The First Time I Saw JenniferbyCockatoo©
The first time I saw Jennifer, I thought she was fairly pretty, but it’s not like my jaw dropped to the floor. My eyes didn’t bug out of my head, I wasn’t tongue-tied, or even nervous. You know what I said? “Nice to meet you.” That’s it. Really. Sure, I checked her out a little, but that’s automatic. All men do that. A quick up-and-down when she’s not looking. I saw brown hair, nice blue eyes, a pleasant smile. She had a mediums build, about 130 pounds or so, 5’5.” Cute little butt. I’d guess a 34B bra. I didn’t see anything remarkable. She was just like anyone you’d see walking down the street. I went back to work and didn’t give her another thought.
So, why I woke up the next morning with my own rock-hard cock poking uncomfortably into my belly was a mystery to me. Then I remembered the dream. God, it was the most explicit, horny, sweaty, dream I’ve had since I was a teenager. There was no plot. It was Jennifer, and she was just naked, and spread open, and fucking the bejeezus out of me. I could taste the sweat on her skin. I could feel the tight, wet resistance on my cockhead as I positioned it to push all the way up into her. That’s the thing about sex, about how it’s NOT all glamorous and comfortable like in the movies. You see, hear, and smell EVERYthing, and if you do it right, it ain’t pretty. You make a mess. You get all red-faced and hoarse from all the grunting and heaving, almost like you’d been laughing or crying too hard. You’re sore and soggy and aching.
That’s the kind of sex I was dreaming about with Jennifer. Thinking about it again brought my dick to the crest of its swell, demanding attention. I started stroking and thought about Jennifer, about the exact way her titties would look if she took off her bra- I thought they’d be sort of cone-shaped rather than round, with rosy pink nipples, tipped with pencil-eraser points that stick straight out… Oh, damn, that did it in no time at all! Left hand goes for the Kleenex box in one practiced motion, grab the goo as it squirts out… there’s really a lot this time, and I can’t believe how hard this thing is! It stays up, bobbing up and down like a hungry bird as I hobble off to the shower. It doesn’t go down for another ten minutes.
The next time I saw Jennifer, I must have looked at her differently. I was sitting at my desk, which covered my semi-soft erection pretty well. Maybe there was something in my voice. I tried to play it cool, but I’d been nervous about seeing her again all morning. It must have shown, I must have faltered, because she cocked an eyebrow at me this time, and walked away with a little extra swing in her hips. They held my gaze like my head was in a harness. There it is, there’s that ass. There’s that pussy, right in there. And there’s the small of her back, her skin must be so smooth, look at the curve of her spine, I can just see how it would flex as she bends forward and opens her ass cheeks so I can get at her tight little butthole and reach in front for her pussy, Oh god it’s sopping wet… Okay, that’s enough! Down boy! Down! You don’t want that circus tent in your pants here at work!
I never saw her turn her head back at me. I wasn’t looking at her head. But she must have glanced back at me. She must have seen me staring, because five minutes later, I got an e-mail from her on the office intranet: “Caught ya looking! Sweet dreams.” She knew, damnit, she knew. Oh, god, what was I gonna do? I’d be fired for causing a sexual harassment lawsuit. I had to cool it. I’d be polite, but nothing else. Nothing at all. I could think whatever I wanted, but I’d never let it show like that again. Never. Never never never. But then again, she didn’t seem upset. I think she might have even liked it. “Sweet dreams.” Does that mean it’s okay if I think about her like that? Was she flirting with me? I’m sure it’ll be all right, just be calm, play it cool, and don’t do anything stupid.
Easier said than done. I don’t know if you’ve ever really looked at women’s office clothes, but they’re really very revealing- a lot more so than you’d think, if you weren’t a man with an eye for such things. Take a dressy silk blouse, for example. If it has buttons up the front, there will be gaps between the buttons, visible from the left, if the front isn’t held perfectly taut. If the girl is sitting down, chances are you’ll be able to see down in there. And if she’s bending over and the blouse is hanging down, she can forget modesty altogether. Skirts? Don’t even get me started. They look frumpy if they’re cut below the knee at all, and most women will wear ‘em cut right at the knee, or an inch or two above. You can see right up there whenever they sit down, no problem. Given the choice between showing a little skin and dressing like an Amish matriarch, just about all the ladies go with the former. So did Jennifer. After a few weeks, I got to know what most of her underwear looked like through those little sneaky-peeks. This one time, she wore a v-neck blouse under a bulky suit jacket, and as she reached up to get something one-handed, her blouse stuck to the jacket and rode away from her clavicles, exposing almost all of her left bra cup. Her strap was drawn straight and tight, pulled away from the softly curving flesh of the upper half of her breast as it faded into her shoulder. I can still see it like she’s right in front of me: the image scorched itself into my retinas, like I couldn’t forget it if I wanted too.
I found myself making excuses to see her at work, to talk to her about little things or nothing, to brush her fingertips with mine as we passed documents and things back and forth. Everytime something like that would happen, I’d get a little zing. Once in a while, we’d find ourselves having lunch together. I never asked her out, it just happened a few times. I was taking a lot of trouble NOT to flirt with her. Oh, I was very friendly, I just tried to pretend I didn’t have a dick. But sometimes the little guy would seize control of my eyeballs and rivet them onto her body. Then, one day at lunch, as I was gazing stupidly between her buttons, she finally said something.
“Like the view?”
“Huh? Oh! Oh, god, I’m sorry. I didn’t mean… I’m, I’m sorry.”
“Oh, lighten up. Guys look. It’s a fact of life. I don’t mind it so much. In fact, I kinda like the attention. I’ts flattering.”
“You caught me looking before. You were a very good sport about it.”
“Thanks. You weren’t. I spent a week wondering whether or not you were going to do anything about it.”
“I didn’t want to be rude. Or forward. Or for you to get the wrong idea.”
“What wrong idea? That you find me attractive?”
That’s it. “Um.” This pleasant-but-plain-jane lady had me tongue-tied. What could I say? That I’d been dreaming about her day and night? That I masturbate daily while thinking about every little tiny detail I’d ever noticed about her? That she’s directly responsible for about a quart of my semen, measured out a spoonful at a time? How am I supposed to express the almost supernatural attraction that has infused every thirsty cell of my body like this? I’ve never been this strongly drawn to anybody before, and it’s scaring the crap out of me! Jennifer is not a model with long shining blond hair, tits that defy gravity, and legs that cause traffic accidents! She’s just an ordinary-looking girl, and I want her like I never knew what desire even was before this! You want the truth, lady? You can’t handle the truth! One word is all you get!
“Well, shit, I’d hate to think of how you’d treat me if you thought I was ugly.”
“Listen. Okay. That’s fair. Yes, I find you attractive. You probably don’t realize how much. I don’t understand it myself. I think it’s kind of scary, and I don’t want to be, y’know, that kind of guy.”
“What kind of guy? The kind that will ask a girl out? Man, you really know how to make a lady feel special, don’t you?”
“Um. Well, I’ve never picked a girl up. I’ve never really done that. Every woman I’ve ever been involved with was a friend first. A friend who ended up jumping my bones.”
A look of shock ran across her features- that adorable crinkle she gets in the corner of her eye when she smiles was ironed flat. Her mouth was opened in a perfect oval. She almost dropped her fork.
“Oh, god, you’re one of THEM! Do you have any idea how frustrating men like you are? Jesus Christ. Girls are taught from infancy that Prince Charming is going to swoop down and rescue us from spinsterhood, and then guys like you come along and just act all POLITE, like swooping should be the last goddamn thing on your mind! The only way to get your attention is for us to throw ourselves at you. Do you know how hard that is? Do you know how humiliating that can be when we get turned away?”
“See, you’re yelling at me. This is the kind of thing I was afraid of.”
“Arrrrgh. Look, things would just be a lot simpler if you’d only say what was on your mind. It’s never a bad idea to compliment a lady, okay?”
I didn’t have a response ready. Time to back it up and lighten the mood, I thought. Hey, I think she might be into me after all!
“If I’d thought that you were ugly, there’d be no problem. We’d be friends and associates, and that would be that. Simple.”
“Right. But instead, you wanted to be friends and associates while secretly hoping I’d eventually pounce on you like a hungry tiger.”
“Well, that’s what it would take, right?”
“Listen, buddy, you aren’t getting off that easy. You’re going to tell me exactly what you think of me, in excruciating detail. Right now.”
I muttered something woefully incomplete, which she accepted cheerfully, but it wasn’t even the beginning, and we both knew it. I asked her out, and she said yes, and we’ll be seeing each other tonight. That’s why I’ve written her this story. That’s why THIS is the beginning.