Sissy Loser Stories

14,444 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Just Another Story

by neoview on Oct 15, 2017
Transsexuals & Crossdressers

Once upon a time... "Wait, wait, wait! We're not actually starting the story like this, are we?" Said the short fat kid in his mid-twenties. "I'm neither short nor fat." He said while swallowing his stomach and lifting himself on his toes. "I'm not doing any of that. STOP GIVING THE READERS FALSE INFORMATION!!" The angry non-short, non-fat kid yelled. "H...

A Visit to a Mistress

by fun4all6969 on Sep 19, 2017
Fetish

I have always craved humiliation ever since I was with a girl who humiliated me for my premature ejaculation and my small penis. I saw an ad online for a girl who loves submissive guys and we chatted back and forth for about 2 weeks before my business trip took me to where she lived. She told me it would be $250 for the domination session and that I had to p...

Rose Blossoms Ch. 02

by The_Technician on Sep 17, 2017
BDSM

= = = = = = = = = = = = = = = = = = = = Rose has disappointed her Master by losing a Greased Gladiator match at the club. This is the story of the aftermath of that match told more or less from Rose's perspective as she comes to grips with the Master's punishment of silence and then is slowly led into the truth of who she truly is and what her Master has d...

Hero Losing Himself

by lol159 on Jan 8, 2019
BDSM

Since Mark was a kid he dreamt about being a hero. He wanted to be someone who did the job on his own. He wanted to be the macho just like his hero The Jaguar Man. He was the proudest man about himself. Having been grown up in an orphanage after his parents were both killed by a robber, he knew best that no kid deserved to lose his family. That's the reason...

Cream Puff Ch. 03

by RubixStu on Mar 25, 2019
BDSM

I was naked except for my wig, my makeup, my stockings and my heels. I sat on Roger's lap, his erect cock deep inside my ass. He was watching a nature program. My legs were spread and his arm was wrapped around me while his hand lazily toyed with my little boy parts. He wasn't fucking me, he was simply impaling me, filling me with his masculinity while I rev...

Find the Cheerleader, Save the World

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It started with my brother Holt. A year younger than me he's...he's turned into a fucking cuck sissy faggot. I'm serious and I'm not just spouting off. Holt's always been a dense guy but this...he starts hanging with this loser from high school and I mean a loser. AV club, geek stuff, nothing in Holt's yearbook that said anything but loser, geek and loser...

3 AM: She Finally Comes Home

by siscuc on Sep 16, 2017
Fetish

I had nervously been awaiting my wife's return for the last two hours after finishing all my chores. The house was spotless and i had done all the washing and ironing she had left for me to do. I was ready to greet her at the doorway with a curtsey just as she had told me to. I was still wearing my new maids outfit, with fishnet stockings, lacy black pantie...

Forced To Get Dumped

by footcucknerd on Sep 16, 2017
Transsexuals & Crossdressers

James looked at himself in the mirror and shuddered, wiping another tear from his eye. He had to refrain from crying today, it would only make everything worse. Crying would ruin his make up and earn him a stern punishment before bed. Not to mention, his Mother would probably make good on her threats if he didn't perform perfectly today, and there was no way...

What am I

by AnalOnlySissy on Apr 29, 2025

Brittani: What do you want to watch Amber? Amber: Whatever you want to watch Brittani. I thought about it for a minute while Amber played on her phone. I walked over to the tv and bent over to grab the remote when I heard a camera flash. Still bent over, I turn to look at Amber and she took another picture. Amber: That one is sexy girl. Hahaha. Brittani: Wha...

Open in Reader

The Clothes Shop... Pt. 01

by Manndee on Apr 10, 2018
Transsexuals & Crossdressers

I looked at my watch, "Fuck it...nearly six, ...I bet they will be closed!" I parked the car and walked towards the shop. It was raining, it was cold, a typical January Saturday. "Bradley will fucking kill me if I forget my suit!" I smiled to myself. "The man's a dick for getting married anyway!" I walked towards the door, 'Fuck, is it open?' The lights we...