“Maybe this was a bad idea.” Will muttered as he shuffled nervously outside of the door to her room.
“Look it’ll be fine.” Dawn dawn called from behind the door. “None of your classmates know me anyway so they’ll never know I’m your sister.” She beamed as she opened the door and beamed to him. She was wearing a tight red dress that showed off her curves nicely and showed a lot of her ample cleavage. “I’ll just be your mysterious hot date.” She grinned without noticing how Will flushed when he looked her over. “Now come on, dad said he’ll let you borrow the car as long as you promise to stay away from the punch.”
—
Will pulled the car into one of the parking spaces furthest from the dance hall and killed the engine. His hands fell into his lap as he just looked out of the window towards the lights and noise of the dance hall.
“Hey.” Dawn said as she took his hand and gave it a little squeeze. “It’ll be fine okay?” She said in a soothing voice. “We’ll just sit here for a while okay? Until you feel ready, no pressure.” She pulled his hand up and gave it a small kiss. “Take your time, I’m here for you.”
Will nodded and kept looking out of the window towards the colorful lights. “I really don’t think its a good idea-” He began again but was interrupted when Dawn took his shoulder and turned him to face her.
“Don’t focus on them, focus on me.” She smiled as she stroked his hand. “I’ll be right next to you this entire time, whenever you need a break from it all just look into my eyes and it will be just the two of us there.” She smiled and kept his eyes on hers. Slowly but surely she felt the tension bleed out of him, his shoulders falling into a relaxed position and his back straightening a bit.
“Alright, I think I’m ready, thanks sis.” He smiled as it was his turn to pull her hand up and give it a kiss.
“You’re welcome, I’ve gotta make sure my date enjoys his prom afterall.” She winked as they got out of the car.
—
“Alright we’ve been talking, and this whole thing-” Rob gestured to Dawn and Will who had been sitting at a table chatting over some snacks. “Its not real.”
“W-what do you mean?” Will said trying hard not to show how bad he was freaking out.
“You’re not a couple.” One of the other kids added in.
“Of course we are.” Dawn replied sounding offended.
“No you’re not.” One of the girls chimed in. “You’ve only danced once, and you haven’t kissed a single time since you got here.”
“Besides, you’re way too hot to settle for that dweeb.” Rob added and gained a chorus of chuckles from his little band of followers.
“I’m pretty sure I don’t need someone who can’t even tie a tie correctly to validate who I date.” Dawn spat back with ice in her voice.
“I- I know how to tie a- That doesn’t matter, you’re not a real couple, you’re probably like his cousin or something.” Rob almost yelled as he fumbled with his tie.
“We’re not cousins.” Will began, feeling the last of his resilience give away. “We’re-”
“Together.” Dawn cut in and stood up and took Will’s hand to get him standing as well. “If we were cousins would we do this?” She asked and leaned closer. Will’s eyes went wide with surprise as her lips came closer, he wanted to pull away until he caught her eyes, she was there for him, just like she promised. Her lips caught his in a long soft kiss, he closed his eyes as his arms instinctively went around her and came to rest on her hips as they kissed. It was just the two of them, just like she had promised, the prom didn’t matter, it was just the two of them enjoying themselves.
When she finally broke the kiss Will felt it linger on her lips as she looked over her shoulder at Rob. “What? No more stupid theories?” She asked with a sugary sweet voice as she pushed herself a little closer to Will, pressing against his body with her own. “Or maybe you’re just hoping for a show because you couldn’t get a date yourself.” She smirked and with a grumble of profanities Rob and his group scurried off.
She turned her attention back to Will. “Are you okay?” She asked softly, looking slightly down at him in her heels.
Will nodded silently and just stood there with his arms around her. “You- you didn’t have to do that for me.”
“Of course I did.” Dawn smiled. “I said I was going to be there for you, and I meant it.” She said as she put her arms around his neck as the band began playing a slow song. “I’m not going to let them spoil your night.” She smiled and began swaying to the music.
“Thank you.” Will blushed as he had no choice but to follow her lead and slowly sway with her.
“If you want to thank me, just make sure you enjoy yourself.” Dawn smiled and gave him a kiss on the forehead. “That will make me the happiest.” She caught his eyes again and the two of them danced the night away all alone in their own little world.
—
“I’m sorry, I swear its the last time.” Will apologized nervously as they got to the party. Summer break was almost over by now and since prom Dawn had gone to 3 private parties as his girlfriend. “When I go off to college next month I’ll stop seeing these people and you don’t have to do something like this anymore.”
“You don’t need to apologize.” Dawn smiled. “I like going to parties with you, you’ve come so far.” She beamed proudly. “Now, do you wanna go in, or should we wait a minute?” She asked supportively.
“I think I’m ready.” He said after steeling himself for a few moments.
“I’m so proud of you.” She smiled as she leaned in and gave him a small kiss. “Then lets get going honey.” She winked.
—
It wasn’t a massive party, only about 20 or so people, but it was enough that the house was crowded, and the volume had been turned up high enough to guarantee a noise complaint. It was the last place in the world Will wanted to be, and yet here he was. At least Dawn was enjoying herself, dancing to the music without ever straying too far from him. Everyone was looking at her or talking about her in the corners, the polar opposite of Will’s complete nonexistence in the eyes of the rest of the partygoers.
“Whoa, I am so done for now.” Dawn sighed as she came dancing over and almost tripped over her own feet as she gave him a hug. “You still doing okay?” She asked and giving him a little squeeze.
“Yeah, I’m okay.” He smiled up to her and put his arms around her hips. “Just… you know, having fun.” He said and gave her a small kiss.
“Liar.” Dawn said and gave him a kiss on the nose. “What’s got you down?”
“… Everyone is looking at you, talking about you, thinking about… you know… doing it… with you.” He muttered. “Do you really like that?”
She thought it over for a moment before answering. “Yeah, I do.” She beamed. “Just think about how jealous they’re all getting of you, all the stuff they want to do with me but can’t because I’m in your arms.”
“But-” Will flushed red and composed himself before forcing the rest of the words out just as the music skipped to the next song and the house got way quieter for a moment. “But we haven’t done it.” His face turned pale as a dozen heads turned in their direction.
“Dude, you haven’t done her yet?” Some drunk college aged guy Will recognized as the guy throwing the party. “She’s been throwing herself into your arms all night dude, you gotta give a girl what she wants.”
“Yeah dude, if you’re gonna call dips on the hottest girl at the party at least make something out of it.” Someone else yelled from the crowd.
“Besides, you’re off to college soon, you’ve gotta make sure she remembers you, if you know what I mean.” A third guy chimed up. “Don’t make my mistake, she’s gonna run off with someone willing to take care of her needs if you don’t.”
“Look dude, take this, and head up the stairs, third door on the left.” The guy throwing the party slapped a key into Will’s hand. “Condoms are in the nightstand, just don’t make a mess.” He said as a small crowd began to push them towards the stairs with a chant of: “Fuck fuck fuck!”
Barely able to stay on his feet Dawn took his hand and led him up the stairs before she shouted down to the crowd. “Shut up you pricks!” In a playful voice. “If I’m gonna show my man a good time you’re gonna have to stop yelling at him for 5 seconds and go back to your booze.” She declared to the sound of cheers and plenty of cups being refilled as Will and Dawn vanished into the third door on the left and locked it behind them.
“I am SO sorry.” Will blurted out almost immediately as the music and party noises started ramping up again below them. “I never thought, oh god I want to die.” He blushed as he sat down on the bed.
“Yeah… that was the worst.” Dawn agreed with a small laugh as she sat down next to him. “You gonna be okay?”
“I don’t know.” Will sighed and stared off into the air.
“Just a few months ago you would have been crying right now.” Dawn said softly as she stroked his shoulder. “You’ve come a long way to just be really shaken by something like that.” She said with a smile. “And you’re gonna keep making progress.”
“That… that’s what I’m worried about.” Will admitted and found Dawn’s eyes with his own. “When I go off to college and you’re not there anymore, maybe I’ll slip back again.”
“You wont.” Dawn said surely.
“How do you know? You’re the only reason I’ve been changing at all and I just don’t know if I can do it without you.” He said before Dawn gave him a kiss to quiet him down.
“You can.” She said surely. “You’re getting so strong and you’re so sweet, even if I’m not there, I know there will be plenty of girls there who will want to take care of you.”
“I’m not sure I want plenty of girls.” He admitted. “I already have the best girlfriend I could ever ask for.”
Dawn blushed and kissed him again. “Thank you brother, but we’re siblings, fooling a few drunk students is one thing, but in the real world, it just won’t work.”
“I know.” Will sighed and put his arms around her. “I just don’t want this to end.” He muttered.
“But it will end.” Dawn said plainly. “But we decide how it ends, and I think we should give it a happy ending.” She said as she reached over to the nightstand and found the condoms.
“You’re not serious.” Will gasped, turning red as a tomato.
“Not like that no.” Dawn giggled and took his hand, placing it in her lap. “I was just thinking we could spend some time making each other feel good.” She smiled as she placed a hand on the small bulge in his pants. “Nothing over the line, just enough to enjoy ourselves.” She smiled. “Don’t you think that sounds nice?” She asked as she began to stroke his bulge softly.
“It- it does.” He swallowed as he reached his hand under the dress and she spread her legs for him. He found her panties and rubbed his fingers against them.
“That’s it.” Dawn purred as she felt his cautious fingers brushing against her. “I’m gonna make sure you feel good too.” She smiled and undid his belt while his fingers explored her panties.
“Can I- can I touch your…” He nodded towards he chest.
“Go ahead.” Dawn said with a small blush as she unzipped him and pulled his pants down a little. She put her hand on the bulging in his underwear the same time as his hand found her breast and began to massage it. He was gentle as she had expected, but how quickly he reacted to every little shiver of her body came as a surprise. Whenever he brushed up against her nipple, or by coincidence ran a finger over her clit and her body shivered he was quick to notice and follow up on it.
Dawn moaned as she stroked the bulge in his underwear for a few moments, content just enjoying her brother’s treatment. Eventually she pulled his boxers down and his cock sprung up, it was hard as a rock but not exactly impressive in size. She could feel his hands freeze in place and she found his eyes again. “Relax.” She said softly as she wrapped her fingers around his cock and began stroking it. “Its just the two of us here, I’m here for you.” She assured him as she gave him a deep kiss. “You don’t have to worry about anything.” She smiled as she felt his hands beginning to move again, even more eager than they had been before. “Let me just…” She reached down under her dress and pulled her panties down. “There.” She smiled to him and led his hand in between her legs again. “All yours.” She smiled to him and his fingers quickly found her clit again.
Dawn opened the condom wrapped as Will turned made her wet, one of his hands were fondling her nipples and the other was slowly beginning to explore her lips. She rolled the condom onto his cock and began to stroke him once more. Will let out a moan as she stroked his cock and his own hands made her breathing shallow and ragged. She found his lips with her own once more and locked him into a kiss as they pleasured one another. His moans were getting louder fast, despite Dawn keeping her stroking of his cock slow and steady. With a grunt and a thrust of his hips Will came in her hand, his cock pulsing and pumping his cum into the condom.
“I-I’m sorry I never la-” Will began but Dawn cut him off with another kiss.
“Keep doing what you’re doing.” She moaned and felt one of his fingers push inside of her. She let out another moan as he found a particularly good spot inside her and began to push in and out of her in long smooth steady motions. “You’re so good.” She moaned as another finger pushed inside of her. She abandoned the kiss and just held on to her brother as he finger fucked her. “I’m, I’m close.” She moaned and this time he was the one who found her lips, forcing her into a deep passionate kiss as his fingers pushed her over the edge. She cried out in ecstasy as her sex clenched around his fingers and he kept going for a little while longer until her cries turned to soft moans of satisfaction.
“See?” Dawn moaned softly. “With fingers like yours, you never have to apologize.” She smiled and gave him another kiss. “You’re more than good enough to be the best you you can be.” She assured him.
“Thank you.” Will said sincerely. “I don’t know what would have become of me without you.”
“I’m just glad I could be of help.” Dawn smiled. “And maybe when you come back from college during breaks, we can go to a party or two together?” She suggested with a smile.
“I would like that.” Will smiled and gave her another kiss.
Dawn reached down and pulled the condom off of him, making sure not to spill any of his seed as she tied the end closed and headed over to the window. She pushed it open and instantly the volume of the music went up. She leaned out of the window and looked down at the open window below. “HEY PRICKS!” She roared at the top of her lungs. There were a few yells from downstairs and the music got turned down significantly. Dawn tossed the filled condom in through the window on the ground floor, landing smack dab in the middle of the party room. “HAPPY NOW?”
A massive cheer erupted from below as Dawn went back to the bed and crawled into Will’s arms. He had a goofy look on his face as she gave him a kiss to the sound of the party below chanting: “STUD STUD STUD!”
Source: reddit.com/r/sexystories/comments/c1g8l0/building_confidence_mfinc