Sissy Secretary
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Sissy Secretary
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The Office: Sissy Secretary Published: Oct 21, 2021
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Andrew Worthington had always coasted through life, riding on the coattails of his family’s wealth and influence. Heir to the Worthington fortune, he grew up a brat and turned into a sexist, misogynistic pig, landing a plumb role in upper management without having to lift a finger. He was overly hands-on with the secretary pool, abusing his position to let it be known that if they ever reported him to HR, their lives would be made a living hell.
That was, until Laura, his immediate secretary, discovered that Andrew had been a very naughty boy, treating the company credit card as his own personal bank balance, costing the company tens of thousands in a way that Daddy couldn’t cover-up. Armed with the evidence, and a mountain of complaints against Andrew’s behaviour, and with the threats of exposing his misdeeds to the board of directors, Laura proposed sweeping it all under the carpet if dear Andrew was to receive a suitable punishment.
Laura delighted in Andrew’s rage when she told him that he had been demoted down to the secretary pool until such times as HR deemed his attitude to have been adjusted. A long overdue lesson was about to be had in how treating women like objects would feel for the wealthy brat, for he was to be made the lowest of the low, beneath all the girls who helped support the company in everything it did.
He would be made to wear the skimpiest outfits, loaned out to anyone known to be a closet pervert, or otherwise at the back and call of every single secretary he had ever made a passing comment to, touched inappropriately or made uncomfortable with a lack of respect… See the uncensored version in our Patreon page for free!
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When it comes to becoming a feminized sissy, it’s often useful to have at least some help. For most this can mean coming under the mentorship of an experienced Master or Mistress. They not only help coerce the individual in the feminine role but provide the support that a sissy needs to become her trus self.
Masters are particularly useful when creating a feminized sissy as they can play the role of the Alpha Male, something which is needed to guide and convince the person under training to submit to the role. A Master will often work with a subfemale or a Mistress in order to make sure that sissy begins to learn the true meaning of femininity.
This doesn’t just mean learning the right sexy clothes to wear and becoming proficient in makeup, it includes how the feminized sissy is able to take the ultimate step and please a man.
For some, the road to feminized sissy is a quick one – they are hardwired to learn how to look good in a panties, bra and stockings and love to wear high heels. Most targeted for feminizatioin, however, offer some resistance and don’t want to be changed. This initial steps implemented by the Master, therefore, are absolutely critical.
It’s about first breaking the feminized sissy’s will and then remoulding them so that they begin to live their girly self and forget that they were ever a man. To do this, the Master needs to exert complete control and exude total confidence.
There are several roads to feminization. The most often used by an experienced Master is the use of blackmail. This often works best when someone is reticent and can make a big difference on compliance. One Master I knew would get a potential sissy drunk and convince them to wear panties and bra – taking pictures that could later be used to encourage acquiesence.
Another route is to get a female partner or sister, even a mother or aunt, to play a role in the feminization of the individual. These often work on the initial stages of the transformation while the Master sits in the background like a puppet master. Sissies will often acquiesce to a stronger female role model and do as they say.
Certain tools can be used to push sissy further into their new role. That includes hypnosis which can be applied covertly to induce the right state of mind for the feminized sissy. Under the tutorship of the female role model, they can then begin to head down the rabbit hole and start wearing sexy lingerie and high heels.
This can often start as some form of sexy play but it is always recorded so that the protagonists can use evidence to further blackmail and coerce the sissy. Each time the feminized sissy is put in women’s clothing, their bond with playing the girly role grows stronger. It may not be long before they begin to accept their new future and even start to enjoy doing their own makeup and shopping for female clothes, particularly underwear.
It’s important at this stage to start keeping your feminized sissy in very pretty clothes. Stockings should be worn at all times and soft silky panties, even when they are working in their male role. When they return home, they should put on ultra-feminine clothing, do their makeup and act completely as a girl. It’s useful to also introduce some submission training here – for example, getting the feminized sissy to dress as a maid and do the housework. High heels are also a must and it’s important for sissy to get used to walking in a sexy and provocative way.
At this time, the feminized sissy should also be introduced to the concept of pleasing men. Allowing her to watch racy videos where scantily clad women or other sissies are shown giving men pleasure can help reinforce this mental attitude.
If the Master has remained hidden up until now, it’s important that they are soon seen by the sissy as the dominant person in the partnership. This could involve taking the feminized sissy out fully dressed for the first time and arranging a meeting with the Master at a local bar or in a nearby park. Make sure that sissy feels vulnerable and is wearing a very short skirt along with sheer stockings and their favourite silk panties.
Once this stage has been reached, your feminized sissy should be easy to subvert, making them the perfect slave for Master. The moment that sissy is deflowered in her sexy outfit is a pivotal moment and can determine what happens next. It’s important that she wants to be with a man so the conversion so far needs to have been effective.
Master will normally start slowly with sissy, wooing her and complimenting her on her appearance. Perhaps he might ask sissy to dance with him at a nightclub or enjoy a dinner together. It’s at this point that Master will start to set down the rules and tell the feminized sissy what is expected of them from now on.
The deflowering of sissy needs to be meaningful to her and she must enjoy it, whatever Master plans in the future. This is critical because the next step is to move sissy into her new life and leave her old one completely behind. This means setting up home with Master and only having access to female clothes and underwear. This might be a good time to commence physical changes such as taking the feminized sissy to their first appointment at a salon. It could also include taking feminizing hormones and having breast implants.
When sissy now looks in the mirror, she should see only a female who is subservient to her Master. She will be eager to please and will, at all times, maintain the illusion of complete femininity.
At this stage there really is no going back for sissy and they will have no choice but to embrace their role. The Master may wish to take things further, for example, putting their feminized sissy to work pleasing men for money. He may simply want a sissy maid at home who can satisfy his urges when needed.
Sissy will delight in buying new clothes and spending hours looking sexy for her Master. She will never be seen in anything but pretty frocks, skirts and silky blouses and her heels will always be high, revealing her silky calfs. Sissy will also practice daily how to please her man and making sure she is always ready for her Master.
"When Emma first came to me she was certainly very inexperienced and needed a strong hand. Now you wouldn't even think that she had ever been a male before." Mistress Zelda SUBHEADING What is a sissy mistress? A sissy mistress is someone who has experience and delights in transforming wayward…
Sissy training requires time, effort and plenty of patience on the part of the wife or girlfriend of the person involved. It's not just a question of putting him in a pair of panties and a bra and hoping he becomes the girl you want him to be. The total…
Ever thought of turning your guy into a girl? We offer you a complete guide to sissification. From waxing to hypnosis you can change the way your guy looks and feels about himself. Soon he’ll love the feel of lingerie next to his smooth skin, and he’ll be giggling…
Fiesty Tgirl with plenty of opinions. Erotic novel writer with a quirky smile. Trans domme for beta males who want to be feminized.
Now available on Smashwords! Crossdressing Tales: The Feminization of Mickey by Emma Laverne at #smashwords https://www.smashwords.com/books/view/1124387
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Amazing Male to Female Transformations https://youtu.be/9XzgsB-wMKU via @YouTube
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