My Estranged Sister Eve

Story Info
Merry Xmas/Incest - Wincest sissy w/ his transgender sister.
30.9k words
4.67
87.8k
250

Part 1 of the 2 part series

Updated 06/09/2023
Created 12/21/2018
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Warning - Story contains incest, transgender girls sticking their dicks in sissy boy butts. Feminization, sissifications, anal, blowjobs, a gangbang/orgy and lots of lewd sex.

All characters involved in sexual activities are of the age of 18 or older. This story is based on true events that take place in the near future. If none of these suite your fancy, I apologize. For those of you that like it, please do enjoy. Also comment what you like or dislike about the story in the comment section!

*****

While I sit on the plane I have plenty of time to take it all in. I'm still in shock that they're gone. My parents were murdered... The crime was left unsolved. My parents were strict Catholics no-nonsense kind of people. They were church going people. They gave to the community. They were loved by everyone... How could someone do this?

My life in Santa Barbara is over. I don't know what lies ahead. All I know is that I have to go live with my estranged sister, Eve, in Michigan. My sister is much older than I am. We were never very close. She and our parents never got along, which is why she left a long time ago.

I barely even know her. We've barely ever spoken. Our parents avoided all conversations about her and took all her photos down. I never understood why. What could she of possibly done to elicit such actions? I know my parents can be strict, but she's their daughter after all... Right?

As much as I miss my parents, it'll be nice to have a fresh start. Back in Santa Barbara High, I wasn't popular. To be honest, I was bullied... A lot.

One reason has always been because of my figure. I'm not like most boys. My body has never fully developed. I don't have ripped muscles or hairy legs. In fact, I don't even have a single strand of hair below my dirty blonde eyebrows. To make matters worse, I've been given a body with a somewhat feminine figure. You could say I have what most would call a bubble butt. In fact, I've been confused for a girl more times than I can count. You have no idea how humiliating it is to be constantly referred to as a girl. And at Santa Barbara, most kids purposely made it a point to let me know how much of a sissy I am. Although, if I'm being totally honest, there is a part of me, a large part of me that feels that they're right. Deep down, I feel more like a girl than a man. I've always fantasized about wearing women's clothing and sometimes I have dreams about sucking a big fat cock. I've dressed up before and I love the way it feels to look and feel beautiful. To feel vulnerable and feminine. My parents, may they rest in peace, never found out about my secret, but I already knew back then that they wouldn't approve.

The only friend I did have back in Santa Barbara totally understood. She'd even help me dress up. Her name was Zita. She was my best friend... She wasn't popular either. She's transgender and got ridiculed often because of it. But she understood me and I understood her. It's hard to come by that in this world.

As much as I'm going to miss her I know where I can reach her. We would spend hours online in Aratheon. Mostly because both of our real lives weren't a good place to be at. The virtual world was somewhere we could be ourselves. I was a majestic female elf priestess and she was a brutal female warrior. We were the perfect duo. But we're practically on separate sides of the country now, but that doesn't mean I still don't worry about her. She has a tough life. She lives in foster care with no real family. We shared everything together. Now she's all alone in Santa Barbara.

Now that I'm going to live with my sister in Michigan, hopefully, she'll understand. I've never actually had the chance to visit her. In fact, I've never even stepped foot outside of California. Moving to Michigan at the end of November will be a new experience altogether. I've never seen snow before.

The plane begins its descent into Detroit. As we dip below the clouds, the city comes into view. What a sight to behold. Three gigantic skyscrapers rise above the rest, connected together by several walkways. The towers are surrounded by a beautiful park and several other large buildings. It's hard to believe this is Detroit. I learned in history class that Detroit used to be a city filled with despair and poverty. Now, thanks to John Farrell, the wealthiest man in the world, it's become the most advanced technological hub in the world. His company Prometheus Corporation has its headquarters here in Detroit in one of those towers along with Gennecho University. The school he built that allows free tuition to all its students. He just opened it recently. The man is a legend and one of my idols.

We finally land. After I get off the plane, I make my exit through the TSA checkpoint. That's when I see her. Eve, my sister, is standing at the gate waiting for me. The sight of her sends a shiver down my spine. She's wearing a tight mini thigh high black dress with a black leather jacket over it. A pair of black boots that come up to her knees to top it off. Her dark brown hair, the same hair that both of our parents share, falls gracefully down to her shoulders. Her bright hazel eyes connected with mine as she chews on her bottom lip with those pearly white teeth. Absolutely stunning. What am I saying!? She's my sister!

Before either of us say a word, she pulls me into a hug. "It's so good to see you, Shay, even under such sad circumstances."

"Let's grab your luggage and head out. The drive back to my house, or should I say our house, is a couple of hours. It might take us longer with the weather," she says. "By the way, please tell me you brought a jacket. It is December in Michigan..."

"I didn't even think about bringing a jacket!" I sigh looking down at my jeans and t-shirt. "I don't even own a winter jacket."

"It's okay, we can stop and pick one up," she says with a smile.

I grab my suitcase and follow Eve out. As soon as I step foot outside, the cold air hits me like a bag of bricks. I go temporarily blind as the brightness of the snow reflects into my eyes. Goosebumps appear on my skin as small little white flakes pelt my face. "It's freezing!" I say shivering. After my eyes finally adjust it really doesn't make a difference, all I can see is white. The fluffy white snow is completely covering almost everything as it continues to fall from the sky with such persistence.

"What did you expect, it's Michigan in winter," she laughs. We finally arrive at her SUV and it's completely covered in snow. She pulls the keys out of her pocket and hits a button which opens the hatchback. I set my luggage in the trunk and get in as she grabs the scrubber and cleans the rest of the car off as I get in the front seat. Holy crap, it's a Mercedes! How can she afford such a car?

She gets in after she finishes scraping the snow off and we finally take off. It has an automated drive system, so the car practically drives itself. Thank god! Because you can barely see the roads with all the snow coming down, it's a complete whiteout. I'd never imagined snow would be like this. So blindingly white.

It's not long before we're on the highway. We push through the storm in complete silence. I don't know what to say. I don't remember the last time we've spoken. She didn't even show up at the funeral. To be honest, it's hard to believe we're even related. We barely know each other at all, now I have to live with her...

After what seems like forever, we take the exit ramp to a place called West Branch. She has the car pull into an outlet mall and parks in front of a clothing store. "I bet we can find a nice winter jacket for you in here," she says.

Following Eve into the store, I notice how upscale it is. After browsing through the winter jackets, Eve pulls out a white down coat with fur around the rim of the hood and black snap buttons. She places it in front of me and takes a long glance. "This would definitely look good on you," she says with such a hypnotizing smile.

"Isn't this for girls?" I ask, even though deep down I think it's beautiful.

"No, it's unisex... Just try it on," she says. Hesitantly, I do what she says. It fits quite snuggly. I'm surprised by how comfy it feels.

"Oh my, it looks so perfect on you! We're getting it!" she gasps with excitement.

I slip it off and she grabs it from my hands and heads up to the checkout. After she purchases it, she forces it on me. "You look so adorable."

Adorable, just what every man wants to be called... But I can't lie, deep down inside I love it.

We grab a bite to eat before getting back on the road. During our travels Eve finally decides to break the ice. "So... Shay, tell me about yourself."

Her words echo around inside my head. What is there to know about me? "Well... I like to play video games with my best friend Zita and I'm a huge bookworm. Mom and dad always said it was rare to see me without a book," I say. I see a tinge in her expression and I can only assume it's because of mom and dad. What happened between them?

"What kind of books do you read?" she asks.

"Well... Right now I'm huge into the Aratheon series. Zita and I are big into the MMO game and I can't help but become obsessed with the story."

"Aratheon? Really?"

"Yeah! It's a fantasy realm full of elves, dwarves and what not."

"I know what it is, I'm just surprised to see you're a big fan of it. I've read all of the books myself and I absolutely love them! I played the game for a bit, but I'm far too busy to get really into it." I can't believe it. She's an Aratheon fan!

"No way! I can't believe you're into Aratheon!" This made my life!

"Of course I'm into it! Did you think I'm some kind of prudes like mom and dad?" she asks and I can't help but tense up upon hearing their names.

She's quick to take notice. "I'm sorry, Shay. I didn't mean that."

After traveling for I don't know how long in silence on the icy, slick, roads with what seems like a wall of white snow falling from the sky, we finally pull off on an exit to a city called Gaylord. We take a left at the stop light and it's not long before the city is in the rearview mirror. We take a few zigzags, hills, turns and loops, all encompassed in trees covered in snow. Finally, as the day grows dark, she turns off on a long winding driveway. The sight before me about blew me away. It's the biggest house I've ever seen!

It's got a garage with three large doors. The garage itself is covered in stone with a large wooden patio built on top of it. There is a set of stairs just next to the garage that leads up to the patio, with a large welcoming door to the house that appears to be made out of logs.

The garage door on the far right opens up and we pull inside next to a Lamborghini and a huge ford truck. How can she afford all of this?

"Where did you get all this money from?" I ask.

"Ha, I'm a top-selling author on Amazon. I make a killing off my books," she says. "Now grab your things and I'll show you up to your room."

As we head inside, we enter a small room with a coat rack, a washer and dryer and a place to put your boots with another door that leads into the rest of the house. As we walk into the actual house, I'm blown away just by the living room. The far wall is almost all windows looking out into the most amazing view of the woods down the hill all covered in snow. There's a glass door in the middle that leads out to another patio. The floor is all wood with a giant carpet in the middle surrounded by two comfy leather couches and several side tables that look like they were made out of the roots of a tree. The wall on the opposite side of the windows has a giant flat screen above a huge fireplace made out of stone.

Past the couches in the corner just below the overhanging loft is a long rectangular dining table with 8 chairs around it. On the opposite side of the room is the kitchen, which is completely underneath the loft that extends all the around the room. The kitchen is huge with the left side completely covered in countertop and cupboards that swing around the wall all the way to the right side connecting to biggest stainless steel fridge I've ever seen. There's a giant stove on the left side of the kitchen with an oven. The top row of cupboards stops at the end of the left side and a row of windows takes over the far wall where the sink is. An island takes up the middle of the kitchen. To the right of the kitchen is a set of stairs that lead up to the loft. On the left side of the kitchen next to the door, we just came in is another set of stairs that go down into the basement. And between the door, we came in and the fireplace is the giant welcoming door to the patio.

Tugging my luggage, I follow Eve up the stairs to the loft, which is less of a loft and more of its own floor with multiple rooms. We continue through the balcony that overlooks the main floor and she stops at the second door and opens it for me. The room is rather small compared to the rest of the house, but it's still bigger than my old room. The floor is covered in a nice soft brown carpet and the walls are all wood. It's got a nice cozy bed in the middle, the frame is made out of logs. There's a dresser with a tv on it across from the bed and a desk next to it. There's a window that looks out into the driveway next to the bed. On the other side of the bed is a small closet. There's a bench at the end of the bed I set my suitcase on.

"Why don't you make yourself comfy and then meet me downstairs for dinner in about twenty minutes," she says. "Once we've eaten, we can relax and get to know each other better. How's that sound?"

"Yeah, sounds good," I say.

"Great," she says as she takes off downstairs.

I open up my suitcase and pull out my tablet and my VR set and put them on the desk. I take out my clothes and fold them neatly on my bed. After I put them away in the dresser, I stuff the suitcase underneath the bed and head downstairs. The smell of pizza takes over my senses. I notice an empty box of DiGiorno sitting on the kitchen island. Eve strolls out of a room on top of the balcony in a silk black nightgown with a silky grey robe on top. The nightgown comes down to the middle of her thighs, showing off the most mesmerizing pair of legs. She looks down at me, biting her lip. Our eyes connect with such tension it causes my knees to grow weak. She finally breaks her gaze away and makes her way down the stairs as she closes the robe around her.

I hear the alarm go off for the pizza as she enters the kitchen. She grabs an oven mitt and pulls the pizza out of the oven and sets it on top of the stove as steam seethes off of it. "Let's give it a few seconds to cool down," she says. "Why don't we make ourselves comfy on the couch while we wait."

"We might as well go over the ground rules now," she says.

"I've already taken the time to have you enrolled into a homeschool program. You'll be finishing up your schooling from here if that's okay with you," she says. The news is music to my ears. I was so afraid of starting over at a new school. The thought of trying to make new friends sounds awful. The outcome was going to be the same. No matter what school I go to I will always be bullied. That's just the way it is. But being homeschooled, I don't have to worry about that.

"Really!? That's awesome!" I say with excitement.

"I'm glad you're alright with that. Also, if you don't mind, I could use your help around the house," she says. That doesn't sound all that bad. I mean, she is letting me live here with her, the least I can do is pull my weight.

"With as big of a house as this is, there's quite a lot to do to maintain it. I have a cleaning crew come once a week to do the floors, bathrooms, and windows, but there are still quite a few tasks left for us," she explains.

"How good are you at cooking?" she asks.

"I've never really tried before, but I'm a quick learner," I tell her.

"Well, it can't be any worse than my cooking, as you can see Digiorno is about the best of my cooking skills. If you don't mind cooking, I'll do the dishes," she says.

"Honestly, I'll be more than glad to do both, this your house and you've got a really important job. I'd be more than happy to take over some of the chores like cooking and cleaning the dishes. I can even do your laundry for you as well. I want to help out as much as possible," I explain.

"That would be wonderful! Thank you so much!" she says with excitement.

"No... Thank you for allowing me to live here," I reply.

"I could never turn you down," she says with a smile. "Now let's eat."

She then gets up and heads over to the kitchen and pulls out a pizza cutter. After she cuts up the pizza, she grabs our plates and fills them with a few slices. She takes both plates over to the dining table and sets them down, as she sits at the head of the table.

"Be a dear and grab us some drinks," she says crossing her legs as the silk robe and nightgown reveal more of her thighs. I start opening cupboards, searching for cups until I find them. Then I head over to the automatic ice/water dispenser on the fridge and fill up both glasses. Finally, I take my seat next to Eve and dig in.

"Shay, as glad as I am to have you stay here with me, I have a fairly strict routine that I would like to stick to," she says as she takes a bite of pizza. "Every morning I'm up by 5 AM. I like to have a cup of coffee while I read to get myself in the right mindset. I'll usually eat breakfast by 8 AM."

"I like to work out and shower after breakfast. Then I'll spend most of the rest of the day in my office working on my writing. I'll take a break around 1ish for lunch, then it's back at it until around 4ish. I'll usually end up relaxing a bit before dinner with some wine and I either end up in the hot tub or I'll put on a movie before hitting the sheets for the night."

"I'll try not to disturb you while you work," I tell her.

"I appreciate that, while I'm working I value my privacy, besides you'll have homework of your own to finish. But that doesn't mean that we can't spend time together. Trust me, Shay, I want to spend as much time with you as possible. We should have never of been strangers. I promise you there will be plenty of time for us to spend together if you'd like that."

"Yes! I would love that!" I say.

She smiles with delight. "Me too!"

"Now how about we go downstairs and watch a movie after we clean up the mess in the kitchen and I show you the rest of the house," she adds.

"Sure!" I grab her empty plate and mine and head over to the kitchen. She grabs some zip lock bags and puts the leftover pizza in them and stores them in the fridge while I start cleaning the few dishes. She then grabs a dry towel and starts drying the dishes I've cleaned. It doesn't take long before the dishes are all cleaned up and put away.

"We sure make a good team, don't you think?" she asks with a smile.

"Yeah!"

"Now let me show you the rest of the house, we'll start with my room," she says.

I follow Eve upstairs. We enter her room, which is really nice and cozy. She's got a little furnace in the corner, a giant bed full of pillows right next to it. There's a little stand next to her bed with two-picture frames standing up on it. I notice one of them is of me as a kid. I don't recognize the other, it's a woman with gorgeous blonde hair, a lot like mine. There are several paintings hung up on the walls. The floor is wood, but there's a giant fur rug covering most of the room. She's got a corner room so there are two windows. One looks out onto the backyard and the other looks out onto the side. She's got a giant closet next to a door to the bathroom stock full of clothes.

"Here's my room, it can get nice and cozy in here," she says as we walk into the bathroom, which is just as amazing. The floor is made out of stone and the walls are all the same wood covering most of the house. She's got a giant tub on the left and all the way to the back is a walk in shower with multiple shower heads and all sorts of nozzles. On the right is a long counter with two sinks and a giant mirror. Just before the tub is a little cubby with a hamper full of her dirty clothes on the other side is the toilet. "This is where you'll find my dirty laundry. You don't have to do my laundry, but I really appreciate it."

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