Accidental Help for Little Sister

Disclaimer and Foreword: All characters in this story are over 18 years old. This story was written for one of my very dear friends, my best of friends actually. She's an amazing woman and has kept me on... not exactly the straight and narrow path but an honest one. I love her to bits and hope she enjoys!

*****

"Michelle, I have a problem..." Susan sighed as she sat on her big sister's bed in her sorority house. The tall brunette looked over at the curvy blonde fixing her makeup for tonight's party. The older girl glanced back and smiled before brushing on a bit more mascara and batting her eyelashes at the freshman.

"Only one?" Michelle giggled, teasing her ward and walking over to plop down on the bed next to her. Every incoming pledge like Susan was assigned to an older girl; a 'big sister'; to look after the candidate and help her through the initiation process as well as her general wellbeing. Typically, this involved just answering questions and being an instant friend to a new girl in an unfamiliar setting such as college. However, occasionally unusual situations arose.

"Yeah, yeah." Susan blushed, trying to find the words for what she wanted to ask. "College has been... amazing, such an eye-opening experience. I can understand why my brother never came home except on holidays." She started, working her way up to something as she wrung her hands. "And the girls at the sorority have been awesome and it's given me a chance to reinvent myself and gain some con-"

"You're a virgin. I get it." Michelle grinned, interrupting her 'little sis' and left the younger girl flustered. She gave her 'little' a hug before standing up to finish fixing her hair.

"Well, I mean... I..." Susan sighed, hanging her head a little before flopping back onto the bed. "Yes." The freshman blushed, placing her hands over her face before she sat up straight and sighed. "I just... I can talk to guys, but I always lock up when... I just don't have... experience." She rambled, trying to put words to what she was feeling. "I want it to be over with. I think if I can get past the whole virgin thing then I'll be able too, you know. Be normal." She grumbled, trying her hardest to sink into the mattress out of embarrassment.

"Listen, Susan," Michelle said as she straightened her hair and grinned into the mirror. "This confident embodiment of sex and beauty you see standing before you wasn't created overnight. You might find it surprising, but I was in the same situation as you were when I arrived at school. So I'm going to do for you what my Big Sis did for me when I pledged." She grinned and curled the tips of her silky hair. "I'm going to get you laid."

"What?" Susan gasped, sitting bolt upright.

"I even know the guy for you." Michelle mused and set the curling iron down before she tapped lip with a fingertip. It was clear she was on a mission now. A mission of...well, not love. "He's older than you. An athlete, gorgeous really. And he has the most amazing cock." She mused, eyes glazing over a bit as recalled their last encounter. "He and I have an arrangement of sorts, but I'll happily lend him to you for the night. He's an amazing lover, just he's always too busy to be nailed down into a relationship. Trust me, I've tried." She sighed and shook her head. "But for purposes of getting you on your feet; or back I suppose;" Michelle giggled, confident of her plan "he'll do perfectly."

"You're not serious," Susan told her and clutched one of Michelle's stuffed animals across her chest. "You're messing with me." She breathed, knowing already that when her big sister made up her mind about something she stuck to it. "You're not messing with me." Susan frowned, as her Michelle's grin widened. Michelle wiggled her eyebrows a bit and let the younger girl work through the math. "Wait, TONIGHT?" Susan squeaked, blue eyes going wide as she realized the implications.

"Of course, tonight is perfect. I'm going to the Beta Rho Omega toga party tonight; they always put on a fun event. Plus, your mystery lover is a Brother there." Michelle explained and searched her desk for her phone to remind herself to call Susan's 'date' after she left. "Pledges aren't normally allowed in, but it's kind of a roman masquerade thingy so as long as you keep your mask on no one would know." She figured, thinking out loud. "Plus, you wouldn't even know the guy at all, or his name or what he really looks like. Just the fact that he's a hunk, hung and has my stamp of approval. You get your V-card punched by a really great guy and then your problem is behind you, leaving you with a clear head and a full pussy." Michelle grinned, glancing over at Susan before she grabbed her hand. "It'll be great, you'll see. Now let's get you ready!"

Chris's cell phone rang on the way out of the gym. He had just finished practice with the swim team when he plucked the buzzing rectangle out of his bag, read the name and grinned immediately. He had been feeling the stresses of school, swim team, the fraternity, midterms... the list went on and on. Michelle was always good for some relief and honestly an amazing fuck. Perfect. He answered the phone and placed it to his ear "Chris's piledriving service: For when you absolutely positively need to have the bottom knocked out of it. Chris speaking, how may I direct your call?" he answered.

Giggling on the other end of the line let him know that Michelle was amused, as always. "You ass." She laughed, glancing out of her sorority house window to watch Susan hurry down the street to go meet her brother for lunch at the Student Center. "Listen, I have a favor to ask of you." She asked.

That got Chris's attention, his eyebrows popping up. Michelle never asked for favors. "Anything. What's up?" he asked, unable to hide his curiosity.

"There's this girl here..." she began, only to be cut off by Chris and his smart mouth.

"At the sorority house? Get out." He grinned at the heavy sigh at the other end of the line.

"Listen, can you quit being You for a minute and just listen. You're going to like this I think." Michelle sighed, running a hand up through her hair. "There's this girl, who's dealing with a bit of a crisis of confidence. I see great potential in her, but she's hung up on one thing. She's a virgin."

"Ah," Chris said. Even a meathead like him could figure where this was going.

"So, I'll bring her by the house tonight for the Roman party and introduce you and you... do your thing." She asked.

"You know I don't like virgins, right? They get clingy and..." He began before being cut off.

"Hey dum dum, it's a toga party. Everyone will be wearing those silly masks. You'll never have to see her again if you don't want to. Only I will know who she is and I won't tell her who you are, so if things go well maybe you get another filly in your stable." Michelle explained, reminding Chris of his own party plus some added benefits as a sweetener. Chris never hung out much with his own fraternity, being too wrapped up with the swim team. That he kept his distance from the rest of the ingrates was probably what helped him maintain his charm. Also, he was discreet Michelle she could fuck his brains out every once in a while and not be the topic of rumor for a week.

"Fine, I'll defile this virgin for you. But you owe me." Chris teased, getting a snort in response.

"Whatever, you know I'm good for anything." Michelle laughed.

"That I do, kitten. I see my, Sis. Gotta go. I'll be wearing the white toga with the purple lining and the gold-flecked mask." Chris quickly explained before hanging up and pocketing his phone. Susan was waving excitedly from the student center entrance at him.

Ever since his little sister Susan started attending college, Chris had been noting a change in her. The siblings had always been close and decided to meet every other day for lunch in order to stay caught up with each other and not lose touch in the chaos of campus. After a few short weeks of being at college, he could tell Susan was becoming more confident. More outgoing. Chris was attributing this change to having joined a Sorority. When he first attended school Chris was far more bookish than he would like to admit, even with his athletic accomplishments in high school. Social situations never came easily to him. Joining a Fraternity was the best decision he ever could have made. He couldn't hide behind his books and his swimming anymore and forced him to learn to interact with others, with the opposite sex. He was hoping it would have the same effect on his little sister.

Susan took the last few steps over to her big brother and practically leaped into his arms. Chris laughed and caught her, squeezing her tight and gave her a kiss on the cheek. He buried his face into her dark hair and breathed deep her familiar scent. "Hey Munchkin." He mumbled into her ear. Susan was a former basketball standout in high school and gifted with a tall 5'11" athletic figure, so Chris always found the pet name 'munchkin' hilarious. He himself stood at 6'3" and in amazing shape. He was on the swim team; he'd be kicked off if he wasn't. Therefore, he was one of the few people who could actually pick her up and Chris knew she enjoyed it. He grinned and tightened his muscular arms around his little sister until she gave a satisfying squeak before putting her down, kissing the top of her head. Chris slipped an arm around her waist and walked into the student center with her to get lunch.

Looking at the pair it was easy to see how similar they were. The siblings shared the same light blue eyes and warmly tanned skin. Chris's light brown hair was far more sun-bleached than Susan's rich brunette from spending a fair amount of his free time in the pool or at the beach. Both wore what was essentially athletic clothing all the time having grown up spending the majority of their childhood on the playing field or at practice. Having just come from the gym Chris wore loose basketball shorts and a tank top which did an impressive job of showing off his toned arms and chiseled chest. Susan, on the other hand, wore yoga pants and tight spaghetti strap tank top and a thin jacket over it, as she was planning on hitting the gym after her late class. Not to mention making any guy within a twenty-foot radius check out her ass.

"You seem to be in an unusually perky mood today. Having a good morning?" He asked and arched an eyebrow slightly as he checked out his sister for anything unusual. Susan looked great, as she always did, but noticing it was second nature to him. Chris knew his sister had an amazing body like he knew she had blue eyes. Just something she always had.

Susan blushed and grasped her tray tight as she reached for a premade salad. "Just hung out at the sorority house this morning is all. My big sister is... helping me out with something." She smiled, remembering the morning's conversation. Which lead her mind to tonight's party and her cheeks to redden even more.

"Well, I'm happy to see you fitting in there so well. I told you it would be the best decision you would make." Chris couldn't help but smile at his little sister's reaction. He purposely kept out of her sorority affairs even though he was a member of a fraternity. He honestly didn't attend his own house's functions as often as he wanted due to the demands of the swim team. Next semester would be different and he could go back to full-time party animal. Chris wanted his little sister to forge her own way in the Greek system as well as grow a bit on her own without her big brother always looking over her shoulder. Plus, it would be a bit... awkward to walk in at a party and see her grinding on some guy. Did Susan even dance? He couldn't remember seeing her do it, actually.

Susan giggled a little as they found a table off to one side to chat "Yeah, yeah. You were right. There is more the school than just studying and basketball. I should have never doubted you, older brother. Whatever shall I do without-" she grinned as her big brother's eyes threatened to roll back into his head.

"Har har," Chris smirked through his sandwich, devouring it quickly to feed his ever-present appetite. "I'm just happy with being right. Don't you forget it." He winked, wiggling a French fry at her which she promptly stole and ate. Susan just blinked her eyes innocently at her older brother and smiled, giggling as they finished their lunch as topics gravitated back toward class and things back home.

"Same time on Monday?" Susan asked as they cleaned up, walking with Chris out to check their mail downstairs.

"Always. Anything for my favorite girl." Chris smiled, kissing her on the cheek again before locking his mailbox. "Gotta run to class. Text me if you need me!" he waved, jogging off to class as the bell rung.

That night Chris was nursing his second beer as he subtly glanced around the main reception room of his fraternity house. His blue eyes peered out from beneath the gold flaked theater mask he 'borrowed' from his former roommate, a drama major. He kept scanning the room for Michelle. That crazy girl was always throwing some sort of crazy twist at him like this, but that was part of her charm. He took another sip of his drink. Chris just hoped this girl was hot.

Chris adjusted the mask along with a few sprigs of the bush out behind his bedroom window that was twisted into a crown of leaves. They added leaves actually did look pretty good, earning him a few compliments on his Caesar look. Paired with leather sandals and a white toga with one edge lined with purple made for an impressive outfit for the evening. The toga; which was just a high-quality bedsheet with the edge dyed; was wrapped around his waist and over one shoulder and displayed his physique in a strategic way without letting his bait & tackle hang out. However, it was easily apparent that he wasn't wearing anything under the sheet with how it drooped low on one hip. He wore briefs under the Toga his freshman year and received a metric ton of shit from the older 'brothers' in the Fraternity. He wore it traditionally ever since. In fact, as he looked around the room it was very easy to tell that the majority of the partygoers attended without undergarments. Their togas allowed for varying degrees of decency; some were intentionally lewd while others hilariously kept trying to keep their bits covered while drinking and dancing.

"Where is that crazy minx?" Chris muttered to himself, watching the room slowly begin to ever so slowly slip into debauchery as he awaited Michelle's arrival. He'd be lying if he wasn't curious about this girl that he'd be meeting. He grinned into his drink, deciding to show this girl a good time regardless of her impending deflowering. Most likely she was a bundle of nerves, so he wouldn't force her to do anything despite what Michelle asked. Chris wasn't the kind of beast to force himself on a girl, but they were here for a purpose. If the girl said No, he'd report back as such to Michelle and make damn sure she'd still pay up.

"I can't believe you talked me into wearing this..." Susan blushed and gripped her big sister's hand tightly as she stared across the darkened street. The fraternity house was clearly active, all sorts of noises coming from the front door but the windows were blocked by heavy curtains. The tall girl was wrapped, loosely wrapped, in a blue sheet that accented her eyes. Her toga was draped over her shoulders and tied around her waist it constantly felt like it was going to pop open to display her goods. Only two pieces of double-sided tape kept the eyes and hands away from her ample bosom.

"You look fucking hot, don't worry about it." Michelle grinned and sipped from a small bottle before sticking it back in her purse, then thought better of it and handed it to Susan. "Take a few sips and you'll be good to go. Just don't overthink it." She told her 'little sister'. "One night with this guy and you'll realize what you're missing. Your life will never be the same." She assured her.

Susan took the bottle and looked at it, then took a deep breath and put it to her lips. Three large gulps later she winced and sighed. "That's what I'm worried about." She whispered under her breath before handing the bottle back. Michelle took it back and tucked the nearly empty bottle into her purse, resisting the urge to roll her eyes.

"Oh, quit being such a worrywart. You're killing my buzz and I need to get laid tonight." Michelle giggled, taking Susan's hand and crossing the street. One of the brothers was in front of the house checking 'invitations' and making sure the party remained private. Michelle walked right up to him and whispered something into his ear which caused him to grin beneath the black mask he was wearing. His eyes flicked down Susan's body, his smile not wavering as he reached back to open the door and gain them entry.

"What did you say to him?" Susan asked, unable to hold her curiosity in check.

"I'll tell you when you make full Sister." Michelle grinned, giving her hand a squeeze as they entered the loud house. Music assaulted their senses and from the sound of it, there was a hell of a party underway. Most of the noise is coming from the main hall, which in the low light made for a passable dance club. The back of the room near the kitchen was set up like a bar, with people wandering to and fro refilling their party lubricant. A winding staircase climbed one side of the room to a darkened landing, but from the occasional noise and lights, there were... things going on upstairs. The TV room off to the side was set up as kind of a quiet place to talk and chat and avoid the noise of the dance, plus a few other closed doors where an occasional half-naked guy in a bedsheet entered or exited.

"Wow!" Susan breathed, taking the spectacle in as her eyes wandered over the room. She'd only been to the rush parties that the sorority house held, but this is her first true fraternity party.

"They put on a good time, right?" Michelle grinned, grabbing Susan's hand and turning her to face her, making sure she got her attention by looking her in the eyes. "Listen," She said, giving Susan's hand a squeeze. "I trust this guy, completely. He's one of the good ones. Not all of them are." She warned, giving it a tighter grip to gather her attention. "Do. Not. Leave. His. Side." She said, smiling. "Pledges aren't even supposed to be here, so I'm doing you a favor. There are things that go on here that are pretty... uh, advanced." She giggled, her lips spreading into a huge grin. Clearly, she was here for some of those activities. "But stick with him, he'll be good... well, not GOOD but he'll keep you safe." Michelle winked as Susan kept nodded at the sage advice. "But above all, have fun! Remember, he doesn't know you! Grab him and get what you need out of him. If he likes you, trust me, he'll be wanting to meet you." She grinned as she looked over Susan's shoulder as she saw Chris approach.

"Ok, ok... how will I know him?" Susan asked, breathing deep to steady her nerves as she leaned close to be able to hear Michelle over the loud music.

Michelle just giggled. "That's easy." She grabbed Susan by the waist and turned her around to face Chris, who had just pushed himself through the crowd to stand behind her. Michelle leaned close, kissing Susan on the cheek and gave her bare ass a squeeze through the thin blue sheet. Releasing the younger girl, she waved to her accomplice and blew him a kiss. "You kids have fun!" she grinned and melted into the crowd.

They stood there and eyed each other for a moment, just openly checking each other out with the freedom that anonymity gives. Chris smiled broadly though, loving what he saw. This girl was tall; a rarity; but her body had the curves to it that he was definitely interested in seeing. Chris reached out and took her hand in his and pulled her into the crowd and toward the dance floor. "Let's dance." He said, pulling her along as he stepped back into the throng. Minutes of awkward conversation skirting the subject as to why she was here wouldn't do anything for mystery girl's anxiety, so like a band-aid being ripped off he slipped his arm around her slim waist and drew her to him.