A Brief Window of Opportunity

Finally, she stood up. She was wearing something— the shape was thong-like, but the waistband was made of heavier material. Like it was meant to support a lot of— Of my god, that's a strap-on. God damn, I'm an idiot. 'I hope my dick could get a break.' Careful what you wish for, jackass.

She threw her forehooves onto the mattress, confirming my fears, as a massive rubber horsecock bounced around over the foot of the bed.

"No no no no no!"

"Oh... Did I... um... do something wrong?"

"No! I— It's just... I don't want to do that."

"Oh... I'm sorry... I just... You said you wanted me to be happy... I've never been able to do this with anypony before..."

Oh dear god, no. Not that face. Not those puppy-dog eyes.

"I... I do want to make you happy! It's just... Really?"

"I'm sorry, it was crazy. I'm sorry." Her hooves fumbled at the straps. As much as I wanted to let her take it off and just use me the same way the others did, there's something about the look in her eyes that tells me I'd never be able to forgive myself. I'll have to spend the rest of my life knowing that, during my sole opportunity to meet her, I made Fluttershy sad.

"Never mind, I was stupid. Do whatever you want, Fluttershy."

"Really?!" She gasped, completely lit up about the news. As if that wasn't cute enough, she blushed and uttered that intolerably cute squee. She threw her front hooves over my legs and around my midsection. "Oh, thank you, thank you!"

"Wait!" I protested, "Don't you need to, like, lubricate me first?"

"Not really," she replied bashfully, pressing the tip of the strap-on against my butthole. Great. I don't think she knows how anal actually works. Hopefully she'll stop to figure it out once she sees how much pain I'll be in. I turned my head away and clenched my eyes — just like getting my blood drawn — if I can't see it, it won't hurt. Right?

Wrong again. She pressed against me with quite a lot of force, and my body resisted the deformation she was trying to apply to it fervently. It probably wouldn't have been so bad if the tip had been rounded, like human genitals, but it was anatomically correct for an equine, having less of a tip than a flat end. I squealed a bit as she first penetrated me, my sphincter muscles burning from having been stretched a little too far a lot too fast. I grimaced and took a deep, sharp, breath.

Noticing my negative response to her hurried start, she slowed down considerably. Very carefully, she pushed in an inch, pulled back three-quarters of an inch, pushed in another inch, pulled out three quarters, and on and on like that, slowly stretching me a little further than I would have guessed was possible. It really only hurt a little bit, and I can't say that I didn't get the occasional twinge of pleasure when she applied force to my prostate. Whatever material it was made out of slid in and out of me effortlessly, as if by magic. Probably was magic. I'm getting plowed by Fluttershy, who's wearing a magic strap-on. What a day.

After about a minute, whatever pain there was subsided. It was still kind of uncomfortable— I basically felt continuously like I needed to take a huge dump, but all in all, it wasn't that bad. At least Fluttershy was happy. Happy and determined. I'm not sure what she's driving at, actually, I highly doubt she's going to be able to finish like this, and I probably won't, either.

She pulled out, and examined my ass, which felt a bit like it was gaping open, though I wasn't sure. She started untying my left leg.

"Flu—" Twilight began, but she was silenced by Rainbow's hoof against her mouth.

"Shhhh... I wanna see where this goes."

Confirmed for sadist? Maybe, maybe not. At this point the choice between Pinkie and Dash next is still way up in the air. Fluttershy moved my loose leg over the other one, and tied it to the same post, leaving my back end sideways, suspended, and exposed. I really hope that whatever she's planning is over soon. She used a little more care in entering me than she did last time, though it was hardly necessary now, given that I was already so stretched out.

The best thing I could say about the last position is that it didn't hurt, but this new situation was completely different. She had managed to find an angle for which every single stroke delivered pressure against my prostate, and the feeling was quite intense. There was still that awkward discomfort of having a stuffed-full rectum, but I was definitely starting to feel the sexual aspect of this experience. My heart was beating pretty fast... Oh!

I was about to come... Any second now. Er... Wait for it... This doesn't feel right. It's like I'm paused right on the edge of orgasm, but I can't get there. Finally, I feel it. My penis twitched, trying to fire off its third load in the last hour, but nothing came out. I know I wasn't dry, Twilight cast that freaky refilling spell on me...

Finally, it dawned on me. It was the fucking strapon, jammed into my ass. It was pushing on my insides and squeezing my urethra shut. That, I didn't see coming. Wait. Didn't... Coming... I think there's a pun there, but my sex-addled mind can't put it together. After a couple more seconds, she worked out that I was done, and pulled out suddenly. My ejaculate shot further than I'd ever seen it go before, probably on account of all the built-up pressure. The floor, the curtains, the bedpost... All covered in my seed. I'm really just glad none of it got in my eyes; that would have sucked, with my hands tied up.

She crawled up into the bed and nuzzled up against me. I tried to focus on her warm, fuzzy body, and her downy wing draped around my torso, and ignore the fact that the artificial penis she had just fucked me with was pressed against the small of my back.

"Good job, Fluttershy." Twilight noted. I couldn't see her, the way I was turned, but I heard her scratching at the parchment with the quill. "That was the fastest run yet."

Fastest?! That easily took twice as long as Rarity's thing. Even Applejack's drawn-out grind-fest didn't even take that long. I demand a recount! Hell, it wasn't even over, really. My asshole still felt like it was twice its normal size. Before I could spend any more time being angry with Fluttershy, she whispered "That was wonderful," into my ear, and slipped out of the bed. God damn it. I'm so damn conflicted about what just happened.

"Next?" Twilight repeated.

Damn it, Twilight. Come on. I've done three in... what, forty-five minutes? There's plenty of time for the others. Just give me ten minutes, please.

She magically unhooked the leg that Fluttershy had moved in order to violate me more effectively, and re-tied it at the proper corner of the bed, while tapping her quill against the paper. "Next," she parroted.

Ugh. Rainbow Dash or Pinkie Pie. After Fluttershy, I have absolutely no idea what to expect from either of them, logic means nothing.

"Rainbow," I responded, sighing.

"Don't you sound excited," she commented, strutting up to me. She looked back to the others. As if by an unspoken understanding, everyone except for Rainbow and Twilight went up the stairs, into the room above. That was a little unsettling. "You know, I would really prefer to be alone for this," she told Twilight.

"It's just a precautionary measure," the unicorn replied, "It's my ass on the line if anything goes wrong. Besides, I need all the data I can get."

Data... So she is recording information about me. So like Twilight... Huh. A thought occurs. She's saved herself for last so that she can use all of the information she collected about me, on me. That's a rather unique combination of cute, thoughtful, geeky, and creepy. Which, I guess, was Twilight down to a T. Well, I guess it was Dashie-time. Twilight cast the spell on my genitals once more.

I looked down at my sore, throbbing, involuntarily-stiff member, and then looked at Rainbow, my eyes pleading for mercy. With a playful smile, she made a wing assisted leap and landed on top of me, before pressing her muzzle against my nose.

"Don't worry," she said "I won't ride you hard like the others."

"You won't?" I asked, feeling an odd combination of relief and disappointment.

"Nope. You're gonna have to work to earn my love!"