Dares Turn Into More

Authors Note: All characters in the story are over 18.

Gabe was drunk off his ass. He'd arrived at Ronnie's house, his best friend, a couple hours before everyone else came and they had the smart idea to pregame the pregame. His twin sister Brooke had come to the actual pregame with plenty of cocktail ingredients and he downed drink after drink, amazed at how he couldn't even taste any alcohol. Then at the bar, he'd met a cute asian girl celebrating her birthday, and like the gentleman he was, he had to buy her some drinks. Of course he couldn't let her drink them unaccompanied so he had a couple more alongside her. Though he managed to cop a feel over her tight white jeans and got a nice handful over her spaghetti strap crop top, he didn't go home with her. Instead, he found himself back at Ronnie's, their group dwindling down to the two guys, his sister, and two more girls, Vanessa and Melanie.

The whole group had plenty to drink, the stench of alcohol emenating from all of them. They sat in a circle and were in the middle of a game of Truth or Dare, though they came up with a new rule where they had to take a shot if they picked truth, which explained why Vanessa and Melanie already had their shirts off. They sat there both in simple lace bras, Vanessa's double Ds held up by a white one while Melanies perky Bs were held in a pink one.

"I don't know what else I expected, letting you two be the first ones to go", Brooke said, shaking her head at the two boys, drunkenly smiling and unashamedly looking back and forth between Vanessa and Melanie.

"Well since it's my turn, Gabe, truth or dare?"

Brooke had to repeat herself to get his attention, too entraptured by the way Vanessa's tits bounced around when she got up to get herself another drink.

"Dare obviously"

"Put on Vanessa's top and send a pic in our family group chat"

"Psh easy," he said, eager to take off his top and show his muscles to the girl. He'd been hitting the gym during college, at first to try and pickup girls, but instead found a group of guys as gym buddies and began really enjoying his workouts. Ronnie was one of those buddies. He went religiously with him and his hard work had paid off.

Even Brooke had to appreciate his chiseled muscles, happy that she would get photo evidence that would come in handy later when she was alone in bed.

"My turn?" Vanessa exclaimed, eager to get the game moving.

"Ok then, Brooke I dare you to-"

Melanie hit her on her arm, "You gotta ask her truth or dare first"

Pouting, she asked her, getting a "dare" in response. Brooke knew she could NOT handle another shot.

"Well since I know you don't have a bra under that top, it's only fair that you take off your jeans. We can't be the only partly undressed girls here"

Brooke looked over at her brother, seeing if he would object but he was back to looking at Vanessa. Sighing, she took her jeans off, careful to not peel her light blue thong along with them. She sat back down, cross legged and trying to cover her panties with her top, grateful she decided to shave before going out tonight.

"Ronnie, truth or dare?" Melanie asked.

"Dare"

"Show us your cock"

All three of the girls giggled at Ronnie's reaction, but after some coaxing, he pulled down his pants and boxers, sporting a good sized erection that Brooke licked her lips at. He sat back down and asked the question to Brooke.

"Dare"

Brooke looked at Gabe in surprise after Ronnie dared her to blow him, but his seemingly interested reaction gave her the confidence to push Ronnie to lie down and began to lick him from the bottom of his shaft to the top. Looking over, Vanessa and Melanie decided to forgo the game and pounce on Gabe, stripping him of his pants and boxers as well as Vanessa's top. She caught a glimpse of his cock as they started pulling him upstairs, feeling herself get more wet as she was enthusiastically bobbing on Ronnie's cock. After a couple minutes of sucking and playing with his balls, she got up and squatted over him, slowly lowering herself on his cock. She took off her shirt and her nice C cups came into view, perky and with small nipples. Brooke leaned over, riding cowgirl and gave him a nice long kiss, her toungue exploring his. Her brown hair tickling his face as they continued making out. She could feel pleasure start to build up and starting riding faster, moaning so loudly that the three upstairs could probably hear.

Meanwhile, Gabe found himself in heaven with Vanessa on his cock and Melanie on his face. He had somehow managed to undo their bra clasps at the same time and was rewarded with both girls on their knees, Vanessa focused on his balls while Melanie sucked him off. Gabe felt Vanessa switch from ball to ball, giving each a long suck and tickling them with her tongue. Melanie managed to deepthroat him, the feeling of the back of her throat almost tipped him over the edge.

After the second time he told them to stop in fear of cumming, he was then pushed onto the bed where Melanie started off riding him and Vanessa sucking on Melanie's cute, perky tits, occasionally stopping to make out with her. Vanessa switched with her after a bit, even tighter than her friend, and began slamming down on him, getting him closer and closer to orgasm. Melanie took her place right over his head and began smothering him. With Melanie's pussy suffocating him, he couldn't let them know he was about to cum and started to unleash inside Vanessa. He grabbed her hips, slowing her down on his sensitive tip, enjoying the waves of pleasure washing over him. He could feel Melanie shaking as he brought her to orgasm and she collapsed on his left, one of his arms wrapped around her naked body and feeling her tits smushed against him. After resting a bit with Gabe still inside her, Vanessa got off and assumed the same position on the right, giving him a kiss on the cheek before snuggling against him. Gabe fell asleep with the largest smile plastered on his face.

Gabe and Brooke were on their way home when she decided to bring up what happened that night.

"Well that was something," she said laughing. "I hope you enjoyed Vanessa and Melanie"

Gabe just smiled and gave a chuckle.

"Truth or dare was kinda fun too"

"Oh yes"

"You just enjoyed seeing the girls in their bras"

"Well I didn't get to see all the girls, but definitely yes"

Brooke blushed at his comment.

"Anyways, dares are always fun like that. It always gives me a rush for some reason"

"Why don't we do it at home then?" Gabe offered.

"You think so? Ok," she replied. "How about we each get one a day, but they can only last for the rest of the day?"

He nodded, thoughts already racing through his mind.

"I go first then," he blurted out.

She gave him a pouty look. "Fine"

When they got home they both took a shower and regrouped at the table where Brooke started whipping up pancakes for them. Their parents were hardly at home, always taking care of their clients in overseas countries. The siblings were used to their absence and settled into a normal routine without them.

"Brooke, my first dare is that you go braless today"

Booke looked up at him and then looked down at her own outfit. She was wearing some short cotton shorts, a loose black tank top and a simple bra underneath. She smiled at him and reached back to unclasp her bra. As she took it off without taking her tank top off, Gabe's eyes were glued to her chest, hoping to catch a peek of nipple. She threw the bra at him and went back to whisking the batter. He could see her boobs jiggling in her tank top, no longer confined by her bra. When she pulled her hands back, he could see her nipples poke out. His cock was at full mast now.

Throughout breakfast, Gabe's eyes were glued to her chest. She reveled in the attention and felt some wetness building up in her panties. She decided there to spend the rest of the day in the common areas where Gabe could watch over her.

Other than Gabe following around Brooke the whole day, nothing further really happened. He caught quite an eyeful of cleavage whenever she bent over and plenty of sideboob. But when the two parted at night for bed, they both furiously masturbated, him with lotion and her with her vibrator.

In the morning she was waiting for him at the breakfast table with a smile on her face.

"Your turn. Drop those shorts and put these on"

She threw a pair of his compression shorts at him. He chuckled and smiled back.

"Fair play" he said, turning around and putting them on. He turned back and put his arms out. Brooke's eyes wandered down, stopping at the outline of his cock. The thin compression shorts did little to hide it, and she could tell by his erection that he was excited by her dare. He sat down at the table but she shook her head and told him to stand up.

"I gave you a show so I think I should be given the same"

She didn't know how, but his cock stayed hard the entire time. After breakfast, she watched him mow the backyard in just those shorts, his shirt off because of how hot it was. Though no longer rock hard, his cock made a sizeable outline in his shorts. She sat on the couch after, watching him walk around the house doing various chores, eyes glued to his shorts just like his were to her tits the day before. At night, they did the same routine as the last night, but her horniness made Brooke a little more vocal, which Gabe could hear if he tried hard enough.

The next morning, Gabe was waiting for her at the table. On it was a pink bikini. She held them up, seeing the bottoms were fairly cheeky and the top was slightly too small for her. They didn't have to say anything to each other, Brooke already knew what to do. She turned around and stripped, Gabe able to see a glimpse of her pussy as she bent over to get her legs in the bottom. She adjusted the top and turned around.

"Ta-da!"

She looked down at his crotch, a bulge slowly growing in his pajama pants. She giggled and went over to the fridge to start breakfast.

By midday Gabe was torn on what to do. His sister was watching TV with him while he watched her. His cock was straining against his pants, the urge to jack off growing by the minute, but he didn't want to miss out on his sister in her new bikini. She was laying belly down on the carpet in front of him, her legs spread and he could faintly see the outline of her pussy lips through the bikini. She looked back seeing the expression on his face and the bulge in his pants and spoke up.

"Will you let me have my dare today? I think you'll like it"

"He nodded, wondering what she had in mind. She knelt in front of him and said,

"Let me watch you jerk off. I've never really seen a dude jack off before"

He quickly nodded and got his pants off, Brooke finally getting a good look at his bare cock. To her, it was beautiful, the round head and a thick, girthy shaft. She saw him looking around for lotion so she went ahead and just spit on his cock. She smiled innocently at him.

"Nice dick bro"

He got the spit on his hands, so turned on by what just happened. He decided to not take it slow and started stroking furiously, staring at her boobs barely confined in her top. Brooke's hand disappeared under her bikini bottoms, her eyes entranced by his blurred hand. Gabe could feel that he was about to cum and looked around for a tissue but couldn't find anything close. He felt himself go over the edge and the first spurt went high and landed on his sister. The next ones he tried to get onto himself, and by the time he was finished he was pretty covered in his cum.

"Mmm," Brooke said, tasting the little bit that got on her tits. "You taste pretty good, but it's a bit too bitter for me. A little salty"

Gabe's cock jerked at the sight of his siter tasting his cum. She quickly nabbed a couple tissues and handed it to him.

"I can't wait to see what you come up with tomorrow. But I do have to warn you, I'll be out most of the day running errands. I have to get groceries and renew my license at the DMV and you know how long that can take."

Gabe just nodded, stupefied after his orgasm.

The next day she found Gabe smiling as she came down. On the table next to him was a small vibrator, and in his hand was his phone, open to an app she figured out really quickly. She just chuckled and shook her head.

"I was hoping you weren't going to make me wear another bikini, or a really sheer top for going out today, but this should be good"

Today she decided not to give him a show and just took it upstairs. She came back down in leggings and a crop top, a casual outfit for running errands.

"Ready to go Gabe?"

In response, he just turned on the vibrator in her panties with his phone.

"This will be a good day," he said, looking at his sister already shaking a little at the lowest intensity.

Their first stop was the fast food drive through to get breakfast.

"Yes I'll have o-o-one breakfast burrito please," she managed to stammer out as Gabe turned on the vibrator.

"And a- oooh"

"Sorry what was that?"

She hit her brother as she struggled to make her order. The worker was a middle aged guy, smiling at what was going on when she pulled up to the window. After a couple of moans, he figured out what was going on, giving Brooke her items one at a time in order to keep the show going. She moaned her thanks at him and sped off, eating the food on the way to get groceries.

Once they got to the store, she grabbed a cart, knowing she would need something to hold onto. She almost dropped an orange when he suddenly brought it up to full intensity. Some of the other shoppers glanced at her. Brooke sheepishly continued shopping when she suddenly stopped, recognizing an older lady passing by. Her face lit up.

"Mrs. Pemberton!"

"Oh my if it isn't Brooke and Gabe. Oh you two look so grown up now."

Mrs. Pemberton was their old middle school teacher. She had both of the siblings in her class, back when they didn't get along and had to separate them often.

"Well it has been q-quite a while r-right?"

Brooke looked at Gabe in alarm, surprised that he would turn the vibrations on while they were talking to their old teacher. Gabe just smiled in response. Mrs. Pemberton looked at them funny by continued to chat with Brooke, not knowing she was close to orgasm.

"Do you remember when you two used to fight every day? Oh that was so cute to watch, I hope you are both a lot closer now and get along"

"Super close now," Gabe said with a knowing smile.

"Sorry Mrs. Pemberton but we have to go now," Brooke said in a high pitched voice. She gave her a quick hug and speed walked down the aisle, shaking and holding onto the cart as she crouched down at the end of the aisle and orgasmed. She stayed there and recovered, hitting her brother when he showed up next to her. He smiled back.

"That was probably the most intense orgasm you've had huh?"

She shook her head, grinning. The thought of getting caught had turned her on so much but she didn't want to tell Gabe. Turning away, she went towards the meat section.

Brooke had managed to have two more orgasms at the DMV, the long wait leading Gabe to play around with the vibrator app more than usual. The two college guys waiting across from them seemed to enjoy the show, but Brooke didn't seem to notice, focusing on the vibrator smushed against her pussy. When they finally got home and changed, she threw the panties at him, the bottom lining soaked.

"See what you did?"

He laughed as he held up the panties. "Seems like you had a good time today, was it four times?"

"Just wait for tomorrow," she said walking towards the kitchen, already thinking about what to make.

That night, Gabe used the panties to masturbate, first smelling his sister on them, slightly sweet and musky. He wrapped it around his cock and in no time was shooting cum into a tissue. He laid them out to dry, hoping to use them again soon.

Gabe found Brooke already waiting for him on the couch. She was wearing a cute sports bra, but he ignored that once he saw she was bottomless.

"Today, you have to make me orgasm more than I did yesterday. So... five times. You better get started"

She held out a vibrator towards him.

"I find I orgasm fastest with a tongue in my pussy and this on my clit"

He quickly grabbed the vibrator and knelt down. Here was his sister's pussy right in front of him, the pink slit looked perfect to him. Her lips were big and inviting and he could already see that she had gotten a head start without him. He quickly licked it from bottom to top, tasting her. She moaned as he got a delicious little bit of her and began to go to town. After just a couple minutes of work, she started shaking and moaning louder.

"Ohhhh Gabe," she exclaimed, grabbing his hair and smushing his head closer to her. Her orgasm subsided and she got up, not bothering to put on any pants.

"Thanks, I'll let you know when I'm ready for the next one," she giggled. Brooke brushed his rock hard cock with her foot.

"But no cumming for you until I say so. Trust me, it'll be worth it"

Gabe made a sad face, but was looking forward to the rest of the day. After breakfast, Gabe came back downstairs to find his sister on a picnic blanket in the back. She had taken the sports bra off, for a more even tan he presumed, and was laying face up. He quickly grabbed some suntan lotion and joined her outside. He squirted some suntan on his hands and started working on her chest. She figured the rest of her body would be neglected so she'd already put some on her legs and arms.

"Take those off," she said, pointing at his shorts. She grasped his erection and quickly gave it a few teasing tugs, making sure he didn't cum.

Spending too long putting way too much suntan lotion on her boobs, she lead his hands down to her pussy, already close to another orgasm. With suntan lotion on his hands, she instructed him to use his tongue. With his previous experience, he was able to get her to cum quickly.

"Ohh brother you have a nice tongue," she moaned as she orgasmed. He continued to lick until she became too sensitive. After, she got him to stand and knelt down in front of him.

"I'll get you back a little, but you're not allowed to cum. If you do, then my pussy is off limits"

He nodded enthusiastically, just grateful to get a little bit of action. She gently fondled his balls and wrapped her lips around his tip. She swirled her tongue around the head and made eye contact with him.

"Brooke," he moaned, so turned on by his naked sister giving him head and staring directly in his eyes.

He grabbed her head and pulled her off.

"No more or I'm going to cum," thinking about what she said earlier, thoughts of her beautiful pussy keeping him disciplined.

She giggled and gave him a teasing smirk.

"Don't forget, you still owe me three more. I'll make it worth your while"

She walked back inside, her hips swaying and Gabe wondering how he was supposed to get through this day without cumming.

Thankfully she gave him time to cool off, asking for one orgasm after lunch and another before dinner. Both times she was in her room, still naked and her legs spread for him. She had at least licked up his precum as he was leaking profusely, but to her relief he still didn't cum. He was wondering when his last time of eating her out was when she walked down the stairs in black lace lingerie. Gabe was sitting down on the couch and started to get up, but she motioned for him to sit down.

"Here's your reward," she said smiling, pulling down his pants revealing his already hard cock. She put on some music with her phone and started dancing, her hips swaying and tits jiggling. She would give him a couple strokes or a quick deepthroat every so often until she finally felt like he was at his limit. Brooke peeled her panties down and leaned over the dining table, presenting her pussy to Gabe.