The Alpha Academy - Chapter 3 (part 3/3)

Previously:  

Chapter 1 - Part 1 | Part 2 | Part 3
Chapter 2 - Part 1 | Part 2 | Part 3
Chapter 3 - Part 1 | Part 2 

***

He bent and pulled out the most massive butt plug I had ever seen from under his desk, though it didn’t seem too out of place when compared to the size of the arm holding it.

- You use smaller toys like this one to warm up the cunt. Proceed slowly and gradually, you never want to cause an injury. There’s no worse setback.

- Smaller than this one, Sir?

- Ha! This one is small, my boy, he chuckled.

He walked around the desk and put the toy on my lap. Holy shit that thing was heavy. These looked easier to maneuver in those Internet videos I used to jerk off to…

He sat on the desk, leaned backwards and pulled his legs up, revealing his soft, malleable cunt once more. It deformed hypnotically at every slight motion of his body. His cock dangled to the side, with a half erection that told me his real but not excessive. Nothing out of the ordinary for Sir Wyatt. Of course, nothing about me could impress a man like him. I noticed a small stream of precum coming out of his piss slit.

- Push it inside.

- Shouldn’t I lube it up first, Sir?

He threw his head back as he burst into sudden and loud laughter, causing me to jump and nearly drop the toy. He laughed so hard his face turned red, and his pussy pulsed, clenching but never closing, with every jolt. He finally took and deep breath, and said more firmly:

- Push it in, boy.

I felt humiliated and inexperienced, but at the same time I couldn’t wait to see the toy being swallowed. Holding the odd shape with both hands, I started pressing it against his sloppy opening. His lips deformed leniently and no resistance was met.

- Yeah boy, that’s it. Aaaall the way.

As I pushed the toy deeper, his hole became fully stretched, and for the first time no wrinkles at all were visible on it. All the tiniest details of the transformation mobilized my entire attention. I was fascinated. Finally, the widest part passed through without any noticeable resistance, and the rest of the toy was sucked inside him, leaving only the massive, round base visible.

- Very good. That’s enough, we’ll leave the top training at that for now. There’s another matter we must see to.

I sat again and he rose up, then leaned on the table. There was no way to tell from his posture that an insanely big butt plug was filling his insides. His cock now dangled closer to my face, and I noticed his leak dropping on my naked thighs.

- My fellow Men must suspect nothing about these encounters we’ll be having. I’m afraid we’ll have to give them a reason to believe you came in here to be taught a boy’s lesson.

- What… kind of boy lesson Sir?

- I hope I’ve convinced you there’s nothing unmanly about a little butt training. Have I ?

I gulped.

- What plug size are you able to take, boy?

- Sorry, Sir... I’m not sure I understand…

- Plug size, boy. When you plug, what size do you use?

I was abashed. He was asking this so matter-of-factly. Did everyone know their plug size? I had, yes in fact, already plugged in the past, out of curiosity… but I’d never given it so much thought as to even notice there’d be measurements.

- I don’t know, Sir. I haven’t really plugged all that much…

He gave me one of these teasing fatherly smiles, and put his heavy hand on my shoulder. Weirdly, in that moment, it felt like the larger size I could name, the more he’d approve of me. But I had literally no idea what to say.

- We’ll find out together boy, no worries.

His kind tone made me feel so relieved. We’d find a plug for me and it would all be alright. Apparently, everyone had a plug size – regardless of being boy or Man. It was just a trick to help me get upgraded to men. Yeah, that made sense.

- Show me that hole, boy.

Not boy training, I repeated to myself. He moved to the side, and I laid my body on the desk, spreading my legs to the sides.

- Wow, we do forget how tight they begin, Sir Wyatt noted. Let’s see.

I heard him gather spit in his mouth, and suddenly a thick, warm substance ran down my ass crack. Two fingers started rubbing firmly, pressing all around my hole. It did feel good – any massage did. And I felt like I could trust the guy… He had showed me Men also got their holes played with after all. This was necessary in any case. The growing strain in my cage was nothing to be concerned about. Wyatt suddenly let a deep grunt out, and I nearly whimpered in response, but prevented myself just in time.

- Size “2” will do, you relax fast enough.

Immediately, there was a pressure on my hole.

- Relax, you’re doing very well, boy, he said in a comforting tone with one hand massaging my sphincters. The pressure on my hole was increasing. Relax and open up. You’ll be coming here a lot, you know. Are you eager to learn more about that fat dad pussy you tasted earlier?

The feeling of his soft cunt came back to my mind and I noticed the smell was still on my face. The strain peaked in my cage and my hole suddenly relaxed, letting more of the plug in.

- Very good. You liked that fat Daddy cunt, didn’t you boy? The way it let it all in?

- Fuck yes, Sir.

Another shiver of horniness sent through my cage, and entire body, and I let some more of the plug in.

- Daddy’s pussy is trying to squeeze on that plug you just shoved into him. But he’s too sloppy and the plug is too small, he can’t do it.

Another expert massage move and I opened up to let the whole of the plug in. The feeling of the size surprised me – it was invading my rectum quite uncomfortably. My hole felt stretched as though a big cock was stuck in it. I realized I had no idea just how big was a “size 2”.

- There. That should do it. Don’t worry about it too much boy, it’s so small it barely even counts as a plug. You won’t even remember it later on. Now go back to your mates, you can take the plug out in the changing room. If you cross paths with Academy Men, make sure they can see you’ve been taken care of. Remember, no one must suspect my plan to have you upgraded to the Men.

I did my best to act unbothered as I stood up. For how supposedly small it was, the plug felt huge inside me. It was an effort to think of anything else.

- Got it, Sir. Thanks, Sir, I can’t wait.

He patted me on the shoulder and gave me an understanding nod while staring right into my eyes. He looked proud! Any apprehension suddenly left me and for the first time I felt like the Academy wasn’t so intimidating after all. I started for the door, and as I went past him I felt a small tap on the plug which resonated on my prostate and my locked nub. I turned to him and he winked at me with a smile. No words were exchanged and I left the room, and I knew I was blushing harder than ever.

End of Chapter 3