1 comments/ 246517 views/ 38 favorites Sleepless Night By: happypsycho 3:30am, what was a man to do? John could not sleep, that much was certain. It had been a difficult day and those damn kids he was trying to teach history to were just too thick-skulled and annoying to learn anything. And his private life wasn't that great either... Such as the divorce with his wife of three years. What a pain in the neck that had been. Alimony, bitterness, lawyers, the whole nine yards. Thankfully, she let him keep the house, well... the apartment. But she took everything else and the law would make sure that she'd keep on taking from him on the first of each month. Strangely, though, that hadn't been the worst. The worst was that his sister had lost her job and had asked him to move in with him. He didn't mind her company at all, it's just that... well, it's just that his old feelings came rushing back... He remembered when he was eighteen and his sister Diana was fifteen. At this age, John was pretty much thinking of sex twenty-four hours a day. When he wasn't masturbating in the bathroom over a worn copy of Penthouse, he was thinking of new ways to masturbate. And of course he imagined himself with the various girls at his school, like Courtney who always wore thigh-highs and had legs to die for. John imagine licking those legs from the ankles to the thighs and then higher and higher... And there was Devon, the beautiful brunette who supposedly gave great head if you asked her nicely to. One day, as John was by the pool, imagining Devon giving him a blowjob, he heard the patio door open and saw Diana step out. "I'm just gonna tan for a bit, okay?" "Sure..." He sat up and tried to hide his hard-on, hoping Diana wouldn't notice. Apparently, she didn't; she just walked to the side of the pool and laid down on her back, catching the sun. John suddenly felt his hard-on raging again. Diana was simply stunning! At fifteen, her breasts were fully developed into perfect perky 30C's, her legs were long and smooth looking and her belly was flat and slightly muscular. Her long blonde hair fell past her peach colored shoulders and her lips had a constant pucker, as if she was waiting for a kiss. John kept staring at her, forgetting that she was his sister. He felt precum wet his swimming trunks and so he had to run inside and masturbate feverishly in the shower. Then, guilt took over, but also a strange feeling of pleasurable taboo. After that, John acted differently with his sister. Their parents were delighted that they didn't fight anymore and Diana seemed to wonder from time to time why he was so kind to her, but she didn't give it another thought. Meanwhile, John kept imagining him and his sister in different sexual positions and when he went out with his girlfriend, he imagined he was going out with his sister. When he finally left for graduate school, he was sad but also relieved, since he knew these feelings were wrong. And so, little by little, he forgot about the desires for his sister and went on with his life. Until she asked to move in with him. He accepted, thinking nothing of it, but after a couple of days, he walked in on her as she was stepping out of the shower and he quickly turned away, apologizing. He went to his room and sat on his bed, out of breath. Diana was now a woman. And she was more beautiful than ever. Her legs seemed longer than ever and her whole body, glistening with water was just too much for John. Her breasts still looked perky and she apparently shaved her pussy hair. John locked the door to his room and masturbated in a way he hadn't since he was living back home. It felt wrong. It felt good. And now it was almost 4:00am and he couldn't sleep. He thought of getting up and getting some warm milk or watching some TV, but he knew that if he got up, he wouldn't sleep at all. Better to keep on trying. As he closed his eyes, he heard a slight knocking at his door. "Yeah?" The door opened and Diana walked in, wearing her red silk nightgown. "Are you sleeping?" "No, I can't..." "Yeah, I heard you moving around... I can't sleep either..." "Come in..." John thought nothing of it, just a talk between siblings. Diana gave him a smile and sat on the edge of the bed as John sat up. "So, what's up little sister?" "I don't know... I guess I miss Michael..." "Michael? Oh, right... your boyfriend." "Ex boyfriend..." John gave her a supporting smile. "Right." "It's just... I shouldn't tell you this, but..." "What is it?" "Well, we broke up five months ago and I haven't... you know... since then." "What? You haven't what?" She hesitated for a moment. "Had sex." "Oh..." John felt uncomfortable, not knowing where this was going. "Can't help you there!" He laughed a weak laugh and was a little surprised to see that Diana was not smiling. "Are you sure?" As he was about to ask her what she meant, he felt her hand on his thigh. The touch of her palm on his naked skin sent electric waves of pleasure up his spine and into his brain. He could actually feel his pupils dilate. All these years of fantasies and he didn't know what to do. "Wha... what do you...?" "I know you look at me like I'm a woman... not just your sister." "No, I don't, I..." "Ever since that day by the pool, when I was fifteen... I followed you when you ran in and I heard you jack off... and I heard you moan my name when you came..." John didn't know what to say. He was petrified, but he could also feel his dick harden. "I thought of you too, especially since you walked in on me the other day... That turned me on like you wouldn't believe... I again heard you jack off. But this time, on the other side of the door, so was I." "It's... it's wrong, I..." "Yeah... that's why it feels so great..." To this she smiled and looked at his crotch. The hard-on was obvious. "My oh my... you're even bigger than I imagined..." She giggled and he smiled, not knowing what to say. "Let's see if you're as sweet as I think you are..." She looked him in the eyes and put her hair behind her back before licking her lips. Then she masterly got his dick out of his shorts and looked at it. And then he felt her tongue on his cock. It felt amazing, it felt like heaven. She licked his whole cock, as if it was a popsicle and then she started to hungrily suck it. "Oh my God, oh... that's... Oh my Goooooddd..." He tilted his head back and closed his eyes. He felt her hands on his balls, fondling them and the feeling of her tongue on his shaft was just too much. He put his hands in her hair and started pumping his hips up and down, fucking her mouth. He saw Diana start to rub her clit with her other hand and she started to moan. "Diana, I'm cumin', I'm..." He exploded in her mouth and she avidly gulped down every drop. He kept cuming and cuming and the sucking sounds she made as she drank it all made him want her even more. Then she looked up at him, smiling, a little bit of cum on her lower lip. "That was nice, big brother..." John was out of breath, he didn't know what to say. More importantly, he wanted his sister more than ever. His dick was still hard and he still wanted her. "My oh my... you're hard to please, aren't you?" She smiled and straddled him, slowly removing her nightgown as she did so. John barely held back a gasp as he saw his tanned sister, naked and so close to him. He put his hands on her shoulders and they felt softer than he imaged. He ran down his hands down to her hands and she smiled. He then put his hands on her ass and up the small of her back and pulled her to him. For a second they stared at each other and then their lips locked in a kiss. They closed their eyes and let their tongues meet and explore each other's mouth. They moaned in unison and soon John could feel Diana's pussy juice on his lower belly. Her hands were in his hair, caressing it feverishly and his hands were on her ass, appreciating how firm and perfect it felt. As they kept on kissing, he felt her move her weight and suddenly he felt her eager pussy on his rigid cock. The feeling was more intense than anything he had ever felt. She was tight and she was wet. She slowly lowered herself on him and it felt like slipping on a velvet glove. When his dick was completely in her, she broke the kiss and smiled. Her breasts were quickly moving up and down with every breath. He put one of her nipples in his mouth and started flicking it with his tongue. Diana moaned and started to move her hips. John almost cried in pleasure and he helped her move up and down with his hands on her ass. Soon, the bed was creaking with their movements. He could feel his dick slide up and down her wet pussy and seeing her breasts bounce in rhythm and seeing the pearls of sweat form on her neck made him even more excited. He started to go faster and she cried in surprise. He went faster and faster until Diana screamed out in pleasure every time he rammed his cock in her. "Oooh! Fuck me! Fuck me, John! Fuck me! Oh God, yes!" John grabbed his sister's head and pulled it to his and he started kissing her mouth, nibbling on her tongue and on her lips, pumping harder and harder. The bed was knocking against the wall and the mattress was squeaking. Diana was moaning and so was John, faster and faster. Their sweat mixed on their bellies and their nipples rubbed with each movement. Soon they were two glistening bodies, wet with sweat and lust. "My God, John! Yes! I'm coming! I'm fucking coming! Fuck my pussy! Fuck me, John, Yes! Yes! YES! YEEESSS!" He felt her pussy contract all around his cock in waves and waves of orgasms. As she started to kiss him madly, he also came, unloading his cum deep into his sister. He could still feel her pussy contract and she was shaking with every new spasm. He kissed her and gently bit her tongue as the cum exploded in her belly... Afterwards, things were better and John was able to sleep, a hand on his sister's thigh. Before morning broke, they would make love one more time, and they would stay together and be happy. Truly happy. For once in their lives. Sleepless Night I was awakened from a nice slumber... a dream.. a noise maybe? Whatever it was it was I don't remember. Your arm wraps around me, pulling me closer. I love it when you hold me while asleep. I closed my eyes in hopes of falling back into dreamland. I lean back into you, trying to get comfortable, I feel your cock pressing into my ass. Hmmm I wonder what you are dreaming about. There was no way I am going to fall back to sleep, the longer I lay there awake feeling your hardness pressed against me the more wet I became. Only one way I was going to get back to sleep. I roll onto my other side, your arm still around me. I place my hand on your chest, finger tips gently exploring. As my fingers brush over your nipple I notice your breathe caught for a moment. Not in a deep sleep it seems.. so I do it again. This time a sleepy moan escapes your lips. I lean in and kiss you softly, whispering against your lips "wake up luv". My hand now moving down your chest, over your stomach...searching. Ahh there...my hand caresses your cock...still hard. I kiss you again, while continuing to stroke you. You moan against my lips, your hand moving to my bare hip, squeezing gently. I let out a quiet giggle, "you awake luv?", this time I get a response...You kiss me back,moaning a "mhm" against my lips. I stop stroking your cock and move my hand back up to your chest, I press gently indicating I want you to roll onto your back... you comply. I slide a thigh across your stomach, moving to straddle you. I whisper "I have a job for you." Then I kiss you again, you part your lips to my probing tongue...I could kiss you for days. My breasts pressed against your chest, your cock trapped between us. Your hands move to my hips, holding on. "And what job is that" you gasp as I slide further up, pressing my breasts against your face. You let out a moan, and flick your tongue out against my nipple, teeth holding onto it, lips pulling it into your mouth. My hips, already moving in circles against your chest as you suckle my breast... I let out a moan of my own. "It is a little repetitious" I reply in a teasing tone as I move further up, placing a knee on your pillow and then the other.. straddling your face. I hear you swallow and let out a groan, feeling the heat of your breath against my skin. I give a little whimper... waiting. You are killing me anticipation, "please" I whisper, reaching a hand down to part my lips. You let out a low animal growl, grabbing hold of my hips.. pulling me in. Your mouth covering my pussy, tongue delving into me. I let out a squeal of surprise, hands reach out to grab the headboard. You attack my flesh violently with your tongue, licking, sucking my my pussy. Lapping at my slit..moving your way to my clit. You stay there, sucking it between your lips, then lashing it back and forth with your tongue. I feel my thighs tremble, my hips wanting to buck, but stay still by your hands holding me in place against your face. I arch my back, reaching behind to find your hard cock, wanting to feel it. As I wrap my hand around it, a begin to stroke you as you continue to eat my pussy...you let out a low moan, the sensation vibrating against my clit. Your breath coming almost as fast as mine. You make this growl from deep in your chest as your tongue dips into me again...that sound puts me over the edge..."god baby, I am gonna cum" I warned. You focus on my clit again, making my body shudder... you let go of my hips letting me writhe. So you could slide two fingers deep into my pussy. My pussy clamps down immediately and I begin to ride your fingers as well as your mouth. I let out a scream as my orgasm hits.. cumming all over your fingers. I didn't have time to think...you grab me and roll me onto the bed. Kissing your way up my body till your reach my mouth. Letting me taste myself on your lips, tongue. You part my thighs with yours, forcing them to open wide. Reaching for your cock, I grab hold..aiming and guiding you.. wanting to feel you inside me. You pause.. my god you are going to have me beg for it. "Fuck me baby, please" I whimper. You know what you are doing to me.. and let out a light chuckle. Sliding a hand behind your neck and pulling your mouth back down to mine...losing myself in your kiss. I feel your body give slightly as I drew your tongue in deeper, moving my hips up, attempting to bridge the gap. The tip of your cock teasing my clit, sliding up and down my wet slit...but not in. You let out a moan to go with mine as I pull at your cock, tugging, rubbing you furiously against my sensitive clit. I wrap my legs around your waist as you begin to ease up, holding you against me, rocking your hard cock between us. I am not letting you get away...it is not a want.. I need to feel you in me before I lose my mind. You were not giving in to me easy. I let out a frustrated moan...you want to play it like that fine. I push you off playfully, furstrated but amused. We roll together on the bed, kissing, I end up on my back again, you slide down between my thighs, tongue working against my pussy again. God I love it when you do that, but it wasn't enough this time. I reach for you, begging.. finally you gave in and moved onto your back. Letting me crawl over your body, as I head towards your cock, stopping me when my pussy reached your hungry mouth and probing tongue. Taking you into my mouth, feeling your soft skin as I suck on you. Your hips move with my motion, but your attention from my pussy never wavered. Flicking steadily over my clit as your fingers explore me, sliding two deep into me. I let out a gasp and suck on your harder,as add a third finger, fucking me hard with your fingers, stretching me. Not letting go of your cock, moving you in and out of my mouth faster as I feel my climax begin. Rubbing the tip over my outstretched tongue, feeling you throb against my lips. I grip you harder as my climax takes over. "Easy baby" you tell me... I relax my had a little. Licking the pre cum that has formed now on the head of your cock. You shudder and moan as I do this. "Please, luv.. fuck me..." I plead as I look over at you. I see a slight smile on your lips... I let out a yelp as you grab at me, pinning me face down on the bed. Spreading my legs wide with your thighs. Your hands moving up my back, as you lean into me. Now kissing and nibbling at my shoulder, moving to my neck. You gently bite me as you thrust your cock hard and deep into my wet pussy. I let out a cry, digging my nails into your arm that is now wrapped around my shoulder and neck. You thrust harder into me again...deeper this time.. almost to the point of pain. But the sensations was pure pleasure. How I wanted this..I love feeling you inside me...your cock buried deep. "Oh god, yes.. harder" I shout out.. urging you on. You pull out, I back into your trying to prevent it, almost whimpering as you you moved off me.... grabbing my shoulders you flip me over. Before I knew it you were back back inside me ...fucking me harder. Bringing my hands from around your neck..pinning then above my head. "You want it harder Kitten?" you suductively whisper in my ear. Moving down to nuzzle my neck, I am unable to speak, the pleasure I am getting from you is to intense to even form words. I try to say yes, but it sounded more like a garbled moan. You chuckle against my neck as you kiss me. "Leave your hands where they are" You tell me as you lift up, bringing my legs up over your shoulders. Thrusting deeper still into my pussy. Using all my willpower not to reach up and touch you... you have me screaming with pleasure. I can't take it anymore...you are gonna have me cumming again. I tell you I am about to, to push me over the edge you reach down and play with my clit as I watch you fuck me.. How I wish this would never end. I buck my hips up to each thrust...you are getting close too. I can feel you throbbing inside me. "I'm cumming" I shout out... as I cum you rub my clit harder and thrust deep into me. Can anything feel any better? "I am going to cum soon baby...where do you want me to cum?" you say in a gasp. I want to taste you, but I don't want you to pull out of me. "Don't stop luv, cum deep inside me, don't stop fucking me." I plead. My climax has been reached but it feels to good to stop. You lean down to me...my legs still up on your shoulders...you bite at my lips then kiss me as you give your final thrusts and cum in my pussy. You lift off me a little, I let my legs back down onto the bed... pulling you back to me. I love feeling your weight on me after... as you stay inside me still. Both catching our breathes... Now laying against you, arms wrapped around me...maybe I will find sleep. Sleepless Night This happened back in the summer. I was staying in a hotel in Zeeland for work. Because of my job I spend a lot of my time in hotels. Some of them are better than others. This one was sort of middle of the road. It wasn't a slum but it wasn't the Ritz either. It was also one of the few places where I have a bit of a communication barrier as Dutch is very much my third language. It was a bit of a dull trip really, work was going okay but the people were dull and most of the other guests in the hotel were senior citizens. I was counting the days till I moved on to Amsterdam, which would at least be a little more fun. One evening after I had a shower I wanted to have a drink from the Mini Bar. I was only going to have cola but needed to get some ice. The ice machine was down the corridor so I pulled my robe on and took the bucket down there. When I got to it I found that it was out of order so I had to go up a flight of stairs to the next level to get the ice. I felt both a bit odd and a little turned on as I got into the stairwell. For a start the cold concrete under my bare feet and then the fact while I was able to use my door spy hole to see if anyone was there I had no idea if someone was on the stairs or the next level. I walked up and got the ice and then trotted back to my room. I didn't see anyone and I don't think anyone saw me. I thought about it and wondered why I had felt a bit of a tingle from it. The thing was the robe I had on was thick and secure I was also wearing my panties. Large comfortable panties the sort of panties that could be mistaken for a chastity belt from a distance. I then thought back to two nights before when I had gone to the hotel bar for the evening; it was a warm night so I had worn a light summer dress. I had not worn a bra with it and had worn more sexy underwear. I had not felt a tingle then. I guessed it was the connotation of wearing the robe. I had a bit of trouble getting to sleep that night and I felt like I wanted to do something. But I just wasn't turned on enough to really get going. I tried to let my mind wonder and all I could think of was being naked on that stairwell. By this time it was around one in the morning and the lights in the corridor outside of my room were dimmed. I stood in front of the mirror and took off my pyjamas and looked at myself. I'm tallish just under 5'10 and I keep myself fit. I have a neat hourglass body, large breasts that are matched by the hips. I keep my pussy trimmed rather than shaven and have thick raven black hair. I took a deep breath and picked up the room key card and looked through the spy hole I couldn't see anyone. I opened the door and stepped out, I stood there for a few seconds and let the door close behind me. I then headed for the stairwell. This to my surprise was still fully lit. I guess that it was a fire escape. The harsh yellow light reflected off of my pale skin and I again felt the coolness under my feet. I slowly climbed the stairs and exited onto the floor above. The lay out of the floor meant that there was a sort of circular route. I could follow the corridor around and come back to the stairs. I turned left and slowly walked down the first corridor. Next to the ice machine was a coca-cola machine the red light glowed and in the low light lit me up in red. My pin-up body nude bathed in red light must have looked very sexy but there was no one there to see. I got to the end of the corridor and turned right. This corridor only had the one very low light so it was a lot darker than the last, I slowly walked along it, one foot in front of the other feeling the carpet under my feet. I got to the end and turned right again. This corridor had the elevators in it and the green light above them glowed. I stopped at the end and looked to see where the elevators were. The indicators both read 'LG'. Like the first corridor this was a long one, as I walked slowly I started to hear something. I thought for a moment that it was someone else and I froze momentarily. Listening carefully I could hear that the sound was coming from one of the rooms, it was a man snoring. I started to walk again, one foot in front of the other the snoring grew then started to fade. By the time that I was level with the elevators I could no longer hear it. I glanced up at the indicators one of the elevators was now shown to be on the third floor, I was on the fifth floor and my room was on the third I held my breath. The little arrow to the left of the indicator blinked on. The elevator was going down and I started to breath again. I turned right again and this time I could see the green sign for the stairs in front of me. I think my pace quickened. Soon I was back in the stairwell the coldness under my feet. I started down and then I could hear another sound this time it was voices. Two men speaking in Dutch, I couldn't make out what they were saying. I looked quickly over the railing. I was between the fourth and fifth floor, they were at the bottom of the stairwell. I froze against the wall and then I heard the sound of a door open. Cool air caressed my skin I heard the men's voices fade and the door shut. They were using the exit to leave the building. I slowly walked down till I got to my floor. I had to walk past three doors till I got to mine and when I did I was surprised by how loud the bleep of the card was in the door. Once in my room I threw myself on the bed. My legs open wide and I plunged two fingers into myself. I was surprised at how wet I was and how quickly I was able to bring myself to shuddering orgasm. Once I had calmed down a bit pulled the covers over me and slept. The next morning I was a bit jumpy. I looked around the breakfast room to see if I got any knowing glances from anyone. But I didn't. It is not an experience that I will forget although I don't think that it is something that I will repeat.