The Education of Billy Boy

Billy Boy meets his new boss, Sean O'Toole under strange but sexy circumstances. Big Jim, the photographer, gets Billy stoned and "things" happen.

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  • 1135 Words
  • 5 Min Read

Jorge handed Billy a jock in a plastic bag. The four seniors members of the Tennis team silently stared at him. Nervously Billy dropped his shorts revealing his mesh black bikini. The seniors whistled, hoots and hollers. were laughing. "Got a hot date?" "Come on take them off." He pulled off his shirt and dropped his underwear. Standing naked he opened the package and put on the new jock. The men broke into an applause.

"Parker explain to Coach Noff why we wear our jocks for every meeting."

"First to show we have nothing to hide. Secondly because when we wear the school jock ... we are all equal. We all have a say in our sport, no one is showing up fancy or with expensive clothes. Staff included."

"Well done Parker. Guys hit the showers." He turned to Billy. "Welcome." He gave Billy a big manly hug.  "Did you find a place to live?"

"I did. Palm Grove Apartments. Couple a miles south."

"Come on let me give you the tour." 

"It's okay to wear jocks in the building?"

"It's Sunday no one is here. Palm Grove. I hired a photographer in that apartment complex to shoot the players individually and group. He was a big guy and reeked of pot."

"That's him. He seems very nice."

"Okay. The door to the left is the basketball court and the one on the right is visitors locker room." He led Billy through the basketball court and to door on the opposite side and down a hallway. "This is your office ya got a desk, phone, filing cabinet." Pointing to a door. "That's a bathroom we share. My office is next door. Down the hall is the teachers cafeteria.  Wanna play a  few rounds?"

Billy was taken back. "Outside in our jocks?"

"No! We have an indoor tennis court. And there is a certain freedom when you play tennis nearly naked."

Billy nodded. "I get that!"

As they walked to the court, Billy thought Sean O'Toole was one of the best looking man he'd ever met. From His ginger crew cut to his pale skin white as a cloud. His thighs were  a mass of muscle. And his ass ... his perfect ass ... so round and sprinkled with rust colored velvet hair. 

When they started playing the game the first thing Billy noticed was Sean's bouncing cock beneath his jockstrap.  It mesmerized him. It's got to be a huge dick, he thought. 

Billy started sweating. Damn Sean was a good tennis player. He had the new comer running from one side to the other. They played for another half hour and called it quits.  Billy needed a shower. They met at the net and shook hands like gentlemen. 

Back in his new office he dropped the jock and opened the bathroom door at the same time as Sean opened his. They were both naked. "I'm sorry, you go first Sean."

"Hell no, the shower is big enough for both of us. Come on." Sean turned on the water then turned Billy around wetting his back.  Coach O'Toole soaped up a wash cloth and began washing Billy's back. Slowly went down further essentially washing Billy's butt.  He silently prayed not to sprout a woody. Billy grabbed a second wash cloth soaped it up then washed Sean's back his crotch. 

Sean poured some shampoo on Billy's head, then Billy did the same thing to him. They started laughing as they rinsed off. Looking down, for just a moment Billy witnessed a twitch from Sean's 8-inch cock.

While toweling off in Billy's new office. Sean got a little serious.

"You are the man I wanted for my assistant coach. A dude who could take a shower with another dude and not think anything of it. Straight A student. I've watched yer naked ass running around the court today and you played so damn well under pressure. You're just a talented man."

"That's the nicest thing anyone has ever said to me.

"Welcome aboard!" Sean gave Billy a manly hug. It was the greatest hug he'd ever received.  

"And before I forget, you need to get a physical. You can use my doctor. Most of our players go to Dr. 

Billy smiled as he put on his new school jock on and pulled up my shorts. He didn't bother putting on his T-shirt knowing it was in the high eighties outside. Driving home it occurred to him that he didn't have his underwear, the black bikini. Oh, It's probably in my new office.

When Billy pulled into the driveway of Palm Grove apartments he saw Big Jim taping a note to his door. Closing the car door caught the old man's attention. "Hey Billy, I remembered you're working with Coach O'Toole. I took photos of the players and the coach last year. He had me take a nude photo of him ... for his girlfriend.

"Big Jim will you take a photo of me naked?

"Why sure I will, come on in".

His apartment had been turned in a photo studio. The dining room had multiple lights. There was a French sofa, an old leather saddle, several boxes and so many beautifully framed photos of naked men. "Billy will you put the saddle on the sofa." Big Jim pulled out a joint and lit while he positioned his camera. "Get out of your clothes." 

As Billy stepped out of his shorts, Big Jim laughed. "And you're already in a jock. You want a hit." He past the joint to Billy. 

"I've never tried it." Billy took a big hit

"Now is your chance. What I want you to do is get into the saddle stomach down and arch your back to make your buns even better. I love the straps from the jock.  Billy turn your head,  look at the camera. Billy heard click a few times. 

"Turn over. Pull your hand out of the jock, spread your legs and lay a finger on your butthole."

"Whoa, I feel dizzy!"

More clicks. Billy could see the old dude's hard-on. "Now I want you to insert one finger up your hole."

"Big Jim. I've never had anything up there. I've never had sex with anyone and no not my ."

"That needs to change." Big Jim put some lube on his own finger and rubbed it into Billy's beautiful butthole. Then he took two of Billy's fingers lubed them up and shoved them in Billy's anus. He got hard instantly. Click. Click. It sounded like Big Jim was taking a lot of photos.

Finally Big Jim got what he wanted. Good photos. Billy was dazed.   "I'm heading home." I'm hungry. "Say Big Jim, do you think Sean O'Toole is gay or bi?"

"I wouldn't have a clue. Nice big dick."

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