Conflicted thoughts on dressing for Halloween

[danam]

My company has a Halloween activity. We can dress up at work. One of the executives of my organization looks enough like Dana (me in femme) that I could conceivably dress up as her. OMG would that be crazy!

Actually, I think that would be a little too weird. I would not have any fun dressing up unless I dressed up "all the way" as Dana. However, this would be really awkward, because I know that I look good enough that I might create quite an awkward scene. And how would I field questions about my shapewear? After all, during the other 364 days of the year at work, I am a quiet and reserved "techie" type. This would be totally shocking to everyone involved! So I'm leaning against dressing up.

Any thoughts?

[Rachel Morley]

This is a tough one. In the past before when I was more closeted, I would go to costume parties as a French Maid or a School Girl and I would get comments of: "ut oh .... that's just a bit TOO good!" :o

You could just say you decided to do something so different and out of the "norm" just for Halloween ... and just for fun.

[Tasha T]

No sense dressing up if it's going to create awkwardness for you at work the rest of the year.

However, if you can figure out a way to put a funny, exaggerated twist on your character (as opposed to just being super realistic) you might be able to pull it off. Or...maybe even better...perhaps you could talk to her and get her to go as you and you as her. Make it a partners thing. That might take some of the pressure off.

Just some thoughts.

[Melinda G]

My old girlfriend had a crude saying, "You don't shit where you eat"! She was referring to messing around at work, but it would also apply to CDing.

[trannie T]

It is your one chance to go to work dressed. I disagree with Melinda above, you are not dumping on work, dressing up is much different from having sex with your secretary.

Dress up, everyone, including yourself will enjoy it. Have a good time.

[kristytv]

you know i thought alot about this, so on holloween i will be kristy, btw i work in car dealer, be it as it may.

[goofus]

My company has a Halloween activity. We can dress up at work. One of the executives of my organization looks enough like Dana (me in femme) that I could conceivably dress up as her. OMG would that be crazy!

Actually, I think that would be a little too weird. I would not have any fun dressing up unless I dressed up "all the way" as Dana. However, this would be really awkward, because I know that I look good enough that I might create quite an awkward scene. And how would I field questions about my shapewear? After all, during the other 364 days of the year at work, I am a quiet and reserved "techie" type. This would be totally shocking to everyone involved! So I'm leaning against dressing up.

Any thoughts?

I think your decision should depend on the culture of the place and/or the open-mindedness or lack thereof of your coleagues. If your co-workers are a bunch of conservative tight asses (especially the bosses!) then it might not be a good idea to crossdress. But if they're generally the more laid-back type, I say, carpe diem! :D

[docrobbysherry]

My old girlfriend had a crude saying, "You don't shit where you eat"! She was referring to messing around at work, but it would also apply to CDing.

I believe the phrase is more like, " U don't get your meat where u get your bread". Point well taken, Melinda.
RS

[Sophie_C]

A factor to be brought into this is that people are a lot sharper than they used to be.

If a man crossdresses on Halloween, people KNOW he does it outside of there (even in his own home) and it isn't him "being funny" or doing a one-time deal.

If you think your work is comfortable with that, go right ahead, but people will react with complete awareness of your personal life there, from that moment forward... :eek:

[Angie G]

It's Halloween hun go for it I am :hugs:
Angie

[Daphne Renee]

Have fun with it. Halloween only comes around once a year.

[Melinda G]

I've been CDing since I was 14. That said, I don't understand why so many of you are so obsessed with dressing at your place of employment. The only person I ever came out to was my ex wife, and she was gone a few months later. You really need to enjoy crossdressing for what it is, and keep it private. Many of you seem to be seeking some kind of approval, or acceptance, or green light, from everyone around you. Your wife, kids, neighbors, employers, and friends. A few of you will get it. Most of you won't!
You probably won't be attacked and beat up, but most people still consider crossdressing to be strange or wierd behavior, even if they are wrong.

[dee4127]

Have worked to hard to try and pass. It would let the cat out of the bag if i tried to do it at work.

[DonnaT]

After all, during the other 364 days of the year at work, I am a quiet and reserved "techie" type.

If you remain as such when dressed enfemme at work on Halloween, then no one will think you are doing this as a costume representation of said executive. In this case, I would say forget it.

If you think you can mimic her while dressed, then no one will think anything other than you are dressing as her. In this case, I would say go for it.

[Carroll]

You know, you only get one chance a year to dress at work. Like you I am allowed to dress for halloween. There are a few that know that I am a CD, and they are the ones that are looking forward to seeing me. As far as those questions about you shapewear, just say "Like my work, I never do anything half a$$"
:2c:
Carroll

[Phoebe Reece]

Way back in the early days of my career, I went with a group of friends from work to Mardi Gras in New Orleans. Our company had a division office right on the main parade route and we made arrangements to meet some of the staff there on Mardi Gras day to watch the parade. I went dressed fully femme (wig, makeup, dress, shaved arms & legs, hose, heels, etc.) - much to the amusement of my coworkers (some of whom I came out to later about my crossdressing). At the New Orleans division office I even met the Vice President of that division for the first time, with me fully dressed. If he was shocked or dispproved in any way, he certainly didn't show it. Less than two years later he was heading another division in another city and I ended up working as part of his staff there. Mardi Gras was never mentioned after I joined his staff. He did appreciate my work and I got a promotion and a number of raises while working for him. I had developed a reputation as a risk taker - and that was considered a plus in my job.

So, Dana, you can never know for sure what will happen until you do it. But doing something unusual (like dressing as one of the female executives) may get you noticed in a positive way. You might consider privately approaching said executive and asking her if she would be offended if you impersonate her on Halloween. If she responds positively that would be a good clue as to how it will go down with the rest of the office. Who knows, she might even offer to let you borrow some clothing item of hers for the event.

[Susan.]

At my office, I will get to wear mascara, a wig, earrings, panties, and silky pants, a blousy shirt, but... I'm going as a pirate. :D

[Christine Kelly]

My company has a Halloween activity. We can dress up at work. One of the executives of my organization looks enough like Dana (me in femme) that I could conceivably dress up as her. OMG would that be crazy!

Actually, I think that would be a little too weird. I would not have any fun dressing up unless I dressed up "all the way" as Dana. However, this would be really awkward, because I know that I look good enough that I might create quite an awkward scene. And how would I field questions about my shapewear? After all, during the other 364 days of the year at work, I am a quiet and reserved "techie" type. This would be totally shocking to everyone involved! So I'm leaning against dressing up.

Any thoughts?

If you don't dress up, you might regret the opportunity to do so.

If you do dress up and go as Dana, it might be one hell of a fun day for you. And who knows? You might find support for your dressing and want to do it every day! :happy:

[Suzy Harrison]

We don't have halloween over here, but some years ago they had planned a christmas party at the place where I used to work.

Someone came up with the idea that the guys come as girls and vice versa. I wasn't happy because I knew that I couldn't just 'half do it'. Basically if I went to the party I would be outed in a second. You don't look as good as we all do if you haven't had a lot of practice.

Luckily they changed the theme.

It seems a nice idea as a fantasy, but the reality is different.

[Kate Simmons]

As much as I enjoy being Sal, I enjoy being Rich just as much. It wouldn't be my personal choice do do it with the people I work with as I have a lot of respect there and while I am easy going and get along with everyone, I don't think it would be my best choice for that occassion. I can be Sal anytime really. I would look at it as a challenge to come up with something different. You never know just how creative you can be until yot give it a shot.:happy:

[KarenSusan]

That said, I don't understand why so many of you are so obsessed with dressing at your place of employment.

I think the reason, at least for me, is that you get to do the things you do every day dressed as you would like to dress every day.
I one time worked with a woman who told me that she suspected every guy who dressed as a woman for halloween was a crossdresser.

[Brianna Lovely]

What's the big deal?
I thought it was NORMAL for guys to dress like girls and girls to dress like guys, on Halloween.
I can't believe there are so many girls so up-tight about this.

You could always wear glasses with bigger frames, too much lipstick, too red blush, flashy bouse, etc. if you're worried about offending your manager. Of course, you could ask if she would mind.

By the way, anyone heard about ENDA?

[Ðarissa]

If you have the opportunity to dress up you should take it and enjoy it.

[megan163]

Dress for Haloween, Dana :thumbsup: You'll kick yourself later if you don't. And who wants to be kicked with pointy heals?:heehee: To keep them guessing, go dressed a little "over the top" - too much blush, a frumpy or loud outfit - think Mimi from the old Drew Carey show. You could have a lot of fun with it and then be ready for going out later that evening in full glam - pretty up and go out on the town, or the next town where you won't be recognized if you like.
Happy Halloween!

[Denielleinheels]

hmmm, Well I am going to work dressed on Holloween... However, I am a musician working a bar so I may get lucky, I know sick joke. For me it is the one day a year where I get to go "out". So I say go for it.

[chrissietoo]

I agree that any discerning co-workers will see that you are much too happy dressed to not have some kind of cross-dressing DNA. Some will notice that, peg you, and be happy for you. Some will notice and not realize they noticed and enjoy you. Some will notice and could be disturbed, and you need to think about what that might mean for you.

I think it's a great idea to ask you co-worker if you can dress as her--not as a "cover" (you will still shine), but because her participation (it would be wonderful if she loaned you some distinctive pieces of clothing) will give you acceptance and agreement, and could smooth over sticky situations.

[Joann0830]

I would tell them if anybody asked that you went to buy a costume and when you were undecided the sales person, a GG said to you why dont you go as a girl and you said I dont know where to begin and she stated that she would help you, The reason I said this is because a friend of mine who is not a CDM just told me this happened to him, I showed up as me Joann and he showed up as denise and explained to me the story, as the saying goes people just want to make money selling you something, this girl worked in a store where they sell clothes and costumes for both me and woman. :heehee:
Joann

[Michelia]

I just do not think it is worth it. Does not make sense to me. I work in a technical environment. Conservative types. It would not be worth affecting the rest of my life for one day of crossdressing.

Michelia

[Sherilyn]

Just tell them it's a rented bum.:D I would.

Sherilyn

[immike]

I really wish I could find a Dallas Cowboys Cheerleader uniform/wt the
stars,one that looks very much like a real uniform,the vest,the blouse&
the shorts,I'd love to dress up in the uniform,with pantyhose&boots

[Sophie_C]

What's the big deal?
I thought it was NORMAL for guys to dress like girls and girls to dress like guys, on Halloween.
I can't believe there are so many girls so up-tight about this.

You could always wear glasses with bigger frames, too much lipstick, too red blush, flashy bouse, etc. if you're worried about offending your manager. Of course, you could ask if she would mind.

By the way, anyone heard about ENDA?

It is EXPECTED, but not considered "normal" by any remote stretch of the word, today. There's always that one guy at any large party who does, but that does not mean people are comfortable with it or that they don't know what's up.

And, as far as i've seen, TG's are still going to be completely screwed by the bill, although I know that Bush will veto it and that there's not enough people in the Senate and House willing to overturn it, so it doesn't matter for the moment.

It'll bounce around until Bush leaves, and then the next President will pass some variation of what we see now, likely without any 'T' in it.

That's my forecast.

The damage is done.

[Jamie001]

I also work in a technical environment (sofware development) however the folks are not conservative. The executive management expects software engineers to be somewhat "artsy" or eccentric. The only place that I have seen really conservative types is in the financial sector or technology. In other words, companies that develop financial software or folks that do IT work in the banking or securities trading industries. It would be interesting to know what type of technical environment you work in.

:hugs: Jamie


I just do not think it is worth it. Does not make sense to me. I work in a technical environment. Conservative types. It would not be worth affecting the rest of my life for one day of crossdressing.

Michelia

[JazmyneCD]

I did last year and was hesitant as I sat in the car.

Once I exited and made my way to the office, it was a rush. Everybody in the office was shocked and highly entertained since I'm a rather a quiet type at work. All the ladies really dug it; only a few guys gave me funny looks.

Will I do it again? Not sure this year. It was such a hit that I just might, but I sort of got it out of my system so to speak since this was only my 2nd time "out."

I'll pack the clothes in case people ask for an encore. But the bottom line is...it's Hallowe'en. Go for it and have a ball.

[ShortSkirtCindy]

Hello Everyone,

Just want to share with you my experience I have going to a Halloween Party last Saturday night.

First thing I did was go over to the house Saturday afternoon where the
party I attended that evening was being held and met with the hostess
with some on my clothes and asked her if she would help me pick out a
girly outfit to wear to her party.

She was more than happy to help me out, so after going through some
of my outfits (which I told her I picked most of them up at the
Salvation Army), she settled on my white miniskirt, pink blouse and
brown anklestrap heels, along with a Red Wig that she had and wanted
me to wear.

I told her that I would be back in a few hours for the party and if I
showed up early, if whe would help me accessorize the outfit, and
replied with a happy "Sure Amber", the name I was given for my last 2 previous partys I attended showing up dressed.

I returned home to get ready, so I started off by shaving my legs,
applied Jergens "Softh Shimmer" followed by a pink bra, pink thongs
and a pair of sheer nude hose and finished by putting on the skirt,
blouse and wig.

I have to tell you that my heart skipped a beat, as when I looked at
myself in the mirror, it was the most feminine and girly feeling I had
in some time, especially looking at my legs with no question that
anyone who would look at them, would no doubt see that they were
shaved, given the sheer nude hose that hid nothing.

At that point, I said "What The Hell", hopped in the car and headed
for the party.

I walked into the door about a half hour early to allow time for her
to finish off my look, and all she said was "Nice Look Amber".

She started out with straightening my wig, then came the Make-up,
followed by a bracelet, necklace, with the finishing touch by
appliying Pink Nail Polish to my fingers to match my blouse.

When she was done, all she could say was "God you look Hot".

Not a word about my obviously shaved legs by her or anyone else. The
only comments I got from Male & Females at the party was I looked
very cute and what "Killer Legs" I have and how great they look in a
skirt and heels:)

Needless to say I had a great time with no rousing. As a matter of
fact, there were some people at the party that were expecting me to
show up dressed, again, as a girl.

I attached a picture I took upon return from the party, unfortunately I left my camera at home with all the excitement.

Dressing on Halloween for years was a boundry that I internally couldn't cross, but as time goes by, I think I am just more comfortable with who I am that I carry myself in a way that doesn't make me skiddish.

However, I do suspect that I have "Outed" myself to several that were at the party, based on my look, how I carried myself, as well being the third year in a row that I showed up as "Amber", my vanilla girl name given to me by the friends at the party.

Do you think my friends are wondering given the above info??

I hope you enjoyed my experience as much as did sharing it with you:)

Happy Halloween,

Cindy

[Stephenie S]

Oh my goodness! I can't believe how upset and worried some of you are getting about this.

It's Hallowe'en for goodness sake! You are supposed to dress up. You are supposed to do a good job at it. At many parties they give a prize to the best costume. People put a LOT of work into their costumes. What's wrong with working hard to do the best job you can with your female costume? How does that POSSIBLY "out" you?

Would doing a REALLY good job dressing as a punk, or a thug, or some other unsavory character damage your future? Would it "out" you as a punk, or a thug? Of course not! Nor will doing a really good job dressing female at work only one day of the year.

This is a non-issue, girls. A non-issue brought on by your own self conciousness and guilt about what you do.

Relax already! It's Hallowe'en.

Lovies,
Stephenie

[Kimberly Marie Kelly]

:heehee:Got the courage to dress up for the office, Going with Red asymetrical mini-skirt, white short sleeve v-neck sweater, Push up bra, light black panty hose and brownish pumps 2" heels. Legs, arms and upper body shaved with Pink glossy nail polish and nice silver necklace. Excited and scared but several people I leaked the ensemble too, say you gotta come in fully done up. The receptionist has given me the most encouragement to dress up. I figure its the only time in my life I could do this without repercussions. I will say the pumps hurt to wear so I will bring sneakers as backup footwear.:heehee:

[Billijo49504]

Are you sure you won't be dumping on a promotion??? If you piss off a exec, you might pay for it all year. If you did a generic girl, that might be different. How good of is this persons sense of humor???? It might make a difference..BJ

[Wenda]

Hello Everyone,

Just want to share with you my experience I have going to a Halloween Party last Saturday night.

..........
..............
Not a word about my obviously shaved legs by her or anyone else. The
only comments I got from Male & Females at the party was I looked
very cute and what "Killer Legs" I have and how great they look in a
skirt and heels:)

Needless to say I had a great time with no rousing. As a matter of
fact, there were some people at the party that were expecting me to
show up dressed, again, as a girl.

I attached a picture I took upon return from the party, unfortunately I left my camera at home with all the excitement.

Dressing on Halloween for years was a boundry that I internally couldn't cross, but as time goes by, I think I am just more comfortable with who I am that I carry myself in a way that doesn't make me skiddish.

However, I do suspect that I have "Outed" myself to several that were at the party, based on my look, how I carried myself, as well being the third year in a row that I showed up as "Amber", my vanilla girl name given to me by the friends at the party.

Do you think my friends are wondering given the above info??

I hope you enjoyed my experience as much as did sharing it with you:)

Happy Halloween,

Cindy

Cindy, you look great. My Avatar shows my slightly trashy side on Saturday. My photo shows a somewhat more refined demeanour. w.

[ShortSkirtCindy]

Thanks You for the compliment Wenda,

Looking back at Saturday night's party, I really am happy that I went dressed up, as I have no regrets.

I luv your Avatar. I hope you had fun Saturday night as well. I couldn't see your photo, but would luv to.

Hello Dana, I am not sure I would be able to pull off going to work decked out, especially dressed up as one of my female co-workers, for reasons many here have expressed.

First and for most would be my career as a priority over the possible ramifications of showing up at my job dressed as a female, co-worker or not.

That said, you must have a good handle on your work enviroment to make an educated decision as to whether you can pull it off.

I for one wouldn't do it unless I "Put out the Word" that I was thinking about doing it ahead of time, so I could get some feedback and if it was positive, that would be my Green Light.

In no way would I want to be on the fence about whether or not to do it, simply because it would not be fun, wondering down the road if I put my job in jeopardy.

Either way, it is your decision and hopefully it will be the right one.

I hope that for some reason you decide NOT to do it, you have an outlet to go somewhere after work to let your hair down and be "You" for a few hours.

Happy Halloween & Be Safe,

~~Cindy~~

[danam]

This site is amazing--I have gotten some really thoughtful advice and a lot of varying opinions.

I decided not to dress. Sorry if I disappointed anyone!

I'm still coming to terms with my own desires to do this stuff. I'm going to let this desire to dress up on Halloween at work percolate in my head for a year. Maybe by then I'll be able to have fun with it. If I did it now, I would take it so darn seriously because in a lot of ways it is, well, a truly erotic experience. So I decided that that isn't really appropriate for work. At least, not now. Maybe I'll chill out a bit in the future and will be able to dress up as a laugh with the co-workers...I think that is possible. Just not this year.

Oh, I had to give two presentations today and I had to walk several blocks between buildings...imagine doing that all dressed up!! Whoa, that would have been a trippy experience...both for me and the people watching me. Whoa.

Thank you again for all the advice! You all really helped me make what I think is the right decision for me, right now.

[DeeArel]

This is a wee bit late for the occasion but may help in the future.

Dressing in and of itself is not a really a costume in the true technical sense. One must also create a "real" costume that a female would wear, i.e. witch.

From experience, others will talk and make assumptions no matter how "innocent" you proclaim the dressing event. So, be prepared to live with it forever. It will subside as time goes on but invariably some one will always bring it back up when you think it has run the full course.

I have seen this to be true even for the guys who do it just on a lark and are never dress again in their lives.