When Henry accepts a challenge, he finds out that family really helps in every possible way.
Back with Henry and Regina. I hope you guys like it!
Henry never understood the fascination his friends have with boobs.
Sure he understands its biological role in human life and this is pretty much what they meant to him over the years. He thinks he never had him the opportunity to contemplate how erotic boobs can be due to his very unique childhood along with some particularly stressful teenage years. He heard his friends at college talking about ways to convince girls to at least show their boobs to them during the summer. A challenge ensued between them and 900 dollars were on the line for the best proof any of them could bring of them at least touching a boob.
Henry shook his head, smiling. He thought this to be useless in his case, but he joined the challenge anyway. He knew he would not win the money because he didn't have any way to get to touch a girl in Storybrooke. Him being the son of the two most power women in town kind of set him off limits to every girl.
One month into summer and nothing happened. Henry called Paige and tried to get something going. It didn't work, her father wasn't very friendly. He spoke to some of his old colleagues, but nothing happened. When July came he was already sure he would have to see someone else winning that money. He sighed heavily and went down stairs in a Sunday morning, looking for his mother.
That's when winds started to blow in his favor. He saw himself hardening, cock twitching inside his boxers, when he saw Regina with her face covered, topless and bathing in the early sun. Her steady breathing made her boobs rise and fall in a way that seemingly hypnotized Henry enough for him to only realize he was staring when she snapped her fingers right in front of him.
"Mom," he blinks, desperate. "I…" He is speechless, unable to form a coherent thought to explain why he was staring at her. Worst, his hand is inside his briefs and he didn't even notice it.
"You were staring at me and touching yourself," she points out rather obviously, looking into his eyes and… smirking. Why is she smirking? Also, why is she still topless?
"I'm sorry, I didn't mean to…"
"You clearly did mean something because otherwise you would still not be with your hand inside your boxers," Henry yanks his hand from inside his shorts and lowers his head, mortified that he was acting like a creep with his own mother.
"I'm sorry, mom, I really am," he begins, looking down and feeling his cheeks burn with pure shame.
"You don't need to be, baby," Regina speaks softly, cupping his face gently, raising his face for him to look at her.
"Of course I do," he begins, closing his eyes and stepping away from her touch. "This was wrong and I apologize," he finishes and turns his back to her, slowly heading inside the mansion.
"You stop right there, boy," her voice reaches him when he's about to cross the threshold of the kitchen door. He fidgets nervously and waits, knowing full well that she's about to lecture him. Henry just didn't expect to feel her hand touch his still very hard cock over his boxers.
"Mom, what are you doing?" He asks with wide eyes, trying to sound horrified, but actually moaning when she pushes her hand inside his boxers.
"Tell me, Henry," she begins, her voice huskier than usual, eyes studying his face curiously. "Why were you staring at me like that?"
He groans when she frees his cock and starts pumping him slowly. His head falls back against the doorstep with a thud, heart racing madly in his chest. He says nothing because he simply can't. His mind is apparently frozen and incapable of doing anything but enjoy the way her small hand is wrapped around him.
She suddenly stops her ministrations, stepping away from him.
"Why were you staring at me like that, Henry?" Her voice is serious and demanding, snapping him out of his trance.
"Boobs," he blurts out.
"What?"
"Boobs, that's why I was staring at you, mom. I was mesmerized within a few seconds and I'm sorry," he lowers his head again and takes a few steps back away from her.
"There's no need to be sorry about it," she begins, taking two steps forward. He takes two more back.
"This is wrong, and you know it," he tells her weakly, taking another step back when she takes one more forward.
"Is it wrong? Do you really believe that?" She gets closer to him trapping him between her body and the wall opposite to the kitchen counter.
"I don't know," he tells her, looking into her eyes without seeing her real intention with those words.
"You don't know?" She asks, and presses her bare boobs to his naked chest. Henry groans loud enough to get someone's attention, good thing there is no one in the house. Regina's hand pinch one of his nipples, making him gasp, before it heads south to pump his cock a feels times before she kneels before him.
"Mom, what are you doing?" His voice is shaken and the muscles of his thighs are quivering with anticipation. He knows what's going to happen, and although he still thinks it's wrong, he doesn't care anymore. Something this exhilarating can't be wrong in any possible way.
"Proving to you that I don't think this is wrong," Regina slowly pulls his briefs down his legs, lightly caressing his legs down and upwards until she's facing his cock. He's hard, and she smirks with pride knowing she is doing this to him. She takes the head of his shaft into her mouth, sucking it gently, swirling her tongue around the tip a few times before taking him into her mouth.
Henry looks down when Regina slowly runs her tongue up and down his length, flicking the tip of her tongue along the underside of his shaft, teasing him with tiny flicks around the head before she takes him fully into her mouth, bobbing her head up and down in slow motions.
It's so good to have his mother sucking his cock that he completely forgets he was opposing to this a few minutes ago. He feels his balls getting heavy when the warmth of her mouth envelopes him with each downward motion, his cock swelling further inside her mouth.
She releases him with a wet pop, smirking and licking just the tip before getting up, winking at him before turning her back, swaying her hips in her way upstairs.
Henry is apparently frozen in place, gobsmacked with everything that's happening to him. He picks up his boxers and runs after her, catching up when she's sitting on the mattress, crossing her legs and waiting. He closes and locks the door, turning to look at her, waiting for her next move.
"Have you ever…" she uncrosses her legs and points to her pussy, a question he can proudly say he knows how to properly answer.
Regina looks down when her son kneels between her legs, looking up at her with a joyful smirk on his face. He runs a finger between her slit, feeling it hot and wet. He strokes it up and down a few times before he pushes it inside her. She moans and falls back on the mattress.
She shifts her hips, propping her feet on the edge of the bed, legs wide open for Henry, and he wastes no time. He rapidly flicks the tip of his tongue against her clit while he rubs a finger against her entrance, feeling her wetness surge forward.
She moans when he gently nips her pussy lips, lightly touching the tender skin with the tip of his fingers. He then dives in, stroking his tongue between her folds from her entrance to her clit, making her legs quiver when he closes his mouth over her pussy, mimicking a kiss before pushing his tongue inside her.
It doesn't take too long for Regina to reach for his hair, pressing his face against her more firmly, telling him without uttering a single word that she was about to come. Henry closes his lips around her clit, thrusting two fingers inside her, fucking her with quick thrusts, the wet sounds filling up the silence of the bedroom right before her shouts of pleasure echo through the space.
Placing gentle kisses upon her thighs and up her body, Henry reaches her beautiful face, smiling at the sight of her sweaty face and satisfied smile.
"Was it any good, mom?"
"It was fantastic! Where did you learn to be this good?"
"Frat parties and focus on the girls," there's a smug smile on his lovely face. "My dad told me that, to always pay attention to what the girl wants. It has been effective so far," he winks at her and lies down by her side.
Minutes go by in comfortable silence when she gets up heading to the bathroom, legs a bit wobbly but steady enough for her not to fall.
Henry hears when she opens the cabinet. He has no idea what she's looking for, but it doesn't take too long for her to come back, putting a small bottle over his chest. He gazes at it curiously for a moment before he realizes what she wants.
She straddles his hips, fitting his cock between her pussy lips, moving her hips up and down his length, wetting him with her arousal. Yes, she's throbbing for him again, but first…
Regina takes Henry's big hands and put them over her breasts, covering them firmly, encouraging the young man to massage them. She guides his hands to the right places, showing him how he should squeeze them. He sits up and licks her puckered nipples, one at a time, before taking each boob into his mouth, sucking them enthusiastically.
He spends a long time just playing with Regina's boobs. Her groans and whimpers working like a fuel to his heart.
"Henry, wait!" Her voice is husky and deep, almost pleading because she feels like she can come if he keeps playing with her boobs like that. She's breathing rapidly when she puts her hands on his shoulders, pulling him away from her.
"What is it, mom?" He asks, mouth reaching for her breast again. She stops him, cupping his face again and making him look at her.
"Why are you so interested in my boobs now?"
He looks around the bedroom, considering his options before going for the truth. Henry explains everything to her from his lack of interest in anything related to boobs to the challenge his friends threw at each other. She giggles when he tells her about the conditions to win the challenge, a devilish smirk gracing her beautiful features.
"You will win very easily," she tells him, picking up the bottle she put over the bedside table earlier.
"What do you mean?"
"I mean that you have the entire summer to play with these boobs and take pictures, even record some videos and sort out the best and win this money," she speaks excitedly, pouring some of the oil over her breasts.
"Mom, I'm not interested in this challenge anymore. I got a lot more than I bargained for," he reaches for her, placing hot open mouthed kisses from her neck up to her jaw until he found her earlobe, nipping it gently.
"Oh, but you can have everything in this case, darling, fuck your mom and get the money," she chuckles and he shakes his head.
"You are crazy, mom," he tells her, stroking his cock and just trying to imagine what she will do.
"Maybe, but you are not complaining, are you?"
"Not at all, I'm quite pleased, actually," he winks and catches the bottle Regina tosses his way.
"Pour some of these on your cock," she commands and he complies readily.
"Come here!" She orders and he gets to her quickly. Regina shifts on the bed and leans her back against the headboard, looking at Henry's cock and considering her next move. "Listen carefully," she begins, his eyes focused on her. "I'm going to hold my boobs together like this, and then you stick your cock between them," she explains and he frowns. "What, Henry?"
"I don't get it," he seems really confused and Regina smiles.
"Baby, you're about to fuck mommy's boobs," she smirks.
"Oh!" He groans and closes his eyes tightly. Henry can't believe what is happening to him. He's quite sure he's dreaming or something, but he will do whatever she tells him to do, and if she's willing to help him win the money, so be it!
"Can I?" Henry asks when Regina pours more oil over her breasts. She nods and he kneels in front of her, sitting on his heels, and reaches for them, massaging and squeezing, swirling the tip of his tongue around her nipples, moaning when she pumps his cock.
Henry kneels in front of her, the tip of his cock teasing her. She's really determined to help him win this challenge, not to mention she'll get laid for the rest of the summer and quite frankly he being her son isn't a problem at all.
"Come here now, baby," she takes his hand and sighs when she feels his cock brushing against her tits. "Do your best, this is only the first time, we'll have time to improve," she takes his shaft in her hand guides him to the underside of her breasts, positioning him and helping him with the first handful of thrusts before he takes over.
Henry covers Regina's hands with his when he steadies his thrusts. His cock is sliding easily between her tits, and he feels her squeezing them around him every time he thrusts up, tossing his head back when he feels his balls tighten with each push of his cock.
Regina looks up, watching his face contort in pleasure, mouth hanging open. She takes her hands away from her boobs and places them in his ass, massaging the firm muscles, her hands wandering down his thighs before coming up again to fondle his balls, squeezing and pulling them gently.
Henry quickens his thrusts, grunting when she puts her hands over his tightening the grip around his cock and when he moans loud and deep, he frees his cock from Regina's grip and strokes himself coming hard, emptying himself all over her boobs.
He collapses beside her, breathing erratically, and throwing a hand over his eyes to prepare himself to the reality of never doing this again.
"So, was it any good, baby?" She mirrors his early question, hands running up and down his chest. Her voice reaches him with the force of a reality he doesn't want to face.
"Of course it was, mom," he speaks breathlessly, looking at her who's still leaning on the headboard of the bed, a satisfied smile all over her face. Regina picks up her phone and snaps some pictures of her boobs covered with his seed.
"What are you doing, mom?"
"Gathering proof," she says simply, snapping a few more photos before putting her phone back on the bedside. She lowers her body and absentmindedly runs her fingertips in circles over his belly.
"I don't think we should keep doing this," he begins and she looks at him, putting a finger over his lips. She covers his mouth with hers, just a light pressure of lips, turning her body towards him, lying on top of him.
"I think we should keep doing this," she replies and sits up straddling his hips again. This time there's no playfulness in her eyes, just love. "I know this is uncommon, but I love you and you love me," she entwines their fingers and speaks as seriously as she can. "And everything we did here felt good and natural, at least it was for me. I don't think there's nothing wrong if we commit to keep this between ourselves and be discreet," she smiles again, adding with a naughty glint in her eyes. "Besides, this is not finished yet, my boy," she leans down, hovering her lips over his, licking the corner of his mouth. "You still have work to do, after all you still didn't fuck me properly."
He manages to gasp and groan at the same time, feeling his cock twitch, hardening when she takes him in her mouth once again, her skilled mouth doing her magic, making his cock throb for her. She lies on her back, legs opened, and the happy look in her face erases any hesitation left.
Henry runs the tip of his cock up and down her slit, pressing it against her clit, right before pushing himself inside deeply, earning a guttural moan. She presses her heels against his lower back, cupping his neck and pulling him down to her, kissing him deeply, pushing her tongue inside his mouth. He does the same, his tongue mimicking the motions of his hips. He's rocking back and forth, shifting slightly his pelvis rubbing deliciously against her clit.
Soon they find a rhythm, their sweat mingling, hands exploring, hips rocking together, gasps of surprise and moans of pleasure filling the bedroom alongside the smell of sex and wonder. Henry pounds and pounds her, his whole body sings with pleasure when she runs her nails up his back, marking him as hers. Grabbing a boob in his hand, he squeezes it hard enough to make her gasp, her walls fluttering around him when she comes.
And Henry pounds her faster and harder, quickening his thrusts, mesmerized by the smell of her perfume and tightness of her pussy, and when he comes the only thing he can clearly think about is the 900 dollars waiting for him.
Reviews are always appreciated.
