I confess I've been fucking a homeless woman for the past 5 days, and have been paying for her cheap hotel room, buying her food too.
It all started last Friday on the 11th of June. I went to the store and this woman was on the sidewalk, her head between her hands looking down at the ground. She had a small sign that read, "hungry and homeless please help." She had dark brown hair, tan skin - and from what I could see a nice figure. She looked to be in her mid 20s, and I approached her, put $5 in her cup and turned around to go inside the store.
I heard a soft, "thank you."
Not looking back I casually said, "no problem, I hope things get better for you."
I went in the store and bought some items, but also thought I should get her something to eat too. So I did. They had sub sandwiches for $5, and I got her one, plus a box of chocolate chip cookies as a desert.
I got out of the store, and she was still there, head between her hands. I placed the sandwich and box of cookies next to her and turned around to walk away.
"Why are you being so nice to me?" she asked, with her soft voice.
I turned around and she was no longer sulking, or hiding her face. She had no makeup on, but was absolutely beautiful. Her blue eyes penetrated me, and then I noticed she had a black eye and a few bruises on her neck.
"Holy shit," I was horrified, "are you okay?"
"I- I am fine. I don't need your pity. This is what happens when you hook up with an abusive asshole. Thank you, god bless you for helping me."
"Look, whoever did that to you..." I searched for the right words, "I hope you don't have any contact with them anymore."
"I don't, that's why I'm homeless. I don't want to go to a shelter, I tried that and someone stole everything I had."
Someone walked by smoking a cigarette, and she asked to bum one.
"Get a job," the guy mumbled.
I pulled out my wallet, "here's two dollars for a cig."
He stopped and pulled a cigarette out and gave me one.
"Be more empathetic," I told him. He shrugged and walked away mumbling under his breath.
I handed her the cigarette, she already had a lighter and with a tiny flick of her thumb it was lit.
She inhaled it deeply, and I noticed she seemed far off and distant for a second as if she was thinking of a better time.
"Not too many people give a fuck about people like me..." she said.
"I try to - but the way society is, well we're all pretty much fucked." I told her.
"Yeah, well you probably got a white picket fence and a house, and me - well I make a lot of bad decisions, as you can tell." She lifted up the cigarette gesturing that smoking was one of them.
My dick started thinking for me at this point. She was pretty, had a nice body, nice tits. Her face was rounded with nice cheek bones. She was a bit dirty. Her shirt was stained, and she obviously wasn't wearing a bra. Her jean shorts were faded and ripped.
I was attracted to this woman, and blurted out, "If you need a place to stay..." I stopped myself. I didn't know her, and certainly couldn't invite her back to my place.
She looked me in the eyes and I could tell she was about to cry.
"If you need a place to stay I could get you a hotel for a few nights. Get you some food, try to help you get on your feet. Help you apply for jobs."
She smirked as a tear rolled down her dirty face, "No. I don't need you to be my savior. I'll be okay, really."
"I'm not looking to be your savior, nothing like that. I try to help people as much as I can. I don't have anyone in my life that I have to pay for, I'm a 38 year old loser to be honest. Sure I have a good paying job, I have my own place - but... well. What do I have to show for it."
"You have a house, probably a wife, kids..." She said looking down at the sidewalk.
"I don't, that's what I mean - I don't have anything to show for all of my accomplishments... so if I can help you, it makes me feel better about my life. Understand?"
She put her cigarette out on the sidewalk, grabbed her backpack and got up. She was sexy, with toned legs, nice hips, perky full breasts - her nipples poking through her stained shirt. If she took a nice hot shower, she would clean up well. Perfect 10 in my book.
"I'm in a bad situation, I guess I need all the help I can get at this point."
We walked to my car and I opened the door for her, she laughed a little.
"And they say chivalry is dead," she said as she shut the door.
I got in and started my car. I knew there was a cheap hotel a few miles down the road. We had a bit of small talk, she said she went to college for finances but dropped out because she met her ex that she 'fell madly in love with,' but that the relationship turned out to be a complete nightmare.
I asked if she had parents, or siblings that could help her out, and she got pretty quite.

"When I was a teen, my family went on a road trip that I refused to go on. They didn't even leave the city and their car was hit by a drunk driver. I lost my mom, my dad and my brother. The police showed up at the house and that's how I found out. So I got put into the foster care system until I reached 18... then I left. No aunts or uncles, nobody. Grandparents passed when I was a child, I don't remember them. I'm all by myself, and I have been since my parents died. My foster parents were loaded. They paid for all of my college, but when I dropped out because of my ex, they pulled all their funding and disowned me... which is completely understandable but I just can't forgive them for turning their backs on me. I know I'm not even their own flesh and blood, so they didn't even need to pay anything after I left."
I didn't say anything. I felt bad for her. She was completely alone.
We got to the hotel, $55 a night, which wasn't bad. I could surely afford to house her there for a few days.
I went in and paid for 5 days. With tax it was just under $300. I got the key and went back to my car and handed it to her.
"It's all yours. Just don't trash the place okay?" I said laughing.
She laughed, "Hey you're welcome to come in, I like talking to you. I haven't talked about this shit in a very long time."
My dick woke the fuck up, "Sure, it's good to get bad things we've experienced out of our systems. I'd be happy to talk to you about anything you want!"
We went to the designated room and she unlocked it, she went in first and I followed her.
Someone had the air conditioner cranking full blast, and the room felt like it was 50F degrees.
She turned it off, then turned around towards me.
"Look at me, inviting a guy to a hotel room and I don't even know his name..."
"I'm Jason, nice to meet you..." I left it open because I didn't know her name either.
"Judy," she said as she plopped her backpack on the bed. She opened up her backpack and pulled out some red and white underwear and walked over to the sink. She turned on the water and soaked them, using soap to scrub them.
"Ugh, I barely ever get to wear clean clothes - so I do my best to keep at least my underwear clean!"
"I mean, yeah - I'd probably do the same thing too if I was in your situation."
She stopped washing them and hung them over the ledge of the counter near the sink to dry. Judy tried to fix her hair up in the mirror as best she could, but she really needed a brush.
"Hey, if you want I can buy you a brush or whatever... do you need anything else?"
She paused and looked in the mirror at my reflection still standing by the door.
"Am I a kept woman now? Are you going to buy me all these things and keep me locked away in your tower?" She seemed a bit agitated.
"No! I'm not like that, I just wanted to help you out. Look, I'll let you be - I just really understand how things can really get bad."
I turned to open the door, "Take care of yourself, ok?"
"Hey wait, I'm sorry... I'm just... No one has ever tried to help me like you have... tell you what, you can get me deodorant and a brush. Maybe some red lipstick and some blush? A toothbrush and toothpaste? See, I'm getting greedy now." She was smiling.
"Ok, consider it done!"
"I'm going to take a shower, clean up - can you go get that stuff? I'd love to sit down and talk to you more."
I did. I went to a store and got her everything she asked for. I thought about getting a pack of condoms but then thought there wasn't any point. I was there to help her, not fuck her. Yes I wanted to fuck her but given she was abused, she's probably not going to want to have sex. So about 25 minutes later I was back at the hotel room, and knocked on her door.
She opened the door, her hair was still wet, she changed her shirt to a black shirt that revealed a lot more cleavage, and I could see a perfect outline of her tits. Her nipples were very obviously erect. She also changed her pants to jogging pants. She smelled of hotel room soap and shampoo. Her eyes caught me checking out her tits, but she didn't say anything at all. She was very beautiful all around.
I went in and sat down in the single chair that occupied the hotel room. She bounced on the bed and found the TV remote on the side table, clicking the TV on. She flipped through some channels and then turned to me, ignoring the TV.
"So what's a nice guy like you single for? I mean not that I'm any catch or anything like that... but honestly - no girlfriend? No wife? What's up with that?"
"Judy, sometimes life throws bullshit at you, ya know?" I said, kinda looking down, a bit embarrassed about being single.
"I was engaged once. I was going to marry someone but she decided she liked a fat tow truck driver instead... so one day I came home early from work and this fat greasy bearded ugly dude was fucking my fiancé, right on the bed. She yelled at me like it was my fault. Her tow truck driver fuck buddy got off her and charged at me, so I got into a huge fight with him. He fractured 2 of my ribs, I busted his eye socket and jaw. Cops came, he was arrested for assault. That was 10 years ago."
"Oh damn Jason, I'm so sorry. People are such assholes."
"That, they are."
She pointed to her black eye, "see this? This is what happened to me when I caught my ex doing meth. I smelled something funny and when I found him he was smoking it. Something broke in him, idk what happened because the next thing I remember I was waking up on the floor with a pounding headache. That was a few days ago. I packed a bag and left. It's not like things were good between us anyway. He was fucking this other woman, I really didn't care because I'm bisexual and ok with open relationships, but he started paying more attention to her. Turns out she was doing heroine, and he started to do it too. Then they got into meth, and I warned him that I'd leave him if he didn't clean himself up. It got worse, and I fell out of love with him. I just stayed there because I had no where else to go, and no one else to turn to. Well, after waking up when he knocked me out I knew it was time to leave." Judy looked sad as she remembered the traumatic events.
"Hey, I'm sorry that shit happened to you, but you're safe now ok? Judy look at me."
She did.
"You are safe now," I said again.
"Hey Jay, come over here and join me on the bed so we can watch some stupid program that we don't even give a fuck about," she said wiping a tear away.
I sat on the bed, away from her.
"Get over here!" she pointed to the empty spot next to her, "damn you're so fucking shy it's cute!"
I moved next to her. She put my arm around her and snuggled into my chest. She put the remote down and looked up at me, and kissed me. I felt her bite my lower lip, and then her tongue (which was pretty long) push deep into my mouth. My tongue found hers, and I pulled her body close to mine. My cock was throbbing hard. Poking through my jeans. I didn't want to make any moves, I wanted to take things slow, out of respect for her - but she had other plans.
Her hand found my cock, she unzipped and unbuttoned my pants. She took her shirt off revealing perfect breasts. I slid my pants off, then took my shirt off as we passionately embraced each other.
She took off her jogging pants, revealing that she hadn't shaved her pussy in a while.
"I haven't fucked anyone in 6 months," she panted. I laughed and she gave me a confused look.
"I haven't fucked anyone in over 5 years," I told her.
Our lips met again, my hands cupping her breasts. They were so soft! My hand glided down to her beautiful round ass, which was just as soft as her succulent tits! She pulled away from my kiss and licked and sucked my neck. Judy pushed me down on the bed and engulfed my cock in her mouth.
She moaned as her mouth slid up and down my shaft. My hand found her pussy and I slipped a finger inside her. She was soaking wet and dripping. Judy began to ride my finger, and I put another one inside her. I felt her muscles clench around my fingers as her tongue licked and flicked the tip of my cock. Then she mounted me. When she did, she screamed with pleasure. I grabbed on to her waist, looking up at her perfect body.
"Oh Jason, yessss" she moaned.
I was already feeling like I was going to cum, it was building up and my dick was getting even harder inside her.
"Oh Judy, slow it down babe, it's been a while..." I panted.
She sped up, she tightened her juicy cunt around my cock and smiled.
"Ohhh you're going to like this Jay..." she said, sliding me in and out perfectly.
And I did. I liked it. I came so hard in her I nearly passed out. All of my nerves convulsed, I could feel each ejaculation pumping inside her, filling her."
She could feel me too, and she loved it. She kept bucking as I came, and moaned louder. My erection didn't go down and she kept fucking me. I turned her over and started drilling her missionary. I kissed her lips as her nice tits bounced to each thrust I pumped inside her. I must have cum inside her a lot, I could feel it dripping down my balls.
"Oh right there," she moaned.
So I kept pumping her in the same spot. Her body twitched and her eyes rolled back.
"JASON, I'm going to cum all over that cock!" I increased thrusts and started pumping her harder and harder, I was going to cum again, I was going to cum too!
I filled her again.
We laid down and held each other for hours.
The first thing out of my mouth, "obviously you're not on the pill..."
"Obviously," she said as if it was a stupid question.
I stayed the night in her arms. Saturday, Sunday, and Monday I fucked her and came inside her even more. I offered to pay for her hotel a few more nights, but then decided to let her stay at my place.
"Would you like to come home with me? I mean, I just am offering..."

So that's where I'm at. She agreed to give it a try, to see if it will work out. I asked her to be my girlfriend, she said yes. Today is Wednesday, she's at my house - I'm at work. She's looking for a job.
So what do you think? I've never been with a woman that is so sexy. She cleaned up really well. I've gotten her more clothes, and she puts makeup on even though I tell her she doesn't need it.

I do have feelings for her, and even my brain is teasing that I have a future with her - maybe even marriage... but I asked her something...
"Why would you even be interested in me, I'm not handsome."
"Feelings have nothing to do with looks, and honestly you're not ugly at all, give yourself some credit. Plus, I have a fetish for older guys and you fit my fetish quite nicely, daddy."
I laughed.
"No, I'm serious - it's a kink. If we're going to be together we need to be open and honest with each other. If you ever want to fuck another woman, now that we're in a relationship, we'll have to have that talk ok? Don't get me jealous, it's hard to do but being deceitful will wreck what we have."
"Honestly, you're the first woman I've been with in a very long time Judy."
SO that's where we are at rn. In some ways, I kind of hope I got her pregnant... but I'm also worried that she's gonna run back to her old boyfriend and leave me. I know it's a long story, and for that I do apologize... peace.