Jack in Equestria

by bigmacintosh2000

First Time

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I barely closed the door of Fluttershy's cottage before she jumped into my arms and pinned me against the door. She was lighter than I expected (Are pegasus bones hollow? I wondered). I held her up with my arms under her forelegs and her hind legs pressed against the sides of my abdomen. We kissed passionately, over and over. I kissed her long neck, and she nibbled my ears. I got hard as a rock, and her juices began to wet my shirt.

"Let's go upstairs," I said.

She practically pulled my arm out of the socket as she fluttered up the steps, leading me along while I held her hoof. Inside the bedroom, she jumped into my arms again. We kissed more, and I tenderly laid her down on the bed.

Suddenly she hid a turquoise eye behind her pink mane again, looking up at me with a nervous glance. "This, is, uh, my my my..."

"I know," I reassured her with the most serene look I could manage in my lust-engorged state. "I'll be gentle."

I pulled off my t-shirt and began kissing her. I started with the frog of her right hoof, slowly working my way up her hind leg. As my lips met the fur of her hock, I reached up with my left hand, cupping her left teat, and gently caressing. I worked my way up her inner thigh. I planted a few kisses around her dripping vulva, then one on her throbbing clit (she shuddered), before moving up to her right teat, sucking softly. She moaned with lust and sat up, using a forehoof to pull my pants down. My dick was harder and bigger than ever before as she kissed it and licked up my length. She looked up at me meaningfully, then grabbed my hips with her forehooves and laid down, pulling me toward her. Her face was at a convenient place to suck my nipples while I began to prod at her vagina.

"Fuck me," she groaned.

I slowly pushed the head of my cock, but it was tight. For a moment, I thought I wasn't aiming at the right spot. I had to push much harder than I expected, until finally I was inside her, tearing her open. She tensed in pain. "Are you alright?" I asked.

She nodded, lips pursed. "Mm-hmm."

I worked the head of my dick back and forth a few times. With each gradual thrust, I went in a little deeper, and she tensed in pain. Each time, she gritted her teeth, and her pussy tightened around my shaft. Soon, I was in her to the hilt, and she seemed to relax. "I'm going to start to move, okay?"

"Uh, okay, but do you think you could take it slow? If that's alright with you."

Resting on one elbow, watching Fluttershy's face under my chest, I began to move very slowly. Her pussy tightened each time as I worked my shaft out, and gave away easily as I thrust in. Each time she cringed less in pain and moaned more in pleasure. Her pussy felt so good. It sucked me in, and it felt way too good. I wasn't going to last long at this rate. I pulled out, putting a disappointed look on her face. "I want this to last a little longer. I straightened my back, looking down at a trickle of blood coming from inside her and staining the sheet. Rubbing my shaft between her pussy lips, I cupped her teats and pulled gently on her nipples a while.

When my excitement ebbed enough, I forced my way into her again, and she moaned in pleasure with a pained look on her face. I began thrusting slowly, very, very slowly, leaning over her and running my fingers through her mane. She looked up at me, in pain and love, with parted lips, her entire body tensed. As I neared the edge, I pulled out again, sitting up to rub her clit with my thumb. She gently rocked her haunches in response, juices coming out of her in increasing quantity. I lay down next to her, kissing her deeply, while I continued to play with her slippery pussy.

She pushed my hand away with a foreleg. "Fuck me, please."

I positioned myself over her again, grabbing her ass cheeks in either hand, and pushed my way inside once more. It seemed to hurt her a little less now, and as I thrust against her wonderfully tight folds, her body rocked back against me in response. I moved slowly, but she was still too tight for me to hold on as I reached climax all too soon. I whispered to her, "I'm going to cum."

She looked up at me, with a desperate, begging look. "Cum inside."

With a few more thrusts, I came. And came, and came. It poured inside her, but some wouldn't stay. It came splashing out around my dick, trickling down over her asshole and mixing with the thin, red blood.

"Fluttershy, you feel so good."

"It was amazing," she agreed.

"Did you?"

"No, but that's okay. It hurt too much this time. I'm just glad you liked it."

I laid down next to her again, putting my hand on her sloppy vulva. "No, it's not okay. I'm going to make you cum." I kissed her, our tongues entwining, as I began to stroke her clitoris. It didn't take long before she held my arm in place with her forehooves and started bucking at my hand. More juices poured out of her, mixing with the mess that was already there.

She kissed me on the neck, tucked her muzzle into the crook of my neck, and fell asleep. I listened to her breathing, my hand on her heart.


Author's Note

I added A LOT of detail and anticipation to this scene. I hope you enjoy the improvements.

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