My decent into submission began on a rainy night in downtown Pittsburgh. I wasn't a regular hustler on the Mellon Square track but spent time there when I needed the money and action. I was 23 and had older guys salivating to get at me. Most wanted to suck a young guy's cock and gladly paid for the opportunity. On occasion I got the kink guys who usually wanted some verbal domination and fetish action. I really liked these johns because I was kinky and the gigs were easy. Most wanted spanked and some desired body worship.
The rain limited the johns that night. But a regular guy kept making the rounds in a van. He was known by the hustler's as Big Bad Bob or simply BBB. He liked rough kinks and paid really well. He looked me over a couple times before motioning me to the van. He was a stocky bearded guy and I had not done a gig with him before. He said that he'd take me in the van to a secluded spot outside of the downtown area. He asked if I did kinks and said he wanted an hour and would pay $200. Most johns only wanted to spend $50 or less. I wanted that cash!!
He said, "I want you naked in the back of the van. I want to feel you up and smack your ass. You don't have to suck me but I want to make your ass red. It will get me hard and I'll jack on your face. You have to take the spanking to get the cash. And wear my cum like a good bitchboy."
I was used to being on the Dom side of things and had not been used this way before. He could see the look in my eye. He said, "I want your answer now boy!! Tell me you'll be my bitch or stand in the rain and you won't make shit."
His attitude meant business. And I wanted the cash. I figured he was mostly talk as most of the guys were. I thought my young ass would get him off quickly and I'd have his money in a lot less than an hour. I looked him in the eye with a smirk on my face and said "I'll be your bitch for $200."
My attitude must have pissed him off. He put his meaty hand on the door and told me to bow my head and kiss it. "Bitchboys follow orders to get this kind of cash." I wanted that cash and bowed my head in the rain and kissed his hand.
"Now get in the van and kneel while you strip and I'll take you to your discipline" he said.
I got in the side van door and onto my hands and knees while he pulled away. As he drove silently I stripped off my clothes. I was kneeling naked and felt different because I was usually in control of the gigs I did.
He drove out of town and pulled into a rest stop area off an interstate. He parked away from the truckers and other cars. He told me to bow my head down and he got out of his captains seat and pulled blinds down to cover the windows. He turned the radio up to muffle any sounds.
He told me I wouldn't get paid until my face was covered with his cum and then I would have to take the money in my mouth from between his bare toes. My head was bowed but I could hear him removing clothes. Suddenly I felt him grab my ass cheeks roughly. Then a hard smack that made me jump. "Stay fucking still bitch and take your spanking and earn that cash." I didn't answer as expected and got a much harder smack on the other asscheek. "Did you not hear me boy?" he said.
"I'm sorry Sir please have mercy." I begged. Only two smacks and my ass felt like it was on fire. I immediately got two more really hard smacks on one asscheek. What the fuck had I gotten myself into.
"Thank you Sir!" I was learning that this would not be easy cash. The words were barely out of my mouth when he blasted my bare ass with four more very hard smacks. With tears welling in my eyes I kept silent but whimpered slightly. He clearly had done this enough to know that he had me right where he wanted me. My ass was burning. but I was afraid to protest and lost the pay. I was being quickly tamed and trained.
He made me kneel there for a couple minutes before he continued my torment. I felt his bare foot placed on my back as I knelt in naked submission.
I blurted out, "Please have mercy on me Sir."
"If you want mercy you have to earn it." he said and with that he took my head by the hair and lifted my head. He was naked from the waist down and had a muscle shirt on. He was a big burly guy and I felt very intimidated naked with a burning ass. He sat in a side seat in the van and lifted a big, bare foot to my face. "I can make your ass hurt as much as I want because I paid for your ass bitchboy." he said with a wicked smile. "But if you show me you'll lick and suck that foot the way I like your ass gets a short break."
"Do we understand each other bitchboy?"
"Yes Sir." I said in submission as I pressed my lips and tongue to his bare foot. His foot tasted of sweat but I licked and kissed his soles and toes in earnest to earn some mercy for my burning ass. "Good boy now suck the toes." he said.
"Yes Sir!!" I replied quickly. I now feared the smacks on my ass.
I went to work on his pudgy toes and sucked like the slave I had become. I did not look up at him and concentrated my efforts on his pleasure. I heard a moan from him as I sucked the toes and ran my tongue between them to save my ass and hopefully gain his favor.