6 comments/ 140387 views/ 4 favorites One Strange Night By: littlesquirt I had just gotten home from work, when the phone rang. It was my sister Jennifer, she wanted to come over for a bit, so I said sure why not. Jennifer at 5'5", was good-looking old blonde. She was 20 years old, two years younger than I was. I guess you would call her sexy, but being my sister I never really thought of her that way. She always had a boyfriend, and when she broke up with one there was always several more chasing her. We had a pretty normal relationship, it wasn't totally uncommon for her to invite herself over. We would sit around, watch TV and talk for a while before she went back to her place for the night. 20 minutes later Jennifer arrived, she let herself in like she usually does. Steve, her current boyfriend was with her. I wasn't expecting Steve to come along, but I invited them in the living room, then grabbed some beers from the kitchen. We made some small talk while watching TV. We had a couple more beers each, when Jennifer asked me about my current situation. I had broken up with my girlfriend only a couple of weeks ago, and since then hadn't had a date. She asked, "So you haven't been with anyone in that time?" I thought that was a weird question, especially in front of her boyfriend. "No I haven't," I answered. "Do you have any interest in guys?" she continued. That caught me totally by surprised. "What? No! Why would you ask that?" "Well Steve is curious, and wonder what it would feel like to suck another man's cock. We figured you hadn't had any action in a while, and maybe would be up for a blowjob. Nothing more." I have never even considered doing anything with another guy. I thought this is crazy, no way would I do something like this. But then my cock twitched a bit. No I thought, I can't do this. Jennifer continued, "He's not gay, he just wants to experience it once. He wants to do it tonight, then we'll get outa here. What do you say?" "No fucking way, you think I'm gay? I won't have anything to do with that shit." My cock twitched again. What the hell was going on here, I'm not getting turned on by this, am I? "This doesn't mean your gay. Besides whats the difference who sucks your dick, a guy or a girl? Your dick is in a mouth, you enjoy it, you blow your load, relieving all that pressure that's been building up these past couple of weeks. You go to bed happy." Maybe it was the beers, maybe it was the pent up frustration, but for some reason I said, "Maybe a blowjob isn't a bad idea, after all I won't touch him, so I'm not gay." Steve smiled a bit, looked a bit nervous. "Alright," I said. "We'll go in the bedroom for my blowjob, Jen you wait here." "Oh no, do it right here." "No way, not in front of my own sister." "Yes right here so I'll be able to instruct if Steve runs into a problem," she said. "Besides I want to see my man give his first blowjob." I must have been out of my mind cause I agreed. "You sit here," she said, motioning me to the center of the couch. "Now take off your pants." I hesitated, I've hadn't been naked in front of my sister since we were little kids. "Don't worry, its just another cock, I've seen plenty," She said. She then moved over to me, undid my jeans. "Stand up," she said, and I did. She pulled my jeans and underwear down quickly, and I stepped out of them. There I was standing naked from the waist down in front of my sister and her boyfriend. "Lets get this off too, so you can get real comfortable." And she pulled my T-shirt over my head. Now totally naked she looked down at my limp cock, then pushed me back onto the couch. "Sit back, relax and enjoy this." She reached down and gave my cock a quick squeeze before she sat down on the chair across from the couch. "Go get him Steve," she said. Steve came over, but not too quickly. He kneeled down between my legs, looking at my cock, probably the first time he's seen a cock up close. He looked at me, I just smiled, closed my eyes and leaned my head back on the couch. I was gonna imagine it was Lisa, the sexy babe at work with a great body. He tentatively took my limp cock into his hand, give it a little squeeze. My cock twitched a bit as he cupped my balls with his other hand. He started jerking me slowly, and my cock started to respond. After a little bit I was hard as a rock. Then I felt his tongue on it. He slowly licked the tip, circling it. Then he licked down the shaft to my balls then back up. Oh man this was pretty good I thought. He took my cock into his mouth, just a bit at first, then slowly taking in more and more, until he had most of my 7 inches. He bobbed back and forth, grabbing the lower part of my shaft with his hand. I could feel his tongue running over my head as he continued to bob up and down. With my eyes closed I was fantasizing about Lisa, wearing one of her short mini skirts, blowing me. As this image was running thru my mind I felt my orgasm building. He kept sucking and I blew my load in his mouth. He choked a bit, but did swallow most of it. Jennifer got up from her seat, leaned over and kissed Steve right on the lips. "mmmm," she moaned. "That was so hot, seeing you suck another cock. And I can taste his jizz on your tongue." She kissed him again. "Now its Steve's turn." She said looking at me. Jennifer pulled Steve to his feet, undid his pants, pulled them down. She then yanked down his boxers, and pulled off his shirt. She then pushed him down on the couch next to me. I expect her to go down on him, but she pulled me up and pushed me towards him. "No no," I said. "But you owe him one." She insisted. And pushed me again. I resisted, after all I wasn't gay. But suddenly I had this desire to suck Steve's cock. I dropped to my knees in front of Steve, his cock already standing at attention.. I've never done this before, I had no idea what to do. I grabbed it with one hand brought it towards my mouth. Then I licked it just like he did earlier. I licked around the head, then on the hole, then down his shaft to his balls. I sucked his hairy balls into my mouth, while slowly wanking his shaft. He moaned. I ran my tongue around his balls, tasting them, feeling all that hair. Oh God what was I doing, but at the same time I was enjoying this. I worked my tongue back up his cock, swirled it around the tip, and then sucked it into my mouth. I worked the lower part of his shaft with my hands while I continued to suck his cock. There was another moan, I looked over and there was my sister, leaning back in the chair, her skirt was up around her waist, her hand buried in her panties, obviously working her clit. She was getting off watching me blow her boyfriend. My cock started to return to life, I was so horny. I turned my attentions back to the rock hard cock in my mouth. I could feel his orgasm beginning. His cock got even harder, then exploded. I tried to swallow all his hot sticky cum, but some escaped out the corner of my mouth. "Oh God that was so hot, it got me so horny I could fuck anyone right now," Jennifer said. She looked hot, her hand still in her panties. My cock was hard again and ready to go. So I turned towards my sister, grabbed her by her ankles and pulled her to the floor. She lands flat on her back. I put one hand on her shoulder to pin her down. "What are you doing?" she asked as I pulled her panties down, then ripped them right off of her. Her shaven pussy is now fully exposed. I positioned myself between her legs, she struggled to get free but I had her pinned down pretty good. "You just said you could fuck anyone right now, I'm anyone," I said. "Stop it, stop it!" she yelled as my cock brushed up against her slit. "You're my bother, oh my God no." I rubbed my cock back and forth over her wet slit a couple of times and then buried it deep inside her in one thrust. Her eye's opened wide. Her pussy was so hot and wet. I kissed her on the lips, some of Steve's fresh cum drained into her mouth. "I just sucked off your boyfriend cause you wanted to see it, so now I'm fucking you!" As I thrusted in and out of her she seemed to relax. Before long she was moaning with pleasure. I ripped her blouse open, sending all the buttons flying. I pushed her white lacy bra up exposing her breasts. She had nice C cups, little nips that were sticking out as hard as my cock. Playing with her nipples I continued to pound her. She spread her legs a little more and brought her knees up, allowing me to go deeper. "Oh my God, oh my God," she was moaning. "Yeah fuck me, fuck me hard, oh yeah." This got me going even more. I exploded deep inside her. I collapsed on top of her. Then I remember Steve was here, I turned and looked, he sat on the couch staring at us wide eyed like he's never seen this before. Well he's probably never seen siblings fuck each other. He was stroking his cock which started to come back to life. "I haven't cum yet, I need to cum," my sister moaned out. I pulled my shrinking cock out of her, then worked my way down to her clean shaven pussy. On my hands and knees I rubbed my nose on her clit, then tongued it. She shivered a bit. Then I shoved my tongue deep in her pussy, tasting both of our love juices mixed together. I lapped up my cum leaking from her pussy. Second time tonight I've tasted a man's cum. I continued to work her pussy and clit, she was shaking and moaning. Slipping one, then two fingers in her, I scooped out more of my cum, then popped those fingers in my mouth. Then I felt Steve behind me. He spit in his hand and rubber it on his cock. He spit again, this time on my asshole. I felt his hard cock head against my asshole. Slowly he pushed it in me. At first it didn't want to go, but he pushed again and the head was in. I stopped working Jennifer's cunt so I could concentrate on getting Steve's cock in me. He pushed forward, I rocked backwards, and his cock was in. It hurt a bit so I remained still for a minute. The pain subsides and I rocked forward to let Steve know I was ready to go. With his hands on my hips he starts thrusting in and out of me, slowly at first but then picks up his pace. I return my mouth to my sister's pussy, tonguing her clit again. Suddenly she starts quivering, and she explodes, her juices flowing all over, soaking my face. I suck up all her juices that I can. Steve is still pounding my ass, his balls slapping against my ass. I can't believe how great this feels. My cock in coming back to life again, even though I've already cum twice already. "Hold on Steve," I said. "What? You don't like this?" he asks. "Man I love it, I just want to fuck my sister again while you're fucking me." With that Jennifer scoots her butt down until her pussy and my cock are lined up again. "Yes fuck me brother. Fuck me now," She says. She reaches down, grabs my cock, and guides it back into her freshly eaten pussy. It hotter and wetter than it was before. "Alright lets go," I say. As I push into Jennifer, Steve pulls back. When I pull back from Jennifer Steve buries his cock deep in my ass. At first it's awkward, but the three of us finally get a good steady rhythm going. This goes on for a while. Steve pounding my ass, my cock pounding my sister. "You like my boyfriends cock in your ass don't you? Take it all you slut you," she moans to me. I feel Steve's cock swell a bit, then he unloads his wad into my ass. I can feel his hot cum in my ass. He pulls out and falls against the couch. I continue to slam into my sister, she keeps moaning, "Fuck me fuck me big brother, fuck me with the big cock of yours, yeah." I can feel my orgasm building. Just then Jennifer explodes with her own orgasm. Her pussy grips my cock even tighter, and that's all I need. I explode in her again. "Yeah cum in me brother, fill me with your cum." I pound into her a few more time, then I slip out, and roll off onto the floor next to her. "That was intense." I said. They both agreed. One Strange Night It started out just like any other Wednesday; I had class from eight till noon, and then I worked at the Bistro until nine. I walked home from there; it took about fifteen minutes. The full moon was just rising, floating just above the horizon like a great shiny penny, huge and orange. I was beat. Wednesdays are rough. I wasn't sure if Jennifer, my girlfriend would be home. Her younger sister Andrea was in town, and I thought they might be out having fun. Andrea was eighteen, three years younger than Jennifer and in her last year of high school. She was thinking about coming to the university where Jen and I went, so she was staying with us in our apartment for the week. I didn't mind, not one bit. Truth be told, I had already harbored some nasty thoughts about Andrea. She looks a lot like her older sister, and yet quite different. Jennifer is a big girl. Not fat, not by a long shot; just big: tall and curvy, athletic and sexy as hell. She has beautiful long brown hair and big coy brown eyes behind her glasses. Andrea, on the other hand, is tall dark and lithe, almost waiflike. She stands almost six feet tall, an inch shorter than her sister (and me too), with small pert boobs and a tight little butt. She has short jet black hair, and always wears a black leather choker and black doc martins. A cute little punk rock girl with a sassy demeanor. It wouldn't be the worst thing, I had thought, if I happened to walk in on her taking a shower. Of course I wouldn't do any such thing, not intentionally. The idea, tickling the back of my mind like a little devil though, of having both lovely sisters in one bed just wouldn't quite leave me alone. Jen had never given me any reason to think she might be bisexual, or willing to experiment. Still, it didn't hurt to daydream. And I did daydream, walking back to the apartment that evening. Nobody seemed to be home. No surprise, really. I opened a beer, and went to take a shower. I had a lot of homework, but nothing that wouldn't wait. I thought I heard a noise in the bedroom, which is probably why I didn't blunder right in on them. I opened the door slowly, not really knowing what to expect. What I saw, however, was so far out of my experience that I didn't know what to think. I just stood there, not even breathing. Jennifer was nude, on her hands and knees, facing the foot of the bed. Andrea was behind her, nude as well, but for the black leather choker, and a strap-on harness. Jennifer's strap on harness-- she was wearing the very dildo that had penetrated my own rear end just last weekend. I knew it well, it was about the same size as my own penis; but purple and ribbed. It was made of silicone, and buzzed delightfully when a small vibrator was tucked inside it. Now it was being rubbed all over Jennifer's pussy. Andrea was wielding her silicone tool aggressively. Thick gold rings pierced her nipples, and her small firm breasts shook delightfully as she worked her sister like a puppet. "Did ya miss me Sis?" she cooed as she grabbed a big handful of Jennifer's long brown hair. "Did you miss licking my pretty little pussy? I've missed yours." A pang of jealousy that I hadn't know I had in me rocked through my body, making my knees weak and my stomach ache. At the same time, my cock swelled in my jeans. I couldn't look away. "Yeah Baby" Jen answered her, her voice thick and raspy "I missed my baby sister and her sweet little pussy. I've missed you so much Andrea." "Did you miss my dick too?" Andrea asked, slapping Jen's shapely buttocks with the purple tool. "Oh yeah Little Sister" Jennifer cooed "I've missed your big dick in my pussy so much." "I've missed you too Big Sister." whispered Andrea. "Are you ready?" "Oh yes, I'm so ready." I had never witnessed Jen getting fucked from this angle before; my view had always been from behind. Her hair was wild, cascading down over her face. Her boobs dangled down, covered in a sheen of sweat. Her rump was thrust up in the air, like a cat in heat. I realized that I thought she looked beautiful like that. Andrea seemed to savor the moment, caressing her sister possessively with one hand as she held the silicone phallus with the other. The rings in her pink erect nipples gleamed in the low light. Jet black pubic hair peeked out from beneath the strap-on harness. With one sure motion, she guided the artificial cock into Jennifer's pussy. Jen sighed, burying her face in the covers, letting her sister fuck her wide open pussy. I could actually hear the slurp of the dildo moving in and out of her vagina and the slap of their bodies clasping together. Andrea leaned forward, taking Jen's big full breasts in her little hands, hugging her sister tight as she fucked her. It was too much for me. I didn't know what to think. I was too freaked out, turned on, jealous, and intrigued to deal. I carefully closed the door, leaving the amorous sisters to their lovemaking. My mind was reeling. I went to the kitchen and finished my beer, and then headed over to the school. Maybe that homework couldn't wait, after all. The design building was left open all night for students working on projects. I made my way downstairs to the Design Studio, where my midterm project was waiting for me. I had planned on spending most of the weekend working on it. Spending tonight drafting would give me a good head start. The place would probably be deserted tonight; everybody else would have somewhere better to be than in a windowless concrete walled room, laboring under the fluorescents. As I walked the hall toward to studio however, I heard voices. "Baby you got what Temple needs?" "You know it Baby. I've been saving it all for you." I walked softly to the open door of the design studio. Long ago, long before I had started school here, somebody had donated a couple ugly old couches to the design department. They stayed in the studio for the comfort and convenience of the students. I myself had slept there quite a few late nights. Sitting on one of the couches now was Nathan, a freshman who I hardly knew. He was tall, a beanpole; pale skinned and slightly effeminate. I didn't know him well, but I had kind of assumed that he was gay. Standing next to him was Temple, the late night cleaning lady. Temple was always very sweet and friendly to those of us who worked late in the studio. She was big, black, in her forties, with a wild head full of flaming red hair. I wouldn't say she was unattractive; I had simply never thought of her in those terms before. As I stood in the doorway watching, I saw Nathan unzip and pull down his slacks, revealing the biggest penis I had ever seen, outside of porn. Mine isn't small; I would guess its average sized, or even a little larger. Nathan's tool looked to be a good three inches longer than mine. I was fascinated. He held it out invitingly, showing off his girth. Temple, meanwhile, was peeling off her blouse and unsnapping her bra, revealing a pair of gigantic brown breasts with long erect nipples in the center of large dark aureole. She got down on her knees, resting her bosom on Nathan's thighs. She then did something that really threw me for a loop. "Honey" she said "Let me tell you, I been looking forward to this all day!" She reached into her mouth, and took out her false teeth, setting her dentures carefully next to Nathan on the couch. Then she lowered her toothless mouth onto Nathan's huge cock. She took the whole thing in her mouth. I could hear her slurping and sucking. Nathan was playing with her breasts. I backed out of the room, leaving them to do their thing. It was a weird night; there must be something in the air. I decided to go for a walk. On my way upstairs, I imagined that I heard something. It must be an overactive imagination; I had sex on the mind now. I still didn't know what to think about what I had seen at the apartment, but my cock hadn't gone soft since I had first seen them. Watching Temple and Nathan together hadn't done anything to cool me down. There was no mistake though; from up the stairwell I heard a moan and then a giggle. Two people were having sex up there, there was no doubt. I walked softly up the stairs, and found myself looking into Professor Bushnell's office. The door was wide open, and Professor Bushnell was there, naked and spread eagled on her desk. Doctor Kaufman was there too, naked as a jaybird, kneeling between Professor Bushnell's ample thighs. Professor Bushnell was the department head; sixtyish, plump and cheerful, with grey hair that she usually kept up in a bun. She looked like your quintessential Midwestern grandmother who baked pies and cookies and went to church every Sunday. She had a gentle sense of humor but could be bitingly critical, and had a brilliant eye for design. Doctor Kaufman was a physics teacher. He was in his fifties or sixties, and looked (and acted) the part of the archetypical absentminded professor. He was tall, with a shock of graying hair, and a salt and pepper beard. He had a bit of a paunch, and the worst taste in shirts: loud and plaid. "Oh Ralph, you sexy beast! You lick my pussy so nicely!" Professor Bushnell giggled, pulling and tweaking her nipples. Her large pendulous breasts and her round tummy were fully visible to me. Doctor Kaufman's head bobbed between her thick legs. His ass was pale and hairy, and his legs were spindly and thin. "Come on up and fuck me now darling!" Doctor Kaufman stood up, revealing his own bobbing erection. His balls hung down low, and his beard was wet with come. I got my first glimpse of Professor Bushnell's vagina: her bush was furry and graying, and large meaty lips pouted open. Doctor Kaufman slipped his penis inside her, and absently played with her clit as he fucked her. "Anne" he gasped "your pussy's so hot! It feels so good to be inside you." "Do it to me" Professor Bushnell encouraged him "Fuck me harder!" They humped like two horny teenagers; Professor Bushnell wrapped her legs around Doctor Kaufman's back, and they fucked hard. I was fascinated; I couldn't look away. "Ralphy" Professor Bushnell gasped "I want to taste myself on you. Let me suck your prick." Doctor Kaufman complied, pulling his cock out of her vagina and offering it up for her to suck. She enthusiastically devoured him, sucking him like a lusty cheerleader on a date. She cupped his pendulous balls, and her head bobbed up and down. A few grey hairs had come out of her neat bun, and made her hair look wild. "I'm going to come soon Anne." Doctor Kaufman warned. "Then stick it in my ass." Professor Bushnell said, lifting her head up off his penis "I want to feel you in there." She lifted her legs high in the air, still lying flat on her back on her desktop. Doctor Kaufman guided his wet cock between her buttocks. He seemed to have no problem finding her entrance. Professor Bushnell moaned loudly as he entered her anus. "Do you think that's sexy?" The whispered voice shocked me; it came from right beside me. It belonged to Margaret, a rather mousy girl in my design class. Margaret is one of those girls whom I tend to forget exists. She is talented, especially with small, intricately detailed stuff, and always seems to be around, but rarely speaks out in class. She is short and plump, of Asian descent (Chinese and Malaysian, I think), with longish brown hair and a kind of squeaky voice. She always seemed rather shy and introverted. She must have come along while I was gaping. "This seems to think its sexy." She went on, tentatively stroking the bulge in my jeans. My erection responded electrically to her touch. "I hope I'm still that randy when I'm their age, don't you?" I gulped "Yeah, I sure do." I whispered. "Want to come up to my dorm?" She whispered "I think they're nearly done." Indeed, Professor Kaufman was fucking Professor Bushnell's ass hard and fast now, and their passions seemed to be reaching a peak. Margaret and I left, hand in hand, hurrying over to the dorm building. We didn't speak as we crossed the quadrangle, still holding hands. The full moon had risen high in the night sky. It seemed smaller now, and had lost its orange tint, shining pale white. We cast long bluish shadows on the grass as we walked silently across campus. Her dorm room was tiny, neat and organized, and crowded with knickknacks and art supplies. As soon as the door was closed, she started peeling off her clothes. Off came the sweatshirt, revealing surprisingly large breasts unconstrained by any bra. Her nipples were erect, and pointed skyward at odd angles. Off came the sweat pants. She wasn't wearing any panties, and her pussy was covered with a healthy bush of dark brown hair. "I'm not normally this forward." She said, frowning slightly "But I'm feeling really randy tonight. Would you mind licking my pussy first?" I didn't mind one bit. She fell back onto her bed; I pulled off my shirt and jeans and crawled between her spread legs. She was clearly very aroused; her pussy was wet and the lips pouted open, swollen and purple. Her clit peeked out from its little hood, pink and precious. I started licking, slurping up and down her slit and teasing her clit. She tasted unlike any girl I had ever licked before; sweet and salty, almost like apples with a hint of spices. She enjoyed my tonguing, tugging my hair and rubbing herself onto my face. I enjoyed pleasuring her. Suddenly she pushed me away. "Hold on" she said "I've got a condom somewhere." As she rummaged around in her dresser drawer, I took the opportunity to get my jeans off from where they had bunched up around my ankles, and to pull off my socks and boxers. She handed me a wrapped condom, which I tore open and rolled down my engorged shaft. Margaret got back on her bed, drawing her knees up to her chest. "I can't let you fuck my pussy." She said apologetically "I'm saving it. But I'd like it if you'd put it in my ass." She pointed out a small bottle of lube on her dresser. "Use plenty of that." She said "and you don't have to be too gentle." I squirted a lot of the clear lube on my condom clad penis, and made my finger all wet and slippery too. I probed between her ass cheeks, massaging her anus. She seemed to open right up for me. I let my finger slide into her asshole. She was hot and tight. "Please hurry." I replaced my finger with my cock, placing the head right at her opening. Her pussy was dripping juice down her crack onto my cock. I pressed forward, and she bore down on me. It was incredibly tight. We worked at it, slowly burying my quivering cock into her tiny asshole. Her eyes were shut tight, and she pulled and twisted her nipples. Finally my entire penis was inside her anus. I couldn't believe how tight she was: my cock felt like it was squeezed in a hot and slippery fist. "I'm not going to be able to hold out long" I gasped "I'm going to come soon." Margaret reached behind her head, grabbing something from her bedside table. "That's ok." she said "Go ahead and fuck my ass hard. I'm going to come soon too." I fucked her ass hard and deep. As I fucked, she worked her clit with a little Hello Kitty vibrator. I could feel the buzzing transmitted through her flesh. I felt my orgasm rising up from my toes like an express train. I slid my hands under her ass and lifted her hips up, balancing her on her shoulders, burying my cock as deep as it would go into her asshole. I roared aloud, thrusting hard again and again as I filled the condom with what seemed like quarts of come. She came along with me, cooing and wiggling, legs kicking as she ground Hello Kitty onto her button. Her breasts heaved and shook, her chest flushed, and her eyes were clenched tight. Her stomach spasmed and her breath came in tiny little gasps. Finally it was over, and my cock slipped out of her butt. We lay still for a little while, resting and enjoying being naked together. "I don't want to get married or anything" she said "but if you ever want to play again, you're always welcome to come up." "I have a girlfriend." "I know." She smiled. I got dressed and walked home, replaying the night's events in my minds eye. Thousands of bright stars filled the heavens above me, and the full moon still shone bright and pale. When I got back to the apartment, Andrea and Jen were in the kitchen, drinking coffee. Andrea was wearing sweat pants and a lacy black bra; Jen was wearing an oversized t-shirt and apparently nothing else. "Where've you been?" Jennifer asked "We've been waiting up for you." It was after one in the morning. "Down at the design studio, working on my project." "Come on" Jennifer said, taking my hand and tugging me toward the bedroom "Andrea's got something to show you." The giggling girls pulled me into the bedroom, where we fell, a tangled mess onto the bed. It had been an exceptionally weird night, I thought to myself, and things were only getting stranger.