The next day came very quickly. I was in a severe state of confusion and regret. The inescapable nature of the predicament I had gotten myself into was weighing heavily on my mind.
I didn't want this. I wanted to be going out with my friends. having drinks and living the uni life. Instead I was stood on the road like a cheap hooker waiting for a man to pick me up and do god knows what to me.
He arrived earlier than last time. On this day he was not getting out of the car. The fake pleasantries he had used to charm me the previous day had been dropped.
He barked out of the window, "Get in the back seat, now."
I climbed in and closed the door behind me. I look to my left and there is a burly looking man sat next to me. He had multiple neck tattoos and his arms were the size of my thighs.
My stomach turned as the blood rushed out of my face. I tried to open the door but the childlock was set. My captor looked at me with a wry smile and said "Come now boy, don't do anything you'll regret."
With that I sat down, quivering with fear. my legs felt numb but the nerves in my arms felt electrified. I could feel the fight or flight response battling it out inside me.
My captor instructed me to take off my clothes and give them to the man sat next to me. "If you don't do it in 5 seconds I will airdrop the video of you to the nearest phone. I assume that would be your housemate, right?"
I gulped and started to reluctantly undo my trousers. I pulled them down along with my boxers. My cock was shrivelled and pathetic as all the blood had rushed out of it in my stress. I then took my T shirt off exposing my slim torso.
The man next to me flicked my tiny dick and laughed a booming deep laugh. I whimpered but sat still. Resigned to my current situation.
"Oh how rude of me." said my captor. "Let me introduce you, this is Carl, I like to call him my little helper." He grinned smugly. "And from now on you will call me Master, understand?"
I didnt respond. I just sat there with my head down, shaking.
Carl started rummaging around in a bag at his feet and pulled out a chastity cage. Now, I was no expert but this one looked expensive.
My captor looked at me and asked "Do you know what that is?"
I nodded although my mouth was too dry to speak.
He chuckled, "Of course you do you dirty slut, now Carl here is going to fit this on you and you're going to let him, is that clear?" once again I nod.
Carl grabs my cock and balls in one hand and starts feeding them through the plastic ring, my two balls went through first and I yelped at how aggressively they were being pulled.
"We have to make sure it won't come off pal, its gonna hurt a bit but once you're in you'll be sound." said Carl.
With that he grabbed my limp cock and pulled it through the ring. he flicked it again and laughed. "What a pathetic little clitty."
No one had ever called my cock a clitty before and I was absolutely disgusted by the word.
He slipped the cage part over my ever shrinking penis and clicked it into place. He inserted the locking bolt and turned the key, removing it and handing it to Master.
The cage fitted snugly, my flaccid cock was touching the end and the sides, but it didnt pinch anywhere, almost as if it had been made for me.
"There ya go." Said carl as he gave it a little pat that made my cock and balls rock in unison.
"Can I put my clothes on please?" I asked very quietly. So quietly it would appear no one could hear what I said.
"What?" Said my captor, "speak up boy."
I repeated myself just enough for him to hear but still very subdued, as if I was scared a passerby might hear me.
With this Master and Carl started absolutely howling with laughter. I was having trouble processing the situation but I knew at this point the previous day was a walk in the park and today things were going to get bad, really really bad.
We pulled up to my captors house and he gets out and opens the car door for me. I don't move, silently praying that this is all a dream and I will wake up in my bed back at my house.
He slaps me in the face, snapping me back to reality. Gesturing to the house, he instructed, "Go to the door."
It wasnt open yet and I was completely naked. There was no way I was doing that in the middle of the day! However all Master had to do was take out his phone and show me the video from the previous day ready to upload to a popular porn site.
With that I gulped, looked around and saw that the coast was clear. I ran to the front door, my locked cock flopping up and down with the extra weight. I was desperate for no one to see me, my head felt hot with embarrassment and I was sweating profusely.
I reached the door and pushed myself up against it. Willing it to open under my force alone. Carl and my Master sauntered slowly as I begged and pleaded for them to hurry up.
My captor started to talk very gently. "Okay I'll make you a deal, you can either stand out here, completely naked for half an hour so everyone in the area knows what a faggot little bitch you are, or I can let you in but you have to complete 5 challenges of my choosing. It's up to you. but if you decide to go inside, theres no going back, and remember, I still have the video."
I didnt even need to think, I saw a car approaching at the end of the road so I squealed "The challenges, please I'll do the challenges, just open the door!"
He unlocked the door with an evil smile and just like before gently pushed me inside.
This time however I wasnt directed upstairs. Upon entrance Carl led me past the stairs and to a door underneath them.
I was kinky enough to know what was probably behind that door and my heart sank.
Carl unlocked the door and told me to go down the stairs. I followed the instructions, as by this point I knew there was no use in fighting it.
Carl and my Master followed me down. locking the door behind us. I reached the bottom of the stairs and stood in a cavernous brick walled room with white tiled floor slopping on all sides to a drain in the middle.
I looked around with bewilderment. It's in the category of what I expected but it goes way beyond anything I could possibly imagine.
the walls were covered in hooks and shelves that were full of every possible toy you could name, rubber fists, large anal beads, a series of bad dragon toys, increasing in size. You name it, they had it.
there was an electro kit on a metal trolley. and a shock spot fucking machine on wheels. A sex swing hung from the ceiling and a spanking bench sat next to it beside a cage on the floor. Multiple other pieces of furniture I couldnt even figure out littered the room.
Chains hung from all over the place and there were metal hoops littered across the walls and ceiling.
I stood there, terrified and in shock. Unable to move until Master spoke. "Okay you little slut. your first challenge starts now."
"the first one is an easy one, as we already know, you're a proper little anal slut so you should breeze through this."
He grabbed a large and aggressive looking plug from a shelf. It was black and had three knots on it. each one larger than the last moving towards the base. It must have been 6 inches long and at least 3 inches in diameter at the widest point.
I looked at it in fear, certain that I couldn't take something that large.
"Okay, so you have 10 minutes to get this all the way inside you. If you fail we add a challenge to the end. and let me tell you, they start off easy."
