Sissy Gambling Debt Pt. 01

When I woke up from the bumpy sounds and rumbling feelings beneath me, I tried to make sense of what just happened. Feeling tired and mildly dazed, I opened my eyes to realize I was placed in the back of a van. My body felt numb and I couldn't move much. As my memories slowly started to come back, the last thing I could remember was making a sexual deal with a casino owner, and then someone from behind injected me in the neck with some sort of sleeping sedative. It for sure knocked me out pretty good as I don't recall how I got in this van. The deal I made with the casino owner was to become his degraded sissy sex slave to make up for my gambling debt. I owed him about $500,000 with 15% interest rates annually, and definitely didn't have the money to pay this back. Every year, I would have an additional $75,000 added onto my debt, and this ruined me financially. I had all my possessions taken away, and ended up on the streets homeless.

I was told that I could be sent to jail at anytime, but being a perverted fuck the casino owner insisted my gambling debt could be paid back sexually to him, and I foolishly accepted thinking it wasn't going to be a big deal. It was either that, or I faced the consequences of being sent to jail. Having a small body stature and being only 5'4'' tall with a small 3 inch dick, I wouldn't last a minute in jail without getting some unwanted sexual attention. I've heard of stories of smaller men like me getting fucked up their ass by bigger inmates, being peed on by multiple men, being forced to suck a lot of dicks, having foreign objects inserted into their anal cavity by alpha males, and being anally probed by prison guards. The idea of going to jail sounded like a lot more sexual work and more damaging to my asshole; so I chose to become a degraded sissy sex slave to one man, instead of becoming an abused sissy whore to multiple men.

Over time, the sleeping anesthesia started to wear out, and I started to recover more from being drugged up. It was then that I started to realize I was dealing with a very sadistic man. At this point, I didn't know what could have been more sexual, being sent to jail or being sexually humiliated here in my current position. Not only did he have me drugged me up with sleeping sedatives, he had me tied in bondage restraints. I had a ball gag in my mouth and all I could do was moan desperately at what was going to happen to me. The most noticeable thing however was that I felt an anal hook lodged up my ass, and it was tied to a rope connected to my neck. My legs were folded back and tied to my arms. This caused my back to curve back, accentuating my ass to stick out like a bitch as if I'm getting ready to be fucked. The only way I could relieve some pressure from the anal hook stretching my ass, was to arch back more. But this was tiring so I just relaxed to let the anal hook continue to stretch my asshole. I didn't think this casino owner had an appetite for my sexual suffering. Nonetheless, I felt sexual pleasure of being tied like a sissy bitch, and my tiny pathetic dick twitched from being excited. It even dribbled a bit of cum making me feel wet.

A few hours later, the van was still on the move and I was placed in this degrading position the entire time. Every time the van hit a bump on the road the anal hook tugged on my ass even more bringing me a lot of sexual pleasure. At this point, the wetness from all the precum dribbling out of my dick felt quite noticeable. It felt like I created a puddle of precum beneath me. The wetness made me feel like peeing, and I eventually gave in and peed myself in the van. This pee went everywhere as the van went uphill and downhill, causing the pee mixed with my own precum to slide all over my body. I never felt so degraded before, but I'll have to admit, I kinda liked the feeling of being degraded like this. Maybe I'm just starting to learn my place in this world, and I can do so while making up for my gambling debt. After a few more hours of having my own pee and precum sloshing everywhere, the van came to a stop. The doors opened and I could see the casino owner standing there and smiling at me sadistically.

"Well, it seems you have finally arrived! As my degraded sissy sex slave, you shall now be referred to as Amber, and you shall obey all my sexual commands. Are we clear?" I mumbled incoherently with the ball gag in my mouth and nodded, with the anal hook moving up and down in my ass as I nodded. The casino owner replied "Excellent! My name is Lucien, and I'm excited to start sexually degrading you. It seems you have made quite a bit of a mess in the van, I'll need you to lick up the mess you made in there." Lucien then untied my arms and legs to allow me to move, but left the anal hook in my ass which was still attached to my neck. Lucien then said "consider this your first sexual command." I obeyed Lucien like a docile bitch, and attempted to lick and swallow all my pee and precum in the van. The anal hook made it awkward for me to do this, but after an hour, I eventually licked the entire van clean, and swallowed all my pee and precum.