Lily’s Anal Curiosity

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She loses her anal virginity (on film).
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HeyAll
HeyAll
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Part 1 of 3: The Ass Revealed

She was named after the lily flower. That was no surprise, considering how her mother was an avid gardener who was drawn to blooming plants.

Oddly enough, she soon realized that her mother's lily flowers often blossomed to look like a person's asshole. Lily thought of this while daydreaming in the middle of a conversation. She was sitting in a cafe on the college campus, a hot drink in hand, while her best friend was speaking.

"Lily, are you even listening?" Miranda asked, peeved at the rudeness.

"Huh? Yeah, of course, I am."

Lily took a sip of her coffee and tried to act like she was listening.

"If you were listening, then what was my question?" Miranda asked with a sharp gaze.

"Something about assholes."

"I asked if you've ever had anal sex before."

"Jeez, what the hell kind of question is that anyway?" Lily responded incredulously. "At least buy me dinner first, for goodness sake."

"It's a relevant question. Just answer it, and I'll tell you why."

Lily sighed, "Sort of. I've experimented with anal, sure. These days who hasn't? But it's always been painful and I've never gone all the way. Basically I'd consider myself to be an anal virgin."

"Sounds like a series of disasters."

"That's exactly right."

"Perfect," Miranda smiled.

"You're starting to creep me out, you know that?"

"On the contrary, I may have a small job offer for you."

"A job offer that involves anal disasters?" Lily asked.

"Let me explain," Miranda said, preparing her offer. "As you know, I have an internship for a small downtown film company. They want to make a medical instructional film about anal penetration. You know, rectal exams, prostate stuff, things like that. Since I'm the only person in the company who currently attends college, I offered to find our model. I hope it'll help me land a full time job there."

Lily flashed an 'are you kidding me?' look to her friend.

"Seriously? You're looking for an asshole model and you came to me?"

"That's not the entire offer," Miranda insisted. "I told them that you're an aspiring screenwriter."

"Aspiring novelist too."

Miranda shrugged, "I told them that you're a great writer and you could write some of the dialogue for the instructional film. It'll look good on your resume."

It was an attractive offer. Lily was looking for experience writing and this was certainly a nice place to start. But the anal part was a deal breaker. That wasn't her thing. Especially on film.

"Can't I just write the thing and someone else can do the modeling?" Lily asked, almost pleading because she wanted the writing job.

"It's a package deal. They're looking for a model, if you're interested in being the model, they'll hire you to write."

Lily sighed, "I still don't understand why you came to me with this. You know that I'd never do anything like this on film."

"Because you're perfect for this, whether you realize it or not."

"How am I perfect for asshole modeling?"

"Well, you've got a great body, a killer butt, you're adventurous, and you've got great skin. Plus we need an anal virgin to help show that these techniques actually work." Miranda crossed off on her mental checklist. "So will you do it? Please?"

Lily paused, slowly coming around to the idea. "No face, right?"

"No face at all. Just your bare legs, crotch, butt, and of course an intimate closeup of your little asshole."

Lily put her hand on her face. "Oh god."

"Oh yes."

"Why me? Why? There are so many beautiful girls on campus who'd get naked for free."

Miranda patted her friend's shoulder. "Honestly, I'm embarrassed to ask anyone else. I don't want people to know I'm involved with videos of people's rectums. They'll think it's porn, but it's not. It's for medical purposes."

It was a decent point and Lily understood her friend's motives. It was also a win/win situation for both of them. Lily would gain experience writing for an instructional video, which would help boost her resume. And Miranda would look good to the company, helping her land a coveted full-time job.

"This is no easy decision," Lily sighed. "But I'll give you a tentative agreement, assuming we can work out the details later."

Instead of being elated that her friend had finally agreed to this, Miranda sharpened her eyes and gave a long hard stare. It was like she had detected something, only she didn't know exactly what it was. All she knew was that there was something there. Something worth exploring.

"What?" Lily finally asked. "You're making me uncomfortable with that look on your face."

"I somehow get the feeling that you're kind of excited about this."

"Excuse me?" she asked incredulously.

"You heard me," Miranda replied.

"Wow, the nerve. Don't forget, I'm doing you a favor. Not the other way around. I certainly don't need my ass violated by strangers, while the whole thing is recorded on film."

Miranda doubled-down and sharpened her eyes more. "I think I've finally figured it out. You have some sort of anal curiosity."

"Interesting. I didn't know you took psychology in high school? Or was it middle school psychology?"

"I'm being totally serious here. I've been an intern long enough to know when the subjects are aroused by their participation."

Lily's eyes widened. "Whoa, wait a second. I am not aroused by this at all. Okay?"

"It's really nothing to be ashamed of. Plenty of the subjects who agree to this are secretly aroused in some way. It's perfectly normal. Some of the women who do this have an anal fetish they want to explore. Others are exhibitionists while others love the medical thing. But of course, nobody admits this outright. It's like a dirty little secret that everyone kind of knows."

"You know what? I quit. You can go find another model. We can still be friends, and I'm still going to sit here because it's comfortable and my coffee is still hot. But I won't be participating in this anymore."

"Lily, you're being over dramatic here."

"Me!?"

"Yes, you're being over dramatic," Miranda insisted. "Look, would you get offended if I said that you enjoy sex or masturbation?"

"No, but..."

"That's the point. Everyone enjoys sex and masturbation. It's still pretty taboo, sure. But no one denies it. So why would you deny enjoying your participation in this medical instructional?"

Lily sighed, "I'm getting confused."

"It's actually fairly simple. Deep down, there's something about this that you enjoy. In my opinion, it's probably the anal thing, since you've done it a few times before."

"Attempted to do it," Lily clarified. "The mission was never fully accomplished."

"Right. What I'm saying is, you've obviously had a desire to experience anal intercourse in the past. Maybe the curiosity is still there? And that's okay. At our age, everyone wants to experiment. So why not experiment with the doctors and professionals? They'll treat your ass right, literally."

Lily raised an eyebrow. "So they're experienced with this?"

"Obviously. The people doing the procedure are doctors with special techniques for anal insertions. Believe me, I've seen them work. And I've seen women having orgasms from the anal insertions."

"Just fingers, right? No tubes or metal devices."

"Of course, just fingers," Miranda nodded. "Lubed fingers covered by soft latex gloves. Only your anus will be filmed. The purpose is to demonstrate the best methods for anal penetration. It's to train new doctors. Just think, you'll be contributing to the medical community."

"So very awesome," Lily said, half-sarcastically.

"Come on, let's go, there's something we need to do in your dorm."

Miranda grabbed her cup of coffee and left. Reluctantly, but with curiosity, Lily did the same and followed.

***

The girls entered the dorm room. No one was there at the moment since there were several classes still in session. Once the door closed, Lily turned to her friend for answers, only to see her take her phone out.

"What are you doing?" Lily asked, wondering what the heck was going on and why they needed to be in her dorm room of all places.

Miranda flipped through her phone. "I need to take a picture of you to show to the company. They'll need it to decide whether to hire you or not."

"Don't you already have tons of pics of me on your phone? We take pictures all the time."

"I need a picture of your butt," Miranda smiled.

"Oh jeez..."

"Hey, it's understandable, don't you think? They're not going to hire someone who's butt-shy. They need to know that they can work with your ass."

Lily flashed a frustrated look. "You're making it hard to be your friend."

"Right now, I'm the best friend you've got. Who else is giving you job opportunities?"

"Touche."

"Now, undo your pants so I can snap a few pictures."

There was no point in arguing any further since Miranda had already shown her persistence on the matter. Plus, it made perfect sense that the company would need pictures first. Lily had applied for internships before where she had to submit writing samples. Why would this be any different.

She undid her jeans and pushed them down to her ankles, standing with her thin white panties showing. The friends looked at each other and Lily gave an 'are you happy now' expression.

"And the rest," Miranda said.

Lily slid her panties down to reveal her cleanly shaven crotch. As friends, sure they had seen each other in undergarments, bikinis, and a few other states of undress. But the level of skin they had shown each other had never been this explicit.

"Let's make this quick," Lily insisted.

"Will do."

While lily stood still with her bare bottom and crotch exposed, Miranda got behind her and snapped different pictures of the naked ass. Each picture was taken from a different distance and angle.

"Now grab ahold of something and bend over," Miranda said, with her phone ready to take more pictures. "I'll need to take some more intimate pics.

"You've got to be kidding me."

"Afraid not. Asshole please."

Lily gave a deep sigh. She didn't need to hold anything for support. The girl had great balance and flexibility. She simply bent over and put her face in between her knees while her legs remained straight. Years of deep stretching was now serving its purpose.

"Damn girl," Miranda briefly admired. "You're flexible. Plus you've got a perfect bottom."

"Lots of yoga and pilates," Lily said with her face upside down.

More pics were taken.

"Now reach behind and spread both cheeks," Miranda said.

Without losing balance, Lily reached behind and gave her butt cheeks a nice wide opening, by grabbing a hold of each of them and spreading herself. She was vulnerable like being in a doctor's office. But of course, a doctor would never be taking pictures of her little hole. No, only her friend would do that.

"Got it!" Miranda said with a sense of excitement. "Here, have a look."

Lily stood upright once again and gladly pulled her panties up, along with her jeans, and fixed her appearance before facing her friend. God knows she had been exposed enough already.

When she turned around, there was Miranda holding her phone out to show a highly revealing picture of Lily's pink anus. It was stretched wide open, showing every single line of the anus, every shade of color (shades of pink and brown), and of course the little black hole in the center which led to her rectum.

"It's actually kind of weird seeing myself this way," Lily said.

"I think it looks pretty."

Lily squinted her eyes. "Okay, this is getting weirder."

"Don't be so over dramatic. I'll speak with the doctors and professionals at the company. Hopefully they'll like you, which I'm sure they will."

This was all happening so fast and everything started sinking in. Gosh, was this actually happening?

"Can I be honest?" Lily asked rhetorically. "You were right. Anal has always been something I've been curious about."

Miranda smiled, "Thought so. I knew there was something in your expression that revealed something."

"Let's hope this goes well. I'm willing to give it a shot."

***

If Lily was truly honest with herself, anal sex had been something she had wanted to explore for the past few years. In her own private time, she had come to enjoy watching free porn sites which included acts of wild anal sex and women screaming in pleasure as a result. That's ultimately where her fetish came from.

Sure, she had tried it with a few ex-boyfriends and hookups, but it had always turned out to be a disaster. It seemed like men had a natural tendency just to shove it in. So the idea of doing it, and learning from true medical professionals sounded like a great thing.

The only problem was, she'd be getting her ass played with in a room full of gosh knows how many people. Plus, it would all be recorded and watched by countless others.

Internally, she made peace with these facts. She tried focusing on the brightside, which was that she'd be in good hands (literally and figuratively) and that she'd be helping medical professionals in the process.

To prepare for this, and to boost her confidence, she went to the gym later that day in a tight pair of yoga pants. She focused her workout routine on squats and other lower body workouts. Every so often, she'd check her backside in the mirror, even in front of other gym members, as if she was obsessed with her own ass.

There was also the waiting. Every time her phone made a beep, she immediately checked it to see if it was Miranda. She had quickly become restless. But as it turned out, she didn't have to wait as long as she had expected.

Part 2 of 3: The Ass Lubed

It was a few days later that Lily finally got the message she had surprisingly been excited to receive. Miranda had gotten the answer from the company she worked for and wanted to meet with Lily as soon as possible, and in the privacy of a dorm room.

When they finally met in private, Lily was beaming with enthusiasm while Miranda remained in a calm business-like manner.

"Well, what did they say?" Lily asked impatiently.

"Good news and bad," Miranda said. "Well, they're both good news depending on how you look at it."

Lily sighed. "Let's hear it."

"The good news is that they really like you. In fact, they think you're awesome. They like your body and tight little anus. They also like that you have a curiosity towards butt-stuff because it means you'll be inclined to the process. And they love your flexibility."

"Sounds like I'm their ideal candidate."

"So much so that they're willing to pay you five thousand bucks. That includes your writing services too. They're interested in having you co-write the instructional."

Lily smiled. "Five thousand bucks eh?"

"Yep, and, here comes the other news."

Lily sighed again. "Of course, the bad news.

"I see it as good news, actually."

"What is it?"

Miranda gave a sly smile to soften the blow. "Well, the company sees so much potential in you that they want you for a different instructional video instead. It's purely a business move since the company is kind of struggling right now."

"Just tell me already. I'm dying of suspense right now."

Miranda looked her friend straight in the eyes. "They want you for an anal sex instructional video. They feel you'd be much better suited for that given your beautiful body and flawless butt."

It was the revelation that changed the game entirely. Now things were headed towards a whole new level. One that could potentially have life altering ramifications.

"Anal sex?" Lily finally asked, eyebrows arching.

Miranda nodded. "Correct."

"As in, sexual intercourse in my ass?"

"Yes, correct."

"This sounds like a fucking porn shoot."

"It's an instructional video," Miranda countered. "Remember, there will be doctors in the room and everything will be treated with the utmost care."

Lily counter back, "A cock going in and out of my ass for sexual pleasure sounds like a porn video to me."

"Look, I'm sorry. I went to the company and this is what they're offering now."

"What about the anal instructional video for doctors?" Lily asked. "The one for medical exams."

"Apparently they've found a couple of girls willing to do that. But they want you for the anal sex video because of your fantastic body and flexibility. And also for your desire to experience anal sex."

Lily took a long pause and gave her friend a hard stare. For the past few days, Lily had gotten herself excited for this, but only because she thought it was for the medical instructional video. A sex video is a whole new ball game, and with her ass of all places. Nevertheless, as daunting as the whole thing seemed, the curiosity still lingered inside of her.

Opportunities like this don't come around very often. And deep down, she knew she might regret it if she rejected the offer.

"Suppose I agree," Lily said, with a business-like mindset. "The rules will still be the same right? My face won't be shown, right?"

"That's correct. No face. There will be a narrator and host for the video."

Lily sensed something was wrong. "What about the rest? Are the rules still the same?"

"There's been a change in the offer," Miranda said tensely. "Since this video will feature anal intercourse, you're expected to be nude the entire time. That's in addition to the closeups of your anus and the closeups of the actual anal penetration."

"Jesus."

For a moment, Lily briefly battled with a feeling of vertigo, like she was suddenly about to fall over from a dizzying feeling. But she managed to stay on her feet. Being naked? Being naked in front of a bunch of other people? Being naked while filmed? Closeups of her anus while being fucked anally?

This was all becoming too much for her. She was mentally prepared for an anal insertion video. That would be no problem. But this?

The irony was, the more frightened she felt inside, the more aroused she became. This would be the ultimate sexual taboo, at least to her, and her limited sexual history.

"Keep in mind, you're dealing with professionals," Miranda said, sensing her friend's apprehension. "They've seen this plenty of times before. No one will be acting like a creep or a pervert."

Lily gulped. "And the guy? Who is he?"

"He's a nice guy. You'll meet him later if you agree to this. Trust me, he's a pro."

"How big is his penis?" Lily inquired.

"About 7 inches."

"Holy sheesh. 7 inches for my first time? I've never even had a cock that size in my vagina. Did you forget that I'm an anal virgin?"

"All the more reason you're perfect for the part," Miranda said with a light smile on her face. "The whole point of this video is to prove that there are scientific methods to opening an ass."

"Did you just say 'opening an ass?' Really?" Lily asked incredulously.

"Hey, we're dealing with doctors here. They open and close things. That's their lingo."

"Whatever they want to call it, this all sounds so daunting. I'd be okay with the anal instructional. You know, with fingers. But with an actual cock, I don't know. Especially not one that's 7 freaking inches."

Miranda nodded. "I sincerely apologize for getting you so excited for all this. I really mean it. When I first heard the offer, I thought it would be fun if you did it. I had no idea they would only offer you the anal sex video."

"It's not your fault, Miranda. You've always got my back. That's why I love you."

"And that's why I love you too," Miranda smiled.

"What a heart-felt moment during such an awkward time," Lily joked.

"Yeah, you're right. But does this mean you're not going to do it? Is this a definitive 'no' answer? I have to let the company know right away. They want to make these videos as soon as possible."

HeyAll
HeyAll
22,148 Followers