Cuckold Sissy Stories

12,909 results
Orientation
Length
Source
Infinite Scroll

Silken Panties For Me

by Dayguy on Sep 16, 2017
Transsexuals & Crossdressers

It would be beneficial to read the previous chapters of this seemingly endless saga for it to make the most sense to you. Well, I guess that word of my and my talent was spreading, discreetly and confidentially, but spreading none the less. It was sitting at my desk enjoying the beginning of a wonderful Wednesday when my private office phone line rang. On...

Night Out at the Pinky Finger Ch. 04

by Cap_N_PieSissy on Sep 16, 2017
Transsexuals & Crossdressers

Sometime later they pulled apart again and nuzzled each other. He kissed her little nose and trailed his lips down her neck, sucking gently on the skin of her shoulder. She nibbled on his ear lobe, sucking and flicking it, which he found deliciously erotic. They trailed off, content in each other's arms until Ken stirred and asked, "Well, what else can we d...

Admissions

by pinkpony2 on Sep 16, 2017
Transsexuals & Crossdressers

I closed my eyes. I knew what I wanted to say, but was unsure I could get the words out. The silence on the other end of the phone began to become chilling. Finally, incredibly patronizing, "You wanted to make another tape of me dominating the hell out of you, didn't you Steven!" "Well, I..." my face grew red, my pride pretty much shot, dying to give in to...

Polish Maid

by johnnysdirtysecret on Sep 19, 2017
Transsexuals & Crossdressers

'You want to get tips,' I explained to Marek, our Polish cleaner, 'You should be more a maid more like her.' Across the street was a girl of about 19, dressed in a fancy dress French maid's costume stumbling home, presumably from a party the night before. She was dressed in a tiny black dress, low cut with a short skirt, white apron, stockings and heels. M...

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...

Big Dick Advertisement

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...