"Moms."

Their son's voice cracked as he said the word, and it caught their attention immediately.

"What is it, sweetheart?" Regina asked softly, looking at her son, who was averting his gaze.

Emma added, "Is everything alright?"

"I'm scared to have sex."

The women went silent at this, completely shocked by the young man's confession. Neither of them had discussed more than the basics of the birds and the bees with him, and that had been years ago, except when Emma had offered a quiet, 'Always use protection' reminder on his sixteenth birthday. The fact that he had just turned eighteen and was apparently still a virgin surprised his mothers greatly.

When Emma realized that Regina was too deep in shock to respond – even though she was obviously trying hard to formulate a response – she decided to jump in with, "There's nothing wrong with that, Henry. Sex can be intimidating, especially the first time. Can I ask you, though… Why are you bringing this up now?"

"Well… I'm going away to college in a few months, and… and I figure… I don't want to be a virgin forever… but I'm scared I'll be terrible or mess it up or… or…"

"Oh, Henry. No one's first time is perfect."

"But, Emma, I… What if… What if I-"

"Henry. When the time is right, it'll work itself out. It's not something you need to stress over. Good sex comes with time and practice, to be totally honest. You learn what you like and what your partner likes and how to make that work for you both."

"What was your first time like, then?"

"Henry, that's…"

"I'm just asking."

"It was with your father. And it was pretty much horrible. It was rushed and quick and basically over before I could blink. We did it in the back of a car I stole. It wasn't very romantic. I'd regret it, except it got me you, and you are the most perfect thing that's ever entered my life."

"But Mom… I don't want my first time to be bad. I want to be good in bed and make whoever I'm having sex with happy, you know? I don't want it to be some rushed, shitty fuck that she regrets."

"Henry!" Regina finally cut in. "Watch your mouth, please!"

"Sorry," the young man mumbled, looking down at his full dinner plate.

"You should finish eating," the brunette told him nervously, nodding at the food on his plate.

"I'm… I'm too stressed to eat. I can't stop thinking about it."

"Listen, Henry," Emma sighed. "It's normal to have hormones, and it's normal to think about it, and it's normal to be nervous, but you don't have to be scared, okay? Even if it's not perfect, it'll be alright. You just need to not rush the choice of a partner. When you find the right person to do it with that you trust completely, it'll work out. It might not be great the first time, but together, you'll both figure it out and eventually, it'll get better."

"Did it get better with Dad?"

"No, Henry, it didn't. But that's because I like women, not men, and I was trying to force myself to enjoy a sexual encounter that I didn't really want to have. I felt like it was the right thing to do, so I did it."

"Well, what about now? What about with Mom?"

"Henry!" Regina cried. "That's totally inappropriate!"

"Regina, it's alright," the blonde told her, putting her hand on the mayor's to calm her. Then, she turned to their son and said, "It's much better."

"But why?"

"Because we-"

"Henry, our sex life is none of your business, and-" Regina interjected anxiously, pulling her hand away from Emma's.

Her wife cut her off quickly, saying, "Regina, if he wants to know, I'm going to tell him. Who else is going to be honest with him about how sex works, if not his mothers? He deserves the honesty and openness that we expect from him in return."

Biting her lip, the mayor looked down at her plate and tried to will away the embarrassed blush that was rising to her cheeks.

"Anyway," Emma continued. "It's better because we listen to each other. Verbally and physically. We pay attention to each other's bodies and how they react to different touches, and we care about those reactions. It's not just about one of us getting off. It's about both of us making each other feel good and enjoying that intimate connection. Being in tune to each other is part of what makes it so special."

"Was it always like that, though?"

"No. I mean, it was always good, don't get me wrong. But it got better and better every time, because we learned from each other, and we paid attention to what the other person liked and didn't like. It was a process."

"But I don't want it to suck my first time! I don't want to be bad in bed!"

"Henry. You're not going to be Don Juan the first time you have sex. It's just not going to happen."

"But I'm gonna embarrass myself! I'm gonna be horrible!"

"Henry, honey, why are you getting so upset about this?" Regina cut back in, looking at him with concern in her eyes.

"Because I'm scared and I just… I keep having… urges… and I…"

"It's okay to have urges, darling. Everyone does."

"Yeah, but these are… they're… It's all the time, Mom. And I don't know how to make it stop. And what if it's horrible for whoever I'm with and they never want to talk to me again? And what if the urges don't stop? And what if-"

"Listen, bud. You're gonna be fine in bed," Emma told him. "It's just gonna take practice."

"Well… Can't… Can't you just… teach me?"

"What?!" Regina gasped.

"Henry… What do you mean?" Emma asked cautiously, feeling a lump rising in her throat.

"I mean, you're my moms, right? Aren't you supposed to teach me how things work? Aren't you supposed to teach me about love and stuff?"

"We're supposed to teach you about sex, Henry. Not… Not how to have sex…"

"Why? Why not?"

The women's eyes went wide, filling with shock once again, as both of them attempted to formulate some kind of coherent response.

"Henry, that's…" Regina tried. "Adults aren't supposed to… to…"

"But why?" Henry protested."Why shouldn't I learn the most important things from my moms?"

"Hen, that's… It's not… It's not right," Emma explained. "You're our son. We're not… We're family."

"Do I gross you out?"

"What?"

"Do I gross you out? Is that why you don't want to teach me? Am I really that disgusting? No girl in my school wants to touch me. They all call me a nerd and-"

"Henry, no," Regina countered quickly. "You don't gross us out. You're not disgusting. You're…"

"I'm hideous. I'm not-"

"Stop it," Emma snapped. "Stop it right now. You are a very handsome young man. But parents and their children don't… It's not right. It's not okay."

"I don't want to learn how to have sex from just anyone. I want to learn it from you."

Sternly, Regina ordered, "Go to your room."

"But, Mom! I-"

"We answered your question, and the answer is no. The conversation is over. Now, go to your room."

He could tell she was serious, so he stood silently from the table, pushed his chair back in, and made his way up the stairs, hot with embarrassment.

His discomfort quickly grew as he pictured his mothers together in bed – he couldn't help himself – until the pressure was too much, and he resorted to pleasuring himself.

Once they were in bed together, the two women lay quietly beside each other and breathed deeply, both processing the evening's strange conversation.

Finally, Regina asked, "I'm worried about him."

"Why?" he wife replied, looking over into the woman's dark eyes.

"What do you mean, 'why?' Because he asked us to-"

"Don't you think he's just scared and nervous and curious? He feels safe with us. That's all it is. He's not really… I don't think he understands what it really means is all. I think his hormones and curiosity are just going crazy, and his anxiety is just making it worse. We just happen to be the ones he's closest to."

"But no boy is supposed to want to have… to… you know… with his mother…"

"I don't think it's that he wants to have sex with us necessarily. I think he's just scared to do it with anyone else first. He wants to learn from people who won't judge him, and he knows that we won't. Except… I think… I think he's probably feeling pretty judged by us right now, based on our harsh reactions…"

"What are you talking about?" Regina squeaked, her voice strained. "He asked us to-"

"Regina. Calm down. I really don't think this is anything to worry about."

The woman sighed but went quiet. After a while, she turned and looked over at her wife.

Eventually, she said, "Did you mean what you said to him? About the sex we have getting better every time?"

Emma smiled at her and replied, "Absolutely."

"I love you."

"I love you too, darling. Now… Why don't you try to relax… and take your mind off things a little…"

"And how should I do that?" Regina asked, her tone teasing and playful.

"You should let me make love to you."

Regina quickly realized that what Emma had told their son was very true. Every time was better than the last, and this was no except. However, Regina quickly found herself shocked to find herself picturing her son as her wife helped her reach her climax.

"Babe?" Emma asked anxiously, seeing the suddenly look of horror in her lover's eyes. "What's the matter?"

But Regina had already begun to cry.

"Baby… Baby, what's the matter? What happened? Did I hurt you?"

Regina shook her head vigorously and let out a loud sob.

"Babe!" Emma pleaded. "Talk to me. What happened?"

"I… I can't… I…"

"Honey?"

"I just… I was feeling… and I just… I was picturing… but I didn't… I didn't mean to, and I-"

Eyebrows raised in response, Emma asked, "You were picturing what, exactly?"

"I…"

"Regina…"

"I'm sorry," the woman sobbed, covering her face with her hands. "I'm disgusting. I'm a horrible mother. I-"

Instantly, Emma gripped ger wife's wrists and pulled her hands away from her face, sternly telling her, "You are not disgusting, and you are not a horrible mother. Do you hear me?"

"But I was-"

"Maybe Henry's right."

"What…?"

"Maybe you should be the one to teach him."

"Are you serious?"

"Would you rather it be you, or some random girl we don't even know? Besides, he asked you. He trusts you. He-"

"I can't, Emma! It's wrong! And what do you mean me? What about you? He asked us."

"If it's so wrong, then why were you thinking about it?"

Looking ashamed, Regina whimpered, "I don't know."

"Baby," Emma said softly, cupping the woman's face in her hands. "I'm his biological mother. You're not. All that means is that he's not really related to you, and… well… He's not a minor anymore…"

"Emma! You can't be serious!"

"I think you should do what he asked."

"He asked us."

"We're related by blood. That is what's not right."

"I raised him!"

"So?"

"So, I'm still his mother!"

"Yes. Yes, you are. But not by blood. Therefore… it's not… it's not really wrong. And if it's what Henry wants, why shouldn't you? I'd much rather he learn it from you than someone else, to be honest."

"But-"

"I think you want to, Regina."

"Emma, I-"

"No. It's okay. Pretending like you don't have sexual urges about other people would be a lie. And I don't want you to lie. Urges are healthy and normal, just like you told Henry."

"But I don't! I never have before! I just… I don't know why tonight was different. I'm so sorry."

"I don't want you to be sorry. I want you to take care of our son."

"I'm…"

"Go check on him. I'll be here, okay? I'm gonna get some sleep."

"No way. I couldn't possibly-"

"Yes, you can. Now, go to him. Show our little boy how to be a man."

"But you're not… You're not angry?"

"Of course not. I trust you. I trust him. I want him to be happy and comfortable with himself. And I think this is the way to accomplish that."

"Are you sure?"

"Yes. I'm sure."

With some hesitation, Regina slipped out from under the covers and left the room.

She knocked on her son's bedroom door softly, her hands shaking.

When his mother got no response, she called out, "Henry?" but it wasn't loud enough for him to hear, and he was distracted by the pleasure his own hand was bringing him as he squeezed his eyes shut and breathed heavily, nearing his second climax of the evening.

Regina opened the door to his room slowly and opened her mouth to call out his name again, but when she saw the motions his hand was making beneath the sheets, she froze. When he started to grunt softly as he jerked himself off, she coughed to interrupt him, too embarrassed to say anything.

"Shit!" Henry cried out, finally realizing her presence. "Mom! Fuck! I-"

"It's alright, Henry. I just came in to talk to you. I… I'm sorry that I… interrupted you. I didn't think-"

"No. Mom, don't be sorry. I was… I shouldn't have been-"

"Henry, there's nothing wrong with masturbation. It's okay to get a release when you're feeling worked up."

Gathering as much bravery as she could, Regina stepped forward and sat down beside him on the bed. Instantly, Henry began to sweat, feeling the closeness of his mother's body, even though she wasn't touching him. Not to mention, he couldn't help but stare at the curves of her breasts as they bulged from the top of her nightgown, exposing her cleavage.

"You have nothing to be ashamed of, Henry."

"But, I-"

"I need to ask you something."

Swallowing hard, Henry replied, "Okay," and slowly sat up, scooting back and leaning against the headboard.

"Have you really been thinking about your mother and I sexually?"

Too embarrassed to speak, Henry simply nodded.

"And do you really want to be taught how to have sex? By us?"

Again, he nodded.

"If that is what you truly want, and if you're absolutely sure, your mother and I have agreed that it would be okay for me to… teach you… what I know."

"What about Emma?"

"Henry… We also agreed that, because she is your birth mother, and you're related by blood, and it would be wrong for her to-"

"I don't care about that! You raised me! You're just as much of a mother to me as she is!"

"Oh, sweetie," Regina sighed, reaching out to stroke her son's warm cheek. "I know that. The point is that the act would be even more inappropriate between you two. If you want to be taught how to be intimate with a woman, I will do my best, but your mother-"

"I want you both to teach me. Together."

"Henry, that's-"

"I don't care. I want you both."

"Emma and I both-"

"I don't care. I don't care if she's my blood relative. I don't care. I want my moms to be the ones teaching me. And not one of you. Both of you."

With a sigh, Regina studied her son's face. He was determined, and she could tell that he wasn't about to give up the argument easily, so she nodded her head and said, "Very well. We'll go ask."

Taking his hand, she stood up and led him to her bedroom, where they both found Emma rolled onto her side, facing the opposite wall.

At first, they thought she was asleep, but when she said, "Hey, babe. You okay?" and started to roll over, they both jumped.

She was just as surprised to find Henry with Regina.

"Henry! What are you-"

"Mom," he said, letting go of Regina's hand and advancing on the bed. "I want you too. I don't want to learn from just one of you."

"Henry, that's totally inap-"

"I don't care! Emma, please. Please. I don't want my first time to be without you."

Emma turned red at this. Suddenly, she was thinking about her son's first time, and being a part of it. She hadn't pictured it yet, the same way Regina had, but now that she was thinking about it, it was vivid in her mind.

When the room went quiet, Henry said a soft, "You're both so beautiful. Please. Please, show me how to do this. I'm scared, and I just want both my moms to be the ones there with me when it happens."

"Alright. Come here. Lay down next to me."

Heart suddenly racing from the invitation, Henry crawled onto the bed and positioned himself beside her. Regina followed suit, putting her hand on his hip. Emma rolled to face him and began to look him from head to toe. She was surprised to find that there was already a small bulge forming between his legs, and she was even more surprised to find her thighs clenching in response.

"We're gonna go slow, okay?" Emma said softly. "Mom's gonna take off your boxers. Is that alright?" When he nodded, she added, "If you get uncomfortable at any point, you say so, understand? You tell us, and we'll stop as soon as you say so."

"I don't want to stop."

Emma nodded to her wife, who then used slow, shaking hands to slide the young man's boxers down and off. The cool burst of air from the air conditioner softened him slightly, but when both of his mothers began to remove their clothing and stripped down to their panties, his mouth began to water, and his member began to harden again as a new wave of heat flooded his body. Both their nipples were hard, and noticing this only excited him further.

"I'm gonna touch you now, okay, Hen?" Emma asked softly, hovering her hand over his crotch.

When he nodded, she gripped his member lightly at the base and stroked upwards to the head, earning a gasp from his lips.

"Regina," Emma said, nodding to her wife.

The woman took the hint and placed her hand below Emma's on her son's hard shaft, stroking upwards when the blonde repeated the movement. This went on until Henry started to groan.

"What position to you want to try first?" Regina asked her son, once she and her wife had stopped their movements and removed their hands from his length.

"I… I don't know…" he replied. "Which one do you like best?"

"Everyone has different preferences, Henry…" Regina told him.

Emma just smiled and cut in, saying, "But your mother likes a good ride."

"Huh?" Henry asked, looking confused.

"She likes to be on top."

"What do you like then?"

"I'm pretty traditional and boring, really," the blonde chuckled. "I enjoy missionary."

"What do you want to start with, sweetie?" Regina asked her son, stroking his hair back.

"I… Maybe I should learn the basics first…"

"You don't want to practice with your mom first?" Emma questioned, looking a little surprised at his preference.

"I… I want you…"

"Alright, Hen. Take my panties off and kneel between my legs."

Blushing at the gentle command, Henry did as he was told, and once he was between his mother's legs, he felt himself aching. When Emma looked down and saw the precum on the head of his length, her breath hitched, and she was surprised to find herself growing damp at the sight. She'd never been one to enjoy the touch of a man, but something about her son's body was earning a reaction she couldn't control.

"I feel… I feel stupid," he suddenly blurted, pulling away slightly.

"Sweetheart," Regina said, kneeling behind him and putting her hands on his shoulders. "We love you. Don't feel stupid, honey. Remember, it takes practice to get comfortable. We're here for you. It's okay if it's not perfect. You'll get there. Now… Go ahead and spread her legs."

With shaking hands, Henry leaned forward and gently pushed Emma's legs further apart.

"Now, lay down on top of her," the brunette coached Henry, giving him a small push. "Let your bodies fit together."

As he moved in closer, Emma reached up for him again and carefully guided the head of his stiff member to her entrance.

"Good boy," she cooed, stroking his hair back with her free hand and wiping several beads of sweat from his brow. "Now, move nice and slow."

"But what do I-"

"Just push it into me, Hen… It's alright."

When he hesitated, Regina told him, "Look at her. She's ready for you. See how wet she is?"

His eyes widened as he looked down between his mother's legs to see her entrance slick with her own arousal.

"That's for you, Henry," Regina whispered, kissing his neck from behind. "You're already doing a good job. Now, just do like I told you and push in until your bodies fit together."

His movement was clumsy at first, like he'd expected it to be – and his heart leapt when he heard the sound of Emma moaning as he pushed most of his length inside.

"Is… Is this okay?" he asked anxiously, breathing hard, after he'd recovered from the pressure surrounding his cock.

"Keep going, Hen," she breathed, gripping his hips loosely.

"Pull your hips back a bit," the brunette instructed him.

Again, he did as he was told, pulling back. He was slightly startled when Regina pressed her body against him and rocked his hips forward again, pushing his length back into Emma's core. The blonde let out a soft gasp, letting him know that he was definitely having an effect on her, and the noises she was making grew louder as her wife helped him by pulling his hips back again. Slowly, they worked up a rhythm, and Emma gripped her son's hips a little tighter.

Of course, being his first time, he didn't last long, and when his body started to shake and his groans become louder, his mothers knew it was close.

Shuddering, Henry started to pull away, but Regina slid her hands down his back and cooed, "It's alright sweetie. You can finish."

"But I… I… Oh, fuck. Mom… Fuck," he moaned, as Regina gently pushed against his rear to push him back into Emma's core.

She groaned when Regina sandwiched him between their bodies and she felt Henry's cock buried deep inside her. She pulled him even closer, closing the last thread of space between them as his body jerked and he cried out, louder this time, as he spilled himself inside her.

"Shit!" he cried, as soon as he'd recovered. "I'm so sorry! I didn't mean for it to be that fast! I… I…"

Although he was clearly distraught and Emma did want to comfort him and reassure him that it was fine, she was sweating and gasping for breath, leaving her just a little too flustered to speak.

"It's alright, Henry," Regina said softly, kissing the boy's neck from behind. "It's quick for most men their first time."

"But what about Mom? Shouldn't I-"

"You're going to use your fingers to finish her."

Henry's eyes went slightly wide. He'd never fingered a woman before, and he was obviously nervous about the prospect of not doing it properly.

"This is her clit," the brunette told her son, moving to sit beside them rather than behind Henry and reaching out to press two fingers gently against Emma's swollen bundle of nerves.

"Gina," Emma gasped, her body shocked by the sudden stimulation.

"But what if I-" Henry started, but Emma quickly cut him off.

"It's okay, Henry. I know you can do it. Touch me just like Mommy, okay?"

Demonstrating the desired movements, Regina rubbed her wife's clit a few times before guiding Henry's hand to the same spot.

His touch was more clumsy, and he used a little more pressure than was necessary, so between gasps of pleasure, Emma told him, "Easy, honey. Not so hard."

"I'm sorry!" he squeaked, looking horrified, thinking he'd hurt her. "I-"

"No, sweetie. It didn't hurt. It's just… It's a little better if you're nice and gentle, okay?"

Nodding his head, Henry continued his movements, until Regina took his hand and moved two of his fingers to Emma's opening.

"Now, push your fingers into her slowly."

He did as he was told, earning a soft moan from Emma's lips.

Then, Regina told him, "Now, curl them forward gently."

"Ah!" Emma cried out, feeling his fingertips pressing against her clenching walls.

"It feels… Mom… I can feel you, um…" the boy stuttered, amazed by the way she felt around his fingers.

"That's good, Henry, if you can feel her tightening," Regina explained. "That means you're doing a good job. It means her body likes it, and it feels good."

"Henry," Emma moaned, as the boy curled his fingers again.

"Alright, Hen. Just a little faster, okay? Pretty sure your mom is getting close."

"I am," Emma confessed, looking up into her son's shining eyes. "I'm… Fuck. Henry!"

She clenched around his fingers and released a new wave of arousal around them, soaking his hand. When her hips lifted into his touch, Henry smiled.

"Was that okay?" he asked.

It took Emma a moment to recover, which scared him slightly, but she replied with a nod and a smile as she reached up to stroke his cheek.

"You did a great job, honey."

"There. See? That wasn't so hard, was it?" the brunette asked with a matching smile.

He smiled back at both of them, then leaned back until he was sitting cross-legged on the bed.

"You're beautiful, Mom," he told the blonde.

She blushed. It was strange to hear this coming from her son, but coming from the young man who'd just made her climax, it was more than flattering.

"Alright, big boy," Emma said, sitting up slowly. "Think you're ready to give your mom some of that special treatment?"

Looking over at the brunette sitting beside him, he nodded.

"Alright," Emma said. "Lie back."

He did as he was told, and Regina straddled his lap. He was flaccid, but when she rubbed herself along his length and he felt the slickness of her arousal coating him, blood began to fill and stiffen his length.

"That's it, baby," Regina said softly, biting down on her lip to stifle the moans as his length stimulated her clit.

"Let Mommy get you hard, baby boy," Emma told him, stroking his abs and kissing his cheek.

As she continued to rock her hips backwards and forwards, her heat warming his member, Henry quickly got hard again. Soon, he was stiff enough to fill her, and Regina lifted her hips to kneel over him.

"You ready, honey?" she asked, reaching down to stroke some hair out of his face.

When he nodded, she gripped his hips and lowered herself onto his cock.

"Henry," she moaned in surprise, feeling herself growing full. "Fuck."

His eyes closed at the sound of his name being moaned, and he lifted his hips slightly to meet her. She pushed down on him, though, with the palms of her hands, and started to grind down onto him. He groaned as soon as she started to move. Rocking her hips forward, she moved his member inside of her and guided his hand to her clit.

"Rub her clit, Hen," Emma said softly, her hand sliding over his chest.

"Mom," he whimpered, as she started to bounce on his dick and cry out as he rubbed her a little harder. "Mom."

"Yes, Henry, yes."

"Am I-"

"You're perfect. It's perfect."

"Don't stop, Hen," Emma warned him. "Look at her face. She's gonna cum for you."

Hearing this made his muscles clench, and soon, as he lifted his hips up to meet every thrust, he felt her walls fluttering around the hard length of his cock.

Both of them cried out at the same time, saying each other's names, as they reached their peaks. When her orgasm had ended, Regina melted into her son, and he instinctively wrapped his arms around her. He didn't pull out as he softened inside of her, his come sliding out and dripping onto her thighs.

"That wasn't so bad, was it?" Emma asked him with a smile, curling her body against them as she draped an arm over them.

He shook his head and smiled, saying, "No. I feel much, much better. Thank you both. Thank you so, so much." When both smiled but neither spoke, he added shyly, "When do we get to do this again?"