You know how sometimes, when you’re looking for something, you’ll find the thing you were looking for last time? I guess it happens to everyone, but once upon a time it happened to me every day for a week, and it was the strangest week of my life…
I’d overslept that morning, I was running late for a fairly important meeting, and I couldn’t find my watch. I’d got to the desperate stage thirty seconds before the end of the five minutes I told myself I had to find it: I was looking to see if, by some strange chance, I might have left it in the oven, that sort of thing. Anyway, right at the last second, I looked in a drawer where I was certain it wasn’t, and found a watch I thought I’d lost ten years ago. I decided it was close enough, and ran out the door.
During the meeting I remembered why I hadn’t cared much ten years ago when I couldn’t find the watch I was wearing: it was a bit too big, and rattled around on my wrist in a way that made it uncomfortable to simultaneously wear it and jot down notes. I wasn’t jotting down anything of Earth-shattering importance, in fact I was mostly just trying to look busy, but taking the thing off still made me more comfortable, and helped portray the image, to boot.
The meeting was with Lyle Standish, a client we all cordially hated, because he was so obviously insecure about his status. His watch was no ill-fitting plastic cheapie, but a Rolex, naturally. If you asked him he’d probably claim he bought it for everyday wear to keep the Cartier pristine. The same went for his suits, his car, and, most odiously of all, his PA, Jenny. We all cordially adored Jenny, and not just the guys, either. When Mr. Standish (as he insisted on being called) all but told her to run along because it was time for man talk in the big boss’ office, she would pass the time with us cubicle-monkeys out in the bullpen. She would always remember our names, ask after anyone we’d mentioned the last time, that sort of thing, and when we asked her what it was like being a status symbol for a guy with such an obvious inferiority complex, she’d just turn about a million candelas of smile on us and say “I can’t complain. It’s easy work, and he doesn’t chase me around the desk.”
We were all glad to hear that, though some of us wondered how the old boy restrained himself. She really was beautiful, and still is, I assume: naturally she was blonde and blue-eyed, that much was almost a job requirement. But there was more: I could wax rhapsodic about how she had the cutest little ever-so-slightly upswept nose, or how her cheekbones were so fine they could cut glass, or how she had the kind of body businesslike, but figure-hugging charcoal-gray pantsuits were made for, but I won’t. After all, I’ve got a story to tell.
So, after the meeting broke up, we were all going our separate ways when I heard an unmistakable voice behind me.
“Hey, Tony?” Jenny was calling. I turned around.
“Can you tell me what time it is?”
“Sure,” I said, “it’s…”
As I lifted my arm I noticed that her attention abruptly shifted: she seemed to be following the motion of my hand. I didn’t have time to look down at the watch before she suddenly darted forward, ducked smoothly under my arm and turned around. I could swear she actually pressed her caboose against me as she took my left arm in her right hand and turned it so she could see the watch-face. The contact was over as swiftly as it had begun: she twisted around again and seemed to unwind herself from me along the length of my arm, ultimately capturing my hand with her cheek for a brief moment before breaking the contact.
“Got it,” she said, as cute and breezy as ever. “Thanks!”
I was dumbfounded. Even accepting that she might find me attractive (which seemed unlikely. I mean, I’m not hideous, but I am a bit heavy, plus I’m about ten years older than her), Jenny just didn’t behave this way, at least, not in the office.
As I was making my way dazedly back to my cube, I realized that in among the distracting sensations I’d felt during our unexpected moment of intimacy had briefly been the feeling of her hand in my left pocket. I checked, and sure enough, I found one of Mr. Standish’s business cards in there. Jenny, I remembered, was in charge of handing them out, as though any contact less manly than a firm and dominant handshake would be demeaning to the “great man”.
On the back of the card I found two important data: one was a phone number, the other was the words “Call me” written in a distinctly feminine hand. There was also a smiley face and a rather creditably-drawn pair of puckered lips, but these were less important. I put the card down and tried to concentrate on my work.
At lunch, when my hands stopped shaking, I took out my cellphone and dialed the number.
“Jenny Bain.” Her tone was so professional I thought I had to have imagined the way she’d given me her number. Then I remembered she didn’t have my number, so she didn’t know it was me calling.
“Hi, Jenny. It’s Tony.”
“Oh, hi Tony! I was hoping you’d call.”
OK, so she sounded happy to hear from me, but I was still hoping she’d give me a few more clues. I couldn’t manage repartee more scintillating than “Great, umm…” Fortunately, she came to my rescue, bless her.
“Listen, would you think I was totally shameless if I asked if I could come over to your place tonight?”
“Uh, I guess not.”
I know, I know, very suave of me. But you get how that was approximately the last question I was expecting to hear at that point, right? She didn’t seem to mind, at least. In fact, she gave a throaty, sexy chuckle that went straight for my spine and raked it up and down.
“You’re a lousy liar, but that’s OK. You have any movies?”
“Great! We’ll chill out, watch one, open a bottle of wine… I feel like having a night in, but I also want some company, you know?”
“Sure, I get it. Hey, how about I cook us some dinner?”
“And he cooks as well, wow!” she said, with laughter in her voice.
The rest of the conversation went as smoothly as if it had been on rails: we agreed she’d come over at seven, I promised to text her my address, which I promptly did, and, just like that, I had a date with Jenny. I felt like I was dreaming, and I really can’t vouch for anything I may or may not have done at the office that afternoon.
In between the time when I came home and got the pasta puttanesca started, and when Jenny rang the doorbell, I was about as nervous as a teenager. Should I have cooked something else? What if she’s allergic to anchovies? Will she like any of my movies? What if this is all a great big practical joke? What if I’m about to be raped by a black guy dressed as Batman?
That last one was a bit far-fetched, I acknowledge, but so was the situation. A beautiful younger woman, who’s never shown any more interest in me than in anybody else, suddenly gives me her number in the most flirtatious way possible, and when I call it, she invites herself over to my place. Anything could happen, I thought, and checked my watch yet again.
It’s lucky I had that watch, really, since it means I can tell you that, objectively speaking, thirty-five minutes passed before Jenny arrived. If you’d asked me to estimate it, I would have gone way over. But, well, eventually seven o’clock did come.
When I opened the door I learned that Jenny also has the kind of body that tank tops and jeans were made for. When she saw me her eyes lit up and she grinned as though the door had been answered by a freshly-buttered Brad Pitt.
“Hi! Come on in. Dinner’s almost ready.”
“Cool! What are we having?”
“Pasta alla puttanesca,” I said with a flourish.
“Well, how Freudian,” she replied with a mischievous grin. “This ought to go well with it.”
“Oh, hey, you didn’t have to bring wine.”
She giggled. “Well, I did spring this whole thing on you, so I didn’t know how prepared you’d be.”
“It’s true, I was never a Boy Scout, but I have my moments.”
So saying, I went to impress her with what I call my “Kitchen-Diner Maneuver”, in which I seat her comfortably at the table and let her watch as I manipulate my culinary tools with consummate skill and perform the last couple of steps in whatever recipe I’m following. Damnedest thing is, I think it actually worked. I flatter myself that she enjoyed my cooking too.
Now, I swear to you that I didn’t decide to keep my DVDs on the bottom shelf with this in mind, but I have to admit that I did find the view very enjoyable as Jenny browsed my collection. The thin denim clung to her hips like a second skin, and she was wiggling her supple backside around more, it occurred to me, than was strictly necessary.
“You know,” I said, “I can’t believe you don’t have a boyfriend.”
“Oh, I do,” she replied, looking back at me with that same mischievous smile, with the wickedness turned up a couple of notches.
“You do?” I couldn’t hide my disappointment. “Then how come you aren’t having a night in with him?”
“He’s out with his buddies,” she replied shortly. Then the grin came back: “When the cat’s away…”
Before I could press the point, she straightened up with an air of decision and said “Nope, these aren’t really what I had in mind. You got any pornos?”
Once again I was paralyzed and dumbfounded. She turned around and looked at me: indulgent amusement at my expression was written all over hers.
“No?” She asked, in a butter-wouldn’t-melt tone, then took two slinky steps towards me.
“Would you admit it if you did?” Two more steps. Now she was looking down at me as I sat back on the couch, hypnotized by the sudden sensuality that infused her every word and movement.
“No? Oh, well,” she said, and whipped off her top. She wore no bra. Well, I reflected, she didn’t really need one. Her breasts were two perfect, perky handfuls that didn’t seem to know the meaning of the word “gravity”. I watched her cute little nipples descend perfectly vertically as she folded her knees, putting her hands out to steady herself on my thighs as she, um, went down.
“I guess we’ll just have to do like Grandma’s always saying.”
My confusion at what I hoped was a non sequitur was evidently plain to see on my face, since she looked me in the eye and provided amplification:
“Make our own entertainment.”
It’s not easy for a girl to sound or look ingenuous when she’s just bared her tits to you and is now on her knees fiddling with your belt buckle, but, well, this was Jenny. Sweet, considerate, adorable, wholesome Jenny, I thought, has just delivered herself of innuendo as though it were the most innocent thing in the world. Aaand, now she’s got my dick in her hand.
I looked down into her baby-blues as she dragged my pants down: they were full of amusement at the effect she was having on me. Without breaking the eye contact, she moved her pretty face agonizingly slowly towards my member, and the connection was only lost when she went under it and started licking my balls.
I couldn’t help thinking that every time I saw her after this night, I’d remember this moment. She’d never quite be sweet, wholesome Jenny the office angel to me any more, now she’d be gorgeous, naughty Jenny the office temptress.
What of it?, my mind demanded of me as she licked slowly up the base of my shaft before ringing the head with her pretty lips. The truth is, she was neither an angel nor a succubus, but simply a fellow human being. Like the rest of us, if you prick her, she only bleeds if you’re doing it wrong.
OK, OK, I admit it, I’ve post-edited my thoughts a bit. You try summoning up apt Shakespearean references while getting a blowjob. Seriously, try it, it’s fun.
She was hard at it now, holding onto my calves and bobbing her head and shoulders up and down with a will. She wasn’t looking up at me with those teasing eyes any more, so I let my head fall back and concentrated on trying not to shoot my load too soon.
Arguably, I failed. It’s hard to say, really: as you can imagine, I sort of lost track of time, and I wasn’t in the mood to look at my watch. Anyway, as I say, before too long she must have felt me start tensing up, because she took one hand off my leg and grazed my balls ever so lightly with a french-manicured nail just as I came. That scratch, light as it was, was the most intense sensation I’ve ever experienced.
As I sat and let the aftershocks subside, Jenny got up briskly, making her boobs bounce prettily, and took a sip of wine. Enough blood returned to my brain for me to realize that she must have swallowed, and I guess she saw that I realized, because she winked at me.
“Now let me guess,” she said. “The bedroom’s… that way, right?”
I nodded, she winked again and I watched her still-covered butt disappear through the only door out of the room she hadn’t already passed through. Presently I got back enough energy to follow, which you can be sure I did with alacrity, shedding my clothes along the way.
I got to the bedroom just in time to see her on her knees on the bed, facing directly away from me. As I came through the door she leaned forward and slowly peeled jeans and underwear at once off her beautiful ass. When it was fully revealed, and she’d come just far enough forward to reveal a hint of neatly-trimmed blonde bush to me, she looked back at me saucily and said “You got your second wind yet?”
I had to look down myself, but when I did I discovered that the butt-reveal had done the trick. I was, to my surprise, back at full mast.
Wordlessly, under the spell of my siren, I advanced on her sexy posterior. I took hold of her hips as I’d imagined doing earlier, and she gave a throaty noise of encouragement at my forwardness. Just at that moment, though, my better nature unexpectedly came back for a flying visit.
“Protection? Don’t worry about it,” she said.
My brows knit together. “Are you sure?”
She nodded emphatically. The intensity of the moment, combined with some residual feeling that, well, this was Jenny, were insuperable together. I placed my glans at the gates of paradise.
She gave a little shudder at the first contact, which threatened to shake me loose, but recaptured my dick as she settled down. I pushed forward, very slowly. She gasped and started to push back, but I shifted my hands round to her firm buttocks and held her still, relishing being the one to set the pace.
I bottomed out inside her and paused for a moment, savoring the feeling of our thighs touching, her ass pressed into the base of my stomach, and, of course, my dick totally encompassed by her little pussy. I pulled back until I was in danger of slipping out entirely, then set up a leisurely rhythm, working my whole length in and out of her.
When Jenny’s moans reached what seemed to me to be the right pitch, I started to pick up the pace, until eventually I was sacrificing depth for speed, staying deep inside her but pulling out no more than half my length at a time, with swift snapping motions of my pelvis. She seemed to like it.
Her cries reached fever pitch alarmingly quickly, in fact, and as I was contemplating slowing down to try and get us both across the finish line at the same time, she flushed suddenly and had a shuddering orgasm underneath me. I slowed down a little, but I was pretty close myself so it wasn’t long before I got back into that fast rhythm. She was just starting to whimper in time with my thrusts again when I buried myself as deep as I could go and unloaded inside her.
Shortly afterward, my legs became insistent in their refusal to hold me up any longer, so I pulled out and flopped down onto the bed. Jenny got up, let her jeans fall to the floor, stepped out of them and joined me, snuggling her naked self up to me in the crook of my right arm. After a while, she got yet another rise out of my dick and climbed aboard, riding me to a mutually satisfying conclusion, but after that she snuggled back down into the same position as before, and that’s how I fell asleep.