The Desperate School OutfitbyEsotericNiceGuy©
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."
I sighed. "Yes Kate." Then swallowing more pride than anyone should, "Thank you Katie." More laughter. What a rotten Halloween this was going to be, I thought to myself.
I was wrong.
So Halloween last year found me hiding from mall security at the bottom of one of the parking garage stairwells.
I was dressed like some kind of B-rated horror movie slasher victim, while waiting for the man of my dreams to come and take an embarrassing pic of me so that he and my evil sister could have some fun at my expense.
I was not having a good Halloween. I mean, even for me, this was pretty crappy. My nose and ankle hurt. I wondered if my nose looked bruised. After about an hour of hiding under the stairs whenever people came by I finally got a text from Ryan asking where I was.
To my knowledge he hadn't had my number before. Katie must have given it to him. His text read
I had had plenty of time to waste with nothing to do but think. Not a small portion of that time was spent fantasizing about rewarding my would-be knight-in-shining-armor on my hands and knees. What can I say, I had it bad for him.
I texted back.
From my window in the stairwell I saw Ryan park his killer Spider on the bottom floor of the garage. He got out and stood by his car typing into his phone. Texting me. I was nervous. He was dressed in black slacks and a blue button up shirt. I could see him through the windowed door to the stairs, but he had not spotted me.
My phone buzzed.
I mean true, last night I thought I looked hot, but looking hot wasn't fun anymore. That and my hair was a mess and I wasn't wearing any of my make up, and my top was torn so badly I had to hold it closed. It made me feel... more exposed than sexy.
I pulled my bangs down in front of my eyes to hide my face and pulled my skirt down as far as I could, which is to say if I stood straight and you were taller than me you probably couldn't see my thing. I held my shirt closed and I marched my barefoot ass out to his Spider to face the music.
"Damn," Ryan said, "when Katie said you would look like a slutty beat-the-hell-up school girl, she neglected to mention how hot you have become. When did you start looking so gorgeous?"
I turned beat red. Let me clarify, Ryan had never said anything flirty to me before that day. I had dreamed about him flirting with me for four years. Dreamed about him breaking up with my sister and letting me take care of him. Dreamed of him dumping her for me. Dreamed of him just getting drunk and making a glorious mistake with me, but not once had he said anything to me that showed even the slightest hint of interest.
Now, on what could have easily been the worst Halloween ever, he lays into me like I were someone he could want. Sure it was probably just to cheer me up, but I smiled in spite of myself, got a little wet, and my tits grew a little more firm and noticeable through my shirt. I tried to adjust the way I held my shirt to hide that fact, letting a little bit of slack into it, but I think the gesture was useless.
He had my number alright.
Then he pulled out his phone and turned on the camera. Oh yeah... Hello, reality. He took more than one pic of me too. Click click click. He even asked me to spin, to which I said "No." of course.
"I am only sending the first pic to your sister. The rest are for me." He said with his good ole' boy smile and wink.
Wait, what? Blushing again, I gave a quick spin, fast enough to show my ass. He was smiling broadly as he sent my sister a pic. Maybe he was sending them all, but still, he implied that he would want them for himself, and that was awesome enough to make me happy, even if it wasn't true. Aren't crushes sad? "Here is the cash from your sister." Ryan held out the green. I took it, and was suddenly furious.
"Ten bucks? I can't buy an outfit at the mall for ten bucks!"
"That's what I told your sister. She just laughed and said it wasn't our problem. She said let the slut walk or hitchhike to Goodwill. I love your sister, but she can be a real bitch."
"Yeah she can! Damn it what the fuck am I supposed to do?" My sister never cussed. I don't know that I had ever cussed in front of Ryan, but it made him laugh.
"I was asked to get the pic, hand you ten bucks, and drive away. I am supposed to call and tell her how it went." He just stood there smiling at me, and I realized how horrible I must look. I guess I was ungrateful for not appreciating the ten dollars, and a fool for trusting my sister at the same time.
So then Ryan says, "Thats what I am suppose to do. Tell you what, I don't have any plans today now that Katie is out of town again, and I do like that sexy little outfit. What if I turn my phone off.. If you are willing to keep me company for a bit before you get changed, and if you can keep this a secret from Katie, you can buy whatever you want." With a flourish he was suddenly holding a credit card out to me. He had to have had it out of his wallet before he made the offer. Well, I guess he knew I couldn't refuse... not that I would want to!
My heart was racing. I mean, sure I needed the money, but who cares? Was Ryan trying to get in my pants? Did he know he didn't have to try at all? Or was he just fucking with me, trying to make me feel better about my bad luck?
I mean, I doubted Ryan would want to cheat on his woman with the kid sister, but if we had one of those flirty-tension-but-just-friends kind of friendships growing here, it would make up for how crappy the Halloween gods had been to me so far.
He had to know I had a crush on him, the way I would follow him around and blush every time he spoke. "Where could we possible go with me dressed like this? I mean, I am not holding my shirt closed for fun, its buttons were ripped off..."
"Besides shopping in the mall? I had meant we could hang out while you shop, but I am definitely up for hanging out after if you don't have any plans." His smile and tone hinted that he knew damn well I would take him up on the invite. God he was so hot! "My place?" He offered. "I figure I could smoke you up, maybe we could watch a movie, and drop you off after you change whenever you are ready to leave."
Ok, so he didn't say 'My place to fuck', like I hoped he would, but maybe it was implied? Besides, hanging out with the man of my dreams and getting stoned was way cooler than having to call my dad. "Deal! Katie said you have killer weed." I offered cheerily.
So then Ryan went shopping with me. He was like, right beside me the whole time, encouraging me to spend whatever I wanted. I would pick up an item on sale, and he would insist I find something full price just so he didn't have to worry about whether I was trying to go easy on his wallet. I bought two outfits before we were done. One to wear home that night when I saw my parents and one to wear out and about. His eyes never left my chest or my ass.
When I flirtatiously offered to go into the lingerie store he stopped me from going in, explaining that he didn't believe women should wear underwear at all when they were with him. He refused to buy me any "on principle". It was obviously a joke, but the way he eyed my short skirt when he said it made my heart race. Did he understand he could take mine off anytime he wanted?
More and more people were arriving at the mall, and my manually-held-together-outfit was sticking out like a sore thumb. With Ryan looking at me with obvious lust in his eyes I had almost forgotten to be ashamed. I had slipped into the heels he had purchased for me already and it was not until I convinced him to settle on a pair of cute flip flops for my wear home outfit that he let me lead him back out to the parking deck.
He opened my car door for me. No one had ever done that for me before. He put my seat belt on for me, which brought his beautiful face fairly close to mine. His breath smelled fresh and I wanted to run my hand along his stubble. He took a shameless peak at my breasts when my shirt fell somewhat open, and gave me another of those lazy boy smiles with the bad boy wink.