En Femme Halloween

Halloween is fast approaching and as we all know is the greatest day of the year for crossdresser; it’s like having a pride parade without having to come out of the closet or is it reveal the rest of our closet?  Now admittedly I have not been out en femme for Halloween in a few years which as we know is a cardinal sin in our community however I have my reasons.

– I have been worried about some of my friends reactions.  I don’t have any homophobe friends, not all are the most comfortable either, and I’m not gay but for some reason people that are completely comfortable with homosexuality are very disturbed by crossdressing.  I would prefer not to create too many issues though this is ridiculous as some of the costumes in the circles I run are really offensive.

– Crossdressing isn’t a joke to me and I don’t want to make it one.  I feel compelled to do a reasonable job of crossdressing as it is an expression of me.  However at 6’3” 260 lbs I’ll always look a bit ridiculous but I choose not to make my dressing a joke either.

– What happens if I do too good of a job?  Looking good in a dress is one thing but the silicone breast forms, padded panties, size 16 heels, the authentic corset and the not cheap wig all show that perhaps I am better at this then I should be and as I have said I am out to certain people not all.

– Then we have the Facebook issue where I’m tagged in photos for my whole family and several coworkers to see in women’s clothing.

But I have decided this year that it’s about time for me to find my balls push them up to where from once they came puff my silicone enhanced chest out and hold my made up head high as I step out for all hallows eve.  Well actually the Friday Saturdays surrounding Halloween since it’s on a Wednesday and I defiantly have to be at home to hand out candy, so maybe four times but once for sure.

This decision has some risk associated with it but the worst possible thing that could happen is I’m outed for all the world to see and I lose some friends, have to put up with some bullshit from the others, some strange looks at work and have uncomfortable family dinners at holidays.  I am not concerned about anyone attempting to cause me physical harm as first gay bashing is rare here and as stated I’m a large imposing man.  Basically I’m looking at possible social and familial alienation and the frustration of filling out a police report with press on nails.  I would be injured but would survive to fight another day.  Worst case scenario if I don’t go en femme this year is I miss yet another year of socially acceptable crossdressing where I can have a fun time enjoying fully who I am.  I know your expecting me to say that not going out is worse however it isn’t, truly total social annihilation sucks.

The likely result is that I go en femme people compliment me on my dedication to shave my chest and legs.  I wouldn’t wear my heels as I’ll likely be drunk anyways, corset may be overkill for this presentation, panties would be funny if found and birdseed in some pantyhose still make effective breasts.  I make sure that no tags can go on Facebook without my approval and it goes down as a legend the year I went in drag. So assuming this is the likely conclusion to what is going to happen then not going out and suppressing this side of me for yet another year is defiantly much worse.  That and my Girlfriend is going to go out dressed as a man so it is a funny him/her costume, thankfully.

So this brings me to what to wear?  Somewhere on a web site or forum I read something about not going out simply in a dress as that isn’t a costume but in a female costume.  This makes perfect sense to me as my femme clothes are my clothes not a costume and women’s costumes do look like fun.  So potential ideas are:

– Bride and Groom but finding a wedding dress my size is not easy

– Pick a decade theme may be the easiest and still fun

– King and Queen

– Morticia and Gomez Addams, actually this one sounds kinda awesome

– Dominatrix and Slave but SM gear is so expensive and not something I want to borrow

So blogosphere I’m looking for suggestions as to what to wear for Halloween this year as my first re-entering en femme Halloween dressing.

7 thoughts on “En Femme Halloween

  1. Hi Jess,

    I’ve been meaning to comment on this since you posted it early yesterday, but I haven’t had a chance until now, and I’m genuinely shocked that I’m the first to comment, because I know how important Halloween is to crossdressers and as soon as I read it I had a number of things to say.

    That said, your concerns seemed to have done a good job summing up how I also feel about crossdressing on the holiest of crossdressing days. This year will be my third year crossdressing on Halloween, and my first year doing it now out to a number of people. I think by the end of the night, I will probably be out to everyone at the Halloween party.

    Your thoughts on choosing not to dress up for Halloween as your female self are interesting. I agree in theory, that our female clothes are not a costume, but that doesn’t mean you can’t dress up in them with a Halloween twist. For Halloween this year I bought myself a little black dress, orange belt, and I plan on getting some cute Halloween jewelry. Still myself, but with a spooky twist.

    It’s awesome that your girlfriend is going to dress up en homme, as I think that definitely decreases any nervousness about criticism or comments – I almost wish my girlfriend would consider something like this. If you’re still looking for some good themed costumes might I suggest you try to pull from pop culture….. I’ve always thought the The White Stripes would make a good costume. I know a couple that once went as Barney and Robin from How I Met Your Mother (not crossdressed) and that costume went over well.

    I look forward to a follow-up post with your Halloween results!


    1. Thanks Justine. I agree with you that adding a spooky twist to our standard femme wear just like many GG’s do would be dressing up. I was more referring to just dressing up in our standard femme wear with nothing special added seeming less than authentically festive for us. I also don’t seperate the him and her parts of me, I’m just me but that’s a post I’m working on for later. The white stripes is a good idea if we can find the appropriate clothes. Mad Men could be fun but for some reason I seriously doubt I could pull off Joan, shame real shame (I only wish I cold look like that). I also started thinking that perhaps just going in drag (not femme) would be a good way to kick off as then we can continue the his/her reversed themed costumes for a few years without too many raised eyebrows. That and I recently came out to a friend who did FTM drag for years, don’t ask why it took so long, so she would be able to really do us up in extreme drag. Though I do hold certain reservations about drag as I feel it perpetuates the public perception of that being Crossdressing, and simply put they just don’t appreciate the clothes like we do.
      As for you congratulations on a Halloween coming out I hope it goes well, one day I’ll likely have the guts to come out publically but I doubt it will be this year.

      P.S. I also enjoy your Crossdressmas reference.

  2. Hi Jess,
    This is causing you unnecessary anxiety and worry. Because you are a crossdresser doesn’t mean you are obligated to crossdress as a woman on Halloween. You are correct about your concerns with the social fallout. You need to weigh the social risks with the benefit to and for you crossdressing in public, even on Halloween.

    Maybe let you girlfriend pick out your costume and explain to her you want to go En femme. Let her let tell people it was her idea and you just went along for the ride being the great sport you are. Let her friends help and make suggestions. I would anticipate your girlfriend and her friends would love to feminize you beyond your wildest dreams.

    I do like the idea of King and Queen because gender role reversal is a relevant topic and telegraphs a certain level of adoration and power exchange with your girlfriend which will elevates her status among her friends. I would be careful not to be too “queerish” among your vanilla friends.

    Another alternative is a change in venue. You could go full dress-up but just attend Halloween events where no one knows you and you can feel free from peer pressure and expectations. You could have a more traditional “safe” costume for your friends and family. This is the safest route.

    You should have fun on Halloween free from stress and anxiety no matter what costume you wear.

    Just a few suggestion but in any event, god luck!


  3. Jess, your entire post was tightly organized, well-reasoned, and thoroughly entertaining. But all that aside, the line that left me doubled…no…QUADRUPLED over with laughter was, “I’m looking at possible social and familial alienation and the frustration of filling out a police report with press on nails.” The visual impact of a man your size wearing press-on nails while filling out a police report will remain in my alleged mind for years to come! Thanks!! Hugs, Randa

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