A Most Unlikely Fantasy

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A guy in his 30s finds himself with a woman in her 70s.
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Humpdee84
Humpdee84
113 Followers

Jack moved into what he called, his 'closet' right after splitting up with his wife. It was essentially just a bedroom with a kitchen and bath. "Studio" was over stating the situation but since it was all he could afford in a short time period, who was he to argue? He hit it off with the landlord upon their first meeting so the rent wasn't what it COULD have been. And Jack liked the fact that the building was just big enough that he could just sort of blend in and not have to really connect with his neighbors. Working nights was a huge help. Jack would get home around the same time they were all going to work. He'd be out the door in the evenings to visit his friends. Life would work in this temporary housing.

Across the hall however was Lucy. Lucy was ALWAYS home. She seemed like a nice enough person, a women in her late 60s, early 70s. Jack found her pleasant but didn't even give attraction a thought. Her age was one thing, but she was rather overweight (not that weight often mattered with Jack, but....), used a bit too much make up and smoked...A LOT. Yech. Jack enjoyed the two or three minute conversations by the mailboxes, and was fine with keeping their relationship that way.

One morning he got home, exhausted, and went right for his door. Suddenly Lucy's door opened and she stepped into the hall. "Jack," she began, "I'm so glad you're home. I'm a little bothered. There's a spider and It's HUGE. I'm normally happy to kill them, but this one...."

Jack stopped. He looked at the floor and then at Lucy. He was so damn tired, but hell, this wouldn't take long. "Sure, where is it?" He followed her into her kitchen and damn it all, it WAS huge. Jack, not one to shy away from a challenge, grabbed some paper towels and slowly approached the spider and....BAM, he got it. Jack didn't want to admit anything, but he had been a bit shaking and as he heard the spider crackle in the towel, he got slightly queasy. Gross.

Lucy thanked him profusely and offered him a cup of coffee. "Lucy, I'm heading for bed, the last thing I need is coffee, but you are sweet to offer," he said politely declining the offer and desperate to get out of that stale smelling apartment. "You know something Lucy, maybe next time...." He caught himself, "No, there will be NO next time."

She looked crushed until he added, "No more spiders in here! Tomorrow I'll come by with some really good bug spray and we'll prevent those devils from coming in again." Lucy was tickled pink and hugged Jack which made him cringe. In his mind he screamed but openly he said, "There, there Lucy, no worries."

The next day Jack came by at about 8 o'clock in the morning. He had worked but it hadn't been too crazy so he wasn't about to slip into a coma. Plus, he had promised his neighbor to rid her apartment of bugs. He knocked a couple of times with no response. Just as he figured Lucy might be still sleeping...or God forbid, DEAD and he was going to go into his own apartment, the door opened and there stood Lucy in a towel. Jack was dumbstruck. Should he run? Should he ignore the situation? He just went with the flow.

"Jack, I'm so sorry. Were you waiting long?" Lucy began. "I was in the shower. I almost forgot you were coming by."

"It's all good." Jack entered the apartment and was struck by the fact that it wasn't as stifling and stale as the day before. He noticed she had opened the windows and lit a few candles. "I guess even Lucy can't take that shit for TOO long" he thought. He entered and asked Lucy, "I'm sorry I got you out of the shower. I can come back when you're dressed."

"No, no, don't worry about it. You're doing me a favor and I should not keep you waiting. Just give me a minute." And off she went to the bedroom to dress. As she walked away, the towel fell. Jack's eyes popped out of his head and his lunch almost from his stomach. It wasn't a long look, it was quick, but, oh hell, a guy his age did NOT need to see the naked body of a woman his GRANDMOTHER'S age.

When Lucy came back, she was in one of her Muumuus ("God Bless the Hawaiians," thought Jack.) and Jack set about spraying all the corners of the apartment, along the baseboards, behind things, under things, he was a spraying machine! When he was done, Lucy thanked him with a hug and a kiss on the cheek. Jack said it was nothing and he left without further incident, off to bed and the expected nightmares.

Things for the next few days were normal. A brief chat by the mail boxes or in the laundry room with Lucy or maybe another neighbor but for the most part, Jack was enjoying the solitude.

A week or so after seeing Lucy naked, Jack was chatting with her and she happened to mention that her birthday was just around the corner. Jack, being who he was asked, "So, turning 30? Well, it's about time!" Lucy laughed, "No, I'll be 78." Jack was surprised. No, she was no kid, but he didn't figure she was that old. "Good for you, hun. What day?" he asked.

"Tuesday." She replied and Jack made a mental note. They chatted a bit more and then parted.

That Tuesday, Jack had decided to surprise Lucy. She was a sweetheart and seemed lonely and Jack had nothing going on and just so happened he was off that night. He bought her a big bottle of wine and a dozen roses and showed up at her door. He knocked and when she opened the door, she nearly fainted.

"OH MY GOD!" she exclaimed, "Why did you do this? Oh, you are so sweet. Oh please, come in, come in and please, PLEASE share some wine with me?!?" Jack did.

They had a lovely visit and again, Jack noticed she had cut down her smoking and the apartment wasn't the equivalent of a gas chamber. Visiting wasn't going to be such an invitation to cancer as he feared. He sat and Lucy opened the bottle, pouring both a healthy glassful. They sat and talked for over an hour about all sorts of subjects and Jack was actually really enjoying her conversation. She was an interesting person and the more he looked at her the more he thought she had a nice quality to her. His mind stopped short of finding her attractive. In fact at one point he sort of squished up his face and shook his head. "You OK?" asked Lucy.

"Oh, oh, yeah, I'm sorry. Funny enough sometimes I get this weird feel from wine, but it passes as fast as it comes," and he held up his glass for a refill.

After about 3 hours of gabbing, ("THREE HOURS?!?!?" thought Jack) he excused himself saying he had to get up early in the morning. He didn't get anywhere. When they finished the wine, Lucy had brought out a bottle of Sherry and they polished THAT off too. Jack was not lightweight, but...

He got across the hall and went into the bathroom to relieve some pressure on his bladder. When he was done he started picture Lucy naked. He found himself almost getting hard, but he caught himself, changed and slipped off into a coma for the night.

A few days later Lucy again needed a favor. She couldn't reach something on the top shelf of her cabinet and asked Jack if he could get it. He did and next thing he knew they were sitting over tea chatting away. By the time an hour had passed the subjects had been very random and at one point, sex had become a topic.

"So, believe it or not, I've had more than my share of guys, well, back in the day, " Lucy had blurted out.

"I don't doubt it, Lucy, you still GOT IT GIRL!" replied Jack, not sure if he actually believed it or was being polite. She did have a quality to her, but....eeeeyooo.

The conversation ended not long after and Jack left. He felt that was an odd twist that never got explored.

A few more days went by and Jack was feeling down in the dumps. It was Jack's night off. All his friends were busy and he just needed to chill thinking about the impending divorce. Lucy saw him coming in the building and met him in the hallway. "You don't look happy." "No, I guess I'm a little low, but that's life." Jack replied with no real commitment. Lucy invited him in for a glass of wine, Jack readily accepted.

It was a great visit. Jack and Lucy laughed and talked about so many things as seemed to be the normal thing for them. Lucy made Jack a sandwich. Things were normal but that was when she 'accidentally' dropped some mustard on her lap. "DAMN," she exclaimed. "That's going to stain." And she jumped up and whipped the muumuu off right there in front of Jack. Standing there in just her panties, she went under the counter to get her anti stain bottle and began to rub it onto the mustard. Jack just sat there staring as she wiggled and jiggled. Lucy went down the hall, seemingly oblivious to Jack's reaction, and got another muumuu.

She sat down and started the conversation as if nothing had happened. But like a previous visit, the subject slowly turned to sex. As she talked about some of her exploits in her younger years, and some NOT so younger years, Jack began to get hard. In his mind he kept trying to think about Baseball, puppies, dead rats, ANYTHING to keep himself flaccid, but it wasn't working. Then Lucy changed the subject. Jack's mind screamed out "WHAT THE FUCK?!?!?!"

The visit ended and Jack went across the hall where he lost his mind and whacked off like he'd never whacked off before. He felt he was losing his grip on reality.

He didn't see Lucy the next day, or the next for that matter. He was getting concerned, especially with how he was beating off to her, almost on a daily basis. It scared the hell out of him. What was becoming of him? He needed to meet a woman his own age, not this BLOWESER! He immediately regretted his choice of words and just as fast thought, "It's NOT like she can read my MIND! What do I care?"

Jack was in a very confused state.

He knocked at her door one evening wondering if he had done something wrong since they hadn't spoken in several days. She came to the door and greeted him like an old friend, invited him in and offered him a glass of wine. "You don't have to work, do you?" "No," replied Jack, "I was curious why I haven't seen you in a few days. Everything O.K.?"

"Oh of course, I wasn't feeling too wonderful and just needed extra sleep is all. I'm so sorry if I worried you," she replied handing Jack a large glass of Merlot. "Plus I was a bit embarrassed."

"About what?" asked Jack.

"I've been parading around without even thinking about it, showing myself off and it's not right. I sometimes don't realize I'm doing it." She answered, looking at Jack and then the floor and then Jack again.

"Lucy," started Jack, "Don't give it another thought. Don't be embarrassed. You gave this guy a little thrill, to be honest." He WAS being honest and again, that made him feel very awkward. "Lucy, if you EVER want to show yourself off to me, you go right ahead, even if it's unintentional." Did he really just say that? Was he really losing it?

"Jack, you're just so sweet."

And as always, it seemed like sex was off the table again. Lucy talked about how the construction in the neighborhood was so loud and how she was thinking of giving up driving and various other subjects for about an hour and two glasses of wine. Jack was thinking, "Are we going to take this somewhere or is she screwing around with my head?"

"Jack, you have no idea just how long it's been since I've seen a man's penis." She suddenly blurted out with no warning what-so-ever. Jack nearly shit himself. He sat in stunned silence for what seemed like 10 minutes but in reality was only about 10 seconds. His mind processed what she just said and how he should react and then, as if a switch was thrown he said, "Well, I could get naked right now if you want. I mean, if mine would do." And he stood not even waiting for a reply, took off his shirt, kicked off his shoes and socks and dropped his pants and skivvies. He was flaccid but his mind said, "Not for long!"

"Come here, please," said Lucy and he approached her chair. She bent over a bit and stared at his member. "May I touch it?" she asked. Jack sheepishly said, "I would like that." And she did, just a short small brush of her fingertips around his cock and under his balls. Jack's member, jumped just a bit.

"It's pretty" Sighed Lucy.

Jack thought, "Pretty? Never heard THAT before." He was a bit self conscious since, he wasn't all that big; Irish Curse and all. "Thanks," he added.

"Do you masturbate?" she asked. He replied, "Of course, doesn't everyone?"

"Could you masturbate for me?" Lucy asked him. She seemed to have an almost childlike innocence to her when she spoke. It was odd, Jack thought, like she was exploring something very unfamiliar, especially after the stories of her exploits, though she never did go into any real detail. Jack thought, "It might be fun, why not. Should I? Is there something wrong with this picture?"

As all these thoughts were racing through Jack's mind, Jack began to caress himself, pull at himself, and tickle his own scrotum. Lucy watched intently, like a scientist watching an experiment, waiting for something extraordinary to happen. Jack got hard, very hard. He began to stroke himself, slowly at first. His eyes were closed but he would occasionally look down at Lucy sitting there glaring at his actions. It was turning him on immeasurably. Lucy showed no emotion, just stared.

"A little faster please." Requested Lucy. Jack complied. Lucy just watched. Jack was now staring at Lucy, studying her as much as she studied him and it was turning him on, VERY much. Having this old...no, OLDER woman watch him jerk off was actually a BIG turn on. Within a minute, he felt himself about to cum. He said nothing to Lucy and then, it shot out of him right onto Lucy's muumuu. Lucy didn't move and Jack finished himself right where he had started. He put his hand on Lucy's shoulder to steady himself. Lucy slid one finger up his shaft from base to head and felt his semen on her hand. She smiled at Jack, Jack smiled back.

Jack's head was a bit light and he needed Lucy's shoulder right now and she knew it. She put her hand on his and smiled up at him again. "I liked that. It's still a pretty penis, but now I can see how manly it is." Lucy smirked. She got up, got him a towel and cleaned him off a bit as Jack regained his composure. It had been a hell of a climax, especially since he had gotten HIMSELF off.

They chatted just a bit and Jack said he really needed to lie down. He dressed himself and somewhat staggered across the hall and fell into bed, his head trying to wrap itself completely around what had just happened.

The next day he saw Lucy by the mail boxes. She looked at him and said, "Jack, could you come over tonight and show me that thing you do again. It was lovely." Jack didn't hesitate. "Yup. What are you doing right now?"

Off they went to her apartment where once again, Jack jacked. This went on for a few days. On the following Friday, it happened twice, the second time Lucy got naked and had him cum on her breasts.

The weekend was dead. Jack was working overtime and Lucy was visiting an old friend in the city.The whole time, Jack just kept looking forward to Monday. He hoped that Lucy would become a more active participant this time. He thought it might be nice if she at least cupped his balls, maybe let him play with her tits. It had been a bit sterile up until then, like he was a lab rat in some kind of sexual experiment. He was OK with it all, but it was becoming a bit routine. Then again, an orgasm with a friend is better than one alone or none at all.

On Monday, Jack got home from work a bit early and knocked on Lucy's door. She asked who it was and when Jack announced it as he, she opened the door and grabbed his wrist, pulling him in. She was naked as a jaybird and brought jack over to the table. She sat down positioning him in front of her and started to pull his pants down. Jack, not wanting to be rude stripped off his shirt and carefully kicked off his shoes. Now both were nude. Jack reached for himself but Lucy slapped his hand away and while looking up at him, engulfed his cock with her mouth. He became rigid in less than 5 seconds. "HOLY SHIIIIIIIIT!" whispered Jack, though he believed he only thought it. Lucy's tongue was pretty damn agile even if the rest of her wasn't. She sucked and licked and kissed his genitalia like a pro. "Was she a pro?" That one Jack DID just think to himself, luckily.

As jack began to get tense, Lucy sensed he was ready to cum. She grabbed him with a death grip and began to pump him like he was a bicycle pump, all the while keeping her mouth wrapped tightly around the head of his erection. Jack began to moan, then he got louder, then, not even realizing what he was saying, he growled out, "SUCK IT WOMAN, SUCK IT!"

And she did.

Jack nearly exploded. He had rarely ever cum with such power. He swore the neighbors must have heard him, and he was sure the people in the next building heard him and maybe even his ex-wife three miles away. He found himself almost yelling, "You WISH you could do this so good!" at the woman who wasn't even there.

Lucy was confused but later when she asked, Jack explained. In the meantime...

Jack nearly fell over. Lucy finished him and when she was done, he didn't even need a towel, there was nothing left to clean up. Lucy giggled, tickled his balls and got up. As Jack stood there shaking and trying to regain his balance, she put one foot on the chair, grabbed his hand and placed it between her legs. He got the message and began to rub her, sliding his fingers inside of her and using his thumb to stimulate her clitoris ("She still has one I assume"). She didn't feel gross as he anticipated. Just wet, VERY wet like any woman who was worked up sexually would be. He ran his fingers all around her, into her over and over again. Lucy stopped him, took him by the hand, led him to the couch and then flopped onto it pulling him with her, his hand still in her crotch.

Jack was lucky to be still functioning after what Lucy had done to him, but somehow he managed to fall beside her and keep rubbing until Lucy let out such a scream that the walls shook.

"HOLY FUCK, I hope no one thinks Lucy's being murdered. I could go to prison. Fuck, fuck, fuck" went Jack's mind. Yet he kept going. He kind of had to, Lucy would NOT let go of his wrist.

Once she was done, she let Jack go. The two of them sat with their heads back, lost and spent for about an hour. Jack had the disadvantage of already being tired from a long night at work, this did NOT help. Lucy, who had slept well all night, would sleep much better tonight, but it was only Eleven O'Clock in the morning!

Once they had recovered, Jack took his leave but as he left, Lucy said, "I want you to fuck me next time and the time after that, I want you in my ass." And she closed the door.

Jack stood in the hall for a few minutes. Eddie, from down the hall came out of his apartment. He was on his way out but as he started to pass Jack, he stopped and said, "Man, I don't know if I could do that. You my hero, dude." Then he left the building. Jack went into his apartment and collapsed. He slept until his alarm woke him at 10 p.m.

A couple of days went by and Jack didn't see Lucy. He figured she must be visiting her friend again and let it go at that. He also realized that, in spite of their 'relationship' he never did get her phone number so he couldn't even call and leave a voice mail. Well, he'd see her soon enough.

He still would have those moments of disbelief. "I'm doing, HER?!?! What the FUCK?!?!?" But overall, he was having the time of his life and there was NO commitment. The only downside was that since he was SO well taken care of, he had stopped checking out other women and didn't even consider asking anyone out, even though Jerry at work had mentioned that a girl, Pam had shown an interest in the newly divorced guy. Whatever.

December brought about some cold weather and some hot sex. Jack and Lucy were going at it like rabbits. She would suck him off, he would fuck her brains out. It was almost daily but now and then, without explanation, Lucy would be M.I.A. Jack just figured she was visiting her friend. He was having an amazing time with this woman but since he didn't "OWN" her, what right did he have to ask any questions. He had noticed she was losing weight. "Well, she's looking pretty decent, though..." He never finished that thought. He always felt guilty as hell when his mind brought up negatives about Lucy and he quickly dismissed those musings.

Humpdee84
Humpdee84
113 Followers
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