The Newbie's Prize

Rachel giggled. "Yip, yip! I'm coming!" She replied. Getting her head and shoulders through was easy, but quickly her boobs started smooshing against the wooden bar. "Nngh...here we go..."

Janet clapped excitedly, being a cheerleader for her friend as the redhead tried to make her way through the chair. “Come on, Tracy! Come on, you can do it!” she yelled, bouncing up and down as Rachel got her head and shoulders through within the first thirty seconds of the challenge. “Youâ€re doing great!”

As expected, however, Rachel ran into trouble when her breasts smashed against the wooden frame. Janet kept clapping and yelling, trying to give the girl what encouragement she could.

Rachel groaned as she braced her arms alongside her. "Uhhhhhahg! Come on, fit!" She cried. Her lovely orbs were simple squished between the opening, half in and half out. She wiggled and jerked, slowly but surely going to get them through. She couldn't imagine how much she must be wasting.

The one minute mark passed by. Then, the two minute mark. Rachel slowly but surely slipped her two lovely, jiggling breasts through, but, by the time she had gotten her whole chest through to the other side of the opening, almost half of the allotted time had passed. Janet really wanted to see her friend succeed, but it didnâ€t look like that was going to happen.

“Keep going, Tracy!” Janet said, pounding her hands on the floor to try to encourage the redhead to make a greater effort. “Youâ€ve still got two and a half minutes!”

Rachel surged.forward. Her hips struck the wood and held her up. "Damn it!" She cursed, applying extra force to shove them through. Once they had squeezed past, she pumped her arms, slamming her bum against the frame. It hit and jiggled, causing the redhead to gasp at the new stimulation from her plug. She planted her hanes on the wooden legs and heaved, her ass squishing against it like a beautiful, tanned beach ball.

By the time Rachel had managed to squeeze her hips through, three and a half minutes had elapsed. Now only a minute and a half remained for the redheaded girl to try to squeeze her deliciously plump derrière through the wooden opening. Janet got to her feet, running around to the other side of the chair and leaning in close to try to see if Rachel was making any progress.

“Come on!” she yelled. “Come on, Tracyâ€s butt! You can get through there! Go! Go!”

Rachel laughed. "Are rooting for me or my ass?" She called, pushing and straining. A tiny inch, maybe two, of movement, but not enough to notice. "Nnngh! Ngh, ngh, nghnghnghNGH! She groaned, jerking forward in a desperate attempt to get through.

Janet laughed and gave Rachel a soft slap on the rear end. “Both! I love both of you so much!” she said. “Now, come on, Tracy! Come on, Tracyâ€s butt! One minute left! Push! Push!”

Rachel squirmed in the wooden tunnel. "Unnngh! Commmme...onnnnnauuuugh!" She groaned loudly, her butt barely a quarter of the way through.

As much as Janet wanted to see her new friend succeed, she now had only ten seconds, and her butt was only a quarter of the way through. A smile slowly spread across the Native American girlâ€s face; as great an accomplishment as it would have been for Rachel to succeed in pushing herself through, her failure meant a fun play session between Janet and the redheadâ€s incredible ass. “Ten seconds,” Janet announced, watching Rachel make her last few desperate pushes with intense interest. “Nine…eight…seven…six…”