Secretary fanstasies usually involve some form of playing secretary. Variations include recpetionist, office worker, or other clerical job. Bondage is often added.

upskirt picture of secretary courtesy of Michael’s Sin, Sex & Pleasure: Lingerie
picture courtesy of Michael’s LIngerie

trannie office girl in blue dress and rope bondage    Office girl in bondage, with clear tape over her lips, and then finally an ace bandage over that! —courtesy Trannies in Trouble

trannie secretary wearing blue dress in rope and chair bondage

trannie secretary cinched in ropes and cleave gagged    He overcame her so quickly that she hardly knew what was happening. But once the wrist tie was cinched down, all hope was lost for poor office girl Sandra. —courtesy Trannies in Trouble

office girl in blue dress rope bound and gagged in front of a mirror    Sandra as an office girl bound in a blue dress with a tight and effective over-the-mouth gag. She sadly looks at her own reflection in the mirror. —courtesy Trannies in Trouble

trannie secretary in chair bondage with cleave gag    She never thought that her new secrretarial job would lead to such a predicament — tightly bound, a handkerchief shoved in her mouth and a cleave gag to hold it in place. —courtesy Trannies in Trouble

trannie secretary in chair bondage with cleave gag

office trannie tightly rope bound with strapped-in ball-gag    The tightly strapped-in ball gag left office girl Sandra in her humiliating predicament — drool dripping from her lips while the intruder rifled through her office. —courtesy Trannies in Trouble

trannie office secretary in severe chair bondage    Cleave gagged and bound with blue rope, office secrretary Sandra awaits her rescue, almost dreading her eventual humiliating discovery. —courtesy Trannies in Trouble

trannie secretary in white blouse and black leather miniskirt is tightly bound and securely tape gagged.    Office receptionist Sandra gets grabbed and taken away. Tightly bound and securely gagged, she helplessly mmmpphs and ponders her sad fate. —courtesy Trannies in Trouble

trannie office secretary in chair bondage    Overpowered at the office, Sandra ’s mouth is stuffed with a handkerchief and held in place with a painfully tight cleave gag. She struggles helplessly in her chair, defeated, abandoned, with no hope for escape. —courtesy Trannies in Trouble


    I was a REAL secretary for about 5 years. I worked in a real estate and insurance office that was almost entirely women. My interview and my first few days in the office were a bit nerving for me as I had to fully admit to everyone that, yes, I was a sissy. Of course the women quizzed me a lot about everything and asked the usual questions. And they were certainly curious about any outfits I wore to work (I almost always wore a skirt or dress).
    But after about two weeks, when they concluded that I was not any kind of perverted threat to them, and as their initial amusement wore off, they simply accepted me into their sorority of secretaries and business women. Soon, I found myself like any other working woman—every morning having to put on makeup, primp my hair, put on panties, bra, garterbelt or girdle, stockings, slip, dress, shoes—and then grab my purse and coat and head for the office downtown—and simply living from paycheck to paycheck as most secretaries have to do. Pretty soon, a sissy will find herself spending 8-10 hour days in panties, stockings and skirts, exhibiting feminine mannerisms, and hardly thinking about it. Just like any woman.
    But it is such a wonderful and free feeling to be able to wear a pretty dress or skirt to work everyday and feel the sunshine on one’s nylons and the city breezes fluttering one’s skirts and hearing one’s own high heels clicking on the sidewalk. It’s a feeling that any sissy will never become complacent to—kind of a little constant reminder that she is a weak, infibulated,helpless feminine sissy and wearing a dress or skirt in broad daylight in public where everyone can see. Being a secretary is a wonderful experience and billet for any sissy and quite a good asset to have for any working woman office manager or boss. —sissynancy

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a sissy forced to wear feminine office wear


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    Last Updated: October 25, 2012

    Created: May 21, 2004

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