Milf Sissy Stories

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"Sissified": 12 Days of Sissy-mas

by silkstockingslover on Jan 7, 2019
Transgender & Crossdressers

Summary: Straight man is turned into a submissive sissy by.... Note 1: This is my 400th story release. To mark the occasion, I thought I would try something longer... mixing many of my themes into one long, complex story. Thus be warned that with over 40,000 words, this story is a marathon not a sprint, and it includes a variety of themes including: cross d...

My Mom Versus My Bully

by blizzardy12 on Sep 19, 2017
Mature

All characters are 18 and over. I knew Mom would overreact when she saw the black eye Seth had given me at the skate park. Being a scrawny and short guy, I got picked on and beaten up a lot. Mom was always the first one to really make me feel inadequate though. I knew how it embarrassed her that her pathetic son was too much of a pussy to defend himself....

Hiring a Well Hung Bull

by Mag58 on Sep 14, 2017
Erotic Couplings

Until a year ago I would never have dreamt that I could ever be cuckolded; let alone actually hiring the Bull for my wife. As a young man I had many lovers; all ages, sizes and classes then I met my wife to be in 1997 and fell madly in love. I was 32 and she 24 at the time; and when we had sex sparks would literally fly. We did absolutely everything two...

Las Chicanas

by AnnabelleRaven on Sep 17, 2017
Non-Erotic

17 year old Alicia Garza lay cradled in the arms of her new boyfriend Tony Torres. Since Alicia and her mom had moved across town before the school year, she quickly became one of the hottest young coeds at the affluent Palm River High School, and she was very interesting in finding a guy that would give her attention, affection, and comfort. Palm River was...

Futanari World Transmigration Ch. 02

by Gregory8 on Feb 3, 2020
Transgender & Crossdressers

**Author's note: All characters in this story are over the age of eighteen. This story contains scenes of incest or incest content (Kind of but kind of not, as the person gets transported to another world so the people in it aren't really related to him.)** *** A dribble of jizz run down his chin, forming a small droplet that fell down to the ground. Antho...

HotWife Iris Does Young Bros Again

by Aynsley on Sep 13, 2017
Loving Wives

As I gazed across the hotel room that we had just checked into, I caught an air of flirtation from my voluptuous MILF wife, Iris. If you caught our first story, you know that I had surprised Iris, by having her new young lover, Jack (28yo), bring his younger, virgin brother Jason (22yo), to our last 'date'. That night went really well, and Iris had asked me...

Fuck the MILF Slut

by RiaBella69 on Sep 13, 2017
Group Sex

Maria is a slut, she knows this, and she never hid that fact. For thirteen years she has been shackled in a loveless relationship. Perhaps loveless is not the word. Perhaps the correct description is lust-less. Her ex-husband at first did care for her, at first, he would buy her chocolates on holidays, and talk to her sweetly, call her things like “baby” or...

MILF Summer

by NobodyImportant on Aug 4, 2018
MILF

It's summer but there is definitely something in store for you from spring break. Even though you have a college degree in [use fantasy], it's become pretty pointless since your wives are taking in large amounts of money from their divorce settlement, investing it wisely, and making it so you never have to work a day in your life. All of you have come to liv...

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Dinner Date With a MILF

by NobodyImportant on Jun 20, 2015
MILF

Background: After winning a bet with an entity in a dream, you are able to mind control whomever you please. Characters: Mrs. Busty: A 5'4" orange haired milf with H-cup titties, a luscious ass, and the best blowjob lips you've ever seen. After thoroughly dominating her, she becomes your 24 hour fucktoy. Mrs. Done: A 5'3''asian MILF, in her thirties, ha...

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Mind Over Management Ch. 04

by SEVERUSMAX on Sep 15, 2017
Group Sex

I was balls deep inside Cheryl, with Jess sucking my balls and Jamie rimming Cheryl's ass, when Jen came through the door from work and immediately started to disrobe. Before I knew it, Jen's cunt was in Cheryl's face, and the blonde went to town on her snatch, licking away like nobody's business. We fucked for several more minutes, while Cheryl sucked Jen's...