The Sissy Files – Book Two

The Sissy Files – Book Two

Sexually dominant women who prefer their men more feminine – and more obedient – are the theme of this new collection of compilations featuring the subject of transgendered fiction.

Book-Two of “The Sissy Files” contains two works from one of the queens of the genre in Miss Irene Clearmont: “Return to Innocence” and “Aunties’ Candy”.

Contains: forced feminization, male chastity, enslavement, etc.


“Return to Innocence” 

“Your jacket?” said the maid.

“Er, I’m fine,” he replied.

The maid stood by the door stock still with her hand extended and Daniel reluctantly took of the leather jacket and passed it over. He watched her go back into the hall and hang it on a hook by the door. He could see the badge on the lapel. Somehow he would have to get it back in his hands without exciting suspicion. He realised that fixing it on the jacket had been a silly move.

For a minute, he was alone in the room and moved to inspect the photos perched on an old-fashioned chest of drawers. The woman that he had seen at the top of the stairs posed next to the petite Sixteen.

Through the open door, Sixteen entered the room. A few days ago, she had been casually dressed, tight jeans and T shirt. The Sixteen that stepped into his sight was quite a different creature. A pencil skirt, a tight tube to her knees. Slick maroon stilettos with needle sharp heels, a short cane in her hand that tapped on her thigh with an impatient rhythm.

She ignored the smiling maid and slowly walked around Daniel, making him turn to face her as she circled him in a leisurely fashion.

“Strip!” she said.

He found it almost comic. She barely came to his shoulder even in the high heels. A tiny, adorable creature that spoke that single word in a high voice that was almost that of a child.

“I said, ‘strip’,” she said in a hard tone. “You will learn that I do not like to have to repeat myself. Take off your clothes and Elsie will dispose of them. I want to see what I am thinking of buying!”

Daniel glanced at the maid, but she had not moved and just stood smiling at him as he hesitatingly started to slip off his T shirt. Sixteen just tapped the point of the cane on her shoes as his hands slipped to his belt. When his clothes eventually lay in a heap on the floor she pointed at them with the bamboo rod.

“Dispose of them, Elsie and call Julianne down, she should be dressed now.”

Half erect, Daniel stood nervously desperately wanting to cup his hands over himself but not daring to incite the tiny woman who inspected him.

“This won’t do,” she said looking at his swelling cock. “Put these on.”

Her hand drew a pair of handcuffs from the waist of her skirt and offered them dangling on one finger. Daniel played with them for a moment and closed one loop onto his right wrist.

“Not in front, behind,” said Sixteen.

Daniel put his wrists behind his back and fumbled with them before the second clasp clicked closed.

“Good, that’s the first lesson. Obey at the first command. You are here for me to assess your suitability for use, nothing else and don’t you forget it.”


“Aunties’ Candy”

“Now that you are eighteen, there are a few things to sort out,” said Aunty Janet. “We need to discuss your education and all of that as well as some other bits and pieces. Would you like to do that before the party or after it?”

“As you like.”

“Good boy, that’s settled then. Aunty Joyce will be here in a minute with two friend of hers and we can get it all out of the way, so that we can relax and enjoy the party. How about that then?”

Orland nodded and sat at the table, a glass of orange squash in his hand. He looked up at the woman who was no longer his legal guardian and smirked a little. Now he was at last eighteen, things would have to change. Of course he would have to live here, his poor marks at school in the last year and the constant bullying at school had held him up, but soon he would be able to retake his exams and move to university.

Already he had chosen Newcastle, it was so far away. His thought turned to the two women that ruled his life. That they slept together was strange, after all they were sisters. He was sure that their relationship was more intimate than they ever admitted, how could it be otherwise?

“Oh, that’s them now, I’ll just show them in…” said Aunty Janet.

Aunty Janet opened the door to the kitchen and Aunty Joyce and her friends came in and sat down. One of the women with Aunty Joyce was dressed in jeans and a loose top. She smiled as she put a briefcase on the table and opened it. The other was dressed like Aunty Joyce, prim and proper she had a huge handbag that she carefully placed on the floor.

“This is Miss Clark,” said Aunty Joyce introducing the prim lady first, “and this is Miss Hirst. They have come along with me today because at last our boy is eighteen.”

Orland winced at the word ‘boy’. He hated it all the time, but, when others were there it embarrassed and humiliated him and made him blush. In front of the beautiful Miss Hirst the shame was excruciating.

“Now that you are eighteen,” continued Aunty Joyce, “we have to pay attention to a few details, but I’ll let Miss Clark explain it all… she’s the expert.”

Miss Clark pulled a folder from the open case in front of her.

“As you know, Orland. Your parents left a considerable sum including insurance and their house in their will to you. Some of this money has been used by your Aunts to look after you, some is set aside for them until you are twenty-one so that you have a home and a place to live. At that point, according to the will, the fund will be passed your control in its entirety, to provide a pension for the rest of your life.”

Orland listened with growing interest.

“The yearly stipend is currently running at a hundred thousand pounds, give or take a few thousand. What happens now that you are eighteen, and congratulations by the way, is that you are considered by the law to be an adult. That means that you become a signatory to the arrangement and you have to sign that you do not dispute the terms of the will. Do you understand?”

“Mm, I’m with you so far…” said Orland.

A cross look crossed Aunty Joyce’s features that Orland did not address Miss Clark by her name, but she managed to hold her tongue.

“Excellent. What I need you to do is to sign this release with two witnesses and then I can register it as a commissioner of oaths.”

As she spoke she placed a pen in front of Orland and pulled the documents free of their file.

“There are three signatures needed; here, here and here,” she said as she pushed the papers to Orland, carefully overlapping them so that the line where he had to sign was exposed.

Aunt Joyce took out her phone and started to film.

“This is a big moment,” she said as she stepped back a little and held the phone up. “I have to record it.”

Orland’s eyes took in the top form. ‘Non Contestation of A Will After Probate’ was the heading and her signed three times where her finger pointed. The forms were passed to Aunty Joyce and Miss Hirst who countersigned as witnesses before Miss Clark stamped them and wrote the date just below.

“Good, that’s done then,” said Miss Clark. “I have to be on my way now, so have a great party and enjoy the day!”

Orland said, “Goodbye”, and then stood to open the door for Miss Clark.

“That’s the first part,” said Aunt Joyce.

For some reason she seemed relieved and actually smiled broadly.

“Now we just have a last bit of business. Miss Hirst will explain,” she continued.

Miss Hirst nodded and reached to her handbag.

“In cases like this, it is best to be sure that the legal guardians are free to assert their rights as well. After all it is only fair that the hard work and forbearance that they have shown is rewarded. Of course, this is already built into the terms of the will, but your Aunt here…”

She looked over at Aunt Janet who now held the phone pointing down.

“…would like the assurance that you will allow the previous maintenance payments to be confirmed and those for the next three years as well.”

“I’m sorry, but what is this all about?” asked Orland.

“Listen to Miss Hirst,” admonished Aunt Joyce. “She’s telling you, don’t be so rude!”

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