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A Diary of Sex

Aimless with Amy, Lucky With Lara

2005-01-31


(Yes, there's sex - you'll have to skip down a bit to get to it.)

So another week begins. But I do want to say thanks to sandbeacher, lildebkitty, and double-life for giving me a shout-out over the weekend. And also thanks to the extremely sexy Sheridan Claire for being the 25th person to list this diary as a favorite. I so have a secret crush on that girl... I wonder if I could convince her to come to Sin City for her spring break this year so I could fuck her? Yeah, I kinda doubt it too.

double-life sounds like he's ready to take the bull by the horns and start taking advantage when he sees an opportunity. Good for him! Hell, he may get shot down more often than not, and of course that sucks. But I'll tell you something - I've gotten shot down, or stood up, or disappointed, or whatever on plenty of occasions. Easy come, easy go. It's the chances I didn't take that keep me up nights, even now.

Here's one from when I was back in high school. My sophomore year I was in the big spring musical. I actually had a pretty big part - not one of the leads, but I had a lot of lines and stuff (I was the sidekick to the villain - talk about typecasting!). My character was supposed to be really old, so my costume and my makeup was very elaborate - lots of robes and a cape and stuff, and lines on my face to make it look all wrinkled and shit.

Which brings me to Amy. She was a senior and had a small part - she had a few lines in the first scene and then my character gets rid of her and she doesn't appear again. But offstage, she wound up being in charge of my makeup. Because it was so elaborate, it took a couple of hours to get me made up each night. We did the show three nights over a weekend, plus dress rehearsal, so for four nights I spent a couple of hours sitting in my costume backstage, doing nothing while Amy did my makeup. Despite the chaos going on around us, it wound up being pretty intimate. We'd be back in a corner, talking quietly while she leaned over me, working on my face. We got to be very good friends. And naturally I had a horrible crush on her, because she was sweet and gorgeous. Friendly, great smile, not the brightest girl I ever met but relatively intelligent, and a nice body. Taller than I usually go for, and medium-size tits, but a nice ass and great legs.

But here was the best part. After doing my makeup, Amy had to get into her own costume. She didn't want to get makeup on her regular clothes, so she would just put on an oversize button-down shirt to do my makeup before she got into her own costume. She'd button it up just above her tits, but no higher. So picture this - she spends two hours standing right in front of me, leaning over painting my face and blending my wig into my hairline. What that means is that I spent those two hours looking right down the front of her shirt, and I assure you she wasn't wearing much underneath. She favored bikini panties, and apparently saw no reason to wear a bra while she was working on me. Yep - I had an excellent view of pretty much all of her charms, and I had to spend a couple of hours staring right at them, less than a foot from my face, night after night. It's lucky my costume fit like a tent, because otherwise it would have been obvious to everyone around us that I was sporting one of my own.

At the time, I think that was the second-most-naked I'd ever seen a girl. To this day, I have no idea if she was aware of the fact that I spent almost all my time staring down the front of her shirt at her bare tits and teeny-tiny panties. I'm not entirely sure how she could have missed it, but she never said a word. We spent a lot of time together over the next few months, and there were a couple of occasions where I absolutely, positively should have made a move on her and didn't because I was a chickenshit. As you can imagine, I'm still kicking myself about it.

(HERE is where the good stuff starts.)

I hung out with Amy quite a bit over the last couple of months of school, and we saw each other a fair bit over the summer but I'd blown my chance. Also that year, I spent most of my time in the company of three other senior girls: Julia, Lara, and Winnie. They were all best friends, and I'd gotten to be friends with them after the three of them commandeered me to give them a lift to Julia's house after school one day in January, and since then I wound up spending almost all my free time hanging out with one, some, or all of them. They pretty much adopted me. Winnie and I almost hooked up right away, but the chemistry just wasn't right (my call, amazingly enough). But she actually lived in my neighborhood, so we caught rides with each other all the time and had a great relationship.

I'd had a crush on Lara for a while - ever since I saw her perform at a school assembly that fall. Have you ever been to a show and there's one person in the performance who just catches your eye, and you wind up just watching them? That was how I'd been about Lara. Fate had smiled on me that she and I wound up becoming good friends, but fate was also cruel, because she had a Very Serious Boyfriend. So I just enjoyed hanging out with her, because she was really awesome and really pretty hot, and that was that.

Julia, however, was pretty much the ringleader, and she had a huge crush on me. I liked her tons - but not like that. She just wasn't the type of girl that I was into physically at that time (petite, preferably with big tits). But gradually, she wore me down, until eventually we wound up hooking up, and for most of that summer we were going at it hot and heavy, though we didn't wind up having sex (again, my call - I'm not sure what I was thinking, but in retrospect it was probably for the best). At the end of the summer, before we went off to our respective schools (she to college, and me to boarding school for my last two years of high school), she did wind up giving me my first blowjob (and hers was the first pussy I ever licked). At the end of the summer I broke up with her, because I didn't want to go off to school with a girlfriend that I was hardly ever going to see. I loved her, but I was never in love with her. She carried a torch for me for a long time, but eventually she found out something that made her hate me.

Fast forward a year, to the next summer. Everyone's home from school, but things have changed. I'm dating Ally, and it's pretty serious between us, but she lives at the other end of the state, so we only manage to meet up a few times, and keep in touch over the phone. Lara and her Very Serious Boyfriend have broken up, and though I was pretty oblivious to it, she's turned into quite a slut. Winnie was gone most of the summer on a trip somewhere. Julia still has a thing for me, but it's not the same between us, so I don't spend all that much time with her, because the whole situation is just too weird.

About half-way through the summer, I have to work on getting my college applications together. The school that I have my heart set on attending has a program where you can apply early in the fall, and get a decision before Christmas. You have to send in the first part of the application over the summer for this, and so after much nagging from my mother, I sit down to fill out the application.

This is a highly competitive school, so I'm very aware that everything about the application has to be utterly perfect. So immediately, I have a problem. I want a typewriter to fill out the application, because it's important that it looks good, and I have atrocious handwriting (seriously, one year in grade school, I got straight A's in every subject - except "Penmanship", where I got a C-plus). So obviously I can't hand-write it myself, and I have no typewriter, so now what?

Well, Lara had just finished her first year at the same school I was applying to. So, obviously, she had surpassed this particular obstacle. I called her up - turns out she had just hand-written her application. But of course she could, because she had the typical perfect girl-handwriting, just as neat as could be. Once I explained my problem, and that I was applying to go to her school, she immediately volunteered to come over and fill it out for me - I'd dictate, she'd write.

So about half an hour later the doorbell rings, and Lara comes upstairs (my parents were well used to seeing her by then - she was one of their favorites among my friends). We close the door to keep from being disturbed, and she sits down at my desk to fill out the application, and I'm sitting on the bed, which is right beside the desk. After about an hour, it's done. But we keep talking - in all the hanging out I'd done with Julia, Winnie, and Lara, Lara was the one that I'd spent the least time alone with for some reason - she didn't live all that close to me, as Winnie and I did, and obviously I'd never hooked up with her, as Julia and I did. But we were probably the most alike, really. We talked for a long time - eventually I was laying on my back on the bed with my head propped up on some pillows, and she was lying beside me on her tummy, propped up on her elbows.

We talk, getting to know each other a lot better than we did, catching up on everything that had happened to us in the last year, forging a new bond between us. She was prone to some stiffness in her neck - in fact, one of the things I used to do when I was with the three girls in Lara's car was sit behind her and rub her neck and shoulders while she was driving when it was bothering her. She made a comment that it was bothering her again tonight, so naturally I reached up and started massaging her neck. I rubbed her as we continued to talk quietly, getting closer to each other as the conversation grew more intimate. She mentioned that one of the biggest changes for her in the last year was that she'd learned to let things happen to her, and life would throw her unexpected twists. I asked if they were bad or good twists.

"Some were bad... some were good. I guess everything is that way. Hopefully the next one will be something good."

She was wearing jeans and a tight knit top. By the time, I was massaging under her shirt, reaching down her collar to rub her upper back and shoulders, caressing her almost. Her skin was soft and warm and supple. I was acutely aware of her firm breasts filling out her top and her bra so temptingly, and her leg next to mine on the bed, touching me (it was a twin bed, so there wasn't a ton of room on there).

As I kept massaging her, the conversation began to wane. Her eyes closed, and her head drooped forward as I kept stroking her. I took my other hand and put it inside her top on the other side, so I could rub both sides of her neck and both shoulders at the same time. The silence hung thick.

After a bit, she says quietly, "That feels really nice."

"I'm glad," I reply.

"Mmmmmm," she mumbles, almost inaudibly.

This goes on for a few more minutes. Then she raises her head and looks into my eyes, deeply, her brown eyes and my green ones gazing searchingly into each others' souls. Then she leans forward and kisses me.

Instantly we melt into each others arms, mouths open, tongues exploring, dancing, caressing, lips pressing urgently into the other's, her hands running over my arms and chest, my hands running through her long brown locks, touching her back and her head and whatever I can reach.

Eventually, she pulls away. "Stay right there," she tells me, as she climbs off the bed. I straighten my clothes a bit as she opens the door, and I hear her crossing the landing to the bathroom. A minute later, she comes back in, shutting the door quietly behind her. I was thinking that she was going to put an end to this spontaneous necking session that we somehow seem to have gotten ourselves into, but instead it's just getting started.

She crosses the room and gets back on the bed, lying on me, straddling me as our mouths and hands find each other once more. She lifts up a little bit and finally I can touch her magnificent breasts, those gorgeous tits that I have admired for so long and have visualized as I was masturbating time and time again (there were some really great pictures of her in the yearbook, let me tell you!). Her hands go to my belt, and then she's unbuttoning and unzipping and opening and pulling down and then sweet Jesus her mouth goes around my cock and shes licking, sucking, sucking, licking, sucking.

This is like my birthday, Christmas morning, and Halloween all rolled into one. How often do you find yourself in a situation where out of nowhere, a gorgeous girl that you've nursed a secret crush on for years is suddenly giving you a blowjob, and an expert one at that? To this day, I have no idea how it was that my head did not spontaneously explode. But it didn't... at least for a while, and then it was the head of my cock exploding jets of hot sticky white cum into her greedy mouth, swallowing every drop.

"Oh my God," I whispered.

She moved up my body, smiling at me. Once she got back up to where I could reach her, I grabbed her and kissed her, hard. She melted into me, and I turned her over, so she was on her back and I was on top of her, kissing her, running my hands up her shirt to fondle her tits, reaching around with on hand to unfasten her bra so I could play with her nipples. I lifted her shirt over her head so that I could lick them, and kiss them, and nibble on them, those hard little nubs at the tips of her milky white mounds heaving as she panted in pleasure. I kissed my way down her tummy to her waist, and I unfastened her jeans and pulled open the zipper, grabbing and pulling them off, leaving her nude on my bed.

Firmly I grasped her thighs and spread her legs open. Luckily for Lara, after months of eating Ally's pussy I had a pretty good idea of what I was doing, so I immediately applied my tongue to her pussy lips. I licked her slowly, gradually working my tongue into her slit. She was already wet, and soon got much wetter as I fucked her with my tongue, then replaced that with a finger and I moved up to tease her clit. Mindful of my parents directly underneath us, she kept quiet, but her panting and pulling on the bedclothes and curling toes told me everything I needed to know. Relentlessly, insistently, I licked her, and nibbled her, and bathed her, and finger-fucked her, until with a shuddering gasp and an arch of her back she came for me.

I licked her and pelasured her through her orgasm. Now that I had her completely within my power, I was going to fuck her.

I pulled off my shirt, and pushed off and kicked off my own jeans and underwear and socks, leaving us both naked. I moved up over her, my rock-hard cock pointing towards her like a lance, quivering in anticipation. Our mouths and tongues met again as I lowered my cock to her waiting pussy. She was soaking wet, and with only two or three strokes I was buried up to the balls inside her. Slowly but firmly, I fucked her. I kissed her neck, and fondled her tits, and I ran my tongue down to her nipples and licked around them as I fucked her with long, deep, deliberate strokes.

"Oh my god, oh my god, oh yesssssss..." she whispered dreamily into my ear.

Having cum once already, I was able to last a bit longer that I might have otherwise, but I don't think it could have been all that long. Mindful of the need for quiet, I couldn't cut loose and just fuck the shit out of her, but gradually we built towards the climax, slowly, gradually increasing the pace and ferociousness and the urgency of our fucking. Back and forth, in and out, fuck, fuck, fuck. Fuck, fuck, fuck. Fuck, fuck, fuck. We were lost in it - I was just a cock, and she was just a pussy, and together we were just a perfect passionate fuck.

Gradually, the pressure built in my balls, and I felt it coming. I happened to know from something Julia had told me that Lara was on the pill, so I had no qualms about cumming inside her. And that's what I did - my balls contracted, almost painfully, and I shot my wad deep inside her, branding her pussy with my cum. Jet after jet exploded from me into her as I pumped her into the bed, pinning her down, spreading her wide, filling her deep. Cumming.. cumming.. cumming.

Then it was over. Still coupled, we tried to catch our breath, smiling and panting, both of us with shit-eating grins splashed across our faces.

"Well, I told you these twists keep happening to me," she told me once we were both collected. She kissed me, hard. "And I'm glad this one was a good one."

Quietly, giggling, we got dressed and tried to make ourselves presentable. We emerged from my room, only to find that everyone else had already gone to bed. To this day I have no idea if anyone in my family had any idea what was going on in my room with me and Lara - I guess I should just be glad that no one ever opened the (unlocked!) door to check on us before they went to bed!

That was just the beginning of a year of erotic encounters between Lara and I, only ending after Julia found out about it and Lara and I agreed that we had to stop seeing each other. A damn shame, really. But I didn't want to come in the way of their friendship over what was really just sex. Had I been a little older and wiser, I might not have let Lara go so easily. But it was probably the right thing to do. Perhaps some day I will cross paths with Lara again and find out.

***

last fuck - next fuck

A Return of Regular Action? - 2005-03-31
Patience Rewarded - 2005-03-29
Infidelity... It's Everywhere - 2005-03-25
3 A.M. Eternal (KLF is gonna rock you!) - 2005-03-24
A Different Twist - 2005-03-21

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