Guild Initiation

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A young battlemage wants to join a prestigious adventurer's guild. Will the initiation be too much for him?


“Elrick, sir!"

I glanced at the man who had entered my chambers. As head of the Avalon Adventurer's Guild, I was used to my subordinates appearing unannounced. “What is it?"

“We have a new recruit you may be… interested in."

“Oh?"

“He calls himself Rigby. A young battlemage in training from the north."

“Tell me more."

“13 years old, sir. In the shape you would expect from a battlemage of his age."

I nodded. “Tell him I'd like to have a private interview at the first opportunity."


A knock came at my door, and I answered. Standing on the other side of it was a young boy with the plated robes of a battlemage. He had short black hair, and seemed to be little more than 4 feet tall. His skin was slightly tanned from his outdoor training, and his face was round and unmarked. “You must be Rigby."

The boy nodded and spoke enthusiastically. “Yes, sir! I'm here for the private interview!" His voice was filled with a fiery energy and passion.

I smiled. He was perfect. “Of course. Please, come in."

He followed behind me as I led him into my chambers, and finally sat upon the edge of my bed. I gestured for him to sit upon a nearby chair, and he obliged.

“So," I began, “why do you wish to become a part of my guild?"

He took a deep breath before starting. “I've wanted to become part of your guild since I was a small boy. The tales I've heard of the things you've done all around the world… they're truly inspiring to me. Becoming part of that is my dream."

I nodded. “And would you do anything for your dream?"

“Of course, sir!"

Perfect. “Please remove your robes."

The boy blinked. “Wh-what?"

“Remove your robes," I repeated. “Do as I ask, and I will consider you for my guild."

That was all he needed to hear. He set about removing the robes, and within a few moments he stood in his smallclothes. He was a well-built young man, clearly in good shape but with a few patches of baby fat still distinctly visible. His package seemed a bit undersized for his age, but that didn't concern me too badly. I nodded. “Very good." I then unbuttoned the front of my pants. “Tell me, have you ever given fellatio before?"

The boy shook his head, looking at my crotch nervously. “No, sir. What's that?"

I pulled out my 6-inch cock, which was not yet fully erect. The boy's eyes widened, and I spoke patiently. “Quite simply, you are to pleasure my penis with your hands and mouth. Should you do a good job, I will consider your request further. Come, kneel in front of me."

He did as asked, kneeling at the edge of my bed and looking up at me questioningly. “How should I start?"

I smiled patiently. “Begin by placing your hands at the base of my penis." He did so, watching my reaction, and I nodded. “Well done. Now, begin licking it. Base to tip."

Watching me carefully, the boy slowly touched his tongue to my base. He winced slightly at the taste, but did not recoil. “Good job," I said. “Please continue."

He took a deep breath, then closed his eyes and slowly dragged his tongue up my shaft. I shuddered. His inexperienced tongue felt incredible against my flesh. When he reached the head, he pulled his head away and looked up at me expectantly.

“Keep doing it," I commanded. “And pump with your hands, as well. Have you ever milked a cow."

“Y-yes, sir," he stuttered.

“Like that," I explained. Nodding, the boy began to lick again, pumping with his small hands as well. I let him continue like this for a minute or two, nodding in encouragement when he glanced up at me, then finally spoke. “Well done. Now, for the next part."

He stopped licking and looked up at me. “What's that?"

I placed my hand on the back of his head. “You are to take my penis into your mouth and suck on it. Do not bite down."

The boy's eyes widened in fear. “D… do I have to?"

“Of course not," I replied. “You can walk out of my chambers right now, but you will never become a member of my guild."

Hearing that he nodded. “O-okay then. I can do this."

I smiled. “Good." I pushed his head against my dick, and he slowly opened his mouth to take in about a half inch. Though he was clearly repulsed by it, he follows my directions without further question. I groaned at the feeling of his uneasy, hitching breath on me. “Now, please suck on it."

He closed his eyes, a tear escaping, but did as I asked. His inexperienced mouth was incredible. After a few moments, I pushed him further onto my cock, until I had filled his tiny mouth completely. The poor boy's tears were flowing now. After a few moments, I abruptly pulled myself out, a thin string of saliva connecting my cock and his mouth. The boy looked up at me, tears filling his eyes.

“Stand up," I ordered. He did so slowly, trembling. I did the same. “Remove your smallclothes."

“Wh-why…?"

“Because if you don't, you will not be let into the guild. Remove your smallclothes."

He choked back a sob, then did as I asked. His small body had tanlines where he normally wore smallclothes, and his tiny penis - surely no more than 2 inches - was fully erect. It seemed I had awakened something in him. I stood aside, giving him a clear path to where I had sat previously. “Please bend over my bed."

He swallowed and slowly took a few shaky steps towards it before leaning over it, his arms holding him up. He looked back at me over his shoulder nervously. “L-like this?"

I admired his toned ass. He had beautifully wide hips, and his tiny hole was begging to be forced open. “Perfect," I said.

“Are you going to cane me?" he whined

I chuckled. “Something like that." I took a bottle of lotion from my bedside table and uncorked it, sticking my left hand in and coating my first three fingers with the stuff. “This next part may be painful," I warned.

He swallowed and nodded, watching me carefully. I placed my right hand on his back and pushed him down until I had him pinned on the bed, feeling him gasp. With my hand covering nearly his entire lower back, I could feel his ragged breathing. With my other hand, I began to push my lotion-coated index finger into his anus. He yelped and clamped down on my finger, and I could feel his breathing get faster as he winced and gripped my bedsheets. “It hurts!" he whined.

I said nothing, and simply continued to push in, feeling his heavy breathing as he tried in vain to squirm out from under my hand. Slowly, inch by inch, I pushed into him as he tried in vain to push out the invading digit. In a few moments, I finally had my entire finger in. I left it there for a moment until he finally stopped clamping down, then inserted another, following much the same procedure. I did the same with my third.

Finally, I pulled out all three fingers, causing the boy to sigh in relief. Though I still had him pinned to the bed, he turned over his shoulder to look at me, his eyebrows furrowed. “I-is that all I gotta do…?"

“No," I said simply. I placed my left hand on my still-wet dick, and his eyes widened in realization.

“H-hey… You aren't gonna put that in, right?" he said nervously. “It's not gonna fit…"

“It will," I said, then guided my head into his gaping hole. Though he'd been widened quite a bit by my fingers, it was still a tight fit, and I could feel him gasp from the sensation.

“N-no!" he yelped, squirming. “It hurts! Stop!" Ignoring his pleas, I continued to slowly push in, eventually taking my left hand off my cock and gripping his hip instead.

A few minutes later, I finally hilted inside of him. The boy was trembling and sobbing, his ass still clenching desperately against me. There I stayed for a few moments until the clenching finally stopped, when I began to slowly pull out. His breath began to calm, but just before I was all the way out I slammed my cock all the way back in, my balls slapping against his. I felt his breath hitch through his back. With that, I began to thrust, slowly at first, but eventually faster and faster. I listened to the boy's symphony of gasps and moans as I relentlessly pumped in and out of his little ass. After a few minutes, my thrusts slowed as I felt my climax approach. I hilted in him, pushing down on his back with all my might as I poured my cum into his ass. He squealed at the feeling, and I took my hand off of his hip to pull his head back by the hair, causing him to gasp. After a few moments, I was drained, and I pulled out of him with a lewd slurping noise.

I finally took my hands off of him and stood, and the boy practically collapsed on the bed, sobbing as my seed leaked from his gaping hole and dribbled to the floor. His small cock was still erect, but I supposed he'd need to deal with that on his own later. “When you are ready, dress yourself and leave my chambers. I will tell the attendants outside that you have passed your interview, and they will be able to assist you from there." I buttoned up my pants. “However, should you wish to remain a part of the guild, I will be expecting you to meet with me this time every week." I paused, expecting a response, but none came. I shrugged, then left the room.