Chapter 36
As Luke saw the wheel stop, he felt a huge wave of relief rush through him. “Truth from Lucy.”
Lucy didn’t take long to come up with a question for him. “Tell us one of your sexual fantasies.”
Having quite a few to choose from, he was happy with this question. “One of my sexual fantasies would be to wake up with a girl sitting on top of me with my dick inside of her, slowly riding me to wake me up.”
“I see. That doesn’t sound too over the top either.” Lucy said as he gave her the answer. Before turning her attention towards Ellie. “Now then. I guess it’s time for our newest member to take her first turn. Good luck Ellie.”
Ellie took the phone from Luke and placed it in front of her before hitting the spin button. “A dare from Josh.” She announced as soon as it came to a halt. She looked over to him and gave him a subtle wink, hoping that he would be nice to her after she had surprised him the night before.
“Seems like I have to give all the dares today.” Josh tapped the table with his fingers as he tried to make one up. “Okay, I think I got one for you that should not be too hard, seeing as this is your very first dare with us.” He cleared his throat before continuing. “So, your dare is to get in a doggy-style position on the table and either have one of us, or yourself see how many fingers that can fit inside of your butt. You have to start with one finger, then go back out and do two, until you say that you can’t go any further.”
Ellie looked surprised that he went so far on the first dare she was going to do. “Right, okay. I guess I’ll roll and see who will do this to me then.” She didn’t want to seem nervous. So without hesitation, she plotted in their names and spun the wheel. “Okay let’s see… It feels weird to say this out loud, but the one who will finger my ass will be…” She stared at the wheel spin and watched as it slowly came to a halt. “Luke.” She looked over to him. And he seemed to have lightened up a bit after hearing this.
“Here you go!” Josh held out a bottle of lube for Luke to use. “I’m sure Ellie would prefer it if you made this as comfortable as possible for her.”
Luke didn’t say anything back, but he did notice himself getting turned on again, after having lost most of his motivation when Ashley made him cum just a few minutes ago.
“Are you sure you are okay with this?” Ashley hesitantly asked her sister. “It’s not too late for you to back out of this game.”
“I’m fine sis, don’t worry. I said I wanted to be a part of this. Just try not to make a big deal out of this game okay? Can’t you just treat me like one of your fellow friends today? No need to make this awkward between us.” Ellie felt her confidence rise a bit after having to answer her sister. She wanted to prove her wrong, and without much hesitation, she got up on the table and placed herself in a doggy-style position. “Alright Luke, don’t make me have to wait like this for too long.”
“Right…” Luke got up and went over to the back of Ellie. He felt his cock start to grow again as he looked straight at her most private parts, now on full display directly in front of him. He squeezed out some lube and worked it around his finger before moving in on her.
At first he circled the opening a little to spread some lube around before slowly trying to push his finger in. He could feel her resist him a little bit before he got it in, only to hear her make a little sound as he pushed through. Then he slowly slid his finger further in until he had it all the way inside of her. “Everything okay so far Ellie?” He nervously asked as he pulled back out carefully.
Ellie looked back for a second. “I would lie if I said this wasn’t awkward as all hell, but go on.”
Luke applied a bit more lube to his hand and covered two fingers this time before going back in. It felt a bit more tight this time, but he got them both in here and pulled back out again. He made sure to cover three fingers in lube now as he slowly pushed against her opening once more. This time it felt much tighter as he slowly entered her. She also started to move a bit more as it probably felt like a lot, having this much go inside of her without even being warmed up to it.
He made sure to move slowly and with care, and he eventually got them all the way in. He didn’t even care that he was having a rock hard boner again at this point. Because this moment, was something he wouldn’t soon forget doing.
“Okay, four this time.” He said as he reapplied some lube before going back in again. He tried to get his fingers as tight as possible, but he could feel her clearly resist him as he tried to get them all in. After slightly getting his fingers inside of her though, she stopped him.
“Okay, stop!” She called out, and Luke slowly pulled his fingers back out. “I think that is my limit for now.” She took a few seconds to relax before getting back down off the table and back to her seat. She didn’t want to let the others know. But she enjoyed that dare more than she thought she would, despite it getting a little too uncomfortable and painful in the end.”
“You okay?” Luke asked, as he wiped the lube off his hands.
“I’m good yeah.” Ellie answered. “But I guess I’m not used to having that much in there.” She said with a fake laugh, trying to make light of the situation. “Alright next up is Josh then. Let’s see if we can get some payback for what you got me and my sister to do so far this round.” She winked at Ashley, trying to get her more on board with this. And this time she actually gave a little smile back. Maybe she was finally starting to come around to her being in the game with them.