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.

Right,
I'm the only one left in my house before Christmas (we're students)
So I've spent today jacking off into my two housemates things and bra's
Anyone wanna see the material I've been using, and some pics of the girls? (None nude but they'll be looking hot!)

Real doctor from Duncan OK. First time being exposed for the swinging slut wife she is. She's on the right

married slut up for anything, no limits

Hey fellow naughty people of Motherless. Been on here for a few years and had grown interest in a couple taboo fetishes since then. I've always been an open minded kind of guy and very curious. I'm 26 and I have a younger sister that is 24. She has developed very nicely over the years and I've always been trying to see her naked and constantly think about doing more to her. We've always gotten along pretty well for the most part. Have those sibling fights as most do but we have each others back too and trust each other when needed. Now days, I live down south and she lives back home up north with the rest of the family.
Went back up there for the Christmas and New Year Holidays and ended up having to share a room with her since they turned my old room into a work out room. She has a boyfriend at the moment and got to know more about where they stood during my trip. We went out one night and had some drinks. She drank to much and I ended up having to drive her ass home and put her to bed. Her phone was there and there wasn't a lock on her phone and my curiosity took over.
I knew she had to be the type that took photos of herself. She has D size boobs and she dresses in a way to show them off a lot. She's a proud owner that's for sure. And to no surprise her phone had tons of photos including plenty of ones of herself naked and playing with herself and topless. no sex ones though. But a jackpot of sure. I was able to email myself a handful of them before she woke up and put it back to how it was without her knowing.
Also the following morning i woke up to her laying on me chest and her arm on my stomach. With morning wood up and ready and her snoring enough to know she was still fast asleep, I gently picked her hand up and moved it down to where it was resting on my dick. A minute later or so, as I pretended to be asleep, I felt her hand move around and her beginning to wake up and figure out what was going on. Her hand wrapped around my dick and then I pretended to wake up. She acted surprised at first and apologized thinking it was her fault and I said it was okay and not to worry about it. She pulled the covers off of us and got out of bed because she was embarrassed but noticed her looking at my cock that was now exposed. She said she was surprised and that it was really big. I told her that she can touch it more if she wanted and that it felt really good when she did. She thought about it for a little bit then got back into bed and laid there first. thinking. told that it wasn't that big of a deal. both are mature. nooone has to know but us. i grabbed her hand under the covers and put it on my throbbing cock. her fingers now wrapped around it she slowly started moving it up and down the length of it. continued to tell her how good it felt and making her feel more comfortable. I asked if I could see her boobs. She told me to promise not to tell anyone before she took her top off. She put her hand back on my cock and took the covers off so she could see it. Lasted like 10 minutes before I finally came. Some even shooting onto her stomach and chest. I asked during and after if she wanted any help in return and she said no and that it would be to much for her to handle now. She already couldn't believe that she had just jerked her older brother off. Neither could I. We once again promised to keep it a secret and we took turns going to the bathroom to clean up. Nothing else happened while I was home but we have texted a bit back and forth since talking about it and I think next time there is a chance we might do more. We will see. was my first experience with family. Was scary but that orgasm was one of the best and wish I could do it all over again. Thank Sis!

the story of my life and my sister (incest i guess..)

Wow... okay, I wasn't sure if I was ever going to tell anyone about this, but it's late and I'm sleep deprived so i guess I'll just write it now and regret it in the morning

First of all, - just for some background: My mom died right when I was born, (she was actually really, really hot- but this isn't about her. I guess that's fucked up to say, but whatever.) I actually grew up with my dad's family, because my dad has all sorts of emotional issues and he bailed before I was born. So you can see, my childhood was really kind of messed up.

Anyways, growing up I feel like there was always a lot of distance between me and my sister. When I was about 17 or 18 I first noticed that my sister was a hottie.

I don't want to go into to many details about it, but basically what happened is that I accidentally found a video that she made of herself. I knew she didn't make it for me- but I thought she was so fucking beautiful that I watched it twice. (probably would have watched it a hell of a lot more, except that like right around the time I found the video, all this crazy shit went down and I had to leave home. (My dad's family who I was staying with got in bad trouble with the law. I never talk about it).

Sooo... I was totally lusting after my sister at that point. She was also having bad trouble with the law. She was actually in custody when I left home.

My friend and I went to go pick her up. When I saw her that day, after seeing the video, I have to be honest, I just wanted to fuck her brains out. Looking back on it now, it's pretty messed up- but I think she had feelings for me too. She actually kissed me right after we came to get her... and it wasn't a sisterly kiss, you know? I mean, it wasn't like ridiculously sexual or anything, but it definitely wasn't sisterly.

After we left, we all went to crash with my Sister's friends. On the trip there, my friend sort of implied that he wanted to get with my Sister, and I got a little jealous. He's a good looking guy- and even though she was my sister- I just felt like he was competition. Not much else happened between us for a while except some maybe-sexy hugging.

Pretty much everyone in my life at that point was wanted by the government, so we all moved around a lot. I'm not saying that I'm proud of it or anything, but it was kind of a hectic time.

My friend and my sister never hooked up I don't think- but I thought there was some serious sexual tension going on between them. It was around that time that I got really badly hurt in an accident. It was fucked up. I almost died. But when I was in recovery my sister came to see me, and out of the clear blue sky she started gives me this awesome, slow, passionate kiss on the lips.

Sadly (although, I guess for the best) nothing ever came of it. We spent some time apart... and I started to get really religious, so I tried not to think of her that way. It was actually going well for a long time- like I was totally over her. But I have to say, like a year or so after all that stuff went down, we were out sailing (not like a date or anything romantic like that), and she was wearing like the hottest bikini I've ever fucking seen and it brought back all the old feelings. Sigh.

A little while later she actually wound up with my friend from before (the sexual tension guy). I can't say I was surprised.

But even after she was shacking up with my friend, there was one time we were at a party... my friend was inside, and my sister and I were outside alone. It was a really intimate moment. I think something might have happened, except that I killed the mood when I told her that Darth Vader was our father and that I had to go face him.

Hey guys.. I'm Melanie, the stripper who wanted a boob job! I'm making a new post because the other one got too big for me to keep up with lol.

Okay so I put this in my group first but didn't get many replies, so here goes... This is how I got into Motherless. And its all 100% true.

It started a few years ago. I was on summer break, and bored, and got on omegle. I guess I wanted to see some cute boys, lol. Well, this guy (I thought it was a guy) with a video of a snake eating a bird came on. He was trying to get girls to flash, but I told him I'd seen it already. So he starts showing me random porn and it was mostly funny (surprise tranny kinda stuff) so I stayed, and talked a bit. Then he sent me a Facebook link and asked if I knew the girl... It was me!

I found out later that it was just a trick, sent you to whatever Facebook account was logged in. But at the time he claimed to have hacked it and I was stupid so I believed him. He made me tell him my name and where I lived and shit like that. I was soooo stupid! But I did it. Then he made me flash, and then do more. Finger myself, stick a sharpie in my ass, right on myself. It lasted around an hour before my parents almost caught me and he let me go... And I thought that was the end of it.

Obviously, it wasn't. He had my name and address. He found my school, used that to find my account... And then messaged me from a fake account. Told me to set up a Skype account, for another cam session. I was terrified, disgusted, felt dirty. But we got on can, and they were nice. They still wanted me to do things, but they kept asking if I enjoyed it (which part of me did, obviously). Then they got on cam.... And I saw that it was a girl, just a few years older than me! It was freaky, but at the same time really turned me on. Especially when she stripped too...

So, we kept skyping,and before long we were dating. She even came to visit a few times (luckily wasn't too far away), which was a LOT of fun.

Of course, since it was long distance, we started to grow apart. I'd want to break up, date someone here... And she'd make a fake number, pretend to be someone else and threaten me, make me do horrible shit, and then come in and 'save me'. Each time we'd be together for less time, and she'd do more and more vile things... (That's where the pics Jorough captioned came from, BTW. Those are NOT fake tears... But its okay now, they've been repurposed and don't upset me now :))

Towards the end of all this is when she made our motherless account. 'HerMistress'. Some of you may know it vanished really suddenly.... Well, that's because I found out it had been her all along, and (after recovering a bit from the single worst betrayal I've ever felt) told her that if she ever talked to me again, if she didn't delete the profile and my pictures, I would go to the police, tell them everything, and then kill myself. I had honestly already tried once at that point.. And I cut myself. Luckily didn't leave obvious scars.

So yeah, that's pretty much it. I felt dirty and violated for a long time, and basically refused to let anyone get close. But I missed this, having people get off to me and compliment me and so on (call me an attention whore, whatever, its natural and you all know it ha), so I made a new account. And that's basically it.

I confess that I have a program that allows me to get every picture from any Photobucket account (yes even private accounts) so post the usernames of any girl's accounts that you know and I'll post any win I find here.

I confess that I am fucking one of your mothers while your father is out at work. I am currently having an affair with a woman and it has been going on for about 3 months. It is purely physical and I pretty much use her just for sex even though she wants to leave her husband for me. She gives up everything to make sure that I keep coming back for more and screams the loudest during anal sex.

How do I know that it is the mother of someone here? Well, I asked if I could use a computer to check something on the internet so she let me use her son's laptop. When I had a sneaky look at his internet history this site appeared a lot. I couldn't contain my excitement.

I am going to get some photos of her with various objects inside her and my cock in every hole and post them up. I will try and get a photo on my phone of one of the photos around the house of the family too so you will know it is your mother. Hope you enjoy seeing my dick in her!

i have always wanted to fuck a pregnant women. if there are any on her please message me asap. i would love to lick your wet pink pussy and suck on those big prego tities. my cock gets hard just at the thought of fucking you.
~FTP~