Honest Woman

Original prompt from the first thread:
>"I-I'm so sorry I lied to you anon, I was just so scared you'd reject me since I wasn't actually a girl"
>"Please anon, don't go, w-we can make it work right? I could still be your 'girl'friend, no one else would need to know the truth"

Honest Woman
by some person on the internet, possibly TheSymbolDynamic, but who can really say

After months of meeting for coffee on the weekends, getting together after school to study at the library and taking baby steps with your relationship you finally had your first proper date with Sunset Shimmer. At long last it was official. You had kissed before, snuggled up on your couch a few times, but Sunset kept insisting that you weren't officially a couple unless you went on dates.

“It doesn't have to be something big, but I don't think you can say we're dating unless we, you know... date.”

You saved up for a couple of weeks to show her a good time, and at long last your patience had paid off. You went for dinner at her favorite restaurant, then a private showing of a movie, some romantic comedy that made her laugh in that way you couldn't help loving, and finally a walk through the nearby nature preserve. The sun had set hours ago, and the park was probably closed, but neither of you particularly minded that you might be trespassing. There was something magical about being alone together in the woods at night. It was like being in another world, away from cares and worries and other people.

You smiled, looking up at the night sky and the occasional firefly drifting lazily through the air above you. Slowly you turned your gaze toward Sunset, your smile widening. She was laying there in her red dress and reclining on the blanket you brought with you, her eyes fixed on the full moon, looking thoughtful. Slowly,  carefully, you worked your hand closer to hers across the blanket, slipping it around hers. She looked over at you, blushing a bit, and grinned, pulling your hand towards her face and toying with your fingers.

“This has been the best night of my life, Anon... I mean that.”

She slowly brought your hand to her lips and kissed your palm, blushing a bit brighter, and you could feel the color rising in your own cheeks. Her eyes fell upon yours, and you could tell that she was torn about something. She sat up slowly, bringing her knees to her chest.

“I... Before we go any further with this, I have... some things to tell you. I... I'll start with... I'll start slow, and... save the big one for the end...”

You nodded, but something about how she said that made the air around you feel a little colder all of a sudden.

“The reason why we never went to my house is because... because I don't have one. My parents... threw me out. I've been staying with one of my friends ever since. That's... also why I haven't introduced you to them yet...”

You took a slow breath as you processed that. She had met your folks already, and they had gotten along great. You couldn't imagine what sort of monsters would throw out such a kind and caring girl, and you felt a sort of protective anger well up inside you. Sunset looked down, and you waited for her to continue, but she seemed hesitant.

“Sunset, whatever it is you need to tell me, it's fine. You could be an alien assassin from... from Mercury or something. It wouldn't change how I feel. And if you don't feel comfortable telling me, then it can wait. As long as you're safe, and... not going anywhere...”

Sunset's eyes widened and she looked right at you, almost panicked.

“Anon, I'm not going anywhere, I promise! I... I'm just scared that after I tell you about this... you'll want me gone.”

You nodded slowly, bracing yourself for the worst thing you could think of.

“You've been... seeing someone else...?”

Sunset shook her head vigorously, looking a bit hurt at you words, but she pressed on.

“When I was little, I had an uncle. He wasn't a blood relative or anything, he was my dad's best friend, but he made me call him uncle... He used to come over all the time and babysit me when my parents were away.”

A small smile formed on her lips, but you could see her eyes watering, a pained expression slowly settling onto her face as her gaze drifted away from yours once more.

“He used to... play dress up with me. We'd wrestle and play house. He'd be the daddy, and I'd be the mommy...”

You tensed. She didn't need to tell you any more than that for you to understand where this was going.

“My parents found out eventually, he wasn't careful... I would walk funny after he left, and... the stains on the sheets... They got him arrested and thrown in jail...”

You pulled her into a tight embrace, and heard her sob against your chest as you cradled her body against your own.

“I... I think I get what you're trying to tell me, Sunset... And... whatever he did to you, it's in the past. You aren't dirty or impure or broken, or whatever you think he made you. I still... I still love you, even knowing that.”

Sunset pushed you back a bit, her eyes shut tight, tears leaving mascara trails down her cheeks.

“I am broken! He... he broke me, Anon...”

She shivered, gripping your shirt as she tried to steady herself.

“I... I don't know if it's what he did, or if it was always a part of me... Or both... Maybe he just set it off... But I'm... I'm not...”

You sat there dumbfounded, trying to piece together how to comfort her, when she opened her mouth once more.

“I'm not a girl... Not physically... I was born a boy, Anon... I'm not... who you thought I was...”

You took a slow breath and swallowed, staring at her. Sunset. Your Sunset. The girl you had spent weeks pining for and months wooing, who was finally going steady with you, was transsexual. She was a girl in a boy's body. Somehow that didn't bother you as much as you thought it should have, didn't resonate in your head as the big issue. It wasn't that it wasn't a shock, but...

“Anon...?”

No, the thing that bothered you was the lie. Sunset was Sunset, no matter what was between his... her legs. But she had lied to you, hadn't been up front about something important. What if it had disgusted you? What if it had reviled you enough to tell everyone about it? That thought scared you. It had been a sign of trust to tell you, you realized, something she had probably fretted over and feared all this time. But relationships were built on honesty, and she had been deceiving you all this time.

“Sunset... Why didn't you tell me before now?”

Her hands released your shirt and fell at her sides before she hugged her knees to her chest.

"I-I'm so sorry I lied to you Anon, I was just so scared you'd reject me since I wasn't actually a girl. You were the first guy to really pay me any attention, not just catcall me or compliment my ass. I didn't want to lose you by driving you away..."

After a pause to gether your thoughts you slowly rose to your feet, brushing yourself off, and you could hear her whimpering as she looked up at you. You felt an ache in your chest from the look of grief and guilt on her face, resting her hands on the ground as she tried to stand up without ruining her dress.

"Please Anon, don't go, w-we can make it work, right? I could still be your 'girl'friend, no one else would need to know the truth about me. Nothing has to change..."

You grabbed her hands and pulled her to her feet, a little roughly so she would fall against your chest, and she let out a soft squeak of surprise. You slipped one arm around her waist to keep her close while cupping her chin with your free hand and forcing her to look at you.

“Sunset. Do you love me?”

Sunset nodded, rubbing her eyes, and you couldn't help smiling at the way her smudged makeup made her look adorably scruffy.

“Say it then.”

Sunset hesitated, looking unsure of your intent, before smiling hopefully.

“I love you, Anon...”

You nodded, releasing your hold on her.

“I have a favor to ask then. Take off your dress.”

Sunset turned bright red, stumbling back a few steps.

“What...?”

You looked off to the side before returning your gaze to her.

“I said take off your dress. Lovers don't keep secrets from each other. So... no more secrets. You want to make this work, so... prove there aren't any other secrets. Trust me with what you've been hiding from everyone. There's no one around to see, and... I want to see you. If you're fine with that.”

You shifted a bit awkwardly and scratched your head.

“I'm trying to think of another way to punish you for lying to me that lets me prove that I accept you how you are and I'm coming up short. Cut me some slack.”

Sunset rubbed her arm timidly, glancing at the darkened woods all around you, before giving a feeble nod and reaching behind herself. She unzipped her dress and carefully shimmied her way out of the fabric. She was wearing a strapless bra, and you could tell from where you stood it wasn't stuffed. A little padded, perhaps, but her chest was far from flat.

She tensed as she slide the dress down her hips, glancing at you briefly as she bared her panties, and her secret. The bulge was obvious enough, but you couldn't help the feeling that the situation was exciting her, making the tent in her underwear that much more noticeable. She stepped out of her dress, covering her crotch with both hands and fidgeting, and you gave her a small nod of approval as you took in the view.

“Alright...”

You felt an urge, and the words left your lips before you thought too hard about them.

“...Turn around for me, Sunset. Slowly.”

Sunset's rosy cheeks turned scarlet and she twirled for you, looking over her shoulder as she turned away and meeting your eyes as she spun back toward you. You smiled a bit, and she seemed to relax slightly.

“I... Do I look alright to you, Anon? A-Am I... pretty?”

You shrugged halfheartedly, just to watch her confidence waver for an instant, before smiling.

“I wouldn't say pretty. I mean, you've always been beautiful. Even half-naked, with your makeup smudged from crying, you're gorgeous, Sunset. And having different parts between your legs than what I expected... That doesn't change that fact.”

Sunset blushed, hugging herself tightly and smiling, and you noticed her bulge had swelled slightly.

“A-Anon...”

You advanced on her, pulling her close once more, and she melted into the embrace, burying her face against your chest. She was shaking, either from happiness or embarrassment, or perhaps from being underdressed for the weather, and you held her until she began to calm down. You brushed a stray strand of hair behind her ear when she looked up at you, and leaned in to plant a kiss on her lips when you spotted a light out of the corner of your eye.

“Park ranger, I think...”

Sunset spun around and stared at the light, before scrambling for her dress. You grabbed the blanket and flung it around her, before scooping her up and hoisting her over your shoulder, running with her towards the park's exit. You were glad that she chose open-toed shoes every time her feet bounced against your stomach, though Sunset's hushed protests left you pretty sure she didn't quite appreciate being manhandled like this.

When you got to your car you set her down gently and unlocked the door, motioning for her to get inside while you kept watch. She slipped in to dress, and you kept your eyes on the park. The ranger didn't seem to have followed you, assuming he even spotted you at all. You felt a tap on your shoulder, and turned around to see Sunset Shimmer, dressed up once more, her makeup neatened and her hair brushed tidily once more.

“Um, Anon... About what you said back there...”

You shook your head, smiling and pulling her in for a soft kiss.

“Save it, Sunset. For now... let's just go to my place. My parents are out. I... kind of intended to bring you home to be alone with you after our date. At the very least, it gives us a place to talk.”

Sunset blushed, and nodded a little.

“I... alright...”

You nodded a little and got into the car while Sunset moved up to the passenger seat, and you drove off with her toward your house. She clung to your arm the whole way, like you might just vanish if she let go, and twice you felt her gently nuzzling your shoulder. As you pulled into your driveway you had to practically pry your arm free so you could park, and she released you reluctantly. You helped her out of the car and to the door, letting her latch onto you once more, and led her up the front steps.

“Here's where I planned on kissing you, taking you into my arms and holding you close...”

Sunset nodded a little bit, turning toward you as your hand moved to her cheek. She closed her eyes, parting her lips slightly in anticipation, and you kissed her firmly, pressing her up against the door a bit. You fumbled for your key and unlocked the door, and Sunset turned the knob slowly, easing her way inside without breaking the kiss. She let you push her through the doorway and into the hall as you shut the door behind yourself. You broke the kiss, a little breathless, and smiled at her.

“I was going to lead you down into the basement, make my intentions clear to you, and then head to the kitchen to get us some drinks. Nothing strong, just enough for us to loosen up.”

Sunset blushed profusely, and you gently gestured to the stairs.

“If you go down those stairs, Sunset, then we're going to make love. I'm going to take you, as you are, and make you mine, because I love you and desire you. But you can always say no, at any point.”

Sunset nodded and bit her lip, and you turned to walk away before she could respond. You heard the sound of her heels clicking against the steps and smiled, mixing up some weak screwdrivers, enough to taste a hint of alcohol without it hitting hard. You didn't know if Sunset was a lightweight or not, and didn't want to find out, but you did want to give her every excuse to relax and open up.

You were pretty sure that things wouldn't go too far after what she said about her uncle, and you weren't exactly sure that you'd even be able to get hard for her considering what was between her legs. You loved her, you were still sure of that much, but you had never really thought about sex with a man before, pretty and curvy or not. Part of you hoped that you wouldn't have to learn whether or not her body still excited you the same way.

You grabbed a tray, a pair of coasters, and the rose you had set in the fridge, arranging the drinks with care and carrying them down to the basement with the rose nestled between them. It was as close as you could get to elegant, but you liked to think it was the thought that counted. The basement was dark, and you almost dropped the tray while trying to get the lights, but the sound of Sunset's voice stopped you.

“D-Don't. Not yet... I... Leave the lights off for now...”

You paused, then nodded, and walked slowly into the darkness, feeling your way across the floor using your foot and making your way towards where you heard her voice coming from. You felt the tray shift in your grasp as she took it from you, and you could vaguely see the outline of her body where she lay on the couch as your eyes began to adjust. You could see her dress folded neatly on the floor, along with her shoes, as well as the blanket she had draped over herself. You were pretty sure she was smiling nervously, setting the tray down on the coffee table.

“So... drinks...?”

You nodded slightly and felt around for the rose, offering it to her. She took it and made room for you on the couch, hugging the rose to her chest as you settled next to her and reached for the drinks. You felt her hands on your own, guiding you towards one of the glasses before she took the other and sipped timidly. You took a sip from your own glass, and slowly reached your hand over to her, slipping an arm around her shoulders. Slowly Sunset nestled herself against your side, drinking her screwdriver slowly and cradling the glass with both hands, the rose dangling between her fingers.

“So...”

Sunset glanced at you.

“You were going to make love to me...?”

You nodded and chuckled a bit to try to lighten the mood, swirling the contents of your glass.

“Yeah... A perfect night out, us officially becoming a couple... I was planning to take you down here to be alone, private, away from the rest of the world. The drinks were so you'd have an excuse to let go of your inhibitions, not to get you drunk, just so you know. I guess I just wanted you to feel free to be yourself.”

Sunset rested the rose across the top of her glass and smiled at you, poking your nose with the stem as she set her glass back onto the tray.

“And you were going to be romantic...? All... lovey-dovey?”

You gave her a soft squeeze, leaning in a bit.

“Of course. Because I love you.”

Sunset closed her eyes, and you pulled her just a bit closer as you kissed her, slipping a hand under the blanket and resting it at the small of her back. She shivered at the contact, turning her body toward yours and climbing onto your lap, scooting close and letting the blanket pool around her waist.

“I love you too, Anon...”

You nodded moved your hands to her sides, sliding them up toward her chest.

“I want to show you how much I love you, Sunset...”

Sunset nodded, her hands slipping loosely around yours as you began to gently knead her breasts, earning a soft gasp from her. She shifted her hips slightly, turning to straddle you and resting her hands on your shoulders, kissing you gently. You pushed her bra up slowly, brushing your fingertips over her nipples and pushing your tongue into her mouth as she moaned.

She slid her hands down to your waist, and you reached behind her, tugging the clasp of her bra loose and easing the straps off her shoulders. She stiffened a bit, and you lowered it down her arms delicately, taking your time to give her time to stop you. She covered herself with one arm as you tossed her bra toward her dress, and she smiled gently, exposing her breasts to you bit by bit.

“Wh-What do you think...?”

You gently cupped her breasts, smiling at her as you gave each a firm squeeze. They felt natural, and you liked the way they seemed to fit perfectly against your hands.

“They're lovely.”

She nodded and kissed you softly.

“It... It feels nice...”

You moved your fingers toward her nipples, brushing against the stiffening nubs, and Sunset moaned against your lips. She slipped her hands under your shirt before sliding them down your stomach and working the button on your pants loose. Her hands trembled, and you kissed her cheek, leaning in to whisper to her.

“Don't force yourself... If you don't want to, we don't have to...”

Sunset shook her head, sliding your zipper down and giving you a nervous smile. You hadn't noticed just how tight your pants felt until she let your erection spring free, and she giggled softly as she touched your hardness through your underwear, sounding relieved.

“I want to... to do this with you... I want to be made love to... by the person I care about... I'm nervous because... because I'm scared you'll be disgusted by my body when you see all of me...”

You nodded and rested your hands on her hips.

“Then let's get that out of the way... Turn around for a second.”

She blushed and turned, and when you rested your hands on her thighs, she parted them, letting you spread her legs. You rubbed up and down her legs, gliding the tips of your fingers along the smooth skin of her inner thigh, her rear grinding against your cock firmly as she squirmed. You took hold of her panties and pulled them down, and she gripped your thighs tightly as you removed her last article of clothing, spreading her legs apart once more and looking over her shoulder at you, a terrified expression on her face as she bared herself to you, waiting for your judgment.

You hadn't put much thought into what Sunset's cock might have looked like, but now that it was in plain view it was exactly as you would have expected; small, hairless and almost cute, her shaft rigid. You moved your hand to it slowly, stroking it lightly and kissing her gently. She whimpered, bucking her hips softly against your hand, and you slid your free hand to her chest, toying with her nipple once more.

“You don't disgust me, Sunset. Honest.”

Sunset let out a moan and nodded, panting and guiding your hand towards her rear.

“H-Here... Y-You... proved your point... But that doesn't stop me feeling ashamed of it... Even if it feels good, it's still a... reminder of what I'm not...”

You nodded a bit and licked a pair of your fingers, resting them against her tight pucker and rocking them back and forth, slowly easing them inside her. She leaned back against you, holding your arm loosely and gasping with each push deeper inside.

“How... How much preparation do you need...?”

Sunset did her best to look up at you, panting lightly.

“I... I can... handle it... J-Just let me get you slick first...”

You smiled gently and withdrew your fingers, tugging down your pants while Sunset moved beside you on the couch and rested her head on your thigh. She slid your underwear down, exposing your length and examining it, cheeks reddening as she admired you. She started stroking slowly from base to tip and back, before wrapping her lips around the head and suckling softly, licking back and forth in light circles.

“It's... bigger than I thought, Anon...”

You moved your hand back to her ass, toying with her a little as she sucked.

“Thanks for the compliment, I think...”

She kissed the underside of your cock and looked up at you, her voice wavering.

“I-I only really have a handful of others to compare it to, and... none of them were this big...”

You nodded and stroked her hair gently while working your fingers back into her rear.

“I want to make you forget him, Sunset... He made something special into something that hurt you, made you feel broken when you're not...”

Sunset lapped at your cock, closing her eyes and taking you into her mouth, letting out soft moans around your shaft as she bobbed her head. You couldn't help letting out a groan of your own, moving your fingers in time with her motions, curling them slightly inside her and exploring her body, trying to find what felt best for her and focusing on those places. Sunset took a deep breath when you slid your fingers all the way inside, and leaned forward, sliding her lips all the way to the base with a muffled moan before pulling back with a soft “pop”.

“A-Anon... Be more careful back there... It feels good, but...”

You nodded, sliding your fingers out slowly.

“Sorry... Was it too rough?”

She shook her head, stroking you with one hand.

“N-No, just... If you had gone rougher, it would have been a problem... If we had lube it would be easier.”

You made a mental note to pick some up, and smiled at her.

“We'll go at whatever pace you need, alright? I don't want you to endure this. I want you to enjoy it.”

Sunset returned your smile and nodded, focusing on your cock once more, stroking it and covering every inch with her tongue. You tugged your shirt up and off, and Sunset slowly slid a hand along your stomach, gazing up at you with longing before pulling away slightly.

“This should be good enough... A-And you'll slow down if I need you to... right?”

You nodded, and Sunset slowly moved onto her back, blushing brightly as she parted her legs and you moved over her. You reached down and stroked her thigh while she covered her crotch with one hand, using the other to line you up with her entrance and guide you in. You both moaned as the head eased inside, and you felt her shake beneath you as you rocked your hips, each time driving yourself a little bit deeper inside her. Sunset gasped with each movement, her voice a series of soft, ragged moans. She was tight around you, her inner walls gripping every inch of you as you slid all the way inside.

“Anon... It... It's stretching me... I can feel you inside me... It's hitting deep inside...”

She sniffled and smiled, hugging you tightly.

“I was worried that... that it wouldn't feel good after what happened, but... I've never felt so amazing in my life... I love you, Anon...”

You kissed her tenderly, grinding against her softly and trying to move as little inside her as you could manage.

“I love you too, Sunset...”

You nibbled your way down her neck, biting delicately as you made your way to her chest and took her nipple into your mouth. You suckled softly, delighting in the little noises of pleasure that escaped her as you started to thrust into her. You drew your hips back and drove your cock deep inside her, and were rewarded with a squeal from Sunset. You repeated the motion, gazing at her face as she writhed and squirmed, raising her hips to meet yours.

You slid your hands underneath her, resting your body against hers and assaulting her neck as you pulled her hips against your own, speeding up bit by bit and listening to the sound of her moans. You had never heard anything quite so lovely before as the sound of Sunset whimpering and quietly pleading for you to keep going, to never stop. You felt her hand on your back, her nails lightly scraping against your skin as she hooked her legs around you, locking her ankles together behind your hips.

“Y-You can... cum inside me, Anon... I... I want to feel your warmth inside me...”

You nodded and gently bit her earlobe as you started driving yourself towards your orgasm, thrusting faster and panting almost in time with her, trying to angle your thrusts to hit that sensitive spot inside her. Her eyes widened, and she moaned loudly in response, keeping her body still and letting you pound into her. You felt her dig her nails in just a bit, and from the way she suddenly tensed and arched her back under you, you could tell she was almost there.

“Sunset...!”

She gazed up at you, moaning and stammering out your name before she went rigid, screaming and clenching around your shaft as she came.

“Anon!”

You bucked into her tightening hole, thrusting quickly before slamming your hips against hers one last time and letting yourself go inside her, grinding softly as your balls tensed and your cock throbbed. You held her tightly to your chest, one hand cradling her head to your shoulder and the other around her waist, moving gently with her as you both came down from the rush. Her hands stroked at your back, her legs going limp, and you pressed your lips to her forehead.

“I love you, Sunset.”

Sunset nodded against you.

“I love you too, Anon... I love you so much...”

You grabbed the blanket and draped it over yourself, carefully withdrawing from her and moving to her side. She whimpered a bit as you pulled out, swiftly curling up at your side with her head on your chest, clinging to you tightly. You mused that you could get used to all this intimate contact, and gave her a soft squeeze.

“Now, as for your punishment for lying to me...”

Sunset stirred a little, giving you a confused look, and you simply smiled.

“I want honesty. If I ask a question, you have to answer it. You hid something important, so it's about time you spill the beans.”

Sunset nodded a bit.

“I don't have anything else that I would want to hide from you, Anon... You can ask me anything... I trust you, completely...”

You ran a hand through her hair and nodded, and you enjoyed the sudden blush and excited smile on her face as you asked your first question.

“Wanna do that again after a quick stop at the store for lube and maybe a quick shower?”

She nodded, and you rolled on top of her once more with a smirk, ready to make an honest woman out of her.