Street Hustler Tamed and Trained Ch. 05

BBB had called me the day before and given me a time to report to him. He told me he'd have a surprise for me when I arrived. He didn't go any further with an explanation and I knew better than to ask.

When I arrived at his house I entered as normal and went to the bedroom where I would undress and put on my collar and leash. I did this quickly as I wanted to learn of the surprise and show BBB I valued his time.

I went down the stairs to his dungeon/playroom and before I could get on my knees saw BBB signal me to stay up. He was sitting comfortably on the leather couch and at his feet was a man posed silently. I didn't immediately recognize him as his head was bowed at BBB's feet. His hands were clasped behind his head. His legs were spread wide and his bare feet raised. When I got closer and saw the toe rings on his feet I knew who it was.

I was surprised to find Leo Lyle in this position. He was a young street hustler who was 20 but looked much younger. Folks said his young looks were his calling card as the johns who wanted the fantasy of an underage guy drew them to him .He had a cocky attitude on the streets and the toe rings and pedicured toes were an example. He also kept his fingers manicured. But at the moment he was clearly in submission to BBB. He had always told the hustlers he didn't sub for anyone because he didn't have to.

BBB motioned me to sit beside him. He explained that Leo was in trouble with a couple of powerful johns who he and his girlfriend Andrea had stolen from. They had lifted some jewelry from the house of one john. And Andrea had used a credit card skimmer supplied by Leo in a strip club where she worked part time.

BBB further explained while Leo knelt without movement that the options to settle these problems were Leo's enslavement or prison. Leo was not a tough guy. He feared being jailed and regularly raped and beaten. The john's had connections and could make things very difficult for Leo and Andrea. Leo would be trained and pimped to make restitution. BBB nudged Leo's face with his bare foot. He said tauntingly, "Isn't that right Leo?"

"Yes Master!" was the reply from the suddenly subdued Leo.

BBB told me to take off my collar and leash and fit it on Leo. I did what I was told. I admit I was enjoying this as Leo was not one of my favorite people. As I clasped the leash on the collar I was told to put my bare foot under Leo's face.

BBB taunted Leo, "You are wearing the collar and leash my bitchboy Footsy used to wear. Kiss his feet!!" I could feel Leo's tongue work on the tops of my toes and then his lips caress my bare feet. It felt especially good knowing that mouth had said it was above such acts. BBB had him continue this act of humbling foot kissing for some time.

BBB then told me, "Footsy smack his spread ass and show him his new place." I reached down and smacked Leo's ass hard. Leo squealed and twitched his ass.

"Give him ten more hard ones." BBB commanded me. I went to work slowly and whacked his ass cheeks five hard ones each. Leo continued to whimper and squeal. His ass was pink. I noticed as I smacked his ass his toes curled and that excited me.

"Now give him five hard ones on his asshole." BBB ordered. I went to work and enjoyed smacking his asshole hard and hearing Leo whimpering in what sounded like a cry.

BBB ordered Leo to his knees but to keep his hands behind his head. Leo did as ordered and I could indeed see tears in his eyes. BBB looked at me with that wicked smile and said, " We know what we do with bitchboy tears. Don't we Footsy?"

"Yes Master!" I replied.

And BBB wiped at Leo's tears and smeared them on his big, hairy balls. "Kiss your tears!!" was the command to Leo. BBB took the leash and yanked it down with Leo's face to his balls. Leo flicked his tongue weakly at the hairy balls. BBB was unimpressed and told me to get the cane from the table nearby. Hearing that made Leo start to lap at BBB's balls. But his efforts were too late.

"Stripe his ass and then tenderize his soles Footsy!" was his command to me.

I took the cane and aimed at the pink ass cheeks of the new slave. The first stroke hit the left cheek and Leo screamed. I quickly took aim at the right cheek and struck it with more force.

"AWWWW..Please Master!!" Leo begged. "It hurts sooo bad!"

"Shut the fuck up and take it. Get used to it. Until the guys get paid I own your ass!! BBB barked.

"Now hit him harder on each cheek and each sole!! BBB told me.

The two cane strokes on his ass cheeks made Leo cry. He had stopped licking BBB's balls in his pain and that got him a face smacking.

BBB ordered him to present his soles and now Leo was shaking. He cried as he resumed licking BBB's balls. I loved the chance to cane his soles. I wanted to see him curl the toes and make the toe rings dance. The first cane stroke was on his left sole. It made him cry more and shake in pain. The second on his right foot was even harder.

Leo screamed in pain, "Owwwww. ohhhhhh!!" The pain had to be intense. Tears rolled down his face and his whimpers were proof of defeat.

"Good job Footsy." BBB told me. "You can have your way with his tenderized feet for a few minutes." That was music to my ears as Leo did have very sexy feet. Pale skin and smooth soles. Pedicured toes with clear polish. I sucked his toes and licked the smooth soles. BBB had stuffed his thick cock into Leo's mouth. He was getting his face smacked as he was forced to suck.

After a few minutes of this BBB made Leo bow and pose again as he had when I entered. I was told to get some clips from the table and clip Leo's cock and balls. Leo's cock had shown no response from any of the treatment. I knew this did not please BBB.

I was hard from the action and especially getting to have my way with Leo's smooth feminine feet. I clipped Leo's balls with three clothespins. I lifted under him and put one on the head of his cock and another on some shaft skin I pinched. He cried out but was resigned to his fate. BBB smashed his head down with his bare foot and told him spread his ass wider. The phone rang and BBB answered. He gave directions and told the person on the other end they would be met at the door by me.

I was ordered upstairs to greet our next guest and bring them to the dungeon. I was surprised to meet a young lady who would turn out to be Leo's girlfriend Andrea. She was scared and nervous. I took her downstairs and she gasped when she saw Leo bowing with a red ass and cane stripes. Andrea was slender and had short frosted hair. Not beautiful looking but sexy in an odd way.

BBB explained that she and her boyfriend were in deep trouble because of some stupid attempts to steal from some powerful and important people. Leo had made the decision to become a pimped slave to avoid the ravages of a young punk in jail. Now it was Andrea's turn to make a choice.

Seeing Leo in submission brought tears to her eyes. She was told she could either join him in slavery or spend rough time behind bars. And she had one minute to choose. She dropped to her knees and begged for time to find ways to pay the debt. She was told the debt would include whatever penalties and interest that BBB decided starting today. A phone call would start the legal processes if she didn't agree to slavery. She bowed her head and said she had no choice.

I was told to strip her and put her clothes upstairs. I did so and when I returned she was beside Leo in the same pose. I was hard from looking at them this way but also because they both had sexy feet. She had matching toe rings on long toes. She had a beautiful ass and a shaved cunt.

I was told to take Leo's leash and he took Andrea's hair. They were brought to their knees and forced to view each others tear stained faces. But the extent of their initial degradation was just beginning.

They were ordered into a 69 position with Leo on the bottom. I was ordered to enter Andrea from behind. I lubed her first. BBB sat on the couch and used Andrea's back as a footrest. She moaned as I thrust into her with force. BBB told me to lube a thumb and stick it into her ass. When I did she cried out in pain. BBB took a bare foot and pushed her head down onto Leo's soft cock.

Andrea sucked without being ordered to. Leo was ordered to lift his head and lick my balls. He struggled to do so but lapped my balls and I pounded his girlfriend and thumb fucked her ass. As much as she sucked Leo was unable to respond. The cocky street hustler was reduced to a limp dicked loser. BBB taunted them both.

After several minutes of this I was told to wipe my cock on Leo's face. The slave couple was ordered to their knees. I was ordered to offer the thumb fresh from Andrea's ass to Leo's mouth. He resisted so BBB took him by the hair and I forced the thumb into his mouth. He gagged and choked. Andrea cried and trembled.

Leo was given one more chance to get hard before being punished for failing his captor. He was told to lube and fuck Andrea's ass. She would be on her knees with my cock in her mouth. Again Leo could not perform.

So the degradation would be increased. I would fuck Andrea's ass from behind while BBB spanked Leo's ass while he was on his knees facing Andrea. They were forced to kiss while Leo's ass was beaten. Andrea's ass accepted my cock easier than I expected. She was crying and trembling but I held her hips and drilled her asshole.

BBB spared no mercy in beating Leo's ass. He was crying and looking into Andrea's eyes as their tongues lapped each other. When BBB had had enough of the spanking he stood between the slaves and jacked his cock while spitting on them. This whole thing had me excited and I tore into Andrea's ass. It was not long before BBB unloaded on the slaves and made them swap his cum. I was told to exit Andrea's ass and take his place in jacking on the slaves. Again they were forced to endure a thick load of cum on their faces while swapping cum during the forced kisses.

Between their tears, our cum and BBB's spit they were a mess. But BBB had even more degradation in mind. He ordered me to wipe my cock straight from Andrea's ass on Leo's lips. Leo tried to resist but BBB had him by the head. I wiped it on his lips and smacked his face with it. Then they were forced to french kiss deeply.

Leo was told for resisting the ass cock he would be tied to the poles and punished. Leo cried and begged for mercy. He crawled to BBB and pleaded for a chance to redeem himself. Andrea was weeping and could not stop trembling.

BBB went to the table and brought back a folder. The paperwork inside included a full confession from both for their crimes. it also included a "personal services agreement" for both of them to sign. They both signed.

BBB told them they were owned until all money was repaid with interest and penalty to be determined by him. Leo would be staying with BBB for the weekend. Andrea was assigned to stay with me until further notice. They would no longer be a couple. They would be kept separately. Leo's limp cock would be fitted with a chastity device. The punishment on the pole would not be waived. But it would be administered by Andrea.

I was ordered to take them upstairs and shower them separately and scrub them roughly. BBB would watch and taunt the process. I took Andrea into the shower first and lathered her with soap. I was told to roughly scrub out each fuckhole. I enjoyed doing this and it made me hard once again. I rinsed Andrea and it was Leo's turn. I took him into the shower and lathered him. I especially enjoyed sticking my soaped up fingers into his ass and making him take it. I edged his cock with a soaped hand but he still couldn't get it up. The humiliation of it all left him limp.

Once rinsed they were both taken back downstairs and Leo was tied between two poles. I could see him shaking in anticipation of the pain he would have to endure. I was told to give Andrea a cane. She would have to give him 20 strokes on his ass and legs. Then 2 hard extras for his balls. If she failed to show enthusiasm in his caning she would take his place.

She warmed to the task to avoid her own pain. Each stroke seemed to be a bit harder. Leo was in agony and moaning wildly as the pain increased. His ass was stripped and now his legs were getting it. The tears were streaming down his face as he thrashed with each cane stroke. Andrea was almost dry from her shower. She looked sexy naked and administering a caning to her once boyfriend.

I could not resist a look at her pedicured toes and toe rings as she wielded the cane and reduced Leo to a crying slave.

When she finished the 20 strokes BBB said I would get the honor of caning Leo's balls twice. Andrea handed over the cane and watched as I made Leo get on his tiptoes. I aimed the cane and the first cane stroke on his balls made Leo yelp in agony. He would have doubled over if he could but the bondage forced him upright. He look at me defeated and with a tear stained face shook his head no to implore me for mercy. There would be none. Again I ordered him to his tiptoes. I love watching the toes strain as I made him go higher. Once again I aimed the cane and it landed on his balls and made him scream.

Andrea was ordered by BBB to give Leo one final kiss and caress his damaged balls. She gave him a peck on the lips and caressed his balls which only gave him more pain.

I was told to take Andrea upstairs to be dressed. I was ordered to take her to my apartment and keep her naked there until I got phone instructions on her training. Her feet were mine to use but nothing else until training regiments were set.

BBB told me before I left that he already had a tentative deal for Leo. A gay couple were willing to buy his debt in return for his becoming a feminized "gurl" for one half of the couple and a young "boi" for the other. He would become LeeLee. They would come and inspect him tomorrow and audition him for their use. The couple were both well off and would not need to sell LeeLee to recover their investment. His street days were over. But so was his cocky attitude and his girlfriend. She was mine to use and train until BBB made a deal to recover her debt. I kept staring at her beautiful feet as she dressed. They would get quite a workout in the coming days.

As I left I knew LeeLee was still tied in the dungeon. BBB would probably have his way with him a couple more times before selling him off.