Fifty Years of Halloween Costumes
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My First Halloween (dressed) free porn video
My First Halloween (Dressed)
By tied2ava
I had been invited to a Halloween costume party by a former co worker and
had accepted even though my wife had refused to go saying her usual costume
parties are stupid and a waste of time! After deciding to go I thought
about what kind of costume I could wear? I thought of all the usual
costumes vampire, bum, army solder, batman and so forth then came upon the
idea of dressing up (I have been a deep closet cross dresser for years) I
figure the party was almost fifty miles from my house and other than my
former co worker and her husband no one would know me and the party and
maybe I could pull it off, But how to dress and how to get the clothes
without my wife finding out. Then I stuck on it a nurse costume what could
be better I could get a nurse costumes at one of those Halloween costume
store and wear that it would be perfect I could even wear a surgical mask
to hid my mustache. So at the beginning of October I went to the costume
store and with some embarrassment I bought the most plain of the nurses
costume I could find along with some white tights, I also bought some fake
blood thinking I could splash the dress with blood to make the costume to
look a little more scary and stashed it all away hoping to try it on at
some point before the party.
About a week later I was getting my hair cut and talking to the girl that
cuts my hair and told her that I had been invited to a costume party and
was going to go even though my wife didn't want to go because she thought
they were stupid. She asked me about what costume I was going to wear and
at first I told her I wasn't sure because I wanted to do something
different and out of character for me, she smiled and said I have an idea
why don't you dress up as a woman ! I laughed at first and said I don't
think so because my wife would probably divorce me or have me put away, she
asked me why and I told her my wife was so straight laced that it would be
out of the question, she then told me about how she had dressed her macho
husband up on two different Halloweens and walk away returning with a
scrapbook opening it and showing me a picture of a blonde woman with a
white turtle neck sweater, short leather skirt, black patterned stocking
and black high heeled boots looking away from the camera, the next picture
the person had turned their head and was now looking at the camera
revealing my Amy's husband all made up looking into the camera, a third
picture showed him dancing with Amy who was dressed as a policeman
handcuffing her husband, she showed me a couple more picture of him dressed
including one with them holding a trophy showing that they had won third
place in the bar's costume contest . She then turned the page and showed me
some more pictures this time her husband was in a floor length velour dress
with a brown wig on and wearing high heeled sandals on and black stocking
again his face was made up expertly, followed by a few more pictures of her
husband in the dress having a fun and even dancing with Amy who was dressed
in a three piece suit with her hair slicked back and a fake mustache. I
couldn't believe that her macho construction working Harley riding husband
would wear a dress! And she said so, laughed and said why it's Was just for
a costume party, or two actually. She then told me that this year they were
thinking of going as batman and robin so it's not like he dresses up in
women's clothing every year or something! She then told me that she could
lend me a dress if I wanted. I declined the offer and we continue talking
while she cut my hair. As she was finishing I told her that after our
discussion I had an idea for a costume and asked her not to laugh! She
promised not to. I then told her my idea I said I liked her idea of
dressing up and said "how about this? A nurse's dress and to make it more
along the Halloween theme splash it with blood?" she looked at me and
smiled and said that's a great idea for a costume! She then pulled out a
flyer from a Halloween shop opened it and showed me the woman's costume
page with several nurse's uniforms on it we looked though the different
costumes eliminating three of them as too sexy or silly and finally she
pointed to one that was closer to the traditional nurses dress and said
that's the one to get that one that should do, she then told me I should
buy a large or extra large. I couldn't believe my luck she had pick out the
one I had already bought. I said great but there was no way I could buy
something like that and keep it at home or try it on at home, Amy just said
get it and bring it here that way you can try it on here and leave it here
until the party. I tried to play coy and said I would think about it, and
left it at that, Amy replied when you change your mind give me a call. She
finished up and I went on my way.
A few days later the actual invitation for the party came in the mail and
on the front of the invitation my former co worker had used a picture form
one of their past parties where her husband had dressed up as a French maid
(comical of course with really large boobs and bad blonde wig) and her as a
clown. I called her to say I would be but my wife wouldn't as she didn't
like costume parties! My friend said that was ok then asked me what costume
I was wearing? I took a deep breath and told her of my idea about the nurse
costume; she loved the idea and offered to help me in any way possible.
After about a week I couldn't take the suspense anymore and called Amy up
and told her I had screwed up the courage and bought a nurses uniform and
wanted to bring it over to her house and leave it there, unfortunately she
said when you bring it over you can try it on! I tried to decline but she
said oh no you might as well make sure it fits and then said see you in an
hour and hung up. What did I get myself into?
I arrived at Amy's house to see her standing at the front door waiting for
me. I brought the costume in and showed it to Amy who opened the packet up
carefully and held it up and looked at it, she then said "I don't know it
looks really cheap and short to me! Then she turned and handed it to me and
said try it on I pulled my shirt off and went to pull it over my head and
she said wait go into the bathroom and take your pants off too you're not
going to be wearing them under it anyway. I walked off to the bathroom took
off my shoes and pants and pulled the costume on over my head and attempted
to zip it up the best I could. It was scary I was at someone else's house
with a dress on something I had only done before with a girlfriend years
ago at her behest. I looked at myself in the mirror pulled the dress down
and walked out into Amy's living room for her to see looked laughed and
said that just will not do! The material is too thin you can see right
through it and it's too short even for me as a Halloween costume, unless
that's what you want is to expose yourself all the time and I don't think
you'll even to get a bra on under it, it looks like it barley fits in the
chest area and there no room for you to put some breasts forms in! She then
told me to "wait here "and left the room. When she returned she was holding
what looked like three dresses, she hung them on the fire place and said
try these on and we'll see what one fits and or you like. She first handed
me a red dress that I took to the bathroom and put on, the dress had a
halter top and the skirt portion seemed to be really wide at the bottom and
short I walked out with it on and Amy looked me over and said I like it but
I think you would need to do a lot of shaving to make it look good and
laughed, she then handed me a cream colored dress and said try this one
now, I returned to the bathroom and took of the red dress and pulled the
cream colored dress on and attempted to zip it up the back but found that I
could get the zipper up past my waist it was just too tight, I walked out
with my arms though the sleeves and the dress around my waist and wide open
in the back and told and showed Amy that it didn't fit! She then handed me
the last dress a long black velour dress, I took it back to the bathroom
pulled off the cream colored dress and then stepped into the last dress
pulled it up put my arms though the sleeves and zipped it up the back as
far as I could, the bottom of the dress was on the floor and it had
sequins sewn on around top of the dress around the neck, the back was
scooped and had a brad of material hanging down around where the dress
dipped in the back. I walked out again for the third time Amy told me to
turn around and she zipped up the zipper the rest of the way and told me to
walk across the room and back, I did as I was told then she said well I
think that will be perfect, now you just need some accessories. I asked
what she meant and she said shoes, hose and lingerie, playing dump I said
"I'll just wear gym shoes and stuff some socks or something under the top"
she said no if we're going to do this we'll do it right, come on put your
clothes back on we have some shopping to do!
After putting my clothes back on Amy took me in her car to a Goodwill store
and we walk in and straight to the back where I saw a wall of shoes, Amy
asked me what sized shoes I wore and when I told her eight and a half or
nine, she said ok about a ten in woman's then and started looking at all
the shoes on the wall suddenly she stopped grabbed a pair of what looked
like a brand new pair of shinny shoes with a five inch tall heel and one
inch platform and a strap that went across the top of the foot and handed
them to me and said try these on! I looked at her and said here? And she
said don't be silly no one cares now try them on! I pulled my shoe off and
tried one of the shoes on, it fit fine and pulled it off only to be told
put it back on and the put the other one as well, I reluctantly did so and
was encourage to walk a bit with them on, thankfully the heel was a one
inch square heel and not a spike so I was able to walk in them without too
much of a problem, she then said great, get those and walked to the
registers. I followed her with the shoes in my hand and when I reached the
register I put then down on the counter where the young girl said those are
really nice shoes I wish we had them in my size. I then paid the three
ninety nine for them and left the store with Amy feeling like I had a giant
sign on my back announcing I was a cross dresser! We then went to the local
Wall mart and straight to the lingerie section where Amy grabbed a Black
bra with padded cups and said I think a forty "C" will do! Then she walked
over to where all the panties were grabbed a pair of panties that had a tag
on them that said control briefs large and gave that to me, they felt very
thin but stretchy and slippery, last we went over to where the hosiery was,
where she looked though all the different styles, then and took a packet of
what appeared to be a patterned stocking and handed the packet to me I
looked at it and it said size: long, color: black, Style: patterned. At the
bottom of the packet it said "now with two bands of silicon to stay up
better". I looked at the packet an then at her and she just smiled and said
"those will be better" and said "come on" and once again I had to stand at
a cash register with a young girl and pay for items of woman's clothing
somehow I manage to pay for the stockings panties and bra without anything
being said, we then return to Amy's car and went back to her house.
Once at Amy's house she said ok let's see if some of the items fit she then
said take of your shirt, and when I did she pulled out the bra and had me
put on and after she clipped it on she started adjusting the straps, after
she fixed the straps she said wait here I have an idea and disappeared.
When Amy returned she was holding a pair of suntan pantyhose, some scissors
and a bag of rice, She proceeded to cut the legs off of the pantyhose, fill
them each with about a cup of rice tied them off and stuffed them into the
cups of the bra I was wearing, adjusted them a little and said perfect! Amy
then said go put the dress on again I want to see how it looks with the bra
on and filled. I did so and after being looked over she said that will be
fine. I changed and told her thanks and went home.
All's I could think about during the next few weeks was wearing the dress ,
the my friend called me and asked me if I had gotten my costume and I told
her of my troubles with the dress being too short, thin and cheap! She
asked me what I was going to wear and I said I wasn't sure but Amy the lady
who cut my hair wanted me to wear a dress her husband had worn the year
before, and she said that was a great idea, but then she asked me about my
mustache and I said I didn't think about that and she that was no bother if
I didn't want to shave it I should just trim it as short as I dared then
grow a day or two's growth of a beard and go as a cross dresser it would be
funny and perfect! And that way my wife would be suspicious of anything.
A few days after talking to my former co-worker I spoke to Amy who said it
would be a great idea! She then told me she wanted me to come by a few
days before the party to try everything on and see how I looked.
On the Thursday before the party I arrived at Amy's house after telling my
wife that I was going to meet some friends for breakfast. Once at Amy's I
was handed the dress, panties, bra and rice filled nylons and told to
dress, I went into the bathroom took off my clothes pulled the panties up
put on the bra filled the cups with the rice filled nylons and then put the
dress on the dress and zipped it up as far as I could in the back. I
couldn't get over the feeling of the panties tight but not restricting and
very silky feeling, the feel of the filled bra weighing down on my chest
jiggling as I moved. Once I regained my composure I walked out to where
Amy was standing and spun around she said nice but you're not done yet she
then told me to sit down and handed me a pair of black stockings and said
"these are an old pair of my stocking I want to show you how to put them on
without running them" she then told me to roll them up into until they foot
was the only part showing then she told me to pull up my skirt and put the
stocking on my foot then roll the stocking up my leg to the top, I did so
trying not to show my panties , she then had me do the other leg. Once the
stocking were on she brought out the shoes I bought and put them on my
feet. Amy then had me walk around the house until she felt I was
comfortable, and then she pointed to her styling chair and told me to sit
down.
Once in the chair Amy explained to me as she took what hair I had and
rolled it in rollers and explained that on the day of the party I was to
come to her house and she was going to curl my hair like this as she rolled
my hair in rollers and sprayed it with water, waited a few minutes then
blew my hair dry and took the rollers out showing me how my hair would
look, sort of silly but would give me that cross dresser look, she said
that she would also make my face up too on the somewhat over done look ,
and it would be perfect. I just shook my head in agreement and asked if I
could change and she told me to wait as she wanted me to get used to being
in a dress, we then moved to the living room and said and talked and had a
cup of tea. I was finally allowed to change, she wet my hair to get the
curls out and I left to go home. I went home excited but also scared as I
had never been dressed in front of people.
Well Saturday the day of the party finally arrived and after puttering
around I got ready put on some camo so she my wife would think I was going
as an army guy, I then drove to Amy's house.
At Amy's house I walk in to find her husband and one of her daughter's
there, hesitated at the door only to be grabbed by the arm by Amy and
pulled into the house and was taken to the little room where she does hair.
Once in the room she say okay here's your clothes I'll leave and you change
into them and then I'll get started, I said but I thought I would just get
dressed at the party, but Amy said no I need you dressed before I can do
your hair and makeup she then walked out and said hurry up my husband and I
are going to a party too and we have to get ready with that the door
slammed shut. I stood there stunned and there started undressing, then I
put on my on my costume first the panties then I opened the packet of
stocking we had bought rolled them up and then put them on my foot and
unrolled them up my leg to my thigh where I felt the silicon bands grab
onto my skin and hold the stockings up I next put on the bra, put the rice
filled stockings into the cups and then stepped into the dress (what am I
doing!!) pulled it up, put my arms though the sleeves then I pulled the
zipper up as far as I could and called for Amy to return. Amy returned
finish pulling the zipper up and told me to sit down in her styling chair,
she put a plastic apron around my neck and went to work on my hair she wet
it down then rolled it in several rollers and then pinned them in place,
after that she put my head under a hair dryer and waited a few minutes for
my hair to dry. After my hair was dried she removed the hair dryer then
went to work on my face, she first put eyeliner on my eyes lids followed by
blue eye shadow, then mascara on my lashes and then some bright pink blush
onto my cheeks , followed lastly by a bright red lipstick on my lips,
looking in the mirror I looked garish but with my five o clock shadow it
fit the look we were going for perfectly, then the rollers were removed
from my hair and she sprayed it with hairspray, my look was complete I
looked ridicules but not totally ,more like a guy in a dress it was a
perfect costume. Amy then kneed down in front of me and put the high heeled
shoes on my feet helped me up and handed me a black purse, telling me that
she had put my wallet and I.D.'s in the purse alone a compact and the tube
of bright lipstick that she had applied to my lips. Amy then walked me out
into the living room where her husband and daughter were standing waiting
for me they both laughed then said perfect! Amy then walked me out to my
car and wished me a good time as I climbed into my car. After Amy walked
away I grabbed a jean jack I had in the car and put it on to help hid the
dress I was wearing and pulled my right shoe off so I could drive and was
on my way! I couldn't believe it I was driving in public dressed and loving
it! The feel of the silky tight fitting panties the stockings on my legs
the bra and the weight of the fake boobs on my chest, the taste of the
lipstick it was fantastic, until I realized that anyone who pulled up next
to me would see me (hopefully it was dark enough that no one would really
notice or so I hoped) and someone did as I was stopped at a stoplight
waiting to get onto the highway a car with two girls in costumes pulled up
to me and looked at me and started laughing, thankfully the light changed
and I pulled onto the highway with the image of the girls laughing burned
into my mind and fifty miles to drive, what was I thinking? And why did I
let Amy dress me up at her house before I even got to the party?
The rest of the drive was actually pretty normal other than how I was
dressed I didn't have anyone really look at me or gawk at me as I passed
them or they me. However the sensation of being dressed and out on my own
was enlightening and sensual the feel of the nylons on my legs the weight
of the bra on my chest the slippery tight feeling of the panties, the feel
of the dress I was wearing and the taste of the lipstick, the thing I
always wanted to do but was too scared to do! But now I was doing it I was
actually out and dressed.
After almost an hour drive I was finally at my former co workers house, I
pulled up parked my car and put my right high heeled foot out the open the
door and went to get out of the car and in my first mistake of the evening
ran into a little problem I couldn't get my left foot out of the car
because of the dress, I forgotten about that so before I could get my leg
out I had to turn in my seat and put both legs out together then get up
straighten the dress and step away from my car before I shut the door so I
wouldn't catch the dress in the door, and walked up to the door took a deep
breath and rang the bell. My former co worker answered the door looked then
did a double take and step out and gave me a hug and stepped back and said
let me look you over after looking she said I love the shoes and then asked
me if I had pantyhose or stockings on nylons on too, I reluctantly pulled
up my dress a little so she could see my black patterned stocking and said
stockings she smiled and said nice and then invited me in and as I walked
in she complemented me on my ability to walk in the heels.
I spent the rest of the party enjoying the erotic feel of the stockings and
panties and having people laugh at my costume but also accept it as just a
Halloween costume! I also learned a lot that night some of the girls
instructed me every so often on to wear a dress and how to go up and down
stairs in a long dress and not falling by holding the skirt and pulling it
up above my ankles almost to my knees as I go up or down the stairs so I
don't trip on it.
It was a great night If only I could do it again!!
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