I Dare You

When Brandon left the shower, he called out for me to come to his room. I found him sitting on his bed, naked, his cock semi-erect, laying across his thigh. I don't think I'll ever tire of seeing that massive piece of meat.

"Sit there on my bed," he indicated, pointing to the end. I walked over and climbed on, sitting cross-legged, pushing my short denim skirt down into my lap to hide my panties from view. Maybe I should have changed them after all!

Brandon looked me up and down and I gave him an encouraging smile.

"No one ever knows, right?" he said.

"Of course; like every dare," I replied. He sighed, then took hold of his cock with his right hand, lifting it from his thigh and stroking it. I really did love watching it grow hard as he did it. He kept stroking until it was almost completely hard, then after glancing toward me, dropped his head toward his cock. His mouth opened and the head of his cock disappeared between his lips. I moaned in response. His lips sealed around the top of the shaft and his cheeks dimpled as he sucked.

I pulled my heel in against my pussy and rocked against it as I watched, pushing my skirt down to hide the action from Brandon's view even though he wasn't watching me. He was pumping his cock with his right fist while the left supported the base. I was impressed.

I couldn't help but think it wasn't the first time he'd done it. My suspicion had clearly been correct, that with a cock long enough for him to reach it with his mouth, he'd experimented.

"That's so fucking hot, Brandon," I encouraged him. He glanced my way and I lifted my hand away from my skirt. The denim rose enough to expose my damp panties. I wasn't sure if he noticed their state or not, but I liked to think that he did.

I watched him work himself over, his cock stiff, the veins standing out beautifully up and down the shaft and blood engorging it. He was clearly stimulating himself mostly with his fist rather than his mouth, but I wasn't about to criticise details when the overall effect was so good.

I was tempted to plunge a hand inside my panties to finger myself, but I held off. It was silly given how turned on I was, but it seemed that openly masturbating in front of Brandon was giving something away for free when he was the one completing the dare. That didn't stop me from soaking my panties, though. I could feel how wet they were on my heel as I kept rocking against it.

"I can't wait to see you blow your load Brandon, it's going to be so fucking hot," I purred.

He kept going until he reached the point of no return. I hadn't really given much thought to what he'd do when he exploded. I think I'd assumed that he'd cum into his mouth just like he'd expect a girl to do for him. Instead, he lifted his head, pumped his shaft and just as he exploded, thrust his cock forward and aimed it at me. He gave a cry of release and a rope of cum flew from the tip of his pulsing member. I gave a squeal of shock as it hit me on the chest, splatting against my t-shirt. The next pulse shot another rope at me. It didn't travel quite as far and landed on my skirt. The next landed on my bare feet, and then the last of his load was running down his cock and over his fist.

"Happy?" he asked.

"Very much so, that was amazing" I complimented him.

"Good, now pass me those tissues and you can be on your way," he said, dismissing me. I passed him the box from his desk and made my way out of his room. Within a minute, I was on my back on my bed plunging my hairbrush in and out of my pussy.

My orgasm was intense, and I cried out in ecstasy when it hit, not bothering to hold back. I'm pretty sure Brandon heard me, but I really didn't care. I'd been sorely tempted just to get myself off right in front of him, game be damned.

Things were wide open now. I wondered what his next dare for me would be.

~~~~~~~

I managed not to get pegged for two weeks, but I made the mistake of nodding off watching Netflix on the couch one night.

"Ready?" he asked me after gloating that he'd managed to peg me.

"Sure."

"Okay, I dare you to let me watch you fuck yourself in the pussy with a cucumber until you cum."

"Sure thing," I responded.

"Tonight?" he asked me.

"Are Mum and Dad going out?"

"No," he replied.

"Bit risky then isn't it?"

"Doesn't that just make it more fun?"

"Maybe," I laughed. "Okay, I'll do it for you tonight after dinner."

I made sure to raid the fridge during the day, stealing one of the two cucumbers in there. I figured that with my luck if I didn't get in early Mum would use them in a salad or something and by the evening there wouldn't be one to have sex with. I'd never tried fucking a vegetable before. To date fingers, cocks and hairbrush handles had been my only paramours.

When dinner rolled around, I had to laugh at the speed with which Brandon devoured his food. Just to be mean I slowed down instead, taking extra time to chat with Mum and Dad, and I could tell it was frustrating Brandon. It was so funny. To drag things out even longer, I helped with the dishes as well. Brandon ended up even helping once he realised the after-dinner clean-up would be completed more quickly if he pitched in.

We told our parents we'd be in our rooms, Brandon playing computer games and me watching Netflix. This wasn't unusual, and they didn't bat an eyelid. Brandon didn't speak until he'd followed me into my room.

"You're terrible, Sarah," he claimed as I rummaged in a drawer for the cucumber I'd hidden away.

"I don't know what you could possibly mean," I claimed, all innocent.

"Oh come on, you never talk that much or eat that slowly at dinner."

"Yeah, but don't you find the anticipation just makes it all the more worthwhile?" I asked him, turning to present the cucumber. I couldn't help but wonder how it compared to the size of my brother's cock. It was probably similar.

I stripped off my athletic tights and my black thong, then reclined on my bed and spread my legs.

"What about your t-shirt?" Brandon asked.

"You never said I have to be naked," I giggled. Brandon had given up protesting any loopholes that I took advantage of, and he accepted that he'd at least be watching me fuck myself with the vegetable.

He pulled my desk chair over to watch, and I began by rubbing the end of the cucumber against my pussy. I was already pretty wet, but it still took a few moments to get myself to the point where I could begin to insert it. I spread my lips with my left hand and rocked the free end of the cucumber back and forth until I'd wedged a good two inches inside me. Even that much of it felt like a lot, but there was a lot more to go. Brandon was just staring at the point where the vegetable disappeared between my pussy lips. It turned me on to see the lust on his face. I worked the bumpy dildo back and forth, in and out, sliding it deeper and deeper inside me until I could feel it pressing against my cervix. I then began working it in and out faster, feeling it fill and stretch me, the little bumps on its sides teasing me each time it glided inside.

Brandon was rock hard. His cock was straining at his shorts and he had to adjust himself several times.

"Uncomfortable?" I giggled when I saw him wrestling with the restrained python.

"Well it's pretty fucking hot," he replied.

"You say the nicest things sometimes, Brandon," I gasped, plunging the cucumber deep into my cunt again. As I kept working it, his hand lingered on his cock, kind of half-stroking it within his pants. I really wished I could watch him stroke it, but I knew better than to ask. If I did that, it was guaranteed that he wouldn't take it out. I thought maybe if he was turned on enough, he would of his own will, just to relieve the strain.

I pulled the cucumber from my pussy and Brandon immediately objected, "You have to do it until you cum!"

"I know, but I need to change positions," I explained. I rolled over and got my knees under me, lifting my butt off the bed, presenting my pussy back toward Brandon. I reached back and worked the cucumber once again into my pussy, pushing myself back against it even as I pulled it inside. I rested my head on the bed and reached between my legs with my left hand so I could rub my clit. I heard Brandon moan as the cucumber plunged back inside me. I could imagine what he was thinking. I was pretty sure it would be something about kneeling behind me and shoving that gorgeous fat cock inside his sister's pussy. It was what I was thinking at least.

I was so fucking horny! I worked my clit and pumped my pussy until I exploded and collapsed onto my bed. I looked over to where Brandon was sitting and sure enough, I found him with his cock out, pumping it, pre-cum glistening on the tip, lust scrawled across his face. He saw me watching and I couldn't read the expression that crossed his face. He appeared torn and his hand stilled on his cock.

"You don't have to stop if you don't want to," I said to him, rolling on my back and spreading my legs for him. My pussy was still twitching, probably not enough to be visible, but I was aware of it within myself, and there was no question it was visibly red and swollen from my pleasure.

Brandon didn't say anything, he just resumed pumping. I picked up the cucumber and slid it back inside my tight, post-orgasmic pussy. Brandon sat forward on his chair and aimed his cock at me as he exploded, just as he'd done when he'd sucked himself off. Cum splattered over my hand, the cucumber and my pussy.

"So fucking hot," he muttered before packing himself away and leaving. I was left to clean myself up, glad that our parents hadn't decided to pay any attention to what we were up to.

That night I lay in bed, once again pondering what I could dare him to do next. I was determined not to be the one to escalate the level of intimacy between us. Like, I wasn't going to dare him to stick his cock in my pussy, especially because that would be more like a reward for him. I finally decided to dare him to do something in public again. Yeah, that would work. I'd dare him to masturbate and cum in the back yard.

When it finally happened, it was a bit of an anti-climax. It was fun and it turned me on, but it was just a bit lame really, watching him beat off in the yard until he came. I felt like he was going to get me to do something much more intimate than I'd done to him, so I'd feel like I was behind on the non-existent tally board of the game.

It put me in an unexpected and distracted funk that turned even worse when he pegged me the following day because I wasn't paying attention.

"I dare you to let me watch you finger your ass and then stick a sharpie in it," he said to me with the most annoying shit-eating grin on his face. "You have to be completely naked and doggy-style when you do it too, with nothing covering you or hiding you from me." He was getting better at covering my loopholes. It had taken him long enough.

I'd never played with my butt. Becky had and she kept telling me I should give it a go, but the idea hadn't really turned me on. But I wasn't about to lose the game over it. At least it was just a finger and a sharpie. Shit, if he'd wanted to put his monster cock in there, he might have just won the game.

I wanted to make him wait until Saturday, but he again talked me into doing it while Mum and Dad were downstairs. He followed me into my room after dinner on the Wednesday night and watched while I stripped my clothes off for him. I'd given the performance a little bit of thought and knew that lube was going to be essential, so I had some ready to go. I climbed naked onto my bed and adopted the doggy-style position he'd stipulated. He stood kind of behind and to one side of me, and I was pretty sure it was so he could see my big tits as well, even though they ended up crushed onto the bed.

First I squirted lube on my finger, then I reached around and teased the entrance of my ass. I wasn't sure what to expect, but it felt surprisingly good. I started pushing and probing and soon my finger was just inside, probably only up to the first knuckle. It was enough to get Brandon moaning and when I glanced at his pants, he was already rock hard. I closed my eyes a bit, then as I wiggled and pushed with my finger, I found the tight ring of muscle resisting the penetration. After a while I took a deep breath, let it out slowly to relax and pushed with my finger, sliding it as far as possible inside that tight ring. I gave a surprised little gasp of pleasure at that. It felt good!

I heard a zipper and looked back to see Brandon fishing his cock out of his pants. I slid my finger in and out for a while and saw him start stroking his cock. God, it looked good

It was time for the sharpie. I took the one that I'd placed on my bed before dinner and lubed it up while Brandon kept gently stroking himself, pre-cum starting to glisten on the tip of his cock. I positioned the tip of the sharpie against my puckered little asshole... and pushed. It glided in quite easily, the shape perfect for thie unorthodox use. I pushed it deep, the pleasure surpassing any expectations I'd had of how it might feel. Brandon's hand was working his cock harder and harder, and I started sliding the sharpie in and out slowly, using my free hand to tease my clit.

Normally that would have been the end of the dare. I would have told Brandon I'd fulfilled my task and sent him on his way, but I was too horny! I kept going, and so did he. I worked my fingers rapidly back and forth on my clit and shoved the sharpie up my ass and came with a bitten-back squeal.

"Holy shit!' Brandon exclaimed when he saw my body shaking. He stroked twice more and then aimed his cock at me and exploded, shooting cum all over my ass.

"Hey!" I hissed in protest even though my heart wasn't really in it. There was something about the feeling of his warm cum splattering over my ass that turned me on.

"Sorry," he said sheepishly as cum drizzled from the end of his cock. "It was, um, just too hot." He stuffed his cock in his pants and abandoned me to clean up. As I did that, I came to a very quick decision as to what the next dare would be. Brandon had cracked the barn door a little, so I was going to kick it wide open.

Two days later I pegged him again. I made him wait forty-eight hours before I broke the news of the dare to him, though.

"So bro," I began when I had him alone in his room. "I dare you to finger your ass while you masturbate, and then stick a carrot up your bum and cum for me."

"What?" he asked reflexively, clearly shocked.

"If it's good enough for me..." I suggested. "Unless I win?"

"No way. Fine, I'll do it," he said quickly. He may have inflicted a sharpie on me, but I wasn't beyond escalating things to suit myself sometimes.

We did the self-buggery in his room. I sat on his chair and he lay on his bed, on his side, naked, his massive cock hard before he'd even touched his ass. I didn't know if he'd ever done anything like it before, but I figured he probably hadn't. I'd never met a jock yet who was confident enough in his sexuality to explore ass-play. (Not that I'd ever asked anyone, so maybe I was wrong.)

He began stroking his cock first, then pulled out some lubricant, squirting it over the head so his hand slipped and slid around it, then swirled his middle finger in it until it too was wet. He reached a little awkwardly around his body and I watched as his worked his finger inside his butt hole. He managed to get it in to the second knuckle, his other hand still stroking himself. He had his eyes closed, but his face didn't show any discomfort or disgust or anything.

"Now for the carrot," I purred, my heel pulled up firmly against my pussy. I was rocking against it, completely turned on by what he was doing.

"Fuck," was his only response. He had the carrot beside him on his bedside table and he grabbed it and the lube, making sure it was ready to penetrate his ass. He let go of his cock and used his right hand to lube the vegetable thoroughly before positioning it with the pointy end at his asshole.

"Pull your legs up," I suggested. He was lying on his side and drew his knees closer to his chest, and my view improved a little as he started pushing it inside. I watched as his ass opened up to take it in, and his balls contracted up against his body. His cock remained rock hard. I found myself wanting to help, to be the one either to drive the carrot in or to take hold of his cock, but I held back because it wasn't part of the dare. Hindsight, oh well. He pushed and wiggled the carrot until about half of it was buried up his butt, then he started stroking his cock again. He was biting back a moan, clearly turned on, and I could feel how wet my panties were against both my pussy and my heel. It wasn't enough pleasure for me. I plunged a hand inside my leggings and panties and played with my clit, rubbing it firmly as Brandon wanked.

When he neared orgasm, he grabbed a bunch of tissues and used them to catch his seed. I quickly pulled my hand from my panties with a sigh and sucked my fingers clean as he pulled the carrot from his ass. I left him to his clean-up and fled to my room where I made friends with the sharpie again, pushing it in my ass as I got myself off.

~~~~~~~

I wondered what the next dare would be. As we didn't ever talk about the dares other than to declare them, I had no idea how Brandon felt about my making him stick the carrot up his bum. He hadn't been that keen in our initial discussion, but maybe he'd enjoyed it enough to change his mind. After all, it wasn't like he'd gone soft and couldn't cum during the experience.

As always, I stressed myself out with the desire to find out what the next dare would be and with making it as hard as possible for Brandon to peg me.

He took a leaf out of my book though, and he used Becky to cheat. He never told her why or what the consequences would be, but one afternoon about four days later, he asked her to fasten the peg somewhere hard to find on my clothes while she was over visiting us. We had a long argument about whether I should even have to go through with the dare and whether the pegging counted or not, but in the end, I conceded on the condition that I was now allowed to use a proxy as well. Brandon agreed to a single instance, and we ruled out any further use of them.

When we had that sorted, he came out with his dare. "I dare you to tongue kiss another girl at the party this Saturday night. And I have to get to see you doing it." With his dating Becky it wasn't unusual for us to end up at the same parties, and it wasn't like I'd never done it before, I just didn't make a habit of it. Like, I'd never kissed Becky, butI'd done it to tease a boy I liked a couple of timesrather than say having done it for my own pleasure (even though I have to confess to enjoying it on the rare occasions I did so).

"Done," I replied. Brandon left the room, and I wondered who I'd be kissing. There were a few obvious choices. There were a couple of openly bi girls who would probably be there, and a couple of party girls that would do it for fun, so I had options; I decided just to see how things went down on the night.

Becky came over to our house before the party, and we dressed together and put our make-up on in my room, leaving Brandon to his own devices.

I put on a black skirt that fell almost to my knees, and that flared beautifully if I chose to spin. I paired it with a simple pale blue t-shirt and ankle-boots. Becky opted for ultra-hot slut mode in a skin-tight dress with a hemline that hugged but barely covered her butt. It had a scooped neckline, and the open back plunged almost to the crack of her ass.

"Good God, you'll be swimming in drool tonight," I laughed when she posed for me.