The Most Important Rule

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DISCLAIMER: This story involves chastity, butt plugs, small penis humiliation, and sexual acts between reluctant but consenting adults.

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Recap: Rex and some old co-workers of Chris' came home late to find the letter Chris wrote for Rex about how he was feeling. Chris was made to read the letter aloud to the group. In turn Rex has decided to reward Chris for not breaking the rules and invited him to his bedroom. _______________________________________

The Most Important Rule Part Five

Rex: "Get on the bed. Lay down on your back. hands to your side."

He grabbed my ankles and positioned me to the corner of the bed so my ass was right at the corner and legs hanging over the sides to the floor. He then lifted my legs and told me to grab my thighs and hold my legs open. Even with everything that's gone on over the past few days I've never felt so exposed. I was completely vulnerable and this was a totally new experience. I was unsure what to expect.

Rex: "You were a very good boy today, Chris. Do you know what good boys get?"

Chris: "N-no sir"

Rex: "Good boys get rewarded."

Rex gently took hold of my swollen blue balls and began to slowly slide the cock shaped plug in and out of my butt with his other hand. I began to moan almost immediately. Every time he would press it back inside me he would tug on my balls ever so slightly creating a slow sensual rhythm.

Rex: "Tell me what you're feeling. Thinking. Let me help you"

Chris: "I can feel pressure building in my balls. It feels like I'm about to cum but in slow motion. I'm so close but I'm not cumming. I don't know what's wrong."

Rex: "How big was the plug again? 5 inches?"

Chris: "Y-yes Sir"

Rex: "Aren't you smaller than this plug?"

Chris: "Yes Sir I'm smaller than the plug sir."

Rex: "I don't know Chris. I'm already cheating by giving you something you can't give. Maybe you're just not ready to cum yet."

Chris: "No sir, please. Please keep trying"

Rex: "It's not working Chris, I'm sorry. Maybe another month and we can try again."

I grabbed his wrist and held him from pulling away.

Chris: "Sir? D-do you have a larger plug?"

Rex: "You think that will work? Is 5" too small to make you cum or something?"

Chris: "Yes Sir. I need bigger. 5 inches is not enough. 5 inches will never make me or anyone cum sir. Please."

Rex: "And that's why you're a virgin isn't it Chris? You're too small to fuck."

Chris: "Yes, I'm too small to fuck. I don't deserve to cum but I beg you to let me, sir. Please"

Rex stood up and headed toward his closet. He pulled out a box, laid it on the bed, punched in a combination, and opened it next to me. It was full of sex toys of all kinds. Dildos, butt plugs, diff style chastity devices, vibrators, lubes and other items. Rex pulled out a dildo, about 6.5" long.

Rex: "What do you think? This is the next size up. Still want to try?"

I was so close. I didn't care how big it was. I needed it to push me over the edge.

Chris: "Yes, please. Please"

Rex grabbed a bottle of lube from the box and squeezed out a blob onto the tip of the dildo letting it ooze down the head and shaft before he lightly pressed it against my butthole. He swirled it around helping to lube me up teasing me in the process. He gently pressed the tip into me but wouldn't go past the first inch or so. I couldn't take it and began rocking myself back and forth to try and get more.

Rex: "That's it, you're so close Chris. Come and get it."

I took that as an invitation. I reached over to the lube and squirted some into my hand and then reached down to the dildo to help lube the shaft more. Rex let go of the dildo and let me take control. I began to fuck myself again, but this time it felt very different. The dildo was reaching deeper and making me feel full. I could feel the ridges of the rubber cock head reaching my prostate now. Finally having enough length and girth to apply pressure. That small butt plug was never going to get the job done. I needed something the size of a real cock. It didn't take long for the feeling of an orgasm to come over me again. It had only been a handful of thrusts and I was already at the point that took me all night to reach with that pathetic 5 incher. I could feel my penis leaking now. Rex also noticed as he placed the tip of his finger on it and brought it to my mouth.

Rex: "You're getting close. Almost there baby. When you do finally cum you'll have to eat it up, ok? That's going to be another one of your chores now."

Rex went back to my penis and brought some more to my mouth. It wasn't much but the tiny bit of stimulation he was giving me from pressing the tip of his finger to my penis was getting me close to exploding. He continued to feed me to myself as I continued to abuse my prostate.

Rex: "Just focus on the cock inside you. I'll catch your mess for you. Just let go."

This was it. I felt it coming this time for sure now. My body was almost going numb. My body was on the verge of shaking. I kept fucking myself, harder and faster now - but nothing happened. I did not cum. My frustration was at an all time high. my entire body was tingling but no matter how hard I tried to get myself over the edge it just wasn't enough.

Rex saw this and decided to help by taking control again. He grabbed my hips and flipped me over onto my stomach. He positioned me in a way so that my legs were on either side of the mattress with my butt in the air over the corner and positioned my penis in a way so that it was bent back pointing to the floor. He placed a hand on my lower back and pressed me into the bed with his body weight. With his free hand he then began to fuck me with the dildo. He told me how in this position It would go in even deeper - and he was right. I felt much more opened up and the pressure on my penis against the mattress was helping too.

Rex: "How's this? Let me know if it's too deep."

Chris: "No, this-th-this is good. D-deeper"

Rex slide the dildo in a little deeper now

Rex: "I don't want to hurt you. This should be enough for a little boy like you"

Chris: "N-no, not enough. Deeper. Please"

Rex: "Are you sure? Ok baby, i'll go slow, you tell me when to stop"

Rex started to slide the remaining length of the dildo into me. It was balls deep now. I let out a whimper as I felt his knuckles brush against my balls. He slowly slid it back out and then back in. Each thrust caused me to shiver. I was in a daze. Hard to think straight. All I wanted was release.

Chris: "d-deeper daddy"

Rex: "This is as deep as it can go chrissy"

Chris: "n-no I need more"

Rex: "There is no more. Should I stop?"

Chris: "don't stop..go deeper"

Rex: "There's nothing left, I'm sorry"

I reached back toward Rex and tried to force his hand to press the dildo into me deeper but he was right, it was a fruitless effort. I was fully impaled.

Chris: "d-deeper"

Rex: "Chris, I told y-"

Chris: "you"

Rex: "Yes, I told you."

Chris: "No, you. I need you"

Rex: "Need me? What do you mean?"

I couldn't believe what I was saying. Was I really this far gone?

Chris: "Please daddy"

Rex: "Please what? What do you want? I don't understand"

I paused. I took a second to really consider what I was thinking. It didn't really matter though did it? I needed it. I rolled back over onto my back. My aching penis sticking straight up into the air begging to be touched. I slid off the bed and down to my knees in front of this man.

I looked up into his eyes and told him I needed more than what the dildo could give me. I nuzzled the side of my face against his crotch through his jeans and began to slide the dildo in and out of myself rubbing my face against him in the process. I began to suck and lick at the forming bulge through his pants. Finally, I reached back and slid the dildo out from inside me completely.

Chris: "I need more, daddy"

I reached up to his belt and began to unbuckle it. Rex took over as I unzipped him and helped him slide him out of his pants. Rex was fully erect now. Rex pulled his shirt off and stood before me completely nude. I don't know why his cock always looks so angry when its hard but it did. Maybe I'm just so used to mine looking harmless.

I reached back over to the lube and squeezed out what must have been an 8.5 inch line down the shaft of Rex's cock. I began to stroke him, taking time to tease and edge him while I did so. I must have been doing a good job because it didn't take long for Rex to pull me back to my feet before throwing me back onto the bed.

He grabbed my hips and pulled me into a doggy style position. I could feel the heat of him behind me. He placed a hand on each of my butt cheeks and squeezed and spread them before spitting into my puckered butt hole. He continued to massage my cheeks as he inched closer, until I finally felt the tip of his cock touch my boy pussy.

Rex: "Is this what you wanted?"

I gasped and started to push back into him.

Rex: "Once I'm inside you there is no going back. You will be a full blown faggot."

I pushed back toward him but didn't say anything.

Rex: "Are you a faggot, Chris? A little gay twink?"

Chris: "I'm...I'm..."

Rex: "What are you?"

Chris: "I'm a faggot little gay twink Daddy"

Rex positioned his cock head on my hole.

Rex: "There are two kinds of males in this world, Chris. Men and boys. Which are you?"

Chris: "I'm just a boy"

Rex: "That's right and men fuck while boys get fucked."

With that said Rex pressed his cock head forward and popped it into me. I heard him moan a sigh of relief.

Rex: "That's it boy. I'm inside you now. You're safe."

Rex squirted some more lube on his shaft. I could tell he wanted this too. He must be so fucking horny after everything that went on tonight. I bet he needs to bust more than I do. He deserves to bust more than I do - that's for sure.

Rex: "What are you?"

I've had Rex inside of me orally a couple times now, but this was something different. Something more. It didn't feel much different than the butt plug other than it being wider and warmer but mentally it was very different. A man's hard cock was pushing deeper into my boy pussy. Deeper than anything else I have had before. I felt the fat head of his cock reach my prostate and then push past it. I began to shake.

Chris: "I-I'm a faggot"

Rex continued to slide deeper until I felt his pelvis against my butt cheeks. He repositioned his grip on my hips and began to slowly slide himself out of me. His cock head rubbing my prostate on the way out made me jerk.

Chris: "I'm a fa-faggot"

He slid himself back into me. Again, the tip of his cock rubbing past my prostate caused me to jump. Every time his stomach pressed into me I could feel my penis bounce between my stretched legs.

Chris: "I'm a faggot, I'm a faggot"

Rex started to go faster. He began to really get in rhythm now. Rex took his left hand and placed it on the right side of my hip. He used his right hand to reach up and grab the bottom of my jaw and pull my head back. The he started to fuck. Like really fuck.

His heavy cum filled balls smacking against mine with every thrust. My ass cheeks clapped against him every time he fully penetrated me. The constant back and forth of his cock against my prostate was giving me what the smaller dildo wasn't able to provide and I was in ecstasy.

Rex switched positions now. He laid back and propped me up into a reverse cowgirl position. He grabbed my wrists and pulled them behind my back forcing me to sit up straight on his cock. I was staring straight into his mirrored closet doors now. I looked like a two bit whore. My hair, which I hadn't cut since from even before I moved in, was a mess, my pale skin was glistening with sweat, and my skinny erect penis was dripping precum. I looked down at myself and Rex quickly interrupted.

Rex: "Nuh-uh boy. I want you to watch yourself get the maleness fucked out of you. Look forward. What do you see?"

I motioned my head back toward the mirror and watched as he fucked me. my little body on top of him bouncing outside of my control.

Chris: "I-I s-see a pa-pathetic excuse of a...of a man. Just a b-boy. N-not even a b-boy. I'm..I'm a pussy b-bitch. I'm a faggot"

He was deeper than he had already been with me on top like this and I began to feel the overwhelming sensation of an orgasm start to rise. I felt it in my balls. I could feel the cum inside them. The pressure was getting extremely intense.

Rex: "That's it boy. You're getting close. I can feel your pussy getting tighter."

My penis started to tingle and I began to start breathing heavier and heavier. I can see my chest getting more red. I felt my eyes rolling in the back of my head as Rex continued to fuck me. I was losing control.

Chris: "I-I feel it coming. I think I-I'm going to c-cum"

Rex: "Let it all out boy. Don't hold back. When you cum that will be the last little bit of manhood you have left."

Rex released one of my hands and reminded me to catch my cum. There was nothing I could do to get out of this now. It was too late - but this was different from anything I have ever experienced before. I didn't feel the normal sensation of shooting jets of thick hot cum like I was used to. This felt more like I was peeing. My orgasm streamed from the tip of my penis and filled the palm of my hand.

Rex continued to bury his fat cock inside me over and over again as I finally came.

I felt the pressure in my balls recede but my frustration did not. I still felt just as horny as ever. Something was wrong. I thought I was supposed to cum? My blue balls were gone but I didn't feel like I came at all.

Rex: "Eat it boy"

I looked into my hand and saw 2 months worth of backed up cum before bringing it to my mouth and sucking it down. Rex started to lose it and began to pump my pussy full of his seed now.

Rex: "Fuuuuuuuuckkkkkkkk! Fuck! Take that fucking cum bitch. This is how you fuck. This is how men cum you fucking bitch."

Rex's cock stayed hard inside of me and I could feel him throbbing and pulsing long after he was finished shooting his balls inside me. Rex laid there catching his breath while he rubbed my ass, hips, thighs, stomach, back and chest. I felt disgusted with myself after my senses came back. I wanted to pull off of him and run away back to my room, but Rex had other ideas.