I think that it was about six months ago when Jack was kidnapped by the cartel. Immediately afterwards they had entrusted him to me for a little re-education and some corrections. This time they have given me less time then usual, but I was well known for my professional work and I accepted the challenge.
Back then Jack was only a few weeks short of his 20th birthday. He was a spoiled boy from a wealthy family. Usually his type is very hesitant initially but they can not resist to my training for a very long time. For his first training I had to chain him as he did not want to fully cooperate. Maybe he felt uncomfortable because I had left him naked and locked in a basement for e few days prior the procedure or maybe he was not used to be on the receiving and of the cock. I explained to him that it's only a plastic toy attached to a piston but he still moaned "No" on each thrust of the machine.
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On the 10th day I chained him up in a standing position with a leg spreader on his ankles and his arms chained up on a chain hanging from the ceiling. My inspection was short one as it was only the beginning of Jack's transformation. I spread his butt cheeks. His ass crack was red and swollen and it was slightly loose - I could easily insert something small if I decided. With this observation my inspection had finished.
I called in the nurse. She was a 45 year old woman who wanted to make some money aside from her main job. I think that she actually had really perverted sexuality. I was not paying too much for what she was doing. Either way she knew what to do. She started giving a nice hand job to Jack. This was about to be his last orgasm by a woman hand or at least it was going to be while he is in my training. Something to give him a painful memory of the times when he still looked like a man.
As soon as Jack ejaculated on the apron of the nurse, she took her instruments out. He had nice and big cock, so probably Jack was about to become the shemale with the biggest cock I've ever created. Anyway, his cock was still half hard when the nurse circumcised him. Jack was not very happy about it.
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The following two weeks were dedicated for medical procedures. After all Jack was on a medical leave from training, but time was ticking. The plastic surgeon was very good. During those two weeks he did 4 operations. The results were satisfying. His tits were great and his facial features had become much more feminine. The rest of the small modifications were also perfectly done by the surgeon. After the last procedure Jack received his first feminizing injection.
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Jack quickly recovered from the operations. It was time for the next phase. I chained him up in the same standing position with the leg spreader and his arms chained high above his head. He spent the entire day like that with a dildo fucking his ass. I made sure it was a bigger dildo then the last that was used on him. By the end of the day his ass was loose and ready. I called Malik - an african-american working for me. He came immediately.
I briefly explained to Jack that Malik was about to drop his pants down to fuck Jack's ass and if he wanted to get out of the chains he had to cooperate and milk the black cock in his ass as well as he can. The exercise went well. Malik ejaculated 4 times pumping Jack with his sperm. I was glad to see that Jack was also having good time. His useless circumcised cock was boncing happily as Malik was shoving roughle his cock in the boy's asshole. For the first time Jack was so eager that he even got 2 anal orgasms with his cumm dripping from his semi-hard cock directly on the floor.
When the ordeal finished, I informed Jack that I will now call him Jacklyn. He did not protest.
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The next day was a break from physical feminization. Instead I showed Jacklyn the recording of her being on the receiving end of Malik's cock. Of course I made sure that she is shown all the three camera angles recorded, including the one which captured Malik's cumm dripping from her gaping asshole. I also showed her a few other interesting moments from the tape, giving her a few guidelines how to act and behave during sexual intercourse as Jacklyn. I made sure, that every time I referred to something she was doing with her ass, I used the word "cunt". Jacklyn had to get used to this new purpose of her asshole quickly.
On the other hand the she was coping well with the injections. She was looking more and more like a real woman.
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After a few weeks of training and watching videos in my laboratory Jacklyn had the opportunity to go work for two months in my brothel. A few of the more experienced whores helped her to learn a few tricks including how to use make-up and other important things. Jacklyn even got her first long hair hairstyle and beautiful manicure.
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Imperceptibly the day came when the training ended and I had to hand Jacklyn over to the cartel. I looked over the records of her training program just to be sure that I have not missed anything. She was perfect. Even the results in the brothel looked amazing. According to Madame the last few weeks of her stay in the brothel were big success with her becoming one of the most popular whores in the catalogue. Great success for a boy who was protesting against the plastic cock in his ass. During those two months Jacklyn had served over three hundred clients with about one hundred of them in the last few weeks. I knew that the drug lord was a perfectionist but I was sure she would do just fine. Jacklyn was my most successful shemale.
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Jacklyn entered through the door. She was asked to perform like a fashion model and she did great. She was wearing extremely high heels and a beautiful black dress. The drug boss liked her so much that he asked Jacklyn to dance for him. The dance was ecstatic. In the end of the dance Jacklyn even had an orgasm. The drug lord noticed her strange movements and was curious so he asked her to come closer. He then asked her to lift her dress up. Jacklyn blushed but obediently did as she was told. When she folded her dress upwards her transparent underwear was revealed. The fabric was tight and narrow but it was firmly holding the pulsating circumcised shemale cock. Jacklyn's belly and underwear and the inside of the black dress were covered in her useless shemale cock. The drug lord was fascinated and asked Jacklyn to turn around and present her cunt to him. When she complied the amusement of the boss became even greater. Underneath the transparent panties it was clearly obvious that a small rope was hanging out of her cunt. The boss inserted his hand between Jacklyn butt cheeks and felt the vibration. That was a trick Jacklyn had learned in my brothel. He pressed firmly with fingers against the sphincter of her cunt and started massaging the stuffed fuck hole. The former boy Jack had another orgasm in front of everybody in the room. Once again his sperm leaked in the transparent panties this time the quantity was too much and it started flowing down her thighs.
Useless to say I got paid well for my work.
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The same evening Jacklyn was fucked for the first time by her boss. He fucked her ass cunt mercilessly giving her the possibility to taste the flavor of her own rectum from the tip of his cock. She eagerly sucked.
Then it was turn for the bodyguard of the boss. She was on her fours and her cock continued hanging and spraying cumm on the floor underneath her while he pumped his sperm in her rectal passage.
During the first working night for her new boss, she was fucked by 9 different people and Jacklyn liked every but if it just as she was taught.