panties. I took my underwear off and put her panties on and then got back in bed and fell to sleep. The next morning she woke me up and asked me why I had taken my underwear off, I had left them in the floor. I didn't know what to say and she asked if I was naked under my t-shirt. I told her no I was not naked and she asked what I had on then. I reluctantly told her I had a pair of her panties on. She wanted to see so I raised my t-shirt up and showed her. She giggled a little and told me if I wanted to I could wear them the rest of the day if I wanted. I said no I would put my underwear back on. She told me I could wear them and she would not tell anyone I was wearing them. So I did and loved it. That next night after her parents went to bed we were in her room and she asked me if I liked wearing her panties all day. I told her I did and she asked if I had ever wanted to wear a dress. I told her I had thought about it. She asked me if I wanted to try on one of hers. I told her I guess so. She went to her closet and got me one of her dresses and I took it to the bathroom and changed into it. It was a simple sun dress and I was nervous walking back into her room to show her what I looked like in it. She said it looked good on me. I went back and took it off and put my sleep shirt on. She changed into hers and we got into bed. She asked me if I liked wearing the dress and I told her I did. She told me she would not tell anyone about it but she would like to dress me up someday and I could wear it all day.
Michelle1976 Michelle1976
36-40, T
4 Responses Aug 16, 2014

Wanted to look and act like my sister.

It must have been quite wonderful to have a mentor like this
young lady. At ten years old it must have been difficult to sleep in the same bed without a bit of excitement.

What a great friend you had in that girl, Michelle. Did she dress you up and have you stayed in touch?
Lee

Yes she did dress me up with her mom's help after she told her about it. No have not kept in touch after my Dad and her brother broke up.

That is great that she dressed you up and with her mom's help. Too bad that you didn't stay in-touch but that is life, isn't it Michelle. ;-)
Lee

cute! love it!