Ai Era: Oz Beach Boy's Techie Toss

AUTHOR'S NOTES:

This is an entry in the AI: A NEW ERA 2024 CHALLENGE, so I'd really appreciate it if you could take the time to leave a score.

This story features my recurring character Matt (a muscular, well-hung, twenty-something, sex-addicted male exhibitionist) awkwardly and with limited success attempting to masturbate with a newly created AI sex programme.

This story features CFNM concepts and male solo masturbation. This is a complete work of fiction. All characters are over eighteen.

I am endeavouring to gradually write a CFNM "Oz Beach Boy" story in every Literotica category. This entry: "Humor & Satire".

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It was a freezing cold winter morning in Sydney, Australia. I had the heat turned up, but I was getting hot for other reasons altogether.

I was horny as all fuck, even though my eyes were bloodshot and bleary and I was incredibly tired. The night before, I'd stayed up way too late writing a long, detailed letter to my father, who's currently serving a string of life sentences in Pelican Bay State Prison in California.

I discovered not too long ago that my father is indeed Jack "Bull" Tyson, a former American porn actor who fucked my drugged up, party girl mother when he was in Australia shooting some sex movies -- or "fuck flicks", as he calls them -- back in the 1990s. I was the result of this very quick and barely remembered sexual tryst.

As well as porn acting, my father Jack had a few other unfortunate fringe interests -- drug addiction, bank robbery, violence and murder -- which eventually landed him in prison for a very, very long time. [See Story: "Oz Beach Boy Looks For His Father"] Despite his very dark history, however, Jack "Bull" Tyson is actually, well, a pretty good guy.

If all of that wasn't strange enough, Jack and I now regularly send each other long letters detailing our various sexual escapades...and we've both got a lot to write about! Former porn performer Jack has fucked many, many, many women (and a few guys too), and so have I...just the women, that is. As Jack often says, all he has is time, and we have

plenty

of material to keep each other entertained!

Though not officially diagnosed, I'm a raging sex addict. I'm an exhibitionist in my twenties who loves getting nude, preferably with women watching me. I spend hours training in the gym and on the beach to get my body as ripped and muscular as I can, principally to attract as much female attention as possible.

I like to show off and put myself in potentially sexy situations, particularly around Sydney's many beaches and secluded coastal bays. I also frequently stroll around at night on busy weekends looking for action wherever I can find it.

I am constantly horny, and I've enjoyed a lot of kinky hook-ups in my time. I'm also a chronic masturbator. I'm sex-obsessed and I've found a bizarre co-conspirator in the very peculiar form of my very own father. Just another weird aspect of my very weird life.

The night before, I'd spent hours reliving a very enjoyable experience from a few months back in which I'd been invited to join in the sexual shenanigans of a much older husband and wife while I was in Melbourne on a two-day business trip. It was fucking incredible, and I had a great, very hot time writing about it for my father's perverse enjoyment.

As well as writing this long, sexy, very detailed letter for my father, I'd also weighed up an hilarious offer from my beautiful TV star friend Abbie Chatfield, one of Australia's most high-profile celebrities.

Abbie had rather hilariously sent me an email almost begging me to become a contestant on the next series of her sleazy TV dating show

FBoy Island

. After laughing solidly for nearly five minutes, I decided against it.

"Come on," Abbie wrote, "AI couldn't create a better FBoy than you!"

Though I certainly fuck around a lot, I've never really considered myself to be an FBoy, so I didn't know whether to actually be insulted by the offer or not. Either way, appearing on a sleazy TV dating show was not really for me, so I very politely declined. I hoped Abbie wouldn't be offended...it was undeniably a bit of a thrill having her as a friend...and especially as a friend with benefits.

Despite being up very late the night before, I'd awoken with great difficulty at 3:00am to watch the Australian women's rugby sevens team play the USA for the bronze medal in The 2024 Paris Olympics. It was a tight, thrilling but ultimately crushing match, with Australia very disappointingly just beaten in the end.

Watching the very attractive, super-fit, and sexily strong Australian girls in their tight-fitting tops and butt-hugging shorts had gotten me increasingly turned on during the match. I love athletic women -- hell, I actually love

all

sorts of women -- and these girls are absolutely sexy as all hell.

As the gripping, hard-fought match continued on through the very early morning, I came very close a couple of times to slipping off my sweatpants and jerking off in front of the TV. The crushing final score, however, was a real cock-block and quickly put an end to my rugby-inspired, amorous thoughts of spontaneous self-love.

After I'd had a couple of coffees and worked through my complex feelings about the disappointing rugby sevens loss, I kept thinking about those players in their tight shorts, and the sexy way the thin fabric cinched in around their collective crotches.

I quickly began to once again get very, very horny. It felt disrespectful to jerk off over the Aussie rugby sevens girls at this disappointing time in their Olympics journey, so I began charitably thinking about other means of onanistic self-satisfaction.

I considered the pile of vintage

Playboy

magazines on my living room coffee table; I pondered the much-watched collection of nude videos secreted on my laptop of my beautiful ex-girlfriend Odessa Prince; and I mentally scrolled through the myriad of past sexual experiences that constantly swirled wildly and happily around my sex-obsessed head.

What was it to be? What would be my wank material of choice? I almost whacked it over my recent sexy experience of shooting my very own nude calendar [See Story: "Oz Beach Boy Nude Calendar Star"] with an all-female crew, but in the end, I opted for something completely new that I hadn't tried before...a potential new era of masturbation, if you will.

I don't usually go for sex toys or aids of any kind when I jerk off, instead opting to stay traditional with just my hand, my thoughts, and/or some images or video footage on my phone, but on this cold winter morning, I decided to get adventurous.

I'd heard sometime previously about a new, publicly available AI programme called Chatterbox, and I made the decision to try it out. I grabbed my laptop from my bedroom and brought it into the enveloping warmth of my heated living room.

I sat down, and went to the Chatterbox app, which I'd already downloaded but was yet to use. The concept behind the programme was enticingly simple: you typed in a brief scenario, and the coding would create a whole story, which would then be read out to you in a voice of your choosing. Though not explicitly designed for sex-play, Chatterbox was instantly tagged as a cheap and easy masturbatory aid...like so many new forms of tech often are.

I first went in and chose the type of voice I'd like to hear when my scenario was created and cited back to me: Woman>Older>Voice>Deep. I hoped this would make for some sultry, sensual, MILF-type tones; writing the letter for my father the night before meant I was still thinking about the hot, sexy, much older cougar-style wife I'd so happily fucked while I was in Melbourne a couple of months back.

I then went to the awaiting field in the app and typed in my scenario. I love getting naked for women, so it wasn't too difficult to come up with a concept. I just went to my usual kinks and sexual preferences and hurriedly typed in, "I'm a hot man. Tell me to strip off my clothes." I waited for a few minutes, took a couple of deep breaths, and then hit the "Create" button.

A couple of moments later, a deep, booming female voice came pealing out of my laptop's speakers, almost sounding as if it had risen from the depths of hell. The app had obviously taken the description of a deep voice a little too literally. I jumped in shock, but continued to attentively listen to the most booming female voice I'd ever heard, desperately trying to get in the moment.

"You are hot," said the bass-heavy, powerfully echoing female voice. "You are a man. You have male genitalia, and you identify as a male. Your skin is sizzling. You are burning up. You are sweating. You have a dangerous fever. We must break the fever. You are hot! Take off your clothes!"

"Oh, for fuck's sake," I muttered, and punched the "Stop" button, and then the "Clear" button.

I returned to the now once again clear field in the app. I changed the voice setting, and then typed in my scenario a little more carefully this time. "I am a handsome, fully dressed man," I wrote. "Tell me to take off my clothes." Hopefully that would work a little better.

"You are wearing a Pierre Cardin three-piece suit with a white Van Heusen dress shirt and black Louis Vuitton shoes," came a flat, plain voice that was about as sexy as a migraine headache.

"Geez," I muttered.

"It is time for you to take it off," the voice continued. "You need to take off your clothes."

I'm very easily turned on, and this kind of talk actually got me going a bit, despite the distinct lack of sex appeal present in the Chatterbox app voice, and its flat, wholly disinterested delivery. Just the sound of a woman telling me to strip was enough for a very easily aroused man like myself. I wasn't erect yet, but I was definitely getting turned on.

"Get undressed, you handsome man," the voice continued.

I quickly pulled off my hoodie, and then slid off the t-shirt underneath, pleasantly exposing the smoothly waxed skin of my heavily muscled bare torso to the heated air of my living room. I looked down at my body and smiled. I'd been working extra hard in the gym lately, and I was very pleased with the wholly ripped, utterly shredded results.

"Have you taken off your pants yet?" asked the voice. "You need to take off your pants."

"Okay," I said quietly, and then excitedly slid my baggy, grey sweatpants down my rippling, smoothly waxed legs, stepping out of them with ease.

"Now that you're undressed, it's time to choose your next outfit," the voice said blandly. "How about a sweater vest and chinos? Perhaps a shirt and slacks?"

"Oh, fuck!" I spat quietly in disappointment at the voice's utterly unsexy command. "I don't want fashion advice!"

"I think that would look nice," continued the voice. "You are a handsome man. You will look very handsome in a new outfit. Why not try it?"

Clad in just my tight, fitted, black Calvin Klein boxers, I strutted over to my laptop and quickly hit the "Clear" button on the Chatterbox app. This spontaneous techie toss was certainly not the easiest or happiest wank I'd ever had, but I opted to persist and give the Chatterbox app the benefit of the doubt.

I bent down over my laptop, and went back into the Chatterbox app. Typing quickly and desperate to stay aroused, I entered the words. "Tell me to take off my underwear and go nude. Then get surprised when you see my genitals." I waited optimistically...hopefully this would succeed in getting me off. Getting nude would be a good start.

"You need to remove your panties," the voice said flatly. "You need to get those little things off. Take them off your hot body. Take them off."

This sounded promising. I liked the way the app was referring to my underwear as panties...I enjoyed the sense of ridicule and female domination. That was sexy. It was creative too. I obediently slid down my Calvins, and then kicked them across the room. They slid up against the wall, and then tumbled back in a heap. I stood in the middle of my living room completely naked. Again, I looked down and smiled.

Just like my porn actor father Jack "Bull" Tyson, I am blessed with a big, thick, long, ropey cock that hangs almost down to my knees, and it comes backed up by a big, heavy, low-hanging nut-sack. My huge dick and balls have certainly gotten me into a lot of mischief over the years.

"Oooh, look at that hot little pussy," came the Chatterbox app voice. "It's so tight and wet...so pink and sweet. I want to lick it. I want it."

Pussy???!!! Fuck! I stood shocked in the middle of my living room, my huge cock hanging limp and now utterly non-aroused, further dampened by Chatterbox's latest piece of nonsense. Once again, I hadn't been specific enough. I quickly changed the word "genitals" to "cock and balls", hit enter, and then waited. I gave my huge cock a tight, desperate, hopeful squeeze.

"You have a rooster between your legs and two basketballs!" came the Chatterbox voice. "Your rooster could play a sporting game with those basketballs!"

"Jesus Christ," I groaned, and promptly changed the words "cock and balls" to "penis and testicles", hit enter, and then waited.

"Look at that pathetic little penis," came the voice. "It's like a limp piece of spaghetti. I'm so surprised by its size...so small! And your balls are like two shrivelled raisins. I'm so surprised your penis and testicles are so small and pathetic. It's such a surprise."

"Oh, fuck," I grunted, and disappointingly let go of my dick, which I'd been clutching hopefully the whole time.

Though I enjoyably work in the IT consultancy field, I am under absolutely no illusions as to the limitations of modern technology. Though newly developed tech can be great, it can also be highly frustrating. I think I'd just about come to the end of my patience with the Chatterbox app. I'd had enough...I was done.

I walked over to my laptop with my big dick swinging and my heavy balls dangling, and then closed down the Chatterbox app. That was the end of my AI-assisted techie toss. I was well and truly over it, but I still desperately wanted to get myself off.

Those sexy, athletic rugby sevens girls had got me horny as fuck. I looked around my living room, and there, smiling up at me sultrily from my coffee table, was

Playboy Magazine

's gorgeous 1985 Playmate Of The Year, Karen Velez.

The glow from my ceiling lights glinted beautifully off the blue-hued cover of the special

Playboy

issue, and the supremely sexy Karen Velez's delightfully alluring brown eyes beckoned to me.

With her hair wet, and her wonderfully pneumatic body submerged in rich, blue water, the beautiful brunette looked absolutely stunning. Karen Velez was a knockout...god, what I would do to fuck her! I was getting hornier by the second.

With a big smile of satisfaction, I walked over to my coffee table and picked up the 1985 special edition of

Playboy Magazine

. The hard-copy mag felt heavy in my hands...it was sensually tangible, something that I could feel. There was nothing ephemeral about it. This magazine was a piece of history, a sexual artifact.

I stood casually nude in my living room, and flicked through the magazine's pages. I went past interviews, articles, ads and lesser nude pictorials until I eventually made it to the gorgeously laid out "Playmate Of The Year" photo spread, which featured Karen Velez lolling sexily around an exotic beach somewhere in Fiji.

I gazed in wonder at the exquisite photography and the artistry of the images. These weren't run of the mill photos you could create with AI, or standard images you could just find online. This was much, much better than that.

Though I am a relatively young person in my twenties, I have a very keen interest in pre-internet art, photography, and yes, pornography too. There's something undeniably sexy about things not simply made on a computer or shot digitally.

They might have been published before I was even born, but I love my pile of vintage

Playboy Magazines

. I've collected them over a period of several years, and they're amongst my most cherished possessions.

As well as gazing in awe at the level of artistry evident in the gloriously composed "Playmate Of The Year" photo shoot, I also gazed in awe at the extraordinary body and gorgeous face of the divine Karen Velez. The sultry brunette was truly exquisite -- one of the sexiest women to ever grace the pages of

Playboy

-- and I unmistakably felt myself stiffening.

My cock began to swell and rise away slightly from my taut body as I looked down at Karen Velez's huge, pillowy, low hanging tits, her deeply tanned skin, her flat stomach, her beautifully curved butt, and the huge patch of black, tightly curled pubic hair that nestled sexily between her long, lithe, supple legs.

As I looked at an incredible image of Karen Velez peering down at her nude body and thatch of pubic hair covered in beach water and sand, my cock became completely erect, and I moaned quietly with pleasure. I slowly lowered myself onto the floor of my living room and got a firm grip on my stiff, throbbing cock with my right hand.

I sprawled out nude on the laminate floor, the stupid Chatterbox AI app now happily forgotten and replaced by the sturdy certainty of the

Playboy Magazine

spread out in front of me. This was more like it!

I turned the pages slowly, the paper crisp and clean between the slightly trembling fingers of my left hand. I gently stroked the rock-hard shaft of my cock with my right hand. The muscles of my bare torso tightened and flexed. I sucked in a deep breath.

I jerked myself off with increasing excitement, gazing with delight at the succession of nude images of Karen Velez. I imagined myself on that beach with her, licking at her small, dark-brown nipples and kneading her smooth, tanned flesh.

As I jerked my cock, I fantasised about burying my head between her legs and losing myself in her enormous bush. I dreamed of propping Karen Velez up onto all fours, and penetrating her from behind while I clutched her huge tits and worked them like dough between my fingers.

As I jerked my cock back and forth with my tightly clenched fist, I could almost feel myself thrusting in and out of Karen Velez's silken, welcoming pussy. I moaned loudly as I looked down at the magazine in front of me, pumping my cock harder and harder. After a few more minutes, I felt a wave of pleasure flood from my groin and into the rest of my body. I was coming. It felt amazing.

"Oh, yeah," I moaned. "That's it, baby. Oh, Karen! Oh, Karen!"

Overcome with orgasmic pleasure, I closed my eyes. I felt my cock explode, and then heard the very familiar sound of generous lashings of my semen slapping onto the laminate floor of my living room. I groaned with joy, and then slumped onto my back, the floor cool against my smooth skin. I sucked in a series of deep breaths. I felt wholly, enjoyably satisfied. Against the odds, I had eventually gotten myself off.

As I laid sprawled nude with my legs spread wide on my living room floor, I realised that Artificial Intelligence is exactly that...artificial. And a lot of the time, it isn't actually all that intelligent either.

When it comes to onanistic self-love, sometimes it's better to go old school...after all, it's hard to beat a

Playboy Magazine

, a hot, naked woman, a little bit of imagination, and your chosen hand. A new era of AI? Maybe, but not this time...

Thanks for reading!!!

To read about Matt enjoying some slightly less troublesome bouts of self-love, check out my stories "Oz Beach Boy's Waterside Wank", "Oz Beach Boy's Byron Bay Beach Wank" and "Oz Beach Boy Nudes Up For Neighbors".