Clara Teaches Her Younger Brother

(All characters are over 18)

My brother and I used to be close; best friends even. When we were little the age difference just didn't matter so much. Four years? That was nothing. We'd play little games together in the backyard, me always chasing him into some hiding place and him laughing until I could see tears on his cheeks. His name's Wyatt, I should probably tell you. I guess while we're on the subject, my name is Clara, I'm 22 but basically 40. I mean, I have my own credit card and everything, I have an apartment in New York City and I pay for my own cell phone. I'm an adult by all practical standards.

Anyway. Where was I? Oh right— Wyatt. Okay, so Wyatt and I were best friends. We'd have little sleepovers when we were young, and whenever he'd cry when our parents would yell at him, I'd comfort him. See? I'm a nice sister. I took care of him. I used to sneak him dessert when he'd get in trouble and they'd send him to his room.

You'd think with all that we'd be close now right? Well, guess what. We're not. We barely talk. It's weird. I try to text him like once a month, and he'll just give me nothing back. He just finished high school and I'm like, a little worried about him. He's never had a girlfriend (or boyfriend for that matter). He doesn't talk about dating or anything and I don't even think he's kissed anyone. I mean, as for me, couldn't be further from that. Let's just say, I have fun. I mean come on! I live in New York, I'm on the apps, and if I can be honest without sounding like full of myself, I'm kinda hot. I know I'm supposed to be modest and whatever but I do know I'm pretty blessed in the looks department. Not even joking when I tell you that I get asked to model like once a month by some rando art director on the street.

Okay I bet you want to know what I look like? So I have blondish hair that I dyed pink in some places, and it's pretty long. Like below my collarbones at least. People always tell me I have really puffy full lips, which I have to thank my mom for I guess. I'm white, but not pasty or anything. Pretty thin because I'm also a big time runner. I do a half marathon like two or three times a year. Runners always have pretty small butts but I never let that happen. My butt juts out. It's round. So even though I'm super thin my butt is defined, which I'm pretty fucking proud of. Don't get me wrong, I work on it. But still, some people do squats all day every day and their asses are just nothing special. I'm tall, like 5'10. I know I'm lucky there. I'd hate to be short. I have pretty long legs that are super toned, especially my quads. Google runner's quads if you want to see what I'm talking about. I have pretty nice tits too. They could be better. I always wish they were bigger, but no one's complained so far. I'm a 34C, though my right boob is slightly larger. No one else notices but I always do. It kind of annoys me, but whatever.

So yeah, I'm hot. I go on tons of dates and have my fun. But my brother Wyatt kind of worries me. He doesn't have a ton of friends and he just isn't out there in the dating department. I always try to talk to him about it but he blows me off, just shuts down the conversation every time. I don't know what else to do. I feel a little responsible you know? Like he's my little brother. I can't imagine being 18 and not dating anyone or kissing anyone and then going off to college.

So this is how I got into my current predicament, I'd say. Don't worry, I'll tell you all about my problem later. So I was texting Wyatt during the summer. Just like, how are you, how does it feel to graduate, blah blah blah. Of course he gave me like nothing back. He's so boring over text! But I was determined to try and talk to him about dating and stuff before he went to college. Mom and dad weren't going to, I knew that. Finally I just gave up until it hit me: maybe he just needs to come to the city, and we can have some fun here together. Then maybe he'll relax a little and we can talk. So I invited him to stay with me for a week in my apartment. I live with another girl, Sammy, who's a little older than me. She said she wouldn't mind. I told him he didn't have to hang out with me but could just get out of our boring as fuck home town and have some fun on his own in the city. That seemed to work.

So fast forward, a few weeks later there he was at Grand Central Station, just getting off a train. He looked messy and pretty miserable, I thought. Wearing his wrinkled cargo pants and a graphic tee shirt for some TV show he liked. I made a mental note: get him some better clothes while he's here. I went over to him and hugged him hard. It was like hugging a statue. He didn't move really. As I pulled away from the hug my button-up top got caught on the strap of his cross-body bag, and my top just pulled down. I laughed and moved towards him, trying to free the button, and noticed him staring hard at my cleavage. So he's probably not gay, I thought.

"How was the train in? Crowded?" I asked cheerfully.

"Yeah. It was fine."

"Did you talk to anyone? Meet any fun strangers?"

"What? No. That's dumb."

"That's not dumb, that's the fun part of going on a train! You can meet someone randomly. I get a lot of dates that way."

"Well I'm not getting dates on the train like you." He sounded bitter. This was definitely a clue to me.

I sprung for a cab to get us home faster. He slumped in the corner the whole ride. I tried to get him to chat or look at me, but nothing.

"So... what do you want to do this week? We can do literally anything you want." I nudged him in the rib.

"Ow. I don't care. Whatever you want."

"Maybe we could hang with some of my friends tonight? We're planning to go to a fun show in the city."

"I don't know, maybe..." he trailed off, staring at his phone and scrolling through Instagram.

I gave up and we sat silently the rest of the way. So what I didn't tell him was that this was a burlesque show we had tickets for. The chicks in these shows get like, almost naked, and act super sexy. I figured this would be something totally mind blowing for my little brother, and maybe a great way to loosen him up.

That night, my three friends came over before the show. We all had a few beers and I passed one to Wyatt. He tried to say no but when my friend Jenny gave him one, he abandoned his whole moody thing and actually almost smiled. Interesting, I noted. Jenny always makes people feel relaxed and brings like a ton of energy to everything. She's friendly, flirty, and pretty self-confident. She was wearing a shimmery silk cami and tiny black shorts. I watched Wyatt eyeing her chest and her ass whenever she got up. Her tits were smaller than mine but she always, and I mean always, wore a push up bra. Her ladies were totally out there on display. I wondered if Wyatt had a boner watching her. I know that sounds weird to say but like, I want my brother to get laid someday, you know?

I should say that I also was dressed pretty hot. White crop top, pretty low cut, and black leather wet look pants. My stomach was uncovered so you could see my tattoo, it's Donald Duck as a pirate. Don't ask me why, it's a long story. I sat next to Wyatt on the couch and noticed he let his arm brush against my stomach a few times. I figured that beer was starting to chill him out. He even laughed a little so that was a good sign.

We all took a cab over and I sat on his lap on the way there, so the four of us could fit in the backseat. I'll be honest, we were all pretty buzzed, laughing a lot and being so fucking loud. Wyatt even seemed to be smiling so that was great news for me. I leaned back on him every time I laughed.

My other friend Ava noticed this. "Aw. You guys are so cute!"

"I knowwwwww, aren't we?" I dug into him as I said this, hoping to annoy him but make him laugh.

"Stoppppp!" He said but I looked at him, he was still smiling.

"Hug meeeee..." I put his arm around my stomach and rested my head on his shoulder, pretending to nuzzle him. I was surprised that he actually hugged me back, pulling me into him. This was starting to work!

The show was exactly what I hoped for: steamy, fun, and dark. I knew Wyatt had never seen anything like this. I got him a drink and we all stood in a group near the stage, watching the dancers tease and strip down to just covered nipples.

"Having fun?" I poked him as I saw him like locked onto this dancer's exposed tits.

"This is pretty awesome," he said, not looking at me but his face made this kind of open-mouthed wonder look. I felt proud. I hugged him from the side and laid my head on his shoulder for a second.

I got bold. "I bet you wanna fuck her?"

He stopped gaping and looked at me, smile fading, eyebrows furrowed. "What? I'm just watching the show!"

"Wyatt, it's okay! She's hot. I'd do her!"

"Clara that's gross."

"Why is that gross? She's so hot! Don't you think so?"

He looked down for a second, breaking our eye contact. "I mean, I don't know?"

"Wyatt, Mom and Dad aren't here. You can relax. Don't you like her tits?"

"I said I don't know, why are you asking me this and being so weird?"

Just then Jenny interrupted us. "Hey, I think I'm gonna get going, my friend is at a party in Brooklyn and I kind of need to make an appearance."

I hugged Jenny and whispered into her ear, "Do me a little favor? Hug Wyatt really close and tell me if he's... you know. Into this." I knew I could tell Jenny this without being judged. She understood.

She turned to my brother. "Wyatt, so nice to meet you. Hope we see you again this week!" She went in for a hug and I saw her press her body into his. She held it for a while, released, and winked at me before leaving.

Moments after she dashed out, my phone buzzed with a text. "Boner for sure. Also u prob dnt wanna kno but hes defffff big [winky face emoji]"

I smiled big and looked at Wyatt. "Sooo do you have a girlfriend at home?"

"Nope."

"That's okay, perfect to go to college single and unattached, that way you're free for all the freshmen girls."

"Uh, doubt it."

"What do you mean? You're gonna have so many girlfriends!"

He took a long sip of his vodka soda and said again, "doubt it!"

"Come onnnnn of course you will."

"It didn't happen for me in high school so why would college be any different? I don't think girls like me and I really don't know what the fuck to do with them anyway."

"That's not true, all my friends kept telling me they thought you were cute." He looked at his feet as I said this. So, he just doesn't know how to approach a girl. I can help him there. "So you've never had a girlfriend?"

He shook his head. "Nope."

"Hmm. Okay. I'm gonna help you."

He smiled but tried to keep his lips pressed together. "What do you mean?"

"I'll teach you everything you need to know about girls this week so you'll be a fucking expert. How about that?"

"This is stupid. I don't need that."

"Don't worry Wyatt, I got you covered."

"You're my sister, that's fucking weird."

"No it's not, trust me. Have you ever kissed a girl before?"

His face was stern and embarrassed. He shook his head.

Ava was nearby, and I tapped on her shoulder. I whispered something in her ear. She looked at Wyatt and nodded. She walked over to him, put her hand on his jaw, and pulled his face to hers, planting a soft kiss on him. He was totally off guard and went limp in his body. Ava kept hold, continuing to kiss him kind of intensely. It looked like she was using tongue but I couldn't tell. She pulled away from him and looked him in the eyes. He was stunned.

"Well, now you have!" I said, and Ava and I giggled at him. He looked dazed and smiled big. Ava kissed him on the cheek and beamed at him, turning to look at me as she walked away.

We took the subway home, just Wyatt and me, and he seemed to fall asleep on my shoulder. I did good tonight, I thought. I didn't know how far I would take it, and I kind of wish I stopped after that night. Then I wouldn't be stuck in this situation right now. I know, you don't know what I'm talking about. Just listen, I'll get there, okay?

When we got home it was pretty fucking late and I was tired. I did not feel like dealing with the goddamn air mattress or making up the couch or any of that shit. I just got into bed and told him to go to the other side. Thankfully he didn't fight me on it. What's the big deal, it's just a bed.

I noticed he took off his shirt and pants, which I found a little weird. Shit, though, Jenny was right. He *was* big. I saw the outline of his dick through his boxers and it was thick. He didn't even look hard.

"Um, maybe you can wear some fucking pants?" I said, annoyed.

"It's so hot in here, I'll die. Just get over it."

I was too tired to fight him on it, and the bed was big enough. I turned off the light near me and fell asleep pretty quick.

***

I woke up before him and saw him over the sheets, on his back, passed out. I was groggy as fuck. I was about to turn over to sleep when I noticed he had a full blown boner. My eyes bugged out. I know I talk about wanting to help but this is like, gross. My brother's dick is like, right there. Okay this is kinda weird, I know. But after I got over the initial shock I was just a little curious. Like when you see a bulge like that you kinda have to check it out, ya know? Don't try to act like you wouldn't wonder about it.

So I turned toward him real fucking gentle and slid my nail under his waistband. I pulled his boxers over and down, not touching his hard on. I could be a fucking spy, I'm so good at this shit. My jaw just kinda dropped. There was his cock, looking like a man's dick on a boy's body. I'm sure I've seen bigger but like, so weird to see my little brother who's never been with anyone having this gigantic erection. He doesn't even know how lucky he is. I put his boxers carefully back over him and laid awake, confused. I just saw my brother's dick, I thought. I drifted off back to sleep.

The next few days, I won't bore you with. Like, not much happened. I think I got a little freaked out by what I saw and sorta backed off on the whole thing. We didn't talk a whole lot, and he just kinda did his own thing for a few days.

We came home from seeing a Broadway show a few nights later, and got into bed. I didn't bother with pajamas if he wasn't going to, just wearing a cotton bralette and panties. We were about to go to sleep when he said this:

"Your friend the other night. Ava. That was pretty cool, you know...I can't stop thinking about it."

"Oh yeah? She liked youuuu." I poked him in the chest and chuckled at him.

"What if that never happens to me again? It only happened because you told her to do it."

"Wyatt... of course that's gonna happen again. Don't be silly."

"You don't get it Clara. I don't know how to do stuff like that. I don't know how to talk to girls or kiss or anything."

"You talk to me though right?"

"So what, you're my sister. That doesn't count."

"But like what if I wasn't. I'm a girl, you're talking to me. It's not a big deal. If I wasn't your sister you'd seem cool to me and I'd be into kissing you."

Wyatt was silent after this, I think I surprised him a bit. "You would?"

"Yeah, sure. I mean, you're cute. What else do you need?"

"Okay but like, everyone my age has already done everything. I will be so inexperienced and that will be so embarrassing. It makes me not wanna talk to any girl."

"Wyatt, everyone goes through that. Everyone is inexperienced until they're not. You just need to have one experience and then you've broken the seal, and you'll know what to do." He didn't say anything, so I said: "What exactly are you nervous about?"

"Like everything. I don't know how to kiss good, I don't know what like a boob feels like, I don't know what to do to a girl, what if she thinks I'm gross like...down there? And I like, don't know what to do to like, have sex or whatever."

"Do you ever watch porn? Porn can sometimes help just to show you what it looks like."

"No... That's weird Clar."

I sighed a little, and then did something I really shouldn't have done. "Okay, I have an idea." I turned towards him, and got close to his mouth. I don't know exactly why I did this. I wasn't that drunk or anything. I think I just wanted to help him, but I know it was wrong. He looked at me confused. I leaned in further and kissed him. His mouth was kind of dry, and tight and stiff. Probably because he didn't expect his sister to kiss him. That's fair, I think. I didn't expect to be kissing my brother either, so, we're even there.

I put a hand on his chest and kissed him again. He relaxed a little, arms still at his side. "Wyatt. Put your arms around me and pull me into you. That's how you kiss a girl." He did what I told him. His hands were on my back and he sort of pressed them into me. Good enough, I guess. I slipped my tongue into his mouth. I figured he needed to learn, and I already got this far. His hands went soft and I felt his tongue on mine. We made out for a few more seconds and then I stopped it. I laid down on the pillow next to him.

"See? That wasn't so scary right?" He was just sorta staring at me, I had to try not to laugh. I mean he was cute and all stunned. "Now, you kiss me this time."

"Wh... what? We can't do that Clar."

"Just do it, who cares? It's just a kiss, and it's good practice. I won't tell."

He stared at me for a good 8 seconds, and I gestured towards me. He awkwardly climbed on top of me a bit, all twisted so his legs were still next to me. He kissed me. It was stiff again. I stopped him.

"Wet your lips. Make them soft. Then kiss me." I kept my voice nice and sweet, and I fixed his hair like a girlfriend would.

I closed my eyes. This time he did much better. The kiss took me by surprise, and I felt a shiver. His lips were tender, he licked my lip a little, then got a little more intense. He was definitely getting it. I pulled him in closer to me. I took his hand and moved it onto my right boob, squeezing his hand to help him. He got the hint. I felt electrified by his hand on my tit while we continued to make out. He was still a little timid so I lifted my bra up and put his hand on my bare chest. He breathed out really hard from his nose.

"Squeeze my nipple a little" I instructed him breathily, like a whisper. He actually did well with that and I found myself thrusting up toward him. My brother was turning me on. Shit. I knew, somewhere in my brain, that this was a bad idea. But who the fuck was going to help my pathetic little brother? Okay fine I liked it a little too. I actually had to stop myself from making noise.

My fingers scraped down his stomach til I found the tip of his cock and let me tell you, it was hard as ever. I gripped it over his boxers and he let out a very loud groan.

"Clara, what are you doing?" He said this kinda limp like, so I think he just was confused that it was me teasing his dick. I just kinda looked back at him, smiled and shrugged. I rubbed his package a bit and then decided to do something very bad.

"Get on your back," I told him. He did exactly what I said, looking to me for instruction. I pulled his boxers down and his dick just popped out. It was veiny and swollen and honestly, one of the nicest dicks I've seen. "You have a huge fucking cock, you know that?" He smiled big at me. "I'm going to give you a blow job. Don't cum, okay? Promise?" He nodded helplessly.

I decided not to give him my best dick sucking performance ever. I didn't think he could handle it. I figured he was going to pop at any moment. So I just licked the tip a little, then put it in my mouth. I had a hand around the base of it but I knew if I jacked him off he'd explode. I sucked a bit, taking in like 2 inches of his warm dick and bobbing my head a bit. I looked up at him with innocent eyes and he just sighed loudly. I could tell he was fascinated seeing his swollen dick disappear inside his older sister's mouth.