You are Rarity, checking up on your dear friend. Fluttershy's note was awfully vague, with many words heavily crossed out. You suspect it wasn't even close to the first draft, which is worrying. You knock on her cottage door. You barely hear her call out,
"C-come in!"
Maybe she's sick in bed? You open the door.
"Fluttershy, I got your note, darling. What's wrong?"
On your way to the bedroom, you are struck by how quiet it is. Normally the cottage would be crawling with wild, dirty animals with no manners and- Well, while you do appreciate their absence, it makes you uneasy. Fluttershy's voice is a little louder this time.
"Oh, I wouldn't say there is anything wrong. Certainly not with me. Um."
You find her laying on her belly on top of her bed, looking very much like Sweetie Bell when she's trying to hide a new burn mark on the floor.
"Are you sick? Is that why you sent all the animals away?"
She shakes her head.
"Some of them wanted to watch, but I always respected their privacy, even when they didn't mind. I was very firm with them, which is why I think it's working."
"You're not making any sense, Fluttershy. Why don't you start at the beginning?"
You levitate a cushion over, and sit down on the floor. You know how long these stories can be.
"Um. You know how Discord comes by to talk every once in a while?"
"He did something, didn't he? Don't worry, I'm sure Twilight will find a way to reverse it."
Fluttershy shakes her head emphatically.
"It's not like that. Um. Exactly. He was telling me that if I had this one thing, I would be more confident."
Sometimes you wonder if he reformed at all, or just put up an act so he can play all the pranks he wants at a smaller scale.
"Oh Fluttershy, that's not how confidence works at all. Having some object doesn't change who you are."
"What about the alicorn amulet?"
You revise your assertion.
"No object permanently changes your personality, and the amulet is a good example of why trying such things is dangerous."
"Well, it's not exactly an object. Maybe, maybe if I showed you?"
"Very well, let's see what foolish thing Discord gave you."
Fluttershy nods. And does nothing. You wait a little longer.
"Is it invisible?"
Fluttershy shakes her head, breathing a little more quickly.
"N-no, I'm just building up my courage."
Then she looks you straight in the eye, and sits up. Your eyes drop automatically to what she was covering up- Oh my.
"Is that..."
She nods.
"You see what I mean?"
You feel like you should be vaguely troubled by the fact that Fluttershy is full erect, but it isn't the first time you've had this sort of reaction. Poor Spike can't hide a thing. You've taken to using his hemipenes to hold thread bobbins. They are the right shape, and they are around so often, the first time it was an honest mistake.
"Rarity, is there something wrong with it? You've just been staring at it. Not that that's a bad thing!"
"Sorry, darling, I was a little lost in my thoughts. Is this why you... sent for... "
The implications just occurred to you. She must have noticed, because she laid right back down, and closed her eyes tightly.
"I'm sorry, I didn't know who I could turn to! Let's forget this ever happened. It never happened."
The poor dear. You sit down on the edge of her bed and stroke her mane.
"Forgive me, this is all so unexpected."
Fluttershy inhales shakily.
"I just thought, y-you are so sophisticated and world-wise, you'd know what to do. O-or who to go to."
You sigh a little helplessly.
"Darling, I'm glad you think so highly of me, but it's not altogether accurate. I, ah, haven't done this before either."
She looks up at you in shock.
"You haven't?"
You shake your head.
"It's important who you do it with. If you mingle with the wrong crowd, it could give you a poor reputation. Here in Ponyville... I just haven't had the chance."
Fluttershy stares at her sheets.
"I understand. I guess you can't help me."
You take an honest look at your friend. You have always admired her grace, how demure she is.
"I wouldn't say that. But is this something you really want?"
She looks at you uncertainly.
"I- I think I should at least try. It's something I have often wondered about."
She's wondered about this, specifically? Nevertheless,
"Well, if you are supposed to be improving your confidence, I should be the one lying down."
You turn around and lie on your stomach, facing the headboard.
"R-Rarity?"
You look over your shoulder at your startled friend.
"It's to help one of my best friends."
You had rather hoped your first time would be more romantic, and goodness knows the books you've read all go that way. But this is romantic too, in a way. You twitch your tail out of the way. You'd hate for it to get messy.
"Thank you, Rarity. You are one of my best friends too."
Her hooves sink into the mattress on either side of you, and you can't help but tense up a little. She shifts her weight, and-
"The lower one! It goes in the lower one!"
"S-sorry."
She pauses.
"If, if this is about me being more confident,"
Oh no.
"We should start with, um. Oral?"
Oh, that's not so bad. You roll over onto your back, gazing up at your worried friend.
"I've never been eaten out before either, so that's fine too."
Fluttershy shifts her weight uncertainly.
"I was actually talking about, um. Me."
You look down at the limb dangling between her legs.
"If you could bring it closer, then?"
Goodness knows you can't show uncertainty about this whole business, or Fluttershy will back out immediately. She puts her hooves up on top of the headboard, and straddles your chest. You rest your hooves on her trembling thighs, and stare at her stallionhood. It's only inches from your mouth.
"Rarity?"
Mustering your resolve, you prop it up with one of your hooves. Fluttershy whimpers. You take the head into your mouth, keeping an eye on her face. She clenches her eyes shut, and she starts panting. It tastes funny, not to mention the smell. Much like Fluttershy, a little earthy, but still delicate. As you get acclimated to the taste, you start trying things with your tongue, flicking and swirling and prodding the hole. She whimpers every time, whispering your name. Emboldened, you take more of her into you, feeling it slide under your tongue, then rise back among your molars. You pull back, and take it in again, sliding along the inside of your cheek.
"Thank you Rarity! Thank you so much!"
It makes you smile around her cock. You cup her balls, moving them back and forth, enjoying the heft. She moans. You pick up the pace, dropping the flourishes of your tongue, and just move your head back and forth down her dick. She starts bucking and moaning continuously, and you have to put your hooves on her hips to steady her. Her cock is getting uncomfortable close to the back of your throat.
"Rarity, I'm about to-"
Your eyes go wide as hot cum surges into your mouth. It's all you can do not to let it messily dribble out of your mouth. Fluttershy looks down at you in concern.
"Are you alright? I sort of lost control. Um. Sorry?"
You stare at her insecure expression, and hold back a sigh. You manage to swallow your mouthful of semen, and spit out her penis.
"A little prior notice next time would be nice, that's all."
Fluttershy's voice trembles.
"N-next time?"
Huh, you did say that.
"For future reference, that is."
She nods.
"Um, Rarity?"
"Yes, darling?"
"I think I'm ready for the other thing. Th-the lower one."
Your heart rate surges, but you smile and roll over. You twitch your tail out of the way, and try not to dwell on the taste of cum in your mouth as you wait. The mattress shifts, and once again, she is hovering over you. Her warm breath teases at your horn, making it tingle not unpleasantly. Then you feel her rod press up against your marehood, and you gasp.
"Rarity? Is it the wrong one again?"
"Nnno, you just surprised me, that's all. Please, ah, please continue."
Her head parts your folds, and it feels like nothing you've known before. So warm, yet soft, yet crucially firm.
"Oh Rarity, you feel amazing!"
"You too, my dear. Oh, yes, you too."
You feel her cock press up against your virginity, and know there is no turning back.
"Go ahead, Fluttershy. It's yours."
She whispers, "Thank you."
The pain is brief, but intense. She stops immediately, and you catch your breath.
"We can try another time, if you want to rest..."
You shake your head.
"We've gotten this far. Just give me a moment."
The pain is fading, but it's still rather sore. Fluttershy lowers herself, resting on your back with her member still several inches deep inside you. It moves around a little, bringing back some soreness, but also sparking a small amount of pleasure. After a few minutes, you feel like you can go on.
"I'm ready when you are, dear."
Fluttershy nuzzles your neck pleasantly, and slowly starts thrusting again. It's much better this time around, and you love the feel of her body against yours, especially the surging muscles in her hips as they play across your flank. You press your face into the pillow and let out a muffled moan. Fluttershy giggles, and brings her mouth to your ear.
"Do you like it?"
You lift your face, breathing heavily.
"Oh yes, this is the Best Possible Thing!"
She giggles again.
"For me too."
Then she starts nibbling on your ear, and most of your ability to think rationally promptly disappears.
"Wahahaha~ yes! Rut me! Oh, yes!"
Her breathing gets shallow, and you can feel her thighs tensing.
"I'm going to cum outside!"
"No!"
Not your tail! You clench around her cock as best you can, entwine your back legs with hers, and press your rear against her as hard as you can. She clasps her forehooves around your neck and moans into your ear as she releases. You ride the wave of indescribable pleasure as your pussy milks her for all she's worth. You relax, feeling utterly full and fulfilled. Fluttershy pulls out, and you make a wordless cry of protest.
"It's my fault that I came in you, and I'm going to make it better."
You look over your shoulder at her in confusion. Just as the first drops of cum start dribbling from your hole, she sets to licking. Oh yes, this is nice~. But still,
"That's your own semen you are eating. Are you really okay with that?"
She pauses in her ministrations, and for a contradictory moment, you fear she'll agree with you.
"You ate it too, so this is just being fair."
Her tongue returns to probing and scooping at your depths. You bite the pillow, and before long you orgasm again, earning a giggle from your friend.
"Don't worry, I'll get this too."
Once she's done, you are on the edge of sleep, worn out by the experience. Fluttershy lays down beside you.
"Do you think it worked? Am I more confident?"
You smile at her.
"There were several times you were quite assertive. You really are improving."
She smiles back, and drapes a wing over you. That's just enough to set you drifting.
"Rarity?"
"Yes, love?"
"In the morning, can we do this again?"
"Of course. We can hardly be done after one practice session."
And you fall asleep, eager to meet the morning.
Fluttershy's note was awfully vague, with many words heavily crossed out. I suspect it wasn't even close to the first draft, which is worrying. I knock on her cottage door. I barely hear her call out,
"C-come in!"
Maybe she's sick in bed? I open the door.
"Fluttershy, I got your note, darling. What's wrong?"
On my way to the bedroom, I am struck by how quiet it is. Normally the cottage would be crawling with wild, dirty animals with no manners and- Well, while I do appreciate their absence, it makes me uneasy. Fluttershy's voice is a little louder this time.
"Oh, I wouldn't say there is anything wrong. Certainly not with me. Um."
I find her laying on her belly on top of her bed, looking very much like Sweetie Bell when she's trying to hide a new burn mark on the floor.
"Are you sick? Is that why you sent all the animals away?"
She shakes her head.
"Some of them wanted to watch, but I always respected their privacy, even when they didn't mind. I was very firm with them, which is why I think it's working."
"You're not making any sense, Fluttershy. Why don't you start at the beginning?"
I levitate a cushion over, and sit down on the floor. I know how long these stories can be.
"Um. You know how Discord comes by to talk every once in a while?"
"He did something, didn't he? Don't worry, I'm sure Twilight will find a way to reverse it."
Fluttershy shakes her head emphatically.
"It's not like that. Um. Exactly. He was telling me that if I had this one thing, I would be more confident."
Sometimes I wonder if he reformed at all, or just put up an act so he can play all the pranks he wants at a smaller scale.
"Oh Fluttershy, that's not how confidence works at all. Having some object doesn't change who you are."
"What about the alicorn amulet?"
I revise my assertion.
"No object permanently changes your personality, and the amulet is a good example of why trying such things is dangerous."
"Well, it's not exactly an object. Maybe, maybe if I showed you?"
"Very well, let's see what foolish thing Discord gave you."
Fluttershy nods. And does nothing. I wait a little longer.
"Is it invisible?"
Fluttershy shakes her head, breathing a little more quickly.
"N-no, I'm just building up my courage."
Then she looks me straight in the eye, and sits up. my eyes drop automatically to what she was covering up- Oh my.
"Is that..."
She nods.
"You see what I mean?"
I feel like I should be vaguely troubled by the fact that Fluttershy is full erect, but it isn't the first time I've had this sort of reaction. Poor Spike can't hide a thing. I've taken to using his hemipenes to hold thread bobbins. They are the right shape, and they are around so often, the first time it was an honest mistake.
"Rarity, is there something wrong with it? You've just been staring at it. Not that that's a bad thing!"
"Sorry, darling, I was a little lost in my thoughts. Is this why you... sent for... "
The implications just occurred to me. She must have noticed, because she laid right back down, and closed her eyes tightly.
"I'm sorry, I didn't know who I could turn to! Let's forget this ever happened. It never happened."
The poor dear. I sit down on the edge of her bed and stroke her mane.
"Forgive me, this is all so unexpected."
Fluttershy inhales shakily.
"I just thought, y-you are so sophisticated and world-wise, you'd know what to do. O-or who to go to."
I sigh a little helplessly.
"Darling, I'm glad you think so highly of me, but it's not altogether accurate. I, ah, haven't done this before either."
She looks up at me in shock.
"You haven't?"
I shake my head.
"It's important who you do it with. If you mingle with the wrong crowd, it could give you a poor reputation. Here in Ponyville... I just haven't had the chance."
Fluttershy stares at her sheets.
"I understand. I guess you can't help me."
I take an honest look at my friend. I have always admired her grace, how demure she is.
"I wouldn't say that. But is this something you really want?"
She looks at me uncertainly.
"I- I think I should at least try. It's something I have often wondered about."
She's wondered about this, specifically? Nevertheless,
"Well, if you are supposed to be improving your confidence, I should be the one lying down."
I turn around and lie on my stomach, facing the headboard.
"R-Rarity?"
I look over myshoulder at my startled friend.
"It's to help one of my best friends."
I had rather hoped my first time would be more romantic, and goodness knows the books I've read all go that way. But this is romantic too, in a way. I twitch my tail out of the way. I'd hate for it to get messy.
"Thank you, Rarity. You are one of my best friends too."
Her hooves sink into the mattress on either side of me, and I can't help but tense up a little. She shifts her weight, and-
"The lower one! It goes in the lower one!"
"S-sorry."
She pauses.
"If, if this is about me being more confident,"
Oh no.
"We should start with, um. Oral?"
Oh, that's not so bad. I roll over onto my back, gazing up at my worried friend.
"I've never been eaten out before either, so that's fine too."
Fluttershy shifts her weight uncertainly.
"I was actually talking about, um. Me."
I look down at the limb dangling between her legs.
"If you could bring it closer, then?"
Goodness knows I can't show uncertainty about this whole business, or Fluttershy will back out immediately. She puts her hooves up on top of the headboard, and straddles my chest. I rest my hooves on her trembling thighs, and stare at her stallionhood. It's only inches from my mouth.
"Rarity?"
Mustering my resolve, I prop it up with one of my hooves. Fluttershy whimpers. I take the head into my mouth, keeping an eye on her face. She clenches her eyes shut, and she starts panting. It tastes funny, not to mention the smell. Much like Fluttershy, a little earthy, but still delicate. As I get acclimated to the taste, I start trying things with my tongue, flicking and swirling and prodding the hole. She whimpers every time, whispering my name. Emboldened, I take more of her into me, feeling it slide under my tongue, then rise back among my molars. I pull back, and take it in again, sliding along the inside of my cheek.
"Thank you Rarity! Thank you so much!"
It makes me smile around her cock. I cup her balls, moving them back and forth, enjoying the heft. She moans. I pick up the pace, dropping the flourishes of my tongue, and just move my head back and forth down her dick. She starts bucking and moaning continuously, and I have to put my hooves on her hips to steady her. Her cock is getting uncomfortable close to the back of my throat.
"Rarity, I'm about to-"
My eyes go wide as hot cum surges into my mouth. It's all I can do not to let it messily dribble out of my mouth. Fluttershy looks down at me in concern.
"Are you alright? I sort of lost control. Um. Sorry?"
I stare at her insecure expression, and hold back a sigh. I manage to swallow my mouthful of semen, and spit out her penis.
"A little prior notice next time would be nice, that's all."
Fluttershy's voice trembles.
"N-next time?"
Huh, I did say that.
"For future reference, that is."
She nods.
"Um, Rarity?"
"Yes, darling?"
"I think I'm ready for the other thing. Th-the lower one."
My heart rate surges, but I smile and roll over. I twitch my tail out of the way, and try not to dwell on the taste of cum in my mouth as I wait. The mattress shifts, and once again, she is hovering over me. Her warm breath teases at my horn, making it tingle not unpleasantly. Then I feel her rod press up against my marehood, and I gasp.
"Rarity? Is it the wrong one again?"
"Nnno, you just surprised me, that's all. Please, ah, please continue."
Her head parts my folds, and it feels like nothing I've known before. So warm, yet soft, yet crucially firm.
"Oh Rarity, you feel amazing!"
"You too, my dear. Oh, yes, you too."
I feel her cock press up against my virginity, and know there is no turning back.
"Go ahead, Fluttershy. It's yours."
She whispers, "Thank you."
The pain is brief, but intense. She stops immediately, and I catch my breath.
"We can try another time, if you want to rest..."
I shake my head.
"We've gotten this far. Just give me a moment."
The pain is fading, but it's still rather sore. Fluttershy lowers herself, resting on my back with her member still several inches deep inside me. It moves around a little, bringing back some soreness, but also sparking a small amount of pleasure. After a few minutes, I feel like I can go on.
"I'm ready when you are, dear."
Fluttershy nuzzles my neck pleasantly, and slowly starts thrusting again. It's much better this time around, and I love the feel of her body against mine, especially the surging muscles in her hips as they play across my flank. I press my face into the pillow and let out a muffled moan. Fluttershy giggles, and brings her mouth to my ear.
"Do you like it?"
I lift my face, breathing heavily.
"Oh yes, this is the Best Possible Thing!"
She giggles again.
"For me too."
Then she starts nibbling on my ear, and most of my ability to think rationally promptly disappears.
"Wahahaha~ yes! Rut me! Oh, yes!"
Her breathing gets shallow, and I can feel her thighs tensing.
"I'm going to cum outside!"
"No!"
Not my tail! I clench around her cock as best I can, entwine my back legs with hers, and press my rear against her as hard as I can. She clasps her forehooves around my neck and moans into my ear as she releases. I ride the wave of indescribable pleasure as my pussy milks her for all she's worth. I relax, feeling utterly full and fulfilled. Fluttershy pulls out, and I make a wordless cry of protest.
"It's my fault that I came in you, and I'm going to make it better."
I look over my shoulder at her in confusion. Just as the first drops of cum start dribbling from my hole, she sets to licking. Oh yes, this is nice~. But still,
"That's your own semen you are eating. Are you really okay with that?"
She pauses in her ministrations, and for a contradictory moment, I fear she'll agree with me.
"You ate it too, so this is just being fair."
Her tongue returns to probing and scooping at my depths. I bite the pillow, and before long I orgasm again, earning a giggle from my friend.
"Don't worry, I'll get this too."
Once she's done, I am on the edge of sleep, worn out by the experience. Fluttershy lays down beside me.
"Do you think it worked? Am I more confident?"
I smile at her.
"There were several times you were quite assertive. You really are improving."
She smiles back, and drapes a wing over me. That's just enough to set me drifting.
"Rarity?"
"Yes, love?"
"In the morning, can we do this again?"
"Of course. We can hardly be done after one practice session."
And I fall asleep, eager to meet the morning.
