"We have got precisely one hour and forty minutes until Regina returns home from work." Mary Margaret started to pull off her beige raincoat and light blue sandals.
"Well we better get started then Grandma." Henry grinned at his very young looking Grandmother who was a little over a couple of years older than his birth mother.
"Do not call me that young man!" Mary Margaret pushed Henry down onto his bed with his favourite blanket on it after pulling off her thick woolly jumper and Henry's shirt and t-shirt.
"Hey. I am in charge today and I say you better watch your tone." Henry pulled a now nearly naked Mary Margaret besides her cotton underwear, towards him by her hips.
"Or what?"
"I've got these for starters." Henry held up four pairs of handcuffs.
"How did you get all of them Henry?" Mary Margaret eyes bulged as she thought of the amount of trouble Henry has probably got her into, especially when she will need to find a way to return them all to the Sheriff station.
"Don't worry about that. Ma has a box full of them with her bails bond old stuff. She won't notice them missing so I'll get to keep them here." Henry wiggled his eyebrows at a flustered Mary Margaret before catching her off guard and pressing her down onto his single sized bed and locking both wrists and both ankles to each bed post.
"Henry!" Mary Margaret squeaked out.
"Stay." Henry ordered like he was speaking to a dog before exiting the room leaving her spread out only with a few thin layers preserving her modesty.
She was not left long which she was relieved to see but when felt Henry start to cut off her underwear with the scissors he retrieved, she swore out loud.
"Henry! I needed those. Do you expect me to walk home without any underwear on?"
Henry raised an eyebrow. He looked every bit like his adoptive mother at that moment. "Yes I do. You behave like a slut so I'm going to help you with furthering your career."
Henry heard a gasp but was more surprised not to hear a response from the short haired school teacher, just her chin jutting out in annoyance. So he let his eyes wonder over Mary Margaret's nude body.
She was quite pale which contrasted well with her hair. Her collar bone protruded slightly leading down to two ample sized breasts peaked with large pink nipples.
Henry licked his lips at them. He wanted to devour them then possibly put some nipple clamps on them paired with a clamp on her clit too. His breath quaked at that image as he looked down to his present between her spread legs.
She was shaven but had left a single strip of hair above her clit. The usually small sized bundle was a swollen dark red. Probably the same size as her erect nipples. Below her clit, there was a thick film of pussy juice layered across Mary Margaret's inner and outer lips.
Henry had to use both his thumbs to spread her plump lips to the side to see the entrance to her pussy that would soon be filled with cock. He leaned forward, hearing the older woman's breath hitch saying 'Yes Henry, lick my cunt!'. He decided to tease her instead and took a deep breath in. She smelled divine. He let his tongue travel across where her legs met her body, making sure to stay clear from her pussy. He then let his tongue tickle each bum cheek for a while as his teacher squirmed around on his bed. He saw her other hole then.
"Mmm, what a nice looking ass hole you have. I'm going to have fun with that Mary Margaret!"
"Not there. Isn't that dirty? David has never gone there!" Mary Margaret lifted her head to look down between her legs.
"So your grandson will be taking your ass virginity then. I will be recording this on my phone!" Henry grinned in excitement.
"Who would know that you would be such a dirty boy Henry?" The dark haired woman leaned back and gasped when she felt a smooth slickness brush against her puckered hole.
"Says you who's spread out naked on her grandson's bed begging to be fucked by his cock and getting her asshole licked." Henry laughed before taking another lick of her puckered hole. Then he flattened his tongue and swiped from ass straight to clit making the brunette arch her back and press her vagina into Henry's face.
He then tickled her pussy lips with the tip of his tongue before spreading her plump lips with his thumbs again to gain access to her tight vagina. He prodded once with his tongue, enjoying the sweet taste of her pussy juice before moving up to her erect clit and sucking gently getting it wet with his saliva.
"I think we will put this in a clamp today." Henry stated whilst lightly pinching Mary Margaret's sensitive clit.
"Oh yes Henry. Punish my pussy. Make my naughty pussy be good again."
Henry got the clamps and put one on her clit which made her squeal and squirm; pulling her hands and feet against the handcuffs on the bed posts.
"Behave." Henry ordered, making the woman settle down.
He saw her chest heave with excitement, when he attached the other two clamps to her nipples which where gasping for attention.
Mary Margaret was now restrained with two chained clamps attached to her nipples that traveled down to one single chain that had a clamp attached to her clit. She looked a delicious site to her grandson who stood at the end of the bed taking a few photos on his iPhone for later.
"I can't wait to fuck your ass. These pictures look so hot. Imagine I showed the whole class these." Henry grinned at his grandmother who looked up at him pleading to be taken.
"No. Please Henry. Please fuck me. I need your cock fucking my pussy. I need your cock inside me." Mary Margaret was on the edge of insanity. Her vagina was releasing quantities of liquid soaking the bed and her nipples and clit were burning under the clamps. She needed release.
Henry pulled his jeans and boxers off. His large cock sprung out hard and ready for pussy. He needed to feel the depths of Mary Margaret around his cock, milking his length.
He balanced between her legs and slapped her pussy with his hand a couple of times until it was a light shade of red. He loved the way she squirmed for him before pushing his cock balls deep into her tight vagina.
"Oh yes Mary Margaret. This pussy belongs to me. Daddy is home." Henry shouted with his head looking up to the ceiling, embracing the feeling of his cock being squeezed by a tight, wet, pulsing channel.
"Oh god. You are so big. I can feel you stretching me." The dark haired woman tried to lift her hips, wanting her grandson to start fucking her pussy.
Henry slapped his hand down on her pubic bone. "No. Stay. I choose when your pussy gets a fucking. Do you understand me?"
Mary Margaret had never seen this authoritative side of Henry before, but she liked it. It made her walls unconsciously squeeze the large cock currently inside her pussy. "Yes Henry, I understand."
"Oh I felt that, you naughty girl. Squeezing my cock without permission, tsk tsk. I think we should play a game." Henry looked down at Mary Margaret and lifted the chain resting on her abdomen.
The school teacher looked at the chain in his hands wondering what he was going to do.
"Now you are going to squeeze when I tell you and if you don't do it sufficiently then I will pull this chain a little bit tighter each time until it is done. Do you understand?" Henry toyed with the chain connected to the three clamps as he looked into the other brunette's eyes.
She nodded before confirming with a 'yes'. She felt juices escape from her pussy and run down her thighs, whilst she tried to keep her vaginal muscles from squeezing without permission from Henry.
Henry smiled. He was going to enjoy this game, he grabbed his phone a turned it on to video and pressed record. He hovered over her and pointed the camera down so it would have a clear view of Mary Margaret's entire body with Henry's cock stuffed deep inside her. It was a magnificent site.
He waited for his teacher to calm her breathing a little before starting. "Squeeze."
He felt his cock tighten inside her vagina for a split second. He needed more. He pulled on the chain slightly which tugged on the clamps hearing a groan from the brunette woman.
"This time, keep squeezing until I say stop. Squeeze."
This time he felt his cock twitch with the pressure of slick walls wrapped around his length.
Henry saw her face strain at the difficulty of holding the contraction. He swirled his hips, making his cock move in circles deep inside her pussy.
"Fuck Henry I can't hold it, that long." Mary Margaret breathed deeply with exhaustion.
Henry pulled the chain a little bit tighter. Her nipples were now visibly being pulled away from her body, making them appear longer. Her clit was being pulled upward towards her breasts, making the sensitive nerves more exposed.
The short haired brunette groaned loud with pain and pleasure. She accidentally squeezed Henry's cock which earned her nipples and clit to be pulled more.
"Last time. Squeeze." Henry demanded. He was enjoying this sensation but the view was even better for his arousal. "Stop…Squeeze." Henry wanted to see how Mary Margaret would react, which she responded well and squeezed his cock even harder making him groan. "Stop… Squeeze…Stop"
Henry realised she was getting good so he decided he would trick her. He wanted his cock to be thoroughly taken care of by this wet, tight pussy before she got her ass taken care off. "Squeeze…Stop…Squeeze…Stop. Squeeze. Stop…Stop…Squeeze. Squeeze."
Henry swirled his hips whilst pulling the chain each mistake Mary Margaret made. She now had her back fully arched off the bed with her nipples and clit being pulled to their limit as she squeezed her dripping pussy for dear life onto his cock. It was a beautiful site, Henry thought as his cock felt like it was in a vice.
"And…Stop." Henry let go of the chain and pulled his cock out allowing Mary Margaret to rest for a moment.
He looked at the clock and saw he had around forty five minutes left before his Mom would be back to make dinner. That was plenty of time.
Henry looked at his cock, wondering if he would need any lube. It was covered in thick creamy pussy juice. He had never seen his cock like this and it had never been that big and hard before. He decided that they didn't need lube considering the mess Mary Margaret had made all over her pussy and thighs.
"Henry fuck me please, I need you now. I need to cum. PLEASE!" Mary Margaret pleaded with tears in her eyes.
He nodded and took care of her virgin puckered hole, smearing all of the juice escaping from her vagina in and around her ass. He pushed two fingers into her drenched pussy, swirling them around and hooked them to press into her G spot making her squirm before removing them.
Henry looked at her virgin ass one last time before pushing two digits in. He thrusted them in and out, making his school teacher sigh and moan at the new feeling. She was ready.
"I'm going to fuck your ass. And I'm going to finger your pussy. And you will just lie there and milk my cock with your tight hole like a good girl. Understood?"
All that Mary Margaret could do was nod. She just need to cum.
Henry lined his cock up to her slick puckered hole and pushed in slowly until he was balls deep, hearing groans of reassurance from his school teacher. Then he pushed two fingers into her pussy.
He quickly grabbed his phone which was still recording and pointed the camera to Mary Margaret's face then straight to where they were joined. He loved the feeling of her ass. It was warm and tight. But nothing would beat the feeling of her wet pussy.
Henry slowly started thrusting until he was built up to a speed where both his cock and fingers were shooting in and out of his school teacher's ass and pussy.
"Oh fuck, you better cum soon Mary Margaret. Oh you better get that pussy and ass milking my cock soon."
"Ah I'm cumming Henry. I'm cumming." Floods of liquid sprayed out of her pussy.
Henry opened his mouth wide, drinking up the sweet nectar as he felt his seed spraying the walls of her tight ass.
"Henry? Sweetheart what's going…"
Henry and Mary Margaret looked over to the door to see Regina standing there with her hand on the door knob.