A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy.

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Chapter One: The Journey Starts.

Well another night and here I sit dressed in my black satin with white lace maids dress, white sheer pantyhose and a pair of black leather 5 inch spike heel pumps. I have my straight, strawberry blonde shoulder length wig on. I have a made up face and I feel very effeminately sissyish. I'm sitting at my computer surfing through sissy and other crossdressing porn and yes fondling myself imagining that I'm all in such a faggot, sissyish lifestyle.

Another night in what has become normal for me as I balance my everyday working male life and such with this sexualized, crossdressing, sissy life. In such a position I only think about having a real man become my Master. Over my years I have found I only pretend to be a man and I am really a pathetic sissy girl who loves the idea of being an enslaved sissy maid and slut.

As I lust over sissy and crossdressing porn I begin to really jerk my sissy dick. The thought and feeling dressed as I am and in such heat for sissy want drives me to what will be my inevitable orgasm. Most every day and/or night this has become much of my routine. I stroke my sissy dick all the while thinking and wishing I was a sissy maid and sissy slut to a real Master. Soon I can't contain myself though and I grunt as I shoot out a wad of my sissy cum all over my slightly pulled down panty. Of course after this incredible high comes the crash as I deflate, staring now at my cum soaked panty, my pantyhose, my maids dress and heels, I think 'Fuck what is wrong with me? Why am I such a fucked up pansy assed, faggot wannabe sissy? Why can't I be just like any other normal and real man?'

I feel like all blah as I soon get up and begin to remove my sissy clothes. I walk to the bathroom and begin to take off my makeup and I decide to step into the shower as I ease my mind and out of this so erotic sissy lifestyle want.

After I shower and dry off it's now late and I head off to bed. By now my feeling for dressing in girly clothes returns. I put on a pair of black sheer pantyhose over a back satin panty and bra. I pull on a black satin full slip to then crawl under the covers and drift to sleep.

That is most often how my evenings go. If I do not dress in one of my maids outfits I will then dress up in slutty clothes. Always in the end each night jerking off to lust for sissy slavery and slut duty. I will cum and then decompress.

Once in a while I cruise the Craigslist ads, just reading and seeing what others like and are into. Some ads are very interesting and horny for me. On this night I come across an ad that popped out to my eye and sounded as if it spoke to me. It read:

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Looking for my sissy maid and cock hungry slut.

Attention any and all you sissies. Maids and Sluts. Mid 30's, SWM, Dominant, I need a sissy girl to be at my service, cleaning, tending to my needs both domestic and personal. A sissy maid and slut to be used and shared with by myself and buddies. Come on all you faggot sissies, apply and lets get it on. Make sure to call yourself a 'sissy faggot' in your reply. The more you tell the better your chance to enjoy servicing me and my needs.

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Wow for some reason this ad just rings as if it's calling out to me. The poster lives relatively near by. I play with myself in all my sissy maid glory as I decide to reply. I tell this possible Master that I'm a sissy faggot and that I am a 40 something divorced, white male, estranged from my ex and living my life single as the sissy crossdresser that I am. I tell him I'd like to be available for master/sissy play and domination. I am tall, slim and can be quite effeminate.

I sit and jerk my sissy dick until I cum and all I do is think about what it may be like to role play Master/sissy for this man. A shoot out an exciting load of my sissy jizz, again onto my partially pulled down panty. Always a gooey mess LOL.

As days pass by and I do my quite routine dress up as a sissy maid or as a sissy slut, to mince around and fantasize about being enslaved as such I jerk off and wonder about this man's Craigslist ad. I wonder how and where I may stack up as a sissy maid and slut to role play with. Until and if I find out about his intention I just keep on with my rather pathetic sissy crossdressing life, each night ends with a mess of cum I shoot out from my thoughts and fantasies.

Then one day I notice a reply on my email by this Master and am all nervous about this. I hum and haw but soon I'm replying to his email . The content of it read like this.

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Hi, Sissy Chantel, thank you for replying to my ad about me wanting a maid and a slut to work for me and take care of my needs. My name is Camron, you can call me Master Camron. Again I'm a mid 30's SWM and am into sissies and submissive crossdressers who can be slutty. I expect in my company OBEDIENCE. I am commanding you to reply filling out your answers to the following questions.

1: Are you being forced into applying to role play sissy maid/sissy slut.

ANSWER: No sir Master. I'm doing this of my own free will.

2: Do you look forward to coming to my home as a sissy maid to be put to sissy maid work by me in the role of you Master?

ANSWER: Yes sir Master, I so want to fill this role of an obedient sissy maid.

3: Do you look forward to being put out in public situations as a sissy maid?

ANSWER: Yes sir Master, I want to experience the thrill of such humiliation.

4: I am a Master who also wishes to have a sissy slut serve my sexual desires, are you willing to be a sissy slut in such a role for myself?

ANSWER: Yes I think so sir Master, I've considered this well and I love but am nervous at the thought of being used a sissy slut and to fulfill a roles as filling your personal sexual desires.

5: Would you accept me sharing you in sexual ways to my male friends and acquaintances?

ANSWER: Yes I think so sir Master, I would love to please your male friends and acquaintances in sexual but again am nervous at the thought as a sissy slut.

6: Are you ok with doing this as a recurring role on an as needed basis by myself and fitting in your schedule to come by dressed?

ANSWER: Yes sir Master, I would be open to this very much.

7: If I wish to take this to a level where we will meet and set up these roles will you give me your personal phone number, to move beyond emailing?

ANSWER: Yes sir Master, my phone number is XXX-XXX-XXXX. [reader, substitute in any number you wish as you read].

Thank you for applying for said role position. If I decide to follow up with you please be available for further contact.

Your Master Camron.

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I sent my reply email to Master Camron in hopes I get a chance to role play as his sissy maid and maybe more. I am nervous but wait with excitement whether he wishes for me to role play.

About one week after my reply I get a phone call from Camron. I am so nervous to be in conversation with a real man who is Master type material. The call goes on for a good 15 minutes or so where Master Camron talks about what he likes as a Master and would expect from me if I were to be a sissy maid for him.

I tell him more about myself and what I am able to do as a start. He finds I am ok with dressing up as a sissy maid and driving to his home. I am ok with doing all sorts of sissy maid's house chores and knowing he can punish me if I fail to meet proper sissy maid chores expectations. I tell him I am fully able to do an and all work in high heels.

Master Camron asks about public humiliation and I say I'd be open for such but not at this time 100% sure. He understands that I'm new at the idea of a role play sissy maid but he suggests he will push me to overcome the fear of public humiliation as he feels most every sissy craves such.

Master Camron moves on to discussing sissy slut service. He asks if I'm ok with sex? Of course I explain I'm a 40 something sissy crossdresser but am a virgin to oral sex on a man's cock and taking cock anally. I have experienced getting oral sex by my then wife, now ex wife. He asks if I enjoyed it? I said it was great, cumming inside my then wife's mouth was so fucking hot. But I laugh and tell him as I was doing it my sissy faggot side was wishing it was me sucking the cock and swallowing the cum.

So he asks will I accept giving oral sex on his cock and if he brings other male friends on theirs? I am nervous and say I am infatuated with the idea of being a sissy cock sucker but until I am faced with such I am not sure about it. Camron asks about getting my ass fucked by his and other men's hard cock? I tell him I dream of taking cock anally and go nuts over such but I am nervous and would have to wait and see.

He sort of angrily says, "Fuck what kind of faggot sissy are you? For fuck sakes I'm ok with using you as maid but fuck I want a God damn slut too." He adds,"If I bring you in to role play you must accept doing oral on my stiff cock. You will swallow any and all cum I feed you. I also want your faggot ass to pound, do you get it?"

I nervously reply, "Umm, ahhh, ok yes, you are right Master, if I do this it must be more that me just mincing around in a maid's dress, hose and heels as your maid. I know I better get it on with cock sucking and having my sissy ass pounded by your stiff cock and any of your buddies cocks. So yes, if we do this, please take my anal cherry and show me the way to why I'm a faggot sissy maid and slut.

We agree that I shall come by Master's house tomorrow morning about 10:00am and spend my first few hours as his sissy maid. I am so excited and nervous to do this for Master Camron. Sleep for me is blissful with anticipation.

About 8:00am I wake up and shower and after toweling off I rub sweet smelling body lotion over my body. I give myself a close shave and get on with my make up application. Once done its into a matching white satin an lace bra and panty. I open up a brand new pair of white tights an pull them up my sissy legs. Pull on a full and ruffly petticoat. Next I put on my black satin with white lace maids dress, a white satin apron, black and white lace choker. I then put on my straight strawberry blonde shoulder length wig then my black satin with white lace mini cap for my head. Finally I choose a simple pair of black leather 5 inch spike heel pumps.

I am so nervous as I sit and eat a bit of toast and coffee. I see it's past 9:30am now and I have about a 25 odd minute trip to Master Camron's house. I put personal belongings in a black leather shoulder strapped purse and a black cotton mini crop jacket. I spritz on some Chanel No.5 perfume, look at my sissy maid self in a mirror, practice my curtsies and soon I quickly and nervously scamper out to my car in my heels.

Once sitting inside my car I am near wild with excitement and I start my drive to Master Camron's house. 25 minutes later I'm pulling up his driveway and stopping. My nerves are a buzz. I want to turn around and head for home but I also want to do this and feel sissy maid service to Master Camron. I say, "Fuck it, I'm a damn sissy in a maids dress and I have wanted to experience this my whole adult life."

I open my driver side door and plant my high heeled feet on his driveway. I stand up and feel the cool morning air caress my white tights clad legs. My sissy dick is rock hard in my panty. I close the door and begin my walk in my heels to Master Camron's front door. Click, clock, click, clock they sound as I step. My hand shakes as I press his door bell.

The 10 or so seconds it takes for Master Camron to open the door feels like an eternity to me but soon the door opens and standing before me in all 6'2" and 200lbs of cool, clean, white male domination is Master Camron. His eyes light up as he sees sissy me in my maids dress, tights, wig, makeup and heels. He says, "Well, well, well, it's nice to meet you Sissy Chantel, you look lovely in your maids dress."

I curtsey and reply, "Thank you Master Camron, it's and honour and a privilege to be here before you and to serve you as your sissy maid."

Master replies, " Come on inside Chantel. Take off your jacket and purse and you can hang them on the coat rack here."

I say, "Thank you Master." and curtsey again.

Once I place my jacket and purse on the coat rack, Master walks me around his house, so I get a feel of how it's laid out and will help me with my soon to be chores. Once done we are in Master Camron's living room He sits in a comfy arm chair and orders me to kneel before him. I curtsey and do as he orders.

I'm on my knees as he pulls out the email questionnaire I sent him and he reviews the role of Master/sissy maid. My agreement is clear and I am excited to get my first commands for sissy maid service of him.

He orders, "Chantel stand up, you will go to my kitchen make me a mug of coffee, two cream, two sugar and come back to me to daintily serve me."

I reply with a curtsey, "Yes Master, thank you Master." as I step out and towards his kitchen. I'm a flutter with sissy excitement as I am carrying out my first sissy maid chore.

In the kitchen I careful follow Master's command to make his mug of coffee to his order. Once doing I walk back to the living room, curtsey and with feet close side by side, toes pointing forward in my 5 inch heels, my knees locked and I bend at my waist as I hand Master his mug of coffee. I smile as he takes the mug of coffee and tastes it. I stay bent over at my waist awaiting his comment and commands.

He replies, "Good job Chantel, you are off to a good start in your sissy maid service."

I curtsey and say, "Thank you Master." as rise back up to await further commands.

Master Camron now dispatches me to get his vacuum and to vacuum the upper floor of his house. I curtsey and thank him as I accept his command. Soon I'm vacuuming in my high heels as Master Camron drinking his coffee enjoys watching his sissy maid at work as a good sissy maid should be.

It takes me a good 30 minutes to vacuum his house's upper floor. Once done Master tells me he is pleased with me and then orders me to now clean his main bathroom. I curtsey and thank him as I go to the bathroom and spend another 30 odd minutes detail cleaning his main bathroom. Once done he reviews it and again is pleased with my work.

He is now sitting back in the arm chair and has me kneel before him again. I am obedient as I do and we chat about my sissy feelings and why I love the thought of serving a dominant man. He gets a good feeling about the sissy faggot I am. Soon talk moves from sissy maid chores to now personal services.

Master says, "Sissy Chantel, you know I'm not just looking for a frilly dressed sissy maid. You know I want a sissy who can be slut too."

I'm on my knees, smile, nodding my head as I say, "Oh yes Master, I want to be turned into your personal sissy slut too."

Master says, "Well I think it's time for you to service my hard cock. I feel you will enjoy servicing my cock as you are a faggot sissy who loves being a slut too."

I excitedly look up at him and say, "Oh yes Master, I'm nervous as I have never sucked a man off before but I do want to do this."

He replies, "You had no problem having your then wife suck your cock when you were pretending to be a man in you marriage to her?"

I reply, "Yes Master, I enjoyed it and I loved cumming in her mouth. But I did wish it was me sucking and swallowing semen."

Master replies, "Good now you will get to live it. Come to me on you faggot knees."

I crawl to him and look up at him from my kneeling position.

Master stands before me and says, "Undo my jeans sissy."

I nervously pop open the fly on his jeans and pull them down to his ankles.

He says, "Now the underwear sissy."

I now pull his briefs down and popping out before my face is Master Camron's oh 6 inch, nicely thick cut cock and his balls hang before me. I am nervous as I await further orders.

Master says, "You like what you see sissy girl?"

I reply, "Oh yes Master. It's beautiful."

He sits back down in the chair and has me now grab his balls with my left hand and take my right hand to fondle his stiff cock. He is now and says, "Ok Chantel, you can suck my cock now, put it in your wet mouth."

I say, "Yes, Master." and I slip his engorged cock into my mouth. I'm nervous but the feeling of slipping his hard cock inside my mouth was intoxicating. I simply can't believe it I am now finally after all these years sucking another man's cock. I begin to slobber all over it and Master gets nice and excited as he moans leaning back in the chair. I am enjoying the sucking as I get into it more than I figure I would. I'm thinking 'cock sucking is quite fun.' I slobber more as I take his cock in my mouth. I am head bobbing as best as my rookie mouth can really trying hard to excite and please my Master here. Master keeps moaning and groaning as his lust builds up and his semen works through his vase. I am so enjoying this and hearing Master Camron moans at my cock sucking is so cool and erotic for me. I feel a sense of immense sissy pride as I work on his hard cock.

"Mmm, keep going you sissy bitch, you sissy slut. A faggot sissy likes you Chantel deserves all this." as he moans.

I work his shaft more and more in my wet mouth. I am really enjoying sucking his cock. I am very hot and horny for his stiff cock. Master Camron moves closer and closer to the joy of ejaculation. He moans and moans some more. I can sense he is coming closer ad closer. He ughs and he grunts as the wad of his glorious cum is about to shoot from the head of his stiff cock. I bob and bob, slobber and slobber as he finally grasps my head with his hands and grunts as he shoots a wad of his thick, gooey and hot cum. It fills my sissy mouth and I have never experienced this before as I taste his hot semen. I as a good sissy slut swallow his load of seed and then pull out as his cock drops before my face. He smiles and pets my head as I look up at him and smile. I open my sissy mouth to show him that I swallowed his glorious cum. I thank him for the honour and pleasure of sucking his cock and for the joy of him cumming in my mouth. He tells me that I did a good job for my first blow job.

I am on my knees as he stands and has me pull up his briefs and then jeans. We enjoy a few minutes of chat on the moment. We agree to hook up again in a few days as we both enjoyed this. Master Camron says he wants to introduce me to his buddy Gage the next time that we meet and I love it knowing I will have two men dominating me and I will have to please sexually.

Soon I'm back in my car and driving back home. Once home I'm so fucking horny from all this and just I have to jerk off until I cum my sissy cum, spraying it over my slightly pulled down panty. It was fabulous to jerk off after such a wonderful sissy morning. I think I may really like doing this with Master Camron and I look forward to meeting with and serving his other buddies. Our next time playing this can't come soon enough :-)

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chapter two to follow shortly.