She was 20 at the time, living with my mom and me in our house. She was going to college, I was in high school at 15 and not a stellar student
My sister Jeannie was 20 years old at the time. I am pretty sure she’d been fucking since she was about 15 or 16. She was 5ft. 7in tall, weighed only 105lbs, C cup tits that didn’t bounce at all when she walked they were so firm. The only thing firmer was her tight belly and the most beautiful ass ever. I eventually saw that she trimmed her black haired pussy, matching her black hair flowing past her shoulders from her head. It framed a beautiful face. She and my mom always walked around in panties and bra, or a tee shirt, always without a bra, sometimes without panties. My mom from the time I was about 11 would change everyday from work clothes when she got home, and then again when she went to bed. She said it was nothing to be ashamed of and I could see her as she really is. I never understood it, but I loved watching her big D cup tits and dark nipples bounce around, her slightly bigger ass than Jeannie’s but they had the same patch of hair on their pubes. Mom had more of a gash, Jeanie had pouting little pussy lips between her legs. I was gawky, 5ft. 11in, 160lbs. I guess a decent cock, I tried not to but sometimes my mom would come in as I was changing and talk to me too. My sister didn’t change in front of me, but always walked around in a tee, or panties bra, panties tee. I’d see up her tee shirt when she’d sit down and saw her pussy lots too. She and my mom were good masturbation fantasies for me. I was really having trouble in school, the teachers told my mom that I might have to repeat if I didn’t bring up my grades.
Mom just kept on me to keep studying, but one time she was gone for the weekend. My sister didn’t have any plans, didn’t go out just stayed home. She talked to me about my grades and I was poo pooing it. Finally she left the room and came back in totally naked. She took my hand and put it right on her tits. Then moved it to her pussy. She held it there on her pussy and looked me square in the eye. “If you get all A’s I’ll have sex with you. At least four times, so we can do everything you want. I’ll suck you, you can fuck me, I’ll even let you fuck me in my ass” She turned around the planted my hand on her ass, then reached back and pulled my face to her beautiful ass. “Kiss it” she said and I did. Then she turned and pulled my face to her pussy. Pushing me back she said “All A’s, understand” not one grade less even in one subject. All 6 subjects, all A’s and I’ll do everything your little weird mind could think up. . . and probably more” All I could do was sit wide eyed as she walked out, watching her tight ass, that I’d just kissed, sashaying away. I shouted “OK” like a total dweeb.
I studied, spent time at the library, took tutoring from teachers after school, did extra credit and in 8 weeks I got my grades, all A’s but one B. I went to the teacher, a guy and asked what I could do to get an A in only a few days. He asked why, I ‘d gone from a D- to a B+ in short time. I kept pressing that I needed an A in all my classes. He pressed and I told him that my fictional girlfriend offered to give me a BJ as much as i wanted over a week if I could pull it off. “that’s a good excuse, the best I’ve ever heard” he said and right there changed my grade to an A. A few days later I produced all A’s. My mom was ecstatic as she was changing her tits bouncing around, her hairy pussy between her thighs. Then my sister. All she said was “We’ll start this weekend” The weekend that my mom was off to her sisters.
On Friday mom left, at 6 that night, Jeannie came into the living room wearing garter and stockings high heels, and a basque that exposed her tits. Her ass and pussy were free too. She sat on my lap and kissed me. “You’ll have to kiss me a lot, it’s time you learn how anyway so you don’t screw it up with a potential girlfriend. I like being kissed when I’m having sex, remember that, always, with all girls” she said. I just dumbfounded said “OK”. She put my hand on one of her tits and told me to gently pinch and roll her nipple. I did and moved from side to side doing it to each of her tits. Kissing her, she started kissing my neck, I did hers. She moved my head to her tits and told me while I knead one to suck lightly on the other. Again I sucked both her nice, firm tits. Then we kissed and she was on my neck and my ear and moved my hand to her pussy. I tried to put my finger in her, she moved my hand down to her vag opening “It’s down her, but not yet” she said pulling it back up to her clit. “Rub her for a while” Kissing and rubbing her clit, sucking her tits her pussy was getting so wet. Moved over and laid down on the couch spreading her legs. “Now lick like you used your hand, lick my button down there’ She got me licking super fast up and down, the pause go all around her pussy lips and even on her fuckhole. Then back up to her clit I went. She started moving her hips and pinching her own nipples, I reached up to do that while I was licking her. She held my head and pushed up. She said she was cumming, she did two orgasms one right after the other. Then told me to stop. I went up on top of her and kissed her again. “You’re getting really good at kissing” she said. Then she stood up, and took me into her bedroom. “We’re going to be staying here this weekend to sleep. We’ll move some of your clothes into my closet” Then she started taking off my clothes, more kisses, even kissing and biting on my nipples, I liked it. Stripped she sat me on the edge of her bed and pushed me over. She got on her knees on the floor and sucked me. I came in minutes, trying to pull off i was telling it was about to shoot out, she pushed away my hands and took my cum in her mouth. She looked up at me leaning over my cock, her tits touching it and she made a big point of swallowing my cum. She told me that any girl who won’t swallow should be dumped immediately, she’s not worth it as girlfriend material. “This will also make you last longer while we have sex” she said.
Being young and horny as hell, having a beautiful naked woman in bed with me, even if she was my sister, I was ready in less than 10 minutes and we started kissing again, feeling each other, and when she was wet enough, and rubbed close to cumming, I was hard and she pulled me over on top of her. She pulled up her legs, and I placed my cock inside her pussy lips, she reached under and pulled it down a bit “right there baby, push in slow” I did and didn’t stop till I was all the way inside my sisters pussy. It was so damn wet and warm, so nice. I couldn’t help but kiss her again. She wrapped her legs around me and I started pumping at her. I was not used to it, and I pulled all the way out a few times. It was about 10 minutes into it and she held me down, lowered her legs on the outside of mine and rolled us both over. She brought herself up on her lower legs and was riding my cock. Taking my hands and placing them on her tits “You know what i like baby, just do it” she said and I went on rolling her nipples, pinching them keading her nice big tits, and was kneading her ass too. She came before I did, then she picked up the pace and I was soon cumming into my own sisters pussy. It was unlike anything I’d experienced before. After that she got off me, we laid together on her bed. “Damn you little dweeb, you take direction well, you’re gonna be great at this after this weekend is over” she said.
During the weekend she said it “We’re going to be like a newlywed married couple, have sex as much as we want, go out to eat at nice restaurants, go swimming and fuck. . . all the time” We did, it was Sunday afternoon, after the pool I’d fucked her pussy about 9 times during the friday night to Sunday morning. I wanted to again, and she said it was time to do the final. I was afraid that she meant our last fuck. But she meant the one thing she promised that we hadn’t done. Her pussy needed some rest, so taking off her bikini, she laid on the bed face down, her tan lines getting me hot already and gave me to tube of KY. Put this on my butthole and all over your cock. I did, then she told me to go very slowly and I slowly inched my cock into her tightest hole. Holy shit this was good, I couldn’t believe how much different it felt than her mouth or her pussy. I pumped slowly, and at her encouragement went faster and faster then she started bucking back into me and yelled that she was cumming, I came at the same time. I stayed with my softening cock in her ass for several minutes, kissing her ears, reaching around and kissing her mouth, I couldn’t thank her enough for that. I eased out, and laid down next to her.
She got up and for the first time sitting on the toilet left the door open. I could watch her pee then poop and get my cum out of her. She took me into the shower where we washed each other. She kissed me deeply out bodies together and told me that was the first time she’d ever cum from getting anal sex. I asked if sex was over now between us, and she said no that mom didn’t come home until tuesday morning. I asked about her pussy being sore, and she said it would be OK by tomorrow, I can do it in her mouth or her butt tonight. After a nice dinner at a restaurant (she made me wear an suit and tie, she wore a nice but short dress with only a bra, garter and stockings, no panties. That night I got another BJ and fucked her tight ass once again. This time she came twice.
We fucked until our last one on Tuesday morning. I moved my clothes back into my room. We kissed long and hard. “You’re gonna make some girl really, really happy. Just don’t take any shit from them just to get laid”. I knew it was over and she did also. I got really jealous when I’d see her go out on dates and come back late. One night I was horny from seeing my mom naked and the evening half naked I went to her room after mom went to sleep and asked her if she’d let the guy fuck her. She did not, but was horny. So that is the way it went, every once in a while I’d get to fuck her again. Until I got to dating. I could drive, had a car and was getting laid. Even she was a bit jealous when I started fucking others, we both got over it though.
It was a hell of a way to learn about sex. I did keep my grades up though and would get a slight reward every semester from her, until she moved out.
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