My Sister Wears Boxers?

"Come on Tony, it's your turn!"

"Alright, dare," I said, leaning back again the wall. My friends and I were enjoying an otherwise quiet summer night by playing truth or dare. You'd think we would have outgrown it once we turned eighteen, but somehow that only made the stunts we did even more ridiculous. Gone were the days of calling a girl's house and hanging up, replaced now by streaking in front of their house and running as fast as we could.

Same idea, more or less.

"Dare..." I said. Jonathan seemed to give it some thought before a light bulb went off in his head. "Alright, well here's an easy one for you. Go grab us a pair of Ruth's panties."

"Yeah!" came the chorus from around me. Everyone seemed to think this was the best idea of the night.

In response, I just groaned. "Really? You want to see my sister's panties? That's a little... I don't know, childish. Plus, if she catches me, she'll kill me." Ruth was only two years my senior, but she played lacrosse in high school and college, and could pin me in a second if she wanted to.

"So don't get caught," Jonathan teased. He threw a solo cup at me, which I barely deflected. It seemed tame enough, so I shrugging, got to my feet, and walked out of the basement to the cheers of my friends.

"So stupid," I said under my breath. "But at least it's an easy dare. Maybe I'll make Harry wear them for the night, get some blackmail on him next time he doesn't feel up to buying the pizza."

I made my way upstairs — my parents were out at some dinner party, and Ruth, thank god, was out with friends of her own. There was a chance I would have just asked her for a pair to borrow and she might have relented, but I was glad I didn't have to take that risk. Pushing the door open, I made my way into Ruth's room. It was a standard room by all accounts, single twin bed, blue walls and a few bits clothes thrown about. I made my way to her dresser and started to open drawers until I found her panty drawer.

"What the..." I started as I rummaged through them, careful not to mess up the folding too much. Inside was a bunch of boxer-briefs; similar to the kind I wore, only a smaller size and more feminine colors. I looked through the entire drawer, but that's all that there was. I opened the other drawers too, even checked her laundry pile, just to make sure I wasn't going insane.

"She doesn't wear panties?" I scratched my head. I was sure I had seen her in panties before but, the more I thought on it, the less certain I was. Deciding I would play it off as a joke, I grabbed a pair of pink boxer-briefs and closed the drawer. It'd still be funny to see Harry wear these.

********************

For the rest of the night and into the week, I thought about my sister's panties. Or rather, lack there of. Not in a weird way, though I did recognize that it wasn't normal for a brother to think of his sister's panties this much. I wasn't even a panty guy; I much preferred what was underneath them. Instead, I tried to remember every time I would have seen Ruth near-naked. She was a private girl, but then again who wasn't when it came to underwear? Still, the more I thought, the more I realized I had never seen her lower half in anything shorter than shorts. She never went swimming, so bathing suits were out. Any lingerie was non-existent (I went back to check), and everything else she had was just... tame. There was something off about it, something I couldn't quite put my finger on.

I had to wait until the next laundry day to put my plan into action. I grabbed my laundry, and threw in the pair of boxers I had kept from the truth or dare night. Since it was summer, both Ruth and I were off from our respective schools, and had the house to ourselves. Normally we'd have jobs, but Ruth's internship at the hospital gave her strange hours, and I was part-time at Target, which gave me an even weirder schedule.

I went downstairs, laundry in hand, and waited by the machine for a few seconds. Ruth was in her room listening to music, which gave me an excuse not to call up to her, but approach her in person, boxers in hand.

"Hey," I said, tapping on the door. Ruth was sitting at her desk, music playing through her laptop as she browsed the Internet. She was wearing capri shorts with a yellow top that fell loosely on her. Her blonde hair was in a ponytail, stretching down to her shoulders. It flopped in the air as she turned to me. Before she could respond, she saw me waving the pinkish undergarments in the air. "These yours?" I asked innocently.

"Oh! Uh..." Her eyes had gone wide at the sight of them, and I saw her dart them quickly to her dresser and back again. "Yeah. Um. Where did you find them?"

"In the dryer," I said with a shrug. "They must have gotten missed. Don't worry, I saved them before they went through another round!"

I laughed playfully as I walked over to her dresser, determined to put them away for her. You would have thought I was going to kick a puppy. The speed at which she moved startled me, because in the blink of an eye she darted in front of me, barely an inch of space between the dresser and us.

"No, that's fine, I got it, thanks," she said quickly. "You can go now."

"That's... what?" I said, actually startled. She tried to take them out of my hands but I held my grip. "What the hell sis?"

"What?" She finally grabbed the underwear and crossed her arms as if trying to hide the pair. "Can't a girl get a little privacy?"

"Well, I mean, sure, but you know I've had girlfriends, right? I think I know my way around folding these kinds of things."

"Sure, sure," Ruth said dismissively. "No need to prove it to me now. You can go." She put a heavy emphasis on the last word.

"Ruth, is... everything okay? You're acting really harshly all of a sudden. I was just trying to do you a favor."

That seemed to get through to her, and her face softened a bit. "Yeah Tony, I'm sorry. I didn't mean to snap. I just... I like privacy, you know that."

"I do," I admitted. "You don't have to be embarrassed if you like boxers," I said, fishing for an opening.

"Ha," she laughed uncomfortably. She shook her head, saying only, "I wish."

"What was that?"

"N-nothing," she said quickly. "Thanks for bringing them up, I'll take it from here."

A silence stretched as neither one of us moved. I did, eventually, take a step back, giving her room to put the boxer-briefs away. But she didn't move.

"I'm not going to leave until you tell me what's going on," I said uneasily. "Something's obviously bothering you, and I want to help. I mean, what else are siblings for, right?"

Ruth's arms were still crossed, but she seemed to consider this. "I —" she started, before falling silent again. Her brown eyes were glued to the floor, and she seemed to be searching for the right words. "It's embarrassing."

"Ruth, I'm your brother, you've done plenty of embarrassing things before," I said reassuringly.

"Yeah but those were things I've done, this is —" She cut herself off again.

"What?" I urged. "Come on, you can tell me."

"It's just... You have to promise not to say ANYTHING, to anyone." I nodded in agreement, but she just shook her head. "No, you don't understand. Not a word to your friends, not a word out-loud in an empty room - Nothing."

"Okay, okay, geez," I replied. "You're acting like this is blackmailable information."

"It kind of is." Ruth turned from me, thinking on something. "Well, maybe... okay, so if I tell you, would you... do something for me?"

"Depends..." I said cautiously. "What is it?"

Ruth shook her head. "No, you have to agree beforehand."

"What? No way," I said. "You could say something like 'Give me all your money' or 'Wear a pink tutu to school for a week'."

"I wouldn't do that..." she said, though I saw the faintest hint of a smile. She crossed her arms. "Anyway, that's my condition. Take it or leave it."

I stared at her, fighting my curiosity with fear of what she would make me do. In the end, my inquisitive nature won out. "Fine, I agree. Do your worst."

She smiled in a mixture of relief, reluctance, and fear. It was strange to see on my otherwise confident sister. She was fidgeting, shifting her weight from one foot to the other, arms still crossed. Finally and abruptly, she lowered her hands to her sides and looked at me.

"So, Tony. I, uh..." Her confidence fled her for a moment, but she recovered. "I wear those boxers because it's easier for me than normal panties. Because of my... my..." Ruth swallowed. "...penis..."

"Ha," I said outlaid, grinning. "Yeah right, very funny." As the silence stretched on, my grin began to fade. Her face was one of resolve, and she looked at me, judging my reaction. I changed from laughter, to confusion, to extreme confusion. "Wait, seriously?"

Ruth nodded her head. "Yeah."

"So you're... a guy?" I asked.

"No!" Ruth pushed at me, knocking me back a few steps. "I'm still a girl, you ass. I was just born with... an extra part." She shrugged. "It happens sometimes, apparently. Mom and Dad took me to a bunch of doctors when I was young. As far as they can tell, there's nothing wrong with me. I'm 99% girl with just a little bit extra."

"Hell of an extra," I said. At that, she let out a short laugh. Then, my brain woke up from the shock. "Wait... so what favor did you need me to do?" I asked hesitantly.

Ruth looked down at her feet again, shuffling them as she spoke. "So... I mean, with this... condition, I haven't really been with anyone. I've kissed a few guys, but never anything further than that. And of course, I'm horny like, all the time." I laughed with her at that; I knew the feeling. "So I was just hoping that maybe... a hand job?" She looked at me, hiding behind a small smile. "I mean, you don't have to if you don't want to, I know it's a lot, but I figured it's kind of just like masturbation for you, and I really, really just want to cum from someone else's actions, you know?"

She was rambling, and I held up my hand to stop her. "Ruth, hey, it's okay, I get it." I sighed. "I agreed to anything, so... that means anything. I'll help."

The relief flowed through her like a tidal wave. "Oh my god, thank you. You don't know how much that means to me."

"I've got some idea," I answered. I rubbed my hands together, getting them warm. I couldn't believe I was going to do this but I tried to stay optimistic. "Alright, so where do you want to do this?"

Ruth looked nervous, but walked over to her bed. She kicked off her flip-flops and pulled down her shorts. She was wearing some dark blue boxers, but she paused with her fingers in the waistband. "No laughing," she warned, and waited until I agreed before lowering them to the floor.

I'm not sure what I was expecting. After all, she told me she had a dick. Maybe part of my still thought she was joking. But as her boxers fell to the floor, and a semi-hard penis flopped out of them, twin balls underneath, I knew there was no mistaking it. My sister had a penis.

"Hunh," I said, staring at it like a deer in headlights. "Kind of looks like mine. Except I have hair down there."

"I like to keep a clean shop," she said, nervously laughing. "At least shaving is the most girly thing I can do for it."

I stared at it for what felt like a long time, before snapping back to the moment. "Alright, let's get down to business." I watched as Ruth sat down on the edge of her bed, her penis already started to grow hard in anticipation. It looked to be a solid five inches, though it was still growing as time passed. I knelt down on the carpet in front of her and stared at the only other penis I had seen in my life, next to my own. Then again, I couldn't put mine a few inches from my face. It had a kind of musk, and I sniffed at it in response to the new smell.

"Sorry, I should have washed it or something," Ruth said, biting her lip. "Didn't really plan on this happening today. I can go clean up first if you want."

"Nah, it's fine," I said, reaching out and grabbing it gently with my right hand. She let out a gasp, and I swore she was going to cum right there and then.

"Wow, oh, sorry," she said, catching her breath. "I just... wow, feels... different."

"Everything's different than your own hand," I told her, starting to slowly move my hand up and down her shaft. "And believe me, everything's better than it too."

"That I believe," Ruth said, leaning back onto her arms. I looked up briefly to stare at her, but she was starting to close her eyes and give in to the pleasure I was starting to give her. I found myself adopting a steady rhythm, trying to remember how I liked to masturbate. The angle was different, but the mechanics were the same.

Her dick had stopped growing, settling around seven inches and an average thickness. Almost identical to my own, easy to wrap my hand around. I kept up the pace, up and down, up and down, from base to tip and back again, almost teasing her in the slowness of my strokes. I wasn't sure why I was doing it that way. Part of me wanted this to be over as fast as possible. But looking up at my sister's face of pleasure, something else in my mind wanted this to last as long as possible

Down below, I felt my own dick start to respond to the sexual energy. I tried to shift positions to give myself some relief, but all that did was cause my erection to grow more. I tried not to pay it any mind.

"Oh, that feels so good," she moaned at me. "Shit, this is... this is great..." Ruth had fallen further onto her arms, almost at a 45-degree angle to me, with her head falling back and eyes shut. I took my other hand and gently groped her balls, causing her to moan again. I imagined her picturing some perfect guy she had a crushed on, finally giving into his desires for her and her penis. She must have been in heaven.

My hand on her cock and balls, my growing erection, and her sensual moaning — it was all starting to get too much. I saw she was lost in the pleasure, and something deep within me gave me an idea. I knew I wouldn't have the guts to ask later, so, in a moment of spontaneity, as my hand reached the tip of her penis again and started it's decent, I leaned forward and took her in my mouth.

"Ah!" she cried out, snapping up and pulling her dick out of my mouth. As it left it kind to smacked me, her erection harder than I think she had anticipated. "Oh, sorry! I just, what, what..." She was looking at me in confusion.

"You didn't like it?" I asked wryly.

"No, It just caught me off guard." She was panting, trying to steady her breathing. She looked at me seriously. "You don't have to do that."

"I know," I said, leaning forward to take her dick in my hands again. The one suck I had given it had left a small trail of saliva, and my hands made a slick sound now. "But... I don't know, I just want this to be the best possible for you."

"I..." she started to say, but I leaned forward again and took her in my mouth. Blowjobs were not an uncommon occurrence for me in my life, but being on this end definitely changed things. I moved my mouth as far down as I could, relatively surprised that I could take more of her on my first try. I made careful moves to keep my mouth free of teeth as I sucked her back up to the tip of her penis, licking the tip as I did so. "Daaaaaamnnnn..." she moaned. I chanced a look up at her, and saw that she was looking down at me. Our eyes met and I gave her a wink before falling down on her cock again.

I bobbed my head in a steady rhythm like I had with my hand earlier. My tongue danced around her cock as I let my lips massaged her girth. I felt her start to take control so I took my hands to her hips, holding them for balance as she started to thrust herself, her penis dictating how it wanted to be pleasured. That was fine by me, since my jaw was starting to get a bit sore. But I persisted.

I wasn't sure what was going through her head, but I knew I was getting extremely turned on. My dick was pitching the hardest tent it had ever made, and it twitched with excitement every time the tip of her penis hit the back of my throat. She let out another long moan, and I knew she wouldn't last much longer.

I let go of her right hip and grabbed the base of her cock, jerking her as I sucked her, moving faster and tighter. Saliva dripped around my hands as I tried to give her the best blowjob of her life.

And then, it happened. In the back of my mind I was prepared for it, but there's only so much mental preparation you can do before being faced with the real thing. The first stream of cum hit the back of my throat so hard that I completely stopped the blowjob. This didn't stop Ruth, of course, and she kept thrusting along my closed fists and open mouth. I regained myself quickly and continued to milk her balls dry, but as the fourth and fifth stream of cum filled my mouth, it became apparent that there was only one option available to me.

To even my surprise, I swallowed the cum. My head kept bobbing along her shaft, speed decreasing as I gobbled up each drop of my sister's cum. It didn't taste that bad, and as I swallowed I felt an immense wave of pleasure overtake me. With one last shudder, my sister let out a final spurt of cum before collapsing onto the bed, body still twitching as she gasped for air.

Somewhat begrudgingly, I took my mouth off her penis, the release making a 'pop' sound. I found I had to catch my own breath, and looking down I discovered why: I had cum myself. Somehow, near the end of my sister's blowjob, I had gotten so turned on that I creamed my own pants.

I heard some giggling, and looking up I saw Ruth looking down at me. She was propped up again on her elbows, but her hair was falling out of the ponytail, and she looked like she had just run a marathon. "That," she said, smiling the euphoric smile of the recently-cum, "Was... I mean... and you did that thing... it was..." She leaned towards me, pulled me to her by the shirt, and kissed me. The shock of her tongue dancing with my own, licking the remaining bits of her cum, caused the last of my own cum to leak out of my dick. When I came to my senses, I kissed her back, enjoying the feeling of her lips on mine.

"You're welcome," I said when we broke the kiss. "That was... unexpected."

"You're unexpected," she said, falling sideways on the bed. Her limp dick looked completely spent as it glistened with my salvia and a little bit of cum mixed around it. "I didn't expect... any of that. The hand job, the blowjob, and you swallowing. It felt... amazing."

"Yeah, I didn't expect that either," I said, getting off my knees and sitting on the floor. Looking up at her, we smiled at each other, each trying to steady our own hearts.

"Well, we better get cleaned up," Ruth said, standing on shaking legs and reaching out a hand to me. I grabbed it and stood, marveling at how I stood almost a head taller than her.

"How's that?" I asked. Then, I remembered my pants. "Oh, right. Not sure how that happened. Guess I really do need to do laundry after all."

Ruth laughed. "Well try to recover quick, because I think I owe you." She took a few steps towards the bathroom and turned to me. "After what you just did to me, I need to show you the real world's best blowjob."

"Really?"

"Of course. I'll be damned if I let my brother suck me off without returning the favor." She smiled as she walked into the bathroom, and I heard the shower start. "I'd be labeled the world's worst sister, and I couldn't take that."

Smiling to myself, I followed after her.