Confessions tagged with 'homeless'.

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#5576

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I have an older sister by 8 years. When I was 5 she started playing with my clit. Over the years she would lick and suck my nipples and play with and lick my clit. At age 16 she started fingering my wet pussy. From the beginning she would put her big tits in my mouth and rub her beautiful shaved pussy against mine. Around age 8 she started riding my face so I’d lick her clit and stick my tongue deep inside her. I loved fingering her. She liked rough action so I’d hump her and / or finger her pussy - hard. I loved humping her. She had me put on her strap on dildo when I was 13 and I got to fuck her. It was so good. After I’d fuck her with the dildo she would eat me out till I would cum in her mouth. When I was about 14 daddy walked in on me sucking my sister’s big titties while I fingered her tight, wet pussy. He stood and watched us - shocked.

He went to my sister and slapped her asking how she could be doing this to me. He ordered us to get dressed and said it better not happen again.

Only that night I woke up with daddy in my room masterbating and looking at me. I sleep naked. He must have pulled my covers down. I felt slightly scared at first, but my hormones took over. I started rubbing my swollen clit and he gasped.

He pushed my legs open and started ramming his finger in my juicy little pussy.

“Ohhhhhh yeah. That’s a good, little pussy. You’re so tight baby.”

He kept jacking off.

Then he leaned between my legs and started licking my little wet slit.

“Mmmmm that pussy tastes so good baby. Daddy likes this pussy. Daddy is going to lick you for a while. Have you ever come baby?”

“Yes daddy” I said. “ my sister makes me cum every day” I told him.

“Oh fuck, that’s so fucking hot”

He licked my pussy and jacked off. Once I came he left my room quickly.

A few days later, as my sister and I were jumping and rubbing our pussies together - daddy walked in again.

“Yesssss my girls are so sexy”. He came right over and started grabbing at my sister’s big tits.

“I want to join, girls” he told us.

My sister had me start rubbing her with daddy’s cock inbetween our pussies. He came so fast. Then he left the room with out a word.

Then, that night he had my sister go into my room where he met us. He wanted to watch my sister lick my clit. She spread my legs - wide. She started rubbing my pussy- getting it wet and juicy. She started licking my clit and finger fucking me while daddy jerked on his cock. Then she told dad it was my turn. She got me to sit on her lap as she spread my legs in front of daddy’s face. My knees were drawn up and daddy slipped a finger inside me. When he started licking he would start on my sisters pussy and lick up to mine. It was so sexy. But I think dad wanted my sister. Like really bad. He had me get up and he placed himself between her legs. He grabbed the vibrator laying next to her and he shoved it up inside of her. He was aggressively fucking her with the toy. I couldn’t help it. I had to masterbate as I watched. Finally he slipped his long thick cock up in her tight pussy. He fucked her so hard that he was panting and grunting like an animal. He had her by the hips just thrusting as hard as he could into her.

He didn’t cum. He instead pulled out of her and grabbed me. He threw me on my tummy on the bed and jammed his cock into my virgin pussy. I cried out. In fact I kept crying. He didn’t care. He rammed his cock in and out and viciously grabbed my tits until he unleashed streams of cum into my pussy.

Daddy didn’t come back into my room again after that. At least not for sex. Well not until my sister’s baby was born. When I was 16 my sister gave birth to a baby girl. I was elated. She would always have me babysit, which translated into me molesting that little girl. I was constantly licking and touching her nipples and tiny pussy. I loved to lick her pussy alllllll night when I’d babysit.

One night daddy walked in on me when my head was between the baby’s legs.

“Oh fuck” he muttered.

I didn’t stop. I slowly licked her with long strokes. Daddy came closer and unzipped his pants watching.

“ I like molesting my niece “ I told him. “ I like liking and flicking her nipples with my tongue. But I LOVE licking her clit and stimulating her with my fingers. “

Dad had unzipped his pants. Never moving his eyes from me diddling my niece’s pussy, he started rubbing his hard cock.

“Do you really like this daddy? Me diddling your granddaughter? You like watching me molest her little cunt? You want to help, daddy? Because my sister’s boyfriend watches us diddle her. He loves getting off watching us molest the baby. Do you want to also, daddy? Or do you want to diddle her yourself?”

Daddy stuttered and stammered. I took the baby and held her up, naked, right infront of his face.

“Lick her daddy. Lick this tiny wet pussy. It tasted so goooood. I love licking her pussy. Little girl pussy is amazing daddy. It tastes so fresh and I’ve gotten it used to the tip of my tongue.”

Daddy started licking her pussy. Such a sight to see. Such a beautiful sight. I let him hold her as he molested her little pussy with his tongue. Then I started playing with daddy’s dick.

Fuck it, I thought. I got on my knees and took daddy in my mouth. With daddy licking the baby and me sucking and licking the head of his big cock, he came in just a few minutes.

But the whole thing made me real horny.

“Daddy I know you came, but it’s my turn now. You will need to help me. He looked ecstatic. As daddy got between my legs to lick me, I put the baby over my mouth. Omg I love how she tastes. As I licked her, as daddy licked me - I came in a few moments.

So 10 years have passed. Our family is still the same. Both my sister and I have had a few more kids. All girls. We’ve had 5 total between the two of us. Two girls are daddy’s. We each had one of his children.

Nothing is hotter than when we pass the girls around. But the hottest is when daddy is molesting one of the daughters he’s had with me and my sister.

Lately I’ve started getting our girls to diddle eachother. I love watching these sisters and cousins performing incest. And my sister, daddy and I all help.

Bath time is my favorite. I love to use the shower head on their little pussies.

My 8 year old daughter started having friends sleep over. I don’t know how or why, but the little girls that come over are usually quite cooperative and let us molest them so so good. My daughter seems to already have lesbian tendencies. She loves loves loves their bodies and private parts. She’s also quite aggressive - which really turns me on. I love to watch her nibble and bite other girls. I realllllly love to watch her finger other girls. She has them play house and she’s the husband/father. She will suck the tits real hard and finger them furiously. She also is very vocal. Saying “you like that. You like my finger in your pussy”. Omg I get so wet hearing her.

My sister enjoys bringing other men over - just to watch. I let them play with me and I suck their dicks while they watch all our little girls being so sexual. I love to make these old perverts cum on the girls’ tits and ass. Then I rub it alllll in to them and I’ll lick my fingers clean.

I have been wanting to find a teen prostitute. A girl. I want to pay her to let me take advantage of her. And I want to pay her to be the babysitter who molests them as I watch. Pay her to let daddy fuck her as hard as he’d like. Maybe even let a strange man watch as she licks and fingers the girls.

The best of the best is when we go to the park. The park nearby has a homeless shelter right next to it. So the park is always filled with bums. I love bums. Dirty unshaven. Sloppy. They are always desperate for anything related to sex. When I see them I start by going up to one and taking one of their hands. I place it on my tit. I start rubbing their hand into me. Then I slide their hand down between my legs.

“Do you like that?” I’ll ask

As soon as they confirm to like it, I surprise them by putting their hand on whatever girl is w me - on her pussy. They will realize immediately that there is no diaper or panty on the girl I’m holding. I love the look they all get. Excited. Mesmerized. Horny. Eager.

I suggest we go for a walk on the trail. It leads to my parked car in a secluded area. Once we get to my car I’ll let them be alone with her in the backseat. I sit in the drivers seat.

“You can lick, suck, and finger. Always gently. But no real penetration” I tell them. And I always tell them”make sure to lick her up reallllllll good, you understand? They always understand.

This last bum that diddled the 6 year old was real eager. He quickly undresses my daughter and started licking her nipples. He immediately started licking and lapping at her pussy and worked the tip of his finger into her wet pussy. I told him “take your dick out. Slide her up and down your shaft. Three or four strokes of my daughter's pussy along his shaft caused him to cum almost immediately. He moaned so loud. I took my daughter back into my arms as he cleaned up.

“Lady thank you” he said

“Oh no problem. I can come back for a replay for you. A different girl. A different age. “

“Holy shit! Are you serious”

“I am” I said and smiled.

I see him now twice a week.

#5455

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It was a late night at work. I left in the dark, it was after eleven. The night was cold and wet. I noticed I needed gas and stopped at a gas station. This man came up and asked for money. I told him I didn't have money but I would buy him a dinner at McDonald's which across the highway. He got in the car, and he smelled of garbage and urine. We went through the drive through and I bought him a meal. While he ate his hamburger I blew him. I sucked his cock to completion and licked his cum off and swallowed it.

I'm not proud of what I did. But I don't have negative feelings. I always wanted to suck a cock to see what it was like. I'm glad I had the opportunity and he got a free meal out of it.

#4548

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i have a fantasy where i get a homeless guy lick my daughter's pussy while i watch and rub my pussy. she is just over 1 year old. I masterbate several times a day thinking about it. to watch some dirty, old, perverted, homeless man licking her little pussy and get off watching would be so hot. i'd probably let him lick my pussy too.

#4376

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I’m 15f and I love to get my pussy licked. Especially by old men. I love a guy daddy’s age or grandpa’s age licking my clit, flicking my pee hole, tonguing my pussy. I will go to truck stops and get licked good by 2 or 3 guys. I’m always going to the park at night to let some man lick me in the bathroom. I even went to the part of town w a lot of homeless people. I went up to a man in his 50s and asked him if he’d please lick my pussy. He was in a sleeping bag in an alley. He told me to get in the sleeping bag with him. He pulled up my tshirt and started sucking my tits 36D. Then he started rubbing my pussy under my skirt, over my panties. It felt so good. Then he made his way down and started licking my clit. He got faster and more aggressive. He was tonguing my pussy and grabbing at my tits. He licked me till I came. I’m really in the mood for a 70 year old. I want his face hurried in my pussy, then I’ll ride his face.

#2595

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I was walking home from work at night. Until i passed by a homeless still awake waiting for a person to give her money. At first i don't care much as i just walk pass her. But then my dirty mind racing in my head. I stopped and walk back to her. It was a quite road. So i talked to her about everything. We talked for at least 30 minutes. After that i offer her a lot of money. But before she could take it, i give a condition. She'll let me fuck her this night and i'll give her a lot money. At first she was disagree. And she was silent for 5 minutes until she nod a little to me. So i gave her birth control pills. As i always cum in every girls i fucked. From mouths, pusssy, and ass. So i yold her to take the pill. And she take one. I took her to nearby empty alley and found a good corner to fuck.

So then, i told her to be on her knee. And took out my cock so she could suck it. She was a bit nervous and tried to resist when i pulled her head to my cock. Even when i deepthroat her she still tried to resist. I kept forcing my cock into her mouth. After a few gagged, i told her to stand and bend ti the wall. Open her pants and started to fuck her pussy. She moan so loud that i'm afarid we will get caught. But as i look around nobody was there. After that i star ro fuck her ass. Anal sex is my favorite sex. When i fuck her ass, she cried and scream. And begging to let go. But i refuse and kept on fucking her ass. After 5 minutes on ger ass, i told her to lay on her back to the wall and i raise her top, showing her quite a huge boobs. I fuck her deep in her pussy. I love her moan and scream. So we fuck like that for anothe 5 minutes until i cum inside her. And we both were cum together. I still let my cock inside her warm pussy. When i pulled it out, i satidfied when i saw my cum flowing out from her pussy. But it wasn't finish yet. I decide to fuck her mouth again and made her drink my cum. I like to see her struggling when i kept deepthroat her. And her legs kept struggling to resistit. Until i finally cum and forced it to her throat. Her hand try to push me away. But i told her to swallow it or i'll never pull it. Until quite a bit long. I finally heard her sawalloing my cum. She take a break and breath out of exhaustion. After that i gave her the money even double than what i was offer. Then i told her if she need any money, just call me. She nod a little, then i took her back to the place she slep. And then i left.

Two weeks later she called me because shen needs. Another money. I agree but this time i take her home and let me stay until she could afford her own house. She stayed with me for two years. And we fuck everytime i like it. Now she has her oen house and worked on the general library nearby. And we still fucked until now.

#2586

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This happens2 years ago and still happen today. I am a 19 uears old teenager. My parents were always out of town for work. So i stay at my house all alone. Being discipline is not easy anyway. I started to work on loval cafe and helping a friend selling vapes near there. I'm able too get money for my own from that.

So one night after i worked, i went home a bit late. Before i was able to get home, i saw a homeless woman outside the cafe. And she looks hungry. Since i couldn't bring her inside, i bring some food outside and give it to her. When i was about to give the food, the lights on the terrace give a clear look for her face. And i recognize the face. I believe she was my junior high school teacher. She was known fpr her beauty and all of my friend love her. Despite that, she was known to struggle for a lot of things back then like debt, divorced, etc. And i was a bit surprise to see her to be homeless.

I tried to talk to her. Calling out that we knoww each others on junior high school. She finally remember me. After some talk, i told her that i could giver money, monthly. Her response is tgat she will do anything for it since she has already given up on everything. And suddenly something crazy crossed my mind. I jokingly told her that if she's willing to spend a night on the bed with me i will give her a money. We were laugh for that, abd then there's like a minute of silence. Then she said that she will do it if i kept my promise. I'm a man of my promise so i kept my promise.

After that i took her toy house. In which the house were empty since my parents return only on last month. I took her in, and we go straight to my room. We take or time, talking to each other recalling junior high school. Until she said that now she's sleeping with her student. That still crazy she said. I respond it with yeah its crazy. And started on opening my pants showing my cock. I pull her arms giving her a sign to get on her knees. At first she had a doubt. She's a bit shy. But i kept making her to not feel shy. And so it started. She start on sucking my cock. Whenever she hesitates to do sexual things with me, i forced her making her to not hesitates. So we then spent the night together. And on the climax i toured all my cum inside her pussy. A pussy that should have no longer tight. And the next morning we fuck again and cum inside her again. Its a bit crazy since its my former teacher that i fuckrd. But everything goes on. And so i gave her a quarter of my saving.

So everytime she needs money, we spent the night together. And if she ask for money on the same month despite she already got it for that month, i give her a quite pain anal and creampie, with cumthroat on her. I like her screaam when i do anal to her. And its still goes on till i write this confession.

After some times, she said she's not feeling well. And i took her to local hospital by telling the doctor that she's my sister. After that the doctor diagnose that she actually pregnant, but the 3 and a half month old inside her belly didn't make it. So after that we were more becareful and i told her to take on the birt control that i bought for her before we fuck

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