Author's Note

Contains: Little porn content, just character interactions and setups.

I'm planning on making Sunset Shimmer a regular in this story, because how can she not be?

The Sexual Adventures Of Sunset Shimmer: Initiation

Twilight knocked on the door to Rarity’s house, the one belonging to her friend’s human counterpart, a few hours before night was turning to morning.

After some clicking from the locks, the door opened a smidge, and Twilight could see the bleary eyes of Sunset Shimmer eyeing her wearily and warily.

When Sunset registered who was standing outside the door, it opened fully, and Sunset quickly stepped aside with a relieved look on her face.

“Twilight!” she breathed. “I’m so glad you’re here.”

Twilight quickly stepped up and embraced Sunset, holding her face against her shoulder. “It’s okay, don’t worry.”

Twilight reached behind her and took Sunset’s hands in her own, guiding them down towards her buttocks, and encouraging Sunset to play with them.

As Twilight was under the effect of a very well-crafted illusion spell, Sunset failed to notice anything out of the ordinary, and simply welcomed the pleasant sensation.

As Sunset fondled Twilight, she took a few calming breaths, and Twilight felt Sunset’s heartbeat slow down, before Sunset asked, “Did you say you know what’s going on?”

“I think I do,” Twilight said, and kicked the door closed behind her. “Let’s check on them so I’ll know for sure.”

“We were having a slumber party, and we went to bed,” Sunset said. “And then I woke up from something, I think it was too quiet, and saw them like this.”

They entered the bedroom, with Rarity’s enormous enormous bed, and some foldable ones as well, where the five of her friends’ human counterparts lay, limbless, rubberized, and looking at her with a scared expression.

“Oooh,” Twilight cooed, and quickly gathered them up, sitting down on the bed and holding them against her. “It’s okay, everyone. Don’t worry, I can fix this.”

“You can? You’re sure?” Sunset asked.

“Yes. I’ll need to bring them back to Equestria, but once we’re there, it shouldn’t be a problem.”

“What’s happened?” Sunset asked.

“To help answer that, let me just cast a spell.”

“A spell? Twilight, you don’t have a horn,” Sunset said, before Twilight reached back and pulled at her panties, before inserting two fingers into her rear and pulling out a purple horn.

“I do, actually. I managed to trick the transformation spell on the mirror, and keep mine,” Twilight said, and pointed it at her friends, like a wand, lighting it up and covering them in magic.

“What are you doing?” Sunset asked, before her eyes became wide, just like all her friends’. “Whoa…! Twilight,” she breathed.

They took in Twilight’s shape, her full form, healthy and radiant. It was now that they finally registered how she looked. How her skirt couldn’t hide her curves or how her blouse struggled to contain her breasts, and the stylish thigh high stockings.

They stared at her perfect hips, and the soft shape of her belly, and how she absentmindedly put her finger to her lips as she thought.

“Twilight,” Sunset breathed again. “What happened?”

“Well, the short version is this…”

After a short rundown, Sunset was still staring at Twilight in disbelief.

“A sex doll?” she said, as the others stared wide eyed at Twilight.

“Yes. Don’t worry though, it’s quite nice once you get used to it,” Twilight said, and smiled at Sunset.

Sunset finally registered that she was once again trying to take in Twilight’s great beauty, and shook her head, looking away with red cheeks.

“It’s… that’s… that’s why you’re acting... provocatively?”

“Yes. I’m sorry, I don’t actually mean to. It’s actually my new cutie mark,” Twilight said, when her face lit up. “Speaking of which, I brought some cutie marks for all of you!”

“Brought cutie marks? You can’t…” Sunset said, before petering off.

“I didn’t believe it myself, but this whole business has taught me a lot about magic and cutie marks,” Twilight said, and opened a small bottle she had in her shirt pocket.

Out of the bottle floated five identical marks of a bright red heart held tight by chains, glowing in the air, before Twilight directed them to the waists of the transformed human girls.

They quickly fastened themselves to the five dolls, who looked on with open fascination, before they huffed wordlessly and looked away.

“It tickled, right?” Twilight asked, and the dolls nodded, when Twilight turnen to Sunset. “Alright, let’s get you all back to Equestria where I can work on getting new bodies for everyone who wants them. You might want to be transformed as well, Sunset. You might feel a little left out if you don’t.”

That was three days ago, and Sunset had to admit that her life had definitely improved since then.

She was now a rubber doll just like her friends, of her own choosing, with an improved version of Twilight’s illusion spell that she had helped develop, where she and her friends could mentally command the the direction and power of the illusion at will, and also covered outright outlandish things. They could, for example, drop the part of the illusion that made people not consciously register how voluptuous or raunchy they were, but also have them not notice anything out of the ordinary.

Rainbow Dash and Applejack had had a lot of fun pulling each other’s clothes off in class as pranks, with the only reaction being that the rest of the students had trouble concentrating on their work and the teacher telling them to stop unless they wanted detention.

It was quite a strange experience, to be the former ‘bad girl’, not at all above using unspoken promises of sex to get her way before changing her way, and suddenly seeing her bashful and ‘pure’ friend, Twilight Sparkle, the way she was.

But there was nothing ‘dirty’ about Twilight. Sure, she might have been very eager to have pretty intense sex, and when Sunset experimentally lifted Twilight’s skirt and touched her friend’s bum, Twilight was nothing but happy.

There was a wholesomeness to Twilight, and presumably the other sex dolls in Equestria. Behind that voluptuous shape that threatened to spill out of her clothes at all times, there was nothing sinister. No manipulation, or domination, or greed. Just sex. Happy, wholesome sex.

Sunset looked around her apartment. Her small studio apartment, which she had, with her great sense of interior designing from living in Canterlot Castle during her formative years, made to look a lot more expensive than it actually was. It was cozy and homey, despite the cheapness. And it was cheap, because Sunset didn’t have a lot of money.

Her friends had helped her out after she mended her ways, and stopped shaking down other students for money, and pawning stolen goods for a fraction of their value, in order to keep living where she did. And while her friends assured her that it was no problem, in her mind she was still racking up debts, along with the sudden wall of debts she had when she decided to be a better person, and tried to make up for her past misdeeds.

She walked over to her fridge, and opened it, seeing nothing but a sad slice of pizza and a half empty bottle of soda.

This would have been a problem, if she still needed food and sleep, but it just helped fuel an excitement in her belly.

She no longer needed to spend most of her hours between school days sleeping and resting, and while eating and drinking was as good as ever, she didn’t need to spend her means on that either.

What she needed was sex, and while she was very much a novice compared to Twilight, which was still a bit strange to consider, she could perhaps use that to further her goal of making money.

She looked down on herself, jiggled her new, large breasts, ran her hands across her form, and smiled. “This is a money maker if I ever saw one.”

She sat down by her computer, thinking as it booted up. She could perhaps just look for a graveyard shift at an expensive high rise, working the night behind the reception and touching herself when no one was around, but that felt like a waste of opportunity.

She looked up “gentlemen’s clubs” in the area, hoping that no tech-savvy student she had tormented was spying on everything she was doing with some strange computer magic, but stripping didn’t feel right, as it could undermine the new image of nice girl she was trying to build for herself, teasing poor guys and gals with things they weren’t allowed to touch. Same deal if she eschewed the club and used her webcam.

No, with the access to sites dedicated to the trading of goods and services, she decided to take an approach where she felt she could have more control. With her abilities, she felt confident trying her hand in the oldest profession in the world: prostitution.

She was careful not to word her ad in such a way as to draw the attention of the authorities, because unlike Equestria, here it was illegal to offer sex for money.

When she at first learned that it was illegal, it had been a strange trivia, but gradually it had started making sense. Unlike in Equestria, there was the risk of very dangerous diseases, the workings of the dangerous inner cities at night, the lingering effect of the lack of contraceptive and the scores of desperate children and lone mothers as a result, as well as a slew of other factors.

That wasn’t the business she was looking to get into. She was going to have the approach that the prostitutes of Equestria had. It was just a service; companionship for money.

Sunset often wished she had seen prostitutes while she had the opportunity. The princess might have approved if she did; back when she was, frankly, a stuck up bitch. Perhaps everything would have been different if she tried just walking up to the guards’ barracks, asking them if they could recommend anypony, and have a hunky stallion show up in her quarters a few nights and pound her tensions away and her mind blank, she might still be living in a castle, her ambition never morphing into megalomania.

Still, it was probably best not to wish for such things. As it turned out, she had wonderful friends, and a good life that was looking better all the time.

Sunset finished her post, and hovered over the send-button. It was exciting in many ways, but one reason was that she was an archmage of Canterlot, a scholar of dangerous lores, and a vanquisher of evils, and she was about to become… a whore.

No… not a whore, a prostitute certainly, but she was to bring the class of an Equestrian lover-for-hire to this world. Still, it felt a bit as if Princess Celestia was to grab her sword and set out banish evils that threatened her world with her own hands. The high and mighty stepping down from her lofty position and getting her hands dirty- the number of books about that in Equestria were beyond count.

She clicked the button. She was now Sunset Shimmer, aspiring call girl.

Sunset looked at herself in the full body mirror. She was wearing a bodysuit made of black latex straps snaking their way across her body. It covered her crotch and her breasts, but left little else to the imagination.

“This is wonderful, Twilight,” Sunset said happily, as she spun around in front of the mirror.

Twilight, looking at her from the propped up book on the table, nodded her approval.

“You look amazing, Sunset,” she said. “Do you notice those straps by the brassiere? Try pulling them.”

Sunset did as instructed, and the fabric covering her bosom fell away, landing on the floor.

“Ah!” Sunset exclaimed in a happy surprise, touching her breasts, before looking at Twilight again. “Thank you so much! Where do you get these things anyway?”

“Well, with Rarity having so many more hours in the day, she’s branched out and is by now really good with latex. I’m learning a lot too. I don’t have them with me, but I’ve made a few dildos I’m really proud of.”

There was a chime from Sunset’s computer, and she bent down to read it, leaving Twilight with only the nice view of Sunset’s behind, bare except for the small bit of latex covering some of it up.

“My first customer is responding!” Sunset said excitedly. “We’re going away for the weekend tomorrow.”

“That’s wonderful,” Twilight said. “Just look at you, you’re going to make them so happy!”

“Thank you, Twilight. This feels really good. I’m so excited for this.”

“What about the other girls?”

“Everyone is busy this weekend. Don’t worry, I have a gps tracker on me so that they can see where I am, in case my first customer is up to no good.”

“I wasn’t thinking along those lines,” Twilight noted, with one eyebrow raised.

“Well it’s just that people in this world can be a bit weird,” Sunset said, still typing on her computer.

“You don’t have to worry about your safety, Sunset,” Twilight said. “I’ve had my brain scooped out of me and I’m fine.”

“Yeah, but you know, in case they kidnap me.”

“If you’re worried about that, you can come over and my brother can teach you to fight even as you’re picked apart.”

“You have a brother?” Sunset asked, looking up.

“Yeah. I guess I never told you. He’s a doll too. We can practice how to fight together.”

“I might take you up on that offer. I’m also curious what a stallion looks like when they’re turned into dolls like us.”

“Hunky,” Twilight immediately said. “Very hunky, not difficult to look at at all.”

A ray of sunlight snuck its way past the gap in Sunset’s curtains. “Wow,” Sunset said. “Is it that late already? Or maybe I should say early?”

“I suppose so,” Twilight said. “Is it time for school?”

“Soon. I’m going to have to try out the rest of the outfits later, before my client picks me up,” Sunset said, and walked towards the door.

“Sunset! Are you sure you want to go to school like that?”

Sunset looked down on her topless body, still dressed in the exciting getup.

She shrugged and looked at Twilight teasingly. “With your illusion spell, no one would mind.”

“That’s true.”

“Still, I might as well stick to normal clothes. To keep this clean for one thing.”

Sunset sat on the bench in the park, looking around.

She was at the exact spot she had agreed on with her client, spying out for a man with black gloves sticking out of his pocket.

It felt like a spy thriller, and she was starting to slightly regret her decision. This wasn’t as wholesome as she had imagined it. Still, she was determined.

After a while, she spotted a man by the fountain, with black gloves like they had agreed. Nice build, handsome, good hair, clean clothes, and the expression on his face helped put Sunset at ease.

He was whistling softly to himself as he idly scanned the park, and she looked at his eyes as his gaze gently swept across the park, letting him spot her on his own. She willfully dropped parts of her illusion, letting people around her register her amazing figure.

He stopped whistling when he saw her, and started walking up in a calm gait, and they gave each other a smile as they neared.

“Sunset?” he asked.

“That’s me,” she answered, a bit of nervousness in her belly.

“Would you like to come with me?” he asked.

“I’d love to,” she said, grabbing her duffle bag, and rose, following the man.

They kept the same pace, at enough distance where they could be everything from business partners to family.

He looked back at her, and quickly scanned her up and down, smiling openly.

“My car is across the street, we can do introductions there,” he said, in a quiet voice.

“That sounds good,” Sunset agreed. The park wasn’t exactly crowded, but it was worth putting off talking for half a minute to be on the safe side.

They walked across a street, to a small, secluded parking lot, where a woman was waiting.

At first, Sunset’s legs felt weak, wondering who this person was, if this was a sting operation or something, before she steeled herself. That was television stuff, and not something that actually happened.

She felt further reassured when the woman openly studied her figure, and smiled happily.

“Now then. Sunset, was it? My name is Night Light, and this is my wife, Twilight Velvet,” the man said.

Sunset was taken aback, before rallying. “I’m sorry, but you’re married?”

“Why, yes, dear,” Velvet said.

Sunset looked at her, which certainly wasn’t painful to do. Her name and haircut reminded Sunset of her friend Princess Twilight, which helped put her mind at ease.

“I’m sorry,” Sunset said, shaking her head. “I just wasn’t expecting… you know, a married couple.”

“It’s not a problem I hope?” Night said. “You did say you were fine with both men and women.”

“I am,” Sunset said, readily. “I’m sorry. I guess I have some preconceptions.”

Velvet tittered. “So did we. We were expecting someone pretty, but not someone so glorious,” she said, and gestured at Sunset’s figure. “Just look at you.”

Sunset smiled bashfully, before looking around.

“You’re right,” Night said. “Perhaps we can invite you into our car for privacy?”

“Thank you,” Sunset said, and sat down in the rear seat, while Velvet sat down next to her, behind her husband.

“I’m going to start driving,” Night said. “Say the word, and I’ll stop and let you out. If you change your mind at any time, we’ll take you wherever you want to go.”

“It’s no problem,” Sunset assured him. “But thank you all the same. May I ask, you know, now that we’re speaking in private, what you expect from me?”

“If… you’ll allow us to be frank, dear, we want to hire you as a prostitute over the following days,” Velvet said.

“Then we’re on the same page,” Sunset said, happy that they were moving along, both figuratively and literally, towards their goal.

“Good. I hope you’ll be patient with us. We’ve never done this before,” Night said.

“You haven’t? You seemed so sure when you wrote to me,” Sunset noted.

“That was me, dear,” Velvet said. “And thank you.”

“Well, it’s my first time as well,” Sunset said.

“Now that I find hard to believe,” Velvet noted, smiling at Sunset as she studied her up and down. “Just look at you. With a body like that, you must have been fighting both boys and girls off with sticks.”

“It won’t be my first time being intimate with someone, but it will be my first time being paid for it.”

Velvet cocked her head. “How do you feel so far?” she asked in a concerned voice.

“It feels good. I need money for a good thing, and hopefully you’ll be happy as well.”

“Ah yes, the payment,” Night noted, his eyes on the road. “We never agreed on your rate.”

Sunset’s bashful smile got a degree of confidence. “I’d like your happiness to determine that.”

Night looked at her in the rear view mirror, and Velvet did the same from the side, before they smiled. “That was sexy, wasn’t it, honey?” Night asked.

“It certainly was,” Velvet agreed.

“Very well, if you insist, we’ll discuss it afterward. Don’t be afraid to bring it up during the next few days,” Night said.

Feeling that they were bonding a little, Sunset decided to carefully push ahead. “If you don’t mind me asking, you two seem happy together. Why hire a prostitute?”

“We are happy together,” Velvet said, putting her hand on her husband’s shoulder, who put his hand on her’s. “In large parts because we’re open and accepting with each other. For example, I agreed to spend a few hours in ‘the box’, and Night agreed to be tied up and be my plaything, and we found out that we liked it.”

Velvet looked at Sunset and smiled. “Too much information, dear?”

Sunset shook her head. “Not at all. This is actually really sweet. You wanted to try having a third lover?”

“Yes,” Velvet said. “How willing would you say you are to trying new things?”

Sunset thought back to Twilight, and the gear she had send her, which was stuffed in the duffle bag between her and Velvet. “Very. Do you guys have any more stories about things you tried?”

They drove out to a secluded house by a lake in the woods. A gorgeous view of the water and hills, fresh air, a little jetty and a hill mostly bare of trees besides a house that was both rustic, yet clean and with modern comforts.

“Wow,” Sunset said, standing with her duffle bag in her hand and looking out across the water. “This is wonderful.”

“Thank you, dear,” Velvet said. “Some know-how of my husband, and booksmarts and strong arms from our children, and we rebuilt the rustic old cottage to this. We’re kind of proud of it.”

“You should be,” Sunset said, before registering what Velvet had said. “You have children? Who are old enough to help build houses?”

“We do,” Velvet said. “You sound surprised.”

“You just look so young,” Sunset noted.

Velvet smiled sweetly at Sunset. “Oh thank you. What do you say if I say that we don’t expect it to be long before we’re grandparents?”

Sunset opened her mouth, and closed it again. “No way,” she said, inspecting the practically-grandmother and her practically-grandfather husband. “Really?”

“It’s true,” Night said. “Our oldest and his fiance has trouble keeping their hands off each other.”

Sunset tittered a little, before Night got a serious look on him again.

“Now, Sunset. I want you to know that at any time, you can just say the word, and we’ll stop, and take you back into town.”

Sunset gave him a reassuring look. “It’s okay, I’m looking forward to this. We can start whenever, with whatever.”

Night looked at her for a moment, trying to spot any sign of a lie. When he didn’t, he smiled, and put his arm around his wife.

“I think I was afraid that when we corresponded you were just pretending, and that you’d actually be a sad and tired young woman, but you are really into this aren’t you?” Velvet said.

“I am,” Sunset said, happily. “Oh, also, I should show you what I brought.”

Sunset took her duffle bag, and unzipped it to show what was inside.

It was full of restraints, sexual toys, and interesting outfits. A lot of it was shiny and black, but there were some pure whites and pinks as well.

“I have a friend who I’m gonna work with to make outfits for every situation,” Sunset said. “So far I have some pretty standard stuff.”

“You call this standard?” Velvet said, her mouth open in shock.

Night silently crouched down and retrieved a butt plug with a white bottom and a pink heart on it, as well as a bottle of lube.

Sunset stood still, with an expectant smile on her face, as Night stood up and took a step towards her.

“Do you want me to act in a certain way?” she asked.

“No,” Night said, and shook his head. “I don’t want you to act at all, I want to see how well you like this.”

“Okay,” Sunset said, as Night placed a hand on her back and gently pushed her forward. She bent over and thrust her behind out, looking back with an expectant smile.

Night lifted Sunset’s skirt and placed it over her back as Velvet watched in silence. Night put his hands on Sunset’s panties, right on her sex.

Night took a deep breath in response to what he felt, and pulled Sunset’s panties down, before coating the plug with some lubricant, and gently inserting it into Sunset.

“Mmm,” Sunset happily moaned.

“She’s so pretty,” Velvet noted to her husband. “Do you want to ravish her, dear?”

Night chuckled, and Sunset stood up. “I do, but it makes me want to ravish you as well.”

“Oh I don’t even know where to start,” Velvet said.

“Some roleplaying after this perhaps? Sunset suggested. “Perhaps one of your childrens’ girlfriend that you’ve seduced without them knowing?”

“Naughty,” Night said with a smirk.

“And I’m curious about this ‘box’ of your’s.”