Life was going pretty good. I had a good job and a smoking hott girlfriend. Sometimes I couldn’t believe my luck especially when it came to her. She was way out of my league, but she seemed love waiting on me hand and foot, always cooking for me and even doing whatever kind of kinky sex I wanted. We had barely started dating when I found myself moving into her place. It was about six months into our relationship when I started noticing changes in my body. I lost a ton of weight and what fat I did have seemed to be in all the wrong areas. I brought it up to my girlfriend, but she just comforted me and assured me that it was just my imagination, always making sure to rock my world for good measure. It was only a month after that I started to get really worried. My chest was getting really tender and puffy, and swore my dick was getting smaller. I tried to express my concern to my girlfriend, but once again she tried to downplay it. Something was going on, and as much as I hated to admit it, my girlfriend was in on it. I started snooping around and found a bottle of female hormones and male hormone blockers in her medicine cabinet. When I confronted her, her entire personality changed. Gone was the sweet girl, who was enamored with me. Now a fierce, dominating woman stood before me. She offered little explaination, but told me I had better go along with things if I didn’t want anything bad to happen to my dad. I knew my dad tended to do business with some pretty shady people, so the threat was real enough for me. I wanted to talk to him, but something told me that would just get us both into trouble. I went along with everything, from the hormones, to the wardrobe change, and even the facial feminization surgery. Before long I was sporting a sizeable rack, even my girlfriend, or I guess ex girlfriend at this point, was surprised but pleased at their size.
One day she came into my room, handed me a huge pink dildo, and made a deal. If I could deep throat the entire dildo, my father’s debt would be forgiven, and I would be able to move out. I practiced on that thing night and day. It was torture learning to control my gag reflex, but this one task was all that stood between me and freedom. It took weeks but I was finally ready. I called my ex in and showed her. She simply smiled, got up, and left. I was so confused, but I would have all the answers soon enough.
About an hour later, my girlfriend came back, followed by a group of some pretty rough looking bikers. It turned out these were the guy my dad owed money to, and he offered me as payment for his debt. My ex was the daughter of the gang leader, who just so happened to have a thing for ladyboys, and tasked her with my transformation. To her credit, she didn’t lie, and I would be moving out. After everything was explained, the gang leader decided seal the deal by “breaking in” my mouth. He undid his pants as he approached me, and it quickly made sense why my ex gave me that task. If I was going to be this man’s whore, this was going to be a very useful skill to have.