Where my Fantasies Come to Play

[femininedestiny]

[starfuckstranger]

[sissyjamiedreamer]

Poor Percy. He knew his mother knew about Margaret dressing him up, but he was sure she would put a stop to Margaret's plans to make it permanent. To his dismay, she seemed to love the idea.

[sissyjamiedreamer]

Another Recreation.

Even at 21, Percy was still sent to his mother's friend, Margaret's house when she was away on business. Percy's mother's knew Margaret liked to dress him up and was perfectly happy with it. This time though Margaret planned to make things more permanent and expose him to all the women in the area. Would poor Percy be saved by his mother on her return, or would she fully endorse Margaret's permanent feminization of her son.

[sissyjamiedreamer]

Successful entrepreneur Janice had built a massive fortune for herself. So much so she decided to retire in her mid 40s. She wasn't interested in getting married or relationships, apart from the odd fling. But she did enjoy a project to keep her very active mind firing. And her latest project was Jamie. Jamie, formerly her ever loyal PA James, was 25 and on the surface a normal man in his mid 20s. But the perceptive mind of Janice knew he was different and not so long after becoming her PA she worked out his secret sissy fantasies. So when she retired she invited him over to her sprawling mansion and put her theory to him and offered him a position as her personal maid at her home. Through a combination of her own expert negotiating skills and his own desires, he agreed. But she had three non-negotiable conditions. One, she was completely in charge of him and he couldn't refuse any order or decision she made for him, (she assured him she would always act in his best interests). And two, this was not just dressing up and having some fun, he had allow her to completely feminize him , and three, be in chastity, in which she would be in control of his sexual release. James.es agreed and started in his towards becoming Jamie. She was a reasonable and caring Mistress, and allowed him to her as Miss Janice, and even encouraged him document his transformation on social media. In the scene above, Jamie was posing for a live stream, and she saw a golden opportunity to embarrass him. She new he secretly loved it and it would give his audience a thrill to see him bossed around, especially as Jamie had thoroughly washed and polished her car the day before, and given his followers a lovely and teasing show on a live stream as well.

[sissyjamiedreamer]

Continuation of previous post.

He was starting to get worried about how far she was going to take things.

[sissyjamiedreamer]

When 25-year-old Eleanor discovered her brother James was stealing from the company he worked for, she decided to take full advantage off the situation. Threatening to go to the police, she gave him the option of prison or becoming her maid. Thinking being her maid was the easiest option he chose that option. Little did he know prison might have been the less humiliating situation.

[sissyjamiedreamer]

The Maid. Part 4.

[sissyjamiedreamer]

The maid. Part 3.

[sissyjamiedreamer]

The Maid. Part 2.

[sissyjamiedreamer]

The next few posts will be based off a piece of artwork I came across. My appreciation to the original artist.

The Maid.

A growing trend amongst wealthy or aristocratic families, that are matriarchal, to deal with unruly young men, is to feminize then and have them serve their female relatives as sissy maids. Poor 22-year-old Rupert here has been earmarked for such treatment by his mother and sisters. Tired of his bad attitude and lazy nature, and his constant rudeness towards them, they finally had had enough. They had heard on the grapevine among wealthy families about a woman who specialises in turning men into simpering, and very obedient sissy maids. No one knows her real name, or how to contact her, she simply shows up when the word goes round that a man needs her attention, and she hears about it. She is always in the guise of domestic maid, but it soon becomes clear she is a very strong willed and highly skilled dominatrix. She doesn't charge a fee, just requests to stay at the house of whoever needs her services. In the scene above, she has had to restrain Rupert, an already effeminate man, as he was somewhat uncooperative when she was getting him ready to be presented to his mother and sisters where they will gleefully explain what going to happen. She spent two hours on him, even gluing fake breasts on him with a long lasting, but harmless glue. Hopefully Rupert would learn to be a little more appreciative of her efforts.

[starfuckstranger]

[alwayscute]

Happy birthday @ivyrosetglued !

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