I think it will be easier if I put some lotion on my hand."
He watched as she squirted some lotion on both her hands before wrapping one hand around his stiff member while using the other to cup his testicles.
Slowly, she started to move her hand up and down, making him groan with pleasure as she jiggled his nut sack tenderly.
"Maybe we should make out some more while I do this for you. Liz said guys like that . . . kissing while being touched."
Unlike his father twenty years ago, Jimmy was not destined to last all that long. Ellen, much more experienced and confident now, of course, knew exactly how to give a man a hand job.
Ellen also knew how to kiss, and as she swirled her tongue expertly in his mouth, while working her hand up and down at varying speeds on his hard shaft, she was supremely confident she could make him come as quick or as slow as she wanted.
Wanting him to witness the grand finale, Ellen pulled back, positioning herself on her knees. She looked down at him, smiling, before starting to stroke his cock in earnest as Jimmy watched.
His eyes were glued to that pretty colorful bra of hers as she worked her hand up and down his cock and when his legs began to thump up and down on the bed she knew he was close. Reaching down, she added the final touch by jiggling his balls lightly as her experienced hand flew up and down his cock.
"Oh God, I am . . . I'm going to . . ."
His cock exploded with a new batch of fresh sperm, coating the back of her hand.
"Hmm, I think it is game over," she whispered to him before disappearing to get the wash basin for the second time on this fateful night.
The next few day passed in a pleasant haze for Ellen as Jimmy doted on her with the utmost care, bringing her breakfast in bed one day, bringing her candy and flowers the next, and then finally, he presented her with a beautiful diamond necklace. When she asked why he simply smiled and said, "Because you deserve it for being the world's best mom . . . ever."
Ellen was walking on clouds for those few days as her son plied her with his best boyish charm. And then suddenly, without warning, his mood changed.
On the fourth day after their naughty adventure, a Saturday, he woke up sullen and moody and stayed that way all day. When she asked him what was wrong, he snapped, "Nothing," before practically fleeing from her.
His surely mood lasted all the way into and through the next week. Ellen did her best to ignore it at first, believing he was trying to blackmail her in being naughty again but finally on Friday night over dinner she brought the subject up.
"You have been moody and sullen all week, Son. What is wrong?"
"Nothing," he mumbled.
Sighing, she slammed her fork down on the table before fixing him with her hardest glare, which never failed to break his spirit. It worked, of course, as Jimmy sighed himself before finally saying, "Fine I will tell you."
After dinner, sitting side by side on the sofa he quietly outlined why he had been sullen all week. "It's just that I have nothing to look forward to Mom. I mean I know you would never agree to do . . . that . . . again and . . . well it was so good, Mom, I mean really, really good."
Ellen's heart swelled with pride at him thinking what they did together was "so good". On the other hand, had she created a monster by doing what she did?
If she had created a monster, which considering his sad and sullen behavior of late, certainly seemed to be the case, it would be up to her to control it.
"I never said we couldn't do it again, hon."
"Really," he said, smiling for the first time in days.
After a long drawn out discussion, they finally came to an agreement. For the past year or so, every Friday night had been popcorn and movie night. It was a tradition they both immensely enjoyed. Ellen, with a sly smile, promised to add something else to this tradition: a nice little hand job.
For the rest of the week, Jimmy was so utterly charming to his mother, totally sweeping Ellen off her feet.
Friday Night Movie Night became simply heavenly for young Jimmy. His mother would wear some nice outfit to the movie, sometimes it was cute, sometimes it was something over the top sexy, sometimes it would be both, and then during the course of the movie they would gradually ease their way into her hand job.
It would start with a few kisses, but not too many as Ellen was afraid of things spinning out of control. During their light kissing session, on rare occasions, if she was feeling frisky she would allow him to feel her up a bit through whatever cute or sexy top she was wearing, although she would never allow him to snake a hand under her top or to go between her legs.
Finally, after sensing he was ready she would slip a hand under the blanket they were huddled under, slowly undoing his jeans, before pulling his hard cock out and giving him the promised hand job.
The experience was something Jimmy so looked forward to all week. So much so he could barely make it to Friday without bursting. After four straight Friday night hand jobs things were going about as good as he could have hoped before things hit a snag.
The snag was due to the one stipulation Ellen made to him about what she was doing: if his grades started to slip, even a little, meaning if he received anything less than a B, or if he was being graded on a percent basis the threshold was anything less than 84 percent, on any paper, assignment, quiz, test, etc. their fun and games on Friday night would immediately cease for at least one week, and if it happened a second time, the penalty would be a month. A third time . . . he didn't even want to consider that!
She made him turn over all his graded assignments, tests, and quizzes on a weekly basis, and being she was a vice principal at the school, it was easy for her to keep tabs on his progress.
In early December, it was going into the fifth week after their agreement started, Jimmy was called to his mom's office at the school just as he was about to go on his lunch period. It was a Thursday and Jimmy, as usual, was beside himself with anticipation for the school week to end and for Friday night to get there.
As he trudged down the hallway to her office, he had a pretty good idea what she wanted to talk to him about. His suspicions were confirmed when, as soon as he walked into her office, she hit him with her best icy glare: fucking algebra.
Yeah, damn algebra. He was struggling with the weekly quizzes Ms. Sanford was giving. The reasons for this was multiple. First of all, Ms. Sanford was a substitute and her quizzes were much tougher than old man Whitmore's.
At first, Jimmy was not too worried, after all she was only a sub and Mr. Whitmore was only supposed to miss a week, or two at the most, because of some operation he was having at the hospital. But then he developed complications and his mother gave him the inside scoop he would not be back probably until late in the school year, if at all.
She also informed him, Ms. Sanford would be staying on as the sub until he returned. Not good news, thanks to the little crush Jimmy had developed on Ms. Sanford.
This new substitute teacher was, in Jimmy's mind, a perfect mature beauty. If he had to guess she was probably in her early fifties, with pretty blond hair, styled fashionably short and wore outfits, while not over the top sexy, after all the teacher's had a dress code to follow just like the kids, hinted at her having a pair of rather prodigious breasts under the somewhat tight blouses she wore in class. Her skirts tended to be on the tighter side, probably skating just up to the border line of the dress code while not actually crossing it.
In class, she tended to call Jimmy's name out more than the other students and unless it was just his imagination, she seemed to almost flirt with him in their interactions. He told himself she just possessed an outgoing friendly personality but still . . . in the dark of night, alone in bed, he often fantasized about Ms. Sanford.
It didn't take long for the rumors to swirl around school that the outgoing and friendly Ms. Sanford might have been a lesbian. The word was she had never been married, and considering her short hair style and her friendly attitude toward the females in her class, the rumor mill was working overtime.
The fact of these rumors, combined with how friendly she was toward Jimmy, as opposed to the other boys in her class, made him feel almost special and only increased the developing crush he had on her.
During class, as she was up at the board showing the class how to work out the assigned problem, or standing in front of the class giving her lectures, Jimmy often became lost staring at her. As his concentration wavered in her class, so did his grades begin to fall. Making it doubly hard was her weekly quizzes fell on a Thursday, when poor Jimmy was at his most desperate in pent up anticipation for his weekly session the next day with his mom.
As he entered her office before he could sit down, his mother, hit him with the bad news. "I have your quiz score from last week in algebra. B minus," she snapped at him. "You know what that means. Anything below a B . . ."
"Yeah, yeah I know," he grumbled. "No Friday night fun." He plopped down in the chair across from his mom hopping she wasn't going to give him too much grief. It was bad enough he would be missing out on his Friday night fun as it was.
"Better do better on her quiz tomorrow, Son or--"
"I know . . . a month penalty."
Ellen looked at him. He looked like a little kid who was told on December 24th Santa would be skipping his house this year. Yes, he looked that pathetic as he slumped down in his chair.
Softening her voice, Ellen said, "I talked to Ms. Sanford. She says you act like you are day dreaming and not paying attention while she is showing the class how to work stuff out on the board. You got to pay attention to her son. I mean, algebra, you were doing fine in it under Mr. Whitmore."
"Yeah, well, things were different then, Mom."
"Different how. She is teaching the same stuff you aced before. She is has not changed the curriculum."
"Yeah, but . . ." He hesitated, not sure if he should actually tell his mom the truth about his feelings for the beguiling mature Ms. Sanford. What if she got jealous, then again, she had tried to convince him needed to take an interest in other girls . . . although Ms. Sanford, at her age, was anything but a "girl", of course.
"Yeah, but what . . . let me guess. You have a crush on her . . ."
Jimmy sat up straight in his chair. How the fuck did she know? He thought about denying it but his mother always seemed to know when he was lying so he thought better of it. Instead, he smiled wanly, shrugging his shoulders. As usual his mother read him like an open book.
As she stayed silent that only meant one thing: she wanted to hear more.
"Yeah, maybe . . . I mean a little." Then the rest of the truth came pouring out before he could stop himself. "I have a hard time concentrating on her lessons, Mom, because . . . because I don't know . . . I mean I think she is attractive, not as much as you, but still . . . and then, on Thursday, her quizzes are tough because by then, I'm . . . well, you know, its . . . it's been like six days since . . . you know . . . our last time and I am so ready, so anxious for Friday, that I can't like at all concentrate as she lectures us before the quiz."
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.