Date: Wed, 24 Feb 2010 15:01:42 -0800 (PST) From: Jimmy Thompson Subject: babysitting a show off-5 Babysitting a Show-Off - 5 by Jimmy Thompson soxandboxersboy@yahoo.com (Note: I haven't submitted anything in a while, so decided to add a quick chapter to my story; it is short, but if people like it, I can try to add more in the future) Bobby was excited; his favorite babysitter, Jack, was coming to stay for the weekend since Bobby's dad was going out-of-town. Jack arrived at the house and received his last-minute instructions from Bobby's dad before the man left. As soon as the door closed, Bobby rushed over and gave Jack a big hug. Jack could feel that Bobby already had a boner in his pants from being so excited. Jack took Bobby out to eat at a pizza restaurant that also had an area with video games and places for kids to play. The good thing was that the parents ignored their kids, so they were pretty much free to do what they wanted. Jack and Bobby sat down and ate first. Bobby kicked off his sneakers, and Jack could feel the boy's socked feet rubbing his legs under the table. So Jack slipped his shoes off as well. He rubbed his feet against Bobby's, then slid one foot up his legs and into his crotch. Jack rubbed Bobby's boner through his jeans with his socked foot as the boy giggled. After they ate, the boys went to the games area, and Bobby began to play a videogame. Jack came up behind the boy, reached around his waist, and undid his jeans. Bobby giggled as his jeans slid down to his ankles, then he stepped out of them and kicked them away. Jack gave the jeans another kick out of the way. As the boy continued to play, Jack managed to get Bobby's shirt off, and he tossed that away too. Now the boy stood in just his socks and cartoon undies playing the game. The other boys playing in the area couldn't help but notice Bobby in his underwear, and Jack noticed them all whispering to each other. Soon two other boys took off their shoes and clothes as well, getting down to their underpants. Before long the rest of the boys were all undressing, and soon every boy was playing in his underwear. Jack noticed all kinds, from boxers to white briefs to colorful and cartoon undies. Many of the boys were as hard as Bobby. Jack continued to stand behind Bobby, and as the boy played, he wiggled around, grinding his bottom into Jack's boner. Jack began to subtly hump the boy, grinding himself against the boy's briefs-clad rear end. Jack undid his jeans enough so that he could hump the boy with just their underwear between them. Now many of the boys in the games room were noticing the two. As Jack continued to rub up against Bobby, he also reached around and began caressing the boy's hard dick through his briefs. Bobby began to moan with pleasure, but continued his game. Jack began to hump harder, and rub the boy's boner more rapidly. He would look around occasionally, and he noticed that several of the boys, all still in their underpants, had stopped to watch him and were masturbating themselves through their undies too. Jack was grinding harder, his pants falling to his ankles, as Bobby moaned and pressed his buttocks against his babysitter's hard dick. Within a few more minutes, Bobby let out a grunt, and Jack could feel sperm filling the front of the boy's underpants. Jack pressed himself against the boy hard, and at that point shot his load inside his underwear. Once both boys had cum, Jack looked around and saw that a few of the boys watching now had wet patches on the front of their underpants. He also noticed two boys humping each other on the floor and decided he had better go. He pulled up his pants but led Bobby out of the restaurant in just his underwear, leaving his clothes behind. The next morning the boys were sitting in their underwear and eating cereal for breakfast while they were talking about what to do that day. The doorbell rang and Bobby ran to answer the door, still wearing only his underwear and socks. Jack watched as he opened the door to a delivery man with a package. As Bobby chatted with the driver for a few minutes, he reached down and rubbed his erection that was tenting his briefs. Jack watched as the boy masturbated the entire time he was talking to the delivery man; and the driver couldn't help but notice as well. That gave Jack an idea. The boys dressed and headed for the mall. In the car on the way, Jack gave Bobby instructions as to what to do when they arrived. The pair first went to a clothing store for young men, and Bobby approached the salesman working in the store. As the two talked, Bobby began to undress as Jack had instructed. The man looked surprised ad Bobby stepped out of his shoes, then unbuttoned his shirt and dropped it to the ground. But after the surprise wore off, the salesman enjoyed watching as Bobby continued to undress, unbuttoning and unzipping his pants and letting them drop. Bobby stepped out of them and was in his socks and underpants with pictures of race cars on them. Bobby and the salesman continued to talk as the boy now began to masturbate through his undies in front of the man. The sales clerk began to show Bobby some clothes, walking the boy through the store, still in underwear and still masturbating. The man would help the boy try on some outfits, taking time to fasten the trousers carefully. Then he would help the boy out of the clothes and onto something else. Jack watched everything from a corner of the store, and he noticed other men watching as well. The salesman led Bobby to some nice dress clothes made of material that was very soft and silky. He helped the boy into the shirt, then before putting on the pants, Bobby pulled his underpants down and off. The man helped him into the silky trousers, and as the clerk slowly zipped them up over Bobby's boner, the boy gasped. "Oh no!" he said, "I'm cumming!" And with that the boy began pumping his load of semen into the pants as the clerk, Jack and a few customers looked on. After Bobby had shot his load, he apologized to the man for messing up the trousers. The sales clerk said it was no problem as he helped the boy out of the pants. The man stashed them behind the counter, and Jack suspected he would use them again later. The man helped Bobby to dress, and he and Jack left the store. The boys went to the food court for sodas and took a seat in one of the booths. Jack noticed a father and son sitting at a nearby booth, and he also saw that the father was watching and smiling at Jack and Bobby. Jack whispered in Bobby's ear, and the boy nodded and got up. He pretended to be getting napkins, but instead he ducked down and crawled underneath the booth where the father and son sat. When he felt hands untying his shoes, the man looked surprised. He looked under the table to find Bobby smiling up at him. The man smiled back and relaxed. Soon he felt Bobby undoing his shoes and pulling them off. Then he felt hands on his zipper, so he positioned himself to let Bobby undo his pants and pull them off. Bobby played with the man's hard cock through his briefs, then finally pulled down the elastic waistband, freeing the man's erection. When he felt Bobby's mouth on his hard cock, the man gasped. "Are you alright dad?" asked the man's son. "Oh yes, son, just fine!" the man answered. He was clearly enjoying having Bobby's mouth slowly moving up and down on the shaft of his hard cock. He closed his eyes, lost in the pleasure of getting an incredible blow job. The man's son became curious about what was happening, so he looked under the table to find Bobby there. The boy crawled under the table and watched, then Bobby stopped so that the boy could try. Soon the boy was sucking his father's hard cock. As the boy continued to pleasure his father, Bobby returned to the table to watch with Jack. The two masturbated as they watched the man's son giving him a blowjob. The man grunted as he came, pumping his cum into his son's eager mouth. When he had shot every drop, the man opened his eyes and was surprised to find his son was not sitting there. He was even more surprised when he looked under the table to find his son there. The man quickly pulled his clothes back on before quickly leaving the mall. On the way home the boys made one more stop - in the park. They decided to play Bobby's favorite game, Clotheszilla, but this time with a twist. Jack pretended to be the monster and chased Bobby. This time as he would catch the boy, Jack did not just pull an item of clothing off - he tore it off. The first time Jack caught Bobby, he pulled the boy's shoes off and through them. Bobby continued running around the park in his socks. When Jack caught him again, he pulled on the boy's shirt. A ripping noise was heard as part of Bobby's chest was exposed. Jack chased Bobby around, and each time he was close enough, he would rip away more of Bobby's shirt. Scraps of cloth hit the ground as they continued, until finally his shirt was completely ripped away and Bobby was bare-chested. By now other boys playing in the park had stopped to watch them. Jack continued to chase Bobby, and the next time he caught him, he pulled on his pants. A rip was heard as the side seam split open, exposing his briefs. The next time he caught up with him, he tore the back of his pants and Bobby's underpants-clad rear end was on view. This continued on as Jack pulled scraps of cloth away, until finally the pants were reduced to torn pieces of fabric on the ground. Bobby was now running in his underwear and socks. Now several of the other boys in the park began playing the same game. They would chase each other, and if a boy caught another boy, he would rip his clothes. As this continued, more and more of the playing boys lost their clothing. Soon most of them were also running around in their underwear, their clothes nothing but scraps of material lying around. Jack sat down on a bench to watch the boys, and Bobby sat in his lap. Jack undid his pants to expose his hard cock so he could rub it against Bobby's rear end. The boy wiggled around, enjoying the feeling of Jack's dick against his bottom as he watched the boys in their underwear play. Soon Bobby felt the back of his underpants become wet as his babysitter lost his load, shooting sperm all over the boy's underpants. Afterward the pair continued home, ready for more fun.