Most awkward place to crossdress?

[Allison Chaynes]

Per Beverley Sims' suggestion in another thread, where would you say is the most AWKWARD place you have (or could think to) crossdress?

For me, I'm going with the night I thought I was having a heart attack and went to the ER in an ambulance, underdressed. And my parents and uncle showed up... no one saw anything, but you can imagine how it could have gone.

[Dana44]

At least you was not dressed fem. LOL. If that happened to me i would most likely be dressed. It might be pretty awkward then. But I read that in Jail they even put a male dressed crossdresser in the woman's solitary cell and kept them there. For like six moth's or more. That would be awkward.

[dawn459]

Hospital ER : pantyhose
Cutt off with jeans &splinter off of screwdriver
In your leg and hoping they
dont askyou to remove your jeans for xray&tetanus shot in hip
But I got mine in my arm
Thankgoodness.

[docrobbysherry]

Cambodia. Changed into and out of my Laura Croft outfit inside Angkor Wat. In a dark, 1000 year old, decaying mud floored, alcove with walls missing and guards walking all around.

But, it was WORTH IT!:D
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[Danitgirl1]

Phew... Haven't had any truly awkward experiences...
My most nerve wracking ones were situational rather than geographic.

One Saturday I was at the mall and walked right past (literally) three work colleagues, on separate occasions, in the space of about 10 minutes.
I was so close to one that we literally brushed arms as I passed her.
Nothing was said. I don't think they recognised me.


On another occasion I was coming home from a TG/CD party at a gay bar and I drove up to a police road block (it is South Africa our police are allowed to stop you without suspicion). The police woman was very polite called me "mama", asked if I had been drinking (which I truthfully denied) and waved me on my way... Here is the full slightly humorous account if you are interested: https://daniellaargento.com/2015/12/17/crossdressing-modus-operandi-time-for-a-change/

[Micki_Finn]

Hm, a Klan meeting?

[Stephanie47]

I would not want to be transported to any emergency room when en femme. One of the things I have been told by medical staff in the profession it is better to be transported in an ambulance than just showing up. When an ambulance is enroute the paramedics are stabilizing you and calling ahead. The patient is taken immediately to a care room. If you show up by yourself off the street you have to sit and wait too long in the ER for care. I'd rather have the fem garments taken off me in private rather than sit in the ER. Earlier this year I went to the ER accompanied by my wife and son with a kidney stone attack. The amount of time it took for the admission people to get to me and ask all those questions about insurance was enough to make me reach out and strangle someone.

When I do go out en femme I always make sure to stay off the freeways and main drags (no pun intended) so, if my car were to breakdown I would not be blocking traffic or get stuck between freeway exits waiting for the State Patrol to happen along. I always carry a change of clothes back to male mode just in case of a breakdown.

[MelanieAnne]

That EMS ride to the ER can easily add $1000 or more to the bill, depending on your insurance or lack of.

[sometimes_miss]

At my front door when '60 minutes' comes to interview me with TV camera front and center. Yeah, that would be awkward.

[Lana Mae]

Melanie, try $3000! Hugs Lana Mae

[NicoleScott]

At my front door when '60 minutes' comes to interview me with TV camera front and center. Yeah, that would be awkward.

That's a door I wouldn't open, crossdressed or not. Publishers Clearinghouse is another matter.

[Jeri Ann]

Awkward? That's easy. Kendra Scott Jewelry store next door to MAC in Rice Village, Houston, TX. Lauri and I had been to MAC for makeovers and I insisted that we go into Kendra Scott. I was looking for earrings and matching necklace for a special occasion. The place was packed with young women in their teens, twenties and thirties. To make matters worse they were all about four feet tall. I'm 5-11 and Lauri is a little taller. We felt conspicuous towering over so many younger girls. Lauri will never forgive me for dragging her in there. Lol

I have been to Home depot, Bass Pro and Academy Sports and Outdoors, no problem. Kendra Scott, tough!

[Lauri K]

Awkward? That's easy. Kendra Scott Jewelry store next door to MAC in Rice Village, Houston, TX.

Yeah but we went twice in the same day because Kendra Scott was so packed first trip with GG's out the kazoo, that we ran out of time and had to get over to MAC so you could flirt with the make up artists then after the MAC thing we went back to Kendra Scott for the 2nd trip in there, except this time there were a few guys in there and they had no idea what to do with us ..............but I think they like what they saw just saying

If you can survive Kendra Scott in Rice Village you can go anywhere in the world, airports are a breeze I tell you....

[Nastasha]

Went and got fitted for a bra 2 towns over. Tried on multiple bras and ended up talking to the sales lady, joking, laughing getting fit tips and tricks, was with her for about an hour.

Ran into her about 2 weeks later at an event, was with my wife. So how do you 2 know each other? Uhhhhh.....

[Allison Chaynes]

Hm, a Klan meeting?


Think we have a winner....

[Princess Chantal]

Most awkward place I experienced was actually at a friend's house warming party in which all the people (other than me) attending were either in the process of transitioning (most), have transitioned (1 person) or are questioning their gender (1 person). The awkwardness created was from their assumptions that I was deep in the process of transitioning, the questions that were asked from those assumptions, the preaching, the constant statements that I am in denial, the unacceptance of me describing my dressing as an enjoyable interest and then assumptions that I am closeted or lacking out of the house experience.....

[Scarlett398]

In a phone booth! Good thing they don't exist anymore! HA HA!

XOXOXO Scarlett :tongueout

[JennyLiz]

For me its a public beach. I am scared just at the thought of it. I am planning on going to Atlantic City for a weekend to dress completely Even going down to the beach. I am scared silly of it. I just wish I had a friend to go with to help take the edge off you know.

[ginapoodle]

Tripoli, Libya on business trips...in hotel...and dealing with intrusive security traveling, and within hotel.

[Allison Chaynes]

For me its a public beach. I am scared just at the thought of it. I am planning on going to Atlantic City for a weekend to dress completely Even going down to the beach. I am scared silly of it. I just wish I had a friend to go with to help take the edge off you know.

I did this last year in Hawaii... we drove around the island one day until I found a stretch of beach that was relatively empty. Allison threw on her swimdress and took pictures with Mrs. Allison. Only time she has really been out in public except for a Womanless Beauty Review years ago.

- - - Updated - - -


Tripoli, Libya on business trips...in hotel...and dealing with intrusive security traveling, and within hotel.

Girl, you are brave!!!!

[Alice B]

No one can top Doc Sherry for having fun while creating a strange situation - Dressed!

[Jeri Ann]

Oh, I remembered another one. A couple of months ago I had a date for lunch. He had chosen a highly rated Mexican restaurant on the east side of Houston. When he opened the door for me and I stepped in, the music stopped, everyone in the place turned to look at us... Well, there wasn't music, but that's what it felt like because we were the only gringos in the place. Not only that but the menu was in Spanish. I know a little Spanish but I didn't recognize anything on the menu because it wasn't a Mexican restaurant, it was Salvadoran. Everything turned out well. There were no issues. I never have had an issue even though my list of awkward places is growing. Lol

[Aunt Kelly]

Oh, I remembered another one. A couple of months ago I had a date for lunch. He had chosen a highly rated Mexican restaurant on the east side of Houston. When he opened the door for me and I stepped in, the music stopped, everyone in the place turned to look at us... Well, there wasn't music, but that's what it felt like because we were the only gringos in the place.
I know that "music stopped" feeling. Dressed or not, it's unsettling, when every eye in the place turns to look at you. It's usually just our biases making us feel that way, and if you just smile and carry on, the music starts up again, and it's all good. Still, I'd say it's a good sign that your friend didn't bolt and leave you there. :)

Most awkward place I've ever been to dressed... You know, that's tough. I want to say that first outing in Vegas, but once I got past the terror, it was fun for the rest of the night. Everything since then has been neutral, at worst. I've got it! The first few times I was ever out of the house dressed it was to support group meetings back home in PDX. They were held in a restaurant banquet room, so pretty safe environment, right? But that very first trip to the ladies room would have to be it for me. Decorum is way different in the ladies room. It was utterly new territory. Again, things went just fine, but for the first few minutes, awkward doesn't begin to describe it.

[Nikki A.]

Most awkward for me was being dressed in an "LGTB friendly" bar in Indianapolis on a week night. Now I consider myself pretty open, but this place was a bit too crazy for me. On the other hand the BBQ chicken cubes on a stick was pretty good.

[Maria Blackwood]

Zero gravity

[SunHun]

It would likely be at work for me.