My name is Sissy Ann. I am a 16-year-old biological male, 5 feet and 7 in. tall and 120 lb. I am a sissy and have a very small cock. I have been a crossdresser since my birthday, but I am not permitted to indulge in that activity alone. All of that is directed by my mother, Cherie.

Cherie is 38 years old, 5 feet 9 inches tall and 128 lb. She is a very imposing woman, forceful, strong-willed, and successful. She doesn’t like me as a boy. She wants me to be very sweet, effeminate, and submissive and has become quite demanding of me in that regard. In particular, she says that I must learn to show respect and deference to her and to all the other female members of both my immediate family and my extended family. She is adamant about that.

Cherie recently went so far as to take me to court to have me legally declared a sissy. She prepared a brief and filed it with the District Attorney who prosecuted the case against me. I was not permitted to have a defense attorney. Losing the case to my imperious mother meant that I have no civil rights and that I legally belong to her. She owns me.

Cherie and the DA had to establish that I was naturally a sissy, and that due to her maternal guidance, I was already in an advanced state of sissyhood and submissiveness. She also had to show that my little cock was locked in a hard plastic chastity device 24/7, 365 days a year.

To make her case even more persuasive, Cherie dressed me in a tiny thong, a tight coral sequin dress that barely covered my pretty ass, and strappy high-heeled sandals. I was a vision of sissy sexiness and beauty. She topped it all off by paddling my ass red before court time. She thought if I had a freshly paddled ass and tears in my eyes that would make her case overwhelmingly clear.

The courtroom was packed.

You have to understand, I wanted to be submissive to my mother. I even wanted to belong to her. But the gravity and finality of the legal procedure was overwhelming. I would never be able to enjoy any male activities ever again. Why did my mom have to be so overwhelming?!

In court, Cherie sat confidently beside me in her black suit. Her eyes sparkled with maternal pride. The room’s silence was broken only by the excited whispers of the onlookers, which included my aunts and my female cousins.

The bailiff, a barrel-chested, virile-looking man, cleared his throat, and called the room to order. The judge, a stern-looking woman with a severe bob, peered down at me over her thick wire-rimmed glasses. Her eyes lingered on the brief Cherie had prepared, her brow furrowing slightly. I felt the weight of the world—or at least my world—on my shoulders, and I couldn't help but fidget in my too-tight dress.

"Young man," the judge said, her voice a low rumble, "are you aware of the proceedings about to take place here today?"

I nodded. "Yes, Your Honor." My voice was a mere whisper. The plastic chastity device that caged my cock was painfully tight, reminding me that my chances of not being declared a sissy were nil.

The DA, a hard-faced man, approached the judge with a stride that suggested he'd already won. "Your Honor, the state and the boy’s mother have compiled overwhelming evidence that proves beyond all reasonable doubt that the defendant is naturally a sissy, not really a boy at all."

He slammed his evidence folder onto his table, the sound echoing through the room. I well knew what was in that folder. The pages were filled with photos of me in various states of sissy attire and sissy sexual activity, all compiled by my mother.

The first witness was called: Dr. Marquez, a psychologist with a specialization in gender identity. She took the stand and confidently said in a measured, clinical voice, "Your Honor, I have examined the defendant extensively. It is my professional opinion that he is indeed a submissive sissy and, by law, should be stripped of his rights and placed under the legal ownership of his devoted and loving mother."

The room was a blur of faces, some sneering, others smirking. It felt like everyone in the room could tell that my dress was clinging to me like a second skin, and that my pretty thong was riding up between my ass cheeks with every shift of weight.

The doctor's voice droned on, detailing my supposed sissy tendencies—how I craved to be treated like a girl, how I loved my spankings, how my cock responded to humiliation, and the pleasure I derived from having my ass spanked. All of that was true, but it didn’t make the finality of the proceeding any less terrifying.

The prosecutor held up my chastity key for all to see, a cruel smile playing on his lips. "Your Honor, we submit this as Exhibit A: the instrument of the defendant's constant confinement and a symbol of his willing submission to his mother's will."

The jury, a mix of stern men and judgmental women, leaned in, their eyes flicking between the key and my crotch. I wanted to shrink away. Resistance was futile. This was the culmination of Cherie's masterful manipulation of my life, her ultimate victory over me. I loved her, but this shit was over the top!

As the trial proceeded, my heart raced, my palms sweated, and my cock, trapped in its plastic prison, throbbed with a desperate need to be free. And the sting of my freshly paddled ass was a painful reminder that no matter what happened next, I would always be my mother's sissy. I craved that, but did it have to be so final and so complete?

The next witness was a neighbor, Mrs. Jenkins. She testified to her firsthand knowledge of my deep-seated sissiness. Her words cut through my soul. She told the court how she'd seen Cherie spank me in public, and how my cries of protest had only been half-hearted. She said, “The boy didn't even try to squirm away like a proper boy, Your Honor! He is such a fucking sissy! Pardon my French, Your Honor. This subject gets me worked up!”

My mother's hand rested gently on my knee, her nails digging in just enough to keep me in line. She whispered sweetly in my ear, assuring me that all was well. "You're doing so well," she cooed. "Soon, this will all be over, and you'll belong to me forever." Her words, though meant to comfort, only fueled my dread. My submission to my beautiful and sexy mother had always been offered freely and lovingly by me. Why did it have to be required by law?

The DA displayed the final piece of evidence: the chastity device itself. The bailiff removed it from his briefcase and brought it to the judge. The judge held it up, scrutinizing it with curiosity and thinly disguised amusement. Then she turned to me and intoned. "Is this true, young man? Have you been living like this? Like a locked-up little sissy?"

I couldn't meet her eyes. I couldn't meet anyone's eyes. Instead, I stared at the floor. "Yes, Your Honor," I murmured. My voice was barely audible.

The room seemed to close in on me. The judge nodded, setting the chastity device back down with a clatter that sounded like a gavel. "Very well," she said. "The evidence is clear. Both the state and the mother have made a compelling case."

My heart sank. The end of my boyhood and my maleness was near. I had enjoyed being two things—a boy and a girl. From this point, I would forever be one thing—my mommy’s sissy! The spectators waited with bated breath as the judge made her final deliberation.

The prosecutor strode over to me, a smug look on his face, and placed a hand on my shoulder. "Don't worry, son, Your mother knows what's best for you. You're in good hands. Loving hands. You are a lucky sissy." His grip tightened, and I felt my little cock grow hard. What would it be like if he fucked me? And what about that bailiff? What would his cock feel like inside me?

The judge finally spoke, her voice cold and final. With her eyes piercing through my soul, she declared, "Based on the evidence presented, I hereby declare you a legal sissy, property of your mother, Cherie."

The courtroom erupted in a loud murmur.  But all I could focus on was my throbbing little cock.

I was now officially my mother's sissy. And then I realized that not much had changed. This wasn’t so bad. Then it started feeling sorta exciting and sexy!

As Cherie led me out of the courtroom, the crowd parted like we were in an old movie. But all I could think about was what was coming next. There would be endless days of submission, with both pain and pleasure, all wrapped up in the tight corset of my mother's love. And as we stepped into the hallway, she leaned in close and whispered, "Welcome home, my sweet little whore!" My god, I loved my mom!

Once home, she took me straight to my room. She sat me down on the bed and ordered me to strip. I did as I was told. She then took out a bottle of baby oil and started to massage it into my reddened ass, which she had thrashed that morning before court. Her touch was tender. She worked her fingers in slow, circular motions, soothing the ache.

"Now," she said, with her voice quite firm, but not unkind, "it's time for me to teach you more about being my sissy, Sissy Ann!"

I swallowed hard. She was holding a strap-on dildo, the same one she'd used to train me before, but now it felt different. It was not just a toy anymore—it was a symbol of her newfound legal power over me. She fastened it around her waist, adjusting the straps until it was ready to pillage my village. My cock, still trapped in its plastic prison, gave a pathetic twitch at the sight, begging for the relief that could only be found as an act of my mother’s mercy. She did not look merciful.

"On your knees," she commanded, and I obeyed without hesitation. She stood before me with the dildo jutting out, threateningly. "You will learn to serve me, to serve all women," she says, her voice like a melody that fills me with both dread and excitement. "You will be the perfect sissy. I will be so proud of you!”

Her hand moved to my neck. Her grip was firm as she started to pound my ass. "Look at me," she hissed.. "Look at me, and tell me you love me."

My voice was hoarse but clear, "I love you, Mommy."

My mom's eyes were gleaming. "Good sissy," she purred, and then she jammed the strap-on into me. I gasped, and my eyes watered. The sensation was overwhelming. Both the pain and the pleasure destroyed all remaining vestiges of my male identity.

Then she fucked me long and hard until I shot my little cock’s big load, making a mess of my chastity cage.

That was followed by a very sound paddling for making the mess. Through my sobs, I apologized to her from the bottom of my heart.

Then I fell asleep for the night in her loving arms.

The next morning, Mom ordered me out of bed early for she had a visit planned for me with her sister, my Aunt Vicky, and her two horrible teenage daughters, Kagney and Shawna. The thought of facing my two worst tormenters filled me with sissy dread. 

The first thing I heard when I entered Aunt Vicky’s door was Kagney exclaiming, "Oh my God, like, totally!" her voice a high-pitched squeal that grated on my nerves. She and her sister, Shawna, were sprawled across the velvet sofa in Aunt Vicky's opulent living room, their legs entwined, and their eyes gleaming with malicious delight as they watched me approach them so stricken with fear.

"Yeah, we totally heard about your little... legal situation," drawled Shawna, her lips curling into a smug smile as she flipped her hair over one shoulder. At 18 and 19, respectively, she and her sister were about the same age as me, but their immaturity was reflected in the way they spoke and acted, a stark contrast to the sophisticated environment to which I was accustomed.

"Mom says you're gonna, like, start coming over every Tuesday to wash our asses," Kagney said, popping a piece of gum in her mouth. "It's like, the best thing ever. Finally, some structure in your sad little life! Youi can show that, like, you have respect for this family!"

My face burned with humiliation. Washing the asses of the two girls who had made my childhood a living hell was not exactly how I'd envisioned my Tuesday nights. But Aunt Vicky had agreed with my mother that this was what I needed, and who was I to argue with those two?

"So, like, what do you think, sissy, Mr. 2-inch guy?" Shawna piped up, her voice dripping with sweetness that didn't quite hide the sarcasm beneath. "You gonna be a good boy and, like, do as you're told? Maybe I should say good girl! Either way, you're gonna be our bitch to the max!"

I gulped, my eyes darting to Aunt Vicky, who sat regally in an armchair, sipping on a glass of wine. She offered me a small smile and a nod of encouragement, reminding me that this was all part of her favorite plan for me.

"Y-yes," I stuttered, my voice barely above a whisper. "I will show you the respect my mother says you deserve from me."

"That's what I like to hear!" Kagney crowed, clapping her hands together. "Now, come over here and show us what you've got. Don't be shy, we're all family!"

My knees trembled as I made my way over to the sofa, my eyes locked on the two pairs of perfectly manicured feet before me. I knelt down, reaching for a wet washcloth that lay on the coffee table. My heart was racing, and I could feel my own tiny member straining against the fabric of my dress.

"You know," Aunt Vicky said, her voice a purr, "it's not just about washing their asses, Sissy Ann. It's about respect. You need to show them just how much you appreciate their time and effort in helping you become the best sissy you can be."

I nodded, my eyes flicking up to meet hers briefly before I turned back to the task at hand. Kagney was naked and bent over the back of the sofa on her stilettos, her ass perched high! She glanced over her shoulder at me, delivering taunts and orders that sliced through my soul.

"Mmm, that's the spot," she cooed, as I tentatively began to clean her. "Are you sure you haven't done this before? It seems that you were, like, born to have my ass in your face!" I washed every inch of her gorgeous ass, giving extra attention to her ass-crack. I thought I was gonna die right there on the spot!

Shawna was next. "Don't forget, I want both cheeks cleaned, ass-washing boy!," she instructed, her voice laced with superiority and amusement. "And the crack. You wouldn't want to miss that, would you? I certainly wouldn't want you to miss that! And the two of us are the bosses here, you tiny-dicked wonder! Maybe I should say blunder." Then she assumed the position, bending over the back of the sofa and arching her ass in the air. I had never liked her, but she did look like 10 million bucks! I desperately wished I had a huge cock and could fuck her harder than she had ever been fucked! But that wasn't my lot in life. My lot in laugh was washing her ass and not being able to come!

I bit my tongue, the smell of soap and their natural scents mingling in the air as I obeyed my mean cousins. My hands were shaking so badly I could barely hold the washcloth, but somehow, I managed to clean Shawna's ass without missing a beat.

"Good sissy," Aunt Vicky murmured from her chair. "You're learning what respect means."

As I finished, Kagney and Shawna both leaned back, their eyes never leaving mine. "You know," Kagney began, her voice a purr, "we've got some ideas for how you can show us even more respect. We deserve a lot of extra respect for a motherfucker with a fucking mini-dick like yours!"

"Both of you are so hot and so pretty. That makes everything you say true. I’m a better person because I got to wash your pretty asses," I said as I packed up my little ass-washing kit that had been gifted to me by Mom  earlier that day. I kissed both of them good-bye on the ass, waved to Aunt Vicky, and my mom and I returned home. I was in the clear, at least until next Tuesday evening. OMFG!

Mom was waiting for me when I arrived home, lounging in a silk negligée on our new California king size bed. She had moved me into her room, declaring that I was now officially her girlfriend. The room smelled of her expensive perfume, and the walls were adorned with framed photos of the two of us at various high society events, a stark reminder of my new role as her trophy sissy. She looked at me with a mix of love and ownership, her eyes gleaming with satisfaction at the sight of her well-behaved pet.

"How was your date?" she asked, a knowing smile playing on her lips. She knew full well what had transpired, but she enjoyed the charade.

"It was... enlightening," I replied, trying to keep the tremor out of my voice.

Mom's smile grew wider, a predatory glint in her eyes. "I'm sure it was. Now, come here and tell me all...