Sissy Pills Stories

15,811 results
Orientation
Length
Source
Infinite Scroll

Hubby Makes My Deepest Fantasy Real

by Sexylover1979 on Feb 6, 2018
Interracial Love

Let me tell you a little about Rick and me; My name is Diane, I am forty-two years old, natural blonde, 5'2" and 49 kg. I have 32A breasts with very sensitive nipples, trimmed but not shaven, and have been married to Rick for twenty years. We have two children. Since our second child was born, Rick had the snip which allowed me to come off the birth control...

Moondust Hollow Ch. 05: Model

by LilithMoonstone on Mar 6, 2018
BDSM

[continued] Elsie fell into bed clutching to her chest the money Kevin had paid her. She'd counted it twice already, just to reassure herself it was all there: one hundred in soft, worn bills. He hadn't tried to stiff her. She was lucky, she knew; didn't lots of men try to avoid paying for sex work after they were finished? But Kevin had dealt honestly with...

Turning into Jane

by AnonymousPerv on Sep 5, 2018
Exhibitionist & Voyeur

I have this next story mapped out from top to bottom, a tale of a modest actress in an immodest film. I'll do part two and gauge reactions from there, on whether to pursue it to the end. I'm digging the way I'm building the characters, but be warned: it's a slow burn, and may turn some of you off. This first part is entirely softcore. Comments and criticis...

It's a Hard Hard Rain

by komaalrani on Nov 19, 2018
Erotic Couplings

When the evening is spread out against the sky Like a patient etherized upon a table... Dusk was dawning on glass panes of his window, smoke rubbing its muzzle, peeping from outside , streets following like tedious argument, ...every evening, it reminded him of Prufrock's love poem, more than 12 years has gone, him occupying this cabin, but today was to b...

Spring Break for Horny Toad

by EgmontGrigor2018 on Mar 21, 2018
Erotic Couplings

Smoothly confident, Lucas Hunter (18) joined the Spring Break exodus from his college in Denver, taking one of the lined-up buses to the airport to board a 2½ hour flight to LA. Aunt Laura. his mother's youngest sister, had arranged to meet the flight to take Lucas to her townhouse in Santa Monica. The student considered his 32-year-old aunt rather hot, d...

Wife Fucked Mom's Black Boyfriend

by Nojustice2 on Jul 3, 2018
Interracial Love

My wife Kit and I are both 30 years old. We have been married for five years and do not have any kids yet. Kit comes from a family of money. Her father's wealthy, and she grew up living in a wealthy suburb. Two years ago, Kit's mother and father went through a big divorce. Kit's mother's name is Beth. She's in her 50's but looks 40! She really takes care of...

Yours Lustfully Ch. 10

by Dontouchme on Dec 11, 2018
Erotic Couplings

Have you ever had two dreams come true on the same day? Rory was thanking his stars he could fuck the gorgeous Steffi on the backseat of his car. But the rain gods are offering him Maya too! Can this night get any more giving for Rory the driver? ... "Yes, ma'am," Rory answered the phone, as he turned into Steffi's neighborhood. It had been a quiet journey...

Won't Make It Easy Ch. 02

by VintageVixxxen on Sep 13, 2017
Interracial Love

*** After Nathan had left, neither of them having come to any sort of resolution on where they stood, Amara played back the message her answering machine took from earlier. 'Hi, this is Cardelia Nichols. I bought a skirt there on Wednesday---anyway, it doesn't seem to fit right. Just looking to exchange sizes....' Amara called back the number the custome...

Deep in the Night Ch. 03

by KimMarie on Sep 15, 2017
Romance

This is one chapter of a longer crime/romance story that is connected to the other parts. To fully appreciate the story, please start at Part 1 and read through. Thanks Part 3 Jordan Meets a Strange Beautiful Woman Around mid-afternoon, detectives Gary Matthews and Casey Samson had completed the database search. They now had a list of 120 men who fit into...

Wife Loves Two Men Ch. 02

by Vic5 on Sep 19, 2017
Loving Wives

Ann and Andy had entertained their very good friend, Jim, over the weekend. Jim had been so lonesome since his wife’s recent death. Two months before her death, the two couples jokingly agreed if one of the four died, the other couple would take care of the remaining spouse’s sexual needs. Ann and Andy felt obligated to comply. Jim was so thrilled to taste A...