The Babysitter

She laughed. "That would just be gross," she said. "Anyway, when I told him that, he blamed it all on me."

"On you? Because he left a condom wrapper in the couch? How's that?"

"Because I make him use the condoms," she said. "He told me if I'd just do it like everyone else and get on the pill or use that whole timing thing, none of this would've happened."

"He sounds like a real prince all right," I said and then blurted out something I wouldn't have had I not had a drink and a half in my system. "Why do you use the condoms anyway? Shouldn't you get on the pill if you're going to be sexually active?"

She was unoffended. "I'm not that sexually active," she said. "Carl is only the third guy I've ever done it with and he's only the second one I've done it with more than once. If I got on the pill my parents would find out about it and would think I was a total slut." She shook her head. "No, I'm not ready for that yet. Maybe when I get a real boyfriend, one who likes me for me and not just so he can screw me, maybe then I'll think about getting on the pill, but I don't think that's gonna be happening anytime soon."

"No?"

"No," she fumed. "I'm starting to think that maybe the lesbians have it right. Guys are a bunch of assholes—excuse my language."

"You're excused," I said. "And you're right. A lot of us are assholes... present company excepted."

Another laugh. "No, you're not an asshole at all. In fact, you're very sweet. When I finally find the right guy, I think he's gonna be someone just like you."

"A married deputy DA with two kids?"

She slapped at my arm. "No, silly, just a nice guy. A guy who knows how to listen." She downed the rest of her drink. "One more?" she asked.

"Okay," I told her, taking her glass. "But that's it. You drink any more after that and you'll be smashed. I don't really want to explain to your parents how you got smashed at my house."

"One more," she agreed. "And I promise I won't rat you out."

I made her a fresh drink and, even though my own was still half full, I refreshed it as well. When I sat down on the couch I saw that Courtney had turned towards me a little more, which served to open up the view of the hem of her shorts again. It was even higher than it had been before, not quite high enough to get a peak at her panties, but up there. The crotch had also pulled tight, outlining the swelling of her mons and giving more than a hint of the split that lie just beneath. I had to tear my eyes away from this sight to keep from springing an erection.

"Thank you," Courtney said as she took her latest drink. "These really are good."

"I'm glad you like them," I said.

She took a thoughtful sip and then slapped at my arm again. "Did you know that I used to have the biggest crush on you?" she asked.

Actually, I did know that. When we'd first employed her as a babysitter—back when she'd been a tomboyish fifteen year old—her puppy love for me had been obvious. But I played dumb. "No," I told her. "I didn't know that."

"It's true," she said whimsically. "I used to dream that I was married to you, that you would take me to my prom dates, that you'd pick me up from school and drive me home." She shook her head. "Silly little girl dreams, I know."

"I'm very flattered," I said. "I trust you're over that now?"

She gave me a saucy look. "Maybe," she said.

Now it was my turn to flush. For the first time the inappropriateness of what was going on here tried to worm its way into my brain. I opened my mouth to tell her that maybe I should go get my checkbook and pay her so she could go home. But before I could do that, she blindsided me.

"Did you ever feel that way about me?" she asked.

Now it was my eyes that were having difficulty meeting hers. "Uh... well..." I stammered, unsure what to say.

"It's okay," she said, a slight frown touching her face. "You don't have to answer. I'm just a fat little girl. Someone like you would never be interested in me. Forget I asked."

"You're not fat, Courtney," I told her. "Not even a little."

"You don't have to make me feel better," she said. "I mean, look at me. They're never going to ask me to model bras in the newspaper."

"Maybe not, but those models are all emaciated freaks. You're a very beautiful young woman."

"You're just saying that," she said.

"Not at all," I assured her. "You're very cute, very nicely proportioned, and, if you don't mind my saying so, I think you're sexy as hell."

"Really?" she asked, beaming, scooting just a tad closer. In the process, her shorts rode up just a little bit more, finally exposing a hint of the panties beneath. My eyes dropped involuntarily down, seeing that they were pale pink in color.

"Really," I said, swallowing nervously and putting my eyes back on her face. "If I were your age and single, you'd had to fight me off."

She smiled. "You're sweet," she said. "And I wouldn't fight you very hard, either."

"That's uh... good to know," I mumbled, stealing another quick peak of her exposed panties. I just couldn't help myself.

"So... so... are you saying you have thought of me that way?" she asked me.

"Yes, Courtney," I admitted. "I have thought of you that way."

She let her legs fall apart just a little more, widening the view of her panties. I could now see a stretch more than half an inch wide, more than three inches long, including the elastic portion along the edge. The combination of the conversation we were engaged in and my fleeting views between her legs caused my cock to begin the normal biological reaction.

"Are you thinking of me that way right now?" she asked softly.

"I'm uh... going to have to take the fifth on that one," I replied.

She swallowed a little more of her drink. "You are, aren't you?" she asked, leaning a little closer. "Can I tell you a secret?"

"Uh... sure."

She gave a nervous giggle. "The first time I ever... you know... had an orgasm, I was thinking of you."

I quite literally didn't know what to say to this. My mouth dropped open as a surge of adrenaline went shooting through me and the rational part of my mind tried to activate the warning system that things were getting out of hand here.

"I shocked you," Courtney said, seeming far from upset by this. "I'm sorry. The booze is making me say things I shouldn't."

"That's uh... okay. Once again, I'm uh... flattered, but..."

"I'll never forget it," she said, before I could finish.

"You won't?"

"No," she said. "I was lying in my bed and I started... you know... playing with myself. I'd done that before, of course, but never to... you know... completion. But I was really horny that night, the horniest I'd ever been before."

"Really?" I said, knowing I should make her stop but unable. The vision of her lying in bed and playing with herself was powerfully erotic.

"Uh huh," she confirmed. "And that was when my crush on you was the strongest. God I was so hot for you. I would've done anything for you. So there I was, my hand in my panties, my fingers going crazy, and it started to feel better and better. And then I started imagining it was your hand down there. And then I started to imagine you were kissing me and touching my boobs. I got hotter and hotter and really really wet. And then I imagined you... you know... taking out your... your thing and putting it inside of me." She shook her head and sighed. "That did it. I exploded right there on my bed. I moaned so loud my mom asked me if I was all right."

My cock was now a solid ramrod in my pants. I had had many women talk nasty to me over the years—on the phone, in person, in text messages, in email—but never had mere talk aroused me as much as what Courtney had just said. It wasn't so much her words, it was the matter-of-fact, almost naïve way she'd told the story, the way she blushed as the words came out of her mouth, the way her eyes sparkled with a mixture of embarrassment and arousal.

Her eyes dropped down to the crotch of my pants where a prominent and obvious bulge had formed. "That turned you on, didn't it?" she asked, not with teasing, but with something like awe.

"Yeah," I had to answer. "Very much."

"Wow," she whispered. "It turned me on too. It always turns me on to think about that."

End this conversation right now! a part of my mind screamed at me. This is leading nowhere good. I didn't listen. Perhaps I would have if not for the fact that it had been almost four weeks since Cathy and I had last had sex, that it had more than a week since I'd even whacked off. I had a major back-up of testosterone going on and sitting before me was an attractive young girl telling me that she had masturbated to my image, that my image had in fact been responsible for giving her her very first orgasm. And her legs had come a little farther apart as well, showing more of her pink panties to me, more of her smooth inner thigh.

"I still think of you when I play with myself," Courtney told me, pounding a few more nails in the coffin.

"Do you?" I asked her.

"Yes," she whispered. "God, Steve, I'm so wet right now."

Courtney, you really need to leave. I meant to say that. I opened my mouth to say that, I swear before all that is holy and sacred. But that's not what came out of my mouth. "Are you?" I asked instead.

She nodded. "Very," she said, her hand dropping down to her upper thigh. "Would you think I was sick if I..." She took a deep breath. "If I were to... touch myself right now?"

I nearly choked. "You mean... right here?" I asked.

"I feel like I'm going to explode if I don't," she said, her fingers creeping a little further up her thigh.

"Courtney," I said, my voice shaky, my hands trembling, "this is a really bad idea."

"Please?" she pleaded, her fingers now touching the elastic edge of the panties, one fingertip stroking along it, one manicured nail scratching on it. "I'd really love to look at you while I play with myself, Steve. To see your face as I make myself come."

My tremors grew worse, my eyes now unabashedly staring between her legs.

"You could do it too," she said. "We could watch each other. There's nothing wrong with that, is there?"

There was, of course, a whole lot wrong with that, but her logic combined with the alcohol and my horniness refused to allow my brain to acknowledge that. She was offering to show her pussy to me! To play with it in front of me! To allow me to play with my cock while I watched her do this! And it wasn't really cheating. Not in the strict and legal sense of the word. It was just visual stimulation. Nothing more, really, than looking at a pornographic video, right? "No," I said. "I guess there really isn't."

She smiled nervously and licked her lips. Her left hand came down and slid into the edge of her panties. Slowly, she pulled them to the side, dragging the crotch of her shorts there with them, revealing her bare pussy to my gaze. It was beautiful, exquisite, everything an eighteen-year-old pussy should be. The area surrounding the lips was shaved smooth. The lips themselves were pink and slightly swollen, glistening with moisture.

"This is so hot," she whispered as she leaned back into the corner of the couch and spread her legs a little wider. While her left hand continued to hold her shorts and panties to the side, her right began to play, the fingers sliding up and down between her lips, delving a few millimeters between them.

"Jesus," I whispered, enthralled, my cock now begging for release.

"Take it out," Courtney told me, begged me. "I want to watch you do it too."

I reached down, opening my belt and unbuttoning my pants, doing it entirely by feel, not moving my eyes from her pussy for even a second. I unzipped and then raised my hips up a little. Doubt tried to push its way into my brain again—you're not really going to take your cock out in front of Courtney, are you?—but I pushed it right back. This was just visual stimulation. Nothing wrong with it. It wasn't like I was going to fuck her or anything.

I pushed my pants and underwear down to mid-thigh, allowing my rigid cock to spring out. Courtney's eyes locked onto it as it hit the air. Her breathing took on a heavier tone and her fingers began to move faster in her slit, to slide further inside of her body between strokes.

"Play with it, Steve," she told me. "I've never seen a guy do that. Play with it."

I started playing with it, taking myself in hand as I'd done a thousand times before. I slid my hand slowly up and down, knowing that if I went after myself aggressively I wouldn't last thirty seconds. Through it all I kept my eyes glued to Courtney, drinking in the sight of her masturbating for me, watching as her lips grew wetter and more swollen, as her clit popped out of its hood, begging for attention of its own.

"Oh... Steve," she moaned. "This is so hot, isn't it?"

"Yeah," I breathed, my strokes going a little faster now as she started playing with her clit.

"Do you like my pussy?" she asked. "I just shaved it this morning."

"Yes," I said. "It's beautiful."

"Mmmm," she moaned, flicking at her clit a little more. "Ohhhh, oh, Steve. Your cock is so nice. So big and hard. Will you put it in me?"

I swallowed nervously. Hadn't I known she would ask that at some point? I tried to maintain my willpower. "I can't, Courtney. Let's just keep doing what we're doing, okay?"

"Oh please, Steve," she moaned. "Just for a second? I've never had one inside me without a rubber on it. I just want to know how it feels to go bareback."

"Courtney..."

"Please," she begged. "Just put it in once and then you can take it out. Just let me feel what it's like?" She stopped diddling herself and spread her lips open instead. "Just once?"

I found myself standing up. My pants and underwear fell down around my ankles. It wouldn't really hurt to put it in her just once, would it? I mean, the poor girl just wanted to experience the bareback sensation. You couldn't blame her for that, could you? And it wasn't really cheating if I just put it in and pulled it back out. Not really. It was more like an education thing, right?

"Just once," I told her. "Just once."

"Yesss," she moaned. "Just once."

Her legs opened wider as I stepped forward. I put my knees on the couch between them and leaned forward. Her left hand stayed in her crotch, continuing to hold her shorts and panties to the side. Her right hand came up to my face and stroked it. I leaned forward, supporting myself with my right arm by putting it behind her head. With my left, I took my cock in hand and aimed it between her wet, slippery lips. The head made contact and I slid it up and down a few times, prepping it for its one (and only one) trip into Courtney's body.

"Do it," Courtney panted, her hand sliding down onto my neck. "Put it in. Let me feel it."

I pushed forward with my hips. My cock met a little bit of friction for the barest of seconds and then slid slowly and smoothly inside of her. She was hot and wet and tight. We both moaned as I bottomed out, as my balls came to rest against her ass.

"That feels soooo good," Courtney said in my ear.

"Yesss," I whispered, just sitting there, unwilling to pull it out just yet.

"Just a couple of strokes in me?" she asked. "Just for a few seconds?"

I didn't even bother trying to rationalize this one. I just nodded and allowed my hips to start moving. I gave her a grind and then pulled back until my cock was just about free of her. I slid back in, bottoming out once more and giving another, longer grind. Courtney moaned loudly in obvious approval so I did it again. And then again. And then I did it even more, starting to move a little faster within her, to push a little harder against her.

"Lay on top of me, Steve," she said. "Lay on me while you fuck me."

I leaned forward, allowing my chest to press against hers, feeling the softness of her breasts beneath her shirt. She pulled my head down to hers and kissed me, her tongue sliding into my mouth. I kissed her back enthusiastically, swirling my tongue with hers, sucking on it. She tasted strongly of apples.

We kissed and rutted against each other. I could feel her juices wetting my balls now, could smell the sexy aroma of her musk permeating the air around us. Her free hand slid down to my ass and began to stroke it, to squeeze it. My free hand slid under her shirt, worming its way upward, probing beneath her bra, until I was cupping her bare tit.

Courtney broke the kiss. She was panting like a dog, sweat breaking out on her flushed face. "You're gonna make me... make me... I'm gonna come, Steve! Don't stop. Don't stop!"

I didn't stop. In fact, I began to fuck her harder, almost slamming her with each stroke, angling my hips upward in order to stimulate her clitoral nerves. Her hips began to rise and fall against me in response. Our mouths came back together and we kissed hotly, wetly, obscenely as her orgasm overtook her, as her body shook and shuddered against mine.

It took her almost a minute to work her way through the spasms. As it faded she broke the kiss and locked eyes with me. "Come in me," she whispered. "Come in my pussy, Steve. No one has ever been able to do that before. I want to feel it. I want to know what its like."

"Yes," I said. "Oh yes."

"Ohhh, do it," she moaned. "Give it to me!"

I gave it to her. It was a simple matter of moving my thrusts into overdrive, of squeezing her tit a little harder, of kissing her sweet mouth and sucking her tongue. The pressure built upward and the waves of pleasure began to spread. She felt the tightness of my body and began to moan against me, saying, "Do it, do it, do it" between kisses. The peak built up rapidly but with a power I'd not felt in years. I began to shake and shudder. My breath tore in and out of my lungs. Courtney stuck her tongue as far down my throat as she could, her pelvis thrust back at me, matching my erratic strokes. And then the peak arrived and I exploded, blasting the inside of her body with solid jets of hot come.

"Yesssss!" Courtney screamed out, the sensation apparently sending her into another orgasm of her own. "Yes, yes, yessssssss!"

And finally, it was over. I collapsed atop her, my wilting cock still buried within her body. She removed her hand from between her legs so she could put both of them around my back and pull me tighter against her. We shared another long, luxuriant kiss, this one sexy and sweet instead of lustful.

When the kiss broke at last we looked at each other, both of us unsure what to say, what to do next.

"That was incredible," Courtney finally whispered. "I never knew it could be like that. So... so... hot and sexy."

"Yes," I said, feeling guilt and doubt wanting to work its way into my consciousness but keeping them barred for the moment. "That was extremely erotic, Courtney. You are very sexy."

She smiled, leaning up to give me an almost chaste kiss. "Thank you," she said.

We lay like that for quite some time, not talking, not thinking, just holding each other and sharing the occasional kiss. We knew that when we let each other go, the time for thinking would begin. And that would lead to the time for talking about what had just happened. I think both of us wanted to delay that moment as long as we could. Neither one of us were ready to wonder about what would happen tomorrow.