Sissy Stockings Stories

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From a Husband to a Dutiful Sissy Ch. 05

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Five: I'm going to be more than just a sissy maid. Waking up Sunday morning, I sit in my bed and think about my slut duties last night at the rest area. I get into the shower and it all floods back to me as I shower, then dry off, moisturize and get back to my maids quarters and do my makeup, put on my bra, panty and maids outfit, black one today wi...

Mommy's Boy? Ch. 02

by yr_sissy_toy on Sep 13, 2017
Transsexuals & Crossdressers

I skipped home from school, an expression of the giddy joy I'd felt for the last week. I'd gone from a pansy boy who got teased after school to my mommy's special sissy, who was swathed in the finest femininity the moment I got home. It was delicious, intoxicating even, and I was almost bursting with joy. I'd learned so much in the last week! I could slip i...

Sissy Life Pt. 02

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I scurried to the bathroom, tears streaking my face. I was dripping cum on the bedroom floor as I went, but I didn't stop. I just wanted to get out of the room. I couldn't believe how badly things had gone! 20 minutes ago I was stood in my May babydoll, black stockings & red heels set for some intimate time with my wife, my Mistress, but now? Now things were...

Christening Dany

by SissyPantySlut on Sep 13, 2017
Transsexuals & Crossdressers

You hear your doorbell and your heart immediately races a mile a minute. You pull up your athletic shorts and a sweatshirt over torso. You rush to the door, swallow and then open it up. I'm everything my picture promised and more. Perfectly femme, you'd swear I was a curvy woman in a satin dress and high heels. I step in and give you a quick kiss on the lip...

Powerless

by siscuc on Sep 16, 2017
Transsexuals & Crossdressers

I was alone in the house, Tina was at work. It was 4 in the afternoon and i was looking over some pictures when the phone rang. It was Tina, "Hi Sweetheart" i said. The tone of her voice was harsh "Start getting ready, tonight you will be my sissy, you can choose to wear any of my clothes except the ones in the top drawer, I'll be wearing them." That was all...

Sissy Instructions

by FrostShard on Sep 13, 2017
BDSM

Dear sissy, I trust you are preparing yourself well for our session next week. This session will be your final plunge into the realm of sissyhood. Thus far, you have simply dabbled in it, all the while essentially staying a man. All that will change starting from this session. Starting now, from the moment you finish reading this letter, one thing will cha...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

Pantsed Again

by grgy56 on Sep 16, 2017
Transsexuals & Crossdressers

Lori ensured I was always appropriately dressed by picking out my sissy girlie things for me everyday; school girl, cotton, bikini panties with support to make my bum round, my padded training bra with built-in forms and knee socks; all white. Lori selected high heeled Mary Janes for me to wear around the house. When I was allowed out or had to go to work,...

Creating Ginger Ch. 08

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Michelle awoke to the smell of coffee, which as of late had become her...

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....