Hey guys, I know I said in Chapter 3 I was gonna wait a while before posting 4, but I had a couple ideas I wanted to write down, and before I knew it, all of Chapter 4 was completed. I guess just like many of you, I can’t wait to see what happens to Sam and Ryan :)
I received a lot of ideas about what I could incorporate in the story, a few of you had some good ones, but unfortunately the storyline for Ryan and Sammy is set with milestones that have to be met, so details can change but plot cannot. I did take a few ideas and add them to the story, just not in the exact way they were given to me. Hopefully it adds a better quality to my story :)
Just a heads up if you’re unfamiliar with my writings, my stories are just that: stories. They do contain plot, not just sex, so please bear with me if you are impatient. Once again, due to comments I have received, I feel obligated to let you know that this story details the sex life of a 16 year old boy and his 11 year old sister, however this is just a work of fiction, and no part of it is based on any people, places, or events that have occurred in my life. Enjoy :)
My birthday is in a few weeks. I can hardly wait. Seventeen years old. Yeah it probably isn’t much different than sixteen, but then I’ll be able to go into R rated movies by myself and buy my own video games. It’s a big deal to me. And I can hardly wait because I’m sure Sammy will make it extra special.
For those of you a little lost, my name is Ryan Brooks. I know a lot of you know my story, but I’m going to repeat it briefly. In a lot of ways I’m confused but nevertheless happy with what my life has turned into. About seven months ago, my parents got a divorce. A lot of kids find that traumatizing, but to me it was a relief since all my parents did was fight. My sister and I now live permanently with my mother, since my dad never filed for partial custody.
Then a little less than two months ago, my mom decided she wanted to go out and have fun, meet new men and hopefully find a new soul mate, if there ever was such a person you could meet going to bars on a Saturday night I have never heard that fairy tale. But it meant I was going to have to start babysitting my sister, Samantha, on those nights she was gone. Without giving too much detail, one thing led to another, and it has made my weekends filled with sexual acts between my sister and myself. Samantha’s birthday is just a little over a month away from mine so she’s just shy of twelve.
To catch you up on what you’ve missed, it’s been two weeks since I promised my little sister that I’d be the one to take her virginity. Honestly I think both of us are really anticipating the opportunity, but true to my word, I want it to be safe, for both of us.
My name is Ryan Brooks, and this is my story.
A few things have changed over the last couple weeks. Jeremy is over more often. I am fortunate that they choose to still go out on Saturday nights, but honestly having Jeremy around all the time is kind of annoying.
My mom wants me and Sammy to get to know her new boyfriend, she says that he might be a part of the family someday and she wants us to get comfortable being around him. I think me and Sam both realize that we have almost nothing in common. Oh well. I’ll just play the part and my mom will be satisfied.
This has hindered Sam and I from having our sexual encounters during the week as we had planned and I’m beginning to feel really frustrated. Since the one time me and Sammy were able to mess around in her bedroom with my mom downstairs, we have tried during weekdays after school, but with Jeremy around it’s not happening as often as I would like.
As for my promise to Sammy, I deeply want to fulfill it, but I still don’t want to risk pregnancy. When I think about it, all it would take is a simple denial from me and I have no responsibility to care for a child, but it wouldn’t be fair to Sam, and I feel it would be easier to just avoid the problem all together. Sammy’s friend Kylie is now supplying her with the pill, but I would still rather use a condom, since I heard that even with the pill there is no guarantee that she won’t get pregnant. But where would I get condoms? My dad had always been the one to hand me those. “Better safe than sorry kiddo”
This is a shortened version of all the thoughts that were in my head as I walked home from school Friday afternoon. Along the way I passed a pharmacy. Would they sell condoms to a sixteen year old? Maybe if I told them I was eighteen? But then what if they asked for an ID? Wait isn’t there a law that says they HAVE to sell them if I ask for them? Am I being too paranoid?
I didn’t stop long and continued walking. Once again, the better solution was to just avoid the situation all together. But it didn’t solve my problem.
I got home and let my backpack drop by the door.
“Hey sweetie, hurry up and shower, all of us are going out to dinner tonight.” Mom was washing dishes over by the sink. “Alright mom” I called off and trudged up the stairs. I must have been making a lot of noise because as I passed my sisters room her door opened.
“Hi Ryan. Are you ok?” honestly I was feeling a little sick. A whole day with just me and my thoughts as teachers babbled on about equations I didn’t feel were worth remembering and laws of science which I’m pretty sure no one cared about seemed to be a potent concoction for sickness.
“Yeah I’m fine, just got a lot on my mind,” I replied trying a vague smile. She glanced down the stairs and moved forward to give me a quick kiss. “Is there anything I can do to make you feel better?”
“Right now?” I looked down the stairs half expecting my mom to be standing there eavesdropping. Maybe I WAS getting too paranoid. She smiled at me and tugged on my hand.
“If I heard right, you have to take a shower. Come on I’ll help you right now and then you can help me later. You’re not scared are you?” she winked at me and then she led me to the bathroom and I could not help but give one last look back at the stairs to make sure they were empty.
Once inside Sammy closed the door and locked it, then turned on the shower water.
“There we go,” she turned and smiled at me. Now that I felt safe, the familiar rush was coming back. Sammy, all mine, right here in front of me and we were alone. I leaned down and kissed her, she returned my kiss and wrapped her arms around my neck for a few moments, then she trailed her hands down and unbuttoned my jacket. I tore it off suddenly feeling like my clothes were on fire, and as she started unzipping my pants my pulled my shirt off over my head and tossed it on the floor. I leaned back against the sink and watched Sammy pull down my pants and then my boxers right after.
As soon as she had open access, Sammy began using her hand to work my shaft, and gave an almost “purr” of delight as it grew to its full length under her touch. She used her lips to move back and forth on the side and I tilted my head back giving a silent gasp. She was teasing me and she knew I couldn’t do anything about it, so she began flicking her tongue along the head causing a little bit of my precum to hang from her lip and on her chin. It was a very sexy sight, my sister grinning with my cock in her hand and a little bit of precum dribbling on her.
After an agonizing few minutes of teasing me in this fashion, she finally took it in her mouth and bobbed her head back and forth a couple times, keeping her lips sealed tight. I groaned quietly, hoping the running shower water was enough to cover the noises we were making. I put my hand on top of Sam’s head and stroked her soft silky hair as she continued her business with my dick.
I could feel my balls clench and knew I was close to cumming. Sammy sensed it too and worked moved her mouth even faster over my shaft, taking care to run her tongue up and down as she was doing so. I was struggling to hold my load in, letting it build up as much as I could, but I finally burst and gave my sister a mouthful of cum. She continued sucking my cock more, getting every last drop and using her finger to scoop up what little had been forced out of her mouth.
“Mmm I love your cum, brother.” She stood up and kissed me deeply. Strangely, it didn’t bother me even though I knew she had just swallowed my cum. I was still very horny and slipped my hand down her shorts and I could feel her pussy, already wet. It was pretty evident that she was extremely turned on.
“Sammy!!” a loud call came from somewhere outside the world Sam and I were in.
“Fuck!” Sam exclaimed as we broke off our kiss. I was pretty pissed off too. “You’ll take care of me later right?” she asked as she straightened her hair out and fixed her shorts.
“Of course,” I replied, pretty annoyed at having been interrupted in the midst of our playtime.
“Good, now go take a shower dirty boy,” she gave me a quick peck on the cheek and hurried out the door, leaving me standing there naked and hard.
“Just my luck” I muttered before stepping into the shower and making the water cold.
An hour later I was clean and dressed in decent clothes since we were supposed to be going to a nice restaurant. Jeremy was down stairs lounged in the love seat, my mom hurrying around making sure me and Sam were socially acceptable.
“Now Sam good behavior understand? This is a nice restaurant so don’t be fooling around” She gave her a stern look to show she meant business.
“Yes mom sheesh, you act like I’m going to start a riot.” Sam rolled her eyes, just like I had seen her mother do several times.
“I don’t know about you sometimes. And don’t roll your eyes like that.” She turned her attention to me, “ Ryan, you’re old enough I shouldn’t have to tell you how to behave.”
“Got it,” I replied as I tucked in my undershirt.
We left our house in Jeremy’s car and hopped on the freeway. Sam and I were mirror images in the back seat, staring out the window utterly bored. I glanced at her and saw she was wearing a skirt. I thought of all the times she had teased me while we were having our fun. I smiled to myself and stared back out the window watching all the cars pass us by in the fast lane. Maybe dinner wouldn’t be so bad after all.
The restaurant was of Venetian décor (don’t ask me what exactly made me note that) and served Italian food, which I am actually a huge fan of, but tonight a delicious chicken parmesan was the last thing on my mind. The lighting in the restaurant was pretty dim, which I guess is supposed to be “fancier” but I did appreciate it all the same. We requested our table, which we had reserved, and still I was stuck waiting for about ten minutes with nothing to look at but a bunch of pictures of Italy and the Canals in Venice. Not that it wasn’t beautiful, but I found myself becoming more and more impatient to start my games with Sam.
We were seated at a booth near the wall closest to the parking lot, which provided a lovely view of, well, wall. Jeremy and my mom took their seats on one side of the booth and I allowed Sammy to enter the booth first, ensuring she would be trapped between me and the wall. A waitress came by and took our beverage orders. Once that was taken care of, mom and Jeremy decided to turn their attention towards me.
“So Ryan, almost your last year of high school. Any idea what you wanna do?” Jeremy asked with apparent interest, although I can never tell if he really cares or if he just wants to look good for my mom. Under the table I slowly “walked” two fingers over to Sam’s leg and placed them on her thigh over her skirt. She snuck a questioning look at me but didn’t say a word.
“Well to be honest, I’m looking to do something with engineering. I took an auto shop class this year, and next year I can be a part of the ROP program which should help me find a job.” I kept my words even, loving the fact I was in control. I tugged up Sam’s skirt balling it up in my hand so I didn’t have to reach down too far. She shot another look at me and tried to push it back down without being too obvious.
“Oh that sounds good. I never took a class but my old man taught me a lot of what I know about cars. Did you know…” I was looking right at him but tuned his words out. I slowly allowed my fingers to brush the inside of Sammy’s thigh. She gave an involuntary jump and banged her knee on the bottom of the table.
“Sammy, are you alright?” My mom looked at Sam, but it was with more of an apparent concern that the night should play out smoothly.
“Fine mom. I just uh thought I felt a spider web underneath the table.” Sam’s voice faltered a little and my mom fired a “you better not make a scene” look in Sam’s direction. Mom turned to Jeremy and started telling him something about the way we used to act when we were out to dinner as little kids. Now with the two of them not even paying attention to us, I reached over more and grabbed a hold of the thing piece of cotton panty that separated me fingers from Sammy’s pussy. Pushing it up so my hand was in between, I began rubbing circles in between her legs. I felt her close her legs automatically and give a deep intake of breath, but my hand was already there and I continued my silent probing of my sister’s mound.
“Okay so who got the Pepsi?” my hand shot out quick and Sammy flattened her skirt hastily as the waitress came back with the drinks. With the drinks passed out, she took our orders and then our waitress vanished to the back. Sam looked at me already knowing I was thinking of going back and mouthed the word “Why?” I did my best to put on her trademark grin, shrugged, and whispered so only she could hear, “You’re not scared, are you?”
Without another word my hand disappeared back into her panties and I could feel she was soaking wet. As soon as I began rubbing again she did her best to sit up straight and pretended to be interested in a desert menu. I pulled out my phone and started opening random folders and apps, while the whole time rubbing my sisters pussy just a foot away.
I decided to take it a step further and pushed a finger inside Sammy’s slippery hole. I saw her bite her lip hard and she glared at me, but I could see just beyond that glare, there was a huge amount of lust in her eyes. I started moving my one finger in and out. She closed her legs again, but I was already penetrating, and I could see her struggling to not moan out. The best part was her pussy was practically gushing with wetness and I swear I could hear small noises as I moved in and out. Her thighs began to quiver and finally she blurted out, “Mom can I go to the bathroom?” Jeremy and my mom both looked at her. I continued to rub her while I could since I knew she was about to get away.
“Well yeah Sammy, you don’t have to ask permission, just ask your brother to move.” I put on a biiig smile showing off my teeth and waited for her to ask. Another lust-filled glare.
“Ryan, move please,” I scooted out of the seat and bowed slightly as she got out of the booth. “But of course, Madam” and as she walked away towards the bathroom, I could clearly see some of her wetness had spread onto her legs, and she adjusted her skirt as she walked to try to hide this. I sat back down on the booth and looked onto the seat next to me I could see a wet stain. I laughed to myself and wondered whether I should clean it or not. I decided the latter and waited for Sammy’s return.
She came back about five minutes later and sat down without a word. Under the table she passed me something, and I realized instantly what it was. It was my sisters panties, covered in cum and I grinned at her before tucking them away in my pocket. I didn’t care if the pants got stained, all I know is the fact that my sister had just gotten herself off in the bathroom just on the other side of the room we were in was a complete turn on. I was getting a bulge in my pants, but I knew I could do nothing about it until tonight, so I tried to focus on dinner. It lasted far too long for my liking.
We drove home in the dark. Mom and Jeremy were chatting like they always did, and a seat away my sister stared out the window. I couldn’t resist and I lifted up her skirt. Even in the dark, I could vaguely make out Sammy’s pussy, and I was horny beyond belief. I wanted Jeremy to speed and get us home quickly, but obviously he was driving in the slow lane for whatever reason again.
We got home and my mom announced that Jeremy was spending the night. (This wasn’t the first time but I still wasn’t exactly used to it) she just told us to keep it down and make sure we got a good night’s sleep. She put her purse on the counter and went upstairs, leaving Sammy and I alone. It wasn’t for very long, however, Sammy went upstairs to her room to change and I went to mine.
As I was undressed down to just my boxers, I wondered if I could even go see Sammy tonight. My mom’s bedroom was right across from hers, and even if she and Jeremy were doing the do, there was no guarantee that she would be oblivious to me sneaking up there.
“Bastard,” I turned around to see my sister standing in my doorway. She crept forward closing the door behind her. She set something on my dresser but I couldn’t tell what it was because it was so dark.
I grinned in spite of myself. “I think you forgot these?” I pulled out her panties and tossed them at her. Then she too smiled.
“The only reason I’m mad, is you promised you’d take care of me, but instead, I had to do it myself.” She moved forward and wrapped her arms around me kissing my chin. “But now is your chance to make it up to me”
I held my prize in my arms and kissed her lips deeply, which she returned passionately. Even an hour later, I was still just as turned on as I was at the restaurant. She pushed me down on the bed and carefully stepped out of her shorts and crawled up on my bed. She apparently still hadn’t put on any panties and she mounted my face not giving me time to prepare. I felt suffocated, only able to breathe in the scent of my sisters sweet cunt, and at the same time more turned on than ever before. I quickly recovered and grabbed my Sam’s thighs holding her down as I pushed my tongue inside her and brushed up and down her cunny. She ran her fingers through my hair and started speaking dirty to me.
“Mmm that’s right, this is for not taking care of me, almost making me cum in public like a whore!” Her voice was getting me riled up more and my tongue worked her more determinedly. She began moving her hips back and forth, essentially riding me. She whispered more words to me but I was beyond myself. It was almost an out of body experience, and the scene I was playing a part in was too good to be true. I had never tasted anything as delicious as my sister’s cunt, still strong with the taste of her orgasm from before.
Finally I felt the normal quivering in Sammy’s thighs which signified she was close to cumming. I put her clit between my lips and sucked the way I knew she liked. She put her hand over her mouth to muffle her loud moan as she climaxed all over me and my bed. She kept her hip motions going which smeared a little around my mouth, but I was never all too concerned with sanitation.
I thought my oral services were over, but she had more plans. “That made up for the blowjob, but I told you I would make you regret sneaking up my skirt.” She turned around and repositioned herself on me. “Lick”
I knew immediately she was talking about her asshole. I hesitated for a brief second, then pretty much had a “oh what the hell” moment and allowed my tongue to make contact with her anus. It was not nearly as bad as I thought it would be, and I think the mere thought of how dirty this was actually made my boxers even wetter. She was making small noises of pleasure and pulled her cheeks apart to allow my tongue easier access. She bounced up and down slowly making sure my tongue was brushing against her the whole time, and after a few minutes she turned around and laid on me kissing me sharply.
“Now I think we’re even” she licked my ear slightly and then said, “go get what I have on the dresser.” I got up and crossed over to my shelf. I smiled when I realized it was our sex oil. I turned around and she was on all fours on my bed, wiggling her ass at me and giggling a little.
I pulled my dick, which had been begging attention for hours now, through the hole in my boxers and carefully spread it around her anus, and pushed a finger in her ass for good measure. She sighed her delight and shook it back and forth for the entirety, enticing me more to push my cock inside her.
Finally, when I thought she was well lubed, I took my position behind her and began pushing in. She gave a squeal of pleasure, then reached over and grabbed a pillow. As I began my small thrusts into her ass, she buried her face in the pillow to keep quiet, but I could still hear the noises she made and it was a complete turn on.
Teasingly I spanked her ass sharply, and I was surprised to hear her let out a quick moan. I did it again and she made the same noise again, this time mixed in with an “Oh big brother…” so I soon started thrusting a bit more and would every once in a while give her a quick smack, inciting the same moan every time.
Pretty soon Sam’s anus started to loosen up and I moved with more ease. I was still unwilling to move as fast as I could, but I quickened the pace and Sammy’s breath fell short, each of her pleasure noises coming out with her gasps. The combination of events that occurred during my heated evening meant I wasn’t gonna take long to cum, and I knew it. As Sammy’s ass muscles pressed on my dick I felt the familiar stirring and prepared to cum. I hastened the pace, pulling Sam’s hips back to meet my every thrust, and her gasps soon became one long continuous muffled moan.
I pushed my cock in balls deep and Sam lifted her head up almost forgetting herself for a second before covering her mouth to groan loud. Cum poured into my sister’s ass and began to drip onto my bed. Sam moved forward to let me out with a pop, and then lay on her stomach facing me and began licking up the fluids that had dripped out onto my bed sheets.
Sam then got on her knees and pulled me close to her, and I kissed her forehead slightly.
“Can we tonight Ryan? I’m on the pill, isn’t that enough?” I thought carefully about my answer.
“Sammy, you know I wanna wait til I can get a…” I trailed off mid-sentence as one innocent act at dinner replayed in my mind. “Wait one second, I’ll be right back” I hurried and threw on a pair of gym shorts and left my room, leaving behind a bewildered Sam. I stepped lightly into the kitchen and on the counter was the possible answer to my problem; my mom’s purse.
Now I don’t normally go through my mom’s things, but I really wanted tonight to be the night for Sammy and me, and there was only one hope I had. I dug through my mom’s purse and came up with what I was looking for; Jeremy’s wallet. I silently thanked him for putting it in my mom’s purse and then most likely forgetting about it. I flipped it open and on the inside sleeve, sure enough, he had about three or four condoms.
I took one, not caring if he would notice or not in the morning, and glided back to my room. Sammy was waiting on the bed. I triumphantly held up the thin square and crossed over to her. She kissed me again, much softer than before, wrapping her arms around my neck.
“So tonight Ryan..?” She whispered.
I nodded my head. “Tonight”
We kissed again, and this time I laid her down gently. I slipped on the condom as I had done several times before, but this time I felt a little nervous. I relaxed easily though as Sammy opened her legs, allowing me to lay between her and brought me down for another kiss as she rubbed her hands up and down my back. This was my first time truly noticing that I was beginning to care more and more for Sammy.
Taking her hands in mine and carefully pinning them by her head, I pushed the tip of my dick just past her opening, and her lips parted as she inhaled and held her breath. I had never been with a virgin before, so I was extra careful I slowly began probing and penetrating my sister. I could only get my dick so far in before a grimace would appear on her face and she would whimper a little.
“Please don’t stop brother, please, please give me everything,” and although I was concerned, I did as she asked, pressing my dick forward and taking my sister’s virginity. She cried out loud but I silenced her with my lips, and she kissed back still whimpering but I held it inside her, letting her body adjust to the foreign object penetrating her.
I could feel her body slowly relax and I didn’t stop kissing her until I knew she was at total ease. Still being cautious, I pulled myself partway out of Sam and then pushed back in. The change in her voice was obvious, and I knew now that she was getting used to it. Choosing a slow rhythm I began moving in and out of my sister, and she wrapped her arms around my neck and held on tight as she received her first fuck. She opened her eyes to look at me and I could see her shock and awed delight, and I began moving a little bit faster, still trying to be mindful of her sensitivity.
Sammy held on and eventually, started moving her hips towards me meeting every motion of mine as best she could. Her breath became shorter, as did my own and I knew both of us were close to cumming. I came first, forgetting in a moment that I was her first and pushed in a little further than I had been. The noise she made was an odd mixture between a moan and a squeal of pain, but then her body shook and I felt her pussy clamp down as she climaxed and lifted her pelvis up towards me.
A couple of seconds passed with us panting for breath, and then my sister wrapped her arms around me and pulled me into the most passionate kiss I had ever shared with her. I closed my eyes and it felt so natural that I let my senses take over as I slid over next to her.
After a long moment our kiss ended and our lips pulled away gently. “Oh big brother… Thank you so much” I pulled off the condom and put it in the trash can, hoping I’d remember to dispose of it in the morning. She curled up and intertwined our legs, and at that moment I didn’t notice or care that Sammy wasn’t upstairs in her bed where she should be, that if anyone walked in right now, I’d be in the biggest, most fucked up situation of my entire life. I didn’t care that the room was chalk full of evidence of the actions me and Sammy hand undergone. All I cared about was Sammy, and the world that we were in where no one else existed. No thoughts, no negativity, no regrets, I simply enjoyed having Sammy in my arms, in my bed, and before I knew it, we had both drifted off to sleep.
Thanks for reading once again, hope you enjoyed the story, please comment and rate, and once again I love reading comments, positive or negative so be sure to give feedback. I still consider this my first story so I am always looking to improve, thanks everyone :)