Tony was the owner of a security software company. It had been a hard week trying to finalize a very lucrative contract but they could not reach a compromise so they decided to take the weekend off and reconvene on Monday. After the potential clients left the conference room mid-morning, Tony took a deep breath but still felt he was wound as tight as a spring and he did not want to feel like that all weekend. He wanted to go into the meeting Monday with a clear head and de-stressed body.
He made a quick phone call and three hours later his private jet was taxing down a private runway to a vacant hangar on his favorite island getaway. As soon as his plane touched down on the runway, it seemed as if the stress just melted away. When he stepped out of the plane onto the tarmac, Tony stopped for a moment to stretch and take in the tangy smell of salt in the air. Paradise. I should chuck it all and move here permanently.
Taking another deep breath, he turned to face his pilot and flight attendant. “We will leave out of her Sunday afternoon,” Tony told them. “Enjoy your time but make sure that you are back here then,” as he handed them each an envelope, which contained spending money for the weekend.
Tony strolled over to the waiting car with them and soon they were at the hotel. After everyone checked in, they went to their rooms. Tony opened his suitcase and pulled out a pair of swim trunks and went into the bathroom to change. Until Sunday afternoon when he got back on that plane, he was no longer Tony the billionaire who owned a security software company but just plain Tony who wanted to party and have fun.
As he stepped out on the small front porch, he checked to make sure that he had his keys before shutting it behind him. After forgetting his keys and getting locked out a few times, he always made sure that he had them before closing the door. Stretching, preparing for his jog to the beach a couple of miles away, he took that time to reflect on his life.
Sure, he didn’t have a condo by the beach but the small studio apartment he rented was close enough that he could jog there in a few minutes. He had the ideal life. Although the job he had barely paid more than minimum wage, the tips he received helped him live a comfortable but simple life. For the past two years, he had been working as a bartender and part-time exotic dancer at The Clamshell. The club did not open until five in the evening so he had the day to himself doing what he loved best; being a beach bum, sitting on the sand, soaking up the rays, and swimming in the ocean.
Feeling that he was warmed up enough, he started his jog to the beach. He was a little later than normal for his beach time but he had worked extra hard the night before as the club had three grooms parties and they kept him hopping behind the bar with no breaks. When he had gotten home, he crashed and overslept.
Arriving at the beach, he saw that it was pretty crowded so he headed for his special place, hoping it was not already taken. Once there, seeing no one around Drake spread out his towel and sat down, putting the small insulated bag beside him; this carried a few bottles of water and granola bars. Laying back, he settled his mirrored sunglasses on his face, listening to the sounds of children squealing as they played in the sand and ocean several hundred feet away.
After an hour of catnapping, Drake sat up and got out a bottle of water, taking a couple of drinks before turning his attention on the beach in front of him. It was at that time Drake noticed that there was another towel spread out about six feet to his left but there was no one occupying it. Gosh, I hope it is not some female tourist. I am not in the mood to fend off her hints of hooking up. As he sat there, debating whether to move or not, Drake saw a man emerging out of the water and walk his way.
Drake knew it was not polite to stare but he could not take his eyes off the man. As he got closer, Drake saw that he was maybe a couple of inches taller than his 5’8” frame, was very buff with a six-pack any man would be proud to own, and short blond hair. Not wanting to be caught staring, Drake quickly averted his eyes and turned his attention back to the water bottle in his hand.
“Hi,” the man said as he flopped on his towel. “Sorry if I am invading your space but the rest of the beach was pretty crowded. Would have asked if you minded me putting my towel down but didn’t want to disturb your nap. By the way, I am Tony,”
“I am Drake and this is a free beach so you can put your towel anywhere you want,” Drake answered back before he finished off his water.
“May I ask what type of work you do? I work in security software,” he asked making general conversation. “Vacationing or a resident?”
“I am a resident and work as a bartender,” Drake said, not bothering to tell him he was also an exotic dancer because many thought that was just a fancy word for a stripper and he didn’t feel like explaining. “I work at The Clamshell,”
“Are you working tonight? If not, want to grab a bite to eat?” Tony asked impulsively. “Maybe you can show me some of the nightlights that a tourist might miss on their own without someone from the island showing them.”
Drake took a deep breath, one part wanting to say yes while another part wanted to say no. He wasn’t sure Tony would fit into any of the places he sometimes frequented on his days off.
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“Sure, I would like to grab a bite. What hotel are you staying at? I can meet you there in about an hour. I need to go home and change first,”
“I am staying at The Seaside Resort, Room 605,” Tony said. “We can eat at the restaurant there. My treat of course,”
At the mention of one of the most expensive resorts on the island, Drake almost made an excuse to not show up. “Okay,” Drake said standing up, picking up his towel and bag. “See you in an hour,”
As Drake jogged off, Tony watched his ass move side to side, feeling himself starting to harden. Damn, I hope he is gay. That is one fine looking specimen. Wonder what he is packing under those swim trunks?
When Drake walked into the lobby of The Seaside Resort, he looked around, expecting someone to come up to him and asked him to leave but he made it to the restaurant with no incidents. Approaching the entrance, he saw Tony sitting on a couch.
Standing up, Tony approached him and said, “I know I promised you a meal at the restaurant but I could go for a great burger so where would you suggest we go?
“There is an awesome burger joint about ten minutes from here. Do you mind walking?”
“Not at all,”
Glancing at Tony, he was relieved to see that like him, he was casually dressed in jeans and a tee-shirt, sandals on his feet. When they walked into The Burger Barn, the smell of grease and fried onions filled their noses.
“Hey sexy,” a young blonde waitress called out as she walked by, stopping to kiss Drake on the cheek. “Be right back to seat you,”
When they were seated, she gave them a menu and walked away. Tony looked at the menu, which consisted of at least 20 varieties of hamburgers, fries, and milkshakes, and colas.
“What can I get you?” she asked turning to Tony because she already knew what Drake wanted.
“Try the Texas Chili Burger. It is topped with their homemade chili and cheese,” Drake suggested. “And one their homemade shakes.”
“Sounds good and I will have a strawberry shake,”
She gathered their menus and walked off, leaving Tony with a bewildered look on his face as to why Drake had not ordered.
“She knows what I order every time I come here,” he explained seeing the look Tony was giving him.
When their meals arrived, they were so absorbed in eating that all talked ceased.
“Damn, you are right,” Tony began, “this is delicious. Thanks for suggesting it,”
After they finished, Tony insisted on taking care of the check. Walking back to the resort, Tony let his arm brush against Drake’s arm several times. Taking a chance, Drake grabbed his hand, intertwining their fingers together as he turned his head and smiled at him, the tip of his tongue licking his bottom lip. The sensual vision of that tongue on his cock seemed to send all the blood rushing to that area.
When they got near the door to the lobby, Drake let go as he didn’t want to embarrass Tony if he was trying to keep that side of him a secret.
Stopping, Drake leaned close to Tony and whispered, “I am not a prostitute but I want you,”
Drake gave a little nod of his head, following Tony inside and over to the elevators, being careful to keep a safe distance between them. When they got into the room and the door closed, Tony grabbed Drake and pushed him against the door, his lips hard against his as his tongue demanded entrance. Drake put his arms around Tony, grabbing him by the ass to pull him closer as they devoured each other’s mouth, grinding against each other.
Breaking apart, each was gulping in deep lungful’s of air, waiting for the world to right itself. Tony stepped back and pulled his tee-shirt off before reaching down and unfastening his jeans, pushing them and his boxers to the floor as Drake was doing the same thing. Once they were undressed, Drake reached out and grabbed Tony’s shaft, wrapping his hand around it, squeezing it.
As if one mind, they stood there stroking each other as they leaned in for a kiss. Drake broke the kiss, leading him to the bed by his shaft. Pushing Tony back on the bed, Drake leaned over him, hands on each side of his chest as he took first one and then the other nipple between his lips, sucking and nipping at them while he rubbed himself against him. Tony had never had his nipples sucked before so he had no idea they were so sensitive. He laid there and moaned, the pressure of Drake’s cock against his almost sending him over the edge.
Slowly Drake kissed his way down Tony’s body, down one thigh, and back up the other before lightly wrapping his lips around his shaft, almost sending Tony off the bed.
“Oh fuck,” he moaned as he fisted the bed, trying to raise his hips to push more of him into his mouth but Drake put his hands on his hips, holding him in place as worked his tongue over the head and down the backside, his lips still lightly encasing him.
Gradually Drake tightened his lips until Tony felt like Drake’s lips had him in a vise grip as he pulled the skin taut moving back until he just had the tip in his mouth, his tongue swirling over the head. As he did that, Drake could taste the pre-cum on his tongue. Replacing his mouth with his hand, Drake scooted down farther, spreading Tony’s legs until he could get to his balls, swiping his tongue up and around, sucking first one and then the other while stroking him.
Hearing the change in Tony’s breathing, Drake moved back to take Tony deep in his mouth, his hands massaging Tony’s balls. Tony tried to hold out as long as he could until he gave out a cry, filling Drake’s throat with spurt after spurt of his cum until he was drained. Crawling up on the bed, Drake kissed him, letting Tony taste himself as they kissed.
Flopping back beside Tony, their feet hanging off the edge of the bed, they just laid there, neither saying a word. Soon they maneuvered around on the bed until they were stretched out on the bed. Tony reached over and pulled Drake back into his arms, his head on Tony’s forearm as Tony’s free arm dangled over his hip, his hand playing with Drake’s shaft.
Drake moaned and pushed a little closer, feeling Tony pressing against his ass. They continued to lay there, Tony’s hand stroking Drake’s cock, feeling it growing in his hand. As Drake kept pushing against him, Tony could feel himself coming back to life. Moving his arm from under Drake, Tony pushed him against the bed as he turned to take Drake in his mouth. Tony tightened his lips against his shaft while his hand squeezed his balls. Reaching out, Drake began to stroke, Tony.
“On your side,” Drake demanded gently nudging him
They moved around until Drake could capture Tony’s shaft with his mouth, hand moving to his balls. Tony and Drake laid there side by side, stroking, licking, and sucking each other, pulling back with the other got close until they were both breathing heavily. Finally, Drake could not hold back any longer, filling Tony’s mouth and throat. Soon Tony followed, emptying himself into Drake’s mouth. When it was over, both flopped back on the bed, slowly coming back to Earth.
Damn, just what I needed. I am so relaxed I could take on the world Tony thought as he absentmindedly rubbed Drake’s leg. “Do you have to work tonight?”
“No, this is my night off, why?”
“Well, I thought we could rest and recuperate, then take a shower together, and order room service….and play some more,” Tony suggested. “That is unless you have plans tonight,”
Drake did not want to appear too anxious but he did want to spend more time with Tony. And the shower sounded heavenly. “That sounds awesome,”
Tony turned around in the bed, scooting close to Drake, kissing him lightly while running his hands up and down his hip to his upper thigh. “Ah…do you….ah….” Tony stammered, not sure exactly how to ask the question as this was his first pickup. Generally, he used an escort service when he was on the island and they knew exactly what he wanted.
Drake laughed and said, “Not sure what you are trying to ask but yes, I am both. What about you?”
“Giver,” he answered. “Sorry, I don’t mean to sound so awkward but you are my first pickup,”
Drake pulled his head back and looked Tony in the eyes. “Why me?”
“I am not sure. I was just attracted to you like a magnet but honestly, I figured you were straight.” Tony said. “But I am glad things worked out the way they did,”
“Me too,” Drake said leaning in to kiss him. “Have you ever thought about being a receiver?”
Tony could feel his face flushing as he looked down at the comforter. “Yeah, but been a bit scared to try.”
“I was too the first time I tried it but there is no other feeling like it. If you decide to try it, find someone who is patient and gentle,” as he rolled off the bed and went to the bathroom.
Tony soon followed and they took a shower together, doing a lot of kissing and touching but neither had the desire to go farther. They wanted to wait until later for more fun. Curling up on the bed together, they looked at the menu and Tony placed their order. They ate and then began to kiss and make-out, not holding back this time. After several minutes of intense foreplay, Tony extracted himself from the bed and went over to his suitcase, bringing back some packs of condoms and a bottle of lube.
Drake crawled to the end of the bed and drew Tony into his mouth, his tongue swirling all around it. Taking just the head and sucking it almost caused Tony to drop the supplies in his hands. Pulling back and sitting on his heels, Drake smiled at him.
“Someone looks like they are ready for some more action,” as he reached out and ran his fingers lightly over the shaft.
Tony stared at Drake for several long moments before saying, “Teach me,”
Drake reached out, took the stuff from his hands and put everything on the nightstand, then patted the bed. While Tony got settled, Drake put lube on his three fingers. Leaning down, he began to work his cock before sliding one finger inside. Once he was comfortable with that, Drake put another one inside, and finally the third.
“Put a condom on me and lube it,” Drake instructed.
Once he was ready, he moved between Tony’s legs, bending them forward toward his chest. Pulling his fingers out, he slowly pushed himself inside, taking it nice and slow until he was all the way in.
“Are you okay?” Drake asked as he moved a little.
When Tony nodded his head, Drake began to move in and out, slowly at first but gradually increased his speed. Tony reached down and began to stroke himself. As Drake reached the point of no return, he gave one final thrust and emptied himself in the condom. Very slowly he pulled out and took the condom off, taking it to the bathroom. Coming back to the bed, he watched Tony stroking himself, his eyes closed.
Removing his hand, Drake replaced it with his mouth until he got him just to the edge before stopping. Quickly he grabbed a condom and put it on his shaft, then lubed it up, laying down beside Tony, turning his back to him. Tony put some lube inside of Drake before he slipped his cock in. Drake let out a moan and squeezed his ass together against Tony’s shaft.
Tony draped his arm over Drake’s hips as he worked himself in and out, slow and steady until he found release. After he disposed of the condom, they laid facing each other, rubbing each other’s sides, kissing until they drifted off to sleep.