Crossdresser High Heels Mature Crossdresser


Not every crossdresser outing turns into an adventure but the ones that do are usually memorable. Sometimes it’s the fun of interacting with other crossdressers at a conference or convention. Other times it involves just yourself with a fashion emergency or something that involves a few others.

If you are a regular reader of my blog, you know that I am always experimenting with different ways to improve the crossdressing experience. One such crossdresser outing comes to mind when years ago my wife and I were on a couple’s crossdressing trip to San Francisco. I believe this particular night we were at a Lilly Tomlin show next door to the Farallon restaurant where we had a wonderful dinner.

I was seated next to my wife in the theater when she became annoyed with my constant squirming in my seat. When she asked what in the hell are you doing? I had to tell her that Little Willy had escaped his enclosure and was in serious trouble. Beyond that there wasn’t much I could tell her, but she said go fix it.

Confused? Let me explain.

When we dress in women’s clothes, we have to make arrangements to hide our male (Willy) parts and still be able to use the bathroom. It was never something I felt comfortable asking a guy about, so I put my imagination to work on solutions. My recent stroke of genius was to cut the cotton gusset out of my pantyhose right along the edge of the hem or seam. That way I could just move my underwear aside and pee then put Willy back home and move on.

On this particular crossdresser outing night Willy partially escaped and got trapped between the hem and my body resulting in not only pain but loss of circulation. I knew Willy’s life was in danger and I needed to do something fast to save him. I wiggled back and forth in the seat trying to break things loose but to no avail. My wife told me to go to the lady’s room and fix it so off I went.

Things only got worse when I got to the lobby and saw the line for the lady’s room. This crossdresser outing was in the early 2000’s and I was never comfortable using the lady’s room even today I go to great lengths to avoid them. I did not want to create more problems for myself standing in line with pissed off women and a painful look on my face. I mean what would they think when I finally freed Willy and let out a deep voiced sigh of relief in a stall of a women’s bathroom.

Things were getting serious by the minute with me not knowing how long Willy could live without blood. Desperately looking for some way to address the issue I found an exit or something with stairs leading down. I went down a couple of flights of stairs to what was most likely a dark basement with nobody around. I could not hear anybody or anything, so it was now time to fix things. Up came the skirt, down came the pantyhose and out came Willy. A sense of calm came over me as the blood flowed and I repositioned Willy in a safe place.

I made it back to the Lily Tomlin show before it ended and told my wife all was well.

I don’t want to say that the event scared me but, I have worn thigh high stockings ever since.

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crossdresser season


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