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Welcome Back, Jack - Part 2

"Frustrated after a confusing encounter with her friend's dad, Jackie retreats to Trevor's room where the two catch up on life, school and romance."

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Author's Notes

"This is part 2 of 2 in a short story intended for adults. There are no plans to continue it any further. It features persons between the ages of 16 and 38 engaging in sexual acts that include, but are not limited to: Gay, Trans, Felatio, Cumplay. <p> [ADVERT] </p>Continue forward at your own risk. All characters are purely fictitious, any resemblance to an actual human being is coincidental. This story is copyright 2024 Bojac."

As soon as she got upstairs, Jackie flopped onto the bed and buried her face in Trevor's pillow. She didn't cry or mope, she was more confused than anything else. Everything had been going so well. Her heart was beating, her fingers started to tingle, and she felt alive. But just as she started to get intimate with that cute man, she found herself isolated and alone. It was exactly what she had been afraid of since she walked through the door. Jackie heard a creaking noise and lifted her head.

The door to the bathroom slowly swung open and hot steam poured into Trevor's bedroom. It rolled across the carpet like a deadly fog in a very low-budget film, and it was so thick that Trevor seemed to float mysteriously on top of it. His ankles were completely shrouded in mist.

As unusual and unexpected as his grand entrance was, Jackie was thankful for it. She needed the distraction. But still, she eyed her friend suspiciously. "You sleep like that?" she asked.

"What? Oh yeah, well not completely like this. I'll put something on after I'm dry," Trevor replied, dabbing at his hair.

He had emerged with only a big blue towel draped around his shoulders that hung down to his knees. He tucked it under his armpits and then joined her on the bed. His wavy black hair wasn't completely dry yet and dripped onto the sheets. Jackie turned her head away.

"I heard you made the cheer squad," Trevor said.

She shied away from Trevor's smile and gazed back down into the mattress. Tracing her finger over the neatly made bed, she said, "No, yeah, I did. It was hard—at first. In fact, they were mean. I don't think it was their fault though, they just haven't, you know, seen anyone like me before. But I'm glad I stuck with it, they're so nice to me now, like they're proud of me, like they think I'm brave."

"That's great! See? Everyone has always loved you," Trevor said.

"I don't want to be brave, I just want to be normal. Like I don't want this to be a big deal every time I try to do something."

"It's just the way it is, you'll get used to it. I'm just glad my dad wasn't weird with you though, I was worried about that."

Jackie sighed. "Yeah, I guess..."

"Wait, what's that look? Did he say something?"

"No, no! It's fine," she insisted.

Trevor stared at the sullen girl and eventually just shrugged his shoulders and let it go. They didn't say much for a while or do much of anything, really. Jackie scratched her calf with her toe and Trevor rang some water out of his wavy hair. He did it like a girl would, wrapping a corner of the towel around it and ringing it out. But his hair wasn't quite long enough to make it work yet since he had just recently started to let it grow. Eventually, when the silence got too loud, Trevor cleared his throat.

"So, do you like, have a boyfriend—wait you like boys right?" he asked.

"No..." Jackie admitted. "I mean, yes, I like boys, but I don't, you know have a boyfriend. And if I did—Trevor?"

Trevor snapped his head around after she'd caught him peeking at her bottom. He could only blush and look away. "I, uh... Yeah—no! I just..."

Jackie waited patiently while he tried to explain himself. But it was agonizing watching him stumble over his own words so she quickly put an end to it. “"Well, what about you?" she asked.

"Huh?"

"Do you have a girlfriend?"

"Oh, uh, no."

Jackie hit his shoulder. "Come on! I don't believe you. You're cute, I'm sure all the girls like you!"

The boy playfully rubbed at his skinny arm, pretending that her gentle touch had actually hurt him.

Jackie looked at him thoughtfully. "Do you at least like anyone? Are there any pretty girls at your school?"

He shook his head. "Kind of, I mean there are some people I think I like, anyway. But I'm not sure if they're into me, not like that anyway, and I'm not just going to go up and ask them either. I just get kind of nervous, you know?"

She scoffed. "Hello? You do see me right?"

"Yeah, but you're hot! So it's probably easier for you, I mean, I'm just kind of plain, and I'm still little. I still look like a freshman. But that's just how I look! I drive and I have a job! I think I make more money thank my uncle."

"Oh please, you keep saying that I'm hot—but you, you've always been cute. Remember Cynthia? And Alexis? Oh! And Jessica? Yeah, they were all in love with you."

"Yeah, like a thousand years ago! But now they all like older guys—much older guys. I think Sarah is dating our teacher, and she might even be a porn star already."

Jackie buried her face in the mattress and laughed. When she brought her head up and saw her friend fussing with his hair again, she took a quick peek back behind him. The towel loosely clinging to his body had wedged itself between his cheeks, making the contour of his bottom that much more obvious. He dabbed at his hair and then turned to her, but instead of being embarrassed about getting caught, Jackie just stared right back at him.

"You have a cute butt," she said bluntly.

"Yeah, maybe—wait! What?" Trevor's face turned the color of a tomato. He narrowed his eyes. "Jackie?"

But Jackie only doubled down and stuck her tongue out at the cross young man beside her.

"Jackie! What has gotten into you? Why did you say that, what did you mean?"

She blew her bangs out of the way. "What did I—really? I meant what I said, it's true." When Trevor cocked his head, she explained, "Look, I'm a girl now, right? I'm allowed to say stuff like that. If Cindy said that to you, you wouldn't be mad, would you?"

He shook his head.

"And again, it's true."

"Maybe," he admitted, "but girls don't really care about that, they don't notice it."

"Well, guys do—that's what I've found, anyway. And I bet girls secretly do too, I know I do. But seriously, everyone stares at me."

When Trevor made no reply, Jackie scooted a little closer to the center of the bed. She propped herself up on her elbows and inadvertently flashed the top of her cleavage. Jackie was oblivious and still not good at remembering how to behave like a lady. And she certainly had no idea how badly her best friend was struggling between his legs. The next question that popped into his mind just made it worse.

"Jackie, I was wondering... Have you like, kissed a boy? You know, since you've changed?" he asked.

Jackie curled some more wild strands of hair behind her ear. "One," she said, but offered nothing more.

Trevor beamed. "Oh my God! Who was he? You have to tell me about it! Jackie!"

"There's nothing to tell!" she insisted.

The bed rocked as Trevor positioned himself closer. He kept scooting until their hips touched and their shoulders came together. His bottom wiggled, and the towel crept further inside. "Please, come on!" he begged. "What was it like? Did he know that you're, you know..."

Jackie almost didn't hear him. She was distracted by the shape of her friend's lower back, marveling at how feminine it appeared even under the thick towel. There's no way she was jealous, Jackie reassured herself. She shook her head. "Huh? What did you say?"

Trevor didn't mind that she was interested in him, it actually flattered him. He arched his back and elevated his bottom. She might have interpreted that as something more, but he was just trying to get comfortable and free his erection which had become trapped between his thighs. It slipped forward and settled under his tummy.

When she realized he wasn't going to drop it, Jackie provided a little more information, hoping it would still his curiosity. "Well, it was my friend's brother—she's not a cheerleader. But still, I guess she's in that same circle. Anyway, her brother is our age and he, uh... He's cute, he kind of looks a little like... Like you in a way." She stopped and gauged her friend's reaction. It was a lot of information, a lot of very personal information that she knew she shouldn't be divulging. But she was glad to be rid of it, to get it out there as hard as it was. Jackie waited.

Trevor only blinked at her. His shoulders rose and fell as he breathed.

Each second that ticked by just compounded that awkward feeling in her stomach until it became unbearable. "Trevor, I'm... Was that too much? I don't know why I—ugh! This is so confusing!"

But the angry, scathing response she anticipated never came. Instead, she felt a hand gently touch down between her shoulder blades. "Hey," Trevor whispered, "what's wrong? Are you OK?"

"I just thought that you'd, I dunno, that this would be too much for you. You're not weirded out—are you sure it's OK that I'm sleeping over?"

"Yeah, why wouldn't I be? I've missed you, way more than you know. The only thing is, I'm kinda sad you didn't come to me first, I would have been there for you."

She caught herself nearly purring as his hand washed side to side between her shoulders. "Oh my God, thank you! And I know I should have come to you first, I was just afraid."

"Well, you can start by telling me what it's like to kiss somebody. I've, you know, never done that with anyone. Like who started it? And what does it feel like?"

Jackie considered. But just before she looked like she was going to share her secret, she closed her mouth. Jackie very slowly rolled over, making sure Trevor's arm stayed right where it was. When she was on her back and his hand resting just under her breasts, Jackie took a deep breath. "The thing you have to understand is that cheerleading uniforms are tough, and even tougher for me. The underwear is obnoxious, and I dunno—unpredictable! Every other type of girls' clothing I can figure out, and you know, hide myself. But not in those."

"But what does this have to do with—"

She swatted his hand. "I'm trying to tell you. Stephanie was driving us all home after practice. Her minivan was full, there were probably like seven or eight of us in there. And well, me and her little brother got the back seat since we'd be the last people to drop off. No one really noticed us. I was still new after all so it's not like they were constantly asking me for my opinion or anything. It was kind of nice to be invisible just then because I didn't want to be anywhere else than with him.

"Her brother was cute, but also really shy. Seriously, he's basically my school's version of you, and I was all alone with him. Then, out of nowhere, I felt his hand. He put it right here, right on my hip."

Trevor peered down in time to see Jackie guide his hand down lower. She set it on her jeans. "He just... He... Right here, like this?" Trevor croaked.

She nodded. "It scared the crap out of me at me first. I seriously couldn't even look at what he was doing. But then he started tapping me with his finger. I turned my head and immediately knew what he was trying to tell me.

"I was horrified! I thought I was going to die! Trevor it... My skirt was already too short, but it was crumpled up, and my... My... It slipped out of my panties and was kind of sliding down my thigh. And I didn't even realize it."

Trevor pumped his hips into the bed. He knew Jackie was watching his butt flex as it drove downward, and she might have even noticed the despondent look on his face, too. He shook his head. "Wait, seriously, how is that even possible? Like oh my God I can't believe I'm going to ask this, but how big are you?"

She blushed and tried her best to be modest. "What? No, it's not like that. I mean, it's just regular, I thought?"

"It doesn't sound regular—mine's regular!"

She rolled onto her side and faced him. His hand slipped onto the soft, white flesh of her waist. "Come on, I bet yours is beautiful. Why are you talking like that?"

"Because I've measured, that's why! Have you measured yours?"

"You have? Oh my God Trevor, tell me! How big is it?" Jackie asked, then slumped a little further forward.

He knew she was getting closer, almost climbing on top of him. He might have even been pulling her onto him. When he felt the top of her panties under his fingertips, he blurted out, "Four inches. I'm only four inches!"

"That's not bad. Hey, listen to me, that's perfectly normal. That boy I was with was probably the same size. And you're still in High School!"

He did a double-take. Then again. "Wait, wait, wait—wait a minute. You saw his too? I thought you said you just kissed?"

"Actually, I kind of lied. I still haven't kissed a boy. But I did, well, let me explain..." Jackie leaned a little further into him. And with each subtle detail of her story, she seemed to slip a little more. "This boy, Alex, he just rubbed my leg for a while, like right on top of my skirt. But after we dropped off the first girl, he started moving. Then, a little while later, I could feel his fingers on my skin. I wasn't even looking either. I was staring straight forward, but I could feel him down there, touching my thigh.

"Then, after the next girl left I remember watching her through the window. I remember the color of the ribbon in her hair and the way she was holding her backpack—I just had to look at anything other than what was happening under my skirt. Because, Trevor—" she gulped "—I could feel Alex's knuckles rubbing against me, against my...

"I looked over at him, basically shouting 'Are you crazy?' But he just carried on until his fingers were completely under my skirt. But there was something else. He'd undone his uniform too, and his dick was right there. When his hand started moving, I couldn't think straight anymore, so I just reached over and grabbed him, just like he was doing to me."

Trevor humped hard into the mattress only to find it wasn't only him. Jackie had mounted him and was pressing her pelvis into him. The small boy's eyes fluttered as he turned his head and rested it comfortably on his cheek. Jackie slowed her hips but didn't stop.

"Is this... Is this OK?" she asked.

But Trevor didn't hear her. His eyes finally opened, and they were full of anticipation. "Then what? What was it like—when you touched him?"

"Well, there's nothing like it in the world. I mean, I thought it was going to kill me. I thought I was going to pass out, I was so scared and nervous. But after a minute, I realized I loved it. I loved everything about it. I loved peeking over and seeing his face kind of, I don't know, fight it? Like he was trying so hard not to show he enjoyed it, especially since his sister and some other girls were in the car. I was jerking him off right behind them."

She halted again, but this time it was to spread her knees a little wider so she could get more comfortable. Jackie lowered her chest into Trevor's back. She was close enough that her lips hovered just above his ear.

"Keep... Keep going," Trevor whispered up to her. "What happened next?"

It was almost unbearable to see him like that. It was too similar to that boy she had been in the van with. But Jackie couldn't help herself then, and there was no stopping her now. She brought her mouth closer and whispered so quietly that he could barely hear her, "I'm so hard right now. Trevor, do you feel that?"

He grunted and raised himself into her, trying desperately to signal for her to continue, that he wanted more, that he had to know more. He had seen that outline in her jeans growing down her leg earlier, but now he could feel it. And as constrained as it was, he knew she was special. It didn't bother him at all that she may have been twice his size; it just excited him more.

"It was just like this when I was with Alex, it had gotten this hard and just kind of kept growing. It just wouldn't stop. Even as he held it in his hand, it got bigger. But, that's when—"

"Oh my God Jackie, just tell me, how big are you? Please?" Trevor said, interrupting her. His eyes flashed open and managed to stay that way. He lifted himself onto his elbows and craned his neck around even further. That distinct shape growing down her thigh confirmed everything he'd imagined. But still, that wasn't enough. "Come on, please?"

"I don't know, honestly! You're the first person who's ever asked. No, seriously!" she replied.

"Can you do this one thing for me? I won't ever ask again, and I won't tell anyone."

"OK... What?"

"Go into my desk, in the top drawer, get my ruler—and come right back. Please! Hurry!" he pleaded. Trevor did his best to point at the desk as if Jackie would ever have any issue distinguishing it from his dresser, bed, or even the picture on the wall.

Jackie raised herself and sat back on her heels. She waited awhile, unable to move, staring as if in a trance at what had become of his towel. She felt numb. The clean, blue cloth had scooted up all the way from the backs of his knees to his buttocks. And there, right between his milky white thighs, were his balls.

"Jackie!" the boy huffed.

"Oh right," she said, then got to her feet.

When she came back, she took...

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