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by VeryDirtyMind (Edited with Ginger)

 

Emily Grant had lived in the same house most of her life, and while the little bungalow had seemed too small when her husband had been there to share it, now it seemed too large for just the widow.

At 67 Emily now had time on her hands, and more and more she found her thoughts going to places that she had left alone for a long time. Dark and naughty places, so when the neighbour boy had told her recently he would be going off to college soon, Emily thought that might be for the best.

Jimmy was the sweetest thing, a wonderful boy who had been a godsend to her over the years over the years, always offering to run errands and do odd jobs like mowing the lawn. While the boy’s mother might have instigated those things at first, Emily knew that Jimmy did them on his own now.

It was hard to believe that Jimmy was now 18 because he was still a little fellow in many ways, only being about a half foot taller than Emily’s barely 5′ height, and he didn’t outweigh her by all that much either. Jimmy was becoming a man though, and when she thought about the boy that way Emily felt dirty.

It didn’t stop her from thinking about the lad that way though, and one day when June was turning to July Emily let her dark side take over.

***

“On the counter would be wonderful Jimmy,” Emily told her neighbour as he carried the bag of groceries into her kitchen, clutching the top of her robe together while a shiver went through her body at what was going through her mind and the twisted scenario she had concocted.

“I can put these away for you if you would like Mrs. Grant,” Jimmy offered.

“Oh you don’t have to do that. I’m so grateful that you went to pick these goods up, but since you seem to know where things go better than I do…”

“No problem,” Jimmy replied with a smile, and as Emily walked over to the sink her eyes went over the little fellow, cursing herself for what she was thinking.

“You’re so sweet. Some girl is going to get herself one fine husband someday,” Emily told him, enjoying the blushing on Jimmy’s dimpled face. “I wish I was 50 years younger myself.”

Jimmy was wearing a baggy tank-top with a character from some video game on it along with blue shorts that he swam in, and as the lad reached to put up some cans of soup Emily was enjoying the faint ripple of muscles in his skinny arms.

“What am I going to do without you around?” Emily said. “You’re like the grandson I never had.”

“I’ll be back around during breaks and stuff,” Jimmy said.

“Jimmy going off to college,” Emily proclaimed. “I remember when you were knee-high to me and now you’re all grown-up and a man.”

“Not grown up all that much,” Jimmy lamented, the fact that he had never gotten very tall always on his mind.

“Nonsense,” Emily said as she patted his bare shoulder, and as he put a box of pasta on the top shelf her eyes went under his upraised arm to the wisp of fur that was exposed. “Look at you, you’ve even got hair under your arms now.”

Jimmy almost dropped the pasta as his face turned red, the cheeks that likely had never felt a razor now beet red at the mention of his practically non-existent body hair.

“A little hair on your legs too I see,” Emily noted regarding the down on the insides of his calves, adding, “Just enough. My Warren rest his soul – he was so hairy all over – and I loved him dearly but it was like hugging a bear.”

“My friend Eddie, he’s like that,” Jimmy responded. “He’s even got hair on his chest and he kids me because I don’t.”

“Well I wouldn’t worry about that,” Emily said before changing the subject. “That young lady Priscilla? She doesn’t care about that I reckon. I haven’t seen her lately. Are you two still…”

Jimmy shook his head sadly and Emily felt bad at his reaction, leaning over and putting her arm around his shoulder, the feel of his warm bare skin making her heart flutter.

“I’m sorry. You’ll do better anyway. Once the girls at college get a peek at you, watch out!” Emily suggested, and when she saw Jimmy’s eyes going to the top of her open robe she was tempted to pull the robe together but didn’t, surprised once again that he would find the sight of her sadly hanging teats in the nightgown under the robe worth looking at.

“Maybe,” Jimmy responded, and as Emily gave his shoulders a squeeze she recalled that this was far from the first time she had caught him looking at her like this. “Well, that’s it for the groceries.”

“I know we’re going to start our usual battle,” Emily said as she grabbed the two crumpled bills from her robe pocket and tried to press them into the boy’s palm, and after he resisted she got upset. “Use the money for books.”

“I’m okay,” Jimmy said as he made her take the money back, and as the two faced each other his eyes went back to the open robe and to the very worn and now off-white nightie.

“What can I give you?” Emily asked. “I want to thank you.”

Jimmy shook his head but kept looking, and while he had often peeked this was more like a stare. While Emily had no idea why a young man like Jimmy would want to look at a woman whose small breasts hung almost to her waist, she didn’t care.

“Tell me honey,” Emily said and then repeated the words as a plea. “Tell me what you want.”

“I dunno,” Jimmy said, drops of sweat beading on his forehead under his shaggy light brown hair.

“Tell me honey please,” Emily said as her nipples stiffened under the thin silk, wishing that instead of the banana boobs her breasts were perky once again. “You can tell me anything.”

“Can’t…”

“Yes you can,” Emily responded, and although she had fantasised about this moment many times recently and had even practised the move once before Jimmy got here, the senior was surprised when she actually did it.

Emily shrugged her shoulders, and after a second effort the robe dropped off and onto the linoleum, leaving her trembling and feeling naked despite the tattered nightie still being on.

“You should have seen me back in the day,” Emily apologised, but Jimmy shook his head.

“I look at you – a lot.”

“I know honey. I don’t care,” Emily assured him. “I like you looking at me even if I don’t know why.”

“Sometimes at night when your living room light goes out I sneak out and go out back and look through your bedroom window when the curtains are open,” Jimmy said in a quivering voice, and when he saw his neighbour’s shock at that revelation he added, “I know it’s wrong and I feel dirty afterward but I can’t help it. I can’t really see good from out there but I do it anyway. Please don’t hate me for this.”

“I don’t know what to say honey,” Emily finally managed to get out. “One thing I would never do would be hate you. I adore you and you’re very brave for telling me this, even though I don’t understand.”

“I’ve always loved you for as long as I remember,” Jimmy confessed. “You’re like a little doll, so tiny and perfect, and I cringe about the things that go through my mind when I think of you.”

“That’s okay Jimmy,” Emily said as she took a step closer and took the lad’s trembling hands. “I think things about you too.”

“You do?”

“Yes, although I feel like a predator because you’re so young,” Emily said. “I keep telling myself that you’re 18 now, but then I would say that I was being silly because you’re so young. Why would a cute fellow like Jimmy be interested in someone like me?”

“In bed at night sometimes I pretend the pillow is you, and I kiss it and hug it and imagine that…”

“Here,” Emily said while bring Jimmy’s hands up and onto her breasts, clamping them to her doughy cones and squeezing them tight. “Can’t compete with your Priscilla I’m afraid.”

“You’re perfect,” Jimmy said as he kneaded the very soft flesh, the memory of his chunky ex-girlfriend’s breasts way in his rear-view.

mirror.

“Do you want to go to the bedroom with me?” Emily asked, her plump nipples throbbing from the touch of a man through the fabric.

“I don’t know how to…” Jimmy replied.

“Sure you do,” Emily said, trying to relieve the tension. “It’s right down the hall.”

“I mean…”

“I know what you mean. If it’s any help I’m scared too,” Emily responded as she took Jimmy’s sweaty hands off her breasts and took him down the hall, to the room where only one man had been before.

***

“Been a long time since there was a man in here with me,” Emily told Jimmy as she gently tugged his tan-top from under his shorts, the room having become decidedly more feminine since Warren’s passing. “Upsie-daisy”.

Jimmy obediently raised his arms so that Emily could lift the shirt up and over his head, and after she set the shirt aside put her hands on his pale scrawny chest, a ghostly white compared to his tanned arms and neck.

“I can feel your heartbeat,” Emily told him as her fingers rested on the boy’s heaving chest and lightly rubbed her hands over it. “So nice and smooth and soft your skin is.”

“Do you like this honey?” Emily asked as her wrinkled fingers toyed with the tiny pink nipples, making Jimmy’s upper torso quiver as much as his knees were, and when he didn’t answer she asked, “You okay honey?”

“You can talk to me Jimmy,” Emily advised. “Do you want us to stop now?”

“No,” the lad’s shaky voice replied.

“Do you like your nipples played with?” she then asked, and after he nodded and croaked out a yes, the silver haired senior leaned down and suckled lightly on the little buds, first the left and then the right.

“Oooh…” Jimmy responded as Emily kissed her way up and around his collarbone and neck before kissing him on the lips.

“Still nervous?” she asked, and after he nodded she smiled and as she let her hand slide down his stomach and onto his shorts she said, “Me too. Haven’t done this in a long time.”

“No,” Jimmy said as he caught the old lady’s wrist before her fingers found what they were looking for. “Please.”

“No?” Emily asked quizzically.

“I’m… it’s really small,” Jimmy stuttered.

“I don’t really care about that so why should you honey?”

“Priscilla – we were going to – you know – do it? The night of the dance last month?” Jimmy explained. “When she took my pants off and saw me she laughed.”

“Sounds like a silly girl,” Emily opined.

“She’s done it with a bunch of guys so she knows.”

“So have I Jimmy,” Emily replied. “Not lately but in my life I have, and I can tell you it doesn’t matter.”

“Don’t let a horrible comment by a mean girl haunt you for the rest of your life honey,” Emily told Jimmy as her hand worked free of the lad’s grasp, and when her fingers found what she was looking for she smiled and said, “There. Now just relax.”

Emily kissed Jimmy’s cheek as he twisted his eyes shut, massaging what was definitely not all that easy to hold onto through the layers of clothing until she finally let go and took hold of the elastic on his shorts to ease them down.

“Let me get these off you,” Emily said as she bent down to get the shorts from around Jimmy’s ankles, glancing at the modest bulge in the tight white underwear before straightening up. “Now where were we? Oh yes, I was trying to get you to relax. Not sure which of our hearts is beating faster. There, now just relax.”

Softly Emily’s hand massaged the pouch, trying to bring a little life down there, and after a while let her hand slip under the elastic, sliding down through the downy wisp of hair until she found his penis, which like the tautly wrinkled pouch below seemed to be trying to crawl up into his body.

“My hand cold?” Emily asked, and after Jimmy said it wasn’t, finally used it to work his briefs down.

“You aren’t that little honey,” Emily lied as she cupped the tight scrotum, looking down at the tiny wrinkled tube resting on the back of her hand. “You’re very beautiful too.”

Patiently Emily’s hand kneaded Jimmy’s balls as best she could, and after a minute or two the hairless pouch relaxed and she was soon rolling his balls in her palm.

“That’s it Jimmy,” Emily sighed as she moved up to his dick, softly pulling on the circumcised organ while nibbling on his neck, and when he seemed to be responding a bit she added, “That’s my boy.”

Jimmy finally opened his eyes, and when he saw the senior beaming up at him he smiled back, prompting Emily to say, “Let me take this off.”

Because the nightie hung on her so because she had lost so much weight in the years since she bought it, instead of lifting it up she simply shrugged it off and stepped out of it.

“Always wished when I looked in the window at you that you would take that off,” Jimmy said as he stared at the naked neighbor for the first time, and his voice was breaking when he added, “You’re so gorgeous.”

Emily started to tell Jimmy he was silly, that while she might not look horrible for her age, the fact was that she was still 67. Her breasts sagged and although she was slender she still had a little belly, and her legs that had once gotten whistles were now showing their mileage, but she said nothing because it was obvious that Jimmy didn’t see her like that.

“Doesn’t look so little now does it?” Emily winked as she moved closer while palming the lad’s erect penis, and while the slender throbbing prong barely filled her hand, he was a whole lot more impressive now.

“I love you,” Jimmy said, the eyes welling up as they hugged.

“Make love to me then,” Emily responded as she went down to the bedding, pulling him onto her and guiding his manhood between her legs, deciding against foreplay for fear something would go wrong.

Besides, Emily reasoned, not only was Jimmy’s member slender, she was so wet already that the combination would make entry no problem despite her years of abstinence, and she was right.

“OH!” Emily cried out, dramatizing for both their benefits the sensation of Jimmy’s dick sliding between her plump labia and into her sex, and as her hands gripped the boy’s butt and pulled him close the look in his eyes was priceless. “Yes! Yes!”

Emily didn’t know how long it lasted – not much more than a minute – and while she was prepared to fake an orgasm, after Jimmy’s energetic thrusting reached its peak she felt a long dormant wave rush over her, so her clawing and screaming was not an act and feeling the boy’s seed spurt inside of her only made her cum harder.

“Omigod,” Emily gasped after it was over, the sight of her teeth marks in the lad’s collarbone making her wince, but Jimmy too bust crying and hugging her to feel anything but what seemed to be the most joyous moment of his.

“I did it! I really did it,” Jimmy sobbed.

“Of course you did honey,” Emily chuckled as she shared his enjoyment. “And you did it very very well too.”

“Priscilla…” Jimmy started to say but Emily put her finger to his lips.

“Doesn’t know beans,” she finished. “Her loss was my gain.”

“I want to do it again, Mrs. Grant,” Jimmy announced.

“First of all, I became Emily to you a few minutes ago, now and forever more,” she informed him. “As for again, I suppose so. We can relax a few minutes and – huh?”

Emily’s eyes opened wide when she felt Jimmy’s manhood, spent and sticky a minute ago, was now hard again inside of her.

“My word!” Emily declared, stunned that the boy had recovered so quickly.

“Been practising with my pillow a long time for this,” Jimmy said in a voice that had lost the quiver. “Sometimes I go for hours, and that’s with only a dumb pillow and picturing you in my mind.”

“In that case,” Emily responded as she rolled around and put Jimmy on his back, and after mounting him and putting his prong back into her told him, “Let’s try this.”

“Oh man!” Jimmy exclaimed as Emily braced herself by putting her hands on the headboard, a position that Warren had especially liked back in the day. “This feels even better.”

“Yes,” Emily hissed as the stiff dick moved in and out while he humped him, the ancient headboard creaking like it used to, and went the young man’s hands cupped her dangling breasts she cooed, “Oooh – I like that too.”

“Didn’t imagine they would be so big!” Jimmy marvelled as he squeezed the plaint flesh.

“Didn’t get bigger – got lower,” Emily grunted, and as Jimmy tenderly caressed her breasts he told him, “No need to be gentle. They like being played with rough.”

“Like this?” Jimmy asked as his fingers dug into the giving flesh.

“Yeah – harder honey,” Emily implored him, and he got progressively rougher until he was practically pulling them off her, making her cum again before he spurted his load into the senior.

“Whew!” Emily exclaimed as she rolled off of her lover, collapsing onto her back and staring at the ceiling while suddenly feeling that she was not a spring chicken any more.

“It didn’t hurt honey,” Emily told Jimmy as he rolled onto his side and gingerly touched her breasts around the marks his hands had left. “They’ll go away soon.”

Jimmy’s eyes left the breasts that were flattened by the woman being on her back, and when Emily saw where he was looking she tried to lower her arm, having used it to prop up her neck.

“No don’t,” Jimmy said as he held the reed thin bicep down against the bedding.

“I must stink,” Emily frowned as she glanced over at her moist armpit that the boy seemed fascinated by.

“No, you always smell nice Emily,” Jimmy said in finally using her first name, and after he leaned down and pressed his lips against the smooth and softly scented hollow he commented, “You shaved.”

“Oh!” Emily replied, and not wanting to admit to prepping in hopes of being seen like this she explained. “What with warm whether coming on and all – but how on earth did you know?”

“I look at all of you all the time,” Jimmy admitted. “I think it’s kinda sexy when you don’t shave for a while, but this is nice too. So smooth.”

“Jimmy! What are you…” Emily giggled as the kid kissed his way up and down the deep pocket, squirming but not stopping him because it felt so good.

“Am I weird?” he asked after raising his head.

“Yes, but in a sweet way,” Emily replied as Jimmy’s eyes went down her waif-like torso, leaning down to take a look at the orifice he had just entered twice. “What are you up to now?”

“Exploring,” Jimmy said as he toyed with the sparse wisp of hair around Emily’s sex, stroking the prominent labia which would have been hidden in the bush before it had thinned over time, and as his seed bubbling out between the lips he gushed, “This is so beautiful.”

“OH!” Emily groaned as the lad buried his face in her sex, licking away like a gleeful puppy with enthusiasm making up for his lack of skill, and knowing that she was likely done cumming for the night pulled him over so his twig and berries were at eye level.

Emily leaned up and took the entire pouch on her mouth, suckling on the wrinkled orbs and delighting in hearing Jimmy’s muffled reaction as he lapped away. The senior nursed on the seed makers, even letting her tongue glide up the ridge underneath his scrotum before going back to his balls for more affection.

With her mouth full, Emily couldn’t say anything up course, but if she could have she might have uttered something like, “What in-tarnation is wrong with the boy?” because of what was lurking ominously above her mouth.

Jimmy’s penis was hard again, the underside of skinny spout stretched and straining as it quivered there like a pointer, and while his modest organ wasn’t any more than four inches long at best, there was no denying his virility.

Emily let go of Jimmy’s balls and moved her mouth up to the stiff tube, first licking the olive sized glans and then sucking on it, her lips sliding down to the base as Jimmy groaned in ecstasy.

After a couple of aborted attempts at moving her mouth up and down the short distance, Emily decided just to suck on the boy’s tool like it was a thumb, using her throat like a vacuum as she tried to swallow the dick.

Soon Jimmy was barking like a seal, or at least that was what it sounded like with the lad’s crotch covering her ears, and then she felt the teen’s dick jerk a couple of times as he spurted a modest load down her throat.

“I’m never going to forget this day,” Jimmy told Emily after he let her rest for a minute.

“Me neither honey. Me neither,” she sighed as she went back to looking at the ceiling, the guilt in her heart diminishing and Jimmy’s spooned up next to her.

It might have been the most emotional and exciting day of the summer but it was far from the last as Jimmy spent part of nearly every day at Emily’s house, culminating in an all-nighter the day before he made the 400 mile trip off to college.

“What am I going to do without you?” Jimmy asked before he said goodbye.

“That’s my line,” Emily interjected. “Now just remember to study and get out into the college community. Find yourself a nice girl.”

“I did,” Jimmy said, but after Emily gave him an admonishing look he shrugged and said, “I’ll try.”

“And you’ll succeed,” she assured him. “Trust me.”

“I’ll be back for Thanksgiving,” Jimmy reminded her.

“And I’ll save up my energy,” Emily answered.

***

Epilogue…

“Hey Jimmy,” his roommate Kurt chirped when he got back to the room after class. “No candy if you don’t say trick or treat, although the mask is funny.”

“Maybe the more times you say it the funnier it will get – I hope,” Jimmy replied, enjoying the ribbing he got from his newest friend.

“Hey, your grandmother stopped by,” Kurt said as he reached over his textbook for the note.

“My grandmother?” Jimmy asked in confusion.

“Yeah, I guess that’s who it was, although she didn’t say,” Kurt explained as he gave Jimmy the message. “Cute little lady with silver hair? She said she was passing through and wanted to say hello. She’s at the Comfort Inn over on – hey? Where are you going?”

“Later,” Jimmy called back over his shoulder as the door swung shut behind him, and as he raced down the hall laughing wildly he wondered how fast he could get to Room 347 of the Comfort Inn from there.

The End.