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My Sister has a Bigger Dick than Me

We'll just start with the basics, first thing is my name is Carter. I'm a 18 year old boy and currently a freshman in college and living with my parents and sister. Some things about me: I'm an athletic person and I play a couple different sports (football and swimming), and I also generally get pretty good grades. I think I'm relatively smart, but if you're smart you also tend to question whether or not you're actually smart and who really even knows anyways? I wouldn't say I'm very popular, I'm a much more introverted person and because I grew up with my twin sister and we've always had each other I've definitely put less emphasis on having best friends.

Anyways, as far back as I can remember I've always had a sister. Growing up we were actually quite close, we did everything together and I'd say we honestly probably barely experienced being lonely at all. There's a reason I say I only remember having a sister, though. See the thing is, her and I were both born as males. Fortunately for her and for all of us, my parents are both medical professionals and are fully aware of the gender issues some kids struggle with and actually spotted the differences between us from a very young age. My sister got pretty lucky, and she got to grow up purely as a female; albeit a female with a pretty large dick.

As we get older we actually probably don't hang out as much as we used to, we both tend to just do our own thing a bit more now that we're kind of developing our own interests and hobbies, but when we did spend time together it was really like nothing had changed at all.

Which brings us to where we are now, sitting in our living room late on a Friday night trying to find something to watch on tv.

"Come on sis just pick something already, you've been searching for like ten minutes," I whined to her, getting annoyed at her indecisiveness.

She looked at me with a pouty face, "we've already seen all these movies, do you wanna just watch Captain America or something again?"

"No not really..." I sighed, looking at the tv and caught my eye on the channel below it, "looks like it's that time of night, though, wanna watch some skinemax?" I cheekily asked my sister, with a grin on my face.

Her next action really took my by surprise as she actually switched to the softcore porn, "eh why not, nothing else is on,"

I looked at her with a slightly surprised look on my face. My sister was definitely the innocent and good one between the two of us. We had tentatively broached the topic of porn before and I knew that she didn't watch it by herself and she knew that I definitely enjoyed it.

She laughed suddenly and brought me out of my reverie, "god these people suck at acting so much," she said.

"Yeah, just show us your tits already!" I joked with her at the TV.

She gave me that look, when I said that and chuckled a bit, "you're such a pervert, Carter, all you care about are tits."

"I resent that! I also care a great amount for the ass!" I responded in a joking tone as I winked at her.

I could tell she was getting a bit flustered by this unusual conversation for her, but she seemed like she was trying to be brave and just push on.

"Pussy doesn't do it for you, huh? You'd rather have the ass and the tits?" She questioned me, trying to get a rise out of me. "I didn't think you swung that way, Carter, but I'll still support you even if you are into dick and guys."

"Haha, very funny, no I'm not into guys thank you very much. But to me it's not the genitals I necessarily focus on when I think whether or not someone is attractive. It's the whole idea of femininity that I enjoy, you know... tits and ass" I chuckled a bit at the end as I answered, being a little more serious now. As I told her what I thought she gave me a look that I really couldn't decipher what she was thinking at all.

She looked thoughtful for a moment longer and then asked, "Do you think most guys feel that way?"

"Are you asking me if most guys would care that you had a dick?" I just straight up asked her, knowing what she was getting at.

She smiled, used to me being blunt by now, "yeah, I never really considered dating much to be honest with you, I always thought guys just wouldn't be interested in me and the surprise would be too much for them if it ever came to that point."

"I mean, you're gonna run into all different kinds of guys as I'm sure you're aware, but yeah the truth is some guys definitely would be unhappy with it. But hey, it's their loss right? They don't know how awesome you really are, Em." I scooted over and put my arm over her shoulder as I said the last part, and she smiled and leaned into me.

We both just watched the skinemax for a little bit and it switched to a scene with a guy jerking it, it got a bit awkward at this point until my sister asked me, "is that how you're supposed to do it?"

I wasn't quite sure how to respond, "what do you mean, is that how you do it? Is that how I do it specifically? I doubt I look like that when I do it, he's trying to make pornography and I'm not."

She laughed a bit, "no no I mean is that how you're supposed to jerk off? I've never actually tried it before..." she said.

I was a bit shocked at that, "how have you never even tried masturbating before? That's like, inhuman," I said.

"Well... when I was younger I was going through a bunch of hormone therapy, and that kind of affected the way I responded to things sexually. Now that I'm older it's a lot more balanced out and I just don't know how to do it now, but I feel those urges I guess?" her explaining this made sense why she would want to watch the skinemax now.

"Huh, well yeah then that's the basic concept of it. You just grab your dick and rub your dick, pretty much. Although I guess there's quite a bit of technique involved and you really sometimes need to put in the work to find the sensitive spots," I said, getting kind of thoughtful about how much practice I'd put in to masturbating and how much technique I probably had now that she would have to learn at a much older age than me if she wanted to.

"Would you... would you be willing to teach me how to do it?" she asked me shyly.

I was pretty much speechless at this request, it's not every day your sister asks you if you will show her how to get off. It wasn't that I didn't think she was attractive or that it would be gross, but it was just a big request.

She got insecure when I didn't answer immediately and changed the channel back to Captain America, "just forget I said anything, I'm sorry if that was too weird for you," she said quickly.

"No it's not that it's too weird, I think it's completely normal to jerk off. After all, I've been doing it for years at this point. It's just that I've never even thought about teaching someone how to do it, let alone my own sister," I was quiet for a second after that, just watching the show with my sister.

"Okay, if you promise to not tell anybody and also clean my room, I'll teach you how to do it," I said, smirking a bit at my request for her to clean my room.

"I won't tell anybody, but I don't think I want to clean your room - that place is a mess," she responded back seriously.

"Well it was worth a try, right?" I laughed, "okay, ermmmm I'm not sure how we're really supposed to get this started, though... do you wanna just take it out and I'll teach you how to do it or what?"

She got kind of nervous at this point, "uhmmm yeah I guess if that's the best way to do it, sure," she was still covered by a blanket at this point, but I could see her moving around under there and saw her pants and panties drop down to the floor."

I started getting a bit nervous myself, not sure how to walk someone through jerking off, "Okay, first just go ahead and grab your dick," I didn't tell her to move the blanket yet because I knew this was a bit awkward for her and I didn't want to embarrass either of us. I saw her move her hand under the blankets and could see a pretty decent sized tent poking out from where her fist was. "Damn sister, just how big is that thing?" I asked with my eyes wide.

She giggled a bit at that, "I'm not sure, I've never measured it. Probably about 6 inches or so," she replied while holding her dick under the blanket.

"Seems like it might be a bit bigger than that, okay go ahead and start stroking your dick then and just tell me how it feels and we'll go from there," I said.

She adjusted herself and put both her feet on the couch with her legs spread and leaned more back into the couch. I saw the blanket move up and down slowly as she pumped her dick at my request, and she bit her lip while she was slowly jerking off. I couldn't help but get pretty damn turned on at the sight of it. I wanted to see it at this point, I was feeling very curious.

"How about you take the blanket off so I can see exactly what you're doing and help you out a bit more?" I said, my words rushing out a bit through my nervousness.

"Are you sure? I don't want to weird you out or anything," she replied, stopping her stroking for a bit and looking me directly in the eyes.

I smiled at her, thinking she looked beautiful when she was vulnerable like that.

"Yeah, let's see this monster. I want to know what I'm working with," I told her with a smirk.

She giggled at that and then pulled the blanket over. She still had her shirt on, but she was completely naked from the waist down, and her hand was currently holding the biggest dick I'd ever seen in real life, not that I'd seen many but still. I whistled appreciatively at her cock and she chuckled a bit at that.

"Are you sure you're not gay, little brother?" She teased me.

I rolled my eyes at her, "yes Emily, I'm sure I'm not gay." Just to fuck with her though I reached down and cupped her balls, which were also definitely above average. She squeaked and jumped at this, and her face flushed a bit and turned red. I think I'd found a weakness of my sisters.

"Woooahh that feels so good," she said, still not moving her hand on her dick as I just gently massaged her balls with my one hand, occasionally squeezing and rubbing them in my palm.

I was super turned on at this point, and I figured since I'd already gone this far I might as well just make it worth it as far as educational value goes. Without saying anything I took my other arm from around her shoulders and brought it down to take her hand from her dick and put my own hand around it. She tensed up a lot as soon as I grabbed her dick, and I could tell her breath kind of hitched a bit in her chest.

"I think the best way to teach someone is just to give them a proper demonstration of what it looks like, notice how firmly I grip it and how I'm not stroking the skin so much as just pulling it up and down along the shaft? We don't want to cause too much friction because that can just hurt you," I said as I was gently pumping my hand up and down along her dick, while mostly just holding her balls in my other hand.

She wasn't really paying much attention at this point, her legs spread further just giving me more access to her cock and I could tell she was having a hard time focusing through the pleasure. I decided to quit talking and just continued to stroke her softly. She leaned into me pretty heavily and I was doing my best to just drag it out. I could tell that she had an overly sensitive dick, probably from not ever really touching it when she was younger, and I didn't want her to cum too quickly.

No matter how slow I went I could tell that she was getting closer, her breathing was getting heavier and her body was starting to hump my hand as I stroked her.

Without a warning from Emily or anything, I felt her dick start to pulse in my hand and knew she was coming. It actually felt pretty cool to have that feeling of power and just feeling the pulsing in my palm. The first jets of cum started to shoot out and I knew right away this was going to be a big load. I was shocked at the amount of cum that came out in the first spurt, and it went all the way up and hit my own sister in the face. I was so insanely turned on at this point I'm pretty sure my dick could have cut diamonds. Jet after jet of cum was shooting out of my sister, I wasn't sure if this was just the buildup of years without release or if this was normal for her, but the amount of cum she sprayed all over her body and face was just unreal.

She was breathing really heavily at this point as if she had just ran a mile, and she smiled at me, "thank you so much, that was the best feeling I've ever had in my life," she said to me.

I smiled at her, "that was surprisingly fun, I don't mind at all," and I really didn't. I hadn't ever really entertained ideas of my sister in this way before, but I think she just unlocked a part of me that I never really knew had been there all along.

She was still trying to catch her breath, "need to go clean up, I really made a mess didn't I? Is this normal?" she asked me, innocently.

I laughed at her, surprised at how little she knew, "Uhm, yes and no. You just have a lot more cum than most people do, definitely a lot more," I said.

She looked embarrassed about this, "I'm sorry..." she told me.

I reached over and ruffled her hair and grinned at her, "there's nothing to be sorry about, I just hope this was educational for you."

That's all I have for now, maybe I could have ended the chapter a bit earlier or something IDK.

*****

Anyways, if you have any feedback on this or requests or anything you'd like me to write about (preferably related to this, but it definitely doesn't need to be) just let me know! I really want some requests and feedback. I had a lot of fun writing this and I hope you enjoyed it. :)

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