Becoming a Sissy Maid & Slut Vol. 04

Story Info
More on my sissy journey, this is vol. 4 and will be Ch.10.
3.4k words
4.51
27.8k
19

Part 4 of the 14 part series

Updated 06/08/2023
Created 07/13/2016
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Preview: Here is another chapter of my multi-part "Becoming a Sissy Maid & Slut Story." I so hope you all are enjoying this story. I'm no professional writer so excuse me for any writing errors. But I have a flood of sissy maid, slut, crossdressing ideas, thoughts and fantasies to share. I will add more chapters to this unfolding multi-part story now ONE chapter at a time until my story runs its course. Enjoy!

*****

Chapter Ten: Off to Work I Go.

The alarm clock goes off now becoming as typical for my new sissy life at 7:30am. Oh, another day, I awake still groggy from last night. But I know I can't waste time, a sissy's life is one being under the thumb of her Master. I take off the clothes that I sleep in, my black satin slip, a black, satin and lace bra, with a black, satin high cut panty and black, sheer pantyhose. I love sleeping in pantyhose. These are all folded and kept under my sissy pillow, for my nightly sleep wear.

Off to the bathroom I go and to give myself another enema. I give myself an enema each day now to start my day out nice, fresh and clean. I then shower, dry myself off, spread on sweet, fragrant, body lotion and give myself a close shave as I may be a sissy girl but I still have face shaving to do. Then it's another morning of makeup application. This is something men do not have to do, but like most real girls, sissies do makeup everyday. I takes me about 25-30 minutes to shave and apply makeup. So by 8:15-8:20am I'm ready to put on a maids dress for the day.

Today, I'll show myself in one of my light pink, maids dresses. I start with a white, hip length satin slip over a white, satin and lace bra and white satin high cut panty. I put my breast enhancers in my bra. Today, I'm going to open up a new pair of light, pink, sheer pantyhose. I slide these feminine pantyhose with joy up my smooth legs and over my sissy hips. Ok, it's frilly petticoat and then dress time. I top it off with my white satin and lace apron, pink with white lace choker and pink and white lace cap on top my strawberry blond wig. Finally I pick out a pair of light, pink, patent, 5 inch spike heel pumps. Standing in front my full length mirror I look at my sissy maid self and tweak and adjust my outfit. I'm thinking, oh I look so cute, dainty and pretty, Master will surely enjoy this look too. It's now up stairs to the kitchen I go to make Master's breakfast. If I'm in the kitchen by 8:30am, then I know that I'm on time.

With breakfast for Master now on the go, I then begin making myself a morning pot of gruel. Soon Master arises and enters the kitchen. I turn to him and give him a cute, sissy curtsey, saying "Good Morning Master."

Master eyes me in my pretty pink satin maids dress. "A very pretty maids dress today Chantel," he says. I curtsey and thank him again.

Soon, I'm serving him his breakfast and pouring him a fresh, hot cup of coffee. After serving I curtsey and wish him to enjoy his breakfast. Master tells me to pour a bowl of gruel for myself and to fill my sissy cup with some day old, cold black coffee as per usual now in my sissy life. I do as I'm told. He then allows me to sit at the table with him, remembering to only speak when spoken too.

As breakfast continues, he asks if I'm looking forward to my first day working at the adult store? To which I tell him I'm very excited at doing this job today and in my pink maids dress, pink pantyhose and my pink spike heeled pumps.

As Master finishes his breakfast and then heads off to his work place, I curtsey and wish him to have a nice day. He sternly tells me to be on my best behavior at my sissy job and to make sure all required household chores are also done by the time he comes home from work. I curtsey with a, "Oh yes, I will, Master."

I wash the breakfast dishes and tidy up to then get my pink, sissyish purse and white cropped jacket on to head to the adult store. On the way there I had to stop to buy gas for the car, I thought, Oh boy a quick little humiliation thing as I do such at a gas station. Once at a gas station I had to step out of my car in all my pink, satin maids dress, pink hose and heels glory. It was electrifying and embarrassing as others filing up soon notice sissy me.

So I am now fumbling through my pink, sissy purse trying to find my debit card. Once I find it I begin the process of filling up my car's gas tank. A few others look at me and smile, one lady says I look very pretty in my pink dress and pink high heels. Of course I curtsey and thank her. She giggles as she walks to her car. A couple woots and whistles by both males and females and soon I'm finished. Back inside my car and off to the adult store for four hours of sissy work for a whole $20.00 of net pay.

Once at the store and parked I step out of my car and more public exposure of my faggot, sissy maid self. I'm nervous but also so excited as I step inside the shop. As I walk up and to the main counter, I see Christa is waiting for me. I curtsey for her and say, "Good Morning Miss Christa, sissy Chantel at your service."

Christa replies happily, "Good Morning Chantel, you look so very pretty in your frilly, lacy and satiny pink maids dress," she adds," Those are lovey, pink heels and yes pink nylons look so good on your sissy legs."

Of course I curtsey again and say, "Thank you ma'am."

She goes on, "Nice job on your make up too, so very girly."

Oh I'm so excited at such talk, if my sissy dick was not all caged up it would be so rock hard, but I say, "Oh, I'm so grateful for your compliment Miss Christa."

Christa next, dispatches me to the back room where I can put my pink, sissy purse and take off my white cropped jacket. Then she gets me started on some tasks. It seems the store owner, Mark has a few boxes of newly arrived merchandise that needs to be opened, priced and put out on display. I curtsey and get on with the task at hand.

As I am placing out products, tagging with price stickers, making sure all is on proper display, customers come in and about. Christa basically carries on discussions with customers as well as selling to them. But I am noticed by all customers who come in pretty well right away. I mean a sissy maid in a pink maids dress, pink pantyhose, pink high heels, a wig and makeup on well how can one not notice me.

Christa explains that I'm a new hire and the owner likes the idea of having a sissy work here for inexpensive labour and lots of in store entertainment. Most customers enjoy what they see. Some come to me and tell me that I look cute and very sissyish. Of course as per usual I thank each person and curtsey.

Not too much later a gentleman enters the store and strikes up a conversation with Christa. I keep busy, pricing and placing out merchandise but with each customer who enters the store I can't help but to look. It seems this gent looks to be rather a regular customer and is returning some videos. But he also notices me as he looks at me. He and Christa are talking, I can't make out all they are saying but it is surely about me. But it seems he is asking about the sign at the counter where it states "Ask us about private time with Chantel."

Soon I hear a 'ding' of a counter bell and Christa is calling me to come to her. I curtsey and say, "Yes, ma'am, I'm coming ma'am." as I scamper in my high heels to the counter. Once arriving I curtsey again and ask Christa, "How may I be of service?"

I seems this gentleman who is a mature gent, average height, weight and looks is interested in the 'private time' with me. Christa tells the gentleman that I'm quite the submissive, sissy girl and besides doing regular work chores here, that I also like to be made available for some private times. She introduces me as sissy Chantel.

I curtsey and say, "Yes sir my name is Chantel and I would enjoy being of service to you."

The gent replies, "My name is Ralph and I really like the way you are dressed, so pink and girly," he adds," You look like a fine, sissy maid."

I curtsey again and reply, "Yes, sir Ralph, I am a happy sissy maid."

Christa now says, "Chantel, Ralph has given us a suggested donation of $20.00 to take you in back in the privacy/video booths for about 20 minutes of free time," she goes on," Be a good girl and do as he asks."

I face Christa, curtsey once again and reply, "Yes, ma'am, I will happily go in back with Sir Ralph."

He then takes my right hand in his and we begin walking to the back area of the store where the privacy/video booths are, my pink, spike heels clicking with each step.

Once in a booth he says for me to kneel down before him, to which I do as a good sissy girl should. I can sense that he is excited and growing with lust. He tells me again how cute I look in my pink maids dress, hose and heels. He tells me my makeup has me looking quite feminine.

Feeling quite proud and special I say, "Oh thank you sir, I really try to look as feminine as I can."

He says, "I can tell and you are a lucky sissy as your features come out quite girlish."

I'm now gushing with sissy pride and say, "Thank you sir."

Ralph now has me undo his pants, pull them down and then pull down his boxers. It's always now a nervous but exciting moment when I pull down a guys pants and underwear. Waiting to see another man's stiff cock. Ralph's is quite typical about 6 odd inches hard, cut and of good girth. Don't get me wrong as a sissy slut I love all cock, I worship all cock and I do want to service all cock given to me. Ralph is getting more and more hot and horny. He sits on the booth's chair, legs spread open and me on my sissy knees before his engorged cock. He excitedly tells me that he wants me to suck him off and make sure to swallow any cum he will feed me. As I look up to him I smile and say, "Oh yes sir, I will happily suck you off and I will swallow your man juice as my last name of Swallows notes."

He smiles and lays back on the chair. I cup his balls with one hand and grasp his hard on with my right hand as I slip his cock through my wet, lipstick covered lips. I hear him moan and smile. I then run my tongue around his shaft with a lot of saliva wetting it all up. I moan and he moans. I begin more and more sissy head bobbing on his stiff cock. We keep working at it and our lust is ever more hotter. Ralph is so enjoying a sissy slut like me suck his cock. I'm happy as a sissy slut to oblige.

About 8 or 9 minutes of this and I can sense he is moving towards orgasm. His moans become clear and his stiff cock is nearing its eventual explosion of man goo. Ralph still leaning back in the chair takes his right hand and begins to press my head down on his shaft, not too hard but enough for me to know when he blows his thick wad it will spray nicely in my sissy mouth. Not a few seconds after thinking that, it then happens, a flood a creamy and warm cum fills my mouth. He grunts as he shoots and soon he pants a deep expelling breath. My mouth has the pleasure of tasting his warm goo and swallowing it.

As I slip my mouth off his shaft and lick it clean. He looks down and tells me the lipstick all over his shafts is cool and fun to look at. I am to then tuck his manhood back in his boxers and pull up his pants. He tells me that he enjoyed that blowjob very much. On my knees I look up then bow my head and say, "Thank you sir." He then steps out of the booth and walks back to the front of the shop. I fix my lipstick, get back up on my heels and too walk out to the front.

Ralph is chatting with Christa as I come out front. Christa tells me that I'm a good girl, Mark the owner will be pleased. I curtsey and thank both Christa and Ralph. Christa tells me to get back to my store chores. I curtsey and say, "Yes ma'am." and walk back to the merchandise I was placing out. Ralph walks out of the store, Christa, yells back to me, "Good job as a little cock sucking, sissy Chantel." I curtsey and thank her again.

Over the next three or so hours of me doing tasks in the store as a sissy maid, I did have two other gents take me in back for some private times. In both cases they enjoyed blowjobs from me and enjoyed getting off in my sissy mouth for a fair donation into the pot of $20.00 each. This all totaled $60.00 in private time donations to which will be split 50/50 with my Master. Of course as a sissy maid and slut I get none of the money.

About a 1/2 hour to go in my first store sissy shift, Mark arrives to check on things. Christa calls me over to great Mark. Of course I do as I'm told and greet him with a curtsey and a hello sir. I stand silently looking down as Christa tells Mark of my day and of the three men I had some private time with in back. Mark is pleased and then has me follow him upstairs to his office. I daintily walk behind him up the stairs and once inside his office as to be routine, I kneel before him.

He says, "So a very nice first day on staff here for you Chantel."

I reply with a voice of satisfaction, "Yes, sir it was a very nice first day."

Mark adds, "You even did some private servicing of men today, three men from what I see here," adding, "$60.00 of bonus grab cash to which you will deliver $30.00 in an envelope to your Master today."

I say with a sense of pride, "Oh yes sir, it's a nice little gift that I made to share with you and my Master."

"Christa tells me you were very good at following on floor orders by her today and completed all tasks she had you do," He says, "Plus you were enjoyed by customers in the shop today. You were said to be very pretty in your pink maids dress, pink nylons and pink high heels."

I reply with joy, "Oh yes sir, I hoped that I was very polite and entertaining."

Mark next moves on to putting $30.00 in an envelope that I shall give Master at home. He then has me sign off on my 4 hours of labour and the official $50.00 pay out. This is our pay records. I then am handed two $20.00's and one $10.00 bill. I then as a 'privilege to work tax' hand back $30.00 to Mark. This nets out my true sissy pay of $20.00 for four hours of sissy labour. Very good pay for a faggot, sissy like me. Mark lets me place the $20.00 into a 'pay' envelope that I will also give my Master when back at home. I am allowed to rise from my knees and curtsey with a thank you to Mark

Mark, next has me clear a space on top of his desk. I do as I'm told. Mark then grabs a tube of Astroglide, lubricant. Orders me to bend over the top of his desk, pull up my dress and petticoat. He then comes behind me and firmly pulls my pantyhose and panty down to my knees. I now hear his belt loosen and his pants zipper be pulled down. I am staring to my front and not look over my shoulder. Mark now squirts out some lube on his fingers and begins to lube up my butthole. "Ohh, ohh,mmm, feels good sir." I say.

Mark replies, "That is nothing, I'm gonna bang you hard with my hard cock Chantel, fuck you like the slut you are and know that you want to be."

"Mmmm, sounds so good sir."

Soon he begins probing my butthole, it hurts as he stuffs his hard cock up inside me, but once in, it begins to work ok. He thrusts gently at first, working his hard cock, the lube up my butthole to where we can be in to it as if we are one. The sound of us moaning in lust was so hot. I stare in front of me, my upper body laying flat on the top of his desk. Mark moans and pants. His rhythm and trusting does get more intense. I almost feel as if I'm going to fall off my 5 inch heels. Minutes pass and both of us are into it BAD! I so want him to shoot his load of creamy, cum juice up my rectum. I can feel he is now getting closer to doing so.

"Ahh, ugh, ummm ohh." I repeat over and over.

Mark moans and groans over and over, each pelvic thrust inches his wad of goo moving up through his hard cock, until it's bam, and a jet of hot semen fills inside me. Mark groans with joy, I just give a deep ugh and mmm. His thrusting slows and then stops. He smoothly pulls out of my butthole and steps away.

I'm now slowly getting back up off his desk and begin to turn towards him as such he tells me to drop back on my knees and take some tissues on his desk and wipe his dick clean and then tuck it all back in his underwear and pull up his pants. I happily do as I'm told. He then walk as out telling me to clean myself up and put myself back together, I bow and say "Yes, sir."

He chimes back, "Don't forget your two money envelopes as you come back down stairs."

"Yes sir." I say.

I get myself all back together after wiping the lube and semen from my backside with some wads of tissue. I then gather the two envelopes and head down stairs to the store front. Mark is talking with Christa as I get my cropped jacket and pink purse from in back. As I'm about to leave for the day, Mark and Christa tell me that I'm a good girl. I curtsey and thank them. Christa says, "See you tomorrow at 10:00am Chantel."

I curtsey and reply, "Yes, ma'am, see you at 10:00am." as I step out and back into my car. I am now on my way back home and to get on with my household chores and soon dinner before Master arrives home. He will be pleased with my first work shift at the adult store.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
Lolilol47Lolilol47over 4 years ago

Doesn't she take pleasure for being fucked? You don't describe this at all. I guess you need to be trained to cum while being fucked in the ass but it can be done...

WantstotryitWantstotryitover 7 years ago
re:its not biaring

Well said. Can't agree more

AnonymousAnonymousover 7 years ago
It's not boring.

For a sissy it is a sexy story with alot of the things we want to have done to us and make us feel like a true fem crossdressing sissy bottom. You go gurl. Lacie Bottoms,sissy tranny

AnonymousAnonymousover 7 years ago
great story.

Well written story from a sissy perspective. Cant wait for next installment

Share this Story

Similar Stories

A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
From a Husband to a Dutiful Sissy Ch. 01 How I went from a loving husband and to a sissy for my wife.in Transgender & Crossdressers
Sissy Girl Forever Pt. 01 Feminized sissy is trained by loving Mistress.in Transgender & Crossdressers
His Sissy Bitch Ch. 01 A man's employer uses him for more than an employee.in Transgender & Crossdressers
A Jamaican Vacation Ch. 01 White guy finds BBC, and himself, in Jamaica.in Transgender & Crossdressers
More Stories