Crossdress For Halloween
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  • What is my age:
  • 46
  • Nationality:
  • Senegalese
  • My sexual preference:
  • Hetero
  • What is my sex:
  • My gender is girl
  • Figure features:
  • My body type is athletic
  • My favourite drink:
  • I like absinthe
  • In my spare time I love:
  • Travelling
  • Smoker:
  • Yes


Emily Shugerman. Looking back on family photos, he says, he can tell his smiles were faked. But after moving to Chicago for college, he started exploring other facets of his identity. In the back of his mind, he knew that Halloween would be the perfect time to debut this new part of himself: a person who identifies as male, but enjoys dressing as a woman.


Welcome to the first installment of my Chrossdressmas posts. As denoted earlierthis will be a five part series that details the many aspects of Halloween and my relationship with it as a crossdresser. October Let me more personally set the scene.

My girlfriend and I are shpping for Halloween costumes, with just a few weeks to go before the event. At one of the local seasonal Halloween stores, I suggest to my girlfriend that she dress as Robin from How I Met Your Motheror more specifically Robin Sparkles, the 90s teen popstar persona that Robin had back in Canada.

She laughs at the idea, but rejects it. She wants something a little bit more creative. We always make our own costumes — always. I jokingly suggest that I would be Robin Sparkles instead. I admit, I have done no scientific studies, and this cannot in fact be proven. It just makes sense. Halloween is how he is not-so-subtly telling you. After suggesting that I go as Ms. Sparkles, my girlfriend laughed.

I quickly searched for a picture of Robin and listed the clothes I would need. Frilly petticoat, fishnet stockings, pink shirt, denim jacket, wig. Anyone could do that.

Dress-opposite party

We browsed the store for another half hour or so, picking up the items we could find, and I left the store with everything but some neckles, the pink shirt, and the denim jacket. Can you tell which is the real Robin Sparkles? At home, I ordered a denim jacket online. The costume was set.

How halloween taught one college student to accept his true self

Halloween arrived. When getting dressed for our annual Halloween party, my petticoat housed another erection, and this time my girlfriend noticed. I laughed it off, making a slight remark about how the fishnets was a bit of a turn on. Nothing crazy.

Fast forward to Bruno Mars is still probably a thing, people begin to question what they ever saw in Cee Lo, and yes, the Mets still suck. Halloween is once again fast approaching. For the first time, my girlfriend and I live together! Now that I live with my girlfriend my crossdressing habits have jumped up a notch.

My first idea, months before Halloween, is to dress as a sexy cat. I can find some curves and fit into a skin tight black body suit. Get a wig, a tail, some ears. A simple and sexy costume.

I hide the package away discreetly. At Party City I purchase a black body suit. When the time comes, I try everything on. I think it might weird people out, and besides, who crossdresses for two years in a row?

Jump back to two days before Halloween. I tell her the inspiration came when I was at the 99 cent store and saw a cheap hipster fedora.

This is only a partial lie. The hat really did inspire me, but I set out looking for something to claim as inspiration. Using a mixture of my girlfriends clothes, my own clothes, and a few other things from the 99 cent store I semi-hastily assemble a costume. This year I have a nicer wig, and even use a little bit of lipstick. Halloween comes, and I dress.

Crossdressing halloween party costume

That night, after de-costuming, for the second Halloween in a row we have really mind-blowing sex. I stay up most of the night, wondering what would happen if I told her I was a crossdresser. Crossdressing never comes up. This year is different, though! When I told my girlfriend I was a crossdresser back in July I immediately began working on a Halloween costume.

Chrossdressmas, part 1: a halloween carol

One of the main things I was looking, and will probably always look for in a Halloween costume and while crossdressing in general is long-sleeves. I narrowed my options for this year down to either Supergirl or Sexy Black Dress. Long-sleeve black dress.

Plunging v-neck. Black heels. Orange belt. Probably some Halloween themed jewelry. At this point — it might be obvious. Three years in a row, you know? Regardless, anyone who asks me about the costume, I plan on being blunt with them and saying the following.

How to enjoy and celebrate halloween as a crossdresser

Yes, my girlfriend knows, and she is supportive. If you have any more questions, feel free to ask. What I want to avoid is a hijacking. The party should be about Halloween, drinking and having fun. Not asking questions to a crossdresser. This is something I hope will be solved, and not exacerbated, by a few drinks. Flash forward. Not the terrible TV show, but Cee Lo Green has died in a terrible dirigible accident, and yeah, the Mets still suck.

I think a lot depends on how this year goes. After some thought, I agree with this statement philosophically, but I also understand that to most other people, it still is a costume. So there it is. Take that, Dickens.

Part two of the series will focus on what Halloween means to me as a crossdresser. With that said, I will go before I bore you to death. First Great post though Dickens may still have an up on you, blame his marketing machine. Second in my defense the idea of not just going femme was found on another site of forum as I noted, and will now make a serious effort to find and cite it.

A cross dressed halloween

For me the whole point of Halloween is to have fun and we sometimes take dressing too seriously, so if hanging out in a dress and heels is fun then go for gold. Third shaved legs, chest and arm pits are awesome.

Thanks for the comment. Apologies if it seemed so. I think the idea of balancing seriousness and fun is interesting, and Halloween should definitely be on the fun side of the spectrum. Halloween should be the happiest of occasions.

Defense in this case was more in a joking manner to open a comment for me to clarify my point in relation to your post. No offense taken, no apology needed but appreciated none the less. Ping is term from IT that has entered the common vernacular. You are commenting using your WordPress.

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In fact there are crossdressers that only dress at this time a year.