Benefits of Hindsight Ch. 03

I didn't have the heart to leave you very long. It turned out that the thought of you lying tied up on the bed, desperate for an orgasm, with that vibrator buzzing inside you, was too compelling to allow me to focus on anything else. I managed a drink and sat down in front of the TV for a while, listening to your frantic noises, muffled by the distance and door between us. Hopefully it was long enough to seem like hours of torture to you in your state of agonised arousal. Finally I could stand it no longer. My cock was getting hard yet again at the thought of you, and I came back to find you exactly where I left you on the bed.

You made an awesome sight as I stared at you. You were lying on your front, arms and legs still confined by the hogtie I had fashioned from your tights. By this time your head was resting forwards in defeat on the bed, but the way your hair was tousled around it told me that you had been thrashing in your bonds, probably attempting release from your frustration as much as escape. As I approached you I could make out the beads of sweat standing out on the skin of your back, which was naked but for the bra straps. Evidently you had worked up quite a heat in your struggles. By now you had become aware of my presence and lifted your head. I removed your blindfold and immediately saw the reproachful look in your eyes as you looked up at me, your tormentor.

I sat down beside you on the bed and wordlessly rolled your body, still exquisitely helpless in its bondage, onto its side. The strain on your wrists and ankles, attached to each other behind your back, caused you to open your legs, which were facing in my direction. It wasn't a very ladylike position, but I don't suppose that was your greatest concern at that moment. I untied the knot at your belly which held the stocking in place through your crotch and pulled it gently from your sex. Even with my caution, you were so sensitive by this point that it drew a yelp from your lips. By this stage the garment was saturated with your juices. With this obstacle removed, the way was clear for me to bring you to fulfilment.

Reaching my hand forwards I used one finger to stroke your clit. You gasped audibly after only the slightest contact and I responded by keeping things gentle. Along with the persistent action of the vibrator inside you, it was all you needed. Your arousal was so extreme that within seconds you were arching your back, already bent by my restraints, and announcing your climax with an increasingly intense series of squeals. Only then did I pluck the vibrator, still buzzing, from your pussy, and switch it off. Finally you had been given release.

As your breathing subsided I freed you, step by step. First I removed the remnants of the crotch rope by untying the stocking loop around your middle. Then I gave relief to your poor breasts by untying the ribbons which held your nipples so painfully captive and kissing each one tenderly, listening to your groans as the blood ran back into them. Having done so I unclasped the bra at your back, leaving it hanging loose for now. At this point you were still hogtied, but I untied the knots which connected your ankles to your wrists and those which held your feet together, allowing you to stretch out your legs stiffly. Finally I took the handcuff key from my pocket and unlocked the bonds which you had put on yourself at the very beginning. Now you were completely free.

Bringing your hands to your front you rubbed each wrist tenderly where they had been shackled for so long. I slid your bra straps down your arms and helped you out of it altogether, before stooping to help you out of your heels. You deserved a bit of comfort after all your exertions on my behalf. Finally I piled up the pillows behind you, leaned you back against them, knelt in front of you, pulled your panties down and removed them. I lifted your hips to the edge of the bed and delved my head between your legs until my tongue met your sex. Gradually, tenderly and slowly I gave you your second orgasm, using only my mouth. There were no fireworks this time and not a hint of teasing on my part. I just brought my girl some well-earned satisfaction. It was the least I could do for you.

............

I'm glad to say that this time I don't make the mistake of feeling awkward about what has passed between us. I greet you the next morning with a grin and suggest we should try the same thing again some time. You respond by suggesting that it might take you some time to stop feeling stiff, but I can see from the expression on your face that you can't wait.

I'm nothing but considerate and dutifully give you some recovery time. After a week or so I consider that long enough has elapsed and I suggest we go out for a meal together.

You raise one eyebrow quizzically. 'What, on a date?' you ask.

'Yeah, I suppose so,' I reply. 'Is that ok with you?'

You smile before answering in a playful tone. 'It depends on whether it's the sort of date which ends with me getting a nasty surprise.'

'And what sort of a nasty surprise might you be referring to?' I continue, knowing full well what you mean.

'Hmm, let's see. How about the sort which involves me being tied up with my arse in the air while you stick things in various parts of my anatomy and give me a damned good thrashing before having your wicked way with me?'

'I am flabbergasted,' I bluster in mock outrage. 'Whatever gives you the idea that I would do that to a respectable young lady like you?'

'Well, just a couple of weeks ago this respectable young lady spent an evening tied to her own dining room table while a respectable young gentleman took a cane to her backside. Then only last week she got trussed up like a pig going to market and was made to squeal in a most undignified fashion while she got excessively familiar with the taste of that same respectable young gentleman's cum.'

'Clearly this young lady needs to think more carefully about the young gentlemen she chooses to accompany on her evenings of leisure,' I reply, with mock concern.

Quick as a flash you have an answer. 'Which is precisely why she wants to make thorough enquiries before embarking on this date which you propose.'

'And would the prospect of a nasty surprise at the end of the evening make the young lady more or less likely to accept the offer of the date?'

You give no answer to this, but the smile which plays around your lips tells me everything I need to know.

............

I make my preparations carefully, arranging things exactly as I want them. I check what colour you are planning to wear and make some online purchases accordingly. Hindsight tells me not to worry about upsetting you by being too rough. Our encounters so far have given me ample evidence that you are every bit as into this as I am. Besides, our conversation about the potential surprise has given me a certain license in my dealings with you. But I want the surprise to be just right, and I want it to actually take you by surprise. For that reason I decide to spring it on you at the start of the night rather than at the end.

The evening we have chosen for our date comes at the close of a hot summer's day, and the temperature is still warm when we are ready to set out for our meal. I sit at the table in our flat, waiting for you to finish getting ready, my hand resting on a package which contains one of the items I have bought. I have wrapped it up especially for you. Then you appear, and my mind is whisked right away from my plans by how stunning you look.

You have chosen a summery dress with a floral pattern. It has a halter neck which leaves your shoulders and arms uncovered. It is short, but not wantonly so. Beneath it your legs are bare. The temperature is warm enough for this and your legs certainly don't need anything to enhance them. On your feet you have a pair of blue high heeled sandals, which pick out the colour of the flowers in the dress. You manage to look both innocent and sexy at the same time. I find the combination irresistible.

'How do I look?' you ask cheerily, giving me a whirl as you speak. I notice that the back of the dress drops low, but I see no tell-tale strap. A closer glance when you are facing me once more confirms that you are not wearing a bra. Evidently somebody intends to be a bad girl this evening! I'm certainly feeling encouraged about my nefarious plans for you. The lack of bra will give me less to remove later.

'God, you look amazing!' I reply, with genuine enthusiasm. Then, recollecting myself, I get my plans back on track. 'I'd just like you to put on one extra thing to make the outfit perfect.' As I say this I hand you the package on the table.

Your face lights up at the prospect of a present. 'You're so sweet,' you say, 'but I already chose my jewellery.'

I don't bother to respond to this, but simply watch your delicate fingers as they remove the wrapping paper to find a box within. It has the appearance and feel of luxury about it.

'What is it?' you ask in delight.

Once again I leave you to find out the answer for yourself, waiting for your gasp as you lift the lid and open the tissue paper which covers my gift. Sure enough, I am not disappointed as you make your discovery.

'You can't be serious!' you say with feeling as you hold up the butt plug, blue to match your outfit. 'You expect to get that thing inside me later? You're going to have to get me very drunk first!'

'That's not the plan at all,' I reply calmly. 'I'm going to put it inside you right now. Whether you get drunk or not while you wear it is entirely up to you.'

Of course, I'd never force you, and you only have to refuse, but I'm pretty confident I've calculated correctly. I'm betting that your mind will contain enough curiosity about a potential new experience and, more importantly, nascent excitement about the prospect of obeying me, to outweigh your reluctance about the likely discomfort. Besides, we both know from prior experiences that discomfort is hardly a turn-off for you.

You hesitate before answering, and in that hesitation I sense that I am right. Your eyes tell me that I have you exactly where I want you. That plug is as certain of its destination now as it will be in a few minutes when it's filling up your arse.

'What the fuck is wrong with me?' you ask rhetorically, resigning your butt to its fate. 'Three weeks ago I wanted sex, normal sex with a decent, considerate bloke, and now you've got me doing this! You're a first-rate wanker, you know that? Go on, get it over with. Where do you want me?'

You can talk all you like, but the only fact that matters is that I'm about to shove that plug up your arse and you are going to let me do it. This is a moment I want to savour. 'First we need to get my toy ready,' I tell you, taking the plug from your hand. 'We wouldn't want to put it in dry, would we? That would make your poor arse so sore!'

So saying I hold it up to your mouth and before you fully realise what is happening you have embraced the degradation and are kissing the very object which will shortly be invading your most intimate opening. Not content with that I insert it into your mouth and watch in aroused fascination as you welcome it with your lips and run your tongue around it. My cock stiffens as the memories come flooding back of how you pleasured me orally the previous week.

But I mustn't get distracted. I remove the plug from your mouth and return to business. 'Bend over there!' I order you, indicating the back of one of our armchairs, which is facing away from us.

You turn to obey, spreading your legs slightly as you do so and leaning forwards over the fabric until your hands are gripping the arms of the chair and your upper body is draped downwards towards the seat. Your arse is now raised prominently, just as I require. This action has drawn your dress upwards to reveal more of your thighs and I complete the picture by taking the hem of the garment and flipping it up and over so that it rests on your lower back. I am left with the now familiar, but no less exciting, image of your toned and pert butt, this time encased in a delightful pair of baby blue panties.

I tug the panties down and off your arse, leaving them bunched around your thighs with your rear end exposed and vulnerable to its imminent invasion. I'm pretty confident that if I went for your pussy right now I would find it already wet, but all that can come later. For now I have to focus on getting your butt ready.

I can't resist giving one upturned cheek a quick slap with my hand, enjoying the squeal it brings from you. This has more to do with surprise than pain. Later on I'll give you something genuinely painful to shout about.

'Spread your legs further!' I tell you, kicking at your feet as I do so to illustrate what I want you to do. With some difficulty you shuffle them further apart. I open up a jar of lube which I bought for the purpose and smear it liberally between your arse cheeks, working it into your tight opening with my finger. You say nothing at this point, but I can sense your arousal at the humiliation of being greased up by me. It is coming off you in waves.

When you are suitably prepared I wash my slippery hands so I can grip the plug, which is still slick from your saliva, and slide my index finger through the ring at its end. Holding it to your opening I give you a word of advice. 'Hold on tight and stay completely still while I do this,' I admonish. 'This thing is going inside you no matter what. If you struggle I'll have you tied in this position in no time and we'll start again.'

You know better than to answer back, but I see you grip the arms of the chair as I suggested. Now my moment has come. I slide the narrow end of the plug into your opening, pausing as you stiffen involuntarily at the intrusion, then continuing to work it inside you. At first it seems as if I will never succeed, but slowly, surely, it enters you and I know that each millimetre which disappears from my view is a millimetre more of exquisite discomfort for you.

Finally I get the thing home and your anguished gasp tells me that it is having the desired effect. I stand back to admire the view, enjoying the pleasing coordination of the blue ring emerging from your butt with the blue panties gathered below it, the blue sandals at the end of your stretched legs and the blue flowers of your pretty dress above. Then I pull your panties up and draw them over the intruder, making it a secret to which only you and I will be privy.

Having done this I bring your dress back down into the appropriate position and tell you to stand up. You do so uncertainly, testing the sensation of the plug deep inside you. You turn to face me, the cheeks of your face flushed from the blood which has rushed to them while you were upended and also from the shame you feel at what you have just allowed me to do to you. I hold out my hand and you step towards me. The distance between us is only a couple of metres, but it is sufficient for me to notice you hobbling slightly as you get used to having your butt plugged. This is going to be even more fun than I had anticipated.

Without further ado I offer you my arm, you take it and we leave the apartment together. To the world outside we are a respectable couple going on a respectable date. Men will glance lustfully at your legs and women will do the same with a sense of admiration tinged with envy. But none of them will know what is concealed beneath that dress and the debauchery it promises when the meal is over.

............

The food turns out to be everything we had wanted and it is complemented perfectly by the wine. The service is attentive and the atmosphere classy but not stuffy. In short, the date is turning into a very enjoyable evening, regardless of the unspoken object occupying your butt.

But its existence pervades our interaction and adds a sexy tension to everything we say and do. When we sat down at our table I noticed you do so gingerly, knowing that your position on the chair would push the plug further inside you and that you would feel it throughout the meal. The thought of it causes my cock to be semi-hard as I eat, anticipating an evening of action later. You are lucky that the seats are covered with leather to soften them a little. Even so, I dwell on the fact that even the slightest adjustment of your position must be complicated by the presence of the plug and that each movement must be awkward, to say the least.

And yet, to our fellow occupants of the restaurant, we appear unflustered and relaxed. We chat casually about a wide range of things as we sip our first glass of wine and enjoy our starters. As flatmates we already know most of the things about each other which most people would discuss on a first date, so we are able to flit from topic to topic, making each other laugh about the tedious absurdities of our everyday lives. We've always enjoyed each other's company, and tonight is no exception.

Just as the main courses are about to arrive, you start to rise to visit the toilet. Before you can leave I put my hand on your arm to detain you for a moment. 'When you come back,' I instruct, 'I want you to give me your panties.'

You pause in surprise and open your mouth as if to reply, but my voice has a note of finality and I am prepared to brook no argument. Sensing this you turn to leave. I watch you walk between the tables, sashaying slightly on your heels, still treading in a pained way, for reasons which I, and only I, can explain.

I sip my wine for five minutes and then see you returning across the restaurant. A glance at your face, which is flushed pink in shame, tells me that you have followed my instructions. Anyone seeing the colour of your cheeks would think I had made you strip completely.

You take your seat again, grimacing slightly as the butt plug once more makes its presence felt against the chair. I look expectantly in your direction. When you do not respond immediately, I speak. 'I told you to give them to me. Where are they?'

You know exactly what I mean. As your face turns an even deeper shade, you reach into your handbag and when you withdraw your hand it is clearly clutching something. You reach across the table, still concealing the contents of your hand as well as you can. When I take the panties from you I am much less discreet, allowing some of the fabric to show as I take a look. To my delight I can feel a substantial damp patch on the garment's crotch, which tells me exactly how you feel about your treatment this evening. If only you knew the full extent of what I have in store for you!

I put the panties safely inside my jacket pocket and ensure that we resume our conversation, behaving in as relaxed way as I can, bearing in mind that I'm sitting opposite a beautiful woman, who is naked beneath her flimsy dress and who bent over earlier to allow me to push a plug up her arse. Soon the main courses arrive and we resume our meal, savouring every delicious mouthful. Before we know it we have finished, the plates have been cleared away and I have insisted we order dessert to make the best of the meal.

As we wait once more, I tell you, without lowering my voice, to pleasure yourself. You gape in my direction, so I urge you a little more. 'Go on!' I say. 'Make yourself come right now!'

You have gone too far down the road of submission this evening to turn back, so you drop your hands below the level of the table and I see you wriggle as you hitch your dress up around your thighs. Thankfully for you there is a starched white tablecloth which drops low to afford you some protection, but anyone taking a closer look would realise immediately what you are doing.

Leaving you to get to work on yourself I survey our immediate neighbours in the restaurant. To my right a couple of men in suits are talking earnestly over what must be a business dinner. One of them sees me looking at him and I nod and smile. On the other side a couple of a similar age to us are gazing lovingly into each other's eyes. Meanwhile a larger group is sitting behind you. It is made up of young women, one of whom seems to be celebrating her birthday. They are not noisy. The restaurant is too classy for that, but they are clearly enjoying themselves and I suspect their evening will take a more raucous turn later.