Sissyboy Stories

140 results
Orientation
Length
Source
Infinite Scroll

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...

Sandra and Stevie Ch. 21

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the twenty-first installment in a series entitled "Sandra and Stevie". If you have not read the previous twenty episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I strongl...

Sandra and Stevie Ch. 43

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the forty-third installment in a series entitled "Sandra and Stevie". If you have not read the previous forty-two episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I stron...

P.A. for a Day

by susanxdresser on Sep 13, 2017
Transsexuals & Crossdressers

The gates swung closed behind Charles as he slowly drove his car up the sweeping driveway. Even though he was looking forward to the erotic delights which were in store for him that day, the cares of the world seemed to weigh heavily on his shoulders. As he drove up to the garage he mused about the dullness of the life which seemed to stretch endlessly befo...

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. 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...

Mistress Kate Pt. 01

by corduroysissy on Feb 7, 2018
Transsexuals & Crossdressers

L. Jordan Bains wasn't sure of what to expect when he stepped into the large wood paneled office, but he knew whatever it was it wouldn't be good. He was in a lot of trouble, the Leprechaun wasn't known for having a forgiving nature. Jordan had never seen him, he only knew him by reputation, when you hung around the poker tables of Waller City you heard all...

A Mistress to Obey Ch. 05

by gbr2004 on Sep 12, 2017
BDSM

Continuation of this story that involves forced fem, forced bi, discipline, humiliation and submission. Not your thing, move on to another story. * We got back to her house and she opened the car door and let me out. I followed her into the house and she went and set down in her chair and I just stood there in front of her. 'Present sissy boy.' I droppe...

Jennifer Monroe & the Ladies Ch. 01

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Jennifer Monroe & the Ladies -- Chapter one Jennifer held Debbie's hand as she led him down the stairs and into the finished basement. It was a large single room with a sofa, a few comfy chairs and a queen-sized bed at the far end. Seated on the sofa and chairs were five ladies, all of them dressed in corduroy outfits. Jennifer ignored them as she whisk...

Sandra and Stevie Ch. 44

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the forty-fourth installment in a series entitled "Sandra and Stevie". If you have not read the previous forty-three episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I st...