Erotic Stories On Aastr By White Socks Sissy Boy Stories

367,635 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Mistress Chronicles Ch. 05

by MistressMtoyou on Sep 25, 2017
Fetish

Background: This story involves my on-line subject Nancy, who I introduced in Mistress Chronicles 4. We've had no in-person relationship. In fact, in all of our sessions Nancy has never actually seen me. I have sent him pictures that I have told him look similar to me, but never an actual photo. * By way of background, Nancy is a computer nerd. Brilliant...

Introduced to Black Dick

by Phantom8JMF on Sep 16, 2017
Transsexuals & Crossdressers

This is a story that is one of many in which it is time for me to share. In a nutshell, my name is Dean, my mother had a thing for Dean Martin it seems, but I go by Dina. I am a 26 year old white pre-op transsexual that has no interest in switching my outside in, if you know what I mean. I was born to a single mother, never knowing who my father was. Conside...

Wife in Control Ch. 03

by wifetoy on Sep 25, 2017
Fetish

This is the third chapter in the story of my submission to my wife for punishment for failure to control my orgasm. My full offer of punishment for my transgression is fully set out in the first chapter for your reference. Each part of this story is true and is told as it actually occurred. As with the previous chapters, my wife told me to let the readers kn...

House Rules Ch. 09

by EROTICbearscribe on Jan 22, 2020
Transgender & Crossdressers

AUTHOR'S NOTE: This story contains characters and references to events in two previous stories I have written: Just Across The Hall and PIXIE: Sissy Stripper. It is not necessary to have read these two story chains. This chapter of House Rules could stand on its own for entertainment purposes. If, however you want context, please read the other two stories f...

Panty Posers Ch. 04

by EROTICbearscribe on Sep 21, 2020
Transgender & Crossdressers

I must tell you of an experience Daphne and I had one Saturday night. I know, I know. You're dying to find out if I ever finally met Daddy. All good come things to those who wait. I really am a sissy tease. Aren't I? I think you'll enjoy this side trip though. *** It was a lazy Sunday morning. Daphne and I were sipping coffee and nibbling on some danis...

Taken by a Real Man

by gbr2004 on Sep 2, 2017
Fetish

Fictional work. Reading is at your option, sure you understand what this story is about. ***** Just got to my hotel room in LA. Nice room, 27th floor, good view, some floor to ceiling windows. My name is Steve, I'm 24, married, no kids, 5'8", 145. I am naturally pretty smooth and I'm in pretty good shape for my age with brown hair, longer than most, reachi...

Stevie's Journey

by gbr2004 on Oct 7, 2019
Fetish

I remember being so excited landing a position as a legal assistant at such a good law firm. My boss Mike Maddox seemed to be a great guy and I was looking forward to learning from him. I never imagined what it would be that I would learn from him. This job has changed so much and I can't even decide if I regret what has happened or if it was where my life w...

Mistress Chronicles Ch. 03

by MistressMtoyou on Sep 25, 2017
Fetish

Title: Decision time Background/update Even if you've been following the last couple of stories about my subject, Muffin, you might want to read this background as there are a few new points of note. Muffin is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professe...

Sharing

by thetoy on Sep 12, 2017
Fetish

My wife and I over the years had developed a relationship between Domina and submissive sissy that was utterly grounded in love. Indeed, that was the only thing that had allowed us to go as deeply into the perverse and bizarre as we had. She had a marvelous ability to anticipate just what I would be able to stretch to reach. I trusted her absolutely and deli...

A New Life Ch. 04

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

The man's Skype camera was still showing black, but I could hear him breathing heavily as he watched me pulling the chains that attached to the clamps on my nipples. I was pulling hard enough and steady enough to begin stretching my titties...as mistress requires me to call them. It was extremely painful as the clamps themselves were little more than metal t...