If you really want to “not out” yourself, skip the makeup and wig and just find an ill-fitting dress at a thrift store and throw it on over guy clothes. This way if you need to be “professional” you can pull the dress off for a bit and be appropriately dressed underneath.
Last edited by Micki_Finn; 03-08-2019 at 12:48 PM.
It sounds to me like you set a pretty high bar for your team and ask for their best. I'd keep with that mode and go all out to look professional. As for worrying about outing yourself, you've already insulated yourself from that by the context of the event. I'd be more concerned about being comfortable all day, than what they thought. I am inferring that there is a good bond among the team or the bet wouldn't have been made in the first place.
As a rule, we all spend a lot more time worrying about what other people think about us than we should. Have fun with it and there's lots of good advice about mitigating any doubts in previous posts, asking female members of the team for help and stuff like that. Again, have fun and wear comfortable shoes.
I am Me and Me is OK!
Shelby
I think I would "own it!" with the help of the woman that volunteered to help. Do your best to look the part. Now the mention of 4" heels would be a dead give away because not many, if any men can slip on 4" heels for the first time and walk in them at all. Keep the heels down to 2" or so.
If you play the part too well it will be a dead give away, but you can dress up well in a nice outfit and be a clumsy man in a dress.
Last edited by Pumped; 03-13-2019 at 09:52 PM.
I say go for it. Be the best dressed female executive in the office. Keep it to a business level, but go for the heels, wig and makeup. My suspicion is most everyone will respect you for the effort. And for those who don't - tell them to be careful what they ask for.
I have never regretted the days I have dressed to the max, only those I didn't and could have.
Dee
Team reinforcement 101 will tell you that you should reward the group with something they want not something you want. The whole thing sounds bogus to me. And, I'm saying this as someone who dressed in drag for a Halloween party with mostly Company employees (not sponsored by the Company). During my work career I would have been appalled if I put in extra effort to accomplish a goal only to have my boss show up in drag thinking that was positive reinforcement for me. And, I probably would have been fired by my boss if I were the one in drag. Don't be worried about being outed as a CD. Their first thought will be that you are gay and their second will be that you want to be a woman (as in transsexual).
I'd suggest doing the very best you can, making the best possible presentation of yourself. Let them reach their own conclusions. They probably already have
Remember always that you not only have the right to be an individual, you have an obligation to be one.
Eleanor Roosevelt
I'm with the "go big or go home" crowd. It's 100% understandable that you'd look good if someone was helping you with your makeup and presentation.
Michaela
If you choose not to decide, you still have made a choice. - Rush
I would definitely seek the help of a trusted female employee. Tell her that you're going to need help with makeup and getting the right clothes together to make a positive impression. Tell the female employee that you want the employees to have some fun at your expense, and boost morale. If necessary, you are willing to go all out, but you're not sure how to accomplish that. Tell her to use the internet to send you suggestions.
Just as an added thought. If I were you I would be very nervous about crossdressing at work. As it looks like your employees will meet their challenge, I would announce a change to my promise to dress in drag. I would say something like, the boss is supposed to set the dress code for the office and that day should be no exception. So on that day all the men in the office are encouraged to show their support for their boss by wearing a dress to work. Tell them this is completely voluntary, but you don't want to be the only man in a dress. So their support is greatly appreciated.
Last edited by Confucius; 03-11-2019 at 01:58 AM.
I agree with DeeDee. Be the best dressed female executive on the site that day. As I mentioned previously, have coworkers (female) help with the presentation and till them to go all out for business executive. You are willing to go along with all reasonable expectations. Have fun.
joank
Southern California
Keep in mind the reward for them is your “humiliation.” If one or more females have fun helping you that could help contribute to that, but f your only dressing for yourself, that does nothing for them. Let the women decide how you look, even if it’s not the way you want to dress.
I say go for it and have fun. Don't forget to post pictures.
Follow the expected office dress code and let the female employees lead the way. If they suggest pantyhose agree to it and if they say you have to have shaved legs in a dress hem and haw around on it then eventually cave in and agree to it. You may wish to get kitten heels so it does not look to obvious.
If you do this more than once people will defiantly start talking.
Let's face it, you made the offer, joking or not, because deep down you wanted to do it. You still want to do it, but are worried about the repercussions about dressing.
Personal aside: I think the ship has sailed about being thought of as gay because you cross dress; people know more gays, and 99.9% of the gays they know don't dress as women.
You live in Salt Lake City, which is obviously a conservative area, so your concerns about repercussions are probably valid.
But you made the offer, and if you value your team, and want to show them your word means something, I wouldn't half-ass the effort. Actions speak louder than words. Besides, you want to dress nicely, don't you?
Here`s my two cents.
I think you have to wear a dress, nylons, and heels. Nylons means shaving your legs.
You can find a new dress at either a thrift (you can likely find something suitable at Savers) or go to Nordstrom, which is extremely TG friendly. I know both are in SLC.
For makeup, find a makeup artist, or book an early appointment at Sephora to have the makeover done. Plan to go into your office around noon if you choose the Sephora route.
Get your nails done the night before.
For the wig (assuming you have one), fib and say you borrowed it from a friend. If not, buy one.
Heels from Payless (before they close) or Nordstrom Rack, or DSW.
AND take pictures of the process; shaving your legs, getting your nails done, buying the dress (in drab), the makeover. Make fun of the process--because you are going to make it fun (trust me, getting a Sephora makeover is a lot of fun).
Show up at work dressed, send out an email thanking your team for meeting the goal, attach the pictures you took, and enjoy the day. Make the big reveal a Friday so you don't have to take off the nail polish until Monday...
When it's all done, post the pictures here.
Your rational does not support your premise. I agree that the general public does not immediately assume you crossdress just because you are gay. But my experience and many comments on this forum suggest that most of the general public does indeed assume that you are gay if they see you crossdressed.Originally Posted by TheHiddenMe
Said differently:
• Being gay does not mean you are a crossdresser.
• Being seen as a crossdresser suggests you are gay (or want to be a woman).
We know that 2nd point is not true but the GP doesn't yet know it.
Last edited by Taylor186; 03-12-2019 at 12:17 PM.
Sounds like you set the bar high for the team, set the bar high for yourself I have worked in corporate America and the team will generally appreciate the effort you put into dressing.
Just dont forget about which bathroom you will be using LOL
hugs and more hugs
Rhandi
Heidi, dressing at work isn't an option for me and may not be for many years if ever. Still, your bravery has my deep admiration. BTW - I'd love to chat endlessly - almost- with you!
I bird never knows it can fly until it tries. This could be your push out of the nest. Give it your best effort. Who knows where it might take you.
LadyStig please keep us informed about developments. It sounds like you're just starting.
The girls from work and making this just perfect for me. They are picking out everything. One of them has a wig she’s going to let me use. It’s red. Not normal red, like devil Halloween costume red. They found a skirt for me to wear and we found a pair of heels at the mall for cheap that I’m wearing. And they are going to do my nails before work that day. In looking forward to it. And the best part is everyone knows the girls are dressing me so as long as I don’t do anything stupid, I think I’ll be safe from being outed. I’m sure people will talk but I can live with that.
First, have fun. Wear heels. I would go with the outre wig and over-the-top makeup. Most important, don't shave, show hairy legs and arms. Make an Entrance! Congratulate the team on their performance. You can lose the outfit after a couple of hours.
Well, tomorrow is the big day. Just got back from getting my nails done for the first time. Got my outfit ready. And I’m stopping by one of my co workers house tomorrow before work so she can”fix me up” before going into the office. I also just decided to wear my forms too. I figured why not. Wish me luck!
Can’t wait to hear all the details! Have the best time LadyStig!!
and if possible, don't forget the pictures. I have a feeling this event will be well documented.
joank
Southern California
Good luck today, can’t wait to hear how you did.
Crissy
Well, going to work was so just awesome and embarrassing. I feel like I looked just enough like a guy in drag to not be outed. I wore my thong and forms but no one would be able to tell that. Then wore some tights vs nylons, a skirt and top from one of the girls at work, and the red wig. And 6 inch dancer heels (which helped a ton with not being too comfortable walking around). It just felt so nice to be dressed up and in public. Going to be doing that much more often. Only bad thing was I’m now officially out of the closet. My wife caught me because I’m stupid. I got out my box and got my forms and thong out and left it out in my storage room in the basement. Bad thing was my wife needed to light the water heater because the wind or something had blown it out so she found the box. So I got home all dressed from work expecting her to be gone and she was there we had a long talk about it. I guess she had suspected for a while. And she was “ok” with it but not with me keeping it from her. She was super upset about that because I had to tell her how I would get gift cards to buy cloths without telling her. Come to find out, one of her ex’s was also into dressing. So after talking for a long time, we are working through it. So might have been a very good thing. Only time will tell.
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