Tennis or Dress Shoes
by The Gambling Cowboy

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After a few more stops, more than half of the passengers got off, and there were only people in the seats.

No one was standing, but I decided to stay where I was at, because I was eye level to everyone’s feet. On the other side of the trolley, just within my line of site, there were four rough looking guys laughing and talking loudly. They seemed like the kind of guys that does what they want, whenever they want, to anybody or any place they feel like. One of the guys was sitting with his back towards the front of the car, and his feet were flat on the floor.

He had a white t-shirt and blue jeans and the most interesting pair of tan shoes I could imagine. The main part of the shoe looked like a dress shoe, but the rest of it was like a tennis shoe. His white socks were soiled as if he had been wearing them for a few days. I kept on looking at those shoes trying to figure out if they were dress shoes, or tennis shoes.

Well at some point he must have seen me looking at his shoes, because he stretched and crossed his legs to where his feet were slightly in the aisle. I continued to get a better look, but couldn’t figure out which was which. He then started moving his foot from side to side, waiting to see if my eyes would follow them. Of course, my eyes started moving back and forth with his feet, and I know he noticed because of the smile he had on his face.

He was talking to the other three guys, which I couldn’t hear what was being said, when they started laughing. They started looking at me out of the corner of their eyes without turning their heads to see if I was really watching his feet.

After a few more stations, I finally came to my stop and proceeded to leave the trolley. I was so excited from the businessman, and still curious about the shoes, that I began walking home. Normally I would have taken the bus, but I just missed it by a few minutes, and the next one wouldn’t arrive for another half hour, so it was just a quick to walk home. The sun was setting and it was starting to get dark, but the street lights were not on. The first street was a two way road with no center line and ran along the tracks. When I came to the intersection, I made a left down a four lane divided street.

Halfway down the street there was an undeveloped parcel of land that had tall grass growing. I would cut through the area as a shortcut to the next street. As I got halfway through that patch of land, I heard the rustling of footsteps rushing up to me. Before I could turn around to see what was happening, the four guys that I saw on the trolley ran in front of me and stopped. I continued to walk and go around them, but they just kept moving in front of me.

I then said, “What the fuck you think your doing?”

The guy that I was watching spoke up and said, “We want to have a few words with you.”

I replied in a cocky voice, “I’m in a hurry to get home, and I don’t have time to speak to you, so just let me get by.”

“You’re not going anywhere until we get some answers.” He said in a forceful voice.

“I don’t feel like giving any fucking answers to you or anyone else, so fuck you.”

“Is that what you want to do, is fuck me. That seems to be the only words coming out of your mouth. I don’t think your man enough to fuck me, but I know that I am man enough to fuck you. I bet you would love for me to fuck you, wouldn’t you?”

Just then, one of the guys grabbed my arms and pulled them behind my back. I felt the tension and the pain of them being stretched.

“Please let me go, don’t hurt me. I’ll do whatever you want, but please don’t hurt me.” I said in a shaky scared voice.

He then said, “Why were you looking at my shoes back on the trolley?”

I said, “I was just trying to tell whether they were dress shoes or tennis shoes, I couldn’t tell. That’s why I was looking at them, trying to figure it out.”

He then said, “Well then, get down there and take a closer look.” Then I felt a foot bearing down on the back of my head, pushing me down to the ground. With my arms being raised higher and the weight of his foot pushing down on my head, I finally fell to my knees with my head directly above his shoes.

That’s when I hear a voice say, “Now tell me whether they are tennis shoes or dress shoes, punk.”

It was too dark to get a good look so I said, “It’s too dark to tell, and I can’t see them very well.”

“Well then I guess you’ll just have to lick them to find out what they are.” He said with an evil grin.

That’s when I felt the full force of the foot on my head, pushing my face within inches of his shoe.

“Now lick my shoe, or your head would end up against the ground.”

I slowly stuck out my tongue and started licking the top toe part of his shoe. The smell was that of old worn leather with dirty sweaty feet smell blended in. The smell of dirty sweaty foot odor mixed with worn leather instantly gave me a hard on. I continued licking up towards the laces then down around the arch towards the heel, then around the other side until I got back to the front of the shoe. I then moved my tongue up the middle of his shoe until I reached the hi-top part of the shoe. I was able to see the top part of his sock and noticed all the dirty spots on it. After I finished, I was still not able to tell whether they were tennis shoes, or dress shoes. The top and the side parts of the shoe was hard leather, probably hardened from time, and the soul and tops were canvas.

Then he shouted, “Well you better give me an answer now, because if you’re right, then I’ll let you get on your way, but if you’re wrong, then I’ll be giving you you’re punishment.”

Figuring I had a 50/50 chance, I said, “It had to be a dress shoe.”

With that answer I heard a big loud laugh saying, “Wrong you fuck head, they’re tennis shoes, now you have to answer to me.”

I repeated my previous plea and said, “Please, don’t hurt me, I promise not to say anything, please don’t hurt me. I’ll do whatever you want, but please to don’t hurt me.” Just as I finish, someone grabbed my head and jerked it up. It was too dark to see who it was, but then I felt a rolled up dirty sock being forced in my mouth. I tried to turn my head, but they were just too strong to stop, and another guy took another sock and blindfolded me.

“As long as you do as I say, you will not be harmed. We’ll take you to our place, but don’t want you to know where it is. We will then drop you off back at this same spot shortly. Do you understand me?” he snapped.

“Yes I understand.”

They stood me up and proceeded to guide me towards their place. They took me around in circles for I would lose my bearings and not know which direction I was going. After about five minutes, we entered a house and I was thrown down to the floor.

“Stay there until we get ready for you,” Said the first guy.

While I sat their waiting for them to decide my fate, I could hear them talking across the room. I couldn’t make out what they were saying, but it seemed like they were saying what each one would be doing. Just then, the blindfold came off, and the sock came out of my mouth. All I saw was four tall good looking men all looking down at me, smiling. They were all facing me, with one directly in the front, one directly in the back, and one of each side of me.

The guy standing in front of me told me to sit up on my knees. I stood up on my knees, and my face was directly in front of his crotch. I was able to see a bulge starting to form and I stood staring afraid to move. He then put one hand on each side and slowly pulled my face into his crotch. I was able to feel the heat and the scent of his sweat. He started rubbing his crotch all over my face while making sure his bulge was rubbing across my mouth.

He then said, “You kept on saying fuck you earlier, now it’s my turn to fuck you. Have you ever been fucked in the mouth before?”

I thought about it a few minutes and said, “No.”

“I’ll fuck you so hard and good, you’ll want to suck dick all the time.”

Just then he unsnapped and unzipped his pants, opened it up and slid them down around his butt. All I saw was a pair of white shorts with a big hard dick pointing up. He then grabbed me and pulled my head towards his crotch.

“Pull down those shorts with your teeth?” he commanded.

I grabbed his shorts with my teeth and pulled them down far enough that his dick sprang forward and hit me in the face.

I closed my eyes when he said, “Keep your eyes open, I want you to see every minute of it.”

I kept my eyes opened as I pulled his shorts farther down around his balls, down to his knees.

He then said, “Look up at me.”

I lifted my head towards him and he started hitting my face with his cock. The more he hit me, the harder it got. It must have been at least 10 or 11 inches.

“Now stick out your tongue, I want you to lick my dick like you did his shoes. Start from the balls and work you way back along the shaft towards the head. I want one long slow continuous lick, and then reverse it back to my balls.”

I stuck out my tongue and put it on the top of his balls. It had a sweaty salty taste as I started moving my tongue along his shaft. I felt his vein pulsing as I moved my tongue toward the head of his dick. When I got to the tip, he jerked as he moved the head of his cock around my tongue. Then he said it’s time to go back. I slowly moved my tongue until I got back to the top of his balls.

He then said, “I want you to suck on my balls, open your mouth and put both of them in.” I opened my mouth and took both balls inside my mouth. I used my tongue to lick them while sucking at the same time. He then lifted them out of my mouth and told me to open my mouth wide. As I waited for him to deliver, I felt calm and relaxed, knowing that he was in charge. He slowly stuck his cock halfway in my mouth and told me to put my lips around it. I wrapped my mouth around his huge cock and felt the warm moist flesh on my tongue. He slowly shoved it deeper and deeper into my mouth until he had his whole shaft in my mouth. I went all the way down my throat, and I gagged a little but took every inch of it.

“Suck on my dick baby, like a big lollipop.” He said in a soft caressing voice.
I started sucking a softly and intensely as I could when he started pushing it back and forth in a slow steady pace. As his cock started getting more lubricated from my mouth, he started shoving it in and out faster and faster. He placed both hands on each side of my face and started bringing my head into him for more action. I did not know what it would feel, taste, or be like when he first started, but was now beginning to enjoy it very much. The faster he went in and out, the more I tried to please him to the point of getting a boner myself. This went on for quite a while when he finally squeezed both hands tightly on my head and began tensing up.

Then I felt the explosion inside my mouth from his throbbing cock. It started filling my mouth so fast that I had no choice but swallowing it. The first swallow felt kind of strange, but soon felt that I had to swallow every last drop. After the last drop he sat down on the sofa behind him and pulled my head down with him. There I was, lying on his lap with his cock still in my mouth enjoying every minute of it. He patted my head and told me to just relax and enjoy. I was very pleased that I made him so happy, and I knew from this day forward, this is where I was to be. He then pulled my head off and told me to get back on my knees for the next task to perform. He was correct when he said that once I sucked his cock, I would want it all the time.

I sat up on my knees waiting for the orders from the second guy.

After the first guy was finished the second guy standing to the right of me slowly moved directly in front of me. He had button down blue jeans, light colored construction boots and immediately commanded me to take off his boots. I started unlacing his left boot and immediately smelled the aroma from his dark socked foot. I pulled the boot off and saw that the sock was formed perfectly around his foot. I then proceeded to take the other boot off when he placed his left foot directly on his face. “I’ve haven’t done any laundry for over a week and these socks have been on my feet for three days.” He spoke in a tone as if to shock me. One of the other guys grabbed my hair and pulled my face up until I was looking directly at him. He had an evil grin as he slowly rubbed both feet all over my face. I started moving my head around to make sure I got every inch of his feet. After about 15 minutes he told me to put his boots back on. I immediately placed his boots back on and was told to wait for the next guy.

The third guy was dressed in a white t-shirt, brown collared shirt, and leather work boots. At first they looked like State Trooper boots, but I know they weren’t. Untie my boots using your mouth only and don’t stop until you get them both off. I went down to untie his right boot and could smell the aroma of leather. That was one smell I always had was the scent of leather, especially leather boots and the smell of socked feet inside them. I got his right boot untied and he used his left foot to remove it. The sweet scent of sweaty leather permeated the air as I took in a deep breath.

I then took off the other boot and began rubbing both his feet. The souls of both feet were wet with the sweat of a full days work. “Now unbutton my fly with your mouth and make it fast.” He said. “Yes sir, right away.” I replied. He pulled his underwear down and grabbed his big cock. He started shaking it up and down and said. “Open your mouth and get ready for another manly cock to worship.” I opened my mouth and he pushed his cock all the way in my mouth until it touched my throat. I started pushing his throbbing cock back and forth moaning louder and louder with each push. All I could do is feel the hair above his cock rub against my nose. He must have not taken a bath or shower for a few days, because the man sweat from his crotch was very pungent. Just as he was about ready to cum, he pulled his cock out and squirted all over my face. .He gave me a napkin and told me to wipe my face and get ready for the fourth guy.

Now the fourth guy was the original guy with the tennis/dress shoe combo that got me in this situation to begin with. He started out by saying, “Lets see how big and cocky you are now.” He continued, “You are now going to show me the respect that I deserve.” “Look at me boy when I am talking to you.” I looked up to see his face staring back at me. “Now you are going to answer me, Yes Sir and Master,” he said. “You will always say please and thank you, or you will be punished.” He continued. I softly said, “Yes Sir. Thank you Master.” He had a pleasant smile on his face. He sat down on the chair and turned on the television and said, “Turn around and lean your back on the edge of the couch.” I was sitting between both legs as he took of both his shoes.

He had on a pair of white over-the-calf socks that were stained from several days of wear. He placed each foot on my shoulders with the souls touching each side of my face. They had a strong musky odor about them. He then bent and placed his toes right up against my nostrils and said, “Take nice deep breaths until I tell you to stop.” “Yes Sir and Thank You Master.” I said in a pleasingly voice, after all I did tell him that I would do anything he wants. He started rubbing his toes against each nostril while rubbing the souls of each foot against the sides of my head. I just continued sniffing both feet not letting him know that I was enjoying every minute of it. As I looked at the TV, I noticed it was a straight porn movie about some guy getting his dick sucked. As we watched the video, he slowly scooted down from the chair to where his crotch was rubbing against the back of my head. “You want to make me very happy so you can go home, don’t you boy?” I said, “Please master, I do.”

After about 15 minutes of worshipping his beautiful size 12 socked feet, he stood up in front of me, turned around and pulled his pants off. His semi-erected penis was the biggest I have ever seen. All I could do is just stare at it. “I have saved the best for last.” He told me. He bent his knees and rested them on my shoulders placing his dick right in front of me. As he held his cock, he leaned forward inching closer to my mouth. “Do you want to suck my cock, boy?” he said in a bold voice. “Yes sir, please.” “Open your mouth big and get ready for your punishment.” I opened my mouth and could feel his throbbing cock entering my mouth. His big cock filled my entire mouth, from one side to another. Not only was it long it was thick. He began pushing it in and out as it got harder and harder. It finally made it all the way back down my throat and almost made me throw up.

I didn’t want to do that, so I just sucked on it as hard as I could. He moved his big cock in and out of my mouth for more than 15 minutes. My mouth was getting sore and tired, but I continued to take every inch of his pulsating piece of meat. My neck was pressed against the edge of the seat cushion softening the pounding. Then he just froze and all I could feel was a huge gush of cum hitting the back of my throat. I started to swallow as fast as I could as more and more cum continued. I made sure I swallowed every drop. As he pulled his cock out, he looked down at me and said, “Did you like your punishment?” I said, “Yes sir.” He then sat back in the chair and placed his socked feet in the same place he originally had them.

He continued to watch the video and told me to just relax and worship his feet. I sat there watching the video while enjoying his lovely socked feet. I was very relaxed and happy to be at his feet knowing I have done my duty to serve him. After about five minutes, one of the guys got up and put another video disc in. When the video started, I was shocked and stunned at what I saw. The entire incident was video taped and put on a DVD. He kicked me in the head when I started to say something about it as he said,” Shut up and watch the damn video.”

I watched to entire video of the entire night. After it was over, he told me that I was to start making this a weekly event, and if I didn’t come back, the video would be placed on the internet. Especially You Tube and Facebook. He told me that I was free to leave, and I said, “Yes sir, thank you master.” He replied, “You’re welcome and get ready for some more action next Friday at 7:00 pm .” With that said I got up, made sure all of my clothes were together and went home. I couldn’t sleep at all that night thinking about all the excitement that I had and what was to come.