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When I was in my early 20s, I waited until everyone had gone to sleep (pretty sure my father wasn’t at home or no longer living with us at the time) and went downstairs. I put on my mom’s short blonde wig, women’s clothes and a jacket (I grew up in New England). It was very late, guessing around midnight or so. I left the house and started walking down the street. Five minutes later, two men, a father and son, I believe, were walking their dog and heading in my direction. I immediately ventured off into a wooded area between two houses to avoid having to speak with them. I eventually made it back home without any other encounters. Not sure if I passed or not. I was certainly thin enough at the time in terms of having a female-like figure.
- 28 Dec, 2025
- 12 likes
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One night I dressed indoors and then covered the LBD and black stockings with jogging bottoms and sweatshirt. With a pair of heal in a carrier bag along with two pairs of socks I went out to the car. I drove out about 10 miles from home into the countryside. Removed the sweats and filled my bra with said rolled up socks and put on my 3" heels and left the car. I still can't believe the sensations that ran thru me feeling the cool night air nibbling at me thru my femme attire. I strutted up and down the road a few times in the headlights from my car then saw headlights in the distance. I scrambled back into the car and drove off . I passed the oncome police car a minute later.......don't know if they were called about me or not....hehehe. xx