Fiction by Miss Ivy Ohmigosh

I was bad, very bad, and that’s why I’m laying in bed now in a pink flannel nightgown, naked underneath except for the chastity tube on my pee-pee. Mistress Colette never put me in chastity before but I know I earned it. She says it’ll just be for tonight, so I won’t play with myself while she’s out with her a man; but who knows? Mistress can do as she pleases, and she might keep me up locked longer. Depends, I suppose, on whether I can get back to being a good sissy for her.
I was pretty good, for the most part (after all, what sissy is perfect?), until she told me she was going on a date tonight. Dating and flirting and opening her beautiful legs for the hard penis of a man who meets her standards as an equal. (Not like me.) How foolish I was, thinking it was just going to be Mistress Colette and me, Sissy Jessica, living a happy little life together forever, she going to her job and me keeping house as her maid. Amazing the things we can make ourselves believe when we want them so badly.
Mistress was going to tie my wrists to the headboard, but she made me give her a Solemn Sissy Promise not to put my hands under the covers to touch myself. Sure, I can’t touch my pee-pee in the tube, but I could rub my nipples and finger my sissy pussy, right? Maybe I could cum in my tube just from that? But then Mistress would see the puddle clouding the tube when she came to check on me later and she would know, and she would punish.
Ohmigosh, what have I gotten myself into? And why do I love it so?
I’m crying now, crying, balling up my fists tight over the covers, my red polished fingernails digging into my palms, crying because I’m a sissy maid for a beautiful lady executive and I love it so dearly it makes me cry like the girl I have carried within me my whole silly make-believe life.


It all began when after a number of fruitless years I finally realized my acting career had fizzled out and I was fooling myself about any future possibilities of lucrative theatrical or cinematic success. I decided to get out of New York City and move to a less expensive town and try to have a regular life with a normal job, instead of being a waiter or flyer distributor or seasonal department store salesperson, or doing other “survival” just-paying-my-bills gigs while going to auditions.
With computer and administrative skills I’d used from time to time on office temp jobs in Manhattan, not long after I got to my new town I secured a position as an assistant to Colette Bezniff at her own small advertising agency. There were only a few other people in the company and it seemed like an ideal place to do a straightforward kind of job and reinvent myself as a person content with life, instead of always dissatisfied and yearning.
But my tendency to lie to myself was not something I could escape. From the first moment I met Colette, I wasn’t really thinking about the job anymore. Her statuesque beauty, always showcased in chic and exciting outfits and shoes, excited me into immediate fantasies. I wanted to be her sexual slave, not her employee. I wanted to kiss those high heel boots she wore to dazzle her clients in meetings…I wanted her to even slap me and chew me out if I made a mistake on a document!
But I had a strategy. I told myself I could keep these desires hidden and just use them to make the job enjoyable. Yes, I’d just masturbate at home after work, visualizing Mistress Colette (as I loved to call her in the privacy of my mind) getting ready to cane me, or cruelly milking my cock with her sleek scarlet-manicured fingers until I had no more sperm left to shoot over my submissive daydreams. What lovely daydreams they were!
Oh but self-deception is so rich when it is practiced by a master such as myself! Even as I came home at night from work and ate from a dog bowl on the floor of my kitchen, imagining Mistress Colette was making me do it while tapping her pedicured foot in a strappy stiletto sandal, I put out of my mind the fact that my kinky sexuality had long ruled my psyche to such an extent that it had no doubt limited me my entire life, making me circumscribe my acting career and personal relationships so that I could live my existence in a precious isolation that enabled me to stroke and squirt endlessly over my various castles in the sky, or better I should call them “dungeons in the sky,” wherein I fantasized myself forever at the service of mistresses who knew all my secrets and used my perverted whims for their own dominating purposes!
Ohmigosh I feel so breathless as I tell you my story!
I knew now that I had done what they call in psychotherapeutic circles a “geographic.” True, I could physically leave New York for a new city, as I had done; but I had brought along my desires, and each time I saw Colette in the office, I sank deeper and deeper into my visions of serving her however she decreed.

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Read the entire story in Enslaved Sissies and Maids 37