Sissy Wedding Stories

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Infinite Scroll

Shango's Hot Time in Philly

by dsoul on Sep 16, 2017
Interracial Love

The taxi deposited me in front of this quaint and simple suburban home. It was a hot Saturday, the sun was out in the sky with no prediction of rain for the next three days. I haven't been in Philadelphia before, but I was there on an assignment. Some bitch-ass white hubby whom I'd been communicating with online finally caught my attention and begged me to c...

The Virgin Tranny & the Bride Ch. 02

by yano on Sep 25, 2017
Transsexuals & Crossdressers

This is part two of a confession related to me by my transvestite friend Roberta, and like the first part, is so sexy without any further elaboration by me. Having seen some of the photographs, I can only say that she strays very little from the truth. Meantime I am trying to convince her to let me publish a few on the Internet. Watch this space. Exactly tw...

A Twisted Wedding Night

by FrostShard on Sep 18, 2017
BDSM

"Did you really think that you were going to consummate this marriage, my dear?" giggled my newlywed wife. "I know we're married now, honey, but that doesn't mean I'm a different person now. I still have the same needs." Alicia was absolutely gorgeous in her bridal wear. The very picture of innocence. If people only knew. "But, Alicia, it's our wedding nig...

The Pantysissy Diaries Ch. 01

by JPantyboyVSL on Sep 2, 2017
Fetish

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. ***** Jay was on his way back to New York from a weeklong work conference in Chicago. He decided to take Amtrak back to NYC. He got on the train in Chicago and noticed a hot young blonde woman in her 20s s...

Tatum's Friend, the Bully

by justincbenedict on Jul 31, 2019
BDSM

Pearson checked the lip gloss in the mirror. He looked perfect. Pearson knew he really didn't look like a woman, just a pudgy little man, chubbiness poking out of the hideous pink nightgown that he and Tatum had purchased through the tranny site. But he liked this-he would go into the bedroom, and Tatum, gorgeous in her own lingerie, would make him suck her...

Eve Quest Pt. 04

by JJ Neal on Sep 12, 2017
Transsexuals & Crossdressers

Chapter 16 Monday morning I was told to wear my red panties, bra and ribbon; my white collar, bracelets and heels and a red sleeveless dress. Sheila and Jenny ate breakfast, got dressed and loaded me in the car. They dropped me off in front of the beauty parlor and Jenny said. "If Hilda finishes today. You should give her a tip." I went inside with that d...

Double Wedding

by Tomsparty on Sep 18, 2017
Transsexuals & Crossdressers

I was about to marry my childhood sweetheart Paula Rother. I loved her and she loved me but it hadn't been straightforward. After school she went to Manchester University while I went to work at a local accountants as a lowly paid junior clerk. She said we where inseparable but during the two years she was away she met Graham. I was heart broken and knew I w...

The Sexy Cuckold Couple Pt. 07

by cuckcpl4play on Sep 19, 2017
Loving Wives

The Day of the Ceremony is Finally Here Part 7 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 demoral...

Black Cop's Stress Relief

by puzziboi on Jan 20, 2020
Transgender & Crossdressers

"We think you're doing a hell of a job, Corporal," the bronze-skinned police lieutenant explained. "But at this time we're going in a different direction." "Alright. Thanks for letting me know, Lew," replied Christopher Patterson with a fake smile. "Is the candidate internal or external?" "External," the supervisor revealed. "Alright. I'm kinda tired," Cp...

Cream Puff Ch. 03

by RubixStu on Mar 25, 2019
BDSM

I was naked except for my wig, my makeup, my stockings and my heels. I sat on Roger's lap, his erect cock deep inside my ass. He was watching a nature program. My legs were spread and his arm was wrapped around me while his hand lazily toyed with my little boy parts. He wasn't fucking me, he was simply impaling me, filling me with his masculinity while I rev...