Again, I am pressed firmly against my sister’s breasts, Kaylee called Jennifer back letting her know there had been a change of plans. I have been sitting silent for the past thirty minutes during the car ride so there wasn’t really much I could do. Kaylee’s nipple was taking up my entire view and it didn’t help that it has long since been erect and pressing against my face. If Kaylee felt at all uncomfortable, she gave no indication of it as she continued to chat with Jennifer about various different things. I have yet to see this Jennifer and don’t really know what she looks like. I do know she has this huge fixation with me based off of what she has been telling my sister. I wonder if Kaylee will ever tell her about me and my situation. Based off of their conversation today, I managed to pick up that we were going to the mall. Other than that, I have no idea what the day has in store for me. So I make myself comfortable and doze off.

Kaylee and Jennifer arrive at the mall and run into Kaylee’s mom. Kaylee felt that it was odd that her mom didn’t mention that to her but dismissed it as her just needing a relaxing day after a long work week. Kaylee has always been the most understanding of her two daughters. Drake, well, Drake was just Drake.

“Hi mom,” Kaylee says while approaching her in the food court, “what are you up to today?”

“Hey sweetheart, and oh nothing, I was just trying to get a little bit of time to myself to relax is all. Hey Jennifer, I hope you two have been keeping out of trouble.”

“Oh yes ma’am Ms. Dobson. Kaylee is certainly the one you should be worried about,” Jennifer says as she winks at Kaylee and nudges her shoulder.

“Oh hush you. Yeah mom we have been staying out of trouble. Just came here to shop around and get out of the house.”

“That’s fine hun. Just remember to be home before too late. You know how worried I get when you’re not home.”

“Yes ma’am. I will be sure to keep to my curfew.”

“Good girl,” Ms. Dobson says as she leans in to kiss Kaylee on her forehead, “I Love you sweetie, see you tonight.”

“Love you too mom.”

At that, two parties parted ways and Kaylee and Jennifer were off to go shopping.

I woke up to a sudden jolt at my side. I have no idea what that was but I heard the voices of my sister and my mom. Upon hearing my sister and mom part ways, I hear Kaylee mention shopping. That’s when I hear Jennifer say,

“Hey Kaylee! Let’s go in this one!!”

“Jen, come on now girl, you know that is a lingerie store. I don’t even know if we can walk in there because they actually sale toys there. It’s practically porn central!”

“Aww please Kaylee!! Just to try on some sexy stuff? You know we don’t have to buy it, and I don’t get to wear things like that often. And you and I both know we can pass for eighteen year olds.”

Oh no.. What if Kaylee decides to try on things? What about me?

“Awww okay, I guess we ca—“ Kaylee stopped in mid-sentence.

She didn’t stop because she thought about me though. She probably stopped because after I heard her give in, I immediately started letting her know I did not approve. So I started punching, kicking, and biting and her nipple.

“Ahhhh,” Kaylee breathed in really sharply.

“Uh.. Kaylee are you alright?”

“Ye… yeah. I am fine. Just had some chills run through my spine that’s all; let’s find some things to try on.”

At that Jennifer turned around and led the way. While Kaylee looked around to make sure nobody was looking and bit her lower lip at what she was about to do.

“So you want to play that game huh Drake,” she says very softly to herself, “then how about this?”

At that, she take her right index finger and presses me and my whole body into her nipple and starts rotating it around in a slow sensual motion.

“Kaylee! What the Fu—faf, what the fuck are you do—ffigng?”

I was constantly and rhythmically being pressed against her nipple and she wasn’t letting up. I was saved by the bell after Jennifer stopped at a rack of clothes. Kaylee then stopped her massaging and just gave me and her nipple a soft playful pat. I did not expect that from my sister. Of course, I guess she didn’t expect what I did either so I guess that makes us even.

“Oohh Kaylee, you HAVE to try this on after me!”

Jennifer runs up to Kaylee and flashes a very skimpy bathing suit that was lime green with a frog on the ass. The words under the frog said, “Croak for me.” It also came with a matching top where each top cup was an eyeball.

“You know you how cute frogs are Kaylee, and you know you can’t resist how cute this set is.”

“Jen, that looks so tacky though.”

“Yeah but, just for to try on okay?”

“Fine, I’ll try them on with you.”

Smiling brightly she excitedly runs into the changing area to get changed. Upon coming out, Jennifer was envious of her friend because of how tan her skin was. Especially compared to hers. Her dark brown hair also seemed to perfectly curl down to her shoulders.

“Well, what do ya think?”

“Well.. It’s different that’s for sure,” Kaylee said while trying not to smirk at the two eyes on her breasts staring at her.”

“Okay your turn! I will leave it in the room for you!”

Kaylee took this time to pull me out and have a small talk.

“How are you doing in there bro?”

“I’m good, just been hanging in there.”

Looking at me slyly she says, “You seemed to have found something to occupy yourself with,” as she points down at her nipple.

“Oh about that.. I just was trying to tell you I didn’t approve of the trying on different clothes thing.”

“Oh bro, I am sorry, but you know a simple tug would have been just fine. You.. You can’t be doing all of what you did earlier. Okay?”

“Well, why not? It seemed to have worked as getting your attention.”

“Yes. But.. But you just can’t do THAT anymore. I can’t explain why but just don’t do that okay?”

“Okay agreed dear sis.”

Smiling for only a second before it instantly fades into aggravation, “Shit where am I going to put you? If I tried on the top with you in there she will definitely see you through it!”

“Oh gosh, sis I don’t know. Maybe leave me in your pock- wait you don’t really have pockets. Shit.”

Looking down at me with an empathetic look she slowly shakes her head and says, “I am sorry bro but there is only one other place I can put you.”

Kaylee things to herself a moment and realizes that after that little stunt that Drake pulled earlier with her nipple, she was much too aroused to let Drake go in the front of her panties. Not that he would accept going there himself either. Biting her lower lip nervously, she knew what she had to do. Regardless of what Drake says.

“Well where sis?”

We were interrupted by Jennifer heading out of the changing area and Kaylee quickly shoved me back in her bra.

“Whew, it fit pretty tight on me. But you’re about my size right?”

Kaylee actually was a little bit bigger than Jennifer, which wasn’t going to work out in my favor at all.

“Yeah close enough,” Kaylee says while heading into the dressing room.

Once she striped down completely naked, she had me sitting on the bench behind her as she adjusted her top. Upon seeing her breasts about to fall out at any moment I shook my head at her and said,

“Yeah there was no way I was fitting in there without suffocating to death.”

“Yeah I know,” She replied nervously as she pulled up her bottoms. They fit perfectly around her bare ass conforming to its perfect shape.

“That’s why I have to do this.”

“Wait what??”

Without another word she picks me up and starts positioning me behind her while pulling back the strap of her bottoms.

“Wait, sis. There has to be a better place than there. Please. Don’t do this. How about your hair?! Or just rest in your hand?”

Kaylee wanted to admit that her brother made some good suggestions. But in a way, she WANTED to do this. She wanted to feel him squirming around behind her. She knew he was her brother. But they were always so close, and even though she knew she would never have sex with her brother, or develop feelings like that for him, she still wanted to experience that feeling. While he still assumed she was innocent and just doing this ‘for his own good’. She would never hurt her brother or abuse him either. She is just curious. So without another word she simply drops him into her bottoms and lets them snap shut.

All I remember is trying to reason with Kaylee and then feeling butterflies in my stomach. Looking down I saw what her decision was, and I do not like it one bit and there is nothing I can do about it. I realize how helpless I am to stop my sister from doing this to me despite my pleas. She had a point though. Her top was way to small it would have given me away instantly so maybe she is doing what she thinks is best. As I fell I tumbled down and bounced off of each of her ass cheeks back and forth with progressive grunts and yelps until all light disappeared and the bathing suit material pressed against my back and catapulted me forward straight between her massive ass cheeks. Being only a half an inch tall, each of them were like two giant sheds or small cabins. I am not sure how far the material launched me inside, but I do know that her ass cheeks enclosed around behind me and I was met with an intensive smell which didn’t come as a surprise to me. I’ve experienced Kaitlyn’s ass as well, but with the adrenaline and activity that ensued I didn’t have much time to reflect on the smell like I do now. Breathing was also getting hard due to her ass cheeks pressing inwards on me and lack of circulation. All I could do to ease the pressure was to turn my body outward and allow myself to be spread eagle, with her two ass cheeks sandwiching me. Then she started walking and things became ten times worse. With just one step, the cheek in front of me shifted upward with tremendous force while the one behind me stayed in place. The sudden jerking and squeezing motion caused me to let out a low grunt. Then her other leg moved and the cheek behind me shifted upwards, while the front one shifted downwards essentially grinding me in between them. My dick was getting hard from the simulation and I could feel myself blush knowing this was my sister. But she kept walking. How much further until she reaches Jennifer? I was brought on the brink of releasing my load all over my sister’s ass when she finally stopped. Attempting to recover, I heard Jennifer’s voice say,

 “Ohhh Sexy!! And look at your ass! It fits it waaay better than mine!”

With that she reached over and gave Kaylee’s ass a big slap.

I was slowly starting to recover from getting off to my sister’s ass when I felt a sudden jolt and then felt tons of tiny tremors reverberate along my sister’s ass cheeks. This threw me over the edge and I came all over Kaylee’s ass cheek while watching my cum drip down and disappear among the rest of it below.

Exhausted from what just happened, I just collapse and let my sister’s ass cheeks hold me in place.

Kaylee had sensations of her own. After snapping her bottom’s shut, she immediately felt the tiny form of her brother settle in between her ass cheeks. It surprised her how far he got wedge in. She started walking and immediately felt her ass cheeks conforming and squeezing her brother. She immediately got wet from this and kept walking trying to imagine what it must be like for him. As soon as she reached her friend Jennifer, she was complimented on how well her ass fit and right as she was about to thank Jennifer for her compliment, she gets slapped on the ass. All she could do was make a nervous smile after feeling her brother get jostled around yet again.

“Alright Jen I think I am going to go change back now.”

“Alright girl, hurry back!”

Kaylee walked back to the dressing room trying to savor the feeling of her brother before she had to take him out.

Reaching around her back she chose to take her bra off first. Then bending down at her waist she feels her brother start slipping out of her ass cheeks. Once she slides her bottoms down just a bit, she sees his tiny body fall out and land in the hammock of her bottoms. She was about to ask him if he was okay when Jennifer barges in and says,

“Hey sorry Kaylee I just want to try that suit on one more time. My mom wanted me to show her a picture of me wearing it.”

Kaylee panicked, and not wanting to give away Drake, she just let the bottoms fall to the floor.

“Uhh.. Sure.. Jen.”

“Oh don’t worry it’s just me girl. You can stay in here with me if you want I’ll just be a second.”

“Yeah.. I’ll just wait right here,” Kaylee says while putting her normal clothes back on.

“Fuck,” Kaylee says In her head.

“How could I have let this happen? What the hell is going to happen if Drake gets discovered by her? How am I going to explain it to her? How am I going to explain it to Drake?”

Kaylee curses herself privately as she watches Jennifer position herself over the bottoms and prepares to lift them up.