Confessions tagged with 'sister'.

#2368

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I had just turned 18 and was caught by my 20 year old sister shoplifting some condoms. She video'd me with her phone and said that when the time came I would have to do whatever she said or she would show that video to our parents and the police. I didn't think too much of it but knew my day of reckoning would come. A couple of months later it came. She said we were going to her friend Tom's house and I would have to do what she said. I thought "Whatever. I guess I'll do what she said. How bad could it be?"

She drove me over to Tom's house and when we walked in he offered me a beer. I was only 18 but had drank beer before so I took it. She said I might need to be a little drunk to endure the night. After my third beer she said it was time to go to the basement. I thought "Sure, whatever." We walked downstairs to the basement and there was a guy sitting in the corner chair naked. I didn't think too much of it as I knew she was sexually active. Then they led me to the other side of the room. I saw two 4X4s about four feet apart with a bar between them. She led me to them and they proceeded to tie my hands apart on the 4X4s. I said "What the fuck is this?" She told me that this was my punishment for stealing. I figured one of them was going to spank me but she had other plans. She told tom that she would be back in an hour and he could do whatever he wanted. That scared me a bit. He walked around to the front of me and undid his zipper. He said I was going to suck his dick or I'd be sorry. I said "Fuck you. I ain't sucking nothing." He zipped up and walked out of sight. A few minutes later I felt my pants being undone and pulled down along with my underwear.

A minute later someone, either Tom or the other guy knelt down under me and undid my shirt. Then I felt something being clipped to my right nipple. Then my left nipple. There was something pulling them toward each other. It hurt like a bitch and I yelled. Then Tom said "Too fucking bad. You're mine now bitch." Then someone had their hands on my ass and was rubbing up and down my ass crack. I felt something being squirt on my asshole and then a cock being inserted. It hurt like a fucking bitch. About that time Tom walked in front of me totally naked. When the guy with his cock in my ass pushed forward I opened my mouth to yell and Tom stuck his cock in my mouth. I was being fucked from both ends. I wasn't gay and had never had a cock in my mouth but he just kept fucking my mouth. The cock in my ass hurt like a mother fucker and I noticed I was crying as he fucked me from behind and Tom was mouth fucking me.

About that time I heard my sister say "This is your punishment for being a little fucking thief. Now, you're gonna take everything they have to give you or the video goes public." Tom was fucking my mouth and the other guy was fucking my ass. Then I saw my sister with her phone stand in front of me videoing me sucking Tom's cock. I knew I was stuck. I couldn't do a fucking thing about it. Tom came in my mouth and the other guy came in my ass. When they were done the let me loose and sis drove me home.

That was bad enough, but then she informed me that I would lick, suck or fuck her any time she wanted. That summer there were plenty of times she was drinking and her boyfriend wouldn't fuck her. Those were the times she called me into service. That was almost 20 years ago. Since that time I have gotten used to sucking or fucking anybody she said. I guess she's sort of my pimp even though she's my sister. I fuck her occasionally but mostly she makes money off of me sucking or getting fucked by the men she knows. I don't mind too much and actually have fun doing it. We live together and make a pretty good living with me being her bitch.

#2303

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My sister is two years older than me. She had filled out nicely by the time she was a high school senior. I used to film her taking a shower and marveled at how big her tits were. I especially liked to jack off watching her finger herself in the shower. This was on my phone of course. On Fridays she would go out with her friends and come back drunk. One weekend our parents were out of town and she came home super drunk. I offered to help her get ready for bed. I stripped her completely and helped her under the covers. I just stood there as she closed her eyes and within literally seconds she was passed out. I stood there for a couple more minutes to make sure she was out. I shook her and she merely moaned a little but didn't open her eyes.

I lifted the covers off of her and stared at her gorgeous tits. I reached out and put my hand on one of them. She didn't move. I got a little bolder and played with her nipple for a minute. My cock was rock hard already. I had never fucked a girl but had read all about it and even watched some videos. I rolled her onto her back with the intention of fucking her. Instead I thought I might be able to put my cock in her mouth. I took my pants off and stepped up to the bed. I pulled her head forward a little and put my cock against her lips. I pushed a little and she opened her mouth just enough for me to force my cock past her lips. I fucked her mouth for a minute or so and had a wild thought. I pulled out of her mouth and crawled on the bed. I straddled her and put my cock between her tits. I pulled her tits over my cock so it created a tunnel. I started to fuck her tits. She was totally out and didn't notice a thing.

I was getting closer and closer and when I knew I was about to cum I scooted forward a little and put my cock back in her mouth. I fucked her mouth a few more thrusts and started cumming. By reflex she started swallowing. I couldn't get all of my cock in her mouth but got enough so my cum couldn't escape. When I was spent I stayed right there until my cock started to get hard again. I finally pulled out of her mouth after about five minutes of resting it there until I was hard again.

I scooted down and spread her legs a bit. I could smell her sex and I lifted her legs up so her feet were flat on the bed. I scooted up and put my cock against her cunt. I slowly pushed in, watching her face all the time to make sure she was asleep. I fucked her for the next 15 minutes. Occasionally she would let out a moan, and one time she mumbled something that sounded like "Fuck dad, fuck me deeper." What the fuck? I thought. Is she fucking dad? Then I get even more excited to think my sister fucked our dad. I wondered how big his cock is and if he fucked her for a long time before filling her up. This was so fucking erotic that I was cumming before I could react. I didn't pull out right away but bent over and sucked on her tit for a couple of minutes before I crawled out of her and went back to my room.

I couldn't jack off again so I went to sleep. I got up early and went into the kitchen to eat a bowl of cereal. When I was just getting done with my cereal she came in. She acted as if she had no clue what happened last night. Mom and dad were still asleep and she was holding her head. She obviously had a headache. I sat there a minute longer than I needed to and she was drinking orange juice. I got up and put my bowl in the sink. I started to head for my bedroom when her hand reached out and grabbed my cock through my robe. She looked up at me and smiled. "You have a really nice cock and your cum tastes really good. I was so embarrassed I wanted to run but was frozen in place. "Don't worry stud, nobody will ever know. And by the way, I don't have to pretend to be drunk for you to fuck me. Next time just ask." The next time I did, and she said yes.

#2108

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I've been blackmailing my sister to suck my cock ever since I saw and filmed her fucking the dog. I try not doing but forcing my cock into her face feels so good. I also watch as I make her fuck the dog and film it. Slut.

#2051

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My sister stayed at my house for a few days and one afternoon came out of the bathroom wrapped in a towel. She was on her way to her bedroom and when she passed me I pulled the towel off to see her body.

For a mid-30 woman her body is average. I did manage to tough her breast and got hard immediately. Sister did try to get the towel back from me and we wrestled around some. I took out my penis and stared masturbating while she still tugged on the towel. Sis watched me, alternating looks from penis to my eyes. I shot my load in a kleenex and thanked her for her assistance.

Next day i walked around naked after shower and in the end of her stay we lost all our inhibitions. She trimmed her pussy with one leg up on the bathroom counter, with door and lips open.

I want to pursue a sexual relationship with her and will bring it up next time she visits.

#1894

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my sister had some bad friends before she was kicked out of the house when she was 15. those friends would give her cash they stole from their parents, she gave me the cash, and i gave it to my uncle to buy vodka that i would give to her to drink with those friends. im three years older than her, and have been spying on her with hand mirrors and smelling her while she slept since she was 9. she started getting wasted at 12, and i would kick all her friends out of the garage whenever she passed out, so that i could lick all over her body and grind on her. i even started using my allowance just to get her her own private bottles. she would get drunk in her room, and i would have the time of my life. penetrated her 2 months before our dad found out that she had been doing this and told her she needed to go live with her bf. she never ratted me out because she thought all that time i was just doing it for her. our parents were super religious and strict. my dad died in 2016 in july, and my sister texted me last week looking for a place to stay and some extra money. i have a well paying job, so i can afford to support her and her habit. i know she's in a tight spot and she's had a few abusive bfs before, so i'm going to take advantage of that. i asked if she wanted to get sexual for the money, since i was single, and she agreed. so now, not only am going to cum in my sister's mouth everytime she wants 50 bucks, but i've started filling my pantry with booze so i can also molest her while she sleeps. i'm just so excited about how good my life is right now that i juust had to share. she's taking a bus down from seattle next weeek. i hope i don't get struck by lightning before then.

#1807

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I was exposed to sex at a very young age. I think I was 6 or 7 years old when my gay cousin, who was 16 I guess, started molesting me. It didn't last long, because he moved away. 3 short years later though, at the age of 10, his brother, 14, started messing with me.

Im not gay at all, so when my second molester showed me how to French kiss and masturbate, I showed my 7 year old sister, who let me do these same things to her, because she was too young to understand. He never tried having sex with me, but did ask once if I would like to penetrate him, I was 10, so I passed on it. #2 was, for whatever reason more interested in teaching me about sex and my body. He would kiss on me and jack me off, I hadn't hit puberty so he just made it sore. However this went on until I was 13 and he went off to college!

When my second molester left, I wasn't sure what to do with this knowledge about sex, I couldn't handle it. I was always horny masturbating wasn't enough anymore.

That's when I became the molester. I would sneak into my sister's room at night, lure my youngest sister, 3 years younger than me, away and have her jack me off. I tried putting within her mouth a couple times, but she didn't know not to use her teeth (and I didn't know well enough to tell her not to)

I kept messing with baby sis for the next few years off and on. Mostly when I didn't have a girlfriend and when she would allow it. My sister had started realizing what I was doing to her was wrong so she didn't always help me get off.(only hand jobs) My little sis, over those few years, turned out to be my greatest weakness, and when she turned 13, she stopped letting me touch her and jacking me off. I was passed and horny!

She,my sister, developed fast and well! Her breasts at 13 where a perky C Cup and she was so thin (90-100lbs) but had a small bubble butt on this 4'11" frame, I couldn't help but plot ways to try and be her first and have her be mine!

Every time I was alone with her or could sneak away alone with her I would try groping my little sister. When I would pick her up from after school functions or take her to drop a friend off, I was trying to molest her, but she would quickly shake me off. "Why do keep trying to do this, you're my brother," she'd say.

The longer I went without molesting her, the more aggressive I became with her. Dropping off her friends would turn into 45 minute errands because id always take thaw long way home to make sure I got something off little sister. Putting my hand down her pants and feeling her pubes for the first time, making her pull up heat shirt so I could see her magnificent tits and eventually put them in my mouth.

The last car ride she would take with me, we drove her friend home. When I missed the turn onto our street she started right away, "please, Im you're sister, don't you feel bad?" she said almost crying. I said, "right now I just feel like getting off." I pulled into an empty lot in the middle of a dirt road and pulled out my Dick. Her eyes red and her pleading to think about what I was doing. I pulled up her shirt and bra, and her big beautiful tits with small pink nipples,just plopped out. I crawled over the center console almost directly over her, my Dick in my hand! I put it between her tits to titty fuckin little sister for a second, and then got back over her, jacking myself off and nutted all over her perfect teenage tittles.

She cried on the way home. I always felt bad after, but only after. Sis would make sure she was never alone with me again. It was back to square one for me then on, until one summer night a perfect storm.

My parents had went out for the night, my other sister was staying with a friend and my brothers were at school functions out of town. When we got off the bus, little sister realized, she was alone with me and nowhere else to go. My balls tingled, but I didn't act on it...right away, that is.

The Sun started setting, and my 16 year old urges grew unbearable. "Sis, can you come here?" I called her to my parents room. She was very reluctant to acknowledge me at all, and with very good reason, I was just raging sexual hormones with eyes! Eventually she made her way to our parents room, where I stood waiting. She kept her distance, making sure not to step through the doorway, "what, what do u want?" looking at me very annoyed. "I need your help, right now." I told her. "With what?" she asked as she followed my eyes down to my crotch where a pant tent was tall and still growing. "Leave me alone." she said, "go do that by yourself!" I played along saying "not really, look its just a pen!" when she relaxed for a minute and let down her guard. I moved to the door and locked her in.

"What are you doing?" she asked me, realizing she was exactly where she had been avoiding. "I need you to help me cum, and ill leave you alone" I tried convincing little sis. And again, "Im your sister, why can't you get someone else or do it yourself?" she said with shaky voice and glossy eyes. "Cause, you're already here and Im tired of my hand!" she was quiet thinking for a minute. "Ok, fine, then you leave me alone!" I ripped my jeans off, as she reached for my thick 8" cock, which might as well be 18" in her small hands. I pulled away "take your shirt off," I said, she pull it up over her big tits, "Now, take off your shorts." I demanded. "No, why!?" she was nervous. "You always just want my hand."

She said confused, but with a sense of knowing exactly what I was asking. "Not this time little sister, I need to put it in something for once, so Im gonna put it in you." "NO! LET ME OUT OF THIS ROOM, IM JUST GONNA TELL ON YOU!" she yelled at me.

"Look, u can get on your back, take off your shorts and ill be done, or Im gonna take it." I threaten her, hoping she would just let me fuckin her. "No, I don't want you to do it to me, plus your thing wont even fit inside me!" she said trying to discourage me but knowing she wasn't totally wrong and hoping I would do the right thing. I was fed up, it was the car ride all over, I pushed my sister on the bed and start undoing her shorts, "please don't, Im ur sister!" "don't hurt me, please brother, your thing isn't gonna fit anyway!" she said sobbing. I start to crawl on top of her when she turns on to her stomach fully clothed with her shorts undone. This is all turning me on more, my Dick is dripping with pre cum hard as a rock! In attempt to get between her legs I slip my cock between her thighs and it went under her shorts and panties with ease.

"OWWWWW!" little sister sheiks at the top of her lungs and starts balling face red and wet. Because, seconds before, trying to keep me from popping her cherry(and mine) she squeezed her thighs together making my Dick slip upwards. The second she screamed, bloody murder, I felt sudden tightening around my Pecker, as if someone put a rubber band on my Dick. But alas,her squeezing her thighs to keep me out of her sent my dripping hog right up her asshole! "BROTHER, STOP, IT HURTS!" she begs me crying. "I bet you wish, you would have listened, now, huh?" I say content. "Please, Please, take it out!" she says barley able to breath from the pain and tears. "Ok....after I cum." after about 5 minutes of no mercy stretching sisters asshole butt pounding angry virgin anal Im getting close, one....more...pump...to this day I don't believe I've shot that much cum as I shot into my poor little sisters virgin asshole. I don't know why, but she never told, even though she couldn't sit for two weeks after I tore it up. Not just because the pain, also because my jizz was still coming out of her ass for a while after. We have families now, but sometimes I just feel like giving it to her again,her husband aint got enough for her...but I do, eventually

#1775

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My sister is two years younger than me. When I was 15 with hormones raging I started to notice her developing body. Our parents were away for a week and I was in charge we were supervised by our aunt & uncle who lived above us in a two flat building. We'd start to wrestle in the evenings and I'd get bold and cup her beasts over her clothes. she didn't protest and I got bolder shoving my hand inside her jeans & panties to feel her pussy that was sprouting hair. She seemed to enjoy this and I'd just gently cup her pussy & insert a finger into her while gently finger fucking her. I eventually got her to remove her top so I could see her budding tits & suck on them. This went on for a couple of years, though we never went further than feeling & petting.

I'm 63 now & about 3 years ago my mom had a problem with her garage door opener. My sister had stayed overnight at my moms. While I was out working on the door my sister came out wearing a cotton nightgown and she was clearly wearing no underware. It was a chilly morning and her nipples were really standing up on her large breasts. She was asking how it was going and if I needed any help. I asked her to get up on the ladder & see if the chain was skipping as I operated the door up & down as she climbed the ladder I got a nice view of her legs up to her hairy cunt up to her tits. It was hard to concentrate on the job I was doing. I was not sure if she wanted more attention from me or if she just got off knowing she was teasing me. I think I missed my chance.