I’ve noticed that my schedule has been undergoing a slow change over the past few weeks. I find myself spending more and more time with Derpy. Any free evening, any day off, any time we can find, we seem to spend together. We do all kinds of stuff: dinner, shopping, Lyra’s Hearth’s Warming Party.

On a side note, Goldy and Lily were there. I hadn’t seen them since that session; they appeared to be doing better. Derpy’s also been saying that they’re on better terms. If nothing else, they seem to have stabilized. At the party Lily told me that she’d be moving in soon. Truth be told, I feel like things are going a little too well on that front. My inner skeptic is still worried that that’s going to blow up in my face somehow.

Three days ago, however, I was not concerned with the inner workings of lesbian relationships. I was concerned with something else entirely.

“Are you sure this is okay?” I asked Derpy for what was likely the third time. We continued along the dirt path out of town.

She rolled her eyes. “Yes, Guilty. I asked her at market yesterday; she said to stop by any time. Besides, I wanna see this thing.”

“But are you sure it’s okay if I go with you? Did you mention that you were bringing ‘the whore’ with you?”

She gave an annoyed sigh. I was worrying too much again. This has become part of our dynamic. I worry, she reassures. “Fluttershy’s not like that. Besides, didn’t you say that you were on her good side after you rescued this thing?”

I took a breath to calm myself. “Well, yes, but... I don’t like to show up unannounced like this. Ponies don’t react well when I… jump up on them.”

“Relax, Guilty, you’re not ‘jumping up’ on her. I said I’d be bringing a friend,” she attempted to reassure me.

“But did you say that it was me?” Clarification is important.

She shrugged. “I don’t think I had to. Everypony pretty much knows we’re dating at this point. She probably knew I meant you.”

“I’d feel a lot better if that last sentence didn’t have a ‘probably’ in it. Just saying.”

She sighed and placed a wing over me. “Guilty, relax. If it’s an issue, we’ll deal with it.”

I leaned into her. “Okay.” I didn’t really feel better, but I felt I’d bothered Derpy enough. I was mostly worried that Fluttershy, fragile creature that she is, might not be able to handle the shock of seeing the escort she halfway-propositioned. She might blush herself to death.

In all seriousness, I was worried she’d have a panic attack at the sight of me.

As we approached the cottage, my eyes went wide. Fluttershy’s home was damn near alive. There were birds and critters everywhere. Beavers and doves and lizards and just... fucking every animal. All the creatures were darting around the cottage in the center of the plot. It had an actual grass roof. It’s not a small place, either. I think it’s a little bigger than my place.

We walked across an actual moat and Derpy knocked on the door.

“Just a second,” came Fluttershy’s delicate voice. Moments later, the door opened to reveal the lovely young Pegasus. “Oh, hello Derpy. Hello… G—” Her eyes shot wide as she realized who I was. Called it. “Oh, my… h-hello M-Mister Pleasure. Um… h-how are you this fine day?” I could sense Derpy fighting back a groan. This wasn’t the first time somepony had been awkward around me, and Derpy was beginning to get sick of it.

“I’m fine, Fluttershy. Derpy said we could see the ray today?” A good way to deal with awkward is just to keep the conversation moving.

“Oh… of course, right… that’s why you’re here.” She seemed relieved. “Just let me put on a coat.” She disappeared briefly once again.

“Okay, you were right, Fluttershy kinda panicked,” admitted Derpy. “But it wasn’t that big a deal.” She leaned into me once more.

“Yeah, you’re right. Just a hiccup.” I leaned back.

Fluttershy reemerged, donning a coat and scarf. “He’s just around back. Follow me.” The back of Fluttershy’s house was even more impressive than the front. Chicken coops, pig pens, houses for every kind of animal conceivable— life littered this place.

We, however, were led to a strange looking structure. A dome made of tarpaulin and wooden beams. “What is that thing?” asked Derpy. “He lives in here?”

“Oh… yes… Twilight helped me build it. It’s based on something called a ‘sweat lodge’ that the Buffalo build. It keeps it very warm in there.” She gently knocked on the… tarp. “Poncho? You have some visitors. That nice pony that saved you is here.”

A massive body of grey burst through the flap before swerving into the sky. Derpy jumped back about a yard, wings ready to take flight. The ray began to circle overhead, analyzing his guests, or so it seemed.

“You named it Poncho?” I asked.

Fluttershy giggled. “Actually, Pinkie Pie named him.” The ray began to descend slowly, floating impossibly in the air. He delicately landed on my back. Even through my thick jacket, I could feel his warmth. Derpy watched in amazement as the beast levitated daintily. “I think he remembers you. He never really warms up to new ponies,” said Fluttershy.

“I think he’s a bit bigger, too.”

“Yes, he’s still a growing boy.” She sauntered over and petted him. “My, aren’t you affectionate today?” I could feel his little horn doo-dads kind of wrap around my neck.

“HE’S SO COOL!” shouted Derpy as she ran towards me. “He hovers, Guilty! He HOVERS!”

“Oh? Last time you saw them you were afraid of them.”

“That’s not fair, there were a thousand of them, and I didn’t know what they were. AND, I thought they were gonna eat me.” She eagerly reached out and petted the ray. “What does he eat anyways?” she asked Fluttershy.

“Oh… he’s a filter feeder, he eats ash and dust in the air. He doesn’t go hungry, as long as there’s a burning fire.” Fluttershy blushed. Even if all eyes were on Poncho, Fluttershy felt on the spot. Still, she smiled, happy to talk about the ray.

“I wonder if he’ll fly with me,” said Derpy. “Lemme see. If I…” With a single flap Derpy shot into the air. The ray quickly shot off my back to follow. “Woo-hoo!” Derpy called from above.

Fluttershy smiled as she watched Derpy and the ray soar off. “Rainbow Dash did that, too. It’s because Mantle Rays swim in schools. His instincts tell him to follow what’s moving.”

“You really like animals, huh?” I gave her a charming smile. One can always take the time to plant a seed of seduction.

Fluttershy blushed up to her ears. “Oh… I… um… yes.” She stared down at the snow beneath us. Her hooves absently twirling through the slush. She looked as though she was about to say something.

‘Is she trying to work up the courage to ask for a session?’ I examined her movements. Twice she almost moved to speak. She evaded eye contact. Whatever it was, she had something to say. ‘If I don’t make a move she never will. Ask her? No she’ll deny it. Tell her.’

“Fluttershy?”

She looked up in surprise. “Y-yes?” She was so nervous, scared even. Afraid of judgment. She needn’t worry about that from me.

“There’s something you want to ask me, isn’t there?”

Her eyes shot wide. “Oh, umm… no no… nothing at all.” A hoof nervously shot to her pocket. I heard the crinkle of paper.

‘She talked about letters last time you talked to her.’

“Is that a letter for me?”

“Oh, um…” Reluctantly, she revealed a letter. “…Umm… I…”

‘Help her, Guilty, she’s drowning.’ I raised a hoof. No words, just an open hoof. Taking my invitation, she quickly placed the envelope into my grasp. It was a worn thing. Written ages ago. It even had a stamp. She never worked up the nerve to send it.

I just smiled and pocketed it. ‘Hopefully the letter isn’t for a specific date. Oh, this is going to be awkward if it’s addressed for the past. Oh well, I can always write her back if that’s the case. At least now the conversation has been started.’

“S-sorry,” she mumbled.

Reassuring grin. “Don’t apologize. You’ve done nothing wrong.”

She peeked out from behind her mane. “O-okay.”

Above our head, Derpy enjoyed her flight with the majestic creature. It followed close behind her, matching her every move. “That thing’s gotten much healthier.”

“Oh yes, he’s come a long way since you found him. Still, he can’t get very far in this cold. He’ll have to wait till summer before he can go anywhere. Not to mention, Twilight says no one knows where all the Mantle Rays went. They’ve dropped off the face of Equestria.” A sad look graced her face. “I hope he finds his family again.”

Reassuring smile. “I’m sure he will.”

She smiled back shyly. Moments later, a streak of grey rocketed past us back into the tarp structure. “Oh dear, looks like he’s cold again. He doesn’t last too long outside in this weather.” And like that the ray had vanished, back inside his little dome.

Derpy landed beside us. “Yeah, he started slowing down after a bit. Still it was super fun. He’s so fast, Guilty.”

“Yeah, I remember from that day they were chasing you.” I stuck my tongue out at her.

“Ugh… I’m never gonna live that down, am I?”

“Nope.”

“Jerk.”

“That’s me.”

Derpy smiled and gave me a punch in the arm.

Fluttershy laughed at our antics, before stifling herself. “S-sorry, I didn’t mean to laugh.”

I shook my head. “It’s fine. We should probably get out of your hair. Thanks for having us.”

Derpy agreed. “Yeah, it was awesome. Thanks again, Fluttershy.”

“Of course. No problem.”

We waved goodbye and made our way back to town. I find that now, we walk so close together, usually with me under a wing. We’ve become so… coupley.

And wouldn’t you know it, just as we were leaving Fluttershy’s, somepony was there to bear witness to our coupley shenanigans.

Or rather, somezebra.

“Guilty and the mail mare, I almost didn’t see you there,” Zecora sang. She walked up the path along with her cart.

“Oh… Hi Zecora! You know Guilty?” asked Derpy.

“You are surprised at such a notion? Where did you think he got his potions?”

“Oooooooh,” responded Derpy.

“And that reminds me, Mr. Pleasure. I have for you quite a treasure.” From her cart she quickly produced a small white vial wrapped in a scroll. “I did promise you a gift, for my… burden you did lift.” She hoofed me the phial.

“Oh… thank you… I’d forgotten all about that.”

“It was not an easy brew, it took some time to make for you. There are instructions on the scroll. Now please, continue with your stroll. I have potions to sell to the mare that here dwells.”

“Oh… okay then…” I stared confused at the potion that had been thrust into my hoof.

“Bye, Zecora!” cried Derpy.

She waved goodbye as we walked past.

“Well, that was a fun little encounter.”

“Yeah, I haven’t talked to her in forever. I bought a cream from her a long time ago for a rash I got. It helped so much. I made her muffins as thanks.”

“Sounds like you,” I snarked.

“Shut up!” she shouted in mock hurt. “That was so much fun, Guilty! The ray was pretty cute up close, even if you can kinda see his ribs through his mouth. That part was actually pretty creepy.”

I nuzzled her slightly. “Well, it’s certainly an upgrade from before. When I found him he was covered in blood and dirt.”

“Aaaw,” Derpy responded. “He seems pretty healthy now. I mean, I’m not an expert or anything, but he was pretty lively.”

“Yeah, he was.”

“Well, I’m glad we did this. I’ve been wanting to see that thing forever.”

“Me, too. I kinda wanted to check in... see how the little guy was doing.”

Derpy nuzzled me aggressively. “Aaaww, Guilty cares about the little ray he saved.”

“Yeah well… I kinda feel responsible.” I leaned into her affectionate nuzzle. Our dynamic has changed… well... a lot in these past few weeks. We’re always so… close. I mean physically. We just sort of hang off of each other without even meaning to. It just sort of… comes naturally. We’ve been friends for so long. Now that we’re something more it’s… weird that it’s so easy.

Maybe… we’ve both wanted this for a long time. Maybe below the surface this is something we’ve wanted for longer than we knew. Then again, maybe it’s just because we know each other so well. It might just be that our relationship as it was wasn’t so far off from a romantic one. Further still, there’s always the notion that we’re just good for each other. Maybe we’re… just a perfect fit.

Whatever the case it’s still a little... scary, being in a relationship. This is all new territory for me, and I’m constantly worried I’m going to screw it up. So much of it comes so natural, but even more is so foreign. I’ve never had any trouble treating mares right. I know how to go out on a date, I know how to keep a mare entertained and interested. I know how to be a good partner… in bed or otherwise.

But I’ve never had a relationship that was… give and take. I find myself trying too hard, trying to always be the good boyfriend. However, in doing so, I deprive Derpy of the opportunity to be a good girlfriend.

We fight about that sometimes.

And fighting is new. I never fought with Derpy before; our relationship was too simple for it. But now… we fight sometimes… and it honestly freaks me out. I didn’t know I could get so mad at Derpy. Hell, I didn’t know I could get so mad at anyone.

But still, for all the weirdness and all the fighting... I really love being with Derpy. Now that I’m with her, the time we spend together is… so much more special than it was before. She was always my favorite client, but now… now It’s almost like I have… a whole new level of happiness that I didn’t know existed. A heretofore unknown elation.

I’m beginning to appreciate Crook’s attitude towards dating. He always had a girlfriend or two, and I always used to wonder why he bothered.

But now I get it. I get how it feels to be… well… loved.

At least, I assume I am.

We haven’t… said it or anything.

Not… not that we have to just yet. It hasn’t even been a month yet.

Now I’m worrying again.

Moving on!

Derpy had promised to take Dinky to a movie and I had a client, so we knew it was going to be a short date. I walked her back to town, said goodbye, and made my way home. Honestly, I was eager to get home. I wanted to tear open Fluttershy’s letter. There is often fun to be had with a new client.

The letter was positively covered in eraser marks. The nervous mare must’ve spent hours poring over this letter, because she seems to have second guessed every word on this paper alone. No telling how many sheets she went through attempting to get something she found acceptable.

It was… well… it was rather pathetic, full of “I’m sorrys” and “If it isn’t too much troubles”. Ultimately though, there was a date set. Friday. Not a particular Friday, just Friday. Thankfully, a free day for me. I just had to hope she would actually show up.

Fortunately for me, she did. Her quiet, first-timer knock was impressively soft. I actually almost missed it. I thought it was just my house settling.

When I opened the door, I was met with a mare hidden entirely behind her own mane. Her legs were shaking as she desperately tried to stand on her own four hooves. She seemed ready to flee at a moment’s notice. “H-hello,” she said in a voice as fragile as crystal.

‘Okay, Guilty, you are in full blown comfort-mode. This mare is about to pass out from fright.’

“My goodness, you’re shivering like crazy. Come in, come in. It’s warm inside.” I knew it wasn’t the cold making her shake, but better to seem ignorant than make her more uncomfortable.

“Th-th-thank you,” she spoke softly as she came inside.

“Have a seat. I was just about to put on some tea. Do you have a preference?”

As I took her coat I noticed she’d brought with her a small saddle bag. “No no, whatever you’re having will be fine.” She was determined not to be a bother.

‘Hmm. What’s the play? Insist she pick a tea? No that will just put her on the spot. Go with Chamomile, she doesn’t need anything else making her jittery. Just keep a level head, and an even tone. We just need to focus on not scaring her off.’ I put the kettle on, and returned to my nervous wreck of a client. ‘Reassuring speech time.’

Fluttershy’s face remained concealed behind her mane, avoiding eye contact at all cost. Yes, this was definitely the time to act. “You know Fluttershy… I can tell you’re nervous.”

“I’m sorry.” Her response was a swift as it was pathetic.

“No, Fluttershy, listen.” A single eye peeked through her part. “You don’t have anything to be nervous about.” Warm smile. Gentle tone. “The moment you walked in the door you began paying me for my time. This house, the tea… even me. It’s all yours until time is up. There’s nothing you can say or do that will make me upset. You can do whatever you like, and I won’t think any less of you for it. You’re worried something might go wrong, but… nothing can.”

“I… I guess…” Still unconvinced. Still shy.

‘This isn’t working. We need her to open up.’ I pondered for a moment. I was running through standard techniques of mine, when I realized I already had an in. ‘She likes animals. Just use that.’

“So, I was really happy to see the Ray the other day. Or, wait, I guess he has a name now.”

“Oh… yes… Pinkie named him. Oh dear, I already said that, didn’t I?” This mare couldn’t calm down if her life depended on it.

“So, I like the name. Is it because you can sort of wear him like big poncho?” I decided to just keep talking. If the conversation was dead in the middle of her comfort zone, she’d relax eventually.

She nodded. “Pinkie kept trying to put him on, but he would just fly away. I think she’s a little too energetic for him.”

“I know the feeling. I can barely keep up with her,” I said with a calculated chuckle.

“Y-yeah.” Her visage disappeared behind her mane once more.

‘Keep in animal centric, she’s too shy for anything else.’

“So, it must be interesting taking care of a magical creature like that. Do you have any other magical animals you take care of?”

“Oh, yes. There’s a Cockatrice who stops by every now and then…”

After that, Fluttershy managed to relax a little. We chatted over tea, I even got her to laugh a few times. She really is a passionate pony once you get to know her; she’s just got trouble speaking up about it. I spent a good 15 minutes getting the mare to warm up to me, more than I would’ve liked. But it was worth it. She actually answered when I asked my important question.

“So, Fluttershy. What can I do for you today?” I opted to skip the sultry I-wish-it-was-baritone.

“Oh, well… it’s… it’s kind of embarrassing.” She twiddled her hooves. “See… there’s this… what I mean is… I brought…” She took a deep breath. “One moment,” she rose, and walked to her saddle bag by the door. She returned carrying a large piece of equipment that I recognized as a polaroid camera. “G-guilty, W-w-would you t-take p-p-p-p-ictures of me.”

‘Interesting. Are they a gift for somepony special? A confidence booster of sorts? I mean, it’s certainly doable. But, what’s the motive?’

I’d done this sort of thing a couple times before. One mare wanted to give her husband a birthday present. Another just got off on having photos taken. Regardless of her reasons, I moved forward with the session. Gentle smile. Friendly tone. “Sure thing.”

She looked surprised. “R-really? That’s okay?”

“Of course.” Take camera. “But before we move forward, what kind of pictures did you have in mind?” Betray nothing. No innuendo. She’s too shy for it.

“Um… you know… p-porny pictures.” Her blush could make a tomato jealous.

I wanted to laugh at the word ‘porny’ but I stopped myself. “No problem.” Nothing but supportive and reassuring. “Do you want to start right away?”

“Oh… um… I guess so.” Her eyes searched the room. “Just right here?”

“No, we’ll use the bedroom.” Friendly smile. “Follow me.” I led Fluttershy into the “studio” as it were.

She seemed intrigued at the myriad chests and phials and bric-a-brac. “What a lovely room,” she said weakly.

“Yes, it’ll make a good studio don’t you think?”

“Oh… um… yes…” She dragged a hoof absently across my floor.

‘It’s like, the moment you make a move, she’s back to square one shyness.’ She was proving a tough nut to crack. ‘Maybe you should just take charge. She may respond well to instruction.’ I briefly considered this course of action before deciding against it. She may well comply, but she might not get what she wants. She might just acquiesce because it’s easier for her. I would have to stay gentle.

“So, how did you want to do this? I was thinking of just having you on the bed, but what do you think?” Appear eager for input, make sure she knows I want her to talk.

“Oh, um… that’s what I was thinking, too.” Not a lie. Good.

“Okay, hop on up, and we’ll get started.”

Fluttershy, now more anxious than ever, flew onto the bed with a couple beats of her wings. That said, it was a good anxious. An excited anxious. She wasn’t scared or worried; she just couldn’t believe this moment was finally happening. I’m sure she’d spent hours—perhaps even days—dwelling on this exact moment. How long had it been since she’d written that letter? How much time had she spent wanting this to happen? It was my duty to make sure that this little photo-shoot lived up to what had been built up in her head.

“So, first of all, how far… do you want these pictures to go?”

She didn’t seem sure how to answer that. “I, um… I’m not sure.”

Stay gentle. “Well… do you want them to be of… you know… your pussy?”

She blushed. “Uh-ummmm…” She swallowed hard. “M-maybe?”

“Okay, well, we can cross that bridge when we come to it, okay? If you're ever uncomfortable let me know, we’ll stop right away. Don’t let me do anything you don’t want.”

She relaxed slightly. “O-okay.”

My rules taken care of, I decided to begin our little photo shoot. “So to start, why don’t you just lie down? We’ll get a few shots of you in repose. Sound good?”

She seemed happy that I’d decided to start slow. Obliging, she lowered herself onto the bed.

As I looked through the viewfinder, I couldn’t help but frown. Her legs were curled next to her, almost desperately. Her mane once again obscured her face. I was going to have to gently pry her out of that shell. If I didn’t, she’d hardly be satisfied with the end result. These were not sexy pictures.

I took a breath. This was excruciating work. “Fluttershy, your mane is in your face.” I took a few deliberate steps toward her. “Can I get that for you?” The touch barrier is a big step for some ponies. The moment when you allow someone new to come in physical contact can be quite frightening. It’s especially true for mares, if you’ll pardon the stereotyping. As an escort, I’m something of an expert of making that transition almost seamless.

She nodded, of course, I’d asked in such an innocent way: “Let me fix your hair.” See, the question needs to be hidden inside something else. You can’t just come out and say “Hey, can I touch you?” It’s fucking creepy and weird. But, “Would you like a back rub?” That’s perfectly alright.

I moved my hoof forward slowly. I was literally avoiding sudden movements at this point. With a small brush, I revealed the mare’s frightened face. Amused smile. “Smile, Fluttershy. You’ve got a lovely smile, I’ve seen it. Now let’s show it to the camera.”

She gave a sour smile. “That’s awfully nice of you to say…”

Lo, a mare who does not realize that she’s attractive. What else is new? Thankfully, I have plenty of experience with this sort of thing. I may not be able to change her mind about herself, but I’ll at least be able to get her to open up long enough for a session. “Fluttershy, you’re a beautiful mare. I’m saying these things because they’re true. I won’t have you passing off my compliments as courtesy. I compliment you, because you’re worth complimenting.”

A small grin appeared on her face, and she nodded again. Her entire body began to relax. I stepped back again, and when I looked through the viewfinder, I found a picture worth taking.

A sultry-eyed, curvaceous, confident vixen, lounging on a cloud, stared hungrily into the camera. Where had this come from? I was just trying to get her to smile, but suddenly she took to the camera like a duck to water.

I took the shot. The photo paper slid out of the camera and onto the floor. “Wow, you’re… marvelously photogenic.”

“Oh um… thank you.” She blushed. “I actually… used to model… for a little while.”

“I believe it,” I replied instantly. She just showed up well on film, I couldn’t have been the first pony to notice. “Let’s get a few like this. It’s a good position for you.”

I snapped away at the feminine paragon in front of me. Her pose was impeccable. Her curves were accentuated, her gaze was smoldering. She was blushing, but that only made it sexy. I could not begin to fathom why she stopped modeling. After a few exposures I opted for a change of pose. “Let’s get a few from behind if that’s alright.”

Her blush amped up once more. “O-o-okay,” she said. She shifted her position, putting her rear end in center frame. She has a slim figure, but her ass is so toned. I couldn’t help but admire it. However, above that sexy well-toned ass, was a nervous face staring back at me. ‘Is she going to need a confidence boost after every shot? Well for now, let’s just get that nervous face out of frame.’

Confident smile. “Why don’t you stare off into the distance? It adds to the mystique.”

“Um… sure...” she turned her head. “Like this?” Suddenly that goddess of photography returned.

“Perfect. Don’t move.” I clicked as quickly as the Polaroid would allow.

It was exquisite. Her back-turned gaze was barely visible. It provided just a fleeting recognition of the viewer. “Yes, I know you’re there. What of it?” she seemed to say. She was an icy temptress: Cold and distant, but powerfully attractive.

I could feel myself getting worked up. I was excited. I could feel my face getting warm and my pants getting tight. I wanted her. She was an exceptional mare, and I wanted to pleasure her. To serve her. To know her physically.

I pushed my desires down. Now was not the time.

I took a deep breath to calm myself. “Let’s switch it up again. Something a little more… playful.”

“H-how do you mean?”

“Here… try this.” Breaking the touch barrier early was already bearing fruit. My hooves guided her body into a new position. I delicately moved her onto her back, hind legs up in the air. I then guided her front hooves downward, concealing her marehood.

“Oh… oh my,” she said.

“Is this okay?” Ever gentle. Ever caring. “It’s very sexy, you know?”

“O-okay,” despite her nerves, she seemed to be enjoying herself.

“Now, stick your tongue out at me.”

She wordlessly obliged. Once again, she was stunning. A naughty little mare, teasing the camera, her wonderful prize hidden cattily. Her playful grin, her dainty hooves, she was breathtakingly cute.

I took four shots of the impish Fluttershy before coming to a realization.

I had no idea how many pictures I would be able to take. “Fluttershy, how many exposures were loaded into this camera?”

She perked up. She’d sort of fallen into a trance as I’d been taking pictures. “Oh, um… thirty, I think.”

I looked down and counted the photos I’d taken, strewn across the floor. Some were beginning to develop. Ten in total. That left twenty pictures to get more and more of Fluttershy on film. I decided to accelerate my progress. “Ready to take it a step further? This will be a big one.”

“Y-yes,” she said with determination.

“Can you… move your hooves for me?”

She looked shocked. “Oh… oh, my…”

Too far. Backpedal. “You absolutely don’t have to. We can keep things a little more tame.”

“I… um… I…” She was internally debating it. I could tell she wanted to take things further, but she was scared to.

I decided to play it safe and simply waited for her to decide.

After several tense seconds, she moved the hooves covering herself. She was still being covered, but the bottoms of her lips were peeking out. She was wet, impressively so. Her juices were glistening at her entrance. She was loving this. “I-is this enough?”

“That’s fine.” I lifted the camera once again. Her face now a mask of pure desire, a perfect “come-hither.” Her whole body was screaming to be taken. She was a veritable queen of desire. I took three shots. Her nethers pulsed with each shutter snap, her lips grew redder and wetter with each picture taken. Even as her arousal began to build, her exquisite expression never faltered.

“Was… that okay?” I didn’t really need to ask, this was bliss for her.

She nodded. “What next?” Now she was eager. Too hot and bothered to be shy, it would seem.

‘Well, she’s asking. Time to get creative.’

“Why don’t we do this? Sit up and spread your hind legs, and bring your forehooves down In front of you.” She shifted her position. For an instant between poses I had an unobstructed view of her sopping pussy.

Excellence.

Once she was in position, she instinctively stuck out her tongue again. She’d gone back to her impish little character, a playful little mare wanting to tease the viewer. Two more pictures. ‘She manages to change character to match the pose without effort. Sex Goddess. Playful tease. Icy queen. She’s a natural.’

“Okay, how about this? Why don’t we get a few of you standing?”

“O-okay.” She slid off the bed. “How… how should I stand?”

“Okay so, turn away from me. Okay now… bend your… well, your ass a little more toward me. Now, turn almost away, just keep one eye on the camera. Perfect, now make a serious face. Stupendous.” She followed my instruction to the letter. Her pose was perfect, statuesque. “Now… if you’re okay with it… why don’t you… raise your tail?”

Only a moment’s hesitation. She raised her tail high, glorious marehood in full unobstructed view. It was perfect. Chubby wet little lips on display. Her icy visage. I took three pictures. She shifted slightly, and her lips parted a little bit, revealing her pink moist entrance. I took two more.

‘Ten left. Make them count.’

“So… are there any particular poses you wanted to do? Anything strike your fancy?”

“I kinda wanna… do one thing,” she admitted. She moved back to the bed. Before I could ask what she meant, she laid on her back, and reached down between her legs. Rather than covering herself, though, she spread herself wide, exposing the deepest parts of herself. Her breath grew labored. Her blush reached new heights. "I-i-is this okay?” she managed to ask.

“It’s exquisite,” I replied. ‘Fuck making them count. Just take ten of these.’

I snapped and snapped away. With each click of the shutter, Fluttershy’s back arched more and more. After three she actually began to drip onto the sheets. After seven I could see her inner walls beginning to pulse. Her model’s gaze began to falter. At ten she actually came. Her entire body shook for a single moment. It wasn’t a grand or glorious climax, just a tiny little orgasm.

“Having fun there?” I asked, hoping for a positive response. I did not get one. In retrospect it was a bad move. I should’ve played dumb.

“Oh… Oh my goodness.” She looked mortified. “I’m… I’m… eep.” She dove behind her mane. She grabbed a nearby pillow in an attempt to hide herself. She was in full blown panic mode.

‘Your client is freaking out. Engage emergency protocol! Extra gentle? No, it hasn’t produced results as good as I would’ve liked, she’s still nervous after a while of that. Downplay it.’

Casual tone. “Don’t sweat it… that ends up happening a lot of the time.”

“W-w-what do you mean?” she peeked out from behind her pillow.

“Fluttershy, I’m a whore. People usually come here to get off. That’s what I do.” I started gathering up the pictures that were taken. Acting like nothing happened was also a valid strategy. “Come on. Let’s have a look at these. I think there are some really good ones in here.”

She, cautiously, followed me out of the bedroom, and joined me at the table.

We spent the next few minutes looking over the photos. A distraction was the perfect thing to get Fluttershy to stop panicking. “These came out pretty good, don’t you think?”

She nodded. “I… I look sexy.” The smiled, blushing.

“You do. And I’m glad you like them, I was worried you would think they went too far.”

“N-no… they’re perfect… well, most of them.” She did her best to avoid looking at all the pictures where she was drunk with pleasure.

“What are they for, if you don’t mind me asking?”

“I… I was going to give them to somepony,” she admitted.

“Oh yeah? Your special somepony?”

“He’s… well, not yet… I mean… I hope he will be someday.”

Red flag.

“Fluttershy, are you going to use these to… profess your love for somepony?” Such a bold move struck me as being beyond Fluttershy.

“I… I wanted to at one point. Rarity talked me out of it. She said it would send the wrong message.” She admired the photos again. “She was right, I think. But, I always wanted to… to do it. To take… naughty pictures. I could always give them to him some other time. They would make a good Hearts and Hooves Day gift, wouldn’t they?”

I felt relieved. If Fluttershy embarrassed herself like that, I might’ve taken some flak. “I think they would.”

She smiled. “More than anything though… I… I wanted to know that… that I could… could do it.”

“Do what?”

“Be… be sexy for somepony.” She smiled. “I… I really can, can’t I?” She admired the pictures further.

“Well you weren’t a model for nothing.” I met her gaze. “Why did you quit? You’re very photogenic.”

She let out a heavy sigh. “It was… scary. So many eyes staring at me. I was… always so nervous. I hated it.”

A waste of talent, in my humble opinion. You get over that sort of thing if you try hard enough. I know I got used to something like that. Something even harder, I would deign to say. Still, I chose my path, and Fluttershy chose hers.

She regarded the photos once more. “I hope he likes them… if I ever get give them to him, that is.” She began to pout. “I don’t know the first thing about relationships.”

“Me neither,” I almost said. It was my de facto response. My old, practiced “I know what you mean” line.

But… but that wasn’t true anymore. I had a little over a month of relationship experience under my belt. Derpy and I were… dating. I understood infinitely more about relationships than I had a month ago. I’m no longer the unable to help in this department. There’s… some wisdom I can offer.

“I don’t know much… but I do know some.”

She looked up at me. “You… you’re dating Mrs. Hooves aren’t you?”

I hesitated, but ultimately nodded. “For about a month now.” This was okay right? Derpy told me I could tell ponies. She said people mostly already knew about us. “It’s my first real relationship.”

“Wow... I thought I was the only one who hadn’t been with anypony for this long.”

“Yeah, I felt kinda the same.”

She worked up the courage to ask a question. “How… How did it happen?”

“You mean, how did we end up together?”

She nodded. “How does that sort of thing just… happen?”

“Well…” I hadn’t told anypony this yet. “… It’s actually kind of silly.” I cleared my throat. “My first date with Derpy… wasn’t a real date. It was a practice date, Derpy felt like she was a little rusty, so we went out to dinner.” I smiled as a reminisced. “At the end of the evening I asked if she wanted to try again for real.”

Fluttershy tittered. “That’s really sweet.”

“She punched me in the chest,” I stated, much to my client’s surprise.

“W-what?!”

“When I asked. She punched me square in the chest… like, a lot.” I rubbed the long healed bruise. “Apparently somewhere down the line, I’d mentioned that escorts aren’t supposed to date clients. She got mad that I’d lied to her.”

“You… you aren’t supposed to date clients?” she inquired.

“Well… that was an old rule. Back from when I worked in a stable. But… well… I fell for Derpy. Some part of me decided that that rule wasn’t going to stand in my way.”

“That’s still kinda sweet… even if she did hit you. What happened after that, though?”

“Well, after she calmed down, she said she’d be willing to try a real date. So we did… and things just kind of went from there.” Fluttershy hung on my every word. “We make an effort. Our schedules don’t always match up. We fight sometimes. But we’re still together. It’s only been a month, but… I dunno… It’s…”

I realized I didn’t have a word for how I felt. There’s been so much change since I started dating Derpy. Changes with us. Changes with me. I find myself always thinking about her, and not just in the day-dreamy sort of way. Every move I make, every decision, it now all takes Derpy into account. I’m forever planning around her, it’s exhausting, but I somehow love it. It’s like we’re on a team, Derpy and Guilty against the world. And I’ve learned so much about her. Not her hobbies or her past or anything like that, but… how she looks when she’s mad, what sets her off, what pet names she likes to be called. Things that nopony else really knows about her. Things I don’t really know about anypony else.

There’s so so so much to know about somepony and the scariest part of it is that Derpy has probably started noticing the same things about me. I never thought one could know this much about somepony else. And now, there’s somepony who knows that much about me. I’ve never been this close to anypony before. Not to Close. Not to Ms. Smile. Not to Sunny. This is… love. Real romantic love, and it’s…

“… a trip,” I finally said.

“Is… is that a good thing?” Fluttershy asked.

“Yeah… it’s a good thing.” I glanced at the clock. “Well, your hour is almost up. Were you… planning on staying longer?”

“N-no, I... I think I should get home.” She gathered up her photos. “Um… thank you, G-g-guilty. It was… it was very… nice… today.” She reached into her bags and produced my fee. “M-m-m-maybe I-I’ll finally be able to… to a-ask him out. After what you told me, I… I kind of feel like I can.”

“Well… I hope things work out.”

“Thank you Guilty... Umm… Bye.”

“Bye,” I replied. And with that she left. Leaving only a wrinkled bedspread and the scent of her arousal. I hope things work out well for her and her mystery stallion.

It’s probably Big Macintosh.

Oh, I forgot to write about that potion Zecora gave me. It actually sounds pretty awesome. According to the label it’s called “Thunder’s kiss.” I’m supposed to apply a single drop to… wherever… and the affected skin should “provide pleasure unmatched.” I’m gonna try it out with Derpy at some point. It should be fun.

Author's Notes:

Thanks as always to Blackskulls, aquapunkchick, JakeTheArmyGuy, and coandco. WIthout them this fic would be far less amazing.

I'm fairly pleased with this chapter, I feel pretty good about Fluttershy's characterization.

it was kinda rough pumping this chapter out, my vacation was a little busier than I was expecting, and I barely got the first draft done before school started. Time kind of flies when you're running around doing paperwork.

Still, hopefully the next chapter won't be as long. It's going to be a big one.