Jillian’s eye-opener - Part One.

Hi everyone, I’m Jillian and I’m from Surfer’s Paradise on the Gold coast in Australia. I’ve only recently found Pixie’s pages but I just luuurrrve them. The other girls at work and I am wasting more time than we should reading stories, and now we’ve actually decided to start sending them in ourselves. We’re finding it hard to make them up, so we said we’d just tell some true stories about ourselves. It’s funny how you can recognise your friends’ writing styles. I read a story by “Elouise” which sounded so familiar I’ll have to ask my friend Louisa if it was actually her. (Duhh!) Anyway, if it is you babe, here’s my story about pretty much the same thing. Enjoy it girls (and I know the guys will as well, even though they might find out some of our secrets).

Have you ever wondered how hard it is for a girl? If we just motor up to some cute man and ask for sex, we must be sluts. If we don’t make things really obvious, we often as not miss out (and end up spending lonely time in the shower trying to get rid of that heavy feeling inside which stops a girl from sleeping). Thank God for the occasional boyfriend who hangs around for longer than a couple of months. By then he should at least have an inkling of when we do or don’t want some action, and also when those days are that action is definitely out of the question. The other benefit of keeping a guy for a while is that you can try some of those things that you’d consider too risky early in a relationship. I’d always been curious about my last remaining “virgin” territory, but I didn’t want some short-term lover walking out and forever referring to me as the “up-the-butt-chic”.

Gareth was my current squeeze, and he was an attentive, considerate and gentle lover. When you are going to offer your bottom for the first time, you are naturally a little hesitant, and you want a man who will take his time. To be honest though, since the girls at work had all been talking about anal sex so much, I was starting to feel a degree of urgency. I didn’t worry too much because the general opinion was that it was something that all guys were desperate for. The girls were always laughing about how their partners were always trying to bring the subject up, or would casually brush, bump, tickle, or get a bit “lost” in the dark and try to “accidentally” penetrate their little winking eyes.
My friend Jeannie kept us all giggling with tales of her new man, Mick, who tried to penetrate her date with his nose whenever he was down for lunch at her front door. We all thought it was pretty funny too when we asked Kerry, the youngest of our group where the strangest place she’d had sex was. “Ummm, up my bum actually… ‘coz Dave was so insistent.” (Needless to say, Kerry is a true blonde….heck, so am I.) What really kept making me so curious was that even though a few who had tried it didn’t like it, those who did like it couldn’t stop going on about how fantastic it was. They couldn’t properly describe what was so good, they just kept saying, “Try it sometime and see for yourself”. Then they’d gaze off into the distance with this flushed expression on their face. I couldn’t stand not being in on the secret any longer, and I was going to have to use Gareth to gain entry to the club.

Well girls,whoever said, “you can lead a horse to water, but you can’t make it drink,” must have been thinking about Gareth. I never realized just how hard it might be to get a guy to fuck my little ass. I’d decided that today was going to be the day long before we got to bed. I’d been thinking about it all morning and my little cunny was pretty much saturated. I also had this strange expectant feeling “back there” which I knew could only be filled one possible way.
I’d taken Gareth down to the beach for a nice long afternoon walk, and I knew he hadn’t missed the sight of the dark wet patch seeping out from the fork of my pale green bikini bottoms. Not only was it clearly visible, but I kept catching delicate wafts of my own scent. Gareth had to be catching them as well, and I knew that my smell turned him on. Out of the corner of my eye, I watched the growing bulge in Gareth’s straining Lycra Speedos and I knew it was time to head home.

I live in a nice condo on a canal just off the Nerang River, and in the afternoon the sun shines into my loft bedroom which overlooks the water. It gives a lovely soft warm quality of light for lovemaking, but it’s still bright enough to give you a good view of the working parts. By the time we’d got through the door and up the stairs, Gareth and I had managed to shed our skimpy swimsuits, and we fell onto the bed for a tasty prelude of oral sex. This had been part of my cunning plan, because I knew that while G was down there, I could give him an eyeful of my own squinting eye! Being a normal red-blooded male, he’d surely try to avail himself of its potential. This would save me having to ask for “it” and consequently risking the possibility of looking like some hungry-arsed anal-loving slut. Well, as they say, “the best laid plans etc etc”.
While G was doing his best work down there, I was almost oblivious. I was too busy with my own plans. G was lying on his back while I crouched over him and sucked on his schlonger. He had a very lovely, thick, circumcised number, and it was only now when I knew that it might soon be up my donut that I realised just how big he really was. “Hmmm, stop worrying girl and concentrate on the immediate issues,” I told myself. I figured that this position was giving Gareth the best possible view of my delicate little “chocolate starfish”, and he’d surely take the bait. Well, to his credit he just kept giving me the most tremendous head and never strayed from my clitty or labs at all. Maybe if I could just get him to shift a smidgeon backwards? I lifted my top half up a bit and arched my back more while pulling slightly forwards. I knew this was pulling my date closer to his tongue, and I pushed my legs wider to open things up a bit. I couldn’t believe it. He pulled his chin down and s! hifted away from my freckle. What was going on here? I started circling my bottom round and round to keep drawing my freckle within his reach. Every time I did, he seemed to avoid it again.
Oh well. Time for a change of strategy. I turned and pulled him up, and I knelt in front of him in his favourite doggie-position. I reached behind with both hands and roughly pulled to spread my cheeks as wide as possible. This time however, I arched slightly lower than usual, and I realized that if I pulled my knees slightly closer in than usual, then my buttocks would open a little wider. Surely he couldn’t fail to miss now. I felt Gareth rubbing his head down along the slit between my legs, all the way from my hood to my fork. I knew his penis would now be slick, and I braced myself for…..nothing! Well not quite nothing, as he had slipped into my cunny with a very wet sounding slurp. He started his usual energetic pumping, and although this would normally get me off, today it was very much the consolation prize. I was really wet though, and as he slapped in and out, I could feel the hot moisture of my juice running out of my cunny and down my legs. I was also aware of some ! of it spilling upwards and I knew that it was wetting my arsehole. In my mind, I could see it there, boldly on offer and yet neglected. Knowing it was now glistening, I started trying to both clench it and push it open to see if this would catch G’s eye. Sadly, it seemed that the only result of my exertions was to bring G to a peak, and he nearly climaxed right then. No you don’t , I thought, and I realized that a new tack was required. I dropped so that I was lying on my side and I pulled my top leg up and open. Gareth dropped down behind me and I knew he was now seeing my spot in all its splendour. I could also feel that this position actually let me push my date open even more. Surely he couldn’t resist. Surely the fleshy pink crater had to look like ground zero. Surely it would act like a magnetic homing device that would draw his penis to it.

Splash! Back into my cunt he plunged, and this was now really frustrating me. Did I need some bloody giant neon light on my back, pointing to my freckle, and flashing “Fuck here!”? Sure he was trying hard, but that slurp,slurp,slurp was really getting to me. Maybe I was just going to have to demand it. Then I got worried. What if he really hated anal sex? Had he realised what I had been up to and been politely ignoring it? Did he think less of me? What was I to do?

Thankfully “reason” then left me and “cunning” swung back into action. What I needed to try was one last change of position. Without a word, I swept out from beneath him, and lay back as if in classical missionary position. As Gareth moved towards me, I pulled my legs up as high as I could and tried to roll even further back. Damn hanging my legs over his shoulders; they were so far past my ears if I got them any further back now they’d be over my own shoulders! I knew the afternoon sun streaming in the window was spotlighting my holes; could he possibly resist now?

Fuck! He’d stuck it up my cunt again. I wanted to scream out, “Ass stupid, Ass. Stick it up my ass!” Garth was totally oblivious and pumped away without a word. In exasperation, I pulled as tight as I could, and suddenly G was spurting into me. He gasped and went to pull out, and as he did, he shot a load all over my wretched arsehole. Then I noticed his face!!! He was kneeling in front of me, but his gaze was locked between my legs. I didn’t need to be Einstein to realize that he wasn’t staring at my slot, but about two inches lower. Was this a minor success after all?

Gareth started stammering and trying to say something. He was umming and ahhhing and couldn’t seem to get the words out. Then I heard the most magnificent thing….. “Umm Jilly, I don’t really know how to ask this, but I’d really like to try anal sex. You don’t mind do you? Um, we don’t have to if you don’t want to….but I can’t help it! I’ve been transfixed by your hole all afternoon. Can we try?”

And that dear girls is how I got Gareth around to trying it. The story about how we actually did do it will have to be “Part Two”. (I think my boss has noticed that I’m flushed, breathing deeply and typing furiously; I’d better get back to work before I stick to the seat.) Let’s just say it wasn’t quite as easy as I thought it might be, but I’m definitely a convert.

Love Jillian.

(PS Gareth is past history, so if anyone “willing to start at the bottom” is ever travelling through the Gold Coast, drop me a line to [email protected] If you sound like my type, I might even give you a wink!)