Losing his Clothes by Jay Thomas showmeursox@yahoo.com
Jimmy was always undressing and losing his clothes in public places. He was always getting into trouble with his dad and getting teased by other boys, but that just made it more exciting for him. Ever since he had learned to jack off, Jimmy seemed to always be playing with himself, and he would get so excited that he would just start undressing wherever he was. Sometimes he lost his clothes and ended up in his underwear and socks or even less, and this gave him a thrill too. Often other boys would tease him and pick on him and even take his clothes from him, all of which got Jimmy even more excited. He loved to get caught without his clothes as well as getting caught when he was jacking off.
Jimmy was sitting in English class, his favorite, not because it was the last period of the day, but because he had a crush on his teacher, Mr. Bryant. He was just out of college, young, and handsome. Jimmy got a boner in every class and often rubbed it under his desk just staring at his sexy teacher. When he had walked into class today, Jimmy was thrilled to see that Mr. Bryant was wearing a pair of very thin linen pants in an off-white color. He noticed that Mr. Bryants boxers were showing right through! It was as if his teacher weren't wearing pants! Jimmy immediately popped a boner and half-heartedly used his books to hide it as he took his seat. He heard one of the boys behind him say to another boy, "Hey, look at that fag, Mr. Bryant, you can see his underwear showing through his pants! He must get off having us guys checking out his undies!" Hearing that just got Jimmy more excited, and he started to masturbate through his uniform pants under his desk.
As class began, Jimmy slipped off his dress shoes and kicked them behind him under his desk. He continued to play with himself as he watched his teacher writing on the blackboard, his underpants clearly visible through his thin trousers. Then he heard another boy behind him say, "Look, Jimmy the faggot took his shoes off again." As he said it, the boy picked up Jimmy's shoes, handed them to the boy next to him, and whispered something to him. Jimmy watched as his shoes were passed around the classroom. Then when Mr. Bryant turned back to the blackboard, a boy quickly got up and tossed Jimmy's shoes out of the open window. Watching his shoes disappear just got Jimmy more excited, as did the boys snickering behind him, so he rubbed himself harder through his uniform pants.
As Jimmy watched his teacher walk around the room with his underwear showing, he found himself getting more excited and unbuttoned and unzipped his pants. He was now rubbing himself through his briefs. Then he heard a boy behind him say, "Hey look, faggot Jimmy is jacking off again," and his friend say, "Yeah, he wants us to see his undies like faggy Mr. Bryant." The boys continued to whisper and snicker as they watched Jimmy masturbate.
Jimmy was close to cumming as he played with himself while staring at his teacher, but the bell rang so he quickly zipped his pants back up. He walked out of class without shoes in his dark cotton socks while he heard boys talking about it and laughing at him. Jimmy tossed his books into his locker and left the school to walk home. When he had gotten a couple of blocks away, he heard a voice behind him say, "Hey faggot!" Jimmy turned to see several of the boys who had been making fun of him in class. "Are you some kind of queer who likes guys to see your underwear like that faggot teacher? Why don't you let us all see your undies!" With that the boys grabbed Jimmy and pushed him down to the ground.
Jimmy felt the boys pulling on his shirt. Soon it began to rip at the seams, and he felt it tearing away from his body. He heard the ripping sounds as his uniform shirt was torn from him, leaving him naked from the waist up. Then Jimmy felt the boys' hands on his uniform pants, pulling at them and tearing them. He heard the ripping as his trousers were torn to shreds, exposing his white briefs. "Oh, sick man," said one of the boys, "he has a hard-on!" As the last shred of his pants were ripped off, Jimmy looked down to see his boner tenting his underwear. The boys all laughed and called him names like faggot as they walked away with the scraps of his clothes. Jimmy stood up and looked around, realizing he was now outside in just his underpants and socks.
Jimmy continued walking home in his underwear, now so excited to be in this state that he jacked off as he walked. He headed for him, rubbing himself through his undies the whole way. Anytime a car drove past he rubbed faster, excited at having people see him. A few cars honked at him. As he walked through puddles his socks became wet and he got more excited. By now he was leaking so much pre-cum there were wet spots on his tighty whities.
As he approached his house, a car pulled over, and Jimmy saw that there were older boys inside. They called him over, and Jimmy approached the car. The driver asked, "Hey, what happened to you?"
Jimmy replied, "Some boys from my school stole my shoes and clothes."
The driver said, "Looks like they forgot something," and reached out, grabbed a hold of Jimmy's briefs, and yanked them down. Jimmy was startled and moved backward, and as he did he ended up stepping right out of his underpants. Now naked except for his socks and with so many guys seeing him like that, Jimmy couldn't hold back any longer. He began to cum, squirting his load all over his feet and the ground.
"Gross, man, the kid is jizzin' all over himself!" said one of the boys in the car. They all laughed and the car drove off, the driver still holding Jimmy's briefs. Jimmy walked the rest of the way to his house naked and still dripping cum, aware that his next-door neighbor was watching through his window.
The next day was Saturday and Bob, Jimmy's dad, took him with him to run some errands, ending up at a diner for lunch. As he ate, Jimmy became aware that some older boys from his school sat down in the booth behind him. They noticed him too and began to call him names and snicker at him. Jimmy found himself getting excited again.
Jimmy slipped his sneakers off under the table and wiggled his toes in his white socks. He kicked the sneaks under his seat, hard enough that he knew they would end up under the table behind him. He heard one of the boys say, "Hey look, the faggot's shoes are over here." Then Jimmy heard them start to kick his shoes around under their table.
By now Jimmy had a boner, so he unzipped and unbuttoned his jeans so that he could rub himself. When his dad wasn't paying attention, Jimmy lifted up his hips and slid the jeans down. They quickly ended up at his ankles, and Jimmy pulled his feet out of the jeans and also kicked them under the table. He heard one of the boys behind him say, "Dude, look, the faggot is takin' off his clothes! His pants are over here!" Another boy said, "Yeah the queer is probably jackin' off again, what a faggot!"
As Jimmy pretended to listen to his dad, he was secretly listening to the boys behind him and rubbing his boner through his briefs under the table. He was excited at being half dressed at the table and jacking off right in front of his dad who didn't know. When his dad was talking to the waiter, Jimmy quickly unbuttoned and slid his shirt off. Since he was wearing an undershirt, he figured his dadn't wouldn't notice right away that he had taken the outer one off. Jimmy dropped the shirt onto the floor and kicked it away. He heard the boys behind him laughing as they were passing around his clothes.
Jimmy could hear the boys laughing, and he also heard ripping sounds. He knew the boys were ripping up his clothes. Bob didn't notice but did realize his son's shirt was gone, so he asked Jimmy, "Where's your shirt?"
"Um, I took it off 'cause it was uncomfortable," said Jimmy.
"Well you have to put it back on; we've talked about your taking clothes off in public many times - you can't do that."
"Um, well, I lost it," said Jimmy.
"You lost your shirt?" asked Bob. When Jimmy nodded, his dad said, "This is why you can't undress in public places. We've talked about this before, and you know you are not supposed to."
Jimmy was looking at his dad and nodding, and under the table he continued to masturbate because he was so excited. He loved to get caught without his clothes, getting embarrassed, and even getting in trouble for it.
"Come on, let's go," said Bob, getting up. As Jimmy stood up, his dad looked at him in just his undershirt, briefs and socks and said, "Did you take off all your clothes?" When Jimmy nodded his dad asked, "And did you lose all of them?"
Jimmy nodded again, excited at standing in the diner in his underwear with everyone looking at him get in trouble with his dad for it. He knew the boys at the table behind him were looking and laughing at him. When his dad went to the counter to pay, Jimmy couldn't hold back any longer. Standing in the middle of the restaurant and right next to the older boys, he began to cum. His whole body convulsed as he filled his briefs with spunk. The boys burst out laughing, and one said, "Look, the faggot is making a mess in his undies!"
Jimmy walked out of the restaurant in his socks and underwear full of cum knowing everyone was watching and laughing at him.
The following Saturday Jimmy's father had to go to work, leaving Jimmy on his own for the day. Jimmy decided to go out and have some fun, hoping to lose all of his clothes by the time he got home.
First he got on the bus to head into town. Two of the bullies who picked on him at school saw him and sat behind him. On the bus he took off his sneakers, and as the bus turned a corner, his shoes slid away from him. The sneaks ended up under the seat behind him. The boys saw them and one said, "Hey look, it's the faggot's shoes." The other boy said, "Toss 'em out the window," so the first boy slid the bus window down.
As Jimmy watched, his sneakers were tossed out of the window of the moving bus. Jimmy got so excited he started to rub his boner through his shorts.
"Oh look man," said one of the boys, "the faggot is playin' with himself again." The other boy said, "That's sick, dude," as both of them watched Jimmy rub his crotch.
Jimmy got off at the next stop, walking off the bus in his socks as he heard the boys laughing and continued rubbing hiimself through his shorts. Jimmy walked to a strip mall and went into a clothing store. Inside he saw some of the older boys from school looking for clothes. As Jimmy browsed around the store, he was aware that the older boys were watching him and snickering. While Jimmy was looking at a rack of shirts, he heard one of the older guys behind him say, "Hey, I like this shirt." The boy then grabbed a hold of the shirt Jimmy was wearing. "I think I'll take this one," he said as he pulled Jimmy's shirt off over his head. The boy put the too-tight shirt on over his own t-shirt and said, "Yeah, I like this, and it's a good price too - free!" With that the boy walked away with his laughing friends, leaving Jimmy in the store now naked from the waist up.
Jimmy walked out of the store and padded in his socks down to the restroom. He had to pee but, instead of using a urinal, he went into one of the stalls. He pulled his shorts down to ankles and his underwear down to his hips and sat on the toilet. As he peed, Jimmy heard some boys come into the restroom. They noticed Jimmy in the stall and whispered and giggled. Then suddenly one of the boys reached under the stall, grabbed Jimmy's shorts, and yanked them off his feet.
Jimmy stood up, flushed the toilet, and walked out of the stall, now dressed in just his underpants and socks. The boys in the restroom saw him and and laughed at Jimmy standing in his underwear. Jimmy walked out of the restroom to head home.
Now Jimmy knew he couldn't take the bus again, so he had to walk home. He was so excited to be walking home in his underwear and socks that he couldn't keep from jacking off as he walked. He knew anyone that walked or drove past would see him masturbating in his underwear.
Jimmy kept walking through puddles, getting his socks wet, and muddy places, getting his socks dirty. He decided to cut through a field and walked right through a mud puddle. Jimmy sank right in and his feet got stuck. He had to pull his feet out of the mud, and as he did, his socks came off. He had to leave his dirty socks behind and continue home barefoot.
Soon Jimmy was back on the sidewalk, now wearing only briefs and jacking himself off through the thin material. Suddenly he heard a group of boys on bicycles riding up behind him. Jimmy took a step to the side to get out of their way, but one of the boys rode his bike right by Jimmy. The boy reached out and grabbed a hold of Jimmy's underwear, giving them a yank. The older boy was strong, and with a loud rip, Jimmy's underpants were torn right off. He was almost knocked over from the force. The boy laughed and yelled to his friends, "I got the faggot's underwear!" He threw the torn briefs into a mud puddle, and all of the boys rode over them whith their bikes.
Jimmy was now so excited to be naked in public where boys could see him that he couldn't stop masturbating. He continued to jack his dick as he walked toward home. Then Jimmy heard a car honk and pull over to the curb. Jimmy walked over to the open window and saw his favorite teacher, Mr. Bryant, at the wheel. "What happened to your clothes?" he asked.
"Uh," stammered Jimmy, "some boys took them." Suddenly the sensation of standing completely naked in front of the object of his schoolboy crush with a boner was too much excitement for him and he started to cum. He began to shoot his load right in front of his teacher, spewing sperm all over Mr. Bryant's car. "Uh oh, uh oh, I'm sorry Mr. Bryant, I can't help it," said Jimmy, now overcome with a feeling of intense excitement.
"That's O.K.," said the teacher, "sometimes that happens. Why don't you get in and I will give you a ride home?"
Jimmy grinned and hopped in the car, naked and still dripping cum. "Thanks, Mr. Bryant." Jimmy wondered if he would be able to keep himself from playing with himself in the car with his teacher. He knew for certain he couldn't wait until the next time he lost his clothes.