Jenny gave you a smirk and then flipped her panties down. She had a monster of a cock, and it was only half-hard. It easily dwarfed your dick - you weren't the biggest but you weren't below average either which is why you felt confident coming onstage in the first place.
Jenny looked haughtily over at your cock. She gripped her large, but feminene, dick in one hand and gave it a jiggle. It clearly had some heft.
"Well, well, well, folks! Looks like we have a clear winner before we even start!" Cass bellowed, "But never count anybody out - perhaps our young buck here can still measure up! Go ahead and get started!"
You were pretty sure it wasn't going to be close. You started working your dick nice and fast. The burning humiliation and the thought of losing 2 full inches from your pride and joy actually seemed to turn you on... you gave a sidelong glance at Jenny.
She wasn't even jerking it all the hard. She - and the crowd - seemed to savor every stroke. She ran her surprisingly petite hand up and down her girthy shaft. She was already leaking precum at the thought of dominating your dick. It was starting to stand a long and proud 8 inches and she still had a little more to go.
You meanwhile strained as hard as you could. This was easily the hardest, most erect you've ever got. You've measured it a handful of times, it fluctuated around 6 inches. The thought of humiliation and Jenny robbing you of inches just caused your dick to strain harder... you estimated it would be 6.5 maybe 6.75 inches long at this point. And it'd probably be the best you could do.
Cass let you two continue before judging that your erections were complete.
"Well, folks, our young competitor gave a valiant effort... but it seems clear that our Jenny here will measure up the most." Cass said.
With a flourish she produced a tape measurer, the flexible kind tailors would use, and had you two stand side by side. Jenny was tall and stood at essentially your height (maybe she was half an inch shorter). Her cock stood proudly at, 9 inches maybe? It easily dwarfed your cock. You felt a pang of embarassment.
Cass rolled out the tape measure on your dick from tip to base.
"Hmmm, looks like 6.7 inches to beat." She said, giving you a nice stroke.
She turned to Jenny. Admiring it with mouth agape. She playfully rolled out the tape measure. The crowd was silent and almost held its breath as one... Cass rolled the tape measurer gently and slowly from the top of Jenny's cute, huge dick to the base. It crossed 1 inch... 2 inches... 3, 4, 5 and only just passed halfway, it passed your length with another 3 or so to go... finally she hit Jenny's firm abs.
"Looks like... 8.9 inches folks!" Cass said with a jump.
The crowd bellowed with a mix of joy and surprise.
Cass produced some lotion with TRANSFER written on it.
"Alright, kiddo, I'm going to lather on this lotion and rub your two cocks together. I'll get you to transfer 2 inches over to our winner while putting on a show..." Cass said with a wink, "Try not to cum before the big finish, little man."
Cass had you two face eachother. The heat from Jenny's cock poured over yours, her thick balls dominated yours. You gulped as you looked at her monster.
"Oh my husband is going to love this... a full 10 inches?" Jenny whispered, "Give me what belongs to me."
You nodded. Cass started to rub you two sensually, easing the lotion over each of your dicks. You felt a tingle as your saw your dick shrink, slowly but surely. Jenny's member rose measurably but almost imperceptably - it was easier to tell you were losing rather than she was gaining. You tried to contain some moans, but between Cass's deft work, the tingle of the lotion, the burning humiliation of losing, how hot Jenny looked with her smirk and her domination and her curvy body, you couldn't resist letting out a deep groan.
Soon you leaked some pathetic precum. It aided the lubrication. Cass kept the tape measure close - only another inch to go.
"C'mon, little man, hold it in, okay?" Cass said, "I know you can do this. Don't cum until I give you permission."
She clearly picked up that you were getting off on this power play... no matter. Her encouraging words kept you holding your load in. Jenny let out a moan of pleasure as her cock continued it's inevitable rise. You'd never seen a cock over 9.5 inches before, except maybe porn, but it look huge in person. It looked even huger on Jenny's smooth and curvy body for some reason.
"Alright, I'll count down and let you finish, okay sweetie?" Cass whispered.
You nodded. You hadn't paid attention to your own dwindling member but looked now. It was as small as it was during middle school... a pathetic little thing. But it was eager to let a load of cum out.
"5... 4... 3... 2... 1!" Cass said.
And your dick complied, allowing you to orgasm a comparitevly enormous load over your and Jenny's dicks. Jenny, likewise, exploded with cum. You buckled at the knees and fell over. Cass produced some soft, war clothes and washed you both down. You got up and sheepishly moved off stage.
"Well, folks that won't be the last of our challenges tonight! Let's see some more takers!" Cass said as a cleaning crew wound there way behind her.