His house looked like each one around it in the suburban cul-de-sac, an echoing imitation of those on either side. When Joey started his regular visits, he had to double check the address, but now there was no question. Shivering a bit from the night air on my way up the path, Joey rang the doorbell and waited for an answer. He inspected his outfit, his heart beating a little faster as he grimaced under his mask. This had to be the most ridiculous outfit request yet: it was some kind of cheerleading uniform. Of course, as a straight guy, Joey hated wearing girly clothes, but he had no choice. It's what the dude wanted. He adjusted his skirt, hoping the pleated fabric would hide his panties which had an embarrassing bulge under them.
The door swung open, revealing the owner of the house. Joey didn't know his name, as he insisted on an alias: 'SudoAnon'. He was huge. He must have been 6'3", with shoulders like a blacksmith. A greasy wife-beater undershirt clung tightly to his body, accentuating its sculpted muscularity. He held a grizzly smile on face to complete the look of an off-putting thug. "Back for more money?"
Joey gave him an annoyed look. "Yes, money. I can't believe I have to wear this stupid outfit."
"What's wrong with it? You're pretty enough," said SudoAnon.
"I'm straight! I don't want to dress like this!"
SudoAnon chuckled at that. "Sure, whatever you say. Come in then." He ushered Joey into the house, his large hand coming down upon Joey's shoulder and propelling him forward. The contact made Joey feel a twitch in his panties. "You've been taking your pills, right?"
Joey gritted his teeth. "Yes, the stupid estrogen pills. You know, I have to wear baggy clothes now, or people will notice I look like a girl! This is so dumb."
As they stepped into SudoAnon's room, he shut the door behind him, and then turned to face Joey. His voice became quiet, serious, but not threatening. "If you don't want to do it, stop coming back here."
"That's extortion," snapped Joey.
"You know it's not. You want to use Sudowrite to generate AI stories, you need money to pay for the service, this is how you get money. You could get a job, but you're here. You could do anything else, but you take estrogen pills and wear girly clothing, so obviously you enjoy dressing that way." Joey glared at him, but his body betrayed his reaction — his dick was already stiffening against the tight fabric of his panties.
"Just... tell me what you want me to do," he huffed, awkwardly shifting one arm to cover his crotch. His face mask was hiding his flushed cheeks, and muffling his heavier breathing.
SudoAnon smiled. "I'm glad we understand each other. Get under my desk."
Joey followed orders, stepping beneath SudoAnon's workstation. It was cramped, with Joey barely able to fit underneath the desk. It smelled like old cigarettes, sweaty gym socks, and too many beers. As he squatted there, Joey felt his penis grow harder, causing him to groan quietly.
SudoAnon sat down at his desk, trapping Joey beneath it. "Alright, get started."
Joey stared up at him through his legs. "With my hand?"
"I want your mouth this time. Go on."
Joey sighed. "Fine."