My best friend in middle school was Carrie McLeod. We hadn't known each other in elementary school but in sixth grade, we just became the best of friends, BFF's.
We began spending the night at each other's house where I found that not only was Carrie my very best friend in the world, I also liked her older brother, Oliver. He was nice to us and, especially, to me, even though he was older–four years older. I really expected him to just ignore me like I wasn't even there but every time I would come to Carrie's, he would always say hello and ask me about school and stuff like I was a real human being.
There became times when he and I would just talk with each other, I was interested in hearing about how high school was like and he was very open about it. Being in middle school, it just looked to me like high school was miles-different, just like another universe.
But Oliver told me a lot about it, how kids seemed to form groups, even more than in middle school, that you had to feel strong to resist the peer pressure that was inevitable and about how boys and girls got along in high school compared with middle school.
He was really nice and I felt like he was a friend, even though he was eighteen and would be off to college the next school year.
I did see him once in his underwear, though I'm sure he didn't see me at the time. He was coming down the hall from the bathroom and he had on white briefs but I didn't see much of the front. Oh, well.
Carrie and I talked about sex, of course; we were fourteen, our hormones were in control, it was much of what we talked about.
It was a Friday night in March, we'd just put out the light when Carrie said, softly, "I did it, Sara, I really did it."
"You did what? Not sex?"
"Yes, yes, omigod, I really did."
"Who was it? Was it good? Did it hurt? You're on the pill, right? Did you bleed? Did you get off? How many times? Was his thing big? Omigod, you've really done it. Tell me, tell me all about it."
"It was, oh, you can't ever tell anyone ever, ever right? It was Robbie Vincent. And, no, it didn't hurt, not at all. And, yes, oh, it felt lots better than good."
"The rest, tell me everything," I pleaded.
"We did it all Wednesday afternoon. I didn't count times, we just kept doing it. I had two orgasms and he did too."
"Was it better than getting yourself off?"
"Oh, Sara, just wait. Oh, lots better, like lots stronger and it lasts longer, too. And you should see the boy when he does it, the look he gets. It must really be awesome for a guy, too."
"Did you suck on it?"
"Oh, I loved it, wait 'til you feel a boy's hard dick in your mouth. You're gonna love it. And when he cums, oh, so cool, I drank every drop."
"What's it taste like?"
"Um, a little salty, not much else, it's real thick and slippery."
"Did he, you know, give you oral, on your pussy?"
"Oh, girl, the best. Just wait, just wait. I'm going crazy right now just thinking about it. I loved the fucking but, well, even the oral might have been the best."
"Really, that good?" I asked, I just had to know.
"Really that good. It's just awesome. If you think you've had an orgasm, well, get a boy to lick you out. I just went crazy. Once he does it, you're just never the same again."
I was having a hard time understanding just how good she meant but knew it must be just the best.
"I have him do it to me every time we're together, I just can't get enough."
"So, was it real big? Did it go in okay?"
"His is the only one I've had so, well, I don't know. It was big enough for me, that's for sure. It went in good, we had to try some, I got as open as I could and wiggled around while he pushed, but it went in good. Oh, then, when he started fucking me it was amazing, it made my pussy feel so good, every time he went in or out, oh, it just sent shivers all over me. You've got to get fucked, girl, it's the best. You've got to do it."
"I need a boy, Carrie, I can't do it to myself. I mean that's what I'm doing now. I need a boy," I said frustrated.
"Is there anyone at school you think might be interested in you?"
I thought about it and, well, sure there were boys I knew, of course there were. But, well, did I take that kind of interest in any of them?
"No, not really. I mean there's Rick Moody but he's got all the girls chasing after him."
"Oh, yeah, forget him, he's kind of stuck up anyway. Mister Bigshot. Um, how about not in our grade, any boys you like? In the neighborhood, even?"
"There is a boy that lives behind me but he's kind of nerdy, a computer geek, kind of," I told her.
"Come on, Sara, shit, there's gotta be some boy you like, some boy that likes you, come on."
"Oliver?" I said softly.
"My brother? You really mean it, Oliver?"
"Well, he's always nice to me, I like him, he treats me like I'm a real person, yeah, Oliver."
"But he's eighteen, you're fourteen."
"Okay, I know that. Does he have a girlfriend?"
"No, I'd know that if he did, no, he really ... I don't think he's ever had a girlfriend."
"You don't think..."
"No, no, he's not gay, I'm sure of that. He's got a stash of Playboys that I found and his laptop has some videos on it but nothing with guys. It's all fucking and blow jobs. With girls."
"So, he's like hetero, that's good. Do you think he'd, well, do me if I asked him?"
"He's a guy, Sara. Damn, don't you know anything about boys? They want to fuck, it's as simple as that. Sure, he'd do it, are you kidding?"
"Well, I'm just a girl, I just started wearing a B-cup bra last month, he's a senior in high school, I've seen those girls and they're awesome; big boobs, long, sexy legs."
"But I've seen you naked, Sara, you're a hot girl. Come on, quit being so down on yourself. Your body is every bit as hot as mine."
"I don't know, I'm really not sure if he would like me that way."
"Shit, why not go ask him? Go see if his light in on, knock and ask to come in, that you have a question for him. See how it goes. Make it happen, girl, I did."
"How do you mean, you did?"
"Well, I decided that I was going to give it up to Robbie so I asked him over one afternoon to help me with pre-algebra, he's good at math."
"So you kind of started it?"
"Oh, did I. I brought him up here to my room and said I'd be right back and went in the bathroom and took my clothes off then came back into my bedroom. Trust me, Sara, boys react one way to a naked girl. I know, I know for sure."
"But, it's your brother."
"So? Hey if he's still a virgin, there's no one better than my best friend to take his cherry. You're on the pill, what's keeping you? My parent's bedroom is downstairs, they never come up here. I had Robbie up here last night, we fucked like bunnies. They never knew a thing. Oliver's right down the hall. Go knock on his door. Oh, and go like you are, that's a cute nighty on you."
"But what if something happens?"
"Then, be glad. It's what you want, right? I'll be fine if you don't come back, stay with him, have fun, I sure do with Robbie."
I laid there in the dark, my head whirling. Should I? Would I be a slut? Did I care? What if he laughed at me? Oh, that was the worst. I didn't want to be humiliated.
But, then, I realized that my hand was in my panties and I was rubbing myself; I was so turned-on.
"Okay, wish me luck," I whispered and got up from her bed as I heard, "You won't need it, Sara, you're a hot girl. Go have fun."
I opened her door and crept down the hall and, there it was, light filtering from under his door. I stood there looking down at the sliver of light, wanting to knock on his door but dreading it as well.
I really don't know how long I stood there, nervous, horny, scared. Then I softly tapped on the door, "Oliver, It's me, Sara, can I talk to you for a minute?"
I had my eyes closed to keep from realizing that I was really doing this, I was really going to seduce my best friend's brother.
"Oh, come in," I heard as I twisted the knob and pushed the door open.
There he was, sitting up in bed, his laptop on his lap, a teeshirt showing.
"So, what's up, Sara. You ... um..." he said, stopping, looking at me as I stood there in front of him in a nighty that had to be pretty sexy.
"I wanted to ask you something, Oliver, we're pretty good friends and I need a guy's opinion."
"Sure," he said, "ask away."
"Well, you probably know your sister has a boyfriend, right?"
He laughed and said, "Yeah, I've heard them some afternoons. Carrie gets kinda loud sometimes."
"Oh, yeah, I didn't mean that, um, well, I was wondering, well, I don't have a boyfriend, and I was wondering if maybe it's the way I look? What do you think? You're a guy."
"Sara, I think you're the prettiest girl I've ever seen. And, well, don't be mad but, well, in that nighty you look fantastic. Any guy would want to be with you."
My two words hung in the air between us.
"Sara, I've dreamed of being with you so much. Are you really asking me?"
"I'm really asking you, Oliver. Would you have sex with me? Be my first boyfriend, take my cherry?"
There, I'd gotten it out and now the stage was set as I tried desperately to keep from shaking.
"Sara, there's no one I care about more than you. I don't want to do anything you might live to regret, that you might some day be sorry for."
"I won't regret it, Oliver, I will only regret it if we don't. I may not be as sexy as some of the girls you've done it with but I'll try, I'll really try."
"I ... I really haven't ... I'm like you, Sara. I'm a virgin, too," he admitted.
"You are? You're what, eighteen? I just thought..."
"Well, I haven't. It just didn't happen. Maybe I'm too shy. Are you really sure about this? I mean Carrie will wonder where you are, right?"
I laughed and told him, "Carrie knows I'm here," I told him, then I added the crucial information, "and she knows why."
"She does? She know's what you asked me just now?"
"Yes, and she's not expecting me back to her room tonight, Oliver, she expects me to sleep in here with you. I hope you want me."
He jumped out of bed, now I saw he had boxers on and the front was all stretched out. He put his arms around me and we had our first kiss. I opened my mouth to him and he put his tongue inside which I began to suck.