The Interview | APPRENTICE SHEPARD | Chapter 1

Something has changed in me since joining the Order. I don’t have enough words to say exactly what I mean, but I guess, under their watch, I’ve started to feel a little bit more like a man.

It helps that we have to dress formally here. I never leave my room these days without wearing a shirt and tie. It makes me feel so grown up! I love the way the pants cling to my legs. I enjoy the soft kiss of the cotton shirt against my torso and the way that the dart at the bottom of my silk tie sometimes brushes against the back of my hand.

I find myself looking at other guys in the complex, wondering if they’re having similar thoughts. I find myself drawn to the Masters in particular, because they are always so spectacularly well-turned-out. They always smell real good, too; I love passing them in the corridor and allowing myself to be engulfed by the cloud of expensive scent which always follows in their wake.

When I was told that my interview would be with Master Figata, I felt a rush of adrenaline. Last week, he delivered a talk to the new apprentices which I found life-changing. I just stared up at him, astounded by his pearls of wisdom while allowing his deep, resonant voice to massage my ears.

I entered the interview room and Master Figata told me to sit down next to him. I couldn’t take my eyes off him; up close, he was even more attractive. All sorts of crazy and inappropriate thoughts were bouncing through my head. Yet, there was something about the way he was looking at me which told me that my thoughts were okay.

He instructed me to stand and remove my tie, shirt and pants. For some reason it felt like the most natural request in the world, so I did as told, never once even thinking to question why. He watched me intently as I undressed. My dick rose immediately. I knew it would be tenting like crazy in my garments, but realized there was nothing I could do to cover it up.

He sat me back down again, took my arms, and then tied them behind the chair. Again, there could have been no other circumstance in the world where this would have seemed anything other than terrifying, but as I felt his huge fingers brush against me, my wrists yielded to the knot. My dick throbbed.

He started to touch me so softly and gently that, before I knew it, my entire body was covered in gooseflesh. I’m not going to lie—I am very inexperienced when it comes to intimacy. I have, for some time, known that my sexual urges were of a homosexual nature, and although I’ve never attempted to suppress them, I suppose the right opportunity had never presented itself to me. If this was to be my induction—right here, right now, with this beautiful older man—I could surely count myself as the luckiest guy on the planet, right?

And then, everything seemed to go silent. I was suddenly aware of the sound of my breath, the distant hum of a faulty electric light, and the rustle of Master Figata’s fingertips as they drifted across my undershirt. He was so handsome in his white suit. At that moment, I would have done anything he asked me to.

He touched me all over my body. Every time his fingers came to rest, I felt somehow more alive. When he started to run his fingers up and down the shaft of my dick, I genuinely thought I was going to explode. He pulled down my underpants and exposed my dick to the room. My instinct was to reach out and touch him, but since my hands were firmly tied behind my back, there would be no such reprieve. He was entirely in control. In my mind, I begged him to continue.

He licked his finger and pressed it against my hole. He teased me. He knew I wanted it, but he kept me waiting for what felt like an eternity. I closed my eyes in a state of pure excitement and, when I opened them again, he was holding a toy which I figured was some sort of dildo. He carefully rubbed oil into it before positioning it against my hole…

The next moment, I felt him pushing it into me. Nothing had ever been up there before and the sensation was somewhere between agony and ecstasy. The more it hurt, however, the better it felt; I could feel the precum forming on the tip of my dick. I didn’t know how long I was going to be able to last. I willed myself not to cum.

He took his jacket off and rolled up his sleeves. My mind started dancing, wondering what was going to happen next. He rubbed oil into my dick, and, before I knew it, he was jerking me off. The dildo was still deep in my ass, pushing me open. Waves of pleasure crashed through my body with each jerk.

I knew I was about to shoot. I held on for as long as I could but it was all too much. He started to bite my nipple. Just the brush of his lips was what tipped me over the edge. My dick exploded into the palm of his hand. It was a remarkable moment; more intense than any orgasm I have ever experienced.

Then he kissed me tenderly and, at that exact moment, I suddenly and finally understood exactly who I am. Somehow, any and every interaction with The Order brings such clarity.