Tomboy Titties

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

He was spent and needed to rest some more. But the sight of Cathy moving up the trail toward him sent a rush of fear racing through him. He threw his water bottle down to the side of the trail, let out a loud battle cry, and ran up the trail like his life depended upon it.

As he made it closer to the top, he barely had any energy left in him. His battery was completely drained. He could no longer run. He couldn't jog. He could barely walk. He lurched forward like a zombie. Each step took a massive amount of effort. His breathing was fast, deep, and heavy like he was on the verge of hyperventilating. His heart pounded in his chest. But he eventually made it to the top and placed his hand on a rock at the highest point of the hill.

In any other circumstance, he would have danced around with his arms up in victory, but he was so exhausted that all he could do was lay flat on the ground. Titties, he said softly to himself. Titties.

About ten minutes later, Cathy finally made it up to the top of the hill.

"Good game," he said raising his hand in the air and she slapped it as hard as she could.

"Good game," she begrudgingly replied.

"I won."

"I know!"

"Well?"

"Right here?"

"Sure. No one's around."

Cathy scanned around her and he was right. There was no one else around.

"All right! Fine!"

Teddy quickly got up and sat down Indian-style right in front of her. She lifted her t-shirt exposing herself for a split second. It was quick, and her titties were covered by a tight, black sports bra causing Teddy to whine and complain.

"Oh come on! I ran all the way up the hill. I deserve at least a count of ten."

"Five."

"And you have to pull up your bra too."

"What?"

"That was part of the bet. You knew that. Oh, come oooooon!"

"All right. All right!"

She lifted her shirt and then pulled up her sports bra as well. Her beautiful titties dropped and bounced into place almost in slow motion. They were so perky that they stood out on top of her chest like they defied gravity. The sight of Cathy's titties took his breath away.

"One, two, three, four, five," Cathy counted out loud and then turned away from Teddy to cover herself back up again.

"I can't believe you made me do that," she said and then she screamed out. Her cheeks were flush but she was smiling and looked more excited than anything else. "I can't believe I just flashed you. I've never done that before."

"You should do it more often. You're really good at it."

"I am?"

"Yeah," he said then he thought about it again. "Well, actually. No. Never mind."

"What? Tell me!"

"It would have been nice if you gave them a little shake. Your titties look really good when they jiggle."

"Okay, thanks," she said sarcastically and stuck her tongue out at him. "Good to know."

"But honestly, Cathy. Your titties are very pretty. They're fucking beautiful."

"Best titties, you've ever seen?"

"Best titties ever."

Teddy stood up and immediately got a boner. His shorts started to tent up. It was embarrassing but more than that it was uncomfortable for him to stand. There was no way that he could walk, so he stumbled over to a rock at the side of the trail and sat down.

"You okay?" she asked.

"Yup, just resting. All good."

Cathy stared at him for a moment. He was hunched over and was trying to hide his crotch.

"Did you get a boner? Are you sitting down cause you got a boner?"

"No. I'm just more tired than I thought. My legs gave out."

"Oh my god, Teddy," she said with a big smile on her face. "Did I just give you a boner?"

She went over to him and grabbed his arms. She spread them out and made him sit up so that she could look at his crotch. His shorts were tented up holding back a huge boner.

"Oh my god, I gave you a boner," Cathy screamed out.

"Get off me," he said and pulled his arms back down to cover himself back up. "Will you just give me a minute? Will you? Will you give me a minute?"

"Sure, whatever you need," she said with a mischievous smile. "By the way, how long does it take for a boner to go down?"

"I don't know. Will you just chill? Will you? Just chill and enjoy the view. All right?"

Cathy stayed quiet for a moment. She smiled like she was holding something back. Then, she cracked up.

"Dear diary," Cathy said. "Today was a very special day. I'll remember it for the rest of my life because today, I gave Teddy Kim a boner."

"Shut up!" he said as he laughed. "Don't be stupid."

They rested for a moment staring out at the valley below. The view was amazing. Life wasn't too bad, Teddy thought. After they rested some more, his boner finally went down to half-mast. It wasn't down completely but just enough to get up and start walking again.

"Okay, I think I'm ready," Teddy finally said.

"Finally," she said and got up. "Race you back down?"

"Okay."

"Last one down buys lunch?"

"Deal."

"I want a hamburger. No, a cheeseburger. I want a..."

"Hey, you can't say that yet..."

"Teddy," she said making him turn to her. She pulled up her shirt and her sports bra again exposing her perfect titties to him. She shook her chest back and forth making them jiggle. Teddy froze in his tracks. His erection came back in full force. Cathy laughed as she watched his shorts tent up again. He sat back down on the rock he had just gotten up from.

"Damn it! Cathy!" Teddy yelled out as he covered himself up again.

"Was that better? Did you see? I added the shake."

"Yeah, I saw. And yes, it was better. It was fucking perfect!"

"That's what I thought," she said as she skipped down the trail. She turned around and yelled out, "I want a hamburger. No, a cheeseburger. I want a hot dog. I want a milkshake. I want potato chips."

"You'll get nothing and like it," he said quietly to himself. It was half-hearted because he knew it was a lie. She would get whatever she wanted. All she had to do was show him her titties. Oh shit, he thought. Oh, shit.

Tennis

They saw each other a few days later to play a game of tennis. Once again, Teddy tried to act normal, but he couldn't, especially after what had happened on their hike. He had seen her titties three times by then, but instead of curing his curiosity, it did the opposite. He wondered about them even more.

At that moment, all he could think about was touching them. He wanted to grab them and play with them. He could only imagine how good they felt. He would die happy if he could touch them just once, he thought. And if he never got to touch them, he would be left wondering for the rest of his life. The thought drove him crazy. It drove him mad. He was completely obsessed and as they warmed up hitting balls back and forth to each other, touching Cathy's titties was the only thing on his mind.

He couldn't concentrate on anything else. He miss-hit a shot, and it bounced off the rim of his racket sending it over the fence into the other courts. There were three other courts and they were all occupied with other players. The ball landed in the middle of a heated point between two older guys. They had to stop playing to retrieve Teddy's miss-hit ball.

"Fuck!" he yelled at himself. Then he turned to the other players, "Sorry about that."

One of them hit the ball over the fence back to Teddy.

"Why are you playing like shit," Cathy yelled over. "What's wrong with you?"

Teddy looked over at the other people playing and motioned for her to the benches where they sat down and rested for a minute.

"I can't stop thinking about them," he admitted to her.

"What? My boobs? Still?"

"Yeah, it's getting worse. I'm totally obsessed."

"You want to see them again?"

"Yeah, but now I want to touch them too."

"What? Yeah, I don't think so. That's too much."

"Please, I'm begging you. The curiosity is killing me."

"What are you so curious about?"

"I'm dying to know what they feel like," he said. "Ever since I was a little kid, and I saw my first pair of big titties, all I've ever wanted was to touch them. Touch them just once. And yours are so big and beautiful. Feeling your titties would be like a dream come true."

"You're such a horndog. I swear."

"Seriously. I've never begged anyone like I'm begging you," he said and then got down on his knees in front of her. He put his hands together as if in prayer. "Please, Cathy. Pleeeeeeease."

"Teddy," she said looking around at the other people playing on the other courts. "Get up."

"Just let me touch them once. Just once."

"God, you really want to touch them that bad?"

"What about we make another bet?"

"Bet what? A game of tennis?" she said laughing to herself a little. "Are you serious? You think you can beat me?"

"Just give me a chance. That's all I'm asking for."

"What's the bet?"

"If you win, just like before, I'll stop talking about your titties. I'll erase them from my memory and just deal with it," he said looking up at her still on his knees. Cathy stayed quiet. "But if I win, I get to touch them. I get to touch them under the shirt."

"Under the shirt? Not even!"

"Just for like five minutes."

"Five minutes! That's way too long."

"Fine, then. One minute," he said. "You're way better at tennis than I am. You beat me all the time. You beat me, like what, four times out of five."

"More like nine times out of ten."

"So, what are you worried about? You're not chicken are you?"

"I'm not! I just don't want to hear you cry after you lose."

"I won't cry. There's no crying in tennis."

"Stupid."

"So, it's a deal?"

"Fine! Deal!"

Teddy extended out his pinky and Cathy grabbed it with hers. Then they both got up from the benches and made their way to their side of the tennis court. He got into position and readied himself to play the best game of his life.

She didn't hold back either. Her first serve rocketed over at him, but he was ready for it. He moved his feet in little stutter steps like he had been taught and hit it back to her forehand. The ball landed in the corner. It was an excellent shot. Cathy backed up but was late and had to overextend her arm. She took a swing. The ball came back low and into the net.

Teddy didn't celebrate. He didn't want to piss her off in that way because it only motivated her to play harder. Instead, he just gave her a nod, moved to the other side of the court, and got ready for her next serve. His focus was crystal clear. His attitude was dead serious.

Since she was better than him, he had to play as smart as he could. Her backhand was more consistent than her forehand. So he made sure to hit the ball back to her right side and kept it away from her left. He also noticed that when he hit it back to her with a lot of power, she would use that energy and slingshot it back to him with twice the force. But when he hit it soft, she would try too hard to slam it back at him. The ball would either hit the net or go long. When she did manage to hit a good shot far outside of his reach, he let it go instead of chasing it down so that he could conserve his energy.

He stayed in control of his emotions as well. He didn't let himself get too excited when he won a point, and when he lost, he didn't let himself get too down. When she tried to taunt him, he just brushed it off. When she started to build momentum, he'd give her compliments which confused her.

"Nice shot!"

"It was in! That was obviously in!"

"I know. I said, nice shot! That was a really good forehand!"

"Oh, okay," she said staring at him suspiciously.

While Teddy controlled his emotions, Cathy's got the best of her. She was frustrated with the fact that Teddy was winning and confused about the way he was treating her. And it showed in her game. She tried to beat him with overpowering strength, but she ended up overplaying instead. She tried to force her game which caused her to make a lot of unforced errors.

Teddy, on the other hand, played well above his abilities. He was in a zone, physically, mentally, and emotionally. His play was inspired. At times, it was even brilliant. The possibility of touching Cathy's titties brought out the best in Teddy.

In the end, the score was so lopsided that there was nothing that Cathy could do. She eventually gave up and on the last point, she lazily hit the ball into the net.

"Good game," Teddy said as they both met up at the center of the court. He extended out his racket for a high-five, but she didn't respond. "Seriously? You're going to leave me hanging?"

"Good game," she finally relented and high-fived his racket with hers. "You suck. I hate you."

"What? What did I do? It was a fair game. I played my heart out," he said. "And I haven't even said shit to you. I'm being totally cool about it."

"You're right. You're right. I can't believe I'm saying this but you played a really good game," she said. Then almost to herself, she added, "God, you must really want to touch them."

"Oh shit, I almost forgot. I get to touch your titties," he said as he reached out for her chest.

"Oh my god, Teddy! Not here," she said. Her eyes went wide as she pushed his hands away and covered herself. "In my car, you fucking horndog!"

Teddy grabbed all of his gear and quickly packed his things up. Then he raced over to Cathy's car and stood by the passenger door waiting patiently. Cathy shook her head as she took her time.

When they sat down in the car, she turned her body to the side so that she was facing him. She took out her cell phone and set the alarm for one minute.

"Go ahead."

"You're not going to pull up your shirt for me?"

"You have one minute," she said and then hit the timer on her phone. "Starting now."

He quickly pulled up her t-shirt and then pulled up her sports bra. It was tight, and it took him a few seconds to expose her breasts. He knew because she kept count.

"Fifty seconds," she said.

He looked at them for a split second. He had already seen them before and wanted to touch them more than anything. So he held is breath and dove in. He reached out and grabbed them. He was a bit too enthusiastic, and it caused Cathy to flinch away from him.

"Easy, they're not basketballs," she said. "Forty seconds."

"My bad," he said and was more gentle with the way he handled them. He first gave them a pet like they were cute little puppy dogs. He stroked the top of her titties. Then the side. Then he cupped the bottom of her boobs. He lifted them just to feel their weight. Damn, he thought. They were hefty.

Then finally, he squeezed them. It was what he had been fantasizing about ever since he saw them, and they felt better than he could have ever imagined. They were so freaking soft and felt so good in his hands that he got rock hard right away.

"Thirty seconds."

Then, he played with her nipples. He pinched them and flicked them causing Cathy to flinch and let out a surprised squeal.

"Teddy!"

"What? They're part of your titties."

"Fine. Twenty seconds."

He went back to squeezing her titties. They were larger than a handful, and he squeezed them together. There was so much cleavage and her nipples almost touched. The sight almost made him lose his load.

"Ten. Nine. Eight..."

For the final seconds, he just held them softly in his hands and tried to cherish the moment as best as he could. He closed his eyes so that he could better concentrate on the feeling of holding her beautiful titties in his hands. They were so big and soft and her nipples were so hard. He felt like he was about to explode.

"...Three. Two. One. Time," she said.

He lifted his hands off of her like he was putting up his pencil after a test. She took a moment to put her titties back into her sports bra. She scooped them back into place and made a few more little adjustments until she was comfortable again.

They sat there for a moment. Teddy's eyes were still closed as he relived the memory over and over again. He did his best to memorize every little detail. He tried to soak it all in.

"That was kind of a religious experience," he said putting a hand to his chest. He bowed his head a little. "Thank you."

"Dork."

"What? It's not every day, a dream comes true."

"Okay. Okay, whatever," she said. "Now, show me yours."

"What? I mean, I don't mind but why?"

"We'll be even then."

"Even?"

"Yeah, the next time we see each other, I'll be totally embarrassed. And you'll be fine. It won't be fair. But if I see yours then we'll both be embarrassed, and it'll be even," she said. "Besides you said it yourself. If you had titties, and I wanted to see them, you'd totally show them to me. Like all day, I think you said. Come on dude, let me see your cock."

That made him crack up. Fuck it, he thought and unzipped his tennis shorts and pulled them down with his boxer briefs. His cock sprang out like an eager soldier standing at attention.

"Is it always like that?"

"No, playing with your titties got me all excited."

"I swear, you're such a horndog," she said. "Okay, I'm going to touch it now."

Teddy shook his hips from side to side making his cock flap around. She laughed and gave him a playful slap on his shoulder.

"Stay still."

Cathy held her breath as she reached out and touched his cock. Her fingers lightly glided over the tip and then down the shaft. She took hold of his shaft and gave him a few pumps. Then her hand went down even further until she reached his balls. She played with them almost like he had played with her titties. She lifted them to feel their weight. Then she gave them a little squeeze.

"Easy," he said mocking her. "They're not basket..."

"Shut up or I'll stop."

He did exactly as he was told and didn't say another word. Instead, he leaned back as she stroked his balls. Her fingers glided up and down them. She cupped them and held them softly in her hand.

"Okay, I'm done," she said. Then abruptly, she took her hand off of him and started up the car.

"What? Wait... But still.... That felt... Damn it," he said. All he could think about was how her titties just felt and how it felt having her hand on his cock. He was having a hard time thinking about anything else. "You can't just leave me like this."

"I never said I'd jack you off," she yelled. Though she acted like she was angry, it didn't look like she was mad. Her face was flush and she was holding back a smile. "No way!"

"Cathy, you're killing me. I'm dying. I'm dying!"

"Gross. Jack yourself off."

And that's exactly what he did. As soon as Cathy dropped him off at his home, he raced to his room and jacked off. It didn't take him long to finish, but even after he came, he still felt frustrated. This time, jacking off didn't release him from his desires. It just stoked the flames. He jacked off again but still, his balls ached.

It was then that he realized that he had blue balls and that feeling wasn't something that he could get rid of by himself. Cathy was the only one who could release him from the tension that he was feeling. He started thinking of all the ways, she could give him some relief and his imagination took over. Oh fuck, he thought. Oh fuck.

Movie Night

Other than their competitive nature, they also liked to watch movies together. They liked to watch sci-fi, horror, comedies, and old cult classics. They watched everything except for girlie flicks and romances.

Teddy's parents were out to dinner at a friend's house and would be gone for most of the night. It was a perfect time for them to catch up on some movies. Teddy was also hoping for more, but he wasn't sure what that would be. He was frustrated but also a little confused.

All he knew was that he felt like being nicer to Cathy. In the afternoon, he went to the local Asian market on his bike to get snacks and drinks that he knew she liked. When he got home, he cleaned up the family room and even took a shower.