Amy's Smile

Not that I wasn't aware that enough time had passed. I knew. And so did my royal member, who was still upset about not being asked to join in the fun earlier. Now he was spitting mad and drooling all over Amy's clean sheets. I was just about to break that bit of bad news to her when I realized there was a question I needed to ask her first. Well two actually.

"Um Peanut, we need to discuss protection." It had occurred to me that as a first time participant this might have been something that Amy hadn't thought about and since sex was the last thing on my mind when I'd stormed out of the house, I wasn't exactly prepared myself. For one heart stopping moment I thought that maybe the night's entertainment was going to have to be called on account of safety. But again, I hadn't taken into account Amy's zest for details.

"Oh," she giggled, "I almost forgot." Amy twisted around and opened the drawer on her nightstand. "I wasn't sure what kind to get so I just picked out a few different styles." She pulled a black cardboard box out and upended it onto the bed.

The thought occurred to me that Amy was a lot better prepared than she should be for a spur of the moment decision to fuck, and I was just about to ask her about that when I looked down at the pile of prophylactics in front of me. Apparently Amy's definition of a few and mine were a little different. "Shit, sweetie, they must have thought you were getting ready to host a hooker's convention."

"I bought the Condomania Pleasure pack off the Net," she admitted. "I went to the drug store, but I couldn't make up my mind and the pharmacist started looking at me a little funny after a while when I kept asking her questions."

I had no doubt that was true. The bed was littered with about a dozen different styles and sizes of condoms. Safes as my father used to call them, as in better safe than sorry I guess, but I could never quite get rid of the mind picture of some guy encased in black metal with a combination lock over his balls. I started to sort through the dazzling array. I found assorted Trojans, Durex, Trustex Flavored, LifeStyles, inSpiral,... the list went on. I picked up a Magnum XL and waved it at her face.

"Planning on getting a pony?"

Amy giggled, "I bought those extra, just in case."

I dropped the packet and choose something else, a red condom on a lollipop stick with a big smiley face. "And this is for the paperboy's next visit, I suppose?"

Amy sighed and rolled her eyes, "Could you just pick one?"

"Okay, sheesh, getting a little testy are we? I was just trying to have a little fun." I teased and then mentally kicked myself when I saw the look on Amy's face.

"I'm sorry," she whispered. "I know this is asking a lot of you..."

I stopped her with a fierce, hard kiss that shocked me as much as it did her. "Don't think for a minute that right now I'm not exactly where I want to be."

Her eyes searched my face, looking for a sign that I was lying. I let her look. Eventually, she sighed and a small smile played around the corners of her mouth. Her thin arms wrapped tightly around my neck and she pulled me to her with a strength I hadn't known she'd possessed.

"Charlie I..." She looked at me and smiled, then shook her head.

"What?" I said.

She lowered her eyes and shook her head again. "It's nothing."

"Oh don't do..." That was as far as I got as Amy decided to copy one of my tricks. She pushed her face into mine and latched onto my lips with a vengeance. A minute or two of that and I forgot how to think, let alone wonder what she'd been about to say.

But there was something that kept niggling at the back of my mind and finally I broke our kiss and pulled away so I wouldn't get drawn in again. "Amy?"

"Uh huh?" She yawned on the last part. Hmmm, now who needed a nap?

"Remember those zucchini you bought?"

She stiffened slightly in my arms. "Yes?"

"What did you do with them?" I watched her cheeks grow rosy and had to restrain myself from kissing them.

"Well I meant to - you know - but then I got this urge to make ratatouille and I didn't feel like going to the store again so..."

"So you ate them," I finished for her.

"Well it isn't ratatouille without zucchini," she said reasonably.

She had a point. But now the other thing she had, still had, as I'd been surprised to discover, was a hymen. Who'd have guessed that a modern 24-year-old woman could still possess such a thing? Jesus, didn't this girl ever fall off her bike or a horse or something as a child?

"And how did you know I..." Amy's eyes grew wide, she might be shy, she might be innocent, okay not as innocent as she was an hour ago, but still pretty naïve. What she wasn't however was dumb. I watched her face as she answered her own question. "Ohhhh."

"Yeah," I nodded sadly. "Oh."

"The books said that a lot of women break them by accident before they ever have sex," she mused aloud.

"We've already established the books can be wrong."

"I guess so."

I wasn't happy about the fact that I was probably going to hurt her a lot more than I'd been expecting to when I thought she'd had an up close and personal experience with a vegetable, but there was nothing I could do about that now. The look on her face told me it would be far worse if I tried to play the gentleman and ended our tête-à-tête.

I took my hand and stroked the side of her little face. When she smiled at me I took it as a go light and kissed her softly on the mouth. Oh well, I'd gone this far with Amy I wasn't about to stop now. But I was also damn sure I was going to make this as pleasurable for her as possible.

And that meant slow. Not that my own little prince was happy about that decision. (Shit, why do I keep using that adjective little?) As usual, he was only interested in immediate gratification, but for once I ignored him and followed my big head instead of the other way around.

My mouth found its way to one of Amy's delectable tits and licked it like it was the best thing I'd ever tasted, which thinking about it was pretty close to the truth. Amy tasted like vanilla and cinnamon and a hint of chocolate. Yeah, I could take it slow, especially if slow meant spending time like this. However I soon found out that Amy was a little impatient herself.

"Charlie, don't make me wait," she moaned when I continued to nibble on her breasts instead of moving further down.

"Peanut, haven't you ever heard the saying, getting there is half the fun?

"Uh huh, and I've also heard the one about a stitch in time saves nine. So what?" She thrust her hips up as a reminder of where she felt my attention should be.

To appease her, I slid my hand between her beautiful little thighs and stroked. She was right, she was as ready as she was going to get. Her pussy was soaked and gaping - just waiting for me to make my move.

I slid a finger into her hot center and felt her muscles contract around it. Shit, I wasn't sure I could get another finger in that tight little tunnel, let alone my dick. I wiggled around a little and felt for proof of her virginity. I was half hoping I'd been mistaken when I'd done my earlier reconnaissance of the area, but nope, there it was. I poked at it gently and Amy gasped.

Shit.

"Peanut," I studied her face for the truth. "Are you really sure."

"Charlie McKee," jeez she was using the same tone of voice my third grade teacher Mrs. Galuski, used to use when I didn't turn in my homework. "If you think you're going to stop now..."

"Okay," I muttered. "I just hope you're not a hard grader."

"Huh?"

Better to ignore than try to explain, I reasoned. "Look, I just don't want to hurt you, Peanut."

"God, Charlie, don't be such a wuss! How bad can it be? I mean woman have babies come out of there for heaven's sake. And it's not like you're really..."

"...big," I finished again. This conversation was getting real repetitive and I decided that if I wanted to stop it there was only one thing to do. "So, do you want me to put on the condom? Or do you want to do the honors?"

Apparently she was willing, because she rolled over and scanned the packs that were now scattered all over the bed. "Is this one okay?" She flashed a condom past my eyes.

"Um," I took a look, inSpiral was the name and if I remember correctly they were fun, but also funny looking and I wanted Amy moaning in ecstasy not moaning because her sides hurt from laughing. I grabbed another one off the pile. "This might be better." It was a Trojan Her Pleasure, which I thought was fitting for the occasion.

I handed it to her and she tentatively took a hold of it. Then she looked at my crotch. "I think we have a problem," she murmured.

I was just about to deny indignantly that I needed a smaller size when I realized what she was really talking about. Apparently the delay for our discussion on safety had made my dick sulky and now he was doing his turtle imitation.

"Well," I said. "What are you going to do about it?"

Amy grinned, like I told you, naïve - not stupid. She handed me the condom and then grabbed hold of my cock with a masterful grip. God she was a fast learner.

In no time at all she had my little prince over his pout and after one false start armored for battle. Now we were both ready for me to do a little storming of the palace wall.

Not that I figured on much of a fight. All through the ceremonial robing I'd been stroking Amy's pussy and it couldn't have been more appreciative of the attention. Now, I replaced my fingers with my thrilled dick and slowly ran it up and down her dripping slit.

Amy moaned contentedly. If she was nervous, she was better at hiding it than I was. I was already sweating as I slowly dragged my cock up and down her slit making sure to make content with her love button at one end and to gently push on her very wet opening at the other. I'd thought this might be a good way to prime her and apparently I was right because it didn't take long for her muscles to relax and she opened up in a welcome. I swear to God it felt like she was trying to suck me into her hot channel. I know every time I touched it, it gave me a kiss hello.

I looked down at her half closed eyes and winked. Amy responded by thrusting her hips up to meet me and since I was right there...

"Oh my," Amy's eyes shot open.

"You okay?" I managed through clenched teeth. Damn she was tight! My dick wasn't used to such close quarters though it seemed to be adapting pretty well. Apparently a cock has no issues with claustrophobia. Well not mine at any rate. I hadn't gotten very far though, only the head was imbedded in Amy's compact love canal. My dick being the greedy bastard he was twitched with impatience and I moved forward as Amy spread her legs even further to invite me in.

Oops, roadblock. I stopped at the barrier and looked into Amy's wide-open eyes. It didn't take a genius to see she was uncomfortable if not in out right pain.

"I'll go slow," I promised.

"If you do," she panted, "it'll hurt more."

I wasn't exactly convinced of this and Amy seemed to realize how I felt. As I made a half-hearted thrust Amy pushed her hips into mine hard. I felt something give and then we both gasped as my cock slid all the way home.

I froze; Amy closed her eyes and flared her nostrils as she breathed in deeply. I was just about to ask her how she was doing when she gave me that update on her own.

"Yikes!" she gasped.

"Oh God, I'm sorry! Let me..."

Amy wrapped her legs around my waist and held me in place. "Charlie, don't you dare move. Just give me minute or so to get used to it. You feel so big." She looked up at me startled and I grinned and winked. Amy started to giggle, then stopped abruptly when tense muscles let her know she wasn't quite ready for that kind of maneuver.

"Everything is relative," I whispered. The prince thought so too and positively flexed in pride. Amy's eyes shot open and her hands grabbed my arms and gripped me fiercely, as at the same time her right leg slid down until her foot rested on my tailbone where she proceeded to give me light warning kick.

"Sorry," I said, though I wasn't really, but I wasn't ready to risk a broken coccyx for the sake of honesty.

Amy decided to believe me and closed her eyes to concentrate on the new sensations she was experiencing. I took that as an opportunity to nibble on her neck and shoulders a bit, but always keeping my eyes on that heart- shaped face, waiting for the sign that she was ready for more.

I watched as the corners of her mouth relaxed and the small stress lines between her eyes disappeared. When she opened her eyes and smiled at me I knew she was expecting me to take that as my cue. But I had other plans.

I slid my fingers down her soft arms until I'd caught both of her wrists in my hands then I gently pulled them up until they met over her head. "How ya doing?" I asked softly.

Amy sighed, "This is an amazing feeling."

"Good." I went back to nibbling on her neck, but my hips stayed still.

Amy didn't say anything, but after a minute or two began to get a little restless. I ignored her and kept on tasting. Her legs gave up their death grip on my hips now and instead started to slowly slide up and down the back of my thighs. I felt every millimeter of movement, but still I did nothing.

"Charlie?" Amy sounded breathless and a little puzzled.

"Hmmm?" I bit down softly on an earlobe and felt her shiver.

"Um, don't you think we could uh, get going here?" She was almost whining, but not quite.

"You have somewhere you need to be?"

Swear to god, Amy growled. I laughed softly, but it turned into an oomph when she kicked me again, harder than that last, and finished it off by grinding her bony little heel into my ass.

"God dammit, Charlie, fuck me!" she demanded.

"Such language," I murmured, "and I'm not sure you're really ready. Maybe we should just wait for another twenty or so minutes and let the suspense build?"

Which was absolute bullshit. If I had to wait another twenty seconds my heart would explode but I was counting on Amy being too naïve to figure that out. I just wanted to string it out for a little longer and make sure that when I did move, Amy would be relaxed enough to enjoy the experience. Of course there was also the perk of driving her nuts in the meantime.

"Maybe," I continued in a voice that barely quavered, "we could just tal..." I ended in a groan. "Holy fuck!" I could barely form the words. "Where in hell did you learn how to do that?"

Amy gave one more satisfied squeeze to my cock and looked at me.

"The Internet," we said at the same time.

"You," I gasped as she undulated her muscles yet again. "Have got to give me the URLs for some of those sites."

"Maybe later," she hissed, "now fu..."

It was her turn to stop in mid sentence as I slowly slid out of her steamy channel. I watched her face as she processed the feeling, then monitored it again as I made a return visit. There may have been a slight twinge as I passed by her recently torn virginity, but other than that, I was happy to see nothing, but pleasure in those round chocolate eyes. I began to stroke smoothly, in and out, in and out, whispering how good she felt and taking little licks of the salty sweat that was forming on her top lip. I watched as her eyes widened again as real pleasure started to replace the initial feeling of fullness. Her legs started to make these little involuntary twitching movements and her hips rose to meet me as I kept sliding, sliding back and forth in her hot, liquid center.

She was still the tightest space my cock had ever visited, but now she was relaxed enough and wet enough that I moved easily, gliding down into her oh so soft tunnel, surrounded by a buttery smoothness that still managed to create an almost unbearable friction. I wanted this to last forever, but I knew I was too close, too overwhelmed by the fact that I was here - in Amy's house - in Amy's bed - in Amy.

I loved the way she felt in my arms, the way she gasped as I hit bottom and then made it even better by twisting her little bum to rub my pelvis into her clit. Her hair was damp now and curled in ringlets around her face and I loved the way they tickled my nose as I kissed away the tears that were still in the corners of her eyes from when I'd first entered her. I loved the taste of her, the smell of her.

Oh Christ, I thought, maybe I just loved Amy.

There it was, the truth I'd tried so carefully to put out of my mind. I loved Amy. And even as my hips quickened and the sweep of my orgasm began to dull my brain, that thought lit up my heart and then broke it as the realization that even though my feelings were real, so were hers and they weren't for me.

She gasped and I looked down at her, "Charlie?" She whispered and her eyes dulled as her back arched and she came hard.

That wasn't supposed to happen. Not the first time, not with just my cock to stimulate her. But Amy didn't know that. I felt her clench down on me, and then it was me who babbled nonsense words and gasped out her name as I slammed back into her pussy and held myself there as I filled the condom with cum. There was no thought now, nothing but this, nothing but Amy.

Dimly I heard her calling my name again, but it was her warm hands kneading my back that made me realize that I was in danger of crushing her. I was still sort of resting on my elbows, but it was close. With a last burst of strength I slid my arms around her and flipped us over, still joined, so that Amy now rested on my chest. I stroked her hair and waited to recover. I wasn't sure there was enough time left in my life for that, but it seemed like it was my only option.

Amy was quiet too. Her body bonelessly draped over mine and except for the feel of her warm breath on my chest and the trembling of her shoulders under my hands, I might have wondered if she was still alive. The trembling grew and an alarm bell went off in my head. I struggled to look up at her face, but she was turned away.

Oh god, I thought, she already regrets it. The greatest experience of my life and now I'm going to find out that Amy can't believe she made such a huge mistake. How could I have thought this would be okay? Amy loved Liam. He was the one she wanted, not me. Now, too late she realized that.

"Peanut, what's wrong?" I had to ask even though I already knew the answer.

"I'm... I'm cold," she finally whispered back.

Relief flooded me. Cold was something I could deal with. I gently disengaged myself from her and slid out from under her hot little body. I wasn't chilly, not in the least. Amy had a furnace that ran pretty hot for such a little thing. But then, it wasn't my ass sticking up in the night air.

I sat up and looked for a place to get rid of the condom. All I found was a wicker wastebasket. That wasn't a good idea. I reached for the quilt we'd managed to kick down to the end of the bed and pulled it up over Amy.

I kissed the top of her head, "That better?"

"Uh huh," was the muffled response as Amy had her face buried in a pillow.

"Okay, I'll be right back."

I kissed the back of her neck and stumbled my way to the bathroom where I proceeded to clean up a little. I grabbed a washcloth and soaked it with warm water and then returned to the bedroom. I hadn't been gone five minutes, but it looked to me like Amy was asleep.

I stared at her. God, she looked so vulnerable. She'd flipped over onto her back and the huge thick quilt I'd covered her with was pulled up to her chin. She was so thin she barely made a mound under it. I sat down cautiously, not wanting to wake her, but the movement must have registered because she raised her head and looked at me sleepily.

"Hi," she said.

"Hi yourself," was my brilliant comeback.

"Where'd you go?"

"To the bathroom." Amy nodded and closed her eyes. I leaned over and kissed each one gently. "I brought you a present."