A Sissy Saga

Part 23 Jacinda who used to be Jason

Lisa watched through the kitchen window as Jacinda battled a stiff breeze to simultaneously hang the washing and keep her skirts from blowing up, on the second count she was losing. How life has a habit of dealing it's own justice, mused Lisa. Jason had been so pleased with himself to drop Lisa in it and had crowed to all his mates and now he was Jacinda hanging out washing and scrubbing floors, oh, and on arrival had to curtsey to Lisa. 

Sarah for the last year had been Jason's boss at work as well as his boss out of it. He still had his old one bed flat but that had changed. At Sarah's insistence he had recently redecorated in a more feminine style to the point that anyone who didn't know would think it was a girls apartment. Sarah had been gradually separating him from the loudmouth boorish crowd he used to run with. As she said to Jill 'he is not a natural sub like Lisa, I have to slowly brainwash him', she saw it as a challenge. Above all Sarah was patient and calculating, she was winning. There was always the prospect of Jason actually bedding Sarah but somehow he had not managed it yet. She seemed to be able to get him to a sexually charged point and then make him cum, usually before he even got his trousers off. Sarah would, of course, sympathise with his unfortunate premature ejaculation problem. 

What he didn't understand was that he never had the problem before and now the problem had cemented itself in his head. Sarah told him that most girls were too polite to point that out or that the girl would fear violence if they mentioned that the guy's performance was less than satisfactory. 'You didn't suddenly become premature with me sweetie' she said as if talking to a child. Jason was confused but maybe she is mistaken and said as such. 'How many girls came back for a second sex session?' Sarah said in a sweetly condescending tone. Jason did not want to answer that but she insisted that he did, 'none' he grudgingly conceded. 'Never mind dear, denial is a classic sissy trait' Sarah slipped the knife between his ribs, he reacted 'I am not a sissy', Sarah smiled 'of course not sweetie' she said patting his hand. The germ of sissydom was now in his ear and would not be dislodged. He began to question everything about his macho self that Sarah had told him was just armour to throw others off the truth about a more sensitive side. She also mentioned, seemingly at random, that all men have a feminine side, boys deny but real men can admit it. Jason began to feel uncomfortable with his macho mates and gradually moved away from them.

Jason remembered the first time he proudly exhibited his erection on her suggestion, it was bound to impress he felt. Without showing any emotion she simply said 'oh well, never mind, we shall make the best of what we have'. Jason felt deflated but before the inevitable wilting she took him in her hand and with only a few deft strokes promoted ejaculation. It was quick and he knew it was quick, persuading himself that it was the circumstance that made it so but the excruciating memory never left him. Later he would not be able to put his finger on anything derogatory Sarah had said. It was small comments and often what she had left unsaid but intimated. It was a drip feed that together added up over time and all contributed to his insecurities.

Jason had never been attracted to strong women preferring those of easy virtue that would just go home afterwards. Sarah was a strong woman who had got into his head and was living in his brain, rent free, before he knew it. Jason was unable to match her intellect or her quick wit, at times she made him feel like a naughty little boy.  

There was the time when she said she wanted him to perform oral and said if he did really well then she might let him fuck her, that had not happened yet but he always lived in hope. She had also said it would turn her on massively if he wore panties. He was unsure but she had bought a pair just for the occasion, deep, pink and satin and made the oblique reference to 'real men wouldn't worry'. He put them on and actually liked the feel of them. Sarah sat on the bed, parted her legs and laid back. Jason put a hand on each thigh before burying his face, Sarah had to admit the power sensation was good and Jason showed some talent, she had her first orgasm. She was well on her way to a second when she felt one hand lift off her thigh. Looking down the length of her body she could see Jason's shoulder moving but could not see the arm. Reaching down she grabbed a handful of hair and forced his face into herself as she orgasmed a second time, his shoulder was working faster. 'Stand up Jacinda' she used the pet name time to time, often enough that he was now used to it. Red faced he stood up, she looked at his soaked panties 'no point asking you for a screw now is there', Jason squirmed and shrank inside. Sarah maintained a slightly annoyed look but was inwardly pleased. Jason stammered an apology so Sarah softened her look and said 'don't worry Jacinda, sissies are well known for inability to control themselves', she knew it was another blow to his masculinity, Jacinda could not think of an answer to that. Jason brightened when she said 'we can try again later' but she would thwart him again.

Jason never saw it as a deliberate policy by Sarah, she had persuaded him of his own inadequacies by playing on the insecurities that most men harbour. Men, in general, are extremely sensitive about their own sexual prowess. Doubts can be easily introduced and even a seemingly innocuous comment about performance falling short of expectation can have a devastating effect. Once a seed of doubt is planted it takes on it's own life. 

Jacinda was wearing panties all the time now, even to work where Sarah had made him her P.A. His male co-workers largely avoided him now, oddly the female co-workers were more friendly. His macho, leering attitude had vanished and he was dressing in a more gender neutral way, there were mutterings among the male workforce that Jason had gone gay and at the same time resented his close working proximity to the gorgeous Sarah who they all fancied not realising why their chances with her were less than zero. The women were more observant and could see that Sarah was making subtle changes to Jason and that he was very deferential to Sarah and by extension them, Jason had never been deferential to any woman before. The girls began to defend him if the boys were critical, for Jason that was a wholly new experience. He had to admit he liked his relationship with the girls now and went out of his way to be helpful.

As Lisa watched Jacinda wrestling with the washing while trying to keep his dress down she mused how far Jason had come. Mistress Jill had told Lisa what Sarah was doing and the end goal was to fully feminise Jacinda, including at work. Sarah was taking longer, Lisa was told, because he is not a natural sissy as Lisa was. With that in mind Sarah was taking things slowly so that each step is irrevocably cemented in before the next progression. He was already wearing panties all the time and occasionally tights to work and sometimes pink shirts. After Sarah praising how good he looked in nightdresses he slept in one every night.