Diamond's Dilemma

Questionable Vengeance

It had been a tense day for Diamond Tiara. It hadn’t been because of something that happened, but from something that could have happened. Babs was in town for the Apple Family Reunion. After a promising start, things quickly went south after the Summer Harvest Parade when the CMC came to Babs’ rescue. Admittedly, Silver Spoon and Diamond Tiara deserved what happened and probably more. Diamond Tiara had the most reason to regret what she did. Babs had been a godsend, and she wanted to consider Babs her special somepony, but blank-flanks stick together and Silver Spoon and Diamond Tiara had made it their job to tease them.

The Diamond Tiara and Silver Spoon had spent the day avoiding the train station, Sweet Apple Acres and all the paths in-between. Still, she had been waiting for a knock at the door. It was at least going to be Babs, probably with Apple Bloom and maybe the other CMCs; at worst it could include Applejack and/or Babs’ parents. For someone to come and complain to her and her dad, Diamond Tiara didn’t even want to think of what the punishment would be.

But the day had come and gone with no incidents, even her dad hadn’t seen any of the Apple Family or their relatives all day. After 8:00 in the evening Diamond Tiara breathed a sigh of relief as she was sure that she was off the hook. Even though she had most of the day hiding indoors she was exhausted from all the worrying. After taking her evening shower she slipped into her bed, feeling a slight tinge of regret for what she had done to Babs but glad that the day was over.

***

Diamond Tiara stirred from her sleep when her blankets seemed to disappear from on top of her. She groaned as she started to reach down to pull them back up over her. A hand covered her mouth and pushed her head into back into her pillow as someone else started to climb on top of her! Diamond Tiara’s eyes shot open and adjusted to the darkness just at whomever it was finished pinning her down. It was Babs!

Diamond Tiara squeaked in fear; Babs looked angry and there was no telling what she was going to do. “So you think you can get away with tormenting my friends huh?” She asked in a harsh whisper, her face getting close to Diamond Tiara’s. “Especially after what we did together? You’ve got some nerve.” Tears started to form in the corners of Diamond Tiara’s eyes, she knew Babs had every right to be mad with her, but sneaking into her room in the middle of the night was extreme.

“I know how you liked it,” continued Babs, “So now I’m going to make you hate it.” Babs kept her hand clamped over Diamond Tiara’s mouth as she sat up, revealing that she was naked. Babs had lost a fair amount of weight and put on some muscle in the weeks she had been away. She looked sexier that she had before, but she was also much more intimidating. Babs turned around, not caring if she happened to kneel on any part of Diamond Tiara, and lifted her hand of off of Diamond Tiara’s face just long enough for her to take a gasp of air before Babs sat her crotch down on Diamond Tiara’s mussel.

“Now lick it,” she ordered, “and I’ll let you breath.” Babs still had a fair amount of junk-in-the-trunk and was doing a good job of cutting off Diamond Tiara’s air supply. Diamond Tiara tentatively stuck her tongue out of her mouth although Babs wasn’t making it easy for her. “You can do better than that,” taunted Babs, still not satisfied. Diamond Tiara forced her tongue along Babs’ folds, hoping for a respite. “Eat my pussy like a little fuckin’ whore,” said Babs as she started to rock her hips from side to side.

The motion finally gave Diamond Tiara some space to breath, but it was very rough. She tried to lick Babs’ cunt as best she could but the way she kept moving was forcing Diamond Tiara’s head around. If anything it was like Babs was using Diamond Tiara’s face as a grinding pole. Babs started to slide her hips from front to back over Diamond Tiara’s mussel, smearing her juices all over it. “Tongue fuck me,” she moaned. Diamond Tiara attempted to slide her tongue into Babs’ folds as best she could, but as soon as she did Babs pulled away.

“Get it stuck up there,” sighed Babs as she brought her hips back down on Diamond Tiara’s face. Diamond Tiara and Babs grunted with one another as Babs brought her lower lips down over Diamond Tiara’s tongue again and again. With one final vigorous slap Babs wiggled her hips over Diamond Tiara’s mussel as she came. Diamond Tiara sighed though her nose hoping that the struggle was over.

But Babs had no intention for it to be over yet. With Diamond Tiara still pinned under her hips and stomach, Babs pulled her bottoms and panties off. Diamond Tiara tried to keep Babs form doing so but without being able to see what she was doing and Babs having more leverage she could only slightly delay the inevitable.

Babs finally lifted herself off of Diamond Tiara’s lighter frame. “Turn over,” she ordered as if she hadn’t climaxed at all. Diamond Tiara didn’t have much room to comply so Babs took her by the hips and worked to flip her over. Babs forced Diamond Tiara’s stomach and hips flat against the bed before pulling her tail to one side and lying on it so Diamond Tiara couldn’t use it to cover anything. Diamond Tiara grunted as Babs flopped on her. Diamond Tiara could feel Babs’ breath on her cheeks as she quietly chuckled.

Babs started to run a finger over Diamond Tiara’s backside. “You really have a nice ass,” complimented Babs. Diamond Tiara tried not to make any sounds as Babs continued to tickle her butt. “So round and firm,” whispered Babs as she moved to the other cheek. “It seems so innocent,” there was a pause, “But I know the truth, don’t I?” Babs stuck her finger in Diamond Tiara’s rosebud up to her knuckles. Diamond Tiara moaned as her anus clamped down on the invading digit.

“You might want to scream into that pillow,” whispered Babs, “Wouldn’t want your dad to see you like this.” Diamond Tiara pulled the piece of bedding around her mouth to cry into as Babs started pumping her finger in and out of her tight asshole. Babs started to lick and nibble at Diamond Tiara’s butt cheeks to elicit varying moans and squeals. Diamond Tiara flexed her legs and knees, trying to get Babs off her back or at least get her to stop, but the futile effort only seemed to make Babs giggle even more. Sometimes Babs would try and sink her teeth into as much area as she could, making Diamond Tiara groan in more annoyance than pain. Other times she would nip at the slightest fold of flesh to make it actually hurt, though never hard enough to draw blood.

All of a sudden the pain was washed out by a sudden rush of energy in Diamond Tiara’s nethers. Babs stopped everything she was doing to listen to Diamond Tiara moan through her pillow. “You just came, didn’t you?” asked Babs. Diamond Tiara didn’t answer. She felt scared and ashamed of what just happened. “Wow, you really are a dirty little butt slut,” taunted Babs. Diamond Tiara could feel herself about to cry. She just wanted it to be over.

“Well then, you’re gonna’ love this,” whispered Babs as she sat up and reached behind her. Diamond Tiara watched her hand as it reached to one side of the pillow to grab something that was out of her field of view. As Babs brought it up he held it so Diamond Tiara could look at it for a second. Diamond Tiara’s eyes went wide in horror. It was a double ended dildo about a foot and a half long. It was made of a clear plastic and was thicker around than Silver Spoon’s vibrator by almost a half a width. “Like it? I got it just for you,” teased Babs. Babs lay back down on top of Diamond Tiara pinning her tail to the side again so there would be no obstructions.

“No!” Diamond Tiara whispered in panic, “I’ve never used anything that big before!”

The protest didn’t stop Babs. “Well there’s a first time for everything,” she gloated as she pulled one of Diamond Tiara’s butt cheeks to the side.

“No!” begged Diamond Tiara as she felt the toy make contact with her other cheek. “Please don…” her voice got caught up in her throat as Babs slid the toy into her anus. Diamond Tiara’s back arched as much as it could from the sensation of her hips being pushed apart more than ever before. Diamond Tiara’s jaw trembled in a silent scream from the feeling of the head and fake veins of the dildo rubbing against her rosebud as it made its way inside her.

Babs continued to chuckle as she slowly sank six inches of the toy into Diamond Tiara’s ass. She then reversed course pulling the dildo out until only the head remained lodged in Diamond Tiara’s tight pucker before pushing back in again. By this time Diamond Tiara had the pillow wrapped around her face, moaning and crying uncontrollably in pleasure and frustration. Babs picked up speed, enjoying how easy it was getting to slide the phallic device in and out of her victim, Diamond Tiara’s anus turning red around the toy.

Diamond Tiara wasn’t sure how long Babs had been pumping the toy into her before extracting it and letting her rest but it took at least a minute before she could fully get a hold of herself and look back over her shoulder. “I told you you would like it,” gloated Babs. Diamond Tiara wasn’t sure if she had experienced one long orgasm or many in a row.

“What now?” asked Diamond Tiara, the worry barely showing through the fatigue in her voice.

“I’m going to see how deep this little pony-hole goes,” whispered Babs as she turned back to Diamond Tiara’s ass.

“What?!” the panic returning to Diamond Tiara, “That thing is huge! It’ll never fit!”

“Let’s find out together,” replied Babs undaunted. She slid the dildo back into Diamond Tiara’s already loose and wet tail hole. First the six inches that she used before went in. Then another two. As the ninth met resistance Babs bent and twisted the toy in circles stirring up Diamond Tiara’s insides and causing her to groan even more. The toy started to slide freely again, Babs slowly turning the dildo along its length as it wormed its way further in, pushing the breath out of Diamond Tiara as it went. The sensation of the toy running through her rosebud overpowered the pressure that she started to feel in her lower stomach. Diamond Tiara’s screams turned to whimpers as it became harder and harder to get a lung-full of air.

At last Babs stopped when her fist, which was wrapped around the last few inches, presses against Diamond Tiara’s swollen ring. “Wow, you took almost all of it.”

Diamond Tiara could only speak in a barely audible whisper. “Take it out…Take it out…”

“Okay,” Babs replied, matter-of-factly. Babs yanked the entire length of the toy out in a second, not fast enough to hurt or cause any damage, but enough to make it an uncomfortable surprise. Diamond Tiara’s eyes flew open and her mouth dropped in shock as the dildo was ripped from her ass. She barely remember to plant her face firmly in her pillow before letting out a bloodcurdling scream.

Diamond Tiara didn’t know if she blacked out but the next thing she remembered was Babs flipping her onto her back. Babs crawled back up over her but kept herself on her hand and knees so Diamond Tiara could breathe. Babs held up the toy, pointing to a wet line at one end where she must have stopped pushing it in. It was no more than four inches from one head of the dildo. “I’m impressed Diamond,” said Babs sounding genuine, “your ass took most of it.”

Diamond Tiara pleaded in a soft whisper, which was the strongest voice she could muster, “No more. Please, no more.”

“Don’t worry, we’re done for the night,” Babs said as she got closer to Diamond Tiara, “Just remember one thing.” Babs took Diamond Tiara’s chin in a few fingers to make sure she was looking her in the eyes. “No matter what you do, or who you fuck, your ass belongs to me.” Babs planted a familiar romantic kiss on Diamond Tiara’s lips, completely catching her off guard. Diamond Tiara sighed as Babs pulled away, taking the dildo and sneaking to the window before climbing out. Diamond Tiara lay still listening as she heard Babs quietly land on the roof of the shed below her window and then to the grass. There was some more rustling which she guessed was Babs pulling on her clothes before she finally slipped away into the night.

Diamond Tiara’s thoughts shifted to the confusion of what had just happened. The fear she had felt, the pleasure Babs had forced upon her, the dull ache in stomach, the wetness between her legs, between her cheeks and on her bed. There was no doubt Babs had been angry with her. But that kiss was just so passionate. And what did she mean by “belongs to me”? As much as Diamond Tiara wanted answers, her body demanded sleep.

***

Diamond Tiara dragged herself down the stairs the next morning. She had slept solidly and woke up in the same position as she had fallen asleep but was still exhausted. Her hair was a mess and her pajamas were horribly wrinkled.

“Good morning,” said her dad as she shuffled into the kitchen. “Are you feeling okay honey?” he asked seeing her disheveled appearance.

“Rough night,” she groaned as she opened the fridge to get breakfast. At least her stomach felt normal again, although her ass was still tender.

“Well I’ve got something that will cheer you up,” said her dad, upbeat again now that he knew she wasn’t sick.

“What’s that?” she asked as she turned around with a carton of milk in her hand.

“A business partner of mine wants me to come to a meeting with him, and the host company has offered to pay for five days at a hotel suite. Next month we’re off to Manehatten!”

Diamond Tiara’s eyes went wide for a second before she forced a smile. “Great…”