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Surprise At The Sleepever

"Riley and her friends catch her brother during a sleepover and take advantage"

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7.3k words 7.3k words

Author's Notes

"I've been trying to construct a story like this for a while and this one just kinda hit me. I hope you enjoy!"

“How are you still a virgin?” asked a girl sitting on a beanbag in the corner of the light-pink-walled bedroom. She was Hispanic with tan skin, brown hair that was about shoulder length and quite wavy, and brown eyes. She was wearing a black tank top and a pair of gray sweat shorts. “You didn’t fuck Cory when you dated him?” she asked incredulously.

“N-no. We never got around to doing anything like that, really. We just ... hung out a lot.” Riley was sitting cross-legged on her bed, wearing an oversized white t-shirt and a pair of light blue panties. She had yellow blond hair tied back in a ponytail and blue eyes. She was a bit taken aback by her friend Isabella’s forwardness and disbelief. Why was it so hard to believe that she hadn’t engaged in any activity like that yet? She was only eighteen!

“Not even a blowjob? I guess we know why they broke up now,” giggled a third girl, Naya, who was sitting on the floor, also cross-legged. She was a black girl with medium-dark skin, brown eyes, and dark brown hair set in dreadlock braids that extended to her shoulder. She was wearing a light blue tank top and light blue boy shorts.

“Don’t be too rough on her, now. She’s always been a bit more reserved. She’ll find the right time to do it eventually,” advised the final girl, who was sitting on the floor between Isabella and Naya. This was Riley’s best friend, Abigail, although Riley usually just called her Abs—both for short and because she was on the soccer team and actually had great abs. She had red hair, blue eyes, and was wearing a gray and black bra and a pair of black panties.

“Yeah, maybe she’ll be one of those girls that goes into college a virgin and then ends up sleeping with half the boy’s dorm by the end of freshman year,” Isabella replied with a slight grin.

Riley wasn’t sure if she was being serious or still making fun of her.

“If she does that, then good for her, but if she doesn’t, it’s okay too. There is no right or wrong time to do this stuff,” Abs retorted back, flashing an understanding look up at Riley.

All three of Riley’s friends were more ambitious when it came to sex than she was. They had all lost their virginity by sixteen, and here Riley was, at eighteen, and she hadn’t even seen an actual penis in person yet. Not even her recently made ex-boyfriend's, the two of whom had mutually agreed to break up a couple months prior.

Riley sighed. “Anyone want some drinks? We’ve got Coke, Dr. Pepper, and Sprite,” she interjected. She wanted to reset the conversation and thought grabbing drinks would help.

“Dr. Pepper,” Isabella answered.

“Sprite,” Naya chimed in.

“I’ll come with you,” added Abs, standing up as she said so.

The pair got up and exited the room.

“Don’t let those two get on you," Abigail started once she thought she was out of the immediate earshot of the room. "They are just concerned for you in their own way, is all,” she continued, wrapping her arm over Riley’s shoulder.

The pair then heard some grunting from one of the side rooms on the way to the kitchen. Riley decided to poke her head in.

“Hey Darren,” Riley said, standing in the doorway. Darren was her older brother, at twenty, who was home over the summer from college. He was wearing a gray t-shirt and black board shorts and had light brown hair and blue eyes. He was holding a black video game controller, which he was using to play on his console in front of a big TV in the room. He glanced up after a couple moments.

“Oh hi. What’s up?” he asked before looking back at the game.

“Nothing. Did you want anything to drink?” Riley asked in return.

“No, I’m good,” Darren droned, motioning to a bottle of half-finished mountain dew sitting next to him as he continued to concentrate on his game.

“Alright. Have a good night. The girls and I will probably be heading to bed in a couple hours,” Riley concluded before heading off.

“Alright,” Darren flippantly responded, only half paying attention.

“Hey Darren,” Abs then announced in an intentionally sultry voice, taking Riley’s spot in the doorway. Darren looked and did a double take, seeing Abigail’s athletic body in only a bra and panties.

“Uh, oh, hi Abigail. What’s up?” Darren stammered, clearly a bit unnerved.

“Nothing, just saying hi,” Abs teased before letting out a giggle and leaving to follow Riley to the kitchen. After a few more steps down the hallway, she let out a bigger laugh. “The look on his face ...”

“That was mean!” Riley chided, although she was also smiling and giggling.

The pair arrived in the kitchen and opened the fridge. Riley grabbed two bottles of Dr. Pepper—one for herself and one for Isabella. Abs grabbed the bottle of Sprite for Naya and a bottle of Coke for herself. The pair then turned around and returned to Riley’s room, distributing the soda bottles.

They started talking about their upcoming time at college, which was going to start in about a month. They had all decided to attend the same nearby state university, although the housing requirements ended up having them split off into different randomly assigned residence halls and rooms, but they all hoped they could rent a place together in following years.

“Which residence hall are you in again, Riley?” Isabella asked.

“Oh, it is Watkins Hall, fourth floor. It is one of the newer residence halls. Let me show you—” She hopped off her bed and got into the chair in front of her computer. She shook the mouse to wake it up and opened the browser. She already had the page bookmarked, so she simply clicked on it, and it opened up the information for the residence hall.

“Oh, I think that’s right next to mine. Awesome!” Naya cheerfully remarked.

"Meanwhile, I’m on the other side of campus,” Abs lamented.

"Yeah, so am I. Abigail and I got the same building but different floors,“ added Isabella.

“I’m sure we’ll be able to make it work out. Freshman year will be chaotic anyway,” Riley reassured, trying to cheer everyone up again.

“I heard their rec building is awesome with a big pool. Where does it talk about that?” Abs interjected.

Riley searched the site, soon finding the page for the university’s student recreation building. It was relatively new—built in the last ten years—and seemed to have everything: a track, basketball courts, an Olympic-size pool, and even a field outside to play whatever field sports students wanted. One of the big pictures on the page was of students playing Frisbee on the field.

“I wonder if one can lay out and get some sun there,” Isabella pondered.

“You would do that,” Naya quipped with a laugh.

“What? I like laying in the sun! Also, would give our two white girls a chance to tan up as well.”

Riley and Abigail were pretty pale, especially compared to their two friends. Abs often had a tan, at least when soccer season was in swing, but Riley usually stayed pretty white.

“I mean, I guess I could try,” Riley muttered.

“I think the quad would be the better place for that. Less likely you’ll be run over by a flag football game,” Naya proffered.

At that point, Riley’s computer suddenly displayed the most dreaded screen to ever show itself to computer users: the blue screen of death.

“Not again!” Riley exclaimed with frustration. “This is the third time this week!”

“Isn’t your brother a computer nerd? Why haven’t you asked him to look at it?” Isabella inquired.

“I don’t know. I just always forget to,” Riley lamented.

“Well, he’s still up. We just passed his room. I’m sure he’s still playing video games. I’m sure he won’t mind having to hang out with us for a few while looking at your computer,” Abs proposed with a laugh.

“Okay, okay,” Riley relented as she got up to go fetch her brother.

“I’ll come with,” Abs said as she got up as well.

“I think I will too. Need to stretch my legs,” Isabella added.

“Well, I guess I’ll join the fun too, then,” topped off Naya.

The group walked down the hall, their bare feet plopping on the wood floor. Riley could hear some grunting from the room again as she approached. He definitely still appeared to be playing his games, she thought to herself.

“Hey, Darren, would you ...” she started to say as she entered his doorframe again. However, mid-sentence, she stopped. Darren was sitting on the couch, completely naked, the top of his fingers pressed against his rather sizable cock.

“Oh my god!” Riley exclaimed, putting her hands over her eyes and turning out of the doorframe, putting her back against the wall in the hallway.

“What is it?” Abs quickly asked and once again replaced Riley in the doorframe. “Oh, fuck me!” Abs blurted out in a voice that Riley wasn’t sure was excitement or some other emotion.

She heard Darren urgently snap from his room. “Can you please ...”

“Look at this shit! Oh, no, it’s too late to try to cover yourself now,” she heard Abs say as her friend entered Darren’s room.

“Oh shit!” she then heard Isabella blurt out as she entered the doorway. “Nerd image completely shattered,” she declared, as she followed Abs into the room.

Riley then heard Naya give out a loud whistle. “Boy, you fine.” Naya then followed the other two friends into Darren’s room.

Riley stood outside, having now moved her hands down to her mouth. She had just seen her brother’s fully erect, hard penis in the flesh. Is that what they look like? How is that supposed to fit ... anywhere? Her head was spinning.

She then felt someone grab her arm.

“Oh, you aren’t hiding,” she heard Abs announce.

“Wait—no!” Riley protested as she was pulled into the room with the other girls. She got another full view of the scene before blushing bright red and looking away to the side of the room.

“So, what are we going to do about this?” Isabella pondered in a teasing voice.

“We—we should probably leave,” Riley chimed in nervously.

“Yeah, what she said,” Darren quickly asserted.

“Oh, I don’t think so. What do you think?” Isabella asked, turning to Naya.

“I get what you’re putting down, I think,” Naya responded. The two girls then approached Darren.

“What—what are you doing?” he nervously asked.

“You’ll see,” Naya whispered simply.

The two girls then got on their knees next to Darren. Naya grabbed his cock with her hand, and Isabella put her mouth over his head and started toying with it with her tongue. Darren let out a gasp and leaned back on the couch.

Riley slowly turned her head to look at the situation and suddenly found that she couldn’t look away. Naya was now using her hand to fondle Darren’s balls while running her tongue up and down the lower part of his shaft while Isabella was busy sucking off the top half. Is this what they were talking about—that she was missing? It seemed strange watching them do it to her brother, but it was also almost irresistibly alluring.

“I think I’m ready,” Isabella soon declared. She stood up and took off her tank top, revealing a pair of C-cup breasts. She then kicked off her shorts and panties, revealing a quite shapely ass as well as a shaved pubic area. Naya held Darren’s cock up straight as Isabella straddled him facing away from him and lowered herself onto his shaft.

“Oh my god,” she moaned as it slowly slid in. Darren also let out a soft moan. She started moving her body up and down, with Darren following suit with his hips.

Naya removed her own tank top, revealing a pair of D-cup breasts before proceeding to suck on Darren’s balls from below.

“What do you think?” Abs inquired to Riley, noticing that she seemed to be staring at the situation.

“I-I’m not sure what to say. I want to turn away, but I can’t turn away," Riley muttered, mesmerized.

“How does it make you feel?” Abs then asked.

Riley tried to assess what she was feeling. “I feel like ... something is dancing around down there. Maybe a bit ... hot? I don’t know. It intrigues me so much; I can’t stop watching them.”

Abs giggled. “Yep, you’re getting horny too. Maybe let’s add to the show?”

“What? What do you mean?” Riley queried.

Abs unhooked her bra and let it fall to the floor, revealing her pair of B-cup breasts, then leaned in and kissed Riley on the neck.

“What are you ...?” Riley started to protest. It’s not that she didn’t like it but was just taken by surprise.

“Shh, just go with it,” Abs whispered. She kissed down Riley’s neck until she got to her shirt’s neckline. She then grabbed the bottom of Riley’s oversized shirt and lifted it up, pulling it over her head, revealing Riley’s pair of C-cup breasts.

“Abs! What are you—” Riley started to object, but Abs kissed her on the lips, interrupting her.

Riley was shaking. At first, she thought it was in fear, but then she realized it was in excitement. Maybe some nervousness. This was totally new, and she didn’t know where this was going to end. But she was finding she eagerly wanted to discover what the answer was.

Abs started kissing down Riley’s neck again, this time without protest, kissing down her clavicle and onto her breasts. Abs kissed, then sucked, Riley’s left nipple, eliciting a slight gasp from her, then moved over and did the same to her right nipple. Abs then continued kissing down her side and stomach, down to the top of Riley’s panties.

“May I?” Abs asked, and Riley shook her head in affirmation. She then took a hold of Riley’s panties and slowly slid them down. “We’ll need to fix this sometime,” Abs teased as she revealed Riley’s full bush. She kissed around it down to Riley’s clit, which she kissed and sucked slightly.

Riley let out another gasp. She didn’t notice Abs looking back over towards Darren. Isabella was riding his cock, with Darren’s hands grabbing and groping her breasts. However, Darren was also starting to pay attention to what Abs and Riley were doing as well.

Riley was too engrossed in these new feelings to notice what else was going on. However, that changed when Darren suddenly spoke up.

“I’m gonna cum!” he yelled out.

“I shouldn't, but ... cream pie me!” Isabella moaned out.

Darren let out a strained moan, and Riley could see the muscles at the base of his penis working. Isabella gasped and flushed red.

Riley watched, enraptured, as they both moaned and then seemed to relax. Isabella then slowly lifted herself off Darren’s cock. A white to clear substance started to slowly seep out from inside her.

Is that what cum looks like, Riley pondered to herself. She expected it to be ... thicker? Goopier? And what was she doing thinking about her brother’s cum in the first place?

“Wow, that was unexpected. Raw and inside? Damn, girl," Naya observed with amusement. “Setting the bar down early.”

Isabella stepped aside before taking a seat at a computer chair in the room, allowing her to catch her breath.

Naya then took a position directly in front of Darren. “I guess we have to get you back into shape,” she teased as she took Darren’s softening cock in her hand and then wrapped her mouth around it.

“Here, maybe you should move over there,” Abs suggested to Riley, pointing to the round, cushioned chair in the corner.

“Yeah, maybe,” Riley mused before walking over and taking her seat.

“No, scoot down some,” Abs directed, as she slid off her own pair of panties and threw them aside, revealing a thin, red landing strip.

“Uh, okay,” Riley muttered, scooting herself down in the seat.

“Good,” Abs approved before getting on her knees and slowly putting her face in between Riley’s legs.

Riley gasped. She had gotten herself off before—at least occasionally—but this feeling was totally different. She felt Ab’s tongue flick around her labia folds and clit, teasing her.

“I won’t penetrate too far. We’ll save that for your special day,” Abs added before continuing. She started running her finger up and down Riley’s opening while focusing her tongue on her clit.

“Damn!” Isabella suddenly chimed in. “Finally finding out what you’re missing out on, huh?” She started switching between watching Abigail eating out Riley and Naya giving Darren a blowjob to his nearly recovered cock.

Riley wanted to acknowledge Isabella but could only manage a half-moaned out “Uh huh”. She found her hands attracted to her own breasts like magnets. Her nipples begged for attention, and she started poking and lightly squeezing them. She felt herself get hotter. The feeling in her pubic area, which before was just a tickle, was turning into something that felt like it was yearning to break out and release.

Riley believed she had made herself orgasm before, as she felt the feeling building up. She had felt this sensation before, at times working on herself. But soon the feeling started to exceed what she had even been able to accomplish on herself. She started grabbing and twisting both of her nipples with both of her hands as if doing so would somehow open a spout to release the feeling building inside of her.

In the meantime, Naya was satisfied that Darren was ready again. “Fuck me like a dog,” she demanded, taking off her boy shorts, revealing her own neatly trimmed triangle of hair, before climbing on the couch and hanging over the arm, sticking her butt in the air, inviting Darren.

Darren obliged by getting on his knees on the couch behind her and shoving his cock inside of her and immediately started to go hard. “Oh, fuck yeah. Fuck!” Naya cried out.

Riley heard and saw this but didn’t really comprehend it at the moment. Her own eyes felt like they were starting to roll into the back of her head. She couldn’t twist her nipples hard enough to give herself a release, and she instead grabbed the side of the chair. She started letting out louder and louder moans. She would...

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