Gay Crossdressing Bondage Stories

609 results
Orientation
Length
Source
Infinite Scroll

Cock-Sucker Tales: The Random Rod 02

by tristantrotsky on Sep 14, 2017
Gay Male

We proudly present the second part of the first in a series of unjustly neglected underground classics of erotica, revived and reinterpreted for your entertainment and pleasure by Tristan Trotsky, a noted dilettante of decadent literature. --- 0 --- The earnest literary critic can but conjecture about the state of mind of the author of the sad and perverse...

Winning the Blonde Goddess Ch. 08

by spankednaked on Jan 21, 2020
Gay Male

My name is Scott. I'm twenty-two years old, I'm a professional ballet dancer with the Chandler Theatre. I've had fourteen years of ballet training, I have the coordination, agility and the stage presence that a dancer needs to be a success. I also do nude modeling and sexually explicit videos. At some point during my career at the Chandler Theatre, one of...

Winning the Blonde Goddess Ch. 06

by spankednaked on Dec 9, 2019
Gay Male

It was Sunday morning. I had just showered and toweled myself off. I walked into my bedroom and was about to get dressed when I discovered that I had a text message from Darya on my phone. It said simply, "Meet me in Nari's apartment. I will tell you about test # 9." Darya had promised that I could be her boyfriend if I passed twelve difficult tests of her...

Descent

by EroticMonster on Aug 18, 2017
Gay Male

The sequel to Contraction. ***** "Your future is with me now." With those six words I became Cody's boyfriend and he became my saviour. Jenny and I were over. Two years of an incredible sexual journey had ended with threats and recrimination. I had been thrown out of the house I had shared with her for almost the entire relationship, and a cloud of humil...

All Fools' Day Foolery

by sr71plt on Sep 14, 2017
Gay Male

[For an earlier story in the NYPD vice detective Mike Kavanagh series, see "Inevitable Case."] Mike Kavanagh stood at the French balcony window of his "seen better times" hotel on Canal Street, looking at the festival parade units forming below him, and then beyond to the western edge of the French Quarter. He was lucky to have found a residence hotel this...

Wild Flower Ch. 09

by vanalas on Jan 30, 2018
Gay Male

Comments, critiques and tips are welcome. Hello and welcome to the ninth chapter of this interesting story. Before diving into this story, I would like to say that I love you guys a lot. Thank you so much for your support and love. I just hope this chapter will be really interesting to you guys. Don't forget to drop your comments and rate this story. Happy...

The Exploits of Cockslut Kelly 01

by CSK on Aug 29, 2017
Gay Male

Hello my fellow perverts and welcome to my very first story on Literotica (but certainly not my last. My little perverted mind has so many lovely stories and fantasies to share with you). I love this site because we can share our deepest, darkest and most depraved fantasies (and past experiences) with other likeminded individuals. My stories will most likely...

Failing Upward Ch. 04

by el_wing on Sep 14, 2017
Gay Male

Chapter 4: Hidden Hills I leaned over. I thought of kissing him. I did. But Sid turned his mouth away. "For years you've avoided this moment," Sid said. "Now, it's here, and I don't want it. You know why? Not just because I promised I wouldn't get into your pants, or because you drank too many rum and cokes, or because you've just been through a traumat...

Loren Ch. 06

by jayjayk on Sep 14, 2017
Gay Male

"Thank you." Mac said the next morning smiling across the kitchen table at Loren. Loren didn't even have to ask why he was thanking him - he knew why and simply smiled back. "Are you ready for this morning?" Loren gave Mac a confused look wondering what he meant until if dawned on him that he was talking about the impending visitors. "I guess so. Are you su...

Cock-Sucker: The Rake's Progress 03

by tristantrotsky on Aug 30, 2017
Gay Male

Part 3: In which I fall in lust, and face the consequences... At last I'm free of Luis. I no longer need an 'agent'. But I've learned enough from my time as a 'Midnight Cowboy' to go solo. I look at myself naked in the mirror, pose and preen, Wow, I look good, so hot. Look at me, look at me, the delicious curve of my arse, peach-round and just as succulent,...