Road Trip with Master Jon

I knew Master Jon was traveling for business, and he wanted his slave boy nearby and accessible. My cock swelled painfully in its cage when Master Jon said he might be generous, and let him accompany him on this trip to Saint Louis. I had not cum in over two weeks, so I was too horny to think straight and begged him for the chance to serve him on this trip. I did not have to beg too long before he agreed. Business trips usually suck but having an almost no-limit sex slave to use would make the trip so much better.

This was a dream come true for me. Master Jon had provided me with generous virtual training, and I had the joy of worshiping his sweaty feet a couple of times. I even had a discipline session in my home, but so far I had not earned the privilege of real in-person sex. A week or so earlier, Master Jon had messaged me that he had almost completely brainwashed me now. I'm not sure what he meant, but I wanted his hard cock to touch me in an almost disturbing way. How could I miss and crave something I'd never had? Somehow I did crave the feel of his cock anyway he was willing to give it to me. I instantly accepted and thanked Master Jon for taking me with him, and did not even think about how hard it would be to explain disappearing for 6 nights and days.

It was not easy, but I found a way to take off from work on short notice without looking suspicious. Getting away from home was more of a problem. Saying I was traveling on business would be a risky lie, and who knows, he might want to come along on a business trip if he could get off work. I settled on saying I had to go to east Texas to see family because of an emergency. That was no risk since he always has a "good reason" not to go with me to Texas to see my family. The main thing was I was clear to be Master Jon's 24/7 slave and toy for 6 whole days.

We were to leave on Sunday at 9 AM. Master Jon told me to meet him at Wolfchase Mall and leave my car there. Master also told me what to pack.

Every Jockstrap I own

6 tight tee shirts

6 pairs of white socks

2 pairs of workout shorts

The loosest pair of jeans I own

One polo shirt

Leather belt

My biggest dildo

My biggest vibrator

My best regular butt plug

A remote-controlled butt plug suitable for long-term use (I had to buy this item)

My O-ring gag

A penis gag

Ankle and wrist cuffs

Zip ties

Soft rope and scissors

Red Bandana

The packing list said a lot about what kind of trip this will be. There were more sex toys on the list than clothes. I noticed that my stainless steel chastity cage was not on the list. That was deeply disappointing. The metal cage is a big showpiece and would look so good in posing pics or amateur porn. I was hoping that with so much privacy, Master Jon would take pics and videos of him using me or disciplining me. I would love for Master Jon to use me and record it. If Master Jon hid my face, I would love for him to post pics and videos of training, use, and discipline. I want men to see my Master's' awesome hairy body and how he knows how to use his slave. Let Doms and other slaves see what a good slave that Master Jon has made of me. I think Master Jon would enjoy a video of him raping my throat. That would show my face, but I would still be proud if he shared that kind of video with men he trusted. I would be so happy and proud if he showed me off as his good slave. All this is just wishful thinking. He would have had me bring the uncomfortable but impressive-looking stainless steel chastity cage if he planned to take pics and video.

I was at the Mall early. I'm always early when I meet Master Jon. I don't want to disappoint him and force him to wait, or worse, have him leave me behind. I parked where he said at the most deserted part of the lot. As ordered, I was wearing a pair of gym shorts, my blue jockstrap, and a tee shirt. Of course, I was wearing my purple soft plastic chastity cage. Per Master's orders, my hole was clean and lubed, but not plugged, but I had my best butt plug handy just in case.

I had about 20 minutes to think while waiting for Master Jon. What I was about to do finally sank in. I don't mean the 24/7 submission and use, I more than wanted that. I mean getting into another man's car and driving away with no one knowing where I am or who I'm with. I mean no one knows where I will be and no one will look for me for days. Was I so horny and brainwashed that I had lost all sense? I've met Master Jon in person less than a half dozen times. I think he genuinely cares and even cherishes me, and I have no reason to doubt that. He has been kind to me, and the training has been firm but gentle. He hasn't misused me in any way, and he has led me where I wanted to go. Still, I only know what he has shared with me about himself online, and people get catfished all the time. The first time I get bound and gagged will be on this trip in a hotel that could be anywhere. If he has a real sadistic or violent streak, it will be too late when I find out.

When Master Jon pulled up beside me and I saw his handsome face, all my doubts and resistance faded to nothing. I did what I was trained to do almost like a robot. Standing at attention:

Clay: "Master, may I get in your car?"

Jon: "Boy, come around to the passenger side door. Good boy. Boy, what is a slave's uniform?"

Clay: "Master, a cock cage and a jockstrap."

Jon: "Boy, when you are in the proper slave uniform, you can get in my car."

I didn't know what he meant at first. I was caged and in a jock. Should I be plugged too? When I thought I knew what Master expected, I kind of panicked. I quickly looked around me and saw no one nearby, so I went for it. I did not know how long he would wait. I shucked off my shirt first. Gym shorts dropped off easily. In less than 20 seconds I was naked (except for the jockstrap) and sitting in Master Jon's car.

Jon: "Boy, you did that almost right, so I won't punish you too hard. Boy, where is the right place for a slave?"

Clay: "Master, On his knees and at his Master's feet."

Jon: "Boy, if you know that, why are you sitting in my car? If you are not ready and properly trained, we can call this off now."

Rather than talk, I scurried to my knees on the floor mat and had my head down in the "resting kneel" pose.

Jon: "Good boy. I'm good to my boy. Unlock your phone and give it to me. Good boy, now give me your wallet. Good boy, now give me the key to your cock cage. Boy, what is the longest time your cock has been locked up?"

Clay: "Master, 12 hours."

Jon: "We will shatter that record this week. There is a towel on the floorboard for you to kneel on, easier on your knees boy. Rest your head on my seat between my legs and do nothing more."

The angle was uncomfortable, but I could do it. I had my face about an inch from Master Jon's crotch, and I just relaxed because I was where I belonged. After a few minutes, Master Jon began to stroke my hair exactly like he would pet a dog. I know I should have some pride and resent being treated like a pet, but it made me feel good. Fuck pride and dignity, I'm his slave and he owns me. This went on for about an hour. Master listened to the radio and rested his hand on my head or stroked my hair. This felt so right.

Jon: "Good boy. Very good boy. I think I'll give you a treat."

That said, he pushed the right leg of his shorts up to expose one of his balls. It was hard not to just push my nose and face into the crevice between his thigh and nut, but I was a good boy and stayed where I was and said:

"Master, please! please!"

Jon: "Boy please what? What do you want to do?"

Clay: "Master, please let me lick and taste your crotch and nuts."

Jon: "Boy you have not earned that. But points for enthusiasm." You can push your face forward. Bury your nose in the crevice next to my nut and enjoy your Master's scent."

Master Jon barely got the words out before my face was touching his nut. I could feel and smell his sweat. I didn't even realize I was huffing Master Jon's pheromones till he said to slow down.

Jon: "Boy, slow your breathing before you hyperventilate. You don't need to suck every molecule of my funk into you now. We have time on this trip. I'll make lots more smelly funk for you to suck into your face. I promise. Boy, is your cock cage getting fuller? Looks like you're trying to bust your cage open and your nub is jumping. Do you get this horny just from a sniff? I'm going to enjoy you this week."

I huffed Master's pheromones more slowly but still was so horny. I was almost high. I think Master Jon deliberately tries to keep me so horny that I can't think straight but only focus on him. Master controls when I can touch my cock, when I'm caged, and of course when and if I'm allowed to cum. I went from cumming twice every day before Master Jon took over down to only on rare occasions when Master Jon is exceptionally generous. As generous as he is, he is not generous enough to let me cum frequently. A load has been building up in me for over two weeks, and Master Jon's cock and balls were right at my lips, so yea I was horny out of my mind.

Jon: "Boy you have had your nose in my junk for 20 minutes. Do you want to stop?"

Clay: "Master please no! Please don't make me stop. Please!"

Jon: "Good boy. Boy, I am very pleased with you. I'm impressed you dropped everything for a chance to serve me on short notice, just like a good slave boy should. Going to let you have something you have been desperate for weeks. First, stick all the fingers of your right hand in your mouth. Good, get them good and wet."

Master Jon pushed my head back a little and pulled his gym shorts way over to the left and freed his cock and balls.

Jon: "Boy, beg for it. Say what you want."

Clay: "Master, please! please! Master, I more than want to kiss your balls and taste your ball sweat. Master. please. Master, I need to touch you with my lips. You own me, and I'm your slave, so my mouth needs to be pleasuring you. Master, please be generous with me"

Jon: "That's what I want to hear. Lick my balls slowly and gently. Use your wet fingers to fuck your sex organ. Use your other hand to play with your nipples."

I made one long lick first. I got my tongue as low and close as I could to his taint then licked up to the base of his still-soft cock. I know he showered this morning, but his musk and testosterone flooded my senses. I know Master Jon likes for a sub to make noise. That was no problem. The pleasure of being so close to Master Jon and the pleasure from my hole and tits made me moan like a whore in a porno flick. I should have been humiliated getting so much pleasure because a man permitted me to finger fuck myself and lick his hairy nuts. I was way past being ashamed of what I was, I was Master Jon's slave. I spent half an hour washing his balls with my tongue.

Jon: "Good job boy. I bet your fingers are getting pretty dry. Stop licking my hairy balls long enough to finger fuck your 2nd most important sex hole. Good boy. Do you want to finger fuck your main hole again? Tell me."

Clay: "Master, please let me finger fuck my ass some more and lick your balls more, please!"

Jon: "You can use your mouth again after you correct your mistake. Men have assholes, what do slave boys have?"

Clay: "Master, I have a fag cunt, a boy pussy made to take and serve my Master's cock. Master my only sexual pleasure comes from my hole, Master my hole was made for your use and pleasure, so it must be a cunt."

Jon: "Good boy, you are learning. Go back to finger fucking and enjoying your cunt hole. As a reward for thinking of the right answer, you can hold my balls in your mouth and massage my boys with your tongue."

It was not easy without using my hands, but I got both of his balls in my stretched-wide mouth. I continued to lick the bottom of Master Jon's balls and moan as I played with my nipples and cunt. Master started to stroke my head again and tell me what a good boy I was. I was so fucking happy and horny for 20 short minutes

Jon: "Fuck this is the only way to make a car trip. Boy, are you enjoying yourself? Are you still happy you are my slave and I let you come with me?"

I tried to talk and answer with a mouth full of hairy scrotum.

Clay: "Mastaaa, Im soo appy to uuck ur balls. Mastaa ank u soo uch or eting e cccome ith ooo Mastaa, im soo appy to be ur save."

Jon: "Boy I have no idea what you are trying to say but it feels good. Keep talking or trying to talk. I'll tell you when to stop."

I tried to tell him how grateful I was to get to spend time with him on this trip. I tried to tell him how much I wanted his cock inside my holes and his load in every hole of my body. I talked for five minutes of gibberish.

Jon: "Boy, you make no sense at all. Stop talking and mum for me. Hum the tune to "Sweet Home Alabama"."

Master Jon enjoyed it when I talked, but he fucking loved it when I was mumming on this nut sack. I literally gave him a hum-job. Before I got through the song, Master Jon was a full mast. I was straining in my cage and fucking my cunt as deep as my fingers would go.

Jon: "Fuck boy, you learned a new trick. You'll be doing this a lot in the future. I'm feeling exceptionally generous, so open wide and take my cock head into your mouth, just the head. No sucking or licking, just hold my cock in your mouth. Good boy. Now sing "Ros Row Row Your Boat."

Clay: "Ow, Ow Ow ur oat Gitee own eh steemm. Aherely Aherely Aherely ife is buut a eaaam."

Jon: "Fuck boy, your tongue is dancing on my piss slit. Boy, can you taste my juice? You got me pumping it out and into you, boy."

Clay: "Mastaa I uvve the ttttaist of ur eeecum."

Jon: "That's what I like to hear. Boy, hum the tune to "Bohemian Rhapsody."

I made it almost all the way through the song mumming the high and low notes as loud as I could. The sweet and pungent taste of Master Jon's juice was gushing into my mouth. I could feel him tense and feel his heartbeat through his dick head. It was the most intimate experience I can remember. I could see his nut sack get tight and I thought he was about to cum in my mouth, but I was not that lucky. Master Jon pulled me off him by my hair.

Jon "Greedy boy. Did I say you could make me cum? Your ass will pay for nearly making me cum when we get to the hotel. Get up off your knees, sit in the seat, and act like a man while we get lunch. You can use the towel to hide your caged cock and the wet spot on your jock. At the drive-through."

Master Jon ordered for both of us. He had a burger and fries, and I had only a vanilla shake.

Jon: "Boy, you look perfectly natural sucking cream out of a tube. You look good with your cheeks sucked in slurping up that sweet cream. Get a big mouthful and let me see. Open wide. You look natural with a mouth full of cream too. Swallow and lick up what dripped out of your mouth. If you're a good slave, you may get the cream you crave tonight."

The shake and a few of Master Jon's leftover fries were all I had to eat that day. We were not a long way away from St Louis, and Master Jon let me sit in the seat but not get dressed. We were already downtown when I was allowed to cover my naked body. We were staying at a nice downtown hotel, but not in the same room. Master Jon did not want his coworkers or clients to see a fag sex slave coming in and out of his room. We checked in separately. I called Master Jon on the hotel phone (Master still had my cell) as soon as I was in the room and naked.

Jon: "Boy, I'll be in your room soon. I expect the door unlocked and you in the proper position."

I had learned many poses and many positions for a slave. What did he mean? On my knees by the door? Inspection? Resting front? I quickly settled on the Table pose on the bed with my white buns facing the door that was cracked open. The Table is Master Jon's favorite pose for me. I was in that exposed position waiting for 15 or 20 minutes. When Master came in, I could hear but not see him. The first thing I felt was his finger sliding up and down my crack. As he pushed a finger into my hole, he said

Jon: "Boy, who owns this?"

Clay: "Master, you own my boy pussy."

Jon: "Boy, remember what you are supposed to do."

Master Jon was working his finger in and out of me when I felt the first hard slap on my ass.

Clay: "Master, One thank you, Sir."

There were ten hard painful blows, and I counted and thanked him for everyone.

Jon: "Boy your cunt clamps down tight every time you feel pain, interesting. Boy, don't you ever make me cum without my permission. I decide when, how, and where my seed is given. When you are edging me, it is your job to sense when I'm close and back off until I decide you have earned my cum. Boy, "Kneeling Collar Me" pose

While I was kneeling, Master blindfolded me with a bandana.

Jon: "Standing Collar Me pose."

Master Jon sat on the bed and maneuvered me to face him. He unlocked my cage and started to remove it. Getting the cage on and off is always uncomfortable if not painful when I do it gently. Master Jon's strong hands pushed and pulled my boys around and I cried out in pain. I could not help it.

Jon: "Be still boy. Be a good boy. You can take this."

It hurt but was over fast. Next, I felt the cool slick flow of lube on my cock and balls. For a second, I thought Master Jon might let me cum, but that was not what the lube was for. The cold hard pressure on my nuts told me a stainless steel ring was going around my junk. Master Jon was not especially gentle getting the cage ring on and I whimpered but stayed still.

Jon: "Easy boy. You can do this. This ring is a little smaller than the one you like, but it will go on you."

The pain in my nuts made my hard-on deflate enough to slide it into the ring. I was relieved when I felt Master Jon's hands give my balls a final tug down and let go.

Jon: "Good boy. Feel good? No? You'll come to love it and feel naked without it. I have a surprise for you. One of your slave brothers loaned this to you for this trip. You'll have to message him about how grateful you are. I'm going to take off your blindfold and show you what you get to wear this week."

At first, I didn't know what I was looking at. It looked kind of like an oversized stainless steel thimble with a hole in the bottom. I think Master Jon saw the panic on my face when I realized what he was showing me.

Jon: "Calm the fuck down, boy. Do you trust me?"

Clay: "Master, yes you know I trust you."

Then stay still and be brave. Be Masters brave boy. Don't disobey me and make me tie you down. You will fit into this, no discussion. Your cock will fit in this and you will learn to love it eventually. What does a good slave say now?

Clay "Yes Master, thank you, Master."

My cock shaft was already slick with silicone lube but was too big for this cage. My cock usually tightly fills a standard-size cage, and the one Master would force on me is a small or maybe even a nano size. The length was less than half of a standard shaft cage. I trusted Master Jon but still could not imagine how this could possibly work. As usual. Master Jon had this planned out. He had me lay on my back near the edge of the bed. First, there was the pain to my tits as Master Jon worked them hard, then there was the painfully cold piece of ice on my cock head (Master must have brought a bucket of Ice with him) Two maybe three minutes of the double pain and Master Jon was ready. He used his thumb to first push my cock down. I had shrunk so much that my cock head was covered in my skin like I was uncut. The solid shaft cage went on and squashed my cock down even more. There was no pinching or pain as it was locked in place. I was not sure about this. I definitely was not happy. I never wanted to be in chastity, but Master Jon somehow made me not only agree to it but somehow make it feel right to be caged to focus more on his pleasure and my real sex organ, my hole. We never talked about me wearing a nub or nano chastity cage. I guess it is just another of many soft limits Master Jon has shattered for me. I thought at least the worst is over and I'll only have it on for a few more hours before bed.