How I Didn’t Cum To Lose My Anal Virginity

Once upon a time there were two DJs called ‘Pete Mac’ and ‘Dave the Rave’. Actually, I can’t say for sure whether Dave was a real DJ at all, but Pete Mac certainly was. He did Friday nights at that infamous cattle market described in my previous post – the legendary ‘Norbury’ which you’ll find, if you feel like you must, not far from…er…Norbury Station.

One night ‘Dave the Rave’ (as Pete called him) arrived in tow with Pete who was in fact so keen on my friend ‘L’, had driven from another gig to see her that night.

Looking back, I realise Dave was actually Pete’s wingman; God was I viewed as a ‘Grenade’ as Mike ‘The Situation’ would call the uglier of two girls in a Jersey Shore episode (cultural reference from trash TV – yes I do whore myself intellectually every now and then).

But going back. Maybe I had been a grenade that night.  A pretty big one at that, although one with a pretty face and hopefully one that wasn’t a chore

So, to my best mate L.

L used to be let us say…pleasingly plump. I, on the other hand, was very voluptuous (my now boyfriend might call it Titian-esque – that’s Titian the artist, not Titan as the big ship) so the attention of two DJs (albeit one alleged) was, both to L and myself more than welcome at the time.

In the heady days of 1999 in fact it gave us real kudos.  As any clubber knows, irrespective of the nature of the club itself, being ‘in’ with the DJ bestows on one great status. What was a huge bonus that night for me was to find that, as it turned out, of the two boys concerned, it was Pete Mac who was the actual ‘grenade’ (of the two boys), thus leaving me with the deliciously handsome intended-to-have-been-shotgun rider, Dave.

Don’t get me wrong, Pete was far from unattractive looks-wise, but the fact he had his own place and drove an Audi something-or–another meant little to me but much to those in need of a  trophy boyfriend.  What I can say for sure though is Pete the (real) DJ was definitely, infinitely further down the looks-scale than Dave The (perhaps, might be DJ) Rave.

I thus by chance inherited the looker of the two (Pete’s heat-seeking missile programmed to target the inside of L’s knickers). Allegedly Dave was ‘staying on the couch’ at Pete’s because he was ‘having problems with his girlfriend’. So there we were, the four of us.

How naïve I was then.

To this day, and with a now world-weary cunt (as well as brain) I wonder still whether Dave’s ‘staying on the couch’ was a bait to lure ‘L’ back to the flat;  Pete had thoughtfully ensured her bezzie mate – that is I – would not be neglected so L would be more receptive to the lure of his bedroom.

So now here’s where some confessions are confessed. Over the past ten years it’s been believed I lost my anal virginity that night.

I didn’t.

I don’t exactly know how that rumour came about either.

Except I kinda do.

Basically L was in Pete Macs room and they were indulging and he aimed for a hole which L prissily but innocently informed him, as if his navigation had gone a little awry – ‘Ooops, wrong hole’ (unsure whether this was squealed, murmured, or assertively announced).

I’m told his response was ‘No that was the one I was after’. I can neither confirm nor deny whether L let him do it; if accurate recollection doesn’t elude me my belief remains, she did not.

Later when L was regaling me with her antics, I exchanged what had happened with me – and herein lies the confession.  Perhaps being a novice (you’ll recall I’d only had real sex once at his point) I wanted to look impressive and in all probability lied.  I’m sure I didn’t mean to – that it was inadvertent;  I genuinely believe there was miscommunication going on, but unfortunately it grew legendary, even disproportionate (between the two of us) as I didn’t feel I could ever correct the ‘mistake’ – until now.

Here’s actually what happened Mrs J as you are today, in case you’re reading this.

You and Pete Mac departed to his boudoir leaving me on the couch with Dave the Rave. Remember, I’m then at a time in my life when I was totally unaware of any physical appeal I may have had to any member of the opposite sex – or even mine, come to that,

Dave was the type of man I suppose I should have been ‘seen’ or coupled with in public. He was tall. Easily 6ft-more and broad. He had model-esque looks but on the traditional, bland, mannequin-type side. There wasn’t anything especially unique in his appearance. Attractive, absolutely; but not unusual. Brown hair, dark brown eyes, evenly proportioned face, wide shoulders, thick, hairy forearms – very masculine looking – a man’s man. I remember his build as medium, not overly toned but solid. Something in the physicality of him made me, overweight and tall for a girl, feel feminine while in his presence.

Just sharing a sofa with him seemed treat enough that night – any night in my youthful excitement. I wonder now did he see my chest heaving rapidly in anticipation. When his hand brushed mine as we reached for a drink on the coffee table, did he feel the same electricity as I, or was I merely a ‘favour to a friend’?

It was all so clichéd on reflection. To break the uneasy, randomly pleasant conversation he grabbed the remote and turned on the TV. And what appeared on-screen?

Porn – and not awfully good porn at that.

Oh how very predictable.

I wasn’t shocked – mildly embarrassed and a bit uncomfortable perhaps, but not shocked.

Nevertheless, the whole scenario was foreign to me (including the language of the ‘actors’ on the TV).

My first encounter with this kind of thing had only come only a couple of months earlier when L and I went to Sweden and found our ‘first class’ room furnished with free filth on demand. We spent eight marvellous hours, squirming hornily on our separate beds watching this hardcore new planet unfold. ‘White Angel’ remains a memorable title, if only by title alone.

At that time, babe-in-the-woods that I was, watching a woman swallow, or even have, semen in her mouth, disgusted me. It turned my stomach (oh god how times have now changed!). The material Sweden supplied was very different to the offerings I’d rooted from my older brother’s bedroom as a curious (some would say invasive) teen.  Certainly though after the ‘Swedish Experience’ I was far more at ease with the kind of stuff Dave had flicked on than I would otherwise have been.

And then suddenly it was as if the porn somehow gravitated from the small screen into the very lounge room itself.

Dave looked at me and said: ‘You know what happens now, right? What would happen in this type of movie?’

His heavy arm snaked round my shoulders and he pulled me in for that first exquisite kiss. Back then I was still really romantic. I could get lost in a kiss for hours; well……lengthy durations at least. I still couldn’t get my head round the fact I‘d scored the looker, let alone that he seemed attracted to me.

His hands moved down and I allowed them to explore my upper thighs.

Scenes of losing my virginity flashed back, and  I speedily removed my shoes; one less obstacle to worry about.

His hands became demanding. In my experience men prefer stockings and suspenders as opposed to tights. But as many a girl knows, tights are more practical and affordable for anyone prone to ladders like me.  Anyway, I knew they needed to go and I was all too aware of the control knickers – those reliable friends both holding them up and tucking my tummy in.

Somehow in the time it took me to get off my shoes  he managed to use his size and weight to have me lying on the couch, him on top, I had just enough freedom at my hips to wriggle out of the tights and knickers. It felt strange to feel my bare flesh on the couch. Another totally new experience.

I liked the experience of feeling a little crushed by him, I liked the physical dominance, the fact that he was totally in control. My senses were in overdrive, my dress riding up, my naked flesh feeling the material of the couch and his hands just stroking. The strokes were firm but there was something kind of forgiving in them. Forgiving of my inexperience I suspect.

Hunky as Dave was there was a boundary crossed that night though – the hairy back!

This is so not a turn on – speaking at least for myself.

Running my hands through the fur on his chest felt great; the knowledge of being with a man, not a boy, feeling safe and cradled – if only fleetingly.. But my hands, running over his shoulders and into a veritable forest of hair at the back – yuk! It’s still a no-no for me but that night I merely accepted his gorgeousness, finished at the top of his neck and restarted again, this time safely below the buttocks. This all happened just as Beckham was ruling the world, so being a Metrosexual wasn’t unheard of but for Dave, clearly waxing was not part of his Friday grooming ritual.

We somehow twisted to be lying side by side and I remember his fingers lightly stroking my bum. Normally I’m quite conscience of the size of my behind (these days I accept and embrace its roundness and bounciness) but in that moment I remember how intimate it felt. Ticklish. I had to bite my lip, unsure whether to laugh girlishly or purr like a kitten at the pure pleasure of having someone explore my body so delicately for the very first time.
Reality always bites back though, however young and idealistic you are.

He pushed the coffee table away with his leg.

‘Get on all fours,’ he instructed.

Obligingly I did as requested and felt my black dress bunch up round my waist. His hands gripped my breasts and massaged them. I was never keen on this. It felt weird having them pulled from a bra and I was self conscious they weren’t sexy.

On all fours and totally inhibited one becomes acutely aware of the concept (and power) of gravity -the underwire of the bra was markedly uncomfortable.

But pleasure can easily distract from the rational mind. I felt his cock rubbing against the wetness of my entrance. I didn’t grind against it, or apply any pressure myself.  I put myself completely in his charge.

Big Mistake.

Pleasant as it was, feeling the length of him externally, sliding playfully, darting quickly in and out, teasing my cunt, what I was not expecting was the sudden force of him pushing against, what my darling of today refers to as my ‘chocolate starfish’ (I’ve yet to join the Hollywood elite for a good, old-fashioned anus bleach). My body didn’t have to resist much because my evidently iron-strong sphincter muscles weren’t having any of it. I suspect though the jolt from my entire self didn’t warrant me verbalising his intent was not only highly unpredicted but a nigh-on physical impossibility – certainly not without some severe and thorough prior attention.

Perhaps he was as embarrassed as I because I found us both gravitating back towards the couch, sitting now as two teenagers who fancied each other but couldn’t act on the urge – first cousins perhaps. I felt a little impolite. I was grateful for the attention after all. I instinctively knew I wasn’t going to have sex with him now and the disappointment was crushing. I wanted to rescue the moment or at least have a tale to tell.

I opted for a hand job. This too was a newie for me. I once touched an oriental man’s cock in the toilets of a cruise ship when I was 15, but ran away after he slipped his fingers into my knickers.

As his trousers were down I didn’t have to worry about looking unprofessional in releasing the beast – that bit was done. What was concerned me was the thing which that had been thrusting at my….’rusty sheriff’s badge’ (as my current boyfriend also calls it) seemed to have retreated, diminished – shied away in embarrassment like our words and previous actions had.  The porn, still playing on TV, now seemed distant, contributing nothing positive to what ambience was left. Not even its blurred moans and Teutonic entreaties filled the space we so desperately needed to recover the place that we’d been.

Thank the lord I was a musician. I have a firm grip from the instruments I play and great rhythm – and with those talents I figured I couldn’t go too far wrong. What though – and I have no other word – frightened me was the sleeve of skin I found, all wrinkled and thick, like a fleshy nozzle that seemed to be overgrowing his cock. I’d never seen one. Most men in Australia are circumcised and the few I had encountered…well, let’s just say I’d never seen in that state. I was thus completely ignorant as to how best (or at all!) to deal with it.

The porn on the TV gave no clue or direction in respect of the matter, so I could only give it a guess by sliding my hand up and down. I noticed the head poking out depending on how low I handled this rumpled, alien entity called ‘Foreskin’ (which to this day still sounds to me like a nasty character from some sordid tale courtesy of Brothers Grimm, or maybe an adult Shrek).

But doing so made him moan. This was encouraging, as was the flesh firming up in my hand. Pretty soon that sleeve seemed to have disappeared and looked more like the penises I was more familiar with.

I was able then to get into my stride.

After the debacle of ‘my first’ not having cum (I refer once again to Dick # 1) and being significantly upset about it, I felt it of substantial importance I allow Dave the Rave to deliver his goods this good night.  And he was keen enough.  So keen in fact he was demanding I get back on all fours again, down on the floor. Whether the clenching of my buttocks, the knowledge there wasn’t a condom in sight, or my own mental image of how unflattering a position I felt myself likely to be in, I just pretended not to hear and pumped till the spout was nearly upon us.

Then though, what are you supposed to do with it? Where do you aim? God, it was someone else’s couch – that’s just bad manners at best right? Vandalism at worst. My head flooded with Swedish porn nightmares (not to say what was on the TV) so it seemed the only option was to direct the stuff back on him.

And there it was. A pool of cum – the first I’d ever seen; sitting (and I do mean sitting, like a person in a council-flat room wearing nothing but Y-fronts) there, on his hair-covered tummy.

What inspired me to do it I have no idea, but it seemed then and there a sexy thing to just rub it all in.  Maybe I wanted to rub it out of sight.  After my reaction to the Swedish porn cum-gargling thing it certainly wasn’t going anywhere remotely near to my tongue.

I suspect this lathering (because as everyone knows, it does whip up like shampoo) wasn’t what Dave wanted. He held me politely me for all of thirty seconds then nipped to the toilet to wash off his belly.

I will say it ended sweetly enough. L finished whatever she did or didn’t do that night with the DJ and I slept in Dave’s arms. Later I picked up my shoes, knickers, tights and then left.

But it’s here, I suspect, the miscommunication between L, I and the anal sex came in. Seeing my shoes off, (knowing the trouble they proved when I lost my virginity) L assumed I had had sex with Dave. Her reference to the ‘wrong hole’ and my mentioning Dave’s initial preference for the backdoor entrance somehow got confused. In my best friend’s mind I’d lost my anal virginity to Dave the Rave.

When as you now know I did not.

And, as per much of my life, sadly, all this it was a short lived love affair-cum-scene.

Excited by the two DJs and the potential for where it could lead, L and I were foolish enough the following week to pack overnight bags. If I were writing a ‘Hitchhikers’’ Guide to the Galaxy for Innocent but Sexually Adventurous Girl’ I’d have as Rule Two ‘Don’t bring overnight bag after first fuck.’ But we brought matching, satin, baby-doll nighties, clean clothes for the next day and considered hiring a limousine for our arrival. When we got to The Norbury, there was no Dave to be seen and Pete Mac was doing shout-outs and dedicating songs to someone called PAMELA!

Depending on your stance, age, gender or personal-political persuasion about the pros or cons of this, feeling outraged L and I nevertheless underwent a rite of passage most young women would admit to having experienced at some point themselves. We did a little stalking.  Or, actually, in hindsight, by some standards, quite a lot, but we all know everything is relative. I suppose though over a period of several weeks we did it about five or six times in total

It was a simple series of sorties, and something that kind of became a night out in itself. We’d drive first to Pete Mac’s flat, I’d climb in the garden to see if ‘Pamela’ (or whoever) had gone there and sometimes we’d put chewing gum in the key-holes of his car. Innocent enough I think….or psycho?  We girls know, don’t we, but never say.  Neither Pete nor Dave had a clue.

But….times moved on (they do so more slowly the younger you are) and I remember getting an invite back at some later date and Pete being very surprised L ‘remembered the route’ while I innocently handed round chewing gum during the ride for all of us to feast on, one way or another.

But ‘Dave the Rave’ was for me one of the ones that got away. In a cock sense I mean.

Some years later, I found myself in that Club again with L and this time her younger sister.  He came over to chat and bought me a drink which I took. We were babysitting L’s little sister, introducing her to clubbing and the whole clubbing scene.  As we staggered out, siblings leading the way, Dave pulled up in a red sports convertible – top down, one arm on the wheel the other hanging out of the door.

‘So are you coming back with me or not – last chance?’

It came out of nowhere this invite, and after such a long time.  Perhaps I exuded more sexual confidence than previously, or my slutty reputation in the club had by now grown out of proportion.

It was my last chance and I knew it.

I declined the offer though – for the sake of sisterhood.

Posted on August 3, 2011, in Anal Sex, Disappointing Sex, Teenage / Young Sex, Unusual Places For Sex and tagged , , , , . Bookmark the permalink. 1 Comment.

  1. Very very nice story…..

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