Correspondences with Maddie

Author's Note: The following is a work of fiction and is presented as a pair of handwritten letters sent between David, a much older Sugar Daddy, and his young Sugar Baby, Maddie. It is a bit different than what I normally write, but I hope it is just as enjoyable.

Correspondences with Maddie

To:

Madeline Stevens

247 East Street

...

Date:

9th June

My dearest Maddie,

I hope that this letter finds you well. I understand that actually receiving a handwritten letter is probably alien to such a youthful girl like yourself, what with that WhatsApp you introduced me to so we can communicate more easily and you can send me those pictures and videos that turn me on so much, but I hope that you will forgive an old man his whimsy in finding there is something much more special and intimate in communicating with you in this way.

As you can see, receiving a letter also has its advantages in that it can be sent along with a gift, and I hope that you find what I have enclosed in the package with this correspondence to your liking. I know you mentioned Prada was your favourite brand when we were out shopping last Friday.

I have been thinking about that day a lot recently. Spending time with you is always so magical, but honestly having you with me all day like that was truly one of the best things to happen to me in a long time.

You looked especially beautiful with your auburn hair in pigtails like you had it. It made you look so sweet and innocent, and even younger than your twenty years if that is even possible. Your choice of clothing was exquisite too, that black dress was incredible. The way it clung to your slim, supple body, exaggerating your curves and the mounds of your breasts whilst also showing off your intoxicatingly arousing cleavage... Just thinking about it now has me flustered, I do not mind telling you, my dear.

Do you remember the looks you got from men? The lust in their eyes to see your beauty was palpable, and I felt like the luckiest man in the world to have you on my arm as we strolled around Harrods and Goldsmiths. I still chuckle when thinking about that one particular fellow who mistook you for my granddaughter, the look on his face when you kissed me was priceless. If he was still in any doubt, after your little display, of what our relationship to each other was, I am sure that would have been obliterated had he gone back to our hotel room in the Conrad and witnessed what happened that evening.

Oh, the night we spent in room 187. I can honestly say it will live long in my memory indeed. What was it you said when you had me sit on the bed? You wanted to thank me properly for that Cartier necklace I bought you? Well, did you ever do that you little minx! I do not think I have ever been so utterly worn out by a girl in my entire life. I was lucky my heart did not give out at any point.

Watching you slowly dance and strip for me, peeling down your dress to reveal your lacy bra and then still further until those frilly, French cut, satin knickers and thigh high silk stockings came into view, why it had my heart pounding and another part of my body stirring too.

I so wanted to touch you, to feel your soft youthful skin on my hands, to massage your breasts and caress your buttocks, but you insisted I just watch as you gyrated your hips and moved your supple body for my pleasure. I was glad you did too, because I realised quickly that watching you dance for me was far more arousing and sensual.

How you teased me Maddie, caressing your own body just out of my reach. Your hands sliding over the covered mounds of your big breasts, rubbing the insides of your shapely thighs, slapping your succulent round buttocks as you wiggled it in front of me. I was putty in your hands, my mind under your control as I sat and watched you, and you knew just how to excite me!

The way you peeled off your bra, slowly, making me wait for each inch of your flesh to be revealed, until finally with a flourish you whipped it away and my eyes beheld your breasts in all their glory, so perky and smooth, topped by the most amazing pink nipples. They looked just like little pencil erasers, pink and erect, standing proud and just begging to be kissed. How I wanted to take one in my mouth, wrap my lips around it and suck just to hear your soft moans in response, but you had other ideas, did not you.

You drew my eyes downwards, after caressing those mounds for my enjoyment for a while of course, and teasingly started to play with your knickers, pulling them down an inch then back up, turning around and bending at the waist to show off your peach like bottom covered by that shiny, soft satin to make my mouth water. I could hardly think straight as I watched you playfully slide your hand between your thighs, cupping your crotch and sliding your palm deliberately over the material as you moaned slowly and seductively.

Seeing you touch yourself like that, with those knickers and stockings the only things covering the nakedness of your young, slim and tight body, I do not think I have ever been as aroused as I was by you in that moment Maddie, my dear. You knew it too, did not you? I could see it in the look in your eyes; the way you smiled and your movements. You were immensely enjoying having me in your power, enraptured by your display of youthful femininity.

Those few minutes you teased me, almost but never quite displaying your most intimate parts to me, were by far the longest of my life. I was so aroused it was almost painful, and yet you still would not put me out of my misery, instead only heightening my exquisite suffering by sliding your hand down inside your knickers and cooing to me, telling me just how wet and hot you were as your fingers caressed and played within their confines.

I cannot tell you how much I enjoyed that. Honestly, watching and hearing you as your fingers moved, not able to see exactly what they were doing thanks to your frilly underwear whilst you moaned and talked, had my heart pounding in my chest, and another part of my anatomy stiff and throbbing. I did not think I could be more enraptured by you than I already was, but your playful teasing, the light softness of your voice edged with a hint of excitement, had me intoxicated by you like I have never known before.

When you slipped your hand free I could do nothing else but watch as you brought it up to your mouth, smiling wickedly as you brought your fingers to your lips and parted them, flicking the tips with your tongue and fluttering your eyes as you did so. If I was not already sure I had the most gorgeous and wildly exciting girl in the world in my presence at that moment, then that little act would have left me under no further illusion.

Watching you lick and suck your fingers clean had me breathless. I had never seen such a display of wanton filth from a woman before in all my long life, and seeing it performed by such a beautiful and nubile girl as you... Well, what more can I say? Other than that I fell even more under your spell at that moment.

After you had put on your show of cleaning your digits, finally you put me out of my misery, although that is not the correct word to describe how I was feeling. Misery suggests I was not enjoying your teasing, but nothing could have been further from the truth!

I can still see so clearly in my mind right now when you looked at me directly, meeting my gaze with your perfect blue eyes and holding it, whilst you slowly push your frilly satin knickers down your long stocking covered legs, exposing yourself and almost daring me to break our eye contact and look at the enticingly erotic sight that were now on display for my viewing pleasure.

I could not help myself. I wanted to resist the temptation, if only for a few seconds, to show you that I could, but the allure was too strong. How could I possibly not let my eyes fall downwards when the most beautiful thing on Earth, your womanhood, was mere inches away from my face?

I know I have told you this many times, but I feel I must again Maddie, so please forgive me, but there is no greater pleasure in my life than to see what splendours are hidden between your supple thighs! The pinkness that contrasts with the surrounding white skin, the fleshy folds hiding the wonders within... it is all I can do not to drop to my knees and thank God that he made such perfection as your sex and gave it to the world.

Even now as I write these words to you I am stirring again. Just thinking about your womanhood has my heart pounding and my loins burning with desire. How can any man resist a creature of pure youthful perfection as you, my dear? Merely picturing your nakedness in my mind brings me to levels of desire that no other can match. Seeing it in person, touching, being inside it, those things take me to heights that only the angels can know.

That night, in hotel room 187 of the Conrad, I could do nothing but stare and drink in the beauty of your womanhood. I could see the faint glisten of your arousal on the lips that so enticingly frame and hide the treasure within, smell the unmistakable scent that wafted from you like the finest and sweetest rose. It drove me wild.

You must have felt the same too, given what you did next. Unlike myself you had been able to master your carnal desires much longer, but having my eyes fix on your naked womanhood, devouring it with my gaze as I wished to with my mouth, I can only assume was too much for your resistance.

I know I do not need to tell you what happened next, but forgive an old man his whims, for I am in the flow of memory now, trapped in its tides, and the words are being buffeted from my mind and through this pen onto the page you are now reading.

I will never forget the way you spoke to me in that next moment, the sound of your voice or the look in your eyes as you placed your hands on my shoulders and pushed be backwards until I was lying prone on the bed, telling me to relax, that that tonight was going to be all about you showing how much you appreciate me.

The vulgar way you spoke, the filthy language that came from your angelic mouth, it was all so arousing. In my generation, a girl of twenty would never say such things as you did, nor would they be so forwards as to do the things you did, but your generation know no such bounds of decency and hearing you swear as you grappled with my belt, and then watching as you hastily removed my trousers and underwear, freeing me from the confines to stand proudly, displaying just how much I desired your youthful body, it was like I was in heaven.

It still makes me want to groan now, as I did then at the time, when I think about your lips encircling the tip of my manhood, taking me into your mouth and kissing deeply before you slid down my length, the warmth and wetness enveloping me. I have never known such pleasure as brought about by you Maddie. Few can boast such oral skills as you have mastered at such a tender age, and I, the frequent recipient of your expertise, can attest to that if any should ever doubt its validity.

Watching you bob your head on my crotch, your auburn hair partly hiding your young, gorgeous face from my view, I could only marvel at how lucky I am to have such a goddess as you as my lover. I could hardly restrain myself as I felt the pleasure rising with every slide your lips made downwards and back up, your saliva covering my hard, wrinkled flesh which throbbed in response to the touch of that wetness, to the heat and tightness all around it.

How long was it you sucked me for? How many times did your hand squeeze the base of my hard shaft as your succulent lips and tongue combined to bring about such unrivalled pleasure? I honestly cannot even remember, for I was too enthralled at the moment experiencing that wonderful sensation to make note of something as mundane as the passage of time.

The sultry look you gave me, making way for a wicked grin, when you slipped your lips fully from my swollen manhood finally after sucking me until I could hardly stand the pleasure any longer, was worth everything I had spent on our day trip to London this far, and yet it had only been the beginning of what you had had in mind for me had it not?

I felt powerless to move as I looked into your beautiful blue eyes, and could only marvel at my fortune to be in bed with such a gorgeous creature as you when your lithe body crawled up my body, placing your hands and knees on the mattress either side of me as you moved, your big breasts swaying in the most alluring way possible, until you were straddling my crotch, sat up and looking down with a grin on that angelic face of yours.

You felt like molten velvet around me as I sank into your wetness. Your mouth was hot and your lips tight, but I had almost forgotten in my enjoyment of your oral attentions that it is of no comparison to the true quality of your silky soft womanhood. The heat on my stiff manhood as your body sheathed it was unparalleled, as were the feelings that were brought about by having your young body atop me. Looking up from my back to see your beauty, the mounds of your firm perky breasts jumping, your auburn hair flowing, your face a mask of pleasure as you gyrate and lift your hips, sliding your tight passage up and dropping it back down, my length... It was almost too much to bear.

The sounds that filled the room as you rode me were the sweetest symphony, played on the most beautifully crafted instrument, not even the greatest composers could match it. Warner, Mozart and Beethoven, all would have wept upon hearing the perfection of the gasps and moans that spilled from your mouth as the pleasure grew deep within your body, the slap of your flesh meeting mine as you brought your weight down onto me, the wet slurps that accompanied my hard manhood being driven deep into your nectar filled center.

It was not just the sounds that were intoxicants however, the scent that filled the room was every bit its equal. The heady aroma of your arousal was pervasive, filling my lungs and setting my lusts afire all the more. I am sure you could feel my stiffness grow inside your tight embrace, my pleasure driving it, as you bounced your hips hard and fast, with a vigor that only youth such as you have can bring.

I hoped you would not find my actions crude when I lost my self control and reached up, taking your bouncing breasts in my hands and squeezing those magnificent orbs of flesh. I just had to feel your warmth more, your vitality. It made me feel young again myself as my fingers played with your bosoms, the erect nipples that top them digging into my palms, as you so energetically lifted your hips only to force them back down, taking my manhood deep into you over and over.

I had no reason to worry of course, for you cried out in response to my touch, urging me to grab you more roughly, and pushed your chest out forcing your breasts into my hands. Your hips sped up too, gyrating more forcefully, doubling both of our pleasure as I moved within you and I could feel your wetness flow, and tightness grow around my invading shaft as your body tensed and your moans became hoarsely ragged as you reached the peak of ecstasy.

No beauty can compare to that of a woman in the throes of exquisite orgasmic bliss. The flush of their soft skin, the contortion of their features as the waves flow throughout their body, it is perfection in the flesh, but you are as Venus is to mere mortals, a goddess whose beauty transcends. How could I possibly have held out against such an onslaught as I experienced whilst you climaxed on top of me?

That time we spent afterwards, lying on the fluffy mattress together, your stocking covered leg draped over me, my hands slowly caressing your sweaty supple body as we both recovered, basking in the glow of our pleasure, were almost as good to me as our vigorous love making had been. I was tired out, my limited energy spent. Yet you were raring to go, eager to continue and explore all the possibilities the night offered us.

In the bloom of youth you knew no bounds of age as we of the older persuasion do, but despite my reservations on my ability to keep up with your desires, and my need to rest and restore myself, you still insisted on trying to perk me back into action, not taking no for an answer.

If it had been anyone but such a young, gorgeous girl as you it should not have been possible I am certain, but well within an hour of my climax your deft touches and oral attentions had my manhood standing and ready once more. It was testament to the adage that there is no substitute for youthful enthusiasm, because not since I was fifteen years younger could I be coaxed to perform such sexual congress twice in such a short space of time as you had me do.

It makes me so envious how you achieve such heights of pleasure so often and easily whilst I must only achieve it once at a time. Yet such joy do I achieve from feeling your body respond to those peaks as I am inside you, my manhood squeezed by your inner walls as your strong shapely thighs hold me tightly, I would no more wish to deny you such physical excess as I would dream to try and hold back the tides.

This time it was my turn to be the loud one, although your cries of ecstasy certainly were far from quiet. But since I was now exerting such energy as I lay on top of you, thrusting my hips, I could not help but grunt with the strain, not that you would ever hear a complaint from me at having to ask so much effort of my body when it is spent on you, my dear. There is no man of any age, be they eighteen or a hundred, that would stand before a jury and say the feel of your twenty year old flesh as you gave yourself to them in this most intimate way was not worth any price.

After you had my second offering planted in your depths following that long, slow and pleasurable session we spent with your legs wrapped around me, my manhood sliding back and forth within your warm, wet passage as I fulfilled your repeated filthy requests to make you climax over and over, thankfully you relented and gave me a longer rest than before. The spirit had been more than willing to go on, but the body was most certainly not of the same opinion, unfortunately.

As is testament to both your sweetness and maturity despite your youthfulness in years, you understood my needs. I can still hear your praise of my performance as you laid your head on my chest and simply relaxed with me, your soft hand merely tenderly caressing and stroking through the gray hairs that adorn my upper body.

If you had been older, I should have placed all my entire fortune on our carnal pleasures being over after that second round of shudderingly intense love making was over, but not for the first time since you came into my life I was reminded just how insatiable the youth of today are, and how much the touch and encouragement of a beautiful and voracious young woman like you can persuade even an old man such as myself into feeling like a teenager again. Thus it was of no surprise to me that before we finally retired to sleep, you once more started to cajole and plead for me to make a last carnal effort.

Despite my previous exhaustion, I was able to rally remaining reserves of energy, thankfully a little replenished after the few hours break you had allowed me, and you made it very worth my while, you little minx, by yet again treating me to the exquisiteness of your body and all the pleasures that can be found from it.

Given that I am entering the twilight of my life I am not prone to such feats of physical prowess as a young man your own age may be able to reach, but I do have skills to please my partner accrued over a lifetime that such bucks cannot match, and I used them all on you in those last minutes we shared exploring the potential delights available to us on that hotel bed Maddie.