Nifty Erotic Sissyboy Stories

128,608 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Sandra and Stevie Ch. 42

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the forty-second installment in a series entitled "Sandra and Stevie". If you have not read the previous forty-one 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 stro...

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

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...

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 Mistress to Obey Ch. 04

by gbr2004 on Sep 12, 2017
BDSM

This story includes female domination, forced fem, forced bi and discipline. Not your thing, please find a different story. I follow Mistress into the playroom wearing just the thigh high nylons and heels. I'm so hoping she is in a good mood after watching her have several orgasms with Terrell. Maybe she will be in a more playful mood, hopefully, thinki...

My Wife, My Boss, & I Ch. 02

by James Quiller on Sep 17, 2017
Loving Wives

After our short exchange of words, Candy got up and went to the bathroom to clean up, leaving me lying naked on the bed. I couldn’t think of anything to do at that point, so I cleaned up in the small bathroom downstairs, sat down to read a book and think about what had just happened. Despite the fact that I was thoroughly and erotically involved with what...

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."...

My Wife, My Boss, & I Ch. 03

by James Quiller on Sep 17, 2017
Loving Wives

The layoffs were announced on Friday morning and by the afternoon, three of the men I had started work with a year ago were gone forever. I think they were all quite surprised that I was still on the payroll. It certainly didn't make sense. I mean, what had I done to distinguish myself from them? But then, my wife had the given me an inside rail on the compe...

Sandra and Stevie Ch. 57

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the fifty-seventh installment in a series entitled "Sandra and Stevie". If you have not read the previous fifty-six 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 str...

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...