Unexpected Wrestling Match

James was your typical college junior. Going to class, taking exams, partying with friends and getting drunk on weekends. He enjoyed his intramural wrestling matches with his friends and the occasional game of racquetball. Oh the glory days of college. Camaraderie between roommates who will later become lifelong friends.

James and his current girlfriend, Sandy, had been dating for about a year and a half. It had gotten pretty serious between them. Their sex life was more than fulfilling. The only no no Sandy had was never up the ass. They had tried it once but she stopped it before it really got started.

James had just gotten the head of his penis passed her sphincter muscle when she screamed bloody murder and made him pull out. She explained it was one of the worst pains she had ever experienced.

James really wanted the chance to fuck her up the ass. It was a fantasy of his and with his penis size he didn't think it should hurt that much.

It wasn't that James's penis was too large, in fact it was on the smaller than average size. Many times in the showers at school the other guys in the shower would laugh and call it a baby dick or tiny dick. James knew he wasn't hung but he accepted his size and that was that.

Sandy's birthday was quickly approaching and James, as usual, was low on funds.

He was chatting about his need for some extra money with his roommates one day and Paul, one of them, said, "Hey come to think about it I remember hearing about a way to earn some extra cash."

"Really, how?" James asked.

"It was an amateur wrestling contest at a bar in the next town up the road. I believe the place has one every Friday or Saturday night. The big winner receives a prize of $250.00 cash," Paul responded.

"I overheard it from a guy in my economics class the other day. Next time I see him I'll get more information if your interested James," Paul said. "That should be a slam dunk for you pal."

James thought the same thing. He wasn't a pro at wrestling but he had won many of the matches in his intramural meets. And the money was right. He could get Sandy a nice birthday gift with the winnings.

James was anxious to hear from Paul about the time and place of the soon to be contest.

Paul found James in the room a few days later and relayed all the details he was given. The contest was to be this coming Friday night at a bar called The Meat Packing Dristrict. The bar was located about 25 miles away in a small town. The contest started at 9:00 p.m.and went on till there was a final winner.

Friday came and James's car wouldn't start. He didn't have time to get it looked at but Paul knew how important the cash was to him and volunteered to drive him there. Paul couldn't stay; he had a late lab from 9:00 till 10;00 p.m. but would be back later to pick him up.

Paul was to drop James off at around 8:30 so he could get back in time for his lab. As the two pulled into the parking lot they saw the bar was quite large for being in such a small town.

"Ok bud, I'll be back as soon as labs are over and I can get here." Paul announced.

"Great man, wish me luck, like I'll need it," James laughed.

Paul sped off and James entered the bar glancing around to try and get a feel for the place. It wasn't crowded as of yet. A few tables with two or three people sitting at them and a handful of folks at the bar.

"That'll be five bucks cover charge," James heard from a voice next to him.

James turned to see a guy sitting at a makeshift kiosk. "I'm here for the contest," James related to the guy.

He asked, "You——-your here for the wrestling?"

"Yeah, why, you have a problem with that? It's open to anybody isn't it? That's the way it was advertised, right," James retorted.

Not knowing for sure since he had never actually seen the ad. He was just faking it.

"This better be legit, I had a friend drive me up here and drop me off so I could compete for the cash," James said rather rudely.

"Calm you roll dude, I just wasn't expecting you to be a contestant that's all," the guy said. "Wait here and I'll get the manager to sign you up."

He returned alongside another man. "Hi, I'm Mark, the manager." How are you doing?" he said.

"I'm just fine. I'm James and I'm here for the contest tonight, I hope there's no problem with that."

"No indeed, we're so happy to have you, the more participants the better. That always makes for a better event and more fun for everyone I believe," Mark said. "Ok let's get you in the back and we'll go over the way these contests work James."

James responded, "Great, I'm ready to win this thing, get my cash and go buy my girlfriend a nice birthday gift."

"Oh so that's your inspiration for winning tonight?" Mark asked.

"You got it man. I wrestle intramurals at college and I've won my share of matches so I think I'll have a decent chance of winning." James responded.

"Well this is definitely amateur night and I think you'll find most of out contests are just that, very amateur," Mark laughed. "And our rules and regulations are quite bendable because of that."

James gave him a sideways look not really sure of what that meant.

"Here are the stipulations for winning the $250,00 cash prize. You need to win three matches. The third and final match is what we refer to as the anything goes match." Mark announced.

"Wait I have to win three fucking matches to get the cash?" James said. "That's not fair nobody said anything about three matches!"

"Well yes we did, it's in the advertisement," he responded.

James having never even seen the advertisement had to reply, "Oh yes I remember now, I had just forgotten that part I guess."

"I wouldn't be too concerned about the first two matches, like I said these guys are real amateurs. Some of these guys think they are all that but when they have to prove it they fall way short. At least that's been my observation in past matches," Mark said. "With your wrestling experience you shouldn't have any problems."

"Great, that makes me feel better, I just need to win that prize money really badly," James added.

"It's getting pretty close to time for the first matches to start, let me get your gear and show you where to change," Mark said.

"Oh I brought my own gear so I just need to know where to change,'' James replied.

"You must have forgotten that part of the advertisement too. We supply everything. Each contestant wears one of two colors, white or yellow," Mark explained. "We don't use the wrestlers' names, we just refer to them as the yellow wrestler or the white wrestler."

"Follow me and I'll get your stuff and show you where you can change," Mark said as he walked away.

James followed him to a back hallway and through several stockroom-like areas. They finally arrived at a small dimly lit room. Mark fumbled through several boxes stopping to ask James what size singlet he wore. James replied, "I wear a large most of the time."

Mark searched and searched in the large box finally finding what he told James was a large. He handed him the singlet along with another smaller package.

"What's this small package?" James asked.

"Oh that's a jockstrap, state law requires each participant to wear one when competing here in the bar," Mark stated.

James thought it over and decided, hey it's a free jock, I'll take it.

Mark said, "Just bang on the door when you're dressed and I'll take you out to the ring."

James got undressed and put on the new jockstrap. It felt different, he couldn't determine why but just different. When he started to slip on his white singlet it was tight. It felt too small but maybe because it was new but really tight. James also noticed how thin the material seemed, it just didn't have any substance to it. There was no mirror in the tiny room to check his reflection so he just tapped on the door ready to go.

Mark opened the door and came into the room. Looking around he said, "I better take your gear and clothes to the office, things left out around here have a way of disappearing.

James agreed and handed Mark his clothes and the wrestling gear he brought with him, after all he had no locker or a car to lock his stuff up in.

Mark then said, "Oh James I need your tennis shoes too, no competitor is allowed to wear shoes, being amateurs and all."

James thought this a bit strange but the 'rules' for the bar wrestling were so different from regular rules he wasn't that surprised. So he slipped his shoes and socks off and handed them to Mark too.

Here he was in a strange place 20 something miles from his dorm room standing in a strange bar in only a jockstrap and a wrestling singlet.

Mark guided him to a somewhat larger room where another guy in a yellow singlet stood. "James this is Steve and you two are the first match tonight," Mark said. James and Steve shook hands and nodded a friendly hello. "Guys relax for a bit, have a drink whatever you need. The match will start in about fifteen minutes," Mark added.

Steve asked James if he had ever done anything like this before. James told him that he wrestled at school but he'd never competed for prize money. Steve laughingly told James that he had wrestled but only to see who was going to be on top. James looked at him like, what the heck are you babbling about and thought no more about it.

Steve asked if he had ever been to this bar before and James explained that he was from the college in the next town. And that he had heard about the contest and prize money from a friend. The fact that the prize money would cover his girlfriends birthday gift was the deciding factor.

Steve gave him a wtf look and said, "You have a GIRLFRIEND and you're doing this for the prize money to buy her a birthday gift?"

"Yes, why is that a problem for you?" asked James.

Steve just laughed and said, "Absolutely not a problem for me dude and let me add, may the best man win."

James thought that somewhat strange but a lot of the things Steve had said were strange. No matter James had to keep his wits about him and concentrate on the upcoming matches.

"Ok guys it's almost time for your match," Mark announced. "I'll take you out into the ring and get things started. Both of you have fun and make it entertaining for the crowd, after all that's where your prize money is coming from."

Mark led the two out to the wrestling ring. It was a fairly nice portable ring. James was impressed by the attention to detail.

"Good evening fans," Mark announced, "And welcome to tonight's amateur wrestling matches. This is the first round of three matches to determine tonight's winner. To my right is our white contestant and to my left our yellow contestant. Please support your chosen wrestler with your applause and voices."

"Gentlemen, this round will consist of a time limit of 20 minutes or a count out of ten. I will be acting as the referee and or lord of the ring," Mark continued.

The crowd laughed at the attempted pun on the movie.

"Ok guys on my count of three please wrestle, one, two three!" Mark shouted.

James automatically took his normal stance to start but noticed Steve just more or less bent a little at the waist. James lunged at him but instead of lunging back Steve stepped to the side. This caused James to stumble and nearly fall expecting to entangle with Steve.

James thought what the fuck, that's not a wrestling move. He glanced over to give Mark a look of what's going on here. Mark jus shrugged his shoulders and mouthed, amateur night. Before James could turn his head back toward Steve he felt a force behind him and the next thing he knew he was face down on the floor with Steve on top of his back.

Steve quickly grabbed each of James's arms and held them down and placed his legs on top of James's legs. Steve was just lying on James's back.

Shouts and whistles from the crowd included, "Nice takedown, sweet position and wish I was the white wrestler."

James thought how weird, but was concentrating on getting this guy off his back. He wriggled back and forth and pushed his butt upwards trying to loosen Steve's hold. That move got another round of applause and hoots from the crowd.

"Oh looks like he wants it yellow guy, go ahead and give it to him," came from the crowd.

Finally James was able to shuck Steve off his back and get to his feet. Again he looked at Mark for some clarification on what was going on. Mark went to the center of the ring and announced, "Just to remind everyone this is an amateur match, you don't need actual wrestling experience to compete," looking in James's direction.

James thought ok I can handle this after all I know how to wrestle. At the same time he was thinking, it must be 100 degrees in here, I'm sweating like a whore in church.

James and Steve continued to prance around the ring grabbing and pulling each other. Occasionally one of them would pull the other down and try to hold them there for the count. James found it hard to wrestle someone who didn't know the correct way to do it.

After about fifteen minutes of playing around James got Steve in a good hold and drug him to the mat. He was able to hold him for the count and was declared the winner.

Mark held up James's right arm indicating a win and announced, "Next match in approximately fifteen minutes, everyone get a fresh drink."

Mark escorted James back to the room he had waited in with Steve. He threw him a towel and a bottle of cold water. "Towel off and get some rest before the next match. Your next opponent will be here shortly. And remember these are all amateurs so don't get all bent out of shape if they have no formal style of wrestling. Most are here for the fun of it."

James was relaxing and trying to cool off. He was so hot, his singlet felt damp. The door opened and in walked a stocky guy in a yellow singlet.

"Hi I'm Jeffery, guess we're up next."

"Yep I think so. Have you done this before?" James asked.

"Nah but I've seen a few matches here before and thought it might be fun to try it," he responded.

"Aren't you interested in the prize money," James asked.

"Sure it would be cool to win that but that's not my main objective," he answered.

"Alright guys it's time for your match, let's go," Mark said.

He led them back to the ring and announced round two. "One, two, three go," Mark repeated.

Jeffery seemed even more stocky when they got into the ring. He was heavy to try and move around. James wasn't accustomed to wrestling anyone in Jeffery's weight category. There was much more body contact this match. Jeffery would grab him and hang on. There was a lot more traditional wrestling this match. But in the end James used his knowledge and was able to take Jeffery down for the count.

Again James's arm was raised as the winner and escorted back to the waiting room for his final opponent. While enjoying a bottle of water James hears the door open and in walks another figure wearing a yellow singlet. This guy was about James's height but thicker. Looking him over James noticed his legs resembled tree trunks, much bigger than his own.

"Hi I'm Robert, nice to meet you."

"Nice to meet you too, I'm James. Guess we're the final match tonight, huh?" James asked.

"Looks like it. Is this your first time doing stuff like this, I mean like being a contestant?" Robert asked.

"Yep, I've never done anything similar to this, it's kinda crazy but I need the cash," James replied.

"That's cool, I just think it fun and I get a kick out of performing in front of the crowd, is that sick or what," Robert said with a chuckle.

Mark interrupted saying, "Ok guys it's showtime, let's get out there."

As the three walked out in the hall James noticed his singlet was soaked with sweat from the two previous matches. "Mark I need to change my singlet, this one is wet with sweat," James told him.

"Sorry James but it's time to start the match, you'll just have to make do with that one."

Mark announced to the crowd that this was the third and final round of the night, featuring the winner of the two previous matches, James.

Hey wait a minute, James thought, they weren't supposed to use our real names. Why was Mark using his name in front of the crowd? Oh what the hell in 20 minutes this world all be over and he'd have the cash.

Mark continued, "As you all know the final match is the anything goes match." And with that he counted, "one, two, three————-wrestle."

Robert grabbed James right off the bat, catching him off guard. James heard someone from the crowd say, " Hey check out the white singlet, it's wet and it's practicality transparent."

Another voice agreed, " Yes I can see the crack of his ass through the material."

"He must be wearing a jockstrap if you can see his crack," another audience member sounded off.

What the hell was this, James kept thinking. Could they really see through his singlet. Thinking back to when he was putting it on he remembered how thin the material was. This was getting embarrassing. He needed to win this and get the hell out of the bar.

James decided to get down to business and use some real wrestling moves. He tried a move to escape from the hold Robert had him in. It backfired and now Robert had him in a chokehold with James facing the crowd.

Now James could hear, "Looks like he doesn't have a dick, there's nothing where it should be," and then some snickers from the crowd. Another voice came through saying, "I think he's got a pussy instead."

James was getting frustrated hearing all these personal digs about him, and not paying attention to the match. Suddenly Robert slipped a leg through his and bam James was on his back looking up at his opponent. Robert held him down and the count went to eight before James was able to break the hold and get back up to his feet.

Again James was hearing more digs about his 'see through' singlet. Taking a quick peek James saw what the audience members were talking about. He could see his dark nipples through his singlet. Looking further down his body he gasped as he could clearly see the jockstrap underneath his suit.

James was filled with humiliation and wanted nothing but to get this over with. Still paying more attention to the crowd than his opponent once again he let Robert get a good hold on him.

Damn this couldn't be happening to him. He was a real wrestler, these other guys weren't. He twisted and turned starting to break free. Robert caught him by the back of his singlet and started slinging him around in circles.

The crowd went wild with encouraging hoots and whistles. James felt like a rag doll the way Robert handled him. Faster and faster Robert slung him. James finally heard a rrrriiiipppp and felt his singlet give. He knew something bad had just happened.

When Robert let go of him James tried to look over his shoulder to see the damage but couldn't get a clear view. He could however feel a draft behind him.

James called over to Mark to stop so he could change suits. Mark answered his query with, "This is the anything goes round and that includes this, sorry bud."

James couldn't believe his ears. He was going to have to play with his singlet ripped? Well all the better to make this as short a match as possible.

James had no way of knowing that his suit was ripped down past his jockstrap and revealing the top of his ass crack. The crowd was loving it, more cheers and hollers kept coming.

Robert charged him and got him in a bear hug trapping James's arms at his sides. "Rip it, rip it, rip it' came bellowing from the crowds as James was helplessly held tightly to Robert's body.

Robert reached down, grabbed the ripped part of the singlet with both hands and tore it completely down past his ass. With James only wearing a jockstrap under his singlet his entire ass was on display for the crowd. This brought the crowd to a roar with thunderous standing applause.