Halloween Misadventures

Halloween Misadventures
By RogerGirl

 How did I let myself get talked into this?  I've always had a hard time saying no to people and this time I let things go too far.  I sit in silence and glance shyly up at my dad as he drives me home from the police station.  Ironically, I'm dressed as a slutty cop.  My boobs are front and center for all the world to see, as are my legs and midriff.  I sit with my legs crossed and look at my reflection in the mirror.  My makeup is smudged and my long blonde hair is a mess.  My dad says nothing as we pull into the driveway and go inside.  I know he is going to say something eventually, but for now he is quiet.  My mom hugs me as we walk in and takes me to the bathroom to get me cleaned up.  She helps me take off my jewelry, remove my makeup, and brush out my hair.  Since all of my clothes are at my apartment near the university, she gives me one of my sister's nightgowns to wear to bed.  I take off my knee high boots, fishnet stockings, miniskirt, top, and bra and put on the nightgown.  As I pull the nightgown over my head, I catch the reflection of my naked breasts and the glimmer of my naval ring in the floor length mirror.  My mom tells me goodnight and I go to bed in my old bedroom.  Looking around at my room full of video games and posters of bikini clad women, I feel really out of place.  Oh, I should probably mention that I'm a guy.  

 You're probably wondering why I'm dressed as a woman.  For starters, I'm not transgendered or a crossdresser.  The breasts and vagina are fake and attached with some kind of glue.  Before Halloween I have never dressed as a woman before, nor do I plan to again.  My name is Jamie and I'm a 22 year old college student.  I work part-time as a bartender at the Tilted Kilt and have been dating my current girlfriend for the past year and a half.  I have agreed to keep her identity anonymous for this story so that she wouldn't lose her volleyball scholarship.  While she managed to get away before campus police showed up, if anyone found out she was involved it could result in her being kicked off the team.  She is actually the reason I'm dressed as a woman.  While I normally don't do anything for Halloween, this year she convinced me to go to a costume party with her.  Reluctantly I agreed, but now I wish I hadn't.  You see, this wasn't an ordinary costume party, it was a gender swap costume party.  I found this out when she came over the afternoon of the  Halloween party to show us the costumes she had picked out for us to wear.  Now I should mention that I have always been somewhat small and thin and with my long blonde hair people often joked that I looked like a girl.  My girlfriend, however, is a volleyball player.  She is several inches taller than I am and more muscular too.  As I looked at the costumes I was surprised at the sizes of each costume.

"Slutty cop and a prisoner costumes?" I said as she held the costumes up for me to see, "Don't you think the prisoner costume is a little big for me though?"

"The prisoner costume isn't for you," she replied laughing, "You're going as the slutty cop."

"I don't want to go as a woman," I responded defiantly.

"You have to," she pleaded, "It's a gender swap party.  Everyone is going to be crossdressed."

"You didn't say this was a gender swap party," I said in shock.

"Please," she responded, "It will be fun."

"Fine," I said.

"Yay," she exclaimed happily before kissing me, "Now we have to start getting you ready if we want to win the costume contest."

 What followed was the complete elimination of my masculinity.  Over the course of the next several hours I had my body hair removed, my eyebrows trimmed, my ears and naval pierced, fake breasts and a vagina attached, a temporary tattoo placed on small of my back, acrylic nails attached, my nails painted, and my hair and makeup done.  When she was finished, I was no longer a skinny college guy with long hair.  I was now a sexy campus coed who would have to fight off the advances of every straight male.  My top barely covered my large realistic breasts and did nothing to cover my thin waist and flat stomach.  The skirt sat very low and covered very little of my ass.  My entire body was smooth and hairless and the boots made my long legs look amazing.  Even though I knew everyone at the party would be crossdressed, it was clear that I would probably be one of the convincing ones there.   As I practiced walking in the boots and working on moving and talking like a woman, my girlfriend went to change into her prisoner costume.

 A little while later my girlfriend returned looking more masculine than I could ever look.  Her medium length hair was combed back with some gel and she had fake stubble on her face.  I didn't know at the time who else put this much effort into their costumes, but based on the fake penis she was wearing it was clear my girlfriend was determined to win.  After grabbing a few last minute items, we left my apartment and headed to the party.  When we got to the party, the crowd was pretty much what one would expect.  Most of the guys didn't look very feminine and most of the girls didn't look very masculine.  Despite this, you could tell that some of them put a lot of effort into their costumes in spite of their lack of abilities to makes convincing members of the opposite gender.  There were several at the party who, like me and my girlfriend, could definitely pass as the opposite gender.  As we made our way through the crowd, my girlfriend took my hand so we wouldn't get separated.  She got us some drinks and someone handed me a joint to smoke.  

 After a while I had loosened up quite a bit and started doing things I would never imagine myself doing.  I don't remember much, but at certain points throughout the evening I made out with another guy who made a convincingly hot chick, had sex with my girlfriend in one of the upstairs bedrooms, did a sexy pole dance to the song "Dude Looks Like a Lady," and my girlfriend and I won the costume contest.  As you can probably guess, there were plenty of photos and videos taken of my exploits that night.  Of course, none of this had anything to do with why my dad had to pick me up from the police station.  To further explain that, we should first return to the present.  Since the solvent remover is at my girlfriend's apartment and she is in class and at work all day, I'm stuck as a woman for several more hours.  My mom helps me get ready and gives me some more of my sister's clothes to wear.  Soon I'm wearing another skirt and my mom is doing my makeup.  Luckily I only have an afternoon lecture on Fridays.  

"I've always wanted another daughter," she says as she fixes my hair.

 Once she is finished she has me go downstairs to where my dad is waiting for us to discuss what I did the night before.  Now before you jump to any conclusions, neither of them are angry that I am dressed as a woman.  In fact, they both tell me that I look very pretty as a girl and that I have a nice feminine figure.  They both know that I only dressed up for the party and realize that it was all for fun.  What they are angry about, however, is the manner in which I carried myself the night before.  The drinking, weed smoking, stripping, and lesbian make out session are of no concern to them, but they do not condone the actions that got me arrested.  Those actions have to do with a college football rivalry.  Now my parents both understand the rivalry and even participated in rivalry pranks when they were in college.  Unfortunately, the prank we pulled in our drunken state the night before went a little too far.   

 Late Halloween we were all pretty drunk and high after the party.  The big rivalry game is on Saturday and since Halloween was the Thursday before we were all really pumped for the game.  A few days earlier some students from our rival university had unleashed a prank on our campus.  Now the prank they pulled was pretty harmless and only did some minor damage to the statue of our university mascot, but nonetheless it hit us pretty hard.  While I normally wouldn't participate in pranks, in the condition I was in I was up for anything as evidenced by my earlier actions that evening.  I found myself with a group of my girlfriend's friends sneaking onto our rival's campus in the middle of the night.  Their plan was to cover the mascot statue in bird seed and unleash a bunch of pigeons on top of it.  Everything was going well until campus police showed up.  We all began to run, but since I was wearing heels I wasn't as steady on my footing and fell on the wet grass.  Now so far I had done nothing that my parents were particularly angry about and they even thought all of it was pretty funny.  What happened next, however, is what angered them.  

 The campus police caught me and instead of cooperating and going along peacefully with them, I made the mistake of trying to fight back.  Soon I found myself being tazed and sitting in the back of their car.  They took me to the campus police station and after discovering I was really a guy and that I had no record, they decided to let me off with just a warning.  Unfortunately for me though, they had to hold me in a cell until my dad could come and pick me up.  As I sobered up in the holding cell and the effects of the weed wore off, I began to panic as I thought about how much trouble I would be in.  Even worse, when he came to get me he would see me dressed as a woman.  At the time I didn't know that he would be so cool about that part.  

 That brings us back to the present.  I sit quietly with my legs crossed as my parents tell me how stupid it was to fight a police officer and how lucky I was that they didn't charge me with anything.  Sitting here I begin to realize how badly I could have messed things up for me if I had suddenly had a criminal record.  Eventually the yelling stops and soon we are in the car heading back to campus.  During the drive they tell me to relax and to just continue playing the role of a woman until I can take off the prosthetics.  They drop me off near my class and I hurry in and find a seat near the back.  The skirt I am wearing is pretty short so I want to be seen by as few people as possible.  I take out my laptop and keep my legs tightly closed.  As I wait for class to start, two people sit down next to me.  It takes me a moment, but I soon recognize them as one of my girlfriend's teammates and her boyfriend from the football team.  

"Hey sorry about last night," the boyfriend says, "I heard that you're stuck like that until tonight.  You're lucky you can pass as a chick.  If I was still stuck as a chick I would look ridiculous."

"Yeah," I reply, "I can't believe I'm saying this, but can you just pretend I'm a girl so that I don't draw any further attention to myself."

"Sure," my girlfriend's teammate responds, "You make a pretty hot girl so that won't be too hard."  

 The professor enters soon after and begins his lecture.  For the next hour I take notes as usual and class goes along like normal.  When the lecture is over we all walk to lunch at one of the on-campus restaurants and grab something to eat.  The more sitting I get to do the better.  Walking in heels is a lot of work and they hurt too.  I have to admit they do make my legs look amazing though.  After lunch I call my girlfriend and she tells me she will be later than she thought.  We finish our lunch and head to my apartment off campus.  Luckily I live alone.  I was planning on having this stuff off before I have to go to work, but that looks like it won't be the case.  I call the Tilted Kilt to explain the situation to them and that I will have to take the night off.  Unfortunately, they are short-staffed tonight and need me to come in.  They tell me I will have to work as one of the waitresses tonight too.  Well, that's just great.  I know I've gotten used to wearing the kilt that is part of the men's uniform, but the women's uniform is so revealing.  My boobs and midriff are going to be on full display for the second night in a row.  

 My girlfriend's teammate teaches me a few things about passing as a woman, including working on my voice, makeup skills, feminine body language, and walking in heels.  After a few hours she and her boyfriend head out to get ready for the big rally for the football game and I drive to work.  When I get there all of the waitresses gush over how good I look as a woman and they take me to the back to get me changed into my uniform.  Soon my shift starts and the girls make sure I don't get any difficult customers.  I do, however, have to sing a few birthday songs and get hit on by quite a few guys throughout the evening.  Surprisingly, I get more tips tonight than I've ever gotten in one night as a bartender.  By the time my shift is over, it is far too late to go to my girlfriend's to change back into a guy.  I change out of my uniform and head back to my apartment.  My mom packed me some stuff to wear in case I wasn't able to change back right away, so I find myself wearing another short nightgown to go to sleep in.  Shockingly, even without any makeup I still look like a girl.  

 The next day I'm woken up by knocking at my door.  I open it and see my girlfriend's teammate holding a bag of stuff.  She tells me that my girlfriend had to take an early shift at work and that she will meet me at the game.  Once again I'm forced to spend another day as a woman.  She gives me some clothes to wear for the game including a female team jersey, short shorts, and a pair of sandals.  She also puts some ribbons in my hair and some face paint on my face in the team colors.  By the time she is done I look like any other girl at the tailgate.  We head over to the tailgate and we join her friend's tailgate party.  Everyone treats me like one of the girls and I quickly begin to relax and have a good time.  I have some food and beer and play some beer pong.  A few of the guys I play against I can tell must be going easy on me cause I rarely ever win.  Several of the guys try to hit on me, but my girlfriend's teammate helps me fend them off.  Shortly before the game my girlfriend arrives at the tailgate and tells me how sorry she is for everything I've had to go through this weekend.  I tell her that it is OK and to just enjoy the game.  

 We head to the stadium and show our IDs to get into the student section.  For once I am glad that I can so easily be mistaken for a girl.  Since my name is Jamie, the ID doesn't state any gender, and I have long hair in my ID photo, the man at the gate doesn't notice anything is off.  In fact, as we walk through the gate I notice him checking me out.  We find our seats inside the stadium and everyone greets us casually.  They all know who I am and were all at the party on Halloween.  Once the game starts, all thoughts about my being in public dressed as a woman are gone and I am completely absorbed by the thrill of the game.  Our team scores an early touchdown and we all cheer.  The game continues and both teams score a couple field goals and touchdowns.  By halftime we are down a field goal.  Having had quite a bit to drink at the tailgate, I am forced to use the women's restroom.  My girlfriend and I get in a long line and wait to get inside.  As I wait in line I wish I wasn't dressed as a woman so that I could use the men's room.  The line over there is much shorter.  Finally we get inside and I go inside of a stall.  I pull down my shorts and thong and sit down to pee.  It feels so strange not seeing my penis.  After we finish, we wash our hands and hurry back to our seats.  

 The third quarter starts and our rivals score a quick touchdown putting us down ten points.  In the fourth quarter, however, we go on an offensive attack and score three unanswered touchdowns to win the game.  We all cheer as the band begins to play and my girlfriend and I share a celebratory hug.  While normally I would kiss her, I don't want to draw any unnecessary attention to myself.  After the game, we meet up with my girlfriend's friends and they invite us to go out with them to celebrate the win.  My girlfriend tells them we should get back to her apartment to change me back.  As much as I want to change back, however, I tell her I don't mind spending a few more hours as a woman and we accept their invitation.  We head over to the party and once again I get pretty drunk.  By the time we leave I am far too wasted to change back and my girlfriend helps me change into another nightgown to sleep in.  

 The next thing I know I am waking up late Sunday afternoon.  My girlfriend has left a note telling me she's at work and will be back in the evening.  I get up and take a shower, then put on another of my sister's outfits and do my makeup.  Not having anything else to do I decide to go out for a while.  I put some stuff in a purse and drive to the mall.  Knowing I will be changing back into myself soon I decide to go into a few stores and try on some clothes.  Even though I don't plan to dress as a girl again, my curiosity gets the best of me and I try on a bunch of outfits.  As I look at myself in the mirror, I can't help but notice how natural I look as a woman.  Against my better judgement, I decide to buy a few things including a swimsuit, a couple dresses, a skirt and blouse, several sets of underwear, and a few pairs of shoes.  I don't know if I will ever dress as a woman again, but if I do I want to be prepared.  After shopping, I grab a quick bite to eat then head home to hide my purchases.  

 When my girlfriend gets back in the evening, she has the adhesive remover with her.  We go into my bedroom and tells me to strip down.  Soon I am standing naked before her and she begins to get undressed.  She removes the last piece of clothing she is wearing and pulls me in for a kiss.  As much as I enjoy the kiss, I have to admit I am a little surprised.  She tells me that she enjoyed having sex with me at the party the other night and wanted to have one last experience before I change back.  I look down and notice she is wearing the penis from the other night.  I reluctantly give in and soon we are having sex as a woman and her shemale girlfriend.  I have to admit while I would never do this again, it is actually quite erotic.  

 Finally, an hour later, I am back to my male self.  We take a shower and clean up everything I had used the past few days.  She puts everything in a box and tells me to keep it.  I ask her why and she tells me she wouldn't blame me if I decide to dress as a woman again.  I say nothing and put the box away with the items I bought at the mall earlier.  Soon I am dressed in my normal male clothes and we head out to meet her friends.  They say nothing about my dressing as a woman and treat me like normal.  We go out to dinner and head back home at the end of the night.  The next day I go to class and work like normal and life continues on as it always has.  

 It is now four years since that weekend and we both have long since graduated.  We both later went for our graduate degrees, but at different universities.  My girlfriend and I stayed together for another year, but eventually we broke up.  I have since started dating another woman and we are engaged to be married.  She actually is my ex-girlfriend's teammate who I mentioned in the story.  We have been dating for about a year now and are still friends with my ex.  

 Tonight is date night and I walk into the restaurant where she is waiting for me.  I scan the room and spot her at a table near the window.  She is wearing a suit and has her hair styled back with gel.  I walk down the steps in my little black dress and five inch heels and make my way to the table.  As you can probably guess, I have continued dressing as a woman on occasion.  While I have no plans to become a woman or live as a woman full time, after knowing how good I can look and how much fun being a woman can be, why would I want to waste that.  While I don't dress that often, I try to dress up at least once every couple months.  Sometimes it is for a day, and other times it can be for an entire week.  My fiancee doesn't always dress as a man when I dress as a woman and I don't always dress as a woman when she dresses as a man.  My parents both know that I continue to dress and we've even gotten together with them while dressed.  My sister knows about it too and sometimes gets jealous at how much better I look than she does at times.  As much as I'd like to continue telling you my story, I have a date to get back to.