Milf Sissy Stories

11,621 results
Orientation
Length
Source
Infinite Scroll

Tales of Seth and Travis Pt. 01

by pantywriter on Sep 16, 2017
Transsexuals & Crossdressers

The early June morning dawned misty but cloudless; it was forecasted to be one of those absolutely perfect late spring days with dry air, sunny skies and temperatures in the seventies. Nothing could be better. Whether it was the weather, or just his state of mind, but Seth woke in a wonderful mood. He sang quietly to himself as he made his bed, tidied up h...

Our Conquerors, Our Concubines

by Shendude on Dec 20, 2010
Science Fiction

Millenia ago, an alien race created the Ghirabo, telepathic shapeshifters intended to serve as sexual playthings, able to read their owners' minds and assume a form and personality that will fulfill their owners' desires. But the Ghirabo's Creators were wiped out, leaving them to fend for themselves. In time, the Ghirabo have become a powerful race, creating...

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Sissification Fad

by NaughtyEricka on Sep 30, 2019
Transsexual

Sissification hadn’t just become some sexual fad overnight it had actually become a practical way of life for numerous families across the country. The act of sissifying a male family member and using them as a family sex toy and also as an alternate source of income had started in China and Japan but had quickly spread to and across the US. Now 3 years late...

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Neighbourhood Sissy

by Abusedbyfuta on Feb 7, 2019
Fetish

Your a young man in his late teens. Average build, average height, brown hair, green eyes. You know the type never stood out in a crowd for your good looks but never scared children when you went to the store either. Having just finished high school ou decide to start doing odd jobs around the neighbourhood to raise some money. Maybe it was college, maybe it...

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Mrs C

by pantywriter on Sep 11, 2017
Mature

This is a lengthy story covering many different subjects. Be warned that some fetish concepts are explored. ***** When Mr. Caruso next door unexpectedly passed away, I attended the funeral along with my parents. I think that the entire neighborhood turned out. The Carusos were popular, friendly people and his sudden passing shook everyone. It happened in...

The twisted DM

by Nobody567 on Nov 21, 2019
Fantasy

Authors notes: please like and comment my stuff I desperately desire your feedback and approval. I am new at this and recently redid the intro hope you like it. A being beyond space and time whose goal is to torture, torment, pleasure and change his players in ways that you cannot begin to fathom for his entertainment and pleasure. He sits at multiple tables...

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Spicy Story

by TexanBelgianCutie on Jul 17, 2019
Transsexual

Family Kyle had wildly mixed feelings when he saw his mom walking towards him. He kept his feelings to himself however and forced a big smile to welcome her back from the SpringWood Adult Mental Hospice. He had not seen her since he was child, yet he was glad to see she looked healthy and happy. “Hey Sara”, he grimaced, “How are you? Sara had spent the last...

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Fallout: Sex Adventures

by kin1041 on Apr 28, 2017
Fan Fiction

Let's start with selecting the game.What's next? Fallout 3 Fallout: New Vegas Fallout 4 Fallout 76 Before the fallout What's next? Fallout 3 Fallout: New Vegas Fallout 4 Fallout 76 Before the fallout...

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One Sissy's Night

by Devient_Mind on Sep 16, 2017
Transsexuals & Crossdressers

As I walked out of the restroom of the suite you rented us at the Ritz Carlton, I felt nervous... I looked incredible, long blonde wig fixed perfectly ruby red lips to match my nails, long eyelashes and makeup done perfectly... My tight black dress plunging down my back and flowing to the floor. 4" stiletto heels... Thigh highs garter and they sexiest black...

Sex therapist

by qaz on Sep 1, 2016
Miscellaneous

Who do we follow?What's next? A boy A girl What's next? A boy A girl...

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