Least Expected

Story Info
The girl who never got any attention, gets lots,with a twist.
4.1k words
4.11
190.9k
20
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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
BadLilSis
BadLilSis
100 Followers

A hard worker, totally diligent and outrageous behind closed doors. Problem was, she didn't have anyone to share that 'craziness' with.

She, is Ivy. Ivy is a senior at her high school, and in her own rights beautiful. With mid-length wavy brown hair and penetrating brown eyes. A beautiful smile and perfect teeth. Her breasts are modest, not huge but not tiny. About a 38b. Her only downfall is...her weight. Ivy is a little over weight, but curvy enough to pull it off. Her weight holds her back from nearly everything, especially when it comes to believing in herself. Incredibly smart and outgoing, it's hard to believe that no guys seem to be interested, ever. And this, is what's killing Ivy.

Every day Ivy goes into school, says hello to her pretty, skinny friends. She looks at herself in the glass and her reflection frowns back. She isn't ugly, no. She cleans up real nice, she'd be a pretty girl...she thinks...if it wasn't for her weight. Pushing her hair back on the top of her head while a few strands feather themselves around her face she gets ready to go to her next class. Carrying her heavy backpack, Ivy plods through the stairways and looks at everyone else jealously but at the same time attempting to maintain a nonchalant feel, smiles outward to the world while dying inside.

Ivy's only been kissed once, and it was rather rough. In a guy's car, who's mouth tasted like an ash tray and smelt of alcohol. He was cute, very cute. Blonde, blue/green eyes, thin and a nice body. After a movie, they were parked in the lot and he ravaged her. She loved it, loved feeling sexy under his touch. He grabbed her breasts, rubbed her crotch and she debated in her mind whether or not she should let him fuck her. The passion was that great.

Yet, she's still a virgin.

Finally arriving in her class, a boy whom she is friends with is writing down some notes on a white sheet of paper. He lifts his head, and looks up at her. He smiles, but not only does his mouth smile but his whole face. Eyes, ears and nose! Ivy's face lights up just because of this welcome by her friend. That's all they are, strictly friends, though she wants it to be so much more and cannot tell if he does or doesn't. It seems like, and as her mother says : Everyone else knows. Your friends know he likes you, I know he likes you. Your brother knows it. He knows it, but you don't.

Well why couldn't she figure it out? because nothing, except for that rendezvous in some guy's backseat had worked out. And that ended rather nastily, so basically Ivy had absolutely nothing to look forward to.

Except him, his smile, their playful banter...that was what kept her going.

Ivy sat down next to Jacob. They talked a bit, but then once class got started she just dreamed about how it would be if THEY could have that wild rendezvous in his car.

:::After a week:::

"Go to the grocery store today for me honey? please?" Liza, Ivy's mom asked her kindly.

"Sure." Naturally, being a lazy teen, she didn't want to do it, but figured it would be best to move around a bit that Saturday!

Pulling on a red button down sweater and buttoning up her flared out blue jeans, she found some white flip flops and grabbed her keys.

Getting into the car, she blasted some really bouncy rap music that made her groove a bit in her seat. She loved fast, sexy music about how all these rich rappers wanted to fuck their many kinds of girlfriends. She sometimes wished she was one of them. Or at least, maybe a guy just fuck her! As Ivy cruised the parking lot looking for spots, she finally found one and pulled in. Stepping out of the car, she began to walk to the entrance of the store and before she knew it, some stupid jerk had walked clear into her!

"Ah!...watch it.." she mumbled.

"So sorry, god, I'm sorry." The man said.

Ivy looked up, his voice was so pleasant, and his words of apology seemed to roll of his tongue like velvet. He was tall, had a tan complexion and the most penetrating green eyes. His hair was combed back but a little spiked at the top and light brown. His shoulders were broad, and his black shirt was tight over his chest. Ivy's eyes got a little bigger, and she bit her lip, looking all of 12 years old.

"I was on my cell phone, sorry miss. I really didn't mean to do that, they're right, these cell phones are for shit!" The mystery man laughed and coughed in the awkward silence that followed his statement. He was smiling, and Ivy looked down to the ground.

"It's all...all.. uh, all right." She nodded and looked up again at him. All the sudden, he seemed to look at her funny. His eyes were searching hers, and his head was tilted a little as if he was inspecting this girl in front of him.

"I understand, sometimes these cell phones truly are a blessing and then other times you want to just toss them in the ocean!!!" Ivy made a successful attempt at trying to get him to smile.

He laughed and then introduced himself, "Hi, I'm Julien." Ivy smiled, and gave him her name.

"Well, maybe we'll meet up sometime? Mind if I have your number?" Julien asked, gently.

Her number?! No stranger had ever asked her for her number and I mean, what guy would want to talk to her? On the phone? Or get together? Was this for real? This...amazing...piece of ...well, ass! was absolutely gorgeous and wanted to chat with HER? Wait...there must be a catch.

"Sure, here's my number." She said confidently as she wrote it out on his extended hand.

"GREAT!" Julien smiled and told her that he'd call her.

Walking into the grocery store as Julien walked back to his car, Ivy was floating on air. Buying what she needed, she basically ran back to her car and jumped in and sped the whole way home. As Ivy got into the house, she realized no one was there. There was a note on the fridge:

Honey, I got a call from

Mike, he said he needs me so I won't

be home till about 8 tonight. Fix your

dinner if you want, feel free to go out! Sorry

Vee, see you tonight.

--Mom

Ivy thought for a moment and thought, well, that's cool. Maybe I can do a little playing. She giggled aloud and started to put the groceries away. The phone rang.

"Hello?"

"Hello, is Ivy there?"

"This is she, may I ask who's calling?"

"Oh..mannnnn!...Hey Ivy, it's Julien."

Ivy dropped the yogurt that she held in her hands.

"Shit!...one...uh...ah...one second."

"You all right???"

"Yes...yeah, yes, I was just um...startled? that you called so soon."

"Have I got you at a bad time?"

"NO, no, no not at all, Julien. Give me a sec?"

"I'd wait all day, " he replied sweetly.

Ivy giggled, and cleaned up the mess. After a few moments of Julien being on hold, she picked the phone back up and said hello again. Julien greeted her and the real conversation began.

Julien started with, "I was just wondering...Ivy..."

"Yes? What's up?"

"That's such an interesting name...but (a brief laugh) I was wondering something."

Ivy laughed, "I know, you already said that."

"Oh, ha, well, uh, would you care to have dinner with me sometime? Maybe...if you aren't busy, tonight?"

"Well, why yes, yes I would love to have dinner with you Julien." Ivy's face began to hurt from smiling so much.

"Wonderful, I'll pick you up next Friday at 7 and I promise it'll be a beautiful evening."

"I'm sure." They both bid farewell, and as they both hung up they both retired to their bedrooms to relieve a little tension. Julien went upstairs to the guest room, and laid on his bed on his back and grabbed his cock out of his pants. Slowly at first, he began to jerk it steadily. Then the rubbing and squeezing became more erratic as he jacked off faster and faster, the tip getting really wet. But little did Julien know, Ivy was back her own house on her bed doing almost the same thing. Without a moment's notice, Ivy was off the phone and on her bed with her pants on the floor. Her legs behind her head, she started to finger fuck herself fast. Pumping her pussy, breathing out Julien's name. Julien, at his abode, called out hers. Promising to fuck her tight pussy aloud. A knock at Julien's door interrupted this fantasy and Julien snapped up to attention.

"Hold on! Hold on, man." Julien quickly put on his pants, his cock deflating from being so rushed and ashamed of being caught.

Laughing, his step-brother entered the room, "22 and still jacking it in your room, well then I have something to look forward to, don't I?"

"Shut the fuck up Jacob."

And just as 'Jacob' rolled off of Julien's lips, Ivy came and came with no abandon.

:::The following Friday:::

"Honey, what time are you coming home?" Ivy's mother asked her as she stood in the doorway of Ivy's room.

"I don't know mom? I'm 18, come on, I won't be too long. Promise, all right?"

"All right, all right, sorry. Well you look, fabulous, Vee."

Ivy smiled timidly, and looked back into the mirror. No, she wasn't any model, but she did look really good. A black, very slimming cocktail dress with only one shoulder "strap" and silk flowing out at the ends, she looked...well, almost like a model. Her legs were long, and she teetered upon very high sexy strapped black glittery heels. Sparkling diamonds adorned her ears and neck as well as her ankle. Ivy smelt like an expensive perfume and having had her nails done up in a French manicure, she looked altogether gorgeous. Though, she'd never admit it. Throwing her beautiful hair back behind one shoulder, the doorbell rang.

"I'LL GET IT!!" Ivy yelled and bum-rushed down the steps almost clumsily in her heels. But being, the portrait of grace she slowed as she got near the door and could see Julien through the glass side boards. Opening the door, his smile gleamed and he looked fabulous in black slacks and a white work shirt unbuttoned at the top with a sharp black blazer atop it. He smelt almost as good as she did, and he was holding white roses that made the picture of HIM look even better.

"Aw Julien." Ivy said breathlessly.

"Hello, beautiful."

Beautiful!? Oh goodness.

"H--ha, hi." Ivy could barely contain her smile, and her white teeth, pristine as ever, shown brightly.

"Ready, my lady?"

"As ever, let's go."

Seeing her mother on the top steps, she turned around and waved a little and smiled. Her mother smiled back, proud of her daughter. Julien closed the door after them and escorted Ivy to the car. They got in, and Julien began to explain the evening to her.

"Well, I thought maybe we could go have a really nice dinner at The Watergate. It revolves around on the top, you know? And since you're so beautiful out tonight, I thought It'd be the perfect evening. (A wink) Then, maybe we'll do a little dancing and if you're up to it, dessert and wine back at my place? I promise that's all."

Ivy was still beaming and nodded as he spoke. It all sounded so good. Maybe she WOULD go back to his place for dessert and wine.

"Well, Jule, is sounds great. I'd love to do that, where are we going dancing?"

And the rest of the evening was ultimately just as beautiful as they were a couple. During dinner, they spoke of their families, what they had in common. Likes and dislikes. Ivy told jokes that made Julien laugh and Julien told jokes that made Ivy rear up in laughter. Two hours had passed at dinner, and after finishing off their meals Ivy made it known that she was ready to work it all of by dancing the night away. A little bit later, they arrived at a large hotel which was holding an open ball room. The music was at times, waltz, and then Latin beats. It was a perfect evening. Julien held her close, grabbed her tightly at all times. He was graceful on his feet, and so was Ivy. They stared into each others eyes without having to say much. Pulling her close during a sexy Latin salsa mix, they moved to the right.

"Ivy, I want to take you home and have some wine with you tonight."

Moving to the left in little steps, Ivy lowered her face and looked up at him seductively.

"Do you now?" She teased as he turned her.

"I do now. Have wine and something sweet with me?"

Splitting down the middle while still holding hands, Ivy snapped her head back as he dipped her and whispered in his ear:

"Let's go. And you will most definitely have something sweet to eat tonight."

He beamed, and they left after the song was over.

:::Thirty minutes later at Julien's:::

As the car pulled up to the grand house, Ivy was impressed.

"Lots of a room, for a single guy?" she teased him lightly.

"Oh, it's not my house...I'm just here visiting my step-mother and father." Julien replied as he opened his door to walk around and get hers. She unlocked the door, and he opened it looking down her and gazing at her long legs. Helping her out by the hand they walked slowly over to the front door.

"Where is your family then, tonight?" Ivy curiously asked.

"Oh, I told them I had met a very intriguing girl with the most beautiful smile and a killer sense of humour...they said that they'd beat it. Promised me the whole place till tomorrow."

"Yeah? Well...I'm, quite embarrassed then..!" Ivy smiled.

"Why's that?"

"Because, bringing me over when you're expecting some other great girl to come by later."

Julien howled with laughter and grabbed her around her waist and walked her into the house.

"Go have a seat on the sofa and I'll bring out the wine and dessert."

She did as she was told, and sauntered into the living room and kicked off her heels. Looking around the living room, but then closing her eyes not believing it was finally her having all the fun Julien came in and kissed her forehead.

"Strawberries?"

"I'd love some Jule." She giggled as he slid one to her lips and she took a bite.

"I hope you like chardonnay, that was all I had."

"It's my favorite..." Ivy replied.

"Really?"

"No, but it's almost as good as a rose zinfandel." Julien winced and tickled her stomach.

He looked deep in her pretty eyes and kissed her mouth. Their lips touched each others, and his tongue slid into her warm mouth. He put his hands on her head and kissed her deeply. She placed her hands on his chest and felt his tongue with hers. He slowly slid his hands to her supple breasts and felt them through the soft material of her thin dress. Ivy could feel his hands, big, manly touching her chest and she breathed lightly into his mouth. She scooted up closer to him and was ultimately sitting on his lap.

"Knock, knock..." Someone had come into the room. Julien's head whirled around as did Ivy's.

"Jacob?" Ivy said ashamed as her lips dragged off Julien's neck.

"JACOB!!!!!" Julien had more of an angry response.

Jacob had a look of surprise, disgust and heartbreak on his face.

"Ivy...what are you doing here...." he said, obviously a little hurt.

"You live here? I didn't know, Julien...he...Julien is your step brother?"

"Yeah..." Jacob trailed off. Julien, still fuming from the interruption waited for his dick to go down and stood up.

"Let's go jerk, in the kitchen." Jacob walked into the kitchen and sat down at the table.

Julien grabbed Ivy's breast, squeezed it and promised he'd back in only a moment's notice. Ivy slid into the sofa, and put her hands on her face.

"What are you doing here?" Julien asked as he stormed in.

"Why are you with her?" Jacob asked, ignoring him.

"Fuck that Jake, I met her at the grocery store."

"No, fuck you Julien. I've known her since sophomore year at school and I'm crazy about her."

Julien paused, and looked at his step brother.

"Have you ever told her that?" He was growing impatient.

"No.."

"Ugh, so how do you expect her to react to you if you don't tell her that you dig her bro? She can't do shit if you don't tell her. Now you're too late, and she's mine so deal with it. How does it feel to be on the other end of the spectrum of not being wanted Jake? She's felt that her whole life and you couldn't pick up your skirt and do something about it. So you're too late. Go to bed." Julien walked out, and walked into the living room.

"Julien...I ..I know Jacob."

"I know baby, he just told me, just forget him okay? He's cool with it."

"Maybe I should go?" Ivy suggested.

"No way, Ivy. We were just getting started." Julien grinned slyly.

Ivy thought it over for a second. Julien was right, she had waited so long for Jacob to come around and he never did so why put the chance with this handsome guy totally to shit? Taking charge, she whispered to Julien.

"Let's go upstairs to your bedroom." Ivy grabbed his hand and he led her upstairs to the bedroom. Getting to the room, Julien pushed the door shut lightly and slowly put Ivy on the bed. He reached around her and unzipped it in the back. She shimmied out of it, and was left in nothing but her black panties. Julien's cock was once again at full mass, and he ripped off his own shirt and unbuttoned his pants. Spreading her legs, he laid between them and kissed her all over her face, neck and breasts. She was breathing heavy in his ear and moaning his name a little quietly. His hips were bouncing up and down against her moist crotch. Ivy ground back at him hard and encouraged him onward. The door had opened a little, so you could just see Julien on top of Ivy with her legs wrapped around his waist, getting ready to accept his cock in her cunt. Jacob stood against the wall on the other side facing Julien's room. His dick was hard as he watched Ivy being ravaged by his step-brother. He slowly rubbed himself through his khaki's. Ivy's moaning was getting a little louder, and Julien whispered to her if she wanted to make love. Ivy nodded her head but told him that she was indeed a virgin. Julien looked down at her, and smiled. "That's fine, Vee. I'll make this as wonderful as you always thought it would be."

"You already have, ohhh.." she trailed off as he pushed his cock against her pussy through their clothes. Jacob was outside of the door, listening and pumping his cock harder now. But now it was out and in his hand. Julien was pulling Ivy's panties down and Jacob could see her shaved pussy lips from out in the hall way. Julien yanked down his boxers and his 8 inch cock sprung out. Ivy laughed a little and smiled as she grabbed Julien by his shoulders and brought him down to kiss her. Jacob's dick was dwarfed by his step brother's long rod. Slowly, Julien spread open her legs, and placed the head of his dick on the surface of her wet hole. He placed his muscular arm near her face as his hand pressed into the mattress. Jacob cringed, jerking it still...but dying of jealousy inside. Julien was going to pop her cherry. The girl he had fallen for so many years ago...but Julien was right, he hadn't made his move so he couldn't do anything about it now.

Julien thrust forward gently, and his head fought to enter her. Ivy was breathing hard and shallow.

"Unnnh..unnh..unnh..unnh..oohh..oohh!!" She groaned.

"Yeah, baby, I knew I wanted to fuck your pussy when I first met you." Julien grunted. He had now forced his cock head into her, and then was gradually sliding the rest of himself into her. Finally, after a few moments of struggle, he had the full length of himself inside of Ivy. Ivy was writhing beneath him, bucking up and down. Jacob's mouth was hanging open, and he closed his eyes as she called out 'ohs' and 'ahs' imagining it was him delving into her wet slit. The rustling of the sheets and the sound of skin smacking around was driving everyone wild in that house. Ivy's eyes were closed tight, sharp pains in her groin were quaking her body but the pleasure was worth it. Julien was fucking her deeply, shoving himself into her and holding in place while humping up against her hips. The ultimate fuck. His balls were smashed against her ass, and he bounced his body up and down as he took her pussy. Grabbing onto her pretty young, perky tits, he bit on her nipple a little. Ivy was rearing up and down, up and down loving every second. Finally a man was fucking her, and it was more than she ever thought it would be. Julien shouted that he was going to cum, and Jacob out in the hall was buckling at the knees. Ivy was screaming and locking her back into place.

BadLilSis
BadLilSis
100 Followers
12