7 comments/ 58887 views/ 15 favorites The Desperate School Outfit By: EsotericNiceGuy 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 This was the first time I had gotten a call or text or anything from Ryan. How sad was my little crush that this text actually made me blush? 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. Wink face? That message I read fifty times before I ended up saving to my phone. What was with the wink face? Was he implying he might be turned on by seeing the outfit, or was he just poking fun at my embarrassing situation? 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. Damn it! The man of my dreams was being flirty with me and I looked like a rejected tramp. I was a rejected tramp. 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. The Desperate School Outfit I decided not to hold my shirt in place on the drive back. I wanted him to see I could handle my end of the flirtatious game as well. I looked out the side window to hide how red my cheeks were. On the drive back Ryan started digging into the events of the previous night. I tried not to make myself sound too bad. I explained the girl "accused" me of sleeping with her dumb jock boyfriend and jumped me, and before I knew what was happening my date was pulling me off of her and throwing me out, having bought the cheerleaders accusations. I then told the truth about how Gary was a tool and that I had to beg for a ride home, and how he only gave me a ride here to cop a feel and try to get some head. I told him about ditching the shoes to run the rest of the way to the mall. Ryan was full of sympathy. He said he regretted missing the cat-fight with a smirk and a wink, and he told me the cheerleader was probably just jealous of how hot I looked. He comfortingly placed his large hand on my bare thigh, way up on my thigh, and it stayed there through two whole lights! Obviously I had never actually been to Ryan's apartment, though Katie had described it to me. I walked around, giving myself a tour while he got his baggie and pipe out. There wasn't a single picture of Katie up. Interesting. They had been dating for four years. She had a hundred pics of him all over her room at home. The party they had gone to had obviously been here. There were beer bottles everywhere. Ryan's bed wasn't made. He had to have fucked my sister on it last night and likely today I realized with more than a little jealousy. I put my hands on his bed sheet and imagined him taking me like Gary had taken me... like Ryan had likely taken Katie. Am I over sharing? Does that sound creepy? I am telling you this was a pretty big crush I had for the guy. I even considered dropping my panties since he had said he didn't approve of them, but I was worried he would take any open attempts to seduce him as a childish fantasy and laugh. He was dating my busty bimbo sister after all. Miss perfect. What could he want from me? The flirting had to just be in fun. A way to treat me like an adult and cheer me up. If I took it for more than it was then I would certainly be making a fool of myself. Back in the living room, the weed Ryan had was really ridiculous. I was stoned after the first bowl. As he packed the third, he asked a little too casually "So did you fuck the jock?". I turned beat red. I was way embarrassed but already too stoned and way to nervous to pull off a lie. A simple "no" would have worked, but instead I blurted out, "Fuck, yes! I did, but I really didn't want to." "What do you mean you didn't want to? You like, tripped and fell on his cock? Or did he rape you?" Ryan suddenly looked pissed and protective. Of me. So then, getting increasingly stoned and feeling introspective, I told him the whole story. I even went into the stupid excuse I give myself about how I have low self esteem so I cant say "no" when guys are into me. All guys ever want from me is sex and then they toss me aside, which means I am only good for sex, which sucks, so to feel better about it I go and fuck someone else so that I can feel wanted again. I sounded pretty pitiful I'm sure. It sounds dumb to me now, and that was just a year ago. Ryan put his reassuring hand on my leg and was smiling broadly. "You getting tossed aside has nothing to do with your self worth. You are a catch. Lesson one," Ryan held up a finger, "All guys are assholes." I rolled my eyes. "I've heard that rationalization before." "Well it is true. I should know, because I am an asshole." He winked again. "Now listen, lesson two," Ryan held up a second finger, "any asshole who sees the chance to score with a really hot chic, with no stings attached, is going to take it. I don't care if they are married with three kids, a pastor of their church, or dating the hotty's sister, if you give off the free ride vibe, every man you meet will have their thumb out. Dating the hotty's sister? Did that mean... Man I was getting stoned. Ryan slid over from the love seat to the couch right next to me and placed that large reassuring hand on my thigh again, and I lost my train of thought. I thought that was really funny so I smiled brightly up at him. "Since any asshole who sees you is going to want to fuck you, obviously not everyone who wants to fuck you is going to want to date you too, or be available to date you. Lesson three, the guys who are best at getting into your pants are the guys who are experienced at getting into girl's pants, and are therefore the guys who are most likely only intrested in the fucking." "No one wants to date me." I said feeling melancholy. He was being sweet, but it sounded more like he was just trying to say why I was un-dateable in a really nice way. Ryan shook his head. "No, now pay attention and I will explain why it looks that way." He sounded annoyed. His hand started rubbing my thigh. That was really nice. "There are nice guys, who are still asses just because they are men, and then there are total assholes. Total assholes look for women who are easy to sleep with and sleep with them, and never have any intention of dating them. Like last night's jock for example. Guys like him actively look for girls like you, who are openly available. You meet mostly guys like that because they target chics like you." Apparently Ryan was a real talker when he was stoned. I tried to focus on what he was saying and look like I believed him, but his hand was such a distraction... "Then there are the nice guys who would want more than just sex, and you have probably slept with several of them too, but they see you fucking some other asshole, and they feel hurt and walk away. Take your date Bobby for example. It sounds to me like you hurt his feelings. "Plenty of people want to date you, you just need to learn to say no when a guy wants to use you for sex and sex alone, and make the other men work for it before you give it up." I shrugged. Stoned as I was, he kinda sounded knowledgeable. That date I had was pretty pissed at me. And he had invited me to the party. Maybe he did like me? "How can I tell if someone wants to date me, and how can I tell who just wants sex?" "Not many guys are going to openly say they are just after sex if they think it blows their chances of getting sex, but you can usually figure it out. "If a guy's idea of a first date begins or ends at his place, he is just after sex. If a guy is clearly in a relationship like the jock was or I am, he is just after sex. For example, take me. I've been dating your sister for four years. But when I look at you in that sexy school girl outfit, talking about how you can't say no to men, my instinct is not to give you advice, but to take serious immediate advantage of you. To fuck you harder than you have ever been fucked before, then send you packing." My eyes bugged and my jaw dropped open. Holy crap! He smiled broadly, holding up his hands defensively "No no no, now I am being overly honest of course, but I have not made a pass at you because you are clearly in pain and I want to help. My point is that even the best guys out there are going to be tempted if someone as hot as you are willing to... " "You can fuck me if you want to." I blurted out. Did he want to fuck me or not? This weed was making it so hard to think straight. I figured this conversation might be my only shot. Crap, did he not just say he was not making a pass at me? God I wished I could take that sentence back... "My point is..." he picked back up, giving me a weird look, "... my point is that you can tell that since I am with your own sister, you could tell that if I did make a pass at you, it would only be for sex. Even then, you would still let me fuck you?" he raised an eyebrow at me. Crap! Was he judging me or testing the water? My face couldn't turn any more red, I was blushing so hard it hurt . "Knowing I am serious with your sister you would let me fuck you, knowing that there was no chance for anything more? I thought that after the story you just told me you were tired of meaningless hook ups?" Damn Ryan's killer weed, I couldn't think straight! What was he wanting me to say? "Your not just some guy." I shrugged, hiding my eyes behind my bangs and staring at the floor. "I've always wanted you like that." "So knowing that I have no intention of leaving your sister, you still would let me to fuck you here and now?" "Oh yes." I said, shrugging again and turning a shade redder. Damn it my cheeks hurt! Fuck me or laugh at me. Kick me out. Do something! My nipples were probably hard enough to crush my piercings and tear through my see-through black bra, and I suddenly remembered that I was not holding my shirt closed. Too late to make a modesty play now. I couldn't believe we were even having this conversation. "Well..." He leaned back and took another hit from the bowl, thinking. He was staring at my tits and my tiny little school girl skirt, and he was not hiding it. My heart started racing. "can you promise to at least try not to let your sister know?" I couldn't speak. I wanted to swear it to him, but all I could do was give a tiny nod. Methodically he sat the bowl on the table and took my face in his hands, lifting my lips to his. All of the tension I had been feeling instantly melted to a wet patch between my legs as his tongue slid between my lips and met with mine. At first he was only kissing me, but it was not long before his fingers slid from my cheek to grace my nipples through my bra, and then starting at the knee made their way up my thighs to that wetness he was causing between my legs. There was no fumbling about it, his thumb deftly shifted my panties aside and two fingers slid slowly across my bare outer lips. His other hand picked me up by my ass and shifted me into his lap. I sat in his lap facing away from him, with his hardness sticking into my ass, twisting my neck to meet his lips with mine while he deftly finger fucked me. His other hand slid into my bra and started playing with my nipples, twisting them, pinching them, flicking the piercings. My body shook as I came. "You came already?" He asked incredulously. "I cum very easily." I whispered, feeling somewhat embarrassed about that little fact. It was a part of why I like sex so much. A lot of girls complain that they can't cum in bed at all. When I am really into it I am lucky if I can make it into the bedroom before I cum. "Your sister does not. I always have to work for it." Ryan said smiling. I smiled too. Was he saying he would enjoy getting me off more than he did Katie? "Her loss." I said definitively, leaning in for another kiss. After the kiss Ryan smiled broader than ever. "Lets see just how many times I can make you cum before driving you home." he breathed against my lips. I almost came again. Katie had told me stories of how big Ryan's cock was, and how long he can go in the sack. She also told me that she fights her orgasms to see if she can outlast him. I bet he doesn't know she does that. I also bet he wouldn't like it if he knew. Like I said, her loss. Ryan lifted me up off of his lap to slide my panties down before he laid me down on the couch. He slid onto the floor and that gorgeous face lowered itself between my legs, disappearing under my short skirt. In the short time since I turned 18 I may have had sex more often than I should have, but only two boys had ever gone down on me, and they had absolutely nothing on Ryan. Their goal had only been to make my pussy wet enough to slide their cocks into it. Ryan's goal really was to see how many times he could get me off, and there was nothing rushed about it. He took his time getting me there, but when he pushed me over the edge I lost my mind between the first orgasm and the third, they hit so fast they felt like one huge long climax. After the fourth I tried to push him out from between my legs but he held me in place and kept at it. I felt like I was out of fluids by the time he finally pulled away. I had long since lost my will to fight him. "How many times did you cum?" he asked casually, as if asking about the weather. He got up and walked away. Walked away! Disappearing into the kitchen. "Fuck," I said, but that was all I had in me to say. My mind was literally blown. He laughed from the other room, and came back holding two bottled waters and a towel. I took the water eagerly and drank deeply. It wasn't until he had thrown the towel on me that I realized that I was covered in sweat. The towel was damp from where he had already wiped away some of my cum from his sexy face. I toweled myself off quickly. I started to take my top off but he stopped me, asking me to leave it on. To say I had forgotten that he was into slutty Halloween outfits would be a lie, but the request surprised me. I left it on. "If you want to take someone's clothes off...." he said, stepping in front of where I sat on the couch and gesturing with a sideways tilt of the head towards his slacks. I didn't have to be asked twice. His cock, as hard as it was, looked like it hung halfway down his leg. I rushed through getting his pants undone and pushed them down around his ankles. He must have taken his shoes off in the kitchen because he easily stepped out of them once I had them down. I wasn't paying attention. The biggest, most beautiful cock I had ever seen smacked me in the face as I had pulled his boxers down. He took it in his hand and pointed it towards me, saying "You know.... your big sister really sucks at giving head. Think you can do any better?" I made him wait while I fished my black lipstick out of my bra and put it on. He waited patiently and without complaint. I took the cock from him and eagerly dragged my tongue up its length. Katie was bad at it? Or was he just challenging me? Maybe she was good at it and his standards were really high? Either way, I wasn't going to be second to Katie at sucking Ryan's cock. I took him in eagerly, and did every trick I knew not to gag from his size. I deep throated him, but still only made it halfway down that cock. I wasn't pushing myself on purpose. I knew from Kate's constant bragging how much he liked getting the whole thing down her throat.... His hands came down on the back of my head as he forced more of himself further into me. Katie hated when he did that, but I was expecting it. I took him as far as he wanted to go, which left my nose somehow pressed against his body, and let him fuck my face, desperately trying to breath through my nose. I tried not to, but coughed and spat on his cock as I gagged. My eyes watered and my struggling to breath caused a wierd explosion out of my nose, but if that bothered him he didn't show it. Two minutes into face fucking me, however, he just stopped and pulled himself out of my throat. I gagged and dry heaved as little as possible before I lunged forward trying to get him back in my mouth, worried I had disappointed Ryan in some way. He stopped by grabbing my hair with one hand. "I am sorry," he explained, "but I wasn't expecting to get so carried away. Besides I don't think I can wait any longer before I actually get to fuck my girlfriend's little sister." I know I blushed, as dumb as that sounds. Had he wanted me before today? He picked me up and carried me into his bedroom. He set me down on the bed and started digging through a drawer. He pulled out a pair of handcuffs. I remembered when Katie purchased those and smiled. I wondered if he knew that I knew they were hers. I imagined how mortified she would be to know that I got to enjoy them in her absence. He turned me face down on the bed and lifted my ass in the air, then he pulled my hands behind my back and cuffed them together. This meant my face was buried in the comforter and my ass was stuck up in the air. With my skirt as short as it was and my panties long since removed, this left my bare pussy open to him. His tongue dug in and his lips sucked on my already sore labia. It hurt, but I was not about to complain. His tongue was eventually replaced by his fingers, sliding in and out of my pussy, and they were soon after replaced by the head of his cock. He didn't slide in, not at first, he just stood there with his head pressed into my opening. I tried to press against him, but he stopped me with a hard smack on my bare ass. He pulled his dick away from me as punishment for my presumption. Again he pushed the head, and just the head, back into me, this time saying "Someone has been a very naughty school girl, haven't they?" I nodded into the bedsheet, playing along. "I am sorry, sir!" I moaned. He spanked me again. Again his cock head fell out from how hard he spanked me and I whimpered in frustration and from the pain. That had really hurt. I was sure that I now had two huge hand prints on my ass, one on either cheek. Ryan could bruise me if he wanted, as long as I was his. "Tell me what you've done, little Stephanie." What? I had never roll-played before. "I.. errr, I masturbated in class." Spank! Again he pressed his dick slowly into my cunt, a little further in, but only just barely. "And why did you masturbate in class?" "Because I always wanted you, my professor, to fuck me." I whimpered. This time his hands kneaded my ass sensually. I could hear the smile in Ryan's voice. "Have you now?" "Yes sir." "How badly do you want me to fuck you little Stephanie?" "Very badly!" I whined. "What would you be willing to do if I fucked you little Stephanie? "Anything you wanted! Please fuck me.... please, Professor Ryan!" His hands, which had never stopped feeling my ass, slid forward and took a firm grip on my hips. "Good girl." he said, and slammed his full fucking length all the way inside of me in one solid thrust. I really had never taken a cock that big before, not even close. I tried to yell from shock and pain but the sound didn't come out. By the time my head hit the mattress again he was already back out and shoving in again. I bit the bed as hard as I could. Not just the sheet, I got my teeth latched onto the mattress itself. He let go of my hips and gripped my skirt in a wadded ball at the waist line, trying to hold me against him as his cock and hips kept slamming me forward. My pussy only grew tighter as he fucked me, and I started to cum. After my long batch of climaxes subsided, I realized he wasn't moving his cock anymore, just rubbing my ass. He pulled out, much to my disappointment, and undid my hand cuffs. I fell to the side, rubbing my sore wrists. I missed when he had taken his shirt off, but he was completely naked. I watched as this incredible guy toweled a layer of sweat from himself (the towel had been on the bed) and then just flopped down beside me, still fully hard, and motioned me to snuggle up to him. "I am still sweaty." I confessed. "I could care less." I pulled myself up to him, unrolling from the fetal position kind of hurt, and laid against his chest. I draped my thigh over his hard cock. I was very aware that he hadn't cum yet. I was also aware that he was naked and I was still in the slutty Halloween outfit, but it was obviously that that was exactly what he wanted, so that was more than fine. He kissed me, and I him, and it was wonderful, just lying their in Ryan's arms. My hand pulled gently up and down on his shaft while we kissed. "I have not cum yet." he stated. His cock throbbed in my hand. "I noticed." I said, trying to sound annoyed. He took his arms from around me and placed his hands behind his head. "Well, what are you going to do about it?" His smile could have lit the sky. I think he expected me to straddle him, but my pussy was really sore after the beating he had given it, so I kissed my way down his chest and gripped his cock with both hands. There was plenty of room on his massive cock for my little hands. The Desperate School Outfit This time I teased him more, starting out painfully slow, stroking him, blowing on him, and giving him the lightest of kisses, before I built up to sucking him in earnest. He just lay there, looking gorgeous, both hands behind his head, watching my raven black head of hair bob up and down on his cock using every trick I knew to turn him on. Eventually, as my jaw started to ache I had to start taking it slow. Katie had once said he had never cum from a blowjob. Damn it! I slid up his body and rubbed my pussy against his hard cock, back and forth. My pussy was more sore than before, not less. Biting my lip, I eased his cock head into my pussy. It hurt, and I had to keep stopping short and prepare myself to take in more. Once he was all the way in I just sat there, adjusting to the feel of him. "I am not going to fight my orgasm now." He said, and my jaw dropped. All that work and he had been resisting his climax? WTF! "If you can fuck me, really fuck me little Stephanie, I am not going to last long." He was smiling that cocky smile, and he had never moved his hands from behind his back. For a second I wanted to smack him. Did he know how big he was? But I was not about to stop before I got him off. I started fucking him, slowly at first, but picking up speed. My legs were killing me so I mostly lifted myself with my arms, digging my claws into his abs. At least my pussy was soaked! And I was really turned on... Soon I started to cum again, in spite of any pain I felt. I threw my head back as I bounced on his monster cock, and as I came his hands came in from out of nowhere and pinched my nipples through my school girl shirt and his cock erupted inside of me. I've never in my life came as hard as I did that day. I collapsed on his chest, and Ryan stroked my hair and whispered how amazing I was. I was torn between sheer panic that Ryan had cum inside of me and pure bliss over that same fact. He asked if I was on the pill, and I told him honestly that I was not. He said to meet him tomorrow after school and he would take me to get the morning after pill and take me to the free clinic to start on birth control, and that he would show me how to go about getting refills without my parents finding out. I agreed to meet him. Then he started giving me a lecture. He said he didn't want me to go fuck random guys anymore, that if I kept it up I would end up dying of some disease. He said anytime I felt like I just really needed sex to call him, since I had his number. "I'm selfless like that." he joked. So this wasn't a one time thing? Excited, I kissed him, and he kissed me back. Then he told me about his rules. First I would need to be on birth control, because he wanted to keep cumming inside of me. Katie never let him do that, even though she was on it, he told me. I was to be his fuck, and his fuck alone, if we continued things. If I dated other men, I could sleep with them, but only if we had gone out at least three times first. If I was dating AND sleeping with someone else, I could turn Ryan down for sex, but otherwise if he wanted to take advantage of me I needed to be available for as long as this affair went on, and he would be ready for me if I was in need, regardless of if I was seeing someone else. Since he had dated Katie for four years before he even started fucking me, he said it was fair that he play the other man in my life as well. Not that I could imagine ever turning Ryan down for sex, even now. I thought to myself I would likely be calling him more than he called me and told him I would hold him to the deal. "I assume if you pop the question to Katie you reserve the right to start turning me down?" He laughed. "No, I don't care how serious I get with your sister, I will never turn you out of my bed." Between kisses, he explained again how he was marginally serious about my sister but he didn't think marriage was likely. That said what we had would need to stay strictly sexual or it would need to end. He had no interest in breaking up with Katie for me. He wanted to make sure I didn't try to break them up, so he said if Katie up and dumps him our affair had to end as well. Had I not believed he would end things with me, I really would have broken them up by now. After I agreed to all of his terms he pushed my head down towards his cock, and I took it back in my mouth obediently. It wasn't long at all before he was hard again, and pulling my pouting lips off of his cock. "You are too sore to fuck me again, and I don't cum from head." He waited for me to make another offer. He wasn't as big as he had been the first time he was hard... "You can fuck me in my ass..." I offered. Katie had always made a big deal about not letting him do that. She had told me that before, but had I not already known the delight that lit his face would have told me much the same. Knowing Ryan liked it was one of the reasons I let men fuck me in the ass at all. I had wanted practice, just in case. I lay face down on the bed while he pressed his fat cock into my ass. Had I not just been ass fucked by a much smaller cock just the day before, Ryan would have been way too much for even me, but I lay there gripping the sheets as he grew to his full length inside my tight little ass and eventually came again. He lasted longer than the first time, and I was sure I would have trouble walking for a week. I was crying, but my pussy and my ass were filled with Ryan's cum, a man I had lusted over for four years. That was worth the world to me. He hopped off of me and got in the shower. When he came back I was right where he left me, with my legs spread, face down in a torn and soaking wet school girl outfit, and he told me to take my turn in the shower. That I didn't need to look like I had been fucked all day when he took me home. I guess the honeymoon was over. I agreed. After the shower though, I made the excuse of not wanting to get home with wet hair, so we decided to order pizza. I called my dad and told him I was at a different friend's house, which was true. I dressed in the more attractive of the two outfits Ryan had bought me, and we cuddled on the couch watching TV and eating pizza. After the pizza was finished, I pulled his cock back out and sucked him idly as he watched the rest of the movie. I offered to spend the night, since it was already 10 pm, but he turned me down since I did have to go to school the next day and he had to work, but he assured me we would have plenty of sex once we got back to his place the next day. That next day we got the pills, then went shopping for real outfits and discount sexy costumes, as it was the day after Halloween. I told him he could dress me up anyway he wanted... When I graduated that spring, he rewarded me with my own apartment, complete with a new credit card with a post-it that read "for furniture." I tried to tell him it was too much, but he insisted saying that with Katie moving in with him over the summer he needed a place to reliably get me alone. I was kind of miffed at learning about their plans that way, so I bought really expensive furniture. He was amused, and said if I did not agree to go to college I had to pay it all back. He also said it had to be local so that he could still see me whenever he had the chance, and reasserted that I would be paying my rent to him sexually. Of course I agreed. Today, I sit and type on my brand new Mac that Ryan bought me, while watching my flat screen television that Ryan bought me, and count my blessings. I mean, apartment aside, I never thought I would be going to college at all, nor did I ever imagine being the personal sex slave of my life long crush. And to think all of this is thanks to one crappy Halloween party, a super bitchy sister, and one fantastic Halloween!