I Dressed in public for the first time EVER this Halloween! Pics + what I learned

[Kevin_unknown]

I didn't have any specific costume, I just went to my university dressed as a girl. I know this might be controversial or against many of the opinions of people here on this site, but for me, crossdressing isn't what I am. It is an activity I enjoy not a separate persona.

That being said I had a great time. A good female friend of mine, that doesn't know I crossdress occasionally, helped me pick out an outfit. I was on my feet, walking around in 2" boots, that I found in a thrift store and fit me perfectly, for 10 hours, but for some reason it didn't hurt me really at all. Did I mention that this was my first time in heels of any sort? I didn't get my makeup done, so my face was pretty clearly male, however I did cause almost all of my friends at the university to do a double take (aka checked me out then recognized my face :P).
I even had a female friend of mine say that "You make an amazing women. Where did you get that sweater? I have the same one" and even the person who helped me pick out the outfit was impressed.

Anyways, here are the pictures. I don't have really any from the University, however I did take some at home, and some after I was out. Sorry about the low quality, my new camera is not working right now.

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And seeing as none of those photos really captured my leg/footwear

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All in all one of the best Halloweens I have had so far, I didn't get a single negative reaction. On the way home I even needed to pick up something from the grocery store and even walking around a store, dressed as I was I either passed or nobody cared about someone crossdressing on Halloween.

I did learn a few things though:

1) I am a size 10 10.5 in womens shoes. This is really fortunate because this is pretty much the largest size you can find in thrift stores.

2) Walking in heels (at least 2" ones, I really want to see if I can handle taller ones now) is not as hard as people make it out to be.

3) It is hard to carry things with you when you don't have pockets.

4) A bra, and some homemade rice breast-forms are AMAZING compared to trying to wing it with anything less.

5) Buying womens clothing (including leggings and bras) in stores/thrift stores is simple, almost nobody cares at all (although that is prob because it was the day before Halloween)

6) A long sweater, leggings, and calf boots are all actually surprisingly comfortable. A incorrectly sized pushup bra ... not so much

7) A heel, even a 2" one, makes your legs and ass look much, much better.

[LIKETODRESS2]

you look great hope you had a good time

[Andy66]

Im glad you had fun, Kevin. You look cute. :)

[MissTee]

You do look great. Glad you had fun.

[Princess29]

yes, once you try 4 inch heels (or higher) or stiletto ones, I think you might need to revise number 2 on your list of things you've learned

[lingerieLiz]

Glad you had fun. You are in the prime time to be able to dress and pass so enjoy it.

[Kevin_unknown]

yes, once you try 4 inch heels (or higher) or stiletto ones, I think you might need to revise number 2 on your list of things you've learned

I will consider that at challenge. I will be sure to post if/when I manage to get my hands on some :P

[Princess29]

if you can walk in them Kevin, rock on! I'm glad you had fun on your outing and I'm sure its the start of many more to come

Melissa

[Tracii G]

Do it more often if it was enjoyable.

[Kevin_unknown]

I would like to, unfortunately I still live at home and that is not a conversation that I would want to have with my parents. However there is a drag show coming up at my university, I might use that as an excuse to attend and get dressed up ...

[chelyann]

You look nice
If you man it down a little you could go out girly and no one would notice I think:)

[Kevin_unknown]

Thanks, I know my eyebrows are a little crazy right now :P

[jjjjohanne]

Unless you are particularly tall, I probably would have not paid you much attention and just assumed you were a girl. You were dressed in a non-remarkable outfit. If the sweater fit you poorly or if you walked like a man, clomping around, I might have read you. You probably passed. If so, it was because of your wig (or hair) and hat.

I was going to post this a few days ago...

If you go out en femme for Halloween around your friends, beware. Later in life, if you post any Halloween picture (meaning masculine), there is a risk that an old friend will bring up that funny Halloween that you dressed as a girl. That can get awkward if you dressed as a girl around a different social group a different year. We normally don't want our friends realizing that we dressed up as a girl more than once!! :)

Joey

[Lexi Moralas]

Glad you had fun ! You look great

[Kevin_unknown]

Unless you are particularly tall, I probably would have not paid you much attention and just assumed you were a girl. You were dressed in a non-remarkable outfit. If the sweater fit you poorly or if you walked like a man, clomping around, I might have read you. You probably passed. If so, it was because of your wig (or hair) and hat.

I was going to post this a few days ago...

If you go out en femme for Halloween around your friends, beware. Later in life, if you post any Halloween picture (meaning masculine), there is a risk that an old friend will bring up that funny Halloween that you dressed as a girl. That can get awkward if you dressed as a girl around a different social group a different year. We normally don't want our friends realizing that we dressed up as a girl more than once!! :)

Joey

Don't worry, that won't be an issue, I have already taken that into consideration. Thanks for the advice though.

[Beverley Sims]

As Andy said Kevin, you do look cute.:)
Glad it was successful.

[Marcelle]

Hi Kevin,

I am glad you had a great time. Don't apologize for saying you cross dress for the fun of it . . . we all have our reasons and no one way is the right way. You looked great BTW and it is easy to see how you blended in.

Hugs

Isha

[wannabeGirl84]

wauuu... you looke beautiful... specially that middle picture in first line...

[docrobbysherry]

Nice beginning, Kev. Just a couple of comments:

As others have mentioned, I call 2" heels, "flats". My men's shoes have higher heels than that. Walking in 4/5" heels is not that hard. (Or, so I thot). I did it for years alone at home. All the while destroying my stiletto tips because I didn't know any better! When u go out for hours, spend an evening dancing in 4/5" heels? THEN, u can say walking in them is no big deal! (I do that now and haven't destroyed a stiletto tip in years!)

U went out during Halloween without costume. Dressed instead in blending female atire. People r looking for costumes that stand out this time of year. U may consider that a costume, but most folks won't. My point is, u can go out in that type of conservative outfit any time of year. And, if u enjoyed it then do.

[Adriana Moretti]

awesome sauce....glad you made it out....i love the look too...and you are lucky with that shoe size......amazon will be your best friend soon.

[S. Lisa Smith]

Glad you had a great time!! You have just scratched the surface... You looked great, have fun with it!!!

[Chari]

You do have Kevin, IMO the makings of a cute girl! Consider trying some light makeup while in feminine attire, and carry a purse to solve your item #3 problem "carrying things when you don't have pockets". Thanx for sharing. Enjoy.

[Connie.Marie]

Kevin,
You're lookin' pretty great out there! You even made it back in one piece & enjoyed it.. Amazing feeling, isn't it!
Sounds like you are already looking for more opportunities.

I'd like to comment on a few of the points at the end of your post..
2) Walking in heels (at least 2" ones, I really want to see if I can handle taller ones now) is not as hard as people make it out to be.
Be careful with this one because it's also about how "skinny" the bottom of the high heel is. How much stability it gives you.
Suggestion: Try a 2" - 3" with a narrow heel or a 4" chunky heel before moving to a 4" narrow heel. You'll find it makes a huge difference.

3) It is hard to carry things with you when you don't have pockets.
That's why we all have purses :-)

4) A bra, and some homemade rice breast-forms are AMAZING compared to trying to wing it with anything less.
No doubt about this & you'll find a silicon breast form even nicer!

5) Buying womens clothing (including leggings and bras) in stores/thrift stores is simple, almost nobody cares at all (although that is prob because it was the day before Halloween)
Agreed.. a lot was due to the holiday.. some places might not be as accommodating other times of the year.

6) A long sweater, leggings, and calf boots are all actually surprisingly comfortable. A incorrectly sized pushup bra ... not so much
You'll find that how the clothes "fit" is very important to your comfort & how it looks on your body shape.


7) A heel, even a 2" one, makes your legs and ass look much, much better.
And 4" skinny heels even more so.. and adds an amazing "sway" to your hips..

So shape your eyebrows a little bit ( don't pluck too much).
Try a little makeup.

So CONGRATS on your first time out, may you enjoy many more.
When & where is that Drag show that you mentioned? I'd like to go & watch too..

Hugs, Connie Marie

[Kevin_unknown]

The drag show is not a large one, it is just a small thing that the LGBTQ community at my University puts on every year. I am actually quite good friends with a couple people who run it, kinda hoping they ask me to attend this time round >_>.

[Brandie.n]

Congrats on a successful outing I also used rice breast forms and knee high boots with a 2 inch heel

[Kevin_unknown]

Just thought I would give an update, my parents (who don't know I have ever crossdressed before this) got back home from their vacation and saw some pictures of my outfit I wore on Halloween. They thought it was awesome, that I looked great and my mother even joked that she wants to borrow my boots and that next time I should "use some makeup, (my sisters name) could help you."

Good to know that if I want to do this again, my parents won't be too much against it.

[Sarina Curtis]

You looked great and congrats on a successful night out!! Maybe I'll have worked up enough courage to try it myself by next Halloween!!

[charlenesomeone]

Ditto you look great. Glad you had a great time. Lots of CD spectrum from once a year to everyday.
Whatever makes you smile.

[shawnsheila]

First, that poster of Link in the background is awesome! You are a geeky gamer girl like myself :) I also wear a size 10 mostly, sometime I have to go up to an 11 in boots usually because my feet are kinda wide. You look great and girl it would be a ton of fun to have a sister help with makeup :) Glad to hear your parents are supportive. My mom and my brothers all know and are all supportive. My wife is another story. Keep up the pretty :)

[michellecd9999]

Glad you had such a good time and enjoyed yourself. Also you did learn a lot about dressing and being a woman. I love heels and walk very well in them. I can stand most heels I have for an evening out.

Most people are accepting at Halloween and womanless beauty contest, but be careful at other times unless you are ready to come out.

Michelle