Sissy Stories

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Infinite Scroll

PIXIE Sissy Stripper Ch. 04

by EROTICbearscribe on Jan 20, 2020
Transgender & Crossdressers

Author's Note: There is a category switch in this chapter. The beginning chapters can be found in GAY MALE. Seeing as what happens in this chapter, the new category is TRANSGENDER & CROSSDRESSERS. ***** THE PINK BOY was located in the warehouse district across town in an eclectic area known for its nightclubs and specialty bars. Within a six block radi...

Seductress & Daemon: Sissy Pt. 01

by SeducedKnight on Sep 15, 2017
BDSM

After Eating out my Seductress for the last hour, we hear a knock at the hotel room door. "Go open it." I go to the door dressed only in my rubber wrist and ankle bands with heels and a pink crotchless panty, I have a plug in my ass and a cold metal cage on my cock. I open the door wide in my full nakedness to reveal a prettily dressed sissy outside. "...

The Awakening of a Sissy Pt. 03

by sissyjolie4u on Jan 20, 2020
Transgender & Crossdressers

As i was watching the video of Mistress and I for the 3rd or 4th time, my phone rang. "Hello my sweet Joey, how are you doing? I so enjoyed spending our time together, I'm so proud of you and the progress you are making. Are you still in your pink bra and pantie? That is such a sexy look for you, it makes you look so soft and feminine. Tomorrow we will build...

First time Sissy

by PR Sissy on Sep 29, 2019
Transsexual

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any s...

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From a Husband to a Dutiful Sissy Ch. 06

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Six will compress time a bit more forward in moving the story through time. It will be set two months forward from the original start date of the story in Chapter One, when Helen found out her husband Phil enjoyed crossdressing and fantasized about being sissy maid and a sissy slut. It all picks up with bit of recollecting from Phil who is now Chante...

Becoming a Sissy Maid & Slut Vol. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eighteen: Some New Friends for Chantel. A blissful night's sleep has led me to a wonderful Sunday day off. Master has told me I must accept that special Sunday plans are on the go after 3:00pm but today, this morning awaking at 9:00am I run my routine, enema, shower, put on fragrant body lotion. I then begin a day of dressing just for myself, but al...

Sissy Chantel, New Reality Ch. 09

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Nine: It's Friday, I Have a Full Shift to Pull Today and Tonight. At 7:00am sharp we are all waken up. This is our daily wake up call and soon sissy Traci as our dorm room's head sissy maid has us all up and ready to go to our morning routine which will be a group enema, group shower, shave face and when need be the rest of our body hair then to do...

Thrift Store Sissy

by sissywendi on Sep 16, 2017
Transsexuals & Crossdressers

A story by wendi marie st.clair She was looking at girl's blouses the first time He saw her. Of course, most of the world wouldn't have seen her as a "she" at the moment, but wearing her flare-leg, hip-hugging jeans that were obviously from the junior miss department and the androgynous purple t-shirt that showed that she shaved her body, she looked like a...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

Becoming a Sissy Maid & Slut Vol. 06

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Twelve: Chantel's day off. Ohhh, and ahhh as I awake and stretch in my bed. Mmm a blissful sleep where I see the clock and that it's actually 10:00am. At first I freak out a little bit as it normally would be very late for me. But I soon realize Master has allowed me a blissful and free Sunday off. I then get out of bed, my butthole is sore from the...