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DISCLAIMER: This story involves chastity, butt plugs, small penis humiliation, and sexual acts between reluctant but consenting adults.
The Most Important Rule Part One
I can't take it any longer. I think I'm starting to understand now.
But let's rewind for a second. About six months ago my manager, Rex, called me into his office to inform me that they had to let me go due to the economy. I was the youngest member of the team - only 24 years old - with the least amount of experience so I was the odd man out. Rex's real name was Richard and he was a really cool guy. He was in his early 50's, maybe 6 ft tall. Red hair with a typical dad bod. I could tell that he didn't want to lay me off but had no choice. The order was coming down from corporate. Rex walked me back to my desk and he helped me gather my things before walking me to my car. We said our goodbyes and he told me that if I needed anything to let him know. He will do whatever he can.
I thanked him and went back to my apartment. I immediately started looking for a new job. I only had enough in savings to pay for rent and my other expenses for two months.
My search failed.
As the weeks went by I became more and more desperate. I was two months behind on bills and had no money. I was days away from my cell phone being shut off and as a last resort I texted my old boss Rex.
"Hey Rex, it's Chris. Hope you're doing well. I'm not doing too well right now. Job search has been a failure and I'm really starting to get behind on everything. Do you maybe have any connections or anything to help me find some work? Sorry to bother you, but thought I'd ask"
I barely had a chance to put my phone down before it started ringing. I was a little surprised and nervous to be honest but answered it. Rex asked me about what was going on and so I explained everything to him. He told me that he didn't have anything on the table right now but he would ask around. He said I could stay with him in the meantime. He insisted on it. He felt like it was his fault I was laid off and that it was the least he could do. He insisted on it. I really didn't have much of a choice and so I agreed. I packed up my clothes and other belongings and headed out to my car.
My car was gone. It was repossessed. I almost lost it right there in the parking lot. I sat there staring at the empty spot for what seemed like hours before building up the courage to call Rex back and ask if he could pick me up, which he agreed to do.
That was two months ago now. Two very long months. But that was part of the deal and I agreed to it. I only have myself to blame.
When I first arrived at Rex's house those 8 weeks ago he stopped me at his front porch before unlocking the door and told me that he was glad to help me but that there would be some strict rules I would have to follow if I wanted to stay there. He opened the door and invited me in. He gave me a quick tour and showed me where I would be staying. It was a small office room that was converted into a guest room. It was probably around 10'x8'. There really was only room for a twin bed and dresser but I didn't have much room to be picky or complain.
I settled in and met back with Rex in the living room where he began to go over some ground rules. Most of them were what you would expect. Things like clean up after yourself, don't leave dishes in the sink, make sure you turn off the lights, and stuff like that; however, there were some other more unique rules as well. Since I was living there for free he expected me to do his laundry, yard work, and have dinner ready for him when he got home. On Sunday mornings he asked that I cook breakfast and have it ready by 9am. Nothing too extreme and fully understandable for someone freeloading. I agreed without a hitch. Finally Rex said there was one more rule. The most important rule.
Rex grabbed a small black pouch and handed it to me. He told me to open it and if I knew what it was. I unzipped the bag and inside was a razor, shaving cream, a chastity device and a small butt plug. I was sort of at a loss of words and although I did know what they were I didn't want to admit that I did.
"This device goes around your penis and prevents you from masturbating. There is no masturbation allowed in this house Chris. This here is a butt plug. It slides into, well, your butt. I need you to wear both if you're going to be living here. Are you ok with that, Chris?"
Again, I really didn't have much of a choice did I? Where was I supposed to go? The street? So, I agreed.
"Excellent! Here, why don't you take a shower and shave your pubes so that its more comfortable to wear. When you're done call me in to inspect and attach the lock."
I got up and headed toward the bathroom before he interrupted me.
"Oh, sorry. I'm still in the middle of remodeling that bathroom. You'll have to use the one in my room."
He escorted me to his bathroom attached to his bedroom and turned on the water for me. Told me to take as long as I needed. I got into the shower and washed myself before lathering up my pubes and preparing to shave them off. I didn't have much anyway. I wasn't very hairy but as I began to think more about what I was doing the harder my penis became. I was only around 4.5" fully erect. Maybe slightly smaller if we are being honest. Not very thick either. I could easily slide it into a toilet paper roll but none of that matters when you're home alone watching porn. I started to think about what was about to happen. bringing in chastity and not being allowed to cum. Ive watched so much chastity femdom and cuckporn over the years I couldnt help myself but begin to masturbate. I've thought about being in chastity many times but it was always just a fantasy and it was always some older woman that would be doing it to me - Not my ex-boss. That did it for me. Another man locking my little penis up began to really turn me on. I started stroking faster and breathing heavier. I'm not gay but for some reason I was really turned on my this thought. Maybe because it wasn't just a fantasy anymore. I was getting close and that's when Rex pulled the shower curtains open.
"Ahem! What do we have here Chris? Breaking the rules already?"
I instinctively stopped and tried to cover up, turning myself away from him. He slapped my ass playfully and turned me around to face him.
"Hands on your head"
He turned off the water as I put my hands on my head and turned the brightest shade of red imaginable.
"It's ok Chris. It will take some getting used to. I understand and I'm not mad. The chastity is only to break your bad habits. Eventually you won't need it at all, but because you can't be trusted I'm going to have to finish the job here. Keep your hands on your head for now."
Rex took the razor, pulled me closer to him, and began to shave my pubes for me. My penis was still rock hard with no sign of it going down anytime soon. I was so embarrassed and I think Rex knew it.
Rex was manipulating my penis while he shaved around it. It felt very good and although I tried to hold in my breathing and moaning and let it slip.
"So, how big are you anyway?"
I told him I didnt know which he rightfully called bullshit on. Every guy knows how big they are. The only time they say they don't know is when they know its small.
Rex began to stroke my penis now while asking me to be honest.
"C'mon Chris. What are you 6 inches? 5?"
He started to twist his hand around the head while stroking now.
"You're 4 inches aren't you baby? Tell me"
It felt so good and it was so humiliating having to admit how small I was. I began to moan and repeat that I was only four inches over and over again.
Rex stopped edging me and began to ask other questions while finishing up the shaving. He asked me if I was a virgin, which I was. He asked me if I really didn't know what chastity was and I admitted that I did know. He asked me what my phone and laptops passwords were so he could look at what kind of porn I watch and I have those to him as well.
At this point he turned me around and ordered me to bend over and spread my cheeks. He began to lather around my butthole with the shaving cream asking me if I liked how it felt. He asked me if I had ever inserted anything to my butt before and I told him no, which was the truth. He asked me if I thought I would like it and I told him I wasn't sure. At this point he began to slowly push the plug into me. Gradually pushing it in and out a centimeter at a time until it was fully inserted.
"You can let go of your cheeks now. How does it feel? Not too bad, right?"
It really wasn't too bad. It wasn't very thick or long and I told him it felt sort of annoying but not in a bad way.
Rex began to laugh and say "Thats exactly how a girl would feel if you ever got a chance to fuck one!"
While still laughing at his own joke Rex turned the shower back on but with only cold water this time. I jumped in shock and he told me to take it. He needed to rinse off the shaving cream as well as have my boner to go down so he could put on the chastity device. I sat there enduring the water as he ran the water over my hairless body. Once my penis and balls shrunk down to size Rex began fitting the small metal device onto me.
Rex tossed me a towel and motioned for me to follow him back into his room.
"All locked up and safe now. Any questions?"
Before I could answer his question, he said "You're probably thinking about how this no masturbation thing is going to work. Now, remember, I said no masturbation. I never said no cumming. You are 100% allowed to cum - just not via masturbation. Do you understand?"
I was a little confused. How else was I supposed to cum if I wasn't masturbating? I don't have a girlfriend. I cant have sex with a chastity device anyway. He must have noticed my confusion because he followed that up by saying, "It might be a week. Maybe 2 weeks. A month. 6 months. We won't know till it happens, but when it's time it will make sense."
Two months later and It's finally making sense.
I've never been this horny in my life. Everything is turning me on. Everything. I looked over at the clock. It was nearly 1am and I couldn't sleep. It was time. I slipped out of bed and quietly walked toward Rex's bedroom.
I could hear him watching TV and laughing at whatever was on. I quietly knocked on his door and asked, "Sir, are you awake?"
He invited me in and turned on the light by the side of his bed. Asked what was up and I dropped to my knees and began to beg him permission to masturbate.
"Please Sir, please allow me to masturbate. It's been 8 weeks now and I'm desperate to cum. Please Rex. I will do anything. Please grant me permission. I've been a good boy. I've followed all your rules. It's hard to think straight. Everything is turning me on. I can't focus. I'm desperate for release. Please-"
Rex cut me off with a slight giggle in his voice. He got out of bed and walked toward my sulking little body kneeling on the floor in near tears.
I slowly raised my head to look at him and there it was. A rock hard 8 inch cock as thick as a redbull can at least.
"Tap kiss it"
I guess a part of me knew this was a possibility but I didn't want to believe it.
"We will take it slow, Chris. Just follow my lead. I won't force you to do anything. Tap kiss the tip"
Rex pointed his cock down toward my face. I stared at it staring back at me. It looked angry. Throbbing. I closed my eyes and tap kissed it right on his piss slit.
"Good. Do it again but with your eyes open this time. Look at me when you do it. don't take your eyes off me."
I opened my eyes and stared into his. He guided the tip of his cock back to my lips and I tap kissed it again.
"Again"
I did it again.
"Again"
It was getting easier now.
"Keep staring at me. Now lick your lips and do it again. Just keep licking your lips and giving a kiss. Repeat that for daddy."
I continued to stare into his eyes and followed his instructions.
"Very good, now lets try to combine it. lick your lips while you kiss it"
It took a couple tries for me to get in a proper rhythm but with every kiss I began to get the tip of his cock more and more wet. I did this for another 10 or so times before I felt him pushing the tip of his cock just ever so slightly deeper into my mouth.
"Now, I want you to keep doing what you're doing but open your mouth slightly wider when you kiss it. Dont stop staring at me."
Again, I obeyed. Everytime I kissed him his cock slipped deeper and more easily into my mouth.
"You're doing great Chris. Now instead of trying to lick your lips I want you to use your tongue to lick under the head each time. Get it nice and wet now."
He began to push deeper into my mouth now until finally it was no longer leaving my mouth after each thrust at all.
"There you go Chris. You're sucking cock now. Like a good little boy. Dont stop. Just keep doing it exactly like this. Keep the same rhythm. Don't think just suck now."
I didn't want to disappoint him. I tried to perform like a machine. Every motion exactly the same as the last as possible. The spit was drooling out of my mouth now. I was afraid to pause and swallow. I didn't want to disappoint him. I just continued to do as I was told and I was not told to do anything but suck.
"You're doing a great job. You're making me feel very good. I want you to start thinking about cum now. Think about how badly you want to cum. Think about how good it will feel to shoot a big hot sticky load.
I almost forgot about how horny I was. I needed to cum so bad and how good it will feel after 8 weeks backed up. my little penis was still caged and aching to be free.
"Think about how good it would feel if someone was doing this to you. Pretend the cock in your mouth is yours. Suck it how you would want it to be sucked"
At this point I began to suck harder and faster. Twisting my head when the tip of his cock reached the tip of my mouth. Slurping the drool and spit. He began to take control now.
"I'm almost there Chris. Let daddy take over. You just keep sucking"
Rex had one hand behind my head and another on my cheek. He was doing his best to hold my head steady while he fucked my face. I continued to try and look into his eyes but he held my face forward until he started to slow down his thrusts and remove the hand from cheek. He still had one behind my head but he was now looking right at me slowly pumping in and out of my mouth. His breathing was getting heavier and heavier.
"Ok baby. Daddys about to cum. Don't do anything. Just let daddy shoot. Aw fuck bitch. Fuck. Yea, take that cock you little dick sissy bitch, yea, awwwwww fuckkkkk!"
Rex began to shoot rope after rope of hot cum into the back of my throat. I stayed still and let him finish. He held his cock in my mouth for 30 seconds or so after he was done cumming before telling me to not spill a drop. He slid his cock out of my mouth and told me to show him what I made him do. I opened my mouth for him to see. I'm sure it was a site. It felt like my mouth was completely full.
"Good boy. You can close your mouth but don't swallow yet. I want you to get used to the taste. Swish it around in your mouth."
I did as I was told. it had a sweet and salty taste. Nothing like I've tasted before. A very unique type of flavor, but it wasn't a bad flavor. Just different.
"You can swallow now."
I didn't swallow right away. I didn't think I had the proper time needed to really understand the flavor and so I swished it around a couple more times before finally swallowing.
"Say it"
I was a little confused and gave a puzzled look.
"Say you're a cocksucker"
I responded by saying, "I'm a cocksucker. I'm your cocksucker. Your little dicked bitch cocksucker"
"That's not all you'll be. Now, why did you come here again?"
Still on my knees I looked down to the ground and asked for permission to masturbate once again.
"Masturbation isn't allowed, remember. The answer is no. Now go to bed. I'm tired."