Summary: Regina and Robin are both nervous about their wedding night and seek out advice from friends and family before the big day.
December 13, 1780
She's getting married tomorrow and she's nervous, so so nervous, not because she doesn't think she's making the right choice, she knows she is, but because of her wedding night. She knows (sort of) what's expected of her, but the advice her mother gave her did the opposite of what it was supposed to and left her more confused and anxious than before.
Her mother had prattled on about how she would need to keep her husband happy and show him what he'd be missing whenever he was away. About how important it was for Regina to do it well, so she didn't end up disgraced by her husband's misdeeds and bastard children.
"After all," Cora had remarked, "Just look at his mother Regina, it's a disgrace. You cannot bring that sort of shame to our family. It's bad enough you are marrying him, and you must ensure he doesn't drag our family into disrepute."
Regina had been angered by her Mother's comments about Robin's family, she knew her mother didn't approve and she had naively thought the criticism of Robin would stop as the wedding drew closer. Regina had ignored her last comment because it's not worth fighting with her over it.
"And how do I...um…" she stammered blushing hotly.
"Don't stutter Regina it's unbecoming," her mother snapped back.
She didn't look in her mother's eyes when she asked. "How do I keep him happy, ensure my wedding night is satisfying?"
"Just give him what he wants and focus on his pleasure."
Her face was flushed red when she had asked timidly, "I'm not sure what you mean."
Cora had scoffed, "You are to be married Regina, these are things you need to know, give him your body, however he wants it, whenever he wants it. Ask him what he likes and do that, whatever it is. Make sure you are the best he's ever had. If you play your cards right he'll never stray from your bed."
She knew enough to know that at least the first time it would hurt. "Does it always hurt?"
"No, you get used to, but don't show that it hurts, they want you to enjoy it."
"And um how do I do that?"
Cora had narrowed her eyes, "Don't show it on your face, pretend you are enjoying, really Regina I thought you were smarter than this."
"That's… that's not what I meant, how do I… uh enjoy it?"
"It's not about you Regina, it's about him. Now I think we've had enough distasteful conversation for one night."
She'd been stewing over her mother's words ever since, she wanted it to be good for Robin, wanted to bring him pleasure, but everything her mother told her seemed contradictory. As usual, instead of helping, her mother had just added to her confusion and made her feel stupid.
She's fretting anxiously when her sisters Mal and Mary Margaret enter her room, not bothering to knock.
"Oh Regina, are you excited? Tomorrow you'll be a married woman," asks Mary Margaret excitedly.
"And you have parental approval, no scandalous eloping for you," quips Mal.
"I am," she starts and then sighs, "I'm just nervous about tomorrow night."
Mal nods in understanding, and moves to sit on the bed beside her. "There's nothing to be afraid of little one, the first time might be a bit awkward, but once you know each other well, then it's incredible."
Mary Margaret's eyes widen in interest as she settles on the bed beside Mal. "I thought it was only good for men."
Mal shakes her head emphatically, almost amused. "You need to know this for when you marry David-"
Mary Margaret interjects with a tone that supposed to be convincing but falls flat. "I'm not going to marry David, he's just a farmer, our parents would never approve."
"They are letting Regina marry Robin so I wouldn't be so sure about that, and if not you can always follow my example and elope."
"David and I are just friends I don't… I'm not, it's not like that."
Regina stifles a laugh as Mal responds, "Oh please you are so obvious Peggy; even a blind man could see you like him."
Mary Margaret blushes fiercely and responds hotly, "I prefer Mary Margaret. I'm not a child anymore."
Mal rolls her eyes, and gives her a silent whatever look before continuing, "Now as I was saying, it should be good for both of you and if it's not then that's a problem."
Regina asks, "But how do you know if it's good."
Mal sighs, "Trust me, you'll know, but have you ever felt heat, a longing to touch there before?"
Regina blushes furiously and stares at the floor uncomfortable. She remembers that time she and Robin went for an open carriage ride and stopped in a secluded field, how they had kissed and kissed and his hands had wandered over her dress and the heat that had built between her legs as he touched and kissed her.
Mary Margaret also stays silent, eyes glued to the floor.
When Mal realizes they aren't going to answer her she continues. "You don't need to admit anything but if you've given yourself pleasure then you can show a man how to do it."
Mary Margaret nods in understanding, and great even her naive little sister knows about this than her. Even though she wants to die of embarrassment Regina asks softly, "And what if you haven't?"
Both Mal and Mary Margaret eye her curiously and Regina feels her cheeks burn, this is absolutely humiliating, she's normally the knowledgeable one. Now, with this, she's totally lost. She wishes she just kept her mouth shut. She's never been this mortified before. It's one of those rare times she wishes magic was real, so she could just poof herself out of this embarrassing situation.
Mal quickly soothes, grabbing her hand and stroking it lightly. "That's okay little one, you can figure it out together, you should feel pleasure when you are together, lots of it, and it might not happen the first time but there are things he can do to help."
God she feels like such an idiot, but gathers her courage because she needs to know and asks, "Like what?"
"He should spend some time getting to know your body, and you his, but he'll enjoy it no matter what, so you needn't worry so much about that in the beginning. There will be places that feel good for him to kiss, that will make you want to move on. When you feel ready he should use his mouth or his hands on you."
Mary Margaret asks, "His mouth? Like down… there?"
Mal laughs at her incredulity. "Yes there, trust me it's very pleasurable."
"But isn't that improper?"
"In my view it's more scandalous to miss out on that type of pleasure because of some foolish notion of propriety."
Regina pipes up, "Mother thinks women shouldn't chase their pleasure."
Mal rolls her eyes, "Well then I'm glad I missed that life lesson, she's wrong, it's always better when you are both actually enjoying it, trust me."
Regina is still mortified but finds the courage to ask, thinking of those few clumsy times she was wanting and tried to get some relief with no avail. "What if I can't, what if there's something wrong with me and I can't… uh enjoy it… fully."
"Regina trust me you will, just talk to Robin tomorrow night, I'm sure he's, well maybe not just as worried, but worried too. It's going to be okay, just don't expect it to be perfect right away. Oh and one more piece of advice, and excuse how crude this is, but make sure he stretches you first with his fingers, don't let him shove inside you without any prep or it will be painful."
Robin's nervous, he's so unbelievably smitten with Regina Schuyler and he doesn't want to do anything to mess it up. He fumbled through their courtship, absolutely enamoured, somehow managing to charm her, the smartest woman he'd ever met. Though he was utterly besotted with her, he never thought he'd have a chance. After all, she's a Schuyler and he's just an immigrant, bastard, son of whore, he has nothing to offer her, but somehow she still fell for him and her father gave him his blessing.
Tomorrow they are getting married, tomorrow he gets to marry the woman he loves, and he's thrilled, but the wedding night makes him antsy. He's heard that it hurts a woman the first time, and he does not want to hurt Regina.
So he goes to his friend Killian Mulligan for advice. Killian is quite the ladies man and Robin's knows he's been with more than a couple maidens. Robin's heard far too much about Killian's exploits, knows far more about them then he wants to, but now he needs the advice.
Mal's husband John Little decides to join him for the ride. John and Cora were in the midst of arguing about something when Robin announced he was leaving and John jumped at the chance to escape for a while. Robin hadn't had the heart to say no, as he knows how much John hates Cora. Robin feels the same but is not as open with his disdain and John. If he knew John better Robin might have asked him, they've only met briefly a couple of times and he's not sure how well it would go over with him.
As the night goes on and they drink more Robin finds he and John have a lot more in common than they realized. A racy joke John tells reassures Robin that he won't scandalize John with his questions. Robin is grateful to have another person there to ask, he trusts Killian's advice to a certain extent but it's nice to have John there to verify what is and is not true.
They have a couple more drinks at Killian's estate, talking generally about the wedding before Robin gathers his courage and finally asks. "How do I make the wedding night good for her too? I don't want to hurt her."
Killian laughs, "I bet you regret not taking me up on that brothel visit now."
Not a chance, thinks Robin and his indigent, "No," makes John chuckle.
Killian goes on, "Listen mate it's not that hard, it's instinctual really, as long as she's wet you can stick it in and then the real fun begins."
"But don't you need to... prepare her some way?"
"Nah mate, a couple of kisses, get her naked, play with her tits and you are good to go."
Robin watches John's face turn from horror to disbelief and then he jumps in. "The key is to find out what she likes and then keep doing that. Don't rush to being inside her, take your time, build the anticipation. You have to discover her body and what works and doesn't."
Robin nods, that makes sense to him but it's also vague. "What can I do to take away any pain?"
Killian says, "Don't worry about that-"
John interrupts, talking over Killian until he gives up, "Get her nice and relaxed, turned on. She needs to be really wet and then use your fingers, one at a time, inside to prepare her. And outside, down there, is a spot that can give her intense pleasure, find it, and discover how she likes it touched."
Now that is helpful, Robin has seen a naked woman before, so he understands what John means by down there, at least he thinks he does.
Killian clearly annoyed at being interrupted adds, "Women are hard to please mate don't beat yourself up if you can't do it." He gestures to his drink clearly done with the topic "Anyone need another?"
He and John shake their heads and as Killian walks over to refill John whispers, "Don't listen to his advice I beg of you."
Robin quickly reassures him, "I don't intend to."
On their carriage ride back to the Schuyler residence Robin thanks John profusely, and to their drivers distaste gets a few more tips and tricks about how to please a woman. It turns out the drinks made them much less discrete than they thought. Robin almost feels bad for the driver, until John tips him generously for the inconvenience of listening to such an impolite discussion.
The day flies by in a blur. Regina looked absolutely stunning in her gown and Robin's jaw had fallen open when he saw her. He stared at her in wonder the whole ceremony, paying little attention to anything but her. And when she said I do his heart just about exploded from sheer happiness.
Then they retired to her parents' house for a meal and party in honour of their marriage. There had been lots of wine and ale but Robin only had a couple, just enough to loosen his nerves, but not so much that he was drunk.
Mostly he had danced, he and Regina danced and danced, no longer limited in how many times they could dance together. He reveled in the feeling of her in his arms, the small touches they were now able to share freely and openly. He barely let her hand go once they were married, needing to feel close and connected to her.
He had kissed her, more than once, drawing scornful looks from her mother. The kisses were relatively chaste, lest they give Cora any reason to call him uncouth again and rant on about propriety.
Regina's eyes sparkled, her face lit up with a smile most of the night, right up until her maid came to escort her to their room. He saw the nerves flicker on her face for a second before she steeled her face and calmly said her goodnight's.
It's been enough time, he knows she's up there waiting for him. He makes his way up the stairs to their room, and just that thought has his nerves churning. He doesn't think he's ever been this nervous before, on the other side of the door is Regina, his wife, waiting for him so they can consummate their marriage.
He takes a deep breath and then knocks at the door. At her Come in, he enters the room.
He's been alone with her before, those few times Mal 'chaperoned' them and couple of stolen moments since the engagement but never like this. She's breathtaking, absolutely stunning with her hair down, in her sheer nightgown. He tries to ignore the thought of how it will be to touch her in this, not hindered by layers of clothing or fear of being caught. They need to talk first. He can tell she's nervous like him and he wants to do what he can to calm her fears, despite his raging hormones.
She's looking at him, shyly standing by the bed, and he moves to sit, gesturing for her to join him.
"Regina, my love, you look stunning and I'm so happy to be your husband."
She smiles, "And I'm thrilled to be your wife."
"I'm so lucky to have you," she blushes at that and shakes her head in disagreement. "No truly love I am, you are the most incredible woman I've ever met, and the most beautiful person I've ever laid eyes on. I'm just a poor immigrant, and I shouldn't have had a chance with you but I got one and I will never throw it away."
"I'm the lucky one," she insists, "I'm too outspoken and opinionated for most men."
"It's one of the things I love most about you," he tells her sincerely and watches as her face lights up at his compliment.
"I have to admit, I'm rather nervous about this," he says gesturing to the bed.
"As am I," she responds looking down, "I know what's expected but I've never… and I don't want it to be bad but I don't know what I'm doing."
"Nor do I my love, I know I have a bit of a reputation as a ladies man but it's not true, I've never been with a woman before and I want to make it good for you but I'm flying a little blind."
She laughs nervously, "Mal um made some suggestions."
"As did John, I went to Killian for advice and he came along and I've never been more grateful."
They look at each other, lost in each other's eyes for a second and he wants to kiss her, is about to when she asks, "So um what now?"
"I want to know what you like milady, would it be okay with you if we, uh tried some things, and you can tell me what's good and what's not."
She nods slightly and then he caresses her face softly before leaning in for a sweet kiss. It's not their first kiss, not by any means, but the opportunities have been few and far between. He relishes in the feeling of her lips on his, soft and tentative and as he deepens the kiss, he brings his hands to thread through her hair.
He ends the kiss, pulling his face away only slightly, and she smiles at him and then pulls him in for another kiss, this one more passionate, her mouth opening and her tongue tentatively seeking his out.
As soon as they touch he's lost to her, moves one hand down to her back, pulls in her closer so their bodies are touching as their tongues duel. She's pressed up against him, he can feel the warmth of her body beneath her nightdress and it's enough to drive him crazy. He wants to feel her, wants to try and bring her pleasure, to learn her body.
They kiss heatedly for several minutes as his hands become more adventurous, sliding up and down her back and moving closer to her fabulous ass.
He breaks the kiss to ask, "Is this okay?" and she nods eagerly in response. He wants her so badly, wants to move on, but remembers what John told him.
He plants a few kisses on her jaw and she sighs lightly, taking that as encouragement he kisses down her neck, between kisses he reminds her to tell him what she likes because though it seems to him that this is working for her he really can't be sure.
He figures out what John meant about him knowing what was good when he kisses that spot where her neck meets her shoulder. She lets out a strangled cry and tells him So good, so he spends some time kissing licking and sucking that spot. He learns that she likes a suck but a bite is too much for that sensitive skin. He apologizes for it and he's happy to realize it's not too awkward, she's not offended by his mishaps and it's sort of fun for him to explore her this way.
He's made a bit of a mark there, the skin reddening so he takes that as a sign he should move on, explore other areas.
He kisses her again deeply, their tongue tangling and she moans in his mouth. The sound goes straight to his cock, as he tries to will himself to calm down. He's hard, has been since they began this, but he is determined to take it slow and make it good for her.
His breeches are tight, too tight and he's running out exposed skin to explore so he asks, "Is it okay if this comes off?" gesturing to his breeches and her nightdress.
She nods in response her face twisting anxiously and he rushes to reassure, "We won't do more until we're ready I'm just a bit uncomfortable in these breeches and I'm running out of unfettered places to kiss you."
That seems to relax her and she pulls the nightdress over her head as he unlaces his breeches. Then he looks at her, bare before him and his heart races. She looks at him shyly as he whispers, "You are so beautiful milady."
He takes a moment just to look at her. She flushes under his gaze, but god she's just so beautiful and sexy and he wants her so so badly. Her breasts are wow, so perfect. He's seen a couple of women topless before, but none as sexy as Regina. Her nipples are standing up hard and he longs to suck on them. His gaze continues down her body and he stares at her gorgeous legs and the prize between them. He wants to try what John suggested, wants to bury his face between her legs and try to bring her pleasure but he is throbbing. He gives himself a quick stroke just for a bit of relief and Regina watches him intently, drawing her bottom lip between her teeth.
"Are you okay love?" he asks, "We don't have to do this."
Her voice is firm, "No I want to do this, it just seems a bit unfair that I'm completely naked and you are," she pauses, looking down at his erection popping out of his unlaced breeches, "Almost fully dressed."
"Well I think I can help with that," he says smirking as he takes off his shirt and then she's the one staring as she reaches her hand out and over his chest. And god it feels incredible, her soft touch over his skin he moans as her hand ghosts over his nipple before trailing down towards his cock.
He gasps loudly as she touches him for the first time, wrapping her delicate hand around his erection and it's good, the feeling of someone else touching him, but it's too good, he doesn't want it to ever stop, wants to bury himself in her, but he needs to do more for her, so he grabs her hand stopping it.
At her quizzical expression he answers, "If you keep doing that I won't be able to control myself."
Then she's the one smirking that is until he pulls her in for another heated kiss, their positioning is a bit awkward so she lays down pulling him on top of her and shit, it's amazing the feeling of her warm skin against his.
He kisses down her neck again delighting in the encouraging moans and gasps she lets out in response. He kisses down her chest, then lightly sucks on her nipple. The breathy moan she lets out his name is the most beautiful sound he's ever heard so he does it again, and then sucks harder and she cries out louder. Fuck, he thought he was aching for it before but this, god it's so sexy.
He goes to the other one, gives it the same treatment, starting out soft and then increasing the intensity, but he's a bit overzealous, overestimates how hard he can and she lets out an uncomfortable Mhm before telling him, "That's too much, it's good just not that hard."
He whispers apologies into her skin before returning to the lighter pressure she enjoyed. She moans in response, her back arching as she threads her hand through his hair pushing him closer and he shivers.
His hands aren't really doing anything, just propping him up because he's not quite sure what he should be doing with them. He tries to move his one hand so he feel her curves but he misjudges how his weight is centered and ends up falling slightly so all of his weight is pressed against her.
He mumbles a Sorry but she tells him "S'okay, I like feeling you against me." And that makes two of them. He shifts a bit so his weight is resting on his knees, his breeches falling down and tangling at his knees.
"Is it alright if these come off?"
She nods smiling shyly and he pushes them off throws them aside and re-positions him so his hands are free to explore her.
His mouth meets hers again and there's an urgency to the kiss from both of them that wasn't there before. His hands slide down her back and grip at her hips and then he takes a handful of her gorgeous ass, so round but firm.
She tenses as his lips move down her stomach and he asks, "Is this okay?"
The breathy Yes, he gets in response lets him know it's anticipation and not discomfort, which is good because he would stop if she asked, no matter how much it hurt, but he's never been this hard ever and he desperately wants to feel her.
He finishes kissing down her stomach and now he's at a bit of loss, he can see that she's wet, but he's not sure where that pleasure spot is that John mentioned. He knows he needs to warm her up with his fingers so he grazes his hand down and over the hair to her opening and asks, "May I?"
She nods breathing heavily and he goes slowly, dipping one finger in to her hot, tight wetness. She feels amazing around his finger and he can only imagine how incredible she will feel around him. He's not really sure what he should be doing with his finger, just eases it in and out to start, as he looks down trying to figure out what part is that outer pleasure spot. He moves his finger from side to side, front to back and it seems like there's room for another finger so he slides a second one in slowly, but it's tight and she tenses but tells him, "It's okay keep going."
So he does, ever so slowly, until both are buried inside of her, her walls stretching to accommodate the intrusion. He continues to move slowly, upping the pace just slightly, and she's sighing, but it's not the sharp pleasure he hoped to bestow on her.
He needs to find that spot. He pulls out his fingers, glistening with her wetness and traces them up her folds searching. He hits a little nub and she inhales sharply so he rubs over it and she gasps, "Yea there."
This must be where John was talking about. He keeps up the loose rubs she seems to be enjoying and puts his other hand to work. He starts off slow again, just one finger, but she's more ready this time, can accommodate the second so he crooks it in too. The in and out motion seems to be better now with the light pressure on that outer spot because she's breathing heavily and he feels her shiver when he gives it a bit more pressure.
"Good?" he asks, just to be sure and she sighs "Yes."
He hits a spot inside her that makes her trembles on one thrust of his finger as she hisses out his name, but he was more focused on that outer spot so he's not sure where exactly he hit that was good.
He takes a second to focus on his fingers inside, moving them around hitting different spots and judging her reaction. He takes his time exploring inside of her with his fingers, taking note of the different textures inside her. He hits against a spongy spot along her front wall and she cries out again, so he curls his fingers up and over that spot.
"Oh god, that's…. Oh Robin, yes."
He smiles; it seems he's found the right way to work his fingers inside her. He wishes he wasn't using his left hand because he can reach that other spot with his thumb but isn't sure he has the coordination to do both with his left hand.
He settles for using his right on that outer spot, rubbing over it in quick hard passes that have her breath quickening as she lets out encouraging sounds.
He has barely been touched, but he is so close just from hearing her, the lack of stimulation is getting painful, but he won't deny her her pleasure no matter how badly he wants to be inside her.
But then she whimpers, "I'm ready, I want you." and "Please Robin, I want to feel you." And well he's reached the end of his self control but the two fingers he has inside her don't seem like enough, relative to the size of him, so he tells her to wait and gives her a third. He's less gentle with this one but she doesn't seem to mind, he keeps hitting that good spot and she's crying out, tensing and tightening around him and as much as he wants her, he doesn't want to stop.
But then she's begging again, "Robin, please want to feel you... Ah."
He relents because he needs it too cannot wait a second longer to feel her. He lines himself up with her and slowly pushes himself in, inch by inch even though he is dying to slam into her and feel her all around him. He can tell it's not as good as his fingers, her face scrunches in pain but she urges him to continue.
He stops half way in and watches her take slow forced breaths, trying to relax and he asks, "Do you need me to stop love?" God it would be torture, but he doesn't want to hurt her.
"No, just um…" then she stops her face wrinkling.
"Just what, love, anything you want it's yours." And god he's trying so hard to focus on anything but the feel of her around him, it's amazing and he's so so close to coming.
"I don't know," she huffs frustrated, and no he doesn't want that. He pulls out a little, leaving just his tip in and its absolute torment to stop like this, but he wants to do this right. He shifts so he can reach that little bud and gives it some more firm rubs and she sighs happily. He once again thanks John for telling him about this magic spot, and shudders thinking how much harder this would have been if he didn't know about it.
She whispers encouragingly, "Yea that's good, you can keep going now, I'm ready."
And thank god because he needs to move, but he does it slowly, keeping up the pressure on that spot makes it easier, she's more relaxed now and not quite so tight around him. And god it feels so fucking good and then he's all the way in her and it's bliss, nothing has ever felt this good before. And he needs to move, can't help it, he slides in and out of her and oh god, he's close, so close, his balls are tight and heavy.
He manages a few more thrusts before he can't take it anymore and he surrenders to the pleasure. He comes hard inside her with a cry of her name and then rolls of off her, pulling her into a tight embrace.
"That was amazing." he says breathing into her skin, reveling in having her in his arms.
"Yea, it was, wasn't it."
And maybe it was better for her than he thought so he asks, "Did you uh have one too?"
She seems to get what he means. "I don't know, but I've never and that was more pleasure that I've ever had."
Though he's tired he won't leave her unsatisfied. "You would know if you did."
He strokes his hands down her body, intent on finishing her but she stops him and admits, "I'm a little sore, maybe another night?"
He's quick to apologize, though she swears there's no need, and he vows that next time he will make up for it.
Opening this verse for prompts, if you want to see anything send me a prompt :)