My name is Abby, short for Abernathy. I am a 20-year-old biological male, five feet and seven inches tall, with a slight, even willowy, feminine build. I graduated from high school at age 14, and from UCLA at 16. I am currently a PhD student in comparative literature. I am a legalized sissy, owned by my mother Sondra.

Sondra is divorced, 40 years old, and a stunningly beautiful and well-preserved woman. She is a tremendous beauty at five feet and eight inches tall and 128 pounds. She is bisexual, but her sexual activities are almost entirely confined to other women. She has an unshakeable belief in female supremacy and treats males with haughty disdain. I would say that treatment also includes me, but my situation is tempered by the fact that she truly loves me.

Sondra is an attorney and runs the most powerful law firm in SoCal in Century City. In addition, she is a highly successful investment banker. She has a staggering net worth. Dude, she has mega-bucks!

You see when I turned sixteen my world changed. Sondra wanted another daughter, and what Sondra wants, Sondra gets! Needless to say, she is very authoritarian toward me, and she sat about feminizing me in every way possible.

She demanded that when I call her Mom and Mommy, that I do so in a very submissive tone. That makes her feel respected, and she is a stickler about being respected.

She has also been dressing me in skirts and dresses since my sixteenth birthday on. All of that is reinforced by a regime of chemicals that give me cute little tits and make my pretty ass look like a ripe peach. The downside is that the chemicals are concocted to prevent me from having an orgasm. And they work…usually. Of course, in those rare instances when I do manage to have an orgasm, I find it thrilling beyond measure.

It’s a bummer when I can’t get an orgasm, but since my mother has managed to make me a sissy at heart, and also because I love receiving Sondra’s approval, I’m down for the whole deal! Being Sondra’s sissy almost always makes my life exquisite.

So, not too long after my sixteenth birthday, Sondra went to court and had me declared a legalized sissy. My only defense was that I have a very large cock, 9 inches when soft. Everything in that kangaroo court, however, was against me. I wasn’t allowed to speak, and I had no legal representation.

Because of the decision that was arrived at in minutes, my bitch mom became my fucking owner!

I now have no legal rights, except for ones she might agree to let me have. Such power for one human being to have over another! It’s a fucking scandal, but it’s the law! I think she really did it because she finds the idea of completely feminizing a pretty young male to be a thrill.

Sondra is very self-righteous about the whole thing, and she assures everyone who knows us that she took the action for my own good because of my effeminate and submissive nature. She says she was only protecting me. It’s an extremely unfair situation, but I do love my mom completely and I obey her without hesitation. 

Sondra's primary purpose in legally seizing me as her sissy was to impose a regime upon me that would teach me to respect her and all other females in every way. All of the female members of our family are to demand respect and obedience from me and to assist in my complete emasculation.

So, I have for some time been Sondra’s submissive lover and trophy sissy, held in sexual thrall to her. Over the past year, however, she has relented a little and has been easing her iron grip on every aspect of my life. She really does love me, and she has been granting me little freedoms. I’m now allowed to purchase some of my own clothing, and on most days, I am permitted to dress myself and put on my makeup without assistance.

She has also declared that I’m to start dating. My dates are usually to be with one of my many bitchy female cousins or one of my pretty aunts. I am not permitted to ask anyone on a date, but any of my aunts or one of their daughters is permitted by Sondra to approach me. The intention is to provide me with a more vigorous social life.

There is one weekend not too long ago that I recall quite vividly. It held the promise of another one of Sondra's infamous parties. This time, however, there was an electric current in the air, a sense of anticipation that was palpable. Every time I walked into a room, the conversation would hush, and then, as if on cue, someone would bring up the topic of "dates" and "going out." It was as if they were all waiting for something to crack, and it had nothing to do with me getting my PhD in comparative literature at age 20.

On the afternoon of the party, my Aunt Mia pulled me aside, her eyes gleaming with excitement. "Abby," she said, her voice a seductive purr. "I've got something special planned for tonight. Something just for you."

My heart skipped a beat. Mia was gorgeous, and she had always been the wild one, the one who pushed the boundaries of what was considered "appropriate" for a sissy like me. She was the “cool” aunt. She had a way of making me feel both thrilled and terrified in the same breath. "What do you mean?" I asked, trying to keep my voice steady.

She took my hand and led me into the library, closing the door behind us. "I want to take you out," she said, her voice dropping to a whisper. "On a real date!"

The words hit me like a sledgehammer. A real date? With Mia? The very thought made my knees weak, and my cock pulsed with excitement. "But I've never..." I began to protest, but she silenced me with a finger to my lips.

"I know," she said, her smile wicked. "That's what makes it so much more fun. You're the prettiest and sweetest sissy in all of Beverly Hills. And I'm going to show you what it's like to go on a date with a real woman. This will be your big night, Abby, I promise,” she exclaimed. I was so excited that I was barely able to respond breathlessly, “Please, Mia, take me on a date! This is so exciting!”

So, the party was in full swing when Mia arrived from her home in the Hollywood Hills to collect me. At five feet and eight inches, she looked stunning in a form-fitting dress that accentuated her curves, her blonde hair in soft waves that fell around her shoulders. Dude, she was giving off the vibe that this was not going to be an innocent date that would end with me receiving a peck on the cheek! She took my hand, and the touch of her skin sent a thrill through me. "Come on, bitch," she said, her voice a low growl, "let's go have some fun."

So, she led me outside to her convertible Porsche. She slid in, her skirt riding up, and I followed suit, feeling like Cinderella going to the ball. As the car pulled away from the house, she leaned in and whispered in my ear, "Tonight, you're all mine, sissy." My cock was pulsing double time.

The date itself was pure sensory overload. We went to an exclusive French restaurant, where the maitre d' greeted us with a knowing smile and a nod to Mia, who was a regular. She had reserved a private booth; the candlelight casting shadows across her face and making her eyes seem to dance. Throughout dinner, she touched me, her fingers lightly brushing against my arm, my hand, my cheek, sending delicious shivers through me with every contact. She talked to me like I was a treasure…a sexual treasure. Cock throb! Cock throb!

After dinner, we went to a retro disco club, the kind that didn't ask for ID from me or even bother with a cover charge for someone of Mia's status. After all, anybody who was anybody knew she was Sondra's sister.

The music was loud, the lights strobing through the smoke-filled air as we danced together, her body pressed against mine, her hands moving in a way that left no doubt about her intentions. We were the center of attention, the most beautiful couple in the room. And for a brief, glorious moment, I forgot about the hormone treatments and the gender-affirming therapy that Sondra had imposed on me.

Mia’s moves were fluid and mesmerizing as she led me through a dance that was pure seduction. She whispered some sexually aggressive shit in my ear, her breath hot and her tongue tracing the curve of my earlobe.

I felt a thrill of fear and excitement, my heart racing as she led me to a private booth at the back of the club. She slid onto the velvet cushions, my hand still firmly in hers. I had become her prey! I played along, my knees shaking from the strength of my desire as I wobbled slightly in my high heels. My cock was throbbing so hard that it had begun to feel even larger! Did Aunt Mia know what I was packing?

Once in the booth, Mia’s hand found its way under my skirt. She gripped my thigh firmly. "Do you want this, bitch?" she breathed, her eyes never leaving mine. "Do you want to be treated like the pretty little sissy you are? Do you want me to change your fucking life?" Aunt Mia was getting a little scary.

I nodded, unable to find the words. My voice had abandoned me, leaving me only with the pounding of my heart and the pulsing of my cock. Mia's smile grew wider, and she leaned in to kiss me, her lips soft and insistent. It was a wonderful kiss, a very authoritative one, a kiss that claimed me as hers for the night.

Mia's hands grew bolder, her fingers slipping under my skirt and grabbing my ass. I gasped, my body responding in ways that were both terrifying and exhilarating. She leaned in, her teeth grazing my ear. "You're going to be the most popular sissy here tonight," she murmured. "Everyone's going to want a taste of you."

The thought sent a shiver through me, and my cock strained against the fabric of my skimpy panties. Mia noticed me squirming, her eyes gleaming with triumph. "Look at you," she said, her voice making a dark promise. "You're so eager to be used, aren't you?"

I nodded, my cheeks burning. "Yes," I whispered, the word a confession torn from my soul. "I want to be used, but I want to be used only by you, Mia."

Her hand tightened on my thigh, and she leaned in to whisper in my ear. "Good," she said. "Because tonight, you're going to find out exactly what it means to be on a real LA date! I paid for your dinner, get ready to put out, bitch!" 

The rest of the night continued the whirlwind. She had felt me up, but she had not really felt my cock yet as she expected it to be a minuscule sissy cock. She had no idea. 

The drive to her house was a silent one, the tension in the car thick and heavy. The wind played with my hair, the whorishly short skirt of my dress fluttering around my legs as we wound our way through the Hollywood Hills. The city lights twinkled below us like a sea of diamonds, a stark contrast to the darkness that lay ahead of us. I could feel my heart racing.

When we arrived at Mia's house, it was a modern marvel, nestled among the lush greenery like a gleaming jewel. She led me through the front door, my hand firmly in hers, and into a living room that screamed sophistication and wealth. The walls were adorned with art that likely cost more than the entirety of some poor kid’s college education, and the furniture looked like it had been plucked from the pages of an interior design magazine.

"Let's go to the bedroom," she said, her voice a seductive purr. I nodded, still unable to form words as she led me down the hallway. The anticipation was almost unbearable. I was nearly overwhelmed by a tight coil of need that had been building since she had first touched me in the library that night.

Once inside her bedroom, Mia turned to face me, her eyes smoldering with desire. "I've been waiting for this," she murmured, her voice thick with lust. "To finally have you all to myself."

You do know what dates with you entail per your mother, don't you sweetheart?

"I think I might have an idea," I say, "But Sondra and I have never really discussed it at any length. She enjoys keeping me in the dark sometimes."

"Everyone in the family has received the stipulations for what dating you and seducing you must include," she began. “There are three parts that must occur, but in no particular order. They are intended to instill respect in you for women.”

“The date must consist of you being seriously, I mean seriously, spanked. Sondra insists that the spanking must make you cry.”

“Also, as an act of humility and respect, you are to eat your date's pussy. That is also to serve as a “thank you” to your date for providing you with a fun time.”

“The third element that must occur is that you are to receive a thorough and vigorous ass-fucking from your date. The hope is that it will be humiliating enough that it will make you realize your position in the scheme of things.”

“Listen, Abby, this is your first date. I want to drive it to a successful conclusion and use you to satisfy my own needs as well. You are a fucking cupcake, after all! This is all to be consensual per Sondra, but we both know how important her expectations are to her. I am so excited. Your little ass is mine!"

"Wow," I begin. “All of that is pretty overwhelming. But I trust you Mia. I adore you, and I want to be seduced by you. You are my favorite."

Mia’s eager and confident hands moved to the zipper of my dress, the sound of it sliding down sending a thrill through me. She pushed the garment down, revealing my lace-covered breasts. "You're so beautiful," she said, her voice barely above a whisper as she stepped closer.

Her fingertips brushed against my skin, sending waves of pleasure through me. She leaned in, her breath hot against my neck, and I felt the softness of her lips as she kissed me. Her hand approached my cock without touching it, her touch featherlight, and I moaned, my body responding powerfully and instinctively.

The world outside the bedroom ceased to exist as Mia's hands explored my body, her touch both gentle and insistent. She removed my pretty thong with a deft flick of her wrist. Then Miss Thang Mia received the shock of her life! “Oh my god,” she exclaimed. “Your cock is ginormous, baby!”

And then she was on her knees before me, her lips wrapped around my enormous pride and joy. The sensation was like nothing I had ever felt before. I cried out, “Oh shit, Mia, are all dates really like this?”

Her tongue flicked and teased, her hands gripping my hips as she brought me closer to the edge. I could feel my cock engorging. I was losing control, making me feel less like a woman and more like a man than I ever had.

As the orgasm approached, I felt a strange sense of panic. What would happen when I reached the peak? I had been taking chemicals that were designed to enhance my feminine attributes, but they were also to prevent from ejaculating like a boorish male. Would I be able to come or would the orgasm-destroying hormones that Sondra had insisted on deny me? But my fears were lost in the wave of pleasure that crashed over me, my body shuddering as Mia's hot mouth worked its magic.

And then, it happened. I came like a goddam man! My climax ripped through me like a storm. There was a release like I had never felt before, leaving me trembling and gasping for air. “Fuck! Shit! Piss! Baby Jesus,” I was coming, one gusher after another, down her chin, in her hair, all over her beautiful face. She was stunned and drenched. Bitch hadn’t been expecting this!

But, dear God, my desire was still a raging fire! Mia was a skilled lover, her touch and kisses setting me on fire, dude! We explored each other's bodies with a hunger that was insatiable, each new sensation pushing me further into a world where gender meant nothing and pleasure was king.

It started with an ass-paddling with Mia slapping my pretty ass with a wooden paddle. But I turned the tables on her. I was the one with the giant prong, and I was the one who was going to be delivering the ass-paddling, goddammit!

That beautiful bitch was bawling for mercy by the third blow, frantically trying to squirm away from me. But I was stronger than she had imagined. I easily pinned her against my lap with one hand and continued to whack away at her poor pretty ass with the other. And then I felt her relent, and she whimpered, “Smack that ass, baby boy!”

"Please, Abby,” she pleaded. "My ass is on fire, but paddle me harder. You're wrecking my poor ass, but don’t stop! Then she began to bawl uncontrollably, trying desperately to crawl away from the paddle, then raise her ass up into the paddle, snot profusely flowing from her nose. Finally, though, the world-class ass-whooping I was delivering came to a close. Mia sat down on her hands, trying to...