Started with a prank

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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enmfan
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Started with a prank

Post by enmfan »

Billy is 14 years old he has a younger 13 year old sister named Katy. They get along fine enough and like all brothers and sisters close in age there is a fair bit of pranking and teasing. He isn't a jock, he isn't a nerd he is a run of the mill 14 year old. He is a keen swimmer and most weekends he can be found practicing at the local pool and this is where it all began.

Being a keen competitive swimmer a lot of Billy's free time is taken up practicing at the local pool. It's a straight forward pool with multiple lanes and a few diving boards. A lot of people Billys age come to the pool to mess around. He doesn't get involved keeping to himself and the other teens don't really bother him. On this day Billy found himself in an awkward situation through none of his own doing. A group of people from Billy's class a mix of 3 girls and 3 boys were messing around pushing each other in the pool and being loud and annoying. Billy ignored it as they never really interacted with each other even in school. Billy did know one of the girls there her name was Amy. Amy was a cute popular girl way above Billy's league and didn't look twice at him but her Mother was Billy's maths tutor and was just as cute as Amy. She was young when she had Amy being in her early 30's now it was hard to focus on maths lessons. But back at the pool Amy and her friends were getting closer and closer to the swimming lanes disturbing all the swimmer. Finally the lifeguard had enough and told them to get out. They swam across Billy's lane climbing out the ladder one by one not even stopping to acknowledge Billy. Amy was the second to last out with one of the boys still in the pool. As Amy got to the top of the stairs the boy reached up and pulled the back of her swimsuit down Billy was shocked but could not look away. There was the cutest girl in his class with her bare ass hanging out. He was shocked there was no tan line just 2 we tanned cheeks. Amy let out a scream in shock pulling her bottoms back up and turning around to see her friend laughing his head off and a boy from her class open mouthed with eyes as big as his head. She quickly climbed the final step and could be heard telling off her friend as they walked to the locker rooms. "oh my god that boy saw my ass you dick my mom knows him you idiot"
Billy could not believe what he saw thank god he was in a pool he thought as he felt something stirring downstairs. A small tent had formed in the front of his speedos and he swam it off for the next 20 minutes before heading to the locker room. No sign of the others they had long gone kicked out for the butt exposure. Billy headed into one of the private shower cubicles taking off his swimsuit and hanging it on the peg just on the other side of the curtain with his towel. He got in the habit of turning his back to the curtain side as people would open the curtains without checking if anyone was inside this way only his ass would be exposed and he would have a chance to cover up. Once finished Billy reached for his towel and wrapped it round his waist carrying his speedo in his hand as his key was attached to the swimsuit. He got changed without incident and headed home via bike.

Once home he was greeted by his younger sister who liked to tease him about his swimming habit. His lack of body hair was a great topic of amusement to her as she had walked in on him in the shower more then once. Billy liked to keep clean shaven as he thought it gave him an advantage in competition. "Had fun at the pool today baldy" Katy teased making Billy turn red in an instant. "I told you not to call me that you brat" Billy replied. "What BALDY well what else should I call you it's not my fault you got no hair down there" she teased back. "Shut up I choose to shave it of its none of your business" Billy snapped back. "Oh relax i'm only teasing mom told me to remind you tomorrow no swimming be back for maths" Billy suddenly had flashbacks to the pool and the sight of Amy's ass. Something was stirring in his shorts again he quickly rushed past Katy before she noticed. Well that was weird Katy thought seeing Billy running up the stairs making sure to keep his back to her. Not 30 seconds after Billy had made it to his room Katy knocked on his door. "whats your problem" Katy shouted through the door. "Nothing just give me a minute" Billy called out standing behind his door desperate for Katy not to see him in this state. Billy quickly sat on his bed and put a cushion on his lap just before Katy barged in without asking. "What the hell Katy" Billy squealed "why are you acting like this" Katy said in a stern voice. "I'm not feeling well can you leave me alone please". "Some girl named Amy called she wants you to call her back". Billys eyes nearly darted out of his head even mention of her name triggered a reaction downstairs. He was now desperate for Katy to leave but she was having none of it. "Who is she you have never talked about and Amy before" teased Katy. "Shes a girl in my class we are doing a science project together" Billy replied. "Aww do you like her is that why your acting so strange". "No I told you i'm not feeling well". "Sure big brother if your sick ill talk to her for you and ask". "NOOO" Billy shouted jumping up dropping his cushion on the ground exposing his tent to Katy. "ahhhh" Amy screamed staring straight it then breaking into laughter. "Billy's got a Boner" she teased breaking eye contact with his tent to look him in the eye. "Get out" Billy shouted pushing a laughing Katy out of his room and slamming the door. "Fine ill tell Amy your having a HARD time right now and to call you back at a less exciting time" Katy called through the door through her giggling. Billy was mortified he needed a minute to compose himself it was one of the most embarrassing moment of his life. Even though she had seen him naked before never had she seen him hard. What Billy didn't know is Amy had told Katy what happened earlier in the day she knew why he was acting so strange and gave him the chance to tell the truth. Amy and Katy had given each other their numbers and were now texting back and forth.

Amy: Did he tell you
Katy: No he was too embarrassed haha
Amy: Whats he got to be embarrassed about it was my ass that got exposed.
Katy: Haha I know I think he liked it if that helps
Amy: Eww how would that help
Katy: Haha sorry how can we make this fair
Amy: fair I don't know its not like he did it
Katy: Yeah but why should he have all the fun
Amy: Its so embarrassing I hope he doesn't tell anyone
Katy: We can make sure he doesn't say a word I have a plan
Amy: I'm in this can't get out
Katy: Your mom is coming over tomorrow make sure you come with her
Amy: Aww really I don't want to waste my day waiting for her to finish her lesson.
Katy: Trust me come with her Billy thinks you will be here at 3 but make sure you are here for 2:30 and have your phone ready.
Amy: What do you have planned
Katy: I'm not gonna spoil the surprise but its gonna be something you will not regret missing.
Amy: Ok see you tomorrow
Katy: Bye

Just then Billy had come back downstairs having calmed down. "Whats up big brother" Katy teased looking at his crotch. "Stop it Katy enough did Amy call back". "Relax I told her you would ring back tomorrow afternoon after your lesson". Billy breathed a sigh of relief. "Mom is gonna be home soon so i'm going to get ready for bed do you need a cold shower before I use it" Katy teased when she walked away heading to the downstairs bathroom. After having her shower Katy took all the spare towels out of the bathroom cupboard sneaking them up to her room and hiding them under her bed. She knew Billy never checked before his shower and just expected them to be in there post shower. The trap was set would Billy fall for it.
Jeepman89
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Re: Started with a prank

Post by Jeepman89 »

Enmfan, fantastic start! I look forward to the next part!
enmfan
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Started with a prank part 2

Post by enmfan »

Part 2

Billy spent most of the day shut up in his bedroom to avoid his sisters teasing. Knowing that it was just the 2 of them at home all day because his mom had to work weekends he knew he didn't have to show his face all day. He did venture out of his room to grab some food around lunch time and as luck would have it there was his sister standing in the kitchen. "Hey Billy what have you been up to all morning" Katy said in a teasing way. "nothing just playing on my Xbox why" Billy stammered out. "You sure that's all you have been playing with" giggled Katy looking down at his crotch. "shut up stop looking there" Billy squealed holding his hands over his crotch. Katy laughed at the pathetic sight of her brother with his hands covering up walking off she said "better shower before Mrs Smith gets here you stink baldy" Billy knew he had plenty of time left to shower before his lesson so after he had some lunch he went back to playing Xbox. He almost lost track of time when he looked at the clock and realised he only had 1 hour left till his lesson. He quickly took off his clothes walked to the downstairs bathroom in his boxers having to walk pass his sister one more time. Katy knew she couldn't let on too much that she was setting up Billy so she didn't say anything this time just laughed when his hands shot to his crotch again. She watched him go into the bathroom and shut the door knowing that he took his time before he went in the shower. Everything was falling into place all she had to do now was wait till she heard the shower running. Billy was looking in the mirror he knew he had the beginnings of some muscle definition through his years of swimming but he was still very slim. When he lowered his shorts and put them in the laundry bin next to the door he then spent another few minutes now looking at his nude body. He had a severe tan line from his speedo making his butt and crotch stand out being so white in comparison. For his age he had an ok sized penis nothing special but shaving it made him look a lot younger then he was there are times after swimming where due to the cold he looks very child like hence why he showers alone with his back to the curtain. After almost 10 minutes checking himself out he finally stepped in the shower. Katy was listening from outside the door and at last she heard running water. Now time for her next step in the plan. She turned down the heating in the house making it freezing cold then she went to the door. She opened is quietly and peaked her head in. There she saw her brother watching his hair back to the door and singing out loud. She quickly went to the laundry bin and pulled out the only thing in there her brothers shorts. Walking backwards she looked up and now her brother was facing the door she froze thinking she was caught but his eyes were shut. Both hands on his head he was now fully on display. It took all of Katys power not to laugh knowing she wouldn't be the only one seeing this sight today. She shut the door and put Billys boxers in the washing machine with the rest of the clothes in the and put them on a long wash. Now it was a waiting game. She text Amy to see if she was still coming.

Katy: Are you still coming over
Amy: Yes but I still don't know what's going on.
Katy: I don't want to ruin the surprise but trust me you're going to love it.
Amy: Anything involving your brother I'm sure I wont love.
Katy: Remember to be ready to film this you won't wanna miss this.
Amy: Wow this sounds like something bad for Billy
Katy: Just a prank no big deal ;)
Amy: Ok well we will be there in 10 minutes my Mom said Billy better be ready this was the time he wanted.
Katy: Billy will be fully present tell your mom not to worry.
Amy: Ok bye.
Katy: Bye

Just as she finished texting Amy the shower shut off. Billy soaking wet went to the cupboard for a towel but there were none to be found. Damn it he thought as he suddenly noticed how cold it was in the house. Shivering he knew his only hope was to put on his boxers he just put in the laundry bin and go grab a towel from upstairs. As he opened the lid he gasped in horror as his boxers weren't there. He started cursing and slamming cupboards desperate to find something of cover in the bathroom. Just then there was a knock on the door "you ok in there bro" Katy said in a mocking tone. "No there are no towels and its freezing and I have nothing to dry off with" Billy said in a panicking tone much to Katy's amusement trying her hardest not to burst out laughing. "did you not check before you went in there mum left the towels upstairs in the landing closet". Billy cursed himself for not checking before showing but that did not explain the boxers going missing. "where are the boxers I had on Katy" Billy demanded. "Oh those smelly things I put them in the wash no point letting them sit in the bin all day". Billy was shocked to hear that she had came in whilst he was showering again. "Mom told you not to let yourself into the bathroom whilst i'm in there damn it Katy". Billy shouted in a stern tone. "Oh relax baldy nothing I haven't seen before" By that remark Billy knew that yet again his sister had seen him fully naked again. Even though it wasn't the first time it never was less embarrassing. "you might wanna make you mind up in the few minutes you lesson starts in little more than half and hour". Katy reminded him knowing that they would be here in moments. Billy caught sight of himself in the mirror soaking wet but to his horror shrinkage had fully set in and he looked child like down there. He would have to make the embarrassing dash to his bedroom whilst his sister was there. Knowing Billy was stuck debating what to do Katy used this window to open the front door as she had said to Amy to both let themselves in. Billy knew he had to bite the bullet "I can't let her think shes got to me. How do I play this off I know just own it she wins if she thinks she has embarrassed me this badly. Here I go head held high hands to the side" Billys little pep talk got him out of the bathroom and Katy wasn't waiting for him. "Maybe this is as far as she wanted to go he thought but why is it so cold in here". Billy went over to the heating and saw it was right down and turned it back up to a warm temperature. "Its gonna take a while to kick in I better head upstairs". Billy went through the kitchen door and down the hallway fully naked and uncovered but to his horror there was Mrs smith inside the doorway next to the stairs staring open mouthed next to his smirking sister.

Mrs Smith: What the hell do you think you are doing young man
Billy: I I I I umm
Mrs Smith: "You what speak up. There has to be a reason for your um little display". Mrs smith said whilst looking straight at Billy's crotch.
Billy: "I just had a shower and there were no towels after" Billy stammered still frozen like a dear in headlights.
Mrs Smith: "Nonsense it just so happens you pull a stunt like this when I bring my daughter".
Billys eyes went wide as saucers it cant be true can it. Thats when he turned his head and saw standing in the doorway just behind mrs smith was Amy and to his horror he saw he hold up her phone filming. Billy snapped out of his trance and tried explaining.
Billy: I thought you were going to be here later and I didn't know Amy would be here.
Mrs Smith: It was your idea to start earlier your sister said so.
Billy then looked over at Katy giggling who then put her finger to her lips telling him to sush.
Billy: But but but
Mrs Smith: No buts mr you have got a lot of explaining to do when I tell your mother shes raising a flasher. Was this show for my benefit because you shouldn't have bothered. You have nothing to show off Billy.
Amy finally spoke but it was only to insult his boyhood some more.
Amy: "Where are your balls Billy" she chuckled zooming in as she was still filming behind he mothers back.
That comment snapped billy back to reality as his hand shot down to his crotch and he could feel to his dismay that his balls had indeed fully shrived up.
Amy: Bit late for that Billy we have all had a good look at little Billy.
Katy burst out laughing at that as Billy stood there fully naked embarrassed and defeated.
Mrs Smith: I think you better make yourself decent young man.
Amy: "You saying he is decent like this mom" Amy chuckled
Mrs Smith: Enough Amy young Billy here has learned his lesson I think. He will think twice before parading around infront of ladies with his little willy hanging out.
Both girls burst into laughter and Mrs smith even chuckled as an embarrassed Billy made his way to the stairs. Katy deciding to get one last shot in stuck out her foot and Billy fell face first in the stairs with his bare ass sticking in the air.
Mrs Smith: "Look away girls its a full moon" chuckled Mrs Smith
Amy: It's so white mom but look I think I found his balls.
Billy fully bent over hearing Amys last remark thought it would never get any worse then this moment but to top it off he suddenly felt a sharp sting on his butt. Someone had spanked him he stood up rubbing his ass again giving everyone another frontal flash.
Amy: Welcome back little buddy.
Mrs Smith: Get dressed or ill give you a matching set of cheeks.
Billy ran upstairs to the sounds of all 3 girls laughing. Amy put her phone away before he mother could see her with it.
Mrs Smith: Well girls thats enough excitement for one day. You 2 stay out of trouble whilst I go tutor the streaker. I can only imagine what you girls are going to talk about.
Billy went into his bedroom and the first thing he saw was a towel on the bed and some clean clothes but no underwear. He quickly dried off and just about had his pants up when there was a knock on his door. Mrs smith told him she would be in the study room waiting for him. He threw on a t-shirt and prepared for the most awkward hour of his life. As he walked in he could see the smirk on Mrs Smiths face he tried to not make eye contact and stick strictly to the lesson. Mrs Smith on the other hand wanted to make this a little awkward on him she had caught him a couple of times trying to sneak a peak down her top or when she was bending over so it was nice to make him squirm a little bit. In Billy's rush to get dressed he forgot to zip up his pants so his zipper was open and given that he was warming up again things were returning to normal down there. Billy had not noticed but he was fully hanging out of the front of his pants. Mrs smith gasped when she first saw him hanging out he seemed none the wiser. She had two options alert him or act like she didn't see it. She went for a third option which was tell him at the end after an hour of awkwardness. So she went on making comments about it being a lot warmer now and how he might be overdressed now. She would deliberately lean over him so he could try to get a look down her top. She asked how his butt was feeling now and it wasn't long until Billy started to fluff up a bit. Mrs Smith knew she had her fun and now it was time to give him the final shot. Upon packing her things away and Billy looking really sheepish she stood up and said.
Mr smith: Bit of advice young man if you're not going to wear underwear at least make sure your zipped up.
Billys eyes went wide again as he looked down and there was his semi hard dick hanging out of his pants.
Mr smith looking down one more time said "Well at least you warmed up a bit" Laughing as she left a shocked Billy fumbling to tuck himself back in his pants. Mrs Smith went downstairs into the living room seeing Amy and Katy still giggling and replaying the events.
Mrs Smith: Come on Amy that's enough excitement for one day
Amy: Ok can I say bye to the nudist mum.
Mrs Smith: Hes got his hands full at the moment you will see him some other time.
Amy: Oh I will for sure. And on her way out she saw Billy at the top of the stairs. She shouted up without warning.
Amy: "Bye Willy I mean Billy" whilst waving her little finger.
Mrs Smith: "Amy stop that" She said laughing as they both exited.
Billy couldn't believe what had just happened the last 2 hours was it all a nightmare. Just then Katy walked up to him showing him the video Amy sent him. It was real alright. Katy laughed heading to her room not the best way to get your girlfriend to notice you baldy.
Last edited by enmfan on Sat Aug 19, 2023 5:37 pm, edited 1 time in total.
Jeepman89
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Re: Started with a prank

Post by Jeepman89 »

Excellent Part 2. I hope this continues and make sure he is warm when he is naked again in front of Amy.
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