Author's Note: 16 is the age of consent for most states in the US, including Maine. This isn't a story about pedophilia. On that note, under 18 sex with someone over 18 will be performed. If that's not your thing, don't read it. TW: Incest, underage (still age of consent), voyeurism.
It was nearly one in the morning when Henry heard something slam into the wall coming from what sounded like his mom's room. Getting out of bed, he tiptoed to her bedroom door, which was slightly cracked and saw his mom's back, completely bare down to the dark underwear that barely covered her ass. He watched, noticing she was facing someone, and sitting on his lap, though he couldn't tell who it was yet. Watching as her head tilted back, and the man's head lowered and was doing something to his mom's chest, and from the porn he had watched, he could only guess that the guy was sucking her nipples.
"Oh, David…yes," he heard her moan. Immediately, he stiffened at the thought of his grandpa cheating on his True Love. He decided he had to keep watching to make sure it was really him and not just some other David. He watched as the man picked her up and turned them over, hovering over his mother's body, and allowing Henry to catch a glimpse of her bare chest, almost making him look away. When he tried, though, he found that he couldn't, even when he did realize it really was his grandpa. The sight of her breasts heaving with her deep breaths was too entrancing.
He watched as David bit Regina's nipple, pulling his mouth away, and the nipple with it. His mom writhed beneath David and Henry couldn't help the fact that it was turning him on. He didn't know if it was because he was practically watching porn, live, in his own home, or if it had something to do with how hot his mom is. It was something he's always heard from the guys, that for a former Evil Queen, she was the hottest person in town.
David slid down her body and pulled her underwear off, licking her vagina, and Henry didn't understand much about that, so he made a mental note to look it up. Whatever his grandpa was doing was making his mom moan, her body moving fast and jerky and if he had to guess, she was having an orgasm. The only type of porn he'd ever watched, though, a guy was fucking the woman when she orgasmed. He really had to figure out what David was doing.
Being sixteen, he knew what he was doing was wrong and he tried to walk away, but his dick became hard immediately when he heard a rough moan from his mom. Then he heard her tell David that she needed him to be inside of her. Watching as David knelt between her legs and lifted her long, tan limbs, David put his dick into her and his mom bent her knees, pressing her feet against his grandpa's chest. He'd never seen that done in any porn either, but David was fucking her really hard, and he looked really big, a lot bigger than Henry was.
His mom was almost screaming by the end of it, and Henry couldn't help but hold himself inside his hands, squeezing his cock but not moving. He didn't want to make any noise; he didn't want to be caught. But she was making so many noises, and she obviously thought he was asleep and couldn't hear, and that turned him on even more. Henry watched as she came completely undone, falling flat against the bed, her legs dropping to either side of David, completely limp and obviously unable to hold them up any longer. His grandpa, however, kept moving, and he could hear his mom whimpering and the sound of David pounding against her until he groaned and fell on top of his mom.
Henry's eyes widened at the sudden end, and he backed up slowly, going back to his room with a solemn vow to look up how to make a woman orgasm without his penis, and to study more positions, because there was clearly a lot he didn't know.
Almost two months passed and David came over at least once every weekend, Henry always stayed up late to listen for him so he could tiptoe down the hall and watch. Most times the door was closed, so he would listen instead, the sounds leading his imagination. He expanded his knowledge of sex and different positions over the weeks, and he knew that whenever he was ready to have sex, he would mostly know what he was doing. Sometimes he masturbated, actually, he masturbated a lot, only sometimes to a picture of his mom that he'd always had on his nightstand.
It was Sunday night and David hadn't been by that weekend, so after Henry said goodnight to his mom, on her third glass of wine, he headed up to his bedroom, hiding under his blanket, reading a comic with his flashlight and waited. He waited until nearly 2:30, and when he heard nothing but his mom's movements, alone, in her room, he got up and knocked on the door.
"Mom?" he asked, pushing the door open slightly to reveal her sitting on the edge of her bed in a silk tank top and a pair of silk pajama pants. Her head shot up to look at him, and he couldn't help but stare down her low tank top to the space between her breasts.
"Henry?" she breathed. "What are you doing up?"
"I…was…um, I was waiting up. I…are you sad that grandpa didn't come over this weekend?" he asked, sitting on the bed next to his mom.
"What?" she started, shocked. "Henry…how do you know about that? I…I'm so—"
"Don't worry. I'm not mad at you. I understand it, I guess."
"What do you understand?"
"Why he'd want to come have sex with you," he answered, his cheeks flushing with his words.
"What do you mean, Henry?"
"I mean…like…what guy in their right mind wouldn't want to have sex with you."
Regina listened to his words, and it wasn't necessarily what he said that worried her, but how he said it. "Henry…"
"No, mom. I don't care what you say, and I don't care if it's wrong. I…I've been watching you guys. Sometimes you leave the door open and…the first time it was an accident, but then I just couldn't help it."
"Please, Henry, stop." Regina felt herself begin to grow warm between her legs. Something about being watched while being fucked had her getting wet. "Henry, you're my son. That isn't something you should be doing."
"Yeah? Well, I've watched a ton of movies about civilizations exactly like how you lived in the Enchanted Forest and incest happened all the time! Tell me that it's so wrong."
Regina couldn't say anything, she just sat there, looking at her son who was no longer really a boy, he was a young man, and he was physically bigger than her. He had passed the awkward stage of puberty and he was tall, probably taking after Charming's genes. Henry leaned into her and pressed his lips against hers, moving them smoothly against her mouth. She wondered when he learned to kiss fairly well. After a moment she pulled away. "We can't…"
"Please, mom. Just stop. David isn't here tonight…just let me take care of you." Her head felt fuzzy from the bottle of wine she had drank that evening, and when his mouth latched onto hers again, she kissed back, letting his tongue slide between her lips when he traced it between them. He lifted his hand and pushed it down the top of shirt, finding her nipple and pinching it. Shuddering, she gasped against his mouth.
"Henry…?"
"Yeah?"
"Just…don't call me mom right now." He nodded as he pushed against her, causing her to lie back onto the bed. Every movement they made, the pull in her stomach grew stronger against the denial that was edging her mind, begging to come out of her mouth. When he slid his hands under her tank top, easily pushing it up her body and over her head, her mind blanked and everything became about physical pleasure.
"Regina…" he said, his breath whispering against her skin. Kissing her stomach, he moved up, taking a nipple into his mouth as he had watched David do so many times, and he bit, wondering if she would react the same way to him that she always did with David. Sure enough, she arched her back, pushing her chest into him and he moved his hand to her other breast, rolling the nipple between his fingers.
"Henry…" she whispered, and he lifted his head, moving up to catch her lips in a kiss. He slid his tongue in again, meeting hers in a slow dance. He moved the hand that was on her right breast down her stomach, reaching beneath her pants and underwear, letting his fingers slide between her thighs, feeling the wetness he wasn't sure would be there for him, but was very relieved to find.
"Oh Regina," he said, his voice husky and far deeper than she ever imagined it could be.
"Henry…" she moaned, causing his dick to harden against her hip, where he was pressed against her. He moved off her, pulling her pants and panties with him, sliding them off her legs. Burying his face between her thighs, and not caring that she had her eyes closed, he licked at her wetness, rubbing his nose over her clit. She bucked forward. Inhaling the scent of her arousal, Henry groaned against her pussy. She smelled good, unlike anything he had ever experienced before, but he couldn't quite describe the deliciousness of it. He licked her again, tasting her carefully, reveling in the sweet and unfamiliar taste of her juices.
"Let me fuck you," he said, moving one hand to her face and forcing her to look down at him. Once she opened her eyes, he saw that her chocolate irises were completely taken over in her arousal, black depths looking at him. She nodded, not speaking, and he pushed himself off the bed, pushing his clothes off and kneeling between her legs quickly. He pushed himself into her, hoping she wouldn't care that he was so much smaller than David.
When Regina felt Henry push himself into her, she regretted it for a moment. He is your son, she thought to herself. But the fact was, she was too far gone to stop it. He was young, and it showed in his size, but as he pounded himself against her, she angled her hips so every time he pushed into her, his dick hit the special spot within her and she was so far gone that it didn't hardly take long for her to finish. He was thrusting into her, too excitedly and not rhythmically at all, but it was entirely Henry and she couldn't find herself disliking it. As he fucked her, she took it and she even kissed him back as he leaned down to press his mouth to hers, his tongue eagerly licking the inside of her mouth, every part he could reach.
It didn't take him long to finish either, being so inexperienced. He relaxed with his release, collapsing onto her body with exhaustion, his cheek resting against her bare breast.
"God," he breathed. "That was…that was amazing." He paused, looking up to look at her face. "Did you…um, did you have an orgasm?"
She nodded and gave him a small smile. "I did, sweetheart. Thank you."
"Thank you…for being my first." Regina groaned internally, wondering what she had just done.