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Jess Tells All

Categories Fantasy, Anal, Authoritarian, BDSM

Authror: NathanRex

Published: 07 May 2018

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Jess was late to Ms Enfield’s class. Chloe was finding it hard to concentrate, because she knew exactly what that meant. Jess, her best friend for years, had recently caught the attention of Nathan Oldcastle. Nathan was the only boy: not only in the school, but also the county and most of the surrounding area. Chloe had been surprised that Jess had even registered on his radar – she was certainly pretty enough, but he was a year older than she was and was still (by all accounts) working through the girls in his own year. But sure enough, earlier in the week Jess had rocked up to class wearing a bracelet with a silver eagle as its buckle: Nathan’s symbol, the wearing of which marked his claim to her. While not as binding as the collars that Nathan’s chosen women would wear upon his and their reaching full adulthood, the giving (and receiving) of a bracelet carried with it various assumptions and, indeed obligations: but also privilege. Jess’ reputation in the year had sky-rocketed – going from a slightly awkward outsider to something of a queen bee.

Teachers also were a lot more lenient with claimed girls when it came to dress codes and class attendance – as long as they weren’t baring their goods for the whole world to see or missing entire lessons then they could get away with a lot.

Which was lucky for Jess, Chloe thought, as she breezed into the room – perhaps walking a little stiffly on her heels, clearly sweaty, and with the top three buttons of her blouse undone. Seeing the space Chloe had saved, she smiled and sat down, with a quick “Hi!” Ms Enfield didn’t even stop to acknowledge Jess’ presence, and instead continued on about the sides of a triangle and exactly what one is supposed to do with them. After a short amount of time, she finished and then came over to Chloe and Jess.

Looking at Chloe, she said “Why don’t you go through the exercises with Jess. You can explain what she missed. Just ask if you have any problems.” The look in the teacher’s eyes told Chloe that she doubted they’d get any work done.

With that, she moved around to another group to answer a question.

“So…” Chloe began a little awkwardly “How was it?”.

“Wonderful!” Jess replied, leaning forward slightly. Chloe gasped – Jess wasn’t wearing a bra!

“Uh, Jess,” she said “When you lean forward like that people can see your – you know”.

“I know they can.” Jess giggled. “It’s why Nathan asked me to dress like this. I can hardly pull off Josie’s look, can I?” Josie was one of Nathan’s favourites – she had very large breasts to her name and when in school typically wore blouses several sizes too small to make them even more obvious. Out of school, she was even worse.

“Nathan says that girls with smaller tits, like me, shouldn’t feel embarrassed about it.”

Chloe was shocked silent – Jess’ chest had attracted some bullying in the past and everyone knew that she hated it. Or rather, had done. Chloe couldn’t quite believe the change in her friend.

“Want to hear what he did to me today?” Chloe couldn’t seem to stop herself from nodding – despite everything, she really did want to know.

“Well Emily found me when I was coming out of the toilets halfway through lunch.” Chloe had guessed as much – she’d waited for Jess to come back for fifteen minutes before giving up.

“She took me to Nathan – in that classroom on the second floor of the geography building, you know? The one with the skylight?” Chloe nodded: She had had a lesson there earlier in the day.

“Well he was sitting down at the desk. Josie was there with Sarah – Emily too of course, she came in with me.”

Sarah and Emily were other favourites of Nathan’s. Emily, a short dark-haired girl, was always happy to please and would run around on all sorts of odd jobs for him. Sarah, a very pretty blonde infamous for her dominant tendencies (directed only where Nathan chose, and thus only ever at girls who either preferred it that way or else needed bringing back in line), and Josie with her red hair and massive tits were, in Nathan’s own words ‘less useful but more fun’.

“Nathan didn’t speak to begin with. Emily said she’d brought me, and then Sarah said something like ‘Ah yes, Jess is here for another lesson.’ The girls laughed at that and Nathan smiled.”

“He could see I was shaking so told me that there was no need to be nervous. It really did help… then Emily got the camera out and –“

Chloe re-found her voice “Wait, they filmed you?” throughout Jess’ story up to this point she’d been desperately trying to work through the maths problems and not let the story affect her. Maisy, who was sitting the other side of Jess, had stopped even pretending to work and was clearly fixated on Jess’ story along with several other girls: Jess was loving the attention.

“Oh yes, of course they did. Emily often films us – didn’t you know that? Tell you what, I’ll see if I can get a copy to show you later” Chloe was shocked into silence again – as much by Jess’ use of the word us, meaning Nathan’s girls, than her offer.

“Anyway, where was I. Well Nathan asked me if I was ready to begin, and when I said I was he told Sarah she could take it from there. Sarah told me that she’d be teaching me how something new today, and to take off my clothes and lean over a desk, away from Nathan. Once I’d done that, Emily moved around so the camera was in front of me. Josie was sitting on the desk next to me. She leaned in and whispered in my ear ‘Can you guess what we’re going to do to you?’ – I shook my head and she giggled ‘Oh, you’re going to love it’ she said, to the camera this time.

Sarah got out her cuffs from her bag - ” That at least did not shock Chloe: She’d heard all sorts of rumours about the precise contents of Sarah’s bag. “She’s got these weights which attach to the cuffs – did you know that?” Chloe shook her head. “I’m not sure how she carries them around all day – they’re really heavy – well, she put one pair of cuffs on each of my wrists and put the weights on the other end, then pushed them off the other side of the table lifting me up on my heels and pressing my body flat to the desk. I think I could have pulled away if I wanted to. But I didn’t, of course.”

“Sarah looked me straight in the eyes and said ‘Today, Bitch, you’re taking it up that little arse of yours.’” Sarah never used names: to her, everyone was either Bitch (inferior), Slut (equal) or Sir (Nathan).

"They stopped talking for a little while Sarah went back to her bag - I think, I couldn't see of course. The weights were starting to hurt a bit, and Josie could see so that so started stroking my hair and telling me that I was being a good little bitch. That helped a lot. Sarah spoke up then and said I needed some training before I was ready for Nathan. Josie whispered in my ear ‘She’s just saying that because she wants a go with you herself.’ Sarah must have heard her, because she said ‘Damn right I do Slut. I’m gunna make her squeal."

Maisy was clearly getting rather hot and bothered at this point - and Chloe, who had put down her pen, was now listening intently while absent mindedly biting her lower lip.

“Suddenly, I felt a thwack across my arse - it was Sarah of course, with a metre ruler. She said ‘That was One. Repeat after me every time, and when we get to Twenty it’ll be over.’ She hit me again and again - repeated all of the numbers, but when we got to Eighteen Josie started making out with me - god she’s a good kisser. I said the last few numbers into her mouth but Sarah said that wasn’t good enough so she made me start again. I’m really going to be bruised tomorrow!”

Well that’s why she’s been sitting funny, Chloe thought.

“Anyway, Sarah told me that I’d done well the second time, but now she was really going to get me ready. Josie made a ‘mmm’ kind of noise when she saw what Sarah had got. She looked at the camera and smiled, and then looked down at me again. ‘You really are the cutest little bitch.’ she said. I said ‘Thank you!’ and she laughed and said ‘I know a way you can thank me…’ Then all at once, Josie unbuttoned her shirt, grabbed my head and pulled it towards her tits and Sarah shoved a whiteboard marker up my arsehole. I screamed into Josie’s tits and they both laughed at me. Sarah wiggled the marker a little which made me jolt. ‘Come on you stupid Bitch.’ she said ‘The Slut’s waiting for you to give her chest some attention.’”

Chloe was positively drooling - and was just as wet between her legs. From where she was sitting, she could see Maisy’s hand slowly move up her own leg towards the hem of her skirt.

Jess continued.

“So I licked and sucked Josie’s tits, making her moan a little. She got a lot louder when Sarah pushed another marker inside me and I bit down on her nipple - she seemed to enjoy it really. Once I’d had the two for a while, Sarah said she thought I was ready. She pulled out both pens in one go - making me bite down on Josie again, her other tit this time - and then they both moved away. I heard both of them moaning behind me so they were probably doing each other.”

“And then I heard Nathan’s voice. You know, he doesn’t speak a lot, but his voice is so nice when he does. He just said ‘Are you ready, my dear?’ and when I said I was I felt his wonderful dick pressing on the outside of my hole. I groaned and pushed back a little, and together we got him in all the way. That stunned me for quite a while, but he let me get used to his size before he started thrusting. God that was the best feeling - it hurt a ton, but in a good way, you know?”

Chloe didn’t know how pain could be good, but also had no idea why the thought of it turned her on as much as it did.

“He really started picking up speed, and reached under me to hold my tits with one hand (that was when he said I should be proud of them) and grabbed my hair with the other and pulled back. I felt great - I must have came at least twice like that before I felt him firing his cum inside me. That was the best. Nathan recovered quite quickly - he always does - and asked Emily for a time check. Funny really - she’d just stood quietly filming up to that point. She said it was about fifteen minutes into the next lesson, so we should get going to class. Sarah took the cuffs off and left quite quickly. Josie stopped to kiss me before doing the same. Emily passed me my clothes - but not my underwear. When I asked why, Nathan said I wouldn’t be needing it anymore, and to never wear any in the future. I told him I wouldn’t, and then we all headed out to class. And here I am!”

Maisy spoke before Chloe. “That was amazing.” She said ‘“Really, I’m jealous.”

Jess smiled “Oh, I could put in a good word for you if you like? One of the other girls would have to try you out first, but that isn’t hard.”

Maisy blushed. “I’m not that jealous! Not yet at least. What about you, Chloe?”

“Uh, me neither.” Chloe lied unconvincingly, leading to knowing looks from both girls.

“Really! I’m not. I’m too young for that kind of thing.’

“I’m not, and I’m younger than you!” Jess retorted. “You’re just too scared to try.”

Damn right I am, Chloe thought.

Just then, the bell went. All three girls packed up, and were heading to their next lesson Chloe caught a few comments from some of the girls - apparently, Josie had told the whole story loudly in her class, and word had only spread further from there.

Suddenly, Jess spoke up “Oh look - it’s Gemma”. Sure enough, the statuesque brunette - only six inches shorter than Nathan at 5’10” - was indeed coming their way. She stopped them with a curt order to Jess.

“So.” Gemma said, looking right at Chloe

“You’re Chloe, right?”

“Uh, yeah?” came the reply, itself sounding more like a question.

“Jess here speaks quite highly of you. You’ll be spending the next hour with me - we’ve already cleared it with your teacher.”

“Wait, what? I’m not -”

“No iffs or buts. It’s already decided. Don’t make this hard on yourself.”

Chloe knew she didn’t want to cross Gemma - the older girl loved horses and carried a riding crop around with her everywhere. If the talk was true, it saw more use shutting up unruly girls than it did horses.

Jess spoke up “You’ll be fine Chloe - it’s no different to what we used to do.”

Chloe gasped - she’s never told anyone about the experimentation she had done with Jess.

Jess suddenly leaned in and kissed her full on the face.

“We can all tell you want it - just go with Gemma. You’ll love it.’

Chloe looked from girl to girl, and then nodded. Gemma smiled slightly, and then gestured for Chloe to follow.

Maisy, who had been quiet up to this point, said

“Hey, uh, Gemma. Would you like someone to film you?”

Gemma nodded, and the three girls moved off away from Jess - who was smiling contentedly.

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