Milf Sissy Stories

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Your mom is a MILF - The Story Archive

on Apr 10, 2020
MILF

milf Mom I'd Like to Fuck, or Mature I'd Like to Fuck A MILF is any woman with children who has men that want to have sexual intercourse with her. The term is also sometimes used to describe women above a certain aged (30 or 40+) who are not mothers themselves, but are deemed to be sexually attractive, and also have men that would like to partake in sexual...

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The Dominatrix Order Pt. 02 Ch. 03 - Romance

by Jwwsmith on Feb 12, 2019
Transgender & Crossdressers

The next afternoon, Johanna invited many of the Goddesses of the Council over for lunch. Much to everyone's surprise, Representative Pencalia arrived as an uninvited guest. Pomona prepared a fine meal as the Goddesses deliberated over various issues. Pomona was very accommodating to the guests, serving them tea and salad and shrimp. She even placed cloth nap...

Inga Swenson Ch. 03

by JoMaddox on Sep 24, 2019
Interracial Love

Inga suddenly had second thoughts about what she had just done. But a part of her wanted the street thug and drug dealer to at least come over to her house. Since that day at the party, the Swedish milf had thought about what it would have been like if she had somehow ended up with Tone and his friends instead of with Marcus Jefferson. She could still rememb...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

Another Football Season...

by R_U_Romantic on Sep 14, 2017
Erotic Couplings

It's the middle of August and already my son of a bitch husband has started his annual pilgrimage to his "man cave" to watch football. It doesn't matter if it's college or the pros Barry just can't get enough. From now until the middle of January I'll be a football widow and he'll forget that I even exist. Pre season means Thursday night games of the loc...

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

My Very Own MILF

by Bakeboss on Sep 14, 2017
Mature

After being married to Irene for over forty years, I couldn't imagine her having any secrets from me but I sure found out I was wrong. Our boss wanted to get an early start on the long Labor Day weekend so he closed our office before noon. I came home to surprise my wife and to enjoy our long weekend together. I walked into our bedroom and immediately heard...

Sissy and Paul

by slowhand1234 on Apr 22, 2019
Exhibitionist & Voyeur

Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married sev...

Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...

Sissy Boy Secretary Ch. 07

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine and Tammy had been friends before the unfortunate divorce and still now maintained a good friendship. After all, it was Elaine that helped her get a job as an executive secretary during all of her school breaks, including throughout the summer break. Tammy had known that the company Elaine got her the job at was also Elaine's biggest competitor in the...