Saturday, October 25, 2014

A Mistress Can Make Halloween Very Humiliating

Tonight is going to be my first night in a dress in over 7 years.   When I've told people this, who know about my history, a lot of them have told me that it won't be a big deal because it's Halloween.  There's definitely some truth to that.  It was much easier buying female clothing and wigs at this time of year, but a skilled mistress can make Halloween very humiliating.  

The problem is that once you have mastered your appearance and mannerisms and feminine grooming, it's very hard to just look like  a hairy guy in a dress who never wore heels before.  This is especially true if your mistress won't let you act that way.  While guys dress up as girls all the time, they don't do it with the skill or realism of an accomplished crossdresser.  This is the rub.  It's the part that makes me nervous about tonight.  I'm sure I'll post to let you know how it goes.

From Welcome to College II:

Sure enough, for the next two hours I posed for pictures.  At first the posing was limited to the dorm room, but that soon changed.   I wasn't going to budge, but the girls reminded of just what would happen to me if I disobeyed.  Reluctantly, I followed Amanda out the door for more pictures with the other girls in tow."
"Relax Kylie," whispered Deanna reassuringly, "A lot of guys dress up for Halloween."
"Yeah," said Amanda, "Lots of guys always go to Halloween in drag."
"Sure they do," offered Wendy, "and they shave off all their body hair, wear a corset, and master walking in 3 inch heels.  Lots of guys do that."
I immediately deflated, which I think somehow delighted Wendy.  Deanna was always nice and optimistic; Karen had a wicked sense of humor, but usually didn't go out of her way to put me down; Amanda was definitely in charge, but Wendy seemed to be the one who most delighted in dominating me.
As we approached the dance, I began to have second thoughts, but I didn't have many choices.  I couldn't outrun them if I had been wearing gym shoes.  In my heels, I was trapped.  I hadn't noticed that the girls were dressed entirely in black.  They each added a pair of cat ears and called it a costume.   Meanwhile, I had the elaborate Can-Can Girl outfit.
"Please don't make me do this," I begged one last time, "I'll be a laughing stock."
"Nonsense, you look great," said Deanna grabbing my elbow and escorting me forward despite my resistance and nervous shaking.
Walking into the dance was an experience that I never had before.   Every eye in the place seemed to be on me and it wasn't because they thought I was a guy.  Amanda and her friends beamed like proud parents as they saw me take my first high heeled steps into the room.  I was thankful for the red wig, which was a pretty close approximation to Nicole Kidman's hair in the movie and did a lot to change my appearance from my usual dark black wig.  I hadn't eaten since lunch, but between my nerves and the tight corset, I didn't have much of an appetite.  I did head over to the drink table however, to get a soda.  DuPont College was a dry campus, a fact flaunted by most every student there, but it meant there was no alcohol at official campus functions. 
Sure enough, it wasn't too long before a guy came over to talk to me.  His name was Jon and he was a sophomore.  He was actually a football player in high school and was a pretty big guy, but he was also a pot smoker.
"Hey, I'm Jon," he said.
"H-hey Jon, I'm Kylie," I said in my best feminine voice.  To this point I hadn't really practiced a voice and I know I sounded like a Monty Python character.
"Kylie, eh?  I haven't seen you around before.  I love your costume," he said.
"No, no I'm uhm, friends with some of the girls here," I said.
Suddenly, Jon's eyes grew big.  Between the girl's snickering behind him, my nervousness, and my horrible falsetto voice, he had realized that I was not quite what I appeared to be.
"Dude, that's amazing, but man it's disturbing too," said Jon as he walked back to his friends.
Before long, word spread around the party that I was a guy.  I had a lot of people throughout the night coming over to check on me and make sure that I was indeed a guy.  Amanda told me not to volunteer the information, but if asked I should answer honestly.  The reactions varied greatly from cute girls who wanted their pictures taken with me to guys who felt a little betrayed by their attraction to me.  I was both surprised and relieved to find that even the guys most disturbed by my gender switch had no intention of doing me harm. 
About an hour into the party, Bill and Dwayne approached me and Bill immediately began doing his Three Stooges shtick. 
"Oh, it's a pretty lady," said Bill in his best Curley voice. 
"Hey you, I saw her first," said Dwayne as Moe.  They then pretended to fake fight.
"So, this is why you couldn't be a stooge?" asked Bill.
"It's a long story," I said reluctantly.
"Hey, if you're gay or something, we don't care," said Bill.
"Really?" I asked.
"No, we're your friends said Dwayne.  Would you care if we were gay?  Not that you could tell from all the dates we're getting," added Dwayne.
"I guess not," I said.
"Doesn't he look amazing?" said Amanda, "His costume was my idea."
"I never would have known he wasn't what he appeared to be," said Bill
The girls, Dwayne and Bill, and I spent a lot of time talking that night.  I was thankful for Amanda deflecting any potential awkwardness with my friends, but I was even happier that my friends were open minded enough not to care.  We hung out together in the front lounge where my feminization had all started until 2 AM and Dwayne entertained us with his piano playing before he was told to stop because it was too late at night.   All in all, it was a pretty good night.


  1. Hi Kylie,

    I'm very excited for you!

    I'm sure you'll "wow" them... Even if you'd rather not do so, I'm sure Deanna will help to make sure of that!

    Thanks for sharing, Kylie... It is a lot of fun living "vicariously" through your adventures and your published stories!

    - Jenn

    P.S. You look great in those past costume pics!

  2. I totally agree. You made a much cuter girl than a guy I'm sure Kylie