First Date With A Disciplinarian: Drinks, dinner, and a damn good spanking!

REAL Spanking Short Stories from The Life and Times of...

Those of you who’ve previously followed me for some time on social media platforms will be familiar with my avatar: a short-handled riding whip, draped casually on the seat of a comfy armchair.

This is the story behind that photograph and my slight preference for a cropping when implements are being reached for… and yes, this really did happen on our first date!

As I belted my way down the M6 towards The (beautiful) South, my thoughts turned toward the evening’s proposed events. Namely, dinner, drinks, and a damned good spanking! By now, I was acutely aware that Mr. James was not a man to be trifled with. We had met on two or three previous occasions, the most recent of which was a dinner at The Quicken Tree somewhere near Coventry. We’d had a wonderful evening, conversing and flirting, flirting and conversing, and we’d finally gotten around to discussing my discipline requirements. I was in a fired-up hurry to put in place a professional arrangement that would cater for my rather specific needs, as I simultaneously plotted to take over the world, and run it from my hollowed-out volcano. Well, not exactly, I wasn’t quite such a megalomaniac in my early 20’s, but I was certainly ambitious, and I knew that I would need certain checks and balances to prevent me from becoming such!

As I am sure you can imagine, Mr. James was only too happy to oblige, seeing immediately my potential for sparkling success and - just as likely - unmitigated disaster. Creative types are always on the verge of falling into total chaos by their very nature, and whilst I had my head screwed on better than most artistes I knew, I never-the-less had that devastating potential for catastrophe.

Mr. James and I discussed at length my corporal punishment requirements, motives, and ultimate objectives. I was more than satisfied that I had found a most willing and able accomplice. The not inconsiderable age-gap between us gave me additional confidence that here was a man that would be able to handle me. This was vital, as I didn’t have time for this part of the master-plan to go wrong, I needed my disciplinarian to have his stuff together, and more importantly to have my back whilst I attempted the darn-near impossible, in my parallel professional careers. The guys my age were just a ‘no.’ None of them had ever impressed me, most of my would-be suitors were in their twenties and were still boys. It sounds harsh; however, I didn’t have time to be messing about waiting for my significant other, and/or my disciplinarian to grow up. I had aims and objectives and I needed to make sure my safety net was securely in place, before I let rip.

Now, here’s the rub. This dinner in Coventry was merely a working dinner, though as things transpired, it turned out I actually quite fancied Mr. James and I could tell that those feelings were mutual. This I hadn’t planned for. I’d mistakenly thought that the age-gap between us, estimated at 15 years, would preclude a romantic relationship. After all, I was genuinely after a disciplinarian, first and foremost to prevent me from going off the rails when things got tough in my professional life. It hadn’t occurred to me that, not only might I fancy the cad, but that said cad might also have designs on me. Oooops!

Well, I was over 90 percent happy with the state of play, and I wasn’t going to give up the evening’s ‘work’ for the ten percent problem of romance. That was until he tried to snog me in the car park after dinner! Now, don’t get me wrong, Mr. James had been the very definition of a gentleman before, during, and after dinner. The model professional. However, as he later described it; he’d already fallen for me. The fool!

On the not inconsiderable drive home that night, I had mused on the latest turn of events and tried to square away my feelings for the man, because my career came first. I genuinely wanted a professional disciplinarian to hold me to account. As a high-achieving young creative, the last thing I needed was a grossly inflated ego. I knew that I needed grounding and that this was the correct method for me. I was also acutely aware that high-quality male pro disciplinarians were rather thin on the ground.

Some internet research had taught me that most male tops seemed to believe that the classical male professional disciplinarian was little more than a myth. The thinking behind this belief being that there were so many male tops, and so few female bottoms, that most of these men would happily provide spanking services to women, for free. Let me tell you, gentlemen, nothing could be further from the truth. Not only do I know, but I have also worked with several male pro disciplinarians in both the UK and abroad. How? How does it work, you ask? Simple. Women like me, much prefer to pay for such services, as the monetary exchange actually enhances the perception of a professional relationship. Indeed, it is an additional layer of security that you are not in fact, going to ask us out on a date. Some ladies simply require your discipline services and seriously aren’t looking for romance. So, there you have it! Get cracking!

As I neared home after that first working dinner, I resolved to go for it with Mr. James. Yes, the romantic element had been a surprise, particularly as it was evidently the same in both directions. However, it needn’t be a problem. Assuming he could still do his job, then why knock a gift-horse in the mouth? Besides, I’d just inadvertently killed two birds with one stone. Disciplinarian and future husband nailed in one night. Excellent work, Jacqui!

So, here I was hurtling down the motorway, this time the destination was Maidenhead, for a darn good spanking. This was our first date, but he had also warned me that he would be seeing what, if anything, I was made of. My scant internet research to date, had thankfully been sufficient to avoid any grave misunderstandings. I did smile to myself as I passed Coventry on my journey, it was clear that this time I was required to enter the lion’s den. Maidenhead being far closer to his residence than mine. Coventry had indeed been a half-way point, a more equitable arrangement. Now, now I was required to make the greater effort. Yes, Mr. James was indeed not a man to be trifled with!

On arrival at a swanky hotel on the outskirts of Maidenhead, I immediately checked the time to see whether or not I was late. I had of course hit traffic on a Friday, on the M6 - quelle surprise - however, I already knew that my disciplinarian was a huge fan of punctuality. Time keeping not being my strong-suit, I was eager to pay attention to it, and was relieved to discover that I was a whole 15 minutes early!

I waltzed into the hotel bar, full of myself, only to instantly see that I was not there first! Mr. James was sat waiting for me in a secluded corner of the bar, sipping dry-white wine. I opened my mouth to speak, but my breath caught. Truly shocking for a professional actress, but it happened. I simply couldn’t get any words out. He rescued me.

“Ah, Miss Allen! There you are. May I pour you a drink, Miss?”

“Y… yes please. Thank you.”

I just about managed, inwardly berating myself for revealing such nervousness. So, so unlike you Jacqui.

“How was your journey, young Miss?”

“A little eventful, thank you,” I said, taking the large glass of Sauvignon Blanc.

“Sir, Jacqui. ‘A little eventful, thank you, sir,’ is what I expect to hear.”

“Yes… uh… sir. Sorry.”

“Much better. Anyway, you are at least on time, so you have nothing to worry about there.”

I laughed into my wine glass.

“Something to share, young lady?”

“No, no, I made it and that’s good enough, right?”

“It is indeed, but if you forget to address me properly again, there will be consequences not too long from now.”

“Yes… sir.”

“Consequences that you will feel. Do I make myself clear?”

“Yes, sir. Understood. Thank you.”

I really wasn’t getting the hang of the sirring thing. It was just so weird. I hadn’t called anyone sir since high school and even then, it was kind of ‘on license.’ Which is to say, that I would only use it if I absolutely had to, or if the teacher was of the highest quality and therefore merited it - in my not so humble opinion. Even then, I would use this mark of respect extremely sparingly. Calling your date sir? No. That was just weird… (perhaps I ought to have done a tad more internet research into these matters!)

The conversation meandered and I was relieved and pleased to note that he was far more at ease than I, and this was actually most reassuring. As a confident, dare I say formidable, young woman, it was rather appreciated being in the hands of someone competent enough to run the show himself. Enabling yours truly to take a night off from being in charge - that has its own value.

Sir ordered some food for us both and I do mean he ordered. That got my attention. I hadn’t been ordered for by a man, ever. The last time someone ordered for me I was probably less than 12-years-old. I might have once, been enraged at someone presuming they could make such decisions for me, but I must confess, in this context I rather liked it, and in any case was impressed with the cheeky sod’s audacity. Brave move, ordering dinner for a confident woman in the noughties, brave move indeed.

I do not remember much about the meal or any of the lengthy and enjoyable conversation, save for the fact that it was two-way, immersive, and full of elan. How wonderful it was to meet a man who knew the art of conversation well, took every opportunity to lead the way, and behaved in a dignified manner. Who said chivalry was dead?

You know the saying ‘famous last words?’ Well, yeah… a very short time from that laissez-faire thought, I would be reconsidering what it means to be chivalrous!

The lively, flirtatious, and all-consuming dinner conversation vanished after Mr. James had asked the waiter to put the food and drinks on the room. He turned back to me and in a dangerously quiet voice told me to go and wait for him upstairs whilst he fetched his luggage from the Jag.

I blushed, swallowed, cast my eyes downwards and nodded gently.

“What do you say, Jacqui?”

“Uhm… thank you.”

I glanced back up at him long enough to witness his expression darken, my mind was racing through the possible remaining permutations…

“‘Yes, sir,’ is the phrase you are looking for.”

I looked back up at him with puppy-dog eyes, but he wasn’t buying.

“I will help you to remember it very well, shortly. Now, go!”

Closing my eyes momentarily, to reprimand myself for being so stupid, I otherwise complied with his instructions immediately. I left the hotel bar with the room key and wasted no time in getting there. I wasn’t sure why I was rushing, but I felt sure that being there sooner rather than later was preferable.

My intuition served me well.

On arrival in the room, it was clear to me that Mr. James had already been up there and had prepared things somewhat. I cannot recall how I knew this, but I knew it. He’d definitely been up there and this preparation gave me an appropriate pang of anxiety. This, this was not a man to be trifled with.

I took several deep breaths and checked my hair and make-up in the mirror, before perching on the end of the King-Size double bed. All the while I was telling myself to keep calm and to try to relax as much as possible. Easier said than done when you know you are due a spanking, and especially as this would be my first ever real spanking from a proper disciplinarian. It was in these moments that I became seriously concerned for the first time about how I might measure up. Pain management was very much on my mind, I had no idea what this was going to be like, nor whether I would in any way be able to tolerate it.

I badly wanted to tolerate it too. I couldn’t come this far and then find out I didn’t have what it takes. I felt not unlike how a boxer must feel at his first bout. You can do all the training and all the sparring in the world, but until another boxer lands one on you, you can never be sure whether or not you haven’t a glass jaw! I’m not certain to whom or what I was praying, some god of spanking, perhaps? But I was sure as hell praying that I would be able to cope and cope well with what was to come.

Stewing in my own uncertainty, the door to his hotel room clicked and swung open. There was Mr. James with a drastically different demeanour and a medium sized sports holdall slung over his shoulder. Oh shit!

“Stand up, face the wall, and place your hands on your head, young lady!”

There was no time to process and reply, so instead I simply did as I was told.

“Now, I’m going to give you damned good spanking but first you are going to spend some time reflecting on why you are here, and what it is you really want. Do you have any questions?”

“N… no, I don’t think so.”

“SIR! Jacqui, you will address me as ‘sir,’ each and every sentence.”

“Yes, sir. I’m sorry… I… just forgot…”

“Then I will help you to remember.”

“Yes, sir.”

“Before we are finished here tonight, I assure you, you won’t have difficulty in paying me proper respect in the future.”

“Yes, sir. I’m sorry.”

“You will be, young lady. Now, straighten up, stand still, and await further instructions.”

“Yes, sir.”

I have no idea how long I was stood facing the wall, it seemed like forever, and I must say the décor was especially boring. No intricate patterns on the wallpaper - no wallpaper at all, in fact. Just non-descript paint on plain-boring walls, and my goodness me, did I really start to feel pain in my upper arms. As a devout gym rat, I paid good attention to my physique, so I wasn’t too well prepared to be stood with my hands on my head for any length of time. My lats, traps, deltoids, triceps and biceps had all had a thoroughly decent workout that morning and this was the last thing they needed. I probably wasn’t ‘in the corner’ for more than 15 or 20 minutes, however, I was tremoring with the effort of keeping my arms up for such a length of time. Mental note: do NOT gym on discipline days.

“Come here, raise your skirt, and place yourself over my knee.”

I couldn’t have spoken even if I had wanted to. Everything tightened right up. From my vocal cords down to my sphincter, I was locked solid. Instead, I complied swiftly and with purpose.

“I’m going to tan you until I think you’ve had enough and you are going to be a good, compliant girl and stay down in position, aren’t you?”

“Yes, sir,” I squeaked, face centimetres above the duvet, hands already reaching for something to hold on to.

The first few smacks with his right hand were something to behold. He hit with force, accuracy, and intent. It hurt. I at once feared that I wouldn’t be up to this after all, but as the smacks continued to rain down, I realised that the pain wasn’t intolerable. On the contrary, if I knuckled down - quite literally when taking my grip on the duvet into account - then I would be able to ride this onslaught without embarrassing myself too much.

I gritted my teeth, held onto the duvet tightly, with both hands, and closed my eyes. Every time a blow landed, I tried to relax into it as much as possible. Tensing, I knew from my barely sufficient research, was a false economy and would result in more pain and discomfort in the coming days. So, I resolved to stay as relaxed as possible and to just accept the discipline.

This became more challenging as time wore on. The heat in my rear was building and building, and I had no idea how hot things might get back there. The stinging pain from the extremities of his hand was weirdly subsiding the longer the spanking went on, however it was being replaced with a more worrisome wall of pain. A kind of heavy, pervasive and longer-lasting kind of weight-cum-discomfort. My breathing had accelerated and I had even begun to perspire with the effort of remaining still.

He stopped and used his left hand to test the temperature of one cheek and then the other, through my tights and scanty white frillies beneath. I knew it must be his left hand as it definitely wasn’t the spanking hand. This one was much cooler. I smirked to myself that at least his hand must be hurting too!

“Look at me.”

At first, I thought he’d caught me laughing, which was impossible as I had only smirked, so I was relieved to read a level of concern, rather than displeasure, on his face. Then, clearly satisfied, though I had no idea what he had been looking for, he motioned for me to get back into position, which I did forthwith.

“Let’s have these down now, young lady. Enough messing about!”

He yanked down my tights and frillies in one go and I raised my hips just enough to make it easy for him.

“Good girl, now let’s see what you’re made of, shall we?”

“Yes, sir, let’s,” I chirped back, sounding more confident than I was really feeling.

The smacks rained down much faster now and the sting was really accentuated by the juxtaposition of a clad versus unclad posterior. I really wanted to kick, wriggle, and fight, however I had promised myself I absolutely wouldn’t fight my disciplinarian. Resisting is one thing, and perhaps even necessary in some circumstances, but I couldn’t allow myself to fight that which I very badly needed. So, I instead hunkered down, squeezed my eyes more tightly shut, and pressed myself down into his lap and onto the duvet to prevent myself from trying to get up.

I now had the heavy, deep pain building to a crescendo as well as the sharp, stingy pain from the flesh on flesh to deal with, and I’m not going to down-play it, I was in metal turmoil. On the one hand, I very badly wanted to be up to the task, and to be able to show that I was both willing and serious about having this kind of relationship. On the other hand, it was really hurting now, and I wasn’t sure what would happen should this spanking continue for very much longer.

Alas, continue it did. Mr. James wasn’t done yet and all I could do, as time stood still, was hang on for dear life… or dear pride, at least. I have no idea how long the spanking went on; eternity would be my best guess. I was lost, save for a tiny slither of determination to see it through. I’m not entirely sure where that little bit of desire to gut it out comes from. I suspect it has something to do with my enjoyment of competition. Both sport and acting are highly competitive fields and I’ll wager that my ability to hang on in there just a little bit longer than I am truly able, is down to this competitive spirit. God only knows where it ultimately comes from, even if it is clear to me that my love of sport and theatre has no doubt enhanced it somewhat.

I know that I endured a long hand-spanking, as there were several moments during this second knickers-down phase where he stopped, and insisted that I look him in the eyes, before he then instructed me to get back down. Through the haze of pain, emotion, and sheer, grim determination to ‘not lose,’ I was curious as to why he kept asking me to look at him. I couldn’t figure it out. Being desperately inexperienced about all things Corporal Punishment, I had not the pieces to fit the puzzle together. It was only at the final iteration of this ritual that the penny eventually dropped.

“Look at me.”

“What, sir?”

“You little brat!”

He’d been checking for tears! Ha! All this time I had wondered what on earth he was doing. I hated stopping, my preference was for getting it over with, and all this stopping and insisting that I look at him was most bizarre from my perspective! That was it, he was checking over and over to see if I was crying. Well, that was it, if I needed any further motivation to see this spanking through that was it for sure. If it were tears, he was searching for, then tears he shall not find!

I know, I know… it’s just the way I work.

“Get up and place yourself over those pillows in the middle of the bed.”

I did as I was told, thinking that this slight change of angle, if anything, would make the spanking easier to tolerate. I, of course, hadn’t foreseen what was actually to come. I heard him rustling around in his holdall and it was only then that it dawned on me what it was. An implement.

I heard it before I felt it. It whistled through the air, a real whippy sound. What could it be, I wondered…?

“Right, you are to remain perfectly still. Clear?”

“Yes, of course.”

There was a pregnant pause before I heard that whippy sound again, and an almighty crack followed on, this time. At first, I didn’t realise I had been hit, but that only lasted for a fraction of one second. Subsequently, I felt an almighty blaze of white-hot pain, followed by a cooler, redder pain emanating out from the epicentre of the impact. The sting was almost indescribable, and the build-up of that heavy kind of pain was rapid. My skin felt as though it was raising up to stand tall against a dangerous, storm-affected ocean, and it was! Mr. James used his fingertips to trace the pronounced welt that now stood proud across the meat of both cheeks.

“Look at me!”

“What?”

“I don’t believe it!”

“What? What do you mean?”

“Not a single tear. Not one! I’ve just hit you full tilt with my crop, young lady!”

I didn’t have time to respond, which on reflection was probably for the best, as he dragged me into a passionate French kiss and engulfed me, at one and the same, in an enormous bear-hug. He seemed almost giddy, intoxicated by a new and fascinating entity, I suppose on some level he was.

I felt the warm glow of satisfaction as I lay there in his embrace. I was satisfied that I had come through and not only that but had - at least in his judgement - come through it extraordinarily well.

“You were stoic.”

He kept repeating that phrase, throughout the rest of the evening. I only had a rudimentary understanding of what stoicism was and what it meant, so his wonder was somewhat lost on me at that time. That crop stroke had really hurt, I mean really, really hurt, but not more so than my desire to impress Mr. James, and to cement our slightly unusual first date. I had already decided at some point during that spanking, that he was for keeps, and holding back the tears for one savage crop stroke, post a sustained OTK, was well worth the effort in my book.

I don’t think I’ve ever had a stroke quite like that one, with either the crop or the cane, in the almost 12 years since. He says that I’ve endured much more since that fateful night, however I disagree. Whilst he may be technically correct in terms of force and/or velocity, in terms of meaning, that one stroke is still above all. It was the litmus test, the acid test, and a baptism of fire all rolled into one. Soaking up the immense pain in those brief seconds and minutes without fuss is to this day one of the best things I have ever done. I’d do it again in a heartbeat. Which was just as well…

“Right, Jacqui. We shall now address your forgetfulness. You are to refer to me as ‘sir’ at all times, and I am going to reinforce this fact. Back over the pillows and into position, young lady. If this is the relationship for you, then this is what I expect, and this is what you shall expect if you fall short. Get it up!”

“Yes, sir.”

Jacqui James
Live-Lash-Love

That was from the “PRO” section of my website, more of which can be found here:https://jacquijames.substack.com/s/pro-disciplinarians

[ALL materials ©Jacqui James 2021]