Gay Sissy Boi Stories

901 results
Orientation
Length
Source
Infinite Scroll

Hot Chat with Daddy Top

by BartSavagewood on Aug 31, 2017
Gay Male

Transcript of a hot IM chat I had with a top describing to him my first time: *************************** Dad: tell me about your first time.. with David the doctor Boi: well this was about what 10 years ago Boi: I was 22 Boi: and living with my gf at the time Boi: things were not going well Dad: okay Boi: so we were breaking up and needed to sublet...

Jungle Fever Ch. 6

by ozeboi69 on Aug 31, 2017
Gay Male

"Lions and tigers and bears – oh, my! Lions and tigers and bears – oh, my!" That same song lyric played over and over in my head as I staggered blindly through the thick undergrowth, my face whipped by the onslaught of branches. My panicked mind reached randomly for the familiar; a sense of normality that was lost at the onset of my journey. "Lions and t...

An English Boy Gets Turned Out Ch. 03

by RustyRover on Sep 14, 2017
Gay Male

Mr Tobias was at work earlier than normal today. He had an early meeting with Mick to discuss the new star of their porn website. The Porn industry used to be a license to print money but that had changed over the last few years. Now there was more free porn available than paid for porn. Between Porno YouTubes knock offs, torrents and all these other sites e...

Jungle Fever Ch. 5

by ozeboi69 on Aug 31, 2017
Gay Male

Chapter 5: The Lion Sleeps Tonight Two on one. The final battle had begun. I landed on the far side of the fallen tree stump to a sight that made my hopes surge. Winded from the surprise attack, The Stranger lay sprawled in the dirt, Boi straddling him, powerful hands gripped tightly around The Stranger's throat. It was the first move, only seconds foll...

Just Another Confused 18-year-old

by ChestersBoi on Aug 18, 2017
Gay Male

This is a fantasy story that involves unprotected sex between two virtual strangers. Hey, guys, this is fantasy. Back in the real world, play safe. * I was just another confused eighteen-year-old. And, boy, was I confused. I'd hang out with my mates but, more and more, we wanted different things. Most of all what they wanted was to chase the girls and, so...

Life is Strange Pt. 02

by eviltwin52 on Mar 17, 2020
Gay Male

I recommend you read Part 1 first. Let me describe Timmons to you. Besides being a giant of a man he has a gentle nature. Now if you're smart you won't mistake his gentle nature for a lack of courage. On the contrary. Timmons doesn't need to act brave, use violence, or the threat of violence. Just his stature is enough to chill out even those quick to viole...

Jungle Fever Ch. 3

by ozeboi69 on Aug 31, 2017
Gay Male

It was the fantasy I never knew was mine. Tied to a tree in the humid isolation of the Amazon, my cock throbbed with excitement at the scene before me. My captor, who I knew only as The Stranger, was perhaps the most stunning example of masculinity I'd ever known. His strength was unsurpassable; his passion for me only matched by his violence against all w...

Meeting My Master

by sonicbrad on Aug 18, 2017
Gay Male

After weeks of being dominated by my Master, we were about to meet face to face for the firs time. I had a very clear image in my head on how this day would turn out, we had played out this scene many times since meeting online 5 weeks ago and now I am here, standing at Masters front door, building up the courage to knock the 3 times as I was instructed in t...

Hunger and Thirst Ch. 01

by Corjix on May 29, 2018
Gay Male

Bayler and I grew up together and were close buds. We shared a lot about ourselves. Yeah, and at eighteen we had our firstimes together, too. Bay and I played a lot after that. Then one day he just up and told me this story about his 'desires'. He went way beyond anything I ever imagined for either of us. So it's best for him to tell you himself... Hey, I'm...

The Field Pt. 02

by Tsugaru3000 on Dec 2, 2019
Gay Male

"I am no man. I was made to serve you as you please. Please show me what a real man is." I repeated after him on his command. "Men." He said. "Wha—" I yelped as he entered me. "Be quiet, boi." He said as he began to sink himself deeper into my hole. I stayed on all fours trembling and whimpering as he filled me inch by inch. It felt like he would nev...