Sissy Pony Stories

16,082 results
Orientation
Length
Source
Infinite Scroll

French Lessons

by lipsticked on Sep 13, 2017
Fetish

I first saw the ad on the internet. The website was a listing of Dominant Women on the West Coast. Since I live in Los Angeles, I was checking out the pictures and information on local dominants. The one that caught my attention was unique. Madame Darcy was based in Paris. Her ad stated that she traveled to Los Angeles frequently and had family here. She re...

Strange Feelings

by ChrisLePaige on Sep 16, 2017
Transsexuals & Crossdressers

This is my first story about my life as a sissy. To be specific, it's the first story I'm writing for my Mistress knowing she is going to have me share it with the rest of the world. I've written plenty of journals, stories, and research papers for her, but always with the understanding that they were private, shared only between the two of us. Mistress rec...

The Path to Happiness Pt. 09

by brendachaplin2000 on Sep 28, 2020
Transgender & Crossdressers

A couple of months passed since my weekend away on the film shoot. I wish I could say Chris and I become an item, but sadly I discovered he was already in a relationship with a girl and she was expecting his baby. My life already had too many complications without becoming the "other woman". On a positive note David had started a relationship with Adam, and...

Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

The Society Ch. 04

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

I have a little explaining and an apology to make. The last installment of The Society, called The Society part 4 was uploaded by mistake. If you are following this story you will find that the first part of this installment is very similar to part 4. Please take this story for what it is, parts 1 through 3 and then followed by this installment, part 5. Sorr...

Anklet Adventure Pt. 02

by dometoo on Oct 29, 2018
Interracial Love

Day two of our cruise started with the sun shining through the open balcony slider and a slight, warm breeze dancing over our naked bodies. The rhythmic sound of waves breaking against the hull was memorizing, almost hypnotic. My beautiful wife of 20 years and I lay exhausted on the cum stained sheets she and her bull made without me last night. We were both...

From a Husband to a Dutiful Sissy Ch. 15

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Fifteen: A Big Decision and Telling Mikel. Helen and I are dressed and ready to go to the ladies gym for a morning workout. I love this and dressing in my girlie workout clothes. Today I am going all black, a black leotard, black tights and black ladies shorts. I am going to contrast with my bright pink trainers. My now comfy long, just below my sho...

Jessica's First Time at the Bar...

by Lion24655 on Jul 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Jessica followed Tom into the bar, walking carefully, feeling very self-conscious. Already she had received a number of strange looks, smirks, as she had slowly tottered across the car park in her high heels. Not just the high heels. The bright red lipstick. The eyeshadow. Nail va...

Bedroom Surprise

by wylite on Sep 14, 2017
Fetish

This story is a follow up to the 'Bedroom Research' stories. * I think my minds been messed with; a few months back I would not have dreamed of dressing up in girls clothes but now I was looking forward to a special delivery. Mandy had told me what to order and I had been busy on line picking out a nice pair of frilly pink panties and a pretty sissy dress....

Sarah's Husband

by JJEroticas on Mar 30, 2020
First Time

Sarah's Husband I was nineteen sitting at a table of other nineteen-year-old degenerates. We sat outside, drank rounds of coke, and everyone had their Marlboro packs obscuring the red and white striped table cloth. I ordered a TGIF burger, greasy, a favorite. My body had a secret inside shimmering of nerves, dehydration, and malnutrition from last night's k...