Your Best Halloween Story

[trevor]

let me first say for about the last 6-8 years once in awhile i will wear nylons and heels with my wife on a night when weve both been drinking and have fun doing something different. 2 years ago we were drinking some wine one night and after my wife had drank a couple glasses of wine we started talking a vacation. it was september. i said to her how about las vegas for halloween. weve never really gone out for halloween before. weve been to vegas alot but never for halloween. as we talked she said are we going to dress up and what would we wear. i said i would like to dress up as a woman and it would be fun. she said if thats what you would like then lets do it. lets just say i was never more excited ever in my entire life. we went to a goodwill place to find me a dress. all ugly stuff. i told my wife i wanted to go online and find something a little sexy. she said go ahead. i bought a wig and a very short sexy dress. i already had 5 inch platform pumps and nylons. she bought me a bra and fake finger nails. i also bought some snap on earings. i used one of her girdles to hold my stomach in. i dressed up 2 nights at club studio 54 at the mgm hotel. they had halloween parties like all 5 nights leading up to halloween. i did alot of homework in choosing the mgm to stay at and going to this club. i wrote about everything that happened those 2 nights on here back in 2010 in october and november if its still there and you want to read it. walking around wearing 5 inch heels and 2 girls asking me how can i walk in then was unbelievable. i savored every minute of both those nights knowing that this probably wont happen like this again. every halloween now my wife dresses sexy and i wear the same outfit except for the shoes in which i now have 6 inch platform pumps. we order chineese food drink alot and have fun at home. at least i had that one opportunity. lets here some others.

[kneehighs]

A couple of years ago my friend and I dressed up as Playboy Bunny's. It was amazing. Click HERE.

[ilikekicks]

This is a somewhat long story with a semi-adult theme. You have been forewarned As most know, I am a ' part-time ' musician. Most know where I am from and understand me as I am now. BUT.. Years ago, I worked at a communications company on overnights while I ran my business during the days. I had co-workers and such and it was in an ' office ' environment. The band I was with at the time had an unreliable singer/vocalist. We wound up telling him to ' go away '. What was odd was a known ' artist ' parted ways with her band. She was a committed lesbian and really didnt like guys at all. She had some friends that have helped her with her career over the years BUT.. it always went sour. Low and behold, it was a perfect chance for us to play with a known person. We did some room recordings of some of her material and gave it to my brother ( studio owner where she did all of her work ). He played it for her and she loved it. That is she loved it till she met us. The first words out of our drummers mouth were ' Look at the tits on that thing! '.. just what a lesbian wants to hear from a guy.. Well.. there was a charity event, in costume, for the local children's hospital. She was the second to last act for the night and was going to try and do a kareoke thingi.. My sister in law came up with an idea. ' Girls band ' for halloween. My girlfriend at the time fell in love with the idea and the pressure was applied for the 3 of us to do it. 3 weeks time to put everything together. So.. we had a dress rehearsal about 3 days later and the singer was invited to come see ' a new band ' whom knew all her material. She absolutely LOVED the idea! This was the absolute FIRST time I ever wore any ' womens clothing '. Needless to say, we pulled it off quite well, the singer agreed to it and we started regular rehearsals ( every other day ) for the next 2-3 weeks. Well.. the gig came, we played. I was all dolled up to the point where quite a few people had no clue to who I was UNTIL I said something. We finished playing and one of the guys from the office was there.. with a couple of the other guys.. and they were all drunk, but ' mike ' ( as I will call him ) was absolutely friggin HAMMERED! I went up to the bar at the club we were playing in and one of the guys decided to find out whom I was. So.. we gabbed for a bit then ' mike ' decided to join in on the conversation after staggering across the bar.. drunk.. Some more about ' mike '. Hes a ' ladies man ' ( or so he thought ). He has ' Roman Hands ' and believes no woman in the world cannot be ' conquered '. It was rumored then later proven he slept with EVERY woman in the office AND some of his co-workers wives. Great guy, but just to much of a sex addict. The friend I was talking with gave me the heads up and asked for me to ' play along '. So I did. I didnt really say much, just smiled once in a while but tried to keep ' mike ' off to the side in everything. Our friend played it like he knew me in passing that I was a friend of his sister or aunt or something.. not an every-month meeting type.. Mike just wouldnt leave well enough alone. Hands going all over the place, laughing and asking questions. Well.. The singer we played with saw this going on and decided to intervene. Everyone knew whom she was and she came out of nowhere to ' rescue me '. " IF she gives you her number, will you call it quits for the night? ". ' mike ' was given a phone number and I was out of there. We had fun for the rest of the night. Back at the office that Monday, ' mike ' was rambling on about how he met this hot babe at this club.. Its all we heard about for 3 days. A couple knew exactly what happened but didnt say anything. They were all loving what was really going on. ' mike ' at the time wanted nothing to do or hear about man on man type relationships. ' Lesbos ' were ok though.. So, that friday, ' mike ' asks me for my brothers number so he can find out whom this woman was. He says the number she gave him was for an answering service or a pager or something. So, I figured I would give him my brothers number, game over, we all get a laugh.. HELLS NO! My brother tells ' mike ' that he will ask her if its ' ok ' to give out her number as they are business associates and he doesnt want to invade her privacy. My brother is quite the ball-busting type. What does he do? He gets a cell phone and has his step daughter put a voice mail message on the thing in the most sultry voice possible.. Then gives ' mike ' the number!!!! For 2 weeks, ' mike ' kept leaving messages. It was getting really bad. We were having lunch and he was rambeling on and I asked him " DO you really want to meet this babe? " he was energized at just hearing such.. ' do you really know her? Seriously! Have you been there, done that, how was it?!?!?! ' " Mike.. you hit on me. " ' No F-ing way! ' Everyone just laughed. He STILL didnt believe it when everyone told him about it. So, I went out to my car. I remembered I still had the wig I wore boxed up in the back seat. Brought it in, tossed it on his desk in front of him.. ' Mike ' became very sick. He left about 2-3 minutes after I showed him the wig. He took the rest of the week off.. Needless to say, to this day, ' mike ' is a good friend and hes really changed his ways. He doesnt drink that much these days and my brother ALWAYS busts his balls when he sees him. I didnt think I was ' passable ' as some would say but I was told otherwise by quite a few people. A few that knew me didnt recognize me and it was a good night that raised a truckload of cash for Childrens Hospital. I do occasional work for that singer, but her career isnt where it was a while ago and it wasnt highly established to begin with. Im one of the few ' guys ' she doesnt mind having around. I still have the boots I wore that night Cheers! -Ilk

[bluejay]

Nice story ilikekicks. It was very interesting to read! Happy heeling, bluejay

[Shafted]

One word, "Priceless".

[HappyinHeels]

My best Halloween memory was the only Halloween party I was ever at back on 2005 in Chicago. While I have been to backyard events along with a few outdoor weddings en femme, this was my only halloween party. Sponsored by a shoe store it was billed as a "fetish Party" so most wore sky=high heels and fairly outrageous outfits. I do remember standing in a metallic gold dress with 8" platform sandals in a circle with real girls and t-girls talking and smoking and admiring each others' outfits. It was a great and relaxing night for sure! HappyinHeels

[Dr. Shoe]

I had a thought the other day: Why do you guys wear heels, dresses, skirts etc. on Halloween? Aren't you supposed to dress up as ghosts and ghouls?

[Shafted]

I had a thought the other day:

Why do you guys wear heels, dresses, skirts etc. on Halloween? Aren't you supposed to dress up as ghosts and ghouls?

It's always been said that the way one dresses up for Halloween is just people being themselves.

[Foxyheels]

I must admit I don't understand the reason for it, as the Dr said it's Dracula, werewolves and the like over here.

[thesampeople]

The best thing about Halloween in my City is the fact that as a man its the only day of the year we can dress up as a woman without been judged. Last year i was a mighty fine sexy Nurse. It was a pretty liberating experience Granted not a Great Story though

[Heelster]

I must admit I don't understand the reason for it, as the Dr said it's Dracula, werewolves and the like over here.

You can only have so many werewolves and vampires in one place. Here in the states, your best shot at seeing these creatures is Washington DC during an election cycle

[ilikekicks]

I had a thought the other day:

Why do you guys wear heels, dresses, skirts etc. on Halloween? Aren't you supposed to dress up as ghosts and ghouls?

What if I do an anime character whom wears heels?

You can only have so many werewolves and vampires in one place. Here in the states, your best shot at seeing these creatures is Washington DC during an election cycle

That would be ZOMBIES!

[CassieJ]

oooooooh. Zombie clubbing girl. Might even make the toughest attempt to 'pass' easy.

[Pumped]

I must admit I don't understand the reason for it, as the Dr said it's Dracula, werewolves and the like over here.

State side the Halloween partys tend to bring out the slutty school girl custumes, hooker outfits and the like. I have seen more than one guy in a dress and heels. If my wife was more supportive I probably would try the dress and heels. I think it would be fun! I even thought of wearing a men's three piece suit and my 5 1/2" heels for a more subtile custume and see if people would even notice. Halloween people tend to relax and let thier crazy side out and for the most part anything goes.

[Dr. Shoe]

What if I do an anime character whom wears heels?

Still not a ghost or a ghoul...

[Curt]

Dressing up in heels won't work for halloween for me. A wear them every day. I went to a shoe store, and was looking at kneehigh boots. The sales lady said, buy these, they're $5. Wear them for halloween! I said you don't know me very well! Clarissa

[Bubba136]

Dressing up in heels won't work for halloween for me. A wear them every day. I went to a shoe store, and was looking at kneehigh boots. The sales lady said, buy these, they're $5. Wear them for halloween! I said you don't know me very well!

Clarissa

That wasn't a very nice thing to say.

[Dr. Shoe]

Depends on whether it was said with a smile or not. A few years back I was going into a shoe shop and I missed the stairs up to the mens' department and an assistant said "this is the ladies' department sir." I laughed and pointed at my heels and said, "That doesn't usually stop me!" She giggled as well.

[Curt]

Cool story, dr shoe! Been there, done that!

[MartaGanz]

Hi all! This successful story happened yesterday afternoon. I like dressing up for Halloween and I do (usually imitating glamorous ladies real or fiction). in high heels for 2 years. 2012: Angelica Huston (The Addams). I decided. My boyfriend knows this and doesn´t like (barefoot is 2 inches / 5 cm shorter than me) and I set a trap...for him. BF and I went to my work shop (until USA W 11- 42 EU) and I asked for leather pumps 5 inch black size 42. When my colleague returned, she told me if I wanted to put on them and I said: "It is better if he does it, because he´ll be wearing for hours..." My boyfriend is always pissed when I wear HH. Well, this year he is going to be as tall as me, because I'll be "The pink sheriff" with my pink pants, my shirt, my pink leather jacket pink. And yes, of course, my 3.5 inches pink cowboy boots. Suddenly, his face changed and when he saw me, he knew he has to put on the pumps, yes or yes. And he did. Everything is ready. His black leather clothes and his pumps, and my pink disguise. He assumes his role and I am very happy with his decission.

[ilikekicks]

my pink leather jacket..

That is something I have never seen in person. Have any pics of that Jacket?

-Ilk

[hiheellover23]

Well my best story would be this year where I wore heels to work!!! It's wild right!!!! Well I came dressed as a guy from the 70's. I had on a green fitted t-shirt, a gray and metallic vest, some flare jeans, and my glitter lita boots!!!!! Oh lets not for get I had an afro as well. I was a big hit at the job people were in disbelief that was me. People wanted to get pictures of my boots and could not believe how well I walked in them. One guy mentioned about how much my butt stuck out when I had the boots on. Felt a little awkward at the moment but I took it in stride it was my moment!!! At first I was like I wasn't going to do it but I just said "F" it its Halloween. From what all my co workers said they said that my costume was the best one out of all three shifts. Plus there was a guy that I told about my heel wearing like some years ago. He told me that I had the best costume over everyone and he pulled me to the side and wished me a congratulations on gathering the courage to wear my boots out in the open. Just hearing that was a huge highlight of my day!!! Don't have a picture unfortunately but as soon as I can find one I will get back to you.

[Curt]

That's awesome. I love the 70s. I dressed up in drag to a club with several women on haloween. Well now really drag for me, just a little more femme than usual! The bouncer at the door said" excuse me, young lady, but you can't come in without a costume!" So I flipped my wig! I was dressed too classy. I said to him, next time I'm wearing my slut clothes. All the girls were laughing non-stop! We hang out all the time, and e-mail back and forth beauty tips and pics of heels. I wish I was born female. All these things come naturally! Clarissa (in girl mode)