"What time is it?" Steven asked, wondering if Andrew the waiter would be coming.
"Eleven-Thirty, why do you ask? Hamish responded whilst standing by the bedroom door, naked but holding something Steven couldn’t quite identify.
"Just wondered that's all and I'm also wondering, what do you plan to do with Andrew, after all you must be exhausted after your efforts with me."
"Well, the thing about Andrew is he likes to be spanked and over the years, I have been on a journey to satisfy his desires as well as mine but tonight I would like you to help with his needs because he likes a bit of ritual when being spanked."
"Hamish, what do you mean ritual and I'm not sure I can, my prick is quite sore from your dealing with me, and I don't normally fuck guys anyway."
"I will be fucking him so don't you worry about that. However, put this on and I will explain,” as Hamish handed Steven a black gown. “I want you to assist whilst I spank him. Will you be able to manage that?" Hamish asked with a hint of irritation in his voice.
"Don't see why not, it’s only assisting someone being spanked." Steven said with confidence. “But why the gowns though?”
"Well...the gowns provide Andrew with a ceremonial ritual, of being prepared for a judicial spanking and I will be using this," as Hamish produced a leather tawse handing it to Steven whilst Hamish slipped on a black gown that came down to just above his knees.
Steven looked at the tawse, his heart jumping a beat as he gently slapped his palm with it. The sting was surprising, and he couldn't help but imagine what it would feel like across bare flesh.
Hamish explained, his voice firm. "It's an old-school Scottish implement, and Andrew loves the feeling of it on his backside."
"But what if it hurts him?"
"That's the whole point of it Steven and if you assist and prepare him well enough, it adds to his enjoyment, the ceremonial ritual. Now, put the gown on before he arrives."
He took a deep breath and nodded. "Okay, I'll do it," as Steven slipped the gown over his head allowing it to fall to his knees.
Hamish and Steven looked at each other in their gowns which looked like short dresses or ritual robes depending upon a point of view and they both smiled with an element of amusement.
Just as the clock struck midnight, there was a gentle knock on the door. Hamish answered it, and Andrew, dressed in a white gown of the same design, stepped into the room. His eyes went wide when he saw Steven standing there, looking like a judge holding the tawse. "Hi, Sir," he said, his voice a little shaky as he looked at Hamish dressed like a judge too.
"Good evening, Andrew," Hamish said with a smile. "You know why you're here Andrew?"
Andrew nodded, his cheeks flushing a deep red. "Yes, Sir."
Hamish continued "I reviewed the letter you sent to me that outlined your transgressions since the last time we met, and I must confess it was pretty comprehensive. I have discussed my findings with my colleague here and he agrees that such transgressions cannot go unpunished. Steven, show Andrew the extra heavy leather tawse."
Steven held up the tawse showing it to Andrew who looked at it with awe and fear at the same time.
Hamish thought for a moment. "The laws of Scotland provide that the number of strokes depends upon the nature of the offences and since you have transgressed on multiple misdemeanours the only option we have is, you will receive 36 strokes which is the maximum provided by the ancient law."
"Yes Sir, I know, and I need it in order to atone." Andrew declared dropping his eyes to the carpet.
"Very well Andrew, follow us down the hallway."
Hamish led the way walking down the hallway to a room at the end and keeping the door open, Andrew and Steven followed. Steven's heart dropped when he saw the large wooden bench with leather padding, wondering how Andrew was feeling.
"Right Andrew, stand in front of the bench please." Hamish directed.
Steven became intrigued as Andrew stood at attention, his erection clearly visible, sticking out pushing the cotton fabric of his white gown. Steven looked at the young man, guessing he was slightly older than himself and how would he take the spanking, equally aroused and noticing that Hamish was likewise, excited from a physical perspective.
Hamish then approached the waiter and started a basic medical check commencing with his blood pressure and heart rate with a standard machine anyone can buy from Boots the Chemist. Hamish then used a stethoscope listening to Andrew's heart and chest.
"Andrew, you seem to be in perfect health although your blood pressure is a little elevated. Any reason why?
"Not really Sir, I guess it’s the anticipation of being spanked." Andrew responded as fairly and confidently as he could.
"Very well, let's proceed." Hamish announced.
"Steven, please prepare Andrew for his spanking."
Steven took the blindfold and standing behind Andrew covered his eyes trying it off at the back. He then took Andrew's arm and led him to the bench, placing his hand on his back pushing him down onto the bench. Andrew's chest was well positioned on the leather as Steven fastened the first wrist restraint and then moved round to the other side, repeating the process ensuring that Andrew was secure but comfortable.
Steven then secured Andrew's ankles in the same fashion as the wrists leaving Andrew bent over and secured but still in his gown which Steven now turned his attention too by unbuttoning the material on the shoulders allowing him to pull the gown down allowing it to drop to the floor.
Andrew was now naked and ready as Steven stepped back to watch, something that he had never done before as he confirmed, "Andrew is ready to receive from your hand his punishment."
Hamish stepped towards Andrew, positioning himself within range and then he raised the tawse, feeling the weight of it in his hand. He took a deep breath and brought it down, watching as the leather made contact with Andrew's skin. The sound was sharp, followed by a gasp from the waiter. The redness began to spread, and he felt a strange mix of power and excitement.
Hamish continued to spank Andrew, each stroke a little harder than the last, watching the pattern of red marks form. Andrew's gasps grew louder, his body jerking with each stroke. It was clear he was enjoying it but not enjoying it if that makes sense, and Steven found the sight incredibly arousing as he stood there fully erect and proud under his own nightshirt.
As Hamish's arm grew tired, he took a short break. "Good boy," he murmured, stroking Andrew's flaming cheeks before resuming the deliveries that Andrew desired.
The next few minutes were a blur of sensation and sound, the rhythmic smack of the tawse punctuated by Andrew's screams as the pain became intense mixed in with his pleas to stop. The atmosphere in the room was electric, charged with sexual tension and the scent of desire as Andrew wet himself as he started to dribble with each stroke, but the flood gates had been opened as warm water gushed from Andrew's cock with total loss of bladder control. Down his legs the warm water ran pooling on the floor where his nightshirt lay, wetting the cotton material and turning it slightly yellow.
Hamish finally called a halt at 36 strokes, and Andrew's ass was on fire, a deep shade of red that Steven had never thought possible, and he was panting heavily when Steven released him from the restraints. "Thank you, Sir," he managed to gasp as he stood up and looked at Hamish. Hamish though was breathing hard from the effort and just nodded to Andrew in recognition.
Andrew stood trying to sooth his bottom with his hands, his cock remaining flaccid from the pain and associated distraction. Steven stood trying to sooth his excitement from what he had witnessed, his erection still extremely hard and leaking.
“Andrew, you have taken your punishment well, you will now prepare us for the next stage.” Hamish told him.
Andrew walked over to Steven and kissed him whilst unbuttoning his gown allowing it to drop from his body. He then approached Hamish repeating the process leaving him naked too as both men displayed their sexual readiness for the next part of the play.
"Let's take this to another less formal room," Hamish declared, turning, and leaving the room that smelt of sex, sweat and urine.
Into the bedroom they went, Steven noting that Hamish had already bent Andrew over the bed, and as the waiter moaned in pleasure, he sank his teeth into the tender flesh of his neck, marking him as his own. Then, with a wink to Steven, he slid his cock into Andrew's willing hole, his hips moving in a steady, powerful rhythm.
Steven watched, his cock hard. He knew that this was just the beginning of his education in the ways of pleasure and pain, and he couldn't wait to see where it would lead him.
The sight of Hamish fucking Andrew was too much. His cock pulsating and his balls aching with precum oozing from the tip, increasing in flow the more he watched. He reached to the bedside table and grabbed the prostrate massager that had been used earlier and gently inserted it into his own body and turned it on as he viewed the scene before him. The effects of the device were immediate as he watched as the older man's muscular body moved in sync with Andrew's, the younger man's cries of pleasure mingling with the slap of skin on skin. It was raw and primal, a dance of dominance and submission that had him on the edge of his seat.
"Come here boy," Hamish growled, beckoning to him with a curl of his finger. "I want you to watch closely."
Steven moved onto the bed, massager still active inside, his eyes locked on the sight before him. He had never seen anything so erotic, so intense, and it was all happening right here, with him as an active participant. "Hold him down for me, he's moving too much" he instructed, and Steven complied, placing a firm hand on each of Andrew's shoulders as the device had a firm hold on Steven's gland.
The pressure of Andrew's body beneath his hands and the sight of Hamish's cock pumping in and out of him was too much for him to handle. With a groan, Steven came, his seed spurting out and landing on Andrew’s head and shoulders. The smell of sex filled the room, mingling with the scent of the hotel's no so clean linen anymore.
Hamish noticed "Looks like you enjoyed the show," he said, his eyes gleaming with mischief. "But it's not over yet. Keep that thing in you boy until I tell you otherwise." and with a flick of his wrist, Hamish grabbed the remote of the massager whilst still fucking Andrew, from the bedside table and turned the setting up to maximum. The hum grew louder, and Steven felt his cock twitch in response even though he had just shot his load.
"On your knees boy," Hamish ordered, and Steven eagerly obeyed climbing off the bed to kneel next to the older man. He watched as Hamish slid back and forth into Andrew, the waiter's body arching up off the bed with each thrust of Hamish's cock.
The tension in the room was palpable as the vibrations grew stronger, and Andrew's cries grew louder from the cock inside him as it touched his p-spot with every thrust. Hamish's hand came down on Andrew's ass, adding to the sensation, and the sight was too much for Steven with the device still on and buried inside him.
The waiter's moans grew more desperate, and Hamish leaned down, whispering something in his ear that Steven couldn't quite make out. Andrew's body jerked, and with a final, keening cry, he came, his orgasm spilling out onto the bed in the heaviest spurts of cum that Steven had ever witnessed and what's more, Andrew just kept spurting cum with each thrust of Hamish's cock as if he were being pumped and milked dry.
Steven still kneeling where Hamish had told him too, shot a final load thanks to the device, landing cum on the feet of the older man some two feet away. Almost at the same time, Hamish came with a noticeable grunt and groan filling Andrew’s arse with warmth and cum that Andrew had craved since his arrival.
Hamish collapsed onto Andrew. Steven collapsed onto the carpet still with the device at maximum and Andrew laid flat on the bed groaning feeling spent, exhausted and panting whilst Hamish, on top of him, licked Steven's cum from his back after his earlier deposit.
Steven though was sort of in trouble as he lay there, his body jerking from the continued orgasm he was experiencing, his moaning and groaning evidence of his plight. still erect and throbbing as the device refused to die from over use.
Hamish and Andrew had seperated and they both laid on the bed watching Steven on the carpet begging for an end, the shocks and aftershocks of pleasure still reverberating through his body. "I think we've had quite the evening but I guess Steven, you still have a while to go before I allow you to remove that device," Hamish murmured, his hand tracing patterns on Andrew's back as they both watched.
"You can say that again," Andrew managed to gasp out, his voice hoarse from screaming. "But I'm not sure he can take much more."
Hamish chuckled. "Don't worry, laddie, he will be fine. Let's just watch what happens."
The room was quietening down, the only sound their ragged breathing and Steven continued torture. And then, as if on cue, Steven experienced his first dry orgasm in years, a testiment to the milking he had received during the course of the evening. Hamish feeling satisfied, hit the remote stopping the device as Steven laid there desperately trying the catch his breath, his torture at an end as he managed to pull it out. It was then, the three of them burst into laughter, the tension dissipating into the night air.
Steven recovered sufficiently enough to climb onto the bed and kissed the two men with a new level of passion that had been unlocked that evening. Hamish laid in the middle with his boys either side of him. Steven played with Hamish's pubic hair and cock whilst Andrew was deployed circling and pinching Hamish's nipples with his fingers. Slowly but surely, the exhuasted men drifted off to sleep, tired from their exertions and the lateness of the hour, spent and satisfied physically and emotionally.
Steven woke up early and climbed out of bed as quietly as he could and crept towards the door collecting his clothes that lay all over the place. He paused at the door gazing upon the sight of the naked men in bed, sound asleep and he was proud he had been part of the event. As he walked out of the hotel, he could feel cum still dribbling out of him, his cheap white briefs soaking up the evidence. Finding it erotic, he decided not to shower and to enjoy the smell and feeling of drying cum on his body for the day ahead. He felt changed, like he had unlocked a part of himself that had been hidden away.
He knew that this was just the beginning of his journey with Hamish and Andrew, and he was ready for whatever the older man had in store for him. The highlands had changed thanks to Scotrail’s service from Glasgow to Oban.
