Kinktober Day 15: Wedgies
“Jackie, please!” Silver cried. “Stop it! Why are you doing this?!”
“Why wouldn’t I?” Jackie laughed. He reached out and gave Silver a shove, making him sway back and forth in the complicated setup he was dangling from. “This is awesome, for me at least. And you brought it on yourself! Don’t act so surprised, you had to know someone was gonna find out your little secret eventually!”
Silver cringed in pain and humiliation. “You - you can’t do this! It’s j-just my - !”
“Just your little tighty whities?” Jackie interrupted with a croon. “Just your choice of underwear that literally begs for someone to come and give you what briefs-wearing nerds deserve? Just that?”
“Nah,” Jackie said with a grin. He went behind Silver and groped his ass, kneading his exposed cheeks and tugging lightly at the strip of fabric buried between them. “We’re both having way too much fun for me to stop now.”
“I’m not having fun! Please, let me out of this thing!”
“You are too having fun,” Jackie snickered, reaching around to rub the front of Silver’s briefs. Thanks to the horrible hanging wedgie he was in Silver’s cock and balls were painfully squished between his underwear and his body, but nothing could hide the bulge of his obvious erection. “You’re loving this. I bet I can make you love it even more, though!” He slapped Silver’s ass playfully. “Don’t go anywhere! I’m gonna go get some fun stuff!”
It was too late; Jackie had already dashed away in search of whatever ‘fun stuff’ he was after. Silver was left alone in his wedgie, hanging helplessly in the rig Jackie had put together in mere minutes after catching a glimpse of Silver’s underwear peeking out over the top of his pants.
Tears began to blur his vision and he blinked hard to get rid of them, wishing his hands weren’t tied behind him so he could just rub the tears away. He wouldn’t cry, he wouldn’t show weakness like that, he couldn’t! It would only make things worse! How could Jackie do this to him? How he could act like -
Like a bully, his mind supplied. Like a big, mean bully teasing poor little you, making fun of your tighty whities and giving you the worst wedgie of your life; good thing you enjoy them so much.
“Aw, are you crying?” Jackie was back, grinning at him from the doorway with his hands full of various items Silver couldn’t quite make out.
“No!” he snapped. He tried to sound strong and angry, but his voice wavered and Jackie noticed.
“You almost are; I’ll get you the rest of the way with these.” He stepped forward and showed Silver what he’d gone to find. Silver went pale.
A hitachi magic wand, a cock ring, a sturdy-looking length of rope just like the kind Jackie had used to string him up and bind his wrists, and a twenty pound weight plate from off of a barbell.
“J- Jackie,” he stammered. “Don’t - please don’t - ”
Jackie laughed. “Oh, quit acting like you aren’t living out your own fantasy. I can see the wet spot you’re making on your briefs, you know.” He flicked Silver’s dick through the stretched-out fabric, making him squeak. “How long have you wanted someone to do this to you, huh? How many times have you put your hand down the front of your tighty whities and played with your little dick while thinking about getting a nice, hard wedgie?”
That was enough to push him over the edge; hot tears spilled down Silver’s face as he started to cry, overwhelmed by the humiliation, the torment he knew was coming, and worst of all the truth in Jackie’s words.
“Wow; I know I said I’d make you cry but I didn’t think it’d happen that fast,” Jackie chuckled. “Now let’s have some nice playtime with all these toys here before your tighty whities rip.”