From a Husband to a Dutiful Sissy Ch. 06

Chapter Six will compress time a bit more forward in moving the story through time. It will be set two months forward from the original start date of the story in Chapter One, when Helen found out her husband Phil enjoyed crossdressing and fantasized about being sissy maid and a sissy slut. It all picks up with bit of recollecting from Phil who is now Chantel of the last number of weeks... enjoy.

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Chapter Six: Time has passed and I am fully into a sissy maid and slut life.

I've come quite far in the last two months, my sexy and sex videos are now online and according to Mistress Helen and Sir Alan they are growing in popularity as too are my daily blog writings and musings of my now sissy life. Helen and Alan have also taken me to a new way of earning money. I am offered up on line as a sissy maid to now clean and serve gentlemen, notably bachelors, divorced and widowed men who want an effeminate and cute sissy maid to clean their homes and also to entertain them. Helen and Alan arrange contracts of service and a schedule where I now go out daytime as a sissy maid and clean the houses, service and entertain these men.

You may ask, how can Chantel do that and still have her regular drab male job? Well she can't. I no longer am employed in my long time day job/career. Helen and Alan were convinced ditching this vestige of my old male life will be best for me in my new sissy life. I am now virtually 100% en femme, as a crossdressing sissy girl, who serves as a maid for her Mistress and for now making sissy slut pornography. The surprising thing is my new sissy maid cleaning service is only a month old and already I am being booked up. It seems many men are into such and the sight of a growing more effeminate sissy maid, clean, serve, entertain and if they pay extra give personal services to these men.

It all has been a rather crash course to accept my career is now fully encompassing being a sissy maid for hire and not just to serve my Mistress wife and her boyfriend, but also to make sex videos and help run an online website and blog. Being two months in has been quite an adjustment for sissy me. I've had to endure new realities and learn to accept and embrace my growing effeminate and sissy life.

But as we pick things up here today, it's officially my two month anniversary to me adopting my new lifestyle. Mistress Helen and Sir Alan have me lined up to be off cleaning services to two paying gentlemen clients today. It's a bright sunny Friday morning, during serving of breakfast they give me the work details and addresses to these two gentlemen. First, will be me working and serving a gentleman, his name Raymond. He is a white male, divorced and age 58. He operates an online business and works mostly out of his home office now. He is really into a sissy maid contracted to clean and serve him. I am scheduled to work and serve him for three hours today. So I get myself together in my pink frilly, satin maids dress with a white satin apron and its white lace, the dress is over my fluffy white petticoat and a pair of white sheer pantyhose and my pink patent 5 inch spike heel pumps. Touch up my make up and brush my long wispy light auburn with blonde hi-lights shoulder length wig. It's off to my car and then to drive to the address.

Driving out to Raymond's address has me nervous as he is a new client. Mistress says he is really excited to meet and use a sissy girl like me serving as his house maid for a few hours. He is aware that if he wishes for personal services above cleaning and stuff will be double rates.

Arriving at Raymond's house I pull into the driveway, my nerves are flustered but I am also so excited to bringing on a new client, I hope he likes me. I check my makeup in the car's vanity mirror and I step out into the mid morning sunshine. I begin walking up his walkway, my bright pink maids dress, white pantyhose, pink heels glimmer under the morning sunshine. I then ring his door bell and daintily wait for Sir Raymond to open the door and meet sissy me for the first time.

The door opens and Raymond says, "Well, what do we have here? A cute little sissy maid and in her lovely pink maids dress, pantyhose and high heels."

I curtsy and reply, "Hello sir, my name is sissy Chantel and I am here to be your maid for today."

Raymond replies, "Well come on in Chantel, if you do not know my name is Raymond, sir Raymond to you. Let me get a good look at your girl."

I enter and twirl for him as he sizes up having a real sissy maid in his house. Sir Raymond is very pleased at the sight of me and soon he has us going upstairs me walking up in front as he observes my backside, legs and heels from behind. He really enjoys what he see's.

Once up stairs Raymond sits on the sofa and tells me to review what is contracted today for him. I pull out the work order and go over it with him. He has me get on my knees before him doing such.

I then say, "Sir, I am to do any laundry you have ready to be cleaned, to vacuum your whole house, to make and serve your lunch, to then clean your kitchen including scrubbing floors, iron, fold and put away your clean clothes and to clean your two bathrooms."

Raymond smiling says, "That shall keep sissy you quite busy for the next three hours. I will be working in my office Chantel but I plan to observe you at work from time to time sweetie."

I head bow and say, "Yes sir, I hope it all pleases you."

Raymond says, "I also have the right to receive personal services from you sweetie. I know it means double the rate but Chantel, I am very excited at the sight of you so I will likely have you service me personally as well."

I look at him from my kneeling position and say, "Yes, Sir, if this will add more pleasure for you I will be happy to do so."

Raymond does send me off to his kitchen and pour him a mug of coffee, bring it to him on a serving tray with a bowl of sugar and cream so that I can prepare it in front of him and then serve him the coffee. I do as I am told and a few minutes later come into the living room, place the serving tray on his coffee table and ask how he likes his coffee? He tells me a bit of cream and two spoons of sugar. I then daintily carry out said order and then pick up the mug and go to him to bend gracefully over at my hips and extend him the mug of coffee. Sir Raymond then takes the mug, sips it and compliments me on a fine job. I smile and curtsy thanking him.

Raymond takes couple more sips and says he needs more personal service from me. He has me come in front of him and get on my knees. He then stands up, looks down at me as I look up at him. He in his gentlemanly mature man's way takes his right hand, grasps my chin and tells me to undo and pull down his pants. Of course I do as I'm told and with a smile. He then tells me to pull down his boxers. As I do such I see his average sized white cut cock flop before my eyes, his balls hang nicely. I look back up at him and he tells me to grasp his cock and his balls and of course I do. I begin to feel up and play with both as Raymond shows growing pleasure.

Raymond now says, "Chantel, your manners, you should ask for permission."

I look up at him and politely ask, "Sir Raymond, you have a nice cock and balls, I would be very happy and privileged if you will allow me to suck your cock."

Raymond smiles and says, "Go ahead sweetie, show me how well you look after a man's needs."

I proceed to hold his cock out in my right hand, left hand cupping his balls and lean forward and my bright frosty pink lip colour lips kiss his cock's head and then part open to take it in. I can sense Raymond's pleasure rise as his cock slides in my mouth and over my tongue. I begin working up saliva as I begin to wrap my tongue around his cock and move back and forth on his shaft.

Raymond sighs then says, "Ahh... Chantel... feels nice. This is the first time I have ever ahhhh... ohhhh, had a sissy girl suck my dick, God it feels so... good."

That fact turns me on and I am flush with sissy pride as I work more and more on pleasing Sir Raymond and his cock. Of course being an accomplished sissy now and a good cock sucker my sissy dick goes hard and it really excites me but I temper such with desire to please the man I am servicing. So I keep on working over Raymond's cock, my left hand's fingers play with his balls and my nails tickle them really turning Raymond on. He feels the need to sit back on the sofa so I carefully adjust my position to follow him being seated.

As Raymond moans with growing pleasure he can't help not to put his hands on my head, petting me and playing with my hair. I just get going more intensely sucking on his cock as his moans and sighs turn him and me so on. The intensity of such sounds with Raymond playing with my hair is only more sexually erotic of both of us.

Raymond in greater excitement says, "Jeeez girl... ohhh... ahhh.. fe...feels so fucking good. Keep it up... Ahhhh... soon... good. You are such good little cock sucking sissy Chantel...Ahhhh... ohhhhh... yes... yes."

I really love knowing I please a man as well as I now do. I'm such a sissy bitch, a little cock slut. I work over and over on his cock, saliva all so wet and slurp as I with sissy pride bob on his cock, still feeling up his balls with my right hand.

Raymond is now getting close as he says, "God girl... ohhh, man, yes... yes... yeah, fuck yeah. Soon girl... so ...soon you little slut... ahhh... ahhhhh... ohhhhh... m...ann.. yes, yes, yes... Ahhhh!" as Raymond lets his wad of hot cum go, it gushes well and thickly inside my mouth. So warm, so gooey as he compliments me then he sits back in his chair and he stares at me finishing up draining his cock. I then with lips tight pull off his cock and look up at him as I swallow all of his cum. His smile is beaming and I smile back at him.

Raymond says, "Hun, that was the best blow job I ever had, and to have it done by a sexy little sissy girl like you makes it better."

I smile and say, "I'm so glad you are pleased Sir Raymond. I enjoyed sucking cock, getting men like you off. Your cum was so delicious."

Raymond now sends me on my way to begin the contracted maids duties as he gets himself back down to then go to his home office and I begin to get on to cleaning.

I will be kept quite busy with doing laundry, vacuuming, preparing lunch, cleaning the kitchen, ironing and putting away his clothes and cleaning his bathroom. Ah, such is a sissy maid's life, but one that we know sissies actually crave and desire. As I vacuum I move into Raymond's office and ask him if it's ok for me to vacuum as he works? He smiles and tells me it's ok. I now daintily in my dress and heels vacuum his office as he sits and watches me and he enjoys the sight of a cute sissy maid as me doing my sissy tasks. I enjoy being the centre of his attention for now.

I next move to prepare him his lunch, soup and sandwiches and another mug of coffee. Like a good sissy maid I set the kitchen table and then go to Sir Raymond's office and tell him lunch is served. As he sits and watches me do my sissy duties he is pleased. We chit chat a bit as I serve him and then begin washing dishes.

After lunch Raymond goes back to his office and I proceed with my cleaning. About and hour later I'm in the laundry room and begin folding clothes and to iron many of Raymond's clothes. I hear Raymond walking towards the room and soon he steps through the door. I pause, look at him and ask if I may be of service to him?

Raymond says, "Sweetie, I just enjoy watching you in your cute pink maids dress, pantyhose and heels."

He then moves towards me as I am running the iron over pair of his pants and he takes his two hands and gently places them on my shoulders, standing behind me. He leans forward and tells me my perfume is very pretty. He begins to massage my shoulders and neck and I love it. He says, "Chantel, I can't work right now, you are on my mind. Do you know what I want to do with you dear?"

I'm moaning with him massaging my neck and shoulders, the feeling of a real man on my effeminate body is incredible as I say, "Mmmm feels nice sir, what would you like to do with me?"

Raymond replies, "I want to take you over to the washer, bend you over, lube you up and fuck your sissy girl ass."

I smile and say, "Mmmm ok, sir, I would enjoy that."

Raymond guides me towards the washer and has me bend over, throw my sissy ass out with me standing tall and proud in my 5 inch heels. He lifts up my dress, then white petticoat. His hands firmly pull my white pantyhose and panty down, exposing my sissy bottom to him.

He says, "Hmmm, yum looks very nice girl." as he lightly slaps my butt cheeks and pulls out from his back pocket a tube of lube, he adds, "Hun, let me lube you up with a nice fingering then I will fuck you silly."

I am hot and turned on as I say, "Ok... sounds so good."

Raymond finger lubes my butt hole and soon is unzipped and pants along with boxers

pulled down. His cock is rock hard and he begins playing around my butt hole with it. Soon though he pulls my butt cheeks open and begins to push his stiff cock up my ass. I groan as he works it inside me. Soon he gets his stiff cock inside and begins to get a gentle rhythm on me.

He says, "Your ass is nice girl, feels good. Mmmm.. ahhh..ohhh yeah."

I reply, Um yeah, glad you like it.. ahh...ohhh...ohhhh... yeah."

He begins to work into a harder pumping action and we both start moaning and groaning with growing sexual joy. It never fails me at how fucking good it feels to have a man fuck my sissy ass. I can sense the joy men have with their grunts, sighs and groans, pumping, pumping and pumping me all to get so horny.

Raymond is now really into it, it amazes me at how well a mature 58 year old man can fuck, fuck my sissy ass. We both are growing with pleasure as our breathing and moans almost sing a song of sexual lust between us.

Raymond glowing with sweat says, "Damn girl, you are... ohhh. God... ahhhhh. so.. fucking ... good to fuck."

I reply, "Ummm... yeah sir.. ohhh, you, really, uhhhh give it hard to me.. please give it to me sir."

Raymond really bangs my ass as he is so hot and worked up. He is getting closer to his prize. He fucks me so hard and I feel as if I am going to be drilled into the washer. We both are in sync with this good fuck. Raymond is so hot and so ready to let go and let go he does. Hot jets of his manly cum shoot up inside my rectum. Blast after blast, he fills my insides up. I am in ecstasy and so is Raymond. He slows and soon pulls out and I turn, fall to my knees as I am completely melted into his hands. I lick his cock clean, tuck it back into his boxers and then do up his pants.

Raymond tells me it was a great fuck and I thank him for giving it to me. Raymond went back to his office, I go to the bathroom wipe myself clean and finish my tasks. Once completed I went to Sir Raymond and we squared up the bill. It was 1:00pm and I had to get to my other client by 1:30pm. Raymond said he looks forward to next week as I comeback to do it all over again as he will be a regular client now.

I get into my car by 1:10pm and drive out to my next client, the contract notes him as a new client also and his name is Jamal a 42 year old divorced black male, who is a tech that is on the road four days per week and is home for three. He is looking for about 2.5 hours of cleaning and servicing as he comes home with dirty laundry and has a house to keep clean.

I get to his home and park by 1:25pm. I get out of my car, fix my maids dress and strut in my pink heels to his front door. I ring the door bell and await Sir Jamal to open the door.

As he opens the door I see a 6' tall male over 200lbs and pretty beefcake, he says, "Mmm, who do we have here? You must be Chantel, my new sissy maid?"

I curtsy and reply, "Yes, sir, my name is Chantel and I'm reporting for service, I hope you enjoy what you see."

Jamal smiles and says, "Yes, yes I do, cute lil white sissy maid, quite yummy, you will do just fine girl. Come on inside."

I step inside and Jamal leads me into his front room as he sits he asks I stand before him and gracefully turn around so he can get a good look at sissy girl me. He really loves what he sees and he next has me step closer to him. As I daintily stand before him he runs his hands up and down my pantyhose clad thighs, feels my petticoat and then runs his fingers through the front of my satin pink maids dress and white satin apron.

He says, "Mmmm feels fine girl, you are giving me such a fuckin hard on honey."

I smile and reply, "I'm very happy that I please you sir."

He instructs me to get a frosted mug from his fridge's freezer and pour him a beer then come back to the room and serve him. I curtsy and follow his orders. I find a chilled mug in his fridge's freezer and I open a can of beer, pour it in the mug and gracefully walk back into the front room where Jamal waits and watches me. I stand before him feet in my heels close together, knees tight and daintily bend at my hips as I extend him the mug of beer. Jamal grabs it and sips from it.

He says, "Mmm, good, chilled mug of beer presented to me by a dainty lil sissy girl, it's a great feeling dear."

I smile curtsy and say, "Thank you Sir Jamal."

He sends me to my tasks, sort some laundry then vacuum his house for him. I do exactly as said and it keeps me busy. Lots of vacuuming in 5 inch heels. Jamal checks on me from time to time as he relaxes in his front room listening to music. After I vacuum I find his laundry is done and I put it in the dryer. I am to then clean his kitchen including scrubbing his floor own my sissy knees. Jamal checks on this and loves what he sees. He is so turned on to sissy maid me on my knees scrubbing his kitchen floor he comes to me has me stop but stay on my knees.

He says with a smile, "Girl have you ever done black?"

I look up and tell him, "Yes sir a couple of times already, it was very good."

He says, "Hun, I want you to pop open my pants and then pull my briefs down."

I reply, "Yes sir."

I on my knees, undo his pants, pull them down and his briefs and before me pops out a rock hard 8+ inch thick cut black cock. My eyes open wide as he has me grasp his huge cock and pull on it as I then am to take it or as much I can in my sissy mouth. I open wide and try to take it all in without gagging, Jamal loves seeing a lily white sissy girl take his big black cock in her slutty mouth. I begin to work it as he stands before me, he enjoys watching me work on his manhood. My sissy dick grows rock hard as to be expected with the privilege and pleasure of sucking on a big black cock.

For the next few minutes the both of us groan and moan, the joy we both feel is deep and wild. Jamal tells me he so badly wants too give me a huge mouthful of his cum as he has gone over week without cumming. I as a sissy girl want to bring him to cum. The feeling of that huge cock inside my mouth and my tongue dancing with it was intoxicating for me. Jamal begins to force my head onto his cock as he draws closer to cumming. I love that feeling of a man having such control over me but before I know it Jamal groans as huge jets of his hot sticky cum fills my mouth. It is almost too much, I feel my mouth fill to the brim with his hot sperm filled cum. I struggle to swallow it all, but like a good slut that I am, I do. Jamal once spent pulls out, tucks his cock back into his briefs and pulls up his pants as he thanks me for being a good sissy girl with the blowjob. I of course thank him for the pleasure of doing such. I am sent back on my way to carry on my contracted chores.

I will be finished by 4:00pm to head back home, but Jamal is not finished with me yet. Over the next hour or so he has worked up his horniness again and calls me to him by about 3:40pm. I do as I am told and see he is in his bedroom and in his bed. He has me come to him and sit on his bed as his hand plays with my white pantyhose clad legs. He is very horny again and has me then get on the bed on my my knees, my head and arms on his pillows. He pulls up my maids dress and petticoat, forcefully pulls my pantyhose and panty down. I hear him squeeze a dollop of lube from a tube and he begins to finger lube my hole. I am about to be fucked hard by 8+ inches of cut black cock. I'm already a well seasoned slut over the last two months but 8+ inches of thick black cock still scares me.