Pipsqueak gets all the Ladies

Once again, Pip needed Twilight as a tutor for one one of his math assignments as his homework, and she was more than happy to help him as usual. "Okay Pip," she said. "Divide five from ten."

"Right, right." Pip wrote the answers down. "Listen Twilight, I hope that you don't mind doing this for me again, do you?"

Twilight made a giggle and she replied: "of course not. You're one of my friends and I am more than happy to help out a friend." Bedroom eyes formed on her face and she whispered in his right ear: "especially if you want to have sex with me." Then she kissed his ear.

Pip flushed and he was glad to hear that. "Good."

The tutoring went on for fifteen minutes and Pip was done with his homework. "There! All done." Said the princess of friendship.

"Good. I hope I pass the next test."

"I know you will, sweetie." Suddenly, the magical table of friendship was going on the fritz a little. A few sparks were going off like it was malfunctioning.

"What was that?"

"The table of friendship is acting a little funny." Twilight got a little closer look at the table which contained the map of Equestria and a gigantic white ball appeared above it.

Pip was suddenly sucked into the white portal and it meant he was aucked into a world unknown.

"Uh-oh. I think I need to go through a multiverse again." Twilight said to herself. "Spike!"

Meanwhile, Pip was in an unknown place that looked a lot like the Crystal Empire and the castle looked the same shape, but it was dark and the clouds were orange colored.

The townspeople looked brainwashed and gloomy with glowing green eyes like they were under a spell.

It seemed very scary for Pip to see and it made him think of King Sombra, who was the longtime dictator and tyrant of the domain before the princesses sealed him away to the pits of Hell.

"Oh no." Pip muttered. "I got to get out of here!" He never felt so scared in all his life, and he didn't even know what to think of this.

He knew that Twilight traveled through time before, so he hoped that she will come to this world and rescue him. "Hey you," said a voice that sounded low and menacing, yet calm.

It was a tall, yellow crystal stallion with a black clad of armor and a helmet glowing green eyes on his head.

"You look very unfamiliar in this city."

Pip couldn't really say anything. He was too scared to even yelp or scream.

"Who are you?" The knightlike stallion sounded a little more threatening in that tone.

Pip tried to speak up but he didn't have the strength to even Yelp. "I.... i...." was all he replied to the brute.

"Not one for talling, hmm? Well, no matter. The queen herself will make what to do with you and your kind. Come. Let me take you to her majesty herself?"

"W-who is she?"

"You will see when you enter the throne room. Now, come."

Pip did as the guard told him and he set foot inside the corrupted castle, and he knew that it was gonna go terribly wrong fast. He walked many corridors with the scary guard and he was seeing many other guards with the same color armors but worn different colors of fur, male and female.

Some of the guards stared down at the colts and he was trying so hard not to look back at them all. Ponies like them can probably smell fear and he didn't want them to harass him and call him a coward.

"Heh. That's a thing you don't see every day." Said another guard in a higher voice than the one who was escorting Pip to the queen, whoever that may be.

"A lost kid." Said another male guard.

"Kind of adorable." Said a female guard. "Looks like a perfect teddy bear."

Pip flushed a little but he kept on walking and many guards continued staring at him.

At last, the large double doors revealed the throne room and it had an insignia of a banshee or a face of an evil spirit with glowing red eyes on it.

"Here we are." He opened the doors and there revealed to be a ridiculously large throne, and the room was bleak with dark windows of purple shining from outside.

It was a little dark, but a bright spotlight appeared above the throne and it revealed to be a mare that looked so much like King Sombra, But, it was a female, a queen, like this stallion mentioned before.

This mare has the same color patterns as the king, it she was very slender like princess Cadence. She was sitting in a regal position and she looked absolutely beautiful in this light. She looked down on Pip, and she smiled at him,

“What might we have here, Captain?” Her voice sounded rather soothing, but it still gave Pip a chill down his spine.

“Malady.” Said brute stallion, “I have found this young boy that looks absolutely different from the townsfolk. He seems.... very peculiar with those odd stripes on his fur.”

This female counterpart of Sombra looked down and gave him a seductive smile. "I see." She said in her silky voice. "Do tell me, sweetie, what is your name?"

Pip was silent for a second, but he realized that he didn't want to face an evil Queen's wrath like this one looking down on him. "My name is... Pipsqueak and... don't laugh, please."

"I wouldn't order the queen such a request like that one." The captain flatly warned him. "Make her mad and you will have to have her wrath."

"It is quite alright, captain." Said the female Sombra. "Now, leave us while me and Pipsqueak have a little alone time together."

"Are you sure?"

"Positive, now, leave my presence."

"As you wish, my queen." Then the captain of the guards exited the room.

Deep down, Pip couldn't get his mind off of how beautiful this mare looked to his eyes. She might be one of the most beautiful mares that Pip has ever seen in his life. Deep down, he hoped that he can have sex with her next.

"So, Pipsqueak is it?" She asked

"Yes, your majesty. But, toy may call me Pip, it's what me friends call me by."

"Hmmm. A rather fitting name for a coot of your stature."

"Thank you. I guess." Suddenly, he felt himself being picked up from her magic, glowing green and he found himself on the queen's lap.

"You looked cold there, Pip." Said the mare.

"Aren't you forgetting something, your highness?" The colt asked her nervously.

"Hmmm?.... oh yes, I did forget something didn't I?" She let out an adorable laugh. "Silly me. My name is Umbra, queen Umbra, the feared and glorious queen of the Crystal Empire, and the greatest pony of all time."

"Hmm. That's an intriguing name." Pip remarked.

"Indeed. A very unique name for a unique unicorn like me."

She noticed Pip's cock growing hard and she smirked.

"Oh ho ho. Do i see that you are attracted to me?" She asked with an amused look on her face. "Just look at that penis that became huge."

"Okay, okay, you got me." The comet admitted. "Toy are very beautiful, like, drop-dead beautiful."

"Ho ho ho, thank you." Said Umbra with flattery. "My beauty can surpass any mate in the whole land of Equestria." She sounded more arrogant and self-absorbed than Rarity was. "Tell you what, Pip, I will make you the happiest little foal for being so kind to me. Granted, we only just met, but still."

Young Pip smiled with hope for himself to have his way with her, or she would have his own way with him. "Thank you, your highness." He replied.

He was suddenly interrupted when she began tongue-kissing him and he swallowed something a little nasty and he felt rather sleepy.

"Oh my. Did I overdo it?" Umbra asked teasingly before she was giggling, and then, Pip fell asleep on her lap from the effects of the drug he swallowed.

Over the course of time, Pip was snoozing for about three and a half hours before he came back to reality.

It was a beey large room that he was beholding and the room was a little dark, but a line of candles with red lights glowing on the wicks were lighting it up.

The air was thick with roses, and a fancy girlish smell. It looked a little spooky in the room, but a shadowy figure appeared in the room, her teeth glowing like daggers.

Green eyes were above them and the figure revealed herself to be Umbra, but no crown or cape, she was completely naked.

Pip’s penis grew hard as a rock and he was ready to do some naughty things with her. “I see you have awoken from your nap, Pip.” She Said in her sultry voice. “You can’t move, right?”

The colt was trying to hard to move his limbs, but the drug he took paralyzed him in place. The only thing he could do in this state was sit back, and relax to this, along with moving his eyes and making his dick erect and hard.

Queen Umbra went up to the bed and snuggled Pip close to her like her own little teddy bear. The colt was feeling her left him up with her dark magic, and he was floating in place like a rag doll.

Before he knew it, he felt himself being pulled and his cockamamie as in Umbra’s mouth while holding him in place with her magic. Oh Pip was still loving this kind of feeling arousing through his body. It was literally magical for him, and he hoped that it will last for him to be as happy as he needs to be.

Umbra even has the pleasure of wrapping her sweet, soft tongue against the sensitive skin of the shaft. A rather silly smile appeared on the colt’s face and he began drooling in ecstasy as she was sucking away on him. Of all the mares that were giving him fellatio in his life, queen Umbra was one of the best when it comes to pleasuring him like this, it even made him wonder if she did this with other boys before him.

It didn't really matter, for he thinks that he is the queen's favorite that she has met and he bent his head as he was enjoying this.

He felt the climax about to come rushing through his body and penis, and he began ejaculating inside of the beautiful queen’s mouth, and he did it about five times. Umbra was fascinating by how much cum a colt like him could hold inside his balls.

After she was done, she immediately let go of his cock from her mouth with a loud “plop!” sound and they were both panting. "Goodness me." said Umbra. "That was very delicious and a taste of satisfaction to please me, the queen herself."

"I'm glad you like it your majesty." then she felt her putting him back on the floor with her magic.

"Don't think this is over yet, Pip." said the evil queen. "Think fast!" she suddenly made out with him and locked his lips with her own, and it was so passionate and rather hot for them both. While they were going at it hot and heavy, Pip suddenly ejaculated two times on Umbra's chest, but they moth made out with their cheeks blushing crimson red.

They kissed on for about three minutes and then they stopped their kissing and Pip found himself resting on her back, laying his belly on her, something similar to a humping position, although he wasn't humping her.... yet. "This is so amazing." he panted to himself.

"I'm really glad you're enjoying this as much as i am, sweetie." said Umbra with her bedroom eyes. "But this is far from over. No, this is just the beginning." Then she used her magic to use Pip like a rag doll again, and he found his dick being slowly pushed inside her opening, and it felt so good.

Still, he was feeling tired, but Pip wanted this to go on for a longer time to make him even more happy. He thrusted and thrusted his shaft inside of his sensitive vulva, and they were starting to sweat and their tongues were dangling out.

"Yes!" said Umbra. "Don't stop! Fill it right in me!"

"I'll make you happy!" Pip panted.

"I know you will."

He was humping her on and on for a long period of time and the sounds of sticky flesh were echoing across Queen Umbra's ridiculously large bedroom.

After about thirty minutes of nonstop humping, Pip ejaculated inside of the queen without warning and she let out a wail of an orgasm, something similar to a demonic screech that sounded a little ear-piercing. It was almost like Pip had killed a gigantic, ancient beast that was more powerful than him, someone only he could defeat and kill, and it sounded like he won the battle of good and evil.

"Sweet mercy!" said Umbra, panting and collapsing on the floor, right on her belly. Pip was feeling just as tired as this beautiful yet evil queen. "That was the best time of my life. Even greater when I killed Celestia and Luna, then killed the original king of this kingdom which is now mine."

"I knew you would live this." Pip panted. "I'm happy to make you happy."

"You have no idea how much pleasure you have created in me, sweetie." said Umbra with a warm smile on her face. "let us snuggle."

"Good idea."

they both rested on the bed and began nuzzling one another and they were having another time of their lives.