Shemale Pegging Stories

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Infinite Scroll

A T-Girl and a Tomboy Pt. 03

by AlexBailey on Sep 14, 2020
Transgender & Crossdressers

A Surfer and a Swimsuit Model _____________ Hello! This is part three of a full length novel in four parts. It's a gender-fluid, 'what if everything fell into place,' fantasy about self-discovery, coming out and coming of age. It explores pansexuality, cross-dressing and several fetishes - especially for things like swimsuits and athletic-wear. Some part...

Bought Ch. 02

by Jeremydcp on Jan 21, 2020
Group Sex

Chapter 2. "First" "When I was younger, I liked these to be slightly toasted, but now that I'm older, I like 'em... charred." "You obviously have a thing for flaming balls." Bella's laughter, sweet and melodious as it was to Jason's appreciative ears, filled the late morning air all around them. A rare, precious gem, his bride was brimming with spirit - u...

My New Trainer

by Deeplust on Oct 9, 2017
Transsexuals & Crossdressers

(The story has mistakes in it, and if you want perfection please skip this story.) * The moment I lifted the weight, I knew I was in deep trouble. Although there was no pop sound, I knew something was wrong. Having been in rehab now for three weeks, I thought I was almost done. I just finished exams and was happy that I was almost done with my first year...

Life's Changes Ch. 13

by Scribler on Sep 16, 2017
Fetish

I woke up Wednesday morning feeling quite good. Pam was there with my coffee, and Jeri was still lying next to me. I had a strange feeling that today was going to be a good day. I asked Pam "How is you bottom today?" "It's still a little red and a little sore when I sit but other wise it's fine. Thank you for letting Glenda stay with me last night." "I h...

Sissy Downfall

by davine on Sep 26, 2017
Transsexuals & Crossdressers

This story is about my conversion from a cross dressing sissy to submissive transformed slut owned by Mistress Rebecca George. All characters are over 18. Having been to the beautician for a full body and face wax I check into the hotel to prepare. The suite consists of a large living room and a comfortable bedroom with a large bathroom. The bedroom has a...

Hypnotized at the Costume Party

by Miles63 on Dec 31, 2017
Transsexuals & Crossdressers

Introduction: Merry Christmas, I'm back after over a year with a new story for you. This is a story I started over two years ago and I decided to finish it off. I've had a beginning for years, but it was short and lacked detail and I had no ending. 6 days straight of typing and tinkering with it I have a more detailed story and an ending, I hope you like it....

Cheerleader's Mom: Mom's Lap-a-Thon

by silkstockingslover on Nov 25, 2019
Illustrated

Summary: Submissive Mom has five visits in marathon fuckfest. Note 1: Thanks to hfernandez1983 for doing the visuals for this story. Note 2: Thanks to Tenzin, Robert and Wayne for editing. Recap: In Part One, A POWER SHIFT: 39-year-old mother Michelle decides to try on her daughter Allie's slutty cheerleading outfit. Once she has it on, she begins fuckin...

Leftovers

by LittleBrain on Dec 3, 2019
Romance

I decided to put this in its correct category. Chapter 1 At the age of nearly 30 I would have preferred not to bring a stranger into my house to live on a semi-permanent basis but unfortunately it was a case of 'needs must'. My ex-girlfriend (I would like to point out that she was not 'ex' at the time that we did the deed as that would have been too stupi...

Life's Changes Ch. 14

by Scribler on Sep 19, 2017
Fetish

I awoke to a gentile kissing of my neck. It felt so good that it brought a smile to my lips. I was almost positive that it was Bill kissing me, but I couldn't sure. I enjoyed the feeling so much that I made believe I was still asleep so whoever it was would continue. I next felt my sides being touched then a hand on my tummy "I can see you smiling, you snea...

A Ski Bunny is Born Ch. 03

by Nikki H on Sep 18, 2017
Transsexuals & Crossdressers

Kim and I are thrilled that so many people are enjoying reading about our adventures. We have received so many really nice e-mails from lots of lovely people, its good to know you girls and guys out there are enjoying them! We had promised each other a trip to Europe but hadn't really made any firm plans. Kim and I were relaxing by the sea. We had bailed ou...