Cuckold Sissy Maid Stories

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Cuckoldry

by UpstaterNY on Sep 15, 2017
Loving Wives

Everything had been going so great. I was living with my girlfriend Kelli who I simply adored. We had so much fun together and a great sex life too. But about 2 months ago I noticed something wasn't right in the bedroom. Kelli's orgasms seemed to be less intense and less frequent. I asked her about it and she really didn't say much. Then last week I noticed...

Sissy Construction Worker & Friend Ch. 02

by toontessa on Sep 2, 2017
Fetish

After the crazy fling with Todd, I began to live more and more like a woman. I was amazed at the way I would look at certain men and have an intense desire to suck them off, or my asshole would suddenly feel empty. And the way those clothes felt on me was incredible. How do women walk around dressed like that without having an orgasm every five minutes? I fe...

Chad Joins the Bikers

by Randy4Sure on Aug 31, 2017
Group Sex

The man walked right past him with what looked like a baseball bat in his hands and wound up to hit another fellow who was a few feet away in the back of the head. Chad kicked out at the side of assailant's knee and felt it crack. The man fell to the floor and before he could do anything more than scream Chad was standing over him with his big boot planted...

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by John sixfooter on Sep 12, 2017
Group Sex

Last summer I read the paper almost every day, at least if I got to the paper before Susan threw it away. Susan, as you recall, is my lover, the sexiest creature I have ever seen. She works out at the gym every day, she runs, she swims, she bikes, kayaks, climbs, sky-dives, and, as a college nursing school graduate, works as a school nurse in my old high sch...

This Week; Better Than Last Week

by Cookie5 on Aug 18, 2017
Fetish

She opened the door smiling "hey!" Inviting me in, I walk into the hallway of the ground floor flat, kicking off my shoes, following her into the middle of her rented living room, stepping onto her thick white 'sheepskin' the place where we had very nice sex last week. "I won't have you walking about" she said; dropping at my feet for a few seconds to wrap...

Casual Kink - Jennifer Ch. 04

by ShortStoryteller on May 4, 2020
Exhibitionist & Voyeur

"...Burgundy?! ...Violet!? ...can't be white...no way! You never wear white! ...unless...!! Is it?" "No and nope!" I quip! "Ughh...Jenny! Just tell me already!" "You know the rules Sammy boy! If I tell ya...you lose! You lose you pay!" "Black?! No what am I sayin'! I know you hardly ever wear black! Ummm...Ok...Blue?!" He said almost pleading. "You need...

Ella Cucks Her Patient Ch. 06

by CuckFantasy69 on Mar 3, 2020
Exhibitionist & Voyeur

Continuation of chapter 5. "I didn't expect you to want me to chase you." I said startled trough the phone. "Haha, you really are clueless. I asked Ella before calling you, for permission." Emily said, I felt her trying to hold back her excitement. "Permission for what?" I asked realising that now Emily also will be a part of my secret. "To play with her...

Chinese - Watercolor - Lesson

by JRFreddy on Sep 14, 2020
Erotic Couplings

I was teaching watercolor at the local craft store. Most of my students were ladies between forty and eighty. I was twenty-six, tall and thin, and a walking erection. Not an obnoxious erection, but a conservative one, I hadn't been with anyone in over a year. And every patch of lady flesh was like soft butter smeared across hot bread. I hated my job, the art...

Sissy Powers Ch. 00 - Prologue

by ClarasBestFriend on Sep 29, 2020
Sci-Fi & Fantasy

Hi! My name is Leo Solo. I used to be a normal guy, just like you. Well, maybe not just like you. I have an 8" cock, for starters. And over the years, I've supplemented that with extensive study of Tantra and other sacred sex, learning how to elevate my lovemaking game to the level of the gods. My fiance, Clara, is very appreciative of my devotion to her ple...

Handyman Pt. 05

by lovedart54321 on Sep 28, 2020
Transgender & Crossdressers

I arrived at my hotel and got checked in. There was a bar downstairs in the hotel, so I thought it might be nice to have a drink before I went to bed. I had brought my Rachel clothes with me, at least, my lingerie and make up. I didn't really have a dress, but I had bought a shirt that definitely looked a bit girly, and with a pair of jeans, and my hair done...