Cram session

All the girls knew better by now than to openly protest against Miss Stonebridge. Tatiana, who regularly had to take it up the ass, was unphased by the reveal. Madison began nervously fidgeting with the hem of her shirt while she looked around the room, as if waiting for someone else to raise their concern about what they were about to do.

“After review of your questionnaires, and specifically the disconnect between your questionnaires and your Masters’ wishes, Principal Brown and I have decided that anal sex should be a priority.” Principal Brown probably had quite a bit of credit for that decision. “In order for you to get into the team spirit here, any reward points you collect will be received by the other team member as well… the same goes for any disciplinary points you receive. For things to be fair, since you are a single team member Ashley, yours will be doubled.”

Doubled?!

“Ashley, as you and I will be working together. Bring your mat up in front, then get down on your hands and knees while I gather your equipment.”

Why me?

Ashley shimmied up in front of the other girls and went down on all fours. Ashley watched Anita walk behind the girls to cabinet number three. Inside were five string-closed cloth bags, one for each of them. Walking behind the girls, she dropped one bag at a time in front of them. The bags thudded when they hit the ground. Madison jerked a little with every thud that echoed in the room.

“Ashley, turn your ass towards your classmates, hold your hands in front of you and lower your chest to the ground for a demonstration. Girls, this will be known as ‘Presentation Position’ or just ‘Present’ when given as a command.” Theo taught me that one. Ashley recalled his “training” in the backyard. Are there standardized **** positions? He must have learned them from that magazine that Mom gave him.

Ashley began hyperventilating and clenching tightly. What do I do? What will she do?! She’s going to put something in my ass! I don’t want to do this. Why me?!

“That’s two for not following instructions, Ashley.”

Having seen what they could mean with Anna yesterday, Ashley made the hasty decision to turn around and deal with whatever Anita was going to demonstrate rather than accumulate more disciplinary points. She dropped her chest to her mat, giving her classmates a full serving of g-string framed cheeks. All of Ashley’s focus was now directed at the sound of Anita’s heels coming closer and closer until the clicking finally stopped.

Thud

The telltale sound of another bag hitting the ground almost made her bolt for the door.

“Arch your back more.” Ashley felt her teacher’s delicate hand on the small of her back guide her into the desired position. “That’s it, now you’re in the proper ‘Present’ position.”

“Come a little closer, ladies.” Anita waved the rest of the girls forward while she knelt down in front of Ashley’s round behind. Their teacher opened the bag and took out a long clear rod and placed it in front of Ashley’s feet, repeating it until she had taken out four rods and placed them in ascending order of girth as well as a bottle of anal lube. Having five women crowd around her upturned butt made Ashley blush furiously.

“When you are new to anal, it is important to start small and work yourself up. We will begin with the small one here, since Ashley has never done this before.”

Ashley turned her head back to try and see the size of what Anita was talking about.

“The most important thing to remember is that, unlike your vagina, your behind is not self-lubricating. Meaning, we must introduce lubrication in some other way. For something smaller like this starter, your own vaginal lubrication is enough.”

Anita took the smallest rod she was holding and eased it inside Ashley’s pussy, working it further in and then out in slow pistoning motions, turning it slowly from time to time. In comparison to Theodore’s cock the experience of this thing making its way inside her was laughable. Anita continued to gently fuck Ashley with the rod until her juices made a squishy sound.

It’s still weird being watched. But not as scary as it used to be. But Ashley still couldn’t meet the eyes of the other four students.

Ashley felt Anita’s fingers pull at her thong between her cheeks and move it to the side. This is happening. With the round bulbous tip of the rod pressing against Ashley’s asshole Anita gently massaged it inside Ashley’s ass. It’s inside! Ashley felt the rod sinking deeper.

“Aaaaahhhh” Ashley moaned.

“That’s a good girl, Ashley. Ladies, see how her ass sucks it in once you get past the sphincter.” Anita pulled the rod outward and then pushed it in again. “The hardest part is getting it in, once it is inside like this you can start to move it. Start slowly at first and build up.”

“I remember my first time…” Danielle said wistfully. Anita let it slide to focus on Ashley’s training.

“Aaaaahhhh.” Ashley continued to moan when Anita began to rhythmically move the rod in and out of her ass. Anita picked up the next size and held it forward to Ashley.

“Suck on this one girl, it will be going inside you next.” To the others, she continued. “Depending on your master, you may only get the chance to lubricate it with your mouth. You may offer, but never demand, the chance to fellate him first to get his penis slick.”

Ashley took it in her mouth and coated it with her saliva. She knew it would be going in her regardless of how well she managed to lube it up, and she preferred the humiliation of having to suck on it rather than the pain of having it go in dry. Anita exchanged the small rod for the one she had Ashley lube up. With her ass having been warmed up, the second one slipped inside with more ease.

“See how much easier this one went in, even though it is larger? That is why we train our ass.” Anita’s hand never stopped moving the rod in Ashley’s ass while she spoke to the rest of the girls. “Danielle and Tatiana, Present. You two will start for your teams because you are more experienced. Don’t forget to use artificial lube once you go up in size.” Anita removed the second rod from Ashley’s ass. She opened the bottle of lube and squeezed out a good amount on Ashley’s winking hole - ooooh, cold, cold, cold! - before she pressed the next size up in the girl’s ass. Ashley was amazed she was already on the third size.

“Yes! Fuck my slutty little ass Anna!” Danielle grunted as she was throwing herself back against the rod. Anna, looking almost frightened at the ordeal, only managed to hold it still while Danielle went to town.

“Good job Anna, I think you can go one size up on Danielle now.” Anita said, looking out over the room at the girls. Madison sat on the floor, holding the clear rod in her hands, having yet to penetrate Tatiana with even the smallest size.

“Madison, you should have had that inside Tatiana for some time now. That’s one for the both of you.”

Tatiana growled back at Madison “You put in NOW, or I put fist up your ass when it your turn.” Madison squeaked, and with faltering resolve pushed the sextoy against Tatiana’s hole. It slipped inside without much effort.

Why does this feel so good? Ooooooh. With Anita watching to see how the other girls were doing she failed to notice Ashley sneaking her hand down to her crotch to rub her clit in small circles. Oh oh oh oh oooh. Ashley started jerking, catching Anita’s attention. “Ashley! Nobody has given permission for you to touch yourself! That's a regular two more, making it four for you!”

Anita took out the rod she was working and applied more lube to Ashley’s anus. She grabbed the widest of the toys and **** it into Ashley.” “Heeeeh aah!” Ashley squealed. Her eyes rolled backward when Anita got into a steady pace with it. Her body tensed up and began shaking without the help of her hand pleasuring her clit. “Good girl Ashley, if you can do it without your hand, go ahead and come for me.” Anita said, pistoning in rapid succession. “Ah ah ah ah ah fuaaack aaaaaah!” Ashley yelled as she came.

“Unfair!” Danielle yelled out hearing Ashley’s orgasm.

Anita slowed down to let Ashley collect herself. Removing the rod from Ashley's ass made a suctioning sound, laying the toy down at Ashley's feet Anita spoke reassuringly. "Good girl Ashley, you have done very well. But we both know this is not enough to prepare you for your master." Having already pleasured Theodore's cock many times Ashley knew the truth of what Anita was saying, Theodore was bigger than that last one.

"The one ordering these didn't quite expect such a well-endowed man among your owners." Ashley felt a sense of relief hearing it. Puh, I hope that person was in charge of other purchases.

"Luckily, I like to come prepared." Anita continued.

What? What did she say?

"Stay." She tapped Ashley’s backside. "You girls continue." Tatiana was moaning softly now that Madison had moved on to the third size and was being very gentle with it. "Good job Madison, listen to how Tatiana is moaning. That is not faking it. That's one reward for you both." Anita chirped.

With her head held forward Ashley watched Anita stride to her teacher's bench to collect her briefcase. Once Anita was out of view behind her she heard it click open. More cool lube squirted into her ass, oooh. She felt something soft slip inside her ass, its wide anchor shaped base lodging itself against her skin. Hearing Anita rummaging around, Ashley was still perplexed. Whatever Anita had stuck inside her was much smaller than the largest rod she used to make her come. How is this supposed to prepare me for Theo?

"Anna, concentrate on what you are doing instead of watching Ashley." Ashley heard Anita tell the girl off from far away. "Okay girls, time to switch places. Ashley, you stay where you are."

"Do we have to?" Danielle complained, with Anna nodding in agreement.

"Yes, you too. You wouldn't want to deny Anna from being prepared for her master, would you?" Anita answered, having learned how to talk to Danielle.

"Present." Tatiana commanded Madison.

"Hey you can't just-"

“Present ass now” Tatiana gripped Madison's neck and pushed her face to the floor. She held her in place while she pulled the girl's panties down. Sliding the clear rod across Madison exposed lips left a soft sheen to it. Tatiana pushed the semi dry rod against the struggling girl's anus.

"Ouch! She said to lube! Ow ow ow."

"Not my fault you take too long."

"Easy does it, girls." Anita reminded them, standing up she walked over to Anna to inspect. Danielle had grabbed the largest one first, and Anita gently took it and replaced it with the thinnest size. “Make sure to start from the correct side with her toys, Danielle.” Anna was squirming and breathed heavily when Danielle placed the tip against her butthole. "That's it Anna, relax and let Danielle take care of you." Anita gently patted Anna’s upturned buttcheek.

Ashley didn't hear much complaining from Anna. She seems to be doing fineaaaaaah!

Anita held down a button on a remote in her hand, making the compressor behind Ashley whirr to life, sending air into the buttplug in her ass. Ashley felt her ring muscle being pushed open by the expanding intruder. Oh oh oh oh. Anita let go and the compressor died down in an instant. With the buttplug having stopped at roughly the size of the third rod Ashley had an understanding of the trajectory this was taking. Oh my god, she's going to push me open until I can take Theo in my ass!

“Keep breathing, Ashley. Relax and let it do its work.”

Having made sure that Danielle wasn't rushing things with Anna, Anita moved over to check on Tatiana and Madison.

"What seems to be the problem here?"

"I tell her relax but she not do."

“She’s working it like a stick-shift back there!” Madison complained.

“I am gentle as baby. No crying.”

"Madison, try to relax. You will never be able to accept your master if you keep clenching like that." Madison absentmindedly shook her head when Anita talked about being taken anally by her master.

"Gentle now Tatiana, I think you can go up one size if you use a lot more lube." Anita turned her head to Danielle and Anna. "Same goes for you Danielle, give Anna the next one and don't forget to lube up."

"Sure thing Miss." Danielle answered cheerily.

Wrrrrrrrr

Hearing Ashley's yammering made Madison grip tightly at the rod in her when Tatiana pulled it out.

Meanwhile Danielle had only somewhat followed her instructions. She stuck her face in-between Anna’s cheeks and began tonguing the woman’s asshole. Anita put her hand over her mouth, holding back a snorting laughter to keep her professionalism. Danielle let her drool dribble down onto Anna's butthole and twisted the second rod while she pushed it in, Anna gasped. "Ahhh dios mio!"

Danielle giggled happily from hearing that her new friend was enjoying herself.

Wrrrrr

"Oh my god!" Ashley scrambled to hold onto something, grasping the edge of her yoga mat she clenched her fists.

"Shh, shh, shh, shh Ashley, just breathe."

Ashley took deep breaths, in through her nose and out from her mouth. I will make it through this!

Their class went on for another 60 minutes switching places back and forth in the pairs to play with each other's ass. Ashley didn't get any rest with Anita steadily widening her opening with the inflatable buttplug. The last half hour Anita was primarily involved with Anna and Madison because she had deemed it necessary to focus on them to catch up with their classmates.

Ashley missed the soothing caress on her ass from her teacher and being told that she was a good girl when her plug widened her more. Losing the steady encouragement of Anita that had helped her through the unnerving experience of having her ring muscles stretched open, Ashley felt the need to find something else to give her the strength to endure it. She closed her eyes, trying to relax and set her thoughts on something other than her buttplug. In the midst of the turmoil of her emotions Ashley's mind honed in on Theodore. She saw him before her, smiling at her reassuringly, telling her that everything was alright. Whatever hardship she was experiencing he was going to be there to guide her through it. A calming sense washed over her when she imagined Theodore there with her, telling her how proud he was of her for doing this for him. I can do this for Theo. He will say that I'm his good girl when he enters my ass. But it needs to be trained before he can do that. It will fall to me to prepare it for him. Anita would say it's my duty to make myself ready to receive him.

Despite Anita’s helping hand, Madison had not managed to get past the second size. With some unwanted encouragement from Danielle, Anna had eventually managed to take the third one in her ass. Ashley gasped in relief when Anita finally let the air out of her buttplug and left her laying with her ass in the air. I made it, Theo is going to be so proud of me. The odd feeling of her situation being overshadowed by the relief of her strained ring muscle being allowed some rest.