Ch 15: Blue Indigo & Violet

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Note to reader: this chapter focuses on extreme anal insertions. If that's not your thing, please skip to the next chapter.

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It was about 6pm when Maggie, Riley and Katie arrived back at Katie's villa. Katie had ridden in a cage in the back of the utility van, still wearing her dog costume.

Maggie lowered the ramp and opened Katie's cage and handed Riley the leash. She was surprised, but clipped it to Katie's collar and led her into the house, following Maggie.

The three made their way to the spa treatment area where Maggie and Riley helped Katie out of the dog outfit. Maggie removed Katie's chastity belt and supervised her having a shower.

When she was clean and dry, Maggie had Riley insert a large plug into Katie's ass, then locked her chastity belt back in place.

Maggie handed Katie a robe and sent her to her suite to dress for dinner.

Riley felt energised by the day's events. She had loved being the dominant at the party and with Katie even though she started the day as a submissive puppy as well.

Maggie and Riley showered together, taking turns soaping and scrubbing each other. Riley loved the feeling on Maggie's fingers massaging shampoo then conditioner into her scalp. She wanted to do more, but Maggie said they needed to go to dinner.

They changed into spare spa therapy uniforms and joined Katie, Neith and Farah in the dining room for dinner.

It was always a bit surreal chatting with Farah and Neith. They had been at the party and were well aware of what had taken place. But, they chatted as though nothing unusual had happened. It was like they compartmentalised everything sexual that was going on and were able to act as though none of it had actually happened.

Riley never pushed it, but got the feeling they didn't want to talk about it. It was kind of like having a family meal during a crises no one was dealing with--it was just over polite chit chat occasionally including small hints about upcoming trips.

After dinner, Riley and Katie went to the bar alone.

"You're starting to really enjoy yourself, aren't you, Riley?"

"Yes. I am. It's all new and I'm still feeling my way around...but yeah."

Katie nodded.

"They seem to be good at figuring people out. At the party, I'd thought that girl Eesha was in hell with all that pig stuff. But, she was actually loving it."

They sat quietly for a few minutes.

"Do you know what's next? We still have a lot of time here."

"You know the dildos we've been...using...on you."

Katie went bright red, "yeah."

"There's um...3 more."

"Fuck! Are you kidding? I thought that one today was impossible. I don't think I can handle anything bigger."

"Well. There's three more."

"Are you fuck-ing kidding me? How big?"

"The next one is just a bit bigger than today. The last two are like...unreal. One isn't that big around, but is long. Like very long. The other one isn't very long but is huge around."

Katie took a drink, "fuck. So that's what all the stuff with my ass is...trying to...stretch me. Why? What for?"

"Maggie said Basma hadn't done this before. So, I'm guessing it's just something she wanted to try. There were 7 in total. These are the last 3."

"When...how soon will you be...uh...trying the next one?"

"I don't know. You know how it is here...you almost never know what's going to happen next. I think the next one--blue--could go in with some work probably soon. I don't know about those last two."

"Fuck. The plug in there now is pretty big. I guess Maggie is trying to keep me stretched out."

"I think so. I don't even know if this is possible..."

A few minutes later, Maggie came to get Riley.

"Farah is ready to go back," then she turned to Katie and smiled a bit menacingly, "we see you in the morning. Busy day tomorrow."

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Riley ended up chatting with Addie and Maggie in Addie's rooms, all wearing pyjamas. It felt like ages since she'd seen Addie and it felt good to be back in her company. She squeezed her tight when she gave her a hello hug.

The three of them sat on the couch, with Riley laying on Addie's lap, Addie stroking her hair softly.

"Malik Basma has more plans for you. But, she wants you to complete the rainbow challenge," Maggie said.

"I watched some videos online...I've seen girls fit things like this inside them. But, I have no idea how long they had to...work at it before they could do that."

Maggie told Addie something in Filipino which made her laugh.

"Malik Basma doesn't seem to care about time," Addie said with some humour in her voice.

"She very demanding," Maggie added. "She very happy with you. If you can get the last 3 inside Katie...she will be very very pleased. But, we must work quickly."

Maggie got up and left the room, returning a few minutes later with the largest two dildos--blue and violet.

She tossed the biggest one to Riley. It was over 3" in diameter and more than 10" long. It looked more like a giant butt plug than a cock.

Maggie was waving the other one around, making it jiggle in her hand. It was huge, but just seemed more...possible.

"I think we could easily get these in her pussy. But, her ass will be hard," Maggie said, looking at it thoughtfully.

"They just seem...too big."

Maggie slid out of her pyjama shorts and at the dildo on the floor, standing over it. She squatted down, facing away from the others. She gingerly lowered herself onto it and Riley watched her easily take most of it inside her pussy.

"That's not your ass," Addie said, laughing.

Maggie said something in Filipino and Addie got up and went to her bathroom, returning with a large bottle of lube.

"Eto na," she said, handing the bottle to Maggie.

Maggie rubbed lube on it and carefully squatted over the dildo and slowly lowered herself, using her hand to guide the tip to her anus. She pushed downward, sort of slowly bouncing on the tip.

Riley watched as she slid the first inch or so into her ass before stopping and standing up.

Addie clapped, "very good. But, not enough. If that's all we needed to get inside Katie, this would be easy."

"I got it started. I could have done more...just not all of it."

"Show us how much more."

Maggie frowned and looked at the dildo. She put a lot more lube on it, then squatted down again over it.

Riley and Addie moved over next to her--Addie crouched to get a better view.

Riley watched as she closed her eyes and concentrated. She sort of shook herself, trying to relax more. Then she pressed downward, sliding down until about ⅓ of it had disappeared into her ass.

Addie reached between her legs and started to rub Maggie's clit. That seemed to encourage her and she bounced and pushed down more forcefully.

She started making soft but determined moans with each thrust downward, getting louder and more forceful with each thrust.

Addie pointed her head, calling Riley over wordlessly. Riley figured out what she wanted and began teasing Maggie's boobs through her thin top as Addie began kissing her.

Maggie began fucking the dildo a little faster with deeper strokes. She was moaning, her cries muffled by the kiss.

She was getting closer. Addie broke the kiss and started saying what Riley guessed was encouragement in Filipino--short sentences that sounded like commands.

Riley kneeled down, pulled up Maggie's top and began suckling her nipples, teasing them with her lips, tongue and teeth.

Maggie let out a squeal and came, making a final hard thrust down onto the dildo. Addie pulled her hand away and kissed her softly.

Addie and Riley looked underneath Maggie--she had about ⅘ of the dildo in her ass.

They both smiled. Katie could do this.

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The next morning, Riley went again to Katie's villa and made her way down to the special rooms in the basement. Maggie had arrived earlier and had left a pair of tights out for her in the main room and Riley quickly changed into them.

Riley peeked carefully into each room, quietly opening and closing each door until she found them and silently entered, not wanting to alert Katie to her presence too soon.

Katie was bound laying on her back with her legs in the air, bent at the knee and secured to a bar suspended over the table. Her wrists were cuffed at her sides and her collar was chained to a ring in the table. She had an unusual harness that crisscrossed her body.

She was almost naked apart from her collar and cuffs--Maggie had already removed her chastity belt.

"Perfect time. I just getting her ready," Maggie said jovially. She leaned over and put a ball gag tightly into Katie's mouth.

For the first time since all of this began, Riley thought Katie looked actually scared. Her eyes were pleading, but she couldn't even mumble through the tight gag.

"She wore the big plug to bed last night. I only took it out a few minutes ago. Her ass should be nice and loose."

Maggie slapped the side of Katie's ass just hard enough to make a smacking noise.

Riley stepped forward towards her bound friend. There was a small table sitting next to exam table covered by a black cloth and Maggie's phone was attached to a tripod to film the proceedings.

Maggie nodded towards it and Riley pulled the cloth away to reveal the three dildos, a huge bottle of lube, a box of gloves and some other items.

Riley licked her lips. She'd been looking forward to this since planning it out last night and her wet pussy tingled with excitement.

She pumped lube onto her hand and rubbed it into Katie's ass, sliding two fingers into her butt. Then she pumped a huge dollop of lube onto the dildo and rubbed it over the length of it.

Riley moved closer to the exam table so Katie could see the dildo clearly.

"This is going in today. So, you can relax and help or fight it...and it won't be...nice. Got it?"

Katie nodded, looking nervous.

Riley stepped to the end of the table and put her finger into Katie's ass, then slid a second inside, rotating them slightly. Then she put the tip of the dildo against Katie's anus and began to slide it in.

Katie breathed in, holding her breath as the cock invaded her ass.

"Push more...that's it," Maggie said, encouraging Riley as she adjusted the camera to film what she was doing.

Riley kept up a constant pressure, twisting it slightly. She got it about halfway in before it stopped sliding in smoothly.

She picked up a large, powerful looking vibrator and set it against Katie's clit before turning it on. Katie gasped through the gag as the sensations hit her.

Riley held the vibe in place with her left hand, moving it in small circles, but keeping gentle pressure on Katie's clit.

With her right hand, she pressed the dildo further into Katie's ass. She'd press it in for a bit, then pull it out just a bit before pushing down again. She was slowly but steadily fucking it into her.

Maggie reached down and slid her finger across Katie's labia, laughing, "she loves this! See how wet she is?"

Katie's body suddenly went rigid, then shook slightly as she came hard. She moaned loudly through the gag.

Riley took advantage of Katie's body relaxing momentarily and was able to slip the cock deeper into her ass. But, she didn't let up with the vibe.

"I do that," Maggie took the vibrator and pressed it more aggressively against Katie. She moved it around, even shaking it with her hand making it harder for Katie's body to adjust to the sensations.

Each of Maggie's movements made Katie moan in response through the gag.

"If your other hole was available, this would be so much easier. Maybe I'll fill it with something?"

Katie shook her head no and Maggie laughed, "Pity. You would have enjoyed it so much more."

Riley picked up the lube and squirted a dollop next to Katie's anus. She pulled the dildo out a bit and rubbed the lube on it before pushing it back deeper into Katie.

It was almost in. Riley was pushing it hard down, but couldn't quite get the last 1/2" into her ass.

Then Katie's next orgasm hit her. Maggie's expert use of the vibe made her explode. She twisted as much as she could against her bonds, almost screaming with pleasure through the gag. Maggie was relentless, keeping the vibe on her clit, shifting it just enough to really push her over the edge and made her cum several times in a row before taking the vibe away.

As Katie came, Riley was able to get the last bit of the dildo in. The base was now firmly against her ass.

"It's in!" Riley practically shouted with excitement.

Maggie picked up her phone and zoomed in close to record the achievement.

"Hold it in. I get the next one."

Maggie set the vibrator down and picked up the longest vibe from the table, marked with an indigo ring. It was only about ⅔ the diameter of the blue striped dildo in her ass, but indigo seemed impossibly long. It was simply long and round almost like a snake, but the same diameter end to end with rounded ends.

Maggie began slathering lube along the first third of the long dildo's length then slid her fingers up and down the shaft, spreading the lube evenly.

"Now pull it out. Slowly," Maggie said to Riley.

Riley slid the large dildo slowly out of Katie's ass. As it started to slide out, Katie's anus helped to push it out. She watched slightly fascinated as the dildo emerged almost without any help from her.

When it was fully out, Riley set it on the nearby table. Her ass gaped lewdly, staying open, its ring pulsing slightly. She could sink pink inside her.

Maggie dangled the dildo so Katie could see it. Katie squirmed, looking genuinely scared.

"Ooomf...ooomf..." Katie tried to protest through the gag. Maggie just laughed, then slid the indigo dildo into the gaping hole. It was much smaller in diameter than the last one and went in easily.

Maggie handed it to Riley who continued sliding the snakelike dildo into her ass. It kept going and going into her, easily sliding into the space vacated by the larger blue dildo.

She paused only to add lube to the next part. Could this whole thing really go into Katie's ass? Riley had watched videos with Maggie and Addie. She'd seen women do this...but did they have to work up to it? Was there some special talent they had?

Riley kept sliding it in. It was only when it was almost entirely inside her when she hit resistance.

"How much is left?"

"Just about 5" or so...it's mostly in." Then, after a pause, "does all of it need to go in?"

"We need to pull it out...so maybe the last 2-3" is ok not going in...so just a bit more."

Riley gripped the end of it firmly with both hands and pushed. It was so close and she wasn't going to stop until it was in.

She pulled it back just a bit and edged it forward with slow but steady push/pull thrusts until there was only enough left outside Jatie for her to grasp.

"Perfect. Step back."

Maggie captured their success with the phone.

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Maggie told Riley to pull just a bit of the long dildo out, then said to Katie, "Now, you push it out."

Maggie filmed and Riley watched, almost fascinated as the long dildo began to slowly slide out of Katie's ass. Riley thought it looked like a long snake that just slowly slithered out of Katie's butt. It came out at a slow pace, then paused before continuing until the final but exited and the insanely long dildo fell to the floor. Then there was a long, slow fart as Katie's ass expelled air behind it.

Maggie giggled, then kicked the dildo to the side.

Riley saw that Katie's anus was still gaping like before. The long dildo had stretched it open and it looked like the indigo dildo would easily slide back in.

Maggie put the phone back on the tripod, adjusting it again for the best shot.

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Maggie pulled two blue surgical gloves from the box on the table and put them on her hands and pumped a lot of lube onto them, rubbing her fingers in and out between the fingers on the other hand.

As Riley watched, Maggie slipped two then three fingers into Katie's already gaping ass. She rotated her hand slightly as she slipped in her fourth finger. Then she tucked her thumb under her palm and pulled her hand tightly together, trying to make it as small as possible. Then she gently slid her thumb and the rest of her hand into Katie's ass as the bound woman gasped through the gag.

It was a bizarre site for Riley. Katie's asshole seemed to just...expand. Maggie's hand was fully inside her, with Katie's skin looking almost like a bracelet or something around Maggie's wrist. Her arm just kind of disappeared into Katie.

Maggie turned and twisted her arm a bit making Katie moan and whimper in reply. Then she pulled it out slowly, her fingers spread to make Katie's ass open as much as possible as she removed her hand from Katie's butt.

She smiled at Riley, "She very flexible back here."

She added lube to her fingers again and inserted two fingers from each hand and pulled her asshole open. It looked to Riley like she was going to rip her open, but her ass stretched fairly wide and stayed gaping when she removed her fingers.

She slid her right hand fully inside Katie's ass, pushing in until it looked as though half of her forearm was buried inside her. Then she pulled her hand out, again spreading her fingers to stretch her as much as possible.

Maggie then put all of her fingers from both hands inside Katie's ass. She could only get one thumb in--the other just wouldn't slide in.

"Only one hand. Not two. I think that is ok."

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Maggie removed the gloves and worked with Riley to change Katie's position. They had Katie sit up on the table and bound her arms behind her.

Then Maggie lowered several chains from the ceiling and attached them to Katie's harness. She raised the chains which pulled Katie upward, suspending her from the ceiling. Maggie finished by attaching Katie's thighs to her ankles, then pushed the exam table out from under her.

Katie was left hanging the ceiling in a squatting position. Maggie lowered her slightly so her waist was at eye level.

"Get the violet one ready."

"Ok." Riley picked up the behemoth--the largest dildo of the set. It barely resembled a cock, even though it had oversized balls at the base. It was more like a log with a round end--just long and wide--larger in diameter than the blue one, but not nearly as long as the last one.

Riley licked her lips. She wanted to see this go into Katie. The thought of forcing it into her made her wetter and tingly thinking about it. It briefly made her flush with embarrassment, second guessing herself about why this excited her so much. Was she becoming a sadist? The look of fear in Katie's eyes made it even yummier.

Riley set the dildo on top of the exam table and began rubbing lube across the surface, trying to cover it with the slimy fluid.

While she prepared the massive cock, Maggie put on another pair of surgical gloves and easily slid each hand one at a time into Katie's ass. They went in easily now. Maggie finished by pushing all of her fingers into Katie's asshole and pulling it open slightly.

When she removed her hands, Katie's ass remained open wide.

"Now put it in."

Riley lifted the giant dildo and with Maggie's help pushed the tip into Katie's ass. Despite all the loosening up, it wasn't going in easily with just an inch or two buried in her ass.

"Hold it there--don't let it fall out."

Maggie slid the exam table back underneath Katie and lowered her down until the cock was resting on the table and Katie's weight was pressing down onto it.

Maggie grinned, "Gravity will help us now."

Maggie lowered Katie just a bit more so that her weight was now resting on the dildo. Katie moaned through her gag at the new pressure trying to force the bohemoth into her butt.

Riley wiped her hands off on a towel and got the vibrator she'd used on Katie earlier. She set it to maximum, turned it on and began grinding it into Katie's clit. Katie jostled and squirmed at its touch.