Becoming a Sissy Maid & Slut Vol. 10

Chapter Seventeen: It's time that Chantel Earned Her Keep.

Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master.

I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave and dressing in a maids dress for the day. Today it's back into a black satin with white lace dress, pulling on a pair of Hanes black, silky sheer pantyhose and stepping in black, smooth, leather 5 inch high heel pumps, wig an makeup. I'm in the kitchen to make Master's breakfast by 8:20 am as per usual.

As Master sits and eats a hearty breakfast I sit and as per usual eat another bowl of plain old gruel. Master though has been fine with me drinking fresh hot black coffee though, to which I make sure he is aware of my immense gratitude for such privilege.

He tells me that I am going to be put out on the 'tranny stroll' tonight, it's time I begin to bring in some real cash to this household, a household of immense privilege for me to live as a full time sissy maid and slut. I totally agree with him and tell him I look forward but with fear of me now having to strut my sissy slut self to bring home some money. At this point now three full weeks of live in slavery the sex with men is now pretty routine but as always a pure joy of male sexual domination of me. Master knows it and will keep me at it always.

He tells me of what I shall be doing as a sissy maid today. First, I must run shopping errands to buy groceries and that will be interesting as again no matter how long you live as a sissy maid, the public is a wild card as people who are most often strangers see you and as such you endure their curiosity, pleasures, picture/video taking, giggles/laughter and derogatory comments. Now since I have been living full time for three full weeks, some in the public and mostly staff at stores I am to show up in know me now and most are polite to being totally cool with enjoying my sissy side, look and demeanor. Those contacts have become routine and often enjoyable for them and me. It's my life and I will live it 24/7/365 for the rest of my sissy life, so I must get use it and try to enjoy it all.

After I do the grocery shopping he says I must then mow his lawn, always fun as the neighbors get to watch me in my sissy maid glory do chores. As I noted earlier most neighbors are aware and ok with me living with my Master as his contracted sissy maid. I'm a neighborhood curiosity and they often enjoy teasing and humiliating me. A couple of more 'conservative' neighbors don't much care for me and my happy, sissy maid lifestyle but meh they more or less avoid me.

Master then tells me that I will then do odds and ends chores, make dinner for him and then later begin my preparing and dressing for what will be my first night as a street walking slut for cash. So it's going to be another busy sissy day. But soon after breakfast is completed, Master retires to relax in the living room and I as typical will wash all the breakfast dishes.

After 9:00am I'm finished and enter the living room to curtsey for Master and say, "Master I'm finished with washing all the dishes and am able to go on my grocery shopping errand."

Master sits up, grabs his wallet and says, "Here Chantel is a shopping list and $200.00 cash to buy with. Make sure you return with any change."

I curtsey and say, "Yes Master, thank you Master. "As I get the money and list from his hand. I then put on a black, cropped jacket and my over the shoulder black leather purse and walk out to my car.

In my car I begin the drive to the grocery store, it takes me but 5 minutes. Parking I find it's time for the public to get another look at a sissy maid as me. In the few weeks I've now been living as Master's sissy slave I have done grocery shopping three times so some store staff now know me and customers have seen me.

But stepping out of a car all in my sissy maid style is always a little bit nerve racking. I know many of the public will see me, laugh at me, comment both curious and derogatory at me. Many will take cell phone pictures and/or videos of me. I must endure and really enjoy this.

Stepping out my pantyhose clad legs and my feet in such sex,y black spike heels both feel good and are caressed by the morning air. Click, clock, click, clock, smiling as I pass curious public. Inside the store I grab a shopping cart and begin shopping for the items on Master's list. More eyes upon me, more pictures, more videos, more comments and giggles. I soon stop by the dairy section and one of the girls who work on staff and has talked to me in my previous shopping trips, her name is Jill and speaks politely, "Good morning Chantel, you look very pretty today."

I cheerfully reply, "Good morning ma'am, thank you, I feel pretty." and then curtsey.

Jill says, "So how are things going in your maids life?"

I reply, "Good as ever, lots of hard work as a sissy maid's work is never quite done." and I smile.

Jill says, "I still don't know how you can do all you maid's work in such high heels."

I answer, "Well yes, ma'am high heels can make things harder to do and slower at times, but they make a sissy like me happy and they please my Master too."

She says, "Well, hun as long as it's what makes you happy."

I answer with a smile and a curtsey, "Yes Miss Jill and thank you, I will see you soon." as we both move on our ways.

I am continuing with my shopping and being a bit of interest for the public in the store. I hear what looks to be a teenage girl, look at me and then asks her mother, " Why is that man dressed like that?"

Her mother looks at me and almost embarrassingly says, "Oh probably no reason than some men like dressing in women's type clothes."

The teenage girl says, "But, wow! but a maid's dress? Look at those high heels he is wearing?"

Her mother replies, "Well, again some men enjoy dressing as maids. The heels, well they are quite high but 'she' and dear you should probably say a 'she' looks to be able to walk well in them."

I had to politely interject, "Excuse me ma'am, sorry I could not help but over hear you and your daughter. Yes, I'm a sissy maid, I enjoy living as one and dressing as one. It's sort of my career now. Yes, I do prefer the 'she' reference as dressed as a female. And thank you for your noticing I can walk well in high heels."

The mother says, "Well you look very pretty and probably make a nice maid."

The teenage girl, "Yes, you look very pretty in that dress." then giggles like a teenage girl would.

I reply with a curtsey, "Thank you both of you, thank you."

We all move on, I pick up more items to fill my cart. Minutes pass, the weight of the publics eyes are upon me as I'm a sight to see. One of the men stocking shelves who has talked with me in previous weeks, says, "Hello Chantel, you as expected look very pretty in your maid's dress and high heels."

I reply with a curtsey, "Oh, thank you sir. We both are keeping busy at our jobs, right?"

He chuckles and says, "Yes we are, but I'm not in high heels." as he chuckles again.

I smartly reply, "Maybe you should try a pair sometime, you may enjoy them." I smile and curtsey.

He answers, "No Chantel, I'll leave that to gals like you." with a wink and a smile.

Continuing on I am finishing up and pushing my cart into a cashier line up. In front at two other customers with carts, and they all see me and smile. The lady in front is placing her items on the counter for the cashier to ring up. The next customers are a middle aged husband and wife. She makes a cheeky comment to her husband, "Mmm, hun maybe you should put on a maid's dress one day, because that girl looks quite nice in hers."

He replies, "No babe, I'll leave that sort of stuff to girls like her." as he looks at me.

More cheekiness from his wife, "Come on hun, don't you want to wear high heels and nylons like her?" she adds, "Looks like fun."

He looks at my black pantyhose clad legs and then at my high heels, smiles and says, "Well she has the legs for those, I don't think I do." as he chuckles.

She asks me, "Why are you dressed as a maid sugar?"

I reply with a smile. "I'm a sissy maid, I work for and live with a gentleman. He is my Master and I love it and love the lifestyle."

She says, "Well I bet he is a very lucky man to have a pretty girl like you serving him."

I answer, "Well yes I hope so, I try to be the best sissy maid I can be for him."

She adds, "Well you go girl." As they both move on through their purchase.

When it's my turn the cashier whom I have had ring up previous sales then talks with me. Her name is Angela, "Good morning Chantel, another busy shopping day for you?"

I curtsey and reply, "Good morning Miss Angela, yes it's always work, work, work for a sissy maid like me.

Angela says, "Well at least you look to enjoy your lifestyle."

I add, "Oh yes ma'am, I love it and love serving my Master."

Angela says, "I still can't believe that you work and live only with wearing high heels, don't your feet and legs get sore and tired?"

I reply, "Oh yes ma'am they do but you get use to it and I love strutting around in tall, spiked heels. It finishes off my feminine self."

Angela as she finishes up my sale, "Well hun, you are a lucky one as you look quite feminine and carry yourself very nicely off as such."

I blush and reply, "Thank you Miss Angela."

I pay and soon am off and on my way back home. Once getting home, I put away the groceries and as per Master's instructions now get on to mowing the lawn.

Now being in 5 inch high heels, and pulling a lawnmower out of the storage shed to then have to move it to the back lawn first is a little bit tough on one's legs. But in my sissy maid glory I am then pulling the start cord to get it started, what a sight that must be for our neighbours. I then begin mowing Master's lawn, and if any of you are aware, spike heels and lawns are not the best to each other. Them lovely spikes can't help but dig into the sod and make it hard to walk and push a lawn mover. I have to try to keep my weight forward on the balls of my feet but at times my heels still dig in and the sod grabs my heels pulling my shoes off my feet, I have to stop and slip my pantyhose clad feet back into the shoes. Master loves watching this as I look silly as such, the nieghbours who see this, likely get a kick out of it as well.

So one may think, why wear heels that slip on and off? Why not wear heels with ankle straps or wear high heel boots? Well I've tried both and yes those shoes or boots wont get pulled off my feet as the heels dig in the sod from time to time, but strappy heels or boots still get their spikes stuck in the sod and that only makes me stumble more as the shoe or boot does not pull off but pulls my balance off. So it's half in one and six in the other :-) Anyways I push on, Master enjoys it, nieghbours enjoy it and I as a good sissy maid still enjoy it even with my struggles :-).

Once done I am inside and freshening up. Master then allows me for my lunch two pieces of plain toast and by his kindness a cup of fresh black coffee. Quickly I eat and am to do a few more chores before I make Master's dinner.

Dinner will just be for Master tonight and I will eat my bowl of gruel. I serve dinner at 5:00pm and he enjoys his meal as I eat my gruel. Later I wash dishes and then get ready for my first night of money earning, street walking prostitution. My first night where I will have to ask for money for sexual services.

In my sissy bedroom, I sit and first fix my makeup going extra slutty for tonight. I then put on a black bra and panty. Onto my choice of pantyhose, I feel, ooh la la for pulling on my black, sheer, back seam pantyhose for another night. Gonna let any guys I hook up with inspect how straight my seams are before they have me pull them down with my panty to my sissy knees and plunge their stiff cocks up my slutty butthole. Next a red satin blouse and my black leather mini skirt. Mmm, I feel so naughty. I step into my black 5 inch high heeled velvet pumps with sexy ankle straps. I'm going to strut around the 'tranny stroll' in these lovely, sexy heels.

Off up stairs for my Master's inspection, I'm certain he shall approve. As I enter the living room, Master is very excited by my outfit. So much so he looks at his watch and sees there is time and says, "FUCK IT! Get over here Chantel, on your knees and suck me off."

Of course I do exactly as I'm told, quickly scamper to him and on my knees. I quickly pull his pants and briefs down, before you know it, my right hand is playing with and stroking his manhood. By now in my sissy slave relationship with Master George we are mutual in our lust. He wants it, I give it. It's that simple.

My sissy lips soon lip lock on his stiff shaft and slurping saliva I go with lots of tongue action too. Master is very happy as I work him into a lustful frenzy of wanted desire to shoot a load of his glorious cum into my mouth.

I bob and bob like a good sissy slut should and of course wants to. I can sense my work is bringing forth his eventual explosion of hot jizz into my sissy mouth. Moans and groans and bingo, Master grunts as a shot from the head of his stiff cock and thick, gooey wad of semen and sperm, sperm, sperm fills my mouth and soon slips down my throat into my tummy. We both sigh as I pull off his cock and he pets me on my head. I tuck him back in and I then stand saying, "Did you enjoy that Master?"

He replies, "Of course Chantel, you are a very good slut to me."

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

Well it's now time we got going, it's about a 40 minute drive to 'the tranny stroll' where I will begin my life as a working street slut.

The drive goes well, Master tells me his expectations of me. Because it's my first night of street walking he is going to cut me some slack, I only need to earn $300.00 minimum tonight. His plans are to have me work nights to bring him $600.00 minimum, but will start me out easy for my first week. Of course I take this for his kindness. Kindness in that I'm still a slut who must get it on to service horny males, to bring home the 'bacon' for my Master. My reward is the sex and hopefully working towards building a regular clientele.

Master is going to take me to a part of the 'tranny stroll' an area where commercial/industrial blends to the back side of a local area park. It's about three blocks and a more private/discreet area of a park. An area where prostitutes and mostly trannys work as the genetic girls are about 2 more block up the street closer to a couple of cheap bars and flea bed motels. That is where most of them work.

Master tells me the trannys generally work in customer's cars parked in the empty alleys and back lots of commercial/industrial places and at the darker back area parking lot and bushes of the park here. He says the reason most horny guys who want to get it on with, or are really into tranny sluts like me is to be more discreet. It works for them and will work for me, Master George tells me. I'm very nervous but sheepishly acknowledge him.

Soon we are at my working place. He tells me to strut myself well, be safe, be smart and please men. He says, "For you at age (40 something) you will probably attract, men over 30-40-50-or older as most of them want to be more in line with my demographic. This is good as most will probably be married, divorced, widowed and/or lesser off in looks and less fussy to get their rocks off." he goes on, "Any younger say under 30 year old males will probably be drunk and likely dared by buddies to hook up with a tranny slut like you. They may be more prone to be a threat or force you to do them for free. If so THEN DO IT! Do not fight them."

He goes on and notes the older guys will more likely want to reduce their risk of the law, as a result will likely be less physical or threatening to me or less likely to rob me. By all means tell them I have a real man pimping you with his strong male buddies.

He then says, "HAVE LOT OF FUN! You know you love being a slut. You know you are a lucky sissy slut looks wise as you pass pretty well, you look youth full for a 40 something and have killer legs and butt especially when in high heels."

I blush with sissy pride and say, "Yes Master, thank you Master.


I then step out, it's now about 7:30pm. He says he will pick me up at 12:30am, that's five hours to make $300.00 tonight. I smile and curtsey before he drives off. I'm on my own and am a little bit scared. Yes I've had a couple of weeks of hard core sex but I have not walked to charge for it yet.

It's a cool, dry evening, twilight has settled in and soon it will be dark. The shine of street lamps is all that hi-lights the slut that I am and now on the stroll. I'm nervous but do my best to not show it. I soon notice a couple of other working girls walk towards me, they look like fellow tranny sluts. I hear their high heels clicking and they are casually chatting. I worry if the are not happy with a new girl on their stroll.

First girl says, "Well hello hun, you look new here."

I sheepishly reply, "Ye..Yes ma'am it's my first night."

She replies, "Darlin you do not have to call me ma'am, my name is Star." she asks, "What's yours?"


I reply, "My name is Chantel, nice to meet you Star."

Star politely replies, "Chantel, my friend here with me is Jenny."

Jenny interjects, "Hello Chantel, that's a pretty name."

I happily reply, "Thank you, Jenny."

Star asks, "So you are a newbie to the tranny stroll here Chantel?"

I reply, "Yes Star, my Master has chosen to pimp me out here."

Star curiously asks, "Your Master? and is he really your pimp?"

I answer, "Yes, Star, I'm a sissy slut to my main man who is my Master. He has broken me into servicing men's needs but now he wants me to bring home the cash."

Jenny asks, "So you are ok with being pimped out Chantel?"


I with pride say, "Oh yes Jenny, I happily live with him full time as his sissy maid and slut. It is a culmination to my life long dream." I ask, "Are you ladies pimped or do you work for yourselves?"

Star replies, "I'm totally on my own and so is Jenny. Some trannies are pimped but most here work on their own."

"Oh," I say, "How long have you two been doing the stroll?"

Jenny replies, "I've been working for what four or so years." she adds, "Star how long has it been for you?"

Star answers, "Well I'm 35 years old, lets see my divorce was what eight no, nine years ago. I started the tranny stroll about one year after the wife and I spilt. She was milking me dry in child support. So about 8 years Chantel"

Me bewildered, "You are divorced with one or more kids?" I add, "Why did you choose to be a tranny prostitute?"

Star says, "Well, Hun, my day job pays ok but my ex-wife is ruthless on child support for my kid. I do not want to let my daughter down, so I had to find away to make money. Being a lifelong cd'er I figured 'fuck it' turn my love of crossdressing into some money." she adds, "It keeps my head above water and my kid supported."

I ask, "Wow, does your ex-wife know you are a tranny prostitute?"


Star says, "Sugar, it's ok to call me a slut or a bitch, if you are like us you know these are terms that make us trannys sorta proud. As to my ex, no she does not know, but she does know I'm cd'er, it is a part reason why we are split up. She does not care for any idea of men crossdressing. Meh it's her loss." as Star giggles.

I then ask Jenny about how she got into the tranny stroll. She replies, "Chantel I am 29 and I lost a good job about five years ago. I too love crossdressing and it got to a point of having to make some real money. Regular day time work was not plentiful for me at the time. I sort a fell into prostitution via Craigslist. I think I look good as chick with dick and soon I was making some damn fine money. Not much less than I was with my old day job. So now I work a bland adequate day job but Friday, Saturday and Sunday, I dress and stroll."