Sissy Cuckold Crossdress Cream Pie Eating Stories

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Briefs No. 03: My Wife's Friends

by PatriciaFCartier on Jul 15, 2019
Transgender & Crossdressers

While sliding my silk stockings up my newly shaved legs, I thought about what got me here. My wife, Madison, told me after I'd been transformed that she'd planned this since before we married. She said she'd dated a boi in college for a while until the boi had been stolen from her by one of their professors. Said she'd liked the concept, if not the result. S...

The Reluctant Cuckold

by 62_goo on Sep 15, 2017
Loving Wives

When Ned Snow Jr. married his wife Julie everyone agreed they were a match made in heaven. Ned was the son of a self-made millionaire who had been killed, along with his wife, Ned's mother, in a light plane crash, when Ned was seventeen. Ned Jr. inherited his father's vast business empire and was happy to let the Board of Directors look after the running of...

Die Mädchenschule für Jungen

by Redboom on Feb 12, 2020
Transsexual

In einem kleinen Café: Verträumt blick Leon in den großen Spiegel auf der anderen Seite des Raumes. Das Spiegelbild zeigt zwei Damen in den Enddreißigern, eine junge Dame Anfang zwanzig und ein hübsches Mädchen gerade achtzehn Jahre alt geworden. Zumindest sieht sie aus wie ein hübsches Mädchen: Eng anliegendes dunkelblaues Chiffonkleid mit locker über die S...

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Pink Panties

by DrLuverotica on Mar 27, 2019
Transgender & Crossdressers

It all started with a pair of pink panties. It was sometime after midnight when Jo arrived home from being on-call at the local hospital. She'd received a phone call several hours earlier about a bleeder and had to rush in. Recently her workload had become almost unbearable, but we needed the money so she was working her sexy curvaceous ass off. By the ti...

Valentine, Be Mine Ch. 04

by AngelCherysse on Sep 13, 2017
Transsexuals & Crossdressers

This is a work of fiction. Any similarity between the characters herein described and persons living or dead is purely coincidental. However, if the song excerpt seems familiar at all, I'll 'fess up to that. *** It wasn't a good day at work. Oh hell; it was the pits. I got to work on time – just. I was able to look reasonably presentable, too. It took a w...

The Wedding Ch. 06

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 6 -- Haberdashery, Hedonism and Highlights... We were into Patti's second week being overseas with Dean -- where by day they were supposedly riding around in expensive luxury cars yet by night? I had to figure, or it was safe to assume that is was more like Patti was riding Dean on their shared hotel room bed, stra...

The Ex's New Toy Pt. 02

by Urtoy2be on Sep 15, 2017
Fetish

Dearest Dana, I am writing to talk to you about things that I am unable to say to you face to face. I want to go back to when we were still married and come all the way up to current date. Maybe you will, hopefully, like what I have to say. Maybe we can come to an agreement/arrangement that could be mutually beneficial and satisfying to everyone involved....

Her Friend Came To Visit Ch. 02

by Dewmyne on Oct 13, 2020
Transgender & Crossdressers

When I woke up in the morning, Meg had left for work and Larry had gone to his meetings. I was laying naked except for my bra and one stocking and had dried cum all over me and a terrific headache. I stumbled to the kitchen for a big glass of water and Ibuprofen. Laying on the counter was a note saying "You had quite a night girl and we thought you needed th...

The Sexy Cuckold Couple Pt. 08

by cuckcpl4play on Sep 19, 2017
Fetish

As I drove home from work, I could not stop thinking about how our lives as slave and slut had escalated so quickly. What felt like days ago, I was a powerful executive about to obtain my new and even more respected position, but instead I was driving home soaked in my colleagues urine as the new office demoralized submissive. My wife, who was the love of...

Madam Molly Pt. 01

by corduroysissy on Feb 6, 2018
Transsexuals & Crossdressers

It all started in a chat-room, "Closet Sissyboys." Jesse had been spending a lot of time in chat-rooms in the six months following his divorce. He wasn't looking for love, he just liked to drink and have cybersex while jerking off with corduroy. Yes corduroy. Jesse had a corduroy fetish his whole life and now at the age of 36 it was stronger than ever. He...