The Desperate School Outfit

byEsotericNiceGuy©

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.

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byEsotericNiceGuy© 8 comments/ 52494 views/ 12 favorites

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