Caught By Female Co-worker

I've been going out for walks all dolled up for years. A few years ago I got dressed up during my lunch break and went for a drive. I was wearing a bra, a tight short sleeved red top, a dark brown mini skirt, black pantyhose and sandals with two inch heels. I saw two cute blonds drive by and turn into the parking lot at a college. I couldn't resist following and parking close so they could see me when I would get out of my car. As I was walking towards the college entrance as if I too was going there, the younger girl looked at me and we recognized each other! She told the older one who looked as she could be her mother "I know him" and smiled. She was a clerk from work. My heart was pounding as I turned around to go back to my car and tried to make it look as if I had forgotten something. I was bent over with my upper body inside the car as if searching as they walked away. I did not dare look back to check if they were looking at my nylon clad legs.

The next day it was a bit awkward when we saw each other at the coffee break. She acted pretty normal. I always wonder if she told many coworkers about my cross dressing? I'm pretty sure she told at least one who is close to her outside work. She is no longer working at the same place I do but her friend still does.

One of my main regret about the whole situation is that I was not clean shaven and didn't have makeup on, when she saw me. The lunch brake is a bit to short for doing makeup. Although I'm getting faster with time and sometimes put on false lashes, lipstick and blush during my lunch time outings.

sandralingerie sandralingerie
3 Responses Jan 24, 2013


Too bad indeed that you were not shaved and wearing make up....

What a funny story (trying to see the humor). If you dress enough, you're bound to get caught, or seen, as in your case. I bet with the makeup, it would have been different! You probably would have been somewhat unrecognizable.


Im not sure about that. I once came face to face with a nurse from my hospital in the lingerie dept. I was wearing a short dress, pantyhose (with legs shaved), ankle strap sandles. I had a wig and makeup. She froze in her tracks and seemed to have a look of recognition. We both turned and walked away.