Mary Oaks

Leon’s eyes widened as Mary, the school student supervisor walked towards him, leaving the small circle of teachers. He glanced around the hallway, maybe it was someone else that had caught her attention. But he found no one in his vicinity. He sighed and turned back to Mary. He had only met her briefly when he had first enrolled at the school, a strict, no-nonsense woman. Leon was surprised that he had managed to get a small smile out of her from one of his jokes.

“How are you enjoying your time at the Academy, Leon. I hope you have settled in fine?” Mary Thompson said, stopping before him in the hallway.

Leon smiled at the busty supervisor, his eyes roaming her form. It didn’t look like he was in trouble at least, which meant he could relax a little. She was taller then him, but that didn’t bother Leon at all. It would make it more fun when he fucked her, have her ankles over her head as she screamed. His cock hardened in his pants at the thought, but he tried to control he libido. Leon was nowhere near that stage yet.

“Good, Ms Oaks. This whole school is really nice. The teachers -” Leon mind raced to a few of the full figured teachers in the school. A small part of his mind marveled at the fact that he had bedded three teachers now, and that they came back regularly for more. Now he realised he had his sights set on Mary. “ Are nice, The students are welcoming and the facilities top class. Not much else I could ask for in an Academy, though I hear you are new as well?”

“That is correct, I started this year.” Mary said, moving her purse from one hand to another. She then brushed a strand of her auburn hair out of the way of her eyes, her eyes roamed his body. “As a fellow person new to the school I felt it was prudent to keep track of you. Your grades are excellent, as expected from someone looking to study here.”

“Are you sure that wasn’t the only reason you were keeping an eye on me,” Leon wiggled his eyebrows, and then blatantly glanced down at her figure.

“Leon, I cannot believe you could suggest such a thing.” Mary said, her cheeks reddening. “While you are very hand - I mean you are..”

“I am what?” Leon asked, stepping closer to Mary. She was flustered already, her pupils dilating and her eyes racing along his form.

“I admit...you are handsome, but this line of questions can not continue.” Mary said, regaining some of her bearings.

“Of course Mary, I was only teasing.” Leon said, brushing a hand through his hair. “Though I have to say, you are really beautiful and I wouldn’t mind spending more time talking to you. Professionally of course.”

“Professionally, “Mary repeated the words, then nodded.” Yes, I wouldn’t mind that either.”

“Good, I can’t do anything tonight. But perhaps we could chat tomorrow. I have a free period after lunch,” Leon asked.

“I have as well,” Mary replied. “What would we be chatting about?”

“Anything, we are both new so why don’t we start there.” Leon said, stepping past Mary. He sniffed, taking in her perfume. He couldn’t wait to continue his seduction of Ms Oaks. “It is a good place to start, we can then move onto something else.”

“I would like that, I will meet you in my office.” Mary asked.

“Of course, Mary. See you then.” Leon purred and then walked away. She hadn’t corrected him about the usage of her first name, that was the first step in seducing her.

“Ah...were you waiting long for me Leon?” Mary asked, walking quickly to his desk.

“Not long, I was just reading.” Leon said, smiling up at Mary as she took a seat next to him. They were in the library, which had a few other students sitting inside. Leon had chosen a pair of seats and table far away from others. After all, he wanted to fuck Mary. His seduction would be smoother when there were less people to discover them. “Were you marking some papers or something?”

“No, there was an incident with some students I had to sort out. One of them put in a complaint about one of the teachers. Not that it will go anywhere.” Mary said, frowning at her hands that were clasped on her lap.

“Hmmm, would I know who this teacher was?” Leon asked, reaching forward and grasping her hands.

“Ah...err probably.” Mary blushed as her eyes locked with his. “I don’t really know why I am telling you all this.”

“Well, sometimes you need someone to let out your frustrations.” Leon replied. “I am happy to be that person you cum to for a shoulder to lean on.”

And a dick to ride on, Leon thought. He wondered what Mary would say if she knew his true thoughts. He really liked the way Mary looked, a stunning woman with a no nonsense personality. It would make a huge difference from Kendra and Lily’s more aggressive personalities.

Plus, Lily would never let me live it down if she thought I wasn’t backing her. Leon thought, while he had a healthy relationship with his teacher. He knew Lily was only like that with him. Other people faced the full **** of her wraith, just like the student that got on her bad side. She told him all about the situation, just before he fucked her senseless the previous night.

“I...ah thank you.” Mary said, gripping his fingers tightly. “I am not sure if that is appropriate, but I guess no one ever has to know I confide in a student.”

“That’s good,” Leon said.

“But, that does mean you have to come to me with any issues you have.” Mary said, narrowing her eyes. “This is a two way street, is that understood?”

“That’s fine by me,” Leon said. He knew he had her, what other teachers would accept so readily. “You said you were new to the school. Where did you work before?”

“A public school near the city. They had more students then here, which meant it was more hectic.” Mary said. “What about you?”

“A public school. I needed to move because of some things and found this place, so far everything here has been amazing.” Leon said, the women were the highlight of his time here so far.

“That’s good to hear, but if you have any issues please come to me.” Mary said,

“Why did you leave, would you get paid more in the city?” Leon asked.

“Not as much as you would think, this is a private school after all. Which means the pay is considerably higher, too much for me to say no to.” Mary said, blood rushing to her cheeks as she rubbed his palm with her fingers

“Huh, good to know.” Leon said, as it meant he knew his wealth would be one way he could seduce Mary.

“I think I do need your help.” Leon said, leaning forward in his seat. “Could you like to come round mine this weekend, I have a few issues that I could use some help with.”

“I ...ah why…” Mary asked, a blush forming on her cheeks as she rubbed his fingers. Her eyes widened as she suddenly realised the situation she was in. “Leon….”

“Would you like to come round?” Leon asked, already knowing he could brute **** the situation.

“Of course, if you have any domestic issues you need help with then I am happy to help.” Mary said, regaining her composure with the lie.

“Good,” Leon purred, he enjoyed the way Mary’s blush deepened.

—-

Leon only had a short time to prepare for Mary. Kelly has only left half hour earlier after their post trip fuck session. He had just changed the duvet on his bed when he heard the alarm to his gate go off.

A few minutes later he was opening the door to find Mary standing outside on his porch. She wore skintight jeans and a white blouse, it seemed like even if she was outside of work, she was still fairly smart. Her blouse accentuated her breasts, and her skinny jeans showed off the curves of her hips.

“You’re house is much bigger then I expected.” Mary said, a short time later while drinking some coffee. “I think I remember there being a house this big in the hills. I just didn’t expect a mansion!”

“I’ll show you the pool later,” Leon said. He sat on the couch next to Mary, drinking in her form.

“You have a pool?” Mary said, her eyes widening.

“Yeah, larger then the one in the school.” Leon smiled, remembering his experience with April during the week.

“Okay, I think I need to calm down.” Mary said, a blush forming on her cheeks.

“Ah...sorry, I don’t mean to show off or anything.” Leon said, glancing away at the clock.

“I didn’t mean it like that, I was just surprised.” Mary said, laying a hand on his.

Bingo, Leon thought. He raised an eyebrow at her, noting the deepening of her blush. He tightened his grip around her hands, rubbing his thumb along her delicate fingers.

“Thank you.” Leon said. “You said earlier you just arrived this year at the school, how have you settled in?”

“Yes, it’s been an experience. A private school is much different to a state run school.” Mary replied, shuffling around in her seat until her full attention was on him. “Have you settled in yet, I heard your scores are in the top percent.”

“Yes, it’s been really easy transferring here.” Leon said, leaning in and lowering his voice. “The teacher’s have been helpful, settling in as they have smooth thanks to them.”

“Really?” Mary asked, her voice trembling. Her colder demeaning vanishing under his intense gaze. “Who ...exactly has been the most helpful?”

“Hmmm…” Leon made a show of thinking about it before leaning closer and kissing Mary on the lips.

Mary ‘eeped’, which allowed his tongue entrance into her mouth. Her eyes widened, but they slowly closed as she became more involved in the kiss. Their tongues danced around each other slowly.

“There...have been a few that have helped me, but none more then Lily and Kendra.” Leon said, pulling away and taking a deep breath.

“You...you did...things with them?” Mary asked, placing her coffee on the table.

“Yes, the same things I am going to do to you.” Leon said.

“Ah...Leon, I think we should stop. I didn’t mean for things to go this far, or lead you on.” Mary said, coughing. But the blush still remained on her lips as she gazed levelly at him.

“Really, you come to my home alone and not expect something like this.” Leon grasped her hands and placed it on his crotch. His cock was hard, and pressed against his jeans. “Can you feel it, that’s what has made such stern and harsh teachers like Lily and Kendra my playthings. Just like it’s going to make you.”

“It’s….so big….and hard.” Mary mumbled, gazing down with wide eyes at his crotch.

“Yeah….now get on your knees.” Leon said, spreading his legs and pulling down his jeans. His cock sprang out, pointing up at the ceiling.

“I...err…” Mary mumbled, her eyes as wide as saucers. “God… you are so big.”

“Wait until you feel me inside of you.” Leon said. “Get on your knees and wrap your lips around my cock.”

“So..demanding.” Mary said, narrowing her eyes.

Leon wondered if she would say no, and leave. The risk of rejection was big, he hadn’t done as much prep as he had with the other teachers. But he felt like he had an advantage, there was something strange about Mary’s actions.

“Fine,” Mary said. She moved off the seat and sat on her haunches before him. She gazed up at his cock, which was easily the length of her face. “Fuck.”

Leon was surprised, he didn’t expect her to sweat. His hissed as her delicate fingers were wrapped around his shaft, she pointed his cock at her mouth and then slowly swallowed the tip. He groaned as her tongue lapped at the surface.

“Fuck, that’s good.” Leon moaned, grabbing her head and pushing her farther down his shaft.

“MMPH” Mary moaned, as his shaft disappeared inside her mouth. Until finally the head of his cock pressed against the back of her throat, causing her to gag.

“That’s it, keep it there.” Leon grinned down at her, enjoying the sensations flowing through him. Everytime she gagged, her throat constricted around his cock, sending more jolts of pleasure through him. He then pulled her up his shaft, only to slam her face back down on his cock. “Start sucking, I don’t want to do all the work.”

Mary for her part caught on quickly, as the seconds she gained control of the blowjob and directed her actions. Leon's grip on her head loosened as she started to lick the side of his shaft, coating his cock in a layer of her saliva.

“God...I can’t believe how big you are.” Mary said, before swallowing his cock right down to the hit.

Leon was again surprised at how quickly she managed to learn how to suck properly. He knew this must have been her first attempt, he would have to give her a good score for effort.

“Fuck, yes!” Leon felt his orgasm slowly build at the back of his mind. He could easily cum now, but after fucking Kelly senseless early he wanted his next load to be big. He also wanted to cum inside Mary, something about her shapely arse turned him on. Decision made, Leon opened his eyes and gazed down at Mary. “You are good, but let’s change things up. Shall we?”

“Sure….what would you like to do?” Mary asked, gazing up at him with lust. “I’m so wet, no one has ever been like this to me.”

“Really, well I aim to please.” Leon said, smiling down at her. “Since you’re wet already, let’s fuck.”

Leon reached down and pushed Mary onto her back, she fell down onto the rug beneath her in a gasp. She gazed warily back up at him as he stepped in between her spread legs. Leon gripped the hem of her jeans and pulled them off, they were tight jeans so it took him a few seconds.

“Fuck, you look nice.” Leon said, drinking in her partially naked form. She had a small bush above her pussy, larger then most of the other teachers.

“Ah….please….” Mary said, trying to closer her legs but stopped as he reached down and cupped her pussy. “Ah...god...you’re fingers.”

“You like?” Leon asked, slipping a finger inside her pussy.

“....oh...fuck...yes!” Mary moaned, gazing up at him with lust.

“Huh….thought you would resist a little bit more.” Leon said, smiling as he pulled out his hardened cock from his pants. “Get ready to fuck!”

“Ah...GOD!” Mary moaned, her chest arching upwards as he thrust inside.

Leon raised an eyebrow at the tell-tail snapping coming from inside her pussy. He sighed, letting the sensations coming from her pussy wash over him. Another complete virgin, he could add another tally to his lists.

Slowly, his cock disappeared inside her, almost all of it was inside before he had to stop. The pressure was intense, her inner walls clamping down on his shaft.

“Fuck...that feels nice.” Leon said, reaching down and ripping open her shirt. The buttons snapped off at the motion, revealing her large tit incased in a bra. “Let’s get rid of that shall we?”

“Le...Leon!” Mary moaned, her legs locked around his waist as her inner walls convulsed around his cock. They massaged his shaft for a few moments. “I’M CUMMING!”

Leon started to thrust in and out of her, trying to prolong her orgasm. Mary’s face was deep red and her eyes shut. He reached down and sucked on one of her nipples, biting down on her erect nipple every few moments.

“Oh...oh...GAWD!” Mary screamed, her hands wrapped around his neck. Her motions lessened as she finally opened her eyes, a look of longing on her face. “I….never cummed that hard. The pain...and then the pleasure, it was too much!”

“Hah...I am going to make you cum often.” Leon said, kissing her on the lips for a few moments before pulling away. “Aren’t you happy now that you gave into me? Now you will get fucked on a regular basis.”

“I...am indeed, please fuck me!” Mary moaned, a grin on her face.

“With pleasure,” Leon pulled out. He noted her juices on his shaft, but also the amount of blood. If he couldn’t wash out the blood from the rug then he would need to buy a new one. He thrust back in a moment later, discarding the thought. It was time to focus on Mary and fucking her selseless.

“Oh...god yes!” Mary said, her voice rising in pitch as she spoke. “You’re so deep…. So fucking deep!”

Leon raised an eyebrow at her cursing, he hadn’t expected the normally composed Mary to speak such words. But then again, getting rammed by a cock tended to make all his teachers a bit confused. He leaned down and started to place a number of kisses on her neck, up to her ear and then finally on her mouth. Their tongues danced around each other while they fucked. Mary tried to smash her tongue into his mouth, while he did the same.

Leon felt his orgasm building. He knew he wouldn’t last long now after her blowjob and how tightly her pussy was gripping. He increased his speed, now no longer worrying about holding back. He was now able to get his whole inside her, she was incredibly wet.

“God...fucking hell. I’m cumming!” Leon moaned, pulling away from Mary so that he could breath.

“Meee tooo!” Mary screamed into his ear, nearly causing him to go deaf.

Leon ground his teeth he orgasmed. Followed by Mary’s inner walls twitching around cock as she cummed in unison. He let out a low roar, enjoying the sensation of his balls emptying their contents into her pussy. Her inner walls contracted around his shaft as he held it inside her, to the hilt.

His heart pounded in his chest as his balls were finally drained. The content look on Mary’s face told Leon he did a good job. The ‘just fucked’ look on her face did wonders in keeping him hard, along with her pussy clenching and unclenching.

“Was...I ...good?” Mary asked, her voice barely above a whisper. Her chest rose and fell with each breath, sending her breasts into rocking motions.

“Yeah….you were fucking good. The best first fuck I have had with a teacher,” Leon said.

“With...a teacher?” Mary asked, raising an eyebrow. “I...am not your first?”

“Nope, and you definitely won’t be the last.” Leon said, pulling out of her in one smooth motion. “Get on you’re hands and knees, time to fuck you like a dog.”

“Ah...right.” Mary said, gingerly sitting up and then flopping onto her front. “I...don’t think I can go home like this.”

“Don’t worry, I am sure I have some clothes you can wear.” Leon said, lining his cock up with her entrance. Her arse was nice and round, he couldn’t wait to start slamming into it. “You have the same figure as April, I am sure you'll fit some of her clothes.”

“You...had sex with April...GAH!” Mary said, glancing over her shoulder at him. Her eyes widened as he thrust back into her, her inner walls clenching around his shaft. “Gods, you’re so deep.”

“If...you’re a good girl maybe I’ll fuck you with her.” Leon said, starting to pound his teacher. His eyes were mesmorised by her buttocks, as the skin rippled with each thrust. He was already fucking April and Veronica at the same time, he was sure they wouldn’t mind another teacher added to the mix. They were both literal nymphomaniacs after all. Each wanting to get pounded every day. The two teachers had taken their own relationship to the next level, enjoying each other even when he wasn’t around.

Not that I mind them fucking each other, I will put a stop to it if another guy is involved. Leon thought, knowing how possessive he was. He would never allow another guy anywhere near his woman, they could look, but that was all.

Leon increased his pace as he pounded her, enjoying the power he had over Mary. He brushed a hand through his hair before he started to spank his teacher, laying hard slaps against her buttocks. Her arse cheeks rippled each time he thrust inside, and again whenever he smacked her cheeks.

“OH GAWD YES! FUCKING HELL!” Mary screamed, slamming her hips back against him each time he thrust. “YES….”

Leon ground his teeth, her inner walls clamped down on his cock as an orgasm rocked through her. He was so close, he knew he just needed a bit more and he would cum.

“You arse is mine….right” Leon said, spanking her cheeks one final time before reaching down and grabbing her by the back of the neck. He pushed her face down into the rug, with the extra leverage he pounded Mary.

“YES….IT’S YOURS...DO WHATEVER YOU WANT, JUST DON’T STOP FUCKING ME!” Mary screamed, her inner walls spasmed.

Leon grinned as he cummed inside her. His balls emptied their content inside her tight pussy. Her pussy clamped down on his shaft as he sheathed it inside her. He leaned down and started to kiss the back of her neck, before moving up to her earlobe and sucking on them. All the while a euphoric sensation spread through him as his balls finally finished emptied. Mary’s pussy continued to massage his shaft, sucking out as much pleasure from him as possible.

“AGH!” Mary moaned, her face pressed into the floor.

“Fuck, I could do this all day.” Leon said, pulling away from her neck and brushing the sweat off his brow. He had done it before with Kendra and Lily, both of them were insatiable. But he doubted Mary could last that long on her first fuck with him.

“Ugh!” Mary said, lost in her own world.

Leon glanced down at her, he could only see the side of her face. His cock hardened at the ‘fucked senseless’ look on her face. From her open mouth and tongue sticking out, to how her pupils had rolled upwards.

“You won’t tell anyone else about us, right?” Leon said.

“Huh?”

“I said -” Leon smacked her arse cheek to emphasize his point. “You won’t tell anyone else about us? You do want to keep fucking me?”

“Uh...yeah, I do!” Mary said, licking her lips.

“Good, then you won’t also tell anyone that I am fucking other teachers.” Leon said, pulling his cock out of her pussy before slamming back inside. “Otherwise we won’t ever fuck again!”

“Ah...god!” Mary moaned, breathing deeply. “No! I won’t tell anyone!”

“Good.” Leon said, smiling down at Mary. “Let’s have a break, we can fuck some more later.”