Babysitter Katie (ENM story(epilogue to ENF))

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Wastelander
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Babysitter Katie (ENM story(epilogue to ENF))

Post by Wastelander »

Joe and Jack were brothers both well behaved and had a younger sister Madeline. Although they were getting older they still required a babysitter from time to time and the babysitter of choice was of course Katie! Katie had long brown hair that reached down to her hips and a cute little nose. While she was not that well known to be controlling from time to time she did step over the line with the punishments she would make Joe and Jack endure while letting young Maddie slide with her antiques. Today's story, however, pushed it beyond the reasonable limits and would be Katie's last time in charge of the two young boys and sister and here you'll see why. It all began a fine summer morning when Joe and Jack's parents had left for the day and Katie had just about finished feeding them their lunch. The boys were making a bit of a mess and Katie had ordered them to clean up immediately. The boys had been eating but also painting with their brand new sets the parents had gifted them but at this point it started to spill all over the table. It being the morning the boys made a ruckus and began to argue with Katie at first playful but then more resistant and defiant. Katie wanting to hear none of this started to yell at the boys before ultimately putting the boys in time out separately until she could figure out a suitable punishment to deal with them. She sat in the kitchen alone before putting up her hair in a bun using a hair tie before wiping down the table with a sponge she had just wet. Right then and there Katie got a sinister idea and quickly finished wiping down the spilled paints before resetting all the art supplies and placing down the boys art supplies on the ground. One at a time Katie went to each of the brothers and spoke to them informing them they had just spoken to their parents and that they were in deep trouble. The boys not knowing she was lying had started to panic and beg Katie not to tell their parents of their mis-deeds. Katie informed them she would forgive them but required a punishment each of them had to endure and if they did not listen to what she had ordered them to do they would both be reported to their parents. Katie called down Madeline who had missed most of the punishment and asked her to help. One at a time Katie went to the boys and asked them for their shorts and underwear leaving them bottomless from the hips down in their t shirts. Both of the boys were brought into and reunited with their younger sister in the living room standing on either side dicks drooping down on top of their hanging balls. Maddie giggled and pointed at both her older brothers picks before asking them why they had forgotten their pants.
"They are being punished Maddie they've been bad little boys" said Katie giggling
"We're sorry can we please put out pants back on" said Joe as he attempted to cover up his penis in front of his fully clothed sister.
"Sorry boys not yet, plus I've got some fun activities we can all enjoy with your sister, go and sit down on the couch and we can all watch a movie"
Maddie ran to the couch and sat right in the middle leaving space on either side of her for her nudified big brothees. Joe and Jack sauntered over before sitting on either side of their clothed little sister attempting to cover up.
"Ah ah ah none of that you're being punished so you've got to stop covering up" Katie said with a smile "squat next to your little sister and place your hands on your knees"
Both both shifted their legs up and placed their hands appropriately letting their balls drag on the couch cushion as their dicks began to stiffen and point towards the ski.
"WHOA look at them" Maddie said pointing at the boys dicks. She had never seen anything like it.
"Here's where these come in" Katie said reaching up to her tied up hair and pulling off two hair ties letting her long beautiful hair dangle down. She approached Jack first and with a quick motion tied the boys balls twice with her hair tie letting the boys testicles hang down a bit more and hang freely.
"Go on Maddie now try it with Joe" Katie said handing her the hair tie. Maddie took some time but eventually had her older brothers balls tied up nice and tight letting them dangle as both boys penises began to harden.
"Okay now that thats taken care of let's get some photos shall we!" Katie said smiling pulling out an old pollaroid. Katie gave them different poses to do on the couch some with Maddie holding both the boys sctrotums as they hung low while squatting others while the boys were standing and Maddie was in between them with the boys arms around her shoulders while she held their dicks and sometimes just plain old fun pictures with all of them smiling. Many photos were taken of all angles in different furniture around the living room including the easy chair the couch on the carpet etc but the boys were always in it with their sister. After a while Katie got bored and was ready to give them their next task.
"Alright who's ready to paint!" Katie said smiling pointing in the direction of the kitchen
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Re: Babysitter Katie (ENM story(epilogue to ENF))

Post by Jeepman89 »

Fun story. Loving it. More please.
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Re: Babysitter Katie (ENM story(epilogue to ENF))

Post by Wastelander »

Jeepman89 wrote: Sun Apr 28, 2024 10:04 pm Fun story. Loving it. More please.
Will do! It's gonna have a part two then it's gonna go into a seperate ENF story with the same characters
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Re: Babysitter Katie (ENM story(epilogue to ENF))

Post by Wastelander »

Joe and Jack followed Katie into the kitchen with Madeline closely behind them giving their Butt's a smack and occasionally grabbing their dangling balls from behind then giving them a little tug and getting their picks harder. Katie ordered both boys to go wash their hands and balls by the sink with Madeline supervising and giving extra help. Maddie soaped up her hands into a lather and started to massage Jack's balls first pulling down on them and patting them in the process making sure they were adequately cleaned and free of debris. Joe followed suit having his balls dropped lower Maddie had a fun time pulling on them he begged her to stop for fear of creaming.
"That's the great thing boys, with those hair ties that tightly wound around your little sacks you won't be Cummings anytime soon" Katie giggled as she lay some sheets of paper on the ground and dumped out some paint into a small bowl to use.
"Okay everyone! We are gonna try something different today, you've heard of finger painting but today we are gonna try scrotum painting" she said pointing at the paint and then at both brothers balls as they turned bright red.
"But what will Maddie do she's not tied up like we are and doesn't have balls" joe questioned trying to move himself a bit to cover his exposed penis
"You're right! She's the artist so Maddie is going to get you boys to paint the picture she's in charge" Katie said smiling and placing a hand around her shoulder.
Both boys looked embarrased having to listen to their younger sister while in such an exposed state but didn't want to get into any further trouble. Maddie ordered both boys to squat their hanging balls into the paint one red one blue and start to drag themselves on the paper creating very simple looking smiley faces Maddie took no time at all grabbing them and directing them on different areas of the paper. She was having a great time and to an extent so were the brothers even if they were embarrased. Near the end of their painting activity Katie ordered all of them out into the backyard so they could wash off. Both brothers were extremely embarrased as they had female neighbors around Katie's age that often spent their afternoons in the backyard doing yoga and other activities. Sure enough when they went outdoors two of them were next door Kim and her friend Sarah (we will learn about them in a future story). Madeline noticed the boys balls were becoming very swollen so Katie made the boys face the wall as she turned on the cold water hose washing the nude bottomless boys off as Madeline went into finish the job seeing the cold water had shrunk them down significantly Kim and Sarah watched on with astonishment as the fully clothed Madeline took all the paint off. Katie ordered both boys to lay in the backyard on towels in order for them to dry off completely. Maddie once again being the trouble maker laid a towel in between them and slightly played with her brothers dicks again that had become stiffer as the boys shielded their faces. Katie snapped a few more pictures of the boys before asking Kim and Sarah to get in and take a few as well. Once again there were all different positions taken with the girls displaying the boys tied up balls as trophies or gripping their hard dicks. As she noticed the parents would be coming home soon Katie gave one last order as she approached both boys she ordered them to squat and spread as she removed the hair ties letting their balls breath.
"They look so red" Maddie said as she pressed onto both her brothers balls "do they hurt?"
"Yes but I'm glad to have mine off" said Joe as he brushed away maddies hand and held his junk.
"No covering up!" Katie said "and for that I've got a punishment for you, Maddie grab each of your brothers and start stroking, boys put your arms around your sister and get in for a picture"
The three of them got together and Maddie furiously got to work playing with her older brothers hardened dicks and now free testicles. One picture, two and on the third both boys let out a massive load shooting across their towels as the photo captured it mid air. Both boys blushing with a look of pleasure on their face as Maddie sat in the middle smiling ear to ear. They all cleaned up their mess and made their way in but not before making the boys stay nude with their clothed sister only moments before the parents got home.
"How were they?" The mom asked
"They behaved so well! Especially Maddie if you ever need me to come babysit the boys again let me know!"
"That's great to hear we will be heading out to some future conventions the next couple of months and need someone reliable" said the dad
Katie eventually left the house and got home wondering how she had pulled off such a wild moment in her life. Eventually she drifted off to bed but when she awoke the next day she had a sudden moment of horror as she realized she had forgotten the pollaroid camera and the photos on the table. (End of the ENM - this will continue on the ENF side and I'll post a link when I make that section)
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Re: Babysitter Katie (ENM story(epilogue to ENF))

Post by Jeepman89 »

Fantastic story, Wastelander. I loved them being taken outside where more girls could see them bare naked.
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Re: Babysitter Katie (ENM story(epilogue to ENF))

Post by Wastelander »

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Part 2 of this story if anyone wants to continue reading but it is ENF
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Re: Babysitter Katie (ENM story(epilogue to ENF))

Post by mikewozere »

Nice what are the ages of all the kids? I presume Katie is around 16?
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