Fluttershy gritted her teeth and moaned in pain as she felt Big Mac trying to work the end of his cock into her pussy. He grunted and groaned as he gently pushed it against her slit, but Fluttershy was too tight to allow him entry. That’s when he saw the tears starting to roll down her face. With a heavy sigh, Big Mac backed up and gave the trembling pegasus some room. He looked incredibly frustrated as he turned to Applejack and shook his head no. AJ trotted over to Fluttershy and gently hugged her.

“What’s wrong, sugarcube?” Fluttershy just continued to tremble as AJ held her. AJ felt her tears soaking into her fur as she continued to lie next to the yellow pegasus. “Ah thought you’d be happy.” Fluttershy looked up at AJ as tears continued to flow from her eyes.

“I-It h-hurts.” AJ laid Fluttershy’s head against her breast again.

“Ah know, Sugarcube, but that’s just temperary. After a few minutes, the pain goes away.” AJ heard Fluttershy say something, but she was so quiet she couldn’t make out what she said. “What did ya say?” Fluttershy once again raised her head.

“I-I’m scared.” AJ stared into Fluttershy’s big wet eyes.

“Ain’t nothin’ to be scared about, Fluttershy. You saw how much fun Big Mac and I were havin’ earlier. Ah know, we just need to ease you into it.” AJ smiled. “And ah know just how to loosen up a mare. Just try to relax.” Fluttershy took and deep breathe and let it out. She was still trembling, but she trusted Applejack. With a soft “ok”, AJ began to trace a hoof over Fluttershy’s face. She stared into her eyes, drinking in every inch of this gorgeous pegasus beautiful face while gently caressing her.

Fluttershy closed her eyes as she enjoyed the soft touch of AJ’s hoof. Suddenly, a new sensation erupted from her cheek as she felt AJ’s lips plant a gentle kiss into her fur. With a soft gasp, she moaned as AJ began planting little kisses all over her face, bringing forth sensation she had never felt before. She felt her pussy begin to grow wet as she felt heat radiating from between her legs and making it’s way up her body.

AJ moved to envelope Fluttershy’s muzzle with hers in a passionate kiss. Her tongue ran its way over Fluttershy’s lips, softly poking and prodding until Fluttershy opened her mouth and let her in. AJ moaned as Fluttershy pushed her tongue into AJ’s mouth, and the two appendages danced all around each other in a sensual dance.

AJ began to trace the length of Fluttershy’s body with her hoof, starting at her belly and making her way up to her chest, as she continued to passionately kiss the pegasus. Fluttershy felt her pussy getting hotter as her juices started slowing onto the bed. She wanted AJ to touch her, to help her release everything she had pent up. She knew her own hoof wasn’t going to be enough this time.

AJ broke the kiss and began to plant soft kisses all over Fluttershy’s body. AJ loved the feel of Fluttershy’s soft fur against her lips as she breathed in the aroma of grass, flowers, sweat, and the scent of sex. AJ knew that Fluttershy was almost ready, but she was having too much fun to stop just yet. With a gently motion, she took one of Fluttershy nipples into her mouth and gently sucked on it. Fluttershy let out a very audible moan as AJ let the nipple go and began to run her tounge in circles around it. AJ then took the other nipple into her mouth, and performed the same action, resulting in the same soft moan. AJ placed her hoof on the inside of Fluttershy’s thigh and began to run it over her legs. She would move her hoof close to Fluttershy’s pussy, but then she would move it over to her other leg and run it back down towards her hoof. AJ loved teasing mares like this. It drove them wild with excitement, and it looked like Fluttershy was no exception.

The scent of excitement was almost too much for AJ to handle. She wanted to bury her muzzle into Fluttershy’s slit and drink in all of her juices. But she restrained herself as she reminded herself that this isn’t for her; it’s for Fluttershy. She looked over to Big Mac and motioned him over. Big Mac straddled Fluttershy’s body and positioned his hard cock just before Fluttershy’s opening.

“Ok Sugarcube, I think you’re ready.” AJ nodded to her brother. Big Mac slowly inched his way forward until the tip brushed up against Fluttershy’s wet opening. Fluttershy gasped once again as he slowly began to gently push against her slit, moving his cock slightly up and down to cover the tip with her juices.

Fluttershy clamped her eyes shut as she felt Big Mac slide into her. A sharp pain erupted from between her legs as she sharply inhaled. AJ held her hoof tightly as she brushed Fluttershy’s mane.

“He’s in, Sugarcube, you’re doing great. Now he’s going to move in a little deeper and then pull out a little.” Fluttershy felt herself beginning to cry again as Big Mac began to push his way deeper. Her pussy felt so warm and slick with her juices…and it was tight. Big Mac almost came right then, but through sheer willpower, he was able to calm himself down enough to slowly pull out. Big Mac could feel her entire pussy enveloping his cock as he gently pushed his way back in, slightly easier this time.

AJ felt Fluttershy’s grip begin to slowly loosen as she watched her brother make love to her friend. The sight of his cock slowly going in and out of Fluttershy’s pussy was making her incredibly wet. She felt her juices beginning to drip down her leg as she sat down and spread her leg wide.

Fluttershy felt her pain beginning to fade as new and unfamiliar sensations began to take its place. Fluttershy heard herself let out a soft moan as she felt Big Mac’s cock hit a particularly sensitive area inside of her. The sensation of being filled up with a stallions hard cock was very pleasing, more so than her hoof could ever provide. She looked up at Big Mac who had his eyes closed as sweat poured from his head and dripped onto her. His grunts made her even more excited as she felt something beginning to build between her legs.

She looked over at AJ, and let out a small gasp. Her friend had her hoof buried into her slit and was greedily watching the two of them. Fluttershy smelled AJ’s sex as wet, squishy sounds reached her ears. AJ grinned as Fluttershy moaned and began to grind herself into Big Mac.

Big Mac wished she didn’t do that as he felt himself building faster than he wanted. She felt so good, better than his sister, and he didn’t want to slow down. Her quiet grunts and moans were so arousing, and just watching her face made him almost come over the edge. He then noticed his sister with her hoof buried between her legs, watching them, and he erupted with a loud groan.

Fluttershy saw Big Mac grit his teeth, and then she felt her body filling up with his seed. The sensations of his jizz filling up every nook and cranny inside of her sent her over the edge too. She felt her pussy quickly contracting around his cock, massaging it as wave after wave of her orgasm washed over her like ocean waves. Her mouth was wide as a soft scream flowed from her throat.

Big Mac pulled out as strings of jizz continued to erupt from the tip of his cock, covering her pussy in ribbons of cum. AJ felt herself nearing nearing her peak and began to concentrate her hoof directly onto her clit as her pussy erupted in a flood of pussy juices, shooting out over the panting pegasus. Her scream pierced the entire barn and echoed out over the fields as she collapsed to the ground, panting.

Big Mac felt his legs give out as he too collapsed to the ground out of exhaustion. He felt his dick continue to twitch as cum slowly flowed out of his cock. He stared at Fluttershy, taking in her sweat covered body and heaving chest. AJ managed to crawl up next to the pegasus and planted a soft kiss on her sweaty cheek.

“Now, that wasn’t so bad, was it, sugarcube?” Fluttershy smiled as she looked over at the grinning orange earth pony.

“T-That was amazing.” She said quietly as she leaned over and nuzzled AJ’s neck. “Maybe next time, you can join in too?” AJ laughed as she rolled onto her back.

“Ahm not sure if Big Mac could handle the both of us.” She sat up and winked at the large red stallion. “But we could sure give it a go.” AJ, Fluttershy, and Big Mac erupted in laughter as the three ponies soon fell asleep, dreaming of the next roll in the hay.

Author's Note

This is the last chapter for this fic. I hope you all enjoyed it!