Master humiliates two subs together

This is a fantasy that involves me Malcy, my regular Master and an anonymous other sub who we will call Greg.

Some time back I got to hear of my Master making arrangements to meet a new sub. The guy was in his early thirties, fit and had a large cock – or at least that’s what he’d told Master. He was a Friend of Dorothy’s and very much out. He said he was keen to explore some BDSM including some restraint by ropes. He had told Master that he hadn’t experienced anything like that before but had fantasised many times about participating in something like that and was keen to make it happen.

Master had talked him into letting him rip his clothes from him before tying him up and accordingly, he would come dressed in clothes he did not mind being destroyed and with a change of clothes to go home in afterwards. The arrangements for the meeting had been fleshed out in several WhatsApp messages back and forth over a couple of weeks.

In the end, Master had arranged to meet Greg at a beachside shelter on the promenade of a little seaside village on the South coast of England. Master has a cottage, that’s not his main residence not far from there - within walking distance. They would meet on a Sunday morning when it was quiet. Partially strip Greg by cutting and removing some of his clothing there before a humiliating walk over the short distance to the cottage.

It being Sunday morning it was unlikely that they would meet anyone but there was always the risk that they might bump into someone out walking. That all added to the initial thrill of the session – the fact that they might be seen from a distance or even passed by. It was the type of village though that most people would just walk on and ignore what might be happening in the shelter at that time of day!

The shelter faced out to sea and had a bench seat along one side under a short roof. There was a full wall with no windows between the bench and the roof. If you were walking along the promenade on the other side you would not know there was anyone in the shelter. Walkers, runners and cyclists could however pass on the seaside of the shelter and see what was going on. Also, anyone walking along the beach could see quite plainly into the shelter. Both Master and Greg knew there were risks but were willing to take them to experience the thrill!

Master had also started many sessions with subs like this before and had never been caught although had experienced passers-by who had looked but continued walking or jogging. This had been fully explained to Greg but he was still up for the meeting – I suspect more for what had been promised afterwards at the cottage!

As I said I had gotten to see the WhatsApp messages by accident and had made a suggestion to Master about enhancing the session by joining in. 

The suggestion was that I act as an innocent passer-by – who doesn’t in this case pass on by but rather joins in and we don’t tell Greg that I am in fact in on the arrangements. This would further add to the embarrassment and humiliation that Greg was to experience. Master agreed to my participation – even though he didn’t usually like threesomes or controlling two subs in one session.

It wasn’t agreed, upon or even discussed if I might continue with them back at the cottage. Actually, I had just assumed I would leave when they left to walk to Master’s cottage.

The Sunday morning came and I went down to the promenade on my bike – in my usual lycra gear; cycling bib-shorts and jacket. I would cycle back and forth on the roadside of the shelter until I saw Master and Greg meeting up, give them a few minutes to get started and then cycle past and stop in front of them.

I cycled back and forth quite a few times, noticing that there were a few other dog walkers around this particular Sunday and whilst I saw Master go into the shelter I didn’t see Greg. I wondered if he had arrived earlier. That question was answered about 15 minutes after the time they had agreed to meet up when I saw Greg walk briskly along the promenade and then disappear into the shelter.

Master was not going to be happy! Being late for your first session was not going to go down well and I imagined that Greg’s bum would suffer for that later!

I could now no longer see them but this is what Master told me later had happened…

“Well Greg we’re not off to a good start are we? Fifteen minutes late. What have you got to say for yourself?”

“I’m so sorry Master. I just miscalculated how long it would take me to walk along the promenade from the bus station. Oh, and the bus was a few minutes late too. I do apologise. How can I make it up?”

“Good boy and you will make it up to Master. But that will come later. I think three strikes for each minute late with my heavy leather belt over your bare bottom will go some way to correcting your tardiness. Hopefully, that will remind you never to be late for Master again.”

“How many strikes will that be then?”

“Eeh, three times fifteen sir”

“How many boy, quickly!”

“Forty-five Sir.”

“Good. In a minute we’re going to start walking along the prom to my beach house where we’ll undertake the promised humiliation and spanking session – now along with
your extra punishment. But before then we’re going to make the walk along a bit more interesting. Aren't we?”

“Yes, Sir”

“I’ve set my phone up there on the seat and hit record so, for the video, tell me you agree to what’s about to happen to you. Be as explicit as you can boy. ”

“Yes Sir. You’re going to rip some of my clothing here in this shelter and then we’re going to walk along to your cottage where you will remove the rest of my clothing, tie me up and spank my bottom, Sir.”

“Correct. You remembered to bring a change of clothing to return home with?”

“Yes, sir.”

“Sir, are you sure it’s quite safe to rip some of my clothing here right now? I passed quite a few dog walkers and cyclists on my walk along from the bus station. Are you sure they can't see what we’re doing?”

“Boy, I’ve met many subs like you here and yes, people pass by but they are all too embarrassed to stop and look in for any length of time.”

“We won't get reported to the Police Sir?”

“We won't be here that long boy. By the time they turn up, we’ll be long gone.”

It seems you're already excited by the prospect of what’s about to happen boy if that tent in your shorts is anything to go by. Did you do as I asked and shave down there?”

“Yes, I did Sir”

“Well show me. Pull the front of your shorts and underpants away from your body and let me see.”

“Good now let us get started. Take that rain jacket off and place it on the bench seat there”

“Now take your socks and shoes off. Don’t worry you’ll get to put your shoes back on to walk along the prom.”

“Sir I can see people walking their dogs along the beach. What if they see me or come over?

“Nonsense boy. They are miles away. All they’ll see are two men standing and talking. Taking shelter from the wind. I hope you're not going to get bratty with me and disobey your Master?”

“No, Sir.”

“Now pick up your socks, stuff one in your mouth and put the other in my left-hand trouser pocket”

“Yes, Sir”

“Now let’s see about making the walk along the prom a little more interesting.”

By now I had cycled back and was watching discreetly from the far side of the shelter.

Greg was standing almost with his back to me so I could only see his side and he couldn’t, as yet, see me. I watched as Master first grabbed Greg's nipples through his t-shirt, squeezing them hard before taking his scissors and cutting small holes in the t-shirt allowing the nipples to poke through. The cut material was discarded in the wind.

It was at this point that Master decided to reveal me. Reveal me as an innocent passerby. He knew why I was there and had permitted me to join in specific ways but Greg knew nothing of this.

Master shifted Greg’s shoulders around so that he was more facing towards me. The initial reaction on Greg’s face was priceless. He spat the sock out of his mouth and shot his hands up to cover his nipples!

“What on earth is the matter?” shouted Master.

From the corner of his mouth, Greg whispered “There’s somebody there. Somebody is standing watching us!” Shifting his eyes in my direction to indicate my presence.

I stood stock still, smiled and continued to watch from afar – as had been agreed.

“Great,” said Master “an audience. I wonder if anyone else will join him?” he continued, laughing.

“But we can’t carry on here with him there. We need to stop. Can't, we go to your cottage now?”

“Don’t be silly! He’s not doing anything. He’s just watching. He can’t report us if he’s just standing there. I’m sure this is adding to your embarrassment. Isn’t it? You arranged to see me, to be humiliated. This is perfect!” said Master as he pulled Greg’s hands back down beside his body.

“And judging by that erection we can all see, it’s having the desired effect.”

He picked up the sock from the ground and stuffed it back in Greg’s mouth.

He then reached around and grabbed the waistband of Greg’s white Calvin Klein briefs, pulling them upwards and suddenly with force. Greg jumped up on his toes before settling back down with much of his underwear now on show outside his shorts and over his t-shirt. Master pulled a second time giving him a full-on wedgie with his underpants now very obviously well ensconced between his ass crack.

The look of shock on Greg’s face was amazing. I guessed because of the wedgie but also because it was happening in the open air in the sight of me, a stranger – not to mention the noise of dog walkers in close proximity on the beach. Whilst they were still too far away to realise what was going on, Greg was still very anxious that they might see something.

At this point, Master reached into the rucksack that he had placed on the shelter's bench and pulled out a wide leather collar before fastening it around Greg’s neck. The collar was a good three or four inches thick which had the effect of keeping Greg’s head completely upright. He then took a carabiner clip and forced it through the material of his CK briefs around the waistband before clipping it on the neck collar. This had the effect of maintaining the wedgie much to Greg’s discomfort and embarrassment.

Master then took Greg’s wrists and behind his back placed a pair of sturdy metal handcuffs around them. Greg was starting to realise he couldn’t back out now even if he wanted to!

At this point, Master gave me a nod of his head motioning me to come a bit closer. I laid my bike aside the shelter and moved to stand a couple of feet to Greg’s right side. I myself was already hard which clearly showed through my lycra cycle shorts but I don’t think Greg had noticed yet! Master had though! 

Master then started to take his scissors to Greg’s shorts. They were black nylon football shorts but like those from yester-year; very short. He made several cuts of around an inch around the legs. He then made similar cuts just below the waistband of his briefs before gripping and pulling the cuts wider. Before long Greg was wearing a CK waistband with the brief material only attached in a couple of very small parts at Greg’s side.

At this stage, Master turned to me.

“What’s your name?” Of course, he knew my name but was only keeping up the pretence for Greg!

“Malcy, Sir.”

“Would you like to help humiliate young Greg here?”

Without speaking I stepped closer and nodded my head with a huge grin.

Greg shook his head sideways and mumbled something but Master just said “Shut it. I’m in charge”

“Rip the shorts,” he said to me.

I stepped forward and grabbed two parts of the short material at the bottom of the right leg and ripped the material all the way up to the waistband.

Master took the other leg and did the same.

“Again,” he said as we each took one of the cuts at the back of the shorts and ripped them loudly.

Master then reached between his legs and ripped the crotch in two.

Picture the scene. Greg standing there in public, hands cuffed behind his back, wearing a neck collar with the backside of his underwear attached to it and his shorts now flapping in the breeze showing off his white underwear which would have been covering his genitals if it wasn’t for the fact that his dick was rock hard and tenting what was left of his shorts and underwear.

How embarrassing. How humiliating!

At this point, Master said “Would you like to see more Malcy? Would you like to touch him?”

Greg didn’t know this but it had been prearranged that I’d get to get up close and personal with Greg’s cock if it seemed he was as turned on by the scene as we thought he might be.

Without answering Master, I dropped to my knees taking Greg's gorgeous cock in my right hand, pulling back the foreskin before taking it fully into my mouth! I couldn’t see Greg’s reaction but from the moans emanating from behind the sock gag, he was enjoying the attention.

I started working my mouth up and down his shaft before Greg himself started thrusting his pelvis back and forward to increase the pleasure.

The arrangements before the session were that Master would expose Greg, humiliate him a bit and then one of us would wank him off in the shelter before Master would then take him along the prom to his beach cottage.

Clearly, I was taking things a little further than had been planned! But no one seemed to be objecting. 

As I continued to work on Greg’s rock-hard dick, I suddenly felt a cold draft at my backside! Master had grabbed my lycra shorts and ripped them up the seam exposing my arse to the cold English Channel breeze. That wasn’t part of the plan! I didn’t have any spare clothes. I was going to have to cycle home with my naked ass hanging over my cycle seat.

However, at this point, my sole attention was elsewhere – making Greg cum!

We continued to build up speed, all the while working on his thick mushroom head with my tongue. I could feel Greg's cock start to swell in my mouth. He wasn’t far away. Then with a final thrust, I kept my mouth and face hard pressed against his body as I felt spurt after spurt of hot semen hit the back of my throat before I swallowed many times to take everything he had.

It was at that point I remembered Master had his mobile on the bench videoing the scene and I hoped my face wasn’t visible!

I pulled off his cock and stood up before giving Greg a full-on kiss over his sock-covered mouth leaving strands of his cum running down it.

I reached behind me to feel how much of my ass was exposed but I already knew from the cold wind that it was significant. There’s no way I could cycle home like that!

Master gathered up his stuff and said, ”Right you two, you're coming home with me for more fun.”

He removed the handcuffs and carabiner from Greg but left the collar on. This left Greg with a t-shirt with two holes showing off his nipples and effectively what was a skirt made of alternate strips of underwear and shorts. The slightest wind – of which there was a lot on the coastal promenade – exposed his naked bottom and, by now, flaccid cock and balls to the world. His socks were both tossed into the rubbish bin a the end of the shelter and Master picked up his rain jacket and stuffed it in his rucksack.

I wasn’t a huge bit better. Walking along pushing my bike with almost all my ass cheeks exposed!

Greg and I walked silently side by side with Master following on immediately behind – offering some, but not much protection from being seen. We made an interesting threesome! 

We could see Master’s cottage away in the distance ahead of us and whilst we couldn’t see if there was anyone else behind us we certainly could see a couple of dog walkers coming towards us ahead of us! At least Greg now had his hands free and would be able to stop his ‘skirt’ from flapping around. There was nothing he could do about his nipples, however!

Master’s cottage front door couldn’t come quick enough.

We arrived at Master’s cottage without further incident and with neither Greg nor I having said a word.

He still did not know he’d been set up.

It was his first visit to Master but I had been many times before so had a fair idea of what to expect. I guessed that both of us would lose the rest of our clothing; that we’d be restrained or tied up somehow and that we’d definitely leave with sore bottoms.

I wondered if it were in Master’s mind to reveal to Greg that he had been set up or if he would carry on the pretence for the whole session.

Master showed us through to the main living room of his cottage, which to the uninitiated looked just like a normal, comfortable day room but if you looked closely, you would see hints of what was to come! The metal eyelets screwed securely into the ceiling above our heads were the first giveaways!

Master directed both of us to positions in the room standing directly under these fixings and placed us facing each other before putting our hands behind our backs and placing handcuffs around our wrists. I stared directly into Greg’s eyes but tried hard not to give the game away or any indication of what was about to happen.

Judging by our erections both of us already had some idea though!

Gregs was poking out from between the strips of his ripped underwear and shorts and my own was still constrained, but very visible, beneath the tight lycra cycling shorts I was still wearing.

Before placing my wrists in the cuffs, Master had removed my cycling top leaving me dressed like this.

He had also removed Greg’s t-shirt. Greg stood in front of me, still with the wide thick collar around his neck and a strip of white underwear material hanging down his back and up his ass crack!

Master then applied a similar collar to my neck before placing a thick leather hood over my head. The hood plunged me into blackness. I had experienced these before and knew what was coming next. At the back of the collar was an eyelet and through that eyelet, he would thread through some thin rope before passing that up through the hoop in the ceiling bringing it back down, between my legs and then back up my front passing either side of my cock and balls before being tied in a knot over my head. The rope was pulled slightly meaning I could not stand with my feet fully on the floor. I had to stand ever so slightly on the balls of my feet.

I guessed that Greg would be similarly trussed up. Indeed he was...

I then felt that we were moved ever so slightly closer together. The hoods had no holes other than the ones our heads had gone through but every so often I could feel hot breath on my chest. I guessed from Greg that he was awfully close to me. I wondered if I could feel his erect cock. Nothing yet.

I stood stock still as I felt hands start to feel my chest working their way down to my cock and balls. I was hard as a rock and leaking pre-cum that I was sure would be visible through my lycra. I felt Master start to rub the wet spot and he then whispered in my ear “Is this exciting you boy?!”

I could not nod my head in agreement and could only mumble a yes.

I then felt fingers pulling the lycra away from my skin before feeling the chilly air of the room. Master must have cut a hole in the shorts.

How was I going to get home now?! At that, my cock sprung loose, and I felt it hit what I guess was Greg's erect dick. That’s how close we were. My balls were still trapped between the ropes and behind the lycra until Master reached in and pulled them out too.

Things then went quiet and there was no further touching so I assumed Master’s attention must have turned to Greg.

Soon I heard Master say that it was time to start our punishment – although I’m not sure what I was supposed to have done to deserve any! I remember that Greg was due to get forty-five strikes on his bare bottom for being fifteen minutes late for his appointment.

“Time to turn those beefy bare bottoms red,” said Master.

“You will get your extra forty-five at the end, Greg so we’ll start with my trusty slipper. Greg, I want you to count out the strikes.”

In my head, I thought that meant Greg was getting his punishment first and then I would get mine on completion but what happened next took me by surprise.

All at the same time I heard the strike of slipper against bare skin, then Greg’s body and erect cock pressing against mine as he recoiled away from the slipper strike and then saying aloud; “One Sir.”

This was quite different from anything I had experienced before!

There was a gap of a few seconds as I stood there expecting the next strike and a further opportunity to rub skin-to-skin with Greg.

I heard the brief swish of the slipper through the air before this time I felt the pain of a smacked bottom and I uncontrollably pressed forward into Greg’s body, our erect cocks touching each other once again!

Before I could even draw breath, I heard the next strike on Greg’s bottom, felt his body yet again and then “Two, Sir.” Despite the pain on my arse cheeks, this was ‘fun’!

In previous sessions, Master had often said “I’ll spank you until you cum” and I had often thought that is just impossible. Yes, sometimes I get hard when over his knee but quite often a smacking leaves my willy limp after a brief time. This time he really will spank me until I cum!

The strikes on our arses increased in both ferocity and speed and it was not long before I heard Greg say “Fifty, Sir”! With each strike, my cock would get pressed hard against Greg’s belly pulling my foreskin back and with increasing amounts of precum, it was well lubricated. I was close to spilling my spunk all over his belly – our bellies. Of course, with such pleasure, I was not holding back after each smack of the slipper from Master and pushing myself harder and harder against Greg’s nakedness. I could not be sure, but I felt he was doing similar. But he had already cum today. Could he possibly spurt for a second time?

“I was going to stop at 50 slipperings but you two look as though you’re enjoying this too much?” said Master.

There was a pause before I heard the familiar swish of a cane and felt the vicious sting across both my arse cheeks. I had not heard Greg receive the same and I was confused. Should I be counting? To avoid displeasing Master I said “One, Sir.”

The strike pushed me harder into Greg and I could not help but start to pump myself harder into him sliding my cock between our wet bellies. I was so close to cumming. I was now controlling that rhythm. Not Master with his cane strikes.

Master must have realised this as there was no let-up in the strikes as two, three, four then five rained down on my poor arse. With the sixth, I experienced that heady mix of pain from six of the best and the release of several days of stored-up spunk. I pushed my body tight against Greg’s as my cock pulsed and spilt my seed down our respective bodies. I eventually felt it dripping on the tops of my feet. I wanted to collapse in a heap on the floor, but I could do nothing but stay where I was still being attached to the ceiling!

What next?!

I felt Master’s hands on my head as he undid the hood and the rope. He pulled off the hood and my eyes blinked in the bright light. In front of me was Greg still locked up in his hood, his wedgie attached to his neck collar and his ruined shorts around his waist with the remnants of my semen dribbling down his front and hairless pubes.

“Malcy, strip off the remains of your cycling shorts. Get naked and then help Greg to get naked too. Once you have done that, I want you to help me deliver his ‘45’ punishment.

In a moment I will remove your handcuffs. You will then stand in front of Greg, face to face, and wrap your arms around his upper body.

It’s your job to keep him still whilst I administer the forty-five strikes across his buttocks. “

“If you can't keep him still, I will be forced to tie you together with this rope.”
It was at this point that I realised that only I had received Master’s cane so far and it sounded as though Greg was now about to get forty-five strikes of the cane! Surely not?

I worked quickly to remove the remains of Greg’s shredded clothes before Master removed our handcuffs. I then stood in front of Greg and smiling I wrapped my arms around his back. We were both of similar height, so Master then clipped our collars together before taking Greg’s arms and wrapping them around my back before handcuffing them!

I could feel Greg’s hot body against mine and his heavy breathing on the naked skin of my shoulder. His fat cock was swelling and sticking into my own groin and despite having just cum I was sure my own cock was thickening in reaction to what was happening!

I knew that to stop Greg from moving during his punishment I was going to have to hold on to him extremely tightly. I wondered if Master was going to deliver them in a short sharp burst or slowly over a lengthy period.

The first swish was delivered, and Greg reacted both vocally and physically I realised just how much effort I was going to have to exert to maintain him in position and indeed help him take his punishment. Forty-five cane strikes were going to hurt and potentially leave his arse in a bloody mess. He certainly would not forget this - or be late again.

The answer to my speed of delivery question came after a minute or two as I worked out that Master planned to spread them out over a lengthy period. I was not sure what Greg thought about this – would he prefer to take them in one short sharp burst; how experienced was he in being caned?

After a dozen strikes, Greg was sobbing in my ear. To this point, and despite the closeness and intimacy of everything we had experienced this day, we had not spoken.

I needed to say something. Issue some words of encouragement, some words of comfort.

Master had not said we could not speak. As far as Greg knew I was just some random guy that had happened across his Master/sub appointment!

I said softly “You are doing really well Greg. It will soon be over.” before rubbing his back with my arms.

After 15 strikes Master paused and said,

“Greg as this is your first visit to me as your new master and as you told me the bus was late too, I have decided to allow some leniency and just issue one strike for each minute late. That is your punishment for this time over but let that be a lesson to you. Do not ever be late for an appointment with your Master again.”

With that, he unclipped our neck collars and I released my grip on his body. I got a chance to look him up and down noting he was no longer erect (but it was still a gorgeous, thick penis with a lovely foreskin), and he had tears streaming down his face.

“Malcy, can you rub this gently into Greg’s buttocks please,” said Master as he handed me an unmarked tub of some white cream.

I sat on the nearest chair and directed Greg to lie across my legs. I gently rubbed the soothing creme across all of Greg's butt cheeks taking care when touching the cane stripes and lesions. He twitched and grimaced at some of the touches, but I guessed in time this could only help.

When that was finished, Greg got dressed in the spare clothes that he had brought and then the three of us sat, me still naked, and had a very civilised cup of tea chatting about everything and anything but spanking and what had just happened!

As we finished, I waited patiently for some comment from Master about how I was going to get home – my cycling shorts were ruined and all I had left were a pair of socks and my cycling jacket Neither of which would cover my genitals or ass sufficiently to cycle decently home.

I could not wait any longer “Master have you something I could wear to cover me when I cycle home?”

Master did not say anything other than “Wait here.”

I did think you would be able to ride home like that but if you're uncomfortable then I guess you could wear these holding up a tiny pair of white nylon shorts!

“Thanks, Sir” How embarrassing!

With that Greg and I made our separate ways home. To this day he does not know that I was arranged and not just some random passer-by. He is unlikely to read this, but I suspect that Master will tell him someday! Or maybe not. 

Is that the end? Do Greg and I meet again?

Malcy