I have an interesting problem. First, I’m still totally in the closet with my dressing. Several months ago I started a contest for my employees at work. As part of the contest I threw out there that if a way out there goal was reached, I’d come to work “in drag”. It looks like they are going to actually make it. So now I’m excited but also terrified. My question is, how is the best way to dress to not out myself but to still enjoy myself?
Don't be too good at it if you want to stay in the closet. Unless you can say you told your wife or girl friend and they got into it and helped you out. Sherrii
If you don't want to be out, then you can't look too good. Shoes that don't fit, cheap wig, make up a mess. But if it was your idea in the first place, some people might think you wanted to wear it anyways
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).
What Sherril said. I wouldn't act too comfortable with it and might even pretend to nearly fall down in heels, walk clumsily. You might even mention after help with the make up you can't imagine you ladies that work here how you get to work on time. Most of all remind them of how much you appreciate their hard work to make you have to go thru this.... If you are maybe one day wanting to come out you might tell them towards the end of the day hey you know I look so good wearing this I might just want to do it daily if y'all keep working this hard....
You have to give us a little bit more information. How old are you? I think age has some bearing on the type of clothes a person wears. Big difference between young 20's and mature 50's. Also, what is the work environment? Professional office? Or factory job? Dresses or women's pants. I read some prior postings. Assuming you will wear a bra I'd leave those breast forms at home and go with some homemade forms; rice, birdseed, etc. No non-dresser is going to have a pair of fake boobs laying around the house. If possible I'd enlist the assistance of a female staff member of your group to help with makeup. Maybe, you can elicit ideas from the group to make it appear this is a group effort, and, not just you popping in at work unannounced. Also, if you're proficient with four inch heels that may be a giveaway. Go with a low heel or flats.
Just dress appropriately and try look your best, don't be a clown or a charicature of a woman, have some respect.
Honestly it was your idea so anyone with a brain probably already has figured you out.
Everyone knows that men who are into "forced feminization", don't really need to be forced.
Last edited by Robertacd; 03-07-2019 at 02:48 PM.
Ask for help from the females in your company. Maybe they can turn a wig and shoes that would look better than the 'thrift store' you would present by yourself. It would also get employees involved in the 'payoff'.
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
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.
Thanks for the ideas. For further info, it wasn’t so much my idea. It was around Halloween and someone came into work dressed in drag. Someone else jokingly brought it up and I just kinda kept it going. As for work environment, it’s professional so a dress will be needed. For myself, I’m 40.
So got a little lucky. One of my female co workers “reminded” me about the deal and asked if I needed help when I lost. I played dumb and told her I would need a lot. She’s now going to help with my outfit and make up. She also suggested those super tall dancer heels. I think that’s a great idea because then I can wear heels and I won’t have to fake walking in them. Should be fairly unsteady already.
You would not make that offer if you are in the closet.
Sounds more like you want to out yourself.
Its a pretty common claim to say you lost a bet when its actually you trying to find a way to "come out" without actually saying it.
PS:
Nobody get pissed but I can't tell you how many times I have heard the old "I lost a bet line".
Lol. There may be some truth to that. As of now, no one knows about my dressing. And I may or may not have manipulated the situation so I could dress up. But I don’t really want to let people know how much I like to dress up now.
Dress in an appropriate way, Like Roberta said, But wear your tennis shoes, not your fem or high heals.
If you wear a dress, do not wear pantie hose unless your wife thinks you should. do not paint your nails.
A wig yes, but tell them you borrowed it from a relative or some one. Do have fun, it your chance of a life
time, going out dressed with a license to do so.
Rader
I could not agree more with what Roberta said. Put your best effort into it and put forth your best presentation and be confident
Personally, if a worker is "helping" you, go for the gusto. I did that one year for Halloween, I had 3 girls from the office do my make up and they and my wife supplied the clothing.
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
What person in their right mind that doesn't want to tell would make the bet? That makes no sense.
Its obvious you want to let it be known you just are too afraid to admit it to yourself or others.
Is it you are worried others will make fun of you or they will think you are gay?
How about be unapologetic get out there do your best?
That way there will be no doubt that you are a crossdresser and be done with it.
There will be questions and snide remarks by others but you have just put it out on the table for all to see. The thing is you have taken the fight to the beast and there is no recourse on their part to impune your character.
Dress like a member of the C-Suite!
Cool story, Needs more dragons though.
Before you can love another, you must first like yourself
I Aim To Misbehave
Labels belong on BOXES, not PEOPLE!
Posting Permissions
