My Estranged Sister Eve

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I take off the clothes and hand them to Chantel. "Awe, she's got such a cute little baby dickie. That little ball sack is adorable." I immediately turn red and try to hide my crotch in embarrassment. She grabs more clothes for me to try on.

It seems like we spend hours trying on different clothes. A cute little Christmas outfit, some sexy lingerie, stockings, mini skirts, more underwear and a lot of dresses. By the time we're done, I feel like I just tried on half the store. As I take off the last piece of clothing, Chantel gathers up all the clothes except for the first things I tried on and starts to fold them and goes to take them to the checkout counter, while Eve stays with me as I get dress. I bend over to grab my boxers. I feel Eve's hand on my back and it slides slowly down to my rear. She grabs a handful of my ass. I nearly lose my balance, but she catches me and pulls me close. Her chest pressed up against my back and I can feel her hard on up against my ass. Her arms wrapped around me. "You no longer have to wear boys clothes. I had Chantel leave that pink dress and the underwear for you. You looked so adorable in them," she whispers in my ear as her hands travel up and down my body. The touch of her fingers is like being touched by a flame.

She finally pulls away and grabs the underwear I tried on first. I turn around to face her as she bends down and lifts up my leg. I grab onto her shoulders for support as she slips on the silky undies. Once she has them on both feet, she slowly slides them up, taking extra time to slide them over my butt. Then she grabs the training bra and slips it on over my arms. Finally, she grabs the dress and slides it over my shoulders. She grabs my face and looks deep into my eyes. "You are so beautiful, Shay."

Her lips are on mine as her tongue slips into my mouth. Her thumb strokes my cheek as her tongue rubs up against mine. Finally, she breaks away. "I guess we should check out."

"Wait. You want me to go out there like this? What if people see me in girls clothing? I'm a boy!" I cry.

"Babe, no one is going to judge you and if they do they'll have me to deal with," she says as she grabs my old clothes, unlocks the door, and grabs my hand, pulling me behind her. On our way out, she dumps my old clothes in the nearby trash can. I feel so exposed and self-conscious. I see the other customers glance at me on our way up to the cash register. I can only assume what they're thinking, that boy is wearing a dress!

Chantel has a cashier ring us up as she and Eve chat. "You're bringing that cute little girl to my New Year's Eve party, right?" Chantel asks.

"Oh we wouldn't miss it for the world," Eve says as she hands the cashier her credit card.

"Good! Like anyone else could do a better job. Of course, I'll be cooking the ham. I can't wait to see little Shay all dolled up on New Year's Eve! Please tell me you're going to spend the night like old times? We can have so much fun with her!" she squeals with excitement.

"We'll see, I can't make any promises," Eve says as she takes her credit card and receipt. Eve hands me my coat and I grab all the bags of clothes as Eve hugs Chantel and they kiss. Watching Eve kiss someone else makes me feel a tad bit jealous. Then Chantel comes over to me and kisses me on the cheek as her hand makes its way up my dress giving my ass a good squeeze.

"I'll see you on New Year's Eve, you cute little sissy," she whispers in my ear which makes me feel like I've been struck by lightning. I swallow down my nerves and follow Eve out the store.

I throw the bags in the back seat and hop in the car. "Just one more stop and then we can go home," Eve says as she starts the car.

I strike up the nerve to ask Eve about Chantel as we pull out of the parking lot. "So... ah... Did the two of you have..."

"A relationship?" she asks and I nod. "Yes, we have a kind of friends with benefits type of relationship. We both transitioned at the same time. We've always had each other's back when the world turned their backs on us. Chantel will always have a special place in my heart."

"She seems..."

"Like a sexual deviant?" Eve interrupts.

"I was going to say friendly," I say.

"Ha, she's definitely friendly and she loves to give if you know what I mean," Eve says.

"Not exactly..."

"She loves to be on top and can be very dominant." I swallow hard at the implications. "Don't worry sweetie, I'm not going to force you to do anything you don't want to."

We pull up at a beauty salon. As we walk in, once again Eve is greeted in open arms. "Eve! Just the woman I was looking to see," this beautiful woman with caramel colored skin and a thick Indian accent says. "Oh! You brought a friend! Who's this little cutie?"

"Israa, this is Shay. He'll be staying with me from now on," she says.

"Oh, lucky you! He's so adorable! Are we giving him a makeover today?" she asks.

"Yes! Let's make him look beautiful!" Eve says as she pulls my coat off me.

"Oh that won't be hard, he already looks gorgeous in that pink dress! Oh my god, he's like a present just waiting to be unwrapped!" she says. It feels so erotic the way they're talking about me. As if I'm some kind of pet. Israa gabs my hand and pulls me to a chair in front of a mirror. "It's time to bring out some of those amazing features."

She leans down over my shoulder and looks in the mirror with me. "You are so beautiful. I know just what to do. With a face like yours, we only need to touch a few things up. A little blush, some eyeliner and I've got the perfect lip gloss."

Without a second to waste, she gets to work. She leans in front of me and I stare into those dark brown eyes of hers as she starts to apply some powder to my face. As she rubs it into my cheeks she starts chatting with Eve. "Please tell me you're bringing this cutie to Chantel's New Year's Eve party!"

"Of course, but he's still only 18 years old," Eve says. As she continues to apply the makeup I get a good glimpse at her cleavage. Her breasts look so soft, like mounds of caramel waiting to be licked.

"Like that's a problem... I can think of more than a few activities he can participate in," she giggles as she stands up and leans over to grab some kind of pencil, then I see the bulge in her white pants. It's only a few inches from my face. I see it twitch as if it's trying to escape, desperately seeking a moist mouth to enter. I can feel my own little pecker start to get stiff. She then crotches back down and brings the pencil to my eyes. I flinch as it gets closer. "Don't move hun, don't want to poke an eye out."

She brings the tip against the skin around my eyes. Then she grabs a tube with pink stuff in it. Takes it out and brushes the tip against my lips. "Now smack those lips together for me."

I do as I'm told and rub my lips together. "Perfect!" Once again she puts her head over my shoulder and we look in the mirror together. As I look into the mirror I barely recognize the girl staring back at me. She's beautiful! "You're absolutely gorgeous. Your hair is just long enough to give you that dixie look."

She wheels me around to show Eve. When her eyes glance upon me, it's like she's seeing me for the first time. "Oh my god... She... She looks like Shauna."

Who's Shauna? I guess it doesn't matter. The only thing that matters is that Eve's happy. She looks at me as if I'm the most beautiful girl in the world. "Would you like me to get you the makeup I used?" Israa asks.

"Absolutely! Can I get it in bulk?" Eve asks.

"Of course!" she replies as she rushes to the backroom. There's an awkward silence with Israa's absence as Eve's eyes never leave mine. The way she stares at me is like someone seeing a flower bloom for the first time in their life. I wish she would look at me like this all of the time. It makes me feel beautiful. Eve finally breaks her trance and hands me my coat. As I put it on I can still feel her eyes on me.

Finally, Israa comes back with a large bag of makeup. "Remember it only takes a little of each to really bring out Shay's features. She really doesn't need much."

"Thank you, Israa. I appreciate it," she says. Eve pays her and grabs the bag of makeup.

"Anything for you, Eve! I can't wait to see you at the party. Maybe we can have a repeat of last year?" she asks winking at Eve. Then she turns to me. "I'm really looking forward to seeing you as well, cutie. Don't forget, just a touch of each."

She pulls me into a hug, I can feel her cock through her pants press up against my stomach. She then lays a peck on my cheek before pulling away.

Israa then kisses Eve on the lips. "Tell Chrissy I said hi," Eve says before we finally leave the store. I'm so confused about Eve's relationships.

Eve puts the makeup bag in the back with my other clothes. We pull out of the parking lot and head back home. The ride home is rather silent. I can't stop thinking about Eve. The way she looked at me in the salon. Her relationships with Chantel and Israa. And who is Shauna? Things have gotten so confusing. Especially the way I feel about her and the things I wish she would do to me. I know it's wrong, but it feels so right. I've never felt this way about anyone.

We finally arrive home and Eve parks the car in the garage. I grab all the bags of clothes as Eve grabs the makeup. Once inside, I lay out all my clothes on my bed. I can't believe she bought me all of these. It's practically a whole new wardrobe. I see Eve at the door. "I put your makeup in your bathroom."

I look up at those beautiful eyes of hers. "Thank you so much for all of this!" I say to her.

"Anything for you, Shay," she says. "I need to finish up my story and post it. It'll take an hour max. Afterwards, do you want to help me decorate?"

"Yes! I would love too!" I say excitedly.

"Great! I'll come to get you when I'm done," she says before taking off to her office.

I start to fold and put away my clothes. It feels almost like a weight has been lifted off my shoulders as I fill my closet up with all girl's clothes. As if I'm finally becoming who I was meant to be. My old life ended and my new life has begun.

Oh crap! I totally forgot about the laundry. I quickly rush downstairs and into the laundry room. I take out the sheets from the dryer and put Eve's wet clothes in. I can finish her other clothes tomorrow.

Then I head back upstairs and fold my new clothes and put them neatly away. Once I finish putting my new clothes away, I head downstairs. Eve comes out of her office as soon as I reach the bottom. She goes into her room and a few minutes later she comes out in shorts and a t-shirt and makes her way downstairs.

"Hey, beautiful, ready to put up some Christmas decorations after we grab something to eat? I know I've probably should have put them up sooner with it only being a couple of days away." She called me beautiful! My knees go weak and it feels like a flock of seagulls took flight in my stomach.

I nod my head yes, too struck with nerves to speak. She looks absolutely gorgeous in her simple get up. Her legs are fully on display and her shorts barely fit over her thick ass. They sure don't do a good job of hiding that fat cock of hers. It's practically fighting her shorts to get out. She notices me staring at her crotch. "Like what you see?"

I nervously swallow as I force my eyes up to hers. Again, I'm speechless, all I can do is nod. "How are you going to help me if you can't even put words together to form a sentence?"

"I... ah... I..." She puts her hands gently around my neck and pulls me into a kiss that would give Hallmark a run for their money. The feel of her lips against mine is almost too much. My little cock is instantly hard and already drooling precum.

She pulls back and looks down and giggles. "Looks like someone is pitching a tent..."

My face burns bright as I see my little cock poking up. I look down in embarrassment. She pulls my face up towards hers and looks me in the eyes. "Shay, I love you so much."

"I love you too!" I can barely speak with so much emotion inside me as if I'm going to explode from all of it. As if someone put mentos in a liter of cola and closed it shut. Without thinking I wrap my arms tightly around her waist and bury my face in her breasts. She embraces me.

I can feel her cock twitching against my stomach.

Finally, she breaks off. "If we don't get started decorating, we'll have to spend Christmas without a tree," she laughs giving me one last kiss on the forehead. "Let me heat up that leftover pizza and let's get started!"

She heats up the pizza and we quickly scarf it down.

"The Christmas stuff is out in the garage," she says as she strolls over towards the door. I follow her like a lost puppy that found a home. As we enter the garage, there's another door I never noticed at the far end. Inside it's just a rather large storage closet. There are a bunch of red tubs with green lids and a long box that obviously has a fake tree in it.

After we get everything inside. We open up the boxes and sort through everything. She pulls out two decorative stockings, one with my name on it and one with hers. Why would she have one with my name on it? "You have a stocking with my name on it?"

"Of course! I've always wanted to spend Christmas with you. I haven't seen that in forever! Awe, it looks just as cute as the day I made it! Why don't you go hang them up over the fireplace," she says making me blush. I take them and hang them on the mantle above the fireplace. Then we start hanging garland up everywhere.

"Guess what I found!?" she says behind me causing me to jump. I turn around and see her hanging a mistletoe above my head. She then leans in and kisses me. "Hmmm, now where should I hang this to get the best possible excuse to kiss you some more. Oh! Here's a good spot!"

She hangs it just under the loft where I usually sit at the dining table. I can't wait until our next meal! Finally, Eve opens up the box with the Christmas tree in it. I help Eve set the Christmas tree up in the living room by the windows to the right of the stairs that go up to the loft. We decorate the tree in white, star-shaped lights and snow like tinsel along with little icicle-like ornaments. By the time we finish with the tree, it looks almost as if it got hit with an ice storm, but it looks majestic. Eve grabs a chair and brings it over next to the tree. She pulls out a beautiful star and hands it to me. "Would you do the honor?"

"I would love to," I say as I take the star. She helps me up onto the chair. I blush as I feel her hand go up my dress and hold my ass for support as I reach up and put the star on top of the tree.

I turn to face her as she pulls me down into her arms. I wrap my legs around her waist and my arms around her shoulder as both of her hands latch onto my butt. I look into those deep hazel eyes of hers as she leans up and plants her lips against mine. After a long passionate kiss, she looks up into my eyes once more. "Will you take my virginity?" I ask trembling.

"It would be my honor," she says as she nuzzles her nose against my neck and plants a few kisses there. She walks us up the stairs and before I know it, wherein her bedroom.

She gently lays me down on the bed and leans down to kiss my lips. Her hands run up my thighs, slowly going under my dress. I lift my butt off the mattress as she hikes my dress up. She then pulls me up and I raise my arms so she can take the dress off over my head. As the soft fabric moves past my face, her lips meet mine. I wrap my arms around her shoulders as her tongue slips into my mouth. Her hands slip underneath my bra and start to pull it up. Once again I raise my arms into the air as she pulls the training bra off. Her hands go to my chest as she starts to rub my nipples, they're so sensitive. She gives each a soft pinch before her hands dive down underneath my panties. "You look so adorable in these, I don't want to take them off of you," she whispers into my ear.

I wrap my arms around her neck once more as she lifts my bottom of the bed so she can slide my panties off. I'm now completely naked. She then pushes me up to the center of the bed.

She pulls off her shirt. After she gets her bra undone, she slides her shorts off followed by her own panties. Her cock springs free from its silk-clad prison. She then crawls on the bed towards me as those big soft breast dangle from her chest and I can see her python stiff as a board. She lays kisses on my legs as she climbs on top of me. Her lips travel up my thighs and arrives at my little pecker. "You have such an adorable little cock and a cute pair of small balls to match."

Hearing her say that makes me feel so... Embarrassed. She can see me blush. "Shay, it's nothing to be ashamed about. God gifted you with the most amazing bubble butt I've ever seen."

She lays a few kisses down on my tiny pecker before she takes both my penis and my small little balls inside her mouth. Oh my god! It feels so amazing. The heat of the inside of her mouth makes my little wee wee as hard as it can ever get. But just as I feel like I'm about to blow, she stops. "Not yet my love," she whispers.

She then starts to kiss her way up to my chest. Taking a few seconds to pause at each of my tits, taking each of them in her mouth. The feeling of her tongue swirling around my nipple sends ripples of pleasure through me. She gently bites my left nipple eliciting a gasp from my lips. Then she makes her way up to my neck, each kiss is like pouring gasoline on the already burning fire of my love for her.

She sucks on my neck, I can feel her teeth as she does her best to give me a hickey. Finally, her lips are on mine, her tongue dives deep into the depths of my mouth, seeking treasures untouched by anyone else. I can feel that fat cock of hers resting on top of mine. I can feel the heat of her large python as it overpowers my little pee pee.

I grab her big soft melon shaped breasts. The size of them makes my hands look so small. She lets out a moan in my mouth as I squeeze her boobs. She gyrates her hips, rubbing her massive member against mine.

She gets off of me and in one quick motion, flips me on my stomach. Next thing I know, she's got my ass cheeks spread and her tongue is spelunking down my butthole. I can't help but moan as her tongue prods my rear. It feels so weird but really good. I can feel her press it deep into my tight little pucker as her hands squeeze and spread the cheeks of my ass.

I'm in complete heaven as she lathers my little flower bud with spit. Waves of pleasure crash into me like a storm hitting the shoreline. She withdraws her tongue and suddenly I feel a finger pressing up against my behind. The pressure builds before it finally nestles itself inside my bum. I groan from the way it spreads my little butthole open. Giving me a mixture of pain and pleasure. I grab a pillow and hug it tightly.

It continues to sink deeper into my derriere and it all of a sudden rubs up against a really sensitive spot and fireworks shoot off like the 4th of July. She pulls it back before ramming it back into that sweet spot. I moan into the pillow as she rubs her finger up against it. My little guy instantly goes hard once more. I tense up as another finger joins in, spreading my ass even further. It hurts a little.

She pulls out altogether and reaches over to her bedside table and pulls out a bottle. I hear her squeeze a glob of lube into her hand and rub it all over her big dick. Then she squirts more into her hand and rubs it all over my little asshole. I grab a tight hold on the pillow as she buries her finger once more in my asshole, getting it all nice and lubed up. It's only there for a few minutes before she pulls it out. "Shay, this is going to hurt," she says.

123456...8