Date: Fri, 21 Nov 2008 15:23:33 -0800 (PST) From: Jason Woods Subject: Jimmy Shows Off Jimmy Shows Off by James Woodson luv2showoff4guyz@yahoo.com Jimmy had been showing off since he was a little kid when he would take his clothes off in public places whenever he had an audience. He loved it when older boys or men would watch him undress and show off his underpants. He always got so excited getting caught in his underwear. Now as he was getting older, he found that he got boners when he undressed in public, so he started jacking off too. He loved getting caught by older guys half dressed and playing with himself in public. He hoped that it would soon go even further. One Saturday morning Jimmy was watching cartoons on television. He was only half-way paying attention, mostly playing with his morning borner. Then the doorbell rang. Jimmy's dad had gone to work, so he got up to answer the door wearing his bathrobe and socks. He opened the door to find a delivery man standing there. The man smiled at Jimmy in his robe and said, "Sorry, son, I hope I didn't get you out of bed." "No, I wasn't sleeping. I was just playing with myself," said Jimmy with a smile. The man looked surprised for a few seconds, then smiled back. "Oh, well, sorry to interupt your fun! Um, I have a package for David Woods." "That's my dad, and he's not home, can I sign for it?" "Sure, that would be fine, thanks," said the delivery man as he handed the electronic clipboard to Jimmy to sign. As the boy reached for it, his robe fell open, exposing his blue and white underpants with an obvious boner tenting the front. "Oops, sorry sir," said Jimmy. "That's OK, son, it's not your fault," said the delivery man staring at the boy's cute underpants and his obvious hard-on. Jimmy signed the clipboard and handed it back to the driver. As he did, he noticed that the man had reached his hand inside his pants to feel himself. "You know," said Jimmy, "I cut the pockets out of all my pants so I can reach in and play with myself anytime I want." "Wow, really?" said the driver, now rubbing himself faster through his pocket. "Where do you do that at?" "Everywhere," said Jimmy as he reached down to stroke his boner through his briefs. "At school a lot, or at church, under the table in a restaurant, or just walking around somewhere. My dad doesn't even notice that I'm doing it!" "Wow, you jack off in public, right in front of your dad?" asked the delivery man. He was rubbing himself even faster now. "Yeah, all the time!" said Jimmy, also rubbing his hard-on faster through his undies. "He doesn't know I'm doing it, but other guys sure notice!" "Oh yeah? Do you like for guys to see you masturbating?" asked the driver. He reached over to Jimmy's shoulders and gently slid his robe off so it fell to the ground. The boy was now standing on his front porch in just briefs and socks, rubbing his erection in front of the delivery man. "Oh sure, I love for guys to see me play with myself," said Jimmy, looking down at himself. "Uh oh! I'm just in my underwear! Everyone can see me!" He rubbed his cock even faster as he said it. "Do you like that?" asked the driver as he unzipped his shorts. "Yeah, I love for guys to catch me in my underpants! Sometimes I do things so I will accidentally lose my clothes." "Like what?" asked the delivery man, reaching into his open fly to rub his hard dick. Jimmy blushed and giggled, saying, "No, I can't say, you will laugh at me!" "No, I promise I won't," said the driver. "What kind of things do you do?" Jimmy blushed darker red and said, "Well, I wear shoes and pants too big so they fall off when I walk, or fix the button and zipper on my dress pants to break so my pants might fall when I walk. Or snip the seems of my clothes so they fall apart as I walk around." "I think that's great! My name is Phil," said the driver. "I'm Jimmy." "Nice to meet you, Jimmy. I would love to see that sometime! I mean when your pants fall down in front of people!" "It would be fun to show you!" said Jimmy, getting excited. "Maybe sometime you could come with me to deliver packages and we could see if it happens!" "How about now?" asked Jimmy. "My dad went to work, so I am alone for a while." "Well, OK," said Phil, "If you think you won't get in trouble." "Oh boy, thanks! I'll be right back!" said Jimmy, running into the house. Phil chuckled and tossed the boy's robe which he left behind into the house. He put his father's package in the hallway, then thought he had better zip himself up. Soon the boy reemerged in a pair of baggy khaki pants, a tight polo shirt, and some loose loafers with blue socks. Phil couldn't believe how cute and hot this boy was. He led him to his delivery truck. "I have to make a couple of deliveries to business; you can help me!" Jimmy was grinning as he climbed into the truck. A few minutes later they pulled up in front of a small business. Phil got out and motioned for Jimmy to follow, then just before they entered the business, Phil handed Jimmy the package. The two walked into the business. There was a young man in a shirt and tie at the front desk. He and Phil talked for a minute, and Phil had the man sign for the package. Then he motioned for Jimmy, saying, "My son here has the package for you." Jimmy walked toward the young man using both hands to carry the package. As he did, Phil noticed he was struggling to keep his pants up since they were so oversized. With each step Jimmy took, his trousers slid down a bit more. Then as he handed the package to the young man, Jimmy's pants fell to his ankles. Jimmy looked down and said, "Oh no! My pants fell down! Everyone can see my underwear!" As he said this he tried to use his hands to cover his blue and white briefs and the obvious boner tenting them. Jimmy turned to run, still trying to cover his underpants, as the young man in the shirt and tie smiled and said, "It's OK, you don't have to be embarrassed." The man came out from behind his desk. As he did, Jimmy turned to run out the door. But with his pants around his ankles he lost his balance. The man caught him, and as Jimmy tried to get his balance again, his feet came out of his shoes and his pants. He was standing in just his shirt, underpants and socks. "Oh no! I'm just in my underpants and everyone can see!" said Jimmy, again covering his brightly colored briefs with his hands. Secretly he was able to rub his boner through the material as he did this. "Here, let me help you," said the young man. He picked up Jimmy's trousers, and helped the boy step back into them." "Thanks, mister!" said Jimmy as he ran out the door and back to the truck. "Uh oh, he forgot these," said the young man, picking up Jimmy's loafers. Phil noticed that the man took a whiff of Jimmy's loafers before handing them over. "Thanks for your help," said Phil, "I had better get going." Phil was chucking as he got into the truck and handed Jimmy's shoes to him. "That was great!" "Yeah, it was fun!" said Jimmy. "I love doing things like that!" "I see what you mean! Do you want to do that again?" "Sure!" said Jimmy. Phil laughed again and drove to another business. He handed a package to Jimmy, who followed him in. There were three young men, all dressed in business clothes, in the front room of the business. Phil had one of the men sign, then said his "son" had the package for him. Jimmy walked toward the man, both hands carrying the package, his loose trousers slipping down. The man took the package, and again Jimmy's pants fell to his ankles. "Oh no! I lost my pants!" said Jimmy, putting his hands in front of him. He took a step back, and as he did, started to fall backward. He pulled his feet out of his shoes and pants. "Uh oh, I lost my shoes!" He looked down at himself again and said, "I'm in my underwear! Oh no!" As he continued to use his hands to cover himself, he was discretely rubbing his boner through his briefs. "It's OK, son," said a young man in the business, "don't be embarrassed. I can help you." Phil noticed that the young man had a boner tenting his suit trousers as he helped Jimmy. The man did much the same as the man at the last place. He picked up Jimmy's trousers and got down on his knees. "Here, I can help you back into these," he said as he gently lifted Jimmy's socked foot to guide it into one of the trouser legs. Then he gently led the other socked foot into the other side, and pulled them up. The man looked up and realized that he was eye-level with Jimmy's crotch. He couldn't help but notice that the boy's hands were rubbing against a boner. The man pulled Jimmy's pants up, but not all the way up. Instead he picked up the boy's loafers, then got down in front of the boy again. "Here, let me help you get your shoes back on." The man again gently led Jimmy's socked feet to his shoes. He would rub and squeeze Jimmy's socked feet before sliding them into the loafers, and as he did he stared at Jimmy's hands rubbing his crotch. The man took hold of Jimmy's pants as if to zip him up, but he took his time. Then suddenly Jimmy's body twitched and the boy said, "Uh oh! I'm gonna make a mess in my pants!" Just then Jimmy began to cum, shooting his sperm into his briefs. The man watched Jimmy cum in his undies, then said, "It's OK, no one will know that you had an accident in your pants once I get them up." The man took a whiff of the semen soaking through Jimmy's underwear, then pulled up the boy's pants. "Thanks, mister, I'm sorry about all that!" said Jimmy. "It's OK son, things like that have happened to me, too." "Really?" asked Jimmy, already rubbing his crotch again. The man whispered into Jimmy's ear, "Yep. In fact, I might just make a mess in my own pants pretty soon!" "Wow!" said Jimmy, "Well thanks again, we have to go!" Phil and Jimmy got into the truck, and Phil drove the boy home so he didn't get into any trouble. But he promised to see the boy again soon. That evening Jimmy's dad came home, bringing with him a client from work. They were planning to go to a nice restaurant for dinner. His father invited Jimmy, but warned him that he would probably be bored. Jimmy looked up at his father's client, who smiled at him, and said he wanted to go along. Jimmy got dressed up, wearing blue trousers, a light blue shirt, blue argyle socks and loafers. He wore bright red briefs underneath. The drove to pick up his dad's client, whose name was Bill, and Jimmy hopped into the backseat. Once at the restaurant, they were seated in a booth. The men sat across from each other with Jimmy next to Bill. The first thing Jimmy did was to slip his socked feet out of his shoes. He kicked the shoes away, and they ended up underneath the table behind him. Jimmy began to slide his socked feet around, and bumped Bill's feet. Bill looked down and smiled at the boy. Soon Bill felt the boy's feet sliding against his shoes and up his ankles. Then he felt Jimmy's toes pressing against the heel of his shoe, finally popping it off his foot. Jimmy then used his socked feet to pry Bill's other shoe off, and he ended up in his socks as well. The two rubbed their socked feet together under the table. Bill glanced down and saw that Jimmy was excited. He not only had a boner tenting his pants, but he was rubbing himself through the material. Jimmy looked up at Bill and smiled as he masturbated. When the waiter arrived to take their orders, the young man could barely keep his eyes away from Jimmy's lap as he watched the boy rubbing himself while trying to write down the orders. When the waiter left James, Jimmy's dad, said, "Well I hope he gets everything right. That waiter was barely paying attention to what we said." Bill and Jimmy exchanged glances and smiles, and when they did Bill watched as the boy began to unbutton his pants. Bill tried hard to concentrate on what his dad was saying, but his eyes were practically glued to Jimmy's lap as the boy slowly unzipped his trousers. Soon his bright red briefs were exposed. Jimmy continued to masturbate, rubbing his hard cock through his underpants, as Bill tried to concentrate on what James was saying. The waiter returned to bring Bill and James knives for their steaks, and he almost dropped them when he saw Jimmy. The boy smiled up at the waiter as he continued to play with himself under the table. Bill discretely took the knife and slid it under the table. He slid the blade against the side of Jimmy's underpants as the boy let out a little giggle. Bill very carefully began to slice through Jimmy's brifes. Bill made a few more slices, and the underpants were free. Bill took hold of the material and pulled the remains of the underwear free from the boy's lap. Bill looked down at Jimmy still smiling up at him, now openly jacking his erection under the table. The waiter arrived at the table and almost dropped the food when he saw the boy jacking his hard-on out in the open like that. "That is the worst server," commented James, Jimmy's dad, after the waiter left. "Jimmy, how was school today?" "It was fine, dad," answered Jimmy, still jacking. His dad asked him questions about what he had done in school, and Jimmy sat answering his father who was unaware that his son was masturbating the whole time. Occasionally Bill would reach his hand over underneath the table to rub Jimmy's cock. Then when he would pull his hand away, Jimmy would masturbate again. The boy kept edging through the whole meal. After they had eaten, Jimmy accidentally bumped his father with his socked foot. James peeked under the table and asked, "Jimmy, did you take your shoes off?" "Yes, dad." "Well, you'd better put them back on." "I can't find them," said Jimmy, "I think they slid underneath the table behind me." "Well, that's why you shouldn't take your shoes off in places like this," said his father. "You had better go find them." As they had been talking, Jimmy had buttoned his trousers and slid his dick inside his pants without zipping them. "OK, dad," he said, getting up to find his shoes. The boy walked to the table behind him where a man sat with his son who was about the same age as Jimmy. "Excuse me, sir," he said, "I'm sorry to bother you, but I took my shoes off and I think I accidentally kicked them under your table. May I look for them?" As he talked Jimmy was grinning at the man and rubbing his cock through his pants. The man was watching Jimmy play with himself, and he could see the boy's trousers were unzipped. He even caught a glimpse of the boy's boner. "Of course son," said the man, "I understand. Sometimes my boy here takes his shoes off in places like this too. One of these days I will have to teach him a lesson about losing his shoes that way," said the man with a wink. "Thank you, sir," said Jimmy as he crawled under the table. He was down on his hands and knees under the table, and he watched as the man slipped out of his shoes. The next thing Jimmy knew, the man slid his socked foot into his open fly, popping his dick out. Then the man began to carress Jimmy's hard cock between his socked feet. Jimmy couldn't help but let out a little moan. Jimmy looked around for his shoes, not seeing them. He saw that the man's son was still wearing his shoes; he had not taken them off this time. Jimmy reached over and took hold of the boy's feet. He heard the boy let out a small sigh. He grabbed one shoe and pulled, popping it off the boy's foot. Then he did the same with the other, pulling both shoes off. He heard the boy sigh as he wiggled his toes inside his socks. Just then Jimmy felt a shudder run through his body as he began to cum. He let out a louder moan as he began to spurt jizz, shooting it right into the man's empty shoes. His whole body spasmed as he pumped his load into the man's shoes, then when he was finally done, he quickly shoved his still-dripping cock back into his trousers. He stood up with the boy's shoes in his hands. With the boy and his father watching, Jimmy put the shoes on the floor and stepped into them. "Thank you for the shoes," said Jimmy, grinning. "Enjoy them!" said the man, smiling back at the boy. He watched Jimmy walk away in his son's shoes. On Monday at school Jimmy was called to the office of the principal, Mr. O'Connor. Jimmy wasn't worried, though, as he had been there several times before. Jimmy went into the office and sat down on the chair right in front of Mr. O'Connor's desk. "Now Jimmy," said the principal, "I'm sure you know why you are here." "Yes sir." "One of your teachers caught you, well, playing with yourself in class. As you know, we have discussed this before. You have to be careful about doing private things in public." "Yes sir," said Jimmy as he took off his dress shoes. He went to an all-boys school, and they wore uniforms which included grey pants and white shirts with dress shoes and socks. Jimmy made sure to make some noise as he lifted his feet, popping each shoe off with the toes of his other foot, and letting the shoe drop onto the floor. He wanted to make sure Mr. O'Connor knew what he was doing. "Now I understand that boys have urges," continued the principal. "We all get them. But we have to be careful in what we do about them." "Yes sir," said Jimmy as he kicked his shoes so that they audibly slid on the floor and ended up underneath the principal's desk. "Did you take your shoes off?" asked Mr. O'Connor. "Yes sir, I was just getting comfortable." "Well, that's good, I want you to be comfortable with me," said the principal. "Maybe I will take my shoes off too," he said as he slipped off his dress shoes as well. Jimmy heard Mr. O'Connor's shoes sliding on the floor, and he looked down to see that his principal had kicked his shoes so that they ended up near him. Jimmy began to rub his socked feet on his principal's shoes, and he could tell from the noise that Mr. O'Connor was doing the same with his. "So Jimmy, do you get many erections in school?" "Yes sir," said the boy as he felt a boner begin to tent his trousers. "How often does that happen to you?" "All day long," said Jimmy. "At least once in every class." "Well no wonder you have trouble," said the principal. "Are you getting one now?" "Yes sir." "I see. And what do you do when you get an erection in class?" "I start to rub it through my pants," said Jimmy as he began to stroke his boner through his grey school trousers. "Why do you do that? You must know that that is wrong. You should try to control your urges." "I know sir, but I can't help it. It feels good to rub it." "Yes, I understand. It does feel good to rub it, doesn't it?" "Yes sir," said Jimmy, now rubbing himself faster. "It feels very good." He could tell from the way Mr. O'Connor's arm was moving that his principal was also rubbing himself under his desk. "But Jimmy, the teacher who reported you said you were doing more than just rubbing your erection through your pants. What did you do?" "Well, I couldn't help myself, sir, it felt so good - that I unzipped my pants in class so I could feel my boner through my underwear." As he said this, Jimmy unzipped his pants in front of Mr. O'Connor. "I see, Jimmy, and did that feel good?" "Yes sir, it felt very good to rub my boner through my underwear." "What sort of underpants do you wear Jimmy? Perhaps that is contributing to your problem." "I wear briefs sir, all kinds. I have different colors and some with prints." As Jimmy talked he popped open the button on the waistband of his trousers, exposing the front of his underwear. "Today I have on my spiderman undies." The principal looked down at the boy's red and blue underwear now on view. "I see, Jimmy, aren't you getting too old for underpants like that?" "Yes sir, but I still like them." He was now rubbing his hard-on through the undies. "Well, I understand. So did you continue to play with yourself with your underpants exposed?" "Yes sir." "And then what did you do?" "Well, I was in the back of the classroom, so I didn't think anyone would notice if my pants were down. So I pushed them down and they fell to my ankles. But then I lifted up my feet, and my pants came all the way off." As Jimmy described what he had done in class, he did the same thing in front of his principal. "So you were sitting in class in your underpants?" asked Mr. O'Connor, now furiously masturbating under his desk. "Yes sir, I had my shoes and pants off and was sitting in my underwear and socks." "And you were still playing with yourself?" "Yes sir," said Jimmy as he worked his cock through his undies. "Why did you take your pants off?" "I couldn't help myself. It just felt so good." "Did you like sitting in class in your underpants?" "Yes sir, it felt very good." "Do you like being in your underpants in other public places where people can see you?" "Yes sir." "I see, such as where?" "At the movies, or in restaurants under the table, at the mall, or sometimes at the playground." "I see, you enjoy having men see you in your underpants?" "Oh yes sir, it's fun!" "I see, well then what did you do next in class? Did you take your shirt off?" "No sir, I thought the teacher might see. You mean like this?" asked Jimmy as he pulled off his shirt and dropped it onto the floor with his pants. "Yes, like that. So then what happened?" "It felt so good rubbing my boner that I pulled my underwear down, and then it popped out in the open." While he said this Jimmy pushed down his briefs. They slid down to his ankles, and he let them fall off his feet. He was sitting naked except for a pair of socks in front of his principal. "I see, and do you often let people see your penis?" said Mr. O'Connor, now staring at the boy openly masturbating in front of him. "Yes sir, it makes me more excited to have my boner out in the open and for men to see it and see me playing with it. It is lots of fun and feels good," said Jimmy, jacking himself. The boy used his socked foot to kick his spiderman undies underneath his principal's desk. He saw the man reach down to pick up the underpants, then he heard him unzipping his pants. "Did the other boys in class notice you masturbating with your trousers and underpants off under your desk?" The principal pulled out his hard cock and wrapped the boy's briefs around it. "Yes, some of them sitting around me saw." "How did they react?" "A few boys laughed and made fun of me, and a few watched me and got boners in their pants." "How did the boys make fun of you?" asked the principal as he masturbated. "Did they call you names?" "Yes sir, they called me fag." "Does that upset you?" "No, I don't care," said Jimmy as continued to openly jack off in front of his principal. "It just made me more excited knowing they were watching me." "Do you like to be watched while you masturbate?" "Yes sir, it excites me." "Who as watched you masturbate?" asked the principal as he continued to stroke his cock using the boy's underpants. "Teachers, boys in class, waiters in restaurants, sometimes my dad's friends, strange men I don't know. One time at the movies an usher watched me." "I see, and you don't mind all these men seeing your naked, erect penis while you play with yourself?" "No sir, I like it, it feels, oh, oh, oh, uhn, uhn," Jimmy couldn't help but start moaning as he felt his orgasm building up. "What's wrong, Jimmy?" "Nothing sir, I just ... I ... um." "Are you going to ejaculate?" "Yes sir." "What happens when you ejaculate in public? Does it make a mess?" "Yes sir, I squirt all over myself, or sometimes all over my clothes, oh, oh, uhn." "You mustn't ejaculate here, Jimmy, you should try to hold back." "Yes sir, I'll try, but it's hard, it feels so good, uhn, uhn." "I know, but you should try to control your urges. Do you want men to see your sperm when it shoots out of your hard penis?" "Oh, yes sir, it feels so good, oh, oh, oh." "You must try to hold back." "Yes sir, but it's so hard," said Jimmy as he neared orgasm. "Uh oh! Uh oh! Oh sir, I can't stop it! I can't hold back any longer! I'm going to make a mess! Oh no! Right in front of you, sir, I'm sorry, uhn, uhn, uhnnnnnn," Jimmy moaned as his sperm shot out of his hard dick. His cock throbbed as he continued to spurt jizz that landed all over his bare chest and legs. At the same time the principal was pumping a load into the boy's briefs still wrapped around his dick. "Well I see you couldn't control your urges," he said. "I'm sorry, sir, I couldn't help it." "Well, that's OK, Jimmy, I understand," said Mr. O'Connor with a wink. Jimmy smiled at him as the last few drops of cum oozed out of his cock. "I'm sorry, sir, I made a mess." "That's OK, but you had better get dressed and go back to class." "Yes sir," said Jimmy. His underwear was gone, so he slid his feet into his pants and pulled them up. The semen was already soaking through the material as the boy zipped up his pants. He pulled his shirt on over his head, and it too began to soak up the cum that had spilled all over him. The boy was a mess with obvious wet spots all over his clothes. "Now next time, Jimmy, just be careful who is around when you get an urge like that." "Yes sir," said Jimmy as he walked out of the principal's office full of cum. It was several minutes later after Mr. O'Connor had zipped himself up that he moved his feet, kicking the boy's shoes still under his desk. He realized that Jimmy had gone back to class in his socks. "Oh well," he thought to himself, "I will return them the next time I see him in my office."