My Aunt And Me...

From the time I was seven until when I was almost finished college, my aunt use to have me over to her house for a crossdressing weekend. This happened at least a dozen times. She lived in a different town and had a daughter about two years older than me.

For whatever reason, my aunt truly enjoyed crossdressing me -- first in little girl girls clothes, then later,, as I entered high school and college, she dressed me up more like her maid. She actually put me to work in and around her house.

Several times, at night, she would drive me around the town. I was both terrified and thrilled at being discovered by someone who might know my aunt.

My girl cousin always knew my and her mom's secret but did not tell me until years later. Although my cousin and I discussed the idea, we were never able to get together ourselves to enjoy the the same exciting crossdressing events. Too bad. Maybe one day.
jackyyy7 jackyyy7
46-50, M
6 Responses Feb 6, 2011

Lucky dog, wish I could find me a girl to share my life with. I would like her to dress me as a woman.

My mom had some idea as to what happened at my aunt's house. And I think my mom enjoyed the idea even if she did not know for sure that it actually happened.

Yes, my aunt as well as my cousin know that what was started still goes on to some degree.

Cool Aunt and cousin that you have. Is your Aunt aware of what she started?

Wonderful story, I had an Auntie that liked to dress me in SILK FRENCH KNICKERS and CAMISOLE, it was wonderful.<br />
I have now been addicted to wearing silk lingerie for many years now, I love wearing silk or satin knickers, the feeling next to the skin is wonderful, I will never change back to boring mens underwear.

it's the experience I always want to live, actually I only dream it.