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Lingering Waitress

October 26, 2016

I decided to have an outing during lunch.  I changed into a black skirt, a dark top, and heels.  I went to a restaurant.  There were no customers in the dining room.  I walked up to the counter and asked if I should seat myself.  The waitress was on the phone with a customer.  She nodded.  I seated myself.  The waitress, a young, polite, seemingly normal girl, came to my table and took my order as it usually is done.

When the waitress brought me my drink, she tried to start a conversation with me.  She seemed to be fumbling for words.  She excused herself at one point to take care of something in the back.  When she returned from the back, she delivered my food.  She took my cup to refill it.  I decided to give her something to talk about since she seemed to want to talk.  I asked her why she was not in school.  She told me her whole story about how she is in high school, but she is doing her schooling at home.  I ate half of my meal while we talked.  Eventually, I asked her to go fill up my cup that she had been holding.  She brought me my drink and then she talked to me only briefly.

At one point, someone from the back of the kitchen came to the counter to visit with the waitress.  I wondered if the waitress told the staff in the back there was a dude in a skirt in the restaurant and this person was visiting the front to get a look.

As the time approached a more traditional lunch time, other customers started arriving.  The waitress became busy.  I finished up my meal.  I came up to the counter to pay.  The person from the back left the counter area and visited the drink area.  From the drink area, the person was (conveniently) able to get a good look at me at the counter.  I paid my bill and we said our good-byes and I left.

Not wanting to stop being dressed pretty, I stopped in at an ice cream shop that I occasionally have visited while dressed.  The owner was there, like usual.  She ended up chatting with me while I ate my ice cream.  It was like I was nothing unusual.

Now, have you ever had a waitress or other similar person linger around you while you were crossdressed?  The girl mentioned that she had some social trouble in school and that was what led her to do her schooling from home.  Perhaps she was more alternative than she appeared.  She never did anything inappropriate or “forward”.  She just wanted to talk to me.  Once, I experienced having two young girls try to speak a few words to me.  However, they did not try to start a conversation.  I am curious to know what this means.  It is interesting.


From → True Stories

  1. Wesley permalink

    Earlier this week, I was at a Barnes and Nobles looking at nothing in particular. One of the female booksellers came by and asked the cursory “Is there any thing I can help you with” Initially I said, no, but noticed she was looking at me a little deeper (eye to eye contact, not the once over) so, I said, “well, perhaps the winning lottery numbers.” Which started a several minute long conversation, that signelled interest.

    We did exchange names, and i did not get to speak with her again ;-(

    I will go back. . ..

    I was wearing a pair of green light denim pants, a black synthetic tee shirt under an obviously womens top with a wrap around front, Black trouser socks and ballet flats. . . The outfit did not garner any attention, but she had to have noticed. . . .

    It will be interesting to see where this goes. . . (I am divorced, ex wife knew and approved of crossdressing) . . .

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  1. Lunch Non Event | joeypress
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