Craig didn't mind being naked or knowing that the man would watch him now and then. He didn't mind that occasionally the guy would touch him either. It was part of the job.
"Hey dude we can make some serious money from those rich guys" It started then with Harry and he had finished wrestling in his bedroom as usual.
"Doing what?"
"We do chores and stuff they need. They're usually old and don't do it themselves. We just do whatever they want and they pay us. And if we take our shirts off or wear tight shorts we get extra money." He said grabbing his crotch in the jockey shorts they both had stripped to.
"How do you know all this?" Craig asked.
"Been doing it since summer. I helped a guy clean his apartment and he told another guy about me and before I knew it was cleaning apartments." Harry said "and making more dough then working at Joe Joe's Burger Bin.
"Fuck" Craig thought about it "what about the shirts off and shorts part?"
"Most of em like hot looking young dudes like us. So if we sweat, take off our shirts or wear tight shorts..hell I wore my wrestling tights once and a guy paid me double".
"We don't have to do stuff right?" Craig's cock was growing hard again as it was when they wrestled.
"They ask but all you gotta do is apologize real nice like and say you have girlfriend or boyfriend or somethin. Don't insult them either. Just smile like you like em. They're suckers for a smile. If you want I can get you a gig with me."
"Dunno" Craig said "maybe"
Their first gig together was kind of weird at first. But Craig got used to doing the type of chores he did at home for other people.
He was vacuming while Harry was washing windows. The man, a man older then his grandfather sat on the couch reading. But occasionally Craig saw him looking at them working. He smiled realizing Harry was right.
"Hey man it's getting hot" Harry said. Craig looked over and saw his friend peeling his shirt off. Craig glanced over at the man they were working for who was looking at Harry over the top of the newspaper he held.
"Yea know what you mean" Craig said and stripped his off too. "Sir do you mind if I?" Craig added "I got shorts on under"
The man looked at him first with a scowl then he smiled "no no, do what you think is comfortable"
Craig knew Harry was watching as he stripped his jeans off leaving only his boxer shorts. "Thanks Sir" he added returning to his work.
It became a contest after that.
"I'd take mine off but I forgot to put on underwear" Harry said later as both of them were washing the large windows.
"It's ok, I don't tell anyone" the man said
Harry was naked in a flash. Craig was tempted to join him but his cock which was now hard might reveal something he didn't want to.
"Man we got double" Harry said as they left the house. He counted out Craig's share. "If you had stripped down we would have gotten more".
"Maybe next time" Craig replied feeling the small wad of bills in his pocket.
"Cool you want to do more? Great" Harry said
"So are you two boyfriends or what?" Mr. Damon said. By then they had worked, stripped and entertained several clients. During thier car washing for Damon, they made sure to wear white and get very wet knowing how that would entertain him.
He called Craig for them to clean his house too.
"No Sir we're friends" Craig said
"We mess around, you know wrestling and stuff like that" Harry added.
"Hmmm I'd love to see how you boys wrestle. I used to wrestle in school myself" the man said.
By the time they finished dusting, vacuming and washing the kichen floor both boys were shirtless and wearing the gym shorts they had worn to the job.
"Get the pad there and roll it out" Damon said
"Now you two go ahead and wrestle. I want to see this" He sat on a chair aimed at the pad.
"UH we don't have our tights" Harry said
Craig stared at him questioningly since they never wore tights when they wrestled at home.
"We only wear those during meets" he corrected
"Oh yea, we kind of wear jockeys at home you know when we fool around"
The man sat forward as if suddenly interested "That's ok go ahead and take your shorts off"
Harry, as usual, was quick to strip to his tiny whitie jockey shorts. Craig did the same afterwards.
They grabbed each other and wrestled ignoring the holds, rules and safe grabbing they used to do in school.
It was Harry to grabbed the white cloth on Craig's butt and yanked it until it ripped. Craig almost stopped. But he knew his erection could already be seen by Harry and Mr. Damon.
So instead he grabbed Harry's and ripped it.
Harry was soon sitting on his chest pinning Craig's arms back. All that remained of their underwear was elastic and a bit of cloth.
"I win" He announced
"So what do you win?" Mr. Damon said "That boner you have wants something" the man laughed.
Harry backed off Craigs hands but remained on his chest.
"I think I win a hand job" he said laughing. Craig struggled but not enough to push Harry away.
"It's ok, if that's what you boys do, go ahead I won't mind in fact I'll pay you both extra if I can watch" Damon had moved next to them kneeling back on his ankles.
"Go ahead" Harry said to Craig "it's ok" his cock was in his hand now.
Craig touched the cock he had seen often but never dared touch. He had fantasized about doing that and more with Harry whenever he jacked off himself.
"It's ok" Harry urged glancing toward the man who was obviously excited "he'll pay"
Craig jacked his friend until sperm shot all over his face, neck and chest. "Fuck now get off" he said
Harry still wiping his dripping cock on Craig's chest lifted his leg.
"Now I thought you two were friends" the man said. He was rubbing the obvious growth in his own pants.
"We are" Harry said
"Well shouldn't you make him feel good too?"
Harry looked at Craig's boner.
"Ten more each" Damon added and Harry instantly started jacking Craig's cock until it too shot sperm all over the place.
"You two are nice boys" Mr. Damon said as he counted out money for them as they dressed.
"If you two ever want to uh, do something more, you know secret stuff just between us three, you can do it here."
"Thank you Sir" Harry said and Craig repeated the thanks as he pocketed the folded twenty dollar bills.
"In fact, I have parties now and then and we always like boys like you, you know who aren't inhibited to uh entertain. You can make alot more then this" Mr. Damon said.
Weeks passed. There were apartments. condos, houses to clean. Cars and trucks to wash, storerooms to organize, offices that needed cleaning very late at night, even one boat that needed washing while sailing off shore.
Harry and Craig had bank accounts and balances that were larger then any summer job they had had in recent years.
The parties added even more money to their accounts. First they wrestled for the men like they had done for Damon. Underwear, gym clothes, even wrestling tights got ripped and they wrestled naked until one of them won and had to give the other a hand job.
Another party went further. They hadn't planned it but Harry lost and started jacking Craig. Then to Craig's surprise began to suck him until he erupted. They made much more money then.
A third party repeated the action and they sucked each other performing as the onwatching men instructed until their boy sex was satisfied with Craig's cock inside Harry's butt. He didn't complain or refuse at all.
"Did you uh like that?" Craig asked as they lay on the bed that night. "It was ok. You have a nice cock. Next time I want to fuck you though" he said..they started to wrestle but fell asleep.
It was the fourth party when they were told that the men just wanted them to make love. "You know kiss, explore, act like it's the first time, then do each other"
"You ok with this?" Harry asked Craig. "Hell they're gonna pay us each two hundred" Craig said
The kiss was exciting. Their hands used to grabbing each other moved slower, lighter as if exploring each other for the first time. Indeed for Craig it felt that way. When Harry's cock entered him it was the first time and the grimace expression and eventual pleasure he showed were real. He repeated his insertion into Harry and the crowd seemed to like the fact they fucked each other.
"That didn't mean we're queer" Harry explained "it was for the money". "Yea we're fuck buddies' that's all" Craig said.
He was naked, scrubbing the floor. The man reached to play with his testicals and cock which grew hard instantly.
"Very nice boy" The man said. Craig had taken the job alone. Harry was on vacation with his parents. School would start soon and their summer jobs would end. He had three thousand dollars in his bank account and felt different then he had felt in years past.
"Thank you Sir" Craig said.
"Want me to keep doing this?"
"If you want Sir" Craig said He gasped as his body responded to the man's hand milking him until the clean floor was spotted with his sperm.
"Nice load boy, now lick that up" the man watched as Craig obeyed.
"You're very obedient. Are you a slave boy too?" The man said.
He was tall, hairy chested, muscled legs. His shorts were tented now.
"I've learned to do what I'm told Sir" Craig said his own cock regaining it's stiffness as he looked up at the man.
"Good I can use a boy like you now and then. Maybe you can come by now and then during the school year, like that boy?"
"Thank you Sir" Craig said "Will Master fuck me whenever he wants Sir?"
The man smiled.
"I've been waiting for a boy like you"
Craig knew he'd have enough money for college by the end of the next summer. He wondered of men like this one would want two slaveboys too.
His summer job had become something more.