Tricked and Treated at a Halloween Party

A virgin gets a Halloween surprise of his life.


My whole life has been somewhat of a planned activity. Everyday I had the same routine; go to school, stay after for soccer, go home, clean up and do homework, hang out with friends, and sleep. I didn’t have time much for anything else, let alone a girlfriend, hell I was too shy to even approach a girl I wasn’t already friends with. Don’t get me wrong I watch porn and masturbate a lot, so I have some visual experience, unfortunately I have noone to use it on. This little tidbit of information is why I am most likely the only virgin who attends John Marshall High School, but thanks to my friend Matt’s Halloween party, my sex life took a drastic turn.

Let me fill you in on me and my friends a second. My names Chris, I’m 6’0”, about 180lbs., blue eyes, brown hair, and a fairly decent smile. My only guy friend is Matt, he is the exact look and build as me, except with hazel eyes. My only two girl friends are Terra and Stacey. They look exactly alike with the same long light brown hair, green eyes, both about 5’6”, about B cup tits, and nice firm asses they don’t hesitate to show off, they are very often mistaken for being sisters.

Since this is our senior year in high school, and we passed all our necessary classes, we decided to get a bunch of electives so we could all be in the same class, but it didn’t work. Since Matt was captain of the soccer team he had a little pull around school, so everyone(or almost everyone) knew who he was, so if he did anything, it was guaranteed to have a big turnout. It was while we were sitting in homeroom 3 days before Halloween when he came up with the idea that would change our life.

“Hey guys what are you doing for Halloween this year?” Matt asked.

“Me and Stacey were just gonna chill at my house and watch some scary movies, big fun,” said Terra.

“You know me, no girlfriend, too old to trick or treat, guess I’ll be passing out candy again,” I said.

When I said this Matt kinda got this look like “dude, you gotta be kidding me” and Terra and Stacey both looked me up and down, unusual but with what I just said acceptable.

“My parents are going out of town today, I’m thinking about having a Halloween party at my house, but not just any party,” he grinned.

Matt’s parents were loaded, but you would never know from him, he wasn’t a spoiled kid at all. This meant that their huge house would be empty except for all the kids who would be running rampant through it. Although having a party seemed like a good idea, I just wasn’t into it, I didn’t feel like getting shot down again, especially in a room in front of our peers. Naturally, everyone was upset.

“Oh come on Chris, it’ll be fun! You might even get lucky with someone!” Stacey said.

Terra was pulling my arm and tugging on my shirt. “Chris you gotta go! It wont be as much fun if were all not there! Don’t be a spoil sport!”

I wanted to go, but the idea of rejection kept popping into my head distorting all my thoughts, then I figured, I could dress up and no one would even know it was me anyway, so what the hell. “Ok fine, I’ll go, but it better be freakin worth it!”

When I said that the girls clapped their hands and gave me little half hugs and Matt punched me in the arm and slapped the back of my head, a little too hard I might add. “That’s what I’m talking about! I knew you’d change your mind. I gotta start setting this thing up.”

He pulled the girls to the side and was talking to them about something, I knew it was big when they gasped and started grinning and nodding their head. Why didn’t he tell me? I wanna know whats going on! He probably didn’t on purpose because he’d think I’d back out or something, maybe its for the best. When homeroom was over he pulled me to the side to tell me who he planned to invite, which happened to be a little bit more girls than boys, hmmm.

“Chris make sure you don’t wear a cheesy ass costume, no teletubbies or bullshit like that.”

“What the hell? You must be crazy thinking I’m going as something as gay as that!”

“Ok just checking. Make sure it hides your face pretty good, it’s gonna be an “identity kept secret” kinda party, noone will know who anyone is, for good reason,” he grinned as he walked away.

I tried to keep my mind occupied from the party, but every time I almost forgot about it someone would say something about it to throw it back in my head. When lunch finally came around (one of the few periods we all had together), Matt had showed us the fliers he printed up in study hall. They were colorful with pumpkins and “Matt’s Unforgettable Halloween Bash” in big red letters. He handed us one with a number on them, and said we needed them to get in, as he only invited so many people.

“So what are you guys gonna go as? I’m gonna be Batman,” Matt said.

“Figures. Were going as Tinkerbell and a Playboy Bunny, but we might change if someone has the same costume,” Terra said.

“I think I’m gonna go as Zorro, I still have the costume, and it still fits, so why not,” I said.

“Ooh Zorro? Who you trying to fuck at the party?” Stacey jumped in.

“Me? Sex? We all know that’s not gonna happen, not to me.”

“Don’t be too sure man, you never know what could happen if someone gets drunk enough. There’s gonna be mad vodka at this party. This is gonna be the best night of our lives, you see, and Chris if you carve a “Z” anywhere in my house I’ll kick the crap outta you,” Matt laughed. It was just like him to turn a tense situation into a funny one.

With that the bell rung and we were off to finish out the rest of the day. When school ended we all drove home instead of hanging out like usual, contemplating what to wear and how the party would turn out. I was still a little nervous about the whole thing, but it was way too late to back out now, “hey, it’s just a party” I said to myself, little did I know I couldn’t have been more wrong.

As the next couple days went by, I got more and more anxious. I would see Matt hand a flier to a cheerleader or a girl on the volleyball team, and guys on the soccer team, but mostly girls I would never get the nerve to talk to. We were all distracted at school we didn’t even really talk to each other that much, everyone was worrying about something different that had to do with the party, but I did notice we all gave each other weird looks and blushed at each other, maybe just a coincidence of the upcoming party. When I got home I would go to my room to perfect my costume, eat dinner, and go back to my room. My parents and little sister noticed something weird with me but luckily noone brought it up. I had almost everything I needed for my costume, but I still needed a fake mustache and a play sword. After a bit of thinking I had the perfect solution, my little sister Sarah. She goes to the same school as me and is a junior, and very popular among the guys. Though Sarah’s only 17 she dresses like a full grown woman (not that I noticed) and I know she has some of those fake eyelashes lying around. As for the sword, she just joined the fencing team and that would be a perfect fit. I knocked on her door and opened it. She was spread out on her bed reading a book, with only her long blonde hair and blue eyes poking out.

“Hey bro, what’s up?”

“Hey Sarah, I was wondering if I could use your fencing sword and those eyelash things for my Zorro costume, I need them to make a fake mustache thing.”

“Uhh, ok sure. If I do what are you gonna do for me?”

“Well what do you want?”

“(sigh) I can’t tell you that. How about the new Taylor Swift cd?”

“Sure, no problem, that seems fair.”

“Ok you got a deal, for now.”

She got up and went to her dresser and grabbed a little container, and then went to her closet and got the sword. It had a ball on it but it was usable, and the eyelashes would work perfect as a mustache. “These will work great, thanks sis,” I said as I kissed her cheek, a little close to her lips. I instantly pulled back, and she just looked up at me from her little 5’5” frame and smiled at me without saying anything. I grabbed the stuff and went out her door.