It has been going on for as long as anyone can remember, Applejack and Rainbow had always been making bets and daring each other ever since they first became friends. It first started off with a few simple bets and back then the prize was only a small snack or some change, as the year progressed it started to upscale.
I started school at the same time they did so I watched them, back then when one of them lost a snack in the bet I gave them one of mine as I often had plenty to spare.
As the years progressed I started to become close to Applejack, she was very friendly and open with me. We were just simply friends and thanks to that the competition they had seemed to die down for a bit, Rainbow seemed to have found a way to use this to her advantage when they resumed their competition.
I still remember one time at lunch when it happened, I was eating outside in the sunlight. Applejack sat down on the side a distance away from me, I thought I was seeing things when I noticed the way she was sat. Her legs were open and I could see up her skirt, her green panties were visible for me to see.
After that she had difficulty being around me, Fluttershy told me later on about the bet Rainbow made with Applejack. She made Applejack flash her panties at me due to beating her in their competition.
A few weeks later it seemed like Applejack lost another bet, I was stunned when she came up to me and kissed me.
Not just any normal kiss either, she went full on tongue in my mouth type kiss. I still remember seeing the redness on her face when the kissing finally stopped, her eyes could barely look at mine when we stopped kissing.
That was nothing compared to what I found a few weeks later, I was returning to school from my trip to the hospital. It was just a routine check-up to make sure I was clear from a hereditary illness, I made my way back to school and I saw something tied to the lamp post outside the school.
It was Applejack who was tied upside down, her arms were tied behind her back.
Her legs were tied to each arm of the lamp causing her legs to stay open, but that is not what made my jaw drop to the ground with my eyes popping out of my skull.
She was completely naked, I temporarily broke my staring at her to look at my watch. Lunchtime was nearly over and the front of the school will be active, I had to help her before that happened. But as I started to walk over to her my mind kinda disconnected from my body, I could barely hear her as I drew closer.
Her body was right there in front of me, I looked at her pussy as it trembled in the cold air. Her blonde pubes highlighted it quite nicely, she squirmed as my hot breath accidentally blew onto her pussy. I could feel my cock getting hard in my pants as it made a bulge in my pants, right now it was an inch in front of her face. My hands grabbed her waist allowing me to feel the softness of her skin, my head started to move down to lick her out before I regained control of myself.
I looked down at Applejack “sorry I didn’t mean to”.
She shook her head “it’s ok partner” she said. “Listen if you help me down I’ll” she paused for a bit, “I’ll let you carry on with what you were gonna do”.
I blushed when I heard that, I looked at the ropes that were tied around her ankles. I reached into my pocket and pulled out my pocket knife, I flicked the blade out and carefully used it to cut the ropes on her ankles. When her first leg was free she wrapped it around the back of my head, and after I cut her other ankle free it too wrapped around my head. I held her close as I ran into the building next to the school, it was for washing the school's clothes so it’d be empty at this time of day.
As I closed the door behind me I barely registered the fact that Applejack’s pussy was practically pushed into my face, carefully looking over her shapely ass I cut her hands free.
Instead of carefully climbing off me her hands started to pull my zipper down, “I did promise you that you can carry on” she said. Her hands pulled my member free from my shorts, “consider this my way of saying thanks” her hand ran along the length of my shaft.
As she did that a faint gentle smell entered my nose, I looked at her pussy as it started to get wet. I used one hand to hold her body close to me as my other hand grabbed her ass, I felt how soft yet firm and supple her bottom was. As my tongue started lapping away at her pussy she took my cock into her mouth, she matched her motions to mine. If I licked slowly she suck my member slowly, if I licked quickly she’d do the same. If my tongue went deep inside her then she’d deepthroat me, I held her as I carefully knelt down as my legs were getting weaker from the pleasure.
Once on my knees I carefully reposition myself so I was on my back with Applejack on top of me, after a while of pleasuring each other in this position, Applejack sat up and turned around before moving so her hips were above mine. She reached into my pocket and pulled out my wallet before opening it, she pulled out a condom from it as she cheekily looked at me. “Rarity gave you these didn’t she?” Applejack asked as she placed my wallet back into my pocket, I nodded as she continued “honestly she keeps saying to speak to you about the last few bets I’ve lost. I guess she knew somehow that we’d do something like this”, she opened the condom and put it on my member.
I felt the heat from her pussy as she sat down enveloping my cock in her tight hole, once fully inside her she continued “truth be told I wanted to tell ya earlier but I wasn’t sure how things were after the last few times”.
I sat up and kissed her “I was a bit confused but to be honest I’ve been in love with you for a long time AJ”, I stroked her cheek "I've been wanting to tell you for a long time but you kept your distance especially since the time you flashed your panties at me".
Applejack held me close to her as I wrapped my arms around her, "thanks partner" she said as she slowly started to move her hips. She leaned back a little as she bounced hard enough for her breasts to hit me under the chin, she held my head between her soft pillows.
My hands moved down and grabbed her ass as she pumped her hips up and down, each movement drove my member deep inside her.
She carried on moving her hips until her body twitched as I felt her pussy squeezing me, as her pussy pulsed around my cock it brought me to my limit as I came filling up the condom inside her.
We sat there for a while until our orgasms subsided, I looked at Applejack "so you being tied up like that? was that Rainbow's way of upping your last win?" I asked.
She nodded as I remembered what happened a few days ago, I woke up late in the morning and had opened the curtains to my living room. I jumped when I saw Rainbow tied upside down outside my window in her rainbow-striped underwear, when I got outside to help her I found a box outside my window that Rainbow was in which prevented anyone else from seeing what I saw.
I shook my head at that memory "honestly you two have got to stop doing these dares and bets" I said, something from the corner of my eye caught my attention. I looked at the window and caught Rainbow looking at us, she quickly ran when Applejack saw her. Applejack stood up as my cock slipped out of her pussy, I pulled the condom off and disposed of it as I put my member back into my pants.
Applejack grabbed some clothes from the side that had been washed earlier, no underwear to put on but she did have some school gym wear to put on.
Once dressed we headed outside together, we held hands as we headed to our class.
"Honestly though Rainbow needs to feel the same treatment," Applejack said, "anyone could've seen me" she blushed at the thought "but I'm glad it was you of all people".
