How does a man start working as a secretary? It might be no more than an accident that sets him on the path towards becoming a feminized assistant, or perhaps the natural progression of a bedroom game, but maybe his wife or girlfriend has decided that she wants him submissively employed! Once he's wearing a bra and blouse, he'll find himself falling naturally into the role, it being impossible for a man to pretend that he's charge when he's dressed as a female office worker. Regardless of whether his responsibilities are limited to typing or require him to provide rather more personal services to his superior, you can be sure that the experience will prove excitingly emasculating!
In these erotic stories about sissies becoming secretaries, submissive men must seriously consider a career in skirts, but that doesn't mean they won't have a thrillingly sexy time along the way! Special training, applications and interviews add to the fun as each takes his first steps as a secretary.
Although Gareth has come home for the evening, he's still having to work! His girlfriend is far from impressed with him needing to make last-minute changes to a presentation, with Lindsey insisting that he wears a bra as she teases him about being a secretary! Soon the slides that his boss requires have been swapped for the most shameful of dictation, but Gareth's hunt and peck approach fails to please the woman in charge. Before this submissive boyfriend knows it, he's having to sign up for an online course, which promises to teach him how to type like a secretary! A combination of rewards and punishment encourages him to put in the necessary practice, as you'll discover when you read Touch Typing.
Dressed as a secretary, Steve is having to transcribe a video for his wife's amusement, a task which becomes even more demanding when one of Linda's friends visits. This feminized man not only has to explain why he's wearing a longline bra, girdle and stockings, but must also prove his typing proficiency to learn the women's plans for him. His secretarial skills will be put to the test as he transcribes an old diary, with its provocative pages requiring him to devote night after night in order to turn them into text. Teased by his wife throughout, he'll learn that male submission is nothing new, even as he looks forward to a future full of typing. Follow his progress in Unpaid Work.
Changing into sexy lingerie is only the start of James's preparation for what his wife calls his progress review, with this businessman having to swap his shirt and trousers for a tight skirt and blouse. Kerry is waiting for him in the study, where she makes him drop to his knees and devote himself to her strap-on. Soon James is being bent over the desk, having to read humiliating rejection letters while his wife has her way with him! If he wants to enjoy anything more, he'll need to apply for a secretarial position, but that has unexpected consequences - a video call from a hiring manager, wanting to know more about his experience. Find out if he gets the job in Successful Application.
Luke's girlfriend amuses herself by making him fill in an application form, albeit one that's impossibly suggestive, with Kim requiring her bra-wearing boyfriend to accompany it with an equally emasculating letter. He thinks she's just fooling around with her suggestions of him becoming a secretary, but it isn't long before he's emailing a friend of hers who works in Human Resources. Kim doesn't stop there, however, with her desire for Luke to dress the part seeing him having to buy himself suitable clothes. He's wearing women's underwear as he arrives at the office building, but his skirt and blouse won't be staying in his briefcase! Read what happens in Preparing for His Interview.
Games of secretaries and bosses can be great fun, especially when traditional roles are reversed, but when a man plays the part of a woman's assistant, he can't be sure that their make-believe won't become more serious! In these sissy secretary stories, there's no doubt that the wives and girlfriends are in charge, with the only question being how far they'll want their husbands and boyfriends to go. It might start with only wearing a bra, or perhaps some playful typing, but each of these submissive men will end up doing much more than that by the time he's taken his first steps as a secretary.
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