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Chapter 2
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Chief of the family

Ever since I was born, I had been tutored to replace my father as the head of the Family. The Castelanno Family was an organized branch of the mafia, one of the oldest ones. My father was the current chief, but nothing good can last forever. It was becoming clear, by the wrinkles, lack energy, and his weakened heart, that a new leader would have to be selected and I was the most prominent option. The members of the Family, and every subordinate, congratulated and praised me, "You will be great, my nephew," said uncle Luciano, as he wanted to be on my good side when I finally became the boss. All of them did. My younger brother, Marco, couldn't be more excited. Even, my father was proud of me. He expected me to be able to restore the old glory of the Family name, that was getting subdued by rival families over the decades, he shaked my hand and laughed in an almost maniacal manner, "They will fear the castelanno name once more, Santiago." In just a few days, my father would announce to the other families his retirement and my role as the new chief.
However, that was all cut short a few days prior. A rival gang, upon hearing rumors about my soon to be leadership, decided to dirty their hands to stop it. When me and Marco were returning home after a visit to his bride's house, a white van with three men holding guns appeared. I pushed Luciano out of the way, giving him the chance to take cover behind a car. Instead of a shootout the men grabbed and dragged me to the van, driving off, as their target had been acquired. My Family moved every available member to go on the hunt for me. Father was enraged and threatened to go on war with every other the other families if I was not returned. None of the other chiefs fell for his bluff, as they knew a war would be just a suicide call for our weakened house. Desperation took the lead as an entire year passed and there was still no sight of me. The entire search would come to an end when I was returned to our old mansion. I entered the gates as the members were terrified by what they saw. I had been returned not as Santiago, but as Angelina.
The rival Family, instead of killing me, decided to completely erase the heritage of the castelanno's. In the hideout where was held captive, they stripped me naked and began my feminization. I was shaved of all my body hair, except for my hair and eyebrows, locked my cock in a flat chastity cage and inserted a plug on my rear. My body began to be shaped in a feminine silhouette as all the food they gave me was laced with estrogen and progesterone. Soon it had became impossible for me to dress in male clothes, the budding breasts in my chest grew to respectable 32C cups, preventing me from feel any comfort in my back without a bra. My hips and buttocks grew to envious size, while cock shrunk to laughable measures with each day.
Once the hormones had made enough of a change in my body, the surgeries began. My face was the first, as they restructured my features to a womanly shape, one of my ribs were removed to create a better hourglass shape in my figure, followed by a liposuction to finish the deal. The last moment was the complete removal of my testicles and the inverting of my dick nerves to create a soft, beautiful pussy to be accommodate between my thighs. They called me Angelina, as for them my beauty was divine. A mockery of course.
Shocked and terrified, my Family could not, or rather wanted not, to believe what they were hearing. The bright future of our Family had been reduced to pretty thing in skirts. Father was furious, but there was nothing he could do, his heart was at his last moments, and our reputation is not what it used to be. They allowed me to still live in our mansion, but none of them dared to Interact With me. My previous cheerful cousins, avoided me, some of them made sure to mock when they thought I was not listening. My uncle Luciano could only look at me with disdain, as in his head I had betrayed the Family for what had happened to my body. My father was in his last days, as his heart could was being able to deal with all that unfolded. The guards had forbidden me to talk or even see him, as the sight of my brought pain and shame that he didn't needed to. The only person that still treated me with care was my brother, Marco, now soon to became the new chief of the family. In his eyes, I had sacrificed myself to save him, as he could might as well had been the one in my position had I not pushed him aside. He pitied me, but still tried to treat me with love and respect.
As I stood on the middle of our living room in a tight forming black dress with the expensive and sensual lingerie under it, stilettos, golden necklace and earrings, face covered in subtle yet stylish make-up and hair tied into a bum, imagining what would my younger brother think if he found out that I was the one who orchestrated my "sacrifice" I was the one who leaked the information of the passing of the torch to the gang who kidnapped me, secretly told them where they would be able to find me in a, **** enough, position to be kidnapped and taken care of. I had heard during one of the countless reunions of the families, what the Castrano Family did to their prisoners, sick things for their pleasures, and planned for them to take me. I never wanted to be the chief of any branch of the mafia. It truly sickened me to see all those people dying for trivial stupidities, killing many of my loved ones in acts to protect their territories. The last straw was when a bullet accidentally caught my grandmother during an attack to our summer house. Since then I had made my decision. It would be impossible for me to eliminate organized crime, but I could at least escape it. No woman has ever been the chief of such an old house as ours, so it was only a matter of moving the right pieces of the chessboard.
To give up on my manhood was a difficult thing to do, believe me, but (As my kidnappers commented) It was a small, unnoticeable price for my freedom.
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Updated on Oct 2, 2025
Created on Aug 10, 2025
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