Wednesday, April 3, 2013

Kaily - My First Time

So, I'm still in my nostalgic mood and continuing my series on past romances.  This is a little more erotic than most of my posts, it wouldn't be a very good "how I lost my virginity" post if there weren't a few graphic details.

I was a bit of a late bloomer in the romance department.  Hard to believe, right?  Yeah.  I wasn't always this tall, dark, handsome, suave, fast talking, and chauvinistic womanizer.  Well, I'm all of that except for the tall and handsome parts.  I was one of those quiet, sensitive, artsy high school guys.  We didn't get a lot of play.

In my circle of high school friends was this girl Kaily.  She was kind of like one of the guys, only hotter.  She was into the same music, the same activities (legal and otherwise), and we were all constantly hanging out.  I'm somewhat embarrassed to admit we would probably be considered hippies.  We wore the baggy clothes, some smoked clove cigarettes, other times it was pot, and we listened to a lot of Pink Floyd, Nirvana, and The Doors.  Ok, we were kind of grunge-hippies.  It was the 90's.

A couple of times Kaily expressed interest in me, but I wasn't entirely sure how I felt about her.  She was fun to hang out with but also was borderline preachy at times.  She was vegetarian, nothing wrong with that, but she was also one of those occasionally preachy vegetarians.  One of those vegetarians that will give someone hell about having a milk shake because of the living conditions of all those poor milk cows.  Or about what brands of clothes are more animal friendly.  She wasn't always like that, otherwise we wouldn't have hung out with her, but every once and a while it got ridiculous (especially since she didn't really know what she was talking about, she just blindly regurgitated things she'd heard).

Eventually, just before my senior year, the teenage hormone's won out and I gave in and we started going out.  I'd dated before, but I hadn't been past second base at that point.

Because we'd known each other so long there wasn't much of a getting-to-know you period.  After our first date we ended up in the back of my tiny car.  We were making out, I put a hand up her shirt.  That wasn't moving quick enough for her, she undid her bra and put my hand on her breast.  Her skin was incredibly smooth and her breasts were nice and firm.  We kept making out.  She was a really good kisser.  Again, I wasn't moving fast enough, she grabbed my hand and shoved it down.

 I was reaching new territory, literally and figuratively.  My hand traced down her smooth stomach to her waist band, she pushed it further.  Under her pants was a world of new sensations, a combination of butter-smooth skin under my fingers, the silk of her panties against the back of my hand.  Further down I could feel downy hair, the panties, and the skin all at once.

All those wondrous feelings and it was nothing compared to the wet, velvety softness I felt next.  Her pussy was soaking wet.  I ran my fingers around her lips, savoring every moment.  She moaned, her mouth against mine.  My dick was so hard it was almost painful, pushing against my pants, pushing against her.  I started sliding fingers in and out of her, amazed at the warmth and the wetness.  I couldn't tell what was softer, the silk panties or her pussy.  I had no idea what I was doing, no idea if I was touching her right, or if it felt ok.  I just went with it, lost myself in the experience.

We played like this for quite a while, mouths and hands everywhere.  She told me she really wanted to have sex but wouldn't until we had some condoms.  Not a bad first date.

A couple days later I was at a local grocery store looking for some trojans.  I couldn't find them and was mortified at the idea of asking for help.  I wandered aisle to aisle for what seemed like forever.  Then, when I finally found them I had to face taking them up to the cashier.  It was the middle of the afternoon, so I had to put it on the belt and enjoy the looks from the middle-aged housewives in line.  I have to say it was one of the most awkward hours of my life.

The next time me and Kaily were headed out I borrowed my parents SUV.  It was a lot larger than my car and you could fold down the back seats creating quite a large space in the back.  We didn't have any private place to be together, so I borrowed the SUV and we found a parking spot deep in the woods.

We started out the same way, kissing and groping.  Then the clothes started to come off.  I'd never seen a beautiful, naked woman in person before.  I was almost ashamed to look at her with lust.  Like I said, I was a quiet, sensitive guy.  Or maybe I was just nervous to have her looking at me naked.

When I was down to my underwear I actually sat up, facing away from her, to slide them off.  I looked down at myself, I was so aroused that I almost didn't recognize my own dick.  She sat behind me, draped herself across my back and leaned over my shoulder to look.  Then I started the process of trying to put on my first condom.  It was far more slippery than I had imagined.  I managed to get it on after what seemed like half an hour of fumbling around with it.

We turned around and I laid down on top of her.  We kissed for a few moments, I laid there, unsure what to do next.  Then I tried lining my hips up with hers, did a few tentative thrusts.  After a few seconds she reached down and guided me in.

It was hot, wet, and tight.  And wonderful.

I slid in and out in short, slow, awkward movements.  My knees were rubbing painfully against the car's carpeting but I couldn't figure out how else to position them.  She was so tight and smooth, it was an exquisite feeling.  Each movement was extremely slow and gentle, I didn't want to hurt her.  She laid very still, facing away with her eyes closed, letting me get my own rhythm.

Within moments I could myself getting close to cumming.  I didn't know a lot about sex but it would be embarrassing to come so fast, that was one of the few things I did know.  So I started doing math in my head to distract myself, 1+1=2, 2+2=4, 4+4=8, 8+8=16... trying to ignore her breasts pressed up against my chest, the sound of her panting in my ear, and her pussy so tight around my cock.

16+16=32, 32+32=64...

She was making these little noises, almost a whimpering.  I think I made it to 2048 before I lost count and had to start over.  The math definitely helped me maintain even though I frequently lost my place.

I made it 2048 a couple of times before I reached the tipping point.  I was losing control and no math was going to get it back.  My thrusts started getting longer and deeper.  She started to moan, a flush crept into her cheeks, she grabbed my back and pulled her body into me..  I could feel it, I was there, I thrust into her a deep as I could and came, shuddering on top of her.

We lay there like that for a few minutes, gasping, sweat cooling our bare skin.  Ever so slowly I pulled out of her and flopped down on my back next to her.  Kaily rolled over and put her head on my chest.  We lay like that for a while.

A few months later she left to spend a semester living with her father.  When she came back I broke it off with her, after four months without listening to the preaching I realized it just wasn't worth it.  However, somehow I don't think I'll ever forget her.

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