The Game

Feeling more relaxed as I came back from the spa, I took a short nap on the bed. Luna joined me, snuggling up from behind me, spooning me as I felt her warm waist on my lower back. I highly enjoyed the feeling, but I was unhappy with the lack of personal connections by not seeing her in the face. I turned around and faced her. The look of slight confusion at my motions was absolutely adorable. I stroked down the side of her neck until I finally felt the warmth that greeted my back now go to my own waist. I couldn’t help but begin to feel a little hard. It wasn’t even much longer until Luna felt me poke her.

“Hmm,” she moaned. “Are you turning into a unicorn, or are you just happy to see me?”

“I’m always happy to see you,” I said.

We both laughed as I hopped to her flank and she laid down on her stomach. Feeling invigorated again, I proceeded to have sex with Luna.
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I woke up about an hour later sleeping on top of Luna’s back. She was out like a light, even when I gently nudged myself off of her. Before heading downstairs for something to eat, I gently petted Luna’s flank, causing her to roll over onto her side, sprawling herself out much like a cat would.

I remembered that we were out of pizza, so I fixed myself a glass of milk and a small stack of oreos. After having my pre-fuck snack, I went to my room to find out my next mission. To prevent from waking Luna, I took the dice and cupped them in my hand. I then made my palms flat and rolled the dice in between my hands like someone who was making a ball of out of clay or silly putty. I then let the dice slide quietly off my hand. Ten.

Alright.

The piece moved, and the text appeared:

Show her all your sexual moves, for the mail pony Derpy Hooves.

Oh boy.

I was thrust back into the board.
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I woke up on the streets of Ponyville. Many of the ponies eyed me, probably expecting them to say that its their turn. Unfortunately for them (and to an extent me), they would not be getting dick inside of them for now.

I strolled along looking for the grey pegasus, when who should fly into me from behind and knock me on my stomach but Derpy Hooves herself. Letters from her mailbag were scattered all over the ground. She began raking them all up in her mouth and tossed them in her bag.

“I’m so sorry, mister,” she said, walking up to me.

Her voice sounded like the altered “normal” one that was released on iTunes following her “controversy” in The Last Roundup, but I was happy to look into her trademark crossed eyes to see that they were still the same.

“Wait a second,” she said, “you’re a human.” She gasped her next breath. “Is it finally my turn?”

“Yes,” I tell her, despite my wanting to tell her no.

“Awesome! My first human! Come with me to my house here!”

I followed her. Through out the trip, I would notice as she clumsily veered to different sides as she walked, tripped sometimes, or even on one occasion fall. This is why I was apprehensive about fucking Derpy. As much as I loved her on the show and always saw her as an ideal snuggle buddy, this was not the snuggling that I had in mind.

Having sex with her would feel like having sex with a mentally handicapped person, and I didn't find that sexually exhilarating in the slightest. Who knows? Maybe I’d be rutting her and she jerks her ass to the side and breaks my dick.

I snapped out of my nightmare to find I had been led to a little house on the outskirts of town. She let me in as she set her bag on the floor.

“So, what do you like to do?” she asked me? “Do you like it slow, or do you get right into me from the beginning?” I wanted to prolong this for as long as possible before I did the deed.

“Could we start… with a kiss?” I asked.

“Sure thing. Let’s go to my bedroom.”

I followed her up as she ran towards her bed and jumped. Her back hoof hit the end of the bed, pulling her front forward as she fell with her face forwards as she landed smack-dab onto her pillow.

Jesus.

“What are you waiting for, slowpoke? I’m ready when you are.”

I reluctantly crawled into bed with her as she inched towards me. She leaned her head forward, and I instinctively pulled back.

“What’s wrong?” she asked me.

Realizing what I’ve done, I lie with my back on the bed, contemplating what I might have done to her.

Hopefully she didn’t take that as an insult.

“It’s because of my eyes isn’t it?”

Fuck.

“It’s okay,” she answered, tears beginning to well in her eyes. “Nopony has ever wanted to have sex with me because of my eyes. They think I’m too stupid to have sex with.”

I begin to feel her, and I turn to face her, but she’s sitting up and looking out and away from me.

“They think I’ll slobber over them when I kiss them or give them a blowjob, or I’ll start spazzing out when they rut me.” Her voice is weakened as she tries to control her sobs. “I’d never do any of those things. All I want is to be loved, but nopony will give me a chance.” She finally lets it all out, he tears bleeding from her eyes as they fall onto her covers.

My own waterworks began. I remembered seeing the Save Derpy video on YouTube, and I certainly remembered how sad I felt at how close-minded people could be towards such an innocent creature. It’s only then that I began to feel such sadness over this because now I was one of those close-minded people. I did the one thing that I want to do right now. I reached over to Derpy and gave her a tight hug. Her crying stopped, but her voice still sounded shaken.

“What are you doing?” she asked.

“I’m so sorry, Derpy. I should never have done that. In my world, there are millions of people that love and adore you, myself included.”

“R- Really?”

“You are such a great pony, and I should never have underestimated how smart and intuitive you really are.”

“You really mean that?”

“Every word. Would you please forgive me so we can start over?”

She finally faced me and returned the hug, leading me to grip her like a child with a teddy bear.

I guess getting a real hug from Derpy Hooves really is one of the best things imaginable.

“I forgive you,” she said, her voice much more controlled now.

She then shifted her face to mine and slipped her tongue in my mouth. I realized how good of a kisser she was. She sat in front of me as we leaned towards each other to taste each other’s sweet mouths. I then slipped my hand underneath her and lifted my index and middle fingers up, inserting them into her vagina.

I heard her moan as she continued kissing me, her breath filling the inside of my mouth. I gently swirled my fingers inside of her as she continued kissing me more sensually. My fingers got incrementally wetter as I continued to finger her. However, she eventually seemed to pass out on me, as the pegasus who was sitting before me was now lying on her side with her eyes closed. I was unsure of what to do until she swung her tail in a circular motion, inviting me inside.

I picked up the limp pony and laid her on her stomach, her legs positioned so her ass was slightly up in the air. I got on my knees and positioned them under her waist. My dick was now in line with her newly dampened pussy. I slid into her like a knife to butter, fully appreciating her soft, smooth insides.

Derpy seemed incredibly passive for a supposed virgin, it’s then that I felt the walls of her vagina lightly clamp down on my dick. I slowly pulled in and out of her, causing her tail to spasm due to the pleasure. Looking at the base of her tail as it twitched I saw her clenched anus right below it. Taking my thumb, I inserted it into her ass like fresh pizza dough. This caused her to moan even louder as a tight pressure exerted itself around my penis and thumb.

I broadly encircled my thumb in her anus as I continued sliding my penis in and out of her vagina. I sweetened the deal by taking my free thumb and middle finger and roughly massaged her two breasts. With all three actions in motion, I began doing them faster and harder.

Derpy and I had just about enough that we could handle. With a few moans that turned to screams with greater and greater intensity, she finally came, me following soon after. The muscles in her ass both constricted my penis and thumb as her juices coated my dick inside of her. Using her fluids as lubrication, I slid my dick out of her pussy. She then pushed my thumb out of her anus. After our tryst, she hopped onto me and gave me another hug.

“Thank you so much,” she cried. “I love you!”

“I’m glad,” I said, “because I enjoyed that too.”

“Well, you have to go back now. You have a lot more ponies to have sex with, and I want you to win.” She flew above me, her pussy visible from below.

“Good luck!” she said before she dive-bombed her ass into my face, sucking me into her and back into my room.