In every part of your life—a relationship, a friendship, a job, whatever—there's a single best moment, the climax (stop giggling!) of the whole experience. It's that one point where everything is as good as it's going to get, and nothing is ever quite the same after that. The thing is, you never really know what that moment is until its gone. That's what I'm talking about today.
Sorry, it's me, Rose, again. I guess it's been a while, so I'll try to catch you up in a super-quick way in case you forgot all the scandalous details. Thrilling life experience number one: gave my gorgeous stud of a step-brother head in the cab of his pick-up. Then we became a "couple," by which I mean he let me give him a ton more blowjobs (and more!). Since we're, like, semi-related and all, we tried to throw our parents off the trail by pretend-dating our friends, Andrew and Natalie. When Gabe took my virginity at Christmas, though, Mom found out, though thankfully she didn't freak.
OK—I think you're all caught up now.
I'm not going to start with that perfect, best day I was talking about. Nope, I'm starting with the day before, when I was sitting with my best friend Natalie, trying and probably failing to describe to her what sex was like.
"Does it hurt?"
"Ummm...yeah, but it's a good kind of hurt. And it hurts less and less each time," I assured her.
She seemed to be turning over the idea of "good pain" in her head.
"Is it hard?" she asked. "Like, do you need to be really...bendy?"
I giggled a little.
"It depends. Like, there's lots of ways to do it, you know, positions. The bendier you are, the more you can do."
"Do guys...I mean, I guess, does Gabe want you to do lots of positions?"
"I'm pretty flexible, so, well, yeah. But that's not just for him, either. I like the different feelings."
I could tell Natalie was afraid she'd lack the "skill" to have sex. Maybe my answers weren't helping her.
"Don't worry about that stuff at first, though," I promised her. "A guy will be thrilled to get a chance to de-virginize you. He won't expect you to pull any crazy porn star moves or anything. I mean, he might even like it that you don't totally know what you're doing, so he can show you."
If this would have been some other person, you'd say she was acting really shy, but for Natalie, this was pretty out there, like take charge behavior. It was kind of cool, actually.
"Well, it probably won't happen for a while," she said, sounding a little dejected.
I thought for a second, before realizing what she was saying between the lines.
"You want to do it, don't you?"
She looked panicked.
"I would never—I mean, with Gabe."
"No, of course not. I just meant...you wish you had...ummm...your own Gabe, right?"
She looked like she wanted to crawl into a hole and hide. I wanted to help her get out of her shell, but I didn't want to make her feel uncomfortable.
"Yeah...but what guy in school would do it with me?"
Like, most of them
, I thought.
"Guys will totally fall for you if they think—if they think they have a chance. No offense, but right now, guys probably think you have no interest in sex or even dating, because you're, like, shy. I was too before Gabe," I assured her.
I let her think about that for a while, while we aimlessly flipped through magazines together.
"What do, you know,
thingies
look like?" she asked under her breath.
Keep in mind this is an eighteen-year-old
woman
with an internet connection at home.
"You've really never seen one in porn or anything?"
Natalie always made me feel way more experienced and savvy.
"I'm too nervous to look at that stuff," she said, with a weird kind of giddy nervous energy. "Even though I do, you know, want to see one."
"Anyone in mind?" I said in my most cloying voice.
She turned super red.
"Not Gabe! I promise."
"I know, I get it! We'll just need to find you a thingie to look at. Maybe even more than that," I said, tickling her sides and rolling across the floor with her.
"Natalie?"
"Yeah?"
"Say the word 'cock.'"
She looked puzzled.
"Why?"
"Because you should. It's part of your, like, practice."
Under her breath, like she was reciting some magic word, she spoke: "Cock."
"Good job. Now tell me—no, admit to me—that you would really like to suck a big cock."
I was teasing her a little, but in my own way I was trying to help her. She looked at me pleadingly, hoping I might break out laughing and free from the embarrassment of doing what I told her to do.
"Honey, look at me," I said, slipping into the role of cool, experienced slut that I was finding more and more enjoyable when I was around her. "I know what you want, and you know what you want. It will make things so much easier for you if you can just admit it."
She looked up at me.
"I really do. I want to suck a big...cock. And...I want it—I mean the guy—to, you know...put it in me. I want it a lot."
Guys, don't let your imaginations run wild here. We are not about to start scissoring here.
I've told you all before that Natalie could have been cute with a little work, only she herself would have had no idea what kind of work she needed. In different circumstances, I'd have really tried to build her confidence up, so she could get busy with her boyfriend. Only, her "boyfriend" was
my
boyfriend, Gabe. I like to think I'm a nice person, but I'm not
that
nice, and I sure as hell wasn't going to let her play around with Gabe's cock.
I started looking her over, though. I'm not going to give you precise measurements or a full-on description of her tits, because, hello, I don't know that stuff. I will say she had...potential: long, thick, curly brown hair that could use some hair treatment stuff to tame it, nice, full lips with a nice natural color, since she didn't wear lipstick ever, a good smile thanks to the orthodontist, though most guys never saw it.
Compared to me, she had a longer face, not cute and heart-shaped but more elegant and graceful. She was also taller than me, and looked older and more mature, if she would get out of the hand-me-down clothes she wore. It wasn't that she couldn't afford better stuff, either, just that she never seemed to try. She didn't want to stand out.
Natalie wasn't super skinny, but not fat either. Her body was more feminine than mine. (I hate hate hate having a body like a little girl.) All in all, with a little work, she could be at least as hot as some of the girls that guys in school tripped over themselves to ask out on dates. Her issues weren't physical; they were emotional.
"Natalie, you're totally hot," I told her.
"You're just saying that. Pretty much nobody else thinks that," she replied.
"No, really," I reassured her. "You just need to show that hair of yours that you're in charge. And maybe a few new outfits from this century"
I realize that "make-over" is a totally cliché way to try to transform the shy girl in glasses and paint-spattered overalls into a total high school hottie. Only, in this case, it was meant to be a lot more than that.
My mom had known about Gabe and me for almost three months by this point. That was three months of holding hands, three months of passionate kisses, three (more) months of swallowing Gabe's cum, three months of secret, mind-blowing sex, and two months of getting tied up and spanked, too. Meanwhile, our dad didn't have a freaking clue.
To me, that meant we could drop the whole charade of pretend boyfriends and girlfriends. Gabe didn't need Natalie, I didn't need Andrew. My hope was that her experience with Gabe would give Natalie more confidence with guys. As for Andrew, I had never really understood why he went out with me, and I wasn't worried about his feelings too much. As it turned out, that was a huge fucking mistake that I can see clearly in hindsight.
At the time, though, break-ups seemed like the best thing for all of us. Natalie would be back on the market, fresh out of a relationship with the hottest guy in school (I'm biased), and ready to go on actual dates with actual romantic prospects.
"I've got a great idea," I told her. "Sleep over tonight. We'll go to school together tomorrow morning, and I'll totally dress you up and stuff. You're going to look so hot, and when guys see you, they'll have to roll up their tongues like in cartoons."
"But I'm with Gabe," she objected. "I mean, that's what they all think."
"Yeah, about that..."
***
"Looks like 'slut' was on sale at Goodwill."