2 guys at work dressed up in women's clothes Halloween night, I did not

[RainbowDash]

1 guy dressed in hot pink pants, black top, red haired wig. The other guy, a fellow delivery driver, dressed up as a fictional anime character. When I saw him in his car about to go on a delivery, I commended him on dressing up as a girl, and then revealed to him that I was a crossdresser, but didn't have the courage to dress like this in public, even if it was Halloween.
It made me feel like I should've tried it to, but I just didn't know others were going to do it too, otherwise maybe. Plus I do not really have any Halloween outfits, just regular women's clothes. I do have my Fair Maiden outfit, but that takes quite a bit of effort to put on, and I'd need help with the bodice, otherwise it would not look right. I did have a couple of fancy gowns, the kind a girl would wear to her senior prom. But I was not at a party, I was working and everyone was getting in each other's way. The skirt would have gotten messed up, splattered with food, and I wouldn't have done it much good trying to climb into my vehicle and then sit down to drive, not knowing if that big skirt would get in the way of my feet near the brake and gas pedals.
After the night was over I thought about this little fact.... Men dress up in women's costumes on Halloween night, but they are not crossdressers. They have fun with it obviously, but we get to do it 365 days a year. Another thing I thought of was.... how many of these guys dressing up in women's costumes have a strong enough feminine side to just roll with it like we do? Could they be future crossdressers? Or is it just 1 night for them at that's it? Either way, it makes me appreciate being a crossdresser that much more, and all I wanted to do was have the night be over so I could go home and dress up. Of course, I was the closing driver so I got home late and went to bed, having to wait til the next day.

[KymG]

How did the driver react when you told him?

[RainbowDash]

How did the driver react when you told him?

He was cool with it. Asked him not to tell anyone else, as I only tell people who I feel I can trust. Figured a guy dressing up as a girl could be trusted, even if he only does it for a single night. But then again, he told me he spent $200 on making a homemade outfit, so it'd be a crying shame to wear it only once.

[Vickie_CDTV]

While your coworkers did it and had some fun with it... honestly you made the right call. Keep crossdressing and your job separate. With the world now on fire, don't do anything that could cause problems with your job or your reputation at your job. It won't help you, but it could hurt you. Even telling your coworker you crossdress might not have been a good idea, unless you were good friends with him already.

[Alexis00]

I’m with Vickie_CDTV on this. Had a job where my routine crossdressing got around and it became an issue with some people. Times are better now but you can’t “untell co-workers.

[Stephanie47]

I agree with Alex and Vickie. There is a lot of "acceptance" out there. But, is there really? Maybe, nobody gets in your face or calls you names. But, will you get the cold shoulder from some? Will the promotion not occur? There is a lot of political correctness out there. There is a lot of anti gay and lesbian, transgender, cross dresser sentiments. When in doubt, keep it private. At Halloween there are a lot of venues where a cross dresser can struct his stuff. Would you go to work and casually kick back and tell other intimate details of your life? I doubt it. I hope you read your co-worker correctly, and, he will keep your secret.

[kimdl93]

You never know what anyone is motivated by unless the volunteer the information.

[Krisi]

The problem with being a crossdresser and dressing as a woman for Halloween is, you will do too good a job and people will suspect that you don't do this just once a year. How many "normal" guys have a $300 set of silicone breast forms and a properly fitting bra? How many have a $100 wig that looks real? How many have a $200 set of hip and butt pads? How many have properly fitted women's clothes and shoes?

Depending on the situation, it may or not matter, but you are outing yourself if you do it around people you know.