Gay Apprentice Stories

114 results
Orientation
Length
Source
Infinite Scroll

My Stepdad

by canaigle on Aug 30, 2017
Gay Male

Chapter One I was fortunate to realize at a young age that life in the long run provides us with what we need and not necessarily what we want. I had to learn to stay out of my own way so as not to muck things up and make life difficult, for no reason at all. My father was not a fun guy. He had a load of issues, old baggage he had never dealt with in order...

How I Became a Sissy Slut

by DixeenormousToo on Sep 15, 2017
Gay Male

I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star. After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of...

Free to Love

by Pelaam on Sep 14, 2017
Gay Male

Pelaam(c): August 2007. Vidarr stormed into the small town with the rest of his raiding party. Everyone separated to cover more ground, yelling loudly and swinging either axe or sword. Vidarr powered towards a medium-sized single story dwelling. He crashed through the door as it gave way under his axe's blows and the big man bellowed as loudly as he could....

Need to Be Needed

by sr71plt on Aug 18, 2017
Gay Male

"That's one sweet ass. You are one sexy piece of ass." "I can sing too, and will look good in front of your band," I said, trying to keep the focus on why I was there, in the sleazy hotel room, tinted red by the "O" and the "L" of the flashing neon sign just outside the window. I wondered if he could hear the pain in my voice, although chances were that he...

Bait a Hook Ch. 12

by VaRiverWriter on Sep 25, 2017
Gay Male

Chapter 12: Ebb & Flow I was in my room sitting at my desk when I heard my dad come back home. I heard him as he marched up the stairs and barged in my room. My heart was pounding and my eyes threatened tears as he walked straight to me before pulling me up and into a hug. "I love you Bobby. I'm sorry if I scared you." I let out an audible sigh of relief a...

Tanners and the Banker's Boy

by Acerbicscribbler on Sep 14, 2017
Gay Male

Given that I couldn't find an appropriate place to insert the ages of the characters involved, let me assure you here that all are eighteen or older. * "Wash up, lazybones, and take those furs to Sir Charles," the tanner ordered. The day's chill turned his breath to a liquor-laden mist. "Sir Charles, Father?" Tanners asked, confused. The tanner rolled hi...

The Lunar Life Ch. 05

by musicfreak on Sep 25, 2017
Gay Male

A week passed and things between Will and Thane weren't getting easier, but they weren't getting harder either. After their talk that night a week ago, the two had definitely tried to keep things platonic between them. Of course that wasn't very easy, seeing that the more time they spent together, the more the felt themselves falling for each other. Still, i...

Yes, You Will Swallow

by secondstring513 on Jun 5, 2019
Gay Male

I knock on the door in a very nervous state. I am just getting ready to turn around and move quickly to my car but you answer the door before I have a chance to make my move. "Good afternoon Dennis -- I am glad you were able to make it." You say in a very welcoming and assuring voice. I reply with a rather feeble "Hello." I realize just how weak that soun...

Prison School Ch. 23

by o2byoung on Sep 14, 2017
Gay Male

Chapter 23 – W4 Monday evening (Just to catch you up – at the very end of Chapter 22, Luke had received this letter) "Mike," Luke said, "I received a very disturbing letter today from Sylvia." "Sylvia? Who is Sylvia?" "She is—was my girlfriend. Mike," Luke sobbed, "I don't know what I should do. She wants to make amends, here, just read it!" Luke handed...

Young Jimmy Ch. 03

by MistressAthena on Aug 18, 2017
Gay Male

Mr. Yomoto chuckled, "There now. Don't fight what you are destined for." He lifted up the whip and asked, "Who am I?" Jimmy growled back, "A sick fuck!" Mr. Yomoto delivered two stripes across Jimmy's ass and calmly said, "You will call me Sir. Do you understand?" Jimmy hesitated. His hesitation resulted in two more swipes across his ass. Mr. Yomoto sh...