Sissyboy Stories

563 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Truth or Dare with Sisters

by sissyboy_stacey on Sep 18, 2017
Fetish

Ringgggggg... Ringgggggg... "Sean, can you get that?" "Hello? Hey Gina... what's wrong? Ok, hold on, I'll get her..." "Katie, your sister is on the phone. She seems really upset and said she needs to talk with you." When I heard my wife Katie pick up the phone in our bedroom, I pretended to hang up, but instead, I put my phone on mute so that I could eav...

The Cuckold Ch. 02

by sissyboycamille on Sep 13, 2017
Toys & Masturbation

Since that strange evening the sex with my wife had become very intense. We had gone from having sex once every month or two to a few times a week. She seemed to have discovered a new found interest in sex. Everything turned her on. A few times she came home very late and had me on my knees in the living room licking her pussy for ages, her pussy smelling st...

The Cuckold Ch. 01

by sissyboycamille on Sep 13, 2017
Toys & Masturbation

I sat down and finally relaxed. After a hard day at work it was good to put my feet up. I flicked through the channels on the TV and left it on the news. My wife had made a lovely dinner and was now upstairs in the shower. I took another sip of my wine and looked at the glass for moment. This evening could end very nicely if I played my cards right. I went i...

The Cuckold Ch. 03

by sissyboycamille on Sep 13, 2017
Interracial Love

Things had changed at home. My wife had been promoted at work. Since the children had left home she had been able to dedicate more time to work and it had paid off. She was dressing more professionally and was often coming home late. She had changed too, as she now had less time outside of work she had developed a no nonsense attitude. We still got the chanc...

A Look Into My Mind: Uncle Sissyboy Ch. 02

by rickiee_2002 on Sep 25, 2017
Fetish

I was sitting in my office working. It was very quiet and I was getting a lot of paperwork done. My intercom went off ... "Rich, your sister in law and niece are here. They are asking to see you. Should I send them back," Liz, my secretary asked. My heart began to race and my cock began to stir. "Uh, yea, sure ... Liz ... tell them to come right back here."...

A Look Into My Mind: Uncle Sissyboy Ch. 05

by rickiee_2002 on Aug 31, 2017
Fetish

Lori and Lauren led me into the bathroom. They were giggling and talking to each other so quietly, that I could not figure out what they were saying. My wife, Serena yelled to them as they walked me to the bathroom. "Girls, I bought a liquid depilatory at the drug store. It's in my purse." "We can spread the liquid all over his body and watch the hair just...

A Look Into My Mind: Uncle Sissyboy Ch. 04

by rickiee_2002 on Sep 25, 2017
Fetish

I couldn't believe it ... I was finally going to be able to have sex with my niece. She is so gorgeous and sexy. She is everything I could want. Young, thin, tall, beautiful, full pubic busy, sexy ... WOW. I leaned forward and touched the tip of my tongue to her super wet pubic bush and then the tender small lips of her pussy. There was a white liquid oozin...

A Look Into My Mind: Uncle Sissyboy Ch. 03

by rickiee_2002 on Sep 25, 2017
Fetish

Shortly after I drifted off to sleep, I was awakened by the feeling of something hot and wet hit my body. I looked up and noticed one of the male subbies had just squirted his cum on my body. My negligee had ridden up and the cum was on my side and dripping off my side and onto my stomach. I looked up at him and he just got up and walked out of the room. Lau...

A Look Into My Mind: Uncle Sissyboy

by rickiee_2002 on Sep 25, 2017
Fetish

The telephone was ringing and the voice on the other end was my sister-in-law, Arlene. She asked me, in her usual cold manner, if she could speak to my wife. "Hi Rich, can I please talk to Debbie". There was something about her that I could never really stand, but she was my wife's sister, so I always kept a smile on my face when I was around her. "Arlene, c...

Sucker Boys

by TopsyBFox on Sep 13, 2017
BDSM

We meet in a bar, me, my best sissyboy painslut & you. We are all dressed in everyday office attire; you boys look so professional in your suits. I have on a tight white blouse which strains a little at the buttons, the sheer lace of my bra clearly showing through; a straight black skirt, net stockings & heeled patent black pumps. There are other such groups...