0 comments/ 5055 views/ 2 favorites First Time with Sir By: MakeYouTremble You open the door and slip in quickly. You only have a few minutes to get ready for when I'll arrive. We had spent the afternoon together and you accepted my offer to spend the night together. Since we didn't have much time to talk about specifics we hastily agreed to just keep things lite, mostly vanilla with a few kinky sprinkles. No bondage and even in role playing "no" means no. Looking around it's a nice, but typical hotel room. "Wait for me like you think a good girl should", was all I said when you asked if I wanted you to do anything special. You have an idea of what that should entail. You check the pocket on my bag and verify that the condoms are present. You aren't sure if they are a sign of hope or confidence on my part, but you're happy that they are there. You go into the bathroom freshen up and give your teeth a quick brush. You also brush your hair. Looking in the mirror one last time you smile at what you see and head back into the main part of the room. With a final breath you take off your shoes, dress and panties and put them on the desk. Now naked, you kneel on the floor facing the door and wait. Your knees shoulder width apart, you aren't sure what to do with your hands. After a few moments you settle on gripping your elbows behind your back. It's submissive and shows off your tits nicely. Exposed and waiting your heart beats faster as your wait. Thoughts of the day play through your head. Holding hands and a couple of quick kisses was all we've done so far. You think to the few times when I put my hand on your waist to guide you before me and your nipples harden to think of my hands on your breasts. Of my hands running over your bottom. Of spanking you. Even though the room is cool, you feel hot and you hear the door beep to allow someone in. A moments panic make you worry it might not be me, but the door swings wide before you can react. I look in to see you in your glory and just stand to gaze for a few seconds. Entering the room and closing the door behind me I see you breath out, now that a passerby won't look in and see you. "What a wonderful way for my princess to greet me!" I say, a smile on my face and blood rushing to my crotch. You keep your eyes on mine and whisper, "Thank you, Sir!" Walking to you, I lower my hand and help you stand. Gently gripping your face in my hands, I reach down and kiss you. My tongue running along the inside of your lips. As I feel you move your arms to reach up around my neck, I gently push them back down and hold them behind your back with 1 hand. The other moving up your back to cradle your head. Pulling you tightly against my body we continue our kiss. You feel my hard cock press against your belly through my pants and I feel your hard nipples against my chest. Breaking the kiss, I lower my hands to both hug you and keep your arms trapped behind you. "Have you been a good girl today?" I ask playfully. "Oh, yes, Sir!" "Really? You think good girls go to strange men's hotel rooms and wait for them naked?" my face mock serious. "..." "I think someone needs a smacked bottom," and I shuffle over and sit on the edge of the bed. "Assume the position." You move to the side and bend over my lap. I guide your head and upper body around so that your legs hang free, but your upper body is on the bed. Tapping the insides of your thighs, you spread your legs a little and the blows start fast and furious. 10 smacks in as many seconds, 5 on each cheek. As I run my hans over your bottom, it feels warm. As I dip a little further down and run my hand up your inner thigh I feel a little wetness. Smiling, I repeat another 10 smacks followed by a few seconds of rubbing and then a 3rd set. "Now, lets see if you can behave," I say. You can't see my face, but you can hear the smile in my voice. I roll you onto the bed and get you positioned so that your butt as at the very edge of the bed. I help you get your legs up and put your feet on the edge as well. "Hold onto your ankles and don't let go." Now on your back and spread wide I lean down over you and go back to kissing you. Slowly, I start to work my way down, paying special attention to both your nipples. Slowly I make my way down and I kneel on the floor and drink in the wonderful vision before me. Starting above your clit, I kiss and lick. At first I spend most of my time on your upper thighs and outer labia. I pull back every so often to check and am happy to see the near white knuckle grip you have on your ankles. As you climb your peak, I start to zero in on your pussy opening and clit. Alternating and listening to see what will bring you over the edge. As I hear your breathing get more labored I also slip a finger into your pussy and start to finger fuck you. "Please", is all I hear. "Cum for me baby," my voice a little muffled as I try to talk and lick at the same time. It only takes a few more moments and I feel you cum. Instead of letting you relax as you come down from your first orgasm, I immediately move back in and see if I can bring you to another orgasm. To see if I can get you to release your grip. I succeed in bringing you to your second orgasm, but fail to make you release your ankles. I'm going to spank you again, but I'll have to make another excuse. I move back up your body, kissing and licking my way up. Once over you I kiss you and say, "Okay My little slut, back on the floor, on your knees." And I pop up and wait for you. I enjoy watching you struggle a little, your body clearly not recovered from your recent orgasms. But, no one ever said that submission was going to be easy, so I reach down and help you up by grabbing a handful of hair and guiding you off the bed. You kneel again your back against the bed. Looking up your eyes are still a little glazed and your mouth is slightly open. You look so beautiful. "Undress me." You hear the words and it takes a few moments to both understand the words and the order. I see a smile form on your lips as you realize what I meant and you immediately reach for my belt. "No, do it right. Shoes, shirt, then pants, greedy slut!" I playfully scold. You bend over and untie my shoes and slip them off as well as my socks. Tossing them to the side you start with my shirt. I don't stop you, but make a mental note that you will need instruction on proper protocol later. You untuck the shirt and undo the buttons. I help a little and shrug my shoulders out of the sleeves so you can take it off while still on your knees. With only my jeans still on, you go back to undoing my belt. I watch your face carefully but you don't see me, your eyes focused on the task in front of you. You move quickly, but clumsily. Your body still not fully recovered from your orgasms. You pull down my jeans and underwear down to my knees, my cock bouncing free and smacking you in the cheek. As we both chuckle you reach up and take my cock in your hand. It's not fully hard, but it feels warm in your hand. "No!" my voice startles your and your hand drops from me. "I said undress me, not indulge your inner slut." My voice isn't harsh and as you look up at the surprising command, you see the gleam in my eyes. Playtime is just starting. You finish getting my pants off, your eyes staying glued to my cock the whole time. Once I've joined you in being naked you look up and wait for me. "Hands behind your back and just look at my cock." Your gaze returns to my crotch as you place your hands behind you. As you sit on your heels, my cock is a bit higher than eye level. I step in closer to your face and you open your mouth in anticipation of the order. Instead, I stay just a couple of inches away. "Just look at it, focus on it, and think about it." You're surprised and glance up for a moment, but then refocus on the organ in front of you. Not huge, but not small either. Balls are shaved and the pubic hair around the base is trimmed short. A little precum is glistening on the end. You think about it in your mouth, your tongue caressing it. You think about it in your pussy, pumping in and out. You realize that both your pussy and mouth are in danger of dripping and at least close your mouth and swallow to avoid that embarrassment. "Would you like to kiss my cock and balls?" "Yes, Sir," you whisper. "Proceed." You lean forward, open your mouth and just as you start to take the head into your mouth, you feel my hand pushing your head back. You lick your lips and taste the slightly sweet taste of my precum. "Don't be bad! I said you can kiss it, don't be greedy now!" Chastised again, you lean in and start to kiss my cock. Starting with the head you kiss all over and when you get to my balls you continue kissing, but occasionally slip your tongue out a little as well. You feel my hand on your head guiding you from cock to ball to other ball and back to cock. In seconds I'm fully hard. "Okay, baby doll, you can suck on me. Start with my balls and show me what you can do! Use one hand if you like, play with yourself with the other." You don't need to be told twice. One hand reaches up to work on my cock and balls and the other slips between your thighs. I let you play for a few minutes and I realize that if I don't want my part to finish too soon, I'd best slow you down. "That's nice," I say, pulling my cock from your mouth. You pout at the loss and look up, wondering if you've done something wrong. "Good girls get fed their cum, but you weren't a good girl, were you? You were greedy and tried to touch and suck without permission! I think you know what happens to greedy girls, don't you?" I move and sit in the armless desk chair. You smile as I pat my lap and you resume the position. This time, I not only rub your bottom but reach in and play with your clit and finger fuck you in between spanking sets. You try to keep count, but having my cock trapped between your ribs and my body as well as the attention I give your pussy, you are simply too distracted to count. Still, it doesn't take long for you to reach another orgasm. You're feeling pretty wiped out as I lead you back to the bed and lay you down. I join you and hold you for several minutes as you recover, gently stroking you hair, face and breasts. "We have some unfinished business, don't we?" I ask. You look up at my face, and follow my gaze back down to my now much softer cock. The gentle pressure as I push you down all the encouragement you need to slip down between my legs and to resume your cocksucking. I'm hard again quickly and after a few minutes of enjoying your mouth I reach over and grab a condom off the night stand. You open it up and slide it over me. I pull you up to my level on the bed and roll you onto your back. Holding your hands above your head with one hand I guide myself into you. You're soaking wet and while you've had several orgasms today, only this will satisfy you. I start fucking in earnest, pleased to see the look of ecstasy on your face as you give into the fucking. It's a struggle, but I manage to hold off on my orgasm until yours begins. As I feel your pussy clench down on me I lose control and cum hard, letting myself collapse on top of you and kissing you as we come down together. Later. Is the sex really done just because we are no longer having orgasms? You lay in my arms, our fingers gently running along any skin we find. Wordlessly, you get up. I hear water running in the bathroom and a few minutes later you come back and lead me to the bath be the hand. I sit and then you join me, sitting between my legs. I wrap my arms around your waist and hug you tightly to me as we soak in the warm water. Later. Is the sex really done just because we are no longer awake? Dry again, we're under the sheets. Face to face, our bodies entwined, your head resting on my shoulder. We watched TV and talked until we were both half asleep. Now, in the darkness Sir holds his slut and she holds her Sir. We sleep. First Time With Sis This is an adult read event that took place in my life. If you are not 18 years of age, please leave now. * Hello! Thanks for choosing my story. I hope you enjoy your reading. I have been reading members wonderful experiences and fictional stories here for quite some time now. I finally decided to write my first of many experiences here and share it with all of you. I have had sexual encounters with two members of my family, my sister and my mom. Neither of the two knew I was having sex with the other, even till this day and I think it is better this way. This story is the beginning of a wonderful relationship that happened between my sister and me. It sparked a whole bunch of great events between us and still to the present day. All the events are true with slight modification. I will start with the first time I had "fun" with my older sister. There has been other occasions since and continuing to the present day and will write about them in due time. Sex with my mom did not come till later after my sister got married, which was a little late in her life according to my parents. I will get to those stories out to you later on. First Time With Sis. When my sister and me were still living at home with our parents in our large 4 level, 5 bedroom house. I used to try and get a glimpse at Holly whenever I could. Our family was pretty liberal back then, we didn't always close our bedroom doors when changing or closing the bathroom door when showering, walking naked from bathroom to bedroom, stuff like that. Let me tell you, it was not easy for a horny guy like me growing up seeing two women walking about almost naked at times. I have always had the hots for my sister Holly. We were really close growing up (still are). She is 10 years older than me. She was a really sexy and horny woman, still is now at 53. When I first took notice of her she had a body to die for, 5'9" tall with just the right curves and these wonderful 36C tits, a nice rounded ass, just the right shape and size, long shapely legs and the most well trimmed bush. I used to wait for here to come home from work and go upstairs to change. I would hide in a spot where I could peek around the corner and watch her change. I would get as hard as a bar of steel. When she would finish changing and would go downstairs I would run up to my room for a quick jerk off session. This went on for quite a while, shower peeks, bedroom peeks and in the summer months seeing her in a bikini around the pool. A few years went by. I was now 18 years old and my sister was 28. It was December 31rst, New Years Eve. My parents and some of there friends, along with me, my sister and her fiance were all going out to celebrate the New Year. My parents and their friends went ahead of us. My job at the local fast food joint had me scheduled to close up that night and I would not be out of there till about 9:00pm. My parents asked Holly if she could stay behind and pick me up from work to get me home so I could get ready for the party. She agreed and said she would tell her fiancé to just meet us there. With all things said and done, Holly picked me up and rushed us home so we could get ready. We were both crossing paths, bumping into one another running in and out of the bathroom from our bedrooms trying to get ready in a hurry. You'd think with such a large house we lived in we would have two bathrooms on our floor of 4 rooms. No, we had only one bathroom on our floor. God forbid if we touched yet went into our parents on suite bathroom. Holly had showered before picking me up. I went to my room, got undressed and was walking down the hall towards the bathroom when I glanced into my sister's room and saw her sitting on the corner of her bed. My jaw dropped as I stopped dead in my tracks, like hitting a brick wall. I could not take my eyes off of my sister. There she was, naked, her tits out in the open, putting on her pantyhose. You know, the type you don't wear panties with. One leg up on the bed and the other on the floor, causing her to expose her pussy, what a sexy sight! She stood up to pull the part up over her hips to her waist and looked up at me, stared for a second and said in a sly tone "like what you see kiddo?" I was an idiot because all I said, as if in slow motion, was "Aaaaaaaa... Ya" and walked off with my hard on to the bathroom. I hopped into the shower took in the feel of the water and started soaping up. I lathered up pretty well especially my dick as I started stroking it furiously with the thought of my sister's tits and pussy racing through my mind. I have never seen them that close. I came, shooting cum on the shower walls. I rinsed off, shut off the water and reached for my towel. I had my towel over my head while I stepped out of the shower and started drying off my head not realizing Holly was there doing her hair and makeup. When I pulled the towel down to dry the rest of me I saw Holly looking at me with a shocked look on her face that quickly changed to a devilish look. "Did you rinse off the shower?" she said. I looked at her with a grin. "Wouldn't be funny, for you, if mom found your cum in there." She added I looked back at the shower as she walked off to her room. All the while I was naked in front of her. I blow dried my hair shaved what hair I had on my face, brushed my teeth and the whole time thinking that my sister was there looking at me, at my cock not to mention the fresh image of her pussy in my mind. I finished up, went to my room and got dressed. We left to go meet our parents. While driving we shared some small talk. She had her dress up enough so it would not touch the floor of her car. I couldn't help notice my sister's legs as she drove. She looked at me and said "Quit staring silly, your acting like a virgin" I looked away and down, clenching my hands together and said in an embarrassed tone "I am sis... sorry". Holly looked at me in an angry yet concerned way and said "DON'T BE SORRY!" Then she toned down saying "You're a great brother, kiddo. I didn't mean to hurt your feelings. I just didn't think you haven't been with a girl yet." I responded with "I'm not very popular with the girls" Holly sighed; put her hand on my leg in a comforting way saying "It will come, give it time" The rest of the ride was pretty quiet except for some more small talk. Finally, we got there. While looking for parking spot we saw her fiancé Dan parked sitting in his car waiting for us, we waved as we passed him and ended up parking at the complete other end of the parking lot. Before we got out of the car my sister asks out of the blue in a curious way "Is that why you're always peeking at me, is it curiosity?" "No... Yes... No" I could only answer. I never thought my sister knew I was stealing looks. "Well which is it kiddo?" she asks nicely. Since she knew, I might as well confess. "Well it's like, not curiosity... not curiosity about sex... but... more like curiosity... about... you... I think you're really... Aaa... hot" She sat back against her door in aw "You risk getting caught by mom and dad just to see me... like... to really SEE ME naked... WOW! I just thought you were looking like me as an object, like you do at the girls in your dirty magazine." I was a little shocked as to how she knew about the magazine I hid in my room. "I... I'm...flattered... I don't know what to say." She said with a huge smile. Just then her fiancé Dan knocked on her window. As we got out of Holly's car he kissed her hello and asked "Is everything okay" Holly quickly replied "Everything is fine. I just found out your future brother has a crush on some hot chick." "I see, maybe you should let her know how you feel about her" Dan added while patting me on the back as we all walked to the reception hall. Little did he know I already did. We got in, checked our coats, found our table. It was close to the front where my parents and their friends were sitting. It was getting close to 11:00pm. As we sat down our meals that the waiters were holding for us arrived. We ate as we watched people dancing and partying it up waiting for midnight. After eating I was wondering around the hall laughing at the drunken people and checking out the women and ogling over some of their attires, trying to get peeks at cleavage and legs. I ended up by the bar near the back of the hall and started talking to some guy when Holly saw me on her way to the washrooms. "Hey stud, do you want to dance? " She asked. "Sure" I said. "But first I have to go to the little girl's room." My sister added. "Do you know her" asked the guy. "Nope, do you? I replied trying to look cool. "I don't think she is coming back" the guy said What took forever, I finally I saw her coming towards me with two drinks in her hand. "There she is" I pointed out. As we walked off to the dance floor she asked while holding one of the drinks up to me "Rum and Coke?" "Cool, thanks sis" I happily replied. "Do you mind if we stay back here, there's less people" Holly asked. "Ok no problem sis" I replied. Disco was what we danced to back then, it was really fun. I drank down my rum and coke of the evening and had a great time dancing. It was getting close to midnight now so we went back to the table. The bubbly came around and whet fast and so did midnight. We did the usual kisses and handshakes with everyone and by then the music was back and so were the people dancing. I went to dance with my mom for a bit, Dan and Holly came to join us a few songs later. We were dancing the night away when the D.J. started to play a slow. So naturally I was walking off and my mom said "Hey mister, you just don't leave a gal like that on the dance floor" So I went back and had that slow dance with my mom. The song ended, my mom said she was going back to the table. When Dan told my sister to dance the next couple of slows with me I had a grin from ear to ear. I remember we were slow dancing to a Chris de Burgh song that was quite long. I was holding her with my left hand on her waist and the right one in her hand. We worked our way slowly into the crowd away from the table's view. My sister was different, couldn't put my finger on it. Then all of a sudden she puts my right hand on her waist and puts her arms around my neck. At that point, the guy from the bar I spoke to walked by giving me the thumbs up. My sister's tits pressed into me and our bellies touched. I was staring right into her cleavage and she caught me looking. "It's ok... I like it" my sister said. She then took her hand and slid my right hand down onto her ass. I couldn't help it. I delicately caressed and kneaded it while looking into my sister's eyes and saw her smile in approval. Wow it was like soft and firm at the same time. It gave me one serious fucking hard on. I know my sister felt it because she pushed into it. "Someone better calm down, there's no shower here to jack of in. You'll have to take care of that nice cock of yours that I saw earlier, like you do every night" she said laughingly into my ear. I couldn't say anything and looked away as if ashamed. "I'm just teasing you. Don't worry about it. I do it all the time. I play with my pussy whenever I hear you whacking off in your room." Holly added. "You could hear me?" I asked. "D'uh our rooms are next to each other and the walls are not sound proof. Lucky mom and dad are downstairs or you'd get a beating every night... and not the type you'd like" she said laughing. I was red and now horny knowing my sis masturbates to me beating off. Well the slows were over and we walked back to the table. It was around 1:00am and the sweet table came out. We all got up to get stuff before it all disappeared. After eating there was more dancing, mingling and drinking. 3:00am came fast. "We should all get going before everyone leaves at the same time and it turns into a mad house. I'd like to get out of here before the sun comes up" dad said laughingly. "Are you riding with us or your sister?" my mom asked. "With Holly, she plays better music than dad." I said jokingly Dad and mom said they would see us at home and they left. Dan walked us out to my sister's car. Holly unlocked the doors. I got in the car and Holly had her car door open as she and Dan exchanged a few words between themselves which seemed to take forever. He kissed my sister turned towards me looking through her car door opening. "Good night champ and good luck with that girl of yours, make me proud." Dan said loudly while winking at me. Not knowing what to say, I smiled and said "yeah... thanks Dan" "What an idiot." my sister said laughing after she got in the car and closed her door. I looked at her with one eyebrow up thinking to myself, you're marrying this guy. She let the car warm up a bit and Holly drove us home. We were about 45 min behind mom and dad. Holly and I didn't say much on the way home. I stole a few more looks at my sister's legs, which were conveniently exposed. "No lights on, I think mom and dad are already in bed" I said while we pulled into the driveway. "Probably, dad looked beat tonight. We'll have to be quiet" Holly commented. I walked in first, followed by my sister. While taking our coats off, my mom called down quietly from the top of the stairs to make sure we were ok and tell us they were in bed and will see us morning or rather the afternoon in our cases. I watched my sister's ass shift up and down as we went up the stairs. As we passed my parent's room on our way to the other stairs that go up to our rooms we giggled as we could hear our dad snoring loudly. We reached the top of the stairs and Holly went towards our TV room. "Aren't you going to change?" I whispered out to her. "Getting a blanket... Why? Do you want to watch?" She answered in a naughty way as she walked in to the room. I froze right there. She went in and got the blanket and came right back out and stood in her bedroom doorway. "Well... I'll even let you help?" she whispered to me. I was caught completely off guard, quickly gathered my thoughts and took a chance for once, swallowed and before I could say anything, Holly reached out and grabbed my hand pulling me in to her bedroom. I let out a "Yes!" Holly giggled and shushed me saying quietly. "We have to be quiet." I was already getting hard. Holly put out her extra blanket on the bed and turned her back towards me whispering "undo the snap then unzip me." My hands were shaking, but not as bad as I thought. I undid the snap and lowered the dress zipper. It lowered down to the top of her ass. My heart was racing and my now rock hard cock was trying to bust out of my pants and I haven't seen her front yet. My sister turned around and lowered her straps over her shoulders and then slowly slid down her dress. I was in heaven she was wearing a red lace bra. I could see her perfect tits through it. The dress hit the floor and there were those nylons I saw my sister putting on. As I mentioned earlier, she wasn't wearing panties on. They had a white built in panty, which was practically see through. My sister turned her back to me once again. "Unhook my bra... please." saying. I was so speechless. I fumbled with the bra clasp, but managed to unhook it successfully and slid the straps over her shoulders. She let it fall on the bed while slightly leaning forward pushing down her panty hose from her waist, bending down even further to push them down to her ankles. Wow what a view of her ass and pussy. She must have been really wet because it looked like her whole crack was shiny. Holly stood back up and turned around to face me. My sister was so beautiful and sexy (still is) standing naked in front of me, in her own room. "You like" she whispered softly. I swallowed and just nodded yes. I had to suck my tongue back into my mouth because I think it hit the floor. I didn't know what to do but just stand there. Holly let me take in the sight of her naked body a few more seconds. "Your turn kiddo." She whispered slowly. My turn... I was thinking. My sister reached forward and started unbuttoning my shirt (I had already taken off my tie) and took each of my wrists to undo my cufflinks. She pushed my shirt off my shoulders and I pulled it off the rest of the way. She reached for my belt, unbuckled it, then the pants. Once the zipper was open and lowered below my protruding dick, the pants fell straight to the floor. My dick was sticking out the top of my bikini briefs. My sister put her hands on my shoulders, looked straight into my eyes and winked her right eye at me. She then squatted down slowly, sliding her hands down my sides to the waist band of my briefs and pulled them down to my feet. She looked up at me, looked at my dick, looked back up at me and whispered "Take a deep breath" I breathed in and she swallowed my cock in one shot. She turned and pushed me slightly on the edge of her bed so I was now sitting. My sister kept sucking my cock with still her both hands at my waist. I really couldn't believe this was happening. I wasn't going to last much longer. "Holly... Stop... I'm going to cum, I'm going to cum" I said quickly but quietly. She stopped, looked up at me and said "Slide up a little" As I did she climbed up onto me, she looked at me and eased her pussy onto my cock ever so slowly. Once I was in all the way, Holly moved ever so slowly in an up and down, forward and back rotary motion on my dick. "Your cock feels great in my cunt" she whispered. About five minutes of my sister fucking me, I started to move with her. She leaned forward whispering "Don't move too much or the bed will creek... we'll go wild another time" That was it, I murmured "Oh Holly, I'm..." I was just about to tell her I'm going to cum. She cut me off whispering hard saying "I'm cumming Robbie... cum for me... cum inside me... cum in your sisssssssster... Ooooo fuck I'm Cummmmming" I pushed up into her and I shot my load, spurts after spurts of cum into my sister's cunt. She kept moving about slowly and our mixed juices were oozing out and down to my balls and toward my ass. She finally stopped, were both breathing hard staring at each other from the most intense fuck ever, my only fuck ever. My sister climbed off me, slid down to my cock, looked up at me and licked me from my ass crack, over my balls to the tip of my cock, licking up our sex fluids. When she was done, I collected myself and got up off her bed, bent to pick up my clothes, she then stops me before I turn away, leans in and gives me a deep kiss on the lips. The taste of our juices was so sweet and horny tasting that I kissed her back passionately. Then suddenly Holly broke our kiss. "My New Year's resolution came true." whispering to me. "Mine too!" I whispered back. We giggled at our stupid remarks. My sister then wrapped her hand around my semi hard and sticky dick giving it a couple of light squeezes leaning towards me. "You know I'm going to want more of this. I think WE need to go skiing this weekend?" Holly whispered in my ear. "Yes... but let's not forget our skis" I quickly replied. "Happy New Year bro" she whispered. "Happy New Year sis" I whispered back. I snuck out of her room quietly and entered my room, closing my bedroom door behind me ever so quietly. Just as I dumped my clothes on the floor and crawled into bed I heard my parent's bedroom door open. * I will be posting more of our experiences. Thanks for reading. First Time with Sis My sister, Nicole, and I are one year apart, though we have been in the same grade all our lives because I repeated Kindergarten because we moved around a bit when I was five. Because of this, and since our birthdays were only two days apart on the calendar, we began telling everyone that we were twins. Being in the same grade also had the added advantage that we were closer than I think most siblings are that aren't actually twins. We had many of the same teachers and friends. We did lots of things together, and even had double dates together (though that may be because I had my driver's license first). When Nicole turned 18, we celebrated her big day by going out for dinner at her favorite restaurant. Even though it was my 19th birthday, the night was about her because it was her 18th, the day she became an adult. We'd have a bigger party on Saturday for all her friends, but Mom and Dad wanted to make sure they marked the day she became an adult with the family. After we got home from dinner out for Nicole's 18th birthday, all I wanted to do was head to the den, pop in one of my parent's homemade sex tapes and jerk off fantasizing about my sister. But Nicole wanted to watch some TV with me, which I found out was simply an excuse to talk to me about her boyfriend's plan for them on Friday. Since Mom and Dad had retired to their bedroom and shut their door, which normally mean they were having sex, Nicole and I would be alone and free to talk alone upstairs in the Den on the other side of the house. When we got upstairs, I turned the TV on and sat down on the couch. Nicole joined me. We didn't watch anything, she really wanted to talk. I was a little upset that I wasn't going to be able to sit and jerk off to my dad and sister fucking, but it was Nicole, and she really needed me, so I sat. As soon as I was seated Nicole blurted out that she had agree to let Tim, her boyfriend and my best friend, fuck her on their date on Friday night. "I'm really nervous about Friday," she told me in a near whisper after she explained Tim's plans. "What if it turns out I'm horrible and he dumps me because of it?" She really was quite worried. Tim's parent's were going to be away for the weekend at some business social in Tahoe, he was going to have the house all to himself. She said that the last time they went out, he had talked about having sex while his parents were away then presented her with a small ring and asked her to marry him. Of course, I was shocked that he hadn't told me anything about this, and for a few seconds I was a bit pissed he hadn't said anything. Then Nicole told me that she had said yes, and agreed to going over to his place and have sex with him. "Trust me," I reassured her, "He'll be so happy that you're giving your pussy to him, he'll be in heaven." She bit her lip and raised her eyebrows in a sign of hope. "You really think so?" Unfortunately for her, she knew his reputation. He liked to fuck the hot chicks and then dump them a few fucks later. He was a real douche bag that way. I knew he was hot for her, and really wanted to make this a lasting thing, though. He'd told me he saw himself marrying her in a few years, after college. But he'd never told me that he was going to propose to her. "Trust me, Sis," I told her. "He's really that into you. Having sex is just icing on the cake for him." She smiled at that. Nicole has such a beautiful smile. I wanted to kiss her. I leaned into her and did just that. To my surprise, she let me and even kissed back. This encouraged me. I place my arm around her waist and slid my tongue into her mouth. She quickly sucked it up and leaned into me. I slid my other hand under her blouse and slid it up toward her breast. She grabbed my wrist and stopped my before my fingers reached the bottom of her bra. "What are you doing?" she whispered to me. "I really want you, Nicole," I replied. "I have for years." Not only did I want to fuck my sister, I wanted to be the one to pop her cherry. I thought of it as my right and duty. At first I felt guilty about these feelings I had for her. But then I found something in my parent's collection of home videos that changed my mine. It was a swapping video of my parents. I had know they were swingers for a several years, but I think they thought us kids were ignorant of that fact. Perhaps the others were, but not me. But this one tape took me by total surprise. I had found a tape late one night the previous summer of Mom and Dad swapping with another couple which was simply titled "Denise." I had a habit of waking up in the wee hours of the morning and rummaging through my dad's collection of porn, most of which was homemade videos of the two of them with a few very close friends. I loved watching them. When I put the tape in and settle back to watch, I couldn't believe my eyes. The tape started with Mom laying across the top of the bed fingering her pussy, while Dad was naked sitting on the foot of the bed making out with another woman who was also naked. I assumed she was the wife of the missing man. Then the second man entered the picture, he was the one that started the recording. It was my uncle Rich, which meant that the woman Dad was my aunt Denise, Dad's sister! I sat mesmerized as I watched my dad fuck his sister and then leave her a nice creampie. It was this video that came to mind while Nicole and I were talking about how wrong it was for the two of us to be behaving in this way toward each other. And it seemed like Nicole was trying to argue herself out of the situation. So I kissed her again and when she kissed back, I laid her back on the sofa. We kissed for several more minutes and my hand finally reached her beast. It was soft to the touch, silky smooth, but firm at the same time. It was slightly more than a handful, and her nipple was hard against my palm. I removed my arm from around her waist and began to unzip my pants. The thought of fucking my sister overrode my desire to see Dad and Aunt Denise fucking. "No, wait," she said softly. I stood up next to the sofa and continued to unzip my pant. Nicole watched, but did nothing else. She was breathing hard, her breast rising and falling in beautiful concert. I hooked the waistband of my boxers with my thumb and slid them and my jeans over my hips and let them fall to the ground. My cock sprung out proudly. Nicole gasped when she was my stiff, erect member. "Matthew..."she whispered. I shushed her and reached under her skirt. I slide both hands up her thighs and found her panties. I gripped them in both hands and began to pull them down over her hips. Silently, Nicole raised her ass an inch off the the sofa cushion. I then slid them over her ass and down her thighs, past her knees, and finally over her feet. Nicole was breathing heavier now, and her eyes had the look of a woman who wanted a cock inside her badly. I tossed her panties behind me toward the TV. "I want you so badly, Nicole," I told her. "I want really want to fuck you." "I know," she whispered back, a tear forming in her right eye. "And I think I want you, but you're my brother." it was clear she didn't know what to do. Confused about her feelings and that we were brother and sister, she hesitated in letting me fuck her. But an idea came to me; I could show her that brothers and sisters fucking each other wasn't so strange. In fact, it was more common than she thought. I could show her Dad's incest swapping tape. "I have something to show you," I told her. "I think this will help." I walked over to the treasure trove of homemade porn and took out Dad's incest porn. I waved it in the air for Nicole to see. "What is it, Matthew?" she asked as I walked over to the chest next to Dad's recliner. "Is it one of Mom and Dad's homemade videos? I know all about those, and they're not going to help." She'd caught me watching the once, but she just turned and left the Den. She never told anyone that I watched Mom and Dad's fuck tapes. She knew I came here often and watched them when noone was around, or everyone was asleep. I walked over to the VCR and pushed it in. "Just watch this, then you can decide if it's a game changer or not." I turned and walked back to the couch and realized she was looking at my cock. "Sure you don't just want me to slide this inside of you?" "Don't be gross," she said with a serious look. I didn't believe she truly meant what she said so I shook it a t her.She rolled her eyes at me and I sat down next to her. I slide a hand under her skirt as the video started, but she didn't stop me from sliding my hand up her leg to her pussy. I just barely felt her pussy lips on my finger tip when she suddenly sat straight up. "Holy shit!" she exclaimed. "Is that Aunt Denise?" she asked. "Yup," I told her. "And Dad's about to fuck her." "No way," she said in disbelief. But she knew it was true. "Oh shit," she said softly when she realized Uncle Rick just joined Mom on the bed. While Nicole sat and watched as our parents swapped with our aunt and uncle, I moved behind her. I reached around and slid my hand down to her twat. I could feel the wetness of it and continued to slide my finger down her slit to her hole. She didn't say anything, just leaned back into me as she watch Dad and Aunt Denise making out. She just let me finger her as she watched the of Dad and his sister fucking like old lovers. She came a few times while watching the two of them, going at it. When the video was over, Nicole turn around and straddled my legs. She bent down and kissed me deep and long. After a while she pulled away, slid down onto the carpet. She looked me in the eyes and pulled her top off, then reached around behind her and loosened her bra. She then reached up and pushed the straps down over her shoulders and let the bra fall to the floor. She had the most beautiful breast: perky, firm and perfectly round quarter-sized areolas surrounding a stiff nipple. The she lay down on the carpet. The video seem to have made my point for me. "Come and fuck me," she said to me. I joined her on the ground sliding between her legs. I lifted her legs up over my shoulders and placed my cock in front of her swollen labia. Looking into her my sister's eyes, I pushed forward slightly the purple mushroom head of my cock slid past her swollen lips for the first time but I stopped short of sliding it inside of her. Nicole let out a long moan. I reached down and slid the throbbing head of my cock up and down her wet pussy several times then let it rest at entrance to her tunnel. I leaned down to kiss Nicole and she eagerly accepted my tongue. Then I impaled my sister with the shaft of my hard cock. Nicole nearly swallowed my tongue as my cock disappeared into her pussy. She was warm and tight. It felt as though Nicole's pussy was giving my cock a bear hug. I suddenly worried that I might be too big and I stopped, not wanting to hurt her. "Why did you stop?" she asked softly. "I thought maybe I was going to hurt you," I nearly whispered back to her. "I want you to enjoy it, not hurt." "Don't worry," she said, "it feels sooo good right now." She placed a soft kiss on my nose. "I know you've wanted this for a while, so take it." Instead of sliding the rest of the way into her, I pulled out slowly and pulled her down onto the floor with me. I took off her tank top and laid her back on the floor. Then she spread her legs and beckoned me to fuck her. As I guided my cock back into her pussy, Nicole wrapped her legs around my waist and pulled me toward her. I had wanted to get inside of her for so long, now that it was actually happening, I realized just how much I enjoyed the feel of her pussy over my cock. I also realized that it was too much; I was going to come very quickly. I didn't really care, I was finally fucking my sister, and it was euphoric. With long, slow, deep thrusts, I worked her up into an orgasm and then exploded. The orgasm was so intense I nearly blacked out, or, rather, there was a bright flash of light as my body tensed like never before. My balls quivered and suddenly there was an immense rushing feeling running through my balls and cock emptying deep inside of the warmest, tightest velvety pussy. Nicole yelped as I suddenly filled her with my seed with a loud roar. Then I collapsed onto my sister's chest and she held me there for several minutes. As I lay there on top of my sister, my cock slowly shrinking inside of her, cum dripping from her pussy, I could hear my parent's sex tape; it had auto rewound itself and started again from the beginning while we were fucking. I finally rolled off of Nicole and sat up against the sofa. My sister joined me seconds later laying her head on my left shoulder. We absently watched our parents sex tape as we sat there. "Tim is going to fucking you," I told her "I hope so," she said quietly. "But we can still fuck each other, right?" "Any time you want to, Sis," I told her, and I meant it. "Just like Dad and Aunt Denise." "How long do you think they've been fucking?" Nicole asked me. "Dad and Aunt Dee, I mean." She sat upright and looked at me. "Do you think that's why we're like this, why it doesn't bother us that we just fucked each other and want to do it again?" "Could be," I replied thinking about whether there was a gene that allowed brothers and sisters to have sex and not feel bad about it. "Do you feel bad about what we just did?" I asked, curious. I knew I should feel wrong about what just happened. I wasn't. In fact, I was very satisfied. It felt very natural to be fucking Nicole, even though she was my sister. She may have just told me she wanted to fuck again, and keep fucking each other, but I wanted to make sure she was okay with what we just did. "No," she replied after some thought. "I don't feel bad about it at all." She looked at me with a smile. "I can't believe I was so horrified by the idea of getting fucked by a hot guy," She leaned in and kissed me. "Do you think Tim might want to fuck me with you?" That took me by surprise. I knew he wouldn't have a problem sharing a girl with me, but I didn't know if I wanted anyone to know that Nicole and I were fucking each other. I thought he'd be fine with it though. But the thought of sharing her with my best friend, and the scene of my mother getting fucked by my uncle while Dad fucked his sister really turned me on and I began to get hard gain. "He'd probably love it, actually," I said as I turned toward her. "Now let's get back to teaching you how to be proper slut of a girlfriend. Let's practice blow jobs." It was a long night of sex, but I was sure that when Tim finally fucked my sister, he was going to be in for a little surprise. His good little Christian girl image of her was going to be shattered. First Time With Sister My sister is a 19 year old brunette. She’s about 5’10 with legs that don’t stop, a perfect ass and a medium set of tits. She didn’t hide her body from me at all and I think she knew I liked looking at her. My sister and I weren’t really close when she hit 14, she didn’t like when I was watching her, admiring her budding body. She did like teasing me though. She’d always bend over in a low cut tank top giving me a view of her milky white tits or short shorts giving me a view of her panties. Each time I had to run to the bathroom to jerk off and she knew it. One day she caught me jerking off in the bathroom, I didn’t think anyone was home so I left the door unlocked. I was standing there stroking my cock thinking about cumming on her and she stood there with a look of shock on her face when I started blowing my load and said her name. I heard her gasp and I turned to her and blushed and she ran from the doorway. I cleaned up and pulled up my pants then went to her door. I knocked and she said “come in” so I did. She was sitting on her bed and wouldn’t look at me. I told her I was sorry and she said she wouldn’t say anything. I said thanks and left her alone. A few weeks later I was taking a shower and she was home. She knocked on the door and said it was an emergency, so I opened the door. She ran over to the toilet and pissed so loud I could hear it over the shower. I heard it flush and thought she would leave. I kept showering and didn’t think of her still being in there until I heard the curtain open and felt two tits on my back. My cock started growing and she whispered in my ear “I see my big brother is getting a hard on for me.” She kissed my neck and gripped my cock. She started stroking it until it was completely hard. She told me I had a beautiful cock and came around my front and kissed me deep and hard. I felt her tongue slip into my mouth and she sucked on mine. I squeezed her ass and felt her bare pussy on my cock. I didn’t know she shaved her pussy but what a great surprise! She told me we should get out of the shower and I quickly agreed, we dried each other off and she led me to her bedroom by my very hard cock. She sat on the edge of her bed and pulled me close by my cock. She kissed and licked the head and then my balls. Always the tease. She stroked my cock and asked me if I had been waiting a long time for her to suck me off. My answer was, of course, yes. She quickly took my cockhead into her mouth and sucked on it. I was in heaven as my sister gave me a terrific blow job. I told her I was about to cum and she pulled off and told me she wanted my hot load on her tits. I happily obliged her and sprayed her tits with cum. She moaned in pleasure as I did this. I then laid her down and spread her legs. I slowly licked her very wet pussy lips and she moaned in pleasure, I found her clit and sucked it, she came very quickly. I asked her if she had ever been fucked and she said “no.” I was so hot then, I got to be the first person she gave head to, the first person that came on her, the first person who licked her pussy and now the first one to fuck her tight little cunt. I pulled her legs up and put them on my shoulders and guided my cock into her pussy, it was like a vice. She winced as I broke her hymen, but got used to it very quickly. She started moaning very loudly and begged me to fuck her. I pounded her tight pussy and she groaned and came multiple times on my cock. I felt my cock starting to throb and swell in her cunt and told her I was going to cum. She quickly slid off and sucked me off to a fabulous orgasm. Since then she sneaks into my room to suck and fuck me every night and we do it every time we can. We’ve fucked almost everywhere. She’s a terrific fuck now and can’t get enough cock. First Time with Sister in Law I am in my late 30s and my sex life is pretty much dead with my spouse. I do venture out occasionally to meet with an independent escort who fulfills my needs. My wife and I made the cardinal mistake of going into business with her sister and brother. My sister-in-law is a few years younger than my wife, cute and has a nice body. Her kids have taken their toll, but she still has a rack to die for. I would assume they are at least a 36D...maybe more. She also wears lovely thongs all the time. I sneak a peak when I can and have even masturbated while sniffing them a few times. Needless to say, I would love to get my hands on her body and take advantage of her awesome tits and most likely lovely pussy. Anyway, to get back to the story...we are in business together and they have recently hit some hard times. Of course my sick mind took over when I heard this thinking how can I leverage this to my advantage. I was thinking I could use my escort money to help them out, but wanted something in return. The question was how to approach my sister with my nasty plan without getting in trouble with my wife and ruining my marriage. My sister in law and I have flirted at times, but nothing serious so I knew I might have a shot. She also had mentioned that her sex life was very empty because her husband traveled a lot and when he was home was always tired. I invited Lisa out to lunch to put my plan into motion. She showed up wearing a nice little sun dress which accentuated her large tits. I could see a sexy bra underneath and was assuming there was a hot thong underneath...or better yet nothing. We ordered some wine with lunch and she was very talkative and told me more details about their financial needs. Basically my escort money could take care of them with some left over. When I knew she had had enough wine to loosen her up, I started to tell her that I could help in return for something for me. She had a worried look on her face. I told her it wasn't that bad and explained that I would pay her a sum every time we met and that we would need to meet five times a month to meet her new financial obligations. Her first response was that she wasn't a whore and that my wife would be devastated if she found out. I told here she wasn't a whore and that I was only trying to help us both out...plus take care of both of our sexual needs. That seemed to strike a cord with her and she agreed to at least try it and see what developed after that. We went back to her house and sat on the couch. I asked her to get up and strip for me. It was a little awkward at first, but she came around and started getting into it. She slipped off her dress and started playing with her big tits...licking and pinching the nipples. She then told me...you want to see your slut's pussy...and I went nuts. She danced around in her little thong and finally bent over in front of me and slipped it off. I didn't see a snippet of hair and knew I was in for a treat. I love to eat pussy and shaved pussy is the best. I had her join me on the couch and we proceeded to kiss...awesome, deep, French kisses. I finally got my hands on those tits and sucked them like I hadn't eaten in days. She had the longest nipples and they were very responsive. I laid her back on the couch and kissed my way from those tits down to her lovely, shaved pussy. I passed by and kissed down her legs. She was begging me to eat her and give her some release, but I had other plans. I sucked on her carefully painted toenails and her lovely calves. I then worked my way back up to my feast. I started licking the outer lips and then worked my way inward avoiding her clit. She was pulling on my hair talking dirty and really enjoying the attention. It must have been weeks since being eaten out last. I pushed her legs up and licked down her "taint" to her lovely ass bud. I proceeded to lick her ass and stick up my tongue in it for a few minutes. She was going crazy wanting to cum. I licked my way back up and asked her what she wanted. She told me she wanted to cum all over my face...and I was totally up for that. I attacked her clit while I put two fingers into her tight pussy. She locked her legs on my head and was ready to explode. I nibbled and licked her clit while working my fingers in and out of her. She convulsed and had a huge orgasm. I kept licking while the waves continued to grasp her. I rose up and kissed her again. She was licking my face tasting her sex and basking in her glory. When she got her composure, she pushed me back onto the couch and pulled on my belt. She then reached out and pulled out my messy cock. I leak lots of pre-cum when I am giving oral...it almost gets me off. She said she loved my tool and said it was a bit longer and thicker than her husband's. My brother said that her oral skills were lacking so I wasn't expecting much. I was pleasantly surprised. She attacked my cock with great skill while staring at me while she sucked me. I wanted to get my cock in between those big tits and she read my mind. She wrapped them around my cock while she sucked the head. She had me almost on the verge very quickly. I didn't want to waste my load yet, so I pulled out and put her back on the couch. I had her bend over the couch and teased her pussy with my swollen cock. I told her to tell me what she wanted and she said, "Fuck your whore sister in law with that big cock." I totally obliged and as I slipped it in all the way until my balls were slapping her ass. I reached around and pulled on her nipples as I fucked her. She was screaming and loving it. I pumped her for all I was worth until she started to tense up for her second major orgasm...that put me over the edge and I filled her with my huge load. I flipped her around and had her lick off the remaining cum and her juices off of my cock. It was the first of our new business deal...only time will tell what the future holds....