Twinks Across America: Chapter 1 - Hawaii

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#2 of Twinks Across America (starring Sebastian Drakos!)

Meet Sebastian Drakos, a self-made European billionaire of Doberman/Great Dane ancestry, who is very fond of gay twinks. What's a man like him to do for a vacation? Travel to each U.S. state to sample the local mammals eager to lift their tails for him, of course! That's fifty twinks across fifty states, with one DILF to see it all!

We begin our journey in Hawaii. Enjoy the start of this new series! Have a Happy July 4th, and I hope you enjoy my daily posting of "Twinks Across America"!


My very first U.S. state to spend the next few days in happened to be Hawaii. Such a tropical paradise to start my exploits in, almost reminding me of Greece in the middle of a warm summer. Boats of all sizes floated amidst calm waters, surfers engrossed themselves in the thrills of rising waves, and plenty of gorgeous eye candy for me to covertly look at from afar.

The plane landed around 5:00 in the evening, leaving feeling restless and incredibly lethargic throughout the long flight, but a quick power nap at the vacation beach house allowed me plenty of sleep. Once I woke up around brunch, the rest of my day had been spent recuperating and ordering some dinner while enjoying some privacy for the rest of the night.

It wasn't until the very next morning that I decided to have some fun. After sporting a typical Hawaiian T-shirt with blue and yellow colors, plus one of my tight red speedos (which regularly tested societal rules about modesty as it clung to my bubble butt), I ventured out to the public beach. It lay within walking distance from the beach house I'd rented for the next few days, but I didn't just pick it out so I could lure in a handsome stranger for some same-sex fun within the bedroom; The previous year had been a profitable yet stressful time for me. On top of visiting each US state, I also wanted to enjoy myself. So, with a six-pack of daiquiris in one paw, my smartphone in the other (a vacation didn't mean I couldn't just simply ignore my stocks), and a pair of sunglasses protecting my eyes, I set up a sunbathing chair to enjoy myself.

A couple of hours passed as I basked in the sunlight. As well as wandering eyes directed on my magnificent abs and the proud treasure trail leading to a bulge covered by red fabric.

Quite a few didn't bother to be subtle about it, while most preferred to focus on passing women in bikinis or the beach itself. The minority brave enough to openly ogle certainly wasn't unwelcome, especially when I covertly adjusted myself down there. One bashful polar bear in his twenties certainly liked that, his eyes almost popping out of their sockets like an old 1930's cartoon character. What could I say? I loved some attention.

Speaking of which, I included a photo of myself at the beach on my Howlr profile, and I explored with messages from nearby users. One which led me to a user named Twink2Cum69, followed by a heart emoji. Aged twenty-four, an occasional smoker, not a virgin, and in an open relationship. He and I messaged over a few hours as we learned about each other. He was a native Hawaiian who worked a retail job while also saving to go to graduate school. When he wasn't amongst his other straight friends or visited his religious extended family whenever he could, the lean wallaby preferred to be nicknamed 'Koa' by the biggest dominant tourist to fuck his brains out. A title which I happily provided, after seeing the slender but big-bottomed wallaby with my own eyes when he rang the beach house's front doorbell. Of course, I opened it while wearing only my T-shirt and the speedo.

"Mr. Drakos?" He asked mid-blush. "It...It's me, Koa."

"Nice to meet you, Koa," I invited him inside and we exchanged lewd grins, with his eyes wandering down to my crotch. "So, what would you like to do? We've got all night."

He eagerly giggled, "Well, this may be a little strange but," he paused while nervously grinning, "how about the boyfriend package?"

The wallaby twink turned out to be a hopeless romantic. He allowed me to take the lead yet insisted I treat him like we were long-lost lovers who found each other. Whatever rocked his boat. We had the entire evening to ourselves after all.

We kissed. We hugged. We nuzzled each other. We whisper sweet nothings. We snuggled for close to two hours on the couch, watching soap operas while sweetly holding paws. We talked about various topics while subtly teasing or fondling the other. Then, we made out like lovesick high school teenagers on the master bedroom's soft bedsheets, slowly peeling off our clothes until we lay together in a naked, sweaty heap as the sounds of crashing waves echoed outside.

Making slow, intimate love on a silk-laced bed never got old for me. Sure, the rough and passionate side of homosexual sex never ceased to amaze, but the softer side of male sexuality could also be open to exploration. The simplest touches of your knowledgeable fingertips could leave a twink cumming. And the way Koa lay vulnerable under me, laughing with indescribable lust as my wet dogcock slid back and forth against his ashen-furred thighs, made the young wallaby writhe needily into my torso as his legs kicked the air.

He wouldn't quit moaning and giggling. Not when I possessively cupped his right cheek or jokingly slid the tip of my member against his taint, making his tail smack against the bedside lamp by accident. It did little to sour the mood. A small dollop of lube later and his moans did crescendo into a rumbling composition worthy of Tchaikovsky. His grunts were premature cannons as I helped him cum halfway through my fucking.

I didn't feel too bothered by Koa's ejaculation happening before mine. The wallaby did not mind either, falling into the vast beauty of subspace as I ravished in and out of his pillowed tailhole. He trembled in my strong arms, legs thrashing in euphoric pleasure as I gave the lad his dominant lover fantasy with a climactic, tongue-slobbering kiss. That was around when I finally shot my mixed seed.

We lay together for a good half an hour, panting and out of breath. However, it didn't stop the spent lad from pulling himself into hugging my chest. I promptly held him close, able to hear his racing heartbeat begin to calm itself.

"That was amazing, Mr. Drakos."

"It sure was, Koa."

"Was I okay?"

I chuckled humorously, "Okay? You were great, kiddo."

Truth be told, I wanted to go for another round. Yet I settled on him giving me a post-afterglow handjob as my thumb absentmindedly browsed through updates on my stocks. Redressing ourselves afterwards and having casual conversations about Hawaii's entertainment scene, I also felt tempted to ask if he were interested in becoming another Sugar Twink of mine. That was until he mentioned his open relationship. Turned out, Koa already had a sugar daddy in the form of a Chinese dragon who worked as a traveling international businessman. He let the wallaby lad play with other open and closeted gays as long as he gave detailed descriptions of the acts during video sessions. Did he have a cuckholding fetish?

Oh well. To each their own, and we still had an enjoyable time. He got fucked by a dominant male and I was allowed to breed with that bouncy ass at least once. All that was left until the next flight out was to enjoy the beach house for what it held and go swimming at the beach leading out to the vast Pacific Ocean.

Twinks Across America: Chapter 2 - Alaska

Alaska's climate certainly lived up to its reputation. Flying by first-class airline from Hawaii to the most northern U.S. state felt like traveling from Mercury to Pluto. After stepping out of the terminal and...

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Twinks Across America: Introduction

Picture in your head a man named Sebastian Adalbert Drakos: freelance stock trader, former hedge fund manager, self-proclaimed 'femboi connoisseur' and part-time undercover informant for Interpol. The result of...

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