A Tangled Web - Complete
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Re: A Tangled Web
This is turning into a tangled web! I'm loving it, though. What's going to happen to poor Bailey? Looking forward to the next installment.
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Re: A Tangled Web
I’ve probably contributed a couple hundred views to this story just from refreshing for updates. I keep it tabbed on my phone.
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Re: A Tangled Web
CRAIG
“Fuck that would’ve been hot!” Bryce exasperated after he heard about a failed stripping attempt by the twatarazzi. Adira had been the target.
“Haha, straight up assault, bro. Not that hot,” Jay said.
“Whatever, you would’ve looked.”
“I mean…I guess. No way to avoid it really.”
“Mannnn, you’re full of shit. One of the baddest girls ever at Webberson and y’all act like, ‘no, no, no, we gotta respect women! Can I kiss you? Can I unbutton your top button? Can I unbutton the next button? Can I unbutton the one after that?’ Fuck off!”
We laughed at Bryce’s impression of us.
“Don’t think I ain’t talking about you either Craig. Wastin your time with a chick that would barely even kiss Lando?”
“Man, you guys are REALLY concerned about Bailey and me,” I continued to chuckle. That Peter Stein kid and Bailey’s little brother hovered near us, listening in on our conversation. Bryce spotted them.
“The fuck are you looking at, Forest Gump?” Bryce directed at the scrawny kid standing beside Bailey’s brother; using a nickname people had given him after Brad pantsed the poor boy in gym class and exposed a thick, wild bush on par with Lizzy’s. Peter and Ben began scurrying away. “Craig put his finger in your sister’s bunghole last night!” Bryce hollered after them, then burst out laughing. “Was that what you guys wanted to hear?!”
“Did he now?” Bailey’s voice arose behind us.
I turned and rolled my eyes at her.
“Bailey!! What’s up?!” Bryce said. “You gonna let poor Craig here get some before he graduates or what?”
Bailey ignored him.
“Are you walking to class?” She asked me, a bit timidly.
“Yup!” I said, happy to get away from these idiots. Bryce made a whipping sound as I walked away.
“Can I ask you something?” Bailey asked.
“Why do I hang out with them?” I responded.
“Bryce, mainly. I like Jay.”
“I don’t know. We’ve almost all known each other since kindergarten. Kinda hard to avoid him unless I cut off everyone,” I shrugged.
“I get it, I guess. Hey! I wanna do something…exciting tonight.”
“Bailey, you don’t have to…don’t be bothered by the shit he says.”
“Very presumptuous of you but I'm not talking about that! It’s so nice out, 85 degrees. I got something I think will be a lot of fun!”
“Okay, you got me intrigued….”
Later that night, Bailey picked me up. She drove down some back roads through a wooded area. The route was vaguely familiar, but I didn’t fully recognize it until we passed a row of gated mansions.
“Hey, isn’t this the way to Colton’s aunt and uncle’s?”
Bailey’s lips curled and she raised her eyebrows but remained quiet. She parked the car on the side of the road and grabbed her things.
“C’mon,” she asserted.
I got out and followed her. We walked through the trees on a path by the lake. By the time she took a branched off side-trail I was certain.
“We ARE going to Colton’s aunts and uncles?”
“Shhhhh,” Bailey whispered. “Naomi was trying to convince Colton to host people over here tonight because he told us they were out of town. But he said he felt like shit and didn’t wanna drink or anything. Sooooo…. ”
“….no one’s home,” I finished.
“Nope,” Bailey said. She began reaching up over the fence that barricaded the yard and pool. She’s an athletic girl and had no trouble shimmying up and over. I wasn’t gonna wait around.
“Did you wear your swimsuit?”
“Nah,” she answered casually. Then she began nonchalantly undressing and – oh my God – this was turning into the high point of every teen romcom ever made. Bailey showed off her incredible figure wearing only a pink bra and jean shorts. I watched as she unbuttoned and unzipped the shorts. “You just gonna stand there gawking?” She asked.
“Errr. No,” I said. I was a little concerned, seeing as I had a raging hard-on already. Still, I took my shirt off and showed off my skinny – but cut – chest and abs.
Bailey pulled her shorts down and revealed a skimpy, matching pink thong and Jesus Christ her ass looked amazing. Tight, and round, and perky, there was no going back now. She turned to look at me.
“Coming?”
“Yep! Yep!” I said, too excitedly. I pulled my shorts off and she saw my erection and though it was dark, I could see she was blushing a bit.
“Thanks for the compliment,” she said, then dove into the pool. I followed.
We frolicked and kissed and rubbed up against each other. It was the best night of my life.
*******
“Oh crap, did you hear that?” Bailey asked, just as we had moved from the pool to the hot tub.
“Sounded like a car…”
“That’s what I thought, c’mon, we gotta go!”
Bailey jumped up and out of the tub and ran over to her clothes. A spotlight shined into the backyard, illuminating her scantily clad body.
“Ahhh!” She yelped. Her ass bounced enticingly with each step. She bent over and collected her belongings. I was right behind her and snatched up my own.
“HEY!” A deep voice belted through the night. “Police! Stop!”
We kept running. I made it over the fence first, and helped Bailey. She jumped down with nervous laughter and we sprinted into the woods.
“We don’t wanna lead them back to your car, c’mon, this way!” I whispered, heading to the lake. We reached the dock and I looked back, the cop wasn’t around. Yet.
“We’re gonna have to get in,” I said.
“Okay, you first!” Bailey said, nervously.
Not wanting to make a splash, I dipped into the black water from the side of the dock. Bailey did the same, after tossing our clothes in the small boat beside us.
“Holy crap it’s freezing!!!” She said through chattering teeth. We bundled together, closer than ever. Her soft breasts pushed up against my chest and her doe eyes sparkled.
“There he is…” I muttered, as soft as possible.
The policeman’s flashlight shined down near us toward the lake. We maneuvered ourselves underneath the dock and I prayed he wouldn’t walk down on top of it. The light scanned the area and grew in size as he approached the water.
“Jim, come on. Just a couple of kids. They ain’t coming back,” a second voice called out.
“Right. Alright. I’ll tell the Vanders we scared em off.”
Bailey and I both took a massive sigh of relief. As soon as the light was gone, we pulled ourselves out of the water, still shivering uncontrollably.
“I got towels and blankets in my car,” Bailey said. “Let’s head back before we freeze to death.”
“Good idea,” I said.
We walked back laughing uncontrollably, slap happy from adrenaline.
“Craig, I am soooo sorry!” She said, after we had dried off and she had driven me home.
“For what? That was the most fun I’ve had all year!”
“Haha, yeah a little too much fun,” Bailey said. “Wasn’t how things were supposed to happen…but I’ll make it up to you!”
“Make what up? I told you, that was an awesome night.”
“Just….well, I’ll think of something,” she smiled and kissed me goodbye.
And later that night, she did think of something. She sent me a smiling Snapchat, topless, with her perfect bare tits on display!
“Told ya I’d make it up to you ……. Show anyone n I’ll kill u lol”
Is what the caption read. But I was about to die from excitement right then and there anyway.
“Fuck that would’ve been hot!” Bryce exasperated after he heard about a failed stripping attempt by the twatarazzi. Adira had been the target.
“Haha, straight up assault, bro. Not that hot,” Jay said.
“Whatever, you would’ve looked.”
“I mean…I guess. No way to avoid it really.”
“Mannnn, you’re full of shit. One of the baddest girls ever at Webberson and y’all act like, ‘no, no, no, we gotta respect women! Can I kiss you? Can I unbutton your top button? Can I unbutton the next button? Can I unbutton the one after that?’ Fuck off!”
We laughed at Bryce’s impression of us.
“Don’t think I ain’t talking about you either Craig. Wastin your time with a chick that would barely even kiss Lando?”
“Man, you guys are REALLY concerned about Bailey and me,” I continued to chuckle. That Peter Stein kid and Bailey’s little brother hovered near us, listening in on our conversation. Bryce spotted them.
“The fuck are you looking at, Forest Gump?” Bryce directed at the scrawny kid standing beside Bailey’s brother; using a nickname people had given him after Brad pantsed the poor boy in gym class and exposed a thick, wild bush on par with Lizzy’s. Peter and Ben began scurrying away. “Craig put his finger in your sister’s bunghole last night!” Bryce hollered after them, then burst out laughing. “Was that what you guys wanted to hear?!”
“Did he now?” Bailey’s voice arose behind us.
I turned and rolled my eyes at her.
“Bailey!! What’s up?!” Bryce said. “You gonna let poor Craig here get some before he graduates or what?”
Bailey ignored him.
“Are you walking to class?” She asked me, a bit timidly.
“Yup!” I said, happy to get away from these idiots. Bryce made a whipping sound as I walked away.
“Can I ask you something?” Bailey asked.
“Why do I hang out with them?” I responded.
“Bryce, mainly. I like Jay.”
“I don’t know. We’ve almost all known each other since kindergarten. Kinda hard to avoid him unless I cut off everyone,” I shrugged.
“I get it, I guess. Hey! I wanna do something…exciting tonight.”
“Bailey, you don’t have to…don’t be bothered by the shit he says.”
“Very presumptuous of you but I'm not talking about that! It’s so nice out, 85 degrees. I got something I think will be a lot of fun!”
“Okay, you got me intrigued….”
Later that night, Bailey picked me up. She drove down some back roads through a wooded area. The route was vaguely familiar, but I didn’t fully recognize it until we passed a row of gated mansions.
“Hey, isn’t this the way to Colton’s aunt and uncle’s?”
Bailey’s lips curled and she raised her eyebrows but remained quiet. She parked the car on the side of the road and grabbed her things.
“C’mon,” she asserted.
I got out and followed her. We walked through the trees on a path by the lake. By the time she took a branched off side-trail I was certain.
“We ARE going to Colton’s aunts and uncles?”
“Shhhhh,” Bailey whispered. “Naomi was trying to convince Colton to host people over here tonight because he told us they were out of town. But he said he felt like shit and didn’t wanna drink or anything. Sooooo…. ”
“….no one’s home,” I finished.
“Nope,” Bailey said. She began reaching up over the fence that barricaded the yard and pool. She’s an athletic girl and had no trouble shimmying up and over. I wasn’t gonna wait around.
“Did you wear your swimsuit?”
“Nah,” she answered casually. Then she began nonchalantly undressing and – oh my God – this was turning into the high point of every teen romcom ever made. Bailey showed off her incredible figure wearing only a pink bra and jean shorts. I watched as she unbuttoned and unzipped the shorts. “You just gonna stand there gawking?” She asked.
“Errr. No,” I said. I was a little concerned, seeing as I had a raging hard-on already. Still, I took my shirt off and showed off my skinny – but cut – chest and abs.
Bailey pulled her shorts down and revealed a skimpy, matching pink thong and Jesus Christ her ass looked amazing. Tight, and round, and perky, there was no going back now. She turned to look at me.
“Coming?”
“Yep! Yep!” I said, too excitedly. I pulled my shorts off and she saw my erection and though it was dark, I could see she was blushing a bit.
“Thanks for the compliment,” she said, then dove into the pool. I followed.
We frolicked and kissed and rubbed up against each other. It was the best night of my life.
*******
“Oh crap, did you hear that?” Bailey asked, just as we had moved from the pool to the hot tub.
“Sounded like a car…”
“That’s what I thought, c’mon, we gotta go!”
Bailey jumped up and out of the tub and ran over to her clothes. A spotlight shined into the backyard, illuminating her scantily clad body.
“Ahhh!” She yelped. Her ass bounced enticingly with each step. She bent over and collected her belongings. I was right behind her and snatched up my own.
“HEY!” A deep voice belted through the night. “Police! Stop!”
We kept running. I made it over the fence first, and helped Bailey. She jumped down with nervous laughter and we sprinted into the woods.
“We don’t wanna lead them back to your car, c’mon, this way!” I whispered, heading to the lake. We reached the dock and I looked back, the cop wasn’t around. Yet.
“We’re gonna have to get in,” I said.
“Okay, you first!” Bailey said, nervously.
Not wanting to make a splash, I dipped into the black water from the side of the dock. Bailey did the same, after tossing our clothes in the small boat beside us.
“Holy crap it’s freezing!!!” She said through chattering teeth. We bundled together, closer than ever. Her soft breasts pushed up against my chest and her doe eyes sparkled.
“There he is…” I muttered, as soft as possible.
The policeman’s flashlight shined down near us toward the lake. We maneuvered ourselves underneath the dock and I prayed he wouldn’t walk down on top of it. The light scanned the area and grew in size as he approached the water.
“Jim, come on. Just a couple of kids. They ain’t coming back,” a second voice called out.
“Right. Alright. I’ll tell the Vanders we scared em off.”
Bailey and I both took a massive sigh of relief. As soon as the light was gone, we pulled ourselves out of the water, still shivering uncontrollably.
“I got towels and blankets in my car,” Bailey said. “Let’s head back before we freeze to death.”
“Good idea,” I said.
We walked back laughing uncontrollably, slap happy from adrenaline.
“Craig, I am soooo sorry!” She said, after we had dried off and she had driven me home.
“For what? That was the most fun I’ve had all year!”
“Haha, yeah a little too much fun,” Bailey said. “Wasn’t how things were supposed to happen…but I’ll make it up to you!”
“Make what up? I told you, that was an awesome night.”
“Just….well, I’ll think of something,” she smiled and kissed me goodbye.
And later that night, she did think of something. She sent me a smiling Snapchat, topless, with her perfect bare tits on display!
“Told ya I’d make it up to you ……. Show anyone n I’ll kill u lol”
Is what the caption read. But I was about to die from excitement right then and there anyway.
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Re: A Tangled Web
BAILEY
I decided to try and move things along with Craig. Ben hasn’t stopped creeping on me (and doing more) and there’s no chance I’m going to let him steal all these firsts for me (like touching me down there!). Plus, I feel more comfortable with Craig than any other guy I’ve hung out with in the past.
But this got me in some trouble. We broke into Colton’s family’s pool and had to run from the cops. We escaped, but of course the backyard had cameras. I don’t know why I didn’t think of that. They instantly recognized Craig on the camera and one thing led to another. Next thing you know my parents were mad at me and grounded me after they got done speaking with Colton’s family over the phone. Fortunately, they decided to keep the cops out of it.
“I don’t want you seeing this ‘Craig’ anymore. Not until we have a chance to meet him,” my mom said at dinner.
“Mom, okay, we were taking things slow before we introduced each other to our parents.”
“Breaking and entering to skinny dip is what you call slow, huh?” Dad said. Ben’s eyes perked up and I fired a nasty glare at him.
“We weren’t ‘skinny dipping’,” I said.
“By what Mr. Vanders said, you weren’t wearing bathing suits, either,” Dad replied.
“It’s just not like you Bailey. I know you’re having fun and gonna start dating boys more seriously, but just ask for permission next time!” Mom said.
“Okay, fine, I get it,” I said.
“We’re gonna ground you for the rest of the month,” she said.
“That’s like two weeks!” I protested.
“AND, no more Craig until we meet him.”
“Ugghhhhh, fine!” I went up to my room.
Meanwhile, at school, Craig and I had morphed into the “it couple.” It reminded me of the fall when I was with Landon, except people seemed more supportive this time. Well, most people, anyway.
Shelby, Alexis, Taylor, and their gang were still mean, which I didn’t quite understand. They all had boyfriends, Shelby was with Landon for crying out loud. Why did they care that I was now with Craig?
I decided to try and move things along with Craig. Ben hasn’t stopped creeping on me (and doing more) and there’s no chance I’m going to let him steal all these firsts for me (like touching me down there!). Plus, I feel more comfortable with Craig than any other guy I’ve hung out with in the past.
But this got me in some trouble. We broke into Colton’s family’s pool and had to run from the cops. We escaped, but of course the backyard had cameras. I don’t know why I didn’t think of that. They instantly recognized Craig on the camera and one thing led to another. Next thing you know my parents were mad at me and grounded me after they got done speaking with Colton’s family over the phone. Fortunately, they decided to keep the cops out of it.
“I don’t want you seeing this ‘Craig’ anymore. Not until we have a chance to meet him,” my mom said at dinner.
“Mom, okay, we were taking things slow before we introduced each other to our parents.”
“Breaking and entering to skinny dip is what you call slow, huh?” Dad said. Ben’s eyes perked up and I fired a nasty glare at him.
“We weren’t ‘skinny dipping’,” I said.
“By what Mr. Vanders said, you weren’t wearing bathing suits, either,” Dad replied.
“It’s just not like you Bailey. I know you’re having fun and gonna start dating boys more seriously, but just ask for permission next time!” Mom said.
“Okay, fine, I get it,” I said.
“We’re gonna ground you for the rest of the month,” she said.
“That’s like two weeks!” I protested.
“AND, no more Craig until we meet him.”
“Ugghhhhh, fine!” I went up to my room.
Meanwhile, at school, Craig and I had morphed into the “it couple.” It reminded me of the fall when I was with Landon, except people seemed more supportive this time. Well, most people, anyway.
Shelby, Alexis, Taylor, and their gang were still mean, which I didn’t quite understand. They all had boyfriends, Shelby was with Landon for crying out loud. Why did they care that I was now with Craig?
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Re: A Tangled Web
BEN
Waiting to see if trouble may come is an unpleasant predicament to find yourself in. I had gone too far with my sister, and I knew she was going to rat me out. Every ring at our doorbell over the next few weeks was certainly a police officer coming to arrest me. Every “Ben, come here for a second,” was certainly my parents informing me they’re sending me away for what I’ve done.
But no punishment ever came.
Bailey, whether it was out of self-preservation, or shame, or reluctant enjoyment, remained silent. She’s made sure to have minimal interaction with me, obviously. But it’s become clear, I can take this as far as I want. I get hard just thinking about the possibilities!
*********
“Ben, dude…you GOTTA let us see what else you’ve got of your sister!” Peter begged in the cafeteria one day at school.
“You guys haven’t added anything either,” I said. “The cord’s been dead for weeks – ever since the swim meet.”
“The student body is on guard, Benjamin,” Arnie replied.
“Yeah Ben, you saw how everyone reacted after we blew it with Adira,” Neil shuttered.
“Oh man, could you imagine if we succeeded on that one?” Jared pondered, undoubtedly battling years of pent-up frustration regarding his brother’s gorgeous ex-girlfriend. If he only knew…
“Yeah, but, there’s gotta at least be more selfies kids are hoarding,” I began. “With all the whores in this school?! Just open up some of the older VIP stuff – NOT Bailey! – to trade.”
“We’ve thought about doing that,” Neil answered. “But you know that includes your video of Shelby, right? Everyone at this table can keep our mouths shut, we know what’s at stake. But the other idiots in this school? – no way. Is it worth risking this whole thing blowing up in our faces for a few selfies?”
“Nearly every capture in the VIP sector can be easily traced to individuals at this table,” Arnie announced, thinking he was a CIA agent or some shit.
“Well, what about hacking?” I asked.
Neil chuckled. “Hacking isn’t like the movies Ben, where we just punch a bunch of code into our laptops and we get access to everyone’s secret pics.”
“I’m aware,” I snapped, annoyed.
“Of course we’ve tried it. It’s how we got some of those selfies in the first place. Like Arnie said, people are catching on to us. Almost every account has some form of two factor authentication or alerts someone if their account has been logged on to from a new device. There’s some dumbass chicks at our school – a lot of them – but without having direct access to their phone, it’s challenging,” Neil explained.
“I may be able to help with that,” I said. Four sets of eyes lit up.
“Your sister!?” Peter asked.
I grinned, sheepishly. “If she’s sent anything to Craig, I can likely find them. Then we can blame this whole thing on him,” I laughed.
“Fortunate fucker, everyone needs to face adversity at some point in their lives,” Arnie said.
*****************
My devilish plan took a while to pull off. I barely saw my sister for weeks, but then, she got herself grounded. Still, she made a point to not shower if it was just me and her alone. I didn’t have the balls to try anything while my parents were around.
One evening I shut the library down an hour early because there wasn’t a soul in sight the whole afternoon. When I arrived home, my dad’s SUV was gone and no one was downstairs. The shower was running, but I had no clue for how long.
I had to be fast.
I threw my shit on the ground and didn’t even bother to take my coat off. I jumped up 3 stairs at a time and spun around the corner into Bailey’s room. Her phone laid, defenseless, on her bed.
I punched her password in, cursing, as I fucked up on the first two attempts due to being in a panicky rush. Her home screen opened and I went straight to the text thread with Craig. I had put thought into this. For this plan to work, I needed confirmation that any nudes were sent to him. Pics in Bailey’s deleted gallery would be awesome to see, but useless in my scheme.
I found mostly walls of texts. Boring shit that I had no time or desire to read through. Similarly to Landon, there were clothed pics here and there, but nothing interesting. In contrast though, Craig hadn’t sent any douche selfies to Bailey.
The shower turned off. Shit.
Snapchat was my last hope and my heart was beating a million times a minute. I opened the app and Craig was Bailey’s new top friend. There were a few messages saved in the chat between them.
A cabinet opened and closed. God damn I had to get out of here.
I clicked on the memories section of the app and….VOILA!!!!
It was just one pic, but it was perfect for what I needed. The pic was of Baily showing off her pretty smile – and her pretty titties! The caption read:
“Told ya I’d make it up to you ……. Show anyone n I’ll kill u lol”
Well sis, we’re about to find out. Palms sweating, I airdropped the pic to my phone and got the fuck out of there. I didn’t even make it back to my room when Bailey strutted out into the hallway – in her birthday suit!!!
“AHHHHHHHHHHH!!!!!!!!” She let out a blood curling scream and fired her hands over her privates. She turned to escape back into the bathroom, but hesitated at the entryway. She rotated back around and peaked her head out. “When did you get home?” She asked, hopeless.
“Not too long ago, why?” I squeaked. I was still so nervous about potentially getting caught on Bailey’s phone that I hadn’t fully processed this – certainly welcome – turn of events.
“You’re not gonna leave me alone, are you?” Bailey asked.
“Huh?”
“Uggghhhhh, just shut up, Ben,” she rolled her eyes and her shoulders sunk downward. She let out a massive sigh. “Feast your eyes,” she said, with futility.
...
Bailey walked out into the hallway, bare…. butt…. NEKKKKED!!!
I did as she advised and went bug eyed over her body as she walked uncovered down the hallway – right at me. Her eyes were shut, and she grimaced, but blessed me with an unveiled look at her smokin hot tits and coochie throughout her entire walk of shame. She turned the corner and I turned to ogle at her sporty bare ass.
“There, you got to see, okay? Now STAY. OUT!!!” Bailey shut her door and locked it.
I did as she asked, and went downstairs, elated. There’s no way that just happened!!!
Waiting to see if trouble may come is an unpleasant predicament to find yourself in. I had gone too far with my sister, and I knew she was going to rat me out. Every ring at our doorbell over the next few weeks was certainly a police officer coming to arrest me. Every “Ben, come here for a second,” was certainly my parents informing me they’re sending me away for what I’ve done.
But no punishment ever came.
Bailey, whether it was out of self-preservation, or shame, or reluctant enjoyment, remained silent. She’s made sure to have minimal interaction with me, obviously. But it’s become clear, I can take this as far as I want. I get hard just thinking about the possibilities!
*********
“Ben, dude…you GOTTA let us see what else you’ve got of your sister!” Peter begged in the cafeteria one day at school.
“You guys haven’t added anything either,” I said. “The cord’s been dead for weeks – ever since the swim meet.”
“The student body is on guard, Benjamin,” Arnie replied.
“Yeah Ben, you saw how everyone reacted after we blew it with Adira,” Neil shuttered.
“Oh man, could you imagine if we succeeded on that one?” Jared pondered, undoubtedly battling years of pent-up frustration regarding his brother’s gorgeous ex-girlfriend. If he only knew…
“Yeah, but, there’s gotta at least be more selfies kids are hoarding,” I began. “With all the whores in this school?! Just open up some of the older VIP stuff – NOT Bailey! – to trade.”
“We’ve thought about doing that,” Neil answered. “But you know that includes your video of Shelby, right? Everyone at this table can keep our mouths shut, we know what’s at stake. But the other idiots in this school? – no way. Is it worth risking this whole thing blowing up in our faces for a few selfies?”
“Nearly every capture in the VIP sector can be easily traced to individuals at this table,” Arnie announced, thinking he was a CIA agent or some shit.
“Well, what about hacking?” I asked.
Neil chuckled. “Hacking isn’t like the movies Ben, where we just punch a bunch of code into our laptops and we get access to everyone’s secret pics.”
“I’m aware,” I snapped, annoyed.
“Of course we’ve tried it. It’s how we got some of those selfies in the first place. Like Arnie said, people are catching on to us. Almost every account has some form of two factor authentication or alerts someone if their account has been logged on to from a new device. There’s some dumbass chicks at our school – a lot of them – but without having direct access to their phone, it’s challenging,” Neil explained.
“I may be able to help with that,” I said. Four sets of eyes lit up.
“Your sister!?” Peter asked.
I grinned, sheepishly. “If she’s sent anything to Craig, I can likely find them. Then we can blame this whole thing on him,” I laughed.
“Fortunate fucker, everyone needs to face adversity at some point in their lives,” Arnie said.
*****************
My devilish plan took a while to pull off. I barely saw my sister for weeks, but then, she got herself grounded. Still, she made a point to not shower if it was just me and her alone. I didn’t have the balls to try anything while my parents were around.
One evening I shut the library down an hour early because there wasn’t a soul in sight the whole afternoon. When I arrived home, my dad’s SUV was gone and no one was downstairs. The shower was running, but I had no clue for how long.
I had to be fast.
I threw my shit on the ground and didn’t even bother to take my coat off. I jumped up 3 stairs at a time and spun around the corner into Bailey’s room. Her phone laid, defenseless, on her bed.
I punched her password in, cursing, as I fucked up on the first two attempts due to being in a panicky rush. Her home screen opened and I went straight to the text thread with Craig. I had put thought into this. For this plan to work, I needed confirmation that any nudes were sent to him. Pics in Bailey’s deleted gallery would be awesome to see, but useless in my scheme.
I found mostly walls of texts. Boring shit that I had no time or desire to read through. Similarly to Landon, there were clothed pics here and there, but nothing interesting. In contrast though, Craig hadn’t sent any douche selfies to Bailey.
The shower turned off. Shit.
Snapchat was my last hope and my heart was beating a million times a minute. I opened the app and Craig was Bailey’s new top friend. There were a few messages saved in the chat between them.
A cabinet opened and closed. God damn I had to get out of here.
I clicked on the memories section of the app and….VOILA!!!!
It was just one pic, but it was perfect for what I needed. The pic was of Baily showing off her pretty smile – and her pretty titties! The caption read:
“Told ya I’d make it up to you ……. Show anyone n I’ll kill u lol”
Well sis, we’re about to find out. Palms sweating, I airdropped the pic to my phone and got the fuck out of there. I didn’t even make it back to my room when Bailey strutted out into the hallway – in her birthday suit!!!
“AHHHHHHHHHHH!!!!!!!!” She let out a blood curling scream and fired her hands over her privates. She turned to escape back into the bathroom, but hesitated at the entryway. She rotated back around and peaked her head out. “When did you get home?” She asked, hopeless.
“Not too long ago, why?” I squeaked. I was still so nervous about potentially getting caught on Bailey’s phone that I hadn’t fully processed this – certainly welcome – turn of events.
“You’re not gonna leave me alone, are you?” Bailey asked.
“Huh?”
“Uggghhhhh, just shut up, Ben,” she rolled her eyes and her shoulders sunk downward. She let out a massive sigh. “Feast your eyes,” she said, with futility.
...
Bailey walked out into the hallway, bare…. butt…. NEKKKKED!!!
I did as she advised and went bug eyed over her body as she walked uncovered down the hallway – right at me. Her eyes were shut, and she grimaced, but blessed me with an unveiled look at her smokin hot tits and coochie throughout her entire walk of shame. She turned the corner and I turned to ogle at her sporty bare ass.
“There, you got to see, okay? Now STAY. OUT!!!” Bailey shut her door and locked it.
I did as she asked, and went downstairs, elated. There’s no way that just happened!!!
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Re: A Tangled Web
This just gets hotter and hotter! I must say I love how carefully Ben and the gang are being. It makes the story feel much more realistic, because they know the consequences of being caught, hence they are avoiding it.
My real incidents:
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Re: A Tangled Web
Damn these cliffhangers! I hope Bailey catches on to what Ben did and doesn’t break up with Craig if the picture gets spread. Madison and Drew briefly becoming distant was so heartwrenching for me, I can’t take a repeat of that! For me, their adorable, budding romance is the crucial wholesome balance to the depraved and/or downright malicious actions of literally every other driving character in this plot. I wish them nothing but the best! (Even if I still crave getting to read along as Ben continues to push her boundaries far beyond what she’s comfortable with…)
Also just wanted to add that I have developed an extreme pavlovian response to seeing a new chapter uploaded. My heart rate immediately shot up in anticipation once I saw it today.
Also just wanted to add that I have developed an extreme pavlovian response to seeing a new chapter uploaded. My heart rate immediately shot up in anticipation once I saw it today.
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Re: A Tangled Web
BEN
“Goddamn Ben, you gotta try and catch him taking her to pound town,” Peter said one day after school.
I had asked the crew to meet me at the library. I knew it would be dead. I showed them the topless selfie I’d stolen off of Bailey’s phone.
“Well, you better be quick, cause once we leak this and she finds out, it’s over for him,” Neil said.
“He never comes over anyway, trust me I would have tried,” I said. “That said, I can’t actually confirm this was ever sent to Craig.”
“What do you mean?”
“I mean the captions make it seem like it was…and it probably was, but it was just in the memories section. All the pics sent in the chat disappear unless someone saves it,” I explained.
“Which he wouldn’t have been stupid enough to do,” Neil said. “At least not directly, where she could find out.”
“It’s risky,” I sighed. “If she never sent it….I’m fucked.”
“Up to you man,” Neil shrugged. “If we dangle this out there though, people are definitely gonna bite.”
“Yes, we’ve had numerous offers on our prior MVP subjects,” Arnie said. “This will be no different.”
“Any idea who are in the offers?” I asked.
“Well….the two most intriguing students are Kaila and Maria,”
“Fernandez?!” I interrupted.
“Yup,” Neil nodded.
“You think it’s legit?” I wondered aloud, fantasizing over my sister’s prude – or so I thought – sexy Latina friend.
“No way to know. Don’t even know who it is offering it, since the cord is anonymous. I don’t remember her dating anyone though. At least not recently.”
“Same,” I replied, still in fantasy mode. “Hey wait a sec, why did you say students like that?”
“Was wondering if you caught that,” Neil replied, chuckling. A sneaky grin arose on his face. “Someone is saying they have Ms. Kealoha.”
“NO FUCKING WAY!” I exclaimed, louder than I intended.
“Way. They say it’s an old pic from when she was in high school, but still. They say it’s obvious that it’s her.”
“Duuuuuuude….”
“I know,” Neil said. “Now imagine how hard it’s been for us to hold onto some of this stuff and not trade it!”
“Yeah….” I said, airily. “Thank you, by the way, for not selling me out.”
“No problem, dude. Think about what you wanna do with that pic,” Neil nodded at my phone.
“Already thought about it. Let’s do it!” I pressed send.
*********************
Meanwhile, I was determined to make a routine out of Bailey flashing me at home. I pulled off several more feints, where, I led her to think I wouldn’t be home for a while, but then came busting in on her during her hallway streaks.
The first time, she emerged into the hallway, cupping her tits and vag. She didn’t scream when she spotted me. It seemed; she had expected it. Perhaps I had broken her spirit. Regardless….don’t care!
She released her top hand and let me see her soft, puffy nipples as she gave me the finger and glared at me. She nearly reached the corner, but I cut her off.
“Whoah, whoah, whoah!” I smirked. “Now, the lower half!”
Bailey let out a deep sigh “UGGGGHHHHHHHH,” and pouted. Then, she reluctantly moved her bottom hand and allowed me to examine her sexy little pussy!
“See that’s just….perfect,” I babbled.
She gave me an as if look and marched into her room.
And on it went.
The highlight of my young life, I’ve never looked forward to anything as much as I’ve looked forward to Bailey’s post shower walks.
Eventually, she stopped bothering to cover at all. She just strutted, butt-ass-naked, down the hallway and allowed me to gawk. She had worked up the courage to look at me but she always gave me a nasty scowl or flicked me off. What did I care?! I had front row tickets to my very own nude fashion show! I’m the luckiest kid alive.
“Goddamn Ben, you gotta try and catch him taking her to pound town,” Peter said one day after school.
I had asked the crew to meet me at the library. I knew it would be dead. I showed them the topless selfie I’d stolen off of Bailey’s phone.
“Well, you better be quick, cause once we leak this and she finds out, it’s over for him,” Neil said.
“He never comes over anyway, trust me I would have tried,” I said. “That said, I can’t actually confirm this was ever sent to Craig.”
“What do you mean?”
“I mean the captions make it seem like it was…and it probably was, but it was just in the memories section. All the pics sent in the chat disappear unless someone saves it,” I explained.
“Which he wouldn’t have been stupid enough to do,” Neil said. “At least not directly, where she could find out.”
“It’s risky,” I sighed. “If she never sent it….I’m fucked.”
“Up to you man,” Neil shrugged. “If we dangle this out there though, people are definitely gonna bite.”
“Yes, we’ve had numerous offers on our prior MVP subjects,” Arnie said. “This will be no different.”
“Any idea who are in the offers?” I asked.
“Well….the two most intriguing students are Kaila and Maria,”
“Fernandez?!” I interrupted.
“Yup,” Neil nodded.
“You think it’s legit?” I wondered aloud, fantasizing over my sister’s prude – or so I thought – sexy Latina friend.
“No way to know. Don’t even know who it is offering it, since the cord is anonymous. I don’t remember her dating anyone though. At least not recently.”
“Same,” I replied, still in fantasy mode. “Hey wait a sec, why did you say students like that?”
“Was wondering if you caught that,” Neil replied, chuckling. A sneaky grin arose on his face. “Someone is saying they have Ms. Kealoha.”
“NO FUCKING WAY!” I exclaimed, louder than I intended.
“Way. They say it’s an old pic from when she was in high school, but still. They say it’s obvious that it’s her.”
“Duuuuuuude….”
“I know,” Neil said. “Now imagine how hard it’s been for us to hold onto some of this stuff and not trade it!”
“Yeah….” I said, airily. “Thank you, by the way, for not selling me out.”
“No problem, dude. Think about what you wanna do with that pic,” Neil nodded at my phone.
“Already thought about it. Let’s do it!” I pressed send.
*********************
Meanwhile, I was determined to make a routine out of Bailey flashing me at home. I pulled off several more feints, where, I led her to think I wouldn’t be home for a while, but then came busting in on her during her hallway streaks.
The first time, she emerged into the hallway, cupping her tits and vag. She didn’t scream when she spotted me. It seemed; she had expected it. Perhaps I had broken her spirit. Regardless….don’t care!
She released her top hand and let me see her soft, puffy nipples as she gave me the finger and glared at me. She nearly reached the corner, but I cut her off.
“Whoah, whoah, whoah!” I smirked. “Now, the lower half!”
Bailey let out a deep sigh “UGGGGHHHHHHHH,” and pouted. Then, she reluctantly moved her bottom hand and allowed me to examine her sexy little pussy!
“See that’s just….perfect,” I babbled.
She gave me an as if look and marched into her room.
And on it went.
The highlight of my young life, I’ve never looked forward to anything as much as I’ve looked forward to Bailey’s post shower walks.
Eventually, she stopped bothering to cover at all. She just strutted, butt-ass-naked, down the hallway and allowed me to gawk. She had worked up the courage to look at me but she always gave me a nasty scowl or flicked me off. What did I care?! I had front row tickets to my very own nude fashion show! I’m the luckiest kid alive.
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Re: A Tangled Web
BEN
Welp, that didn’t take long.
The Bailey G! file showed up in the VIP section with the file name visible to everyone on the discord. By the end of the week, all three promised girls had shown up as well.
Kaila H.
Maria F….and friends!
Ms. Kealoha!
HO-LY-SHIT! I needed to pace myself.
I started with my sister. I was curious about the comments, and they didn’t disappoint.
“Hey now, check out Bailey’s BO BOs!!!!!
“OMG what a FAT rack!!!”
“I knew it!!!!!”
“Blast off!!!! (rocket emojis)”
“Thank you Landon!....Or Craig!....or whoever decided to bless us!!!!”
“Oh my God they’re even more perfect than I imagined!!!”
“Someone’s gettin killed LMAO!!!!
“Bahahahaha she a ho fo sho”
“bro should’ve waited till he got more, now we’ll never get to see the rest”
The last comment was just that South Park meme of Randy Marsh covered in semen.
These comments alone were enough to fap to. I wasn’t about to go all hipster over my sister’s nudes, “well I saw her before she blew up….”. I don’t even know how many people had seen her naked by now, but I was loving it!
I moved on to Kaila. There was a new file next to her thong pic at Homecoming. I clicked on it.
DAMN!!!!
A nearly full-frontal selfie showed up on my screen. Kaila was wearing nothing, but had her hand draped over her vag. So close! Fuck! Still, her little titties are NICE!!! They’re perky and sit on the upper sides of her chest. She has cute little brown button nipples. Her body is so sexy and petite. She held the phone up, partially obscuring her face, but there aren’t many Asian girls at our school and she made the mistake of leaving a Webberson High Cheerleading poster – which hung on the wall of her bedroom – visible in the pic. It was 100% her.
The comments were more of the same, only now with some racist shit mixed in. That’s WHS for you, always keeping it classy. The comments on Kaila didn’t excite me nearly as much as they did for Bailey.
Next was Maria. I prayed this one would be better and my prayers were answered when I saw the file was an MP4. I clicked on it.
The video started and it was one of those webcam roulette type of sites. Maria, Jamie, and another girl from Bailey’s grade, Nikki Walker, sat facing the camera and laughing. They were chatting with two douchey looking bros that I didn’t recognize. Well, at least they thought they were. Seems like they may have been played, unless this video somehow ended up on the internet and someone from our school discovered it. Anyway, the two dudes in the video were the exact type of guy that every chick loses her shit over at my school. High cheek bones, little neck tats, stupid ass broccoli haircut.
The trio of girls were giggling and flirting. The early portion of the video was super boring. Only interesting thing that happened was all three girls stood up and spun around. They were all wearing T shirts and those little cotton athletic shorts. They looked effortlessly hot in their casual attire.
“Flash?” One of the guys typed.
Jamie shook her head no.
“C’monnnnnnnn”
“Live a little”
The girls laughed and looked at each other. Then, Jamie shrugged her shoulders, and lifted her shirt up, exposing her white and yellow floral patterned push-up bra.
“Oh shit!” Maria laughed at her friend’s behavior.
“Damn…” The dudes responded, and their jaws dropped.
“Where y’all from?” One of the guys asked.
“Canada.” Nikki typed. Blatant lie. They continued chatting about stupid shit.
“Wanna play a game?” The dudes eventually typed.
“What kinda game?” Maria asked.
“Dare game. You guys win and we’ll do ANYTHING you want! And you’ll end up on the leader board.”
“Hahaha, what’s the leader board?” Jamie asked.
The dudes switched their screen and showed a board with a list of names, locations, and scores. Now I was almost positive that these two broccoli heads were actually just one loser sitting in his basement. But girls are idiots.
“K we’ll play,” Jamie agreed. Maria and Nikki looked more hesitant.
“What do we have to do?”
“Here,” The guy switched to another screen that had a list of dares.
The girls laughed and began playing.
The dares started innocent.
“Wave at the camera”
“Make a heart”
“Do a cart-wheel”
That type of shit. Maria, Jamie, and Nikki played along and all three of them had to complete each dare. I already knew where this was headed.
“Lift your shirt and show bra”
The girls, apparently, hadn’t guessed this is what was gonna happen. At least they didn’t show it. They all looked surprised and burst out giggling.
“I already did that,” Jamie said.
“True. How bout your friends?” The dudes typed.
Jamie looked at her friends. Maria and Nikki smiled and rolled their eyes. Then lifted up their shirts to show their bras. Maria wore a sexy Victoria Secret black and pink bra that showed off her tanned cleavage. Nikki had on a green sports bra, but you could make out her nips poking into the material.
“Show your booty”
Was the next dare. The girls did it all at once and turned to show off their asses. Jamie peeled her shorts down and mooned the camera without being prompted. The dudes didn’t make the other two show bare ass.
“Panties!”
Jamie, once again, was the most willing. She slid her shorts down to her knees and showed off a skimpy white thong. Maria and Nikki just pulled up the waist bands of their underwear.
“TA-TAs!!!”
“Bahahah I knew it!!!” Maria exclaimed, thinking she was Sherlock Holmes. Despite her tanned complexion, some pink was evident on her cheeks. The three girls spent some time looking at each other.
“Jame, do it,” Maria commanded.
“Haha, I will…..but you know they’re gonna make you guys do it too. I’m not doing it if you guys are just gonna chicken out anyway.”
“Hmmm….” Nikki said.
“Hey now…why don’t you guys take your shirts off for us first?” Maria asked into the webcam.
“One sec” The guys typed.
Maybe 30 seconds later the screen switched again and the two bros were on cam with their rippling muscles and six packs on display. One of them had a large tat across his chest.
“Jeeze….” Jamie muttered, entranced. All three girls got up close to the screen. They all looked at each other again, quizzically.
“Ok….” Maria said softly.
“You’ll do it?!” Jamie asked. Maria nodded. “Nikki?”
“Yup.”
…..
All three girls lifted up their shirts and flashed their tits!
Jamie’s averaged sized boobs with giant nips looked as cute as in the soccer shower video. Nikki’s tits are VERY close together, with teeny tiny nips. The contrast between nips was hilariously arousing. Unfortunately, Maria was kind of off the screen. Fuck.
“WOW” The dudes typed. “Couldn’t see the third girl tho” Nice…
“Who?” The girls asked.
“Tan girl”
Jamie and Nikki laughed at Maria.
“Can she do it again?”
“Seriously?!” Maria giggled. Jamie and Nikki got out of view of the camera to make room.
Maria centered herself, making sure she wouldn’t have to do this a third time. She pulled her t shirt and bra up and showed off a pair of softball-sized titties with soft nipples that reminded me of my sister! God damn they’re nice!
“Jesus…” The guys typed. The next dare popped up on the screen…
“Shaved or Bush?”
“Okay, I am NOT doing that!” Maria said.
Jamie just smiled.
“I mean it’s gotta be last, right?” Nikki said, with caution.
“Don’t care. I am not showing that on national…..whatever this is,” Maria pointed at the screen.
“It’s just two dudes, Maria! You’re NEVER gonna see them again! They live across the country!”
“I haven’t shaved!” Maria whispered with embarrassment. Oh man, this was hot.
“Neither have I,” Nikki said. “I’ll do it though, it’ll win us the game.”
Nikki turned away from the camera, and pulled down her shorts, slightly. “See?”
“Oh, come on, you have NOTHING!” Maria protested.
“Oh, sack up, Maria, here, watch,” Jamie stood up facing the cam, pulled her shorts and underwear down, and flashed her shaved clean coochie! “See? Done. Easy,”
Maria pouted, sticking her bottom lip out.
“Come on, Maria. We’ll do it together,” Nikki said.
“Grrrrr, fine. You guys are a bad influence!”
Nikki and Maria centered themselves. They both stood up...and their bottoms came down! Nikki has an outie pussy, you could see A LOT of her lips! I couldn’t make out any pubes though, despite her claiming she hadn’t shaved. Maria’s kitty was nice and neatly trimmed. A buzzed black bush. Super sexy.
“PERFECT” The dudes typed. “Almost there!”
“What?!” Maria groaned. “I thought that was it!”
“Strip Naked” Appeared on the screen.
“OH MY GOD. I am NOT doing that! Sorry guys. NO WAY!” Maria protested. “Hit next!”
Jamie jumped in front of the camera to make sure Maria didn’t exit out of the chat.
“Just….hang on, ok? Let me see if they’ll bargain with us,” Jamie said. She began typing.
“What if just two of us do it?”
“hahaha, bold of you to think I’m doing that with you, Jame!” Nikki laughed.
“Shut up, let’s see what they say,” Jamie snapped.
“Sorry…gotta be all three” The dudes replied.
Jamie frowned. She looked at her friends, and sighed. “Come on, Maria! You’ve already showed everything anyway! What if they do it first?”
Maria stood, with her arms crossed. Her mouth curled upside down. “Ask em,” she replied, in a short manner.
“If you guys get naked first….we’ll do it” Jamie typed.
There was a long period of waiting.
“K” was all the dudes typed.
Their screen switched again and the two dudes stood up, buck naked in front of the camera. Their cocks were MASSIVE and I was now positive this vid was a fake.
“HOLY CRAP!” Maria blurted out. “Is that real?!” Her jaw dropped.
The dude’s video glitched a bit, and then one of the dudes nodded his head, yes. Whoever was controlling this video, was good. The two guys in the video began lightly tapping on each other’s erect dicks, making them bounce up and down. The girls were mesmerized and just stared silently into the camera, not saying a word. Whores, I laughed.
The screen switched back to the game.
“Well?” The guys typed.
The trio of girls glanced at one another again, and Maria was less tense and apprehensive than before. Redness was appearing on her face again…and I could tell she was…at the very least…thinking about it.
“Come on, Maria…” Nikki had given in. “They said they’ll do ANYTHING.”
“I don’t wanna take everything off…” Maria said.
“It’ll be quick!” Jamie argued.
“No…I mean….I’ll do it. I’ll show everything. But ask if we can just, like, lift our shirts and pull our shorts down?”
“K.” Jamie began furiously typing. I’m not sure why, did the girls still not realize that their mic was on and everything they said could be heard? They really are morons.
“That works” The guys typed back, not wanting to be greedy.
“Okay….” Jamie typed.
“Alright, let’s all do it, really quick,” Jamie said.
“Make sure we’re all on the cam, I’m not doing this twice!” Maria said.
Oh my God, my dick felt like it was about to explode. I can’t believe I was witnessing this.
The trio of hotties stood in front of the cam and adjusted themselves. When they wanted to, all three easily fit in view.
“Okay, on three,” Jamie said.
“One…..”
“Two….”
“Oh jeeze, are you guys seriously doing it? This is….this is risky!” Maria said.
“THREE!!!” Jamie shouted out.
Maria closed her eyes. All three girls pulled their shorts down, and lifted their shirts...exposing their bare naked bodies for the camera!!
Ironically, you could see Maria the best out of the three. She was in the center, and stood up the tallest. Her tits were nice and perky as her arms were propped, holding up her shirt. Her belly button is slim and sexy with a sparkling ring in it. Her pussy hair is so neat, a perfect triangle of dark fuzz. I glanced to her sides and checked out Jamie’s big nips and hairless box. Then, Nikki, with her tight rack, barely-there-nipples, and prominent pussy lips. My God!!!
Nothing else interesting happened the rest of the video. The guys tried to get the girls to show and do more on cam, but the girls refused, unless the guys did stuff. Eventually, the girls got annoyed and left the chat. I’m not sure they ever realized they’d been conned. Once this video makes its way around school – and it will – it’ll be interesting to see their reactions!
Last, but certainly not least, Ms. Kealoha. Ms. Kealoha is in her twenties, and drop dead gorgeous. Hawaiian descent with long, curly dark hair, skin, and eyes – a very exotic look for our side of the country. The dudes at school, including myself, go crazy over her. I wasn’t expecting much when I clicked on the file. Oh man, was I wrong.
It was just one picture, that looked, maybe 10 years old. Definitely taken with an earlier generation phone. But boy did it tell a story. Ms. Kealoha was standing up on a stage, wearing a tiara – and NOTHING else!!!! She looked absolutely mortified, and appeared to be screaming. Her tits were big and tan with little nips. Two fat girls were holding her hands behind her back. Her pussy was puffy and shaved clean and bared on stage. There appeared to be a hot black chick laughing while holding Ms. Kealoha’s underwear down around her ankles.
WHAT...THE...FUCK!!!!
I don’t know if this was some sort of beauty pageant, or prom, or fashion show, or what, but it was incredible. Almost unbelievable that something like this happened to someone as hot as Ms. Kealoha. And it was her, no doubt about it. She had the same flower in her hair that Ms. Kealoha sometimes wears and – even more defining – the same beauty spots on the top of her chest. I suppose in today’s day and age it could’ve been AI or photo-shopped, but everyone in the pic had only five fingers and there was nothing else wonky going on. I think this was the real deal. A pic this hot will never disappear off the internet once it’s there. It was just a matter of someone at our school coming across it and realizing who was in it. I wish I knew the full story….
Welp, that didn’t take long.
The Bailey G! file showed up in the VIP section with the file name visible to everyone on the discord. By the end of the week, all three promised girls had shown up as well.
Kaila H.
Maria F….and friends!
Ms. Kealoha!
HO-LY-SHIT! I needed to pace myself.
I started with my sister. I was curious about the comments, and they didn’t disappoint.
“Hey now, check out Bailey’s BO BOs!!!!!
“OMG what a FAT rack!!!”
“I knew it!!!!!”
“Blast off!!!! (rocket emojis)”
“Thank you Landon!....Or Craig!....or whoever decided to bless us!!!!”
“Oh my God they’re even more perfect than I imagined!!!”
“Someone’s gettin killed LMAO!!!!
“Bahahahaha she a ho fo sho”
“bro should’ve waited till he got more, now we’ll never get to see the rest”
The last comment was just that South Park meme of Randy Marsh covered in semen.
These comments alone were enough to fap to. I wasn’t about to go all hipster over my sister’s nudes, “well I saw her before she blew up….”. I don’t even know how many people had seen her naked by now, but I was loving it!
I moved on to Kaila. There was a new file next to her thong pic at Homecoming. I clicked on it.
DAMN!!!!
A nearly full-frontal selfie showed up on my screen. Kaila was wearing nothing, but had her hand draped over her vag. So close! Fuck! Still, her little titties are NICE!!! They’re perky and sit on the upper sides of her chest. She has cute little brown button nipples. Her body is so sexy and petite. She held the phone up, partially obscuring her face, but there aren’t many Asian girls at our school and she made the mistake of leaving a Webberson High Cheerleading poster – which hung on the wall of her bedroom – visible in the pic. It was 100% her.
The comments were more of the same, only now with some racist shit mixed in. That’s WHS for you, always keeping it classy. The comments on Kaila didn’t excite me nearly as much as they did for Bailey.
Next was Maria. I prayed this one would be better and my prayers were answered when I saw the file was an MP4. I clicked on it.
The video started and it was one of those webcam roulette type of sites. Maria, Jamie, and another girl from Bailey’s grade, Nikki Walker, sat facing the camera and laughing. They were chatting with two douchey looking bros that I didn’t recognize. Well, at least they thought they were. Seems like they may have been played, unless this video somehow ended up on the internet and someone from our school discovered it. Anyway, the two dudes in the video were the exact type of guy that every chick loses her shit over at my school. High cheek bones, little neck tats, stupid ass broccoli haircut.
The trio of girls were giggling and flirting. The early portion of the video was super boring. Only interesting thing that happened was all three girls stood up and spun around. They were all wearing T shirts and those little cotton athletic shorts. They looked effortlessly hot in their casual attire.
“Flash?” One of the guys typed.
Jamie shook her head no.
“C’monnnnnnnn”
“Live a little”
The girls laughed and looked at each other. Then, Jamie shrugged her shoulders, and lifted her shirt up, exposing her white and yellow floral patterned push-up bra.
“Oh shit!” Maria laughed at her friend’s behavior.
“Damn…” The dudes responded, and their jaws dropped.
“Where y’all from?” One of the guys asked.
“Canada.” Nikki typed. Blatant lie. They continued chatting about stupid shit.
“Wanna play a game?” The dudes eventually typed.
“What kinda game?” Maria asked.
“Dare game. You guys win and we’ll do ANYTHING you want! And you’ll end up on the leader board.”
“Hahaha, what’s the leader board?” Jamie asked.
The dudes switched their screen and showed a board with a list of names, locations, and scores. Now I was almost positive that these two broccoli heads were actually just one loser sitting in his basement. But girls are idiots.
“K we’ll play,” Jamie agreed. Maria and Nikki looked more hesitant.
“What do we have to do?”
“Here,” The guy switched to another screen that had a list of dares.
The girls laughed and began playing.
The dares started innocent.
“Wave at the camera”
“Make a heart”
“Do a cart-wheel”
That type of shit. Maria, Jamie, and Nikki played along and all three of them had to complete each dare. I already knew where this was headed.
“Lift your shirt and show bra”
The girls, apparently, hadn’t guessed this is what was gonna happen. At least they didn’t show it. They all looked surprised and burst out giggling.
“I already did that,” Jamie said.
“True. How bout your friends?” The dudes typed.
Jamie looked at her friends. Maria and Nikki smiled and rolled their eyes. Then lifted up their shirts to show their bras. Maria wore a sexy Victoria Secret black and pink bra that showed off her tanned cleavage. Nikki had on a green sports bra, but you could make out her nips poking into the material.
“Show your booty”
Was the next dare. The girls did it all at once and turned to show off their asses. Jamie peeled her shorts down and mooned the camera without being prompted. The dudes didn’t make the other two show bare ass.
“Panties!”
Jamie, once again, was the most willing. She slid her shorts down to her knees and showed off a skimpy white thong. Maria and Nikki just pulled up the waist bands of their underwear.
“TA-TAs!!!”
“Bahahah I knew it!!!” Maria exclaimed, thinking she was Sherlock Holmes. Despite her tanned complexion, some pink was evident on her cheeks. The three girls spent some time looking at each other.
“Jame, do it,” Maria commanded.
“Haha, I will…..but you know they’re gonna make you guys do it too. I’m not doing it if you guys are just gonna chicken out anyway.”
“Hmmm….” Nikki said.
“Hey now…why don’t you guys take your shirts off for us first?” Maria asked into the webcam.
“One sec” The guys typed.
Maybe 30 seconds later the screen switched again and the two bros were on cam with their rippling muscles and six packs on display. One of them had a large tat across his chest.
“Jeeze….” Jamie muttered, entranced. All three girls got up close to the screen. They all looked at each other again, quizzically.
“Ok….” Maria said softly.
“You’ll do it?!” Jamie asked. Maria nodded. “Nikki?”
“Yup.”
…..
All three girls lifted up their shirts and flashed their tits!
Jamie’s averaged sized boobs with giant nips looked as cute as in the soccer shower video. Nikki’s tits are VERY close together, with teeny tiny nips. The contrast between nips was hilariously arousing. Unfortunately, Maria was kind of off the screen. Fuck.
“WOW” The dudes typed. “Couldn’t see the third girl tho” Nice…
“Who?” The girls asked.
“Tan girl”
Jamie and Nikki laughed at Maria.
“Can she do it again?”
“Seriously?!” Maria giggled. Jamie and Nikki got out of view of the camera to make room.
Maria centered herself, making sure she wouldn’t have to do this a third time. She pulled her t shirt and bra up and showed off a pair of softball-sized titties with soft nipples that reminded me of my sister! God damn they’re nice!
“Jesus…” The guys typed. The next dare popped up on the screen…
“Shaved or Bush?”
“Okay, I am NOT doing that!” Maria said.
Jamie just smiled.
“I mean it’s gotta be last, right?” Nikki said, with caution.
“Don’t care. I am not showing that on national…..whatever this is,” Maria pointed at the screen.
“It’s just two dudes, Maria! You’re NEVER gonna see them again! They live across the country!”
“I haven’t shaved!” Maria whispered with embarrassment. Oh man, this was hot.
“Neither have I,” Nikki said. “I’ll do it though, it’ll win us the game.”
Nikki turned away from the camera, and pulled down her shorts, slightly. “See?”
“Oh, come on, you have NOTHING!” Maria protested.
“Oh, sack up, Maria, here, watch,” Jamie stood up facing the cam, pulled her shorts and underwear down, and flashed her shaved clean coochie! “See? Done. Easy,”
Maria pouted, sticking her bottom lip out.
“Come on, Maria. We’ll do it together,” Nikki said.
“Grrrrr, fine. You guys are a bad influence!”
Nikki and Maria centered themselves. They both stood up...and their bottoms came down! Nikki has an outie pussy, you could see A LOT of her lips! I couldn’t make out any pubes though, despite her claiming she hadn’t shaved. Maria’s kitty was nice and neatly trimmed. A buzzed black bush. Super sexy.
“PERFECT” The dudes typed. “Almost there!”
“What?!” Maria groaned. “I thought that was it!”
“Strip Naked” Appeared on the screen.
“OH MY GOD. I am NOT doing that! Sorry guys. NO WAY!” Maria protested. “Hit next!”
Jamie jumped in front of the camera to make sure Maria didn’t exit out of the chat.
“Just….hang on, ok? Let me see if they’ll bargain with us,” Jamie said. She began typing.
“What if just two of us do it?”
“hahaha, bold of you to think I’m doing that with you, Jame!” Nikki laughed.
“Shut up, let’s see what they say,” Jamie snapped.
“Sorry…gotta be all three” The dudes replied.
Jamie frowned. She looked at her friends, and sighed. “Come on, Maria! You’ve already showed everything anyway! What if they do it first?”
Maria stood, with her arms crossed. Her mouth curled upside down. “Ask em,” she replied, in a short manner.
“If you guys get naked first….we’ll do it” Jamie typed.
There was a long period of waiting.
“K” was all the dudes typed.
Their screen switched again and the two dudes stood up, buck naked in front of the camera. Their cocks were MASSIVE and I was now positive this vid was a fake.
“HOLY CRAP!” Maria blurted out. “Is that real?!” Her jaw dropped.
The dude’s video glitched a bit, and then one of the dudes nodded his head, yes. Whoever was controlling this video, was good. The two guys in the video began lightly tapping on each other’s erect dicks, making them bounce up and down. The girls were mesmerized and just stared silently into the camera, not saying a word. Whores, I laughed.
The screen switched back to the game.
“Well?” The guys typed.
The trio of girls glanced at one another again, and Maria was less tense and apprehensive than before. Redness was appearing on her face again…and I could tell she was…at the very least…thinking about it.
“Come on, Maria…” Nikki had given in. “They said they’ll do ANYTHING.”
“I don’t wanna take everything off…” Maria said.
“It’ll be quick!” Jamie argued.
“No…I mean….I’ll do it. I’ll show everything. But ask if we can just, like, lift our shirts and pull our shorts down?”
“K.” Jamie began furiously typing. I’m not sure why, did the girls still not realize that their mic was on and everything they said could be heard? They really are morons.
“That works” The guys typed back, not wanting to be greedy.
“Okay….” Jamie typed.
“Alright, let’s all do it, really quick,” Jamie said.
“Make sure we’re all on the cam, I’m not doing this twice!” Maria said.
Oh my God, my dick felt like it was about to explode. I can’t believe I was witnessing this.
The trio of hotties stood in front of the cam and adjusted themselves. When they wanted to, all three easily fit in view.
“Okay, on three,” Jamie said.
“One…..”
“Two….”
“Oh jeeze, are you guys seriously doing it? This is….this is risky!” Maria said.
“THREE!!!” Jamie shouted out.
Maria closed her eyes. All three girls pulled their shorts down, and lifted their shirts...exposing their bare naked bodies for the camera!!
Ironically, you could see Maria the best out of the three. She was in the center, and stood up the tallest. Her tits were nice and perky as her arms were propped, holding up her shirt. Her belly button is slim and sexy with a sparkling ring in it. Her pussy hair is so neat, a perfect triangle of dark fuzz. I glanced to her sides and checked out Jamie’s big nips and hairless box. Then, Nikki, with her tight rack, barely-there-nipples, and prominent pussy lips. My God!!!
Nothing else interesting happened the rest of the video. The guys tried to get the girls to show and do more on cam, but the girls refused, unless the guys did stuff. Eventually, the girls got annoyed and left the chat. I’m not sure they ever realized they’d been conned. Once this video makes its way around school – and it will – it’ll be interesting to see their reactions!
Last, but certainly not least, Ms. Kealoha. Ms. Kealoha is in her twenties, and drop dead gorgeous. Hawaiian descent with long, curly dark hair, skin, and eyes – a very exotic look for our side of the country. The dudes at school, including myself, go crazy over her. I wasn’t expecting much when I clicked on the file. Oh man, was I wrong.
It was just one picture, that looked, maybe 10 years old. Definitely taken with an earlier generation phone. But boy did it tell a story. Ms. Kealoha was standing up on a stage, wearing a tiara – and NOTHING else!!!! She looked absolutely mortified, and appeared to be screaming. Her tits were big and tan with little nips. Two fat girls were holding her hands behind her back. Her pussy was puffy and shaved clean and bared on stage. There appeared to be a hot black chick laughing while holding Ms. Kealoha’s underwear down around her ankles.
WHAT...THE...FUCK!!!!
I don’t know if this was some sort of beauty pageant, or prom, or fashion show, or what, but it was incredible. Almost unbelievable that something like this happened to someone as hot as Ms. Kealoha. And it was her, no doubt about it. She had the same flower in her hair that Ms. Kealoha sometimes wears and – even more defining – the same beauty spots on the top of her chest. I suppose in today’s day and age it could’ve been AI or photo-shopped, but everyone in the pic had only five fingers and there was nothing else wonky going on. I think this was the real deal. A pic this hot will never disappear off the internet once it’s there. It was just a matter of someone at our school coming across it and realizing who was in it. I wish I knew the full story….
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