An Observant Housesitter

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The story involves Jerry Howard, a recently retired 62 year old widower with a lot of time on his hands. Jerry got recruited to keep an eye on his daughter’s house while she went on vacation with her kids, mostly because she didn’t want her ex-husband anywhere near the house. All it involved was feeding the family cats and – oh by the way the bathroom sink is dripping.

There was always an “oh by the way” when it came to his daughter but Jerry didn’t mind and besides, it gave him a chance to get out of his apartment which had started to feel like a tomb.

Besides Jerry’s daughter’s house was much nicer, and the only thing that would have made it better was if she had a swimming pool like the neighbor’s next door, so he decided to stay there for the week instead of driving back and forth to feed and water the cat.

Early in his stay Jerry discovered that there was a young lady next door, a cute plump redhead with freckles on her shoulders and around her nose which made her look like a chubby version of the girl on the Wendy’s logo.

Jerry wasn’t adverse to looking so this was an ideal opportunity to watch something more interesting than Judge Mathis, and while the young lady was not what one consider a raving beauty she was cute in her way and besides, Jerry never minded a lady with a few extra pounds on her, even if the neighbor girl’s extra baggage was probably more like 30 or so pounds.

“More cushion for the pushin’,” Jerry had mumbled to himself when he first saw the dripping young thing emerge from the water, and then tried to remember how long it had been since he had sex with anybody but himself.

Jerry didn’t know that the young lady he was watching was also house sitting in a way, but she didn’t have to be there. She could have gone on that cruise with her parents but she had experienced that once and it was boring enough for 5 days. This current cruise was twice as long and that meant twice as boring. Ten days with Mom and Dad would have been hell enough but the endless buffets were even worse so she stayed home.

What does an 18 year old soon-to-be college freshman do to pass the time, besides working her part-time job at the town library? Swim. Andrea Barney loved to swim and besides, there was no food out there to tempt her. Having lost almost 20 pounds over the last few months with more than that to go, Andrea was determined to enter college a slimmer and hopefully more desirable girl.

Andrea had no idea that there was somebody that found her attractive just as she was, but she would find out soon enough. If she had thought to look up at the window of the house next door and was able to see the old man with the binoculars she might have found out about her admirer even sooner.


“That’s it honey,” Jerry said softly to himself and the young lady emerged from the pool, her still pale skin shimmering in the sunlight. “Such a cute little butterball you are.”

Jerry had remained on watch as soon as he saw the girl emerge from her back door, towel in hand along with a bottle of suntan lotion, and he enjoyed watching the girl oil herself thoroughly before getting into the pool.

Now out of the water the girl went right into the shade to dry off, and Jerry enjoyed that as well.

“Redheads burn easy – or at least that’s what I’ve heard,” Jerry told the empty guest room as the young lady dried her curly locks, adding, “and you dear are a natural redhead. Sweet.”

Jerry had assumed the girl was a authentic redhead because her locks looked too real to come out of a bottle, but seeing the burnt orange stubble that filled the large recesses of her armpits – stubble that was only five o’clock shadow the day before – confirmed it.

Now Jerry’s eyes were drawn lower because something really caught his eye. The young woman’s one piece bathing suit was decidedly modest, only providing a glimpse of what seemed to be a healthy cleavage between her round breasts, but now thanks to one of the leg openings curling back a little Jerry was getting a peek that made his day.

“Oh darling,” Jerry sang when he saw the burnt orange hair pasted on the inside of her thigh, and although she must have felt the fabric had adjusted and reached down and fixed it, the look was enough for the ecstatic senior. “I love you darling.”

Jerry was an old school kind of guy who found the twenty-first century trend of women shaving their pubic hair revolting, so seeing that his little object of attention was a furry thing made his day. The fact that she hadn’t fully corrected the wardrobe problem as the day went on delighted him as well.

Even his own daughter shaved her pussy now, Jerry had just discovered, although he found out accidentally earlier when searching for the binoculars he was watching through.

There was this little envelope of photos hidden up on a bedroom closet shelf, and being nosy Jerry had to look. When he saw they were pictures of his daughter Nancy and her ex-husband naked and doing things to each other that married people do, Jerry put the photos back, but casino siteleri not before looking at them briefly.

He smiled at the ones that her goofy ex took of Nancy sucking his cock, and although Jerry was proud of the way the first picture showed his daughter looking up with her mouth down to his curls, he chuckled when the other picture showed Nancy holding her ex’s saliva coated stiff dick and it turned to be a short fat stub of a cock.

There were pictures of Nancy – probably taken about five years ago – and they were very graphic and fairly well taken. They were clear enough so Jerry could see that Nancy’s left breast was a bit larger than her right, although they were smaller than Jerry would have guessed, but the pictures of his daughter’s smooth mound turned him off.

“Now on the other hand this is what a real woman should look like,” Jerry sighed softly as he wiped his brow with the back of his hand before raising the binoculars back up to watch the girl resting in a lounge chair, and as the young lady brought her chubby yet curvy legs up on the cushion and parted those plump thighs his heart skipped a beat and his right hand went into overdrive.

The old-timer had been stroking his cock for quite a while, his manhood having forgotten it was over six decades old, and getting such an perfect view of the furry gal’s treasures got even better as her feet stayed planted when her thighs opened.

If she was trying to excite Jerry she could not have done a better job because in no time Jerry was cumming, his long grizzled member spurting all over the hardwood floor while he almost doubled over from the force of his orgasm.

A degree of guilt swept over Jerry when after he milked the last of his sap out of his deflated cock and saw the mess he had made but that went away fast.

“You still got it kiddo,” he told himself. “You can still get it up and you still cum like a freight train. You aren’t done yet, although if I keep talking to myself they might put me away.”

After mopping up the warm sticky seed he made a mental note to replace the bottle of hand lotion that he was using to jerk off with because at the rate he was going, that half empty bottle would be gone in no time.

“As for you my little butterball,” Jerry said as he took another peek before going downstairs. “I think it’s time we got better acquainted. Putting a name on my dumpling will make it even better. You look like a – a Wendy. Why not?”


Jerry waited until the girl next door came back outside before making his appearance by the fence, She was unaware of him at first which gave the senior a chance to get a nice look at her in the flesh instead of through a window or binoculars.

When Jerry finally cleared his throat to sort of announce his presence she was clearly startled and grabbed the towel to put it in front of her as he introduced himself.

“Oh,” the girl said. “I saw a light on over there and so I thought maybe they were back from vacation or something. I’m Andrea Barney.”

“Andrea,” Jerry repeated, noting to himself that his guess wasn’t even close, and when he reached his hand over the fence to offer a greeting she nervously shook his hand while fumbling with the towel. “It’s my pleasure.”

After clasping her pudgy paw he bowed a little and raised her hand and kissed the back of it, causing Andrea to giggle nervously. While playing the part of the elderly aristocrat his eyes went to the outline of her nipples through the damp bathing suit and then to the burnt orange peach fuzz under her arm.

Jerry’s look apparently lasted too long because Andrea figured out what he was looking at and took her hand away and lowered her arm quickly, mumbling something about not expecting anybody around.

“You live here with your husband?” Jerry asked innocently, and after a moment of confusion Andrea laughed.

“No. This my parents house. I’m not married,” Andrea explained. “I’m only 18.”

“Really?” Jerry mused aloud. “You seem much older. More mature.”

“Tell my Mom that,” Andrea quipped.

“Well I don’t want to interrupt your swim…”

“No, it’s okay,” Andrea replied. “Stuck out here alone with nobody to talk to – it’s nice to have somebody around.”

“Gee, a pretty girl with a swimming pool,” Jerry said. “I would think the place would be swarming with guys. No friends?”

“I’m not really social,” Andrea admitted, and Jerry noted that when he called her pretty it had an effect on her. “As for boys, well the less said the better.”

“Oh, just go through a bad breakup?”

“No, I – never mind. It’s complicated.”

“Oh well. Anyway, I’ll be around doing some minor repairs and taking care of my daughter’s cats,” Jerry explained and then added, “Too bad Nancy didn’t have a pool installed over there.”

“If you want Mr. Howard, you can use our pool,” Andrea offered. “Nancy’s kids do.”

“Oh, that’s nice of you,” Jerry said. “Maybe I’ll take you up on that, although I don’t know what I can use for a bathing suit. Maybe I can figure canlı casino something out.”

“Hope you do.”

“You know with all this privacy you folks have down at this end of the street – heck you wouldn’t need a bathing suit at all if this house was a little more around the curve. Nobody to see you but my daughter’s place next door and they’re gone for a week.”

“Sometimes at night when it’s real dark I sneak out here without a suit,’ Andrea confessed with a giggle.

“Oh my,” Jerry responded with mock shock. “Maybe instead of getting a bathing suit I should invest in night vision goggles.”

“I don’t think that would be a wise investment Mr. Howard,” Andrea laughed. “Even in the dark I’m nothing much to look at.”

“I disagree. Quite to the contrary. I think you’re a lovely young woman. You have a healthy glow about you,” Jerry said. “Sort of a old fashioned country girl look. I may look like an old coot but my vision is still fine.”

“I’ve been losing weight,” Andrea mentioned.

“All well and good but there’s nothing wrong with a woman having a little meat on their bones so don’t get too carried away with the dieting. So many girls these days look so scrawny and skinny – I know it’s the fashion but still,” Jerry commented before shrugging and adding, “Just one old goat’s opinion. Maybe I’ll take you up on that offer of a swim later, especially if it gets hot again today.”

“Supposed to,” Andrea said as they both retreated from the fence. “You don’t have to knock or anything. Just come over.”

“Okay,” Jerry said as he watched Andrea walk away.

“Nice,” Jerry said while enjoying the view of her backside, the legs chubby but shapely and seeming to be firm, and a rear end that was full and inviting even in the dumpy swimsuit, and after he got inside he continued his appraisal.

“Bigger on the bottom than she is on top… I’d say maybe something along the lines of 38-29-42,” he decided. “Maybe that’s a little kind but that’s my nature, and if I stay in here looking at you Andrea my dick will be hard again and I’ll spend the day jacking off like a chimp.”

With that in mind Jerry hustled out to the car and made it to the mall in record time.


Jerry rearranged himself in the bathing suit he had just come home with, wishing that there was more there so that when the trunks got wet he would make a better impression on the young lady who was going to have a guest shortly.

The six pack of wine coolers was a bit tacky but he figured that young girls probably like the things and who knows? Maybe Andrea would down a couple of them and things would happen from there, he joked to himself at the thought a girl less than a third his age would have any interest in him.

So armed with the wine coolers and a semi-erect dick that had been in that condition since he first saw the chubby chick next door, Jerry wandered over, rubbing his hand over the salt and pepper hair on his chest to fluff it up on the way.

“Hello?” Jerry called out through the screen door, and when Andrea seemed happy to see him his heart quickened.

“Hi Mr. Howard,” Andrea chirped as she stepped out, having put a terry covering over her top but still in her bathing suit. “Ooh! Wine coolers!”

“Never visit empty handed is my motto. Something you like?”

“Yeah, but don’t tell my folks,” Andrea chided the old fellow. “Me and a girlfriend have gotten them a couple of times and gotten really goofy on them.”

“Nothing wrong with being goofy,” Jerry observed, wondering whether being goofy with her girlfriend included getting naked and enjoying each other.

“Just remember to take the empty bottles with you later,” Andrea cautioned. “Mom and Dad will wonder how I got them.”

Jerry started to ask why they would mind the college student daughter to drink a couple wine coolers but then was brought back to modern times.

“Oh, I’m sorry,” Jerry said after the girl reminded him that the drinking age was 21 these days. “I shouldn’t corrupt you.”

“I’m not all that pure,” Andrea giggled as she took the six pack and put it on the table. “Although I do try to make my folks think that.”

“Well I think it’s wonderful for you to be so kind as to invite an old coot like me over for a swim,” Jerry said.

“You aren’t so old,” Andrea said. “What are you? 55?”

“62,” Jerry corrected, and he not only didn’t know if she had guessed low on purpose or not, he didn’t care. “Thank you.”

“You look great for your age. My Dad? Well, he’s lots younger than you and you’re in way better shape,” Andrea said. “And I like the suit.”

“Oh, thanks,” Jerry said, glancing down and noticing that the outline of his dick was showing because he had gotten aroused just by talking to the friendly redhead.

“Want to have a drink first and then swim?” Andrea suggested, and that was fine by him because sitting at the patio table he got to examine the teen more carefully.

The first thing he noticed when Andrea took off the terry covering was that she had shaved kaçak casino her underarms since he was there earlier, the large round craters now creamy smooth.

That was no doubt a result of his staring before, and while it mattered little to him either way the idea that she had gone out of her way to prepare for his visit gave him hope that his interest had intrigued Andrea.

The other thing Jerry noticed immediately was that the grooming the teen had applied to her armpits did not go any farther since when Andrea sat down the flaming red hair peeked out again from the leg openings of the modest suit.

Jerry forced himself not to stare because if Andrea was aware of what he was fascinated by that might disappear too. Instead he focused on the girl’s breasts, round and full if not overly large, and while they might not be the equal of her slightly larger bottom half, the globes looked great to his eyes.

Jerry tried not to wince when he drank the wine cooler, and after they were done they climbed into the pool. The old man kept his distance for a while, preferring to just enjoy the view, but Andrea decided to come over and get playful.

“I swim by myself all the time,” Andrea declared as she tried to dunk the old timer, and that got them to splashing around playfully for a while until Andrea decided she was thirsty again.

They emerged dripping from the pool, and after they twisted off the caps and stood by the table the old man noticed that Andrea’s eyes were looking below his waist.

“Oh dear,” Jerry said, expressing regret he really didn’t feel when he saw that the outline of his cock was now very clear, the result of getting to touch Andrea’s wet flesh in the pool. “I’m sorry.”

“Nothing I haven’t seen before,” Andrea replied. “I would hate to see your friend there when he’s angry though.”

“Uh – my friend as you refer to him – is rather angry already I’m afraid,” Jerry confessed. “That’s the result of not only sharing the company of a beautiful young lady but getting to frolic like we did in the pool. Been quite a while.”

“That’s the second time you called me lovely or beautiful,” Andrea said. “You say it often enough and if we have enough wine coolers I might start to believe you.”

“I should have gotten 2 six packs,” Jerry suggested with a wink and then added, “And you’re sweet to humor a silly old man.”

“I told you that you aren’t old,” Andrea reminded him. “Besides, I seem to get along better with older men than kids my own age.”

“That so? Then there’s a chance for me?” Jerry asked, quickly added that he was just kidding.

“Sure there is, and I’m not kidding,” Andrea responded, and after seeing the old-timers stunned expression she downed the rest of the drink and went back into the pool, her large full buttocks the last to submerge.

“I’ll be damned,” Jerry mumbled to himself before joining his young companion.


“I’ve done more swimming today than in the last 10 years combined,” Jerry explained later as they stood by the wall of the pool after playing water basketball.

“You still have the rest of the week to come over before your daughter gets back,” Andrea said. “And you’re welcome to come over after that, even after my folks get back. They won’t mind, although maybe you should skip the wine coolers – and maybe ease up on the staring.”

“Oh,” Jerry said. “Sorry.”

“That wasn’t a complaint Mr. Howard,” Andrea said as she rested her elbows on the wall of the pool, her breasts thrust out. “I don’t get looked at very much so when it happens I revel in it.”

“Anyone who wouldn’t look is a fool,” Jerry suggested as his eyes drifted over from the cherubic lady’s breasts to her round shoulders beginning to tan despite her best efforts. “Did you do that for my benefit?

“What’s that?”

“Shave your underarms,” Jerry explained as he nodded at the pale hollows exposed my her position.

“You noticed,” Andrea said as she glanced over at her work. “Yeah, I saw you staring earlier and I didn’t want you to think I was grubby.”

“Hardly,” Jerry replied. “I hate to be one of those old farts who says stuff like – Back in my day – but back in my day when I was your age seeing a young lady who didn’t shave her armpits at all wasn’t all that uncommon. The sixties and seventies were much more forgiving of personal freedom and expression I guess. Now it’s all tattoos and piercings that are considered normal and hair is out.”

“I don’t have any tattoos but my ears are pierced,” Andrea explained. “I usually shave my pits every day in the summer when people are around, on account of me being so hairy and it growing back so fast all the time.”

“All women think they’re hairy,” Jerry told her. “I think it’s the way society conditions women.”

“No, I’m hairy all right,” Andrea assured the senior. “One winter a friend and me decided not to shave under our arms all winter and by New Years you should have seen me.”

“I wish I had,” Jerry replied, and that got Andrea to laugh. “Well, it’s the truth. You did a good job though.”

That comment came along with the old man reaching over and letting the back of his index finger slide up and down the smooth wet cavern under her arm, and when Andrea shivered but did not stop him he did it again.

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