My Little (BIG) Stepsister: The Bet

Disclaimer; this story is attended for adults over 18. Everyone in the story is 18 or older. The story features characters in their 20s, as well as a few that are age 18.

The Wrestling Match

"Make sure to hit record. I want to make sure every second of this is recorded and saved so everyone can see it time and again!" Natalie said, grinning ear to ear, obviously confident that she would be the winner. We circled each other for a moment, sizing one another up; a tall, voluptuous girl, and a short, skinny dude about to go at it.

The crowd was now getting super excited, growing louder by the minute. Both her friends and my friends were eager to watch the spectacle. "Are you ready to get your fat butt dominated, little boy?" Natalie said playfully, looking down at me. I was ready. Ready to beat the shit out of her. Ready to shut her mouth, once and for all. After this, she wouldn't even think about messing with me, or bossing me around, or making fun of the size of my butt. "You can keep talking trash all night Natalie, but you're only gonna make things worse for yourself!" Tristan said, not breaking eye contact with the bigger girl.

The audience was told they would need to watch from the outskirts of the room and to not get involved or interfere. They'd agreed the match would end when one sibling made the other submit by tapping or verbalizing that they give up. They circled one another, sizing each other up. Natalie had a mischievous grin on her face, while Tristan was purely focused and ready. As Sean recorded with his phone, he couldn't believe how much bigger Natalie looked than her brother.

As soon as someone shouted 'go', Natalie came charging at me. I was taken off guard, not expecting her to just come at me so fast. I watched nervously as the she came at me, closing in fast. Quickly I attempted to use my wrestling training and went down low, attempting to get Natalie's legs. Natalie had been expecting that, and was able to grab my head, forcing it between her legs, locking me in a tight scissor hold while still standing.

She squeezed her strong legs tightly, putting a ton of pressure on my head and neck. The match had only been going for 10 seconds and Natalie was already in control. "Nice job! Really good tactic Tristan!" I attempted to get my head out, or get away, but Natalie was strong as hell. With me bent over, stuck in her clutches, Natalie went straight for my ass, delivering 10 hard slaps to my jean covered butt. "You said you think I deserve a spanking, well you're about to find out how it feels to be spanked, fat ass!" Natalie yelled out, smacking my ass as fast and hard as she could. I cried out, shocked that she was slapping my ass so hard. I didn't expect any spankings until the match was over and done with, and I certainly didn't expect it to be me being spanked. I put my hand up to protect himself from anymore incoming smacks. The crowd was already laughing loudly. SMACK! SLAP! SLAP!

I couldn't believe how strong Natalie's thighs were. They held me tight, like a vice. "Who wants to see Tristan's big fat butt?!!" Natalie yelled out, almost maniacally. Before I could react, I felt Natalie start fiddling with the front button of my pants, then the zipper. She did this fast and efficiently, leaving me little time to defend or even consider what to do. Suddenly, she yanked down my jeans, pulling them all the way down to my ankles. She then used her foot to step on my jeans, forcing them down further, and then eventually all the way off, leaving me pantless. "Nice whitey-tighties, loser." Natalie said, delivering another hard slap. The crowd laughed hysterically at this. This all happened so fast, I was caught completely off guard. SLAP! SLAP! SLAP! Natalie continued her spanking onslaught. "I told you Tristan, I was gonna whoop your ass! How's it feel shorty!"

I struggled with all of my might, trying to free myself from between her legs. Natalie called her boyfriend Sean over closer so he could film her. Her next move. "Come here bitch. You're getting powerbombed!" Natalie yelled out smugly. Suddenly, I felt Natalie bend over, putting her arms around my waist. I immediately felt my feet lift off the ground as she yanked me into the air. She hoisted me clear up onto her shoulders in a powerbomb position. I couldn't believe her strength. I was terrified of heights and must have looked funny, grabbing onto her for dear life. I expected her to just slam me, but she held me up high, just holding me up, giving Sean plenty of time to record the embarrassing event. I had been a fan of prowrestling growing up, and knew exactly what a powerbomb was. Finally, she did slam me. Then she stood over me and yelled down at me, "Suck it, you little brat!"

Thankfully, she'd slammed me on the couch, but she'd slammed me extremely hard. My back hurt, the wind had been knocked out of me, and the people watching us were now going ape-shit. I had just been forcefully power-bombed by my little step-sister in front of 12 friends of ours. I looked over to see some of my friends laughing so hard, they literally were rolling on the floor. Natalie looked at me, smiling smugly, gloating about what she'd just done to me. "This is just like wrestling the kid I babysit for, and he's a nine year old!"

Before I could get up, Natalie was on top of me again. She quickly grabbed me by the back of the neck, finding my pressure point, and forced me to bend over again. I was still trying to catch my breath after being slammed so hard and could do little to defend myself. Natalie grabbed my tshirt and yanked it over my head, hockey-style. Now I couldn't see a thing and was left struggling with my tshirt. She helped yank it completely off, leaving me in nothing but my undies. I was growing bright red; not even comprehending how easily she had just stripped me down. She held the tshirt up high above me, daring me to get it. "Come on bro! Don't you want your shirt back! Jump for it!"

Instead, using this opportunity to change the tide, I went straight at her, ramming my shoulder directly into her stomach, spearing her into the couch. I could hear her coughing, knowing that I'd just knocked the wind out of her. Finally, I thought to myself; the tides were about to turn. That took longer than I expected. But as I attempted to stand, I felt Natalie reaching over me, finding my underwear. Suddenly, I realized I had made a bad mistake. She grabbed the hem of my undies tightly and yanked with all her might. "Wedgie!!!" She yelled at the top of her lungs. And wedgie she certainly did.

I felt the fabric fly up my butt crack with such force, I was yanked towards her. She still was seated on the couch, with me, her big brother bent over, butt sticking out towards the audience, underwear pulled tightly up my ass. She regripped, now collecting the leg holes of my tighty-whities and yanked again. Harder this time, pulling all the fabric deep into my crack, like a thong. I squealed and grunted loudly from the pain. I attempted to get free and decided to twist around, somehow finding my footing. Suddenly, I was able to stand back up. Unfortunately, Natalie didn't let go of my underwear. She still had a firm, vice-like grip and stood up with me.

Now Natalie stood behind me, holding me tightly by the back of my undies, pulling me up on my tippy toes. They were pulled tight, fashioned into a wedgie thong, a nice handle or wedgie-leash. She had stripped me of my pants and tshirt, so now my wedgie thong was my only clothing. And my socks. My undies were now stretched out, the waste-band now being pulled up to the middle of my back. "You give? Do I get the room? Huh? Wedgie-boy? Or do you want me to keep making you look like a little bitch?"

When I didn't answer her, she kept one hand tightly holding my wedgie-thong in place, and used her other hand to begin slapping my near-naked butt cheeks. With my undies wedgied deep up my ass, there was nothing to protect me from Natalie's spanking hand. No pants, no fabric. Nothing but skin. Due to the skin to skin contact, the sound echoed around the room. Loud, heavy slaps. This was incredibly embarrassing.

I began desperately trying to escape her, running away as far as I could, but not getting anywhere, as Natalie had my undies locked in her hand. She laughed as she yanked me back and forth by my wedgie, slapping my ass and thighs until they were beat red and covered with handprints. When I looked around the room, all I could see were smiling faces, and phones up recording. Laughter everywhere, including my tormentor, my little step-sister Natalie. She was laughing the loudest as she chased me around the room, delivering slap after slap. "Look at that fat booty jiggle!"

I danced around, desperately jumping about, trying to dodge her painful hand, making a complete and utter ass of myself in front of all our friends. Natalie laughed as she pulled the underwear tight again, doubling her grip of the stretched material. "Come here Blubber-butt! You're not going anywhere!" She said, as Sean came in close with his phone, recording how tight my wedgie was getting.

My butt was on fire as I felt Natalie's powerful hand again connect with my bare skin. And then again. And again. Then she delivered several hard swats right on my thighs, up and down to my knees. I was now beginning to really panic. I was embarrassed beyond belief, but now the pain was starting to get to me.

Before I could register what was happening next, I felt Natalie spin me around to face her, and get me in another tight bearhug. "Come here little boy!" She quickly found my undies again with both hands and pulled extremely hard. The wedgie was now pulled so tightly, I felt myself being lifted onto my tiptoes. I could hear Natalie breathing heavy as she again tightened and regripped the wedgie, pulling me even higher up on my toes. I really didn't like where this was going.

"Pick his little bitch-ass up!" Sean said, laughing loudly, recording every moment of my humiliation.

Natalie bent down, preparing herself to lift me. The room went quiet for just a moment. Finally, she stood, yanking my underwear with all her might. Immediately, I felt my feet fly off the floor, almost in comedic fashion. She was so much bigger and taller than me, she was able to hoist me well over a foot off the ground. And not only was she able to lift me, she was holding me up, allowing the wedgie to sink deep into my ass crack.

The whole room was erupting with yells and laughter. As I hung in the air, I gazed at my sister, pleadingly, hoping she'd have mercy. Natalie was wearing an expression of pure joy and pride; proud of herself for being strong enough to straight up dominate me (holding me in the air by my wedgie!), and proud of herself for putting me in my place. "How's that feel, wedgie boy! Wedgie-Bitch!" Natalie yelled loudly, now beginning to bounce me up and down by my wedgie. She would pull me up high, then drop me down, hard, careful not to let my feet hit the ground, making sure all the force hit my crotch region. Then she'd pull me back up.

Then she regripped again and began putting all her strength into it, making quite the visual, yanking me around like a little, wedgie ragdoll. I was in shock, and my ass crack was in agony. Every time she yanked me back up, I could see her smiling, smug face, her neck muscles showing as she used her superior strength to wedgie the fuck out of me. Suddenly, I couldn't keep it together any longer. I broke from the pain. The next thing I knew, I was screaming, and pleading for her to release me.

"Please!" I begged, my voice squeaking as I again was pulled up by my undies. "Ouch! It hurts too much, Natalie! You've proved your point! Now please let me go!" I was now nearly hyperventilating, praying that I wouldn't start crying. Everyone was watching us, and recording it on their phones. This was the most humiliating moment of my life.... So far, that is. Natalie laughed loudly, making a big show of what she was doing; showing off for the cameras. She was so much bigger than me, her step brother that it wasn't even that hard for her to do what she was doing. Now instead of just bouncing me, she was yanking me this way and that, rag-dolling me around mercilessly, barely allowing my feet to ever touch the ground. She was getting her anger and frustration out. Her anger had been building for the last week.

Suddenly, she started doing it even more aggressively, and with more power and fury, truly shaking me about, like a dog with a chew toy. To everyone watching, it was truly a hilarious spectacle; one that would be remembered for a long time to come. I was now screaming loudly, my voice suddenly going high pitched. "Please Natalie! I beg you! Let me go!"

Natalie was red and full on grunting now from the exertion it took dominating me like she was. "Tell me I get the room!" She yelled loudly, still violently yanking me around like a yo-yo. "I said, tell me the room is mine, bitch!" Bouncing back up by my wedgie, I was in incredible pain.

"You can have the room!" I screamed out, my voice vibrating with the bouncing and rag-dolling, hilariously to everyone else. Instead of letting me go, Natalie pulled back, slowly lifting me higher by my wedgie. I felt myself being lifted, slowly getting higher, surprised that Natalie continued to lift me. Everyone grew quiet and watched as Natalie lifted me into the air, presenting me to the audience, like Rafiki in the Lion King lifting the new born prince. I could do nothing but hang there in shame in defeat. My younger step-sister was carrying me, naked except my undies, holding me high in the air by my wedgied underpants. The room was quiet, everyone's' eyes on me. Then I humiliatingly sobbed out loudly, beginning to cry from embarrassment. This caused everyone, including Natalie, to burst out laughing, very loudly.

"Please let me go, Natalie! You can have the room! Just please let me go!" I begged, more humiliated than I'd ever been before. I was in so much pain, I really didn't care about the crowd watching, I didn't care about the room. I just simply needed the wedgie to stop. Finally, Natalie set me back down onto my feet.

End of Part 2