The Man Who Took Him In Pt. 01

The following story is completely fictional. The names and characters are as well. This is a feminization story that will be broken into many parts. The chapters will get longer. This is my first erotica so leave me feedback and suggestions for future stories and chapters. Finally, I don't want this story to minimize the struggle that trans people go through. This is fantasy and fictional and does not represent the struggle, hardship, and decision making that trans people go through. Without further ado... let us get into it!

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Dejected, Craig Robinson wandered the streets with the little amount of clothing he had. The 18 year old was pretty much alone. He had no friends, he wasn't close to his family, and his merit scholarship he earned has just rescinded after his grades slipped beyond the point that his college deemed acceptable.

So here we were in the nicest neighborhood in town. He remembered passing here as a child and dreaming that one day he would live in one of the grand mansions. The houses here were filled with actors, businessmen, lottery winners, and rich men who had the luxury of retiring at the age of 50. It was the first place that came to Craig's mind when he had to leave the school earlier that night.

Up ahead something piqued his interest. While every house on the block had their lights out for the night there was one grand house that lit up the street. "Odd for 3 o'clock on a Wednesday" Craig whispered to himself before quickening his pace.

About 30 seconds later he arrived at the house and after a quick bit of deliberation he gave three quick raps on the ornate oak door. He waited and waited and before long he could hear the faint tapping of feet along a marble floor and the click of the door handle revealing a dapper man. He was about 6 foot 2 with sleek silver hair. He was dressed in a black silk pajama set which Craig immediately associated with the fancy hotels like the Ritz. On the left breast were his initials: JM.

James Maccony was rich. That was an understatement. He had inherited a large sum of money which he then used to create his own media empire. Every blockbuster movie in the past 10 years had come from his company. At the age of 52 he passed on the business to his mentee and decided to live a quiet and secluded life.

Craig did not recognize him. He wasn't interested in blockbuster movies. If you wrote down his interests on a piece of paper it would be more inline with a girl named Britney, not a man named Craig. He enjoyed dramas, and Disney movies, and listened to Katy Perry and Christina Aguilera.

James looked at the sight before him. In the door frame was a young man. He looked him up head to toe and calculated that he was about 5 foot 6 and 130 pounds. Much smaller than James had been around the same age. He was wearing a simple tight white shirt and a pair of jeans, the only thing Craig could afford. He was cute. James couldn't deny this. Maybe even perfect. He was feminine and skinny with pale white skin. The type of person James fantasized quite often about.

"Can I help you?" said James. "Hi! So sorry to bother you, my name is Craig and I just had to leave the only home I had left and I desperately need a place to stay for the night. I can be out of your hair bright and early tomorrow." As he did this he tried to look as vulnerable and desperate as possible, something he had learned to use years ago.

Although James already had his mind made up he deliberated on it for a few seconds before saying, "I guess it couldn't hurt if you stayed the night boy. The name is James by the way but I expect you to call me Sir."

Craig breathed a sigh of relief as he stepped in the house, a grand cavern that was at least 10 times the size of any house in his old neighborhood. It was a beautiful abode with a grand chandelier hanging over the main foyer. Craig spent a solid 20 seconds taking in the sight. James snapped him out of his trance "I only have one guest room that is clean currently and it is well... a bit pink" He of course was lying. He had plenty of other rooms open but this would be much more fun judging off of Craig's slender appearance and feminine behavior.

"That will do just fine Sir" Craig was over the moon! "It justs up the stairs and the first door on your left" James watched Craig all the way up the stairs and marvelled at his rather nice booty. "Oh he will do just nicely" said James as he walked to the kitchen, a plan already brewing in his head.