My Old Babysitter - Cover

My Old Babysitter

by AlwaysWantedTo


Erotica Sex Story: MILF of a babysitter helps a young man take care of his dying father

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Fiction   Oral Sex   Voyeurism   Babysitter   .

Josh Randall flopped down on the dusty couch, exhausted. He loved his father but Jesus H. Christ, what a pain in the ass!

The nurses in the home said he was too sick to get out of bed but neglected to warn him how much attention he demanded. He banged on the wall with anything handy and when Josh removed everything from easy reach he did it with his arm. To stop the bruising Josh moved the bed away from the wall and checked on him constantly. However, whenever he was absent his father rattled the railings of the hospital style bed or rocked the footboard with his feet until he achieved an annoying rhythm. Relief only came when his father slept.

Shit! He forgot to get a beer. Josh dragged himself up and stumbled into the kitchen. He got a beer from the fridge, opened it, and wandered over to look out the back window, tossing the cap into the sink on the way. He took a long pull and gazed out the window, his mind blank.

Overgrown grass, a garden full of weeds, and a hedge grown wild and unkempt met his eyes, an unmitigated disaster to match the house which had been left to decay since his father went into the nursing home. After his father’s money ran out Josh paid the fees and considered it payback for college though he would have done it anyway. In the midst of investigating complications the doctors discovered the brain tumor that would kill his father within weeks. Josh took a leave of absence and, thankful he hadn’t sold the house, returned to honor his father’s wish to die at home.

Josh sighed. Compared to the new neighbors on the right the yard was a disaster. His gaze traversed to the other side, over a decrepit fence and into Mrs. Thompson’s back yard. She lived there almost until the end six months ago but even in ill health she kept the yard and house in better condition than his father’s tumbledown abode.

Josh wondered what happened to her daughter, his former babysitter. Julie left for college when he was six which would make her about thirty-seven now. Tall with long, curly dark brown hair, Josh remembered her better than he did his own mother who left when he was five. In contrast to his dour mother, Julie laughed a lot and teased him mercilessly. Those days were the happiest in his memory.

Josh smiled, relishing the warmth that always accompanied thoughts of Julie. He remembered the day she teased him about marrying her when he grew up.

“It’s true,” she said, laughing. “You and I are going to be married and we’ll live right here in this house.”

“I’m not marrying any stupid girl,” Josh retorted. “And my Dad isn’t going anywhere without me!”

Julie laughed uproariously. “Oh yes you are.” Then her face darkened and she said, “I saw it in a dream.”

“Am not!”

Josh attacked her, landing two blows with his small fists before she could defend herself.

“Are too.” Julie laughed and fell back, fending off further blows.

Creak, creak, creak.

Shit. He’s found the footboard again. Josh tipped his beer and drained it. He put the bottle beside the sink and turned to go upstairs.

“I’m coming, I’m coming,” he yelled.

Three weeks later Josh woke with a start having fallen asleep again on the couch. He stood up and scratched his balls while he surveyed the empty bags of chips, half-eaten pizza, and cluster of empty beer bottles strewn around the couch, floor, end and coffee table. What a mess!

He was a mess! He listened for sounds from upstairs but heard nothing, stretched, and scratched himself again. Hungry, he looked at the remains of the pizza, shook his head, and started for the kitchen. Cereal would be better. After a quick breakfast he’d check on Dad and get out to buy some real food even if he had to leave him alone for an hour.

He was interrupted by a knock on the door. He nodded. So that’s what woke him up. Had he ordered a pizza for the morning? Before opening the door he pulled his t-shirt down to half-cover his shorts. A green-eyed vision from the past was smiling at him.

“Hello. Did I wake you?”

“Huh? Oh no, I was in the kitchen, getting ... Julie? Julie Thompson?”

“Yes, well it’s Belker now. You remember me? You were so little.”

“Yeah, yeah. It’s been a long time.”

“Yeah, you were just a kid but I’d recognize that impish face anywhere.”

She laughed and its tinkle wrapped itself around Josh like a warm comforter.

I didn’t expect you to be still living here. Mom said you left years ago and your father was in a home.”

“Yeah, that’s true but...”

“How is he?”

“Dad? He’s, well, he’s not doing too well. He’s had Alzheimer’s for a few years.”

“Yes, I was sorry to hear about that.”

Sadness gripped Julie’s face. Josh felt like he was intruding on a private moment and looked away.

Julie changed the subject. “I’m so happy to see you. I was just going to ask the new neighbor where your father was so I could visit him. I thought you’d sold the house.”

“Nope, it’s still here and run down. Us too.”

“I’m glad.”

Julie eyed him steadily, expectantly.

“Would you like to come in?” Josh blurted.

Julie shrugged. “Okay.”

Josh stepped aside and she entered. As soon as he closed the door he kicked himself for inviting her in to see the mess in the living room and the disaster in the kitchen with sink and counters full of dishes and discarded pizza cartons.

“Still a man’s house, I see.”

“Uh, yeah. I was about to clean up.”

“Hmmm. I came over to ask where Chuck, I mean your father, is but I could come back later. I’m staying at the Days Inn until I get the house cleaned up.”

“You’re moving back?” Josh asked, hopefully.

“No, selling.”

“Of course. I’m sorry to hear about your mother.”


An awkward silence ensued.

“Your father?”

“Oh yeah. Actually, he’s upstairs.”


“Long story but the short of it is he’s spending his last days at home.”

“Oh. So you came back to be with your Dad?”


“That’s tough.”

Julie surprised him by stepping close. She raised her face and stretched up to kiss him on the left cheek, her palm cupping the other one. She stepped back, smiled and blushed, and said, “Like father, like son. You haven’t shaved.”

Josh nodded. “That’s what everyone always says.”

“Not a bad thing.”

“No,” Josh agreed. “Not a bad thing.”

“Can I see him?”

“Are you sure? He’s quite sick. I can’t get him to eat properly, and...”

“I’m a nurse, Josh.”

“Oh. Well then, he’s upstairs.”

Josh stepped aside and swept his arm toward the stairs, realizing how beautiful woman she had become as he followed her up. She wasn’t as tall as he remembered, maybe five-five or five-six. Of course, to a six year old that was tall. He remembered the luxurious, chocolate brown that cascaded in waves over her shoulders. The black top and stretchy slacks she wore advertised a lithe figure any thirty year old woman would be proud to possess, let alone one encroaching on ... How old was she? Josh was twenty-five now and six when she left for college at—What? Eighteen? Josh whistled to himself. Thirty-seven, and she looked like that?

He tried to pass her at the top of the stairs to show the way to Dad’s room but she strode straight toward it without hesitation and entered. She walked to the bed and waited for his father to see her.

“Hi Chuck. How are you?”

He peered at her, looked at Josh and then back, his eyes focusing on her body, especially her breasts.

“Dad, this is Julie. Remember? From next door,” Josh explained, hoping to suppress the expression of lust on his father’s face but knew it was futile. He barely recognized him let alone someone he’d not seen in almost two decades.

“It’s okay. I’ve worked with lots of patients. How are you today, Mr. Randall? Is there anything we can get for you?”

Julie leaned over to fluff up the pillows and straightened the blanket over his father. His eyes followed her breasts all the way in and his head wobbled from side to side as she fixed the bed. When she drew back he looked at Josh and chuckled.

“Where’d you find this one, Ben? She’s got nice tits.”

Josh blanched. His father often confused him with his uncle. “Dad!”

Julie laughed. “I bet you’d like to see them but not today and not unless you eat all your supper.”

An eagerness filled his father’s eyes. “Well, where is it?” he barked.

“I’ll bring it up later.”

Julie’s spoke in a cheery voice as she straightened the covers near the end of the bed and folded them under the mattress before returning to position the patient for maximum comfort and breathing ability in the pillows. She worked efficiently but with care and, when finished, walked directly to the door with a pair of eyes close behind. Josh gave his father a dirty look and started to chide him but rushed to follow the ‘nurse’ instead. In the hallway, he started to apologize for his father’s behavior but she turned at the top of the stairs, her tears revealing the caring woman beneath the professional facade.

“Oh, Josh. It’s so terrible to see him like that.”

Julie put her hands to her face and sobbed. Josh rushed forward and took her in his arms, berating himself for agreeing with his father when she pressed herself against him. It was strange to comfort her but even with the role-reversal he felt warm and safe the way he always had when she chased away his loneliness with a simple hug. In a flash, he realized he loved this woman from his past.

Over coffee downstairs, Julie asked him how long he’d been looking after his father.

“Oh, three or four months. Maybe longer,” Josh replied, unsure of the correct answer.

“You look exhausted.”

“Yeah, I guess I’m a little tired. It’s constant. There’s no let-up.”

“I’m surprised they let you take him home.”

“Well, he’s better than when they let him out, if you can believe it.”

“I’m sure. They probably thought he didn’t have long to live.”

Josh laughed. “He perked up as soon as we got home. Thankfully ... it’s awful to say this but it’s true ... he can’t get out of bed or I’d never get any sleep.”

“It’s not awful.”

Julie stretched both hands across the table and put them over his left as he lifted his cup with the right.

“I suspect that’s why they let you take him,” she said.

Josh nodded and put the cup to his lips.

“I’d like to help.”

Josh pulled the cup away. “Excuse me?”

“I can help you look after your father,” Julie repeated in response to Josh’s incredulous expression. “I’d like to be part of it.”

The pressure of her hands on his increased. Josh didn’t know what to say.

“It will be better for him if there are two of us and you wouldn’t be so tired. You can’t carry on like this for much longer.”

Josh shook his head but in agreement, not denial. She was right. He was nearing the end of his stick but why would she make such a generous offer? As if sensing his confusion, she went on.

“It’s not completely altruistic. It’s going to take time for me to get the house ready to sell. It would be easier for me, and cheaper, if I could stay here.”

Josh looked at her blankly. This gorgeous woman was offering to help him with his ailing father and wanted to stay here?

“I don’t know what to say. It’s such a generous...”

“Just say yes.”

Josh hesitated. “Yes.”

She shook his hand, then retrieved hers and sat back, smiling. “Well, I’ll get my bags from the motel and put them in the spare room. It still has a bed, doesn’t it?”

“Uh, yeah. It’s probably dusty, but...”

“I’ll put the sheets and blankets in the wash. I’ll probably have to put the whole linen closet in the wash.” She laughed. “When did you last do the laundry?”

Josh made the universal, shrugging expression and Julie laughed again, a sound that Josh now remembered he loved.

“It’ll be like old times,” she said.

A week went by in which Julie spent most of her time cleaning her house or looking after Josh’s father, or Chuck, as they now both called him. The patient had improved tremendously, and so had Josh. No longer tired, he looked forward to breakfast, lunch, dinner and especially the evenings now that Chuck was sleeping better.

“I can’t believe how much better you’ve made him,” Josh said.

“It’s an illusion,” she answered in a matter-of-fact tone. “He’s actually getting sicker every day.”

Josh didn’t believe it. His father lived for his time with Julie and stopped thumping the wall and creaking the bed because she wouldn’t stay with him if he did. Josh had threatened the same thing and it only made it worse but Julie gave him a bell to ring, to only use only in an emergency, and he hadn’t rang it once.

In the middle of the second week Josh crept upstairs to listen because he was curious about how Julie had achieved such a profound change in his father’s behavior. As he approached the door, he heard her singing softly.

The other night dear, as I lay sleeping,
I dreamed I held you in my arms,
but when I woke dear, I was mistaken,
and I hung my head and cried.

You are my sunshine, my only sunshine
you make me happy when skies are gray
you’ll never know dear, how much I love you,
please don’t take my sunshine away.

His chest constricted. It was the song she sang when putting him to bed so many years ago. Cautiously, he moved closer and peeked inside the room. Julie was sitting with one leg bent on the side of the bed and the other stretched out to the floor. Her left hand gently soothed his father’s forehead and her right hand was out of sight beside her hip out of sight, perhaps holding a spoonful of food and awaiting an opportune moment to slip it into his mouth.

It was a beautiful, tender picture but something else made it truly amazing. Julie’s shirt was loose at her sides and was clearly unbuttoned. The cotton flapped as his father’s skinny elbows moved around in front of her. She was letting him fondle her tits!

I’ll always love you and make you happy
if you will only say the same
but if you leave me to love another
you’ll regret it all some day

The expression on Chuck’s face was ecstatic and remained so as he turned to look at Josh whose head was now protruding significantly from the door jamb. Afraid of being discovered, Josh yanked his head back and stepped away. The floor creaked.

“Is that you, Josh?” Julie called.

Josh sucked his breath in hard and held it, staying absolutely still.

“Come in. It’s okay.”

You are my sunshine, my only sunshine
you make me happy when skies are gray
you’ll never know dear, how much I love you,
please don’t take my sunshine away.

Josh stuck his head around the door as Julie finished singing the chorus. With her head turned sideways, she saw him out of the corner of her eye and extended the invitation again.

“Come in. Don’t be shy.”

Tentatively, Josh stepped into full view and Julie turned back to face his father who remained engrossed with her chest. Josh walked slowly into the room until he was beside Julie but slightly behind. She smiled at him.

“Now you know the secret of my ways.” She laughed and continued, “Something you can’t copy.”

Josh nodded his head in agreement and Julie turned her attention back to his father.

“Last verse,” she said.

You told me once dear you really loved me
that no one else could come between
but now you’ve left me and love another
you have shattered all my dreams.

Chuck worked desperately on her chest, obviously cognizant that fun-time was almost over. When Julie’s voice died away, he looked crushed but she immediately swung into the chorus.

You are my sunshine, my only sunshine
you make me happy when skies are gray
you’ll never know dear, how much I love you,
please don’t take my sunshine away.

As she sang with extra gusto, Chuck’s hands became less busy which confused Josh until he noticed Julie’s forearm moving on the other side of her body. He stepped closer and leaned over for a better look. The blankets had been pulled aside and Julie’s right hand was massaging his father’s cock! It was slick with lubricant and very hard, the shaft glistening in the light as her hand moved, revealing and then covering it up, squeezing, twisting and tugging upward with an added rub of the thumb along the underside up to the glans.

The odd movement of her hand drew his attention to something else, something that shocked him. His father’s cock was endowed with the same disfigurement as his own, a deformity that had been an enormous source of embarrassment in the showers during high school. The only difference was it bent sharply about thirty degrees two thirds of the way up, whereas his turned closer to the root. Julie’s strokes were delivered in two parts and her hand slowed as it negotiated the bend in each direction.

Chuck dropped his head into the pillows and stopped ogling Julie’s tits. His eyes closed and as his hands fell away his back arched. He was coming. Fascinated, Josh’s attention returned to the misshapen cock, so much like his own, in time to see a gob of creamy spunk spurt onto the washcloth which had appeared in Julie’s left hand. Weird sounds burst from Chuck’s lips. It sounded like he was being strangled.

“There, there. That’s it. Come on, now. All of it.”

She could have been cajoling him to eat everything on his plate.

“Alright, then. Let’s get you cleaned up and ready for bed.”

The washcloth was folded and set aside. Another appeared in Julie’s hand, a wet one.

“There, doesn’t that feel good? All nice and warm?”

A third was used for drying and added to the heap when the task was done. Chuck opened his eyes to watch Julie button her shirt and Josh was surprised to realize that he had also moved to her front to watch but only in time to catch the barest glimpse of her jiggling breasts before they were covered. He wished he hadn’t been so shy and regretted hanging back out of her direct line of sight.

Julie replaced the covers and folded Chuck’s hands across his chest, then gently closed his eyes. She picked up the soiled wash cloths and walked slowly to the door, singing, and nodding her head for Josh to precede her out the door.

You are my sunshine, my only sunshine
you make me happy when skies are gray
you’ll never know dear, how much I love you,
please don’t take my sunshine away.

Josh felt awkward and wished there was somewhere else to go other than following Julie down the stairs. Still, he waited while she stepped into the bathroom to dump the washcloths in the hamper and wash her hands. She smiled when she exited and continued downstairs.

In the kitchen, she said, “I could do with a coffee.”

They didn’t talk about what happened, then or at dinner. It was like an elephant in the room but neither spoke about it. Instead, they chit-chatted about the state of her mother’s house and how close it was to being ready for sale. Not quite yet, it seemed. Josh didn’t know whether to be happy or sad.

After dinner, while sitting in the living room watching the Sports news, Julie mentioned that Chuck still maintained his fascination with football and baseball.

“He hasn’t forgotten the names of the teams,” she said.

“Not really,” Josh said.

“Oh no, he can rattle off scores from old games as if he’d just seen them yesterday. It didn’t sound like he was making them up. He said them too quick.”

“Yeah, but he’s got the Mariner’s playing the Bears and the White Sox playing the Seahawks, or the Red Sox playing the Steelers.”

“That’s good, isn’t it, that he still remembers the teams?”

“I guess, but the Mariners are a baseball team and the Bears play football.”


Josh continued, “The White Sox play baseball and the Seahawks are Seattle’s football team.”

“I see.”

“And the Steeler’s are...”

“I get it,” Julie snapped.

Josh stopped. He felt like an ass pointing out his father’s failure.

“I know he’s not well but we can make him comfortable and happy while he’s still here.”

“I noticed,” Josh blurted, instantly regretting it.

Julie stiffened and took a deep breath before replying. “I know my methods are unconventional. God knows, it’s not something I would do at work, but Chuck is special. Does it bother you?”

Josh answered honestly because he had never been able to get away with lying to her. “A little, I guess.”

“Do you want me to stop?”

“No. It’s just that, well, it reminded me of when I was little and you used to sing that song to me at bed time. It made me feel warm and safe and ... loved.”

Julie laughed. “Yes, but I never...”

“I know,” Josh cut her off. “I know,” he repeated. “It’s just that...”


“I felt ... jealous.”


“Not that, I mean, I’m not trying to hint...”

“No, of course not. I’m a mother, almost forty, and you’re...”

“It’s not that. I mean, you’re beautiful, but you’re, I mean, I know you’re married and I would never, uh, you know—want you to feel uncomfortable,” he finished up, lamely.

Julie laughed softly. “I’m not uncomfortable and I’m glad you came upstairs and that you came into the room.”


“Yes. I want you to be there because sometimes he gets carried away and squeezes too hard. He’s still quite strong and it’s hard to get him to let go.”

“Yeah, I guess. So, you want me to... ?”

“Yes, if you wouldn’t mind.”

That night, Josh dreamed about Julie’s breasts, about being senile and fondling her tits as much as he wanted, as long as she was singing. In the morning, he woke up with a tune in his head.

You are my sunshine, my only sunshine
you make me happy when skies are gray
you’ll never know dear, how much I love you,
please don’t take my sunshine away.

For the next week, Josh accompanied Julie for every feeding. What he thought was a goodnight ritual turned out to be common practise for each meal. While eating, Chuck regaled her with his sports knowledge by recalling past baseball and football triumphs as if they were his own.

“Who won Superbowl X?” he asked, a sly, mischievous grin on his face.

Julie shook her head. Josh cast his mind back but couldn’t remember. When was Superbowl X? In the eighties?

“In 76 Pittsburgh won for the second time in a row over the Texas Cowboys,” his father announced triumphantly.

Josh didn’t know if the year was right or whether it really was a consecutive win but he knew the Steelers had done it. Maybe his father had the details right but he was way off on the obvious, like the fact that it was the Dallas Cowboys, not Texas.

“Know who the MVP was?” The grin widened.

Julie shook her head but smiled and said, huskily, “No Chuck. Tell me.”

“Johnny Bench.”

Josh winced. Bench played for the Cincinnati Reds and was one of the best hitters ever. His father compounded the mistake with an amazingly accurate statistic that should have exposed his twin error of wrong sport and city, even to himself.

Gloating, he added, “He hit a point five three three average for the series.”

Josh grimaced. Referring to a ‘series’ should have twigged the mismatch with a football game.

“Really? That’s wonderful, Chuck.”

“Yup, that same year the Cincinnati Steelers beat the Yankees twenty-one to seventeen to win the World Series,” he crowed.

“Wow!” Julie exclaimed, matching his enthusiasm.

Josh rolled his eyes, then tried to capture Julie’s attention to express his sadness for his father’s obvious memory failures but she her attention was focused on him.

“Swann was the MVP,” he announced, reaching for the buttons on Julie’s blouse but she deftly turned his hands aside and pushed a spoonful of food into his mouth.

After his father had finished eating all that Julie expected of him, she unbuttoned her blouse and let him play with her breasts while she sang. During the first chorus, she pulled on his semi-hard, bent cock, greasing it with the jelly she had placed in the palm of her hand. Chuck didn’t come much at lunch or dinner but the breakfast and evening loads were more substantial.

Josh was as fascinated with his father’s cock and the way she handled it as he was with her tits. She had nice, medium-sized ones that were shaped nicely with the right sized nipples. They didn’t sag as much as he expected for a woman her age and the bit they did somehow made them sexier.

But, as nice as they were, his attention was drawn elsewhere. He couldn’t get over how much his cock was like his Dad’s. He also couldn’t get over how much attention Julie showered on it. While his father ogled her tits she stroked his forehead and stared at his cock, as fascinated with his bent dick as he was with her tits. In fact, they made a perfect pair with Josh’s fixation on comparing his and his father’s pricks making him a candidate to join the club.

A perfect pair. The thought struck Josh like lightning. He cast his mind back, searching for memories, but came up short. There were dim memories of his mother and father arguing but he couldn’t remember what they were fighting about. He did recall his mother taking a sudden dislike toward Julie before she left which was surprising because she liked Julie. She asked Josh if Julie came over when she wasn’t home. Had his mother left because his father and Julie were having an affair?

Josh couldn’t tell whether Julie already knew about his father’s weird dick or had discovered it in the past two weeks. Certainly, she was well practiced in getting and keeping him hard for a long time and that got Josh off too. His erection started when he followed her up the stairs, his face right behind her ass which was in constant, enticing motion under the black leotards, leaving just enough mystery for his imagination. It tingled when she teased his father with a throaty voice while feeding, prodding him with questions about baseball and football. Of course, his father mixed up the teams, getting the cities and sports wrong, but it didn’t matter. Julie’s voice got huskier as the meal neared the end and his father started getting hard.

His own cock stiffened when his father started playing with Julie’s tits but rocketed into full, brittle, snappable status when her hand rubbed gel on his father’s bent dick. From that moment until his father came, Josh was racked with jealousy. He had to leave the room early several times but more than once his cock exploded in his pants before he could leave, dripping and spurting down his leg because Josh’s cock truly was almost a mirror image of his father’s. Whereas his father’s cock bent upward near the tip, Josh’s bent in the opposite direction.

Bending downward had always been a problem. He had frequently hurt himself while jacking off, his hand tending to curve in an upward arc. Later, his romantic partners sometimes pointed out that bending downward made insertion difficult. One ditz had even asked him if he could bend the other way. Quite often, Josh was left hanging because copulation became too uncomfortable for his partner. He was built perfectly for blow jobs but found few girls willing to take it down the throat or even put it in their mouth after seeing it. One girl complained that it, “just looks too weird” and another couldn’t stop laughing even after Josh stuffed it back in his pants.

So Josh became super jealous of guys with normal cocks even though his was a healthy size. And now, his tall, gangly, former babysitter had turned into a super MILF and showed up on his doorstep only to start jacking off his ailing father in front of him. He knew she was doing it to ease his pain, to give him some pleasure before leaving this world, so there was no way Josh could take his place, especially with his grotesque, hook-nosed cock.

Despite the benefits and improved nutrition Chuck’s health continued to deteriorate, as Julie said it would. One night, after a particularly long description of a bygone season’s best games, egged on by frequent cooing and husky questions from Julie, she turned her green eyes on Josh. She had just grabbed his father’s cock and slid her hand up and down three times, the flat of her thumb caressing the underside of the head. Josh’s own palm was covering the lump in his jeans.

“Would you be a dear and run a tub of hot water for me?” she asked.

“Uh, sure. For Dad?”

“No. Please fill it right up to the brim.”

Josh rose with some difficulty and limped out of the room, part of him wondering why he tried to hide his condition. She must know the effect she had on him. He always imagined it was his cock being stroked and massaged by her silky hand, that it was his hands mauling her breasts, tweaking and pinching her nipples. He knew he could do a better job than his father. He didn’t even suck them or try to kiss her. Julie was beautiful and, though his father was very sick, he knew she would let him if he tried. She was that kind and compassionate.

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