Twink or Dare

Although we were both almost twenty, we still loved pulling our childish pranks around our small town. Sometimes our pranks were as stupid as 'dingdong ditching'. That's where us local kids would run up to the front of a neighbor's house, ring the doorbell and hide in the bushes.

Our favorite house to 'dingdong ditch' belonged to the old German guy at the end of the block. He lived in a ramshackle red brick house with a battered copper roof. His front lawn unkempt, that the overgrown grass would come up way past our knees. The old German would usually come out after us hollering and screaming at us at the top of his lungs. His old beagle would howl in our direction while we hid in the nearby bushes.

The old beagle sounded more like an old broken train whistle. His weird howl echoed loudly into the street. It was usually followed by a few other neighborhood dogs barking wildly, and some very angry neighbors yelling at each other. We were always fast enough to hide from the old German. But it was worth it. It was worth anything just to hear his old dog howl.

Our favorite hiding spot was in the thick bushes behind the church. That's because it gave us a perfect view of the old angry German as he swore away into the night. He probably knew it was us, but he could never prove it.

Sometimes our pranks were a little bit more creative.

One time we broke into the weather station and caused the entire town to evacuate. Stephen's dad was the local weatherman, and we knew the station was empty at night. Stephen also knew where to find his dad's keys. One night we quietly snuck out of our homes, and headed towards the station.

We looked around to make sure nobody was watching, and Stephen quietly unlocked the backdoor with his dad's key. Being a bit of a computer wizard, Stephen was able to easily hack into the weather stations computer. After playing around with their system for less than twenty minutes, he was able to set off a timed hurricane warning.

We quickly snuck back out of the station and ran back towards home. We knew we both had to get back before the warning blared over the town's emergency broadcast. Exactly Twenty minutes later the whole town woke up to a loud emergency broadcast. Our parents quickly woke us up as the town rushed to evacuate.

The crazy part was that nobody ever caught either of us. But I did I feel pretty bad after Stephen's dad nearly lost his job. The weather station blamed the whole thing on a technical glitch, but Stephen's father likely knew we did it. We felt bad about the whole thing, but it didn't stop us. Not getting caught only made us stronger.

Out of all the pranks we played, Halloween pranks were our favorite.

One Halloween we decided to outdo ourselves.

We climbed over the high wooden fence, and stole a little black goat from the farm near the main highway. Under the cover of darkness, we took turns pulling the goat around in an old Red Ryder wagon. We kept feeding it whatever we could find, just to keep it quiet. We even gave it a couple of candies, which it really seemed to enjoy. We finally got to our target. The miserable old witch was really going to get it this year.

We quietly opened her car door, praying we wouldn't wake her up. We cautiously lifted the goat off the wagon, and placed it and a few pumpkins in her car.

Mrs. Davidson was a mean old widow who lived in a small blue house. Her house was directly across the street from the old German man. She spent most of her days sitting out on her front porch, and rocking back and forth in her oversized wooden rocking chair.

She would gently stroke her shabby cat, and yell at anyone who dear to come near her house. Some people around town say that she killed her husband, and turned his body into the cat. Our parents would even threaten to send us to her if we misbehaved. One time the chubby Johnson boy from across the river stole a lollipop from the gas station. 'Tiny mike' claimed he saw his dad bring him there, and nobody ever saw the Johnson boy again.

Most of the younger kids around town would beeline around her house, worried they may also end up as a mangled black cat or disappear like the chubby Johnson boy.

We waited until the middle of night, and slowly walked up her front stairs. The stairs were old and worn out. They creaked loudly under our feet, and we nearly fell through them. Stephen was terrified but he still ran up and rang her doorbell. I was shaking so much that I decided to slowly walk back down the stairs, and hide in the bushes. Her doorbell chimed so loud that the cat scurried up from underneath the house.

We quickly ran across the street and ducked into the bushes. We watched her come out of her house in and bathrobe, and yell loudly in our direction. We had to cover our mouths because we couldn't stop laughing. I didn't want to tell Stephen, but I was so scared that I almost wet my pants.

The commotion startled the goat and it ran frantically around the car. We could see the car bounce side to side as it chewed nervously through the pumpkins. We watched as she headed down her stairs to the car in the driveway. We weren't laughing anymore. We were shaking, and terrified she would head towards us.

She slowly opened the car door, and yelled so loud that two of neighbors came outside. The terrified goat bolted out of the open car door, and ran haphazardly across the street. The goat stood in middle of the street, trying to figure out where to go.

This time we weren't so lucky. We finally got caught. We never got caught.

She somehow spotted us in the bushes. She walked over to the bushes, and picked both of us up by our ears. Not only did we spend the next day cleaning out the old rusty Chevy, she made us run around town finding that stupid goat.

We found him in the big empty lot behind the hardware store. It took us two hours to catch the stupid goat, and another three hours of chores given to us from the farmer. We didn't have choice, and we didn't want our parents knowing what we were up to. We still didn't learn our lesson, but we were happy the old witch didn't do any worse. We were happy we didn't end up like that Johnson boy.

From that day forward, we decided that playing pranks on the old witch was a pretty bad idea.

It didn't mean we weren't going to continue, it just meant we needed to be smarter.

This Halloween Stephen told me to dress up like a like secret agent.

He didn't really explain why he wanted me too. He wanted to surprise me, and promised it would be the best prank we ever played. I didn't think much of it, but was excited to go around getting up to our usual mischief. I looked forward to Halloween with Stephen because our pranks were always so hilarious. Secretly, I felt we were getting a bit old for these shenanigans. Even though I was nineteen, I still wanted to have fun.

I opened up my wardrobe and started searching for something 'secret agent' like. I decided to go with a white button down shirt, and a thin black tie. I grabbed a pair of black leather dress shoes, and slid them on my feet. I wasn't quite James Bond, but my spy outfit actually looked pretty good on me. I was ready for Stephen's secret mission.

I went downstairs and sat down in the living to wait for Stephen.

Usually he rang the bell twenty times, but this time he only rang it once.

As I opened the door for Stephen, I stared at him in disbelief.

Stephen was definitely not dressed like a secret agent!

Usually his hair was tied back with a small elastic band. This time his long blonde hair fell perfectly over his thin exposed shoulders. His hair was much straighter and shinier than it usually was. It wasn't just his hair that was different. He was wearing a shiny pearl and gold choker, which was wrapped tightly around his neck. A thick dark layer of red lipstick covered both his lips, and created a near perfect heart shape. A thin layer of blue eye shadow surrounded the top of both eyes.

It wasn't just his face that was noticeably different. His definitely wasn't dressed like the Stephen I knew.

He was wearing a beautiful flowing red dress. It was the type of beautiful dress that someone would wear to prom, or maybe to fancy wedding. Stephen giggled at me as my eyes kept growing wider and wider. I stood there speechless, still not knowing how to react. There was another part of Stephen's pretty outfit that really caught my attention.

A large slit ran down his left leg, revealing some of what he was wearing underneath. Stephen was wearing a pair of intricate white lace stockings, which ran up his long thin legs just above his knees.

He was wearing cute little ballerina shoes. Each shoe had a little satin bow on the tip.

"Who's the pretty lady?" my mom asked, breaking the awkward silence.

She was admiring Stephen's outfit, and was fascinated by the long white gloves he was wearing.

My mom made it pretty clear even she was falling for whatever this prank was. It wasn't like she had never met him before. Stephen was my closest friend, and had been to my house almost every weekend since we were in kindergarten. I couldn't believe that my own mom didn't recognize him. I couldn't believe Stephen was standing in front of my house, dressed in a dress.

"Are you going to the pretty lady in?" She asked, running her fingers along Stephen's shoulders.

I was still so distracted by Stephen that I barely heard my mom talking to me. She smiled back at me, and grabbed Stephen by the arm. As my mom led Stephen into the house, he turned back and smiled at me. His big blue eyes seem to sparkle as he pressed his thick red lips together. He stuck his glove out, and blew a kiss in my direction.

I was going to kill this idiot. This stupid prank had gone too far. Now my mom had her arm wrapped around him. My mom was head over heels, thinking Stephen was my hot Halloween date.

As soon as we got inside the house, my mom went to get her camera. That's how my mom was anytime I brought anyone over. She was always getting involved in every little aspect of my life, and taking pictures of everything.

I hated every second of this. I hated that my mom was now taking pictures of Stephen. I hated that my mom was so embarrassing. I hated that my mom was so into Stephen. I hated that Stephen actually looked attractive in a dress, and I hated that I was starting to fantasize about him.

My mom stretched her arm out and took Stephen by the hand. Her hand wrapped tightly around his white glove. She walked him slowly up our winding marble staircase, taking her time to marvel at every detail of his outfit. I wanted to yell at both of them, I was really getting upset.

"Come on Michael. Picture time with your beautiful lady"

Before I could say no, my mom let go of Stephen. She went down the staircase, and grabbed my hand. I nearly fell onto the stairs as she quickly pulled me up the staircase. I was still catching my breath when she finally let go of me and positioned me behind Stephen. My mom grabbed my arms and wrapped them around Stephen's smooth belly.

With my face buried in his hair, I realized he smelled very similar to my mom. It was clear he had sprayed a thick layer of ladies perfume all over his neck and shoulders. Did he really have to use the same perfume as my mom? Gross.

"Smile you two lovebirds!" She said, giggling like an idiot.

Mom pushed the camera button down, and we both let out a big smile. Once my mom finished taking way too many pictures, she left us alone to put the camera away. Stephen quickly turned around and planted a kiss on my lips. He smiled at me knowing he left a thick outline of dark red lipstick on me.

Mom came back and took Stephen's hand. Luckily, she didn't see the massive lipstick stain Stephen left on my lips. She led Stephen slowly down the staircase, as I watched from behind. The worst part was that I was starting to think my mom was actually into Stephen. As my mom guided Steven down the staircase, couldn't help but sneak a peek at his smooth backside.

The back of his pretty red dress was open, and only a thick red bra strap was visible. But it was what was just below his thin waistline that caught my attention. As they continued down the stairs, I realized I had suddenly started to become more and more attracted to Stephen. His thin panty lines pushed out, accentuating his perfectly smooth behind.

Mom walked Stephen outside, and I soon followed. I looked back to see her watching us from the living room window. I'm sure she was still admiring Stephen from behind as we walked down the block.

As soon as we turned the corner, I punched him hard in his left arm.

"Don't hit your pretty lady" he said, giggling like an idiot.

He grabbed my arm and held it tight against his. I took a deep breath, and realized I needed to relax. It was Halloween tonight, and he really did look like a pretty young lady. Anyone looking at us would probably think I was the luckiest nineteen-year-old in town.

"Hope I didn't embarrass you too much" He said, kissing the side of my cheek again.

This time he left his lips pressed against my cheek for what felt like an eternity. Or at least long enough to leave a big wet mark on my cheek. I wrapped my arm around his back, and started to play along. I ran my hand down his backside and jokingly squeezed his butt. I squeezed his butt a bit harder, feeling the soft intricate pattern of his panties on my fingertips. Secretly, I had wanted to squeeze his butt so badly. He really did look amazing in the dress.

It wasn't just the outside panty-lines I felt. It was clear that he was wearing a pair of intricate lace lingerie panties. He turned back, and smiled at me as I gently caressed his butt. He turned around again to make sure nobody was looking.

He grabbed my hand and guided it up his leg. My mouth fell wide open as both our hands rested against his soft lace panties. We heard people nearby, and he quickly pushed my hand away. I was so confused, was I suddenly becoming attracted to my best friend? What type of prank was this anyway?

We went back to trick or treating, and we pretended like I didn't just have my hand way up his dress.

As we went from house to house, more and more people commented on how nice Stephen's dress was. A short elderly woman at the edge of Maple Road even asked where Stephen bought the dress. Stephen had actually stolen it from his older sister, but made up some bogus store to get the lady off our back.

It was near the end of trick or treating, and was time for our favorite part of Halloween. It was our tradition that went back since we were little kids.

We waited until most of the lights went out, and people would leave their candy up for grabs. We took it pretty literally, and would take the whole bowl. Yep, we would take the candy with the actual bowl. Then we would stack the bowls in our arms and we walk up to 'nose cliff'.

Nose cliff was just above the big windy river at the edge of town. On a clear night, you could see most of the houses in the city.

We called it Nose Cliff because it hung over the river like a big nose. Sometimes the ice would form underneath it and we would call it 'old man booger nose'.

Every Halloween the older kids would gather all their candy and go up there to finish it. This year it was just the two of us. Most of the people near our age outgrew Halloween, and the other kids were too young to be up on nose cliff.

Another tradition we had was called 'Candy Mountain'. We would take all the candy we had gathered and make a small mountain of candy. Then we would place the stolen bowls on our heads, and eat an insane amount of candy. Of course, most of us would get sick because we would eat way too much candy. Once we ate trough most of our candy, we would throw the bowls in the river and hurry home before we got in trouble. Our parents never realized that we had eaten half our candies before we even showed up at home.

As we ate a near metric ton of candy, I glanced over at Stephen. His pretty red dress was blowing in the wind, and his smooth legs dangled loosely back and forth off the cliff. I couldn't help but stare at his intricate lace white stockings, as I took a quick peek between his legs.

A tingling sensation spread across my body. I started to get hard as I began to fantasize about my best friend. I had never been with a guy in my life, but somehow this felt different.

I reached into our pile of candy and picked up a blue ring pop. Stephen was busy eating candy after candy. I undid the ring pop wrapper, and stood up on the cliff. I tapped Stephen on his soft exposed shoulder, and went down on one knee.

"Will you marry me maaa laady?" I said, loud enough to hear an echo.

Stephen turned around and burst out in bout of uncontrollable laughter. I put my hand out, and he placed his white glove inside my hand. A big smile spread across his face, as I lifted him up towards me. As soon as he was standing in front of me, he let go of my hand and placed his hands against his voluptuous bosom.

Stephen flipped his long blonde hair backwards, and answered with the funniest voice impression I ever heard. It sounded something like teenage girl meeting her favorite pop celebrity.

"Errrmagaawd yaaas!" he shrieked, while jumping up and down.

We both giggled and jumped up and down. We shrieked like loud teenage girls at a pop concert. I got back down on my knee, and extended the ring pop towards him. He smiled at me as I slid the ring pop onto his extended wedding finger.

"You may now kiss the bride" Stephen said, still trying not to fall over laughing.

He leaned down towards me and stuck his tongue out. He tickled the tip of my nose with his warm wet tongue, and then jokingly pecked me on lips. I stood up to face him, thinking our kissing would become more passionate. But I was too scared to make a move, and I still wasn't sure if this was still some sort of prank.

We went back to sitting at the edge of the cliff, and joked about where we would go on our honeymoon. We even started to pick out names for our kids. Stephen suggested we name our kids after the dogs in Local Park, that way it would confuse everyone. I suggested we name them after household appliances that way it would make shopping interesting. Then we talked about where we would send them to school. Stephen said we should home school them, but I said I wanted them to socialize. Stephen interrupted our weird conversation, by switching to something very different.

"So do you want to see what I'm wearing underneath?"

Before I could answer him, Stephen stood up and started rocking his little hips slowly from side to side. He lifted his long white gloves above his head, and started spinning around in slow circles. He started to sing at the top of his lungs, loud enough to scare some of the seagulls off the far edge of the cliff.

"I'm pretty ohhhhhh soooo pretty..."

I couldn't stop laughing at his loud off key singing. He knew I couldn't resist singing along to the song. He knew it was the song was from my favorite musical. We held hands and started slow-dancing together, singing as loud as we could.

He stopped singing, and let go off my hands. He pressed his white gloves against his hips.

"Come on husband help me undo zee dress. Pretend I am one of zee pretty French woman you dream about"

I could barely contain myself, and burst out laughing. His French accent was good and so bad at the same time. But I really wanted to see what he was wearing underneath.

I stood behind him, and his hands fell against the sides of his body. I slowly undid the thin black lace just above his bra straps.

"Oui Oui, I am so attractive. Now undress moi" he said, flipping his hair back towards me.

As I released the lace his pretty red dress fell down past his waist. My laughter quickly died out, and my heart started beating fast. My pupils widened and my jaw fell wide open. He was way more attractive that I imagined he would be. His dark red lace panties we see-thru, and barely covered his smooth behind. He leaned back, and grinded his body against mine. Now it was obvious how attracted I was towards him. I couldn't hide it anymore as he rested his hand against my crotch.