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Ellen let out a soft sigh. She had wanted so badly to be mad at him for the B minus he got on the quiz, for not concentrating in class, for day dreaming, but after his confession—how could she be mad?

"So what is the solution then? I mean we can't very well chastise Ms. Sanford for being attractive enough to capture your attention."

"What can I say? I like mature women . . . you best of all, of course."

"Thank you for the compliment hon, but the penalty still stands. No fun and games tomorrow and if your quiz score today is below a B . . . well you know the penalty."

"Yeah a fucking month. Mom, I'm screwed. I . . . I probably will get worse than a B today. I mean, not only will I, as usual, not be able to concentrate but now I am . . . yeah totally bummed out about . . . tomorrow."

"Well what do you suggest? Talk to Ms. Sanford and tell her to make her quizzes easier so I can keep giving me son his Friday night hand jobs?"

"Of course not, Mom but maybe you could . . . ahhh . . . shit you will never go for it."

"Try me. I mean, after all, if your mom has proven anything by now . . ." Standing up, she circled around her desk so she was standing directly in front of him. "It's she is willing to go that extra mile to make you happy, honey."

"Well I was just thinking if you could like . . . hmm, take care of me . . . before Ms. Sanford's class then I would be able to concentrate on her lecture and probably ace her stupid quiz."

Ellen smiled at her son's ingenuity before answering. "Nice try, but you are in the penalty box this week, sweetie. Or did you forget? I mean what is the purpose of me penalizing you by not giving you your Friday night treat if I take care of you on Thursday."

"If you took care of me today, we could skip the next two Friday's and then we would be back on track. I mean, I am serious, Mom. I . . ." He sighed heavily, looking up at her in quiet desperation. "I can't do badly on today's quiz. I mean . . . a month . . . whole month. I . . . no way."

Ellen leaned back against her desk as she stood pondering things before speaking. "Yeah, but even if I did say yes to your suggestion we hardly have time to do it baby. I mean by the time we rushed home, did it, and then even if we rushed back you would be late for her class." She glanced at her phone. "As it stands you only have forty five minutes until her class so . . . yeah we don't have time to go home."

Smiling sheepishly, Jimmy whispered as he reached out and took her hand. "Who says we have to go home?"

"Wait . . . seriously . . . you want me to take care of you here . . . in my office."

"Yeah, why not? I mean you can call out to Renee and tell her you don't want to be disturbed. You could lock the door even. I mean with Mr. Locke out still you are, like, in charge right so if you don't want to be disturbed . . . no one will disturb you."

Mr. Locke was the principal and was currently on the second week of a two month medical leave so it was true, she was in charge. Everything else her son said also happened to be true: she did have a lock on her office door, and she could call out to her secretary Renee and tell her she was not to be disturbed under any circumstances. If there was some kind of dire emergency Renee would call her first anyways giving them time to not get caught doing anything untold.

On the surface it seemed like a doable idea but . . . but Jesus in her office, in the middle of a school day!

Then he started to beg. "Please, Mom, pretty please. I promise I will fucking ace the hell out of her quiz . . . I mean that . . . I will not get just at least a B but an A . . . or hmm, A minus anyways."

"And if you don't get the A minus then what?"

"Then you can give me the month penalty."

"I don't know, hon. I mean . . . right here."

"Oh c'mon Mom, please. I can't go a month without . . . you." He squeezed her hands tight. "Please . . . I will take you out tomorrow night to any restaurant you want. My treat . . . no matter how expensive."

She squeezed his hand back her will to resist crumbling. "There is that new Italian place on Gilmore. Supposed to be good . . . and expensive."

"Sure, I will make reservations as soon as I get home today. Please . . . I need this . . . more than you can imagine."

"Oh honey . . . Jesus I can't believe I am even considering this."

"Don't consider . . . just say yes."

Ellen sighed again before twisting around. Grabbing the phone, she punched the number to her secretary. "Yeah, Renee . . . listen I don't want to be disturbed for the next forty minutes. I have a bit of a family emergency I guess you could call it to discuss with my son."

There was a brief pause before she said, "Yes no calls and no visitors please until after one. In fact, why don't you just take an early lunch and lock the outer door . . . put a note on the door to just call my cell in case of a real emergency. Yeah, thanks Renee."

Jimmy smiled at his mom.

"You better ace that quiz mister," Ellen said with a sigh.

"Yeah, just like you better ace giving me this," Jimmy said happily as he boldly grabbed his mom's hand, pushing it against his crotch.

"Hmm, I have never failed yet have I, Son?" she purred as she started to rub his cock, Jesus he was already hard, through his jeans.

He started to rise up, doubtlessly as a prelude in trying to kiss her, but she pushed him back down. "Sit down, relax for a second. I'm going to make sure Renee went to lunch already."

Ellen, still trying to wrap her head around how the fuck he had talked her into doing this, crossed her office to the door. Peeking out, she saw the outer office was empty and the out-of-office sign was placed on the door. She twisted the lock on her door, securing it before heading back over to her son.

Approaching him from behind, she placed her hands gently on his shoulders, before beginning to massage them.

Leaning over, she whispered in his ear, "You promise to concentrate really hard in her class today and ace the quiz and I will give you the best hand job . . . ever."

"Really?"

"Really, but you have to promise me."

"I will ace it . . . promise, but can you come around to my front so I can see you."

"Why," she said as she continued to knead his shoulders lightly.

"Because you are the image of professional beauty and I desire to gaze upon such beauty before I receive my just reward."

Ellen did look nice, both professionally and personally, in her dark checkered suit jacket, pale pink colored blouse, and dark checkered skirt that perfectly matched her suit jacket. Her hair was done up nice and her make up applied just right making her a vision of pure beauty in his eyes.

She laughed lightly as she circled around him. "More like naughty reward, hon," she said.

Leaning back against her wide oak desk she gave him a sly look. "So are you ready . . . you felt ready earlier already."

"Hmm, not quite," he said as he decided to try and take advantage of the momentum he seemed to have with her this afternoon.

"Really, not yet. Why not?"

"Because you are still dressed."

His boldness made her laugh out loud. "Seriously, you can't expect me to get undressed . . . I mean what if someone calls on my cell? What if there is an emergency and I'm in my office undressed."

"OK . . . I see your point but can you at least take off your suit jacket? Please."

"Hmm, since you said please I suppose I could at least do that."

She took a step back, before slowly removing her professional suit jacket and neatly draping it over the back of her chair on the other side of the desk.

"Better?' she said as she moved around the desk toward him again as he reclined in his chair.

"Somewhat, but it would be more better if you could continue stripping for me . . . I mean you don't have to get naked just maybe take off your blouse and skirt."

Again she laughed at his boldness. "You are a persistent anyways, Son, but the answer is still no."

But directly after telling him no he looked so totally crestfallen that Ellen quickly throw him a bone. "Tell you want, the chances of an emergency happening in the next forty minutes or so is pretty low so . . . well I suppose I could, at the very least . . ." Smiling at him, she moved her hands to the front of her blouse. "Unbutton my blouse for you, allowing you to catch a glimpse of whatever sexy bra your very professional vice principal, the esteemed Mrs. Grant, is wearing under her boring business attire."

She was about to unbutton her blouse when she suddenly stopped as she hit upon an idea to spice up what was happening. Now if only Jimmy would go along it might be kind of fun.

"I mean, I guess I really don't have a choice since you are, in fact, blackmailing me huh young man?"

Jimmy smiled as he picked up on what she was doing right away. Once again, they would be role playing. "That is a fact Mrs. Grant so if you don't want your secret revealed I suggest you do as I say."

Inspired by her son picking up on the direction she was leading him she quickly replied. "But first tell me, how exactly did you find about my dark past . . . about me working as a stripper and about my time as a comfort girl at a massage parlor?"

"Yeah, who would have ever believed the esteemed Mrs. Grant was a fucking stripper and worked giving . . . ahh happy endings at a sleazy Asian massage parlor? Well I will tell you how I found out. My dad, he is a private investigator, and he ran a complete background check on you . . . unlike the half assed one the school did before allowing you to get hired as a vice principal."

"Hmm, well obviously, Jimmy I wouldn't want those facts to come to light. So what exactly do you want?"

He gestured at her blouse. "Take off your fucking blouse."

"My blouse," she intoned in mock surprise. "Surely you can't be serious. I mean . . ."

"And why not? You are hot . . . I mean for a vice principal and all. I mean, why you think I am always getting in trouble and being sent to your office Mrs. Grant."

Really," she said in a soft whisper. "You . . . like have a crush on your vice principal, young man."

He nodded his head slowly yes before barking, "Now . . . unbutton it . . . and don't make me ask again."

Ellen, her heart pounding in her chest, slowly undid her blouse as she stood in front of him.

When she got it completely unbuttoned, he stood up. Reaching out, he slowly pulled it down and half way off of her so it was hanging about midway down on her upper arms, revealing the sexy pink lace trimmed dark navy blue bra she was wearing. He looked at it closer—the cups were adorned with little pink hearts and other oblong shapes splashed across it as a decorative touch. He found the bra to be, like his mother, utterly gorgeous.

"Now you seen it . . . seen what I wear under my professional attire . . . so that should be enough for you. You should go," she whispered playing the role of being both shy and scared to the hilt.

"Hmm, not hardly, Mrs. Grant. If you want me to keep your secrets you are going to have to give me something a bit more than just showing off your sexy little bra."

"W-what more do you want?"

He took a small step forward. Using one finger, he tilted her chin upwards so she was staring directly into his eyes. "Only what I have been dreaming about all school year, Mrs. Grant. A kiss."

Slowly he moved his mouth towards hers. She tried, not very hard though, to move away but, using one hand, he carefully held her face in place as he planted a small kiss on her lips.

She didn't kiss him back though causing him to whisper to her harshly. "You need to do better than that, Mrs. Grant. Kiss me back . . . please."

"Well, since you said please," she breathed. Their lips came together again and after a trio of light kisses, he snaked a tongue deep into her open mouth causing her to stiffen. As he swirled his tongue inside her mouth, he brought his hands up, first across her bare tummy and then onto the soft mounds of her breasts.

She immediately swatted his hands away as she pulled back, breaking their kiss off.

"Please no . . . you can't."

"Why not?" he hissed at her.

"Because . . . because I'm embarrassed . . . my breasts . . . I mean they . . . they are not very big at all. I wear padded bras usually coz of that."

"I don't care. I bet they are still beautiful big or not. Let me see them . . . take your fucking bra off!" He moved forward menacingly, using the bulk of his bigger body to push her backwards so she was leaning back against her desk.

"Please no . . . how about . . . I'll . . . I'll let you touch them again."

"While we are kissing some more?" he whispered. "And this time Mrs. Grant, you had better kiss me back for real . . . and don't even think of pushing my hands away. In fact . . ."

He took her hands forcefully, pushing them down so they rested on the desk. "Don't you dare raise your hands off your desk."

This time when they kissed Mrs. Grant did indeed kiss her young handsome blackmailer back so very deliciously, punching her tongue deep in his mouth, swirling it around to maximum effect, just as his hands came up and began to softly knead her small tits through her bra.

They exchanged an increasingly passionate series of kisses as he continued to massage her tits, causing her to squirm against the desk.

Sensing the time was right to try for some more, the young blackmailer carefully slipped one hand down and off of her breasts. Slowly he started to stroke her bare thigh, the skirt came down to just above her knee, as she, surprisingly, did nothing to stop him, even as his hand slipped up and under her skirt.

She was wet, exceedingly wet, he found as his fingers easily slipped under the puny protective covering of the skimpy thong panties she was wearing under her skirt.

Mrs. Grant let out a loud hiss as his finger penetrated deep inside of her. He let his kisses fall down now, attacking her sensitive neck and throat as he slowly worked his index finger in and out of her.

Ellen gyrated her hips, her breath coming in shorts gasps now. Jesus if he keeps this up he is going to make me come!

For some reason this panicked her as a small inner voice begged her to STOP HIM.

It tried using reason on her. Surely you aren't going to allow your son . . . you son to make you come here . . . on your desk . . . at your work . . . at his school!!

She gave in to the voice. Reaching down, she grabbed his hand. "Please . . . we don't have much time left . . . before you gotta get to class. Let me . . . let me take care of you."

Leaning back, he smiled at her. "Go ahead."

"Here . . . come over here." She hopped butt first up onto her desk while waving for him to come closer. Reaching out, after he stopped right in front of her, she hurriedly undid his belt before yanking the zipper down on his jeans.

His cock, already a raging hard monster, with her help, came springing out of his boxers.

Reaching back, she grabbed her purse slung over the back of her chair, pulling out the bottle of edible lube. After applying a liberal amount to her hand, she wrapped it around the fullness of his cock.

"Oh God," he moaned as she began to stroke him softly. He only allowed her a few three or four good strokes before he said, "Stop."

She gave him a questioning look.

"I need more than just a hand job Mrs. Grant if you want me to stay silent."

Ellen's heart leaped in her throat. What more did he want, surely he wasn't expecting to . . . to do her right here in her office!

"What do you want young man," she asked quietly in a voice that trembled ever so slightly.

Reaching out, he used both his hands to pull her gently off of the desk and onto her feet. After a brief pause, he leaned in close to her, whispering, "I want you to put it in your mouth."

She shook her head no while mouthing the word, although no sound came out.

"Please, Mrs. Grant. Pretty please. I will never ask you for anything . . . ever again. Please."

Placing both hands on her shoulders, he applied gentle downward pressure trying to force her onto her knees. She resisted, at first, but when he whispered another desperate, "Please . . . pretty please," she caved, allowing herself to be pushed onto her knees.

It was right in front of her, pointed at her mouth like a loaded gun. She stared at it thoughtfully for a good long ten seconds, the tension building before closing her eyes and opening her mouth.

"Oh Christ," he moaned as his hardness slipped into the warm recesses of his vice principal's mouth.

She went slow at first, using her tongue to lick it up and down a few quick times, before taking it deeper in her mouth. She felt his hand tangled in her hair, felt his large cock tickling the back of her throat as she slurped on it greedily, wanting to make him come quickly.

He had to get to class after all.

Up and down, several times she bobbed her head, sucking on it with mature enthusiasm, knowing she was going too far . . . but not caring.

Her efforts were rewarded after a good twenty seconds or so when his cock exploded inside her mouth. As she swallowed his cum, on her knees, in her office, she knew things could never, would never, be normal between them.

After she got herself straightened up, she hugged him tightly. "Go ace that quiz now, honey. You have no excuses."

"Mom, that was incredible . . . or should I say Mrs. Grant."

"I know, it was . . . was something but you gotta go."

After he left her alone, Ellen hurried behind her desk, sitting down, she furiously used her fingers to bring herself a quick orgasm as she thought about her son's hard cock in her mouth and about his fingers playing with her pussy.

The orgasm that washed over was ultra-powerful, made all the more powerful by the sheer naughtiness of it.

Free of his pent up lust, Jimmy was able to concentrate fully on Ms. Sanford's lecture and did, in fact, ace her quiz.

On his way home he stopped at the local flower shop getting his mother a dozen long stemmed roses, knowing he was one step closer to his ultimate dream . . . to give his virginity to his mother.

END OF PART I

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4 Comments
AnonymousAnonymousover 1 year ago

Loved this story but you left us hanging you need to write part 2 still gave it a 5 !!!!!!!!!!!!!!!!!!!!!

Gym52Gym52almost 2 years ago

EXCELLENT..

Seriously looking forward to reading part two of this story. A couple of proofreading errors, at one section Jimmy becomes Billy for a few paragraphs, also a couple of spelling mistakes.

brainkillheartbrainkillheartalmost 2 years ago

would love to read second chapter of this , if you need some ideas , bondage would be really hot

elite723elite723almost 2 years ago

Usually don't read long stories. Glad I did this time. Loved it.

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