Ashley Ch. 01

Whatever I wound up thinking about out must've taken a long time to process because the next thing I remembered was a pillow thrown at my head for the second time that evening. It knocked me into my leather chair. "What's up, Tiger? You look a little sick." Ashley turned on the lamp by my bed, leaving it at its lowest setting. She crawled to the edge of the bed and inspected my change in attitude. "Although 'a little' is probably an understatement."

"Ashley, I... I don't..."

"Don't what?" My sister sat closer, her feet on the warm floor. "Did I do something wrong?"

"No, no way. You didn't do anything wrong. It's just, I'm not sure about doing this."

"Doing... what?"

"Don't do that, Sis. You know what I mean. I'm still..."

"Worried about out there? I'm not that crazy. If there was any chance of getting caught I-"

"No, that's not what I'm talking about either. I'm... ok, I'm just going to say it." She leaned forward, ensuring she wouldn't miss a single word. I took a deep breath and divulged, "I'm a virgin."

Ashley furrowed her eyebrows. Her head craned to the right. I could feel her eyes drilling into my skull. It was uncanny having her stare at me so distinctly. The mix of emotions on her face made it hard to discern what she had on her mind. The way she curiously wiggled her nose clashed with the mischievous licking and biting of her lower lip. At last she asked, "Oh Tiger, why did you have to go and tell me something like that?"

"Um, isn't that something I should be telling you? Before we finally do it, I mean. I don't want to mislead your expectations or anything."

"Tiger... Brian." Ashley's face bounced to normal as she placed her hands on my knees. "I don't expect anything from you. You've done so much for me already that asking for any more would be selfish and greedy. I want to be your perfect little sister." She rubbed her right foot against the inside of my left ankle. "I still am, aren't I?"

I felt better after hearing that. "Yeah, Ash, you're my perfect little sister."

"Good, I want to keep it that way." Ashley took her hands off me and leaned backwards, using her arms to support her from behind. "What did you think was going to happen tonight?"

"Huh? Nothing. Nothing at all."

"Come on, you must've been expecting something if you felt the need to share a big secret like that to me."

"Is there any way for me to take back what I said?"

"Nope. You're not leaving my sight until you tell me exactly what you've been thinking about."

"That's not fair. I already revealed one secret. Isn't that enough for tonight? If anything, you should be telling me one of yours."

Ashley flirtatiously swirled her tongue over her lips. "Ok, sure."

Now it was my turn to furrow my brows. "Really, you mean it? No comeback, no strings attached? You're just going tell me one?

"Yep, ask me anything," she beamed, kicking her feet in an alternating rhythm.

Her offer sent me reeling to the floor. Since when did girls give up classified information on a whim? There must've a hidden price of admission I was missing. I went over her last few lines but failed to find any loopholes. Studying her keen face the way she had studied mine, I came to the conclusion she was one hundred percent serious about the proposal.

As the notion had never occurred to me before, I needed time to come up with an eloquent question. My sister made her feelings for me pretty clear, so that slimmed my choices down by a considerable amount. That left me with 'What color are your panties' and...

"If we did do what I thought we were going to do, would I have been your first?" Although I had refused to explain my reasoning for telling her what I did, I was confident she would pick up on my intent.

"If," Ashley clearly emphasized, "we did do what you thought we were going to do, then... yes."

A huge wave of relief washed over me. I knew it wasn't supposed to be any of my business, yet I couldn't help but feel delighted at the news. When my sister said she had a crush on me, she loyally meant it. By no means did I consider myself the perfect catch, but I could never be truly happy with out relationship if I wasn't going to be her first. Despite our closeness with one another, her love life had been kept very low-key from me. I always felt if she ever wanted to talk about the subject, she would bring it up first. I had never pestered her about that special someone and she had never pestered me about mine. It wasn't until that morning we told each other everything we've wanted to hear.

"Can I ask you another question?" I blurted.

Ashley smiled at my optimism. "Go for it, Tiger."

"How did you get damn sexy? It's impossible for me to keep my eyes off you."

"You really think I'm sexy?"

My sister had to be kidding me. How could I say no having survived her relentless frolicking and foreplay? "Yeah, I do."

"Maybe I should save that answer for another time, or at least until you tell me another secret of yours?" Ashley sensed from my blank expression I had nothing else to share. "Well, to be honest, whenever I'm around you, I want your eyes on me. I love having your attention, to be all you can think about. And when I know I'm on your mind, I feel like the sexiest girl in the world. It's because of you I act this way. I know I said I shouldn't ask more of you, but I guess it's just a lie. Your devotion will always be what I want."

Her answer was infinitely more personal than I had anticipated. Time and time again, she amazed me with her pure emotions. "I don't know what to say, Ash, I-I'm... what happened to waiting for some other time?"

Smiling, she assured, "You don't have to say anything if you don't want to, but there's one more thing I need to tell you."

"You can tell me anything."

Ashley got off her arms and reached forward to hold my hands between us. "I'm not ready for tonight either. I hope you're not disappointed."

I entwined her fingers in mine. "Disappointed? This is the single greatest day of my life. There's absolutely nothing that could change that fact. I should never try to pressure you into anything you don't want to do. After all, it's my job to protect you from those types of guys."

Looking down at our hands, she said, "I know, but it must be hard for you to put up with all my teasing and not get any relief." The way she accentuated "hard" left me wondering if she was really looking at our hands or possibly even lower.

My cheeks began to redden. "Didn't you hear me? You don't have to do anything like that for me."

"I heard you loud and clear. But just because we're not ready for it doesn't mean we can't have a different kind of fun."

"Sounds intriguing. What are you suggesting?"

"Will you go along with whatever I decide?"

"As long as it isn't painful. You don't have any kinky fetishes I should be watching out for, do you?"

"What? No." Ashley jumped away from me. "I don't mean anything like that. Unless you're into it."

"No, no, I'm fine with normal fun."

"Okay, good." With a giggle, Ashley fell back onto her elbows and lifted her sock-covered feet between my legs to my chair. "Although I'm not sure if you'll be able to call this 'normal' fun." Pointing her toes toward me, she began to wiggle them into my crotch. "Can you believe it's only eight? I wonder if mom and dad are awake. Maybe they went to their bedroom."

"Um, ye-yeah. Maybe." Ashley's feet danced dangerously close to my erection. It never fully subsided since we left the living room.

In her infamously sweet voice, she asked, "Can you take off my socks for me?" With a small nod, I pinched the tips of her toes and discarded the feathery white rolls in the corner of my room. "Now, about that massage you promised me."

I remembered our arrangement from the drive home but couldn't quite put my finger on the promise part of the deal. Regardless, with the way Ashley was nibbling on her lower lip, I would've promised her anything.

Attending to her left foot first, I pressed my thumbs on the pliable flesh above her heel. Every one of her toes curled inward as I kneaded in small circular motions.

"Isn't this fun, Tiger?"

"Loads of fun." The devotion she sought from me was hers for the taking. I wanted to give my princess the royal treatment she deserved.

Continuing in circles with my left thumb, I plucked her tiny pinky toe between my right fingers. I wagged the toe back and forth a few times before moving onto the next one. I played with all five toes equally, giving one no more and no less attention than the other. If it hadn't been for her soft moaning, I probably would've forgotten I was supposed to be giving her a massage and toyed with her soft toes for hours on end.

Having spent ample time on one foot, I found the other trembling in need of my affection. My eyes traced her ankles and slender legs to her hips and smiling face. She lay on her back with her hands above her head. Her pink tee had risen past her belly, uncovering a canvas of sinless skin. Her peach-colored curves were undeniable against the dark blue sheets. The gorgeous minx dozing on my bed enraptured my soul.

"I love the way your eyes feast on me," Ashley purred, her sultry tone masking her for an experienced woman twice her age.

I grinned at the likelihood of feasting on her for real. Her lips have only been the appetizer for the main course. I wanted to devour her supple breasts. I wanted to luxuriate in the small valley between them. I wanted to trail kisses down to her most private of areas and taste her greatest inner desires.

But I was getting ahead of myself. I needed to finish giving my sister the massage I promised her. Focusing on the task at hand, I treated her right food as majestically as I did her left. Ashley squirmed more so than she did a minute ago, even though my technique remained relatively unchanged.

"Scoot back a bit," I suggested. Ashley bent her knees as I rolled my chair toward the bed. She crawled backwards until her legs lay flat on the mattress. "More comfortable?"

She fluffed a pillow beneath her head. "Mm-hmm. You're so thoughtful."

"I try to treat others the way I want to be treated."

"That's a new one. Did mom and dad teach you that?"

"Yeah. When I started kindergarten."

Ashley giggled quietly. "Mmm, this feels great. I'll be sure to return the favor."

"Isn't this supposed to make up for the massage you gave me last night?"

"That massage was more for me than it was for you. It felt wicked letting myself go on top my big hunky brother. It wouldn't be fair to hold it against you."

I was so preoccupied with caressing her heels I almost missed what she called me. "Oh I can believe it all right. But you shouldn't underestimate your power over me. It felt fantastic for me, too."

"You really mean that?"

"Best massage I ever had," I firmly replied.

"You sure know how to make a girl feel like a million bucks."

"Then I must be doing a crappy job with this massage 'cause you're worth way more than that."

I triumphantly evoked a laugh from my darling sibling. "How easy is it for you to make me laugh? Because I can't stop doing it when I'm with you."

"I'm only telling you what I'm feeling. There's nothing complicated about that. What I feel is... what I feel. It's as natural as breathing."

"There's a lot more to you than meets the eye."

I chuckled through my nose. Maybe I was more charming than I'd been giving myself credit for. My dates would disagree, but I wouldn't be giving my sister a sensuous massage if I'd hit it off with some other girl. Blessings in disguises, that's what they were. Ashley's the only woman I was destined to love.

Glancing at my clock beside the bed, I figured I'd been caressing her feet for over ten minutes. It was more than I predicted, but the night was still young and our fun didn't need to be rushed. I would have all the time in the universe to enjoy the rest of her body.

I initially planned to caress her legs and up her thighs. As I slipped my hands through the flared sleeves of her jeans, my fingertips encountered into a tricky obstacle. "Ashley, I can't go any higher. Your pants are skintight."

"What do you suggest we do?" she asked calmly, teetering on the brink of full relaxation.

"I could massage over your jeans, but I don't think you really want me to do that." I demonstrated the shoddy technique by rubbing her calves through the sturdy garment. Compared to her skin, my palms felt like they were scraping against sandpaper.

"Isn't there another option?"

I didn't bother sugarcoating what I wished for. "You could take them off."

"Take them off?" Ashley feigned surprise. "Is that all you can think about? Getting in my pants?"

"It's only my advice. If you rather keep them on, I can deal with that."

My words fell on deaf ears. Ashley's hands descended to the front of her jean. Her agile fingers unbuckled the studded white leather belt. As the metal clasps came apart, she pulled the strap from around her waist. A glaring gold button gleamed below her more adorable belly button. All it took was a small snap to make the tiny barrier disappear from the picture.

The only hurdle left was a thin row of copper teeth. Pinching the zipper handle, Ashley guided the key downwards, exposing an ever-growing patch of pink with every opening of a hook. Her hips rose from my bed. Inch by slow inch, she eased her pants down her thighs. Letting go of her ankles, I leaned back to enjoy the rest of the show. Ashley stopped when her jeans reached her knees. "Can you help me finish?"

I nodded, my shaky hands reaching for the waistband. As I pulled it down, I nearly came in my pants. It was the simplest and most erotic striptease I had ever seen.

"Is this better for the massage? I hope I didn't make it harder for you."

Ashley had no idea just how hard she made it for me. God, she looked un-fucking-believable. I've done my fair share of groveling when she wore tight shorts and hiphuggers, but nothing could've prepared me for the sight of her in lace panties. She posed with one leg straight out, the other bent, and forearms crossed under her breasts. The models in Victoria's Secret catalogues couldn't compare to the sexiness of my sister. Ashley was a perfect pink wet dream, and I was quickly becoming a huge fan of the color.

"Let's forget the massage," she said, beckoning me with her hand. "There's something else I need right now."

I eagerly wanted continue the massage now that Ashley was undressed from the waist down, but considering she hadn't disappointed me yet, I decided it would be in my interest to follow her lead. I crawled on top of her, keeping my eyes on her panties during the ascent. Ashley cupped my chin and steered me to her face. She didn't need to give me any more orders on what to do next. I dove down to her lips and covered them with mine.

An "mmmph" was the only sound Ashley could make. Reaching under my shirt, she wrapped her arms around my back and yanked me down until our chests met. Her hands moved along my spine, her nails grazing my muscles. I may have initiated the kiss, but she was quick to take control. She rolled us over and lay on top me. I held her hips and felt the thin string of her underwear. Moving lower, I grabbed two handfuls of her bare ass.

"Ah, you're so naughty," she cried.

"I can't help it. You kind of have that effect on me."

"No kidding. Your cock is rock hard."

It was the first time Ashley explicitly mentioned my cock, and the first time I heard her say the word. Hearing it in such a sweet voice drove me into a frenzy. I groped her flesh as her head dove to the base of my neck. She licked upward to my mouth, sliding her hands out of my shirt. One of her hands joined the fun with mine on her ass. The other slipped between us to size up my hard-on. My erection jumped at her touch.

Ashley giggled into my mouth. "Do you want me to take it out?"

"Hell yes."

"This is going be the first one I see up close. I never expected it to be yours, although I've dreamed about it so many times."

"I could say the same. There were a lot of things I haven't been expecting until you flipped my world upside-down."

"Was it for the better?"

"Definitely."

Ashley lifted herself off of me and sat between my legs on her knees. She grabbed the top of my shorts, pausing for a few seconds to stare at the tent my erection made. "It's already bigger than I imagined it would be." I bent my knees and raised my hips as she had done earlier, allowing her to pull my shorts down. My cock bobbed beneath my boxers. It was on the verge of passing through the front opening.

"The anticipation is killing me, Tiger."

"Now you know how I feel every time I look at you."

Ashley placed her right hand on my erection, tracing it down my left thigh. Her thumb pressed against the head through the flimsy fabric, causing a bit of precum to spill out. My sister could feel it being absorbed into my boxers. "And what would this fluid be? A good sign, I hope?" As she continued to stroke my cock, I struggled to hold in the rest of my cum. The feeling of a woman's hand on my erection was unreal, and this was only the tip of the iceberg compared to what we may be doing in the near future.

Bending down for a closer inspection, Ashley sniffed the scent of my cum. "The smell, it's so strong. You barely orgasmed, too."

"It's precum, not an orgasm, and I'm doing my best to control it."

"Oh. It seems you have a lot to teach me." Images of my sister in a schoolgirl outfit flooded my mind. My cock spurted two more drips of precum. "Wow, I felt it jump. Don't tell me it gets bigger."

"It's already bigger than normal."

"Maybe if I let it out in the open, it'll have room to grow." My sister released her grip on her new toy. I raised my hips, aching to have her take off my boxers. Instead, she reached inside the slit, her fingertips barely making contact with my hot cock. Again, a spurt. "Calm down, Tiger, or else there won't be any left for me."

I held my breath as Ashley gently grasped my cock in her fingers. With a tug, she pulled it out from its confines, finally visible to the goddess that had caused it so many erections. I expelled a sigh of relief for not cumming instantly.

"So this is what it looks like. Have you ever measured it?" she asked.

"I never got around to it," I lied. The first time I became curious about its size was when I was thirteen. It had clearly grown since then, now over half a foot long and a healthy girth all around. I'd never been as excited as I was at that moment, however, and I was willing to bet an extra inch was added on.

"I'll help you measure it the next time I see it." Ashley waved my throbbing rod side to side, occasionally letting it go to watch it spring back to its neutral position. "Talk about hard. This thing could really hurt me if I smack it on my lips."

Another dribble poured out. Was she actually going to give me my first blowjob?

"Oh, and I'm only talking about it." She eased her grip on me, using only her thumb to trace the length of my cock. "Can I have a closer look?"

Ashley leaned forward, her head hovering inches above the tip. It took all my willpower to refrain from letting loose all over her face. But damn, would I love to see her splattered in my cum. I felt guilty for just thinking about it. I revered my sister endlessly, yet the image of her soiled in my cream was all I could see.

With the end of her left sleeve, my sister pressed it against the top of my cock, soaking up the precum. Bringing it to her mouth, she poked her tongue out to lick it. "Hmph, I think I need a bigger sample," she pouted. "Is it weird I'm afraid to touch it but I want to taste it?" Her mouth moved closer to the head until I could feel her breathing on it. My dick twitched at the sensation. "Like that, huh?" She pursed her lips and blew a hot stream of air over the tip. Ashley reminded me of a ten year-old blowing out the candles to a birthday cake. The orange glow from the lamp enhanced the illusion she really was in front of candlelight. "How's your nose?"