Chastity Cross Dressing Stories

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Orientation
Length
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Infinite Scroll

Acting Job Pt. 2

by Linda Jean on Sep 25, 2017
Loving Wives

Act 5: The Final Act After the last show I was sore again, I felt like a used sex toy. Jason (Ben) had only climaxed four times all night, but he was hard every time and he fucked me hard when he was on top and I fucked him as fast and as hard as I possibly could when I was on top. It took some time to get past all the stagehands and rest of the cast and we...

Sixth Period Trig Pt. 07

by notemale on Sep 13, 2017
Erotic Couplings

Thank you Andrea4328 for editing this story. Her help is very much appreciated. I'd like to apologize for the error I made in chapter 6. I accidently copied once but pasted twice. It was a stupid error and will never happen again. I'd like to apologize for the error I made in chapter 6. I accidently copied once but pasted twice. It was a stupid error and w...

More Than Friendship Material Pt. 03

by Story_Spinner on Sep 25, 2017
Romance

Chapter 15 Liz woke up rested and refreshed, but the memory of her first kiss with Todd lingered. She occasionally had that dream. How sweet he had been while she was so upset and in the end, he'd kissed her sweetly. The sort of kiss that made girls want to melt into a guys arms and cock a leg up. Yeah...that kind of kiss. It hadn't even been porn star slop...

The Wedding That Never Happened

by TheKittenCC on Jun 4, 2019
BDSM

Kassandra was sitting at the vanity table in her dressing room. Her wedding was just a few hours away, and soon her last name would be changed forever. Her bridesmaids were already on their way to set up. So she sat alone in a white-laced bra that were barely holding her DDD tits. Nearly pouring out of the low cut, a lace garter that hugged her hips and cla...

Explore the Inner Woman In You

by Tomsparty on Sep 14, 2017
Transsexuals & Crossdressers

I fancied the arse off a girl at school called Sharon. The problem was most of my year did. She was beautiful with long blonde hair, willowy legs, a butt to die for and stunning pert tits. She was way out of my league but quite amazingly we did get on and began to make slow but steady headway. My dizzy ambition was to ask her to the end of year college dance...

Taken in by Demons Ch. 02

by Autarchic4Ever on Sep 14, 2017
Group Sex

Earlier I described how I came to be a club girl for the Demons Motorcycle Club. I moved into their club house and became one of them, giving up what few items I owned in the process. I eventually stopped talking with my family since every time I called I was drunk or stoned and I really didn't have much in common with them any more. I had a new family. My p...

Pretty in Pink Ch. 02

by jealouscuck on Sep 18, 2017
Transsexuals & Crossdressers

I could not believe my good fortune. Not only had Jessica accepted my crossdressing, she had changed her whole attitude toward my fetish. We talked about it afterwards and she told me she was continuing to research the topic. In the meantime she made me promise that we would have no more secrets between us. Over time, she got me to tell her the full extent o...

Email Cuckold Ch. 03

by illicit_writer on Sep 16, 2017
Fetish

Please remember to vote, if you enjoyed the story. And I always appreciate comments both positive and negative. Though trollish, anonymous comments will be deleted. *** *** *** *** *** Karen pulled into her driveway in high spirits. Tonight was girls night out and her whole body had been on the edge of excitement all day because of it. For the past few...

Changing Direction Ch. 02

by deliciousthoughts on Sep 12, 2017
Novels and Novellas

Chapter Two: The Audition Ella's mobile phone buzzed once on the counter of her bathroom, making her jump a little as she stepped out from the shower. She grasped it excitedly, checking the text message as she wrapped the fluffy white towel around her body. Good luck, darling. Show Bruno how much you want this. See you soon. Marilyn x She had spoken to...

Charlie Ch. 01-02

by sweetkarolina on Sep 15, 2017
BDSM

1 There was a persistent knocking, tearing me from my doze. As I awoke the knocking continued. I called out, asking who was there. "My name is Justine Zamora. I'm looking for Charlie Baines. Do I have the right room?" asked the voice on the other side of the door, timidly. "Justine! Oh my God! Let me get dressed! Hold on!" I hollered and slipped quickly...