Joey Needed a Tutor

Story Info
Retired teacher Matilda Ward loves to tutor.
5.5k words
4.46
60.1k
47
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Matilda Ward was a teacher who had retired at age 63, hoping to spend the rest of her life with her husband of 37 years and doing what they enjoyed best, hiking and fornicating as Herbert often put it.

So when her seemingly healthy spouse had a massive heart attack and passed, Matilda was suddenly adrift and while financially secure was alone. Hiking wasn't the same without a partner and a vibrator proved to be an unsatisfactory substitute for a man, and having given up her teaching position Matilda was left with a lot of time on her hands.

With schools cutting back on positions and now becoming 64, Matilda knew she had little hope of catching on somewhere, so she put an ad in the paper offering her services as a tutor. She only got one response from the ad though, but she went and spoke to the woman whose son was woefully behind because of an illness that sidelined him for a time in his younger days.

Now 18 and healthy, Joey Barnes was trying to graduate on time but was struggling and although his divorced mother really couldn't afford a tutor she wanted her son to succeed. Part of that was the fact that high school was no fun for Joey, a shy and meek lad who seemed to be a magnet for ridicule and abuse by other students, and the faster he got out of there and to a college where he would have a fresh start the better.

When Matilda met with Joey and his mother, the teacher could see why he got picked on, not that it was fair. Joey had a bit of a stuttering problem that got only worse when he tried to stop it, and being about 5'7" and maybe 120 pounds soaking wet, that combined with his horn rimmed glasses that made him look even more like a classic nerd almost guaranteed he would be a target.

So the tutoring began, and after a couple of sessions Matilda was not only warming to the young scholar, but she was learning that despite appearances, Joey Barnes was just like most every other 18 year old guy, maybe even more so. That, as it happened, would eventually become alright by Matilda.

***

"Joey's upstairs waiting for you," a harried looking Brenda Barnes said after letting the retired teacher in. "I'm sorry I have to run. I just want to tell you how happy I am that Joey's taking to you and your tutoring so well. He looks forward to seeing you - you must make learning fun."

"He's a delightful young man and he's much more intelligent that you've been led to believe," Matilda said. "He just needs people to be a little patient with him and we're going to get him that diploma too. You watch and see."

Joey's mother left and before Matilda made the trip upstairs to Joey's room she checked herself in the mirror, straightening her blazer and making sure her short silver hair looked good because Joey always gave her a thorough inspection when they worked together.

Matilda smiled at the thought of the way Joey would ogle her as if she was a model instead of an old lady, and the only thing that amused her more than his leering was the inept way he tried to do it subtly.

Up the stairs the tutor went, and when she reached Joey's room she stood in the doorway and looked at her pupil who as always was sitting up straight at his desk with his hands folded in front of him and beaming.

"Hi Mrs. Ward," the pimple-face lad chirped as she entered the little room. "You look real pretty tonight."

"Why thank you Joey," Matilda said as she set her purse down. "You say that every time I see you."

"That's because you always look pretty," declared the lad whose manner reminded the woman of Eddie Haskell on the old Leave It to Beaver show, although Joey's praise seemed sincere, unlike the shallow and sneaky character Eddie was.

"Well that might charm me but it won't help you pass English," Matilda reminded her protege as she reached for the door to close it but then stopped. "Don't need to close the door because your mother left so we won't be disturbed."

"Gone for the night," Joey said way too happily. "She's working a couple nights a week for extra money."

"She's a very industrious woman," Matilda said, and she had noticed that right away, which was why she was charging next to nothing for the tutoring. "Now where were we?"

Matilda took off her blazer, and as she did as saw Joey's eyes widen when he saw the blouse, and while the simple grey and white sleeveless top was nothing flashy, Joey had mentioned last week how much he liked it, which was why she wore it although she feigned ignorance as she asked him why he was smiling.

"That blouse. I really like it," Joey said while grinning widely.

"Oh, that's right. I do recall you mentioning that the last time I wore it," Matilda replied. "How did we do with that homework assignment from last time?"

"Got a 94!" Joey announced as he reached into his book bag and extracted the paper, and as he set it down Matilda put her hands on the desk and leaned over to see what answer he had gotten wrong.

"Very good," Matilda said as she bent down far enough so that Joey could see what he was looking for, stifling a chuckle as the lad looked over the top of his glasses and into the scoop-neck of the blouse.

Young fellows and their raging testosterone, Matilda mused as she let Joey look as long as she dared before straightening up. After noticing the way the fellow had leered at her breasts last time she had gone home and leaned down in front of the dresser mirror to see what had fascinated Joey so much.

The sight of her breasts like that startled her, because even encased in a brassiere her once perky bosom sagged so much. Her breasts had become long tubes with her over-sized areolas completely covering the ends of what her late husband used to fondly call her banana boobs as she aged.

Why a young man would go out of his way to look at as much of a elderly woman's breasts that the clothing allowed baffled the retired teacher, because it made no sense. Then again, neither did the way her nipples stiffened when he looked make sense, or why she let him look.

"So what are your assignments for the rest of this week," Matilda asked as she came around and stood next to Joey as he fished out the information from the backpack, and after he put on on the table they looked at the list, with Joey predictably leaning next to her so he was touching her bare arm.

"This shouldn't be so challenging given the progress you've been making," Matilda declared before her eyes went over to something she didn't approve of. "And what are the rules about this phone?"

"No Mrs. Ward," Joey blurted out as he tried belatedly to stop her from grabbing the device. "Please don't."

"I'm just going to put this somewhere so that - what? What is this?"

Matilda looked to the screen of the phone and then back at her ashen-faced student before holding the photo up closer.

"I assume there is an explanation for this?"

"You can't see your face," Joey said of the photo of her from the neck down with her hanging breasts in full view.

"Why?"

"I'm not good at taking pictures and I didn't want you to catch me taking it," Joey explained.

"That's not what I mean. I'm asking why you would take a picture of me like that? Do you show this to your friends and laugh?"

"Omigod no. Nothing like that. Don't have many friends anyway."

"I didn't see you take this."

"No, that was from last week."

"Are there others?" Matilda asked, and when the silence spoke volumes she demanded he show them to her.

"Just push that button and it goes to the next one," Joey explained, and so Matilda pushed the button, and kept pushing as what seemed like an endless processions of her in various candid shots, few of them flattering or revealing but managing to document just about every inch of her that clothing didn't cover.

"My, I used to be aware of students passing notes or chewing gum, but it seems that I'm slipping because you've managed to get away with quite a bit under my nose."

"I'm sorry. Do you want me to get rid them?

"That would be nice."

"Can I take a real picture of you though?" Joey asked. "Just you sitting there?"

"I suppose, but you could have asked that in the beginning," Matilda replied as she sat down and touched her hair with her hands. "Do I look alright?"

"Yeah - wait. Stay just like that."

"Like what?"

"Pose like you were with your hands straightening your hair." Joey asked excitedly.

"Like this?" Matilda asked as she tried to remember what she had done, and after Joey hit the button several times she announced, "Okay, we're done with that silliness and can get back to work."

"Thank you," Joey said as he looked at his work, and out of curiosity Matilda asked to see the photos.

"Let's see what kind of a photographer you are," Matilda said, and after looking at the series of photos she declared, "Marilyn Monroe I'm not. Happy now?"

"Yes, you look so great, especially in a couple of these," Joey declared, and after Matilda asked him why he explained. "You've got really beautiful arms and your armpits are incredible."

"What?"

"See how your arms are so nicely toned - not like my Mom's because the bottoms of hers hang down when she lifts them," Joey detailed. "And your armpits are so deep and creamy looking, almost always smooth as butter. Mom's always look stubbly."

"Well, I'm glad I shave before I come over," Matilda said in a confused voice.

"It's okay if you don't because the first time you came over you had a little peach fuzz under your arms, and that looked sexy too."

"Sexy?" Matilda repeated. "Joey - I guess I should be flattered but really. I'm old enough to be your grandmother."

"My grandmother doesn't look anything like you," Joey mumbled. "neither does my Mom."

"You should be concentrating on your studies more - but also you should show this kind of interest in girls your age."

"Okay."

"You say okay but you don't say it like you mean it," Matilda said as she watched Joey stash his phone in the top drawer of his desk. "And you probably didn't erase those other pictures either did you?"

"I still have problems with compound sentences," Joey said as he tried to change the subject and close the desk drawer before the teacher grabbed the phone again, but he failed.

It wasn't the phone Mrs. Ward was after though. It was seeing a printed picture of her that got her attention, and when she grabbed the stack of papers she got a look at his secret stash.

"Where did you get these?" Matilda asked as she looked through the very familiar photos which were the pictures of her smiling face that went in the school yearbooks along with the students.

"The yearbooks were on line - most of them anyway - so I copied the pictures from there. They're a little grainy but..."

"It's like watching myself deteriorate in fast motion," Matilda chuckled as she fanned through them. "I wasn't bad back when I was - what's this?"

"Oh shit!" Joey groaned when he saw a very different photo was in the mix, covering his face with his hands as his tutor looked at the crudely photo-shopped picture he had created of Matilda with her head attached to a nude photo of a young woman he got off the Internet.

Matilda had to cover her mouth to keep from laughing at the sight of her head on some busty woman less than half or age, but she managed to keep a straight face and pretended to be bothered instead of amused and flattered.

"I assume this is another one of your skills, doctoring photos? This obviously isn't me," Matilda told Joey after telling him to stop his dramatics and face her. "I can only imagine how horrified the poor girl would be if somebody put her head on a naked picture of me."

Joey shrugged and sat there looking at his handiwork being graded by his tutor, and while it had been fun to create it was less enjoyable right now.

"I'm curious. Do you honor other people with things like this? Your mother for instance?"

"Omigod no."

"What do you think your mother would say if she saw this?"

"You aren't going to tell her are you?" Joey asked/pleaded.

"I don't know. Tell me Joey, you don't have a girlfriend now. Have you ever had one?" Matilda asked.

"Not really. I think with the the way guys make fun of me and stuff, they don't want to be known as the desperate kind of girl that would go out with me."

"Well that's something only you can change and until you stand up for yourself that might continue your whole life," Matilda remarked as she looked at her picture again. "Have you ever seen a naked woman?"

"On the Internet."

"I'm afraid that in the real world most women don't look like this," Matilda informed her protege. "I certainly don't. You don't picture me looking like this do you?"

Joey shrugged and started to say something but stopped.

"My breasts for example," Matilda commented as she held the picture for both of them to see. "Even when I was the woman's age I never looked like her. She's very busty for one thing and her breasts look very firm. Those days are certainly long gone in my case.

"Doesn't matter," Joey murmured.

"Her stomach is so flat and trim," Matilda continued. "Strange though - this woman doesn't have any pubic hair."

"She probably shaves it," Joey explained. "A lot of girls do that."

"Really?"

"You don't do you Mrs. Ward?" Joey asked.

"Of course not. Why would I?" Matilda asked. "Is that something you prefer?"

"No," Joey replied as he fiddled with his hands nervously. "Uh - Mrs. Ward? Is your - you know - silver grey too?"

"My pubic hair?" Matilda asked. "No, while I wouldn't be surprised if a little grey has sneaked in, for the most part it's brown."

"Do you have a lot of it - pubic hair I mean?"

"I'm afraid so," Matilda admitted. "You really need to get a girlfriend honey."

"I know. I figured you had a lot of hair down there on account of that time I saw the peach fuzz under your arms it looked like there was a whole lot of it. More than my Mom when she doesn't shave."

"This conversation we're having Joey. It's certainly not anything that will be on your final exam. What if your mother ever heard us talking like this, or saw that picture you made?"

"She won't. Besides, whenever I ask questions that embarrass her she gets flustered and changes the subject," Joey explained. "I don't care if she finds out I love you or not."

"What you're feeling isn't love Joey. It's a crush and I'm flattered," Matilda said. "Since I've answered your personal questions I would like to ask you something. Last week when I saw you fiddling under the table and I asked you what you were doing, you said you had a itch. Was that true?"

"No," Joey replied, and when Matilda asked him what he was doing he added, "You know."

"You realize honey that I had boys too, and while that was years - decades ago - I remember. It's okay as long as you keep things under control, and for heavens sake don't think that all women look like this woman, or that all men are built like those fellows in dirty movies."

"They aren't?"

"Of course not."

"Can I see?" Joey mumbled in a barely audible voice. "I want to see you."

"Joey..."

"Please. I swear I would never even tell anybody about it, it's just that I think about you all time. About how pretty you are and how nice your smile is and how you smell so sexy," Joey babbled. "A lot of times at night I kiss my pillow and pretend I'm kissing you."

"You realize what you're asking me to do?" Matilda asked. "Parade around naked in from of a 18 year old boy?"

"I'll take my clothes off too if you want."

"That wasn't what I meant Joey," Matilda told her pupil.

"And I'm 18 but I'm not a boy," Joey said. "I'm a man."

"What are you doing?"

"I never - would never do this in front of any other girl but I trust you," Joey said as he stood up and pulled off his shirt to exposed his scrawny chest, the skin pale and smooth.

"Joseph..."

"Mom always calls me that when she's mad at me," Joey explained as he fumbled with his belt. "Please don't be mad at me Mrs. Ward."

"I'm not. You're just - confused."

"See how excited you make me Mrs. Ward?" Joey asked as he stepped out of his slacks, the bulge in his tight white briefs certainly nothing the senior citizen expected.

Matilda actually leaned back in her seat when Joey yanked down his underwear even though the lad was several feet away, her face flushed as her eyes watched Joey's erect penis bounce as he kicked his briefs off.

"See?"

"I see Joey," Matilda said as she tried not to look at the stiff organ and the dangling testicles and didn't do a very good job of it. "I see quite well thank you."

"I know that my dick isn't as big as those guys in movies..."

"You need to forget about those things. Those movies aren't real life and the people that are in them aren't average folks like us," Matilda explained. "I haven't seen all that many men in my life but enough so I can assure you that you're very nicely endowed."

"I am?"

The teacher hadn't expected this - none of it. The brashness of his adoration for her was one thing, but then to take his clothes off in front of her like this?

Then there was the matter of what was still bobbing up and down in front of his, the organ so stiff that it was curling a little bit up towards his face, exposing the network of veins and stretched skin on the undercarriage of a penis that was probably nearly the equal in length of her late husband's.

"Well?"

"Joey, first of all what if your mother came in here right now?"

"She's at work and will be, and besides, she's seen my dick before. She's caught me jerking off at least once," Joey admitted.

"That's not the point. I'm supposed to be here helping your school performance."

"Just show me a little bit of you. Take off your blouse and bra."

"I can't."

"Then just stand there for a minute for me - please?" Joey said as he wrapped his fist around his upstanding plum and began to stroke it. "Won't take long."

"Joey - stop that - please. It's very crude."

"Then take off your top - I swear the camera is put away," Joey pleaded as he let go of himself.

Matilda stood up and found her fingers reaching up for the buttons on her blouse, and although her fingers often trembled they were shaking so hard she couldn't control them.

When he gets a look at me and sees that this soon to be 65 year old woman looks nothing like his pornography girls he'll lose that erection fast, Matilda mused to herself, although there was also another scenario she could envision.

This is the kind of thing you end up on the front page of the newspapers about, or even on the Springer show. Just another freak in the sideshow, yet she had been so lonely without her husband and except for him nobody had ever looked at her like Joey was.

"Omigod," Joey whispered as his tutor neatly set her blouse aside and after brushing a strand of silver from the side of her face reached back to unhook her bra.

As the hooks came loose one by one Joey was standing there shifting his weight from foot to foot, and his member was not only still erect but there was semen drooling out and hanging off of the tip.

The other option was looking at herself in the dresser mirror behind Joey, and when the bra came off and her breasts hung down Matilda realized she looked worse than she feared, and the fact that her pupil's dimpled butt was visible in the reflection made it look even more vulgar.

"I told you..."

"You're so beautiful Mrs. Ward. Your tits - sorry - your breasts are incredible. They're even bigger than I imagined they were, and your nipples are amazing."

"Please Joseph," Matilda pleaded as he came over to her, and even though the senior could have easily fended off the slight lad for whatever reason she didn't when he put his hands on her doughy teats and hefted the giving flesh in his sweaty palms.

"Oh geez," Joey said, his stutter returning to make the words sound comical in a different situation, but with the wide-eyed teen practically hyperventilating as he kneaded her breasts Matilda wasn't laughing..

12