From a Husband to a Dutiful Sissy Ch. 04

A quick note about this chapter. It runs a tad long as I want it to really set things up for Chantel's future, not just some sissy maid for her now Mistress wife, as cool as that can be, but to develop a more varied sissy, crossdressing, maid and slut story. I hope it works for my readers.

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Chapter Four: Moving on to reinforcing my new lifestyle

Saturday morning, I was hoping I could just take it easy, maybe be given some time to deal with the changes in my life and my new relations with my now Mistress wife, but no, I have to get up early enough to shower, shave, do my make up and get into a maids dress, again. As I'm doing this I can't help but think that my wife has a man in her bedroom, a man who made love to her last night and where I watched it happen. I can't help but think as I do my makeup, 'Hell what kind of sissy cuck am I? I basically allowed a man to bind me to a chair last night so I could not escape watching him fuck my wife. How fucked up am I? On top of that I had a hard on too during this time, only relieving myself back in my maids quarters and in my privacy, pulling on my sissy dick with me wearing a bra, panty, slip and pantyhose.'

Once I am all dressed up, today back in a black maids dress, white petticoat, black sheer pantyhose and a pair of black leather 5 inch spike heel pumps that have cute ankle straps I get on to preparing breakfast for Helen and Alan, which I shall serve them as breakfast in bed. It is so humiliating, but I do as I'm ordered. For me I am to make and eat a small pot of plain old oat meal.

By 9:25am I have two plates ready, bacon, eggs over easy, toast coffee and orange juice. I put them on serving trays and place them on a rolling serving table we use. I carefully roll this table down the hall to outside Helen's bedroom. It's now 9:30am and the time I was instructed to wake them up. I knock at the door and soon Mistress Helen says for me to enter. I do as I'm told and once inside I see both her an Alan sitting up in bed and giggling at sissy me in my black maids dress, pantyhose, heels, wig and makeup. I curtsy and say, "Mistress Helen, Sir Alan, I have your breakfast ready to serve."

Helen says, "Very good Chantel, you may serve our breakfast."

I curtsy again and then roll in the serving cart. I pick up Helen's plate and tray first, ladies first and carefully place it in front of her, stand back curtsy and say, "I hope you enjoy Mistress."

Helen says, "Looks very good Chantel."

I move back to the cart and pick up Alan's tray with plate, this is so fucking humiliating to be serving breakfast in bed to the man who made love to my wife last night and me wearing a maids dress. I carefully and daintily walk to his side of the bed and place the tray in front of him. He is so enjoying the humiliation I feel as Helen's sissy husband. I stand back curtsy and say, "I hope you enjoy your breakfast Sir Alan."

Alan says, "Yes, it looks very good Chantel."

Once done, Helen says for me to go eat my oatmeal and get the bathroom ready with towels as Helen and Alan will shower together this morning. I curtsy and remove myself from her bedroom like the good sissy I am.

I sit in quiet in the kitchen and eat my plain oatmeal, I wait for them to finish. Once they are done I am to remove the trays and wash the dishes. They are wearing robes, Alan in one of mine as they move to the bathroom. I move on to washing dishes as they enjoy a fun shower together. Of course they play and kiss all the while, I stand in 5 inch heels and do sissy chores, washing breakfast dishes.

Soon I hear Helen call me and I scamper in my heels to the bathroom. I see her and Alan wet and holding each other in the shower. Helen has me grab her a towel and wrap her as she steps out. It feels good to do this for my wife, I wish I could make love to her, but I can't. She takes a second towel and wraps her wet hair. I am now to hand Alan a towel as he steps out, of course I get a good view of his cock and balls, the very cock and balls that made love to my wife last night. As they dry off and dress I go back to my kitchen work.

They both enjoy playing and tormenting sissy me for a while on Saturday. I endure it as I must now that I am a sissy maid. Alan later leaves and it looks like they will date again. Helen moves on to telling me her plans for this Saturday night. It seems she will invite female friends over and have a girls night at there movies and I will be their sissy maid. Sounds like fun, really it does.

Mistress Helen has me go out shopping in my maids dress to pick up appetizers for the ladies movie night, of course mincing around the local grocery store in my black maids dress, black sheer pantyhose, black leather 5 inch spike heel pumps, my blonde-light auburn wig and makeup was exciting and humiliating. Each day in public will make living as a sissy maid a bit more easier.

Once back home I clean up the house and begin prepping the appetizers. Work, work, work for this sissy maid and it never seems to end. It's hard and yes my heels make it a bit more difficult but my sissy side loves it all. Helen is coming around to having her sissy husband be her sissy maid. Though it helps for her to have a real man as her new lover now.

Other than Jenny the other ladies coming over have yet to see me, Linda from work and Helen invites three neighbour wives, Jill, Alice and Nattily our three next closest neighbours. I guess Helen wants to begin outing me to our neighbours. This will be humiliating but if I am to live more or less as a sissy maid it is to be expected. I carry on with my chores of food prep.

Before the ladies arrive I am to freshen up, spritz on perfume and be all ready for a night of sissy servitude for the ladies. Helen has the ladies arriving after 8:00pm and the first to come are Jenny and Linda. Having me greet them was fun for all of us. Linda seeing me as a sissy maid, knowing I will be dressed as such was totally exciting for her. She compliments Helen for the quick grooming and refining me as her sissy maid.

Once in the home theater room I begin to serve drinks, made to order, the thrill of mincing in my maids dress and heels, serving and doing curtsies was almost too much for the ladies.

The door bell rings and Helen figures the ladies who are our neighbours have arrived. She has me wait in the kitchen a she wants to introduce me to Jill, Alice and Nattily. I am so nervous, these are the wives of our closest neighbours, once they learn that I am now a sissy maid I'm sure their husbands will be told and it will be extra degrading for what is left of any man in me, but it will be as Mistress Helen wants.

The three neighbours come to our home theater room and all are seated when Mistress Helen begins to explain things.

She says, "Ladies, tonight is a girls movie night, but before this I need to explain a few things to you Jill, Alice and Nattily. You see we have a special service tonight. You all know Phil my husband, well recently it was revealed to me that Phil is not quite the man we all thought and think."

I am upstairs and can hear Helen tell all, I am so nervous and soon will feel the weight of humiliation.

Helen adds, "You see I found out that Phil has another side, a strange but now for me and us a growing good side. Phil was found by me to enjoy being well... girlie... he likes, no loves to wear women's clothes. It was a shock to me and I at first wanted a divorce but I soon learned that having a sissy crossdresser has its benefits."

Alice, Jill and Nattily are a gasp but listen on.

Helen says, "Phil really enjoys being a sissy maid and he looks very cute as a sissy girl in a maids dress. I have made servitude contract for our marriage where he is mostly a she now and I am the head of the house as her Mistress wife. I tell you all this as Phil who has a girlie name of Chantel will be our dutiful sissy maid tonight to wait on us, serve us and entertain us."

Jill jumps in, "Helen really, you have Phil live as your sissy maid now?"

Helen says with a smile, "Yes Jill, it's adjustment but boy is it good to have a sissy girl to do any and all maids chores. Other than his daytime work, Phil, err Chantel will dress and live enfeme as my sissy maid and sissy girl. This said I wish to introduce you all to Sissy Chantel... Chantel! Come on down the stairs and show yourself to our guests."

I am near sick with humiliation but I too love it, love the fact my life is more and more irretrievable into a sissy life. I walk down the stairs in my heels and daintily enter the room. Jill, Alice and Nattily eyes go wide as they see me for there first time, giggles are heard as I curtsy and say, "Welcome ladies, my name is Sissy Chantel the happy sissy maid to Mistress Helen and I am at your service this evening." as curtsy again and stand at attention, feet together hands gracefully clasp in front of my apron.

The ladies are full of questions for me and Helen as we go into details as too how I will live as her sissy maid. Helen too tells the ladies she has been dating a man who has been quite wonderful with her. I learn how I am dealing with no longer being a dutiful husband and now live as a sissy maid and sissy girl to Helen. I accept her need to be with a real man and I will get use to it.

Soon we move on to my servitude, I am to take drinks orders and go to the bar in the basement and make drinks to serve the ladies. I have to remember the six orders and make sure to serve them as girlie and sissy-like I can. I then bring down all the appetizers so the ladies can enjoy them as they watch a chick flick and carry on with seeing me as the sissy maid. I am to stay in the kitchen and only come to serve the ladies when Mistress requires me to. She will use a bell and ring it went ladies set an intermission for me to scamper to serve them in my heels and maids dress. It's both humiliating and exciting.

About 10:00pm Mistress Helen tells me they have ordered pizza and I am to receive the order as the delivery driver comes by. This will be more humiliation. In fact they take an intermission break about 10:20pm so that they can witness me take the delivery.

At about 10:25pm the door bell rings and I am to scamper to the front door, make sure my dress is proper and open it with the ladies watching from there back of our foyer. I open the door, curtsy and welcome our pizza delivery driver. His face is gawking at the sight of sissy maid me but he keeps his cool.

He says, "Here is your pizza." as he scans me from head to toe.

I take the pizza and put it daintily on the table as I then hand him the money and his tip, I say, "Thank you." curtsy and ask if he likes my outfit as the ladies giggle in the background.

The driver says, "Um, yeah.. I guess you look cute, well unique, nice shoes.. umm nice legs." he blushes and we both say good night.

I am so humiliated but carry on as a good sissy.

The night unfolds with me at the ladies service until about midnight as the gals all then go home, Jenny and Linda take a cab home, the neighbour ladies walk home. They will surely out me to their husbands, I will be a humiliated sissy but am now more able to be out and about as a sissy crossdresser and maid.

A few days pass by and my journey moves on, short of my daytime work I am virtually dressed as a sissy maid near all the time. Helen is starting to see Alan regularly, they have gone to lunch twice and diner once more. It looks as if they have really hit it off. I must accept that as a husband my relationship especially sexual with Helen is over. Why should I be surprised at such as I am being a sissy.

I find that they are out to dinner tonight again and I'm at home doing sissy maid chores after a long day of work of me. My new life never ends with sissy maid chores.

At dinner Helen and Alan are talking about me and a future with me, where it may go.

Alan says, "You know Helen, we need to make plans for Chantel, I mean we can keep her as a quiet sissy maid, outing her, doing errands or such, or we can turn her into a real positive."

Helen after biting into her salad asks, "What do you see we do about my sissy maid husband?"

Alan sips some wine and takes a bite of his steak says, "Well lets accept, Chantel is a sissy, loves to be a crossdresser, gets off on her growing femininity. She is also lucky, for her she's quite a looker. I mean she's quite cute as a girl. I think we can turn a buck or two from her."

Helen looks up and sips her wine asks, "What do you mean, prostitute her? I don't know if that is wise."

Alan smiles, pauses and says, "No, not a prostitute, well not now anyways... It's too soon for such things if at all. I mean Helen I know she is still your husband and I know you still have love for him even though it's different now." He bites more steak, pauses and adds, "No, I mean make sexy videos. I have buddies who are skilled in A/V and can make us some kick ass sexy or sex videos. They'd be keen on playing with a sexy little crossdresser as Chantel is."

Helen sips some wine and smiles, "Well that can be interesting, can some good money be made from such?"

Alan says excitedly, "Hell yes, you see we make some sexy maid videos of cutie Chantel, put them online free for people to view as teasers getting mostly horny dudes, many who are openly or secretly on with it over crossdressers, sissies and trannies. You would be surprised at how many regular guys get off on hot crossdressers, sissies and trannies."

Helen says, "Well yes, Chantel is quite cute as a sissy maid and probably would look hot if we have her dress as a slut. Not sure how receptive she'd be on this."

Alan says, "Not to worry, my gut tells me she will go for it and not be too apprehensive. Sure she will probably protest a bit at first as she still has some of that man in her, but I feel she will turn out good and will be quite excited at making sexy maid videos and then more hard core sex videos to offer paying guests with an online set up."

Helen bites into her fillet minion asks, "So you see this as an online sex video business? Use Chantel as a sexy maid to bring men into the site and then see them buy more hard core sexy slut videos?"

Alan replies, "You got it Helen. Chantel is a lucky crossdresser as she feminizes well enough and I she will be feminized well in her actions. She will probably be good at the sex videos if we set them up well. The guys I know will make these videos very professional. I suggest we keep them as vignettes about 10-15 minutes long. Enough for horny guys to jerk off too. We can bang out a good number of these sexy vignettes."

Helen sips more wine, pauses and says, "Do you think we can make this work? I mean I don't want to hurt Chantel can we make it safe enough but hot enough for horny guys online to actually buy them?"

Alan smiles, "Hun, Chantel is a cutie and will make a good sissy slut in said videos, I can feel it. But we need to find out how she performs sexually with men first before we invest time and money into these sex videos."

Helen asks, "What do you propose? As far as I know she has never had sex with men, neither sucked cock or got fucked by cock. I do not know if she is lying but my gut tells me she is true and even though a life long crossdresser still a virgin anally and orally on cock."

Alan says as he leans back in his chair, "I figure we put up a Craigslist ad in the casual encounters section, there is that highway rest area about 15 minutes outside of town. Many guys hook up there. It has been a hot spot for quick sex including dude on dude and dude on tranny or CD sex for many years. I say we advertise Chantel as a new street slut looking to finally hook up with men. Have her go there Saturday night say from oh 10:00pm and on. Have her be ready to hook up with dudes who will see her ad in Craigslist and then go out there to check her out."

Helen says, "Well I am not sure if Chantel will want to do this? It will be scary for her."

Alan says, "Helen I'm sure once she gets over her initial fear and to reenforce to see herself as hot looking slut, she will actually want to do this. I'm certain she has jacked off to said fantasies her whole life. After all she has lots of sexy and slutty clothes too and not just maids dresses. She has been privately wearing such for years. I bet she has jerked off many times dressed as such."

Helen sits back smiles and says, "You know, you are probably right. If she can show us she is capable of having hot sex with guys, we know she will probably do it in sexy video making. It will be a good test. What do you suggest she do at this rest area, suck dick only or be fucked too?"

Alan finishes his wine and says, "We need to know she can suck cock well and take good fucking as a slut. I suggest she makes some video on her phone of any sucking and fucking she may get. This way we can size her up for future sex videos based on how she acts during the night's sex encounters."

Helen says, "Well this sounds good, will you take care of the online set up? We can split the money we make from the sales. Will your A/V buddies charge a lot?"

Alan says, "I'll take care of the online set up and my buddies will probably do it cheap to start. If the movies go well they will probably want more money later though."

Helen says, "Ok sounds good, you wanna do the Craigslist ad?"

Alan smiles, "Um Helen I have done it already, for a couple of days now, I figure if you were not into it she would just not show up. But if you were, her ad will run everyday until Saturday. I suggest that we keep any sex she will have with men from this ad to a minimum as Chantel will be nervous. I figure a couple of blowjobs and at least one butt fuck."

Helen chills, sits back inner chair and the asks, "Well what if she digs it?"

Alan replies, "Then she can choose to hook up with more guys this Saturday night. Sunday we can watch any video she made and interview her as to see if sex with guys and her dressed as a slut or a maid may be a thing she will like. Then we tell her about making sexy and sex videos to sell. I suggest we include her in part of the money we will make. She will be a junior partner so to speak but it will incentivize her to work harder." He sits up and says, "Helen this will just be start, I have many money making ideas for and Chantel, so are you on board?"

Helen leans and kisses Alan says, "Sounds good, we may as well make good use of Chantel and I agree I feel she will act like this as it's in her nature."

They also agree not to tell me they are advertising me to be at this rest area Saturday night, until Saturday morning. They do not want me to be too nervous if I find out too soon. Saturday morning reveal will certainly be a shock and interesting to see my reaction to being slutted out.

The rest of the week goes by growing more typical for me an Helen. Yes, after last Saturday night girls movie night the cat was out of the bag, the wives of our neighbours did tell their husbands about sissy maid me. The ribbing I began to take was humiliating, but getting over the secret of being my wife's sissy maid was better. I no longer have to worry about the neighbours seeing me dressed as a sissy maid. The other neighbours on the block soon see me now out an about and though they are not close friends and they may roll their eyes at the sight of me wearing black or pink maids dresses, hosiery, heels, makeup and wig they generally remain polite, curious but polite and keep to their business. I will just be some neighbourhood entertainment and a gossip topic, meh oh well, more stuff for the life of a sissy.

Saturday morning arrives, another morning of me serving Mistress and Sir Alan in bed. Yes another night with him making love to Helen, yes I had to endure knowing such though last night I was not made to watch. I heard it from my maids quarters, though in the privacy of my quarters I could not help but masturbate to it all knowing Helen was being given sexual pleasure by a virile and strong man. For me dressed in my white bra and panty, white pantyhose and white slip, I jerked off to the sounds of Alan making love to Helen, my mind wanders to the though of a man making love to me. As I pulled my sissy dick I thought, 'Shit, what's going on, I am totally on with the thought of man fucking me, all the while in my wife's bedroom man is doing her.' I soon ejaculate and make my fingers sticky, I feel like shit and want to wipe my cum soaked finger on my bed sheets but I do not, I lay still and let my mind go to ease from animosity from my masturbation. It takes only couple of minutes to pass before I build a desire to lick my own jizz from my fingers. Licking my own cum knowing Alan filled Helen with his was erotic for sissy me. God I am going down the rabbit hole of life changing things.