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By TotallyNakedTom


Part One First Day of Class Show Off



They dropped Jason”s bag of clothes in the trunk and then went off in search of a restaurant for dinner. Along the way, Jason ogled some of the guys and some of the guys ogled Jason. Jason in his rainbow shirt with the cut sides, short shorts and flip flops was stunning enough to turn a few heads. Conner noticed the attention Jason was getting and he sidled up to Jason.

“Hey, I have a dare for you.”

Jason grinned a little. “What is it?”

“I think we should ask five strangers to guess what color your underwear is and if they guess right you have to show it to them.”

Jason”s little penis immediately jumped to life. That would be hot, so risky to show off his undies on the street. Then he thought, who would guess he was wearing rainbow underwear? The chances he”d even have to show off were so slim, but the thought that he might have to was so hot.

Jason nodded. “All right,” he agreed.


Conner stopped the first man who was walking by, a young 30-something Black man. “Hey, sir.”


“Jason here has to fulfill a dare. Would you help him?”

The man looked Jason over. “What do I have to do?”

“Guess what color Jason”s underwear is correctly and he has to show it to you.”

The man smiled. “All right.” He looked at Jason long and hard and said, “pink.”

Jason was about to open his mouth and say he was wrong when Conner said, “that”s right, there is pink on Jason”s underwear. Show him, Jason.”

And Jason”s heart sunk. Oh, shit. Conner had tricked him. He was going to accept any color that was on Jason”s underwear as a correct answer. And technically it was true. There was pink on Jason”s underwear. It was a technicality, but that technicality changed the game.

Conner turned to Jason expectantly, grinning and Jason took a deep breath and started to undo his shorts. Now that he was over the slyness of the trick, Jason was excited again to be doing something so risky and naughty. He lowered his pants while Conner and Devlin stood behind him, blocking him from view of the rest of the street. The stranger took a long moment, staring at Jason”s rainbow underwear and the distinct outline of his rapidly hardening cock. He smiled. “Yeah, there is pink on them.” And off the man walked. Jason pulled up his pants and buttoned them.

“That was awesome,” breathed Devlin. “Your ass looked amazing in those.”

Jason burned bright red. He looked to Conner. “I didn”t think all the colors on my underwear would count as right.”

“Of course, they do, why wouldn”t they?” Conner asked, as if Jason had been crazy to think otherwise. “But you”re right, if someone guesses that you”re wearing rainbow underpants I think you should have to give them a special sneak peek.”


“Yeah, I think if someone guesses you”re wearing rainbow undies you should lowered your undies and let them see what you”re working with.”

“No way!”

“Why not?”

Jason wasn”t sure what to say to that.

“Okay, what if they guess correctly, they get to cop a feel?”

“Over the undies?”

“If that”s what you want.”

Jason nodded. “All right. If they guess I”m wearing rainbow undies they can cop a feel.” That would actually be pretty mezitli escort hot, he thought, if that happened. I”d be standing with my pants down on the street while some stranger groped my cock through my undies. Fuck, that would be really hot.

They approached another guy walking down the street. He looked young and he was walking a small fluffy dog. “Hey,” said Conner. “How old are you?”

“Nineteen. Why?”

“Jason here has to fulfill a dare. Want to help him?”

The guy looked Jason over. “Sure.”

Conner grinned. “Guess what color his underwear is. If you guess correctly, he has to show it to you.”

“Blue,” said the guy.

“There is blue on Jason”s undies,” said Conner. “Show the man his prize.”

Conner and Devlin stood behind him again and Jason pulled down his pants, showing off his bright rainbow underwear with his pouch showing off the outline of his little dick.

“They”re cute,” the guy told him, moving on as Jason pulled up his pants.

“Two down, three to go,” Conner told him and Jason licked his lips and Conner and Devlin laughed.

The next two guys chose green and black. Jason didn”t have to show his undies to the guy who chose black since there wasn”t any black on his undies. Conner was a little disappoint about that so when they walked up to the fifth and final guy, a young Mexican dude in tight pants, Conner said, “hey, if you guess what colors Jason”s underwear is he has to show them to you.” And he ran a hand along Jason”s rainbow shirt.

The dude looked Jason over and followed Conner”s caressing hand. “Are they rainbow?” he asked.

Conner grinned. “You guessed it,” said Conner. “Show him, Jason.” And Jason pulled his pants down while Devlin and Conner blocked. “Also, since you guessed not just one of the colors but that Jason was wearing rainbow undies you get to feel him up.”

“Oh, really.”


“Is that true? I get to feel you up?” he asked Jason.

Jason”s mouth didn”t work very well so he nodded. The dude felt his chest, first through the rainbow t-shirt and then around through the slits, teasing Jason”s nipples. Jason hadn”t expected this but he sure didn”t mind it. The dude felt down, running his hands along Jason”s thighs, finally touching and squeezing Jason”s dick through his undies. Fuck. Jason was instantly hard. The dude started stroking his dick through his underwear and Jason moaned a little. Smiling, the dude slipped his hand into Jason”s underwear and started stroking him directly. Jason nearly fell backwards. Devlin and Conner held him up as this random dude on the street stroked his penis.

“Turn around,” the dude told him, and spun him so that Jason”s ass was by the dude. He pulled the back of his underwear down and slapped Jason”s butt cheeks, pulling them apart so that he could see Jason”s butthole. Jason hugged Conner and Devlin as they held him up and the stranger played with his ass.

The dude licked his finger and rubbed it against Jason”s butthole. Jason humped the air. He moaned softly into Conner”s ear. The dude teased Jason”s hole, grinning all the while and then removed his finger. He licked it, watching Jason compose himself. He wandered away, still grinning.

Conner and Devlin still held Jason, but his pants had fallen to his ankles, and he”d stepped out of them and his flip flops pozcu escort in his pleasure. His butt stuck out of his undies. Jason quickly pulled the back of his underwear back up, hiding his ass once more, stepped into his shorts and pulled them back up. He buttoned his shorts as he stepped into his flip flops, his face roughly the color of a tomato. Jason met Conner and Devlin”s eyes and they all burst out laughing.

“That was awesome!” Devlin cried as they continued on down the street.

“It was,” Conner agreed.

“That was so embarrassing,” Jason said.

“Sure, but it must have been hot too. It was hot for us,” Conner said. “I can only imagine what you felt doing it.”

“It was really hot,” Jason rubbed his neck. “I didn”t expect that to happen.”

“I kinda hoped something like that would,” Conner said.

“No more dares for the moment,” Jason laughed.

“No more dares,” Conner agreed.

They got dinner at an Italian restaurant.

“That was so awesome that you did that.”


“You”re the coolest. Honestly. Public stuff is really hot.”

“Yeah, it is.”

“Have you ever done public stuff before?”

“Like sex?”

“Sure, but also like exhibitionism? Have you ever shown off in public?”

Jason smiled. “Maybe.”

“Maybe?” Conner asked, smiling.

“Yep. Maybe.”

“Come on,” said Conner. “You have. You wouldn”t have done this today if you weren”t into it.”

“Well, yeah, I like it. I guess I”m an exhibitionist and I do like to show off so sometimes I do, well, get naked in public.”

“Tell us about it,” said Devlin.

“Well, there”s a hiking trail near my house in Conneticut. There”s a little tree house in the woods. When I was little I used to go there and after I left the trail I”d take all my clothes off and stuff them in my back pack and just hang out in the tree house, naked.”

“Did you touch yourself?”

“Sometimes. Sometimes I just hung out naked, read books, listened to music, you know like normal things, just I was naked.”

“Nice. So, you just like being naked?”

“Yeah, I do.”


They were seated near the bathroom and whenever someone passed through the swinging door they could see the guys peeing at the urinals. Devlin watched them a few minutes then he said, “hey, Jason. I”ll pay for your dinner if you go pee at the urinal with your pants and underwear around your ankles like a little kid.”

“I said no more dares,” Jason laughed.

“This isn”t a dare,” said Devlin. “I”m offering to buy you dinner if you do something for me.”

Jason grinned and sipped his wine.

“Hey, Jason,” said Conner. “I”ll get your drinks and your part of the appetizer and dessert if you take your underwear off under the table and hand it to me until we get back to the car.”

Jason looked at his two new friends and giggled.

“It”s not a dare,” said Conner, smiling and taking a drink of wine.

Taking a deep breath, Jason slid off his flip flops. “Yes,” Conner whispered. Jason undid his pants and pulled down his pants and underwear off and let them slide to the floor. He was now sitting in the booth, naked from the waist down.

Their waiter appeared. “Hey, how are you all doing? Do you need anything?” He was young, around their age and cute.

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Devlin tossed his napkin on the floor, below the table. “Could you get that for me?”

“Sure,” said the waiter and he bent to retrieve the napkin from under the table. As he bent he saw Jason”s pants and underwear on the floor and he looked slowly up Jason”s bare legs to his hard cock. “Oh, wow,” he said. He tried to stand up and banged his head on the table. “Ouch,” he backed up, rubbing his head. He handed Devlin his napkin. “Here you go, sir.” And he walked off.

Devlin and Conner burst out laughing while Jason hurriedly threw his pants back on and handed his underwear to Conner who tucked it into his pocket. “Hell yeah,” laughed Conner.

Jason drank the rest of his wine and downed half his water. He rose, straightening his shorts which had listed too far to one side and was showing off part of his scrotum and strode to the bathroom.

“Is he?” Conner asked.

“I think so,” Devlin answered.

Jason banged through the door, strode over to the urinal, opened his shorts and let them fall to his ankles. Thanks to the wine and water he”d been drinking so far, Jason had to pee. He let loose his stream, emptying his bladder. The door swung open behind him. He didn”t look back. The man who”d entered the bathroom snorted and took one of the nearby urinals.

The door swung open again. Someone took the urinal right next to Jason. Jason was deep into his stream, he had his eyes closed, the release felt so good. He opened his eyes and looked at who had come in next to him. It was the waiter. He had his fly unzipped and his penis out. He was stroking it slowly, looking directly at Jason. Jason smiled at him as he finished peeing.

“Can I shake it dry?” Their waiter asked.


The waiter reached out and took Jason”s penis in hand and started shaking the drops free. He stroked Jason”s penis a few times and Jason quickly grew hard. The man who was a few urinals away was watching avidly now.

“Can I?” asked Jason, reaching out but not quite grabbing the waiter”s dick.

“Sure,” the waiter smiled and Jason stroked his dick a few times.

The waiter released Jason”s cock and put his own away. He went to the sink, washed his hands and still smiling at Jason banged through the doors, exposing Jason”s bare butt to the restaurant again. Jason grinned and looked to the man a few urinals down. He had his dick out and was stroking it slowly. Jason smiled, bent, pulled up his shorts, went to the sink and washed his hands. He returned to his table.

Conner and Devlin slapped him on the back, laughing at his daring. “Damn, that was incredible.”


“You earned dinner.”

“Haha, maybe we can make it so I eat free with you guys all the time.”

They laughed. “We”ll see about that,” said Conner.

Their waiter arrived with their food. He winked at Jason as he set it down in front of them. Jason stuck his tongue out and the three of them at the table erupted into laughter.

After dinner they walked back to Conner”s car. They got in, Devlin and Conner up front and Jason in back. Conner pulled Jason”s underwear out of his pocket and handed it to Jason. Smiling happily, Jason kicked his flip flops off, pulled his shorts off and slid his rainbow undies on. Then he put his pants back on and slipped his feet back into his flip flops. Conner and Devlin watched Jason change in the rearview mirror.

“Money well spent,” said Conner and he pulled out and headed off for home.



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