A West Highland Journey

This is part 1 about Steven on a train from Glasgow to Oban. He is joined by another traveller who asks a question, do men wear underwear under a kilt. He soon finds out they do but they are also quick to give them up.

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"You're brave, wearing a kilt in this weather," the burly man said with a chuckle, nodding at Steven's attire as he settled into the train seat beside him. The early morning air was brisk, hinting at the autumn chill to come.

Steven, a bit taken aback, glanced down at his outfit. Most were in jeans and sweatshirts, but Steven always wore a lightweight kilt in summer. It was a nod to his heritage, a declaration of pride. "Aye," he responded with a smile, "But it's not every day you get to ride the West Highland Line."

The man's eyes twinkled with mirth as he extended a hand. "Name's Hamish. On my way to visit family. What about you, lad?"

Steven took his hand firmly. "Steven. I work outside Oban for the Forestry Commission." As the train jolted to life for the start of the journey.

Their conversation grew more comfortable with each passing mile, the clatter of the train's wheels setting a steady rhythm under their words as they enjoyed the majesty of the Scottish landscape, their shared love for whisky, and the peculiarities of Scottish cuisine.

The scenery was so mesmerizing that Steven didn't notice Hamish's hand brushing against his leg. "Stunning, isn't it?" Hamish said, his voice dropping an octave. "The Highlands have a way of getting under your skin."

Steven nodded; his eyes still glued to the passing view. He felt the warmth of the hand, an unexpected gesture, and for a moment, he wasn't sure how to react. But then he looked over at Hamish, whose gaze had shifted from the scenery to him. There was something in his eyes that made Steven's heart skip a beat.

"It is true what they say that men don't wear underwear underneath a kilt?" Hamish asked.

Steven blinked, torn from his reverie by the sudden question. He felt the heat rise to his cheeks and took a moment to gather his thoughts. "Well, some do, some don't. It's a matter of personal preference. I do as I find it more comfortable and less breezy."

"That makes sense,” Hamish replied, “what sort of underwear do you wear? Let me guess...you look like a boxer briefs guy I suspect. Probably an age thing and modern fashion." 

Steven felt a flash of annoyance at the assumption but kept his tone light. "Nope, just regular white y-fronts. Keeps things simple." 

"Marks & Spencer or Jockey? Hamish enquired. 

Steven chuckled despite the awkward turn of the conversation. "Neither brand. I wear a bespoke brand made by a guy on Etsy. Really comfortable, well-made and they last longer than regular high street names. Let me give you the website address and you can have a look."

“That’s okay laddie,” the man's hand remained on his knee, the playful tug on the hairs a silent question.

"You know, I've always wondered what it feels like to wear a kilt. It must be easier than wearing trousers," Hamish murmured, his gaze locked with Steven's. His hand began to move, ever so slightly, up his thigh, the fabric of the kilt shifting with the movement.

Steven's breath caught in his throat, his eyes darting around the mostly empty carriage. No one was looking. The heat from Hamish's hand was unmistakable, a stark contrast to the cool morning air. He felt his pulse quicken as the man's fingers moved under the hem of his kilt moving slowly until it rest on the thigh band of Steven's y-fronts.

"I like what I'm feeling," Hamish whispered, his breath warm against Steven's ear. "We're just two friends sharing a wee moment and this friend would like to explore more?"

Steven's cheeks flushed, but he nodded, his body responding to the thrill of the unanticipated intimacy. The hand grew bolder, moving over the top of the cotton material until his hand reached Steven's erection hidden underneath his y-fronts.

"Is that for me?" Hamish teased, a hint of a smirk playing on his lips. "I can feel you have developed quite a damp patch on your y-fronts. Been leaking for quite a while, have you?"

Steven's eyes widened, and he swallowed hard. He could feel the fabric of his underwear sticking to him, a clear sign of his arousal. He nodded, his voice a hoarse whisper. "I... I guess so."

"Let me help you with that then. Nothing worse than a leak if you know what I mean," Hamish suggested. "If you stand up, I can pull your y-fronts down for you, so they don't get too damp."

Steven hesitated for a moment, the words hanging in the air, but he found himself standing up as Hamish's strong hands slid up Steven's thighs and pulled his y-fronts down, letting them drop to his ankles as Steven stepped out of them and resumed his seat.

"Better now?" Hamish whispered, his hand lingering.

"Yes, much better thank you," Steven replied.

Hamish's hand slid under the kilt, to embrace the firmness of Steven's cock in a smooth motion. The coolness of the air was replaced by the warmth of Hamish's palm as it wrapped around his shaft, sending a jolt of pleasure through his body. His cock responded eagerly to the touch, growing harder and thicker in the confines of his kilt.

Steven gripped the armrest, as his breath grew ragged as Hamish's grip tightened and his strokes quickened. He could feel the tension building within him, his body coiling like a spring ready to release. Hamish’s finger played with the precum oozing out of the tip, more a flow than a dribble by then.

The pressure grew unbearable, his hips moving almost imperceptibly to meet the rhythm of Hamish's hand. His heart hammered in his chest, and he could feel his orgasm approaching, unstoppable and overwhelming. He bit his lower lip, his eyes squeezed shut as he tried to keep his face neutral, his hand tightening on the armrest.

"You're so hard," Hamish murmured, his voice low and full of approval. "You're going to cum for me, aren't you?"

The question sent a bolt of lust through Steven, and he nodded, unable to form coherent words. The hand around his cock tightened, the strokes grew faster, and he knew he couldn't hold on much longer.

He felt his orgasm build, the base of his cock tightening, his balls drawing up. And then, with a strangled cry that was barely contained by the fabric of the kilt, he came shooting his load in multiple spurts of cum that shot up onto the woollen material of his kilt. “So much cum, wow, you really needed the release me thinks,” as Hamish's hand continued to stroke him through it, milking every drop of pleasure from his body. Steven's head fell back against the seat, his eyes still squeezed shut as he rode out the waves of his climax.

When he finally opened his eyes, the scenery outside had changed again. The fields had given way to the rugged beauty of the Highlands, the mountains now much closer. The mist had lifted, revealing a landscape that was both harsh and breathtakingly beautiful, much like the experience he had just shared with the man beside him.

Steven took a deep breath, his chest still heaving. He looked over at Hamish, who was watching him with a knowing smile with cum on his hands, licking it as if he were finishing a chicken bone. “Yum, tastes nice.”

"Thank you," Steven managed to murmur, his voice still thick with lust and his groin damper than when he started his journey.

Hamish leaned in, his voice a gentle rumble. "The pleasure was all mine, laddie. Now, I shall keep these y-fronts and if you want them back, come to the Oban Bay Hotel this evening at about 7pm and I will be happy to put them back on for you."

"Maybe I might take you up on that offer Hamish," Steven responded with a smile on his face. "Until then, let's just enjoy the scenery and perhaps we can get a coffee from the buffet."

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