u/chuckychuck41

“My little brother has a big dick” part 5: Discovering our fetishes

If you’ve been reading my posts, by now, you know that I had started a sexual relationship with my big sister. These stories, so far, are from the first two months (summer) of our relationship.

In my last post, I wrote about discovering a crazy fetish my sis had, having her feet played with. By just playing with her feet while plowing her, she had the look of a deranged, sex crazed nymphomaniac incapable of forming complete sentences during sex. It was like having a super power over her. It was one thing to have a big “tool”, but utilizing her fetish was even better.

The day after I discovered her foot fetish, she was making every effort to initiate our sex-escapades. It was odd to me bc, normally, I (the overly horny 18 year old) was always initiating by dry humped her ass, coming up behind her and playing with her titties or reaching over to rub her clit, etc. But, this time, while I was drinking coffee, she excitedly ran to me, sat on my lap wearing boy short underwear, and kissed me on the cheek. While still sitting on my lap, she leaned over in front of me and started scrolling on her phone. She started lightly grinding her ass into my crotch. I was a little shocked…Was she really initiating sex? I commented: “Hey sis…If you keep doing that, you know I’m going to get a big ol’boner”. She turned her head towards me, and playfully answered “That’s the point, my little BIIIIIG brother!” as she gave me a flirtatious wink. There was something about her initiating it that drove my horniness into full throttle. I gave her a light push to lean her over more, pulled out my fully erect dick, and started slapping it on her practically bear ass cheeks (since her underwear was always ridding up her big ass). “You want your little brother’s big cock that badly? You want this big dick?!” “yes I do! I want your big cock, little bro!”

As I was about to beat her pussy up, per usual, she stopped me “actually, little bro, I’m not going to lie. My pussy needs a break! You’ve been pounding me two to three times a day.” I was a little bummed, but I understood. “Well, ok then…What do you want?” She had that slutty little smile she’d get, then asked “Could you play with my feet again? The way you did, yesterday? I promise I’ll suck your cock, if you do!” That’s where I realized she, legitimately, LOVED it. And, to her word, when I was done tickling her feet, dry humping them with my dick, as she played with her nipples and lightly rubbed her sore pussy, she gave me one of the best blowjobs she ever gave me while I sat down and watched porn.

It was interesting watching porn while someone else pleasured you. Every so often, she’d look up to see what was going on in the porno I was watching. I recall watching a scene that had a guy sharing his wife with a friend. My sister, puzzled, asked while not skipping a beat slurping on my dick “so…is that…what…*cough…*you’re into?” I looked puzzled, she added “you know? DP’ing a chick? Have you ever fantasized about sharing me with your friends?” She was genuinely curious. I answered “Well, yes. Many times”. She laughed, then said in a high pitched, slutty voice “Is that what you want, bro? For big sis to make a man out of ALL your little friends…sorry, BIG friends…I mean, is it your whole generation who have big dicks, like you?” She’d get me so hard when she’d talk to me like that. She sucked me dry, continuing the “playful big sis” slutty talk until I blew my load into her mouth.
“Maybe I’ll just let your friends take turns with me…Bet you’d like that, huh? You little perv!” She began stroking my dick faster. I felt like I was getting overwhelmed with pleasure. For the first time, my old way of pleasuring myself (porn), had crossed streams with what I wanted so long (fucking my sister). On top of it all, she was (at least for playfulness) telling me it would be ok for my friends and I to gangbang her (which was always one of my favorite fantasies with her. Well, that and my best friend and I trading big sisters to fuck!)

She continued tapping into my fetish. Verbally teasing me with mental scenarios of what she was going to let my friends do to her, as I just sat there getting my dick played with while the sound of the porno echoed in the background. “Do you want them all to cum inside your big sister? Is that what you want? Am I a big slut in your fantasies? Can I handle their dicks, or do I get overwhelmed? Tell me, little perv!” I couldn’t answer. I loved when she treated me this way. I don’t recall all the things she said, but she went on and on, saying things that she bet I fantasized about. I couldn’t take it anymore, and blew my load all over her face, which made her say one last thing “I bet you wish your friends could cum on me too, huh?” If I had anymore cum left in me, I would have sprayed her then!

She sat beside me, hugging me as we finished watching the porn. Now that the sexual stuff was over, we had a legitimate conversation about it. She wasn’t offended, but confused. I explained that my friends voted her as the number 1 big sister to fuck. She was flattered and laughed. Then joked “maybe I’ll take them up on that offer! Do they also have big dicks, like you? lol!”
“Would you…ever let us…you know…” I struggled to ask. Her face got serious. She took a second to answer: “I mean, that would be too many people to include in our little secret. I mean, you want me to fuck your three best friends AND you? I doubt your friends would keep their mouths shut. What if they tell people we’re fucking? It’s not smart, buddy.”

She saw me look ashamed. Ever the big sister, even despite us being free use fuck buddies, she comforted me by playing with my hair. She mentioned that we could always pretend, and that was good enough.

My next/last story will be about finally doing anal with her.

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u/chuckychuck41 — 11 days ago

“My little brother has a big dick” part 4

Since so many people want to hear more about my past long term relationship I had with my big sis, I’ll share more. If you haven’t read my other posts, go back and read them for background info.

After the events of my last story, The way we acted towards each other changed. We started to behave more “boyfriend/girlfriend”ish (for lack of a better word). For instance, if she was bending over, I’d go behind her and jokingly start dry humping her, and she’d giggle and say in a low voice “mom and dad are gonna see! Stop!”. Or, if she was wearing a tank top without a bra, I’d pinch her nipples. With time, she got more comfortable playing along, and would do things like grab my crotch and say “boner check!” If we were watching a movie with a hot chick”.

She may have been in her early 20’s, but I was 18. Sex was still “new” to me, so I wanted it ALL the time! and I had the energy and stamina of a horse. bc of the frequency we fucked, I got a LOT better over time. We practically had an entire summer alone to ourselves (since our parents worked), and I took advantage of it.

In a typical day (back then), our parents would leave for work, and we’d start chores. I always looked for the opportunity to fuck. For instance, if my sister was loading the dish washer, I’d put aside her booty underwear (which she liked to wear around the house) and impale her with my dick. She’d giggle and say “wait! You horn ball!” as I’d keep plowing her. She was right, I was a horn ball. If she was talking on the phone to one of her friends, I’d stand in front of her, pull out my dick, and quickly stroke it while making dumb faces to her. She’d try not to laugh, and quietly lip the words “go away!”. Once though, when I was acting dumb and jerking off in front of her, she gave me a slutty smile, then took off her tank top to give me a show while still talking to her friend on the phone. I didn’t waist the opportunity. I started beating my meat, ferociously, until I came all over her. Her wicked smile, with cum dripping down her forehead and chin forever sealed in my memories…

By mid summer, we stopped being so playful about it and would just act upon our urges. It was anticipated that we’d fuck, at least, in the morning and, if I was lucky, one time before our folks got back from work. But I treated it as practice too. I recall wanting to get better and last longer. I’d take the things my sister said to heart. Her complaints about her ex boyfriends techniques and what the failed to do. If she told me a criticism about how I was fucking her, I listened. Mainly, bc I wanted to dominate her in the bedroom. There was something carnal about me, as the little brother, being able to dominate my older sister in the bedroom. It wasn’t enough (to my knowledge, even today) that I was the biggest she ever had, I wanted to leave my mark on her as the greatest she ever had.

The day when all the “training” paid off was like any other. My parents went to work, and my sister was folding clothes. She knew I’d come in to fuck her so, by this point, she’d wear skirts or these nice underwear that would rise up her ass. While she was leaning over the bed, she saw me come in. So, while bending over, she shook her ass side to side playfully, knowing I was about to go in. “I guess it’s time for my ‘breakfast’ huh? You little horn ball!” She said. “Hey, I never hear YOU complain!” I responded, as I took my engorged penis out, and started slapping it on her big tanned ass cheeks.

“Alright, time to put the hog in the pin!” I said, as I started forcing it inside her. She hated when I made farm, or any other, gross references (I said stuff like that all the time! Lol!). It started off the usual way, but then I started incorporating my hips more. Reading her cues. Noticing certain angles made her moan louder. Certain rhythms worked better with her. That was also the day we both discovered something…she LOVED if I played with her feet while plowing her. It was an accident when it happened. I was holding her leg up in the air to get a good angle and, once I accidentally rubbed her foot, she let out an “OH GAAAAAWWWWD!!!”.

I stopped suddenly….confused by her reaction. She literally was out of breath. Then, she regained her breath and said “That…do that again…please, play with my feet…” I had discovered a fetish, and I intended to use it! I already would beat up her pussy with my size, but now I how the power of knowing she had a fetish. In every position I put her, I found a way to tickle or massage her feet. Her eyes wouldn’t, literally, roll in the back of her head while I would do this. Finally, she made a request, she wanted to give me a foot job. She placed my dick between her tiny feet, making my penis look even larger, and started stroking it while she fingered herself. She went into autopilot with the motions, as her muscles would spasm like she was having a seizure. I couldn’t believe what I had unlocked here. My sister’s kink. “Fuck my feet! Fuck my feet! Please! I beg you!” She was begging me…It was like music to my ears.

I put her feet together, and started fucking them while she continued playing with her clit and nipple. “I love it! I FUCKING LOOOOOOVE it!!!” She said. I couldn’t understand it, but loved what it did to her. I asked her where I could cum, and she told me (knowing my favorite place) to cum inside her. I switched and shoved fat Fred (the name we gave my dick) inside her and banged her like no tomorrow while massaging one foot. The time came when I came inside her. I held the entire length of my dick in her, as I pumped my baby batter in her. She, literally, had a jovial smile on her face.

“Little bro, you were killing me, back there! You…You’re amazing! Please, fuck me like that ALL the time!” She said.

The next day, though, given the banging I gave her, she literally asked for a break! She said her pussy was sore from all the fucking. She did, however, request me to fuck her feet again ;-)

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u/chuckychuck41 — 15 days ago

“My little brother has a big dick” part 3

For those just reading, my sister and I had a long term incest relationship that started off with a blowjob ons. Family camping trip. After an awkward week, we re-ignited the sexual relationship when she gave me a blowjob in a changing room.

I should mention that all this was years ago (I’m much older now), so I’m writing this based on memories. As a sort of “memoirs” of our old relationship (basically, none of this is recent).

This is the story about the first time we had sex. she was fighting with an ex over the phone. They had dated a while, but he really started to talk down to her and do shitty things (ie: he wrecked her car, and never bothered to help pay). She broke up with him after finding out he was fucking one of her friends. He kept trying to get back with her, she’d listen a bit, then a fight would break out. It was a vicious cycle. All the while, I was in the background of all this just wanting another one of my sister’s magical blowjobs. The sex didn’t come right away, things built up to it.

So, one day, my sister was having a bad fight, over the phone, with the guy. There was name calling, shaming, yelling and cursing. I was in my room playing video games, hanging out in my underwear (had no plans to go anywhere). Every so often, I sister would walk by. She was wearing these hot booty shorts style underwear, which rose up her ass, and an oversized sweater. She got so mad, that she hung up on him. She turned and looked at me, while I was sitting on the bed wearing my underwear. She looked right at the bulge of my penis, easily visible from my tight underwear. Without saying anything, she rushed to me, climbed on top of me, and started grinding on my fat bulge. She took off her sweater, revealing her tank top and braless tits, which flopped everywhere as she bounced on me.

“Fuck it! I don’t care!” She said, as she kept grinding on my dick, which was now fully erected. I could feel her labia, massaging my dick with every thrust. It felt so warm and, within seconds, I felt her getting wet. I was speechless from the pleasure, but managed to ask “what’s gotten into you?”
“He fucked TWO of my friends, with his little dick, wrecked my car, treats me like shit! Let’s see how he likes it!”

My sister rode me harder. Her big tits slapping my face, from time to time, making a smacking sound. On occasion, I heard her having sex with her boyfriends from my room, but I was witnessing her in action. Although not full penetration, my bulge would stab her pussy and rub against her clit enough to stimulate her. She was loud, letting out sexy high pitched slutty yelps, like a playful dog. She kept aggressively grinding and riding me like she was a prized bull rider. What turned me on most was that my sister was a “talker”. She’d say the sluttiest things that would just come out. At one point, between her slutty yelps, she’d say repeatedly “big cock…biii…ca…big cock!” She struggled to say the words between trying to catch her breath, from the exhaustion of ridding the shit out of me, and her slutty orgasmic yelps.
“I can’t take it! I want your cock! Your big, BIG cock!”

I wasted no time. I pushed her down on the bed, took my underwear off (practically ripping it off), pulled her underwear aside, and began trying to fit my dick in. For a split second, I paused, thinking “oh shit, this is it. I’m going to lose my virginity to my big sis. I’ve fantasized about fucking her for so long!”. I peeled my long foreskin back, revealing the fat head of my dick, and started slowly pushing it in. I couldn’t quite tell how to put it in.

My sister put her hand on my cheek. It was a moment that took me out of the lust. She said “it’s ok. I’ll help you”. She grabbed my penis, lined it up where it should be, then said “Go slow, little bro…You’re bigger than I’m used to”. I began pushing it in, feeling her pussy gripping my dick in an amazing way. She threw her head back immediately. Barely getting her words out, she said “Shiiiiiit, oof! That’s big! Big cock!” I asked out of concern “are you ok?” She looked at me and said: “I’m fine! You’re just the biggest cock I’ve ever had, by far!”

I didn’t really know how to move my hips. My sister, past a certain point, said “here, I’ll drive!” She had me sit on the bed, leaning against the headboard, and climbed on top of me cowgirl style. She lined my dick up, and shoved it in. It felt as tight as before. She let a yelp and a “FUCK!” as she sat on my dick, taking it all in. She began fucking me like a robot. I just laid there, incapable of intelligent thought. The only thing I thought about was resisting the urge to cum too early. But her pussy was gripping me too tight, and the slutty things she told were like music to my ears!
“Fuck fuck Faaaaaaaack!” She said, as she continued using my big dick like a tool to punish her pussy. She rode me to the point of exhaustion, stopping to take a break. She leaned on me, gasping for air. While she played with my hair, she said “Fuck…You’re just so fucking big, little bro! Fuck. I’ve never had dick this big! I love it! I fucking love it!” As she continued to talk dirty, her hips started thrusting like they were moving on their own. She went into full throttle again, using my dick for her own pleasure. I could take it anymore. Between her hard thrusts, her tight pussy, and the slutty things she kept saying, I couldn’t resist. What did me in was when she shifted her voice, and started talking in a slutty sweet way (I heard her once or twice do this with her Bfs).
“Awww! Look who’s giving their big sis all their big cock! YOU! Yeah! That’s right! My big cock little brother! Yeah you are! Yeah!” She was talking like a high pitched cheerleader! Where the hell did she get this stuff from
“You can fuck big sis’ tight pussy anytime you want! That’s right! Bc you’re my big cock little bro! You’ll always have tight big sis pussy!”

It finally happened. I came so hard I yelled as my legs shook uncontrollably. As I shook like I was having convulsions, my sister continued her slutty high pitched cheerleading: “Oh my goodness! Your big cock is coming! Oh I feel it pumping inside me!” She hugged me, as I laid there in a trance like state. I had my first time, finally. She got off me and began queefing out my cum. “Wow, you did a huge load in me! Good thing I’m on the pill!”

She laid near me, caressing my chest the way you’d do to a lover. She told me “Even me doing most of the work, that was better sex than I ever had with Dan!” (Her ex). She gently stroked my spent, flaccid penis saying “Fuck, little bro! That dick made me sore! I’m gonna have to ice my pussy!” She said, going back into the role of bratty jogging big sis.

Despite not doing much of the action, my first time was amazing. Eventually, I learned how to screw better and, once that happened, I started being able to fuck my sister senselessly.

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u/chuckychuck41 — 16 days ago

“My little brother has a big dick” part 2

If you read my previous post, you know that my sister and I ripped the “incest bandaid” off by her jerking and sucking me off on a family camping trip. This is a follow up of how things changed in our relationship.

After that day, it was awkward being around my sister. Even if she reciprocated, what was our role now to each other? My sister, personality wise, was a submissive person when she’d date. It was odd bc, now, she was being submissive to me. Offering to get me food, would ask me permission to do things, it was odd. It’s like I became the big brother, but also a significant other.

I was still jacking off to her every day, and needed to try and address the white elephant in the room (which was that I wanted us to do sexual acts again).

About a week went by (from memory) and we still had no chance to be alone together. We finally got the chance when we went shopping at the mall. We separated from our parents to check out some clothing stores. It was like she read my mind bc, the minute we were alone, she brought it up. She mentioned that she wasn’t sure how to “view me” and, at times, she was treating me like a boyfriend and didn’t know how to view me, again, as the little brother she used to boss around and care for. The conversation continued in a changing room in a clothing store. She was going in and out of a changing room, as I sat patiently right outside. At one point, she asked me to help zip her up. So I walked in, and was surprised to see her bare breasts, and ass in a thong. I looked at her like a ravenous predator; she looked at me slightly concerned. “Are you ok?” She hesitated, then nervously continued “I…I figured it was ok for you to see me nude…Given…Well, you know…”. This was my sister trying to just make it ‘natural’. It was the first time I saw her body nude since the blowjob she gave me. In a way, I was relieved that this was her giving me a sign that she wanted to continue down that path.

I didn’t say anything. I walked up to her, while she was still bare breasted and in a thong, closed the door behind me, and started kissing her. I started feeling her big breasts, playing with her nipples (this was a new achievement unlocked! Bc I never got to play with her nipples before!). I got eye level with her tits; I took a moment to appreciate her pointy brown nipples. My finger traced the circumference of her wide areola (the circumference was like the base of a coke can!). Once I was done studying them, I proceeded to suck on them ravenously. I remember thinking “for so long, I dreamed of this day! Now, I was finally sucking her big tits!” She let out little moans, then made a joke “well, I guess, all those years, you WERE looking at my tits, huh! Naughty little bro!” She sat down in a chair, as I made a joke back “Hey, remember what you said last week. I might be the little brother, but I have a ‘big’ brother dick!”

I pulled my dick out, large and swollen. She looked at it, as though it was the first time she saw it, still incapable of understanding the size. “How real…HOW are you this big?” She asked. “None of the guys I dated, like NONE, had a dick this BIG! And they’re older than you! Did it, like, get stung by a bee, and never shrunk?!” She said, while she stroked it. It was such an odd thing, that my penis would be the thing that caused a change in our “sibling power dynamic”.

“Please, sis, suck it. Please…”. She began by peeling my foreskin back, then placed the head in her mouth. My knees buckled, as she used her tongue to tease the head (she was showing off her skills). Honestly, I thought I was going cross-eyed from the pleasure. She continued to suck my cock in silence, but what drove me nuts was when she started looking me in the eye with her big brown eyes. It was odd, bc it felt like “approval”. She wasn’t shying away, and was owning the fact that she was ducking her little brother’s dick. I don’t know what came over me, but my hips started thrusting, causing me to “face fuck” her.

She moved her hands, and rapped them around my butt cheeks, as I continued fucking her mouth like I was on autopilot. My brain shut off as pleasure took over. I couldn’t move my gaze away at the site of my sister, who was now my sex partner, being on her knees in front of me as I watched my fat penis filling her cheeks with air with every thrust. This was the woman who, even two weeks prior, was my relative.

Unfortunately, I didn’t last long. I was still new to sexual acts. I was too “brain dead” from the pleasure to think to pull out of her mouth, so I blew the entire load in her mouth. It felt so good, I had to catch myself my leaning on the wall bc my knees felt like jello.

For a split second, I felt badly for cumming in her mouth and wondered “Will sis be mad?” But, her response said it all. She still held on to my dick with her mouth, without hands, and nursed on my foreskin like it was a bottle. Fuck, that felt good! While still grabbing the tip of my foreskin with her mouth, she released it, letting the weight of it flop out and dangle, as she opened her mouth to reveal to me that she swallowed my cum.

“I know guys LOVE when you drink their cum…Plus, I didn’t want to get any on me!” She said. I loved this woman! She then, of course, had to tease me and say “You know, little bro, you’re going to have to work on lasting longer! You got a big dick, but you need to learn how to use it better!”

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u/chuckychuck41 — 17 days ago

“My little brother has a big dick?!”

I’ll never forget when my big sister told me those words. Yes, the title was meant to get your attention, but it’s true. I have a sister four years older than me who babied me a lot. She always tried to be in charge of me, like a second mother. She’d be too cutesy with me, always embarrassing me in front of friends. However, despite her well intentions being annoying, I always fantasized that, secretly, she was doing it all because she wanted me. Many times did I get an accidental glimpse of her big nipples, and her thick ass and thighs and she was careless with her towel after a shower.

When I was 18, I wanted her to start taking me seriously. I started trying to be independent, but she continued to push her advice on me, try to play role of second mother, etc. Well, it all happened on a family camping/canoeing trip. We spend the day on the lake, and I got plenty of glimpses of my sister in her tiny bikini. Her ass always seemed to be swallowing the fabric of her bikini. Her tits were very bouncy, and crescent shaped. She always seemed to have pointy nipples!

When we got back to camp, my parents wanted to run and get supplies they forgot. Originally, my sis was supposed to go with them but, little did I know, she stayed behind. I went into the tent and thought to myself “fuck, big sis was hot today!”. I sat down on the ground in the tent, leaned back, pulled out my long, girthy cock, and started going to town.

I had a terrible habit of saying the name of the chick, repeatedly, that I was jerking off to in a low voice. Well, my sister, last minute, apparently decided not to go with my folks. I heard the car leave, so I felt totally comfortable saying my sister’s name, repeatedly, as I jerked off. As I stroked, I’d say in a low voice quickly “Sara…Sara…Sara…oh God, Sara!” My sister, apparently, heard me saying her name repeatedly and, later, confessed that she thought I was injured. So, while I was stroking the hell out of my cock, my sister opens the tent wide open, gets an eyeful of me jerking while I literally, and no way to deny, was in the middle of saying her name again. She exclaimed “OH MY GAWD! OH MYGAWD!” I yelled “WTF! Just GET OUT! GET OUT SARA!” As she said repeatedly “I am so so sorry! Lil bro!”

I didn’t walk out of that tent for 30 minutes, until I thought “well, now she knows”. I walked out, and saw her sitting in a folding chair. She asked me to join her, then proceeded to tell what, at first, was one of her usual wannabe motherly talks. I am paraphrasing, but she basically said something like “I am REALLY sorry I walked in on you, little bro. I heard you calling my name. You sounding in pain, so I wanted to check on you…Look, I know that you are a man now, and that you have certain…urges…I also know that it’s normal for a little brother to see their big sister in THAT way. I hope you know, I’m not bothered by it”.

For some reason, it turned me on to a level I had never been turned on before. My big sister just told me that she didn’t mind that I jack off to her. We got to talking about sex, girls and, somehow, she put on her ‘big sister’ hat in a sexual way. “I’m just gonna say it, little bro, you got a BIIIIIG penis! I can’t believe I never noticed!” I was blushing, and of course said “I mean, it’s not that big”. She politely kept insisting, saying that it was bigger than all the boyfriends she ever had. Then asked “could I, maybe, see it? I just want to check something. Promise”. I was so fucking horny, I didn’t care. I stood up, pulled it out, and let it flop down so hard, it bounced. “Woah! Easy with that thing, little bro! What do you feed it? Jeez!” She said, being her usual self and making jokes. She delicately grabbed it, moving it side to side, like she was inspecting it. She spoke to me in a sweet motherly voice “This is, definitely, the biggest penis I’ve ever seen…and it belongs to my little brother! I can’t see you the same way, little bro!” I was so proud. I knew I was taking a risk asking, but I was desperate.

“Sis, I hate to ask, but could you play with it? I never had a girl play with it before. Your hands feel so much softer than mine”. I never saw my sister look horny before, nor did I ever see the side I was about to see. “You want me to make you a man? Is that what this is?” She asked. I nervously responded “Yes ma’am. Please…”. She looked like she was deep in thought, then she said “ok. I will”.

She started off by pressing her two fingers on my pubic area, forcing the full length of my dick to be visible. While still pushing, she used her fingers to make my dick swing side to side. My dick looked even bigger than usual compared to her tiny hands. “My little brother has a big dick! Who knew?!” She told herself, laughing as she played with it. She was really getting into stroking me. I felt like I was in heaven. A few times, I caught her biting her bottom lip, and rubbing her thighs together. She was turned on. “Fuck, why can’t your dick be on one of my boyfriends? This thing is HUUUUUGE!” She said, further feeding my ego. “I’m proud of you, little bro! Or should I say, BIG bro!” Despite all her praise and adulation, I could barely talk. I was so turned on, and her continual praise made me hornier. While stroking it, she stopped like she was pondering something, then said “You know what? You’re so sweet. I’m going to do it”. Before I could ask, she started sucking me off! My eyes rolled back in my head, and I started doing my embarrassing thing, where I call out the name of the girl I’m jacking off to. This turned on my sister, as she started to harass me with questions “oh! You’re starting that again! Do you like to jack off to big sis?! Do you like saying my name, when you jack off to me?” I answered with a weak and feeble “Y-yesss”.

She wouldn’t stop. “Do you always jerk off to me?” I answered “Yes, big sis. All the time!” She responded, calling me a naughty boy. She went back to sucking me off, but I couldn’t last. I blew a huge load in her mouth, as my legs felt like jello. She held my dick in her mouth a moment, then released it, causing it to dangle by the side of her face. She spat the cum out on the ground, and let out a laugh!

I thanked my sister profusely for giving me my first handjob and blowjob. She told me to let her know any time I needed relief. It was the start of a beautiful sibling relationship.

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u/chuckychuck41 — 18 days ago

My slutty sis taught me how to masturbate

One of my favorite sexual experiences ever! People find it hard to believe that I didn’t know how to masturbate until I was about 18 (I know, hard to believe, but it’s true). I guess life was just too busy.

Things started to change after my sister got knocked up by her boyfriend. Her body started to change (for the better!). My sister always was curvy, but now her hips were wider and her tits became huge! I found myself having weird feeling for her.

My sister seemed like she was always horny. Always talking about sex, would sometimes joke about my penis, etc. It happened at a changing room at a big department store in the mall. My sister was trying pregnancy clothing on and, sometimes, would ask me for help bc it was hard for her to reach around and zip herself up. I started stealing peaks at her massive tits; the way they wanted to pour out of her bra was giving me a huge boner. She caught me staring while I was zipping up her dress and jokingly said “Geez! At least wait until you’re done zipping me up before masturbating! lol!” I don’t know why, I simply asked “How DO you masturbate? Like, is that a true thing?”

My sis laughed at me, then paused awkwardly when she saw that I was serious. “Holy crap…do you seriously not know how to masturbate? Like, for real? Wow, dude that’s sad!” I reassured her it was true, and that the few times I tried playing with my penis it hurt. Oddly enough, as we talked about it, my sister started getting this look in her eye. She sat down on the chair in the changing room, grabbed me by my waist and started pulling me closer. “Come close, bud…I’m going to do you a favor…Don’t you dare tell ANYONE!!!”

“What are you doing!?” I asked, but she wouldn’t respond. She unbuttoned my pants and pulled them down. She took a moment to stare at my bulge, then commented “Wow, didn’t think you’d have a big one!” as she put her finger under my crotch and started bouncing it up and down. She pulled down my underwear, causing my dick to pop out and bounce up and down. She let out a little laugh as she said “Wow, Jimmy! Not a bad dick! It’s a good size!” as she continued to make my dick bounce with her fingers. It honestly felt amazing.

She grabbed my long, uncircumcised dick and said “I’m going to show you how to masturbate. You’re probably worried bc you have a foreskin. But don’t worry, I’ll be gentle”. She started to peel my foreskin back. I must admit, I had never tried peeling it back that far before. As the foreskin stretched over my penis head, it felt like a mixture of amazing, but also painful. I moved my hip away, as if to resist, but she kept reassuring me it was normal. When she managed to peel the foreskin back completely, I felt an odd almost orgasmic feeling. She began slowly peeling my foreskin back and forth over my penis gland. Honestly, it felt like she was satisfying an itch I had for years. My legs started to tremble with each stroke. The most mesmerizing thing was that, every so often, she’d look up at me with her big beautiful blue eyes. A couple of times, she bit her bottom lip in such a horny way. “Does it feel good?” She asked in a sensual voice. It actually took me a minute to respond and, even once I did, I could barely say: “Yes”.

She stopped stroking me and said “Now you try. Play with yourself”. I started stroking myself. It felt odd, but good. I noticed her hand slid down her pregnant belly and landed on her crotch. She started to rub herself. She looked up at me with a wicked smile, as I beat my meat to her. She saw me starring at her tits, so she said “I always catch you looking at them. Here, let me take them out. Give you a visual aid”. She peeled her bra down, which caused her engorged tits to flop out like boulders. Her aureolas were huge in diameter! A nice dark pink/ light brown. I started to beat my meat faster, as she pinched her own nipples. I’m embarrassed to say that I came so hard, only after a few minutes of masturbating. Being that it was the first time I ever came, my legs got wobbly, like they were going to give out, so I grabbed onto the chair she was sitting on so I wouldn’t fall. I dumped a huge load of cum all over her tits and face. She gave off a wicked laugh. I apologized, but she said she was use to it.

After that day, I jerked off like a champion and, mainly, to my sister. Thanks to her, I have a fetish for busty pregnant women! We had other sexual adventures!

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u/chuckychuck41 — 22 days ago