Hi everyone! Happy Halloween! My name is Stephanie, and I would love to share with you a crazy Halloween story, about last year. All parties involved in any sexual activity are now and were over 18 at the time.
First, I need to admit that I am not a morally great person. I mean, I try to be, and I am definitely a friendly person, but I've just made so many mistakes, and I seem to keep on making them, especially when it comes to Katie's boyfriend.
Let me start over. I fight a lot with my sister Katie. She is four years older than me, and close to graduating from college. She had always been popular and loved, having even been a cheerleader in high school, whereas I had been a skinny, uncoordinated, overly shy girl for most of my life.
Katie was tall with blonde hair, blue eyes, big beautiful boobs and tons of friends. I was always short with raven black hair and brown eyes with the barest hint of green, just enough to notice with my face like an inch from a mirror, and I had for the longest time no boobs to speak of. She was also an 'A' student, where I made 'C's or 'D's in class at best. I thought she had everything. Then she met Ryan.
Ryan was gorgeous. Ryan was in college. Ryan was rich. Ryan bought her anything she wanted. He was popular. He was funny. He was hung like a horse, and an animal in bed, or so Katie would brag to me every single time they hit it. Ryan lasts forever. Ryan doesn't even always cum, especially if Kate hasn't. It was always all about her pleasure with Ryan.
Not a huge leap to guess why I grew the biggest crush on my sister's boyfriend. I was jealous, plain and simple. Back then, I didn't think he even knew my name.
So lets skip ahead to my senior year of high school.
By my senior year I had found my niche. Where my sister had been a cheer slut, I became a goth. I made plenty of friends over my high school career, and came out of my shell quite a bit. Much like my sister I was no stranger to sex, only I hadn't met some amazing guy to take care of my slutty wants or fall into a magical care free relationship. I got passed around.
That year Halloween fell on a Sunday, so everyone naturally decided to celebrate it the day before, on Saturday. I went to this huge Halloween party on the wealthy side of town. I had been invited by this guy who I had been hanging out with for about a month, and had already slept with a number of times. I really liked him, and so I spent a lot of time picking out and customizing my slutty catholic schoolgirl outfit. I wanted him to like it. And I mean come on, its Halloween.
Though I was still short at just five-one, my breasts had finally grown in, and while they were not as big as my bimbo sister's, they were a much firmer C cup, and more than large enough to draw the eye when I wanted them to. The top I bought was out of the kids section, and with only two bottons fastened did a good job of barely covering the girls. I wore a brand new sheer black bra only because I was marginally worried the tiny shirt might snap open, but it looked fantastic poking out of the thin white material and against my pale skin.
At the risk of sounding conceited, I knew that I had a great pair of legs and a nice ass to boot, so I made sure the skirt was as short as I would dare risk wearing, and that night I was willing to risk quite a bit. I mean, it was a Halloween party, and I was going on a date with a cute guy that I really liked, why not dress for a good time?
I kept my hair died super black the way I liked it, with my bangs covering my ugly eyes (I still hated them back then) and carefully applied my favorite black cherry lipstick and nail polish.
My catholic school girl outfit drew a lot of looks that night. The party was at this rich football player's house, a guy named Gary. I was having a fantastic time, and we all got trashed pretty quickly. By one o'clock we were out of beer, so my date along with Gary's cheerleader girlfriend and two of their friends went to go buy more. One of those friends was 21 I guess.
After they all left Gary, who I had never even said hello to before, came and took me by the hand and pulled me along up a flight of stairs and into one of the bedrooms. I knew I should have said no, but Gary was a really attractive guy, and technically he never asked. He must have assumed I would go for it because of my reputation... Besides, he WAS dating a cheerleader, and I really hated living in my cheerleader sister's shadow. It was kind of hot being chosen over a pompom pusher.
He pushed me against a wall facing away from him and dropped to one knee, gripped my ass in one hand (men love my ass, as I mentioned earlier) while he fingered me with the other. I hadn't exactly come close to cumming before he stood and pushed me down on the floor and shoved his cock into my mouth. Once he was hard enough he shoved it into my cunt, then before I had a chance to cum he rolled me over and started fucking me in my ass. He came in my ass fairly quickly, then hopped up and left me there on the floor as he went back down to the party.
Sorry about the lack of detail, but this story is not about Gary the asshole, or even about the Halloween party itself. It is more about the trouble the outfit got me into the next day. On the real Halloween.
By the time my date and Gary's girl came back to the party I guess everyone knew what had happened. Gary and I were both back downstairs, and I spent a good thirty minutes with my would-be-boyfriend before someone grabbed my hair from behind and shoved me face first into a wall. Someone had told Gary's girl what had happened between he and I, or maybe she found the black cherry lipstick I had left smeared all over his cock.
Either way, she came at me out of nowhere. I never stood a chance. As she beat my ass (figuratively boys, calm down) she screamed about what I had done to everyone, that the goth-slut-social-climber had fucked her boyfriend. When she was finally satisfied with the beating she had given me she backed off long enough for my date to pick me up and throw me out into the backyard off the deck.
I could have been really hurt. It felt like the bimbo had broken my nose, I hurt my ankle on landing, and my outfit was torn and trashy looking, more so than I had meant for it to be anyway. Those two buttons I mentioned before had been ripped free during the fight, and I had to physically hold the tiny shirt closed with my hands.
I couldn't call home for a ride that way, and my decent clothes were in my date Bobby's car along with my cell, and the car was locked. Trust me, I tried the door. I didn't have any hope of a ride until Bobby decided to leave, and even then I knew I would have to beg.
When he finally came out of the house an hour later, I begged. He didn't even slow down long enough to look at me as he got in his car and left.
He left without me.
He left with my clothes. He had the decency to toss my cell out the window, though he was halfway down the street before I saw it go flying. After retrieving it I spent the night in Gary's backyard freezing my tits and ass off and trying not to cry. Bimbo never left, and I didn't have the courage to try and rejoin the party.
I woke up in the backyard the next morning after everyone else had left. I still didn't have a ride, and I still didn't want to call my folks with mascara all over my face and grass all over my torn up slutty outfit, an outfit they would kill me for wearing. The only thing I could think to do was to walk up to Gary's door holding my shirt shut and knock. I looked so scary that when Gary opened his front door he flinched.
"Trick or Treat." I said lamely. He said I couldn't come in to wash up since his girl might wake up but he would drop me at the mall if I promised never to talk to him again. He acted like the whole affair had been my fault. He had scratch marks on his face that I am sure came from his cheerleader after I had been evicted from the party. I agreed to his terms.
On the ride I held my shirt closed with both hands until he pulled my hands away and started roughly groping my tits. I have piercings, so this really hurt. He said that maybe I should suck him off as payment for the ride. I told him to go fuck himself.
He kicked me out at the next intersection and sped away. I had to walk the final quarter mile to the mall. I ditched the heels and set out barefoot. People honked at me. No one stopped for me. Looking like I was, I couldn't have accepted a ride anyway without fear of getting raped or killed.
Once there I had to run through the crowded mall to a bathroom to freshen up. That early in the day, it was filled with olds. Mall walkers. Early risers. The kind of people who were not afraid to call me a whore as I ran past. Talk about a walk of shame. My outfit still got plenty of looks, but none of them were looks of approval. I was half certain mall security would come to politely kick me out, after calling my parents of course. I don't think I passed a single person who didn't stare at me.
I promise thing Halloween gets better. And hotter.
So I was able to wash up enough so that I didn't look like I had spent the night crying outside in the cold. I was still dressed more than a little too slutty to just call my dad, so my first instinct was to go buy a decent outfit.
Only there hadn't been any room on the outfit for a purse so I left my cash in Bobby's trunk with my other clothes. I had kept a little cash with me of course, but what I had I took out of my bra and gave it to my date when he went to go buy the beer. God, I was fucked.
I pulled out my phone to call my dad and suddenly remembered mom saying my sister Katie was coming into town this weekend to spend Halloween with Ryan. I had no idea if they were celebrating it last night or tonight, but as she told me once that Ryan was really turned on by sexy costumes, I could easily see her spending a long weekend with him, dressing up for him all day today. I hoped I was right, as that would mean she would be here in town. If she was in town, maybe she could come give me a ride?
I called her cell three times before she picked up. Yes, she was still in town. No, she couldn't come get me. She left her car in Hanover and took an plane. Ryan was dropping her off at the airport and they were already late.
Desperate, I described my night, glossing over the sex but admitting to the cheerleader kicking my ass, where I spent the night, where I was, how I was dressed, and how I didn't have a dime.
She started laughing, of course. Sisters. She put me on mute to tell Ryan. God this was so embarrassing. When she took me off of mute she was still laughing.
Before I could mention it, Katie offered her own idea. "Ok little sis, I gave Ryan a couple bucks for clothes. He is going to drop the cash off for you on one condition; you have to let him take a pic of you with his phone for him to send to me!"
More laughter, and Ryan saying something in the background. "No," says Katie to him, "you don't need to give her a ride anywhere. She made her bed, let her explain to dad why she needs a ride from the mall at least! Did you hear that Steph? Pic first, then the cash, got it? No ride."
