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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: Upon Rex's request Chris completed a written letter describing his thoughts and feelings leading up to and after his initial submission to cock.
The Most Important Rule Part Four
I woke up to the sound of laughter entering the house. I looked over to my phone and it was around 3:30 AM. I could hear Rex and some other voices going back and forth talking and laughing. It sounded like they were drunk as they made a lot of noise and I could hear them bumping into things in the dark. This was out of the ordinary. Rex never brought people over. This was the first time since I had been living here. I tried to make out how many people were there and it sounded like 3 guys and a girl. I walked closer to my bedroom door to get a better listen.
Man 1: "Hey Rex, you got any beer?"
Rex: "Yea, it's in the kitchen"
Woman: "What do you want Greg, I'll grab it."
Greg? The name is familiar.
Man 2: "Hey Amy. Grab me something to"
Amy? Oh no! I used to work with an Amy. I worked with a Greg as well. Too much of a coincidence to not be them. Greg was a short fat Italian man. He was always kind of a dick to me. Amy was probably in her early 20s. amazing boobs, big ass, tiny waist, long blonde hair, about 5'1 and maybe 120lbs at most. I fantasized about her so many times. One time the A/C broke in the office and she was wearing the smallest little outfit. I masturbated twice in the bathroom that day. I even snuck some photos of her that I still have. I always thought that her being so tiny would be perfect for someone like me but I never built up the courage to pursue it.
Amy: "Hey...uh, Rex? What's this letter all about?"
The letter! My letter! Oh God! I totally forgot that I left the letter on the fridge. I wasn't expecting anyone to come over. This isn't good.
Rex: "What letter? Probably a bill."
Amy: "Nah, Rex. This isn't a bill. Who is Chris?"
Rex: "Chris? Ohhhh, that letter. Ok, haha! Man that's funny. Remember that twinky kid who quit a couple months back?"
Man 2: "No way, that Chris? What you doing with his stuff? That kid was so weird man. He would order some crazy stuff."
Rex: "Leave it to Brian to have something nice to say"
Brian? Oh yes, he was the mail guy. These are definitely people I used to work with. Brian was a tall skinny black guy. Probably 6'3" and 170 pounds. Always with his headphones in. Didn't talk much to me when I saw him. Always seemed like I was bothering him when I would get packages.
Greg: "So, what about him though?"
Amy: "You have something you want to tell us Rex...this...um..letter is interesting to say the least..."
Rex: "Ok, alright, cats out of the bag. I wasnt going to say anything but Chris has been living here for a couple weeks. I'm trying to help him get back on his feet, ya know?"
Brian: "What the fuck, why?"
Greg: "Kid quit like a dumbass. How's that your problem?"
Rex: "Damn, you're putting me on the spot tonight. He didn't quit, ok. I laid him off"
Amy: "I'm so confused. I'm too drunk for this right now"
Rex: "Amy, do me a favor. Just read the letter to everyone"
Amy: "Are you sure? I mean..."
Greg: "Wait! It's almost 4 in the morning. Is he here now?"
Rex: "Yea, he should be sleeping upstairs unless you bastards woke him up."
Greg: "If he's here maybe we should have him read it?"
Brian: "Yea, its his letter. Have him read it. OHH CHRISSS!"
Amy started screaming out my name too, then Greg. All three of them were calling down for me now while laughing and having a great time.
Rex: "Alright, Alright, calm down calm down. I'll go get him, promise to be nice."
I couldn't believe what I was hearing. This can't be actually happening. I heard Rex push his chair away from the table and walk toward the stairs. I jumped back in bed to pretend I was asleep just in time.
Rex: "Hey Chris, wake up"
He flicked on the lights and sat on the bed. He shook my shoulder and I pretended I was still sleeping.
Rex: "C'mon Chris, I know you're up. I heard you moving around up here when we first walked in. Don't disappoint me now.
Rex slid his hand under the blankets and across my thigh and palmed my caged penis
Rex: "You've been doing so good. Don't you remember that tweak to the rule we talked about? 60 days, right?"
I rolled over onto my back, his hand still on my cage. I grabbed his wrist to hold it in place and opened my eyes. I told him I was so horny and I remembered the tweak he brought up but to please not make me come down stairs.
Rex: "Come on. You heard them down there, I know you did. They just want you to read your letter to them. Don't be shy. You know these guys. We're all friends here.
I pleaded with him again to tell them I was sleeping or to lie and say I wasn't there. Rex then reached into his shirt and pulled out the chain that held the key to the chastity cage. He reached down and actually began to unlock it. I was frozen, still unsure what to say or do. He went on to slide it off of me and began to give me a handjob. Slow but with intention."
Rex: "I need you to do this for me, Chris. I need you to go down there and read them your letter."
Something about him saying he needef me to do it compelled me to comply. I began to get out of bed and look for my clothes.
Rex: "Uh-uh. Not the sweats. Put on those other short shorts I like. forget the shirt. Snap to it"
I slipped on the skimpy ranger panty style shorts and followed him downstairs. My tiny boner still hard and bouncing with each step. The silky fabric rubbing against me was so intense I thought I might cum from that alone but all it really did was tease me making my situation worse. The kitchen wasn't far so there was no time to calm down before I made it there and was greeted by my old co-workers.
Brian: "Hey Chris! It's good to see you!"
Amy: "Looks like he's happy to see us too"
Amy pointed at my tiny boner pressing against the thin shorts and began to uncontrollable laugh. Greg just kind of grunted at my direction in disgust and handed me my letter with a raised eyebrow.
Rex: "Go on Chris, don't listen to her, just read it."
I stood there beat red but started to read. The sooner I start the sooner I can go back upstairs I thought. I barely got through the first paragraph before the group started to laugh hysterically all over again.
"Dear D-D-Daddy..." "...The no...sigh...The no masturbation rule was scary. Very scary......for a virgin like me..." "...It wasn't the usual stuff I would watch though. Instead of white girls getting blacked or the femdom small penis humiliation videos you found on my laptop, I searched for cock sucking videos..." "...I am not a man..." "...Its is my place to feel the denial and full frustration of what I am not good enough to have... "...then I looked up and saw your beautiful hard cock bouncing above my face..." "...I'm too small and pathetic..." "...The more I sucked you the more I knew this was right..." "...as I felt each pulse of cum shooting inside my mouth..." "...the moment you inserted your cock into my mouth again this morning..." "...thinking about when I'll get to taste you again..."
"...Sincerely, Chris"
I wanted to die. Everyone was laughing now. Even Rex. Amy was literally rolling around on the floor unable to catch her breath. Greg was giving Rex a high-five. Brian was taking out his wallet and handing over $100 to Rex."
Brian: "You son of a bitch. You actually did it."
Amy: "So, can we see it? I want to see it."
Rex snapped his fingers in my direction. He didn't have to say anything. I knew what he meant by it. I began to slowly slide my shorts down my legs.
Greg: "Do it sexy."
Why was Greg always such an asshole to me? I looked at Rex and he gave a nod of approval. I reluctantly started to sway and swivel my hips side to side.
Greg: "Sexier"
I started to sway and jirate wider now. I began to use my knees along with my hips to dance. My shoulders now too. I started to pull down my shorts only to stop and rub my hands over my body.
Greg: "Sexier!"
I spun around and dropped into a squatting position. Everyone in the room started to hoot, holler, and cheer me on now. I felt so sexy. I put my thumbs in my waistband and slowly began to pull the shorts down beyond my butt before I stood back up. The elastic band lifted and forced my cheeks to jut out causing even more cheers.
Greg: "Shake that ass, boy"
Without much thought I started to wiggle it back and forth. For such a small guy I did have a pretty nice butt. Jiggly, smooth, creamy white globes; about the size of cantaloupes. With my back still turned to the group I leaned over and touched my toes before I finally decided to slide my shorts down my legs and all the way off. I was lost in the attention. I wasn't used to being the main attraction and I absolutely wasnt used to it when it was so sexually charged. I was so carried away I almost forgot the whole point of the show. I took a deep breath and turned to face the crowd more proud than I have ever been in my life.
The room was silent.
Amy: "Where the fuck is it?"
I wasn't hard. I was completely soft. My penis looked like a tiny grape sitting on a plum. I was so focused on the dancing and trying to tease everyone that I lost my boner and now that everyone was staring at me I had massive stage fright and couldn't get it up.
Rex: "Wow Chris, what's wrong? Didn't you have a crush on Amy?"
I lowered my head down and managed to mumble out a "y-yes"
Rex: "When he first got here I went through his phone and found some photos of you in there Amy"
Amy: "Oh my god. What kind of photos?"
I was so ashamed.
Rex: "Tell her Chris"
Chris: "That one t-time...that one time the A/C broke. I..uh..I snuck some photos of you in your sundress.
Rex: "A little more detail than that, hun. What did you take photos of specifically."
Greg: "..and why did you take them? I think we would all like to know that."
Chris: "I, um, I took them of your b-boobs and butt. I'm sor-"
Amy: "Don't apologize, it's ok. I think it's cute. But, yea, why did you do that?"
Chris: "I-it w-was so t-that I could look at them when I...."
Greg: "When you what?"
Chris: "masturated"
Amy: "Awwww! Chris is so adorable! Why didn't you ever ask me on a date?"
I froze. I couldn't move, speak, or think. I was so embarrassed.
Rex: "Answer her. Hands on your head. Eyes up. Answer her."
Chris: "I-I didn't think...I mean I knew..."
Amy: "Go on, let it out. Tell me."
Chris: "I knew I would have been too small for you."
Brian: "Way too small bro. Way too small for this slut."
Amy: "Hey, fuck you Brian, haha, stop being mean to him. I don't think you're small baby. Go on, why don't you prove it. Prove Brian wrong. Get it hard for us so we can measure it. And you know what? Maybe Brian should measure his for us too since he thinks he can talk."
I looked toward Rex. He gestured for me to get started. Brian wasted no time and walked right up next to me and dropped his pants to his ankles. I tried not to look but I couldn't help myself. He was soft. Completely flaccid and probably 5 or 6 inches long and around as thick as a half dollar coin.
Amy: "Oh. Oh dear. Wow! Rex, do you have a ruler?"
Rex reached toward the junk drawer and pulled out a measuring tape. The ones used for fabric. The flexible kind. He tossed it to Amy.
Rex: "That's all you"
Amy walked up to Brian and unraveled about 12" of the tape on her way there. She held it up to his soft cock and called out 5.5" before turning toward me.
Amy: "Hello! Looks like someone woke up."
Watching her touch Brian's black cock must had got me rock solid again. She wrapped up about half the tape and handed it to me.
Amy: "Why don't you do it"
I was a little disappointed to be honest. I thought a woman was going to finally touch me for the first time in my life but no.
Rex: "Well?"
Chris: "f-four inches and th-three quarters"
Greg: "Holy shit Brian's bigger than you soft haha. Look at them next to each other."
Rex: "What about the girth?"
I wrapped the tape around my shaft.
Chris: "4.5 inches"
Greg: "How big is the butt plug?"
Brian: "Butt plug? What the fuck?"
Greg: "Yea, the one in Chris's ass. I saw it when he was bending down."
Rex: "Ha! Damn Greg, good eye! Let's find out. Go on Chris."
Everyone stared at me waiting for me to make a move. I slowly squatted down and began to slowly pull it out from inside of me.
Rex: "Guys, look, he's drooling"
Rex pointed toward my penis and the bead of pre-cum forming as I tried to remove the plug. I just closed my eyes and continued to work on pulling it out. It wasn't massive or anything but thick enough for me. I kept going till I eventually got it all the way out with a wet plopping sound.
Greg: "Oh shit, its shaped like a cock too"
I never really thought about it, but its true, the plug was shaped like a cock and I walk around with it inside me almost 24/7.
Greg: "So, how big?"
Chris: "5 inches long, and just under 5" wide"
Rex: "Come on Chris, show some respect. Complete sentences."
Chris: "The size of my butt plug is 5 inches long and just under 5 inches wide, Sir"
Brian: "Haha, your butt plug is bigger than your cock, absolutely fucking pathetic."
Amy: "Smaller than yours though..."
Greg: "What you waiting for? Put it back in, bitch"
I looked at Rex.
Rex: "Do as you're told. Put it back in"
Amy: "Bitch!"
The group laughed as I squated back down and positioned the butt plug against my hole. I began to slowly insert the rubber cock shaped butt plug back into myself. I got it about half way in before Rex told me to pause and slide it back out. And then to slide it back in. And then back out. Rex was having me fuck myself in front over everyone for their amusement. My aching balls began to churn and I could feel my penis began to ooze a small stream of pre-cum.
Greg: "Oh he likes it."
Rex: "Keep going. Let's see how long you can take it before you lose control."
I wasn't sure what he meant, but I obeyed. I continued to slowly fuck myself. As the pressure built I could feel myself feeling different. I began to feel it deep inside myself. It felt like I was on the verge of cumming but nothing happened. I was so desperate to cum at this point I began to whimper and moan. I fell to my back pressing the plug hard inside me while I arched my back and humped the air - and still no release came. I finally gave up. My only success being a small sticky white glob of cum coating the head of my tiny penis.
Amy: "That was hot as fuck. Brian, you need to take me home."
Brian stood right up. Even as a virgin I knew what she meant. Little white girl Amy wanted Brian's big black cock. He looked just like the guys from all the blacked porn I would watch and she looked like the girls. He would destroy her. She was so tiny. A small penis like mine would be perfect for her, but even tiny girls want a man to fuck them. Not someone like me.
Thinking about Amy getting blacked was making me so fucking horny. A thick black cock sliding deep into her. In and out. His big hands making the ass cheeks clap on his pelvis with each thrust, his low hanging balls swinging and slapping into my 2 month backed up ones. The head of his cock pressing against my prostate.
I caught myself. I wasnt thinking about fucking Amy or even Amy being fucked by Brian. I was thinking about Brian fucking me. Jesus christ what has gotten into me?
Rex: "Ok, ok, you can stop now, relax, you're going to hurt yourself haha"
I was snapped back into reality. Brian and Amy were already gone. Greg was just walking out of the door. I sat back up, my balls bluer than ever.
Rex: "I'm proud of you. You went above and beyond tonight."
Rex motioned toward my penis, "What's going on here, huh?"
Chris: "I-I don't know. It just did it on its own. I didn't touch it, you saw me not touch it. I wasn't masturbating"
Rex: "Calm down haha, I know. You're not in trouble. It's ok. What's the number one rule?"
Chris: "No masturbation allowed."
Rex: "Would you like me to help you try and finish what you started?"
Chris: "W-what do you mean?"
Rex walked over and crouched down next to me. He grabbed the base of the butt plug and began to slide it in and out of me with a slight twist.
Chris: "Y-yes! Yes please. Please help me."
Rex got up and walked toward his bedroom.
I quickly followed behind.