Dressing at work

[LadyStig]

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?

[Sherrii]

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

[Jaylyn]

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....

[Asew]

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 :)

[Stephanie47]

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.

[Robertacd]

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.

[LadyStig]

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.

[joank]

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'.

[LadyStig]

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.

[Tracii G]

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".

[LadyStig]

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.

[RADER]

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

[jennifer_cd]

I could not agree more with what Roberta said. Put your best effort into it and put forth your best presentation and be confident :)

[Nikki A.]

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.

[Tracii G]

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.

[Maid_Marion]

Dress like a member of the C-Suite!

[Jodie_Lynn]

Cool story, Needs more dragons though.

[Beverley Sims]

I think you need to dress without makeup and a wig.

You could look more convincing with a wig, do you want your employees to talk about you?

[Patience]

If you opt for a wig, get one in a color not found in nature or get one of those big hats women sometimes wear.

If you'd like to avoid eye contact or at least make it more difficult, get some femi sunglasses.

[Rogina B]

"Let's give them something to talk about..A little mystery to figure out " Look your best and OWN it ! It was your doing...

[Maid_Marion]

Have fun! Take your most comfortable pair of heels for spin!

[Diane Taylor]

The advice the others gave you makes the most sense...but are sure that maybe this idea isn't a somewhat hidden desire to in fact "come out" ?

[Tracii G]

Exactly Diane but the OP maybe can't admit it to themselves .
Thats why they make up a scenario like I "lost a bet" so I have to dress up.
I have seen that excuse used so many times I find it very hard to believe.

[Laura912]

With respect to the others on both side of how to dress, go with what your coworkers come up with. If they do the guiding, then you have them to point to as your advisers. It then becomes a group decision and not solely yours.

[docrobbysherry]

I've found balloons filled with air boobs, terrible makeup, and a stash/beard r the best way to NOT come out!:brolleyes:

[Micki_Finn]

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.

[ShelbyDawn]

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.

[Pumped]

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.

[DeeDeeB]

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 :fairy1:

[Taylor186]

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).

[kimdl93]

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

[Michaelasfun]

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.

[Confucius]

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.

[joank]

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.

[Shayna]

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.

[Lea]

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.

[TheHiddenMe]

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.

[Taylor186]

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.

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.

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.

[Rhandi Spencer]

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

[SusanSpencer]

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!:hugs:

[Genifer Teal]

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.

[Confucius]

LadyStig please keep us informed about developments. It sounds like you're just starting.

[LadyStig]

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.

[Cynthia T]

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.

[LadyStig]

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!

[Lux]

Can’t wait to hear all the details! Have the best time LadyStig!!

[joank]

and if possible, don't forget the pictures. I have a feeling this event will be well documented.

[Crissy 107]

Good luck today, can’t wait to hear how you did.

[LadyStig]

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.