My name is Brent. I'm 22 and graduated college last May, but I currently live at home because I was hired to start work in January. I don't have a girlfriend right now. We broke up several months ago, just before graduation. Don't feel too bad for me, though. While I certainly miss the sex, I don't mind losing the crazy. I'd like to say I'm still single out of choice, there really aren't many options in a small town where most of the people my age are away for college or they work so much that they rarely go out. And now that it's October, I've conceded defeat, waiting for a new opportunity with coworkers at my job.
I have a younger brother, Chris, who is 20 and in college. He stays busy so we usually only see him over holidays. I also have a younger sister, Rose, who is 18 in her senior year of high school. I have a good relationship with all my family, but I'm definitely closest with Rose. She trusts me and likes to tell me all her high school drama shit. I would never think about dating Rose because she's kind of a bitch sometimes. She's spoiled rotten, is slightly smarter than a rock, has a very short temper, eats steak well done with ketchup... I could go on, but you get the point. That kind of terrible person. But damn, she's hot though. She's 5'3", around 135 lb. She doesn't work out, but she has hourglass figure and just enough on her thighs and ass to look really seductive. From doing laundry, I know she wears 36DD bras. Her hair is brunette, and she usually wears it straight, just long enough to pass below the shoulders. Her brown eyes always seem to sparkle.
Rose has obsessed for months over some jock named Aaron. For the past year, she's been doing all kinds of crap trying to get him to notice her and like her. At the beginning of the semester, he asks her to the homecoming dance. She's overly excited every day until homecoming. I guess she was too distracted to focus on being bitchy, so she was abnormally cool for the past month.
-.-.-.-
Homecoming day has arrived. Rose's friend Lakeisha picks up Rose to get dressed with other girls and carpool to the game. Mom and I go to the homecoming game to watch Rose. At halftime, all the girls are escorted onto the field. Rose comes on the track in a Corvette and walks across the field. She's wearing a blue/green dress (I can't remember if she called it teal or turquoise; girls don't know there's only 12 colors). Anyways, the dress is ankle-length and not very tight down her figure. She thinks she's overwieght, and she's embarrassed to have big boobs, so she usually dresses pretty modestly, but this dress was strapless, shoulderless, and tight enough around the chest. It didn't have any cleavage, but you could definitely tell she has a great rack. With her hair and makeup done like a princess, and that beaming excited face, she looks gorgeous. Some spraytanned bimbo with a bigger ass ends up winning homecoming queen, but Rose isn't mad. After the game Aaron comes up to mom and tells her that he will bring Rose home by midnight. Then we go home to let her have fun.
-.-.-.-
I settle in with video games until a little after midnight when my phone rings. I check who it is.
Why is Rose calling? Wait, why isn't she home already?
"Rose? Why aren't you home?"
Her voice keeps breaking like she's been crying. "Shut up. Just pick me up."
"Aaron isn't bringing you back?"
"I told you not to ask!"
What the hell? She usually tells me everything, good or bad (and whether or not I want to hear it)
"Rose, something's wrong. I'll tell mom so you don't get in trouble, but you're going to tell me what happened on the way back, okay?"
"Ughhh. Fine"
I head downstairs to mom's room. She's reading in bed, probably waiting up for Rose. "Mom, Rose needs a ride and she sounds upset, so don't be worried if we end up talking and don't come home straight away."
We live in the boondocks so it takes 20 minutes to get to the dance hall. She's outside sitting on the curb. She gets in and starts to say something, but immediately starts crying. I pull into a parking spot and ask what's wrong.
"Aaron never wanted to come to homecoming with me! He really wanted to go with Lakeisha, but she already had a date, so he asked me just so he could get closer to her. That bitch knew how much I liked him and she still ditched her own date and went with Aaron!"
"Wow, that sounds like a dick move. For both of them."
"I know! And that asshole had the nerve to offer me a ride home. He thought he was being a good guy by keeping his word to mom or some shit. And guess what, he even thought it would be funny to say Lakiesha would sit in the front giving him a blowjob while I ride in the backseat. What the fuck kind of person would do that? And you know what he said when I asked him why he did this? 'I've never been with a black chick before.' Like, what the fuck?!"
I'm pretty sure she started seeing red. She jumps out of the car and starts stomping across the parking lot. I look where she's going and recognize Lakeisha's car.
This can't be good. I don't want her getting arrested or paying for damages.
I get out and run after her. I grab her and manage to say a few things about how she's better than Lakeisha and she shouldn't stoop to her level. After a bit, Rose stops trying to get away and starts crying again, hugging me. She gets embarrassed and heads back to my car. She opens the back door and says, "Sit back here with me. I need a hug, and I don't want to cry out here in front of everyone."
She cries, complains, and rages for several more minutes.
Eventually I ask her, "So why did you even like this guy so much anyways?"
"Have you not been listening? I don't care about the stupid crush. I'm over that asshole! But I really hate how both of them treated me."
"Okay, yeah that makes sense."
She sighs angrily. "Plus Aaron was supposed to make this night special!"
"What do you mean?"
She's suddenly embarrassed. "Well... Umm... Can you promise you won't tell mom?"
"Duh"
"I wanted to lose my virginity today..." She waits for my reaction, but I just look at her patiently. "I know what you're thinking. Aaron and I have never even dated, so I'm just being a dumb kid. But that's not it! I don't love him, but I've heard lots of girls say he's amazing in bed, and I figured senior year is time for me to start learning, and I wanted to learn from someone who knew what they were doing, and this is prom night so it's supposed to be special."
Until she said that, I couldn't help but think all of her story was just more of the same bullshit every high schooler goes through, but now it all makes sense to me. She just needs to get laid. I totally get it now because I also do stupid shit when I get desperate.
"Okay Rose, I completely understand that feeling. But your virginity is kind of serious to give to some random jock you don't even like that much. Are you sure you're serious about this?"
"Well not anymore, obviously! But yes, I've been prepping myself for months, and I've been talking with that bitch-who-shall-not-be-named all summer about it. She knew how much I wanted this and she still took this from me!"
"Woah, now. Let's not talk about her." I can tell that she was starting to rebuild a fury, so I needed to change the subject, but the only thing I can think to say is the question currently gnawing at me. "What do you mean prepping yourself? Like psyching yourself up to do it?"
"Yeah, that too... This is kind of embarrassing, so don't laugh, okay?" I nod and she continues. "Lakiesha told me it hurts pretty bad the first time, and I didn't want it to hurt. She said I should stretch myself out first so it won't hurt."
Cue awkward silence.
After an uncomfortable few seconds, she keeps talking. "Yeahhh... Uh... So I started with a finger, and kept... doing stuff with myself almost every day trying to get used to it. Then after that stopped hurting, I went to 2 fingers, then 3. Then Lakeisha went to the adult store and bought a dildo for me. I've been using it like every day until today."
I make some dumb joke that broke the awkwardness and let us change the subject. And then we shot the shit for a while, until...
-.-.-.-
Okay, I should preface the rest of this by saying incest isn't quite as taboo in our family. Two of our cousins, brother and sister, live together and have 2 kids. Everyone in our family knows, and the family mostly treats them as any other married couple, but they do avoid talking about it when they can. They went public when she got pregnant the first time, which was when I was 9 and Rose was 5 or 6. Our mom (dad divorced shortly after Rose was born) told each of us about it once we were old enough to understand. Mom always emphasized how it could destroy a family if you end up having a really bad breakup, so we got plenty of warnings and lectures even though we never tried anything.
So we were raised from a young age thinking our siblings were fair game as long as we were super careful and thought very hard before starting anything actually romantic. Which means I've been jerking to Rose basically from the day she grew boobs, but I've never acted on anything because, like I said, her personality is totally incompatible with mine for anything other than a brother-sister relationship.
-.-.-.-
At some point during our conversations, I start wondering, What if I gave her that first time? I didn't really want to take that moment for her, but as I mentioned, it had been several months since my girlfriend and I broke up, and I already told you I act crazy when I'm desperate. The more I thought about it, I couldn't really find any downsides. With our personality clashes, it was destined to end badly if we actually started dating, but there's no real reason to avoid being friends with benefits... Or siblings with benefits... Of course we'd have to be extra careful with protection... Would she even want to do that with me? I mean, she did just talk for an hour about how she wanted to lose her virginity tonight... And how long she's been warming her body up to it... And she does look gorgeous tonight...
"Hahahaha Brent! You aren't even listening to me are you?" She snaps me out of my thoughts, and apparently I missed something. I looked at her silently, deeply focusing on how pretty she is. She starts to look uncomfortable, so I better do something. I move in for a kiss.
I kiss her. No tongue, only holding my lips against hers for a second before backing off. She looks confused for a split second, and then giggles nervously. She acts flustered, and her face twists with thought, appearing to be a strange mixture of confusion and excitement. My heart moves into my throat and the next second feels like an hour. Then she gives a "what the hell" look and shrugs her shoulders before wrapping her arms around me.
We make out for what seems like an eternity. When we both start getting into it, I move my hands over her. I try to feel every inch of her beautiful body. My hands move to her back, her sides, her neck, running my fingers through her hair, and back down across her hips and thighs. As I caress her, we slowly inch down in the seat until I am laying on top of her in the back seat, her legs spread and me in between. I reach up and grab her boobs, squeezing and fondling them. I'm amazed at how big they are, thinking that I probably can't grab all of one even with both hands.
Her breath becomes labored as she runs her hands across my back. I move my hand down to her thigh above the knee. I slowly caress her thigh over her dress, working up to her hips. She breathes heavier, but makes no attempt to stop me. Still kissing her, I lift off her and kneel beside her as I rest my hand on the place between her legs. Above her dress, my hand rubs and massages her pussy. I'm very gentle at first, slowly rising up to a good rhythm. She grabs my head and moves me down to kiss her neck. I feel her heavy breath in my ears as she starts moving her hips to match the movement of my hand.
"B-Brent... if you want, you... you can put your hand under my dress"
