Bob the Boat Guy

Sex Stories - A True Story - 3 Jul 2026

Bob ran the catamaran hire business at Glenelg beach in the late 1980s, and we became familiar with each other as I was a local and he was always ready with a smile and a wave when I walked by or went for a swim nearby, as I often did on a warm summer afternoon in my uni holidays.

He was early 50s with a lightly muscular, manly body, hairy chest, and he always had a tight pair of Speedos that left little to the imagination. Of course, that swollen pouch caught my eye, and I think I imagined his cock hundreds of times as I played up a bit to get his attention in my own brief bathers, eventually building up the courage to hire a boat from him and take it out for a sail. I did know how to sail but it was more about getting close t him than sailing an old surf at! It started the conversation and then led to me helping him pack up the boats after the day had finished. I did this a few times, hoping to get closer to him and it became obvious I think that I was there as more than a sailing enthusiast.

During one of these occasions, Bob asked me if I liked boys or girls, which was quite forthright, I thought at the time. I remember that I told him “both,” which was accurate for me as a promiscuous 18-year-old in my second year at uni, very much discovering my sexuality with more experience with girls to that point. But I had been with men too, and I had a strong interest in and desire for a mature cock in my life. And a bit of time on my hands to pursue it.

I guess that would be the 80s version of consent, which I most definitely gave him. There was a moment it became a thing, just a look or two that we shared. And for a few weeks of that summer, he became my gay love interest, mentor, and just a horny, hard, mature cock that I could trust to stuff my bum full of mature dick and pump me full of sperm.

To cut to the chase here, yes, Bob was a charismatic and good-looking man, and I found him very sexually attractive. I think he was the first man I lusted after and objectified, then, ironically, fell for. He had such a sexy, mature body, and it sounds strange, but I’ll never forget the gentle curve of his tanned back and a nice, firm, sporty bum. But the kicker was he had this absolutely fantastic, large, incorrigible penis. It became my obsession. As a young man who’d not sighted too many to that point, it was the best cock I’d ever seen, and I was completely enamoured with it. At around 7-8 inches uncut, it was quite big, but to me, it seemed huge (compared to my 6) and being uncut a bit unusual to me (who is circumcised). It just looked like a throbbing, pulsing, pumped-up, veiny sex weapon, and it made my knees weak, and I felt it belonged in my funpit. It was thick and snake-like, it was heavy and hard with a slight downward bend, so good I can envisage it clearly now, all these years later, and it would still rank in the top handful of big, meaty penises I’ve ever had the pleasure of taking balls deep in my hot, hungry cockholes.

And take it in my happy, hungry little asshole frequently, and increasingly without inhibition, I did! Bob would lick out my shame cave lavishly and poke his fingers into me like a proper gay pussy with an overgrown clit, making me moan and spread my legs wider to encourage him into me and to add another finger until he was 4 digits in. And I would get the prize of his fat, raging todger to suck on and his big, hairy balls to mouth and make sure he was so hard for me. Before, without the need for lube or a moment of hesitation, he would spoon me and slide his slobbered, uncut fuck rocket firmly into my horny young cunt and just fuck me properly hard and firmly like he seemed to intuitively know I needed.

It was all symbiotic. His big snakey dick found a natural pathway deep into my silky pink cock cavern, and we wriggled and writhed until it was just right for him to fuck me in deep, long strokes and exert his dominance over me, something I absolutely fed off and responded with an arched back and guiding his hands to my stiff little cock to grip against his thrusts into my supergay fuck hole. He’d withdraw, and I’d instinctively suck him clean with our eyes never breaking contact, before he would slam it back forcefully into my gaped gay gash and pump me hard until his sperm oozed into my depths, and we would kiss like lovers panting for air and covered in sweat.

Bob would raise my knees up nonchalantly and screw me like a woman and make me feel effeminate in a sexy gay way, so that my inadequacy as a man without a caging was more than compensated for by the depths and joys my insatiable asshole could deliver to him and to me. He would fuck and kiss me and tell me I was cute and pretty, then roll me over and burrow into my anus like he was forcibly settling a penal colony in my bowels. I loved the polarity of it. Start off nice, come home nasty. Just like me at eighteen; all sweet and innocent to start with, and then all horny and begging to be used at the end. I might start off a bit shy, then I’d be gaping my asshole wide for him and pleading with him to split me apart!

This was the first man I lay around nude with after sex, smoking cigarettes and posing for his private Polaroid pics with my asshole spread, oozing cum, and my full face showing to the camera. Happy to give him anything he wanted in return for more of that gorgeous and addictive mature penis. We would tongue kiss and cuddle naked as he’d finger my cum-filled pussy. I’d lick his asshole so intensively and passionately to get him hard again to fuck me again. I’d suck his cock, and he would just shoot a full load of cum down my throat, and I’d swallow every last drop and giggle. It was all so good for a young man, effectively with my L plates on in bed, and he made a fine instructor.

There were a few times when I’d be at his house until after midnight, once he’d dumped his first load in my bum just after sunset. I wanted us to be lovers, but I always felt like I was his toyboy, and in hindsight, it was more transactional for him than for me, and I could live with that. I mean, what did I have to offer him other than my enthusiasm and my body to explore and use? He was a mature, experienced man of the world. The conversation was minimal, but the sex was amazing.

As the weeks went by, Bob got more kinky and pushed me further. He was the first man to insert his whole hand inside my greedy young bum and slowly, gently at first, fist-fuck me. His rather large hand in my asshole was one of the most wonderful experiences at that time. I remember it clearly, thinking how proud of myself I was to handle it and then orgasm with his hand up me, desperately failing to grip against his hand with my ass gaped and surrendered! He fucked my mouth like he did my ass and got me to deep-throat his cock and drool like a drunk after too many drinks, which we had too, and on several occasions, I’d get horny and tipsy enough to take a beer bottle up my asshole after anal. This was as a party trick that I used to show off a bit to men for years after.

For me, this was all at a time when I was still at uni and living at home, so it was a grand adventure. A mature man who invited me into his own home for sex. A man who fucked me like the way I had always wanted to be fucked. And a man who made me feel like a sexy little fuck slut who craved cum and pushed me further down that route, a journey I was ready and willing to undertake.

I might not have won him completely, but for me, it was always about Bob’s gorgeous cock and the lessons he taught me in taking it. I would literally do anything for it. And I think I did everything I could offer then, and he needed more than that. And I needed more too. Which I can understand now; an 18-year-old with a horny gay cunt was never going to be enough for a man like him. Or maybe he felt he’d completed the conquest.

He was still pleasant to me at the beach, we chatted, I flirted, but he stopped inviting me back. If you’re out there, Bob, thanks for the good times.

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