Falling for My Sister Bree

My name is Aubrey, but my family just calls me Aub. I lived with my little family just north of Vegas, me, my mom, Anita, and my lovely sister Bree. I had just turned 18.

My grandfather had been a wealthy publisher and he left each of his children a very tidy sum. That meant that mom, her sister Emily, and her brother BJ wanted for nothing. They had bucks.

Don't get me wrong, after the estate was divided three ways, we weren't in a class with Warren Buffett or Bill Gates, but by almost anyone's measure, we were wealthy. I remember the day when Mom bought our big house with its circular driveway, large foyer, huge kitchen, and 5 spacious bedrooms. She just wrote a check for it like she was buying a turkey at Whole Foods!

Mom refused to indulge in household help, which she could have easily afforded. She wanted to make a home for me and Bree. She felt that was her calling in life.

Mom went through the laughable charade of being a typical MILFy suburban mom who just happened to have a hundred million dollars in the bank. Oy vey!

She dated here and there, but despite being a total fucking knockout at age 38, 5 feet and 5 inches tall and 125 very fit pounds, she was usually content with homemaking...managing the house, baking pies, worrying about my "uneven" development, and keeping Bree, a tornado of sexuality, at least somewhat in line.

I have a very clear memory of one typical sunny Nevada morning. Mom's call for me and Bree to come for breakfast echoed through the house, a melodic yet commanding tune that signaled the start of our daily ritual. Mom loved rituals. They made her feel safe.

I shuffled into the kitchen, my eyes still groggy with sleep, and took my usual seat at the huge kitchen island, which was by now bathed in the soft glow of the early morning sun.

Bree sailed in after me, 21 years old, her long, blonde hair cascading down her back like a golden waterfall. At 5 feet and 8 inches tall and 121 very curvy pounds, she looked like a goddess in her pink, oversized t-shirt that barely reached the bottom of her pretty ass, and she didn't forget to wiggle it while reaching for a piece of toast. She knew exactly how to drive me out of my skull.

Bree and I were polar opposites. I was a nerdish, socially inept, National Merit Scholar, wildly unsuccessful with girls. Bree was a gorgeous, addle-minded, large-breasted bimbo, a beauty queen, in fact, the most beautiful girl I had ever seen. She had many sexual partners, both male and female. And she did not seek them out. She didn't have to. They beat a path to her door.

I had had an enormous crush on Bree since before middle school. She always ignored that, accepting it as her due, and always adopted a very superior air around me and seemed to barely tolerate my existence.

Sometimes she enjoyed teasing me, and that was the closest she ever came to showing any actual affection for me. At other times, she was simply dismissive of me and my hella boring successes as a scholar, and she thought my lack of masculinity was a cause for hilarity. She had a way of always making me feel small and desperate.

"Morning, Aub," Mom said, in her very high and soft girlish voice, placing a steaming plate of eggs and bacon in front of me. Her smile was warm, but there was a glint in her eye that told me she had something up her sleeve.

"Mornin', Mom," I mumbled, my voice still thick from having been asleep.

Bree giggled, a sound that never failed to make my heart flutter. "Mom," she began, her mouth full of toast, "you know what you said to Aub yesterday about his hair?"

Mom's eyes lit up with amusement. "Oh, yes," she said, turning to me with a playful smirk. "How Aub would make a prettier girl than almost all of the ones out there."

"Yeah," I said, rolling my eyes and poking at my eggs with my fork. "Thanks for that."

"It's not just your hair," Mom continued, her voice teasing. "It's everything. Your slender frame, those delicate features--why, with a little makeup and the right outfit, you would be a little Vegas hottie!"

Bree's laughter filled the room, a sound so infectious I couldn't help but smile, despite the embarrassment coursing through me. "Imagine that," she said, "Aub strutting down the street in yoga pants and a tiny crop top!"

"You'd have all the boys--and some girls--chasing you," Mom said, winking at me.

I felt a strange mix of emotions: annoyance at their teasing, a hint of pleasure at the idea of being desired, and a deep-seated ache knowing that, as a male, I would never truly experience having the same allure that Bree had every day of her life...every fucking minute of her life.

"Yeah," Bree said, taking a sip of her coffee, her breasts rising with the motion. "You'd be so popular, Aub. You could be prom king and queen!"

Their banter washed over me, and I couldn't help but feel a twinge of resentment. It was always like this, them poking fun at me in that loving, giggling way that left me feeling both cherished and emasculated.

But I knew better than to argue with them--Mom would always side with Bree, and Bree would always side with Mom. What a pair they made! Bree was the apple of Mom's eye, and I was the awkward sidekick in our little family sitcom.

As we ate, Mom's eyes never left me. "You know, Aub," she said, a hint of seriousness in her tone, "sometimes I think you'd be happier if you had been born a girl. You're so sensitive, so smart. Not goofy like the boys your age. You'd have the world at your feet."

Bree nodded in agreement, her eyes sparkling. "You'd totally kick ass as a girl," she said, reaching over to pat my hand. "You've got the brains, the looks...everything but the right parts!"

Their laughter filled the room, a sweet, taunting melody that made me feel both included and utterly alone in my desires. And as I sat there, watching them, I couldn't help but wonder if they were right.

If only I had been born with those...parts...then maybe, just maybe, my life would have been different. Maybe then, I could have been the one to make Bree's eyes light up with something other than amusement. I knew she was bi. She had nearly as many female lovers as male ones. Maybe if I'd been a hot girl or a big strong guy instead of a useless, femmy boy, I could have been the one to make her heart race, her body tremble. The thought of that almost made me swoon.

Mom must've noticed my silence and its meaning because she leaned in, her still-hard breasts pressing against the table and said, "Don't worry, Aub. You're perfect just the way you are. Besides, if you were a girl, you'd have to deal with all that girl...stuff." She waved her hand, gesturing to her own body, and I couldn't help but think about the "stuff" she was referring to. The same stuff that made me burn with desire for her and for Bree.

Bree took another bite of her toast, her teeth tearing through it with a crunch that seemed to echo in the silence. "Mom's right," she said, her voice sticky with jam. "You're fine being a boy. You can still wear makeup and stuff if you want, though."

I nodded, trying to swallow the lump in my throat. The truth was, I had experimented with makeup before. It was something I had discovered in secret, a way to feel closer to my feminine side. But hearing them talk about it so casually, as if it were nothing more than a costume to be put on or taken off, made it feel...ordinary. Less like a taboo, and more like something I could actually do without fear of judgment.

"Thanks, Bree," I managed to murmur, my cheeks burning.

Mom patted my shoulder. "You know we're just teasing," she said, her hand lingering a beat longer than it needed to. "But if you ever do decide to switch things up, you've got two experts right here to help you out."

Their words hung in the air like a promise, a tantalizing glimpse into a world where I could be everything I ever dreamed of being. And for a moment, I allowed myself to imagine it. The feeling of lace against my skin, the smell of Bree's perfume as we picked out a dress together, the way Mom's eyes would widen with surprise and then warm with acceptance when she saw me. It was a heady fantasy, one that made my cock rustle in my pants.

But reality had a way of crashing down on my fantasies. Always. I knew that no matter how much I wanted to, I couldn't just wake up one day as a girl.

I couldn't have Bree's body, couldn't feel the same way she did when she walked down the street in her tight, torn-at-the-knee jeans and high heels. All I had was this...whatever it was I had. I was a fucking mess. I had a lifelong crush on my sister and I wanted to fuck my mother. It was all weird and fucked up. Was this merely a result of teenage angst, or would I be helplessly locked in my fantasies for the rest of my life?

Bree took another sip of her coffee, her eyes meeting mine over the rim of her mug. I swear she knew what I was thinking. "You know," she said, her voice dropping to a whisper, "we could always play dress-up."

My heart stopped. Did she mean it? Or was this just another one of their jokes, a way to make fun of me? But the look in her eyes, the way she bit her bottom lip, it was...different.

Mom's hand slid down my back, tracing the curve of my spine until it rested on my hip. "What do you say, Aub?" she asked, her voice low and seductive. "Would you like to try on some of my clothes?"

The heat in the room seemed to triple, and my cock was now at full attention, straining to escape from its confinement. "Yeah," I managed to say, my voice barely above a whisper. "I...I think I would."

With a wink, mom stood up and grabbed my plate. "Why don't you two go to Bree's room," she suggested, her tone still playful. "We've got some old clothes that might fit you just right. Except Bree and I are larger in the bust area."

Bree took my hand, her grip firm and inviting. She pulled me out of the chair and led me to her room, her ass swaying in front of me. Intentionally. As she opened the door, she turned and looked at me, her eyes filled with a mischief that was both terrifying and exhilarating.

Her room was a little messy, but not a disaster. There was a pile of textbooks that I was sure she didn't understand. There was also a makeup vanity with a mirror surrounded by lights. It was like a stage, and I was about to become the star. She sat me down in the chair, her hands on my shoulders, her breasts brushing against my back. "Don't worry," she said, her breath hot on my neck. "We'll make you the most beautiful girl in Vegas."

The next hour was a blur of fabric and cosmetics. They pulled out dresses and skirts, lingerie that I had only seen in magazines, and makeup that promised to transform me into something other than the awkward, no-pussy-getting boy I saw in the mirror every morning. Bree painted my face with expert strokes, her fingers gentle as they traced the outline of my eyes and the curves of my lips. Mom hovered in the background, offering advice and encouragement, her eyes never leaving me.

Finally, Bree stepped back and spun me around to face the mirror. I gasped. The person staring back at me was...gorgeous. The makeup had softened my features, and the dress Mom had picked out hugged my body everywhere and it was so short it barely covered the bottom of my ass. My peroxide blonde hair fell in soft waves over my shoulders, and my eyes, lined with shadow, sparkled with a newfound confidence.

"You're...stunning," Mom breathed, her hand over her mouth.

Bree leaned in, her eyes smoldering. "I knew you had it in you," she cooed.

The doorbell rang, shattering the spell that had been cast over us. Bree's grip tightened on my shoulder as Mom called out, "I'll get it!" She practically skipped down the hallway. I heard the muffled sounds of hushed greetings and the click of the front door closing.

A moment later, Aunt Emily sailed into the room, her magnetic smile lighting up the space like a spotlight. She always looked wonderful, blonde, beautiful, and hella sexy at age 42, 5 feet and 5 inches tall and 122 fit and busty pounds.

"Well, well, well," she said, her eyes raking over my transformed figure. "Look at you, Aub! Is that you, Aub?"

I blushed, feeling both embarrassed and thrilled by her approval. Aunt Emily was like a celebrity to me, a successful businesswoman with a flair for the dramatic and a wardrobe that would make a drag queen weep with envy. She was the cool, older woman that I had always dreamed of being like, and now, here she was, in the flesh, looking at me like I was something special.

"What do you think, Emily?" Mom asked, her voice filled with excitement.

Aunt Emily pursed her lips, her eyes traveling down to my crotch. "Anita, I think that we have a situation here."

Mom's smile faltered. "What do you mean?"

"Look at him," Emily said, her voice more than a bit bossy. "He's going to be a problem. He's going to get himself into trouble. We have to protect him."

Bree and I exchanged confused looks. What did she mean? Protect me from what?

"He's going to college next year, Anita" Emily continued. "We can't just throw him out into the world like this and expect him to make the right choices. He's inexperienced. He won't know how to resist...assertive advances."

Mom nodded, her eyes narrowing as she considered Emily's words. "What are you suggesting?"

"A chastity device," Emily said, her voice firm. "We'll get him one, and each of the three of us will have the key. We'll wear them around our necks, on gold chains. This way, we can control the outcome of his urges."

Then she flashed the keys and I immediately grew weak. A chastity device? But as I looked at the keys, the way they gleamed in the light, something inside of me stirred. A sense of...submission? Excitement? I didn't know. All I knew was that the idea of being at the mercy of these three beautiful women was both terrifying and incredibly, unbearably arousing.

"But, Mom," I protested, my voice shaky. "I-I don't know about that. I want to have a chance at freedom!"

Mom's expression softened, but her resolve didn't waver. "Aub, sweetheart," she said, her hand on my cheek. "This is for your own good. You're so innocent, and we don't want you to get hurt."

Bree stepped forward. With her hand cupping my ass, she said, "It's like a promise, Aub," her eyes wide and earnest. "A promise that we'll always be here to take care of you."

"But you're my sister!," I protested. "No guy gets protected by his sister. That will be so humiliating."

"Don't act like a little cunt," Bree exclaimed. "You need to learn some self-control. And we can teach you that. I'm certainly willing to teach you that. You can also learn to obey orders. Do you understand, Missy?"

Hold on! Obey orders? Missy? This wasn't turning out like I had intended.

Then I complained, "Bree, no one places you on some king of protective regime. And you don't exercise any self control! Jeezus. You're a slut on roller skates!"

She shot back with. "Don't talk back to me little-thingy-thing boy or you'll find yourself in a world of hurt with me. Those kinds of rules don't apply to me. I'm Bree! We're gonna keep you in line!"

I did felt a strange thrill at her words. This was a promise of care and protection wrapped in a package of control and submission. And as the three of them closed in on me, their eyes gleaming with something I didn't quite understand, I realized that maybe, just maybe, this was the answer to all of my prayers. A way to truly belong, to be a part of a world that I wanted to be a part of.

They explained the rules:

1. No unlocking by anyone but one of them

2. No sexual activity without the consent of my three superiors

3. No disobedience of any kind.

It was all so overwhelming, but my cock was growing like I had swallowed a bottle of Viagra. This was kinda hot.

Emily whipped a strange-looking device out of her purse. She was always Johnny on the spot! She said it was called a 'birdlock,' and it was sissy-pink and plastic. They all thought it was soooo cute! But as they locked my poor cock in place with a firm click, I felt a sense of peace wash over me. I was theirs now, and somehow, that made everything else seem so much less daunting.

Life with Mom, Bree, and Emily over the next few weeks was a whirlwind of feminine domination. They took turns being bossy in their loving and not-so-loving ways, dictating my wardrobe, my makeup, even the way I walked and talked.

Emily was the strictest, like a prison guard, always watching to make sure I didn't slip up. The paddle she had bought was never far from reach, a constant reminder of the consequences of disobedience. It was dark brown, overlaid by red hearts. But don't be fooled. It was made of Brazilian hardwood, as my ass would soon come to know.

"Sissies need to cry," Emily would say with an air of authority as she'd swat me with the paddle, hard enough to make me yelp and squirm. "It helps them keep their minds right."

And cry I did, my cheeks stained with mascara as I learned to navigate this new world. The sting of the paddle was sharp, but surprisingly arousing, a contrast to the softness of my panties and the sweet scent of the various perfumes that surrounded me. This had all turned into a strange, thrilling dance of pain and pleasure.

But it wasn't all paddling and punishment. There were moments of tenderness, too, like when Mom would stroke my long fake blonde hair and tell me I was doing a good job, or when Bree would kiss me gently on the forehead before sending me off to bed, the smell of her lip gloss lingering on my skin. And they taught me to embrace my femininity, to cherish the delicate, submissive side that I had always struggled with.

The paddle became a symbol of their love and guidance, a tool to shape me into the girl they believed I could be. And every time one of them made me cry, whether from a sharp remark or a well-placed paddle-whack on the ass, I felt a strange sense of belonging. It was as if my tears were a release, a way to cleanse the slate of my former self and make room for the new Aub, the one they were sculpting with the paddle and their scolding words.

The paddle hurt most of all when Bree, the one I loved the most, laid me across her lap and punished me for displeasing her. Before she even brought the paddle down, I was repentant and heart-broken that I had disappointed her. It made me so sad to displease her.

I t also hurt because I had always had a fantasy of being her big strong man, the guy who could fuck her hard and make her say filthy things! And here I was being swatted and verbally chastised by the girl I loved, the one whose approval I needed the most. Bree, the beauty queen! Bree, who had been Miss Teen Las Vegas when she was a junior in high school!

The three of them were a formidable team, each one bringing something different to the table.

Mom was the nurturer, always there with a kind word and a gentle touch, soothing me with her high-pitched girly voice.

Bree was usually the teaser, always haughty and dismissive of my needs and opinions, her superior laugh and playful, but pointed banter keeping me in line. But she sometimes switched things up when she got very angry with me, and she would make my pretty ass pay for it when she laid me across her lap.

And Emily, oh Emily! She was the enforcer, the one who made sure that I never forgot my place. And my place, it seemed, was either under her thumb or across her lap, receiving a world-class, gold-medal ass-whipping that would leave me bawling and begging for mercy.

Together, they were a force to be reckoned with, to be obeyed, a trio of hot dominant babes who left me breathless and eager for more, even when I was tearfully rubbing my freshly spanked ass.

And as the days turned into weeks, and my body grew more accustomed to the tight dresses and the way-too-short skirts, I found myself craving the paddle, yearning for the tears that might win their approval. I wanted them to see me cry! It was a twisted sort of love, but it was mine, and I wouldn't have traded it for the world.