I Dare You

"You see me in my bikini all the time, so I don't get why this is such a big thing for you," I laughed at him as I sat back down in my desk chair.

"That's okay, you don't need to," he grinned. I couldn't help but glance down and notice things had happened in his pants. He left me alone, and I returned my attention to my homework. Well I tried to. I realised that my pussy was tingling and somewhat wet. Why the hell am I wet from flashing my brother? I tried to ignore the fact and get on with my homework, but I ended up occasionally squirming in my seat and thinking about Brandon getting hard from a simple underwear flash.

The next morning, I went to grab a pair of panties from my underwear drawer, and realised that whatever I picked out, I'd have to flash for Brandon. I found myself weirdly torn between finding the ugliest, boring pair that I could, or the sexiest. I wondered if he'd get hard again if I flashed him some boring ones. I decided to find out. I pulled a pair of black cotton boy legs that I hardly ever wore anymore and pulled them on. As I settled them in place, I was conscious that once again, I was wet from thinking about my brother looking at me in my underwear. I rubbed my panties against my pussy, sighed and grabbed a matching, boring cotton bra.

"Hey sis, how're things?" he asked me when he saw me in the kitchen. Dad had already left for work, and Mum was doing stuff upstairs.

"Fine."

"You look nice today, did you make a special effort?" He was grinning when he asked me.

"No, I always look this good, you're just too much of a dork to notice," I replied.

"Well, let me know when I'll get to find out just how normally you did dress today." I stuck my tongue out at him and headed off for school.

I held out on him until it was time for me to go to bed. I went to his room, for some reason feeling that by being the one to go to him, I was still somewhat in control.

"I was wondering if you were going to welch," he said with a grin when I closed the door behind me.

"As if I'd give you that satisfaction," I replied. "Okay, so here it is." I pulled my track pants down so that my boring black panties were showing, then lifted up my t-shirt to show off my bra.

"And the other side," he said when I made to restore my clothes. With a sigh I turned for him so he could get a view of my ass as well. As I turned full circle back to him, I'm sure I caught his hand slipping away from the crotch of his pants. He was definitely stiff. I put my clothes to rights, flipped him the bird and left.

I deduced from my experiment that it wouldn't matter what I wore. The mere fact of my flashing him my underwear seemed to excite him.

Over the course of the week, I found myself selecting nicer and more daring underwear, not that I had much variety to select from. On the final day I wore a pale pink thong, the skimpiest one I owned, along with a balconette bra that threatened to show off my nipples. Brandon was most definitely hard when I left his room that time. I'm pretty sure I heard him groan once the door was closed, and I have a fair idea of what he did next. I was amazed at how horny the thought made me. Brandon was almost certainly jerking his dick thinking about me. His sister! Even worse, when I took my thong off, it was soaked; like totally drenched. I'm ashamed to admit it, but I masturbated that night too.

I needed to come up with a dare for when I managed to peg him back. The more I thought about his fixation with my underwear, the clearer it became to me.

It took me three weeks to peg him, but when I finally managed it, I was excited to tell him what the dare was.

"Okay, since you loved my underwear so much, my dare is this. I dare you to wear my underwear for four days. You have to wear each of the pairs of panties I wore for you, for an entire day."

"What? No way. They won't even fit me," he laughed.

"I think you'll be surprised at how stretchy they are, Brandon. You at least have to try. If you can't fit into a pair, you don't have to wear them, but I know for sure that you'll fit into some of them, so you have to wear something on each of the four days even if you have to repeat one or two of them. Unless you concede, of course."

"Fine." he replied. I clapped my hands, excited for the following morning.

~~~~~~~

"Can I come in?" I asked chirpily from the doorway.

"Sure," Brandon grunted at me. I strolled into his room and couldn't help but notice how much it smelt of him. Not in a bad, stinky teenager way (I could remember how it used to smell!) but in a manly way. I'd not really noticed it recently, but for some reason I did that day. I had a pair of my panties in hand. He was still in bed, so I flipped them at him. He reached out and caught the navy-blue cotton bikini.

"Clearly I have to see you wearing them to make sure you complete the dare."

"Clearly," he agreed somewhat reluctantly.

"So, you going to put them on now or what?"

"Geez, pushy," he moaned. He pulled the bikini under his bed cover and wiggled around. "Okay, well, I guess they're on. Ready?"

"Oh yes," I said with a smile. He pulled the cover aside and stepped out of bed wearing just my panties. They were stretched tight, and I realised two things. Firstly, there was no sign of any other clothing in his bed, so he must have been sleeping naked and secondly, his cock really was massive. I mean, I'm not sure how he'd managed to squeeze himself into my panties without hanging out of them somewhere. I was kind of speechless.

"Right, you've seen me wearing them. Off you go. I have to tell you though, if they start cutting off my circulation, they're coming off."

"Um, yeah, fine," I agreed. After all, I wasn't going to get the sight of him wearing them out of my mind anyway, so I didn't really care whether he wore them the rest of the day or not.

I'd been correct: I couldn't get the sight of Brandon's cock squished in my panties out of my mind all that day, and the more I thought about it, the more I wanted to see it uncovered in all its glory.

At the end of the day he gave me my panties back, and I told him I'd see him in the morning with the next pair. The fact that the underwear that I'd worn over the four days had become increasingly skimpier had me pretty excited. I mean, by the time he was wearing the thong I'd worn on day four, there was no way his cock would fit into it. As obvioius as it may seem, I'd never given though tothe fact that the outsides of cocks take up more space than the outsides of pussies.

As it turned out, I didn't have to wait for the fourth day. When I went in and presented him with the cotton bikini I'd worn on the second day, it proved not to be stretchy enough for him to get them on. The same thing happened when I went back and fetched him the third pair I'd worn.

"Okay then, this is the last pair I wore," I said to him, handing him the little thong.

"Something tells me you're going to be out of luck," he laughed, holding them up and trying to sort out up from down.

"Well, you'll never know until you try," I replied cheerfully. He sighed and told me to turn around. I faced the door to his room.

"Oh, for fuck's sake," I heard him moan.

"Got them on?" I asked, trying to keep the excitement out of my voice.

"Um, kind of," he replied, and I turned around to see what he meant. He was standing with his hands covering himself.

"Come on, you have to show me."

He actually blushed! When he removed his hands, I laughed. The thong held his cock against his abdomen, kind of, but in no way was the fabric generous enough to contain him. He was poking out the top of the waistband. Well, when I say poking, it wasn't just the tip, there was like two inches of thick cock reaching beyond the waistband, and he didn't even look erect! That, and one testicle was hanging comically out the side as well.

"Okay, you've seen me, do I really have to wear them?" he complained.

"Not if you're happy to lose the game," I said to him.

"Fine. I'll wear them then."

"Hope you don't go getting a boner," I laughed.

"You can leave right now," he told me, grabbing a pair of jeans to pull on. He clearly didn't want me hanging around, so I buggered off. The memory of his cock wouldn't leave me, though. I kept wondering how big it would be when it got erect. Possibly big enough to be scary!

At the end of the day, I made sure to catch him before he had a chance to go into his room and change.

"What do you want?" he asked me.

"I just thought I'd see if you kept my thong on all day."

"Yeah, I did. Bloody useless thing that it was. It's not like it was doing much."

"Well I was thinking that if you let me watch you take it off, then I'd let you skip wearing my panties for the next two days, given you couldn't get the other two pairs on even though you gave them the old college try."

He looked at me, clearly thinking about it.

"Okay, deal," he finally agreed. He kicked his shoes off and peeled his jeans down. His cock was hanging heavily out the side of the thong rather than over the top. He wasted no time, pulling the pink thong down his legs and throwing it to me. While I went to catch it, he grabbed a pair of track pants and pulled them on.

"Thanks," I grinned at him.

"Yeah, no problem."

I skipped happily from his room, content with the memory I'd created, and already thinking about what the next dare I could get him to do might be. I called Becky. I didn't tell her exactly how I'd seen Brandon's cock, I just pretended to be freaked out that I'd seen it. I knew she'd want to know all about how big it was, and I was right.

"Damn, pity he wasn't erect," was about all she said at the end of the conversation. "I wish I could see it."

~~~~~~~

About a week later I found the peg hanging from the bottom of my t-shirt. It was behind me. Brandon was grinning like an idiot when I finally presented myself to admit he'd got me.

"What's it going to be, Brandon?" I asked him.

"I dare you to show me your tits for a minute.'

"What?!"

"Seems fair, you got to see my cock," he replied. "And I'm not even asking to see your pussy." I protested and delayed, even though inwardly I was getting turned on by the idea. Freaky I know, but if I was showing him my tits, there was a pretty good chance his massive cock would get hard. Even if it was hidden away, I'd get to see the effect I'd have on him through his pants.

"When?" I asked, and his face lit up as he realised I'd agreed.

"How about right now?" he asked.

"Fine." My agreement wasn't at all grudging this time, I was excited by the prospect! I pulled off my t-shirt to reveal a white cotton t-shirt bra. Brandon was wearing a pair of shorts and a t-shirt. I struggled not to keep glancing down at his crotch. I reached behind myself and unfastened my bra, but I trapped it with my arms so the cups wouldn't fall away from my chest. "Sure you can handle this?" I teased him.

"It's not like yours are the first pair of tits I've ever seen, Sarah," he replied.

"No, it's just the first time you've been perverted enough to ask to see your sister's."

"Well come on then," he urged me. I noted when his hand adjusted his cock. It was definitely getting bigger.

"Timer?" I asked.

"Fuck, okay, he said and he pulled out his phone. I made him set the timer for one minute, then start it before I slowly dropped my bra away. My nipples were hard. Brandon's eyes were glued to my boobs. They're a nice firm DD cup with quite large nipples, and I'm rather proud of them. I stood there, feeling weird in front of my brother, watching the seconds tick away. Part of me wanted to squeeze my nipples, part of me to play with my pussy. I even found myself thinking about sucking his cock. Instead, I just stood there until the chime announced the end of the minute. I unhurriedly put my bra and t-shirt back on and left him, closing his bedroom door behind me.

I walked to my room, closed my door audibly from the outside, then crept back and listened at his door. He was definitely wanking. I don't know why it turned me on to know that my brother was stroking his massive cock right after seeing my tits, but it sure did. I slipped a hand between my legs and rubbed myself, grinding my panties into my wet pussy. I stayed there until it was clear from the sounds that he'd climaxed, then I quickly scooted off to my room and did the same.

In the aftermath, I lay in bed wondering what I might make his next dare be. Things had certainly escalated, and I was surprised to find myself thinking about taking it even further. The size of my brother's cock was certainly a contributing factor to my musings. I found myself wishing I'd been able to see him shoot his load. I wondered if he'd do that for me if I dared him. Would he stroke himself to orgasm for me? But first, could I actually bring myself to dare him to do that? In any case I'd have to peg him first.

It only took me a week to peg him, which was quicker than I'd managed for some time. I wondered if he might have made it a bit easier for me just so I'd give him a dare, but decided he was too competitive for such a ploy. I still hadn't made up my mind exactly what I was going to dare him to do. I thought about telling Becky about my problem and seeing what she'd suggest, but ever since I'd mentioned seeing him, she'd been relentless in asking if I'd done anything about getting a better look. I'd asked her over a couple of times, and she was shameless in her flirting with him. I was even a bit jealous at the attention Brandon paid her. Hell, she was throwing herself at him, and I was surprised that he hadn't just taken her to his room and fucked her. I know she would have agreed in a heartbeat.

I decided to go halfway. I went into Brad's room while our parents were out and sat on his bed while he looked at me expectantly.

"What's it going to be?" he asked me.

"I dare you... to let me see your cock while it's stiff."

"Is that right?"

"Yep, that's what I want to see," I replied.

"Okay. Leave the room and come back in five minutes."

"Five minutes? It takes you that long?" I asked. I'd seen how hard he'd got from looking at my tits, and there was no way it had taken five minutes.

"Well I wouldn't want to get stage fright," he suggested.

"Okay, fine." I left his room and went to mine. I messed about with my phone, texting Becky about mundane stuff before I returned.

He was sitting at his laptop, and closed it as soon as he heard his door opening.

"Ready?" I asked him.

"Yep." He was looking over his shoulder. He spun his chair around and stood up, facing me. My eyes immediately went to his crotch and they widened. 'Impressive' doesn't start to describe the sight of it. It was massive; a work of wonder with long, thick, blue veins standing out along its shaft. He was circumcised, and the last two inches curved upward slightly as it stuck out in front of him. He let me gaze at it for about thirty seconds before using both hands to hide himself. "There, that's it."

He was clearly dismissing me. I left his room with a backward glance as I shut the door. He was watching me leave. When I made it back to my room I sat at my dresser, studying everything on it. I picked up my deodorant spray bottle. It was quite possible his cock was just as big, possibly longer, if not thicker. I turned it over and over in my hand, wondering what it would feel like to slide something that big into my pussy. I wondered if Becky would know. She'd been around a bit more than I had.

I didn't get around to asking her before Brandon managed to peg me again. It only took him three days! I was clearly too distracted by the memory of his cock, because I found myself spending more time with him. Initially the peg game had been driving something of a wedge between us. Our parents didn't seem to care or notice because it meant we weren't fighting and causing them grief. We were both technically adults anyway, so I think they pretty much assumed we were just going our own ways and finding fun with our own friends.

By that time, dares or not, I was enjoying teasing Brandon and making his cock swell up in his pants. If he minded, he didn't say or do anything to discourage me. I wore skirts around the house more, knowing he'd try and catch sight of my underwear whenever he could, and I put more cleavage on display. I was rewarded with regular, visual evidence of his arousal.

That also meant I was easier to peg, though.

~~~~~~~

"So, it's my turn to dare you, hey?" Brandon crowed as I held the peg in my hand, standing in his bedroom once again.

"Seems that way," I sighed.

"I dare you to show me your pussy."

"Um okay, how about tomorrow?" I offered.

"Sure," he agreed with a beaming smile. I left his room and went back to mine. I stripped off my leggings and underwear and checked myself in the mirror. I assessed myself and decided my kitty was too stubbly to be placed on display. It wasn't as if I'd been planning on anyone seeing me, so I hadn't bothered with any maintenance for a while. It was time to change that. I pulled my leggings back on, and headed for the bathroom.

I closed the door and locked it, then stripped completely and took a shower. While I was in there, I shaved my pussy. Usually I kept a neatly trimmed landing strip, but as I pictured myself showing it to my brother, I got horny, so I carefully shaved it bare. By the time I was done, I was wet from more than just the shower water. I directed the spray toward the wall and sat down on the shower floor, my knees spread, and my heels pulled in close to my pussy. I ran my fingers over my freshly bald lips and then teased my clit. I pictured Brandon's hard cock as I worked the fingers of my right hand back and forth over my swollen little nub. I first pictured it in my mind and imagined sucking it. I could feel my juices running out of my pussy, dripping down between my butt cheeks and I wished I had something to slide inside myself. Brandon's cock would work nicely. My pleasure spiked, my fingers working my clit feverishly, and I gasped as I came hard on the floor of the shower.

The next day, I slipped into Brandon's bedroom early in the morning. I'd awakened horny and wanted to show myself to him early in the day. Of course Ihadn't remembered that he slept naked (honest?), and that if I went in early, he might have a nice morning woody going on. That would have been very dirty of me.

"Ready to see my pussy, Brandon?" I asked him as he sat up in bed, clearly not very awake.

"Um, I think so," he replied.

"Well you didn't specify when or for how long, so here goes," I announced. I'd worn my pyjamas into his room, which consisted of a pair of thin shorts and a loose tank top that did little to hide that I was braless. My nipples were hard in anticipation of what I was about to do, and I knew from the glance I'd taken in the mirror that it would also be obvious to Brandon, if he chose to look. (He did.)

I slipped my sleep shorts down to my knees and stood there for a few moments to give Brandon a chance to look. He groaned out loud.

"Spread your legs some more," he muttered, sitting up to try and get a bit closer to me while keeping his bedcovers from falling onto the floor.

"That wasn't the deal," I laughed and pulled my shorts back up. "Have a good day!" I closed the door to his room behind me and went back to my room to get ready for school. I felt a bit silly that I'd been so careful about shaving and then limited his viewing time so much, but I didn't want to appear too eager.

As I dressed, I plotted how I might manage to next peg him, and what my next dare would be.

~~~~~~~

"So have you seen his dick again?" Becky asked me at lunchtime.