Sister's Share

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Charlotte tells her sister about her first time.
5.4k words
4.19
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Part 1 of the 2 part series

Updated 05/04/2024
Created 04/28/2024
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*features massive sizes, male on male, light(very light) domination, trans, incest

"OK, I want an explanation, like right now. Right now, Charlotte." My sister had barely closed the door before turning on me and whispering through her teeth, despite having long ago sound proofed her room.

I sighed as I sat on her bed, crossing my legs. I'd known this was coming, of course, but it really didn't make it any easier. My sister...well let's just say she's very judgy. And more than a little quick to jump to said judgements.

"It's...long. Long and complicated, sis."

She just rolled her eyes and sat beside me, her eyes narrowed, looking me up and down. I couldn't blame her, last time she'd seen me...well I'd been drastically different. Still, it made me feel like a zoo animal, and I wasn't super thrilled about it.

"Ugh, fine. Just...start at the beginning. I wanna know every detail. Every. Detail." She did that thing she'd been doing since we were kids, where she stared hard at me until I gave in. I'd known that was coming too. I sighed again, running the last couple of years through my mind.

"It...I...look, some of it is rather...graphic, and a bit private. I'd really rather no -"

"I said. Every. Single. Detail. The last time I heard from you, let alone saw you, you were leaving for college and fighting with dad again. And oh yeah, your name was Charles, so you come waltzing to my house, you better start talking."

"I...ok, ok. You win. I...I never wanted to hide it from you, sis. It's just...it's not easy to talk about, you know. Especially with how mom was, and dad just following her lead. Doesn't really make for a...stable environment to talk about...well anything."

Victoria, Tori to her friends and family, sighed and lay on the bed.

"Yeah, you got me there. I just...when you cut off contact, you didn't have to leave me too, you know. I know we weren't the closest or anything, but..." her voice trailed off and I looked to the floor. She was right, I didn't really blame her or harbour any real negativity towards her, it'd just been so difficult to talk to her and not see my parents. I sighed and lay beside her.

"I know, sis. I know. I'm sorry, I...I didn't know how to tell you. I...it was just easier, ya know? Just easier to pretend I had no family. Easier than...than the memories."

Tori sighed again and propped herself up on one elbow.

"Look, I decided ages ago that if you came back, I'd hear you out at least. I know we could've been closer and some of that is my fault. But seeing you like...well seeing this, it kinda threw me for a loop. Honestly, I'd always thought you were gay or at least bi, but...well I didn't think I had a sister. You know this doesn't really change us, right?"

I had to hide my smile real quick, happy that she really was exactly like I remembered her. Of course just walking up after years of silence and being an entirely different person...well anyone would have a rather dramatic reaction.

"Thanks sis. That really does mean a lot."

"Pfft, shut up. Now, start talking."

"Start talking, or shut up? Pick one!" I stuck my tongue out at her while she rolled her eyes, a little half smile growing.

"You know what I mean, ass. Were you always like...were you always Charlotte? Also, I don't really know how to talk about it without sounding like an ass."

"Oh, pfft. I don't care, say what ya want, you know that. And...sort of? It's kind of different for everyone. Some know from the time they're old enough to know what different genders are. Some don't know it their entire lives almost. For me...I didn't know. Not...not entirely. You remember Danny?"

"The little girly-guy we used to make fun of? Wait, is that bad to say?"

"Ha, I told you, don't worry about it, Tor. He's more than ok with it. Well, he's my boyfriend. Well, fiance, actually. We don't have a ring yet, but we're together."

I watched her jaw drop and almost snorted. Almost. My sister is super predictable and I'd nailed that prediction. She stammered for a second, then laughed.

"You know, when you were...what, seven I think, I bet Janice that you two were dating. Of course, you both denied that and I lost. Man, I should call her now, get my money back!"

"You bet...on me and Danny dating? Why?"

"Cuz I was fifteen and bored. Why else?"

I snorted then.

"Well anyways, we're together now. It's cuz of him that I learned about me as Charlotte. I guess I should probably stop beating around the bush. I -"

"Do you have one? Not a bush, a vag?" she blurted out. I had to pause so I could laugh.

"Yes, I got bottom surgery. I'm a girl in basically every way."

"Cool. Sorry, that was like my first question, just couldn't hold it in anymore once you said bush." I snorted again. Should've guessed.

"It started in college. Duh. I'd been wrestling with it for a while, without really realizing. How do I...hmm. It's hard to explain. It's not like there was flashing neon lights telling me why I felt weird or why some things just felt wrong. It's not like everything 'manly' was weird and everything 'girly'

wasn't. There's no real clear cut signs, I just felt...different. I know everyone feels different and like they don't belong and whatever, and for a long time, I just thought that was it. I just needed to find my little crowd, my niche, ya know? Well I found them, the nerdy bastards. Dungeons and Dragons, I'm sure you won't be surprised to find out. Danny was there too, but even amongst people who accepted me and lifted me up, I still felt...on the outside, like I was watching myself be someone else."

Tori frowned at me a little, it was clear she didn't fully understand. Not that I blamed her, I barely understood it myself.

"So, like...you didn't know you were Charlotte?"

"Not directly, not yet. More like I didn't know who Charles was, who I wanted Charles to be. I just...I wasn't me, though I didn't even know who me was."

"I...I don't really follow, Char."

I smiled and patted her shoulder.

"I know. It's not really something I can put into words, there's no magical way to understand it. Not really the point though, suffice to say that I was just not yet me. Anyways, you know how we used to tease Danny for how much he looked like a girl? Well I did it then too. Believe it or not, he looks even more like a girl now. Any ways, when we graduated high school, he started getting a bit...weird when I'd tease him. Honestly, I think he was just tired of it, I mean you and I had been doing it for years, and I know others did it too."

Tori looked away.

"I know, sometimes I think about it and feel bad. I tell myself I was just a shitty kid, but so was he, you know. Can you tell him I'm sorry?"

"I want you to meet him soon. Well...re-meet, I guess. He's my fiance, Tor. I want to you in my life...please."

She smiled at me, and just nodded slightly. Just a 'well duh, dummy' look.

"Anyways, whenever I'd mention his girlyness, or call him a girl or whatever shitty thing I was saying then, he'd grab at his crotch and say 'well at least my dick is huge'. Never in public, just between us. I never really had a response to that. I usually just smirked and looked away. I mean, what does one say to that?"

Tori snorted.

"Should've just been like 'not as huge as mine' or something. I don't know." I rolled my eyes.

"Yeah, that would've went over well. I don't know, I didn't really like thinking about my dick. Weird, I know. It...it's not like thinking about it felt wrong or anything, just...I just didn't really think about it. Not counting jerking off, I guess. But that was his habit and I eventually just kind of...ignored it. Not like I was ignoring him, more I just wouldn't bother reacting to it. Anyways, one day we were just chilling in our dorm. We'd each had seperate roommates, but had managed to convince both of em to trade. They got married, fun fact. Danny and I went to the wedding. Nice little place in the Muskokas, I wore a dress. My first one in public. Anyways, that's off topic."

"I can sort of see you in a dress. I mean, you're in a tank top right now, and shorts and all, but you seem like a dress type of person. Is...is that weird to say?"

"Tor, stop worrying about that. I take it as a compliment. I've worked to get this figure, you know. I suppose genetics helped, but still. Where was I? Oh yeah, we were in our dorm just chilling. Danny sneezed. That's what started everything. A sneeze."

Tor stared at me with the most dead pan look. I think she was deciding if she believed me or not. Eventually she whispered again.

"You realized you're a girl because your eventual boyfriend...sneezed."

I snorted, it sounded so stupid like that.

"I mean if that's how you wanna put it. But yeah. It was the girliest goddamn sneeze I'd ever heard, like super high pitch and nasal. Like if you heard it without knowing, you'd just know it came from a girl. His long brown hair even fell over his face and he tucked it behind his ear so damn daintily, I had to mock him. I had to, it was an irresistable compulsion. Like, I swear he had a pinky up and everything. It was the single most stereotypically girl thing I've ever seen. I cannot stress to you just how much I needed to make fun of him there."

Tori chuckled lightly, a small light playing in her eyes.

"Dude....dudette? Whatever, I've made fun of you for less. I get it, I'd mock him too, if it was really that bad, I'd probably be pissing myself laughing." I smiled back, glad she understood.

"So what'd you say?" She asked and I just smiled.

"I don't really remember, not really important. I laughed at him and he, just like clockwork, grabbed his junk and 'at least my dick is huge' and for some reason, this time...I looked. Like, not full on stared or anything, I just followed his hand for a second. The bulge there...you have to know, for most 'guys', looking at another guy's junk is just...well it's weird. Most aren't gonna beat you up or anything, but they will think you're weird. So until that day, I just...didn't. There wasn't really a reason to. I knew I liked guys, of course, but I didn't really make it a habit to stare at my best friend's cock."

Tori raised an eyebrow, I knew from childhood that that was her 'I have a question' look, so I paused.

"Well, why did you look?" I screwed up my face a little, and looked away. Truth was, I had no idea. I hadn't done it before, never even really thought about it. Danny is so girly looking most of the time that even though I knew he's a guy and everything, I'd never really thought of him like that. Not before that day. I sighed.

"No idea. There was never a temptation to, it's not even like I did it on purpose. My eyes just followed the motion, and the rest is history."

"Ah hell no. Absolutely not, you are not getting off that easy. You start talking, right now."

She raised her eyebrows and pointed to the bed, as though she was a mother and I a disobedient toddler. I looked at her and laughed.

"You want me to tell you about me and my fiance's sex life? For real?"

"Char, I'm a thirty four year old single - not by choice - woman with no real girl friends. You're the closest I've got. Besides, if he fucked you so good that you became a woman, that's a sex life I wanna know about!"

My jaw dropped for a second, I didn't even know what to say to that. In the end I just laughed.

"Well, ok then, sis. You know that's not how it works, right?"

"Duh, but it's a hilarious way of thinking about it."

I snorted yet again.

"Fine, fine. But you asked for it. Let me just adjust..." I sat up on the bed, leaning against her pillows.

"So I followed his movements and saw...it. Well, the bulge anyways. And let me tell you...I've seen some pretty big bulges before. Some real, most fake, but his...well, it blew all the others away. He was wearing some fairly tight jeans, and you could see the damn snake shoved down almost to his knee. I could even see the exact shape, where his balls were, down to the circumsized head...in short, sis, he. is. Huge. Like gigantic. And I...I didn't believe it. Like it just looked so fake. Like completely; it had to be, you know? I kind of froze for a moment. Unsure of what to say, or if to say anything. Danny never brought anyone to the room, but he'd gone to a few parties and I'd heard rumours that he'd taken some girls and some guys into some empty rooms, if you catch my drift. I'd never asked him about it, why would I? So at that moment, I just froze."

"You...froze? Presented with the biggest dick you'd ever seen, and you froze? For real?" She looked at me like I was an idiot. I laughed, I'd thought much the same before too.

"I'd never been with anyone before. Plus, like I said, I'd never thought of him like that before, and I wasn't really sure if he'd even meant for me to see it. Also, I wasn't even sure if it was real, there was a part of me that thought he'd stuffed a dildo or something in there. So, yes, I froze. I think my mouth was open a little, though I still couldn't tell you if it was from desire or shock. Probably both, if I'm being honest. He caught my look, of course he did. How could he not? He smirked. I've come to learn that Danny is a definite top, a gentle dom, if you will. For the most part, sometimes he likes it rough too, and well...I do too." I could feel myself blushing a little; I hadn't planned on talking about my sex life like that and definitely not with my sister of all people. But, once I'd started, I couldn't stop. Story of my life, really.

"He slowly stood, and even though I could see him moving, my eyes were still fixed on his cock. I could feel my mind trying to tell if it was fake or not; did the way it shifted slightly seem real? How could a dick that big even exist? It was fake, it was, it had to be. He came closer and closer, me still sitting on the edge of the bed, about chest level to him. He in those tight jeans and even tighter spaghetti strap tank top. His hair had fallen to one side, over his shoulder so it fell just in front of my face. There was...an energy to the way he stood, hands on his hips. A very...feminine energy, despite the huge monster just a zipper away. I... I was hard. Like my dick, I mean. Not that you could tell, not like I had a bulge like that! No, I was average, at best. I've measured before, partly out of curiosity, but mostly cuz it felt like what a guy should do, ya know? I remember, I'd wondered, briefly, if Danny had measured his, if he knew just how many inches I was staring. How many he dwarfed me by, mow much bigger he was, in this clearly soft state, despite the size."

"Well, don't just beat around it, give me some numbers! How big was he, how...not big were you?"

I looked at her in shock; again, not something I'd ever envisioned talking to my big sister about. Ever. I gave in; clearly she was not going to let this go.

"Well, I hadn't measured since grade...nine or ten, I think. I think I was a bit bigger than back then, but not by much. I'd measured myself at five inches long, and a little over one thick. I think by that time, by the time I was seeing Danny's absolute beast, I was probably six and a half, and maybe two thick. Maybe. I didn't measure his dick that day - yes, Tor, I did eventually - but I'd find out that he's twelve long soft, and three thick."

"Nope."

I frowned at her.

"What do you mean, 'nope'?"

She frowned back at me.

"What do you mean 'what do I mean'? Obviously, your bull shitting me right now. That's not real, and you know it. I - what are you doing?"

I'd pulled out my phone and was going through my photos. I'd taken more than a few of Danny, and his god-like schlong. How could I not? I'm a professional photographer, and I love taking pics of him. Mostly nude modelling, of course. I found one where he was soft, just holding it near the middle, the vast majority of it hanging down. There was a table with a lamp next to him in that shot, not directly but close enough to give a relative size comparison. I showed it to her. There was a long moment of silence.

"That...and you didn't edit this? No, you wouldn't, would you. I remember the cameras you bought, the photos you took. Editing is for those without talent, right? Isn't that what you used to say?"

"Pfft, not just me. But no, it's not. He really is that goddamn massive, sis. I'm not bull shitting you."

She paused. Then she slid a little closer, grabbed the phone from me and studied the photo. I don't know if it was cause she liked what she saw, or if she was trying to tell if it was fake still, but I let her do it. Danny had given me permission to share his pics if I wanted, though I had told him I probably wouldn't. Oops.

"Can...can you send this to me?"

That time, it was clear she just wanted it cause she liked what she saw. I couldn't blame her; I did too, very very much so.

"I mean...fine? Just whatever you use it for, I don't wanna know about it, mmkay?"

She smiled and nodded, handing me the phone back. I sent it to her, and leaned back again. What a weird day, I thought.

"So? What happened next?"

"I looked up at him, duh. Not even to say anything, it just felt like the thing to do, you know? He smiled down at me, somehow looking like a shark, if that makes sense. He slowly opened his pants, giving me plenty of time to tell him to stop, to say no, if I wanted...I didn't. I said nothing, just watched as the button popped and the zipper slowly opened, that denim V slowly widening. He had a little hair, though not enough to really be unkempt. He doesn't shave it or anything, it's just naturally like that. I swear, it took soooo much mental strength not to drool there, the moment the root came into view...the moment I could see that it was real, it really was just so big, so...powerful. I didn't, but I came so close to...he pulled it out. Again, slowly, and to see a hand in comparison to it...it just drove home just how massive it really was. He had red painted nails then, and his entire hand looked...just so small, next to the insane baseball bat he had unleashed."

Tori raised an eyebrow. Not questioningly, just raised.

"You...ahem, you're a bit more...descriptive than I remember, Charlotte."

I chuckled.

"Yeah, I know. Danny's more than just my fiance. He's my best friend, my lover, my eventual husband, my photo muse, and my story one too. I don't publish or anything, but sometimes, seeing him, looking for all the world to be a thin tiny woman, with a freaking telephone pole jutting from his waist...well it's inspired me more than a few times to write about. They're made up stories, of course, I don't really want to write about my real sex life, but it's all real in the sense of it's things he's done or can do. Sometimes I send them to people I know, just with changed names and everything. They love them."

She looked at me expectantly.

"What?"

"Well you know you're gonna send them to me too, right?"

"You know, I came here to try to reconnect, ya know? This wasn't..."

"I know, little sis. But you brought this - " and she flashed the pic I'd sent "to me, and you're damn well gonna continue. Sisters share, you know."

I had to laugh. It sounded so ludicrous.

"I'll think about it, ya perv. Anyways, he pulled the damn thing out. I remember the smell hit me and I throbbed in my pants. Hard. Like I swear, I was the hardest I'd ever been. It wasn't the ballsy smell you'd normally expect...I mean, it was, just not...not just that. It was like that, but also sweet and...I don't know, savoury almost? But he just smirked down at me again, waving the huge tip so close to my lips that if I'd twitched, he'd be on them. 'I'm girly, right?' he said. He phrased it like a question, but it felt like a command somehow. 'No' I said. With a beast like that, of course not! He laughed, and grabbed me by my hair. It wasn't long like it is now, but it was long enough for him to get a good grip. I didn't fight it, I didn't want to fight it. 'No, dumbass, I am. I'm the girliest guy you've ever seen. And I like it like that.' I nodded, though it was hard with his hand holding my head. He laughed as he slowly stroked the throbbing monster in his grip.

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