Shemale Cuck Stories

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'''CHAT'''

by Ssrd33 on May 10, 2019
Transsexual

Hi Jhon!, Hi Mike ... I answered lazily ... like all the days, my life had become very routine and repetitive, at home my wife does not serve me as a man or husband, I think I was dating I sneaked in with another man, but at this point in my life I did not care and the children made a mess everywhere. I wanted to escape this prison from which I felt trapped,...

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Swallowing My First Shemale

by Nitromethane on Oct 14, 2017
Transsexuals & Crossdressers

It's been a couple of years now that I've been intrigued by shemales, and though I've met up with a few I've met online, I've still not gone any further than some stroking or letting them blow me. I'm not sure what my hangup is, since I can't seem to stop watching these gorgeous girls on all the websites, but I'm still so nervous about taking that big first...

Cuckold & Netorare Shorts

by grimbous on May 17, 2019
Cheating Spouses

Hello Readers, What follows will be random Cuckold related short stories, set ups, or scenes. I get a lot of cuck related story ideas that I need an outlet for. This is simply a place for me to collect some of the ideas I get from time to time to see how they go over and gauge what is popular and what isn't. Don't expect lengthy or overly involved tales. Do...

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Cuckold Humiliation Story Time

by depositdutchess on Nov 8, 2017
BDSM

If only you were a real man and not a cuckold loser. Then maybe, just maybe someone would actually want to fuck you and I wouldn't have to tell you about my amazing sex every night, haha! Clearly an impossible reality. A cuck likes you gets to sit at home and circle jerk his cock to the thought of me getting fucked by a real man. Honestly, you could never fu...

Pam's Shemale Experience Ch. 07

by majicman21 on Aug 20, 2018
Transsexuals & Crossdressers

Author's Note: While this is quite obviously a continuation of Pam's Shemale Experience, it also follows 'Pam's Gangbang Experience' from the Group Sex category, 'Pam's Lesbian Experience' from the Lesbian Sex category, and 'Pam's Threesome Experience' from the Loving Wives category. Reading those three stories might not be necessary to enjoy this one, but i...

Holiday Inn, Rochester

by dsoul on Sep 15, 2017
Illustrated

Saturday, 12/01/13: 2:15 p.m. -- 8:34 p.m. I hooked up with my favorite couple in upstate Rochester once again. A good thing we found ourselves in Cuckoldspace.net. Ever since I deleted my former Yahoo mail box, I couldn't find a means of getting at them, but as luck would have it, we found ourselves again. The hubby, Robert, and I exchanged cell numbers an...

Derrick Explains Cuckolding Ch. 01

by funcouplelb on Nov 16, 2020
Interracial Love

I couldn't believe I did it. I hit send, and a 15 year old picture of my wife at our wedding and a one month old picture of her naked ass texted to Derrick. You would never have thought that ass belonged on a 43 year old... ********* One month earlier... My wife was a U.S.-born East Indian with a beautiful face and a thick ass. After two kids with extra e...

The Shemale Apocalypse Ch. 01

by cocklover1000 on Sep 15, 2017
Sci-Fi & Fantasy

The first place anyone really heard of it was large outbreaks in Thailand. No one knew what it was but the government played it off as a life choice via simple operation. But it was more then that. Minor cases were reported all over the world until 2011 the government in an effort to quell what they called an infection told the earth the truth about the wond...

Cuckolding: The Lifestyle Ch. 01

by Karenkay on Sep 16, 2017
Interracial Love

Madison sat reading the book that her husband ordered for her online a few weeks ago for the second time. She sat on the living room sofa dressed in black lingerie that Ted bought her along with her favorite fluffy slippers. The book was about the subject of cuckoldry. A subject that Madison just learned about during a discussion recently with her husband Te...

The Arms Of A Woman

by Samuelx on Sep 13, 2017
Transsexuals & Crossdressers

San Francisco. Mariah walked out of the Bordello. She was getting sick and tired of that place. Sick and tired of working endlessly to satisfy the depraved desires of those people. How she loathed them. Since she began working at the Bordello, she had seen a side of humanity she had never thought was possible. The worst imaginable side. She was just anoth...