Mistress and Sissy: A Dialogue, episode 23

Mistress Amelia asks:
How does a male incorporate being a sissy into his everyday life and still work as a man?

Sissy Dani replies:

The obvious response is that he wears feminine attire under his male clothing—panties, camisoles, stockings, possibly even a bra. But that may not be enough to satisfy his own girlish desires or the demands of his Mistress. So what else is possible?

He can make changes to his appearance that are not blatant, but reflect his feminine self. For instance, he may have his hair styled in a unisex or even feminine manner. It could be colored or frosted or highlighted; he might even get a permanent wave. A feminine manicure is a possibility, with a subtle pink color applied. Cosmetics might also be used to hint at a more girlish appearance—a pink lip gloss, or a light application of mascara on his lashes. Careful trimming and shaping of his brows can assist in a feminine look.

Of course, in the modern world, the differences between male and female clothing can be less obvious. A silk shirt in a delicate pastel (peach or lavender, for example) conveys a feminine appearance. The collar can be designed to emphasize girlishness—a long pointed look is clearly intended for a woman. And, naturally, buttons on the “wrong” side will add to the effect. Women’s slacks can also be found in sizes that will fit a male body…and will convey a different look: They generally fit more closely over the ass and have a more flowing, loose fit over the lower leg. Many styles designed for women will have zippers on the side or the back, rather than the front.

Footwear choice can also be important. Patent leather will always seem more feminine…and a mild heel (one-and-a-half inches in height) will enforce a more girlish gait. Visible bows and buckles may also hint at his feminine preferences.

Naturally, there are other things that a “secret sissy” can do. He should always sit when using the toilet (choosing panties and feminine slacks will enforce this). His choices at meals can be more girlish as well—light salads as opposed to burgers or sandwiches, for example. He should act as if he expects to be treated as a female—wait for the door to be opened and held, be served first in the restaurant. He should ask for assistance when handling heavy or bulky packages or going up and down steep stairs. His handshake should be limp-wristed rather than a firm grip; in fact, greeting with a casual wave might be preferable.

As time goes by, and his employer and co-workers become accustomed to his girlish ways, he can begin to increase his outer sissyness until, finally, he arrives at work in dress, heels and full makeup as the sissy he is meant to be.

Sissy Dani asks:
Should a female boss insist on a feminine dress code for all employees—male and female?