My Best Friend's Sister

Prologue

James's POV

I closed my bedroom door, pushing Riley up against it as we kissed. She ran her hands up and down my bare chest, her fingers tracing my abs. She had already pulled my shirt off while we were downstairs. I moved my hands from where they were pinning her to the door, grabbing the hem of her shirt and slipping it off of her, breaking our lip lock. We made eye contact, both of us breathing heavily. My eyes looked her up and down, taking in her appearance now that she was missing her shirt. For a 15 year old, she was hot. Her breasts weren't large, but they weren't small either, and she had the most amazing curves. Riley wrapped her arms around my neck, pulling me in for another heated kiss. I put my hands on her butt, pulling her body right up against mine, before giving her butt a squeeze, causing a small moan. Her arms moved from around my neck again, reaching for the button and zipper on my jeans. Damn, she was serious. I had gotten a text about an hour ago from Riley, saying she was going to come over to help me study. She may be a year younger, but she knows much more math than anyone my grade. I discovered this when she solved a math problem that had both myself and her older twin siblings, Emily and Eldon, stumped. After that I asked if she could come over every so often to help me with math so I could keep my grades up. Now usually when she came over, we actually studied. But today she said that she was busy this week and today was the only time that would work for her. Then she came in and started flirting with me, told me she wanted to hook up, and kissed me. Now I know what you're thinking; James why on earth did you agree to hook up with your best friends little sister? Well, the answer is simple. I'm a 16 year old boy. I'll hook up with just about anyone. Riley pulled my jeans off of me, and I guided her towards the bed. Pushing her to lay on her back, I climbed on top, straddling her. I undid her pants, tossing them aside and kissing down her neck and chest. She moaned as I started sucking on her left breast, leaving my mark. With other girls I might leave hickeys on their necks or higher on their chests, but Riley's different. Eldon doesn't need to be seeing a hickey on her. Riley won't be the first girl I've been with. Nor will she be the 10th. I'm kind of a player, I've hooked up with countless numbers of girls. Of course, even if girls know this it doesn't usually deter any new hookups, case in point with Riley. I kissed my way back up her chest and neck, kissing her lips again, letting our tongues intertwine. Riley tangled her hands in my hair, holding me close to her. I broke our lips, needing to ask a question before we went any farther. "How far have you gone with a guy before?" I asked. Normally it wouldn't be something I'd worry about, but this is different. This is Riley, not some bimbo. I've known Riley for practically my entire life, she's not some girl I just decided to sleep with. She seemed surprised I'd asked her, and slightly nervous.
"Honestly..... Basically nothing." She admitted, her cheeks heating up in embarrassment. That sentence was what caused everything to click in my mind all the sudden.
"Is this about earlier?" I inquired, already knowing the answer. Riley bit her lip, looking down as she was unable to meet my eyes. At dance rehearsal today Eldon and Riley were arguing over something that was most definitely stupid, I didn't care enough to figure out what it was. At one point, Eldon exclaimed that he was right and she was wrong because he knew more about the world than she did and she's practically still a baby. Like any 15 year old would, Riley got pissed at his comment. She tried to argue she knew just as much, and she was not still a baby, but everyone else from A troupe who was there at the time, Emily, Stephanie, Daniel, and myself, all sided with Eldon, saying she still had that innocence of a young child. When Riley's silence continued, I sighed, sitting up and climbing off of her. She sat up as well, still unable to meet my eyes. "Did you really think letting me take your virginity would change anything from earlier?" I questioned.
"Don't do that." Riley sighed.
"Do what?" I asked, raising my eyebrows.
"Lecture me. Act like you're a disappointed parent. It's ridiculous. We're sitting on your bed in only our underwear, we nearly had sex, and now you're lecturing me like you're my fricken parent!" Riley stated, sounding rather angry with me.
"What would it have done for you? I seriously doubt you would've told anyone." I responded.
"It would've proved that I'm not a baby. And I didn't need to tell anyone, you and I would've known and that's enough." She replied, finally making eye contact. She still had anger in her tone as she spoke.
"That's not a good enough reason to lose your virginity. I won't take it from you." I told her. She sighed again, looking furious.
"Can't you just do this one thing for me?" She asked.
"No." I stated firmly.
"Please." She pleaded. I found this situation odd. I'm saying no to a girl who's begging me to screw her. I must really be good friends with Eldon.
"No Riley." I said, my tone expressing my decision was final.
"Alright fine. This was stupid anyway." She sighed, moving off of my bed and walking to grab her clothes. Weirdly enough, as I watched her grab her things, I felt sad. I felt bad for her. She doesn't deserve all the crap she gets about being a child, especially since the people who say it to her the most are a) only a year older than her and b) less mature and/or stupider than she is.
"Riley wait." I sighed, knowing this was a bad move. She turned to face me, looking confused. "Give me a good reason to go through with this." I said. I watched a small smile form on her face as I gave her a second chance. She thought for a moment, before answering me.
"Because if you take my virginity, if Eldon ever asks I can tell him it was someone who cared about me and would never harm me. And I can give him peace of mind that it was someone who was careful and made sure I was okay and we were safe." I sat silently for a minute. That was a pretty damn good answer. I know Eldon worries about his sisters. If I take her virginity I can tell myself it's me doing something to keep my best friends family safe. Plus Riley is really hot and part of me may never forgive myself for not screwing her.
"Alright get over here." I said, causing Riley to smile bigger. She dropped her clothes, walking back over to the bed. I pushed her to lay down and straddling her again, kissing her. Not like before though, much gentler and more passionate. I'm going to make sure her first time is memorable, not some quick hook up to get it over with.