Prison Break

Josh Bishop scowled as his big sister, Paris, made him sit in a chair in timeout, basically.

He’d been talking innocently with Madison Cole (one of the very few girls he could talk to like a relatively normal person) when Paris came over and got upset at Josh for apparently flirting with her friend.

Josh had no idea what that was about, and had gotten angry at Paris.

Paris had then proceeded to make herself Josh’s warden, while a bunch of Josh’s friends and family got to hang out at the party. True, he wasn’t really a partier, but being told he can’t do something really makes that something seem appealing.

His cousin Zack and his hot girlfriend Grace had come by, and then he’d watched Zack go and dance with his mother, who was Josh’s Aunt Monica.

Grace had come back during that time, and discovered Zack gone.

She walked up to Josh.

“Have you seen Zack?” she asked, her green eyes a little worried. Grace Smith was a stunning young woman, and her red dress really accentuated her large tits.

“U-uh, yeah. He went off with his mom.” Josh stammered. The worry in Grace’s vivid eyes cleared up, and she dropped down into the seat beside Josh.

“I’m not big on parties.” Grace confessed to Josh. He glanced at her, unsure why she had chosen to spend time with him. Josh glanced to his right where Paris was distracted talking with a muscular boy with short black hair and tanned skin.

“Y-Yeah, me neither.” Josh admitted.

“Why are you here, then?” Grace asked curiously.

“Uh, my sister made me come.” Josh nodded his head towards Paris.

“Zack made me come. He thinks he’s still the same introvert who he was in high school. He doesn’t realize just how confident and extroverted he’s become.” Grace confided.

“Yeah, he didn’t u-used to be that confident. Or that jacked.” Josh said. Grace laughed.

“Oh, I remember.” she said.

Josh was amazed that he’d made a hot girl like Grace laugh, even if she was his cousin’s sexy girlfriend.

“D-Do you miss him the way he used to be?” Josh wondered, unsure why he wanted to know.

Grace considered that question.

“Maybe a little bit. But I think if I had dated him back then, neither one of us would have grown at all. We were too similar. Now, though, Zack pushes me into growing as a person, even though he has no clue.” Grace said fondly.

Josh glanced over at Paris, and then back at Grace.

“C-Could you do me a huge favor?” Josh asked.

“Depends.” Grace said, smiling, “What do you need?”

“Can you distract my sister so that I can break out of prison?” Josh asked hopefully, and realized that he didn’t stutter once during that sentence.

“Consider it done.” Grace winked, “See you later, Josh.”

Grace got up and went to stand near Paris, at a certain angle so that she wasn’t facing Josh at all. The two girls started talking, and Josh made his mad dash for freedom. Not willing to cross the whole party room, he ducked instead to the ballroom, skirted around the edges, and made his way to the other room full of people, not the one where Grace and his sister were.

This room seemed to be more full of adults than teens, though there were still plenty of teens.

Josh noticed a woman he recognized holding a glass of wine.

The woman had long, wavy cherry red hair, blue eyes, large, ample breasts, and a firm ass. She was Gemma Harlow, the bitter rival of Josh’s Aunt Monica.

Josh moved away from her quickly. Ms. Harlow had a reputation in town, and he definitely didn’t want to get wrapped up in any drama.

That’s about when Josh spotted his biggest crush standing alone.

Josh hurried up to Chloe McRose, and gave her a shy smile.

“Hi, Josh!” Chloe said brightly, “I’m not sure where Holly is.”

“O-oh, that’s alright. I’m not really friends with anyone here. Do you mind if I h-hang out with you?” Josh asked nervously.

“Not at all.” Chloe smiled. God, she was stunning.

“C-Cool. So, uh, how’s Breakwater?” Josh asked.

“Oh, it’s great!” Chloe enthused, “I’m on the soccer team, and I’m also kind of getting into chemistry. So, how’s high school going for you?”

“A-alright. I kind of wish I had more friends, but, uh, yeah.” Josh said awkwardly.

“I remember what it was like only having Zack and Gavin as my friends.” Chloe sympathized, “It’s great having a few friends you’re really close with, but I get what you’re saying.”

“Yeah.” Josh said, looking down. Chloe glanced towards the ballroom, and then back at Josh.

“You wanna dance, Josh?” Chloe asked.

“U-uh, sure.” Josh smiled nervously, and Chloe took his hand and led him out on the dance floor. She looked incredible in her white dress. Chloe lifted both arms and slid them around his neck, and Josh put his sweaty hands on her hips. Chloe smiled at Josh as she stepped closer, so that Josh’s arms weren’t so far out.

The dance felt more personal now, as Chloe swayed to the music with Josh. He had never danced before, so he was hesitant, but fortunately, Chloe seemed fairly experienced.

He wondered where Chloe had dancing experience from.

The front of Chloe’s large breasts brushed against Josh’s chest as they spun for a particularly upbeat part of the song, and when it went back to slow, Chloe didn’t move back, which meant Josh could feel his crush’s large tits. It was an insanely good sensation, but one that was making Josh’s dick rather stiff in his pants.

Chloe was smiling the entire time, and Josh couldn’t help but smile back at her.

“It’s strange, we’ve never really hung out, despite my little sister being your best friend.” Chloe said.

“I… yeah, you’re right.” Josh nodded, “I g-guess you were always busy with Zack.”

“I guess so. You seem like a nice guy, though. You remind me of Zack a little bit back when he was your age. Quiet, shy, and you look like him too.” Chloe teased.

“I look like him?” Josh repeated. Chloe nodded.

“Yeah, handsome in the geeky sort of way.” Chloe said thoughtlessly.

Josh stared at her, and Chloe laughed.

“Joshua Gabriel Bishop!” a woman’s voice exclaimed loudly, and Josh turned sharply to see his aunt Monica, looking heaven sent in her tight maroon dress with that plunging neckline, baring vast amounts of her large breasts to onlookers.

“Your sister told you to stay put, and you snuck off?” Aunt Monica demanded. Josh and Chloe had stopped dancing, and Chloe looked on the verge of laughter.

“S-sorry, Aunt Monica.” Josh said nervously.

“I hate to steal your dance partner, Chloe, but I’m afraid I need to chew Josh out.” Monica said warmly to Chloe.

“It’s no problem.” Chloe laughed, and she waved a goodbye to Josh before walking off.

Monica led Josh to an empty side room, and closed the door behind her.

Josh turned to Monica, and Monica’s icy blue eyes flicked down to Josh’s cock, which was still rock hard.

“Are you…” Monica trailed off. Josh flushed darkly.

“Was it me or Chloe?” Monica asked in a teasing tone. Josh’s eyes flew open and he stared at his aunt in horror.

“Well, answer the question.” Monica said. She glanced down at Josh’s still rock hard cock, and smirked.

“Never mind. I think if it was for Chloe, it would have gone by now.” Monica teased. Josh’s cheeks grew even darker red, and Monica sauntered closer. Josh wasn’t the tallest guy, so he was about eye level with Monica’s gorgeous large tits, which didn’t help his boner.

“Maybe you are pretty into me.” Monica noted, and Josh hastily tore his eyes off Monica’s tantalizing cleavage.

“I-I-I… I’m so sorry.” Josh despaired. Monica reached up and stroked Josh’s cheek, making a soft sound.

“Josh, listen to me carefully. I am not even slightly upset with you.” Monica said, and Josh looked up from the floor at his gorgeous aunt.

“You’re not?” he asked weakly.

“No, sweetie.” Monica said softly, “I know a thing or two about teenage boys. Besides, I made Zack hard plenty of times when he was 18, just like you. It’s a natural biological reaction.”

“I… I guess so.” Josh stammered.

Monica smiled warmly at Josh, a bit of sadness in her eyes.

“I’m so sorry that Louise wasn’t around for you. She was an amazing woman, and I think you would have loved her being your mother.” Monica said gently, “I’ve tried my best to make you feel like you always had a maternal figure, and I know Charlotte feels the same way.”

Josh gave his aunt a warm smile.

“Aunt Monica, you’ve been the best mother a boy could ask for.” Josh said. Monica’s eyes teared up, and she pulled Josh into a tight hug. Remember where Josh’s eye level was?

Josh’s face was pulled right into his aunt’s massive tits as she hugged him tightly, and Josh wrapped his arms around her, too, rather enjoying the feel of his head nestling into her cleavage.

“Oh, I guess you’re liking the hug.” Monica giggled, and Josh realized he was hard again.

Josh stepped back, looking terrified.

“Don’t worry, honey. I’m still not mad.” Monica said in a soft, sweet voice. Josh’s cock gave a throb at her tone, and she clearly saw it.

“You know, there’s something of a tradition in my family that came about my complete accident. A lot of us had our first kisses from family members.” Monica said.

“W-What?” Josh blinked.

“It’s true. My first kiss was my big sister, Mallory. Zack’s first kiss was his cousin, Mia. My little sister, Misty’s, first kiss was with our cousin.” Monica said, “Have you had your first kiss yet?”

“N-no.” Josh admitted, embarrassed. He was 18 and had never kissed a girl.

“Hmm… I think I can help you out there.” Monica said softly. Josh’s eyes widened as his aunt winked at him and leaned in to kiss him.

Josh’s lips brushed Monica’s, and he gave a shocked sigh of enjoyment, and then Monica kissed him properly.

She had to lean down a little bit to do it, and her tits pressed firmly against Josh’s chest while his aunt kissed him.

His cock was rock hard and throbbing while he kissed his aunt back with everything he had.

“You’re a good kisser.” Monica complimented when she drew back, “Are you sure you didn’t lie just to kiss me?”

“I-I’m sure.” Josh stammered.

“Alright. So, good first kiss?” Monica asked gently, cupping Josh’s cheek.

He nodded eagerly. Monica smiled and went in for a hug, but Josh leaned up and kissed his aunt on the lips impulsively. She gave a surprised hum, but then she kissed back eagerly. Josh stumbled a little bit, having to lean up awkwardly to kiss his mother, no… wait, she wasn’t his mother. She was his aunt, despite his very maternal feelings otherwise.

Monica and Josh kissed for a good while, and when Josh drew back, he was panting hard. Monica stroked his cheek.

“You’re really good at kissing. You’re going to make a girl very lucky someday.” Monica teased.

“T-thanks.” Josh said, flushing a little bit. Monica winked and leaned down to plant another kiss on Josh’s lips, this one quick and gentle.

“Whenever you wanna practice, you know where to go.” she smirked, and then walked off, leaving Josh standing there with an achingly hard cock and tingling lips.