Crossdressing Dare Stories

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Orientation
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Infinite Scroll

On My Knees for Her

by albertscwriter on Jan 22, 2020
Erotic Couplings

Until 6 months ago, I would tell you that I had it made. I had a great job, an active dating life, a varied sex life, and nothing in front of me but blue sky. Now all I got in front of me is my boss's cunt. Serving my mistress is, somehow, more satisfying than my old life. I guess I should go back to the beginning. I work at DeClarke enterprises. My job wa...

My First and Last(?) Fling in XXX Theatre

by Sharksgo on Jan 22, 2020
Exhibitionist & Voyeur

It had been seven months since my husband died and he had been invalid for four years before that following prostate cancer. He was a loving partner and encouraged my orgasms with wonderful toys and dildos. However, once his cock could no longer feed my appetite, I missed the explosion and feel of real intimacy and, candidly, exploding under the lust of a ma...

Restructuring Pt. 02

by cathynylons on Jan 27, 2020
Transgender & Crossdressers

During the last three weeks Meg bought me several different outfits and some sexy new lingerie including a garter belt and very sheer, very expensive nylon stockings. I now have several pairs of pumps and sandals, all with stiletto heels. She had my room painted pink and installed a vanity and stocked it with all the best make-up and cosmetics. I was basical...

Just Your Average Workplace Pt. 02

by mwilliamm on Jan 28, 2020
Group Sex

My heart pounded wildly. I mean, this was the woman who had, not even a half hour ago, made me cum all over her face. And then, my boss. I was at a loss for words which is ironic, I know, but there you have it. This was way out of my comfort zone, but the sight of Candice and her full, juicy breasts made me think twice. I bit my bottom lip, contemplating the...

My Cheating Husband Ch. 03

by supplestrawberry on Apr 27, 2020
Loving Wives

The morning was tense for Brad and me. I was secretly looking up exercises to burn calories fast, how to properly diet and portion my food, helpful tips for weight loss. Meanwhile, my husband was glaring at me staring at my phone. "So," he huffs, "What, uh... What are you doing on your phone there?" he questioned, offended. Is he jealous of my phone or somet...

The Ball Field

by RedExploring on Apr 27, 2020
BDSM

Rrrrrrring. My body instantly reacted when I saw his name flash on the caller id. My pussy jumped; my breath caught in my throat. It's Steve, my boyfriend, my Dom. Although it's been many months since Steve and I entered into a D/s relationship, I still feel goose bumps every time I think of him. Every day is an adventure with his devilish charm and creative...

My Best Friend's Wedding

by SlutProblems on Jul 3, 2019
Group Sex

Natasha was my best friend but going back, things had always been bumpy in our friendship. We had met in college and were thrown together as roommates our Freshman year. We bonded over boys and ice cream and it seemed like we would be friends forever. After college, Natasha went to graduate school for international business. She was also studying Italian, Fr...

Split Slave Ch. 04: Trance

by skaetlett on Jul 30, 2019
BDSM

Author's Note: This story contains adult content. Do not read if you are under the age of 18. Additionally, this is not an accurate representation of slavery or non-consensual sex at all, as it exists in a fantasy setting. Non-consensual sex or sexual acts and sex slavery in real life is highly immoral and illegal. All characters in this story are above the...

Office Power Politics Ch. 03

by PaulHub on Aug 6, 2019
BDSM

She was bored. Her team had performed well enough that no one had suspected she was a one-man band but not well enough to get the plaudits she craved. Part of the problem had been her other cravings, mostly for the cock attached to her former subordinate-turned-equal. He'd gotten a little too big for his boots recently as men are wont to do when you give t...

Joy's Story

by PKenny5860 on Oct 22, 2019
Loving Wives

I felt that the reader would want to hear from Joy for some insight into her motivations and role in the events that led to the destruction of her marriage and family. ***** Dearest Peter, As I sat to put words to paper, I struggled time and again to know what to say and how to say it in a manner that doesn't sound humiliating or come across as condescen...