It started when Henry was sixteen years old. He had never seen a woman properly before. Of course he had seen women in his family and the women around Storybrooke. But they had clothes on. He wanted to see a woman without clothes on. He wanted to see Regina, his mom, and he knew just how to get her to do what he wants.

"Sweetheart, what's wrong? You've hardly touched your food." Regina's worry reached her eyes as she watched her sixteen year old son push the food around his plate.

Henry shrugged his shoulders. Inside he was grinning and patting himself on the back for being able to predict his mom's behaviour.

He knew Regina's soft spots. And he knew that if he played the saddened little boy card, his mom would do anything to get him back to being happy, especially if it meant she had one up on Emma.

Just a few more minutes he thought and she will be putty in his hands.

"Is it Emma?" Regina swallowed back the lump in her throat as she thought of this woman who seemed to be trying to steal her life from her.

"No."

"Then what is it dear? You can tell me Henry, I'm your mother." Regina encouraged.

Henry put his fork down and pushed his chin down to his chest, displaying the perfect image of a miserable boy.

"It hurts."

Regina could hardly hear his voice. "What hurts sweetheart?"

Henry smiled knowing she had her where he wanted her. He stood up and pulled his trousers and boxers down, letting his impressive 7 inch cock bounce out of his underwear to stand proudly in front of Regina's eyes.

"It hurts mom and it won't stop." Henry whined and made his eyes water a little for effect.

Regina was in shock. She did not expect to ever see her son like this. To see her little boy – well not so little - stand in front of her with a large cock. She could not help think that Henry's cock did look rather delicious. It was slightly darker coloured than Henry's usual colour and was long and thick for his age. Regina made an audible gulp when she saw a slight wetness on the tip of Henry's cock. It was when she saw a hand gently stroking the length that she looked back up to see her son's twisted smile.

"Mom, please. Help me. I'm in pain." Henry mimicked his earlier whining voice whilst jacking off on front of his brunette mother.

"Hen..." Regina cleared her throat, gaining some sense of clarity. "Henry go to your room now!"

"Mom…"

"Henry, go!" Regina growled out between clenched teeth. She was angry at herself for falling for her son's antics.

Henry was confused. He thought he had her. He thought when he showed her his cock she would surely not deny him her body. But she did. She told him to go to his room like a child. 'I'm not a child. I'm a man!' Henry reassured himself before he pulled up his boxers and trousers and left to go upstairs.

Not even five minutes later whilst Henry lay down on his bed thinking of unpleasant thoughts to try and get his cock to go down he heard his mother walk past his room and shut her bedroom door.

"Shit." Henry breathed out. He screwed up and upset his mom. He didn't want her to be mad at him that was the last thing he wanted to happen.

Henry took a couple of deep breaths preparing his apology in his head before getting up to head to Regina's bedroom.

He silently opened the door, to be stopped in his tracks to the most beautiful site he had ever seen. His mother was spread eagled naked on top of her bed with her eyes closed and a hand working furiously between her legs.

'Oh fuck' Henry thought as he tried to keep his breathing quiet so he could watch the site of his mother masturbating.

"Henry, oh Henry. Right there. Put that lovely cock into my pussy sweetheart." Regina moaned aloud whilst inserting two fingers into her drenched vagina.

Henry froze. She was imagining him fucking her. He decided it was make or break.

He moved into the room closer to the bottom of the bed quietly to get a better view of the first view of a woman's naked body. He started at his mom's relaxed face then moved his eyes down to her chest. Her breasts were beautiful; not too big and not too small – just the right size for his hands to massage them and hold them. Her nipples were dark and erect with arousal. They were begging to be taken care of and he would surely do that for Regina. His eyes then moved down her toned abdomen then feasted onto her dark haired mound dampened with her own arousal. He could not see her sex very well but what he saw he could not wait to see more of.

"Oh yes. You feel so good inside me. I feel so full Henry."

Henry quickly pulled off his clothes and began stroking his hardened cock whilst watching his mom fuck her pussy faster and moving her other hand to pinch her right nipple.

All of a sudden Regina moved her hand from her pussy, showing Henry his first unobstructed wet pussy. It was a delicious site. Henry feasted his eyes. He wanted to tickle that pussy with his tongue.

Regina had an unshaven, natural pussy. Henry wanted to see more but couldn't. He wished his mom was waxed so he could see her secret garden much better but he wasn't going to complain about his first woman.

Henry was too focused on feasting his eye that he almost lost the site of Regina's arousal soaked fingers be swallowed by her red plump lips, sucking them until the delicious cream vanished from her digits.

That was the last straw for Henry. He didn't care to be quiet now. He pounced on the bed between Regina's legs leaning above her. "Is this what you want mom?"

Regina snapped her eyes open. Her pupils dilated with arousal drew to Henry pointing his large cock at the entrance to her pussy.

"Henry get off me."

"Is this what you want? I want you so much mommy. Let me make you feel good." Henry gasped out then placed a delicate kiss on her parted lips not taking it any further.

Regina knew in her mind she should chuck Henry out of her room and place a memory spell on each of them. But she did want him. She wanted to be wanted again by her son and if this was her only chance at it then she would take it.

She placed a hand around Henry's neck, taking a moment to look into the face that used to ask her to read him a bedtime story. But now Henry's face was full of desire and want for her. She pulled Henry's down and captured his lips into a heated kiss before opening her lips for invitation for him to explore with her. Henry hesitated and pulled back.

"Does this mean…"

"Henry I want you. Now make love to me."

At that request, Henry pushed into his mom with one thrust. Regina groaned with the size of his cock stretching her walls. It was huge but filled her so nicely.

"Stay still for a minute baby. You are bigger than what I've had before." Regina whispered into his ear.

"You're so tight and… and wet mom."

"Hmm. And it's all for you." Breathing out feeling her walls begin to accommodate to his length.

Regina moved her hips up towards Henry, hinting for him to start moving. He started off with slow unsure thrusts until Regina coaxed him into a rhythm.

He moved up onto his knees when he was confident to set the pace on his own. He looked down at his mom. Her breasts were bouncing with each thrust into her pussy. Then his eyes met Regina's. They were connected for a second; sharing their love. Until Henry hit a particular spot in the brunette making her arch her back. "Right there, Henry. That's the spot. Fuck me right there."

Henry aimed his thrusts to that spot. His mom's screams and moans building his own arousal deep in his belly. His cock had never been this hard before but he was determined to hold off until his mom had her orgasm.

He looked down where they were connected. He could see more of Regina's sex now. He saw her plump outer lips wrap around his cock and swallow it up each time he went balls deep into her vagina. It was a magnificent site. He wished his phone was handy to take a picture of his mom like this for later but moved that thought to the back of his mind for later.

"Henry, rub my clit please."

Henry stopped his thrusting and looked at Regina with confusion.

Regina understood and took one of his hands at her hips and guided it to her swollen clit. "Rub in circles here but not too rough."

Henry experimented with a few circles earning a few moans from Regina who encouraged him to move with both her hands grabbing his bum.

That was all the sixteen year old needed before he started to thrust again but with more vigour as his mom's screams of pleasure vibrated through the room.

He moved down to kiss Regina, massaging her tongue with his.

They were moaning into each other's mouth as they brought each other to the brink. Regina arched her back up into Henry, pressing her sensitive nipples into her son's chest as she felt Henry explode inside her. His seed coating the inside of her vagina, whilst her walls milked his cock.

Henry collapsed on top of Regina, pressing his face into the nook of her neck wrapping his arms around her shaking body. He didn't want to move. He wanted to stay like this forever with his mom. With Regina.

Regina felt Henry remove his cock from inside her after a minute and rolled them over so she was resting against him with his arms securely wrapped around her. She embraced the moment of feeling safe within a pair of arms after grabbing the bedsheet to cover them

"That was so good!" Henry let out, unable to contain his thoughts.

Regina laughed at his boyish nature. "I'm glad you approve sweetheart."

They both laid there in comfortable silence with each other. Basking in the heat, radiating from bare, sweaty skin.

"Can I ask you something?" Henry waited for a nod.

"Why do you not shave your pus… private area, like the women in Grandpa's magazines?" Regina looked up at Henry raising an eyebrow, "I mean I don't mind. I was just curious."

Regina turned over onto her stomach so she was facing Henry, "Putting aside the fact that those magazines are not for your eyes to see because of our current position. I will say that not all women look the same down there as they do in those magazines Henry."

"I know that mom. I was…"

"…just curious." Regina was beginning to get uncomfortable with the topic and tried to change the subject. "You always were a curious boy. But you are not much of a boy now, are you?" Regina raised an eyebrow when Henry pushed his nether region into Regina's stomach.

"Nope." Henry grinned. "So was it a thing in the enchanted forest or something?"

Regina cleared her throat. Obviously Henry was not going to drop the topic. "Yes I suppose it was a thing in the enchanted forest Henry. Women generally didn't want to look like little girls."

Henry could sense his mom's irritation at the subject when she moved herself off of his chest to his side.

"Is it something that bothers you Henry?"

"No." Henry was quick to answer which earned him a raised eyebrow. Nothing ever came good when he lied to Regina. "It's just that… I can't see you as well."

"Is being able to see my vagina important to you?" Regina asked calmly as if she was asking Henry what he wanted for dinner.

Henry faced Regina deciding he had to be a man and not hide away like a child. "I would like to see your vagina when I make love to you but if it's not something you want then I won't complain."

Regina took note of Henry's new found confidence but decided to toy with him. "You are being very presumptuous aren't you dear?"

"Erm… I didn't… mean to… presume. I was just…" Henry decided to give up. He sat up and put his face in his hands. "I'm sorry."

Regina laughed. "Henry I was teasing. Though it is something we need to talk about dear. We need to know where we go from here." She looked at him, knowing that they needed to have a conversation about what their relationship means.

However Regina didn't want to have that conversation just yet as well did Henry. "But for now, whilst I go and shave my pussy, you should go and fetch us something to eat and drink. We will need to keep our energy levels up!" The brunette woman grinned and walked stark naked to the en-suite bathroom before closing the door.