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A journey of firsts

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Regina doesn’t know anything about pleasure until Daniel kisses her. His lips are warm and soft on hers and Regina closes her eyes and enjoys the feeling. When he pulls away, she is beaming at him. He laughs and wraps her in his arms, and Regina rests her head against his chest where she can hear his steady heartbeat. She can’t stop smiling the rest of the day, earning inquisitive glances from her mother.

Daniel is the first person Regina kisses. He’s the first she holds hands with, the first she cuddles with and the first she loves. When Daniel proposes, Regina becomes the happiest girl in the world. She imagines running away with him and starting a family of her own. She imagines waking up in his arms, kissing him without worrying if anyone sees them, starting a family with him. And she can’t wait for it.

It’s the day before Snow will tell her secret and her life as she knows it will be over when she goes on a ride with Daniel. They stop at their favorite place for a romantic picnic. Regina feels happy and hopeful. Their future is in reach, just waiting for them, and Daniel is smiling at her so warmly, Regina can’t help but kiss him again. Their kisses are sweet, usually soft and tender, modest. But this one is different. Their lips move together at a fast pace, their hearts are beating out of their chests and Regina climbs on Daniel’s lap to feel him closer to her.

“Regina,” he breaks away, his pupils are blown, and he is panting. “Someone could see us.”

She shakes her head, “I’ve never seen anybody out here.”

She kisses him again, chasing that unknown feeling that’s burning in the pit of her stomach. Daniel doesn’t protest and kisses her back, lets his mouth wander to her neck and starts sucking. Regina lets out a surprised gasp and rolls her hips against his lap instinctively. They have never done this before and Regina feels like it is something forbidden, something sacred for marriage. But then again, they're still fully clothed, and also, they're engaged.

Daniel’s hands settle on her hips, and he encourages her to move again, and Regina does. Even through their clothes Regina feels how different their bodies are. Daniel feels hard in the places she is soft in. His mouth is hot against her cold skin. He is strong while she is weak.

Daniel groans into her shoulder and kisses her again, fiercely. Regina’s head is swimming, and she hears herself moaning when his fingers brush over her chest. Daniel looks up at her and deliberately strokes over her chest again and Regina gasps, clinging to his shoulders at the sensation it triggers in her stomach.

Regina almost doesn’t hear the sound of hooves closing in but when she finally does, she jumps up and they pack their things together in a hurry. Luckily, it’s only Father that stops in front of them. He informs them that Cora will be home shortly and that they should get back before she does. Regina smiles gratefully and they ride back together.

When her father has left the stalls, Daniel wraps her in his arms and whispers, “I can’t wait to marry you.”

Regina smiles, “Me too.”



It’s her wedding night when Regina sees a man naked for the first time in her life. 

After the feast, the king escorted them to his chamber and ordered her to get ready for bed. Regina’s heart is aching more than ever with Daniel’s loss today. She imagines how their wedding would have been, how happy she would have felt right now to be able to share her bed with him. Instead, she feels scared, climbing into the king’s bed in her nightgown. Then, the king marches in, naked. Regina immediately looks away; her heart is racing in her chest. She doesn’t know why he didn’t put on his nightclothes. She heard that some people prefer to sleep naked, but she didn’t expect the king to be one of them. Especially since he isn’t alone tonight.

Footsteps stop at her side of the bed, and she feels the bed dip with his weight.

“Lay still,” the king instructs her and then Regina feels him lying down next to her, close. His hand settles on her hip and he starts stroking it. Regina’s breath comes out shallow, but she keeps still, even when he pushes up her gown and lets his fingers wander over her bare legs.

“You're mine now,” he tells her, slipping his hand under the hem to feel the softness of her breasts. “And you will do as I say. Understood?”

Regina manages to nod.

“Say it!” the king orders and possessively squeezes her breast. Regina winces but replies, “I will do as you say, my king.”

The answer seems to satisfy him, and his hands wander lower to pull down her underwear. “Good,” he breathes heavily and Regina blinks away tears when he touches her where no one had before. He grunts unsatisfied and then he pushes himself up onto an elbow and starts kissing her. His hand keeps moving between her legs and Regina doesn’t understand what he is trying to accomplish. Minutes pass by while his sloppy lips press against hers and his hand continues moving.

Finally, the king stops and Regina almost sighs in relief. That is before he climbs on top of her and spreads her legs. Regina feels something hard pressing against her pelvis. She doesn’t know about (male) anatomy, but she had seen this other body part for a short moment earlier when the king had walked in naked. Now, he spits on his hand and moves it between them and then he looks at her again. “Relax,” he orders, and Regina tries to relax her tense muscles, and calm her fast-beating heart, but she can’t. Not when every cell in her body is screaming at her to run.

Nothing prepares her for the pain that follows when he forces himself inside of her. Regina cries out, trying to get away from him but his hands hold her in place, and he pushes harder into her. She starts sobbing, unable to keep her emotions at bay. 

The king presses a hand to her mouth to muffle the noise and continues his movements. It feels like he splits her open with every push, and it’s hard for her to breathe under his hand. Regina thinks she might pass out when the king eventually loosens his grip and stills his movements with a long groan. He collapses on top of her, his heavy body keeping the air out of her. Then finally he pulls away. Regina feels something dripping down her legs, but she lays there motionless until she hears his breaths even out before she slowly sits up and looks down at herself. There’s a white liquid on her thighs, and blood.

 

 

Regina's first orgasm is with Maleficent. She has a lot of firsts with her. It happens after Mal had successfully turned into her dragon form.

Mal teleports them to her castle again and she is smiling widely at Regina, so much that Regina’s stomach does a little flip. And when Mal bends forward to kiss her, Regina doesn’t fight her. Instead, she happily kisses her back, lets Mal pull her to her chambers and down onto her bed. Mal’s hands are everywhere. She caresses Regina’s arms and cheek; she pulls her coat off her shoulders and lets her finger slip under Regina’s vest. Soon Regina can feel an unfamiliar sensation building up in her lower stomach, one she had only ever felt with Daniel. Tears shoot into her eyes, but she keeps kissing Mal, chasing the feeling she had connected to her lost true love.

Mal starts undressing her, doesn’t stop when she notices the tears rolling down Regina’s cheeks. Instead, her mouth wanders hot over Regina’s revealed skin and her hands touch her without hesitation.

Finally, she stops, looking down at her. “Do you want this?” Mal asks. Regina is not even sure what “this” means but she nods.

“Is it going to hurt?” she asks, remembering everything the king had done to her while she had been naked.

Mal’s eyes soften, “Not if you don’t want it to.”

Regina nods again, “Okay.”

Mal kisses her, “Good girl.”

She doesn’t position herself between Regina’s legs like the king had. Instead, she lays down next to her, pulling Regina’s leg over her own hip and starts kissing her again. Her hand finds its way to Regina’s chest, gently squeezing her breast and tugging at her nipple. Regina gasps and earns a smile from Mal. 

“Do you like that?” Mal asks, gently pinching Regina’s nipple again and Regina moans quietly and nods. Mal grins and bends forward, slowly taking it between her lips and sucking. Regina’s body reacts to it by arching forward, closer to Mal and the other woman smiles and lets her tongue flicker over the sensitive bud. Regina moans again, her hands pulling Mal closer to her chest. 

“Tsk,” Mal scolds her. “Who said you were allowed to touch me?”

Regina lets go immediately, blushing, and apologizes, “I’m sorry.”

Mal’s eyes meet hers and the older woman smiles again. “It’s okay. How could you know the rules? It’s your first time.”

Regina returns the smile, relieved she is not in trouble. Mal kisses her on the mouth again and Regina sighs happily. She feels the other woman’s hand brush over her stomach, then over her hip, up and down her leg, until it moves between them. Regina’s breath comes out shallow, fear settling into her stomach. “I don’t want it to hurt,” she breathes out, remembering Mal’s words from earlier.

“It won’t,” the other woman reassures her. “I promise.”

Regina relaxes under her words and kisses her again and then Mal’s hand moves between her legs, slowly stroking her.

Regina gasps, while Mal murmurs, “You’re wet. Good.”

Mal’s fingers move in small circles over the sensitive flesh and jolts of pleasure shoot through Regina at the contact. She whimpers, almost overwhelmed by the new sensation, and closes her eyes until Mal says, “Look at me.”

Regina opens them again and meets the other woman’s gaze.

“Does it hurt?” the dragon asks, and Regina shakes her head, panting.

Mal smiles and presses a quick kiss to her lips, “See? Now stop thinking and enjoy it.”

Regina smiles, “Thank you.”

She lets Mal turn her onto her back and relaxes into the pillows; lets the other woman take care of her, and listens to Mal’s whispered praise and the sounds of pleasure escaping her own throat. After a while, the pressure that has been rising in her stomach with every stroke of Mal’s fingers and every kiss of her lips, becomes almost painful. It’s too much for her and she becomes restless under Mal’s experienced fingers.

The other woman notices. “Regina, do you trust me?”

Regina opens her eyes again and nods, Mal kisses her again, “Good.”

Her lips wrap around Regina’s nipple and just when Regina’s back arches off the bed at the sensation Mal thrusts her fingers inside of her and Regina comes with a surprised cry.

Afterwards Mal holds her close to her. She is still fully dressed but that doesn’t bother Regina. She feels safe and comforted, a feeling only Daniel had been able to give her until now.

From then on, Regina visits Mal more often. She learns about her body, learns what she likes, what Mal likes, and she finally sees the beauty in sex. Regina enjoys the power dynamics Mal establishes in her chambers. She likes to let go and give herself to the other woman. And when she is more experienced and knows Mal’s body as good as her own, their roles change, and Regina is the one in power.

Mal prevents her from getting impregnated by the king, teaches her sleeping spells, so he doesn’t even try to touch her and makes Regina not only feel satisfied, but also almost happy.

However, with Regina becoming more and more skilled and powerful in wielding her magic, they start drifting apart. There’s nothing more Mal can teach her and she visits her less and less until they’re nothing but distant friends.

 

Regina has new sexual adventures with men and women alike at her castle. While Mal had treated her like a subject from time to time and Regina had enjoyed it back then, she goes a step further at her own castle and keeps herself “pets” over which she has full control. Most of them are willing to pleasure her, she only takes the heart out of some to make them hers. Nevertheless, Regina enjoys it, and when she casts her curse she takes her favorite with her, Graham.

 

Sex with Graham is satisfying. Even though he doesn’t consciously remember all her lessons in the Enchanted Forest, Regina is happy to find he does it the same way he had back there. Usually, it’s Regina on top, in control, but sometimes she lets him fuck her from behind and murmur dirty things in her ear. He never once tries to take her when she is lying on her back and Regina is thankful that she doesn’t have to find an excuse as to why she doesn’t like it that way.

 

Not until Robin, of course. He is understanding, doesn’t push her to explain but she can still feel his curious eyes on her, and she doesn’t quite manage to enjoy herself on top of him under his gaze. She climbs off his lap and starts kissing him again, desperate for this to work, for them to work.

“Take me from behind,” she whispers into his ears and his eyes go wide.

“You sure?”

She wants to roll her eyes but nods and smiles. “Yeah.”

He kneels behind her and gently pushes inside of her. Regina lets out a low, encouraging moan and soon his thrusts get deeper, and his pace quickens. She moves against him, chasing the friction that she needs on her clit to be able to come.

“Harder,” she pants, and Robin follows her request and grabs her hips to pull her back against him and Regina finally gets what she needs. Years of experience let her lift her ass in just the right angle for him to hit her in just the right spots.

“Robin,” she moans, and she can feel him groan and fuck her harder. It hurts now but Regina welcomes the pain and comes with a small cry, shortly after him.

When she’s laying in his arms, she feels secure and comforted again, a feeling she hadn’t had in decades. Robin is there for her, caresses her skin, smiles at her and tells her stories about his adventures. He doesn’t judge, he doesn’t push and Regina’s feelings for him grow every day. It shows in their sex life as well. Regina takes her time on top of him, caresses him, kisses him and directs his mouth and hands to where she needs them. She never lets him have her on her back though and Robin never asks for it. With him Regina can imagine what it would feel like to make love. And she does love him. His kindness, his wits and his honor but not in the way she had loved Daniel, not in the way she wants to, not yet.

Robin’s death leaves her wondering if what they had could have become true love. If that was the reason he died - because villains don’t get happy endings. Because villains don’t deserve true love.

 

Regina has given up all hope for a happy ending when Emma comes stumbling to her doorstep, after the pirate leaves her. A baby in her arms and an awkward smile on her lips, she asks if she can stay for a few days until her parents have calmed down.

They haven’t seen each other for a while. After Emma had married Hook, she had stopped visiting her, and only Snow and David had told Regina from time to time how Emma was doing. Regina lets Emma in of course, gets a room ready for her and the baby, and sets a cup of hot cocoa in front of Emma, while she takes Hope out of her arms and moves her onto her own hip. The baby has beautiful emerald-green eyes, long lashes and a tuft of blond hair on top of her small head. Regina can’t help but smile at the smaller version of Emma and when she meets the other woman’s eyes again, Emma is smiling at her so affectionately, Regina’s breath catches in her throat.

 

Emma stays.

 

Regina makes them breakfast every morning and helps Emma with Hope. They develop a routine and Regina feels happy again. While Emma felt almost like a stranger to her when she had first stood on her porch with a baby in her arms, the familiarity had come back soon, and Regina found herself teasing Emma on a daily basis again. With that familiarity, the old feelings for the other woman came rushing back as well. 

Hope learns to walk and speak, and Regina is there to experience it all. She feels happy with Emma and Hope in her house, even more when Henry comes to visit with his own family and the house overflows with laughter and life.

It’s after everyone has left when Regina kisses Emma for the first time. They had been sipping on some wine, reminiscing about old times, Hope already tucked in, when Emma had laughed so freely and beautifully, that Regina couldn’t resist cupping her face and pressing her lips onto hers. After a moment, Emma had kissed her back and Regina hadn’t stopped smiling since then. They had taken it slow, growing familiar with each other until this one night, when they hadn’t stopped after their kisses became heated. That is when Regina makes love for the first time.

 

Regina nibs at Emma’s lower lip, while she directs her to the bed. Emma moans into her mouth, falling onto the bed entangled with her. Regina turns her on her back and positions herself on top of Emma. She strips off the last pieces of clothing separating them and bends forward to kiss her again. Emma’s body feels warm against hers. She can feel the blonde’s muscles working under her soft skin, and she lets her lips wander, worshipping every inch of skin she passes. Emma closes her eyes and lets Regina’s curious mouth discover her body.

Regina kisses the freckles she finds scattered on Emma’s chest, she kisses the scars Emma has collected during her time in foster care, and worships the stretch marks Emma has gotten from carrying Henry and Hope. Emma’s breathing comes out shallow and the encouraging moans escaping her lips make Regina smile. She loves the way Emma’s body is responding to her. How her nipples harden when Regina takes them between her index finger and her thumb, how her legs spread eagerly when Regina’s tongue leads a wet trail down Emma’s torso, how her back arches when she finally tastes her. Emma is more than ready for her, but Regina still asks permission, “Fingers?”

“Please,” Emma whimpers.

“How many?”

“Two, maybe three,” the blonde gasps.

Regina smiles and slowly pushes two fingers inside of Emma, adding a third when they slide in with no resistance. It doesn’t take long for Emma to come. Regina’s experienced tongue and the steady pace of her fingers pushing into Emma let the blonde reach her release after only a few minutes. When Emma’s legs clasp around her head, and she cries out her name Regina thinks that if she were to die this moment, she’d die without any regrets.

Soon Emma’s breathing returns to normal, and she pulls Regina against herself, smiling at her and then kissing her again. Her lips wander to Regina’s neck where they nib and lick at the sensitive skin. Regina closes her eyes and enjoys the attention, giving herself to Emma.

“You’re so beautiful,” Emma whispers into her ear. “I could look at you forever like this.”

She climbs on top of her and settles between her legs. Regina freezes for a moment, waits for her stomach to drop and her throat to tighten but nothing happens.

“You okay?” Emma asks, watching her closely.

Regina finds that she is and relaxes under the blonde. “Yeah.”

“Good,” Emma smiles and kisses her again before she lowers her body onto Regina’s. Her pelvis presses deliciously against Regina’s clit and Regina moans when Emma moves to suck on Regina’s throat. Maybe it’s because she finally healed from what had been done to her all those years ago, maybe it’s because she trusts Emma like she hasn’t trusted anyone before her, but in this moment Regina gives all of her to Emma. She doesn’t tell her what to do, just enjoys Emma’s kisses and touches and the loving things Emma whispers into her ear.

When Emma’s mouth makes its way down Regina’s chest and her lips wrap around a stiff nipple and suck, Regina’s body arches off the bed and a small cry escapes her lips. She blushes and presses her lips together to stop herself from whimpering when Emma’s tongue plays with the sensitive bud.

“Don’t. I wanna hear you,” Emma whispers, blowing against Regina’s nipple. “Let me hear you. Please.”

Regina meets her gaze and nods, closing her eyes again. She doesn’t stop the sounds escaping her lips now. Small whimpers, low moans and high-pitched cries.

Being vocal during sex was a technique Regina had perfected over the years. She knows which moans sound sexy and at what time during sex she has to voice them to show her partner how close or far away from her orgasm she is. But now, for the first time ever, she lets go of all of that. She lets Emma see her, truly see her. Lets her hear her gasp when her fingers enter her, lets her hear the desperate whimper when she doesn’t get the attention she needs on her clit, lets her hear her begging when she is so close she already sees stars exploding behind her closed eyelids.

Emma takes her time and when Regina finally comes, her voice breaks with the intensity of the orgasm rippling through her. Emma helps her through the aftershocks, settles down next to her and wraps her arms around her. Regina smiles and laughs and kisses Emma, and an unfamiliar feeling settles in her chest.

She doesn’t recognize it at first, hadn’t expected to ever feel it again. Then, she realizes what it is, what it means. Something she had chased after her whole life, something she hadn’t thought was possible for her. Happiness, true happiness. The hole in Regina’s heart has been filled. Emma’s love is the last puzzle piece to complete herself again.

Regina finally gets her happy ending.