We were both 15 and best friends. When staying overnight at his moms house, we’d sleep in a double bed in his sisters room (14f) and she’d sleep in his room in his single. His mom really liked me a lot, and trusted me. She was very untrusting with her own two but with me she’d let the girl cook while the mom was gone, let them stay at the house while she was gone etc. His name was Stacy and their house on the interior doors had those old skeleton type keyholes taped over. I got him to move the tape over so we could peep on his mom, his sis and in the bathroom, there was a tiny hole already. We got to see his moms D cup tits, beautiful body, great legs and ass, and a coal blackhaired pussy. His sister had less hair on her cunt and it was light brown. She also only had A cups that we watched grow to B’s.
One night, our playing around in bed, led us to being naked, rubbing each other, and he got on his side and backed his butt up to my hard cock and wiggled it around. I started humping my cock up and down on the crack of his ass. We were trying to be quiet so the bed wouldn’t squeak and alert his mom or anything. He moved to a draw in his sister nightstand and brought out some vaseline body lotion. Using his hand he spread it on my cock, then rubbed the rest in the crack of his ass. He wiped off his hand and moved his ass back to me. “Now do it, rub it up and down like you were” and I did. I warned him I’d cum if I kept it up and he reached back and held my body into his and I came all over his back and butt and on my stomach. He got some tissue and cleaned me up, then him. He took the tissues naked out into the hall and into the bathroom to flush them. He came back. I couldn’t believe, even at 1am that he’d go out naked like that. Under the covers he asked if I liked what we did and I told him I loved it. It was the first time I’d cum with another person involved, not just my hand. He put his hand on my cock, then turned over, and pushed his butt back to my now soft cock and told me “Any time you want or need, I like doing it for you”. We went to sleep.
Over the next afternoon I rubbed up against him in the bathroom and shot off all over his butt. Without any lotion, I used my finger to pick up some of my cum and put it to his mouth. He lapped it all up and asked for the rest. Sated until that night. Alone again in his sisters room he asked me if I would put my cock in him. “You mean fuck you?” I asked. “Yes, fuck me in my butt, I’d like that even better than what we’ve done” he answered. Then he added “Will you? Please? Please, I really want you to and I want to do it for you, I want you to enjoy being with me, anytime we’re together, anytime you want”. I told him to get out the lotion. Him on his belly, legs together, my legs outside of his, I told him to reach back and spread his cheeks open. There it was, his virgin, tiny, little pink pucker. I wasn’t sure it would fit. I pushed more lotion into his ass and lined up. I went slow but steady. He had no reaction other than a gutteral moan and an long drawn out, low sounding “oooohhhhhhhh yeaaaahhhhhh”. Once I was in, I felt so good, his body tight around my cock shaft, 7 inches of total joy right then. I guess I held it there too long “Do it, do it to me, I want it, fuck me” he whispered. I fucked him and after about 15 minutes of trying my best to hold out, I had to cum. I picked up the speed, the bed squeaking and then I plunged deep into his ass, my own fuckhole now. I came, he was telling me he could feel it. He started bucking into my cock. After when I pulled out I realized he came on the sheet.
So whenever we could I had a fuckbuddy. He loved getting fucked, I loved fucking. He didn’t want to suck cock though “That’s for girls to do” he’d say. Then one summer his mom asked if I’d mind staying with him for 2 weeks while she and he daughter went to help her mom after surgery. I stayed over and helped pack the car and that night in his sisters double bed, I fucked my personal piece of pussy again – twice! Then we saw them off, and he went into the house. I followed and he went into his sisters room and shut the door telling me not to come in, to wait in the living room. I was watching a movie and he comes in. His fairly long hair styled, curled, and with berettes at the sides, he had on make up and looked so much like his sexy mom. He was wearing his sisters clothes. He (now she told me to call her a HER) was wearing a mini skirt, pink panties, bobbie sox, patent leather heels, a white blouse open buttons, and a matching bra to the panties. She asked if I liked her, I did. She came and sat on my lap as we watched a movie. She started kissing on my neck, my ear, I kissed hers too, then we kissed on the lips. Her tongue lighting pushing into my lips and my hand going up her mini skirt to her panties. He wasn’t huge, he was kinda tiny in the cock department, but he had it tucked him. I raised the skirt and could see he trimmed his pubes into a patch straight up about 2 inches wide, just like I told him I liked when I saw it on his sister. I aggressively kissed her and reached up under her ass to pull her panties down. “NO, NO, don’t, not yet we have to do something first” she said. I didn’t want to wait I wanted to fuck her.
She got down between my legs, while she was kneeling in front of me on the floor, me on the couch. She undid my belt and pants and pulled out my cock. “You’ve been asking for me to do this, don’t you still want me to?” she asked. “Afterall it is what a girlfriend should do for her boyfriend right?” With that I got my first blowjob. She choked a bit but swallowed it. Then kissed me and went to fix lunch. Sated for a while, I couldn’t wait to get her into bed and fuck her. “Not yet” she said “We need to wait, AND you have to earn it. I think a boyfriend should take his girlfriend out for a date first don’t you?” We went to a movie, grabbed some takeout and went back. After eating she disappeared again, and came back out in one of her moms super sexy black see through lingerie sets. Pulling off her panties in her moms bed, keeping on the basque which had cutouts for his moms big tits, they still pushed up his pecs so he had a little tit for me. It was that way we fucked.
He was my live in girlfriend for 2 solid weeks and then a call and we had 4 more days of being girlfriend and boyfriend. After that it was back to fucking when we could, he’d throw on a pair of stockings, maybe panties or something but that was about all we could do. He was my girlfriend until I got an actual girlfriend. His mom told me that his sister wanted me to take her out. I was not 16 and driving she was 15 and the mom said she could date, but she only wanted to date me. After several dates, and still fucking her brother, the mom told me that she knew that the sis and I would be having sex soon. She cautioned me to get gentle to her, and not use her to get off then leave. She gave me her first hand job, I rubbed her to orgasm for her first time, I ate her pussy, she blew my cock, then I popped her virgin pussy. It was in her bed, her mom knowing we were staying in the sisters room. Stacy saw me through to keyhole we left open as I broke his sisters hymen. It was a year before I got her to let me buttfuck her. During that time, she saw me and her brother, and he said that if I did it it wouldn’t hurt.
When I left for college that all stayed at home. It was a shame, I had two mouths, two butts and a pussy at my disposal. I never got them both at the same time, but wish I would have. I think I should have invited them both to visit me at college. Maybe then we could have had a threesome.
In the years that followed, she got knocked up twice by two different guys, he started living as a woman. The mom told me she wished I’d have been the one to knock up the daughter, and she let it be known she knew about me and her son fucking too.
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