The Challenge: Ch. 10

Since it wasn't a break, the porn never stopped. There wasn't a nice meadow to clear her head.

She laid on the bed in the spot Val had helped her to and tried to relax. But...

The instructions appeared on the main screen--

"There are 10 dildos by the left wall arranged from smallest to largest. Insert at least 3 into your pussy. If you insert any of the largest 4, you'll earn up to 4 days reduction in your contract. Each insertion must be larger than the one before it."

Several arrows appeared on the wall, pointing to the selection. Each dildo had its number on the bottom.

Cassie rolled slightly to the right and propped herself up on her elbow for a better view. The smallest was a slightly large dildo. But, the 10th looked impossibly large and anything from the 5th up looked incredibly challenging to impossible. She didn't think she'd be earning a reduction today.

"I'm going to have to just do the three smallest. These things are ginormous!" Cassie sounded slightly defeated.

Val's voice came over the speaker, "Would you like a suggestion?"

Cassie brightened, "I'll take any help you can give on this one Val. I don't see a way..."

"Ok. In front of the bed...on the left...you'll see a selection of butt plugs. Put in one of those then use the smallest dildo in that group. Then get bigger dildos until you can't put one in. At that point take out the plug. If you can almost get one in...try cumming to...ah...loosen things up a bit."

Cassie laughed softly. Val sounded like some kind of expert in this? Then again...maybe she was?

"Thanks, Val. I'll give it a shot."

Cassie walked around the room. Literally every toy she could think of was laying around here somewhere. The screens were each playing a single video across each wall, three different women inserting dildos that looked like they were in the 8-10 range. Was this some kind of twisted encouragement from Bradshaw or whoever was picking the porn?

She grabbed the huge lube bottle, a small bullet vibe and a medium sized butt plug and set them near the dildos.

"How far in do these have to go, Val?"

"A reasonable amount...it's not like exactly so many inches or whatever. But, like an inch or two won't do it. I'll put something on the screen if it's in far enough, ok?"

"Ok. Thanks."

Cassie picked up dildo #1. It was about 8" long and just a little bigger around than she'd normally go for--but looked ok.

She lubed up the plug and slipped it easily into her ass. It was a comfortable size. She wasn't a huge plug fan, but didn't mind them.

She lubed up dildo #1. She laid back on the pillows, spread her legs and slid it easily inside herself, nice and deep. She was comfortably full, the dildo

A giant thumbs up appeared on the front screen with the words "Success. 1 of 3."

Cassie studied the selection intently. One to 3 were easy...4 a maybe...anything larger seemed unlikely. But, she'd try Val's suggestion.

She wanted to complete the task, so she decided to do three to be safe.

"Can I do more than 3, Val?"

"Yeah. No upper limits. Just at least three and each one bigger...so you can't try 10 then do 6 or whatever."

"Ok."

She picked up #3. It looked a bit thick, but not crazy. Again, she slathered lube on it, lay back on the bed and eased it into herself. This time in pushed hard against the plug in her ass. She felt very full and wondered if she could do muck more.

The screen flashed: "Success. 2 of 3."

She slid the dildo out and looked at the selection. She decided to try #5. If she could squeeze it in, she'd be done and would know of anything larger was possible.

She put a massive amount of lube on it, taking care to rub it from top to bottom. She pulled out the plug and leaned way back on the pillows, raising her hips and pressing the head of the dildo against the opening of her pussy.

It seemed huge. At least 10" long and a little biger around than her wrist. The head was slightly bulbous, so getting the tip in was the hardest part.

She pushed herself against it, setting the base at an angle so she could push against the bed. She could feel every inch of its journey into her. Her lips parted slowly and it slid into her pussy, pressing the walls as it went.

She stopped with it about halfway in. It felt huge inside her. She took a deep breath and tried to relax. She leaned forward onto it and felt it achingly slowly slide deeper into her. When she thought it was deep enough, she spread her legs and pointed towards her pussy.

The screen displayed: "Success. 3 of 3. Challenge complete. Zero reduction earned."

Cassie pursed her lips, thinking. Could she manage #6? It looked much bigger than the monster inside her which seemed to compress everything and full her completely.

"I'm going to try...no promises, Val."

"You're fine either way, Cass."

Cassie squeezed her pussy, making the monster dildo slide out of her. She squeezed tighter a few times and it expelled itself a little faster. She actually enjoyed that sensation. It was too much going in, but the head nicely rubbed her pussy walls on the way out and left her feeling very empty when it finally was out. It felt like it had taken more than itself out, leaving a vacuum behind it.

She looked at the four largest dildos. Number 9 and #10 were just insane. Maybe if she was stretched out after having a baby. She shook her head.

She picked up #6. She drizzled a huge amount of lube into it. Like last time, she rubbed the lube across every inch of it. For good measure, she pumped a big dollop of lube onto her have and rubbed it over her labia and sliding as much inside herself as possible.

She again laid back on the bed. She put the head against her lips and pressed hard against it. It barely entered her. Her body was fighting her, pushing back against it.

The video caught her attention. A tiny blonde woman was squatting over a dildo that looked even bigger than #10. She was basically sitting down onto it.

She decided to copy her. Cassie got up on her knees and positioned the monster dildo beneath her, its tip against her lips.

She bore down onto it, putting her whole weight down onto it. She tried hard to relax her muscles. She tried to slowly fuck it into her pussy. She'd push hard, then relax and let her body push it back out slightly. She kept repeating the process, making very very slow progress.

She picked up the bullet vibe and began rubbing her clit with it. The sensation helped her, making her body more receptive and making her even wetter.

She had a small orgasm and felt the dildo slip into her more easily. She kept using the bullet and eventually, it was so far in it felt like it was rubbing her cervix. She didn't think she could take any more of it inside her. The bullet gave her another small orgasm, then she dropped the bullet.

"Val? Val...is this...is it deep enough? I..."

"Yes. That's enough, Cass. Are you ok?"

"Yeah, but...that's...no more...I'm taking it out."

"Ok, Cass."

She raised up her hips, lifting the base of the dildo off of the mattress. Without doing anything, her body began to expel the mammoth dildo.

She placed her hand on her lower tummy and could feel the thing inside her. She shook her head...this was crazy.

It seemed to take ages for it to fully exit her body. She fell back onto the bed feeling achingly empty. She was almost craving something inside her. She'd never felt so empty. This was bizarre.

The screen displayed: "Success. 4 of 3. Challenge complete. One day reduction earned."

"Are you done, Cass?"

"Fuck, yes. No more, Val."

"Ok. I'm coming in.

The videos switched back to the calm, breezy meadow.

The door opened and Val helped her get up and get to the couch in the outer room. She handed Cassie a clean robe and a water.

"How are you doing?"

"I'm exhausted. But, ok I guess. How much time is left?"

"You actually finished a bit early. So you can take a 30 minute break if you want? Rest here anyway and I'll get things ready."