Letters to a Good Girl Ep. 01

Author's note: these letters are works of fiction, but are dedicated to the beautiful, wonderful real women who inspired them.

19th January 2020

Marylebone

My dearest O,

So, tomorrow is our first night together. It's been great getting to know you. You are a funny, intelligent, kind and infinitely charming person, as well as a considerable beauty. But tomorrow, by your own consent, you will become a fucktoy: a slut for use, a piece of meat for Sir to use as I wish. And you will be marvellous.

I know this because of a single moment. We were under a railway bridge, walking off the Italian food we'd eaten on our second date. Our first kiss still tingled on my lips. Walking by the Regent Canal, we passed under a bridge. No-one was visible, or audible, in either direction. I stopped, put my arm around your slim waist, and pulled you to me. Your big green eyes were looking up, and your lips, that need no enhancement by lipstick, parted a touch. I kissed you, slipping my arms inside the coat you were wearing against the London cold.

Then, slowly, I pushed you against the wall. I knew the brickwork was damp and cold, but you didn't resist—far from it—you seemed to melt as I took charge. I kissed your neck and whispered what I wanted to do to you, and your breathing quickened, became ragged.

But that wasn't the moment. Your dress wasn't exactly short, but it wasn't hard to move a hand under the skirt and rest it, over your tights, on the mound of your pussy. You wriggled a bit and looked around, but bit your lip and looked up at me, fearful and expectant. I tightened my grip around you, and looked down, smiling.

Then, very briefly and gently, I ran a finger over the gusset of your underwear.

Several things happened. You gasped. You tightened your grip on me in turn. And, even through tights and cotton, your wetness was obvious. That was the moment that I knew you could be a really, really good girl.

So, I'm confident tomorrow will be amazing. But, just in case, I thought I would reiterate the rules when we are together.

1. You will call me Sir

2. You do exactly as I say, immediately

3. You speak only when spoken to, unless it is to please me

4. You accept whatever use I have for your body.

I trust this is clear.

I will see you for dinner at seven. You know the place.

With keen anticipation

Sir

21st January 2020

Marylebone

My dearest O,

Well... It's fair to say you have exceeded expectations. You can enjoy your day off on the knowledge that you have served Sir well.

I know that you were nervous at dinner. I must confess I relished your skittishness too much to entirely reassure you. I enjoyed openly appraising your figure through the lovely outfit you chose. The trousers that clung to your round, shapely buttocks, but then fell in wider drapes, so your athletic legs only show themselves in motion, encouraging me to pay close attention. The top was tight but not revealing, and the criss-cross straps would be suggestive of bondage gear only to those in the know. The shirt worn lightly over the top hid your figure from behind, but the open front allowed me to feast my eyes from across the table. And I had my fill. I enjoyed letting the conversation tail off and staring at your pretty face and tight body till you blushed. Not that the conversation was anything but fascinating—I enjoyed you refuting my views on politics, all the more because shortly, your opinions would no longer matter... at least for a while.

I think when we got to the flat, you were expecting kissing and seduction, but you took it in your stride when I simply led you to the living room, sat in an armchair and instructed you to strip naked. I know I said it at the time, but you really do have a lovely body. I especially appreciated the way your stiff nipples looked alongside the cascades of your gorgeous auburn hair and the girlish way you played with your hands while I surveyed my new toy.

I don't even mind that shortly after that you broke a rule—it takes a while to get used to every utterance ending in a respectful 'Sir', and where would be the fun if you were already perfectly trained?

Again, I think I surprised you—no box of implements to punish a disobedient slut (not this week, anyway), just two silk ties and my big hands. You looked so pretty with the first tie round your neck that I kept it on you all night, and you crawled so nicely after me as I used it as a lead for you, placidly accepting your place in punishment, facing the wall on your knees. The other tie secured your hands behind your head, and there I left you, to think about the importance of obedience, and await Sir's pleasure.

I got myself a drink, strolled back and ordered you to turn round. I enjoyed how, robbed of the use of your arms, you had to move so awkwardly to obey my command to turn and face me, and how the awkwardness made you flush. You looked humiliated, and beautiful. And then I spat on you.

I'd never done it. You'd never had it done. It's a simple but demeaning gesture, and it was electric. I let the foamy spittle sit on your face and asked you if you were ready to suck Sir's cock. This time, no rules breach. "Yes, Sir".

You didn't take it all—no-one ever has—but it was an excellent first attempt. I loved that you maintained eye contact, that you were unfazed by not having your hands to control the penetration, and that, when I pulled on your lead enough, and slid my shaft deep enough to make you gag, you kept me in your throat. That's a good fucktoy.

I have a feeling that, of all the lovely parts of your body, your ass will become my favourite. So pert, and round, so pale until my hands have been to work. I laughed afterwards when you said you'd never been spanked that hard, or for so long, before. So many guys think a rushed spanking to get the juices flowing is enough, but a prolonged session, gradually building in intensity till your cheeks are scarlet... that's proper punishment for a whore like you. I didn't even make you comfortable for it—unless bent over my dining table with hands now tied behind your back is your idea of a comfy rest... Maybe in some ways, it is.

But the position meant that, to rest your torso on the table, you needed to spread your legs, which of course gave me easy access to your pussy, first to give a firm spanking to, and then, to your evident relief, to slide my cock inside.

It felt incredible—to have your hot, tight hole stretched around me, to see you writhe and moan, to hear you shout, "Fuck, yes!" as I slid in, then hurriedly add "Sir". The position allowed me access to your whole body, so I could try some things that I think we might develop further—hair pulling, a bit of face slapping, and that delicious-looking other hole...

I know you've never done anal, and I will take it carefully. But it will happen; you will be my anal slut. That hole, like your other two, belongs to me, and I will claim it. The gently probing finger last night is just the scouting party...

Of course, I eventually came on your face. Ever since I first saw it at the window of a cafe in Soho—animated, inquisitive, and pretty—I've wondered what it would look like covered in ribbons of my cum. And now I know—slutty, depraved, and beautiful.

It was all amazing, everything you gave me last night. But almost my favourite moment happened later, as I held you, one arm around you, the other with two fingers in your cunt. I was whispering to you about what we'd done, what we will do, what a gorgeous, obedient slut you are, and you were frantically rubbing your clit. Your orgasm shook you all over, and you screamed louder than ever I expected. The feeling of your vagina tensing around my fingers was incredible. You were asleep almost immediately, and you've been slumbering ever since.

I look at you now as I write—so pretty, such innocence while sleeping—and I can't believe what I've made you do. Of course, it's nothing to what I'm going to make you do, but you know that. We've started on a journey, and I can't wait to see where it goes.

But duty calls. Make yourself at home, O, for as long as you want. I'll see you soon.

You have been a very, very good girl.

Sir

14th February 2020

Marylebone

My dearest O,

It's been really wonderful to get to know you these past few weeks, texting every day about everything, and nothing. But if you're going to be my fucktoy, we need to have compatible appetites. That's what last night was about.

Still, I appreciated your characteristic wit when, walking in and seeing the array of equipment on the table, you pretended shock and said that you didn't know what half of them were for. Well, you do now...

Actually, in fairness, you were blindfolded for at least part of proceedings, so maybe I do need to clarify which painful impact was which.

So, as I recall, I had peeled off your rather elegant coat (see, I do pay attention to things you say you like), and the buttoned shirt underneath (and vice-versa, clearly). I appreciated the fact that you weren't wearing anything else for many reasons—your resistance to a chill night, your braving the Tube in this outfit, but most of all because it meant that I could have you naked, and tied by the wrists to the door lintel between my kitchen and living room, within a minute of being in the flat.

I blindfolded you because I wanted to keep you guessing, to accentuate your sensations by making them unexpected. I gagged you because I have neighbours and planned to make you scream. And besides, you looked hot with the ball in your mouth.

You have such wonderful skin, O. I love how soft it is, the faint freckles across your nose, and the way your paleness looks when offset by my darker hue. But most of all I love how quickly it reddens when punished; it's like a responsive canvas recording the punishment I mete out.

So, when I started with my hands last night, spanking your round ass, it immediately started to show a blush of red. As I increased the intensity, I could make out, just, the outlines of my fingers.

I used the whip on a lot of you, starting from your calves and working up towards your buttocks. You did very well to keep your legs apart, as instructed, especially when the thin strands struck across your breasts without warning. You kept still, like a good girl should, even when I swung the whip and it tickled around your pussy.

By now your body was fairly diffusely red, and I felt that some more specific punishment was in order. I never did show you the metallic object I touched you with next, did I? It was a spatula, long and thin, and, well, you know how much it stings. I concentrated on your ass, producing a pleasing pattern of stripes and some impressive moaning from you. You may wonder when I knew to stop; how I knew that you had reached your limit? Well, you know the safe gesture we agreed, putting your index fingers and thumbs together? I watched for a twitching that suggested that you were thinking about doing it, gave you two more lusty blows, and stopped. But not, of course, before I teased your nipples with the cool metal. Next time.

After the metal, the leather of my small paddle probably felt like a relief, but not where I was using it. You had said your inner thighs were especially sensitive, and I started softly, fluttering the flat surface over your smooth skin as it rose towards your cunt. You knew to keep your legs apart. The cane was placed between your feet and I had made it clear what the consequences would be if you touched it...

You held out so long, my beautiful slut. But I took you by surprise, suddenly bringing the paddle down on your clit, and your thighs snapped together. You knew you were in trouble, but I didn't shout; I don't like to. "Open those legs, fucktoy". You obeyed, and I delivered those five more strokes on your labia with calm savagery, counting them off. You were panting when I finished, and I wanted to see your eyes.

They were wide with pain and arousal, and standing in front of you, looking at those deep green pools, I briefly lost my self-control, smiled, and kissed you passionately. When I pulled back, I was Sir again, and my hand was on your sopping pussy. So, so wet.

But I couldn't get distracted; I had a punishment to deliver. As I picked up the cane you started to struggle and I could make out you saying, "No, please," through the gag, but no safe word, nor gesture. You craned your head back in appeal, but seeing my steely gaze, turned back and dropped your head in submission. As you should, my beautiful fucktoy.

The cane is, I will admit, my favourite implement of punishment. It can be delicate, as I began, tapping your buttocks gently as you quivered in anticipation. It can be precise, as when I placed neat stripes on the join between your upper thighs and buttocks. And it can be brutally painful, as it was when I just thrashed you for the last few strokes while you screamed through your gag. Your ass showed a beautiful criss-cross of long welts, and I couldn't help but stroke it with a gentleness that I entirely felt.

But I wanted to push you in one more way before I gave you what your dripping pussy clearly craved... I came round to the front, and removed your gag, which you were discreetly pushing at with your tongue. I know they stop being fun after a while, and it had served its purpose. Plus, I wanted to hear exactly what noises you would make next, gagless.

The nipple clamps are small, and delicate, with silicone tips to give some degree of comfort. But you had never been clamped there before, and the way your eyes widened when I produced them from my pocket was just delicious. The "yes, Sir" when I told you what would happen was heartfelt and brave. They need a little lubrication to slide onto the nipple comfortably, but fortunately there was no shortage—a quick delve between the folds of your labia and my fingers were slick with juices.

You gasped when the first went on and bit your lip. The second made you gasp again and breath shakily, your eyes watering. But you steadied your gaze, looked straight at me and said, "Thank you, Sir". I could have kissed you (I know, there was lots of that later, but still...).

I was still fully dressed at this point, but rock hard, and it was time to give you the reward that we had agreed—a hard fucking. I stripped naked in front of you, enjoying the way your eyes gravitated to my member, and briefly considered untying you from the door frame so you could suck me, but the position was too perfect. I went behind you, pushed your legs apart, laid a hand on your striped, abused ass, and slid myself into you.

This was the reward you had requested—to be filled with me, stretched by my girth. Your moans as my cockhead reached your deepest places were relieved as much as lustful You told me later how the pain in your nipples and ass blended with the pleasure from your pussy, so the two were hard to tell apart. It all added up to a symphony of stimulation, which is how it should be, fucktoy.

But I had a surprise treat for you. You had been exceptional and deserved something special. The wand vibrator hadn't been in my little display (in case you're wondering, it was hidden in the bread bin, but I promise it was free of crumbs), but I was able to reach it, and place it on your clitoris without breaking my rhythm. You are a good, grateful girl, and had already started to say, "Thank you, Sir" when I switched it on.

Your gasp was so, so pleasing. I filled you as much as I could and held my cock in place as the vibrations shook you. Your breasts shook with the rest of you, increasing the pain from the clamps, but you didn't have enough attention left to ask me to remove them... From this point, you lost yourself. How do I know? Well, from then on, the only thing you said was "fuck" and "me", and you barely noticed when my other hand left your ass to grab your hair, allowing me to fuck you even deeper.

I'm not sure which one of us started to orgasm first. Did my sudden thrust and pulsing cock set you off? Or was it the tightening of your cunt walls that made the urge to release irresistible? Either way, it seemed to go on for ages, until you slumped forward, exhausted, and I leaned forward to kiss your neck. And slip off the clamps.

I'm not usually aware of the age gap between us, but it's my excuse for how much more energetic you were afterwards, and how soundly you beat me at cards. Still, I guess it was my turn...

Anyway, happy midpoint-of-February day, my beautiful slut. See you soon.

Sir