When morning came, Drake felt himself being lifted up suddenly. It startled him, but when he opened his eyes to see Kaylee he was much more relieved. Knowing what she did for him, he felt like he should say something to her as gratitude.

“Thank you,” Drake said passionately. He knew that was all he had to say and from the look on Kaylee’s face, he could tell she knew he was genuinely grateful for what she went through for him. Kaylee herself knew she couldn’t blame Drake for what she did. She was the reason he ended up in the whole situation he ended up in. She didn’t have to bring him along, but he was her brother and she was afraid of not being there for him at all times. Kaylee decided she should speak too.

“I know you feel bad for what happened last night Drake, but please don’t. It was not your fault that I had to get you out of that mess. It was my own fault. I still want to say more to you, but we need to wait until we are back home first okay?”

Drake simply nodded. This time, Kaylee placed him back into her bra cup again and went out to see if Jennifer had woken up. She walked in the kitchen to find a note that said,

“Hey girl! I know it’s rude of me to not be here when you wake up, but I had to head out with my mom this morning.  She said she had to go to town for a few things and wanted me to tag along with her. Help yourself to anything and I’ll just catch ya later. Love you! Kiss Kiss!”

Kaylee thought about calling her mother to come get her, but she wasn’t aware if her mother was awake or not and decided to walk instead. They didn’t live too far apart from each other, it’s just that Jennifer was always too lazy to simply walk the half mile down the street to Kaylee’s. It didn’t take long for them to arrive but Drake had gotten drenched in her sweat that drizzled down into her bra. Upon walking up to the front door, she saw Brad, Kaitlyn’s boyfriend, limping out of the house and head to his car.

“Huh. Strange of him walking like that Anyways,” Kaylee said to herself as she entered the door.

She passed by Kaitlyn’s room to find her passed out on the bed, and her mom was also passed out on her bed. Heading to her room, she walked in and locked the door before sitting on her bed and taking Drake out of her bra.

“Okay Drake, we need to talk.”

“Okay sis I’m here.”

“Right. So you are aware of how vulnerable you are at this condition correct?”

“Y…Yes.”

“And you also know that if you’re not careful then you could easily be stepped on, or worse?”

Drake could see where this was going and he just simply nodded his head in agreement.

“What happened last night was not your fault, but I Love you. I care about you as my brother, and more importantly as my dungeon buddy. So we need to try and find a way to keep you safe. I am not sure how yet, but I wanted to talk to you to make sure we are both in agreement.”

“Of course sis. I know you care about me. I don’t want to be killed out here for sure.”

Smiling, Kaylee nodded and said, “Good. Well that’s settled.”

Kaylee then bit her lip as she had an idea in her head.

“Could I actually convince him to do that? No! He wouldn’t would he? I certainly would get amused by it. Maybe even a little turned on. Wait.. This is my brother! I can’t be turned on by him right? I mean, I guess he doesn’t have to know either. Right? Fuck it, let’s see how far this can go.”

Kaylee then looked down at her brother with a sarcastic look.

“So little bro, I think you owe me one from what happened last night don’t you agree?”

“Y..Yes Kaylee, it must have been hell for you. I’d do anything to make it up to you I promise.”

Kaylee felt a tingling in her groin as she smiled and said, “Good to know.”

“So.. W..What do you need me to do?”

Kaylee didn’t answer as she slowly dropped her pants to the floor along with her panties. She then held Drake in her hand as she crawled onto her bed and laid on her stomach. She then held Drake right in front of her face and spoke.

“I want you to kiss my ass.”

“W.. what?”

“Yes Drake, I want you to kiss my ass. It is extremely sore from last night, and I think it’s the least you could do really.”

Oh God did I really just say that to my brother? This.. This is so erotic. I am about to really make my brother kiss my ass. Maybe I can make him do a little more.

“I don’t mean just my ass cheeks. I mean I want you to kiss my actual ass. That’s the part that hurts.”

“Oh God sis. I…I don’t know, I mean you know I really feel bad for last night but… but this is kinda crazy. I mean you’re my sister.”

“So? You’ve been in my vagina before too and I didn’t complain.”

“Yeah, but that was for my own good. You did that to protect me from your friend.”

“While that is true, I did take an 8 inch vibrator up my ass also for your own good.”

Oh my gosh look at him. He is really going to do this right now isn’t he?

“Oh… Ok… I will do it. Just… Just between me and you okay?”

Kaylee was completely wet at this point and her heart was pounding. She gave Drake a big smile and simply said,

“I promise that me and you will be the only two that know about this.  Let me put you in place.”

Reaching out behind her, she used her hand to make sure her ass cheeks were spread apart enough to allow Drake to fall through and get to her asshole. Taking drake by one arm between her fingers, she pulling him back behind her and dropped him in. She immediately bit her lip and slammed her face in the pillow to blow out some air at what she just did. She could feel his tiny feet walking over her asshole. She started feeling him planting tiny kisses on her ass and she couldn’t believe that she really convinced him to do that.

“Oh good. Just like that Drake, just don’t stop until I say so okay?”

She could hardly contain herself. Another thought rushed into her head and she had been fighting it off ever since she placed her brother back there. However, Drake was doing a great job kissing her. He was doing too good of a job and Kaylee finally gave in to her idea. She bit her lower lip and looked over her shoulder as she took her other hand and slid her index finger into her crack, she was digging to find Drake. He had no idea her gigantic finger was hovering over him, and with one single push, she forced her finger down on Drake and in a split second he disappeared into her asshole.

“Fuccckkk. This feels so fucking good,” Kaylee whispered to herself. She pumped her finger in and out of her ass being careful not to be too rough. She got up from her bed and quickly ran over to her drawer and got her dildo out and ran back to her bed and was laying on her back. With one hand fingering her asshole, the other started inserting the dildo and Kaylee began pleasuring herself at the thought of tricking her brother into being in her asshole. She took care to be as quiet as possible because she didn’t want Drake to know she was enjoying this.

Drake was confused. He didn’t understand why she shoved him into her ass but he assumed she was punishing him for it. He felt like maybe this was her calling it even and decided he should try and make amends. The only way he felt he could do that was by massaging her inner anal walls in the hopes that she would take some form of thanks from it. He had no idea how right he was. Kaylee felt his tiny body rubbing at her inner walls and mistook it as him trying to find a way to escape. This made her double her efforts and in no time she had a massive orgasm.

Collapsing onto the bed, she laid there exhausted for a second and then reached behind her to pull Drake out. She slid him out with a sharp slurping sound, and pulled him up to her face.

“Thank you, bro, I feel much better. You actually are a good Dungeon Explorer after all,” Kaylee said with a wink.

“Well. I mean, it wasn’t so bad and it was to pay you back so I understand.”

Oh my Fuck. Did he really just say he understood and was okay with this? And that it wasn’t so bad?!!!

“Well I am glad you think so. But I think it’s time we get you cleaned up. And me for that matter.”

Kaylee took Drake in her palm and headed to the bathroom to take a shower.

WARNING: Male content ahead!! Turn back unless you want to read this!

*The night before at the Dobson’s*

Poor Ricky was still tapped to the strap on that had just got used on Mrs. Tully and was now in the hands of Kaitlyn. He couldn’t get Kaitlyn’s attention and got confused as to why she was putting on the strap on if she was with her boyfriend. Kaitlyn walked into her room with the strap on already mounted on her. Ricky could see on her bed and saw that her boyfriend was tied to the bed bent over at his waist and butt naked. Kaitlyn walked over slowly to her boyfriend Brad and commenced to smacking his ass as hard as she could with a leather tassel she had in her hand. Brad grunted in pain, but it sounded like he was enjoying this. Ricky was unfortunately still confused as to what the hell she was doing. He had not had any experience with experimenting with sexual acts so he was amazed that the poor dude could even enjoy what was doing to him. He was still wondering why she had the strap on until he saw her reach for a huge bottle and tilt it directly over the tip of the strap on, directly above Ricky’s head. Ricky read the huge letters on the side and saw it read “Anal Lube.” His heart dropped through his gut when he realized what the strap on was for. By then, he was drenched in anal lube and had Kaitlyn’s hands smearing it all over him and the strap on before taking her fingers and shoving two of them in Brad’s ass and getting him ready for the gigantic strap on she was about to pummel his ass with. Once she got his asshole good and lubed, she took her fingers and shoved them in Brad's mouth forcing him to suck on them while she took her other hand and grabbed her discarded panties that were on the floor. Taking her panties and balling them up, she forced them into Brads mouth and then took ductape to seal them in place. 

"I really hope you're ready Brad. Because I am going to fuck your brains out BETTER than you have ever fucked me."

Kaitlyn then took the strap on in hand and was positioning it in place right in front of Brad's asshole. Ricky's cries for help fell on deaf ears and nothing worked. Soon he was face to face with Brad’s asshole and then Kaitlyn took the tip and simply prodded it gently before rubbing the tip in a circular motion along Brad’s asshole. Ricky unfortunately was being shoved face first into it and being smeared all over it.

"No!! Pl--hmmffffhmmff. Sto--Hmmggfdf"

If Ricky ever took time to think about the upsides to his situation, it would be that Brad had hardly any hair at all. Kaitlyn wasted no time in her desire, so she shoved the strap on all the way inside Brad straight from the start. Ricky immediately started screaming and soon found out it was a terrible idea. Brad's asshole wasn't necessarily cleaned out before they started and Ricky soon found his whole body shoved deep into a wall of feces that Brad had yet to discard.

"Nooo!!! Wh-ghurrffllffhdfd"

Ricky was struggling to breath due to lack of oxygen and the fact that Brad’s ass muscles were squeezing so tight everywhere. He obviously never tried this before and was soon regretting it. Ricky could hear Brad's muffled screaming in pain, but Kaitlyn's panties proved to be a good dampener.

"Stay quiet you pussy!" Kaitlyn said as she slapped Brad's ass.

Kaitlyn started fucking Brad's ass in slow, powerful pulses as Ricky was being unknowingly shoved as hard as possible into a giant mound of shit. One thrust that she did caused some to encase around the tip of the strap on and leave a thine layer stuck to it, causing Ricky to struggled for air. Brad was almost limp from exhaustion when Kaitlyn did one final thrust. She then unstrapped the strap on to her body and left it inside Brad.

"Be still you bitch, I'm going to take a piss."

Ricky was covered in residual fecal matter from Brad’s asshole and was now suffocating from lack of oxygen and started blacking out. 

"This is it. I am going to die in some random dude's asshole." Ricky thought to himself.

Kaitlyn returned and took the strap on out of Brad's ass. Ricky felt a rush of fresh air and was just happy that he was still alive. He didn't have much time to celebrate because Kaitlyn then took the strap on and forced Brad to suck on it to help clean it off. Immediately Ricky was forced against the tongue of Brad and started feeling it rotate around the dildo and he felt sucking sensations as Brad was trying to do his best to clean it off. Probably in fear of what Kaitlyn would do if he did a bad job. Ricky was happy that he at least had some of the shit cleaned off of him but he was still clearly covered in residual shit. After forcing Brad to deep throat it for a while, she finally took it out of his mouth with a slurping sound.

"Damn, you can suck almost as good as I can. I'll be back for you later."

Kaitlyn went to the bathroom to wash it off for her mother before she arrived back home. She was almost done but there was this certain spot she just couldn't get.

"What the hell? Come of you peice of shit!"

Kaitlyn held the strap on closer to her until she saw that it actually wasn't a piece of shit.

"Well I'll be fucked. You aren't Drake so who the fuck are you." 

"I..Im-"

"Nevermind it doesn't matter. W--why the fuck were you on my mom's strap on?"

Kaitlyn then suddenly realized that he must have been on the strap on the entire time.

"Wait.. Ha...Hahahah.. You mean to tell me you were on this thing as I was fucking my pussy boyfriend? Holy shit I bet you enjoyed his ass. You look like the type of pervert that would. Being as you somehow strapped yourself to my mom's strap on. I bet you were trying to get some of her pussy huh you little shit?" I would shove your perverted ass back up Brad's ass but he is leaving in the morning and I don't want to forget about you. I already lost Drake and haven't seen him again and I am not about to lose on an opportunity to have a tiny ass bitch to be my slave."

Ricky's heart dropped. He wasn't going anywhere. He wasn't going to see his family ever again. At least she wasn't going to kill him but now what was the point? He would have no life anymore.

"I'll tell you what. I'll put you to the test. I won't keep you if you're a total pussy. But if you can last for a day in my mom's work heels, then I promise that I'll keep you and you will be my slave got it? If you're a pussy, then you are dead anyways so it doesn't matter what happens to you if you can't handle it. So what do you say to that?"

"Uh... Ye--"

"Of course you agree. So let's get started shall we? I'll check for you after my mom gets home and if you're still in one peice then you will get the luxery of cleaning food out of my teeth for tomorrow."

Kaitlyn took some small strands of duct tap and tapped his arms to his sides and tapped his ankles together. She then went into her mom's room and picked up her mom's work heels.

"Ok pipsqueak, which shoe do you want?"

"T--"

"Haha fuck that it doesn't matter. Here you go!"

Kaitlyn took Ricky and tapped him face up inside the shoe with his head laying on the toe end. Kaitlyn stepped back to admire her work.

"Hmmm. Seems fine to me. Now let's see how noticable you are in there."

Kaitlyn took her bare foot and slowly slid it inside the heel. Ricky immediately saw her black painted toes coming at him and tried bracing himself. Kaitlyn's toes perferctly molded around Ricky's head and he was wedged between her big and second toes. Her feel actually felt really soft. They were amazingly smooth, and didn't smell at all. Kaitlyn herself was actually a really beautiful girl, but she was crazy and sadisitc according to Ricky. Kaitlyn then retracted her foot and said,

"Well you can tell you're there. But no so much that you'd have to check what it is. You actually feel good in there. You make a great foot massager, I'll keep that in mind if you make it back." Kaitlyn gave Ricky a wink before turning around and heading out. Before she left, she simpy stoped and spoke from over her shoulder,

"By the way, my mom's feet may look sexy, but they are hideously smelly. So just make sure the smell doesn't kill ya."

Kaitlyn giggled as she walked out of the room.

Ricky tried to go to sleep but he was uncomfortable, smelly, cold, and he couldn't turn over. He had a long night and an even longer day ahead of him.

He cried himself to sleep that night.