The Gaycation He Would Never Forget

The Gaycation He Would Never Forget

FOREWORD: This story was inspired by the time someone close to me told me he met the porn star, Rocco Steele, during a vacation in Europe. He sent me pictures to prove it. I’d so love to meet a porn star! (Sorry, Duke, lol)


Benedict had been planning the gaycation for a long time – an opportunity to disappear from the humdrum his life had become ever since he relocated to the US from Nigeria six years ago. For a long time, his life had taken a routine he’d found increasingly stifling – work, home, church, gym. He was even able to make it to the gym in subtle defiance of the routine he saw colluding to hamper his gay life. It was at the gym that he had an awakening of his desires, as he ogled the taut butts and impressive biceps that thronged this way and that amidst the sea of beguiling testosterone – a crush of men he didn’t have the gumption to engage for the possibility of a hookup.

And so, for six years, Benedict had had no social life to speak of, except for the odd quickie he got on with on Sunday after a reluctant visit to Grindr. He really wasn’t a fan of gay apps. However, it was through one of those weekend hookups that he heard about the word ‘gaycation’, and how he could get away from it all, his life, for a vacation of relaxation and gay sex.

Upon his hookup’s recommendation, he chose Miami South Beach. It was in the spring of the year. The weather was great when his vacation time came around, not too hot and not too humid. He quickly adapted to the leisurely pace of life as a vacationer in SoBe, one which was interspersed by the frenetic interludes of the sex he had almost every night. There was so much sex to be had in South Beach, and Benedict was just hot enough to get most of the action.

On this particular day, he’d logged onto Adam4Adam and found a nice willing ass that was close by. The guy, Caucasian and bronze-skinned from his tan, had a condo on SoBe and wanted to get fucked. Both men made arrangements to meet at his condo in an hour. Surprisingly, it was within walking distance of Benedict’s hotel. He showered and dressed, putting on a shirt and loose, thin, white, baggy, linen shorts, with no underwear, acting on a sudden impulse to free-ball, and then headed out.

On the way, he got several looks from men who were mesmerized by the brazen flash of his dick beneath his shorts. One man was on the phone. As they walked past each other, the man cut off his phone conversation and simply watched Benedict’s dick swing from side to side. Benedict smiled and gave him a wink. Dick sure did have a way of getting another man’s attention. He could not believe the things he could get away with here, that would never happen back home in Nigeria.

He soon arrived at his hookup’s condo, an apartment that was very art deco, which was common to South Beach. He commented on how nice the place was and the hookup, who introduced himself as Leo and was actually Latin American, murmured his acquiescence. That was the end of the conversation as they quickly moved things into the bedroom. Leo started kissing Benedict’s neck and then they tongued each other down. By this time, Benedict was hard as fuck. Leo made his way down to his dick and began giving him a very good sucking. Benedict couldn’t let him give him all that head and not return the favor. So he flipped Leo around onto his back, slid down to his groin and started sucking his thick, uncut Latin dick. It had to be about 7″ around with an upward curve, not very lengthy, but thick as fuck, which served as nothing but motivation. Benedict was Top, but he loved dick. Actually, dick turned him on more than ass. There was just something about a man’s hard penis that tended to drive him insane.

At any rate, they resumed kissing for a few heated moments of grasping hands and sliding legs, and then Benedict positioned Leo on his back with his legs in the air. Like a good Top, he rimmed that clean ass with his lips and tongue, his taste organ slipping and sliding inside Leo’s rectal corners with such mastery that Leo was quickly quivering and moaning, a clear indication that he was enjoying Benedict’s ministration. Slowly, his ass was opening up and getting wetter. Benedict ate it and fingered it so good, Leo was soon panting for his dick.

“Now, please…” Benedict heard him grunt a number of times in between gasps.

He obliged him, wrapping himself up, and then it was on. Let the fuck fest begin! They started out slow and sensual, fucking missionary for a while. Leo’s ass was open and he was taking the dick like a champ. Then they switched to doggie style. That was when the shit got real. Benedict started pounding the ass to no end, occasionally slapping the bronzed skin as he thrust in and out, and eliciting moans from Leo that were muffled by his face buried deep in the pillow. Their orgiastic sounds filled the room. The chemistry was right and the bed was squeaking.

Benedict was feeling great at this point, so he start talking shit. He was growling with each thrust, “Squeeze that ass on my dick, baby…! Squeeze that ass!”

And Leo did just that – he squeezed Benedict’s dick so hard, it felt like somebody’s hand was squeezing the life out of his dick. For one panicked second, Benedict thought his dick was going to pop like a balloon! In an instant, he went from fuck mode to fight mode. He choked out a gasp as he brought down a fist on Leo’s back, one, two, three times, before Leo unclenched and he was staggering back from the ass that had only moments ago held so much promise.

“Man, what the fuck is wrong with you?” he choked out.

“Oh God, I’m sorry…” Leo was apologetic as he straightened up, his face an odd contortion of misery and arousal.

“Don’t be squeezing my dick that hard! Are you crazy!” Benedict could still feel the pain pulsating through his shaft.

“I’m sorry…”

The lovers took a break. Benedict’s dick was sore; however, he was determined to bust his nut. After some minutes, they fucked again and both of them came without incident. While getting dressed, they talked about how Leo’s ass sphincter muscles were so damn strong. Benedict had never encountered an ass that could squeeze like that and he never wanted to again.

They kissed and said goodbye, and Benedict left the apartment. He was approaching the front door when an incredibly fine – and familiar – black man edged past him on the patio. It was Cody West! The porn star! He could’ve fainted. In a flash, he remembered images of Cody West’s massive dick and the times he’d masturbated to it in the past. To see him live was awesome!

The adult entertainer, whose every cum face Benedict had watched and loved in the flicks he downloaded from pornhub and wanked to, glanced briefly at him, and then down at the dick that was back to being lord and master behind the linen shorts.

And he smiled, before saying, “Oh.”

Benedict looked down, and sure enough, there was a big wet spot on the front of the shorts. He chuckled. It was an infectious sound and the other man joined in, and just like that, they exchanged a brief laugh.

Benedict left the building feeling like he was on Cloud 19! (Fuck Cloud 9!) He had just had some good ass and also ran into Cody West! Today was indeed a good day!

Still on Cloud 19, he got a few blocks away and then realized that he left his keys at Leo’s condo. So he called him, and Leo said he was just getting out of the shower and that he had to be somewhere soon. Benedict told him he was on his way back. He got back to the condo and his keys were on the dresser. Since Leo was heading out, he asked if Benedict wanted a ride back to his hotel and he accepted.

In the car, Benedict asked him if he knew that a porn star lived in his building. Leo responded, “Yes, and he’s also an escort. He’s top and will fuck you for $200.”

Apparently, they had messed around for him to know that much info, Benedict thought to himself. And then he wondered if Leo squeezed Cody West’s dick like he’d squeezed his. It was the last thought he had, which brought a chuckle from him, before he got down from Leo’s car and walked the rest of the way into his hotel.

The thought would stay with him for the remaining couple of days of his gaycation, because his dick remained sore, and watered down any desire he had of hooking up again, before he had to return home.

Written by Pink Panther

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  1. ambivalentone
    November 26, 07:56 Reply

    This is how someone has given me unplanned assignment. How to give that sphincter of mine some good, life-choking grip??

      • ambivalentone
        November 26, 09:07 Reply

        Well, that kind of control is enviable. Imagine the possibilities. Murder by dick popping.

  2. Stein Macaulay
    November 26, 08:19 Reply

    I don’t think I can make comments that are on my mind… But, WOW!!

  3. Delle
    November 26, 10:33 Reply

    A top that prefers dick to ass? A bottom that prefers ass to dick here! Oh look at us going over borders?

    Now, I need to train my spincter on the choke hold thing for those ones that cannot hear, “Stop o, I aff taya!”

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