Sissy Maids Stories

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Recruiting of a Sissy Maid Ch. 05

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Five: Chantel Settling in with Her other Sissy Girls "Congratulations Chantel." as Maid Penny tells her today is her 3rd. month anniversary at The Jade Maid Club as they are sitting at the breakfast table with the other girls. Other girls also congratulate Chantel as well. Chantel replies, "Oh thank you all." As the girls eat their breakfast befo...

Being a Sissy for Viv Ch. 01

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

"Even I had to tell my daughter off for looking at a sex site on the internet yesterday. A shame, it did look rather interesting. But even if she is nearly twenty, I really couldn't tell her now could I." "Oh, what was so interesting about it?" I asked. Viv paused for a moment, her eyes on the wine glass in her hands. "It was about turning men into maids....

From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

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. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

Becoming a Sissy Maid & Slut Vol. 08

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Fourteen: Chantel Learns a Lesson. Another bright and early morning for me. Another busy day ahead as a sissy maid and later on as a slut. What plans Master has for me as a sissy slut tonight, I don't know, but I'm sure it will be exciting, with lots of creamy cum for me to taste and swallow as well as good for hard core butt fucking. I'm already ge...

Sissy Chantel, New Reality Ch. 04

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Four: More Sex, Public Humiliation and a Soon to be Turn for My Sissy Life. 8:00am and my alarm clock goes off, I am groggy as I awake but I soon realize I'm about to have another exciting sissy day with Master Camron and Sir Gage. I quickly shower and do myself up as expected in, make up, wig and my black maids dress, black sheer pantyhose and blac...

Becoming a Sissy Maid & Slut Vol. 12

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Bonus chapter added to keep this story moving forward. I felt it should be told and enjoyed. ***** Chapter Twenty One: Sluts at a Party. Our Masters always looking at ways to get the word out about us three sissy sluts all to make sure we become looked for and hunted street walking sluts for sex starved and horny males leads them to putting us out in very...

Sissy's Decline into a Slut Pt. 03

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, Things Look to Begin to Radically Change for Chantel. Well another week has passed by, it's Friday evening and tonight I have to go back to the rest area to hook up with Barry and Ralph as they instructed from last Friday after having me suck their cocks. They promised me that they will fuck me tonight and share me with even more men....

Sissy Chantel, New Reality Ch. 03

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Three: More Fun and a Deeper Push into a Reality. [10:15pm] My phone rings, I look to see who is calling me and I see it is Master Camron. I dutifully answer the call, "Hello, Master, sissy Chantel at your service." "Hey sissy, I need you tomorrow morning, that will not be a problem I suppose?" He asks. I reply, "Oh no sir working afternoons or...

Becoming a Sissy Maid & Slut Vol. 07

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Thirteen: Work, Work, Work, Around the House, At the Adult Store and as a Slut at Night. Monday, morning and back to my sissy maid services. Promptly I wake up at 7:30am. As per usual my morning routine of an enema, showering and dressing. Today I did have to reapply depilatory cream to keep my body smooth and hairless. It takes an extra 10 minutes...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...