Key West Postcard

Travel Diary: A Little Latin Spice to Make My Tropical Vacation Memorable

It’s funny how things don’t work out the way one plans.

I arrived in Key West on a Wednesday night. I expected a build up of ass to peak with a crescendo over the weekend and a tapering off until I left the following Wednesday.

Alas, that did not occur.

Not that I was hunting for hole. In a way, I expected it to find me. I had offers, but I decided to be a bit picky rather than accepting just any ass thrown my way. Interestingly, I think the whole relaxing and doing nothing actually calmed down my hormones and made me crave ass less. Plus I got my fill of naked boys and attention at clothing optional destinations including my B&B and the nightclubs I frequented.

After the weekend concluded and Monday inched along, that itch rose a bit and I realized I’d built a hefty load in my balls that needed to find a home — and soon.

Unfortunately, BarebackRT.com Link Opens in a New Window showed little sign of life, with Scruff and Grindr not too far behind and Jack’d so far netted me nothing. I posted on Craigslist using a generic top looking for bottom post and lucked up with a few potentials. I’d been posting on CL for a while — mostly my “top blogger coming to town and looking for bottom inspiration” ads with little luck (except for the hot guy who’d blown me off).

I got a mixture of responses, a few of which were legit among the flakes. One caught my eye and it wasn’t just the fact he was 20 years old Latino visiting the island. He’d offered his phone number early in the exchange and we began texting almost immediately after when he asked, out of the blue: “Are you the top blogger?”

“Blogger?”

“I figured you were,” he answered, without a confirmation. “It’s really cool if you are.”

“What are my chances if I am?” I wrote back.

“I’d say your chances are really good.”

Within a few minutes, we were meeting on Duval Street and headed back to my B&B.

In shorts, flip-flops and a Hollister t-shirt, he looked like the vision of someone from an advertisement. Smooth with very few specks to even call freckles dotting his face, he was perfectly tan and his wavy black hair just cropped perfectly against his scalp. His deep hazel eyes glanced me over as I took his broad hand into mine and we shook. He was warm — not as much in demeanor as in physically, like he’d just crawled out of a tanning bed.

Our chit chat seemed almost about nothing important as we compared our lodging choices. Soon we were walking through the gate and into the courtyard. I gave a little tour of the property and we ended up in my room. With the enthusiasm of his age, he soon removed all his clothes.

His body proved to be one of those not-an-ounce-of-extra-fat-or-flesh perfection. A mixture of tan and olive, his smooth skin was blemished rarely by a freckle. He didn’t contain any extra muscle either, so he didn’t pack on huge pectorals. His legs were almost hairless and he’d shaved his pubes off. His balls, drawn tight up into his cock, looked hairless as well.

I moved in closer but he pushed me away.

“I don’t really kiss,” he said.

I tried not to seem disappointed, but I was. His fat lips seemed too inviting for me not to lick just a little.

“You still suck, don’t you?” I motioned toward my cock.

He didn’t answer, instead moving toward my half hardness and  moving his mouth over its delicate skin.

He needed more practice but not bad. He kept his lips and mouth frozen while the bobbing of his head provided all the friction to bring me up to full mast. Still, I didn’t care. I played with the hair on the top of his head and then pulled him up and moved toward his cock. All the while I let my fingertips dance across his body until my mouth found the tip of his cock.

Yes, I sucked his cock and he inflated to an impressive 8 inches. Much larger than I dared reach. And fuck if he wasn’t thick with a slight bend to the left. The impressive size seemed even more humongous thanks to all the missing hair. Honestly, this boy wasn’t too hairy or had been shaving for a long while as I didn’t sense any prickly around his cock base.

I went for the balls — a little rougher, mind you, but still very smooth. Youth, it seems, can be so very tasty. As I began to lift his legs, he didn’t stop me and I went in search of his hole by taste.

My tongue found a crevice but it didn’t seem right. I pulled back.

What I saw happened to be among the most unique sights ever.

Most people have a ring around the rosie, so to speak. The external sphincter’s fleshtone appears a little darker or lighter, depending on the man. Sometimes it’s a few rings.

Not him. His skin maintained its perfectly olive bronzed tone up until his asshole, which appeared as nothing more than tiny folds like a quarter-inch crucifix. I’d never seen an ass like his. I wondered if he had any sensitivity in his ass.

As I returned my tongue to his ass, I soon discovered my answer.

His thick 8-incher had been hard but very pliable — like a dildo. But as I went to work and the cross-shaped pucker widened, his cock became more rigid — more similar to a vibrator. Soon it grew even thicker and longer. It stood in place, attention as the most dedicated soldier.

As with any 20-year-old, he hadn’t quite learned to share attention, used to the men who lathered upon him kudos on his good-looks and great body. But he took the subtle direction well as I reached for some Spunklube Link Opens in a New Window and began to spread it on his asshole and use my fingertips to tease that holy hole open just a bit more.

I righted myself, proceeding to poke my cockhead against the hole.

“Mind if I sit on it?” he asked.

“Works for me,” I said, rolling off and onto my back.

My cock too was rigid and pointing at my belly button. A string of precum dangled off in anticipation as he maneuvered in front and slowly lowered himself. But he did so without hesitation, with ease and sat down completely to the hilt within moments.

He was a natural bottom.

We’d never discussed condoms and, as he’d read this blog, knew I’d bareback. He seemed at ease with the fucking and enjoyed it, but didn’t vocalize a lot. Truth is, I’m not very loud either.

His chute adhered to my cock so smoothly, it was a fuck never to forget. Like a key sliding into a slot with just enough space for a perfect fit, his ass walls just seemed to fold into every skin fold of my cock. At first, he would move a lot to try to give me pleasure — something I found humorous since the movement seemed almost robotic, just like his sucking. However, thanks to his perfectly pliable ass, it didn’t feel robotic as the skin’s friction would give way just perfectly.

I soon found myself losing control of my own choice of when to cum.

I suggested he relax and let me do the fucking. Interestingly, he’d read my 11 Commandments for a True Bottom Opens a new window from this blog and attempted to adhere to at least some of them, even asking permission to play with his own cock.

“Just don’t cum first,” I said. “I want to be sure I get to cum.”

“Don’t worry,” he said. “The fucking isn’t over if I do cum.”

That made me want to test it out by having him cum on my cock then letting me fuck him with his cum, but I dare not risk not being able to load this boy up.

We settled into a leisurely pace and soon I put him on his stomach, staring at his hairless and smooth bubble butt before shoving my cock inside and mounting up for the breeding of his life. I snorted poppers and let myself lose control, asking him only once if he wanted it.

“Yes,” he said. “Give it to me.”

That one positive response was enough that I lost it in that perfect hole and began to flood it. And when I say flood, I mean flood. Since I hadn’t cum in about a week, I let loose a torrent out of my balls that soon lubricated that space between my cock and his ass walls. I pushed it in deeper.

“Just don’t cum inside me,” he said.

Oops, I’m thinking. It’s a little too late.

As I’d mentioned, we’d been fucking very quietly so I hadn’t really done the whole, “I’m cumming,” and grunting thing. I just generally don’t make a show of it. And here I am, pushing my cum deeper inside him and he’s asking me not to cum inside him.

I pretend like I’m having a build up to cum and I pull out and grunt, pretending to cum with my head on his back. As he knows about the truth now, he’s probably thinking “did I or did I not feel the splash of cum on my back?”

The funny thing: As I rolled off of him, he climbed right back into my cock and rode it until he squirted. And let me tell you, he squirted all over. Some went over my head, some landed on my cheek, my chest, etc. He looked away for a moment and I tasted it, just to sample some from the fountain of youth. He’d never know. After all, we weren’t kissing.

We chatted for a bit. Luckily he never put on his shirt until he left. I’d gladly have kept him there all night. But I sure as hell missed the kissing part. He asked if I would write about him and I expressed that I wanted to, knowing that I’d bred him and wondering if he’d really noticed.

He requested I withhold his home state and where he was staying as well as any photos he’d sent me, which I reluctantly agreed in order for you, dear reader, to read this. The rest is basically true, most especially the part about me breeding his ass when he asked me not to do so.

If he’d really been reading my blog, he’d know I always make a deposit. I don’t fuck with condoms and I don’t pull out. No matter how hot, how young or how great your ass is. As a matter of fact, the hotter, younger or better your ass, the more I can guarantee I’m going to breed it.

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