Becoming a Sissy Maid & Slut Vol. 09

Story Info
More becoming a sissy maid & slut, vol. 9, Ch. 15 & 16.
4.5k words
4.54
18.5k
9
0

Part 9 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

Prefix: I will be fast forwarding a few days in my sissy maid, sissy slut lifestyle story here. From the last chapter ending on a Tuesday night going into my second week as Master George's full time sissy maid and slut to that of me getting ready for the following Saturday night of slut service.

I feel the story's journey no longer has to follow a linear day format. I have some real exciting upcoming chapters of plot twists and additions. So let me pick up the story at my second Saturday night as Master George's sissy slave. Enjoy!

*****

Chapter Fifteen: Truckers Need Fun Too!

So I have just finished cleaning up from a Saturday night dinner. Master has both Rick and Gage over for dinner as they all look forward to my upcoming Saturday night slut service. I'm sitting at my make up table in my bedroom, fixing my makeup for the night. Wearing a black bra and panty, I next pull on a pair of Hanes, silky sheer, black pantyhose. I put on a red, satin long sleeve blouse and a black, denim, mini skirt. I cut it at the waist line with a wide gold Lame belt. I then put on hoop earrings and my as normal strawberry blonde wig. For sexy foot wear I grab a pair of black, velvet, knee boots with a 5.5 inch slightly thick spiked heel and a 1 inch platform. I joyfully zip up each boot as I pull each over my pantyhose clad legs. I spritz on some Chanel No. 5 grab my white, shaggy, bolero jacket to put on and a matching white purse with all I need for tonight.

The men all loved my look. I will surely attract looks tonight. I am not yet aware what the plan for my Saturday night slut service will be. But Master tells me it will be interesting and should be exciting for me. We soon get inside Master's Dodge Journey SUV and drive off. The three men carry on conversation, I as normal only speak when spoken too. I do feel cute, sexy, fun and flirty tonight. I hope which ever men I service tonight that they all will enjoy me.

The drive takes us about 30 minutes as such it is soon getting to be sun set and then twilight to night. It's actually cool and cloudy so it's looks a bit more dimly lit. But we pull up to a Truck Stop/Diner named 'Alice's Place'. It looks to be a popular truck stop and diner for mostly long haul truckers. I now see that I'm going to be offering myself to men who are truckers this evening. This could be interesting. Master tells me that is exactly what it will be for me tonight. Master tells me that I will spend the next few hours just strolling around the truck stop and diner looking for maybe some horny and or stressed out long haulers who could use a bit of sexy company and relief.

Of course as always I'm nervous as even though I'm prostituting myself still for free, I worry about the reaction of these males, some of them a pretty gruff and rough dudes.

Master just says, "They are likely stressed out, some lonely and some horny, so I should be fine." as he smiles at me. I just hope I look sexy or slutty enough to just have them want to get off either up my sissy ass or down my sissy throat.

Soon though I'm out of the SUV and Master tells me to do my best, getting some video would be cool too and to have fun as he and the guys then drive off. So I begin to strut around in my tall heels and look out for truckers. A few minutes into my slut walk I see a truck pull in and park, I think to myself, well here goes, lets check out this guy and see if he's into a slut like me.

Click, clock, click, clock my heels make as I approach his truck. He has not seen me as of yet as I come around the passenger side, as he steps out the driver's side.

I politely say, "Hello, sir."

The driver is a tall man in his late 20's and of a native North American look.

He stops and looks at me and with a bit of a shocked look he says, "Jeezus, what the Hell?" he stops for a moment, thinks about what he see's and then adds, "Hello, that is quite the outfit you have on. What you doing here dressed like that?"

I reply, "Thank you sir, I'm a slut sir."

He excitedly says, "You damn well look like one. Are you looking to work it here?"


I answer sheepishly, "Yes sir, but more so I am a sissy slut as I have a true Master who owns me as his sissy slut."

He in curiosity asks, "So are you really here to be as a slut tonight?"

I reply, "Yes sir, but my Master is still breaking me in this slut lifestyle and has me here offering myself 100% for free services." I add, "That is I suck cock and I take cock up my sissy bottom, would you like to have one or the other with slutty me? We can hop back in your cab and just do it if you like?"

He replies, "Well tell you what, let me get some dinner and think about it. After I eat maybe we can hook up." as he winks, smiles.

I answer with a curtsey, "Oh yes sir, I'd enjoy that, I hope we can hook up later on."

He then walks away to the diner.

So I keep on my slut walk and a few minutes later out of the corner of my eye I see a white male, oh maybe 30 something, in a check shirt, blue jeans and cowboy boots come out from the diner and I figure to go talk to him. I quickly scamper my heels clicking away as I near him, I say, "Excuse me, excuse me sir."

This man looks at me and stops a bit stunned, after all he sees what looks to be a tall, sexy, slutty looking woman walking towards him, but soon he sees that yes, I'm a tranny slut and he replies, "Yes, what do you want?"

I reply with a curtsey, "Um my name is Chantel, I would like to ask if you are lonely, maybe need some company and a fun time tonight?"

He asks, "So you are what some kind of slut?"

I reply, "Yes sir, but I'm a sissy slut." I add, "I am here by my Master's desires as he wants me out as a slut tonight but I'm 100% for free."

He with curiosity says, "Mmm sounds interesting, you look pretty hot, killer legs in those boots and short skirt. My name is Bill."

I reply with interest, "Mmm you like it?" I give a devilish smile and kink my right leg extending it in its 5.5inch high heeled boots. "Do you wanna have some fun up in your cab?"

Bill stands and looks at me and at his truck, says, "Fuck it, could be fun, why not?"

We walk to his truck on the passenger side and he opens the door for me and extends his hand to help me up into his cab. As I climb up, short skirt, black hose and black velvet knee boots in front of his lustful eyes, Bill catches a wiff of my Chanel No. 5, and says, "Mmm you smell nice Chantel."

I turn back and look down with a smile as say, "Thank you sir."

Soon we both are inside and he has me get on his sleeper's bed and wait on my knees. Bill turns on a light, kicks off his cowboy boots and quickly pops his pants open and pulls them off. His breathing is getting exciting. He next slips off his briefs and his oh 6-6.5 inch cut, cock is popped straight out. I look at and tell him it's beautiful, He fucking loves hearing that. I know men love it when they hear that their cocks are adored.

Bill then straddles the bed and sits back sitting up, his legs now out in front and on either side of me, on my knees. He fondles his cock for a few moments and we make eye contact, he says, "Fuck, you are quite sexy looking Chantel. You fucking tranny sluts have that hot, slutty, but sexy look."

I sexily reply, "Oh thank you sir, I wanna please a real man."

I then move my hands towards his stiff cock and balls, I see he so wants me to play with them. I gracefully cup his balls with my left hand and my right then begins to fondle and pull on his stiff cock. Bill moans with joy. I soon lean forward and down to his cock, I kiss its stiff head and Bill loves that. I then open wide and let his rod slip into my mouth, my wet tongue works around it as if it wants to hug that cock.

Minutes pass and more moaning from Bill. I begin to slurp some saliva and begin my sissy slut head bob. My fingers play with the underside of his shaft near its base and his balls too. He fucking loves it, just loves it. I now moan and he does too. I can sense his cock wants to dance inside my mouth and I know his scrotum and prostrate are bringing forth a good, gooey wad of sperm filled semen.

The man and his near breathless panting is like music. Minutes work by and his cock's head throbs as it wants to shoot out a gush of hot jizz. Moments later with a grunt and a moan his cock lets go and I get the pleasure of another man's hot, gooey cum, all his glorious semen and sperm will be swallowed by me, with sissy pride.

I gently pull off his cock, look at him and see his smile as he pets my head, stroking my hair. He says, "That was fucking awesome Chantel, fuck you know how to suck a guy off."

I smile, wink and say, "I'm glad you liked it, your cum was delicious, it's an honour to swallow it all down my throat and inside my tummy."

I kneel back up and Bill rolls off his sleeper's bed, pulls on his briefs and his jeans, then his cowboy boots. He stands part way up and turns to me giving me a hand to get up from the bed now too. He then carefully helps me out and down from the cab of his truck. I curtsey and say, "Thank you Bill."

He smiles and says, "No, thank you Chantel. I'd love to hook up with you again some day."

I reply, "I bet that we will some day."

He then walks around to the driver's side and gets back in. I with the taste of his semen in my mouth, begin strolling on the slut walk again.

It's pretty well night now and I keep my eyes open for men. Lucky for me the first guy I talked to who said he had to eat first was actually walking around and looking for me.

"Ahh there you are." he says.

I turn and see him, saying, "Oh yes sir it's you again. Did you have a good dinner?"

He replies, "Yes I did I'm just looking for some after dinner fun now. By the way my name is Ed, what's yours?"

I curtsey and say, "My name is Chantel, do you really want to play before you get back on the road?"

Ed says, "Yes, it could be fun," he asks, "So is it true you are walking the stroll here for free?"

I happily reply, "Oh yes sir, my Master is still breaking me into this lifestyle, I suck or you can fuck me, your choice?"

Ed says, "Well you are a pretty good looking tranny slut. It turns me on and the sexy way you are dressed," he adds with excitement, "Lets get to my rig and play."

I say, "Yes, please, lets play, it will be lots of fun."

As we walk to his rig our excitement builds. He too helps me up the passenger side and soon both of us are inside. I kneel on his bed. He pulls off his Dayton's and has me pull down his blue jeans too. He kicks them off and then has me pull down his briefs, and off they go. Ed is a nice, thick 7+ inches of native indian, cut manhood. I look up at him and await his desires.

Ed says, "Get on my bed, lean forward and throw your slutty ass up in the air. Pull up your skirt, pull down your nylons and panties."

To which I do as I'm told but say I need to get lube from my purse. He tells me to do it and hand it too him. I am facing near face down into a pillow my sissy ass up in the air. Ed moves on he bed on his knees and squeezes out some lube on his right hand's fingers. He then begins to work the lube up my butthole, finger fucking me to start. I moan a bit as he does that.

Soon he wipes his had on the blanket and he notices my back side tattoo and tells me he loves it. He says, "I'm gonna enjoy fucking your cum receptacle Chantel." and slaps my butt cheeks causing me to twitch and quiver.

I say, "Mmm, feels good Ed, I want you inside me please."

Ed now spreads my but cheeks and takes his 7+ inches and begins working it inside me. It still hurts a bit as I'm still a fairly tight sissy ass. But soon he is inside me and works me slowly to start. We both do moan and groan nicely as he get his fucking rhythm going. He does work up more and more into an ass fucking frenzy.

Ed moans and groans, I'm ughing and oohing. We are getting it on well and his cock is working up through its shaft from his balls and prostrate that soon to be glorious shot of what every sissy slut loves, male ejaculate, glorious sperm filled semen, hot, fucking cum, call it whatever. It's the prize we get to enjoy for a good slutty job done well.

Yes, it's soon coming forth, Ed is in an ass pounding frenzy now, sweat forming on his brow and he thrusts in me hard. I pant, moan and groan as finally spraying through his cock's head a blast of that oh so gooey hot cum.

Ed slows now and pulls out from my butthole. I keep my ass up allowing his jizz to flow into my rectum. If I was not in chaste I'd probably blow a wad of sissy cum too.

Ed moves off the bed and puts on his briefs, jeans and Daytons. I am still facing forward on my knees, telling him it felt so good. But I then pull up my panty, black pantyhose and pull down my mini skirt. I get up from the bed, some cum flows back and onto my panty.

We both get out of his truck as he too helps me as I'm slutty chick in heels. I curtsey and thank him and soon he gets back in his rig and begins to drive away. I walk to an outdoor garbage bin, pull some tissue from my purse and quietly wipe cum and lube from my butthole.

On the slut walk I go. My sexy black velvet knee boots clicking with each step. Hours pass and I will get it on with seven more horny truckers, helping to relieve their stress and get them on the road with smiles. By this time Master and the guys come back to pick me up. I get inside Master's SUV and tell them of my great night of fun, slutty sex. He and they are all proud of me. I did a get a couple of guys to video our sex with my cell phone camera.

The drive home was quiet, It's about 12:30 am when we get home, I'm tired but I did love my truck stop slut night. I will rest well tonight. I have to because tomorrow is Sunday and it is the Sunday of my ass busting, hard labour punishment day from my earlier in the week theft of part of Master 's money. I need to be ready for it. See you all in the morning.

*************************************************

Chapter Sixteen: A Day of Lesson Learning Punishment.

Well its 7:30am SHARP and the day I have been dreading since last Tuesday when I stupidly stole $10.00 from a $40.00 payout for sex I delivered that by my position of sissy slavery was not my money to spend or to hold.

I quickly do my morning duties, enema, shower, dry off, shave my sissy face, do my make up ad dress in a sissy maids dress for the day. I will put on a black satin one again with white frilly lace. I will pull on a pair of Legg's Suntan coloured sheer pantyhose today and step into my black,velvet 5 inch spike heeled pumps with those oh so pretty ankle straps. A spritz of Chanel No. 5 and I see it is 8:20am and I must get to the kitchen to prepare breakfast. Master, Gage and Rick are all going to be here to witness a hard day of unrelenting labour as my Master told me I would endure for my Tuesday transgression.

Soon all three are up and in the kitchen, I curtsey with a deep good morning call out. I then serve them bacon, eggs, toast, juice and coffee. I have yet to eat. I stand daintily waiting for further instruction from Master. Soon I have a quick bowl of gruel and plain tap water. I ask for permission to be seated. He has me kneel in a kitchen corner facing the wall, shut the Hell up and slurp up my gruel. I'm not to move until I'm finished.

Master says, "Just think Chantel, had you not did the terrible transgression last Tuesday, you would have had today off, could have slept in and had a normal breakfast made for decent people. But nope because of your transgression stupidly you get to slop up gruel on your knees as such. Enjoy it you silly faggot sissy."

I bow my head and say, "Thank you Master." I then slurp up this bland breakfast.

Master now sternly says, "After breakfast and washing up the dishes you will start your long, hard day of labour with starting a wash of my clothes, bedding, and linens. As these all wash through the various loads you will go through my closet, every shirt will be ironed, ever pair of dress pants will be ironed. You will then polish my dress shoes. This will keep your sissy ass busy for a few hours Chantel. Do you understand Chantel?"

I sit head bowed with a, "Yes Master, thank you Master."

"Once all that is done you will come to me for further instruction ok?" he adds.

Again head bowed, "Yes Master, thank you Master."

Soon the men finish and relax in the living room to watch sports and be entertained by my sissy day here. Master calls me, "Chantel, get your sissy ass over here."

I scamper from the kitchen and curtsey saying, "Yes Master."

He adds, "When we need you to serve us I will ring this bell loudly. You will stop whatever you are doing and come to us and serve us, do you understand?"

I sheepishly add, "Yes, Master, thank you Master."

He tells me to get back my chores, I curtsey and thank him.

For the next 2 odd hours I do my first tasks, no breaks, no talking, no anything except to be on my best behavior. I have to stop a few times when the bell rings to serve Master and the other men as they wish. It's now about 10:30am, I am thinking, this is a hard day with no respect, nor appreciation towards me by my Master and his buddies, I must endure.

Once I get these first chores completed I then walk to Master curtsey and ask of my next chores. Master tells me I will vacuum and wash not only his SUV, but Gage's Camaro and Rick's Toyota Tundra. I better do a good job or I will have to rewash all three again. By this point in my sissy life Master's neighbours know I live as his maid and have seen me, I'm sort of the street entertainment. I will be outside on a mild, but cloudy day to vacuum and wash three vehicles and in my maids dress and 5 inch. heels. It will be long, hard work and to know I must do a perfect job or be made to wash all three over again. I will surely take a few hours to do this. I will not be allowed any breaks until I have done this task.

I vacuum each, wash each, dry each and it's hard, my feet hurt, my knees hurt, my back hurts. But by 2:30pm I'm done. I walk into the house and ask for the men to inspect each vehicle. As they each look over the cars, reviewing my work, I stand daintily, head down and silent. I await their judgement. I am nervous because I really do not want to have to rewash all three again. Soon the men talk about themselves and then have me come to them. I curtsey and ask how they judge my work.

Master says, "Good news Chantel, we are pleased, you will not have to rewash the vehicles."

A big smile on my face and a happy curtsey, "Thank you gentlemen, thank you."

Master adds, "Put the garden hose away and clean up the wash supplies."

I reply, " Yes Master, thank you master." with a curtsey.

As I do this Master comes back down and calls me. I scamper to him in my heels. In his hand are four pieces of white bread and two cheese slices. He hands them to me to eat and I must eat them outside here sitting in a chair so the neighbours can see me having my sissy lunch. He gives me a glass of tap water to drink. I am to come back inside when done. I curtsey with a thank you Master.

I sit on a chair by the vehicles I've just washed and some neighbours walk by and talk to me.

"Good Afternoon Chantel. How are you?" the man says.

I stand and curtsey and say, "Fine, thank you."

His wife asks, "Looks like you are being kept busy washing cars today?"

I say, "Yes, ma'am it's a part of my work day punishment."

The man asks, "What did you do to be punished as such today?"

I say, "I tried to keep some money from my Master the other day and that violates our contract of service. He's teaching me a a valuable lesson."

She says, "Well as long as you learn your lesson Chantel."

They smile and walk on after I curtsey to them. 


I sit back down on the chair and eat my cheap meal. Soon it's back inside, curtsey and await my next tasks.

12