I Dare You

"Perfect, really," I replied. "I won't interrupt you two, I just want to get a drink from the kitchen. Is anyone else home?"

"Naah, Mum and Dad went out, said they'd be home late," Brandon replied.

'Okay, cool, have fun."

"Thanks Sis," Brandon replied.

"I'll get the deets later," Becky said, flashing her phone at me, indicating she'd text me as soon as she wasn't otherwise occupied. I gave her a grin and left them to it.

I left my door open and could hear the sounds of the movie drifting up from downstairs. When it ended, I closed my door, knowing if Brandon took Becky up to his room, they'd have to pass mine. I didn't want them knowing I was interested in whether that happened or not.

I smiled when I heard them pass by a couple minutes later. I gave them a little time before sneaking down the corridor to eavesdrop outside the bedroom.

At first I couldn't really hear anything, but soon I heard Becky saying, "Let me see it, Brandon. Let me see the python."

I nearly laughed out loud. The python? What was she thinking?

"It's so fucking amazing, Brandon," Becky crooned. Then she wasn't saying anything. I'm pretty sure she was blowing him at that point. I undid the button of my jeans, slid the zipper down and slipped my hand inside my panties. I stood right next to the bedroom door with my fingers teasing my pussy as I imagined what was going on inside my brother's room.

I considered cracking the door open to see what I could, but I decided that was probably going a step too far. As if I wasn't already being pervy enough! Feeling funny, I went back to my own room shortly after that.

Sure enough, what must have been as soon as Becky got back to her place, my phone beeped with a text from her, asking for me to share details about my date. We swapped messages back and forth, and I found myself in a weird place. Becky started to share details about her and Brandon. It was as natural as it would have been if she were telling me about any other boy she'd been messing about with, but this time it was my brother. I was torn between complaining 'Eww, that's my brother!' and wanting to ask for details because of the small amount I'd listened to. I was mad horny, but I settled for the middle ground of not protesting, but not actually asking for details either. She shared plenty of them anyway. Like after the exchange was over, I knew for sure she'd fucked him. I couldn't believe she'd gone there that quickly. I thought she might have held out for a little while, at least.

"I'm going to send you a pic," Becky sent me.

"Um, I don't think I need to see any pics you took tonight!" I objected.

My phone bleeped again and there was a Snapchat. My finger hovered over the app. Did I really want to see what she'd sent me? How long would she have set the snap for before it would be gone? Should I screenshot it?

I hit the button. The picture was of Brandon's rock-hard cock, with both of Becky's hands wrapped around it. Brandon had clearly taken the photo. Her face was just above it and she was grinning like an idiot. She'd given me all of three seconds. I'm embarrassed to say I screenshot it.

"Look how fucking big it is!" she messaged me a moment later.

"Um brother issues!" I responded.

"Tell me if it wasn't Brandon you wouldn't be all over it!"

"Not the point Beck! I mean, you're right, but he is my brother, so I don't really need to see that."

Another snap came through. I quickly switched apps to look at it.

Brandon had also clearly taken this one. Becky was squatting down, mounted on his cock. It didn't show anything above her navel, but I was confronted with the sight of her bald lips spread dramatically around his enormous shaft. Her juices were evident on him, and I would estimate that only half of his dick was inside her.

"Too much!" I sent back, but I screenshot that pic as well.

"Sooooo much," she responded.

"GOOD NIGHT!" I sent and killed the messaging app. Then I grabbed my hairbrush and fucked myself until I came, memories of holding Brandon's cock and the photos I'd captured of Becky with him fuelling my passion.

~~~~~~~

I managed to avoid being pegged for two weeks through a combination of vigilance and Becky. She didn't know about our game, but she still helped by being all over Brandon, which meant that I didn't see as much of either of them as normal, and from what Becky shared with me, they were fucking like rabbits. So I guessed he wasn't looking for the peg game to give him any additional excitement.

He did eventually catch me, though. I was drying the dishes with Mum and he managed to peg the back of my t-shirt while I was distracted.

"What's it going to be, Brandon?" I asked him while we were watching television alone together later that night.

"I dare you to let me play with your bare tits," he replied enthusiastically. I studied his face for a few moments and then agreed. I told him to start playing something from Netflix on the computer in his room, then to slip into my room so we wouldn't get busted. Brandon jumped up off the couch and rushed upstairs to his room. I couldn't believe how much the whole idea was turning me on. I entered my room and turned to wait for him while standing in the middle of the floor. He arrived less than a minute later, closed the door behind him and I glanced down at his crotch, confirming that the enthusiasm on his face was matched below the belt.

I reached under my shirt and unclasped my bra behind me, then reached into one sleeve to pull the shoulder strap over my arm before pulling my whole bra out the other sleeve. Brandon reacted as if I'd just performed a world class act of magic, and I laughed at him. He was only just coming to the realisation that once again I'd found a loophole in his request.

"Okay, you can feel them now. Just stand behind me and slip your hands under my shirt," I invited him, holding out the bottom of my t-shirt for him to slip his hands under.

"Can't you just take that thing off?" he whined.

"You only specified you wanted to play with my bare tits, not to play with my tits while I was naked," I advised.

"Fine," he grumbled. I turned around and he stepped in behind me and slipped his hands under my t-shirt. His hard cock was pressing against me from behind, but I resisted the urge to rub my bum against him. It wasn't easy.

"Damn," he muttered when his hands cupped my breasts. I bit down on my lip to keep from moaning as he squeezed and played with them. My nipples hardened, and he tweaked them with his thumbs and fingers. I let him pull on them a bit, but then let him know when he was getting a little more aggressive than I liked. He went back to just squeezing and playing around with my tits.

"Okay, time's up," I stated, working hard to keep from vocalising the desire building inside of me. He gave a final squeeze and released them. I felt his cock press a little harder against me, and that time I rocked back into it. God, he was hard. I did groan at that point and so did he, but we quickly stepped apart, neither of us commenting on how tempted we'd just been to go further... lots further.

"Fuck, your tits feel amazing, Sarah," he said.

"They are pretty good. aren't they?" I replied, cupping them through my t-shirt and squeezing them firmly. "I like that they're nice and firm, 'cause like, you know, firm is good, right?" I added, gazing pointedly at his crotch.

"Yeah it is," he agreed and turned to leave, his hand adjusting his cock. I can't say how much I wanted him to take it out so I could play with it. I closed my door behind him, and once again resorted to my hairbrush for pleasure. I pulled up Becky's pics on my phone and tried to imagine my own pussy being stretched as wide as hers was. Damn, I needed a thicker hairbrush!

~~~~~~~

I had a few more dates with Mike over the next couple of weeks, and we progressed as far as hand jobs and fingering. I'm not sure what held me back from just mounting him, maybe it was that he wasn't too pushy. If he was happy to go slow, I was happy for him to do so. It meant I spent a lot more time with my hairbrush, though.

I was shopping with Becky when I mentioned I needed a hairbrush with a bigger handle, not really thinking about what she'd make of it.

"Why a bigger handle?" she asked me.

"Oh, um, well, just so it's more comfortable to hold," I replied, trying to think on the fly.

"Bullshit," Becky called me out. "You want to fuck it, don't you?"

"Eww, gross!"

Becky just laughed at me. "You forget how many times you've told me you fuck your hairbrush, Sarah. I think you've been fantasising about your brother's giant cock, and you want to feel what it's like to take something that big."

"You're so disgusting!" I accused her. "As if I'd be thinking about my brother's cock like that."

"Not your brother's necessarily, just any cock that big," Becky grinned, knowing she had me on the defensive. "And for that, you don't want a hairbrush, you want a cucumber."

"Becky!" I cried out, causing a couple of people in the shop to look at me. I grabbed the brush with the biggest handle I could find; a nice polished wooden handle, stuck my tongue out at her and went to the counter to pay for it.

"We could get you a proper dildo from the sex shop," Becky suggested on the way out.

"No way," I said, even though the thought held some appeal. But I couldn't face going into one of those places and having Becky right beside me pointing out all the toys of a similar size to Brandon.

When I got home I tried out the new brush, quite pleased with the results. While I slid it slowly in and out of my pussy, I plotted how I could peg Brandon again, and what I wanted to dare him to do. Just as I came, I decided.

~~~~~~~

It took me another four days, finally managing to get him while he was preoccupied kissing Becky in our kitchen.

He came to see me the following morning, because Becky had hung around until late, and I'd gone to bed rather than having to put up with seeing them all over each other.

"What's it gonna be Sah?" he asked.

I paused and then just said straight out, "I dare you to get naked and wank until you cum while I watch, but only after you haven't cum for three days."

"No deal. I'll wank for you, but I'm not going for three days without cumming first."

"Okay fine, but it has to be your first load of the day."

"Fine," he agreed.

"So, tomorrow morning?" I asked. Given it was going to be Saturday, there was a fair chance Mum and Dad would head out to shop or take a long walk, and if I got to him in the morning, I'd have him before Becky could get to him again. I was pretty sure she was why he wasn't willing to go for three days. I can just imagine how the conversation would have gone if he'd had to tell her he wasn't allowed to cum for three days. There's no way she would have let him... or me... get away with that!

I left him, promising to visit him in his room the instant our parents left the house, which is exactly what I did.

I had to wake him up. He had a game later in the day, but he didn't have to be there for ages. He complained a lot, but hey, I probably would have too if someone woke me up by jumping up and down on my bed and telling me it was cum time!

After grumbling and moaning for a bit, he complained he had to go to the toilet, so I let him out of bed. He was naked of course, and I was pleased that he made no effort to cover himself. He just rolled out of bed and wandered off, leaving me sitting at the foot of his bed.

When he came back his cock was swinging nicely, not completely flaccid but not all that hard, either. He looked around the room like he was working out where he was going to do it. I patted the bed and suggested he lay back down. He thought about it for a bit, but then did exactly that. I have to admit that I nearly reached out and grabbed him, but I managed to avoid the temptation.

I watched him arrange himself on the bed, propping his pillow against the headboard so he was mostly sitting up. He took his cock in hand and started stroking it a little, not overly enthusiastically. I watched intently as he started to grow. As he hardened, his pace quickened. Every time I glanced up from his cock to his face, I found him looking straight at me. I nearly asked him what he was thinking, but I chickened out. I decided not to speak to him unless he spoke to me first.

He kept stroking, and soon he was at full erection which was of course, mightily impressive. One hand pumped up and down and the other reached down and stroked across his belly. He looked like he was about to ask me something, but he refrained. He kept working his hand on his cock.

After a few minutes, pre-cum started to seep from the little slit at the top. I licked my lips as Brandon's hand twisted up over the head of his cock, smearing the fluid on himself. His bulbous head glistened.

I pulled my heel up against my pussy and rocked against it as his fist continued to pump away. God it looked hot. I really wanted to join in, but that would have meant giving something away for nothing; something that he should have to earn by pegging me. I wasn't about to let that happen when I was having so much fun crushing him with loopholes.

As I watched, his balls seemed to retract and tighten against his body, and his chest began heaving with every breath he took. He moaned for the first time, and I took it as a sign he was about to explode. I was right. As he stroked a final time, he pushed his cock away from his belly so it pointed into the air, but also towards me. A thick rope of cum blasted from him and landed between us on his bed covers, quickly followed by several more spurts. His body shook with his orgasm.

"That's so awesome," I purred as I watched the last of his cum dribble down over his shaft and his fist.

"Well, I'm finished, so you can leave now," he gasped.

"Sure," I replied, standing up from his bed and leaving. I rushed into my room and fingered myself to orgasm, replaying in my mind the sight of the cum fountaining from the end of his cock, imagining how good it would feel to have it painting my womb instead.

~~~~~~~

When he next pegged me, I had a fair idea of what he was going to ask for, and he didn't let me down.

"I dare you to let me watch you orgasm while you're naked and totally uncovered, so I can see every bit of you," he said. I laughed at how careful he was being to ensure I wouldn't be hiding under my bedcovers or anything.

"Fair enough," I replied. He hadn't stipulated how I was supposed to do it, so when it came time, I knew I'd just use my fingers. No point giving him any ideas about what I got up to with my new Brandon-inspired hairbrush!

It was a Saturday morning again, when our parents were out of the house. I woke him up and invited him into my room, and then stripped out of my pyjamas. He was already hard before I'd even finished that! I lay back on my bed and I have to admit, being devoured by my brother's eyes turned me on in a way I should probably be embarrassed about. My nipples were aching they were so tight, and my pussy was sopping wet. I hoped it wasn't too obvious how turned on I was. I propped myself on my bed much as he had, and he sat in my desk chair, rolling it close to my pussy, so he could watch everything I was about to do.

I spread my legs and slid a finger between my bald, freshly shaved pussy lips, gathering the moisture to drag it up and over my clit. That little love button was ready to go, and I shuddered as I started to rub it in front of him. I started slowly without much pressure, building on my already heightened desire. I circled my finger around my clit, and occasionally slipped it down between my lips for more moisture. I could see that Brandon was getting hard in his pants, and the more obvious it became, the more excitedly I started working my clit.

Increasing the pressure and moving my fingers back and forth across my clit had me gasping as pleasure spiked through my body. My body was on fire, and I could feel my juices running down over my anus. I briefly considered slipping a finger in my ass, but I didn't want to give something that major away for free! I moved my left hand to my breast and squeezed it before pulling savagely on my nipple while I used the fingers of my right hand to continue the assault on my clitoris.

Brandon adjusted his cock in his pants. I don't know whether he was even aware he'd done it, as his eyes never left my pussy. The movement drew my eyes though, and it presented me with a clear indication of how hard his long, thick shaft was at that moment. I released my breast and used the fingers of my left hand to spread my bald pussy lips, while my right started flickering rapidly back and forth over my love button. I was getting very close to cumming. I bit down on my lip, gasping as jolts of electricity spiked out from my clit, and my stomach did delightful flip-flops.

With a final flurry of my fingers, I came. I exploded, tipping my head back, my thighs clamping together to trap my fingers.

"No, leave them spread!" Brandon urged frantically. I whimpered, suddenly feeling painfully exposed and vulnerable, but I still spread my legs for him, leaning forward to see what he was seeing. Even though I was still lying down, my legs felt wobbly, and I could feel my pussy clenching and releasing with my orgasm, while Brandon sat and watched intently. My fingers were messy with my juices and I nearly sucked them clean, but instead I wiped them on my nipples and teased them a little.

"All done, time for you to go," I told him, closing my thighs together again. He stood up, his cock straining against his athletic shorts. God, I wanted to rip them down and suck him. I didn't, though. It went against the unspoken rules of our game. Nothing ever happened beyond the dare itself.

I went on a date with Mike that night. Even though I'd had a powerful orgasm, it hadn't done anything to suppress my desire. If anything, it had just stoked it even more. I mean I'd cum, but I hadn't had a real live cock inside me in like, forever!

We had a nice dinner then went to catch a movie. I made sure we sat in a nice isolated part of the theatre where we wouldn't be too closely observed, then I teased him mercilessly throughout the entire movie. When I had my hand in his pants stroking him toward the end of the film, his pre-cum was seeping freely, and I rubbed it over the head of his cock.

"Someone's a bit keen," he said to me with a grin while the credits rolled.

"Um, yeah, I guess I am a bit," I giggled.

"Maybe we should find somewhere quiet to park the car then?"

"Sounds like a good plan to me."

We drove up into the hills overlooking the city and managed to find a parking spot that wasn't too close to another car.

I kissed Mike hungrily, my tongue darting all over his, and in and out of his mouth. His hand was on my breast, and I pushed it against him, needing the extra pressure on my nipple.

"Let me take my top off," I gasped as his fingers sought to tease my nipple through my bra and t-shirt. Moments later I was topless, and his hand was back on my breast, squeezing skin to skin.

"Suck my nipple, Mike," I begged him shamelessly, breaking the kiss again. His eyes met mine, a grin broke out on his face and he dropped his mouth to my tit, sucking my nipple deep inside. He pulled back, catching the nipple with his teeth as it nearly slipped out of his mouth. I groaned as he bit down lightly on it, surprised by the minor aggression, given how timid he'd been at previous times. I reached for his pants and tried to release them, but with him scrunched down to suck my tit, that wasn't happening.