Henry is just turned 17 in this fic, which is above age of consent in Maine.
Friday evening found Henry returning home from an outing with friends, but instead of being in high spirits as was normal when he'd been hanging out, he dragged his feet as he entered the mansion and called out a listless, "Hey, Mom, I'm home." He stood in the foyer for a moment, weighing his options, then went into the living room and slumped down onto the couch.
Regina looked up when he came in, watching him as he sat and frowning. He looked miserable for having just been out with friends, so she sat up straighter and reached over to squeeze his hand. "Hey sweetheart, are you all right?"
"I'm fine," Henry sighed, sounding anything but. He turned his hand over under Regina's and squeezed back, putting effort into giving her a half-smile. "It's just that Violet was there. With her new boyfriend."
"Oh, Henry." She wasn't sure what else to say, because how do you tell someone to not be hurt when their longtime girlfriend started seeing someone else. "I'm sorry. Is he someone you know from school?"
Shrugging, Henry shook his head. "Not really. I've seen him around, but we're not exactly in the same social circle. He's a jock. He's on like, every sports team the school has, all the girls swoon over him." All the girls including Violet, apparently. It had barely even been two weeks, and she'd already moved on with the most eligible guy in school.
Regina squeezed his hand, trying to think of a way to soothe his pain. "I'm sure it isn't all girls that are swooning over him," she countered. "I'm sure there's a girl out there who will be a much better fit with you."
"I thought so, but now Violet's dating him, and I mean, she knows me better than anyone, we dated for three years, and practically right after breaking up with me, she goes straight to him." Henry scuffed his foot against the carpet, frowning. "And if someone who knows me that well would rather be with him, what hope do I have of finding someone else?"
"Henry, because you're wonderful. This is a reflection on her, not you. Some people just don't fit together, and that's not your fault. If she doesn't want to be with you, that is her loss, because she's the one giving you up."
"I guess." Henry shrugged again, sighed. "It just sucks. I still think about her, and she's off with someone else. I didn't think she'd forget me so fast, you know?"
Regina frowned again, bringing her other hand to their joined hands, squeezing his between both of hers. "Maybe you should try to date someone. Or… I don't know. Maybe it would help take your mind off her."
"Why can't relationships be easy? Hit someone with a rock and live happily ever after. Sell your prized possession and get the girl. Get a tattoo and a soulmate in one fell swoop." It wasn't that easy, he knew it wasn't that easy, but right now it sure seemed like it.
"Henry," she chided lightly. "You're forgetting all the hard parts along with all those stories. Love is never easy, relationships aren't easy. If something is meant to be it will work out, and you and Violet breaking up, well maybe that's just your chance to find who can make you truly happy."
"It just seems so hard," Henry complained. "I mean, who would want me? I'm just Henry. Nobody's ever been interested in me except Violet, and now even she's dropped me." Pulling his hand from her grip, he slapped his hands against his thighs. "I might as well give up now, I'm not good-looking enough to catch a girl's eye, and there's nothing really special about me, either. Not compared to other guys."
Regina reached over, turning his face to her with two fingers under his chin. "Henry, you can't possibly believe that. You're very handsome, and so special. You have the heart of the truest believer, you're the author, you're kind and sweet and honest. There's so much special about you."
Henry met her gaze reluctantly, seeing the honesty in her eyes. Her earnestness warmed through him, and he lamented, "You're the only person who thinks that. Why can't I have a real girl see me the way you do?"
"A real girl?" Regina arched an eyebrow, half in amusement and half in challenge. "Am I not a real girl—woman?"
"I mean… yeah, I guess," Henry shrugged awkwardly and looked away. "But you're my mom, so I never really thought…" Glancing back at her, his gaze flicked down to her chest briefly and his cheeks flushed.
She caught his gaze, rolling her lips together and wondering if she could possibly… help him more than with reassuring words. "Just because I'm your mom means I can't be objective about your worth as a person?"
"No, cuz you have to say that I'm smart and handsome and all of that," Henry argued, shaking his head. "But if you weren't my mom, I bet you wouldn't actually think that." The thought depressed him, that even the one person who'd always been on his side would find him uninteresting if the circumstances were different, but he was sure it was true.
"I don't have to say anything. And I would still believe you're all the wonderful things I said, even if I wasn't your mother." She brought her hand to his arm, squeezing lightly. "I promise."
Henry scrunched up his nose slightly, the expression making him look more like Regina than was biologically possible. "It's okay, Mom, you don't have to say that. I can handle the truth, you know, I'm not a kid anymore."
Regina shook her head, bringing both her hands to hold his face. Leaning in far too close, she murmured, "I mean it. You're handsome, and so great. Anyone would be lucky to date you."
Eyes widening, Henry looked down at her lips, closer to his than he could ever remember them being since he stopped kissing her on the mouth when he'd decided he hated her. "Are you going to kiss me?" he asked, his voice high-pitched and almost making him sound like he was back in the clutches of puberty.
She faltered, moving back less than half an inch and almost dropping her hands from his face at the question. Regina didn't want him to get the wrong idea though, regardless of how she should feel about him getting the other wrong idea they were posed with. So, instead, she tilted her head and asked, "Do you want me to?"
Henry's breath stalled in his lungs for a moment, and he swallowed hard. Looking down at her lips again, he noted how full and soft they looked, and hesitantly reached out with one hand, resting it just above her knee. "I… Maybe?" he admitted quietly. It wasn't something he'd really thought about beyond passing acknowledgement that she was a beautiful woman that all his friends wanted to bed.
"Maybe. Maybe you just need a distraction, someone to show you that you're not missing out because you're single." Regina watched his eyes for a long moment, then let her gaze drift to his lips, wondering if she was terrible for even thinking about this.
"... Really?" Henry asked after a moment, squeezing her leg lightly and sliding his hand an inch or so higher. The thought was surprisingly appealing, and he smiled slightly.
Regina nodded slowly, knowing it was probably (no, really) a terrible idea, but she wanted to show him he was deserving of so much. His hand on her leg wasn't helping her clarity of mind, either. After a short moment, she leaned in and ever so lightly pressed a kiss to the corner of his lips. "You are so much more than you believe, Henry."
Henry turned his head slightly to chase the kiss, disappointed when he was too slow. "Thanks," he replied quietly, appreciating the attempt at making him feel better, even if the results were somewhat less than stellar.
When he'd responded, she felt more confident about her actions, and the small way his voice sounded squeezed her heart. So, wanting to prove she meant what she said, Regina leaned in again, this time with a firm press of her mouth against his.
Inhaling a surprised breath through his nose, Henry took a moment to catch up to reality before beginning to move his lips against hers, letting himself relax into the kiss and framing her bottom lip with his own, not quite sucking on it.
Regina let her eyes flutter closed, and she traced her tongue just lightly over his lower lip. He tasted sweet, like the sodas he liked to drink when she wasn't there to remind him how unhealthy they were.
Twisting to face her, Henry slid his hand further up her thigh and brought the other up to cup her jaw, holding her in place and meeting her tongue with his own, deepening the kiss. He had never in a million years expected something like this to happen, but he couldn't deny the way it sent warmth pulsing through him, settling in his groin.
She slipped her hands down his neck to his shoulders, lightly caressing her fingers over them through his shirt as they kissed. It was odd kissing him, because she knew it was wrong, knew she shouldn't be doing it, but it felt so good.
Henry had no idea how far this was going to go, or even really how far he wanted it to go, but he followed the urges of his body regardless, shifting his hand to Regina's inner thigh and curling his fingers, lightly raking his short nails over the satin pajama pants that kept her skin from him.
Needing to breathe deeper than the kiss would allow, Regina pulled her mouth from his, moving it slowly across his cheek. She let out a soft breath against the corner of his jaw, as she rested her forehead against his temple. "You are so wonderful," she murmured in echo of her earlier words.
Henry tilted his head and huffed a laugh against her neck, replying teasingly, "I'm starting to believe you." Moving his hand higher again, his swept his thumb over her inner thigh, just shy of where sons should definitely never touch their mothers. He wanted to touch her, wanted to know if maybe she was wet for him, but he didn't want to cross a line she didn't intend to allow him past.
"Just starting?" she asked, arching an eyebrow and pulling back to look at him. Despite knowing she should go upstairs, far away from him, away from the touch she was only half refusing to acknowledge, Regina couldn't. His hand was warm on her through the fabric of her clothes, and without even thinking of how she should respond, she shifted a little to open her legs wider at his touch.
"We'll see how it goes," Henry answered with a bit of a smirk. When she moved her legs apart, he took it as an invitation, and moved his hand to drag his thumb over the apex of her thighs, watching her closely and holding his breath for her reaction.
Regina shivered pleasantly. He was more confident than she'd expected from his earlier words, and she couldn't help but look down to watch his hand with wide eyes.
She wasn't pushing him away. He was touching her and she wasn't pushing him away. It was almost too much to believe, and Henry looked down as well, watching as he stroked his thumb up and down her sex through her clothes. Hopefully his experience with Violet would serve well enough to guide him through whatever it was he was getting himself into now.
She let out a heavy, shaky breath as arousal filled her body. Swallowing thickly, Regina cleared her throat and looked at him. "This is supposed to be about cheering you up."
"Oh, I'm quite enjoying myself," Henry assured her, leaning into her until she began to twist sideways and lay back, then he used his foot to push her legs further apart, making room so he could kneel between them. All the while he kept touching her, feeling the heat building against his fingers.
Regina's body felt on fire, and she wanted more, wanted to ask him to give her more, but she didn't know how to speak those words, to make that request of her son. Her legs twitched every time he brushed against the right spot, making her grip the couch in her hands in an attempt to calm herself.
Looking up at her face, Henry kissed her again, quickly, then licked his lips, his heart pounding as he asked, "Are… are you wet? For me?" He'd never said anything like that before, his limited experience not including verbal dirty talk, although he had sexted a few times. It was different saying the words aloud.
"I am," she admitted, not even considering the words before saying them. Regina kept her eyes on him, watching his darkened eyes, the slight glisten on his lips where his tongue had swiped over them, then back down to his hand.
Henry swallowed hard, his dick pulsing in his pants as her affirmation sent a heavy wave of arousal through him. "Can I feel it?" he asked, lifting his hand away from her to hook his fingertips in the waistband of her pants.
Her eyes followed his hand, heart pounding in her chest at the location of his fingers. If she let him touch her, there was no going back, but she didn't want him to stop, not really. And she was showing him he was desirable, stopping now would only serve to defeat the purpose of starting this, as well as likely just frustrate them both. So she nodded. "Go ahead."
A little nervously, well aware that it was crossing a line they wouldn't be able to come back from, Henry slipped his hand past the waistband of both pants and panties, pausing when he felt satin under his fingers. "Do you always wear fancy underwear?"
Chuckling softly, glad for the distraction from admitting how the touch felt to her, she nodded. "Most of the time, yes." Regina kept her hands placed safely on the couch cushion, wanting to prevent herself from doing anything he may not want.
"That's hot," Henry said, his mind suddenly filled with images of her in sexy lingerie beneath her mayoral outfits. Now that he was thinking of it, the mayoral outfits were pretty appealing, too. He pushed the thought from his mind, not wanting to get too distracted, and finally moved his hand further down, cupping her in his hand. "Oh," he breathed out, feeling smooth, wet folds under his fingers. "You are wet. For me."
The sound of his words settled in and Regina swallowed thickly, then said, "Just for you." And it was the truth, which was a problem all its own, but at the moment she didn't care. "How does that make you feel?"
Henry chuckled quietly and shifted his balance so he could grab one of Regina's hands with his free hand and press it against the hard bulge in his jeans. "How do you think it makes me feel?" His hips jerked into the touch, pushing harder into her palm.
She was too filled with want to ignore how good it felt to have an erection against her hand, so she gave as good of a squeeze as she could through his jeans and licked her lips. "Good."
Groaning, Henry braced himself with one hand and leaned over her, curling his fingers against her and finding her clit with a fingertip. "You can touch me," he invited, a little breathless. "I want you to touch me."
Regina's core throbbed at his words and touch, so she moved both hands to undo his jeans, then hesitated only a moment before slipping her hand beneath the band of his boxers to slide her palm along his dick.
"Fuck," Henry hissed, tensing and taking a moment to tighten his grip on his self-control. Then he pulled his hand from between Regina's thighs, resting it on her stomach and saying, "Can I see you? Is that okay?"
This was far more than she'd expected, even when she'd kissed him initially. There was no denying she wanted him, though, so Regina bit her bottom lip, slowly releasing it to tell him that yes, it was definitely okay.
Henry wasted no time in pulling open the buttons of her top, revealing her breasts encased in black lace. "Wow," he murmured, his eyes wide. Violet had never worn a bra like that, had never looked that good in her underwear.
Regardless of the fact that Henry was her focus for the moment, making him feel wanted and desirable, his reaction to her in her bra filled her body with want. "What would you like, Henry? Do you want to touch me more?"
"Of course I do. You're gorgeous." Henry glanced up at her, then stood up, pulling her to her feet as well and using the opportunity to push her top off and unclasp her bra. His first instinct was to touch, to cup her bare breasts in his hands and tease the nipples that were already standing firm, but he restrained himself, moving instead to push her pants and underwear down.
Regina felt momentarily self-conscious standing there fully naked in front of her much younger son, but brushed it off and decided to even the playing field. She reached for the hem of his shirt, tugging it up and off him, then going right after for his pants and boxers, shoving them off his hips so they could fall to the floor.
Henry bit his lip nervously as he was exposed to her, aware that he wasn't as muscled as any of the men he knew she'd been with. He was still lean and lanky, almost scrawny without the bulking layers of his clothes, and he was worried she would be turned off by it.
She looked him over, tilting her head to the side. Regina moved back toward him, bringing her hands to rest on his shoulders as she leaned in to kiss him again. He was Henry, he was perfect, and she'd never see him as anything less than that.
Relaxing as she kissed him, Henry brought his hands to her hips, then slid them to the small of her back, pulling her against him. Her breasts brushed his chest, sending tingles through him, but it was nothing compared to the feeling of his dick pressing against her, and he shifted his hips closer.
Regina moved her arms to hang loosely around his shoulders, pressing her body firmly to his as she deepened the kiss. After just a moment, she lowered one hand and wrapped her fingers around his cock, stroking him firmly; she was meant to be making him feel good after all.
Inhaling deeply, Henry nearly swore again, but held it back. Instead he trailed his mouth down Regina's neck, kissing and nuzzling her soft skin, and brought one hand back between her thighs. She was even wetter to his touch than she had been before, and he slid his fingers along the length of her, over her clit and to her entrance.
Gasping at the touch, she widened her stance just enough to give him a little more room to touch her. She tilted her head to the side, giving him more space there as well and letting her eyes fall shut at the wonderful feeling of being touched and kissed on.
"Come here," Henry murmured, sitting back down on the couch and pulling her with him onto his lap, grunting when his erection ended up half-squished between them. Perhaps he should've given her more warning, but all he'd been thinking of was getting her as close as possible, as accessible as possible.
Regina let out a quiet moan at the pressure against her, moving her hands to cradle his face, thumbs stroking over his cheeks. "You're perfect, Henry," she murmured, holding his gaze.
Henry smiled slowly at the honesty in her eyes, and tangled his fingers in her hair, drawing her into an almost rough kiss. "Can I have you?" he asked, the words groaned almost desperately into her mouth. "I want to fuck you. Please."
She nodded. "Me too. Um… here? Or do you want to go to a bed?" Regina wanted him to have it however he wanted; she was amenable in the current situation.
"That's too far," Henry shook his head, then leaned forward and took one of her nipples between his lips, sucking it briefly before glancing up at her again. "I need you now. Is that okay?"
"Of course." Regina shifted her hips back, wrapping her hand around him once more and stroking him. She moved her other hand into his hair, pulling his mouth back to her breast. "Right now?" she teased. "Are you certain you want your mom?"
Henry laughed against her breast and murmured, "You sure you want your son?" Moving his hands to her ass, he squeezed encouragingly and thrust up against her.
She grinned. "I'm in your lap, aren't I?" Regina moved her hips forward, angling his cock so it was pressed to her opening. After a second of enjoying that feeling, she lowered herself down onto him.
Any reply Henry might have voiced was lost to the tight heat of her around him and he groaned loudly. "Holy shit, you feel good." It was interesting, too, to be in this position. The few times he'd had sex with Violet, he was always the one on top, but he was enjoying having his hands free to explore and roam over Regina's curves.
Regina closed her eyes, dipping her head to kiss his shoulder as she took in the feeling of having him inside of her. It had been a while since she'd been with anyone, and while this certainly wasn't an experience she'd ever expected to have happen, he felt so good. So she told him that. "You do, too."
Henry brought his hands to her breasts, cupping them against his face as he kissed along her cleavage and rolled her nipples between thumb and forefinger. He couldn't pinpoint what it was, but everything about the encounter was simply better than it had been with Violet. Whether it was because Regina was more experienced, or because she was his mother, or some other reason, he didn't know, but he was certainly going to enjoy it.
Rolling her hips on him, she pressed a kiss to his hair while he enjoyed her breasts. Doing this with him shouldn't be as enjoyable as it was; she shouldn't even be doing it, but she wasn't regretting it.
"God, Mom," Henry sighed, taking one of her nipples in his mouth, sucking and licking it until he thought it couldn't get any harder, then biting down lightly and rolling his jaw. He almost wished they weren't having sex yet, so he could focus on learning her body without the distraction, but she felt too good to stop.
She moaned at the feeling of his teeth on her, hands squeezing his shoulders as her hips jerked forward in pleasure. "Mm, do that again," Regina breathed.
Henry did, almost reflexively, when she tightened around him, and then he chuckled. "You like that?" he asked, switching to the other nipple and repeating the attention.
"Uh huh." She nodded, closing her eyes just for a moment, but quickly reopening them to watch him. Regina rolled her hips forward again, grinding her hips in a smaller motion to follow, taking him in as deep as she could.
Slouching down slightly so it was easier to lift his hips, Henry thrust against her, one hand going back to her ass. The guys in school always talked about what a great ass she had, but he'd never really paid attention until now, and the firm muscle felt great in his hand.
Regina covered the hand he had on her breast with her own, then dragged it down her body to the small space between them. She pressed his fingers to her clit, dropping her head so her mouth was at his ear. "Give me more."
Henry's brain stalled for a moment, her husky voice short-circuiting his ability to think. "Anything," he rasped out hoarsely once he could focus again, and rubbed firm circles over her clit. His touch made her tighten around him again, and he groaned, too close to the edge.
"Just like that… that's great," she breathed, kissing his ear. She moved her hips faster, working to chase her orgasm.
Henry tried to hold back, pressing his forehead against Regina's sternum and gritting his teeth, but it was useless, his orgasm too close to ignore. Pulling her tightly against him, her jerked his hips up hard and brokenly groaned, "Mo-om," as he released into her.
When his grip relaxed a little, Regina began to rock her hips again in shallower, slower motions to bring him down. Pressing a kiss to his hair and bringing a hand up to stroke through it, she breathed in the scent of his shampoo and smiled faintly against him.
"I want you to come," Henry whispered breathlessly as he recovered, lifting his head to look at her. He began rubbing her clit again once he realized he'd stopped, and added, "Tell me what to do."
Regina's thighs twitched against him when he started rubbing her again. She met his gaze, deciding what would work best to get her off quick. "Faster on my clit," she directed, adding, "and play with my nipples more." She'd always loved that.
Henry did as she asked, sliding his hand up her body from her ass to her breast and pinching the nipple lightly as he took the other in his mouth again. He changed his touch on her clit to a rapid back-and-forth, able to move faster that way instead of the circles he'd been doing.
She let out a moan as he complied to her requests, building her up closer and closer. Regina was surprised she'd made it this long anyway, having been so long since she'd actually been fucked instead of taking care of herself with a vibrator.
Humming encouragingly, Henry bit down on her nipple again, since she seemed to like that, and pinched the other tighter, rolling it between his fingers. He wanted more than anything to feel her come around him, squeezing his cock before he got too soft and slipped out, so he rubbed her clit even faster, losing the rhythm for a moment in his enthusiasm.
The increase in roughness in his touch was enough to help push her over, and Regina let out a raspy moan as a rush of pleasure coursed through her body. "Fuck, Henry," she gasped, as her body tensed from her orgasm.
Henry groaned at the feeling of her spasming around him and he lightened his touch on her clit and slid his other arm around her waist, holding her against him. "That's amazing," he whispered, stringing kisses along her shoulder.
Regina smiled contentedly, tilting her head against his as she panted heavy breaths. "It was," she agreed. There was little motivation to move, both because she was so relaxed from her release, and also because Henry didn't seem eager to let go of her either.
As she relaxed more, Henry stopped touching her entirely and wrapped both arms around her, hands exploring the smooth planes of her back. "I guess I do believe you," he finally said with a small chuckle. "I mean, if you, pretty much the person who has the most reason to not be with me, if you want me, then I guess I'm not so bad after all."
"I think you missed the point." She laughed softly, bringing her hands to his face. "You're not 'not so bad.' You're great, and the right person will see it, and you'll forget about ever having been hurt."
"I'm not thinking about it now," Henry pointed out, grinning and leaning forward to kiss her. "You did a pretty good job of raising my mood. I like your new method." Hopefully it wouldn't be a one-time thing, because he'd never had sex that good, and now that he knew how good it could be, he wasn't sure he wanted to go back to girls his own age.
Regina arched an eyebrow, chuckling in amusement. "Well apparently I'm not the worst at spur of the moment ideas. Although I'm sure your family would disagree with that assessment."
"They don't have to find out," Henry said with an easy shrug. "I mean, it's not like I talk about my sex life with anyone, anyway. So… maybe, if you enjoyed yourself enough… we could…?" He raised his eyebrows, hoping he wouldn't have to ask outright.
"Do this again?" she finished, nodding slowly. "I… uh, yeah, I think we could." Regina still didn't feel guilty, even if she probably should, but she still wanted him to eventually find someone more fitting for him.
Grinning, Henry nodded once and hugged her tighter against him. "Cool. Thanks, Mom." It may not be a relationship, and chances were he was still going to miss Violet again tomorrow, but for tonight, he felt better.
Regina wrapped her arms around him and squeezed in return. "I love you. I'm glad to see you in better spirits." It broke her heart whenever he was upset.
"I love you, too." Henry nuzzled into her neck almost like he had done as a child, except this time he pressed his lips beneath her ear. "Thank you. For this. I didn't even realize it was something I might want, but… it was really great."
"Yeah, it's… it was a surprise. And it was great. I'm glad to have helped." Regina turned her head, kissing his temple. She brought a hand up, covering a yawn and turning her face away from his.
Henry grinned widely, teasing, "Did I wear you out?" Granted, it wasn't too far from the time she usually went to bed, but he was still going to take pride in her tiredness until contradicted.
"Well you did just fuck an old lady." Regina rolled her eyes playfully, scooting out of his lap and getting up to gather her clothing.
Snorting, Henry rolled his eyes, protesting, "You're not old. You've still got like… what, three or four more years before you're old?" he joked, standing and pulling his pants and boxers back on.
Regina picked up his shirt and threw it at his face, then pulled on her underwear. Deciding to skip her bra, she pulled her top back on, then her bottoms, and started button the top back up. "You're lucky I love you, or that joke would earn you a fireball."
"You said it first," Henry laughed, shaking his head. "Would you rather I had agreed?" Slipping back into his shirt, he smoothed the fabric down, surprised at how normal everything felt.
"You're nowhere near old, Mom," she answered, winking at him. Regina bent to pick up her bra, folding it and holding it in one hand.
"You're nowhere near old, Mom," Henry repeated dutifully in a flat monotone, then he grinned. "Better?" Glancing down at the bra in her hand, he remembered how she looked in it and wondered what other lacy pieces she owned that he might see one day.
Rolling her eyes, she shoved his arm. "Brat." She leaned in, kissing his cheek. "Are you going to bed or are you going to stay up a while?"
"I'm gonna just read in bed for a while," Henry answered, still chuckling, but taking a moment to kiss her cheek in return. "See you in the morning?"
"Of course. Sleep well, sweetheart." Regina turned to head upstairs, ready to sleep and to settle in with her thoughts.
"Night, Mom." Henry watched her walk away, tilting his head as he considered her. The guys at school were right, he realized, she did have a great ass. And he'd had his hands all over it as she fucked herself on him. He grinned widely, shaking his head in disbelief. If every breakup was going to end up like this, maybe being dumped wasn't so bad.