Helping The Homeless


Author’s Note: This is a story about an older man helping out a 30 something homeless woman and her young son, abandoned by her husband. A sexual relationship develops between the 30 something woman and the older man. Enjoy.


I’m driving around town doing miscellaneous chores when I see that homeless woman and her son again. They are huddled along the wall of a convenience store. I’ve seen them a couple of times before in the same spot. It’s fall and the weather is not bad but nobody should be homeless in the United States. She looks to be in her mid 30s or so and the boy is preteen, maybe 8 or 9 or 10. She’s a dirty blonde who appears to be slightly overweight although I’ve noticed she’s losing weight. It’s really a shame. Neither one looks like they’ve had a bath or shower in a long time.

I make a decision to do something about her situation. I’m in my late 50s and divorced. My house is almost paid for and I live there alone. My financial situation is not bad. I’ve got a good job in a local factory and since I’m living alone, I decide I could use a maid.

I approach her and kneel down next to her. “Miss, are you homeless?” I inquire.

She looks at me and says “Yeah, homeless and my husband has deserted me. Could you spare some change? We haven’t eaten for two days now.”

I smile and say “Hi, my name is Mike Jackson. I’ve got a better proposition for you. I’m divorced and I live alone in a three bedroom house. I need a maid. I’ll give you room and board plus $100 a month spending money if you’ll take the job. Your son can have a room of his own. All I ask is that you keep the house clean. You’ll have the run of the house and can eat anything that’s in the house.”

She looks at me and says “Are you serious?”

I say “Yes, very serious. I need a live-in maid. I’ve never been good at housekeeping.”

She starts to cry. I say “Why are you crying?”

She says “Just happy. I’ll take the job, sir. My name is Sara Hall.” She slowly gets up and pulls her son up. She shakes my hand and I open the rear car door for her and she helps her son in and puts the seatbelt on him. I then open the passenger side door, she smiles and gets in.

As I get in the car, I say “First thing we need to do is get some food in your stomachs. I was just going to stop for lunch at McDonald’s. Does that sound good?”

She smiles and says “Oh, yes. That’s sounds wonderful.”

I say “Don’t you have any other clothes.”

She says “No, we were thrown out of our house and all our things were in there. They wouldn’t let me take anything except the clothes we are wearing. All we have is what we have on our backs.”

I say “Well, I think there are a few outfits that will probably fit you at my home that my ex left but I don’t know about the boy.”

She says “Johnny. His name is Johnny.”

“Well, after we eat I’ll take you to the thrift store and we’ll get him a few jeans and shirts to wear. Does he go to school?”

She says “He did but he hasn’t gone for over two weeks since we’ve been homeless.”

I go through the drive-thru and buy them each a burger, fries and a coke. I get myself a double cheeseburger, fries and an ice tea. I drive off and head for the thrift store. We eat in the parking lot. When we are finished (it doesn’t take them long), we walk into the thrift store.

We exit with four sets of clothes for her son plus another pair of sneakers. It costs me $18.30. His old sneakers are pretty worn. She says “You are really generous, sir. I don’t know how I can repay you.”

“Please, call me Mike. Just keep my house for me and we’ll be even, okay?”

Again she starts to cry.

Ten minutes later, we pull into my driveway. She says “Oh, that’s a nice house, Mike.”

“Yeah, I like it. My wife didn’t want it. She ran off with another man.”

She says “My husband ran off too. Johnny and I lived in the house until they repossessed it. We haven’t seen him since he took off.”

I get out and open her door. She gives me a big smile and thanks me. I grab the boy’s things and she pulls him out of the back seat. I walk them up to the house and unlock the front door. I say “I’ll have to get you a key to the house.”

I show her around the house and then walk upstairs. She follows. I show her her bedroom and the one her son can use. I throw the clothes on his bed. I noticed he doesn’t talk much.

I show her the linen closet and tell her she can make the beds later. I show her the upstairs bathroom and tell her “Why don’t you give him a bath and take one for yourself too. I’ll be downstairs. By the way, the clothes my wife left are in your closet if you want to take a look at them.”

“Thanks, Mike. You are awesome.”

“No, I’m not. I’m just a simple man who’s a liberal and can’t stand seeing someone hurting.”

I head downstairs to let her get her and her son cleaned up.

I think to myself that she’s very pretty and cleaned up she would be real attractive. She’s a little overweight but not real bad, maybe about 10lbs too hot to handle latino izle overweight. Just like my ex-wife was. She’s got a very similar figure as my ex. I’m guessing 34C-28-36 or so. Roughly about 130lbs.

Forty minutes later, she walks down the stairs in one of my ex-wife’s outfits. It fits her well. June was a tad overweight too. She says “Well, what do you think?”

I say “Looks very good on you.”

She says “Yeah, it does. Your ex must have been the same size as me.”

I say “Yeah, she was about your size.”

She says “I made the beds upstairs and put Johnny’s new things in his closet. I’m going to have to get some bras and panties but the five outfits upstairs will do fine.”

I say “There’s a washing machine and dryer down in the basement if you’d like to wash all the outfits before you and Johnny wear them.”

She smiles and says “Okay, thanks. You are a very generous man. I really appreciate what you’ve done for me and Johnny.”

I smile at her and hand her five $20 bills.

She says “What is this for?”

I say “It’s an advance on your pay. Johnny doesn’t have anything to play with so I was thinking after supper, we’ll run to the store and get him something. You can get you a couple of bras and some panties too.”

She’s crying again. I stand up and hug her. She snuggles into my shoulder. I say “No reason to cry, Sara. I’ll take care of you now until you can get on your feet again or if you want you can stay here with me and be my maid. I really hate to live alone.”

She says “Mike, thank you so much. I don’t know what I did to deserve this but thanks.”

“Well, the world has knocked you down and I just picked you up. You’ll be fine, now.”

A little later, I cook supper. Nothing special, just some hamburger helper. Johnny seems to really like it.

After supper, we head to Walmart and get Johnny some things to keep him busy, a couple of toys, crayons and coloring books.

The next day, I call in sick and I take her and Johnny to the local elementary school to get him back in. After she gets him back in and smooths out all the issues with the school, we head back to the house. At the house, she begins to clean and I get on the internet. At lunch, I make myself an omelet and ask her if she would like one. She says “Yes I would like that. You’re a pretty good cook.”

I say “Yeah, I’m a not bad. I had to learn when my wife left me. How about you?”

She says “I can cook too.”

I say “Good, we can switch off and each cook every other day.”


After lunch, she continues to clean. Hey, the house was dirty. I said I’m not good at housekeeping.

I’m watching TV when she comes into the living room and says “All finished. Mind if I sit next to you and watch TV with you?”

I say “No, I don’t mind.” She sits down and we watch TV. At 2:50pm, she gets up and walks outside. She’s waiting in front of the house for Johnny’s bus. Fifteen minutes later, she and Johnny come walking in. He’s actually got a big smile on his face. “Hi, Mr. Mike,” he says.

I say “Hi there Johnny. How was school today?”

He says “Okay, I guess. Thank you for taking care of mommy.”

“You’re welcome, Johnny.”

He says “I just hope we don’t end up on the street again. I really hated that.”

I smile and say “Johnny, as long as your mother needs to live here, she’s welcome and so are you. I hate living alone. I’m glad to have you here.”

Johnny says “Thank you Mr. Mike.” He runs upstairs to his room.

Sara comes over and gives me a long hug. “Thanks, Mike. I think he likes you.”

I smile at her. “He’s a nice kid.”

The next day, we continue with the daily routine. I’m back at work, Johnny’s back at school and Sara is minding the house.

A month later, Sara is taking a bath, Johnny’s in bed and I’m watching TV. It’s a Friday night so I don’t have to work tomorrow. I’m sitting there relaxing and I hear Sara coming down the steps. I look up and she’s got on one of my ex-wife’s housecoats. She comes and sits on the couch next to me. She says “Mike, do you think I’m sexy?”

I look at her and say “Yes, very sexy.”

“Mike, I haven’t had sex in over three months. I’m horny. Are you interested?”

I look at her with my mouth open. She says “Mike, I mean it. I want you to make love to me. I need it bad.” She stands up and opens the housecoat. Of course, she’s naked under it and looks very good. She says “Don’t make me beg, Mike.”

I stand up, grab her, put my arms around her naked body and give her a long French kiss. I say “Are you sure you want to do this?”

She reaches down and grabs my crotch and says “What do you think? Fuck me, Mike. Please.”

I grab her hand and walk toward the Master bedroom on the first floor. She’s got a big grin on her face.

As we enter the bedroom, she closes the door, locks it and drops the housecoat. She then kneels in front of me, unzips my treason izle pants and unhooks my belt and pants. She pulls my pants down with the underwear and grabs my half hard cock. She smiles up at me and begins licking the head. I tell her “Damn, it feels good. I haven’t been with a woman in over six months. I hope I’ll be able to last long enough to satisfy you. I’m probably going to be on a hair trigger.” She just looks in my eyes as she moves my hardening penis in and out of her mouth. She’s very good. She’s soon taking me all the way in. The head is in her throat. I groan every time her nose touches my pubic hair.

After a couple of minutes of oral sex, I’m good and hard so I pull her up and lead her to the bed. She lays down and holds up her arms inviting me in. Before I get on the bed, I open my top dresser drawer and pull out a condom. They are at least 6 months old but should still be okay. I crawl up on the bed and lay down into her arms. I give her a long French kiss while a begin to play with her left nipple. She starts to moan during the kiss. I pull back and say “I don’t believe you want to have sex with me. I’m old enough to be your father.”

She says “I don’t care about the age difference. You are a good man and very handsome, Mike. I don’t think it will hurt our live-in relationship to share our bodies with each other, do you?”

I smile and say “No, I think you’re right.” With that I spend some more time teasing her nipples. After a few minutes, I head south and kiss down her stomach until I reach her pubic mound. I then skip over her pussy and begin to kiss down her right leg. She moans in frustration because I skipped over her pussy. I kiss down her right leg slowly. When I get to her feet, I sit up and take her foot for more pleasure. I lick the sole of her foot and then suck the big toe into my mouth. She gives me a squeal. She wasn’t expecting that. I suck each of her toes into my mouth and then begin kissing back up the inside of her leg.

When I reach her genitals again I skip over them and kiss down her left leg. When I reach her left foot I give it a good licking and give each toe a good suck. She’s moaning loudly. After sucking all her toes, I start to kiss and lick up the inside of her left leg. This time I don’t skip her pussy. I begin to lick that pussy by running my tongue over her outer labia. Her outer labia are wet. She must be getting turned on. After several times up and down her outer labia, I spread her outer labia out so I can get at the rest of her pussy.

I run my tongue over her inner labia and she moans loudly and says “Oh, God, Mike.” She tastes pretty good and she’s really moaning now. As I continue to lick and suck her inner lips she says, “Oh, Mike. That feels so good.” I use my lips to pull on her inner labia. She’s moving all around and can’t stay still. Eventually, I begin to tongue-fuck her vagina. She squeals when I start that. After a couple of minutes she’s breathing very hard. I move up to her clit and pull the clitoral hood back to take her clit into my mouth. She groans loudly. I begin to suck her clit and flick my tongue back and forth across it. I reach up and stick a couple of fingers in her mouth because she appears to be a screamer. Within a minute she starts to buck and screams as her orgasm starts. I cover her mouth so the scream isn’t so loud. Soon she’s fucking my mouth and has her hands in my hair pushing my face deeper into her pussy. She orgasms for almost a minute and then pushes me away.

She breathing in gulps and says “God…..Mike…..that…..was so….good!”

I move up beside her and wipe my face on the top sheet because it’s covered with her juices. She looks at me, smiles and grabs me for a passionate French kiss. Her tongue is deep in my mouth and she’s growling deep in her throat. “Mike, please fuck me now…..hard, please.”

I smile at her, get into a kneeling position, tear the condom pack open and roll it down my throbbing penis. She spreads her legs wide and says “Fuck me, Mike!”

I crawl between her legs and start to slip my hard-on into her vagina. She’s pretty tight but soon I’m balls deep. She says “God, that feels good.”

I begin to slowly move in and out of her. She says “Faster, Mike.” I slowly pick up speed and she eventually says “Oh, yeah, that’s the ticket.” Within two minutes she’s breathing very hard again and saying “Yeah, yeah.” I reach down and suck her right nipple into my mouth and give it a bite. It’s been so long since I’ve even masturbated that I know I’m not going to last long. I can feel it starting. I do manage to last five minutes and Sara is flushed all over her body and her breath is coming faster and faster. I lose it and begin to cum and she screams to join me. I immediately cover her mouth with mine to stop the scream. She continues to cum and I keep pumping until she slows down a little.

“Oh……Mike……that……was……amazing.” She’s breathing very hard. I give her a passionate French kiss. She loves to stick that tongue true detective izle of hers deep in my mouth. A few minutes after the orgasms, we are starting to both breath a little better. I’m hesitant to pull out of her and she doesn’t want me to either because her legs and arms are tight around me. I decide to just roll us both over so she’s on top.

I’m laying there with a beautiful woman lying on me. She looks down at me and has a big smile on her face. “I haven’t cum like that in ages. I think we will have a wonderful relationship.”

I say “You’re kind of loud. I hope we didn’t wake Johnny.”

She says “Oh, he sleeps pretty soundly. As far as I know, my ex and I never woke him. Although it’s been a while since I’ve cum like that with anyone. It’s your fault, sir.”

I give her a big smile. So the old man didn’t do too badly.

She lays down on me and lays her head on my left pectoral with a big smile on her face. She says “I like the feel of your cock inside me. Don’t pull it out yet.”

I say “Well, it’s getting pretty soft now.”

She says “That’s okay, I still like it inside of me.” We lay like that for a half an hour and then she rolls off. She grabs the condom and sucks the contents out of it. She says “Yum. Man juice,” and laughs.

I laugh at her too. She kisses me again and then lays down. She says “I really like it when you licked my feet. That was a total turn-on. I’ve never had someone do that to me.”

“I’m glad you enjoyed it. I’ll continue to do that for you.”

We lay there for a while cuddling. “I like this, Mike. I could do this forever.”

“Well, like I said before, you are welcome to stay as long as you like.”

She says “I don’t think you are going to get rid of me very soon, especially if you keep satisfying me like you just did. That was something.” She rolls over on me again and gives me another long, passionate French kiss.

A half hour later she says “Well, it’s 11pm. I supposed I’d better go up to my room and get to bed. Thank you so much, Mike. I look forward to our next naked encounter.” She gives me a big smile and another quick peck on the lips, then heads out of my bedroom door.

I lie there awhile thinking about her. This is going to be an interesting time of my life. We appear to be very good together. She’s very beautiful but much younger than me.

Saturday comes and I hear Sara and Johnny up making breakfast. I look at the clock and it’s 8:14am. I get up and throw my clothes on and walk out into the kitchen. Sara smiles at me says “Morning, Mike. Would you like some bacon and eggs?”

I say “Sure, and some toast please.”

Johnny says “Hi, Mr. Mike. How are you today?”

I look at Sara and say “I’ve never felt better, Johnny. Something made me sleep real good last night so I feel great.”

Sara smiles at me and says “Yeah, I slept real good too. Don’t know what it could be. I feel great too.”

I smile and she giggles.

After breakfast, I head out to get the newspaper. I don’t usually get the paper during the week since I don’t have time to read it. But the Saturday and Sunday editions I get and I enjoy sitting, relaxing and reading them.

Back home, Sara has cleaned up the kitchen and is checking the rest of the house for things that need doing. She’s really a good housekeeper. I’m reading the newspapers while sipping some coffee. I notice a used bike for sale. I circle the ad. After I’ve finished reading, I call the number and ask if they still have the bike. They do and it’s only $25. I tell Sara I’m going to step out for a while.

An hour later I arrive back home with a bike for Johnny. It’s in pretty good shape. The tires were flat but I stopped at the gas station and filled the tires. I tell Sara to get Johnny and come outside.

They walk outside together and I’m standing there with the bike. I say “Johnny, can you ride a bike?”

He says “Yes, I can. Is that for me?”

I say “Yes, Johnny. It’s yours. Have fun but stay out of the street with it, okay?”

He says “Yes, sir.” I grabs the bike and starts to ride it. He yells “Thank you, Mike!”

Sara is crying again and grabs me to give me a hug. “Thanks, Mike. That was really thoughtful.”

“Well, I saw the ad and it was only $25. He needs to get some exercise and fresh air. Boys that age are pure energy and if they don’t burn it off, they drive you crazy later.”

We head back in and inside Sara grabs me again and gives me a long French kiss. Wow, that woman has a long tongue.

“Mike, I’d like to thank you for that tonight. Do you feel like being thanked….in bed?”

I laugh and say “That sounds like fun. I’ll be looking forward to being thanked.”

She laughs and hugs me again.

She cooks tonight and makes some pretty good spaghetti. A good cook, a good housekeeper and a good fuck. Her husband must be an idiot.

At 8:30pm, she puts Johnny to bed. He’s very tired from riding the bike and from all the fresh air.

After he’s in bed, she takes a bath and comes out in a housecoat again. She walks over to me and flashes me. Then she gives me a big smile. I tell her I need to take a shower and I’ll be right back. After my shower, I wear a t-shirt and shorts. I walk out and walk to the kitchen and get a couple of beers. I walk out to the front room and sit down. I offer her the beer and she thanks me.

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