sissyjamiedreamer

Meet Phillip, now Phillipa. At 25 he lived with his Aunt Hillary and his younger cousin, 21-year-old Rebecca. They didn't charge him rent, they just expected him to pull his weight around the house. Over time he had done every chore around the house, as did Rebecca and Hillary, but he had never been trusted to hand wash their intimate, until one day when Hillary supervised him in hand washing her and Rebecca's knickers. All was going well until Hillary noticed the bulge in his trousers. After denying her accusations of being some weird pervert, who had probably been going through the wash basket looking for their underwear, she said it could only be that he wanted to wear them. Which unfortunately for Phillip, was the truth. It was his deepest secret and he hate this side of himself, and hid it well for most of his adult life. . She had him strip naked and wear beautiful pair of the smoothest and softest satin knickers. Of course he had a stiffie as he completed the washing. Much to her amusement. The next day she had gone out and bought him a huge array of his knickers and bras, and he was told he would be wearing only them from now on. Both Hillary and Rebecca loved seeing his shame and embarrassed him constantly for his arousal. But worse was to come, as Hillary had come to know of a small but very well respected sissy training academy not to for away. Hillary wasted now time and enrolled him for the full sissification programme. In the scene above he being taught his makeup skills by his matron. And tried to plead with her for her to let him go home. But to no avail.

After his sissification and quite unbelievable transformation of 21-year-old Jamie had served at quite a few gatherings and parties that his domineering Auntie had held. But this one was probably the most humiliating. His auntie had invited his former girlfriend Anna, over to celebrate her 21st birthday with some of her friends. And his auntie had just told him to give Anna the remote control of the nw large vibrator Jamie had buried deep inside him.

Do you agree?

To mark one year since their unwilling arrival at the Ladies Club, the club a held a dinner party for their former girlfriends, female colleagues, mothers and aunts. The two sissies would be kept in a cage on full display, and were required to show the attending women how much they were in love. They would be mad kiss constantly for the duration of the dinner. Both sissies were now genuinely in love with each other but the last vestiges of male pride made this an unbearably humiliating experience. They were keenly aware that were now a world away from the aggressively masculine former selves, and that they now were constantly aroused by their dresses and knickers, and each other. So much so that both of their now excited, and now much smaller clitties, were just about to spurt into their knickers. Tears of shame ran down their cheeks as the women noticed their slight spasming as the squirted into the teasing satin of their knickers. But as their tears mixed, they kept on kissing.

Another recreation of a favourite sardax piece.

Victoria was beginning to enjoy her punishment of Carl and she asked her all female staff to think of something other pointless tasks he could perform in the rain.

Victoria wasn't going to let the opportunity of the bad weather pass by, and she had Carl pointlessly wipe down all the lady's cars.

Carl used to be an employee of Victoria up until a few weeks ago. Victoria considered him her most trusted employees and always had a soft spot for him, and the fact that he was the only male under her employ only made her more protective of him. She even thought of him as the son she never had. So when it emerged that he had been stealing money from her company, she was, to say the least, heartbroken. And although she was a kind hearted woman generally, if you upset her, well, you would know about it, that's for sure. She didn't go to the police, she would handle his punishment herself.

Poor Martin, this wasn't the outcome of his visit to HR that he was hoping for.

Once she was satisfied with her shoes, she revealed the last item of his uniform, a pink ball gag. He politely pleaded to her not to dress him like this, but she just smiled and gently pressed the gag to his lips. He instinctively opened his mouth and she buckled it tightly around the back of his head. She then sat at her desk and had him stand before her, and told him of her expectations for him going forward. And that if didn't like his dress, go and see HR.

Soon she added footstool duties and even had him clean the shoes and make coffee for the rest of the women in the main office, and had him use his tongue to clean her shoes. This was embarrassing enough for him, but then came the day when she told him she didn't think it was appropriate to perform his duties dressed like he was, and she decided to have him wear a uniform.

Another recreation,this time of a Sardax piece.

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.

Poor James. He was once the manager of the store behind them. After meeting Serena, he thought his dreams had come true. A beautiful woman, interested in him? Unfortunately for James, she had other ideas.