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From a Husband to a Dutiful Sissy Ch. 01

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it.

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Chapter One: Sometimes one's most unique secrets do come out.

My name is Phil and I've always been different, since my earliest recollections I've enjoyed crossdressing and as I matured enjoyed the sexual side of crossdressing thinking about life as a sissy maid and a sissy slut. Wild fantasies to fill my crossdressing needs. Now on my second marriage I've had to temper my ever long developing side as a crossdresser. It has been hard at times keeping this girlie, sissy crossdressing side a secret from my wife and others. Though it did not cause the ending of my first marriage, it did not help it though. Being married to my first wife who is name Jill for twelve years and resulting in one child, a daughter, named Sara who is now twenty years old, my divorce to my first wife was acrimonious and my time with my daughter post our break up has been more or less estranged as she and my ex-wife now live in another city about 1,000 miles away.

My current marriage has been exciting and interesting. My current wife named Helen was a rebound wife. We have been married for about eight years. She is a widow and has two children now grown up. A son named Gage who is twenty two years old and in university about 2 hours away living on campus and a daughter named Linda who is twenty years old and lives with female roommates while they all go to cosmetics school. She lives not too far away but is an active twenty something. Helen is two years older than me, age forty six and as such I am age forty four. Helen is a Legal secretary and is a bigger bread earner than me. I am a supervisor for an industrial sales company. It's ok to me to have a wife who does earn more than me, again my sissy side kind off gets off on this.

Our marriage has been up and down being both our second marriage. Helen's first husband passed away in a car crash about nine years ago. I knew him from sales of industrial supplies to the corporation he worked for. With her then widowed with two children and me on the rebound from my marriage we drew towards each other. I did my best as a man in her life and with my step children. Our incomes combined are middle class healthy. I fell in love with Helen as she was a rather strong and exciting woman, tall at 5'9" and nicely weighted at 135 lbs. more or less. She has a nice body, and lovely auburn hair shoulder length. Being a professional work woman she dresses impeccably for work and my girlie, crossdressing side loves her professional work attire. She knows how too look like a woman and loves femininity with power and also enjoys heels as a strength thing. I love it as a man and as a crossdresser. Helen loves me but I never felt it was quite as deep as my love for her, but we have had it pretty good as we stabilize each other. Her kids grew up well adjusted. I think a part of me enjoys my love and marriage to Helen as away to compensate for my secret crossdressing side. It makes me feel like a man as such.

Now that both of her children are grown up, the two of us have more time for each other and ourselves. My hidden crossdressing side was very deep in secret as the kids lived with us. I have had to be very discrete and mostly brought a wardrobe with me on business trips. Dress up in these clothes in my motel room. I never did much but a couple of times I'd get in my car and drive around dressed, thinking I'm a strange town. I'd get scared about getting pulled over by a cop or so or my car breaking downs with me dressed enfemme again usually as a sissy maid or sissy slut. It was always a turn on for me.

It was tough to hide this side to me. A number of times when dressing at home if Helen was out with girl friends or late at work, I'd get off dressing up in the the ways I enjoy crossdressing, with a sissy maid in one of my maids dresses or as a tarty, sissy slut. Helen almost caught me a few times. More than once I'd scramble in my wig, dress, hose and my high heels clicking away on my feet as I ran to the bathroom, locked the door and stripped off these femme clothes to then hop into the shower as Helen would enter the house. It was scary but also so much fun too as it felt so taboo. I'd often quickly jerk off in the shower from the excitement of nearly getting caught.

For me the guilt of never quite measuring up as a real man though bothered and bothers me and has affected our marriage, but Helen and I have been rather comfortable even things are not always so perfect. Our sex life has been very good in our earlier years, but in recent times a bit more on/off as both of us work hard and try to provide a comfortable home. Helen has expensive tastes and we both allow each other pleasures and things that excite us. Helen a nice wardrobe, a nicely furnished house and a life long favourite car of hers a Volkswagen Tiguan. Me I love my hobbies, music listening including a nice DIY home theater in basement and car stuff including my favourite near mid life crisis Dodge Challenger SRT 392. All these dude type things helps me stay a man so to speak, but as years pass by and now the step children grown up, my daughter grown up and living over 1,000 miles away, I find my crossdressing side to grow more intense. I keep all my feminine and sissy clothes, a whole lot of pairs of high heels, lingerie, hosiery, wigs and makeup boxed safely away labeled as TOOLS, CAR STUFF, GUYS HOBBIES in our storage room off our garage. Thankfully Helen has never felt a need to look through these boxes.

Anyways my crossdressing urges seem to grow strong now as I move closer to true middle age. I fantasize dressed up as a maid or a slut and in such my sexual side wants to be taken by men. I enjoy dressing up and playing either safely at home or when I am on the road in my motel room. I have never been with a man though but I dress up and fantasize including jerking off to such fantasies. I feel like shit afterwards and feel I am less of man to Helen even though she has no clue that I know of. But I deal with it all. With the internet I do look at lot of crossdressing and sissy porn stuff while dressed up and it can really drive my sissy and slutty side wild. So my life with my second wife Helen moves along and we have our ups an downs but more or less given we are forty somethings and married near eight years it's more or less ok, stable, generally loving again more my love for her being deeper or more connected than Helen's of me and we make decent money with a few good family friends.

Today though things begin to change... BOY OH BOY DO THEY CHANGE!

Another typical work day ends as I drive home and look forward to a relaxing dinner and normal husband/wife life. My wife and I usually come home from our jobs in an around there same time, usually I beat her home a bit as my traffic is less of an issue. The last few days though the wife has been able to stay at home and do some work there rather than driving to her office. Her legal secretary job offers her that benefit a few days per month. Helen enjoys it as she can kind of balance her career work with some home body things.

I pull in the driveway about 4:35pm and walk up the walkway and enter the front of our modest home on a suburb type street in a rural part of the city. We have about ten neighbor houses on our street and in back a hill that drops down to a stream and has a city park after it. We get some nice privacy. As I enter the house I hear Helen.

She asks, "Phil, are you home?"

To which I reply, "Yes hun." place my keys on the key rack and begin to walk to the living room where Helen is.

She replies, "Can you come here?"

I shout, "Coming dear." Little do I know a shock is about to strike me.

I enter the living room and Helen is standing in behind the love seat, dressed in a white button down blouse, faded jeans that look great on her long legs and her hair pulled up with a head band. I see my boxes on the love seat, again one labelled 'Tools' another 'Car stuff' and the last 'Guys hobbies', my face goes a bit white as I smirk and ask what's up?

Helen sternly looks at me, "These boxes, labeled with your stuff you keep in storage, I opened them up and am shocked at what I found."

I stammer, "Ahhh... ahhhh what is..is the problem?"

Helen reaches in one box and out she pulls a black leather skirt and a red satin blouse, puts these on the love seat, reaches back in and pulls out a black full slip and a couple of packages of pantyhose. She then reaches in a second box, pulls out a black satin maids dress and a pair of black suede spike heel shoes. Next, she pulls from the third box a styrofoam wig's head and a blonde with light auburn hi-lights medium length, wispy wig as she asks, "What is all this stuff?"

I am ghostly white and stammer, "Ahh... ahhh.." as she interjects.

"Is this stuff from your first wife? If so why do you have it?" she adds, "Or are you keeping clothes for another woman to play some kinky sex stuff, I mean this looks like maids play, and hooker play stuff."

I am faint and a loss of words, "Ahh... Ahhh.. I.. don't know."

Helen asks, "You don't now what? Are you cheating on me? Are you into some weird sex stuff with another woman, stuff like french maid or street corner slut?"

I reply, "Ahh... no.." after I say that, I think if I admit to this she will not maybe begin to think they are my clothes, but I'd be lying and she'd think I'm a cheater, shit what to say?

Helen growing concerned asks, "Well, No what? Are you fucking cheating on me, I want to bloody well know!"

I feel I need to come clean, surely she will understand if I say they are my clothes and I like to crossdress at times, after all it's 2017. so I reply, "Hun.. no... no I am not cheating on you, I'd never do that. The...the clothes are...are mine."

Her eyes go wide and brows raise as she says, "What, you telling me these are your things?"

I sheepishly say, "Yes... yes. I like to dress up in women's clothes from time to time. It's really quite harmless dear."

Helen confused and in growing angst, "You dress up in this stuff? Are you some faggot? Do you want too become a woman?"

I reply in fear, "No... no hun. I don't know I have always liked female clothes, shoes, lingerie, make up and hair. I just do it for a stress relief. I hid it from you as I was scared as to how you would think or what you would say."

Helen very upset says, "You tell me after what eight years of marriage that you crossdress and play frilly sissy and stuff. I am shocked you do this and hid it from me, what else have you hid from me?" she adds, "You say you do not want to become a woman? but are you some kind of faggot, do you dress up in this shit to attract men?" "Do you bring this stuff when you are on the road, dress up like a cheap slut or floozie maid and fuck men or have them fuck you?"

With each attacking question by Helen towards me I feel as if I'm being shot. I try to reply, "Hun.. please...please it's not like that, I don't do those things." I try to walk up to her and want to hug her but she backs away.

She says, "No Phil, don't touch me I need space from you right now. Maybe you better freshen up, put your stuff away and we will talk later. I'm going to go out for a while, there are t.v. dinners for you to eat."

I try to interject, "No Helen, please don't be mad I never wanted to hurt you." I add, "I... I will throw the stuff away ok? Please I will."

Helen walking and grabs a jacket and her car keys says, "Phil, we will talk about this later, do nothing until then, I'll be back when I feel ready too, you just get something to eat." as she walks out the front door.

I am dumfounded, I curse at myself and kick at these boxes yell, "God Dammit!" I storm off to the main bathroom and run cool water splashing my face. I look into the mirror and speak to my reflection, "Dammit you silly pervert, fuck you and your crossdressing, I don't know why Helen would want try stay with you, you damn sicko!" I begin to cry as I splash more water on my face. I then towel off and walk to the bedroom, I get out of my work clothes and put on a pair of sweats and a polo shirt as I sit on the edge of our bed thinking, 'well you silly crossdresser, how are you going to fix this? How can you make Helen understand? You need to toss the clothes and shoes away.' I lay back on the bed and try to let my mind go blank from all this growing stress. I have no appetite to eat as I wonder what Helen is doing and thinking, I just wish I could back up time and fix this from happening. Soon I dose off.

I hear a door open and close, look at the alarm clock and see it's 7:45pm. Shit, Helen has been gone for three hours before she came back. I sit up but feel immobile on the bed as I fear what she will say.

Helen asks, "Phil where are you?" I sit and remain quiet with concern on my face. I hear her walking towards our bedroom and she opens the door, "There you are, did you not hear me call you?"

I sheepishly look up and say, "Sorry hun, I was distracted."

She says, "Well I have been thinking and wondering what to do about this, should I file for divorce? Should I try to put this stuff past us? What should I do?"

I reply, "Helen dear, please don't divorce me, it... it's only a bit of crossdressing, I mean no harm, can't you get past this?"

She says, "Phil, the thought of you dressing up as a woman kills any desire for a normal male/female relationship with you. The fact that you have been doing this all these years, and especially likely dressing up as a cheap floozie slut or maid in your motel rooms when you are out of town bothers me. How can I trust you do not fuck or suck off other men? How can I trust you have not been fucked or sucked off by men? You say you do not want to become a woman, but what if one day you come to me and say you need to become one?"

I reply, "Trust me Helen, I do not want to become woman, I just like dressing. I have not been with any men, really I have not."

She sits in the corner chair and asks, "When you dress up, do you think about sex?"

I look at her while I twist my wedding band and say, "Um it depends, sometimes I just put on women clothes other times I feel sexual in them."

She asks again, "Do you think about sex, specifically with men or women? BE HONEST WITH ME PHIL!"

I sheepishly reply, "Well I do... do think about being with men. Bu...but it's not what you think. In my normal life I'd never be with a dude, but dressed all girly, slutty or sissy maid I get off about thinking about being done by men. But.. but I am not gay." I angrily add, "Fuck it I don't know what the fuck I am when dressed up. I do know that I love you."

Helen sits stunned, "You tell me when you dress up you think about sex with men and your not a faggot?"

I reply, "I feel like a sissy, either a slut or a maid and feel effeminately weak to feel the need for a firm man to have his way with me, it's not gay but erotic in a sissy way."

Helen adds as she stands up, "Phill I need to think, I want you to stay out of my way tonight, go do you own thing down stairs and you will sleep on the couch tonight. I will think things through, we will talk tomorrow. In the morning I want to avoid you, we will not eat breakfast together, we will go to work and we will pick this up tomorrow night ok?"

I look at her and say, "Yes, dear." as I walk out and make myself a coffee, once doing so I go to the home theater room and sit down by myself. All this stuff has me so worried and concerned. I really cannot deal with another divorce, surely Helen will make it tough on me if she does. I really have to reassure her I mean no harm with my crossdressing.

I really do not feel relaxed in a chair in the home theater. I want to go upstairs and talk more to Helen, but I respect her wish to not be around me tonight. I try to watch some t.v., check my emails and just sit around. About 10:45pm I decide to get ready for bed. As I head upstairs I find Helen has gone to bed. I wash up and set up a bed on the living room sofa. I turn out the lights and try to get some sleep. It takes a long while before I dose off.

Morning comes and my alar goes off, it's 7:00am and I sit up on the sofa. Soon I make my way to the bathroom, I find that Helen has got up and left for her work already. It sucks that she is avoiding me, I shower and shave and soon dress for work. I grab bite to eat and a mug of coffee and I have to get into work mode, hoping time will sort things out between Helen and myself.

Once at work I try to get things done but my head is not in the game. Roger in the other office can't help but notice I am bothered as he asks, "What's the problem Phil? You look out too lunch and lost."

I look at him from my desk and tell him. "Oh nothing but a few things on my mind from home, nothing you can help with, sorry I'll try not to think about it."

Roger says, "Fight with Helen?"

I say, "No not really, it is just an issue I have to figure out."

Roger says, " Want to shoot it off me?"

I say, "No Roger, really it's ok, I'm ok."

I drudge through the work day and about 1:00pm I get a call on my cell phone. Helen is calling as I answer, "Hi hun."

Helen on the phone, "Phil, I've been thinking... a lot. I'm going to be little late tonight, this will give you time to do the following for me."

I reply,"Yes, darling what?"

She replies,"Ok, I have much on my mind about things between us. I decided I want to see you dressed up. I mean all up, makeup, wig and in one of your maids dresses, hosiery and high heels."

I cough and reply, "Um... really... yo...you sure? I.. I don't think I should."

Helen says, "Phil I need to see this girl in you and I want to see her as a maid, so just do it. I won't be home before 7:00pm. This gives you time to fix your own dinner and to dress up as I expect."

I reply, "Oh..ok, hun.. ok I'll dress up for you... see you then."

Helen ends, " Ok yes I will see you later, don't fail to dress up." and she hangs up.

I sit in my desk chair and hold my face thinking, 'I don't know if this is wise but if Helen wants to see me enfemme, I guess she is open minded to some degree.'

The rest of my work day passes by and my nerves are excited with a bit of fear and hope that Helen accepts my crossdressing. I hope she can get over this and not ask for a divorce.

After work I get home today about 4:40pm and head inside the house. I am all a nervous wreak, I'm hungry but do not have much an appetite. I get a mug of coffee and grab a bit of left overs. I eat but again I have not much of an appetite. I'm finished by 5:10pm and decide I better get ready and dress up for Helen.

I soon shower up, make my self all pretty scent wise. I soon sit at a mirror and grab my box of makeup and begin doing my face. I start with concealer on my beard area and under my eyes to lighten them up. I then do some hi-lite and shadow contouring. I then smoothly apply a neutral foundation for my fair skin. Put on pressed powder, I then begin to do my eye shadow. I start with a light mauve and fill in my eye lids up to my brows. I then take a smokey-purple and from the middle of my eye lid and out in a nice wing fill in the area as well as run the colour under my eyes giving a deep smoke-purple color. I then take a metallic purple and fill into inner eye lids. I then blend all nicely.

I then grab some black eyeliner and rim my eyes all around, this really enhances my rather sexy femme eyes. I then curl my lashes and put on two delicate coats of mascara. As my eyes set I move onto to powder hi-lite and shading to contour my femme face. This makes a man's face go very femme and sexy if done right. I blend a ruby blush but not clown like, sexy tasteful. I then line my lips in a ruby red lip liner and then fill in with ruby red lip stick. I also draw a feminine but neutral shape eye brow arch with earthy colour pencil and shadow. Even a neutral arch as such can feminize eyes. I spritz on some Chanel No.5 perfume and move to dress.
I put on a white lace bra and fill in my average size breast forms. I then put on a cute white satin and lightly padded panty. I then decide to pull on a pair of plain white tights, snugging them nicely over my long and rather sexy legs. I then put on a white satin camisole and a fluffy white petticoat. From this I then put on a black satin with white lace trim maids dress, It's only mid thigh long and my petticoat peeks out with exposure. I put on a black satin and white lace choker and my cute white satin and lace trim apron. I then put on my blonde with light auburn hi-lights shoulder length and wispy wig with cute face shaping bangs. Finally I top off with black satin and white lace trim maids cap.

I go trough my accessories and grab a gold bangle bracelet and then pick out from all my heels a pair of black velvet 5 inch spike heel pumps with sexy black velvet ankle straps. I'm done all dressed up. I think, 'Well girl this is how you will present yourself to your wife. I can't believe it but Helen will see me as a sissy maid soon.'

I walk to a full length mirror, to look at my cute sissy maid self. I do say to myself, "Dear, you are a cutie lil sissy. You do feminize well. I hope Helen enjoys my sissy self." as I curtsy to my reflection. My cock is rock hard in my panty. I can't help but touch myself through my tights and panty. It feels so fucking good, I love dressing like this. I play with myself but do not want to stimulate myself into cumming. I soon think about what Helen will say when she sees me as this sissy maid. What will come of this.

I walk out to the living room and mince around in my high heels and practise curtsies. I go to the kitchen and get another mug of coffee. My nerves are a wreak as I try to enjoy my coffee. I sit quietly and watch the clock as time ticks by. Helen said she won't be home until after 7:00pm. I look up and it's about 7:00pm. I feel nauseous. The guy in me wants to take off these clothes, but I know Helen demands she sees me in them.

I now hear a car pull into the drive way, Helen is home and I'm dressed as a made up sissy maid, soon she will see me in my effeminate sissy glory. I feel like throwing up. I stay in our living room and do not head down stairs to the entrance way. The door opens up and I hear Helen enter but I also hear another voice, I think, 'Shit she is not alone, who is with her? Why is she going to embarrass me?' I soon notice the voice, it's a close co-worker friend Jenny. I guess Helen has talked to her about all this stuff.

Helen shouts out, "Phil! Phil are you home? I need you to come to the front door!"

I am a nervous wreak, I am shaking with fear but also strangely excited. I know I must do as she asks and I begin to walk to the front door and carefully in my 5 inch heels step down each stair step. As I appear before Helen and Jenny I see eyes go wide open, eye brows rise and two women giggle at me. I am about to melt in humiliation.

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Chapter two to follow soon.
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