I Dare You

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It was probably only between five and ten minutes between my hiding in the closet and their arrival, but it seemed like an hour. Finally, they came into the room holding hands. If I'd been wet from anticipation before, I was practically dripping in my underwear when they entered. I watched Brandon turn to Becky and kiss her. Becky had her back to me, and Brandon's hands were cupping her butt as they kissed, squeezing and groping vigorously. As the kiss broke, he glanced over Becky's shoulder in the direction of the closet. I slipped the tips of a few fingers through the slats to give him a little wave. Becky squatted in front of him, attacking his pants.

"God, I need me some python," she moaned as she released Brandon's jeans. When she dragged them down, he was already rock hard. I wondered how much of that was Becky and how much of it was from knowing his sister was watching. Becky grabbed hold of him and started sucking. All I could see was the back of her head bobbing back and forth, though I could hear the slurping sounds as she slobbered all over him.

Brandon looked in the direction of the closet again and I felt like he was staring straight at me. I slipped my hand up under my skirt and down inside my panties, fingers seeking and finding my extremely moist slit.

After Becky had sucked him for a while, Brandon pulled Becky to her feet and grabbed hold of her t-shirt, pulling it off her. Her exposed back revealed the absence of a bra and I had a sudden desire to see her cute little tits.

Brandon pulled his own shirt off and to my delight, managed to turn side on, Becky moving with him so I could see them both in profile. He then kicked his shoes and pants away while Becky reached out and grabbed hold of his erection, tugging.

"Getting naked would be easier if you let go for a bit," Brandon suggested.

"Yeah, but it's my python and I like to play with it," Becky said with a laugh as Brandon nearly fell over.

It was almost funny seeing Brandon trying not to lose his balance as Becky refused to let go of his cock.

"I'm pretty sure it's my python actually, but I'm happy to let you play with it," Brandon laughed.

"That's good, because there's nothing I like better than riding our python," Becky purred, dropping her head to suck him briefly again. It was amazing how she could stretch her mouth wide enough to get around it. Brandon managed to get the second leg of his jeans off and kicked them away, pulling Becky from his cock again. He grabbed her by the waist, lifted her off the floor and deposited her on his bed, her little tits jiggling delightfully as she came to rest.

Brandon unfastened her tight black jeans and grabbed hold of their cuffs and pulled them off her. It wasn't a smooth process because Becky's jeans were so tight, but they finally came off with a bit of wiggling, twisting and tugging. Her black thong was half pulled off as well, and Brandon made quick work of pulling that down her legs as well. I have to say Becky looked really hot laying naked on Brandon's bed, her bare mound exposed. Brandon knelt beside his bed and pushed Becky's knees apart. His head blocked my view, but it was clear that he'd started eating her pussy. Becky's head tipped back, and her hands went to her tits, fingers pulling on her nipples as she moaned and groaned in pleasure. I could see Brandon's long, fat cock and heavy balls hanging between his legs, and I had a sudden urge to step out of the closet, reach between his legs and take hold. I didn't though, I just plunged two fingers between my sopping wet lips and frigged myself.

Becky came with a thrashing arch of her back and a muffled cry of joy: muffled I suppose, so I wouldn't hear her from my room. And then Brandon mounted her, pushing his cock between her legs. I wished I could have seen better, but it was hot, regardless.

"I want to taste us," Becky moaned and pushed at Brandon's chest. He pulled his dick out and stood up. Once again, he was kind enough to stand so he'd be side on to me. I could see Becky's juices glistening on his cock as she took him back into her mouth. She took as much as she could (which left an impressive amount un-sucked) and held her head there, slobbering, saliva running down his shaft, which she took in both hands.

"Oh fuck," Brandon groaned as she released him.

"Lie down baby, I wanna ride the python," Becky demanded. She pulled him across her body to the other side of the bed and moved out of the way so he could lay on his back. Brandon's rock-hard cock laid flat against his stomach, and Becky climbed up and stood over him on the bed. Naked, she looked amazingly hot. Of course I'd seen her naked lots of times when we changed clothes together for one reason or another, but this time the fact that both she knew and I knew she was about to impale her wet, swollen pussy on my brother's python made all the difference. She squatted over him and then knelt, straddling him. I expected her to reach for his cock and guide it into her pussy, but she simply pressed down on his shaft and started grinding along the bottom of it, moving back and forth. I could imagine her labia spread either side of him, slipping and sliding, propelled by her hands on his chest.

"God, I love riding you," Becky groaned.

"Let me inside," Brandon groaned. "I want to feel that tight little pussy sliding up and down on my cock."

"In a minute," Becky replied, "Just let me have some fun first." She kept sliding her pussy back and forth along his cock and Brandon alternately reached up with his hands or mouth to pull or suck on her nipples.

"Now Becky, right now I'm going to fuck you," Brandon told her, taking her by the waist and lifting her up. He moved her aside, clambered up and told Becky to get on her hands and knees, then moved in behind her, once again considerately side-on to my viewpoint. I watched Becky throw her head back in pleasure when Brandon drove his thick cock between her lips. He pushed inside her slowly, then he pulled back and thrust forward. Becky cried out i and Brandon took her hips in his hands as he started working back and forth. I imagined his massive member between my own legs and how it would feel. My fingers were a poor substitute, but they were all I had with me. I brought them up to my clit and started sliding them around it, teasing and stimulating it as I kept watching the hot action on my brother's bed.

"Yeah, fuck me Brandon, fuck my little pussy," Becky demanded.

"So fucking tight Becky, God, I love being in your cunt! I want to paint you Becky, I want to spray cum all over your tits."

"No, cum inside me Brandon, I want to feel you spew your load inside me."

"Please let me cum on you," he groaned. "You look so fucking hot with cum all over this amazing body."

"Oh fuck, alright," Becky conceded. They kept fucking for quite a while until Brandon announced he was ready to lose it. Becky quickly dived forward and rolled over and Brandon took his erection in hand, pumping it rapidly. With a grunt and a moan of pleasure, he exploded, shooting his cum over Becky's tight little body. I rubbed my clit furiously and came just moments after my brother did, my body on fire. My legs shook and shuddered and I had to reach for the wall behind me to steady myself so I wouldn't fall out through the doors.

One bonus of Brandon cumming all over my friend was that she wanted to clean up quickly, so she didn't want to hang around cuddling on the bed. Brandon escorted her out of the room with a glance back toward his closet and me within it. As soon as they were gone, I slipped out and made a bee-line for my room. I wondered how much of my scent would linger in his closet after I'd cum in there.

I heard Brandon's car leave and went to bed, my mind on fire with the memories of what I'd just seen.

As with the other dares, nothing was even mentioned about it in the days that followed, but my brother and I exchanged some odd glances across the breakfast and dinner tables.

I went on high alert after that, sometimes going to ridiculous lengths to avoid being anywhere where Brandon could peg me.

I lasted an entire three weeks before he managed to get me. Mike was a happy beneficiary of both my willingness to be away from the house, and my desire to relieve my sexual tension.

~~~~~~~

When Brandon came into my room the following day, I was anxious to know how far he'd ask me to go.

"I dare you," he said after we'd dispensed with perfunctory greetings," to suck my cock and let me slide it and by it I mean my cock, between your tits until I cum in your mouth."

There. He'd now presented the line that for weeks I'd pondered crossing. My mouth on his cock receiving his cum. My lips sliding up and down his monstrous, gorgeous, wonderful cock. My decision about whether or not to swallow. The tit fucking was unexpected I had to admit, and if it had been only that, I probably would have agreed to it immediately.

"I need to think about it, Brandon," I said.

"I'll give you twenty-four hours," he told me. "After that you lose."

I'm not going to dwell on how tumultuous my thoughts were for those twenty-four hours. I oscillated between enthusiasm and concern. The concern was in essence that that it was my brother and whether there would be any way back if I regretted it afterward. The enthusiasm was that I thought the idea was fucking hot! Eventually I rationalised that I hadn't regretted anything we'd done so far, so I decided to say yes. To say that Brandon was pleased and excited when I told him, would be a gross understatement.

We agreed Saturday would be the day.

I was super nervous that morning, more nervous than I'd ever been, even before a date with a boy I really liked. For once I wouldn't be the one to initiate anything. I probably wouldn't be making many decisions, except for the one when his semen had spurted into my mouth. I left it to Brandon to come and find me rather than going to awaken him, as I had with previous dares. That didn't help with the nerves though, because even though I'd awakened early I couldn't go back to sleep, and I had no idea when he might come into my room. I also didn't want to do anything just to pass the time, so I just lay on my bed, hovering between anticipation and worry.

He must have set an alarm, because it was only about ten in the morning when I heard movement in the passage outside my room. I'd not bothered dressing for the day, because of his request to fuck my tits.

Without knocking... he didn't need to... Brandon cracked my door open and greeted me simply, "Hey there."

"Brandon," I responded neutrally. He was only wearing a pair of boxers and his cock was clearly erect at the prospect immediately before him.

"So, any thoughts on how we proceed?" he asked.

I had in fact given it some thought in the hours leading up to his entering my room, and I suggested that I sit on the edge of my bed while he stood in front of me. It would put him at a good height for me to suck him, though we'd likely have to adjust a bit for the tit fucking. I described my plan and sat on the edge of the bed. I removed my t-shirt so I was in just my panties, and Brandon advanced on me, dropping his boxers just inside the door. My eyes were glued to his cock as he took a couple steps across the room and stopped in front of me. I reached for his cock and wrapped my hand around his thick shaft, stroking him, wondering again at the size of it.

"Suck me, Sarah. I want to see your lips wrapped around my knob."

I looked up into his eyes even though he was focussed on my mouth, and I opened wide. I slipped my mouth over his knob, lips caressing him, tongue sliding under the head. He gasped and his eyes widened. I slid my lips down and back up again, tongue flickering over the tip before sucking him deep. I hummed as I sucked and allowed my saliva to flow down over his length, until I felt it on my fingers, which let me slide my hand up and down the bottom of his shaft while I twisted my head and sucked on the top of his cock. I kept working him and drooling down his cock until my hand was liberally coated. I cupped his balls with my other hand, and when my saliva made it that far, I decided it was probably time to try the tit-fucking thing he wanted.

"Time to slide your cock between my tits, Brandon?" I asked him, letting go of his cock to squeeze my big, firm boobs together.

"Fuck yes," he replied. He kind of squatted as I leaned forward, but the angles were wrong. After a few tries, we worked out that his sitting on the edge of my desk chair with my kneeling in front of him seemed best. Brandon lay his dick against my chest and I squeezed my tits around him. I moved up and down and drooled saliva down over it, holding my tits tightly around him. He was long enough that when he thrust up between them there was plenty of overreach for me to dip my head down to and suck. I kept at him like that for a while, tits mashed around his shaft, mouth working the top portion of his cock.

Brandon moaned and groaned, and I felt his hands in my long blonde tresses. He held my hair close to the roots, hands tight against my scalp. He didn't pull my hair so much as simply hold onto my skull, his rock-hard cock thrusting up into my mouth. I let him fuck my tits and mouth until he announced he was going to cum.

We forgot about the tits, and I let him thrust with my lips glued to the skin of his shaft until I felt him tense and give a final sprint, his cock totally rigid within the confines of my mouth. When I felt the first blast of hot, salty cum hit the back of my throat I opened my lips and he continued spurting into my mouth, but I let the cum run back down his cock. It trickled down his shaft and into my cleavage. I remained like that for what seemed ages of bliss as he blasted his load into my mouth over and over again.

When he was finally done, I pulled my mouth back, looked up at him and pumped his cock with my cum-soaked cleavage while he moaned in appreciation.

"Well that turned out a bit messy," I laughed.

"It was fucking amazing, Sarah," Brandon replied. He grabbed the box of tissues from my desk and passed a handful to me. I cupped them under my tits as he pulled his cock away and his seed slid down my body.

"Good. I'm going to shower." With that, I left the room for our shared bathroom. When I returned, Brandon was gone. As always, nothing more was said. While I'd showered I was once again left with the same thought I'd had after almost every one of Brandon's dares. What would I dare him to do next? Should I ask him to make me cum? Should I get him to eat my pussy, or was that something I should wait for him to dare me to let him do? I knew he did that, because I'd watched him eating Becky. I hadn't resolved what it would be by the time I'd left the shower, but as I dried myself, I had a fantastic idea, something that might even win me the game! But I had to peg him first, of course. Fortunately, I came up with an idea that might even make that easier.

A couple days after the dare, Becky came over to visit with me until Brandon came home from football later that night. We hung out and chatted and had fun like we usually do and then when he arrived home, we all sat in the living room to watch some television for a while. I made sure to have the peg with me. When the show we were watching was getting close to finishing, I knew it was time to make my move. They were clearly going to disappear the instant it was over, and I knew exactly what they were going to do. I'd sat on the opposite side of Becky so she was in the middle and the remote control was on the far side of Brandon. I wondered aloud what would be on next and then rather than have Brandon pass me the remote, reached across both of them. I crushed my tits against Becky's legs and reached with my hand, which put my face right near Brandon's crotch.

"Bloody hell Sah's, Anyone would think you were trying to eat your brother's cock the way you're going," Becky exclaimed.

"Oh, and you'd just love to watch that wouldn't you, ya perve!" I laughed, wobbling my tits against her legs. I couldn't quite retrieve the remote, so I wiggled across their laps until my tits were crushed into Brandon's crotch, and my crotch was against Becky's legs. Becky started spanking my ass with loud slaps, and I knew for sure Brandon would be watching her, so I clipped the golden peg onto the leg of his shorts before grabbing the remote and slithering back to my seat. Talk about hiding in plain sight!

I blew Becky a playful kiss.

"Careful, I might actually kiss you," she teased me. Brandon groaned.

"Can't go turning my brother on that much though," I laughed. "He might burst out of his shorts." Becky and I both looked at Brandon's crotch, where there were obvious signs of arousal. He grabbed a pillow to cover up and we laughed at him. No one said anything about how weird it was for me to be the one noticing his arousal, nor mentioned how it had been stabbing into my tits when I was crushed against him.

The show finished, and they disappeared pretty quickly.

"Shit," I heard Brandon say when he stood up. Becky was ahead of him and turned back.

"What's wrong?"

"Nothing, I just forgot I was supposed to do something for Dad. I'll have to do it first thing tomorrow." He was holding the peg in his hand and shook his head at me.

I quietly teased my pussy while I watched the next show. Im sure that upstairs they went at it like rabbits. My bottom was a little sore from Becky's spanking and to be honest, I was surprised that I liked the feeling.

Brandon came into my room later that night after he'd run Becky home.

"That was pretty sneaky Sis, I have to give you extra credit for that one," he laughed.

"Why thank you. I suppose you're here to ask about your next dare?"

"The thought had crossed my mind once or twice," he admitted.

"Well normally I'd leave you wondering, but this time I think I'll just leave you thinking about it, just like I'll be until it happens."

"I'm not sure that's a good thing."

"I dare you to suck your own cock for me. Until you cum."

"What?" he asked in shock.

"I know you can do it. You're sure as hell big enough that you can, so don't deny it."

"I've never tried," he claimed. I didn't believe him.

"Well then, you'll get to try something completely new then... unless I win the game that is."

"I'll think about it."

"Twenty-four hours."

"Sure." He left my room. For some reason the thought of watching him suck his own cock turned me on more than I'd expected. I masturbated properly then, giving myself an orgasm before drifting off to sleep.

Every time I saw Brandon after that, he had a weird look on his face. He could barely face me. I wished I'd thought of the dare earlier, it was the first time I felt that I'd really put him on the back foot, although his pissing in the back yard way back when had come close. I honestly thought that when push came to shove, he was going to decline. He proved me wrong, though. With an hour to go, he told me he'd do it the next time our parents were out. I couldn't believe how excited I was.

On Wednesday I received a text from Mum saying that she and Dad were off to some function for Dad's work, and that Brandon and I would have to fend for ourselves for the night.

By the time I got home, I was wet as all fuck.

"You got Mum's text?" I checked with him when he came home after football practice.

"Yeah," he said, decidedly less excited than I was.

"So..."

"Yeah, yeah, after I've showered, okay? Let me get that out of the way, then I'll do the dare."

I left him to it, as it was pretty clear that if I pushed too much, he wasn't going to be a in a happy place. When I heard the shower running, I pictured him in there, washing that monster cock, soaping it up and down until it was nice and hard. I doubt that's what he was doing, but it was fun to imagine. I played with my pussy while I did so. The crotch of my panties was sodden. I thought about changing them before the dare, but decided not to, since I was sure I'd need to afterwards.

1...456789