MARK NUMBER WHO KNOWS
"Alright I think I figured it out," said the attorney. "The tasks you failed are normally five and four. The next task, I think will be ten. I'll be there in a second. Pulling into the parking lot now. Hold on."
Eli stared in horror at his marks. The one across his shoulder blades was bad enough, but now he also had stylized drawings reaching from his right biceps to his shoulder and even his neck. The tattoos were in a cool style, but that didn't help that they were clearly squirting dicks.
One of them even squirted black ink drops all the way up to Eli's jaw. There was no way to fully hide it even with a turtle neck sweater.
A man in his forties barged into the room. He wore casual clothes and carried a duffle bag. "Eli?"
"A-are you the attorney?" Eli asked, instinctively covering his crotch.
"Yes, you have to complete the failed tasks anyway to move on or the next ones won't count."
The man opened the bag. "Here, put that on."
"What is that?"
"A cock ring. Do it."
"Cock ring? That one's too small for my dong. You can see I'm fucking hung."
"It's the only one I have. It's just going to get worse. You have to succeed in three tasks. Come on. I'm here to help."
Eli grabbed the ring and with a deep breath he rolled it onto his soft dick and pulled his balls through, assuming that was a necessary part of it. Very slowly his dick turned semi hard and expanded a bit.
"The other half of that," the attorney continued, "is this."
"And what is this?"
"A butt plug."
"No fucking way."
There was another tingling on his skin and Eli watched the third marking appear. His chest received decorative lines surrounding the words "MAKE ME YOUR BITCH".
Eli wordlessly took the plug and spread lube on it until it dripped. How bad could it be? A lot of girls in school had reportedly done anal. Some said it hurt, but those were pussies. As a real man, Eli was surely much harder to impress.
Meanwhile the attorney had taken a spray tube from his bag. "This is extra glistening body oil. It leaves behind a fine layer of glow, but hardly comes off and doesn't stain. You'll be dry while shining like you're wet all over."
Eli was sprayed from top to bottom, turning him into a perversely sweaty looking nude muscle boy. This gave him a moment to consider things. He could get the marks removed by a lengthy laser therapy. The only problem was potentially dying. He'd just have to do three tasks in the safety of this washroom, accept the other marks and find a discrete removal specialist.
Once he was fully oiled up his dick had grown into something a little harder and bigger, standing away from his body.
Following the man's advice he squatted on the floor, with his ass just above the plug. It was extremely embarrassing to do this in front of a total stranger. Not that he would have preferred to do it in front of people he knew. The attorney kept watching the struggling teen who was red with shame.
Then the plug entered him and he let out a scream. How could this hurt so much?
"Relax, Eli. You need to unclench your sphincter and do it fast because we still have one task to resolve before we can even try to complete tasks successfully. Don't keep failing."
With groans and a lot of grimacing Eli made it about halfway down the plug. His ass was getting torn to shreds. The plug hadn't looked anywhere near as big as it felt.
A tear ran down his cheek. "I- I can't... get it in. It's too big. It hurts too much."
The man grabbed him by the shoulders. "Don't scream or someone could hear you."
Then he pushed Eli down with all his force. The boy was stronger than the man but in his deep squatting position he couldn't fight against the pressure from above. It was hard not to scream but Eli turned it into a high pitched whining through clenched teeth.
After it was done the teen kept squatting, shivering and trembling. The pressure on his insides was overwhelming. His dick was fully erect now and straining the ring. Veins popped all over the thick tool as blood pooled into it, making it overly sensitive.
Very slowly the boy rose from his position. He felt too humiliated to put into words. There was a plug in his ass like he was some kind of fag. And he couldn't even take the pain like a man. And a fully clothed stranger was watching him.
"Eli, are you ready for the next task you missed? Then we can finally move on and get you three successes."
"Fine," the boy said with a sigh. "What is it? I'm naked, I'm oiled up, I'm erect and my ass is plugged. How much worse can it get?"
You all know how much worse it can get but it'll be fun to discover all over again.
If you like it let me know.