sissymaidruby Posted July 8, 2020 My time with Mistress Zara – chapter one. My first time Last year was not a good one for me. My employer, an advertising agency where I was a senior copywriter, decided to downsize and ‘let me go’ – albeit with a generous redundancy package. Then my wife decided she couldn’t put up with my cross-dressing any longer. She stated that I was doing it more and more, always wore women’s underwear under my work clothes, and that I’d turned from a husband into a wimpy sissy and she was off to find a ‘real man’. She was not wrong. For some time I’d been aware of submissive desires, and could hardly wait till my next opportunity to dress as a woman. So we parted, reasonably amicably, and sold the house. I was able to a small flat and spent my days looking unsuccessfully for another job. My evenings, however I spent dressed as a woman and combing the Internet. I found sites that sold clothing for effeminate sissies, and sites that offered cross-dressing and makeup advice. But all the time I yearned for a strong dominant woman. I even went so far as to visit a professional dominatrice. The experience was humiliating – though not in the way I’d hoped for - and expensive. One late night I found, on a BDSM site, exactly what I had been looking for. ‘Strict Mistress seeks trainee transvestite maid. Live in, all found, and pocket ***. Send CV and letter of motivation to Mistress Zara.” I couldn’t believe my eyes – my dream job! I spent the next day composing the letter and polishing my CV, and sent them off, hoping against hope for a reply. Days passed and I had all but given up but then there was a message on the site for me. “I have had many replies to my advertisement, but yours stood out from the rest. If you wish to continue, then as your first test I want you have your body hair removed. Report back when this is done.” The next day I made an appointment with a waxing salon. They could see me the same day and I emerged with a wonderfully smooth hairless body – arms, legs, chest, armpits and pubes. I reported back via the site, and She replied “Present yourself at my house on Monday at 6 p.m.” She gave an address in a fashionable part of town. Which is how I happen to be standing outside a large house, summoning the courage to ring the doorbell. Almost immediately the door opens and there stands a real sissy maid, who introduces herself as vikki. She is wearing sparkly pink platforms, white seamed stockings, a blonde curly wig, full makeup including the shiniest pink lipstick you can imagine and the most gorgeous dress I’ve ever seen. It is blue satin with pink ruffles and bows, layers and layers of petticoats underneath, and a white glass silk, full-body pinafore and matching cap. Around her neck is a pink leather collar with little bells that tinkle as she walks. A sissy dream. I start to feel excited – as well as apprehensive – about the immediate future. Vikki beckons me to follow her. We walk down the passage until we come to a studded oak door, with a big iron knocker in the shape of a caged penis. Vikki knocks twice. “Enter” says a strict sounding voice, and vikki opens the door. I follow her down the stone stairs into what I realize is Mistress’s dungeon. There are chains hanging from the ceiling, a St Andrew’s cross, a pillory, a spanking trestle with leather cuffs and a narrow bed covered in black latex and again fitted with leather wrist and ankle cuffs. In the corner is a small stainless steel cage – not big enough to stand up in The floor is tiled and studded with rings set in it. One wall displays an array of instruments of punishment: paddles, canes, tawses, whips, and more. Another wall displays various restraints, hoods, gags, collars, leads, blindfolds and so on. In one corner is a large chest of drawers, and on top of the chest are ranged a selection of butt plugs, dildos and strapons. I gasp with overwhelmed excitement at the sight. In another corner is a desk and chair. Along the last wall runs a large wardrobe with mirrored doors, and in front of that, a sofa. In the middle of all this stands Mistress Zara. Magnificently tall in her black patent spike-heeled shoes and black seamed stockings, she wears a tight black shiny latex pencil skirt with a zip all the way up the front, and a white satin blouse. Her black hair is swept up into a high ponytail, her makeup is impeccable, and she exudes an air of authority. “So,” she says, “you want to be my sissy maid?” “Yes M-mistress” I stutter in a suddenly-gone-tiny voice. “My only desire is to serve You in any way You see fit.” “You do not refer to yourself in the first person in my presence! You will say, “Sissy’s only desire…” Is that clear?” Well, let’s get the preliminaries over with. Take off your ugly male clothes. You won’t be needing those for a while.” She smiles. I take off my suit jacket, shoes, trousers and shirt and am instructed to hand them to maid vikki. She opens the wardrobe, revealing a row of stunning concoctions of satin, latex, lace and PVC. She hangs up my clothes and puts the shoes on the bottom shelf which houses a collection of wonderful sissy shoes. I stand shivering in my underwear: black seamed stockings, six strap black suspender belt, black French knickers and camisole, and underneath the camisole a black lacy bra. “Very elegant,” says Mistress Zara, “but hardly suitable for an aspiring sissy maid. Have you done as I instructed and removed all your body hair?” “Yes, Mistress. I was waxed all over on Friday. Oh,I mean sissy was waxed all over.” “That’s better. Now take off all that underwear, and we will start from scratch” I divest myself of my treasured lingerie and vikki takes it away to the wardrobe. “Vikki,” says Mistress, ”first the satin and lace eight-strap pink suspender belt and a pair of white seamed stockings – just like yours, vikki.” Vikki goes over to the chest of drawers, opens the top left drawer and takes out the suspender belt and a fresh packet of stockings. She fastens the suspenders around my waist. She opens the packet of stockings, shakes them so they unfold and strokes them across my quivering body. She kneels down. I raise my right foot as she rolls up the stocking then slips it over my foot. She unrolls the stocking up my eager leg, smoothes it straight and fastens the four clips. Then it’s the turn of the other leg and stocking. “Bra next,” says Mistress. “The pink ruffled satin one, size 38C.” Vikki returns to the chest, opens another drawer, searches through the bras and returns with a stunning pink satin bra with ruffles. Once again she ds it across my body first, teasing me with the wonderful feel of the satin. I hold my arms out in front of me and vikki slides the bra up them, then walks behind me to do up the clasp. She then tucks a C-cup falsie into each side. “Now for the difficult decision. Panties? Or bloomers? Hard to choose but I think bloomers as they will ***k out from under your dress and be more humiliating.” Vikki returns with a pair of pink ruffled glass silk see-through bloomers. I step into them and vikki pulls them up tight then smoothes the legs down to just above my knee. By this time I am so excited I start to get hard. “Enough of that!” says Mistress, slapping my penis through the bloomers with her riding crop. “Petticoats next! Seven layers in white chiffon, if you please vikki.” Vikki goes to the wardrobe, returns with the oh-so-gorgeous pettis and I step into them. Vikki arranges them nicely, tugging them up and down till they are perfectly even. “Now we need a dress. I think the Felicia, don’t you vikki?” “Yes Mistress,” she replies, “a very good choice, Mistress.” She steps over to the wardrobe again and returns with the most stunning dress I have seen in my life. She holds it up to herself for me to see. It’s pink satin, with a pretty round neck and short puff sleeves trimmed with lashings of baby-blue satin ruffles. Around the hem of the skirt is a four-inch band of blue lace. I am near to fainting with trembling delight as I hold my arms up and vikki slips it on to me. She smoothes down the tight bodice, tugs the skirt evenly, makes sure the puff sleeves are correctly fitted, then zips me up at the back. She then fetches a glass silk baby blue bibbed apron, puts the top strap over my head and ties the sash in a pretty bow at the back. Mistress smiles, gets up from her chair, and walks over. Now I don’t think you’ll ever want to take off this dress, but let’s just make sure.” She produces a small silver padlock which she passes through the two little rings at the top of the zip and s shut. The dress feels wonderful – the bodice is tight and the skirt flies up when I am ordered to pirouette. “Very pretty,” She says “now for the shoes – what size are you?” I tell Her and She fetches a pair of pink patent mary-janes with platform soles and a five inch heel. They have a white frill around the top. I step into them, vikki fastens the buckles and then once again I am padlocked into them. “Hair next” says Mistress , and vikki fetches a shoulder length wavy blonde wig and carefully puts it on me, then brushes and fluffs it. A maid’s cap to match the apron completes the ensemble. I look in the mirror and almost faint with delight. “Very pretty” says Mistress. “Now we have to give you a new name. I think ruby is suitable – trainee sissy-maid ruby!” She smiles and says “I have to attend to some business for a little while, but vikki will do your makeup, teach you to curtsey and as you will be serving Me together you can get to know each other better.” “Oh thank You, Mistress, thank You for having this sissy put in this wonderful outfit. And thank you too, vikki.” “I do like a grateful girl, ruby.” With that, she sweeps up the stairs, and closes the door behind her. “Now for your make up, dear,” says vikki. “Sit in the chair and I will fetch the case.” She opens the makeup case, and takes out a bottle of foundation. She squeezes some onto her hand, takes a brush, dips it in and proceeds to make up my face, with careful smooth blended strokes. “Now some powder” she says taking out a compact and a big powder puff, and powdering over the foundation. Then comes the blusher – two perfectly matching dabs, one on each cheek. Now the eyes – a set of extra-long false eyelashes first, then eye liner and pink and blue shades of eye shadow, and finally mascara. Lipstick next – five layers of ultra-glossy pink, the same as she is wearing, followed by Lipcote to keep the lippy on my lips and not on cups or glasses. I look in the mirror again and a great wave of happiness surges over me. “Now let’s teach you how to curtsey.” Vikki executes the perfect curtsey – one foot back behind the other, bending the knees and holding up the skirts with both hands a she bows her head. I try to copy her – my attempts are pathetic at first but I gradually get the hang of it. We both curtsey in front of the mirror and I am struck by how pretty we look. “Come and sit down on the sofa, ruby,” says vikki, and we sit down together. “So, how does it feel now?” she asks, and I reply “Just divine, vikki!”. She moves closer and takes my hand. I moan with desire – she is so pretty. We lean towards each other, our lips touch and before I know what I am doing we are kissing passionately, our tongues entwining and our glossy lips sliding against each other. I feel myself get hard as vikki puts her hand on my nyloned knee and slides it upwards. By the time she reaches my bloomers, I am panting with desire. I slide my hand up her leg and stroke her stocking tops and pull gently at her suspender straps. She slides her fingers under the leg of my bloomers as I reach her frilly satin panties. Just then the door opens. We spring apart as Mistress’s heels tap against the stone stairs. I am blushing furiously. We get up and curtsey to Her. “So,” says She, “You do appear to have been getting to know each other. Stupid girls – did you imagine that I don’t have a camera in here?” Out of the corner of my eye I see vikki smile. I think I have been set up. “You will both be punished severely for this.” ©sissymaidruby 2020
Deleted Member Posted July 9, 2020 Great start to the story I just wish I could find something like that
Deleted Member Posted July 9, 2020 Enthralling!! I can't wait for the next chapter in Ruby's adventures!!! 🔥💝🔥
Charms Posted July 9, 2020 The only thing i did not like is it ended i need no i must have more. I do wish you could if fount acceptance from your wife. It woukd never bother me if my partner x dressed id even go shoppi g to clothes with. Although i dress alternative most days. Think hippy and colourful does not mean i can not pick out a good outfit for others. Once again a tremendous well written story so far
Ro**** Posted July 10, 2020 When the slave of Mistress Lucy zara was old,she pubblishing a post when find a new joung slave and take the coordinate on website sexpartners20 plus, i contact her because is beautiful and worship her and was her virtual slave for 3 days,send her a my pic and enjoy because am handsome and athletic, when tell me for the practices that doing,answer that am a sub,don't a slave, for me is ok all less strapon',dildo,sissy ***,and practice that can damage me like clinical and ballbusting, don't was very happy,but enjoy if wishing punished very hard with whipp,trample,cigarette or fake pistol , this 3 virtially day with her do't were very good because is authoritarian fancy , severe and for nothing permissive but i wish try because worshipp her for how much is sexy,beautiful and elegant,i respect Mistress Zara,she was honest immediately telling me how she wishing,i the same from before, perhaps she permitt me for to be her virtual.slave(,living far between us)because i'm hansome,athletic and perhaps like me,but for me more that a pleasure was a hard work because wishing always something,she that is an intelligent Lady, think that don't like to be her slave and finish. I don't can never tell bad by her. If someone accept to became her slave had to Accept all for her,ok can that she'll be egoist and don't cuddle her slave from that i hear,never see,but if wishin that is Your Mistress accept how she is or find other! If reading this post wish send You my best regards,Mistress Zara
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