Chapter 38
Hearing him laugh only made Ruby feel worse. She thought she was well underway in the first challenge, but according to him, she had only just been warmed up. His laugh ended shortly after it began and Ruby could hear a bottle being opened, followed by something cold dripping down onto her stomach.
"What is that?" Ruby asked.
"Just a bottle with some lubricant." He answered back.
Ruby could hear the man close the bottle back up and then he started using his hand to spread the liquid all over her pussy, before sliding two of his fingers deep inside of her, to make sure he got it everywhere. “My god, you're tight!” He said, again laughing to himself. "I guess they should have chosen someone with smaller hands for the next part then."
Ruby just stayed quiet, not wanting to say anything to make him angry.
Once he was done with her pussy, he moved his fingers further down, circling them around her ass hole to spread the lube all around it. Then suddenly and to Ruby’s surprise, he quickly slid one of his fingers inside.
Ruby couldn't stop herself from releasing a gasp just as he stuck his finger inside of her. She was expecting him to go slowly, so this took her by surprise. She tried to move her arms to cover her mouth, but they where locked up tight.
"Calm down. You won't get out of those cuff yet. Better not try and resist." He said, before slowly sliding his finger back out from her butt. "Let's see if we can get this thing to fit inside now."
Ruby felt her heart beat faster, Just what did he want to put inside of her? How big was it? She could hear him opening the bottle again, but nothing hit her body this time.
After a bit of waiting for whatever came next, Ruby suddenly felt something pushing against her butt, and it felt quite big. He kept pushing it harder and she started to feel the pain of this object, trying to force itself inside of her. "That fucking hurts!" She screamed out. Her ass hole kept widening as the object slowly went in deeper.
"Almost there, just try and relax. It’ll go easier that way." He answered back.
Right after he said that he gave it one last hard push, and it was finally all the way inside of her. The end of it was a lot smaller, but there was still something sticking out. It had to be some sort of butt plug from the way the shape felt.
Before Ruby even got time to catch her breath, he surprised her and stuck two of his fingers inside of her pussy again.
"Ah yes, i can feel the plug inside of you. But, this might become a problem for the next part, seeing how tight you already are." He said with a calm voice. "Time to see how much you can take inside of you.”
Ruby felt a chill go down her spine just as he said that. "What? What do you mean?"
Before she got to hear his answer, she felt him take the two fingers he had inside of her back out, before he started to push three fingers inside of her this time. Then four fingers, shortly after he took the three back out. She was really starting to hurt now, and he didn't even seem to care as he kept forcing his four fingers deeper inside of her. Ruby kept screaming out and trying to move her arms and legs, but to no success. She was completely locked down and under his control.
"All you gotta do is say the words and i'll stop." He said with a sigh.
Ruby refused to give up. Letting Kate down was not an option, they had come too far to quit at this point. How much more pain could he possible make her feel than what she was already going through? She bit her teeth together as she felt tears running down her face, out from underneath the blindfold. It was all or nothing now.
"Not giving up? Alright then."
She could feel him move his four fingers inside of her, before he started to force his thumb in aswell. He barely had any of them inside of her now, but he slowly started pushing them all deeper inside of her again, stretching her more and more the deeper he went in. Ruby had never felt such pain before, it felt like she was going to rip open. She kept screaming and crying as he kept forcing his hand deeper inside of her.
The man let out a deep sigh as he stopped moving his hand. "Doesn't look like it will fit any more than this, at least not without causing some injuries. If only you had had a bit more experience with bigger things before you came here, this might've been a lot easier for you."
Ruby gave him no reply. And shortly after, she felt him withdrawing his hand back out from her, still hurting. Then the butt plug followed right after, at least that thing went out easier than when it came in.
"Good job, i guess. You passed your first challenge. I'm going to unlock your cuffs now, but don't remove your blindfold, or get up, until you hear me leave the room."
The man left, and the door closed behind him. Ruby sat herself back up in a sitting position on the table, removed the blindfold and looked around her. Everything was the same as when she got in. The room was completely empty again. She still felt the aching pain that he had inflicted on her, but she got back on her feet and wiped her tears from her face. Taking a deep breath, Ruby walked over to the door leading to her second challenge, hoping that the next one was a lot less painful. Almost anything would be better than this.