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Letters to Fluttershy [NSFW, Anthro,]

gasmaskangel
Magical Inkwell - Wrote MLP fanfiction consisting of at least around 1.5k words, and has a verified link to the platform of their choice
Artist -
Since the Beginning  -

Inspired by the work of the ever excellent, seriousb. This is gonna be a different animal than my normal futa-tastic clop, and will contain some stuff that will be off putting to a good deal of people but I hope that it will be enjoyable to some.
 
I’ll be including images that inspired this whole mess with each image, starting with this one!
 
full  
The joys of nudity
 
My Darling Fluttershy,
 
I am so grateful that you’ve chosen to open up to me regarding your desires, and lest you fear that this form of communication is an imposition allow me to reassure you that I fully understand your reluctance to discuss these matters in person.
 
Without further ado, let us get to the meat of the issue. You desire a certain liberation in regards to your sexuality. Well I am certainly the mare to speak to in that regard. I know that I can give off a somewhat fussy air, and that one might interpret my sense of propriety as a sort of prudishness, but I assure you that simply because I am a Lady that I am no stranger to carnal desire.
 
You see my dear, part of being a Lady is confidence in one’s own tastes and desires. One must know what one wants and be willing to pursue it, after all. It is simply that there is a time and a place to indulge in ones desires.
 
I shall not sugar coat things my dear, if you wish to pursue your dreams then you must be prepared for ponies to disapprove. What you have shared with me would be quite scandalous in polite society, and no ammount of confidence will save one’s reputation from those who believe that slut is a dirty word.
 
Believe me my friend, to be a slut is no ill thing. It is not sin to desire and enjoy sex, even that which the ignorant wrinkle their noses at in disapproval. Sin comes only when you rob others of agency, property or life and I know you to be a mare of virtue with no malice in her heart.
 
You simply must rid yourself of these fears me sweet, or you shall never be able to properly enjoy the simple act of seduction.
 
I know that this frightens you, and you’ve my assurance that I will help you every step of the way. To begin we must take baby steps. Begin with simple nudity.
 
You must be comfortable in your own skin in order to be a true slut. Ideally you should be able to disrobe at any time and allow ponies to see and desire your quite comely form at their leisure.
 
Do you recall the Gala a few months back? Specifically when Smooze ruined my dress and Discord’s idea of helping was to strip me naked?
 
I shall let you in on a secret, darling. I loved it. I loved the feel of all those ponies eyes on me, from the sympathetic, to the disapproving, to the lustful. In fact, my flower was dampened quite significantly by that little display, and I had to work hard to conceal my enjoyment from you all.
 
Some did notice of course. If you’d like more details, ask our dear friend Applejack. That is a mare who knows how to treat a naughty little exhibitionist!
 
Forgive my rambling, darling. I must confess it feels quite pleasant to write this missive to you. Applejack understands, but she is an atrocious conversationalist and Pinkie Pie… well you know Pinkie Pie. I doubt the mare realizes that anything about her behavior is abnormal, and as such would not understand the simple appeal.
 
At any rate, nudity should be your first goal. I am not asking you to expose yourself to the whole town. While thrilling, that would be needlessly self destructive.
 
Rather, I encourage you to become a nudist in your own home and on your own property.
 
Again darling, I know that this is much to ask of you. Simply start with your bedroom. During all but the shortest periods within, strip yourself bare and simply enjoy the feeling of the breeze moving across your silken coat, your delicate nethers, your pert breasts and your simply gorgeous legs.
 
Once you have become comfortable with this, expand your territory. In time you shall give not a single thought to being naked in your own home, and I think that you shall be happier for this.
 
If you like after this, bring the show outside and refuse to change for guests unless they specifically ask you to. Always remember that the slut’s gratification is in gratifying others. However, if a pony is happy to simply watch you, then allow them. Watching is always allowable, darling!
 
Now, I’ve a simple exercise for you in those times when clothing is necessary or desirable for you. Please cease wearing underpants immediately. You need do nothing else scandalous with your wardrobe, though if you desire I can fashion you a truly erotic ensemble, simply go without panties or bra. Frankly my dear, you’ve no need of the latter.
 
If I may flatter you for a moment, I adore your bosom darling. Large, but not obtrusively so. Well shaped, and without a hint of droop. Oh darling, I do wish that I’d known your fantasies lay in this direction before now! How I’d have loved to spend time stroking and teasing your luscious flesh…
 
Ah… but I digress again. I do apologize to you for these little asides, darling. It is hard to focus when writing with only one hand.
 
I should close this out by telling you that unless nudism is itself a fetish for you, then you should pursue these exercises only so long as it takes you to get comfortable with your own body. While it is certainly erotic to be stripped bare and be gazed on by friends and strangers alike, making nakedness too normal will rob it of its thrill, and I could never forgive myself if I stole a joy like that from you.
 
Should you desire one on one help, you may ask at anytime and in any way.
 
Your fried,  
Rarity.
gasmaskangel
Magical Inkwell - Wrote MLP fanfiction consisting of at least around 1.5k words, and has a verified link to the platform of their choice
Artist -
Since the Beginning  -

@Pizzamovies  
More is coming soon, and it is gonna get nasty the deeper I go. Haven’t approached the stuff of seriousb’s that I find really hot yet, mostly because I suffer from an odd compulsion to build this stuff up slow instead of diving head first into depravity.
 
I’ll make sure that there is warnings at the start of each letter pertaining to all the stuff that might make people nope the hell outta here.
gasmaskangel
Magical Inkwell - Wrote MLP fanfiction consisting of at least around 1.5k words, and has a verified link to the platform of their choice
Artist -
Since the Beginning  -

On The Proper Use of One’s Best Assets
 
full
 
Darling Fluttershy,
 
My dearest friend, I am simply delighted that you’ve so wholeheartedly embraced my advice! I’d never have dreamed that I’d one day take tea with you in such a state of utterly splendid nakedness.
 
I know that it must have been quite hard for you, but I also suspect it was quite rewarding if the scent you left on the seat is any indication. Goddess, you are gorgeous when you blush.
 
Now, regarding what you included in your last letter. First, let me assure you that I quite understand the idea of wanting to retain that feel of embarrassment when a pony looks at your unclothed form. That fear and that excitement… I certainly understand how that might heighten the thrills of exhibitionism.
 
If you like, I can perhaps arrange the odd wardrobe “malfunction” for you every now and then, however humiliation is a topic for another time.
 
Today, let us discuss how you might better advertise your availability to interested ponies.
 
There are many ways to attract the prurient attention of those around you, darling. The simplest I have found is a tight skirt and a low cut blouse. Frankly, you dress so conservatively that I suspect adopting either would prove quite eye catching!
 
However, anything too shocking might be a bit too much at this stage. Leave your observers wanting to see more of you, hungry for you.
 
Ideally we shall want something with the pretense of respectability which still leaves ponies with a desire to rip your clothing off and ravish you in the street.
 
To this end, I suggest we focus on the exposure of only one of your assets at a time. As the seasons drift on and ponies become used to this, we can begin show casing your other treasures as well.
 
Now, as I quite embarrassingly confessed in my last letter, I’ve a great fondness for your breasts. Their supple curves, the firm yet yielding feel of them in my hands, the way those sweet nipples of yours stiffen at the slightest touch… they are quite simply magical.
 
Similarly your buttocks is a work of finest art. Muscular and fit with just enough flesh to give it bounce. Believe me darling, there are few stallions who do not appreciate a fine ass. You’ll see when they fondle, grope and spank you, all of which might seem scary now but trust me when I say that nothing is quite as erotic as a pony both worshiping and punishing your rump.
 
I could sing praises of every part of your anatomy darling. Your flat stomach which invites the fingers to stroke and caress, your lean arms, your graceful wings, your silken mane and tail, your eyes of softest, sweetest green… but there is but one that I shall praise above all.
 
Your thick, shapely legs. Celestia forgive me but I adore them. Tall and well toned with muscle, your thighs wide and far more powerful than you seem to believe.
 
I swear that I very nearly climaxed stroking my hands over them. If you should ever wish, I shall be more than happy to worship them however you might please.
 
To that end I prescribe two things for you, my darling. First, shorter skirts. We simply must place these beautiful limbs on full display. Additionally, this will allow more of a chance for ponies to catch a glimpse of your bare nethers. We must tempt the hand to explore, and the eyes to gaze.
 
To emphasize the sweet shapeliness of your legs all the more, I also recommend some high-heeled shoes. Now, these will take some getting used to and they can indeed be something of a pain, but the effect is quite worth it.
 
Have no fear, I shall be with you as much as you can to help you on your way. We shall also take the opportunity to teach you how to walk.
 
Yes, that does sound rather condescending doesn’t it? But it is necessary I’m afraid. You will want your every step to entice, to promise unimaginable delight to those around you.
 
As in all things practice will make perfect, but you do have a natural ease and grace that shall make this an easy exercise I suspect.
 
Your friend and servant,  
Rarity
gasmaskangel
Magical Inkwell - Wrote MLP fanfiction consisting of at least around 1.5k words, and has a verified link to the platform of their choice
Artist -
Since the Beginning  -

On Fantasies and Their Fulfillment
 
full
 
My Darling Fluttershy,
 
I quite thoroughly enjoyed your most recent letter, and yes I do mean that exactly how you think that I did. You may just have an undiscovered flair for erotic writing, certainly more so than I.
 
Now, I do not find the idea of rape fantasies to be shameful. Dark, certainly and I must confess that I’ve only indulged in them myself when feel persecuted and put upon, but they are hardly a sin.
 
Nor am I offended by the role that your fantasy cast me in. It was in fact something I rather fixated on while going for my orgasm. I’ve always been quite fond of oral sex, darling, as you well know by now (and incidentally next time we indulge ourselves you can afford to be a bit rougher. I’d appreciate a bit of mane pulling to encourage me to really get my tongue in), and the idea of being forced to keep dozens of stallions hard while they ravish my friend? Magnificent.
 
I particularly enjoyed the way they’d use me as a common rag to clean up afterwards, as well as a urinal. Did you happen to write that for my benefit, pet? I do not believe I’d ever confessed my love of so called water sports to you.
 
At any rate, the only reason to be offended or ashamed by what you’ve written would be if you actually wanted the both of us raped. This is certainly not so.
 
Thoughts are not evil. Fantasies are not wicked. Evil can only be done in deeds, and I know you well enough by now to say, with confidence, that you’d never intentionally commit an act of evil.
 
And before you bring it up, each time you have acted beastly it was under the influence of another, and in the case of Iron Will you ultimately stopped yourself and truth be told if the worst you’re inclined to is being insulting and harsh of speech, then you’ve nothing to fear.
 
Now my dear, I must tell that it is possible to indulge your fantasies to an extent. All you shall need is a willing and understanding stallion, of which there are more than many mares think.
 
This is a case not for sluttiness, but for genuine friendship and affection though. You must approach a stallion which you fancy, and delicately find out how far he is willing to go for you. Some will be appalled by your fantasies, but only because they could never cast themselves in such a role. Be delicate. Do not imply that you could easily see the stallion in question as a rapist.
 
This will be difficult, because I do not think it would be wise for me to assist you on the matter. Rather enough pressure will be on both you and any pony you approach without my fussing about.
 
Further I would suggest delaying any such efforts till we have reached a point where you can have a conversation about sex with a stallion without falling to stammers and whispers. You’ve made much progress, but we’ve still a ways to go.
 
I do believe that it is time we did something about your virginity, darling. My pleasuring you does not count, you will need to experience actual, penetrative sex if you wish to be rid of it. If you like I do own a number of toys which can do the job which you can borrow, or if you prefer I can assist, however I do believe that now is the time for your first big step into sluttiness. It is time for you to meet a man.
 
Your friend and servant,  
Rarity
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