Castrated Sissy Maid Stories

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Orientation
Length
Source
Infinite Scroll

Sissy's Revenge

by Not_John on Sep 12, 2017
Transsexuals & Crossdressers

Ok, My last post received quite a bit of negative responses because my protagonist was a total wimp and let his wife walk all over him. Well in this one, in the end, stands up for himself. Warning: this story contains all the elements of cuckolding save one and feminization of males. If you have a problem with either of those, then quit reading here. Skip...

Helen, my Wife and Cuckoldress

by siscuc on Sep 12, 2017
Fetish

She stood before me, eyeing me up and down shaking her head. "So this is what really turns you on, hey?" she said mockingly as she slowly ran her fingernails over my cock through the lacy panties she had told me to wear. "Look at you getting all excited but your dicky is so small it can't even escape from those panties!" She laughed as she turned on her heel...

Zamindars Pt. 02: Thakur & Champa

by prithvik1947 on Jun 18, 2019
Group Sex

In Zamindars Part 1, I had described the situation that I witnessed on arriving at my friend Vivek's estate. His father, Subhash (The Thakur) was openly having a sexual relationship with Champa who was 20 years younger to him and the wife of his driver. Part 2 is more about what I saw between Subhash uncle & Champa. Champa was sitting in uncle's lap while h...

Please Take Baby Steps

by bawdybloke on Sep 15, 2017
Humor & Satire

She sighed at me, perusing my choice of items from the sex exhibition in the paper bag. "Why?" "Because they are all awesome," I cried excitedly. "I've read about this and ..." "Yes, I know you've read about it," my lover muttered calmly and ran her hands through her flowing red hair. "We discussed this and ..." "Come sit down," she cooed, calmly. I felt...

Some of My Tgurl Adventures Pt. 03

by sexyR2 on Mar 30, 2020
Transgender & Crossdressers

Et.al., as I said in the header of part 1 of this series, it is about the continuing adventures of an owned submissive sissy, whom I still have not yet named, whom is on a trip to a Mexican resort with the instructions from her Mistress to pleasure a minimum of 14 strange men over the two weeks that she is at the resort. Parts 1 and 2 appear to be getting so...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

Recruiting of a Sissy Maid Ch. 04

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Four: Chantel, Fitting Into Her New Lifestyle. Master Holt says, as the two of them walk out from the elevator on the 2nd floor, "This will be the floor that you will begin your life in servitude to us Chantel. Lets go find your head maid Penny and then get you to your room." Chantel grows more and more resigned to this new life as she see's a very...

Sissy Chantel, New Reality Ch. 06

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Six: On My Way to My New Life at The Agency. Well the day has come for my transition in my life to becoming another sissy maid and sissy slut (aka: comfort girl) to 'The Agency'. Over the last two hard and humiliating weeks Master Camron and Sir Gage now as paid agents to my joining the team at 'The Agency' have helped me sell, give away or toss o...

Sissy Chantel, New Reality Ch. 02

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Two: If One was Fun, Two will be Better. Late night I get a call and I look to see that it is my new Master. I answer, "Hello Master Camron, how may I help you?" "Bitch ass sissy, I am gonna need you here tomorrow morning, by 10:00am." he excitedly replies. I reply, "Oh, ok I guess I can make it to your home tomorrow morning Master." "You God Dam...