Gay Sissy Boi Stories

901 results
Orientation
Length
Source
Infinite Scroll

Fixing the straights

by cdbaby on Dec 28, 2016
Gay

You wake up and prepare for your day, unaware that this would be the last day you would be considered straight. You shower as you did every morning and felt the water's warm touch as it cascaded over your skin. You could stay here forever if you could. But you need to start your day and the hot water would run out before long. You wash your hair, then the re...

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There Was Something About Him

by eviltwin52 on Sep 14, 2020
Gay Male

Gay conversion story readers. An older man learns from the next generation how to truly live his life to the fullest. He was younger than I by more than 18 years. He was thin, lithely built, and was only 5'5" tall. More feminine than manly. Yet, when he told me to do something, something about him compelled me to obey. He changed my life and I'd like to thi...

Bikini Boi

by MySissyWorldx on Oct 3, 2018
Gay Male

My Brothers Troublesome friends... Note: everyone is of a legal age, and names have been changed for the sake of this story Enjoy *** My first time was more than a little bit terrifying, but enriching to my life beyond my wildest dreams. It began on a family holiday, just after my older brothers 21st birthday, him being 2 years older than I was at 19. Be...

A Pound of Flesh

by SEVERUSMAX on Sep 14, 2017
Gay Male

I was rather annoyed, to say the least, to be interrupted from my sleep that morning, on one of those rare occasions that I attempted to sleep in. Normally, I tended to be too eager to get things done to stay in bed and waste my day with idle semi-slumber. Then again, at this particular moment, I was overdue for some sleep, but I wouldn't get it yet. I was j...

Sissy's BBC Submission

by tawnysuede on Sep 19, 2017
Gay Male

Chapter 1 - First Contact "Tyler! Snap out of it - you're staring again, and he's noticed!" Jack's voice whispered hoarsely in Tyler's ear as the hot water from the shower drummed across his back. There were just the three of them left in the shower now. Basketball practise had been over for more than half an hour and the most of the players were showered...

My Neighbor Made Me Do It Ch. 08

by CapnSteelBoy on Sep 28, 2020
Gay Male

My Neighbor Made Me Do It Ch. 8 by: CapnSteelBoy ...down, down, down the spiraling rabbit hole we go.... --------------------------------------------------- Chapter 8 bah bah bah bah! That damn alarm again! Untangling myself from my boyfriend's embrace, I moved my hand and smacked the alarm clock off. Heaving a heavy sigh, I got up from the bed, Jamie c...

Sissy Dream Come True

by Sjen451 on Oct 6, 2020
Gay Male

It was Friday and I had one job left before I could start my weekend. I didn't have much planned other than watching some of my favorite sissy porn and playing with a few of my larger dildos. Not too exciting, but it's how I spend most of my weekends when I don't have other plans. Today I wore my red lace panties under a pair of black break-away running pa...

Willing First Time Submission

by nowiamhere on Aug 18, 2017
Gay Male

Enjoy the following story, inspired by a chat I had on the net. I wish it were true... * The wonderful thing about the internet is that it gives you an anonymous freedom to explore. Lets face it, more people are looking at porn than ever before, because it is accessible form home. I am no different. At 30 year of age I am an average looking guy with a girl...

My New Daddy Ch. 02

by sissytoy20 on Feb 13, 2018
Gay Male

I went home and slept well after my session with my new Daddy. My asspussy ached and that aching made me smile. I knew that his cum was still deep inside me and that meant I belonged to him. I couldn't wait to be on my knees for Ted again very soon. I had college classes the next day but I couldn't keep my mind on my studies. All I could think of was Ted po...

Jungle Fever Ch. 4

by ozeboi69 on Aug 31, 2017
Gay Male

Moaning. It escaped from Boi's lips like a gentle breeze passing through the tree tops. Groaning. I couldn't tell if the sounds he emitted were of pleasure or despair. His eye's closed, lips parted only enough for the sounds to escape, Boi's facial muscles were contorted in a way difficult to read from my vantage point above, where I stood tied to a tr...