Trick or Treat With or Without Brad

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Halloween goes all wrong for sissy.
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sissypt
sissypt
5 Followers

It was that time of year again, Halloween! The only holiday you were allowed to dress however you wanted and the sluttier the better! My friends and I had been invited to a Halloween party and were now on our way to find a costume at the nearest shop.

Brad had decided to go as a mummy and Clint was a pirate. Me, a clown no way. Trojan yeah right, I was skinny and barely had any muscle on my body. How about a wizard, Clint asked. Neah I replied.

Maid, brad said holding up a tiny black and white French maids outfit. Come on, it'll be fun! Uh, I don't know Brad, I said. Don't be a drag Brad replied, you have the perfect girl body. Skinny and a big butt he said as he and Clint started laughing. I did have a bubble butt which was my most prized body part. I guess I said. Awesome Brad replied!

Let's see what else you will need, asked Brad as we walked through the store together. "Leggings, wig, shoes. Got it let's go!" Brad, Clint, and I all ran up to the cash register to check out. We had to hurry, we were all going to have to go home and shower before the party.

As the clerk checked us out, she grabbed each costume and looked at it and smiled, when she got to the maids dress she gave me a look like she knew this item was for me! Credit or debit the lady asked while continuing to stare at me with a sinister smile. Credit, Brad said to the lady, his parents were rich and he always bought us stuff without even asking.

We all ran to Brads car in the parking lot and raced home. Let's go guys, Brad exclaimed as it was already 2:30 in the afternoon. Clint and I ran home and Brad said, be ready by 6:00. Plenty of time,I thought as I raced to the local store to grab some Nair, hair remover.

Once I got home, I ran up to my room grabbed the hair remover and lathered up my legs with the stuff, while I turned the shower on. I didn't have much hair so it would work fast I thought. I then dabbed a small amount on my chest which also had very little hair and went on to shave my small boi parts. My ass was good and I was naturally bald down there so I was good to go. I was always pleased that I was mainly a naturally bald person. Brad on the other hand not so much, I thought. He was a hairy guy, I remember him from gym during high school. We made fun of him all the time. He was so hairy and I guess he had enough of us teasing him and then one day he took his towel off and revealed one hell of a cock. The jokes stopped there.

Me not so lucky, I barley had any hair any hair at all and I had a very small cock. I thought shaving would make it look bigger but it made it worse. It showed how small I really was. My balls were undersized as well and I could fit into small panties easily without much of a bulge. Being a maid kinda made sense I guess.

Once I was all cleaned up I hopped out of the shower and ran downstairs to tell my mom and step dad my plans. Not so fast young man, I hated when he called me that. I was 20 and moving out soon but not soon enough.

You have to take your little brother to a party. What, I exclaimed! You serious Danny? Yeah I'm serious, young man! Your mother and I are going out to a party. I'm headed to a party too though, I tried to explain. That's all I want to hear about it. Get it done, Danny demanded.

What time, I asked. 8:30 Danny said. What! Our party started at 6:00 I thought! Fucking great. I was doomed, once my step dad made a decision there was no changing his mind.

I immediately got on my phone and called Brad. What's up dude he answered, aren't you getting ready yet? Party starts soon! Bad news, I replied as I laid in my bed, now 5:30.

Now what, Brad asked. I got to take my kid brother to a stupid party before I can go out, I replied. I'll have to meet you there I explained, as I laid in my bed on my tummy with my legs in the air rubbing my little feet together.

Fuck, Brad replied. I was hoping to go to this party together! Fine, fucking see you there! Wait Bra... click, Brad hung up before I could even say bye.

We had been best buds since 6th grade and I hated disappointing him and he me. He knew my step dad was a dick and didn't like how he treated me. He was almost like my big brother and stuck up for me all the time. He wasn't gay but if he was I knew I'd suck him off in an instant. I felt so bad.

Time seemed to be going by so slow at this point and it was now only 6:30. I laid in my bed and put my hands behind my head catching a side glimpse of the small bush of hair under my pits.

Fuck, I thought, how could I have forgotten this. Maybe this will kill some more time. I got in the shower got all soapy and began shaving the masculine hair off my arm pits. Somehow this made me feel so complete. I double checked my body and my legs and made sure I hadn't missed any other spot. Nope, I was good.

I looked down and saw how regressed my penis was. Geez I thought, I'm so small. Any who. I stopped the shower and wrapped a towel around my thin body. Flat chested with very small nipples, skinny legs, almost girl like, especially now that they were shaved smoothly. I looked in the mirror and was very pleased with what I saw. What should my name be tonight, I thought, as I giggled.

I toweled off and put on a pair of small shorts and a t-shirt. 6:45, what the fuck! Time was creeping by. I went over to check on my kid brother. Hey, Justin, you going to be ready by 8:00, hoping to drop his bratty little ass off sooner. "Doesn't start until 8:30 loser."

You don't want to be late though do you, I asked.

"I don't give a shit," he replied. "Mom and dad said drop me off and that's all I need. I'm spending the night."

Yes, finally a break, I thought. For being 15 he was a very wild kid. Talked back to my mom and step dad and always got his way. He used me as his personal slave it seemed like and when he didn't get what he wanted from me, he would just squeal to my mom and Danny.

I went back to my room and looked at the clock, 7:00pm, ugh! So fucking slow!! I went into my room and grabbed my phone. Missed text from brad.

Brad: Hey loser what's up? Me: lol. What's up dude? How's the party? Brad: Bad ass! Hurry up! Lot's chicks here. Me: Sweet! I'm trying bro! Can't leave without my kid brother. Brad: Hurry! Beer tasting good!

What now I thought as I looked around the room. I looked down at my feet and thought, hey why not. I grabbed black nail polish from my mom's many colors and began steadily stroking my cutie little toes nails. Once complete I turned on my ceiling fan and laid down to let them dry.

I fluffed the pillow under me and thought about how cute I'd actually look in that maids outfit. Brad was gonnna be so jealous and maybe he had gotten drunk enough that he would mistake me for a real girl and we would kiss. I smiled and dozed off for a nap.

Next thing I knew I was being woken up by my brother, Justin. Wake up dude! Huh? Oh fuck what time is it? 8:30 bitch, my brother exclaimed! Ok,ok, ok. Let's go dude! I jumped out of bed and put on the first pair of shoes I could find. I had hoped Justin hadn't seen my toes. No time!

We both ran out the house and jumped into my car. My kid brother was already dressed up and ready to go! My backpack had everything I needed and was already in my car. I ran out only wearing my shorts a T-shirt and Sperry's. Fuck it was cold outside already.

I got my kid brother to his party, which was like 10 minutes away and when I dropped him off, he said he needed twenty bucks. For what Justin? Fuck! "Just give me twenty bucks dude, or I'll tell my dad you dress like a chick. "What, I exclaimed! "I saw your little outfit, maid boi!" Justin said.

Fuck you Justin, I said as I handed him twenty bucks. Don't say anything you hear me? Justin, Justin? Whatever, he stated as he slammed the door and walked away from my car ignoring my pleas. What a little dick! Fuck it, I was free!

I started off to my party and it was now 8:55. Time seemed to be speeding up and now I had more text messages from Brad, likely telling me to hurry! I ignored them and just kept driving.

I stopped by a truck stop along the way and took my bag with me into the men's restroom. The stalls were huge and you could get completely naked without anyone spying on you in there.

I stripped down to my ankle socks, bathroom floors were so nasty, I thought. Then I grabbed my outfit and hung it on the hook of the restroom stall. I opened the package and removed the contents. Dress, head gear and a small duster, cute I thought. Then a small pair or g string panties fell out of the bag. I picked them up and looked at the package. The small box next to Small/petite had an X on it.

They looked awfully small and I didn't even think the outfit would come with panties. I unfolded the bottoms and stretched them out. Hesitant to try them on, I lifted my leg to place a foot into them when my phone buzzed. Fuck, I'm coming, I thought!

I continued on and placed my feet and legs into the panties. They were so small and dainty and only had a small piece of satin cloth covering what should be a girls vagina. They were all black with white lace around the top of the front and a small, very cute, bow I might add.

The material was so silky feeling and it felt great going up my smooth hairless legs. I finally pulled them all the way up and although a little snug, they fit perfectly! The G-string rose up my ass and landed softly on my little asshole. When it did my tiny dick pulsated and regressed again into my body. I could have sworn a small amount of pre-cumm leaked out. No time to check, I thought.

I looked down and my entire package was covered by these small very girly like panties. I felt turned on for some reason but was distracted as my phone continued to vibrate. Ok, ok, I said out loud, sounding like a freak to whoever was in the restroom, I'm sure.

Next, I opened the white stockings Brad had bought me and pulled them out. I sat down on the toilet, gross but had no choice, removed my ankle socks and shimmied the stocking around my foot and slowly pulled it up. It felt kind of weird at first because my legs were so smooth but it slide right on and finally rested at about the middle of my thigh. At the top of the stocking was a black bow which perfectly matched my outfit and panties and was just the cutest little add on!

I grabbed the other stocking and slid it on the same way and up my thigh. They both sat perfectly on my thighs. The stockings looked so cute on me I thought. The material was a little thicker than see through but still made of nylon. I'd always wanted a pair like these just never had the courage to buy any. My phone began buzzing again.

Fuck! I finally grabbed my phone from my shorts and sat on the toilet, feet dangling off the floor. Cute I thought as I could see my black nail polish barely showed through the nylons. It was almost teasing for women to do this and now I was the one doing this to whomever saw me without shoes tonight.

Yuck I thought, as I could feel the cold toilet on my butt,and I could see obvious pee stains around the bottom of the toilet. The floor looked sticky and I dared not place my feet down on any part of it.

21 missed texts! Geeez! All from Bradley too. Mainly saying the same thing. Hurry! Where u at and a few with some pictures of him and other people I didn't recognize. Jealousy overcame me but I shook it off quickly.

I felt obligated to let him know where I was.

Me: Hey dude! I'm getting dressed. Chill! Brad: Hurry dude, isn't the same without you here! Me: Aww, thanks buddy! I'm almost done! Promise. Brad. Yeah! Hurry up! I'm getting wasted man! Me: Ok, ok! Slow down, please! It's still early, Bradley. Brad: Whatever, hurry!

He hated when I called him Bradley, I thought as I giggled. I did it on purpose all the time. Anyway, I stood back up and grabbed my maids dress and put it on. So frilly and girly and the waist was a type of spandex that fit tight around my small body. Gosh it felt so good! My phone buzzed again, Fuck Brad, I said out loud!

Finally the shoes. I pulled them out of the bag and sat back down on the toilet. First my right then my left. Then I stood up and caught my balance. I walked over to grab my bag and nearly busted my ass, but managed to catch myself. I made the hugest ruckus I'm sure of it.

I stopped for a second, feet pointing inward, arms spread out holding onto the stall walls, legs shaking, I regained my balance and stood up straight. I looked down at my wobbling legs and took in the sight!

White stockings with cute little black bows and the cutest three inch, patent glossy, size 7high heels. Fuck if I didn't know better I looked just like a girl!

I finally grabbed all my boy clothes and stuffed them in my backpack. I grabbed my shoulder length wig, put it on and put on a pair of overly large girly type sunglasses to hide my face.

After I gathered all my items and my courage, I listened to see if I could hear anyone outside. I could hear a couple of flushes but figured the coast was clear. I opened the stall door and slowly swung the door open. I peeked out and saw a large man standing in front of a urinal taking a long piss.

I stepped forward out of the stall, and my heel hitting the ceramic tile floor made the loudest knocking sound I had ever heard! I stepped again and even to my ears it sounded like the all too familiar sound of high heels on a hard surface.

The man moved his eyes towards my direction then back towards the front. I walked again trying to step lighter, somehow but couldn't control the loud sound my heels made.

I started walking faster to leave as fast as I could, keeping my eyes forward instead of down where I should have been looking. Then I stepped on something wet on the floor, I don't even care to know what it was.

As I took my next step forward in an attempt to run, my back heel slipped underneath me and my arms went out to the side to catch myself, except this time there weren't any walls near me that I could cling onto. When my brain realized this, my arms naturally went out behind me, palms down in an attempt to catch my fall, and out to the side slightly. I slid on one foot as my other went back to regain my balance but it was too late.

Before I knew it my left heel was flying off and both my feet were in the air! I landed on the cold restroom floor with a thud, and an "oof!" My shoe slid across the floor and hit the man, using the urinal, on his large steel toe boot. This definitely caught his attention. Not that some girl in a maids outfit busting her ass didn't.

He looked down at me in astonishment and when he realized what had happened, he smiled sinisterly down at me and growled under his voice. I looked up at him with the most embarrassed look on my face, knowing he knew I was a guy.

He didn't. Hey baby you alright, he asked. The real answer was, no, but I just nodded that I was. I grabbed my right shoe and took it off while the old trucker helped me back on my feet. There was no time to make small talk.

What you doing in the men's restroom, the man asked. I just looked at him with big doe eyes reached down, grabbed my other shoe and ran out. Hey, the man exclaimed.

No time, I ran out of the truck stop and to my waiting car, threw my bags in the back seat and my high heels in the front seat. It seemed colder now but I was barefooted so that may have been it.

I started my car and exited the parking lot, screaming tires until I was back on the road. I finally calmed down as the adrenaline, from the bathroom debacle, began leaving my body. My hands and arms felt shaky but I tried ignoring it. I kept driving to the party determined to still have fun that night.

I was finally in the area where the party was and looked down at the clock. 9:30 pm! I parked far from the house and put my heels back on. Gosh I hoped I wouldn't fall again. I was about 200 feet from the house so I had some time to practice in my new heels. How did women do it!

I then walked up to the house and entered the front door. I could already hear and feel the music coming from inside the large two story home. It was like a mansion! I walked in and was met by two bouncers. I showed them my ID and without saying a word they let me in. I looked for Brad immediately but couldn't find him. I sent him a text but no reply. I barley had signal.

I continued into the enormous house making my way through the party like some movie. As I did I saw people in all kinds of costumes. Pirates, slutty nurses, zombies you name it, this party had it. Had it been this happening the whole time? It was smoky inside and everyone seemed to be either buzzing or super drunk. My phone buzzed in my hand! Brad I thought! Sure enough.

Brad: Hey loser! I knew you weren't going to make it! Oh well. I hooked up with a naughty teacher dude! She's so Fucking hot! You totally missed out! Oh well, lol. Later!

Attached, to the text, was a picture of Brad with a very cute girl dressed as a sexy teacher, I suppose. My night was ruined! I grabbed a beer from the waitress passing by and sat down at the nearest couch and almost began to cry.

Great! All that for nothing! First my step dad ruined my night, so I couldn't come to this stupid party with Brad like I wanted! Then I slept in and got a late start! Then I fell in some sleazy restroom in front of some old trucker who thought I was actually a girl. My eyes filled up with water and I felt a tear rolling down my face. I felt so stupid at this party and now I was all alone. Brad wasn't here to take care of me.

Suddenly, some obnoxious drunk flopped on the empty couch space next to me, scaring the fuck out of me as he made me spill half my beer everywhere! What's up baby?! Haven't seen you here tonight, the guy said. Guess he had been here all night, and hadn't gotten lucky yet. I was almost glad I was late.

What the fuck dude, I exclaimed! Beer running down my arms and trying to wipe off the excess from my costume dress. You scared the fuck out of me, I yelled.

I rolled my eyes at him and just looked away, pulling out my phone and looking at the picture Brad had sent me. "What's the matter baby. Your man stand you up?" Just the opposite, I thought. I turned and stared at him cutting my eyes in disapproval.

"Don't give me that look you worthless little whore." He said to me. I glared back at him with a look of disgust and awe and grabbed my small purse and began getting up off the couch to leave.

As I stood up he grabbed me by the arm and pulled me down again. Ow, I yelled! What the fuck dude! I'm gonna take you home with me you little bitch! I know what you are, Sissy, the man whispered in my ear. I yanked back as he held me tight against his bod but he was much stronger than me.

With a scared look on my face I looked up at the man in total fear. I pulled my arm back again and only the word, please, came out of my mouth. My cowardice only turned him on more as he stood up, grabbed me by the arm and began escorting me out of the house. As I dropped my beer, it popped and crashed on the floor making quite the ruckus.

We were bumping into people on the way out and he kept apologizing for my drunken state. Drunk, I exclaimed, I haven't even had an entire beer! You're hurting me I yelled, as I looked back at him while he was rushing me out of the house, hoping to get some attention from someone that could help. Then he laid a smack across my face that echoed throughout the room.

It was as if the party stopped. I fell down on the floor and covered my face in embarrassment and also because the asshole hit me pretty hard. I checked my lip for blood but I was good. He stood me back up on my wobbly feet and as he did I was grabbed by another guy. A much bigger guy! They grabbed me and the asshole and began pushing us out of the house. The big man grabbed me by the back of my dress, which made it rise up, exposing my ass to everyone! Geez he was tall, I thought, even with high heels I was walking on my tip toes.

sissypt
sissypt
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