My Sister catching me jerking off was just the start
One thing you learn growing up in a large family is that privacy is non-existent. Living with my Grandmother, two uncles, two aunts, and my three sisters in a half-duplex; privacy was a myth. With the three of us boys sharing one bedroom, night time activities were impossible. Trying to toss off a quick load in the bathroom was futile. I think the longest time I was ever in there was ninety seconds before someone was banging on the door to “Hurry Up!” You might find a secluded spot outside if you wanted to take a big chance. Summertime, everyone in the neighborhood was running around and could catch you at any moment. Wintertime, you would freeze your balls off.
My golden moment came one summer afternoon when I was sixteen. Grandma and Grandpa headed off to a family gathering downstate. Despite their protests, my aunts and uncles were dragged along as well as two of my sisters. My fourteen year old sister Mary had a softball game that afternoon, and had to stay behind. Since I had a paper route each morning, Grandma decided if I stayed behind to watch Mary, they could head out early in the morning. So as soon as Mary left at 11AM, I had the house to myself for a good 4 or 5 hours. Plenty of time to snag a couple of girlie magazines out of my Grandfather’s stash and jerk off five or six times.
So it was that I was stretched out on my bed, naked, flicking through a porn mag with one hand, and jerking myself lubed dick with the other. I had an average six inch cock with a large set of balls, probably from not draining them enough. The room was filled with the sound of my hand going “Whack, Whack” as I spewed filthy remarks at the girls in the photos before me. “Spread your pussy, baby. Let me eat your twat. Suck my dick and I’ll gag you with my load.”
I was so intent on getting my first load off, I did not hear someone coming into the house. I closed my eyes as the first marvelous load of cum shot out of my dick onto my chest. I continued to milk the last remains out of my spent dick. When I opened my eyes, my sister was standing beside the bed with wide eyes. “What are you doing?” she yelled. Pissed off that she came into my room without knocking, I yelled back “Jerking off, busy body.” I made no attempt to cover up, she had already seen it all. I wiped the cum off my chest with some tissue. Standing up, I towered over her. I warned her “Tell anybody about this, and you’re dead.”, usual big brother threat style. Then I noticed she wasn’t looking at my face, but staring at my cock. I sat back down on the bed, and she plopped down beside me uninvited. It was a little strange sitting on the bed naked with my sister still staring at my crotch, strange but exciting too.
“Look, Sis” I said “Really, please don’t tell anybody about this. We would both get in trouble. Besides which, you’re not even suppose to be here.” Finally looking at my face, she advised “The game got called off because of rain.” She picked up one of the magazines off the floor and thumbed through it. “Is this what guys like?” she asked. I said “Yeah, some guys. Some like other things.” She then pointed to a picture of a woman and a guy in a 69 position. Pointing at it, she asked “What is this called?” I told her, and asked “You probably know all about this stuff from school, don’t you?” She replied “No, they told us a little about intercourse, and some of the girls talk about things boys do, but I don’t believe anything they say.”
She leaned over close and asked “Can you tell me what boys like from girls? Not the stuff Grandma says about Church and families, but what guys want to do with girls when they get nasty.” I figured I had nothing to lose at this time, so I shrugged and started. “Guys just want to get their dick inside of a girl anyway they can, and get their load off.” She blushed and continued, “You mean have intercourse, put their penis in the girl’s private area and make a baby.” “No,” I said “ guys aren’t look to make a baby, they just want to fuck. They want to stick it in your pussy, up your ass, in your mouth, between your breasts, hell even behind your ear if it would get them off.” She looked at a little shocked but I didn’t know if it was because of my abrupt language or the thoughts I conveyed.
She looked down and muttered, “I didn’t think there was anything other than intercourse. Tell me more about those other things. What are they like, what do you like?”
For some reason, sitting naked on the bed with my younger sister discussing these things did not seem weird. In fact, my dick was starting to rise. “Look, there are a lot of things that guys and girls can do together. All guys like fucking, putting their dick in the girl’s pussy and jabbing in and out until they cum. But we are afraid of getting the girl pregnant so there are alternatives.” She nodded “Yes, the teacher told us about condoms but said those are for married couples who want to wait before having a baby.” I chuckled, “Teachers don’t tell you the truth about sex; they want to scare you away from it.” Now my cock was sticking straight up, and I noticed she was taking quick glances at it when she thought I wasn’t looking.
“Look, Sis. You promise not to tell anybody about any of this, and I will tell you everything.” She nodded her agreement. “The best thing is putting the guy’s dick in the girl’s pussy and fucking.” I emphasized this by making a sign of one finger thrusting into the circle of another. I continued “But that is how girls get pregnant. Now, condoms can prevent it, but boys our age can’t buy them. You’re too young to be on the pill, and pulling out in time is not safe.” She stopped me to ask “Does it hurt?” I replied “The first time when you get your cherry popped, it will hurt a little. After a short while, it feels great. The next time, it doesn’t hurt at all.”
She looked at me and asked “Well, what other ways can we do it. I mean boys and girls do it.” My dick jumped as I realized where this could go. “Guys can fuck girls in the ass.” She winced a little at that and crinkled her nose. “It’s not dirty or anything, but it will hurt a little each time until you relax. Sometimes, people just dry hump. The guy lies on top of the girl and just rubs his dick on her pussy until he cums.” She stopped me and asked “What do you mean cums?” Sighing, I continued “When a guy gets excited, his dick gets hard and larger.” Pointing, she said “Like you are now.” I nodded and continued, “if you rub a guy’s dick long enough, the white stuff you saw earlier will shoot out. That is the best feeling.” She asked “Do girls cum?” “Sure,” I said “but it is different. They don’t shoot out the same way, but they get the same feelings. Now, some girls let guys rub their dicks between their breasts to get off. Sometimes the girl will use your, I mean her, hand to rub the guy until he comes. Some girls even use their mouths to suck the guy off, a blowjob. Next to fucking, guys like blowjobs best.”
Reaching over, Mary placed her hand on my dick and rubbed in a circular pattern. “Like this”, she said. “No, here let me show you.” I said as I took control of her hand. “Wrap your fingers around the shaft and move it up and down like this.” She complied as my hand guided her. It was great, first time someone other than me had touched my meat. “Just keep jacking it up and down.” I instructed.
As good as it felt, it was a little dry. I told her “It is easier to do if the shaft is wet. Lick it with your tongue to get it wet as you move it.” Obediently, she leaned over further and tentatively flicked her tongue on my dick. I moaned at the touch, and she seemed encouraged to lick more. “Now, that doesn’t taste so bad, does it?” She shook her head no. Encouraged to proceed further, I said “Remember what I said about a blowjob? Just open your mouth and slid your lips down on my dick.” She lifted her head and gave me a blank stare not understanding. I took her other hand and told her “Pretend your finger is my dick and I am you.” I proceeded to suck her finger into my mouth like a mini dick. I moved up and down it, and swirled my tongue around it. I drew back and flicked my tongue across the tip of her finger before plunging down on it again. Inspired by my demonstration, she lowered her head to my crotch and wrapped her lips around the head. It took all my will power not to blow my load immediately. Her closed lips inched down my shaft as my dick proceeded into her mouth. She gagged a little and I told her to back off a little until she got use to it. I had to admit she was a quick learner. I encouraged her by telling her how great it felt, and giving her instructions on covering her teeth. She took to gobbling dick like a natural slut. The drool escaping from her mouth tickled as it coated my balls.
I noticed two things now, she was murmuring her approval of dick sucking and was using her other hand to reach down and rub between her own legs. Now I was encouraged by this to push it a little further. I pulled her up causing my dick to fall out with a “plop”. Drawing her face close, I pressed my lips to hers. With a little pressure, I was able to get her to part her lips and allow my tongue to enter. She moaned her approval. My hands were not idle as we Frenched. I pulled her shirt up and pulled her bare chest against mine. When we broke the kiss, she was panting and wide eyed. I leaned down and sucked one small nipple in to my mouth. She moaned a little as I swirled my tongue around it. When I switched to the other nipple, I reached down with my hand to rub her crotch but had to move her own hand aside. Words were no longer necessary as we each acted instinctively. I knelt to pull down her shorts and panties. Taking a deep breath, I got the aroma of her aroused pussy. She lay back and pulled her knees up to allow me full view of her pussy. I reached out and spread the pink lips to look right into her hole. I reached out and slid one finger into the juices of the desire. My finger found her hole and quickly sunk in as far as the first knuckle. She moaned as my finger worked in and out, gradually going further into her till it was all the way in. At the top of her pink slit, the small nub of her clit poked out of the aroused fold.
I knew it was time for more. Moving up on the bed, I dove my head between her legs. Drawing on my knowledge from reading porn mags, I licked her slit up and down gently. I withdrew my finger and drilled my tongue into her leaking hole. Soon I moved up to her clit as I returned my finger to plunge her hole. Soon, a second inched in as she loosened up. I moved around on the bed so that we were lying in a 69 position. She reached out and took my dick back into her mouth. I was getting off more from having my face in her twat than the blowjob. Her climax was approaching as her hips jerked up and down. Since I had already blown one load jerking off, I was able to hold off longer. She spit my dick out and rolled to her back as her hips lifted off the bed. I kept my mouth glued to her clit as she jerked up and down. Suddenly, she tensed for a second and then collapsed on the bed. Wasting no time, I got up on my knees beside her head and held my dick out to her lips. She responded by swallowing me back down. I got a little excited and humped into her face until she pushed me back. I fell back on the bed as she then knelt between my legs. It was easier for her to control this way. I had to admit she was a natural born cocksucker as her lips stroked up and down, and her tongue seemed to almost curl around my shaft. I reached up and held her head as I felt the cum boiling up in my balls. “Suck it,” I screamed as the first jet of spunk whipped out. She tried to pull off, but I held her steady as I unloaded. “Swallow it. Come on, swallow it.” I panted. She complied.
As the last of my load left, I released my grip. She pulled up with a cough and cum dribbling down her chin. I pulled her down and kissed her full on the mouth. Worming my way between her lips, my tongue savored the taste of my own cum as she also got to enjoy her pussy juice. Breaking the kiss, she fell beside me on the bed. Her chest heaved as she panted to regain her breath.
“Well,” I said “how was it?” “Great,” was her only reply.
I drifted off to sleep for a few minutes. When I woke up, she was fondling my limp dick. Seeing me open my eyes, she asked “Can we do some more?” I said I would need a short bit to recover. I got up naked and went into the kitchen to get a drink. She came up behind me, and wrapped her arms around me as she laid her head on my back. I looked at the clock. We had over three hours minimum before anyone got back. Taking her hand, I lead her back into the bedroom.
Seating on the bed, I pushed on her head for her to kneel between my legs. She complied eagerly. I told her to suck it until it got hard and I would show her some more. At this point, I really wanted to fuck her, but was afraid of getting her pregnant. My rapidly rising dick didn’t care. I pulled her up and looked her in the eye. “I want to fuck you so bad,” I said. She looked down and whispered “but what if I get pregnant.” I lied “I’ll pull out in time.” She was uncertain, and I thought she was going to leave. Instead she said “I can let you fuck me in the ass if you want.” My heart jumped. “You sure? It might hurt a little.” She nodded her consent. I grabbed my lotion from under the bed. I laid her down on the bed and squirted the lotion on her ass. She jumped from the cold impact. Following what I had read in porn mags, I rubbed it between her cheeks and tickled her rosebud. She laughed, and squirmed her ass. However, when I began to push my finger past the puckered ring, she clamped down tight. I told her to relax and reached under to rub her pussy with my other hand. Soon as she got a little excited, her ring opened in acceptance. It was tight, but gradually as the lotion worked in and her pussy heated up; I was able to push further in. I pulled out and reentered with two fingers now. She grunted, but told me to keep going. Soon her pussy was dripping like crazy on my one hand as her ass sucked on my fingers on the other. It was time. Mimicing the mags, I pulled her ass up a little and lined up my dick. With a fresh coat of lube, my dick easily made it past her stretched ring. As I sunk it in beyond the range my fingers had been, she tensed up again. I gently whispered into her ear how sexy she was and how great it felt. I saw a tear on the corner of her eye, but my dick was in control. I told her to play with her pussy. As soon as she started rubbing herself, her ass relaxed and I was able to move in to the base. She yelped, and I froze. Soon she told me it was alright. I pulled my dick back up and slowly sunk back in. Her fingers rubbing her pussy were also jingling my balls when I reached bottom. It only took about six strokes before I injected a final load of cum deep into her.
As soon as I pulled out, I turned her over and dove headfirst into her sloppy pussy. I gobbled up her juices as I drilled my tongue as far as possible into her slit. She started jerking so I clamped my lips onto her clit and sucked like it was a little dick. She exploded in a huge climax.
We lay together, spent. Reluctantly, I told her we had to get cleaned up before people got back. She got up and headed to the bathroom. I watched as cum leaked out of her ass and down her leg. I pulled the sheets off the bed and replaced them. When she was finished, I headed into the bathroom to clean up. Coming back into the bedroom, I caught a whiff of the funk we had made. I had to open the window to air it out.
Sis came over and hugged me. I kissed her on the top of the head. “Remember,” I cautioned “we have to keep this secret.” She nodded and said “Only if we can do this again.” I smiled and assured her I would always be ready.
When Grandma got home, we were sitting in the living room watching tv. She was a little suspicious when she found out Mary had not gone to the baseball game. She checked the bedrooms, and called Mary’s coach to be sure the game had been canceled. For the next couple of weeks, Grandma kept a close eye on the two of us. We acted normal, fighting as brothers and sisters do. There was no opportunity to redo the events of our afternoon sex session, but we did steal a kiss or two and a quick feel cutting through the woods coming home from school. We both wanted more, but were afraid to get caught. It was about this time that Mary started a few babysitting jobs. I always “reluctantly” agreed to go walk her home if the job went after dark. She would either give me a quick blowjob out behind the garage coming home, or I would eat out her pussy. We both wanted to fuck up the ass again, but that would be too dangerous.
About six months after our afternoon of fun, one of the other young girls in the neighborhood got pregnant. I didn’t have anything to do with it, but I got the benefit. Grandma trotted my sister off to the Doctor’s office and had a prescription for birth control pills issued. For another month, she hovered over my sister and me. Once she was satisfied that Mary would keep up the pill, and could not get pregnant; she loosened her guard. In that same period, both my aunts got married and moved out. My uncles never seemed to be home anymore having steady girlfriends. Grandma and Grandpa started going out several nights a week for bingo. This left my sisters and me at home alone. Once the younger ones were in bed, Mary and I had the run of the house. I’ll tell you about the first time when I popped her cherry in another story, but know now we fucked in practically every room of that house at least once, including my Grandparents bed. It wasn’t long before one and then the other sister found out, and wanted their share of Big Brother’s dick. Like with Mary, it was handjobs and blowjobs until Grandma also put them on the pill. Neither of them ever offered their ass to me, but I did get both their cherries.
Of course, when they got a steady boyfriend, I was cut off. This wasn’t a problem as there was never a time when all three had a boyfriend at the same time. Over the next couple of years, some things changed. My uncles got married and moved out, and my Grandpa passed away. This left Grandma, my three sisters and me living together. I had a bedroom of my own now, and usually had one or more of my sisters in my bed almost every night. Grandma never said a thing against it. Mary still let me fuck her ass from time to time, and all three of them fucked and sucked me in between boyfriends. Even later in life, after they each got married and I was living on my own, they would come around regularly for some good old Big Brother fucking. Truthfully, one or two of their kids do look a lot like their favorite uncle.