From a Husband to a Dutiful Sissy Ch. 04

Anyways back to the morning all dressed in my black maids dress, white petticoat, black sheer pantyhose and black suede 5 inch spike heel pumps and preparing then serving breakfast in bed to my Mistress wife and her lover Sir Alan. It is exciting but humiliating for me too. Once they have been served I am sent back to the kitchen to eat my plain oatmeal breakfast.

After they finish shower and dress as I clear and wash all dishes, they are sitting in the living room with coffee served to them by sissy maid me. I am called and to kneel before them, they begin too tell me of what will be going on this Saturday night.

Helen sits up in her chair and says, "Chantel, dear, you are coming along well in your sissy servitude."

I am on my knees and head bow, "Yes, Mistress, thank you Mistress."

Helen goes on, "Alan and I have been doing a lot of talking about your future, obviously as long as you are my Husband and allowed to live here you will concentrate on your sissy servitude, practice and develop your feminine deportment. But we have figured that there is a business model in having you being a crossdresser, sissy maid and sissy slut. Alan and I feel that we should develop your slut skills. You say you have not been with men, but you think about it as your crossdress. Well Chantel we feel you should explore this side of you, after all what girl does not want to be with and please men sexually?"

I reply, "Um.. ahh...ahh Mistress, I think about this but I am quite scared to the idea of turning to men sexually."

Alan interjects, "Chantel surely you see that you no longer shall be with women, a woman does not want to be with a sissy who loves being subservient as maid and who thinks about being a slut. We feel you will embrace your sissy side and learn to enjoy being with men, taken by them. Surely you have thought and think about that much, especially when dressed."

I say, "Sir, ye...yes I see but I am not sure how well I will please men."

Alan says, "Chantel, you are a lucky male, you feminize very well, you are a little hottie, we can see it in how you carry yourself as a sissy maid. You know it, you strut well in heels and you love crossdressing. We feel dressed as the slut you desire will bring out that girl in you who will love to please men who are into girls like you. You should no longer deny yourself. Your future is a feminine one and why not make a business out of it?"

I cough but say, "Yes Sir, but boy oh boy dressing up even when I do dress as slut and being one is scary."

Helen says, "Chantel we have had to adjust our lives, I enjoy having you become my submissive sissy maid, I do want you to explore your whole new side."

Alan adds, "Yes, we feel it's time you explore the slut side of you. You see once we get a gauge on how well you practice oral and anal sex with men who get off on girls like you we feel we can begin to make pro grade sexy and sex videos. Create an online business where we offer to people mostly horny guys who love to fantasize and jack off to hot lil trannies, we will make money off your work. We will create a contract where the profits will be shared even with you."

I reply, "Wow, yes that is exciting and to make extra income will be cool."

Alan says, "So tonight we will have you dress up as the slut you see yourself as and then by oh about 10:00pm will go to the rest area off the highway about 15 minutes from here, you know the one where people cruise and hook up. We have been running an ad in Craigslist, casual contacts about you being a new tranny slut who is eager to develop her cock sucking and getting a good but fucking. We are sure men will arrive to want to hook up with you."

Helen adds, "Chantel, dear, it should be fun, you will get to finally know what it will be like to please men with your mouth and your sissy backside. I know you want to do this, don't be scared, don't fight it, you know you want it, but Alan and I will not force you."

I reply, "Umm ahh Mistress, yes, I do think about such sex... I ... ahh am happy that you are not forcing me into it."

Alan says, "Chantel, I am certain you will enjoy it, you crave cock, you want to dress up as a slut and search out for cock. This will refine you and will let us move you onto making these sex videos, imagine the extra money you will have so that you can buy feminine stuff, more sexy clothes, high heels, make up, jewelry and stuff."

I say, "Yes sir, um you are both right, maybe having you two push me to find my new sexy self. I guess maybe I should follow my true side... OK, I'll do it, lets find out what kind of slut I will be. I hope men will enjoy me tonight."

Helen says, "That is great hun, I'm proud of you, finding your new self."

Alan says, "Yes, Chantel, I feel you will look back on this night as another mark in your new life development. I feel you will make a hot, sexy, slut."

I reply, "Yes Sir, yes Mistress, I will find a sexy outfit and will enjoy finding my new self as a slut I am and want to please men sexually. Yes, I am scared but I know this is part of my new life of servitude to you Sir and my Mistress."

The next number of hours I proceed on with Saturday maids duties, always a busy sissy girl and maid, I'm learning to find pleasures in said maid duties. Yes, it's work, work, work, but a sissy enjoys serving as a maid. Of course I keep a eye on clock as I know I will have to dress up and give it a go as a slut tonight at the rest area. My nerves are both scared an excited. Years, well most of my adult life I wondered and fantasized about being taken by men, dressed as a sexy slut. Tonight I will find out in reality what it will be like for me.

I move on to dinner and serving it to both my Mistress wife and her now boyfriend Sir Alan. My male side still finds serving a man and man who is my wife's new lover very hard to accept, but as a sissy girl I need to accept it, to see a real man begin to please my wife in ways I can no longer do. I am now her dutiful sissy maid and as a growing effeminate my Mistress wife will enjoy seeing me transform more and more into a sissy lifestyle that I know inside that I want.

After dinner and my cleaning up it is time for me to begin my lovely transition from sissy maid to a sissy slut. Mistress takes me to the bathroom and shows me a gift she and Alan bought for me. We both stand in the bathroom, my sexy wife dressed all 5'9" of her in a pair of faded blue tight fitting jeans a white turtleneck and a nice gold necklace, her auburn hair down again in her classic Jennifer Anniston style and in bare feet. Of course I'm still in my black maids dress, black hose and black suede pumps.

She hands me a package and I open it, well I now pull out a home enema kit. Well it looks as if I will need to give my backside a nice freshening up. Mistress Helen says it's going to be important for me to keep myself fresh back there if I'm to please men from now on. Everyday takes me more an more down a path of full sissy servitude. Of course I am bothered by this but honestly I know it is a part of what I really want. She helps me hook it up to our shower and the bag is filled with fresh solution. I am to strip nude and step inside the shower.

Once I do so and am standing naked in my shower, my Mistress has the enema bag's tube ready in her hand, tipped lubed up and I am to bend over showing her by sissy bottom. As I do so she begins inserting the tube and once it is well inside me she opens the clamp as fluid runs down the hose and begins to fill my rectum. The feeling is odd and definitely going to clean me out nicely for this evening. Once I feel I can't take any more I beg her to clamp it off. Mistress does and once I am in a mildly bent over position, she removes the hose and has me stay like that for at least five minutes. It's odd stimulating and discomforting. The five minutes feel like 50 minutes, but she then tells me to evacuate the fluid by getting on the toilet. As I step towards it gingerly she leaves telling me to apply depilatory cream over my body, wait for another ten to fifteen minutes, then shower, dry off, put body cream on and then dress and do my night time make up. By the time I've finished showering and readying myself in a towel to go to my maids quarters its after 7:30pm.

I go through my under garments drawer and pick out a nice black lace bra and matching black lace hi-cut lightly padded panty. I then put in my of modest sized but nice breast forms and sit at my make up table. Ok now all my makeup is around me, my large, lit up cosmetics mirror, I see my clean male face, my mind wanders for a bit as I think, 'Well tonight will be a pivotal night in my life, my new life now living more an more as a sissy girl, a maid and now soon to be slut. I can't believe it but not two weeks ago I was still living a typical male life, married to my wife which was in a normal male/female marriage. Today, right here, right now I am about to do my makeup to put on a face of a slut, a sissy or tranny slut. Men will take me tonight, my first blow job and I will have my anal cherry taken tonight. I am scared but aroused as my whole adult life I thought of and fantasized about such sex.'

I come back from my thoughts and now look at my face to begin my makeup application. I have ample time to do it well, take it slow, get it right. Men will want to see as sexy and hot of a tranny slut as Chantel can be. I first put on some face creme and let it absorb well, making my skin appear soft. I then grab my concealer palate and the nice concealer application brush. I take a light and slight yellowish tint concealer and brush it under my eyes and on my eye lids and up to my brows. This helps hide any dark circles and will help make my eye area pop. I next take this concealer and brush my T zone, of my nose and between my eyes, moving to do my beard area, as even closely shaved it needs to be hid. I think to myself, 'One day I will likely get laser done to rid myself of this beard hair.'

Once the concealer is well blended in all these areas I take a darker brownish choices and do some contouring of my jaw line and the sides of my nose, this will help shape a male's face to being more feminine looking. Ok that is done its on to my foundation a light colour as I have for and soft skin which all helps me feminize nicely. My foundation applicator brush is used as I put a blob of foundation on the back side of my left hand to warm it up and draw from with said brush. It's important to blend there foundation from the centre of one's face out and down, including neckline. Pressing in the foundation will help hide often male sized pours but feathering it more and more lightly blending it into your conturing concealer will make one's face not look so drag queen caked on. BLEND, BLEND, BLEND! is a must.

I let my foundation set and then use pressed power to increase its hold and to make my face more matt. For males a more matt look will usually be better. It's on to my eyes, Hmm what colours do I want to go with? I think a slutty look will be a smokey look. My rather deep set male eyes need a good pop with a base coat of an iridescent ivory colour from the inside areas of each eye and up and out to the brows. I will take a light pale blue and brush the brow area next. Now comes the smoke. A blue-black colour and a chisel brush starting tight under each eye a soft line is drawn. A centre point on the lid to the crease is next, then drawing a line out from the centre of my lids through the crease and a soft wing up from under each eye. I take fluff brush and fill in there smokey, blue-black. Now I grab a mid blue/grey iridescent colour for the middle of each lid to the nose. Then blending brush to soften it all.

I next take my black pencil and draw a strong eye line with it, taking a smudge brush to soften this line and make my eyes more intense and moody. Eye lash curling next and two delicate coats of blue/black mascara. My eyes short of drawing in brows is done. As to my brows a clay/brown pencil is used draw a nice brow arch, filing in with a brownish powder and my brows are feminized well enough.

Face powder to hi-lite under my eyes and T zone, then a darker to contour my jaw line an sides of nose. A delicate brushing with a high quality blush brush, ruby red blush, from the apples of my cheeks and brush gently back. Fill in my lips with a ruby red lip liner and a ruby red lipstick. Finish with a nice brushing of loose powder and a spritz of perfume and look in my make up mirror to see that I'm a sexy bitch.

Ok, back into my lingerie drawer, wow I'm thinking, 'Ha, my lingerie drawer, how many men can say that? But then again how many men surrender their man card to living as a sissy girl?" as I reach in and pull out one of my black lace garter belts and two sexy sheer black stockings. I put on the garter belt and gently slip on each stocking being careful to clasp the garters to each lovely lace stocking top. My sissy dick is rock hard in my black panty. I look through my closet and pull out a cute red satin long sleeve blouse and put it on, gently doing each button up. I then look at my selection of mini-skirts, what to choose? I find a faux black leather mini-skirt which has wide, loose pleats and once pulled on is very short. It goes only down to the top of each stocking's lace tops. Mmmmmmm, I feel so sexy. I grab a wide black cincher belt and use to shape my waist to help create an illusion of my curves. I then grab a new black velvet choker with gold and zirconia decorations in there front, put it on my neck. I can't help but not step in front of my full length mirror but grab my light auburn with blonde hi-lights shoulder length and wispy wig, the cute bangs fame my girlie face and put it on before this mirror to see a transformed me.

'Wow! what a sexy bitch I am.' I think. I smell great of sweet Dior perfume, I look sexy and very feminine and all I need is to pick out some heels and a jacket. I go through my heels and decide to go with a great pair of cum fuck me heels, my red suede, 6.5inch spike heel pumps on 1.5 inch platforms. BANG! I am a slut, a hot slut who should get some serious action tonight.

I pick out a black leather jacket, cut short to the midriff and it makes me look seriously sexy. I can't help but not stare at this hot, sexy bitch of a girl, a tranny slut tonight. I am in sissy, sexy girl heaven. I so want to jerk myself off but I know I shall not. I fill my black shoulder length purse with my I.D. a few dollars of cash, some makeup, a spritzer of perfume and a tube of Astra glide. I say to myself, "Fuck Chantel, you are going to need the Astra glide tonight, you will lose your anal virginity tonight and after all these years."

I look at the clock and see it's now 8:40pm. I put my keys in my purse and figure I need to go to the living room to show my look to Mistress Helen and Sir Alan. I bet they will be happy.

I strut out of my maids quarters and step by step to the living room. Helen and Alan are sitting side by side her head on his shoulder watching t.v. as I step into the room. This causes them to sit up and look towards me. I see eyes go wide and Helen first mouth silently "Holy Shit." Alan also silently mouths, "Nice."

I curtsy and ask, "Does Mistress Helen and Sir Alan approve?"

Helen says with big smile, "Hell yeah, you hot little tart."

Alan adds, "Oh yeah, you are a perfect slut material Chantel."

Oddly enough I am soaking up all this from Mistress Helen and Sir Alan. Knowing they like what they see makes me so excited and in fact looking forward to how any men will see me tonight when I am at the rest area. I am becoming the slut I want too be. I am instructed to give Helen and Alan a turn so that they can see my whole outfit and look. My mini-skirt and stocking clad legs with my sky high heels make me so tall and thin. My 5'10" about 180lb body looks more girly and tall/thin from such. I do tell Helen and Alan that I am very nervous about tonight, fear being beaten up, I do fear having sex with men for the first time.

Alan says, "Chan... you will be just fine, that rest area has been a place for sexual hook ups for years. You are not the first crossdresser to hook up there. You look fucking great, I'm sure many horny guys have seen the Craigslist ad may all scope you out tonight."

I reply, "Thank you Sir Alan, I figure you are right, but still I hope no bad dudes beat me up."

Helen says, "Chantel, you will be too busy getting it on with dudes, just you wait and see. If bad guys try to assault you, you cooperate to reduce any risk, but call the cops as soon as you can. It's not against the law for crossdessers no matter how they look to be out and about. But strut yourself and hopefully you will be kept busy sex wise."

Alan adds, "Yes, we want at least two blow jobs and one butt fuck, One guy will be privileged to take you anal cherry. Make sure you get some video on your camera phone too."

I curtsy and say, "Yes Sir, Yes Mistress."

It's about 8:50pm I have about 45 minutes to relax. I allowed to get myself mug of coffee to ease my nerves, go to my maids quarters and relax to some music until I have to go. I get a coffee, relax to my stereo setup in my maids quarters as I try to get my mind up to the sex I will be having tonight. I can't help but not see sexy, slutty me in the mirror though. I hope tonight will be sexual magic for me. It will change me in ways as I will be a slut having sex with men, all a firsts for me.

About 9:40 Mistress comes to my quarters and tells me it's time to go, to head out for a night of good sex at there rest area. I get up from my bed and curtsy as I thank her, I put on my cropped black leather jacket and grab my purse. As I walk out to the living room I curtsy to Mistress Helen and Sir Alan as I then walk out to leave. The evening is fresh and dry, there was an early evening shower, the breeze is still nice, but it's dry now as I scamper in my heels to my car and then begin my drive out to the rest area.

The drive is about 15 or so minutes and is both exciting and scary for me, as I know I will be having sex with horny men for the first time in my life. I think about sucking cock and being fucked up my tight virginal ass, shivers run down my back.

About 10:05pm I pull into the rest area and slow through the parking lot. There are two other cars parked right now. I pull in about 30 feet to the right of one of the cars. My nerves are very flustered. I sit and my stereo is on and I listen for a minute or two as the music is helping me keep calm. I know I have to step out, I have to strut my stuff as I have been advertised in Craigslist for days now. I swallow hard and open my driver's side door, a woosh of cool evening air rushes into my car and caresses my sexy, long, stocking clad legs. I think, 'Mmm feels so nice, I love my legs feeling fresh and free in sexy black stockings.' I carefully swing out lady-like both of my tall red suede high heel shoe'd feet and plant them on the asphalt. I now get out and stand up tall in my sexy red heels. Keys in hand, purse on my shoulder and I close the car door. This is it I am at this rest area, dressed as a sexy tranny slut. I toss my hair back as I scan the parking lot, again two other cars are currently parked. As I begin to step away from my car in a slut-like fashion, I soon see one car closest to me is empty of a driver, but I soon see in the driver's side of the next car further from me and closer to the walkway heading up to the public bathrooms I do see a male in the driver's side. Another gulp as I swallow, my nerves are very active as I do not think he has seen me yet.

I continue to carefully but sexily walk in my tall heels, that lovely click clock sound of each heel on ground as I step. My sissy dick is growing hard in my panty. I quickly see the man in the car see's me, we do not make eye contact as he darts his eyes away from me as I walk closer to his parked car but now I am on a concrete sidewalk. I keep strutting as I walk up and begin to walk past this car. I see coming out from the men's bathroom the man who must be the driver of the first car. He is about 30 feet up the walk way and begins walking back down. I walk past the intersection point of the two walk ways, he must see me in the dim light of the rest area, but has yet to say anything if he will. As he gets to the point where he must turn to his left, he stops and scans me as I am now about 15 ft. away from him. I look over my shoulder as I gently turn on my heels. He smiles and nods at me, then he walks away after I smile back at him, he turns his head and has a good look at me before he gets into his car. I start slowly walking back the way I just came. This driver starts his car and backs out too then drives away. He toots his horn as he passes me.