Pony Shipping Headcannons

    Rarity was busily working on a huge dress order for Sapphire Shores. She couldn’t believe her luck at being commissioned for such a big order by such a widely known pony. It was the beginning of summer and the new swimwear line just HAD to be in on time and absolutely perfect. Fabric, pins, mannequins and various other colorful items littered the floor of Carousel Boutique as the white Unicorn worked her magic. She had just started in on a new swimsuit when she heard a faint knock at the door of her shop.

“Come in! It’s unlocked, I’ll be with you in just a moment!” The door slowly opens to reveal a shy yellow pegasus.

“Um... Hi Rarity...”

“Oh hello Fluttershy! Please, do come in!” Rarity hastily shoves her work out of the way as her friend enters the room. “Is there anything I can help you with dear?”

“I... I was just wondering...” she stares at the floor. “It’s very lonely at my cottage so you see... um... what I’m trying to say is... uh... do you need any help Rarity? I understand if you don’t... why would you? ohhhh... I’ll just go now...” Fluttershy turns to leave, tears welling in her eyes. Why can’t I just tell her how I feel?

“Don’t be silly Fluttershy! I would love your help! In fact, I’ve been looking for a Pegasus to try on one of my new swimsuits. Would you mind?”

“Oh, not at all Rarity!” Fluttershy turns around, a smile of relief on her face. “What should I do?”

“Hmmm... Stand here please?” Rarity gestures to the center of the room. “Good. Now, here we are...” Rarity levitates a dark blue one-piece swimsuit over to her friend. She uses her magic to gently lift Fluttershy and help her into the suit. “How does that feel dear?”

“Oh my... um... it’s a bit tight...” The stretchy blue swimsuit tightly hugs Fluttershy’s belly, chest, and back. It immediately rides up on her crotch, squeezing against her marehood and emphasizing her firm, round plot. Fluttershy blushes as she feels the swimsuit rub against her cute little pussy.

“You look simply amazing dear...” Rarity bites her lip. Am I being too forward? Can she tell it’s three sizes too small? Rarity tenses as she feels herself getting aroused at the sight of Fluttershy in the skintight suit. I must at least see what she thinks before I continue... “I’d like you to do a bit of modeling for me Fluttershy. Is that alright? It will be between you and me only.” She looks at her friend, hoping that she will understand.

“Um... okay Rarity... just if it’s between us...”

“Of course dear. I know how you feel about modeling. Let’s go upstairs.” Rarity turns and trots down the hall.

“Upstairs?” Fluttershy bites her lip.

“Of course dear! You don’t mind taking some... ah... action shots... do you?”

“um... no...” I wonder what Rarity means about “action shots”?

“Here we are darling!” Rarity stops outside her bathroom. “After you!” Fluttershy enters the luxurious bathroom, still looking confused. “Would you mind getting in the shower Fluttershy? I’m sure it would really help with the suit’s... full effect.”

“Well... I guess... um... oh my...” Fluttershy slowly walks inside the shower. Rarity locks the bathroom door behind her and turns the water on.

“Eep! Cold!” The freezing water surprises Fluttershy and she darts out of the shower and hides behind Rarity.

“Oh I’m so sorry dear! Here, Let’s let it warm up a bit.” She turns a few more knobs. Moments pass and clouds of steam start to rise to the ceiling. “I think it’s ready now darling.”

“um... okay...” Fluttershy gingerly puts out a hoof to test the water. The warm water flows over her hoof and she shivers, enjoying the feeling of the water rushing over her. “That’s nice...” She slowly enters the shower, letting the water cover her body, soaking her mane and tail and making her tight swimsuit shine. She closes her eyes as the water falls down her face, sending a warm, calming sensation through her whole body. This swimsuit does make showering fun... I just love the way it feels... It’s so tight, but I really it...

“Fluttershy... you look absolutely divine!” Rarity shifts her back hooves around, trying to cover up the arousal starting to run down her leg. “Do you mind if I join you?” Rarity looks hopefully at her friend.

“Oh of course Rarity! This water feels soooooo good!” Rarity gets in the shower next to Fluttershy and the two enjoy the hot, steamy water cascading over them. Rarity moans slightly as she feels trickles of water run down her marehood. She stares at Fluttershy, admiring how the tight, shiny swimsuit hugs the Pegasus so perfectly, how it exposes her voluptuous plot, and how it holds her tail up in such a sexy manner.

“Fluttershy?”

“Yes Rarity?” Fluttershy opens her eyes and blushes as she takes in her friend’s beauty. The water shining in Rarity’s mane and tail and the relaxed, happy look on ther face stir something inside Fluttershy.

“Why did you actually come here? You would usually never help me like this...”

“Oh! um...” Fluttershy blushes. “I... I just... you’re my best friend and... I have felt this way for a long time... I... I...” She whispers something inaudible over the rush of the shower.

“What’s that darling?” She COULDN’T mean... could she?

“I... um...”

“Please Fluttershy... you can tell me anything.”

“Iwantyoutobemymarefriend!” Fluttershy hides her head in shame. “I understand if you hate me now... I’m sorry...”

“You... Fluttershy? Really? You feel that way about me? I... I don’t know what to say...”

“Oh no... I... I...” Fluttershy starts to cry. Good job Fluttershy. You just ruined everything! Now she hates you!

“Don’t cry Fluttershy! I didn’t mean...” In a moment of blind frustration, Rarity moves closer to Fluttershy and kisses her on the lips. Surprised, the Pegasus stops crying.

“Rarity? Oh my... I never knew...” She returns the kiss, slowly savoring the feel of Rarity’s soft, firm lips on her own.

“Feel better now dear?” Fluttershy nods. “Good. Me too...”

“Can we kiss again Rarity?” Instead of answering, Rarity smiles and plants another long kiss on Fluttershy’s lips. She runs her tongue along them and they slowly part, allowing her tongue to enter. The two ponies share several more minutes of kissing, running their tongues lovingly across each other’s lips and exploring every contour of each other’s mouth. Rarity slowly breaks the kiss, moving back to admire Fluttershy once more.

“That swimsuit... looks wonderful on you darling. Are you sure it’s not too tight?”

“No.” Fluttershy shakes her head. “I like it. The tightness is nice actually...” She glances behind her, enjoying the warm, silky pressure on her marehood.

“I can tell dear. You smell...”

“I what!? Oh...” Fluttershy blushes. “um... can you... um... help?” Rarity smiles wryly.

“Of course dear. Let me see...” Fluttershy turns around and lifts her tail, exposing her tight little pussy. The shiny swimsuit emphasizes the beauty of her love, tightly squeezing it close to her body. “You are so beautiful Fluttershy! Why don’t we move to the bedroom?”

“I’d like that...” Fluttershy waits as Rarity turns off the water and gets each of them a large, fluffy towel. “Can I keep the swimsuit on Rarity?”

“Of course Fluttershy! You can have it. I think it ‘suits’ you perfectly.” The two giggle at Rarity’s little pun. After drying off, the two go to Rarity’s bedroom.

“You lay on the bed Fluttershy. I’ll be right there...” Rarity rummages around in her wardrobe while her friend curls up on the large, four poster bed. “These should do...” Rarity walks over to the bed carrying two large dildos and a latex strapon harness.

“Oh my...” Fluttershy turns red with anticipation and embarrassment at the sight of the huge toys. “They’re so big Rarity...”

“I know dear.” Rarity gets on the bed. “Do you think you can handle it?” Fluttershy nods slowly. “Good.” Rarity slowly pushes one of the huge dildos up her eager marehood. She flips a switch at the base of the toy and it starts to vibrate. “Aahhh...” She moans slightly as she attaches the other dildo to the black latex panties and pulls them on. The tight latex harness accentuates Rarity’s large, voluptuous plot, keeping her dildo firmly planted all the way inside of her. “Ready dear?”

“Yes...” Fluttershy eyes her friend with anticipation as she position herself with her plot towards Rarity.

“Here we go...” Rarity moves the crotch of Fluttershy’s swimsuit to the side and slowly rubs the tip of the strapon on her marehood.

“ooohhhhh... please hurry up Rarity... I want you inside of me...” Without hesitation, the white Unicorn thrusts, driving the tip of the toy inside Fluttershy’s wet little pussy. She squeezes her eyes shut as the toy enters her love, savoring the pleasure now sliding deeper inside of her. Rarity moans as she pushes the dildo all the way inside Fluttershy’s tight little pussy. “Please Rarity... make me cum...”

“If you insist darling!” Rarity pulls the dildo out of Fluttershy and quickly thrusts it all the way back in.

“Aaahhh! Harder!” Fluttershy squeals as her friend begins fucking her, ramming the huge dildo repeatedly into her. She moans as Rarity continues to hilt the massive toy in her pussy, pleasure building inside of her. Rarity grunts as the toy completely filling her tight marehood vibrates, sending waves of tingling pleasure throughout her body. After several minutes of hot, moaning pleasure, Fluttershy cums, sending her warm juices all over Rarity, who grins as she continues ravaging her friend’s cute little pussy.

“OooOOoooOhhhhhh!” Fluttershy moans and screams as the pressure explodes in her pussy, making her mind go blank with pleasure. Rarity cums as well, grunting and collapsing next to Fluttershy as waves of complete bliss envelop both of them. Fluttershy wraps her hooves around her friend, hugging her tightly. “I love you Rarity...”

“I love you too Fluttershy...” Rarity returns the hug, running her hooves over the tight, silky swimsuit still enveloping Fluttershy. The two ponies fall asleep in each other’s tight embrace, Rarity’s strapon still buried deeply in Fluttershy’s pussy as her own dildo cuts off, still filling her marehood completely.