Prologue
Jane, a successful young businesswoman, lives next to Simon, an almost 20 year old college student. Right out of college, Jane created a talent agency working with exotic performers, and through hard work and a bit of luck, was able to grow her agency very quickly. One of her burlesque shows took off and established a residency in Las Vegas. Other talented performers that she worked with were able to establish successful careers in the erotic arts. This, combined with some shrewd investments, led to Jane being able to buy her own home 5 years ago.
This home, in a quiet residential area, is one of two on a cul-de-sac flanking the entrance to a park. The area is particularly secluded, with woods backing the houses and little to no traffic. The other home, across the cul-de-sac, is owned by Simon's parents. When Jane moved in five years around, young 15 year old Simon barely noticed her. His head was buried in comics and video games.
Only when he turned 18 did he become enraptured. That fateful summer, he realized that he found Jane stunning, in the bloom of her youth, curvy but not overly so, MILFy though likely too young for that label. But it was not that Simon wanted to fuck Jane, like most of the hormonal college boys his age, he wanted to *be* her or at least like her. Simon had never liked sports and he even now he had soft curves for which he was teased.
He longed for a body like Jane's. The wonderfully rounded bottom and breasts that mesmerized him when he saw her in one of her smart business suits, leaving for one of the many business trips what she took. Since discovering Jane almost two years ago, Simon often fantasized about being a woman and had bought some lingerie for himself. He always got rid of it for fear of his Conservative Christian parents finding it and wondering what was wrong with him.
That fall, two years ago, he went off to college in another state and had something of a miserable time of it, not fitting in with anyone. He did manage to bring some lingerie to college and to have some fun when his roommate was not around. This year, he planned to tell his parents that he was going to take a year off to figure out what he wanted to do. He had not had the nerve to tell his parents that he wanted to declare a major in Fashion Design. He knew that they would not understand.
Arrival: Simon
When he came home for summer break this year, he was shocked that his parents had seemed to forget to tell him that the house was going to be renovated and they were going to travel for a year as missionaries.
Simon asked, "What will I do?"
They answered, "Oh, we took care of it. Do you know that nice young woman next door, Jane? She travels a lot for work and, in fact, she has a two month business trip that started yesterday. She said that you can house sit while you are away and care for her cats. During that time, we can figure what you will do for the last month of summer before returning to school. We have the bank accounts set up to give you an allowance and, since you are on a scholarship, we don't have to worry about paying your tuition, room, and board."
Simon swallowed at this news, a mix of feelings cascading over him. He was going to live in Jane's house? Alone? For two months? How could he tell his parents that he had already withdrawn and given up his scholarship? He was tongue tied and his head was swimming as they continued.
"Construction starts in three days, on Monday, we leave tomorrow so we don't have to fly on the Lord's day, and Jane has already left for her business trip. We do wonder what she does! She told us that she bought that house five years ago and that fancy car of hers. We guess that the Lord has his eye on her!"
Simon nodded and said, "Where is my stuff?"
"Oh, we packed it away. There was one footlocker, probably from when you went to camp, that was locked, we hope you didn't need anything from it. We figured that you could use whatever you brought back from college."
Simon nodded and took a relieved breath. That footlocker contained whatever remnants of lingerie he had kept, some things he had used to restrain himself, plus porn and erotica that he did not want to bring to college. The other items that he used more often--the breast forms so that his chest was more like Jane's, the tiny chastity device for his tiny cocklet--had gone to school with him and were packed in his one large bag.
This conversation had taken place in the car on the way home from the airport. Indeed, when they got home, the house was completely empty. His parents told him that they were going to leave the car in the garage since they knew he didn't have a license and would not need it. They were going to stay in a hotel by the airport because their flight the next day ways going to early in the morning. They walked him to Jane's door, gave him the envelope with the keys and the instructions, hugged him goodbye, letting him know that they would keep in touch though might not always have service in the rural areas they would be in and left in their taxi for the airport.
Simon stood at Jane's door for a long moment, finally opening the door with trembling hands. He had never been in her house the five years that she had lived here though he had cut her lawn from time to time and shoveled snow in the winter. He entered the tastefully appointment house, not knowing what to expect, and was pleasantly surprised. Opening the envelope, he read the short note from Jane.
"Simon, thank you so much for taking care of my house and my cats while I am gone. There should be enough food and cat litter for the duration of my trip. Make yourself at home! There is a guest bedroom that you can use. Your parents told me that you don't drive so I stocked up on some food items and you can order more food otherwise. I should be home on August 1st. Here is my email address and phone number. Send me an email when you arrive so I know that you are there. Cheers, Jane"
He sent Jane a quick email letting know that I had arrived and thanking her for letting me stay since his parents had neglected to tell him about their trip. It was hard to hide his snark.
He took a tour of the house--living and dining room, kitchen, master bedroom with en suite bathroom, guest bedroom, other bathroom, office, basement. Though Jane said he could stay in the guest bedroom, he could not help but peek into her bedroom. He walked around, touching all of the surfaces, eyeing the full length mirror, checking out the en suite with its huge jetted tub. He bit his lip and then smiled, thinking, 'I'll stay here, at least for part of the time. How will she know?'
That being said, he did unpack his things into the guest bedroom, not nearly filling the closet or drawers. He had a bite to eat, showered off in "his" bathroom, then thought about what to do. He knew he would not be able to last long without peeking through Jane's drawers. He kept his legs and pubes shaved smooth and he had very little and very fine body hair. No time like the present, he thought!
When he got out of the shower, he first put on his chastity device. It was the latest and most restrictive that he had tried, an inverted or negative chastity lock it was called. The usual metal ring settled behind his scrotum. He had had so much practice that his cocklet barely stirred. The inverted part consisted of a metal cup on a short post attached to a metal plate. There was a hole in the cup and the post was hollow. He pushed the head of his cocklet down inside his short shaft and pushed everything up into his body, first using his fingers, then the metal cup and post, doing his best to line up his pee hole with the hole in the cup. When it was pushed all the way in, he used the custom wrench to secure the two screws holding the plate to the ring. The end result was a small flat plate with a hole in it above his scrotum, his balls secured in place.
