A True Story - Sex Stories

The Melbourne Sessions

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I was working a lot away from home in Melbourne in the late 2000's. The drill, as many of you would know too well, was to travel over from Adelaide on a Sunday evening every second week to work a week with the head office team and then return on the Friday night. The company looked after me well, the pay was good all expenses covered and a nice apartment right in the middle of the city, close to everything. It sounds more glamorous than it is in reality, but there were certain upsides in particular being able to play with men with some anonymity and a central location if required to host.

In that period there were quite a few men that graced the depths of what I think was probably my prime early 30s work-hard play-hard cock loving gay pussy. The internet was a bit clumsy for meets back then, so most of these men I met initially through old school hook-ups at beats and bars and word of mouth connections. And the latter was how I met the stand-out character from this era, a mature gent (as they all were) named James who came to me 'highly recommended' by another lover who thought that he and I would hit it off. And we did.

James was one of those older married guys I always seemed to attract and be attracted to. Late 50s maybe early 60s big bodied and a head taller than me. Mr Average in many way but also well groomed and stylishly dressed in the Melbourne tradition. He was educated and cultured, liked good food and he liked fucking younger men with the added element of delight that he was not only very well endowed but also liked in his words 'a touch of kink' along the way. Even writing that now raises my heart rate a little. For me, a lifelong lover of mature cock and always aboard for a kinky adventure, he was a perfect match and we made a good albeit purposefully discreet couple in and out of bedroom. Especially in the bedroom where James was a standout performer.

I will dedicate one word to describe his impressive cock - magnificent. Large in both length and heft, heavy to the point of a downward bow, handsome to look at, rampantly erect and ready to perform and masterfully controlled by someone who was sexually aggressive and measured in balance. A deadly weapon of anal destruction wielded by a man who knew how to use it effectively and was only too aware of the power it commanded. It's true I had a sexual relationship with James, but perhaps more accurate and shallow of me to confess that I really had a relationship with this man's cock. It was hypnotic. I'd just see it as it sprung from his underwear and I'd feel the endorphins release into my bloodstream. Let alone when I 'd suck it and feel its girth in my mouth, but more than anything else when he guided that fuck missile into my hungry arse and pushed it in flush, balls deep, there was just a wave of pleasure that swept over me as my insides wrapped around him and all my nerve endings tingled in parts I didn't even know I had. It was big enough to be pleasantly uncomfortable and a challenge, it made me concentrate, you couldn't take it for granted that it was entirely manageable. It took all my own experience to firstly cope and then to flourish on it. Even when he removed it from my hole and it stared me in the face his fat pink knob all glistening and covered in our love juices, I couldn't resist the overwhelming urge to mouth it and moan like a whore as I sucked him clean and his big shaved balls dangled around my chin. I felt his cock was made for me and he fucked me like it was custom made for my arsehole. A bespoke cock for a naturally deep anal slut. He told me he was as smitten as I was. It was a win-win.

Our get togethers usually began quite civilised. A meal at a nice restaurant or drinks at a trendy wine bar. He'd always gentlemanly offer to pick up the bill, and we'd fallback to my apartment in the city for a steamy big-cock big-hole fuck session late into the evening before his return from this secret second life to middle class Melbourne suburbia somewhere.

We would kiss and explore each others naked bodies. James particularly liked me licking and sucking on his arsehole and smooth balls which would in-turn produce a mighty bone-hard cock of 8-9" inches that he'd then bury into the back of my throat as I gagged and gasped for air, then plunge full-press raw into my eager bum as I spread my cheeks to entrap as much of his love-rod inside me. He fucked me with authority. He was a man's man and I was a manly bottom for him. It was proper man on man gay sex, he rammed that cock into me with intention, he made me work under him and there was a level of general intensity that was not for the faint hearted. We were both experienced enough to enjoy it that way. He'd pump me with brute force and I'd take a pounding. Every time he'd blow his voluminous load deep inside me, breeding me up with a whitewash of cum into my aching cunt that drizzled out the gape he left behind. It was always delivered with a firm hand and an element of dominance and more than a tinge of humiliation that I appreciated and understood. And grew to crave.

For the week-about I'd be in Melbourne, James would spend one or two evenings, or 'sessions' as we called it, with me at the hotel or otherwise. As these things can do when the chemistry is right, every time I opened my legs for that superb cock of his to penetrate me, he pushed me willingly a bit further along the kinky scale. He was methodical and progressive. I advanced quickly. When you’re doing something you love things tend to happen so you don't even realise it, so as the weeks and then months went by I was doing stuff with James that I had never or only rarely done with a man before and frankly, it was very exciting and anxiety inducing in equal measure. That nervous anticipation and a desire for his gorgeous cock that I wanted to please, added a special electricity to every fuck session.

It became quite normal for James to place his hand around my neck as he drilled exploratory caverns into my arsehole so deeply that I'd lift off the bed suspended by his cock and balanced with my knees raised up and my bum connected to his crotch and 9 inches of rock hard tool holding me in place. I'd feel myself almost lapse in and out of consciousness as he'd turn me into a helpless fuck puppet with his cock making me involuntarily move to his command and my own dick upright and hard without any further encouragement than his actions. I'd fear he was going to paralyse me with that cock so far inside me I was almost unable to move! Sometimes I'd just cum without touching myself. He knew how to play me and I was his instrument for his cock to perform an anal overture that I'm sure the neighbouring apartments heard every moan and whimper, finishing with all the grunts and groans a nine inch dick and insanely horny anal slut will produce on its gallop to the finishing post.

I too would enthusiastically impale myself on James' tool so that every millimetre was within me and we’d tongue kiss like proper lovers as I rode until my arse would be numb and my leg muscles burning. Then he'd flip and doggy fuck me with little resistance and slap my bum cheeks hot pink and stinging so that I’d crave that submission and find myself begging him for more. I was his anal cowboy on bareback mountain. I'd urge him to use me and fill me up, fuck me up and destroy my shameless gay pussy. I'd go somewhere in my head that allowed me to leave myself behind in pursuit of a desire to be fucked and find new meaning to my depraved gay desires. He'd strap my pale white bare bottom with his belt like I was a naughty toyboy and then loop that belt around my waist holding the end like I was a rodeo bull for him to mount and fuck, using the strap to pull me near and far and control my pleasure and pain. It felt good to be bad. I wanted him to make me work for his respect and the more I did the less I got, until he would reward me with his sperm and a wry smile at best. But it was all I wanted and needed. Minimal acknowledgement was fine, but that cock yes please, Sir. I didn't disguise my need for that cock. And James knew he had the key to my desires.

He sometimes taunted me by having me extensively eat his arsehole and suck his big pin-up penis so it leaked pre cum and his balls were all drawn up ready to explode, but refused to fuck me and instead had me finger and fist fuck myself under his instruction so that I'd humiliate myself like a desperate slut aching and begging for his cock. He would taunt me I that I hadn't worked hard enough to please him. That there were other men like me that he knew who were more worthy. I'd be nude awkwardly with my hand up my own arse and a hard cock just pining for him to give me that big bowed dick that I wantonly required. Instead he would deliver a stream of warm piss right into my face and instruct me to open my mouth to take it, something that would set off a chain reaction of thrilling kinky shame resulting in me simultaneously cumming, ejecting my hand from my arse and being drenched in a golden shower to then be given his sweaty bum cheeks to bury my face between and chase it with a taste of his arsehole to complete the manoeuvre. I’d be this wet gaping depraved mess, all embarrassed at myself for being so reckless and unhinged. And I’d still be so horny for him that no matter how much regret I felt in the moment I’d be aching to go again.

There were times he'd fuck me arse-to-mouth and mouth-to-arse and I would be delirious with both holes propped open feeling like I was one gay fuckhole from one end to the other and in between. He would talk me up as the hottest slut he's ever fucked, tell me how good my pussy is and how much he adores my body and what a hot guy I am. Then talk me down as nothing but a fat cumdump and the 'dirtiest little whore on Collins Street' and an 'Adelaide b-lister'. He'd kiss me like a lover and make me certain he was more boyfriend than fucker, then remind me in no uncertain terms I was merely an object for his pleasure and not my own by dumping a pump-load of sperm into my anus and leaving the apartment unsaid while I was in the bathroom. He'd leave me there naked and alone, wondering if I'd satisfied him enough. I'd wake up in the middle of the night naked on the bed leaking cum from my arse and aching from the dicking I'd received with my head spinning. Was I up to it? Had I done a good enough job? Does he still want me? Would he be back? When?

The mind games lived with me day to day and as the relationship developed further this element was as prominent as some of the sexual boundaries he was pushing me through. Sometimes James would turn up when he said he would, other times he wouldn't and just leave me hanging not answering my texts. He'd appear randomly in the lobby of the hotel behind a newspaper like in an old spy movie, or out on the street waiting he'd appear from the ether or I'd pass him by sitting at a cafe watching me, or be waiting in the multi-level carpark for me to turn from work. One time he sent a courier with a plain wrapped box of condoms to my work with a note saying I should go to the gay beat and get fucked by as many cocks as there are condoms (it was a dozen). Another time he left a message for me at the hotel reception with a box with a butt-plug in it and a card saying it was with love from a work colleague, making me wonder who really knew about us and who he'd told. Of course it was all from him, he was the master manipulator and I was his willing victim. It was a titillating game that bordered on the edge of exposure and I found I liked not knowing if and who knew what about me. It was contained to Melbourne, and that feeling o mystery and sexually charged intrigue came over me the moment I stepped off the plane.

One night we got very drunk and on the way back from a bar James dragged me down a laneway next to the hotel, behind the big dumpster bins with my pants pulled fully off and just his cock poking out of his trousers he fucked me raw and dry. In the lamplight, despite us having been at the end of a darkened brick lane, it was still not hard for passers by to see our shameless engagement. He was fast and furious. I revelled in it. He dumped his load in my bum, called me a cheap whore and left me there to collect myself and fumble my pants up with cum dripping down my thighs from the dick hole he'd left in me. I'll never forget the eye contact I made with an upmarket woman passer-by of a similar age to me, as I struggled to pull my pants over my shoes, staggering around pissed on vodka, and the look of shock and disgust on her face as her eyes darted from mine to my exposed bum. It still gets me hard with that uniquely sexy shame now. James meanwhile had disappeared without a trace.

He took me to a very fancy beachfront restaurant at St Kilda and another mature guy I'd never met before joined us and took my hand and placed it on his crotch under the table, revealing a hard cock he encouraged me to rub over dinner. I'm sure the waiting staff knew. I thought he was quite sexy. James and this man whose name I never knew talked amongst themselves like I wasn't there, then we all went back to my hotel and the guy fucked me bareback at the apartment while James gagged me on his beautiful penis and told me how the man knew my boss quite well. The man, in his 60s or even older, knew my name, where I lived in Adelaide and a lot of other details about me as if he'd read it from my resume. He fucked me rough and promptly came in my arse and said my (now ex) wife's name and wondered how she would react if she knew that her husband was taking in strangers cock and loads of cum on his Melbourne work trips. It was all risky, intriguing and if I didn't trust James it could've been a disaster, but he operated within that realm and I had the confidence to push the boundaries with him in control. And he would flirt with that line in the sand but never crossed it, which ironically made me trust him even more.

A few weeks after that incident at St Kilda, another guy he introduced to me at a bar fucked me in similar circumstances and James took great pleasure in watching me squirm as unlike the St Kilda guy, I clearly didn't like him that much. James then joined in himself as this man used me like a free whore as had obviously been arranged for him to do so. It was an out of body experience. They used my holes together simultaneously both cocks in my arse at one point and I thought I was going to split apart! Then I thought my god I am doing this and pushed back like a slut, surprising myself at how well adapted I was for this kind of thing. Then the man fisted me while I sucked both their cocks all while chatting to each other about me and insisting I remain silent or ignoring me if I did speak. I liked to think he was showing me off, that I was all hot and sexy and he wanted others to enjoy me. But he was just getting me used for his own pleasure, and he told me it was a way to get me to appreciate him more. They both came all over my face and in mouth and rubbed it in my hair and I slept like that, naked and alone. James messaged me the next day that I did good. It was all the encouragement I needed.

We went to dodgy pub near the Queen Vic Market one night and he had me play with his cock under the bar and he fingered my bum with his hand down the back of my pants, enough that it could be seen by some of the other patrons. Then we went to the toilet and he pulled down my pants in the cubicle and fucked my arse for a couple of minutes with me wailing as he was so rough and brutish, before pulling the door open with me fully compromised and leaving me to collect myself and disappearing first from the pub so when I came out the whole pub stared at me and I shamefully left alone. He had a bunch of these games intended to humiliate me then he'd fuck me the next time and we'd recall how crazy and kinky it was. And it was. I was slut shamed and as much as it mortified me, I liked it and I wanted more.

One time we went to an art exhibition by quite a famous Australian contemporary artist (now deceased) who I won't name, and James explained at length to me the influences and themes of the art, the backgrounds of the artist and the importance of it all in the modern world. It was all very highbrow and cerebral. Then he took me to meet the artist, apparently an acquaintance of his who spoke with a plum in his mouth and a tilted beret on his easily 70+yr old head. In an upstairs office we drank French champagne and James explained with the same level of eloquence and passion how enjoyable it was for him having 'unimpeded anal sex with heterogenous young men' like me. They laughed, we all laughed. I blushed deeply. I was an object int his discussion, like a vase or a sculpture, a soon to be nude around which they gathered to critique. I then sat in a chair and gave the artist a head job that aroused quite an impressive hard-on from him, at his insistence I then stripped totally naked and let him fuck me bareback and promptly ejaculate inside me right there in the office. At James' request I then sucked him too. I didn't see the art in it to be honest, I think it was just sex. But as I quipped "I don't know much about art, but I know what I like", said with cum dripping from my pussy and mouth, it was surely my own piece of performance art albeit somewhat more lowbrow. "He has all my men" James later told me. Implying the artist was neither impressed with me nor was I in any way important to him. Certainly not of any artistic significance.

There were lots of events like that with James. Six and a half months of it. An entire summer and autumn. He fucked me with that big beautiful cock and my addiction to it and his ever more risqué desires grew exponentially. It affected my work as I craved that man and those quirky shameful experiences more than any career advancement, and took time out or made compromises to my day to meet him early or do things with him at random instead of the work I was being paid for. I didn't care, I wanted that gay big banger of a cock more than any pay rise! I didn't even want normal gay sex anymore, it had to be adventurous and I wanted to be more than just a fuck toy for him, I wanted to be his muse. At that point I would've done absolutely anything he asked me. Nothing was off the cards. I reeked of desperation for it to continue. If I didn't see him I'd masturbate with a big toy in my arse thinking about his cock and our kinky adventures. He occupied my mind like an obsession.

After those intense months where I'd reached the point, at his urging, of considering moving to Melbourne then one day James stopped responding. He disappeared almost without a trace. In contemporary terms, he ghosted me. I called his friend and he said he didn't know. I went to the places he'd taken me and he wasn't around. I even reached out to the artist and received, predictably, no response. Had he been caught out and was in trouble? Had he found another guy to fuck with that beautiful big penis? Was he ok? It all went through my mind but as the days went by I realised I'd reached my use-by date. James had once said to me here was 'here for a good time, not a long time'. And I was the good time. A few months later, when I had anyway been by then seconded to another role where I wasn't regularly in Melbourne anymore, a text from him appeared on my Motorola Razr "Enjoyed your hole. Good luck slut".
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