Fluttershy's session

>She was terrified.
>You had arranged for the most relaxing room in the place, figuring it was a little early for the usual stone dungeon look.
>The space was well equipped, but with its casual decor it felt more like a recroom than the medival torture chamber might envision for this sort of affair.
>Well, your recroom perhaps.
>The carpeted walls were adorned with an assortment of attachment points, but instead of implements hanging menacingly from hooks you find discrete cabinet doors.
>As you saunter in, your bare feet are gently cushioned by a thick layer of matting covering the floor.
>Cozy as it may be though, it was doing little to calm the yellow pegasi waiting for you.
“Fluttershy?”
>She barely manages to make eye contact with you, standing rigidly in the center of the room.
“So.. the day is finally here.”
>You rub your hands together eagerly, hoping she'll relax a bit.
>She doesn't.
>This wasn't entirely unanticipated.
>The first time the two of you had met, you said but a handful of words to each other.
>It took time, but eventually she opened up, and now here you were.
>Her first session.
>Resolved as she had been to finally go through with this however, you feared she'd blurt out the safeword right now.
>You were going to have to be delicate.
>The last thing you wanted was to scare her away forever.
“Alright Fluttershy, I know you said you wanted a proper session, but we'll start things off slow just like we talked about, ok?”
“Think you're ready to get started?”
>”I.. ”
>She hesitates, speaking more to the floor than to you.
>”I-I think, I mean Y-yes, I-”
>You interrupt her with a warm smile.
“Look, we don't have to get started today. Now that you've seen the space it might not hurt to take some more time if you feel you need it.”
>“No, I-I want to do this.”
>You do have to admire her determination.
“Well, alrighty then.”
>You beam enthusiastically, hoping to set a lighter mood.
>”Lets get you into some ropes.”
>As you gathering up what you need from around the room, you can't help notice her nervous glances.
>Her head swivels to follow you as you make your way to her side.
“Keep your eyes forward please.” you say in an unfortunately commanding voice.
>”I.. sorry” she squeaks, her head snapping rigidly forward.
>The tremble in her legs and mist forming around her eyes is plenty indication she wasn't just playing along.
>You mentally chide yourself.
>Delicate damnit.
“It's ok Fluttershy, you haven't done anything wrong.”
“Remember, I'm just playing a role here, just like we talked about.”
“It's all just an act, I'm not actually mad at you.”
>You breath a sigh of relief as she seems to regain her composure.
“Ok to keep going?” you ask, relieved when she quickly nods yes.
>You decide to drop the character for now, at least until she's more comfortable.
“Alright, I'll need you to spread your wings out for me.”
>You watch in fascination as her wings nervously unfurl.
>How these ponies pack so much wing in so tight to their bodies never fails to stir your curiosity.
>Pushing euclidean concerns aside for the moment you get down to work, placing your hand behind her wing for support.
>Almost instantly however her wings snap closed, engulfing you from the wrist down in a tangle of feathers.
>Despite the slight trembles radiating through your imprisoned arm, you can't resist a slight chuckle.
>”..sorry” she peeps embarrassedly as she forces her wings open again, allowing you to get on with your task.
>Rough start aside, she does begin to relax as you build a basic harness around her trunk.
>There's the occasional twitch as you move around her body, but she gradually becomes accustomed to your touch.
>It's not long before you've got her dressed in a snug web of rope.
>You give the rope a slight tug as you tie the final knot, locking everything in place.
>It catches her off guard as the ropes between her legs rub against her mare hood, causing her to stumble forward a few steps.
“Tsk. Tsk. That won't do.” you teasingly scold her, figuring she can handle a little bit of character.
>Sheepishly she steps back towards you.
>You give her a few gentle pats along the side of her trunk.
“Good pony.”
>You circle around her a few times inspecting your work, giving the ropes a few more tugs.
>As you make a final pass, you catch a little encouragement from the corner of your eye.
>It's subtle, but there's definitely the hint of an embarrassed smile.
>It's simple and not your neatest work, but it'll serve the purpose.
>Ropes crisscross around her, forming wide unobstructing diamonds across her chest and belly.
>Each meets up with a pair of ropes that loop through her hind legs, up the length of her back, and over her shoulders.
>You give the ropes a few more tugs, satisfied that everything is solid.
“How's that feel so far? Comfortable?”
>”It feels...”
>Her shoulders shift a bit as she tries to get used to the strange sensations.
>”Different.”
“Not too tight though right?”
>”Oh, no.. it's ok.”
“Excellent.”
>Setting your feet firmly you place both arms under Fluttershy's torso.
“Now then, I'd like you to fall into me.”
“Don't worry, I won't let you hit the ground.”
>Her legs shift a bit as she works up the courage, the edge of her hoof digging a bit into the floor.
>Possibly reassured by the soft mats beneath her feet, she eventually allows herself to go limp.
>You catch her as promised, easily able to support her light body under your arms.
>Moving backwards slowly, you lower her down onto her side, letting her limbs drag out in front of her.
>She allows you to guide her front leg along the side of her body.
>Watching carefully to gauge her reaction you set to work securing the limb in place.
>A little tightness around her fun bits is one thing, but now you're taking away control of her own limbs.
>Taking away her freedom.
>Her ability to defend herself.
>The effect of your work begins to sink in as you roll her over and start working on her other side.
>Her already bound leg twists nervously against the floor.
>She was going to be helpless.
>Her initial fears about coming here were now returning to the surface.
>What if this hurts?
>Her chest puffs in and out as she draws more oxygen with each successive breath.
>It had taken her so long to work up the courage to come here but now the curiosity that lay dormant for years was turning into a genuine panic.
>What if something goes wrong?
>What if she uses the safeword and you don't stop?
>A sharp whistle now accompanies every breath she takes as air rushes violently through her snout.
>You could do anything to her.
>What was she even thinking coming here in the first place?
>Her chest was now heaving violently.
>...
“Fluttershy?”
>You pause what you are doing, resting one hand over your half finished work and the other along her withers.
>You give her a few moments to register that you've stopped before speaking again.
“Do you remember the safeword we chose?”
>You assume she does, but you want to get her to speak.
>Hoping the sound of her own voice will ease her out of the panic.
>”Y.. yes I remember.”
“Any time you want to stop, remember that you just need to say that word and I will.”
>You rub your hand reassuringly across her arm.
“I promise.”
>The effects slowly show themselves.
>After a few minutes her breathing has mostly returned to normal and her limbs once again lay relaxed where you've placed them.
>Eventually sensing that you are waiting on her and having regathered a little courage she speaks.
>”Anon... I think I'm ok now.”
“Ok Fluttershy”, your hands slowly lifting to resume their task.
>”Thanks for.. I'm s-”
>You quickly cut her off.
“It's alright Fluttershy, this is an important part of what you wanted to experience.”
“It's normal to be scared.”
“We'll start slow like I said, but I do want to push you a bit.”
>With that said, you pull her towards you, flipping her over and onto her back.
>The front of her now fully exposed, she begins to feel the full effect of your efforts.
>Her front legs test at the bonds, instinctively trying to cover her exposed chest, but they are held fast at her sides.
>Her hind legs are still free, but in this position they are mostly useless.
>Out of nowhere she lets out a sharp gasp, realizing her modest exposure.
>Her tail flicks up between her legs as she presses them tightly shut around it, doing a fairly good job of covering herself.
>Oh this could be fun, you muse, but she's not ready for that just yet.
>Pretending not to notice, you keep your focus forward towards her face, sliding your hand to the center of her chest, feeling her heartbeat through the palm of your hand.
>She relaxes a bit, far more comfortable with where your attentions lay.
>You slowly circle your fingers around.
>You make figure-eight patterns around her chest. brushing your finger tips lightly through the fuzzy coat of fur.
>Taking your time as you feel around, getting a good sense of her body.
>She begins to squirm a bit as you trace along her sides, making light circles along her rib cage.
>Finally unable to hold it in, a sharp giggle escapes her as she twists a bit in her bonds, trying to escape your touch.
“My my Fluttershy, you're not.. ticklish.. by any chance are you?”
>A hint of playful menace lingers in your voice.
>”I-Yes!” she squeaks, still futility trying to shuffle away from the torment.
>As you continue a brief panic sets in, but quickly subsides as you return your hand to her less sensitive areas.
>This seems a good place to start.
>..
>The next hour of your session goes by quite pleasantly.
>You continue to tease her, letting her experience small amounts of fear and discomfort then backing off to let her soak in the experience.
>Gradually you push her further as she becomes more comfortable under your control.
>She seemed to really enjoy it when you did up her wings.
>You tied long ropes to the side of her harness, then ran them along the floor, securing them tautly through rings in the opposing walls.
>By this point she was fairly comfortable with you touching her and manipulating her limbs.
>She put forward only token resistance as you spread her wings out flat, unsure of your intentions but not especially worried.
>You Tether them with cloth strips at strategic points, binding them to the rope running along the floor and holding them open and immobile.
>Rather than another game of torment you simply run your hand down the length of her restrained wings, pressing them down gently against the soft floor.
>Your fingertips dancing through the quills of her feathers, her wings instinctively flexing against the bonds.
>You could happily keep this pace for the rest of the evening, but you figure it's time to step things up.
“Fluttershy, enjoying yourself so far?”
>Despite you both knowing the answer, she seems surprised as she vocalizes it.
>”I.. I am, yes.”
“Well then, I'd like to try something a bit harder, do you think you're up for that?”
>”Harder?”
>She looks up at you.
“Yes Fluttershy, much harder in fact, but I think you'll look back on it as a good experience.”
“And I think you are ready.”
>”Ok Anon, then I'll do it.”
“There is something very important we need to talk about first though.”
“I want to give you the freedom to explore your emotions, to really let yourself get into the moment.”
“So unless I hear the safe word, I'm going to keep going.”
“You can scream, cry, beg me to stop, but I won't.”
>A visible nervousness creeps across her face, unsurprisingly apprehensive about what exactly you have planned for her.
“If you need me to stop, you absolutely have to use the safeword.”
“Understand?”
>”I.. y-yes, I understand.”
“I know what I've just said is scary, but I want you to remember that you are in total control here.”
“You can say the safe word at any time, and I'll stop, immediately.”
“And I won't be mad or think any less of you.”
“Still willing to give this a try?”
>She gives her answer some consideration this time.
“If you don't think you're ready, we can stick with this.”
>”No, I'm.. I'm ready” she blurts out.
>The determination in her voice is overshadowed somewhat by the apprehensive look on her face, but you feel you'd be doing her a disservice if you didn't give her a real taste, and you're confident she can handle it.
>None the less you decide to start with something familiar.
>You begin drawing familiar circles around her rib cage, as you had done many times before, illicit the usual frantic giggles.
>Only this time, you don't stop.
>Her laughter becomes more pained, more desperate, her breathing erratic and laboured.
>”Ahh.. oh.. hhhaaa!”
>She writhes beneath you.
>Her wings tug furiously against their bonds.
>”S... STOP! Ahhhhh!”
>True to your word, you don't.
>Instead, you begin a vicious cycle.
>Bringing her to the edge of tears before easing off to let her catch a breath.
>Her legs kick wildly, modesty long since forgotten.
>Desperate laughter filling the room.
>”Ahhhh, please! No! I'll.. ah! I'll do anything! Just.. ghaahh!”
>She cries out.
>Pleads with you.
>Begs you to stop.
>But no safeword.
>”Just stop! Ghahgh! Please! NoAHH! No More! I-I can't take it.”
>You make another brutal assault on her tortured ribs.
>Her back arches, head slamming into the matted floor.
>She breaks into a new fit of pained laughter as you curl your fingers in a bit, twisting back and forth in a futile attempt to escape the torment.
>Tears form at the corners of her eyes.
>You decide she's had enough of the stick, time to present the carrot.
“Anything you say..... wellll.....”
>Your voice drips with mock consideration as you let up.
>You keep your left hand on the center of her chest, poised for another attack, while blindly sliding your right hand back behind you.
>She doesn't notice it rapidly approaching her nether region, far too focused on using this reprieve to draw air into burning lungs.
“If this isn't doing it for you, there are other things I could play with.”
>She tenses sharply as you apply a gentle pressure through her tail.
>Her legs pressing tightly around your fingertips.
“No? Well, it was just a thought...”
>You say with feigned disappointment, both hands moving to resume their previous work, signaling an end to this respite.
>”Wait! Yes, please!”
“Please what? Fluttershy.”
>She squirms desperately as you work your hand back along her side, the threat of more tickles imminent.
>”Please.. down.. down there.”
“Down there?”
>You dig your fingers in lightly, illiciting a desperate squeel.
“I'd be more than happy to.”
“But I'm afraid you're going to have to ask me properly first.”
>You return to slow gentle circles.
>Keeping her uncomfortable, but giving her time to think.
>”Please play with me down there.”
>Quickly reaching back again, you work a finger through her tail.
>She gasps as you make direct contact with her lips, sliding your finger gently along her slit.
>Letting her think for the moment that this ordeal is over.
“Oh I think we can do a lot better then that Fluttershy” you coo sweetly.
>She moans pleadingly as you quickly retract your hand and slide it back across her belly.
>You attack her abdomen with your fingertips, eliciting another bout of ragged screams before giving her a chance to rest.
>Her face turns flush with panic as she searches desperately now for what you want to hear.
>You decide to help her out a bit.
“What is it exactly you'd like me to play with?”
>Her face contorts as she tries to think, your fingers crawling slowly along her sides not helping.
>”My.. my.. my..”
>Desperation grips her as your hand approaches the spot just below her front leg, where it'll do the most damage.
>Her voice drops almost to a whisper.
>”Clitoris. Please play with my clitoris.”
“Hmm... “
>You pause, making a show of thinking over her response.
“That's better Fluttershy, but still not quite what I'm looking for.”
>She winces tightly in anticipation, bracing herself for your next assault, but you let her off easy this time.
>Instead resuming your relatively mild circles, giving her time to collect her thoughts.
>She blanches, suddenly realizing what you want her to say.
>”P.. please play with.. with my c...”
>She struggles desperately, trying to fight years of a polite upbringing.
>Her cheeks turn beet red.
>A lifetime spent not offending anyone.
>Of respecting everyone around her.
>She can't bring herself to say it.
>You decide to provide her a little encouragement by wiggling your finger tips under her front legs.
>”hhaAAhh oh.. oh no! NO! PLEASE! Ahhhhhhh!”
>”MY CUNT!”
>”PLEASE.. PLEASE PLAY WITH MY CUNT!”
>Her voice echos loudly through the entire room.
>It hurts you ears.
>Ceasing your torment, you rest your left hand on her shoulder and right hand on her front leg.
>You sit next to her as she soaks in the flurry of emotions.
>In that moment she was completely helpless, desperate enough to say or do anything, it's a lot to take in.
>You can only watch as her chest as it heaves in and out, adrenaline coursing through her.
>It takes several minutes for her breathing to return to normal and the haze to lift.
>”A.. anon?”
“Yes Fluttershy?”
>”I thought you were... you know.. going to play with..”
>You chuckle softly.
“I can if you actually want me to, but we should talk first.”
>You shift slightly into a more comfortable position.
“You've just been through a lot for your first time.”
“We can certainly keep going, but there'd be no shame in calling it a day.”
>”Uhm, well I...”
“You have nothing to prove Fluttershy, and I'm really very proud of you.”
“I'm not going to think any less of you if you want to end now. I'd be happy to do another session with you any time you want.”
>She thinks for a moment.
>”But, I'm already tied up.”
>You can't help but smirk.
“That's ok, I like tying ponies up, remember?”
>”Oh.”
>Her face somehow turning slightly redder.”
>”I.. I still think I'd like to continue.”
>”Just.. can we not.. I mean-”
>She stops as a your grin grows wider, already anticipating the request.
“Of course Fluttershy, I think we've done enough tickling for today.”
>A content smile forms across her face as she lets her head drop, coming to rest on the matted floor.