tagTransgender & CrossdressersRecruiting of a Sissy Maid Ch. 01

Recruiting of a Sissy Maid Ch. 01


[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my readers to look forward to and read hoping to enjoy them.

1: It was written from a 3rd. person point of view. A new style for me and I hope you like it as such.

2: The story begins as a wanting to be sissy, sissy maid and sissy slut story and develops into a deeper sissy maid and slut story with some exciting and hopeful emotional plot twists.

3: It has a good level of eroticism and sexual heat, with very trans girl and submissive writings as well.

I hope this next story will draw and keep my readers interested until its conclusion. It's going to be in my opinion a cool, interesting and erotic story.



Chapter One: Falling into the Web of Sissy Recruitment.

It's raining like cats and dogs tonight, some flashes of lightning and crashes of thunder are seen and heard outside. A night to be inside and bundled up tight in one's own world of thoughts and pleasures. Phil is sitting at his computer, dressed as he often does during his free time evenings wearing women's clothes, shoes, hair and makeup. Phil when dressed is in his alter-ego, Chantel. Chantel is a cute and very feminine acting crossdressing girl and most often a sissy girl in mindset.

Chantel is 44 years old, divorced, estranged, white male, about 5'10" and 185lbs. Generally fit for a 40 something but dresses very well especially with her ability to do her hair (wigs) and makeup. She knows she looks pretty cute as a crossdresser, her fair complexion and soft skin for a 40 something once made up has her easily look 10 or more years younger than she is and she loves looking it.

Phil has after his estrangement and divorce kept a rather simple life, not much family around, a small group of friends, but mostly lives to provide for himself in an ok career job but not one he loves. His originally costly divorce has caused him to keep his assets close to him and his debts low. Crossdressing is his most enjoyable and peace of mind activity. Phil has spent a good sum of money on all of his feminine wardrobe, shoes, boots, makeup, wigs and accessories. His closet and dresser drawer are over flowing with all this lovely, feminine stuff.

Phil has been a good guy in life, normal living, mostly a regular acting dude, but peaceful, lots of life's baggage though. As crossdressing has been a burden for him as much as a joy. He keeps it private, it did come out in his separation and subsequent divorce. His ex-wife and adult daughter are as noted estranged, it's hard for Phil but that is his life now and his cross to bear.

Sexually as a regular acting male, Phil has been heterosexual, but his feminine side as Chantel has always mostly been one of sexual feelings towards strong and dominant men. As Chantel, Phil has felt trans-like and regularly fantasizes about being sissy, sissy maid and sissy slut to strong men. But he has not acted on these feelings as he has lived his life as a male and keeps his crossdressing side as Chantel private. He only has confided and played with a few sympathetic females at times who have helped him get his feminine look down well.

Phil especially as Chantel does a lot of internet surfing of sissy, crossdressing sites and sissy, crossdressing and BDSM pornography. It creates much of his sexual excitement as a crossdresser and sissy. But as time ticks by and his life flutters like a flag in the proverbial breeze of life he often wonders about what it could be like to be some strong man's sissy bitch, sissy maid, feminized and enslaved to a dominant Master, doing much of the sissy, BDSM porn he sees online. It seems to consume more and more of his daily life now. It's as if it becomes a greater calling.

With this storm blowing by, Phil is dressed as Chantel, black bra and panty on, a pair of black sheer pantyhose on her long sexy legs, a black satin maids dress with white lace trim and a white satin and lace apron. She has her face fully made up as lady-like as she can and has on one of her lovely, fun wigs a light auburn wig with blonde hi-lites. The wig is full and wispy down to her shoulders and has cute face framing bangs. Chantel looks very cute and youthful as well as quite passable. Finally tonight Chantel has a pair of black suede 5 inch spike heel pumps on and she loves strutting around in her heels.

Wasting time during this storm Chantel looks at various crossdressing, sissy, BDSM sites and pornography. This has her fiddling with her oh 5+ inch uncut, white, sissy dick. She is enjoying reading up on stuff and watching various sissy, crossdressing and transsexual pornography videos. She brings herself to almost cumming many times but stops in denial to prolong the lust and emotional pain of not ejaculating in her panty. She will save this build up and denial all night long until she has to go to bed. She knows once she blows her load of sissy cum in her panty she will want to get undressed and be back as Phil, regular, normal, predictable Phil. Being Chantel is so much more thrilling and fun.

Chantel comes across a seedier part of the web and finds some info about an opportunity to become a real sissy maid and slut, living enslaved in said world where a large part of the underground sexual world exists. This has her very perked up as she investigates this possible opportunity.

"Wow, what is this site? Hmm a site where they are looking for sissies to be enslaved as maids and sluts."

The website describes what they do. It seems they are recruiters to help match up willing sissy crossdressers to a group of underground type sex businesses. These businesses are located at various cities and often need new sissy maids and sluts. Chantel reads on about the bio's of these recruiters and all they do to recruit train, orientate and break of will any sissy that chooses to sign up into this lifestyle. The team consist of brothers, Mitch and Nate Burrows, both 30 somethings and have been doing this style of underground sissy maid and slut recruiting for near 7 years now.

Chantel's curiosity grows, as she speaks to herself, "Wow, this turns me on, so fucking much. I can't believe such a site and opportunity exists."

Chantel reads on as the content of the website details how willing sissies can offer to be recruited and if accepted the wiling sissy agrees to being groomed, trained, orientated and broken of will with goal, of enslavement into a lifestyle that many sissy crossdressers dream about. It's as if these men are talking to Chantel, she can't help but pull her sissy dick in heat as to this possibility of being enslaved.

They explain the best candidates are the ones who have little to lose and leave behind, few if any real relations, single, widowed or divorced, no serious careers to hold on to, ability to have assets seized or sold off and a desire to follow their sissy desires. Every one of these points align with Chantel as the closeted crossdressing sissy she knows she is. She is turned on to this and for now book marks this site as she finally jerks off and cums in her panty.

Once that happens she decides to turn in for the night but will think about this website... Imagine recruiters to put fag sissies into lives of enslavement. She falls to sleep thinking about this.

Days later Chantel is back visiting this recruitment into sissy enslavement website. The site's section as to applying is open and she reads it.

Chantel thinking says to herself as she jerks her sissy dick wearing her pink satin maids dress, white tights and pink 5 inch spike heels, "Fuck I'm in my 40's living a boring life as a generally bland male. I only get off dressing in women's clothes and often as a sissy maid and jerking off to it all. Seriously this website is my calling. I feel a need and want to apply to Mitch and Nate Burrows."

Chantel begins to fill out the general questionnaire, it gets quite detailed in requests for personal info but Phil guesses if they are to consider her as a recruit to sissy enslavement they need this. So she carries on filling it out. Once filled out Chantel really horny by pulling her sissy dick, reads it over and has to decide if this is what she wants to do. Pulling on her hard sissy dick she is flowing with horny thoughts and heat, it is making her think only about becoming a sissy maid and slut.

She says to herself as she is about to cum into her panty, "Ahh...fuck...fuck it...my life needs a change." as she grunts out, clicking on the submit button and cums a huge soaking amount of sissy semen into her panty. She is in ecstasy as her orgasm is so heighten by the thought of possible enslavement. Chantel sighs and pants as she comes back down from her sissy orgasm.

"Fuck maybe I should not have done this. But I guess I still choose to follow these recruiters into my breaking, training and orientation."

She relaxes and unwinds her latest night of sissy crossdressing.

A couple of days later Phil's phone rings, [he was required to give these recruiters a phone number], he sees it's from an outside caller but he does not know who it is.

"Hello." he says.

On the other end is Mitch Burrows, "Am I speaking to Phil Lasalle?"

Phil replies, "Yes, this is he speaking, what can I help you with?"

Mitch replies, "Well Phil how about I just call you Chantel?"

Immediately Phil freezes up, silent for a moment.

Mitch says again, "Huh, you are Chantel aren't you?"

Phil is quite nervous as he replies, "Umm..ahh...ye...yeah, um it is Chantel."

Mitch says, "Are you nervous? Did you not think myself or Nate would not contact you?"

Phil says, "Um..ummm...well..umm no..I guess I was expecting your call."

Mitch asks, "So are you serious of being recruited by myself and my brother Nate? It will be true sissy slave training."

Phil says, "Umm...I'm very nervous, but yeah I guess I am looking at possibly doing this."

Mitch says, "Chantel, that is your name from now on, so use it when talking to me or to Nate, do you understand you faggot sissy?"

Phil / Chantel stumbles for words then replies, "Um..oh...ok, yes my name is Chantel, sissy Chantel."

Mitch animated says, "Bitch, get one thing straight, I'm a recruiter for slaves, fuckin sissy slaves. My brother Nate works for me too. We take faggots like you, fuckin little perverts who get off wearing women's clothes and break them into being docile, dutiful sissy maids and sluts."

Chantel is quite nervous on this call now but holds onto her control. Mitch tells her that he and Nate will consider taking her on to recruiting, orientation and breaking down of Chantel into being 100% compliant sissy slave girl. Chantel is both scared but is also so turned on as well as she carries on this phone call.

Mitch explains that he and Nate will set up a meeting with Phil who can be in drab and not dressed as Chantel. This first meeting will allow Mitch and Nate to asses if Phil is serious or just another faggot sissy time wasting wanker. They get a fair number of wankers. Phil agrees to a meeting on Friday about 5:00pm at a Restaurant and Bar called Jasper's, where Mitch, Nate and Phil will discuss all to be done in this sissy slavery recruitment process. The call ends and Phil is totally hard with sexual lust as to talking to a guy who is a recruiter of faggot sissies and possibly into sissy slavery. Phil who always wears panties and pantyhose even in drab cannot help but to jerk his sissy dick to the sexual lust he feels. Minutes later his sissy dick spurts out sissy cum into his panty and he is done, winding down confused by his action and want but relaxed as well.

Friday just before 5:00pm. Phil arrives at Jasper's to meet Mitch and Nate about being recruited into sissy slavery. Phil is so nervous as he parks his car he feels as if he will throw up. But he also is so excited about going down a possible path of sissy slavery. The more and more he thinks about it, the more and more Phil knows he should become some owned sissy floozie. Well he will soon see if he can accept offering himself as such and to be accepted by recruiters named Mitch and his brother Nate.

As he gets out of his car Phil nervously walks to and inside the restaurant it is here where the hostess greets him.

She says, "Hi my name is Nicole is it for one person tonight?"

Phil replies, "Hi, actually I'm meeting for some business a couple of gentleman named Mitch and Nate."

Nicole checks the reservations and see the table they are at, "Ok, I see, please follow me."

Phil follows Nicole to the table, it's getting busy in the restaurant but he's more focused on meeting Mitch and Nate. Once getting to their table hands are shaken and all people are introduced. Phil is asked if he'd like a drink and he says, "coffee please."

It's really setting in, sitting across the table in the booth are two men, who know Phil is a faggot sissy who may be looking to becoming groomed for sissy slavery. Mitch makes it clear that they are not into faggot fantasy bullshit. They are here only to size up if Phil is sissy maid, sissy slut enslavement worthy. This both scares Phil and excites him, his sissy dick is rock hard inside pants, under his pantyhose and panty.

Mitch says, "If you are accepted by myself and my brother you will have to sign numerous documents. These are documents that allow us to have you legally be employed by your future owners as a "Domestic Servant, hired help". That is how you will be employed legally, but in essence it's just a cover for your future sissy slavery."

Phil replies, eye raised, "Wow it's odd hearing about how I will become some enslaved sissy to some strong owners. What else need I agree to sign."

Nate interjects, "Next, faggot you will sign legal forms giving us to control and dispense with any assets you have and will list for us, it can be a home, cars, other larger items, money and such. You will only be allowed to keep any and all feminine clothes, shoes, boots, cosmetics, wigs and accessories as well as a minimal amount of other personal effects."

Mitch adds, "You will have to accept to divest of most of all your possessions, this will be a clean break and a new start to your life." then smiles and adds, "Are you fine with that Chantel?"

Phil pauses and adds, "Well it's big change but my life needs a big change. Maybe becoming a faggot sissy maid and slut is what I need. I am ok with this if accepted by you to be recruited, orientated and broken down."

Nate excitedly says, "Sissy, my handle is 'The Punisher'. I take the lead role in disciplining and breaking the sissies we bring on so that Mitch can refine and shape them. I will likely be the last guy you will want around you if and when discipline and breaking of will needs to be done."

Phil is shaking as he says, "Um, ok I guess this is needed and as a tool to break a sissy like me."

Mitch says, "You see Chantel, you may be a sissy at heart, you may play and fantasize being some sissy maid and slut, but fantasy and reality are two different things. We both know that sissies like you have lots of petulance and defiance in their minds. No matter what you may think you are far from broken and groomed."

The dinner goes on much like this as Phil learns about what will be expected of him if he agrees to this recruitment. He also finds out that He will be shipped out of his current city and much farther away so that his new life breaks more easily from his current life.

[NOTE: I will be noting a city Phil/Chantel will wind up living at once sold into sissy slavery. This city is a FICTIONAL SUBURB to a REAL CITY of Toronto Canada. The fictional suburb will be where most of Phil's sissy life as Chantel is to revolve around. The fictional name is Marksville about 40 minutes outside of Toronto proper and is a commercial, light industrial city of 175,000. This is where Chantel's potential new owners operate their business which will be more explained later.]

Phil is offered to be able to take home all documents Mitch and Nate provide, to read over

for a few days, which he agrees to. They end the dinner with Mitch and Nate feeling that Phil is possible good stock and feel good about recruiting him and orientating him as well as breaking his will so that he will be a good docile sissy maid and slut.

[One week passes by]

The second meeting between Phil, Mitch and Nate completed the agreement it was all signed and they begin to put things in motion for Phil / Chantel. Phil will be giving in his notice to his employer and in two weeks will begin his sissy recruitment. All during this time Mitch and Nate will help Phil begin to dispose of many of his assets, ultimately will include selling his modest home, car and other large assets. The agreement will give Mitch and Nate 70% of the final value of assets sold and will put into trust for Phil the remaining 30% and will transfer all of Phil's cash assets into said trust, trust that will then be sent to and held by his/her future owners. The agreement has it that this trust will be used for the day sissy Chantel is retired due to age or health in her sissy maid life.

Over these two weeks Phil has begun to close off life as Phil a typical, regular dude who lived as a closeted crossdresser and sissy and begin to become sissy Chantel. Male terms and pronouns will stop, only female, sissy and such terms and pronouns will be used as Phil becomes sissy Chantel.

As the day to move into life as sissy Chantel approaches Phil gets excited but nervous. Lots of furious masturbation as each day passes closer and he wonders about what Mitch and Nate will do to him as he becomes a sissy maid named Chantel. Instructions are given and directions where to drive to are given to Chantel.

Finally it's morning of Chantel's new life to begin. After showering and seeing how a couple of laser hair removal sessions have gone, Chantel is happy. Only a few more laser hair removal sessions should do it to have her face and body be hair free and more feminine. Mitch and Nate believe Chantel must lose about 20 lbs. as they want her to stay in the 160-165lb. range. They will work on her diet as they train and break her.

Chantel gives herself a full enema as Mitch and Nate demand she stays fresh in her back side. They are aware that she is still virginal, anally but that won't be for long. So as Chantel dresses on her first day into her new life, she begins with a black satin push up bra, a black satin panty and a new pair of black silky sheer pantyhose. She sits and does a full makeup application and looks very feminine and passable. She has prided herself as always been on the passable side. She gets into one of her black satin maids dresses which has cute white lace trim and a white satin and lace apron. She has a cute black satin and lace trim maids cap and a black satin and lace choker. She puts on a pair of black leather 5 inch spike heel pumps. She looks at herself in a full length mirror and feels she is ready for a new journey in her life as a sissy maid and slut.

Chantel loads up plastic tubs with all her feminine items and a few personal effects and she is on her way.

Following GPS she finds that Mitch and Nate have a rural property about 40-45 minutes from Chantel's existing home. As she drives ever closer she begins to get very nervous. She knows that Mitch and Nate are not going to orientate, train and break Chantel by being sweet and polite. She begins to think, this is going to be tough, her life will irreversibly change. Knowing that Nate uses the nick name 'The Punisher' and this scares her. But she realizes that she has chosen to commit the new lifestyle for she is a life long sissy and crossdresser.

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bySissy_Chantel© 1 comments/ 29028 views/ 18 favorites

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