The train pulled into Oban station, the air outside cool and brisk. As they gathered their belongings, Hamish handed him a business card. "Just in case you get lost," he winked.
Steven stepped onto the platform and watched as Hamish disappeared into the crowd, feeling a mix of excitement and trepidation but he had something urgent to attend too as he walked off towards the local menswear shop.
Steven headed straight for the underwear section, his mind still reeling from the encounter. The shelves were lined with an array of Scottish-themed boxers and briefs, but he had something more practical in mind and a lot cheaper than the tourist underwear on prime display.
He scanned the options, his eyes finally settling on a simple, cheap packet of three white briefs. They were nothing special, but they served their purpose. He paid for them, his hand shaking slightly as he took the change from the cashier. Steven then made his way to the changing rooms and put on a pair, noting his cum had dried from the handjob on the train as he restored his personal comforts and stuffed the remain two pairs into his backpack.
His thoughts kept drifting back to the evening's rendezvous with Hamish that was on offer. Should he or should he not attend. "Bugger it," Steven thought to himself. "I have no plans this evening so, what the fuck, why not see what happens."
The Oban Bay Hotel stood majestically by the harbour, the sun dipping low in the sky casting a warm orange glow across its façade. Steven checked his watch, it was 6:45pm and he had developed an erection just thinking about the meeting as he entered the bar of the hotel.
The bar was a mix of locals and tourists, the air filled with the comforting scent of peat smoke and the distant sound of a live folk band. His eyes scanned the room, searching for the familiar face, and then he saw him. Hamish sat at a corner table by the window that overlooks the sea, a pint of beer in hand.
Steven walked over, trying to compose himself, and said hello. Hamish looked up, his eyes lighting up in recognition. "Ah, you found the place. Have a seat," he said, patting the chair next to him.
"I did thank you, and I was able to buy some cheap briefs on the way here as well."
That comment broke the ice as they began to chat, the conversation took a more intimate turn. "So, tell me, how old are you?" Hamish asked, his eyes sparkling with curiosity.
"Twenty-five," Steven replied, taking a sip of his whiskey. "And you?"
"Fifty-five," Hamish said with a wink sending a thrill through Steven's veins. "Out of interest, what briefs did you buy on the way here?"
"Nothing special Hamish, cheap pack of three white briefs for £4.99. They will do until I get my y-fronts back."
Hamish leaned back in his chair, a knowing smile playing on his lips. "Well, you've got good taste in whisky," he said, raising his glass in a toast. "And I'm sure you've got good taste in men, too."
Steven felt his heart racing as he took a deep breath and met Hamish's gaze. "I guess I do," he murmured, the memory of the morning's encounter still fresh in his mind. "What sort of underwear do you wear Hamish?"
The older man chuckled, a twinkle in his eye. "Ah, that's for you to find out later, if you're a good boy." He took a sip of his beer having finished his whisky, his hand casually brushing against Steven's thigh. The simple touch sent a bolt of desire through him, and he found himself leaning in closer, eager to explore this connection.
"What happens Hamish if I'm not a good boy?" Steven asked in a cheeky shy manner. "Does that mean I won't get to find out later what underwear you wear?"
Hamish's smile grew wolfish as he leaned closer, the heat of his breath tickling Steven's ear. "Perhaps naughty boys get punished," he whispered, his hand moving higher up Steven's thigh.
Steven felt his cock twitch at the thought, his excitement building. He'd never been with an older man before, let alone one so confident and self-assured. The thrill of the unknown sent a shiver down his spine. "Sounds good to me," he agreed, his voice betraying his nerves.
They finished their drinks and made their way to the elevator, the anticipation thick in the air between them. The elevator ride was silent, the only sound the hum of the machinery and the occasional ding as they passed each floor. When the doors slid open, Hamish led the way to his room, swiping the card key and pushing the door open with a flourish.
The room was a beautifully decorated suite, with a large four-poster bed dominating the space. A faint scent of sandalwood filled the air, a stark contrast to the masculine scent of the bar. Hamish turned to face Steven, his hand reaching up to cup his cheek. "You're so young, so innocent," he murmured, his thumb tracing a line over Steven's bottom lip.
Steven felt his body respond, his cock stiffening against the fabric of his new briefs. He leaned into the touch, feeling the warmth of Hamish's hand, and kissed him tentatively. The kiss grew deeper, more urgent, as their tongues danced together, exploring the depths of each other's mouths.
With a gentle tug, Hamish undid the belt on Steven's kilt, allowing the garment to fall to the floor. The sight of the young man's bare skin in the dim light was intoxicating. Steven's legs were muscular, the hair on his thighs a soft caress against Hamish's palms as he traced the line of his briefs.
"Let's get these cheap briefs off you, shall we?" Hamish murmured, his voice a seductive purr that sent a thrill through Steven's body. He hooked his thumbs into the waistband and began to peel them down, exposing the hard, eager cock that had been straining against the fabric all day.
As the cheap briefs fell to the floor, Hamish stepped back and smiled. "Now, isn't that a sight for sore eyes?" He stepped closer, reaching out to stroke the soft, curling hairs around Steven's cock, which was now fully exposed and standing tall and then he lifted Steven vest and hoodie up and over his head in one fluid move. Now he was naked and more than ready for what was going to come.
But the real surprise came when Hamish himself started to undress. With a wink, he dropped his trousers, kicking them off, revealing not just his own burgeoning arousal, but also the y-fronts that had been the topic of their earlier conversation. "Look what I've been keeping warm all day," he said, his voice a low growl that sent a thrill through Steven's body.
The sight of the man wearing his y-fronts was more erotic than he could have ever imagined. It was like a secret part of him was on display, a symbol of their shared experience. Hamish noticed the look on his face and chuckled. "It's not often you find someone who fits into your kinks so well," he said, stepping closer to him.
With a gentle push, he guided Steven towards the bed. The mattress was soft, the sheets cool against his skin as he lay down, his legs parted slightly in anticipation. Hamish stood over him, his cock jutting out from the white fabric of the y-fronts, already straining against the material.
He climbed onto the bed, straddling Steven's waist. He leaned down and kissed him deeply, the fabric of the y-fronts the only barrier between them. The weight of him was surprising, comforting almost, as if this stranger were claiming him. Then, with a sudden movement, Hamish pulled down his y-fronts, releasing his cock.
It was thick, veiny and a good nine inches, a stark contrast to Steven's own average length. His eyes widened in a mix of fear and excitement as Hamish positioned himself between his legs, squeezing some lube onto the tip, disgarding the tube onto the floor, his cock poised at his entrance. He took a deep breath, feeling the blunt tip pressing against him, the anticipation making his stomach flutter.
With a liberal measure of lube and a gentle push, Hamish entered him, the pressure building until he was fully inserted as Steven laid on his back. The pain was intense, but it was quickly overridden by the feeling of fullness, of being claimed by this hugely endowed man he barely knew. He felt his body stretch around the intrusion; the sensation overwhelming.
As Hamish began to move, he found a rhythm that seemed to resonate through his entire being. The pressure grew, building until he thought he might break. Then, without warning, it washed over him, a wave of pleasure so intense he cried out. It was his first prostate orgasm, a sensation that had him seeing stars as he shot his heavy load onto his stomach almost reaching his face.
Hamish watched him cum as he continued fucking the boy, the sound of skin slapping against skin filling the room, the scent of sex heavy in the air. Hamish's strokes grew deeper, harder, his breathing ragged. And then, with a final, powerful thrust, he came, filling Steven with his warmth.
Hamish stayed inside the boy as he colapsed on his stomach, panting and sweaty as they caught their breath. Rolling onto his back, Hamish laid there as Steven gently played with his cock waiting for new signs of arousal in the older man which surprisingly didn’t take long. Hamish leaned down and kissed him, a soft, gentle kiss that spoke of satisfaction and a job well done. "I think I’m ready for round two, if you are?" he asked, his voice a low, seductive murmur that had Steven nodding eagerly.
Hamish got off the bed and pulled Steven up to stand as he picked up the y-front briefs, he had worn all day and tied Steven's wrists behind his back, the fabric feeling rough and comforting against his skin. He then used the cheap briefs and turned them into a blindfold so Steven couldn’t see, ripping the material to meet his needs. He then guided Steven to the edge of the bed, bending him over so that his ass was in the air, exposed and vulnerable. "Now, let's see how much of a Highlander you really are," he teased, his hand giving a firm slap to one cheek.
Steven gasped, the sting of the slap melding with the lingering pleasure from their first encounter. He felt Hamish's cock, now fully hard again, press against his opening. This time there was no gentle easing in, no sweet caresses to prepare him. Instead, there was a single, sharp thrust that had him crying out as Hamish used the oozing cum for lubrication.
The man took him without mercy, his powerful hips pounding into him, each stroke sending a jolt of pain and pleasure that made his legs tremble as the cock buried itself deeply into Steven. He could feel his own cock growing hard again, slapping against his stomach with each impact as his chest moved back and forward on the edge of the bed. The sound of their bodies colliding and the grunts of effort from the fucking filled the room, a primal symphony that seemed to resonate in his very soul.
The aggression in Hamish's movements was thrilling, a stark contrast to the gentle, tender man he had been earlier in the day. It was as if the wildness of the Highlands had seeped into his very being, claiming him in a way that was rough, terrifying and exhilarating.
Steven's moans and grunts grew louder as the pleasure began to build again, his body responding to the raw, animalistic need that seemed to drive them both. He could feel the knot of tension coiling tightly in his stomach, the pressure building as he approached his second orgasm.
With each thrust, the head of Hamish's cock grazed his prostate, sending sparks of pleasure shooting through him. His body was a live wire, every touch setting off explosions of sensation. He knew he wouldn't last much longer, the intensity too much to bear.
And then, as if sensing his impending climax, Hamish thrust even harder and deeper as he spoke. "Cum for me, laddie, cum for daddy," he growled, his voice a demand that Steven couldn't ignore.
With a final, desperate cry, he did just that, his body shuddering with the force of his release. The warmth of his seed spurted out onto the bed, mixing with the sweat and their combined scents. Hamish followed, his own orgasm tearing through him, his hips stuttering as he filled Steven once more.
Hamish collapsed onto Steven's back, both spent and satisfied and their breathing loud and urgent as they slowly recovered. "How was that boy?" Hamish asked whilst scratching hard, his nails digging into the back that supported him. "Now I have a real surprise for you boy," as Hamish left steven slumped over the bed trying to breath normally.
Hamish walked over to his suitcase and lifted out a bag of toys and with a smile on his face returned to Steven's slumped body with a prostate massager.
"I know you enjoyed that, but I want to show you something else," Hamish said, his voice thick with lust. "This little beauty is going to make you scream for me, in the best possible way."
Steven felt a jolt of excitement mingled with apprehension as Hamish described the prostate massager. It was a sleek, black device with a hugely curved tip, the very thought of it making his stomach flutter. He had heard about such things before but never experienced one firsthand.
Hamish applied some extra lube even though Steven was still oozing cum from his hole and gently inserted the whole device into him. "Ready boy? I'm going to turn this on and sit in the chair and watch you lose control and cum again whilst I have a drink from the mini bar."
The moment the vibrations started, Steven felt a jolt of pleasure shoot through him, his body tensing as the massager found his prostate with unerring precision. The sensation was overwhelming, like nothing he had ever felt before. The y-front briefs that bound his wrists were soaking wet with sweat, and he could feel the fabric sticking to his skin. The cheap briefs still providing no visual reference and he was oblivious to Hamish getting a whisky from the mini bar and the fact that he now sat, watching Steven bent over the edge of the bed being fucked by a machine.
After what seemed an eternity, Steven tried to hold back his feelings, to savour the moment, but the power of the device was too much as hamish increase the vibration level with the remote. His body began to convulse, his cock jerking as the pleasure built to an unbearable crescendo. Hamish sat in the chair, his eyes never leaving Steven's face, his own cock hardening again as he watched the younger man's reaction.
Steven grunted louder as the vibrations grew stronger, the intensity of the sensation increasing with every passing second. His moans grew louder with another remote increase of the vibrations, filling the room like a symphony of desire. His eyes rolled back in his head, lost in the waves of ecstasy that crashed over him.
With a final, desperate thrust of the massager, Steven came again, his body shaking with the force of his orgasm. The pleasure was so intense it was almost painful, his muscles clenching around the device as he shot his load onto the bed again. The sound of his moan was lost in the buzz of the toy, his body arching as he rode out the waves of his climax as the device continued doing what it was designed to do.
Hamish took a sip of his whisky, his eyes never leaving the spectacle before him. He watched as Steven's body failed to relax as the device still vibrated but now Steven was begging for an end. "Please Hamish, please, I can't take anymore. Please stop it."
Hamish being a caring gentle lover felt sorry for Steven and clicked the stop button on the remote. "Good boy," he murmured, his voice filled with satisfaction. "You took that like a champ." as he gently removed it, setting it aside on the bedside table. Then, he leaned down and kissed Steven, tasting the salt and sweetness of his sweat. "Now, let's get you cleaned up," he said, his voice tender as he removed the blindfold and wrist restraint leaving Steven bent on the bed still, to recover his breathing.
They bathed together, but Hamish took the role of washing away the remnants of their passion from Steven’s body who couldn't help but feel a sense of camaraderie with this man who had taken him to such heights. It was a strange mix of comfort and excitement that left him craving more.
After drying each other, Hamish laid Steven down on the bed whilst he ordered room service. A meal for two and after a while and with the knock at the door, Hamish allowed the waiter into the room.
The waiter looked at Steven lying on the bed, his flaccid cock clearly on display and Hamish only wearing only a towel. "Put the tray on the table please," Hamish asked the waiter. Steven looked at Hamish, mortified that he had been seen by the waiter, but Hamish was quick to assured him, "It's fine Steven, Andrew won't say anything because I normally use him for similar sessions and besides, I own the hotel. Isn't that right Andrew?"
"Yes Sir." Andrew agreed.
"What time do you finish work this evening, Andrew?"
"Midnight Sir," he answered.
"Well, if you fancy some fun, why not knock on the door later." Hamish suggested as he closed the door to the suite as Andrew the the waiter left.
"Do you think he will come back after work?" Steven asked Hamish, liking the idea it might become a threesome for the rest of the night.
"Almost certainly Andrew will come after work. He loves the attention and the overtime I pay him." watching Steven get off the bed, his beautiful body on full display as he sat down at the table.
Hamish and Steven enjoyed the meal and as they finished their dessert, Hamish leaned back in his chair, holding the y-fronts that had been used by Hamish and Steven, "These have served their purpose," he said, “But I think I'd like to keep them as a souvenir."
Steven blushed, his cheeks reddening as he felt ownership of his y-fronts slip away. "If that's what you want," he murmured, his voice still husky with desire.
"Oh, it is," Hamish said with a smile. "And perhaps, we can use them on Andrew later.
