tagTransgender & CrossdressersMy Big Sister Ch. 04

My Big Sister Ch. 04


Paul was a fucking asshole. He has been one of my best friends since first grade, but he is a fucking asshole, always had been and always will be. Seriously, he knew my other best friend had feelings for me and just let me stay in the dark, then he turns around and helps her stalk me with video cameras, and now here he is currently laughing on the bathroom floor after I confronted him about the entire thing.

Yeah, he's an asshole, and rightfully deserved hard punch in the gut I gave him.

"It's not that funny," I told him, as he dramatically doubled over and groaned in pain. "Dude, get up, you're not hurt."

For a moment, Paul continued his sissy whining about me punching him, then he started breaking out into more laughter that made the vein on my forehead feel as if it were about to pop.

"S-Sorry dude," he chuckled, trying to calm himself down. "But...come on, if the roles were reversed you'd be laughing at me too!"

"No, because I'm not a jerk like you," I growled. "Dude, why didn't you tell me about May? I think I deserve to know who's been stalking me since third grade."

"It wasn't my place to tell you, that's her business, I was just helping her along," he chuckled wiping a tear from his eye. "Yeah I wanted to say something, if anything just to piss of May, but then I remembered just how scary that chick is and I decided to let you figure it out for yourself. I didn't think it would take this long though."

"Well did you have to give her those perv cameras of yours?"

"Hey! They aren't perv cameras, they're state of the art equipment that I personally modified to monitor others."

"Namely, the girls in the lockeroom."

"That was only for experimental purposes."

"Whatever," I sigh, shaking my head. "Dude, as much as I love May as my friend, it's pretty weird to know she's been spying on me for more than ten years." And probably jerking herself off to my image, but I don't think I should mention that.

"So? It's not that big of a deal," Paul shrugged. "While we have our...differences, I do have pretty good eyes when it comes to the female gender. She's definitely not hard to look at, if only I could shut that trap of hers. I wish someone with her looks would stalk me..."

I groan, leaning against the sink rubbing my temples. When I had dragged Paul into the boys restroom, I was ready to get on my knees and beg for him not to blurt out my secret, which was starting to become not-so-secret, to anyone in school. But it seemed he didn't know anything about May's extra parts, so everything was alright...for now.

"So...where are my details?" he asked me suddenly, a Cheshire grin covering his face.

I arched an eyebrow in confusion. "Details?"

"Yeah, she told you she liked you right?" he gave me a smirk. "What'd you two do after that?"

"W-Well we..."

"Aha! I knew it!" Paul started laughing again. "You two bumped uglies, didn't ya? Man, I never knew May was the type to give it up on the first date."

"Damn it Paul, fuck you," I grumbled, pushing past the cackling idiot and leaving the restroom, only to find May standing right outside the door. "O-Oh, were you standing outside the whole time?"

"Yeah, I saw you drag Paul in there, is that him laughing in there?" I nodded to her. "What a dick." She then gave me a quick look. "Hmm, judging by your red face, your dark eyes, and your shaking hands...I'd say you asked Paul about the spy cams he gave me?"


"I've been watching you since we were kids, I know all your ticks by now," May shrugged. "And don't worry, he doesn't know anything about me having a penis, and doesn't know that you enjoy having it pound you into unconsciousness."

"Yeah I figured that much out myself," I told her, ignoring the blush crossing my face. "Well, I've got free period so I'm heading up to the roof, I'll see you after class."

"Wait a sec," she told me grabbing my arm, and then slipping something into my hand. "I need you to hold onto this, I've got gym period and I don't want anyone finding it on me." I opened my palm and found a small bottle of lube there.

"May! Why do you have this?!"

"Well you never know, we might get really horny in school," she giggled giving me a wink. "It's always good to be prepared." And with that, she stole a kiss on my cheek and walked off into the other direction, leaving me both stunned and excited.

I shook my head and quickly stuffed the lube into my pocket, hurrying up to the roof, where I mostly spent my free periods and lunch time. I enjoyed sitting up on the highest point of the school and taking in the entire city while enjoying whatever the hell it was I was eating for the day.

"Damn rain," I groaned looking at all the puddles on the roof. "There's not really anywhere good to sit."

"Excuse me," a voice spoke from behind, startling me a bit. I swiftly turned and saw a girl sitting on the small tool shack and giving me a bright, but somewhat alarming, smile. "Would you mind telling me what you're doing in my roof?"

"Your roof?" I scoffed at her. "I've been coming up here for three years, if anything this is my roof."

My retort seemingly didn't faze her as she merely just kept her increasingly creepy smile and said "Well how much did you buy it for?"


"Yes, if you own the roof that means you had to have bought it right?" she asked jumping off the shack and walking toward me. "So how much did you pay?"

"I..." I avoided her gaze. "Didn't pay anything...I just..."

"Assumed that since you were the only one up here that it was yours?" she asked. "How simpleminded of you."

When I didn't give an answer she gave me another smile before a small, somewhat condescending, giggle escaped her lips, which slightly irritated me. "I haven't seen you around before." I told her. "You a new student or something?"

"Of course not, I just hardly ever come to school. I don't see the point," she told me like it was no big deal. "And I definitely don't socialize with those beneath me, so if you don't mind I kindly ask that you quiet yourself and be on your way. I wish to enjoy my solitude...in solitude."

Even while she was being quite obviously rude, the smile didn't go away, I was actually starting to wonder if it were some permanent defect. "Are you trying to make me to leave?" I asked folding my arms. "Just who the hell do you think you are?"

"Moi?" she asked innocently. "Well you'd have to be rather dense to not know who I am, but I'm beginning to believe you're someone of lower status and intelligence. You'd have to be to not know of the daughter of the wealthiest and famous Russian businessman, Vladimir Yelstin."

I rolled my eyes at her condescending tone, of course I know who that guy is, who doesn't? He's only the biggest sleazebag asshole in the city who keeps trying to buy everything he can touch, at least that's what most people, namely May, believes. However, I have firsthand experience with the guy, as he has visited my house on a few occasions, trying to buy out my Mom's company. I can't tell you how many times we've sat down at dinner with him with him going on and on about his ideas for the new company he wants to build after she gives it up to him. I mean, if you were to just sit down and talk with him you would think he was a decent enough guy, and he really is, but some of his business actions have been very questionable to me and it's very annoying how he thinks he can buy and sell anything as he pleases.

Plus, I think he has a thing for my Mom. He always shows up with all these luxurious gifts and takes her out to expensive places. My Mom, being the brat she is, is not one to refuse free stuff from others, even though she already knows she's leading him on.

Now that I think about it though, I do remember him mentioning something about a daughter that he wanted to introduce to me because we were the same age...what was her name? Mina? No, it began with a D. Uhm...Darya? Dina? Diana?

"Dominika." I said out loud, snapping my fingers only to have two hands roughly grab me by the collar.

"I ask that you don't call me that," Dominika told me, and for a split second there her smile turned into a dark frown, but it quickly curved back up in that second. "Just call me Mini, please."

"O-Okay," I squeaked, coming to the conclusion that her creepy smile was much less scary than her frown. "Mini...got it. I won't make that mistake again."

She didn't answer me for a moment, in fact her face seemed to fall into a solemn expression for a second there before she quickly turned her back to me. "State your name," she ordered to me.

"What is this the Middle Ages?" I grumble under my breath. "My name's Peter...charmed."

"I am certain you are," she smiled, flipping her gorgeous dark red hair at me.

Now that I've gotten a full view of her, I have to say she's damn good looking. Long dark red hair, tanned skin, slim athletic body, mouth watering legs, and a nice, big, round ass that I strangely wanted to grope. My eyes then fell to her chest, the one area where she was apparently lacking.

"Wow, they're so small," I accidentally muttered loud enough for her to hear. Before I knew it, I was suddenly pushed onto the ground, face down, with her twisting my arm. I have no idea how she managed to get me in such a position so quickly, but I am strangely turned on right now at this development.

"Excuse me, I'm a bit hard of hearing sometimes," she told me, twisting my arm harder. "What was that last comment of yours again?"

"N-Nothing," I groaned again. "I didn't say anything."

"I figured as much," She let my arm go and suddenly picked something off the ground. "Oh my, what's this?"

"I don't know what you're..." I froze when I saw that she was currently holding the bottle of lube. I had completely forgotten that May had given it to me! Damn it!


"Is there something you'd like to tell me?"

I tried to speak, but no words would form out of my now dry mouth. So I decided to do the only thing I could at the moment and started sprinting down the steps, leaving the lube in her possession.

"Shit! Shit! Shit! It's over I'm done for!" I wailed as I suddenly slammed into what felt like a brick wall. "Ow, what the...holy..." When I looked up, I saw a very large black man wearing a butler outfit glaring down at me. Not wanting to face any more problems than I already had, I decided to forget it and ran past him down the hall, hoping to get away from all this.


"You idiot," May groaned to me. "You dropped the lube?"

"Sorry, I guess it fell out of my pocket or something."

"Damn it, and I was counting on getting some before I got home," she sighed. "Now I've got a hard on and no ass to pound. Woe is me."

"Could you worry about your boner later?" I asked. "Right now we should be worried about more important things, like the fact that Mini's gonna tell everyone in the school and my reputation will be destroyed."

"I seriously doubt that," May shrugged, digging into her ear. "That chick you're talking about, Dominika Yelstin, I have a class with her."


She nodded. "The bitch is keeps to herself and has no friends, which makes sense since she thinks she's so much above everyone," she informed me. "I remember when we were lab partners once, she kept giving me this creepy smile making me get the feeling that she didn't want me there, and then when I asked her to help, she told me that she does not work with peasants. Can you believe that? And who says peasant anymore? She's lucky I didn't knock her ass out in front of the whole class."

So that's how it is huh? I figured she'd be the loner type, her attitude wouldn't keep many people around very long, maybe that's why she doesn't come to school often. Then again, if she wanted friends, she should probably think about changing her attitude...and not twist people's arms.

"So, wanna come over?" May smirked, rubbing her hand on my thigh. "Since I couldn't get any action in school, and April's been wanting to try out a new position on you."

"Maybe later, Kimmy needs my time right now, she's been giving me a real attitude lately," I informed her. "I think she's been getting sexually frustrated, we haven't done it in a few days after all."

"Suit yourself," May said heading toward her car. "Just remember, even if she destroys your ass, I'm still gonna fuck you."

I laughed at her, and walked down the opposite street, my mind still fixated on that Mini chick. I got this feeling that she's got a superiority complex or something, it sure looked that way to me. Maybe if she weren't such an asshole, I would consider trying to get closer to her, after all, she's really good looking, and it would be nice to know a girl that didn't have a dick...not that I don't love my family and my best friend, it's just a bit overwhelming to have all the major girls in your current life owning a dick. My train of thought was suddenly broken when I felt something cold and hard touch the back of my head. It didn't take long for me to figure out exactly what it was, and I suddenly stopped in my tracks, throwing my hands up in surrender.

"Yo kid," the voice behind me was deep and menacing. "I'm gonna ask this one time, do you want your fuckin' brains all over the street?"

"O-Of course not."

"Alright then, get in the car." he ordered. "Now."

At that moment I watched a limousine pull up right next to us, when I turned to face the man, I recognized him as that guy I had run into earlier. "Quit starin' and get in the damn car!" he ordered grabbing me by the collar and literally throwing me into the limo.

"Ow," I said as I felt something land in my lap. Looking down, I noticed it was the bottle of lube I dropped earlier. "Eh? Where did this..." I looked up and noticed that Mini was sitting right in front of me, that exact same smile on her face. "Ah! It's you!"

"You don't address a lady like that," Mini spoke, wagging a finger at me. "It's very rude you know."

"Guess you'd know a thing or two about that," I spat. "Personally, I think it's very rude to have your gigantic butler kidnap me by holding a gun to my head and throwing me into a car."

"Oh, that's just Marcus's way of saying hello."

"He needs to find a better way to do that."

"How about next time I just break all your bones?" Came Marcus's voice from the front of the limo.

I gulped and decided to just leave that conversation there, turning to face Mini. "What do you want?"

"I just wish to talk with you," Mini told me innocently. "Is that too hard to ask?"

"Well, I've actually got something I need to-"

"I'm sorry, I think you misunderstood," Mini interrupted, the frown that scared the shit out of me back on her face. "When I say I wish to do something, then that means it's going to happen. With or without your consent."

That last line set a slight trigger in my head, making my ass start to burn again. Lately this thing has been like a radar or something, and knowing that I quickly began to panic before I launched forward and pinned her to the seat. She didn't seem to mind at all as I shoved my hand under her skirt and grabbed an unmistakeable bulge in between her legs.

"Fuck," I groaned. "I knew it. Just my fucking luck."

"I see that you have experience with women like me," Mini grinned grinding her bulge against my hand. "Then you should have no problem complying with what I'm about to ask of you."

"B-But I have to be-"

Her hand gripped my shoulder like a vice as she frowned again. "Let's go through this one more time," she said in a voice that made my spine shiver. "You have no problem with what I'm about to ask of you, right?"

That voice was immensely scary, not to mention her grip was rather strong for a female. I'm starting to doubt May would have even been able to knock this girl out so easily. Plus I had a feeling that if I said no, then that Marcus guy who's driving this limo might really kill me, I gulped loudly and nodded as she released me. "Good," she giggled. "Marcus, do you mind?"

"Do your thing, girl," he said as he began rolling up the window.

"Wait, you wanna do it in here?" I asked.

"Where else?" she asked.

"Well, I mean can't we go to a hotel or something?"

"Mmm, you talk too much," she grinned pushing my head down where she wanted it to go. "Now, get down and make me feel good."

"Fine," I sighed shifting so that I was in between her legs.

She spread them wide and lifted her skirt so that I could see her bulge better, judging by it's size I'd say that she, like all the other girls, was definitely packing pretty well. I shifted her panties to the side allowing the soft cock to flop out onto the seat. I looked like a sleeping anaconda that didn't want to be disturbed, even in it's flaccid state, it was already longer than my own. "Mmm, yes," she moaned as I began stroking her completely soft cock. "Good boy." I reached further and slowly rubbed her large balls in effort to harden her quicker, however I didn't expect her cock to suddenly jump alive and smack my face.

"Sensitive are we?" I grinned as Mini grabbed the back of my head and shoved it onto her cock.

In it's full capacity, it was longer than Mom's but much less thick so I was able to fit more than half of it in my mouth, however that didn't seem to please Mini as she kept trying to get me to go down further.

"Come on," she giggled, rubbing the back of my head. "I know you can do better than that, the maid's are usually able to get the whole thing down."

"Do I look like a fucking maid to you?"

"Well, you can be if you want, I think you'd look pretty in a cute little maid outfit," She then thrust her hips and shoved it back into my mouth. Now, she was taking control and began pumping in and out of my mouth at a very slow and steady speed. "Yes," she moaned. "Use some teeth."

Teeth? Whatever, it's her cock not mine. I grazed my teeth against her cock earning louder moans from her and causing her thrust to become more quicker and harder. "Mmm, that's a good cocksucker," she moaned as the head of her cock slammed repeatedly against the back of my throat. "I'm going to cum, you'd better drink it all!" Seconds later I felt her hot seed shoot down my throat yet her thrusts still didn't stop, her cock swished the cum in my mouth like it was in a mixer before she finally pulled out, allowing me to swallow it.

"Mmm," she moaned flopping her cock against my face. "Is my cum tasty?"

"Surprisingly, yeah." I said once I'd swallowed it all.

My hands then found their way to her chest as I unbuttoned her blouse and removed it from her. I looked down at her small perky breasts, they were a bit bigger than I had thought earlier, but still pretty small compared to most women.

"I didn't like your earlier comment about them," she told me, referring to her chest. "So as atonement, you have to ride my dick."

"What, no doggy style?" I asked sarcastically.

"That position is for the lower class people who have to work," she smiled. "We aristocrats have our servants do everything for us."

"Lazy bitch," I muttered to which she grabbed my nipple and twisted hard.

"Again with your snide comments," she said spreading her legs and letting her cock stand. "Luckily, I love a man who thinks he can stand up to me. It makes it that much more fun to break them." She then dug into my pocket and pulled out the lube, squirting a good amount on the tip of her cock. She began lathering the substance, filling the entire limo with the slick sounds of her stroking herself. "You like that, don't you?" she asked me, moving her hips a bit. "Come on, you know what to do."

I groaned and crawled up on the seat hovering over her cock, I grabbed it from the base and began to guide it to my hole.

"You're so slow," she sighed grabbing my thighs and shoving the entire thing into my ass earning the most effeminate scream I've ever let out in my life. "There we go, now was that so hard?"

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byDaBlackMamba© 36 comments/ 85457 views/ 210 favorites

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