Jimmy Likes to be Embarrassed by James Thompson soxandboxersboy@yahoo.com
Ever since he was little, Jimmy liked getting himself into embarrassing situations. When he became old enough to get boners, he realized that he got excited from being embarrassed in public, especially if older men were around to catch him.
For instance one day when Jimmy knew it was going to pour down rain, he got dressed in a white t-shirt and a pair of white track pants and took a walk. He made it as far as the park when the rain began, and within minutes he was soaked. His clothes became completely transparent. At first he felt like he was walking around in just his underwear because his briefs were showing right through his soaked pants, and this gave him a boner.
Soon though as the rain continued, Jimmy's tightie whities were soaked too, and they became see-through as well. Jimmy felt like he was walking around naked since his thin, wet clothes didn't hide much. He walked all the way home with an obvious boner showing through his pants, and Jimmy noticed several men driving by would slow down to check him out.
Jimmy soon learned that he enjoyed masturbating in public, particularly in risky places where he might get caught by older men. One night after his father was in bed, Jimmy snuck out of the house and walked to the park nearby. When he got there he saw that the park was closed and the gate locked, but Jimmy knew of a place where he could sneak under the fence. He got down on the ground and climbed under the fence, but as he did his pants got caught on the metal fence. He pulled himself free, but his pants came off in the process. And as he pants got pulled off, his sneakers did too. He found himself in the park, but dressed only in a t-shirt, briefs and socks.
Looking down at himself in his underwear, Jimmy felt both embarrassed and excited and found himself getting a boner. He began to rub himself through his underpants. He walked around in his socks and underwear, rubbing his erection faster and faster. He went to the playground and sat down on a swing. He reached inside his briefs, pushing them down so that his boner popped out. He began to openly jack off. He was so engrossed in how exciting it felt that he didn't hear the man walk up behind him until he yelled at him.
"Hey boy, what are you doing?"
Jimmy flinched, jumped and whipped around. There stood a security guard in his uniform shining his flashlight on him. Now Jimmy knew he was in trouble. "Uh, nothing sir," said Jimmy as he continued to jack off. For some reason he couldn't stop, he was too excited.
The security guard continued to shine the light on Jimmy as the boy continued to masturbate. "Looks like you're playing with yourself, boy," said the guard. "Don't you think you should do that at home in private?"
"Uh, yes sir," said Jimmy, unable to stop playing with himself.
The guard shined the line on Jimmy's underpants, and the boy was further embarrassed realizing he was wearing cartoon undies with transformers on them. "Where are your clothes, boy?" asked the security guard.
"Uh, I lost them sir," said Jimmy, still jerking off.
"I had better take you home then," said the guard. "You had better pull your underwear back up."
"Yes sir," said Jimmy, pulling his undies over his still-hard dick. "Sir, do you have to tell my father about this?"
"We'll see," said the security guard. "Come on," he said, leading Jimmy to his car parked nearby. The guard locked the park gate back up, then opened his car door so that Jimmy could climb in. The security guard walked around and got in the car, sitting next to the boy. Jimmy gave him his address so the man could drive him home. The whole way Jimmy could not stop playing with himself. He was scared and embarrassed, but excited at the same time. He noticed that the security guard kept watching him.
When the security guard pulled up in front of Jimmy's house, the man reached over and grabbed a hold of the boy's boner through his underpants. "Son, from now on you had better take care of this in private." With that the security guard gave Jimmy's hard-on a squeeze.
Suddenly Jimmy felt himself lose control. Feeling the guard squeeze his boner caused him to start shooting his jizz which began to fill up his underpants. "Oh, oh, uh, uh, yes sir, I will sir," Jimmy managed to say as he shot his load. The security guard continued to hold his dick as the boy came. "Oh, I'm sorry sir."
"That's alright, son," said the man. "I don't think we need to tell your father this time."
"Thank you sir," said Jimmy, getting out of the car.
The guard shined his light on the boy again, looking at Jimmy's cartoon underpants, now with wet stains on the front. "You had better get to bed," said the guard. Jimmy closed the door and snuck back inside. Once in bed he had to masturbate again thinking about what had happened. He hoped he would see the security guard again.
The next day Jimmy walked to a movie theater nearby. It was an old theater in disrepair, and hardly anyone went there anymore. But Jimmy liked to go and noticed a lot of men in suits there in the middle of the day for some reason.
The theater was always pretty dirty. As Jimmy walked in, the floor was so sticky that his shoes kept sticking to it. He had left his sneakers tied pretty loose, so they half-way came off with every step he took. Finally he walked through a very sticky patch which pulled his shoes right off his feet. Since his hands were full with soda and candy, Jimmy just continued on in his socks, leaving his shoes behind stuck to the floor. A couple of men noticed and smiled at Jimmy.
Next Jimmy was walking down an aisle to find a seat, and he did not notice that one of the seats was broken and had a big piece of metal sticking out of it. As he walked past the broken seat, his shorts caught on the piece of metal. Jimmy felt a tugging on his shorts and looked down to see they were caught. With his hands still full, he couldn't pull the shorts free, so just tried to pull away.
Jimmy heard a ripping noise and looked down to see that his shorts had torn, exposing his underpants. Today he was wearing batman underpants. Jimmy continued to tug, trying to free his shorts, but they remained stuck and just continued to rip. Jimmy kept walking, feeling the pulling on his shorts as they continued to rip. He took a giant step and heard a loud tearing sound. As he looked down he saw that his shorts had completely ripped away; the shreds of fabric were hanging from the broken seat.
Now of course several men had noticed, and they started at Jimmy now wearing only his t-shirt, briefs and socks. The men smiled at him in his cute undies. Immediately Jimmy felt embarrassed at men seeing him in his underpants, but excited too. He began to get a boner and quickly took a seat as the movie began.
Soon after the movie started the usher came around. He found Jimmy's shoes on the floor and pulled them off, tossing them aside. Then he saw the remains of Jimmy's shorts, so he shined his flashlight on the boy. "Hey, did you lose your pants?"
"Yeah," said Jimmy, "they got caught on the seat and ripped off me."
The usher, a young guy, shined his flashlight on Jimmy's underwear, noticing that they were batman undies. "Oh sorry, dude," said the usher. "But I like your undies! Good choice too!"
Jimmy grinned, feeling both embarrassed and excited. He had worn batman briefs since he was seeing the new batman movie again. "Thanks," he said, rubbing his boner without even thinking.
The usher sat down next to Jimmy, saying "Mind if I sit here?" as he did. He shined his light down and saw that Jimmy was in his socks. "Did you lose your shoes too?"
"Yeah, they got stuck to the floor."
"Oh, sorry man. Well, it's more comfortable anyway. I take my shoes off all the time here at the theater." As he said this he kicked his shoes off, and Jimmy watched the whole time. "Ah, that feels better," said the usher. "You don't mind, do you?"
"No!" said Jimmy, getting more excited and unable to stop from playing with himself.
"My name is Gus," said the usher.
"I'm Jimmy."
"Nice to meet you," said Gus. "Looks like you got a boner. Do you get them a lot?"
Jimmy blushed and nodded his head. "Yeah, me too," said Gus. "At your age I had them constantly, still get them a lot. In fact I have one right now," he said, pointing at his crotch. Jimmy looked down and could see the bulge tenting his pants. Gus reached down and unzipped his pants. "My undies aren't as cute as yours; I'm just wearing tightie whities."
Jimmy looked down as Gus' white underpants came into view. He rubbed himself a little faster now.
"Hey, I have to make a round and check things," said Gus, "but I will be back. I am going to leave my shoes here." Gus got up and walked away in his socks and with his pants still open, his underpants showing through.
Jimmy slipped his feet into Gus' shoes. They were too big for his feet, of course, but they felt so good. A few minutes later Gus came back, so Jimmy kicked the shoes away quickly. He could see that Gus' boner was pushing out his underwear and bulging out of his open pants. Gus sat back down next to Jimmy. He reached over and grabbed a hold of Jimmy's boner through his underpants. "Mind if I help you with this?"
"Sure!" said Jimmy, getting more excited. He watched as Gus popped the button on his pants so the front of his underwear was completely exposed, and enjoyed the feeling of Gus' hand as he explored his dick through his batman underpants.
They watched the movie as Gus stroked himself and Jimmy at the same time. When batman would come onto the screen Gus would stroke Jimmy harder and whisper, "What kind of underwear do you think batman is wearing?" or "I bet he likes to be seen in his undies like you." Eventually Gus worked his dick out of the fly of his underwear, and he pulled Jimmy's boner so that the head was poking up above the waistband of his undies.
A few minutes later Gus said, "I have to make my round again." He buttoned up his pants, but left his hard cock poking out the fly. "It's dark, so I don't think anyone can see." Gus got up, again in his socks, and walked off to check the theater.
Jimmy looked around and realized that two of the business men in suits were sitting behind him. They must have been watching him with Gus. He saw that both men had their dicks out of the fly of their suit pants.
Soon Gus came back, padding in his socks, his dick poking out of his pants. He said down and began to stroke Jimmy's cock as he jerked himself off. Suddenly Gus leaned over Jimmy's lap and took his dick into his mouth. Jimmy had never had this happen before, and it felt so good having Gus' mouth on his boner that the boy quickly lost control. In only about a minute he began to cum, shooting his load into Gus' mouth. The usher kept sucking on the boy's cock as Jimmy spewed his sperm. He felt Gus suck up every drop. When Gus raised his head from Jimmy's lap, the boy noticed that Gus had cum all over his underwear and pants. Gus buttoned and zipped his pants, not seeming to care that he was covered in semen.
"I have to go back to work," whispered Gus, "but maybe I will see you again sometime." He gave the boy a squeeze before he walked away.
Jimmy noticed Gus had forgotten his shoes, so he slid his socked feet into the oversized shoes as he watched the rest of the movie still playing with himself.
Jimmy was back in school, so one day after school he walked to the college library near where he lived. He was still wearing his uniform of polo shirt, dress pants, dress shoes and socks. None of the boys at school knew that he had been wearing Scooby-Doo undies under his uniform all day.
Jimmy sat down at a table and pulled out his homework. He quickly became bored, though, and reached under the table to play with his boner through his dress pants. Suddenly he realized that someone was watching him. It looked like a college student, and he was dressed in khaki pants, a polo shirt, loafers and dress socks. The student smiled at Jimmy and sat down at the table opposite him. Jimmy smiled back, still rubbing his crotch.
The student slipped off his loafers, and the next thing Jimmy knew, he was using his socked feet to pull the boy's dress shoes off too. As Jimmy felt his shoes being pulled off his feet, his boner pulsed and shot out some pre-cum. Soon he felt the student rubbing his socked feet all over his.
Next Jimmy felt something in his lap, and he looked down to see the student's socked feet rubbing his boner. Suddenly Jimmy realized there were other guys studying nearby, and he became embarrassed. But he was excited too, and didn't want the student to stop rubbing his feet against his hard-on.
Then the student got up and left the table. At first Jimmy was disappointed, but then saw that he was motioning for him to follow. He got up and followed the student; both were in their socks and left their shoes behind under the table.
The student led Jimmy behind some bookstacks, where he stood behind the boy and unbuttoned and unzipped his school uniform trousers. The pants fell to the ground, and the student stepped on them so Jimmy had to walk out of them. The student leaned down and whispered, "I like your undies."
Jimmy blushed and put his hands over his briefs, suddenly realizing he was in his cartoon underpants in public. Then the student pulled Jimmy's shirt off over his head, and the boy was standing in just socks and underpants.
The college student got down on his knees and pulled down Jimmy's underpants so that his boner sprang free. He pulled them all the way down and Jimmy, almost without thinking, stepped out of them. Now he was almost naked!
But he forgot about that when the student began to suck on his boner. It felt so good that his knees began to buckle, so the student helped Jimmy down onto the carpeted floor. Jimmy lay there naked except for socks as the guy licked and sucked his hard dick. At first Jimmy had his eyes closed enjoying the feeling, but when he opened them, he saw that they were being watched. One of the guys who had been studying nearby was now standing on the other side of the bookstacks watching the student suck Jimmy's cock.
Jimmy got so excited that he couldn't hold back any longer. He wiggled his toes in his socks and felt himself start to cum, shooting sperm into the student's mouth. He kept sucking in all of the cum as Jimmy kept shooting his load. He knew that the student was cumming too, because he felt his warm semen shooting onto his naked chest.
When Jimmy looked again at the guy watching from the other side of the bookstacks, Jimmy saw that he had a funny expression on his face and was probably cumming too. As soon as the student had sucked up every drop, he quickly zipped up and left, leaving Jimmy naked on the floor. Jimmy got up, found his clothes, and got dressed up. He walked back to the table to get his shoes, but when he got there they were gone. But in their place were the student's shoes. They were too big for Jimmy, but he didn't care. He slipped his feet into the shoes and walked home with the loafers falling off his feet with every step.
A few days later Jimmy's dad had to stay late at work so he left money for his son to get some dinner. Jimmy walked to a fast food place near his house. He sat at a booth in the corner of the food place which was almost deserted. While he sat there finishing his food, a group of boys from the local high school came in and sat down in the booth behind Jimmy.
As the boys passed, they noticed that Jimmy had a boner and was rubbing it through his pants. He overheard one of the boys say, "The little dude at the table behind us is jerking himself man!" Then Jimmy heard the boys laugh, and a couple turned to look at him.
Jimmy felt embarrassed but suddenly got so excited he knew he had to do something risky. Jimmy slipped off his sneakers, then slid them away under his seat. The shoes slid across the floor and ended up underneath the boys' table. The shoes bumped one of the boy's feet, and he looked under the table, saying, "Hey the little dude took his shoes off. They're under the table here!" Then Jimmy heard another boy say, "He's not getting these back."
Jimmy got so excited he couldn't stop rubbing his boner through his pants. He knew he had to go farther. He slowly unbuttoned and unzipped his pants, pushed them down, then let them slide off. He kicked his pants so they slid across the floor under the table. Then Jimmy pulled off his shirt, dropped it onto the floor, and kicked it away too. He was now wearing only his white socks and a pair of pokemon underpants. He was hard as a rock and couldn't stop playing with his boner.
"Hey," Jimmy heard one of the boys behind him say, "the little pervert took all his clothes off! They are under our table!" Jimmy was rubbing himself faster now. "What a little faggot," said another boy, "we're not letting him get his clothes back." Jimmy couldn't stop masturbating as he listened to the boys talk about him.
When the boys finished eating, they got up from their booth with Jimmy's clothes. As they walked past Jimmy's table, they were saying "faggot" and "pervert." Jimmy couldn't help but play with himself as the boys walked past and started at him. He was so excited, and got even more excited when he saw that they were carrying his clothes and shoes out. He even heard one boy say, "gay undies" under his breath.
Jimmy watched the boys walk outside and over to the dumpster. As he saw the boys toss his shoes and clothes into the dumpster and Jimmy knew he was going to have to walk home in socks and underwear, he lost control and shot his load into his underpants. Now he wondered how he would get home.