Family Friend Becomes More

Okay, first of all I'd like to explain that I prefer not to get too caught-up in detailed descriptions – particularly things that the characters wouldn't know. But it should go without saying that all characters are at least 18 years old.

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I was on winter break and loving it. Or at least I had been. Staring out the side window of our SUV I was dreading what would no doubt be another awkward and tedious visit with my parent's best friends, the Petersons. My dad and Jim Peterson go way back, before I was ever born. They've worked together for almost as long.

Jim and his wife, Karen, have two daughters. Jamie, who is only a few months younger than I am, is an absolute knockout. Even though we've gone to the same schools since the 6th grade, we've never really hung out since she and I ran with different crowds. But that didn't keep me from noticing what a hottie Jamie is. She's a tall, leggy brunette, and plays basketball on our school's team. Her body is perfect: firm and lean. And do her outfits ever make that obvious! As if that isn't enough, she has beautiful brown eyes and the prettiest face I've ever seen.

Jamie's younger sister Cassy is another matter. She's a little blond chatterbox, around my height (although she must be two or three years younger). It seems that most of the time she wears round, gold, wire-frame glasses over her brown eyes. Despite Cassy's nerdy appearance, pretty much everything she says reveals that she is a total ditz. Just being in the same room with her can be unbearable. Not only that, but she didn't appear to have much a body to speak of. It was hard to tell, though, because whenever I saw her during my family's occasional visits she was dressed modestly and spent of most of time in the rec-room.

As we turned off into their neighborhood I tried to be optimistic. It was only one evening. But then again we were invited to dinner, which could easily last all evening with table talk. Jamie should be there. Maybe she would even greet us all with hugs like last time. Just the vivid memory of holding her body against mine for that fleeting moment had inspired my masturbation for the next couple of days.

Before I knew it we were parking in the looped driveway in front of the Petersons' giant house, atop the largest hill of our small suburban city. We let ourselves in the side door, since they were expecting us. As we walked into the kitchen Jim and Karen greeted my dad and mom. Meanwhile I spotted Cassy standing behind them, looking fidgety.

"Hi, Cassy." I began.

"Hi-uh." She replied after a slight hesitation, probably expecting me to ignore her as I usually do.

"So, you're on break too?"

"Yep."

"Have you been enjoyed it so far?" I pursued.

"Oh yeah, it's great! I get spend lot's of time with my girlfriends and don't have to go to all those stupid, boring classes." She gleefully replied.

"Hmm, with your girlfriends." I teased.

"Gawd, I mean just us girls. Geeze." She muttered irritably.

With a grin I walked down the hall to use the bathroom. She was gone when I returned. Great, I thought, now what the hell was there to do? My mom was helping Karen prepare dinner and my dad was sitting on the couch talking to Jim about work with the TV muted in the background. I apparently was the only one who would have liked to watch it. So I decided to quietly wander off.

Turning the corner I began climbing the curved staircase. As I approached the top I could hear a TV in the rec-room. Following my ears I found Cassy sitting on the light-gray loveseat, watching "The Fresh Prince of Bel-Air." I made eye-contact with her as I entered the room, then took a seat beside her.

"Hey Cassy, where's Jamie?"

"Jamie's still at school. She said she had some stuff she needed to take care of, but I think she just stayed to party."

"Oh. So, what are you watching?"

"Fresh Prince. Why, are you going to make fun of me again?"

"What? No, I wasn't trying to make fun of you before. I was just surprised that you aren't going out places with guys yet."

"Well, sometimes a couple guy-friends will come with us, but you know how high school guys can be. They're so, like, immature sometimes."

"Yeah, I see what you mean." I said, turning my entire body to face her and leaning in almost imperceptibly. "Every time I'm here you look more grown-up than before."

"Aw." She drew out the sound. "Thank you so much." A subtle blush and quick batting of the eyelids confirmed her sincerity.

I found Cassy's body language encouraging, and was surprised how pleasant she was to talk to. Most high school girls have a special respect for guys that are just a few years older, and I was definitely experiencing it. I continued to speak.

"Pretty soon the guys will be all over you."

"I guess so."

"You don't sound too excited about it."

"I just don't know if I'm ready for that."

"Because you're… uh … inexperienced?"

She squirmed in her seat but said nothing.

"Oh, I'm sorry. If you're uncomfortable talking about it, I understand."

"No, it's okay. There are, like, some things I don't know."

"Alright. You can ask me some questions if you want to."

"What will it feel like?" She reluctantly began.

"At first it's going to be a little unpleasant. You see," I was searching for the most delicate way to explain it to Cassy in terms I knew she would understand. "There's this… material… inside you that a guy will have to push his penis through the first time you make love. If he's gentle and takes his time it won't be so bad. After that it should be wonderful: the most exciting and pleasurable thing you ever do."

"How will I know when I'm ready?"

"Trust me, you'll know when it's time. You will be alone with someone you've known for a long time. Your conversation will naturally become more intimate. You may notice yourself breathing deeply and blushing."

Her entire face was now slightly flushed, and she trembled as each breath was slowly taken. Unable to restrain my passion, I leaned in further and pressed my lips against Cassy's. I could see the surprise in her eyes. But she apparently was as excited by our talk as I was, because she continued to kiss me. My hands slid from her back to her waist. As I prepared to lift her sweatshirt, Cassy pulled away.

"What if they come up here!? I'll lock the door."

Now standing, we began to kiss again. I started sliding my tongue into her mouth, and after a moment she did the same into mine. Mine rubbed over hers. Hers dragged over mine. Back and forth, and all around our mouths they went. I decided it was time to proceed. I stepped back, taking the bottom of her sweatshirt in my hands and pulling it off over her head. Inside her little bra were Cassy's young, pert, still blossoming breasts.

"Oh, Cassy. Your breasts are beautiful." I offered, while she was still fixing her hair. "You can go ahead and take off my shirt."

"Thanks." She replied while eagerly obliging.

Before I knew it I was in only my boxers, taking in the sight of Cassy in matching white bra and panties. Kicking her crumpled pair of jeans aside I stepped closer, allowing her to embrace me. Reaching around, I unhooked her bra and dropped it on the floor. Instead of caressing her soft young body I started planting kisses down her neck, starting behind the ear. After making my way to her shoulders Cassy pulled away.

"I think I'm ready." She whispered.

"Great. I'll be gentle." I tenderly reassured her.

First dropping my boxers to the floor, I laid her back onto the sofa and slid her panties off. I leaned over, giving Cassy deep, lusty kisses to help her relax. As my firm manhood parted her warm, moist slit she threw her head back with eyes firmly shut. Slowly I entered her, lowering my head to hers as I noticed her tearful eyes.

"I had never realized how desperately I need this until now." I tried to comfort her. "Are you ready?"

"Uh huh." She strained to answer.

I worked up a slow rhythm of thrusts. At first Cassy banged her fists against the cushions. Then she grabbed two handfuls of them. I offered her my hands, which Cassy grasped tightly as I made love to her with even greater gusto. Carefully I maintained pace until her orgasmic massages brought me to the edge. I quickly withdrew and sprayed her belly.

Winded, I asked, "How did you like it?"

"You were right. That was amazing." She hesitated. "But…"

"But?"

"But are we going to see each other again? I mean now that we've done this, do you still want me?"

"Of course. I want to be with you more than ever. We just need to think of a way to let our parents know how we feel about each other."

"Oh my God! Our parents! We'd better get down to dinner now."

"Tell our parents? No way!" I thought to myself. "Besides, there's no way it could work out. We live so far apart." We both hastily redressed. Taking turns in the bathroom we both tried to wash away the scent of our passionate act with a couple splashes of sink water, and joined our families at the table.