Little sister the wingman

My half sister is 6 years younger than I am. This story was when I was 17. Her and I never did anything sexual besides talking about sex acts or seeing each other naked. My parents tried hiding the truth but she was old enough to know. I assume she told some of the things I told her to her friends. She had a few close ones that slept over a lot, especially on the weekends. I was almost asleep one night. Long day of school and had a game. My sister tapped my shoulder and I mumbled for her to leave me alone. She whispered that her friend Grace wanted to try sucking my dick. That jolted me awake. She told me Grace was horny because they were talking about sex and wanted to try sucking and try cum. I said I guess that was fine. My sister left to get her. Not that you could see much in my dark room but Grace was cute. She was a little chubby but in a cute way with black curls and nice lips. She came in with my sister and got into bed with me. My sister sat near the door, I assume to listen for the parents. Grace was cute and shy with me. I never looked at her in that way but she was quickly changing my mind. She was so enthusiastic and gasped or moaned even if I kissed her forehead lol. I got her naked and I was down to my boxers. My hands and lips explored her whole body. I got my mini flashlight out of the drawer and went under the covers. Her pussy was better than any I’ve seen. Naturally soft, barely any hair, wet and tight. I had never seen a hymen up close like that. I was throbbing when I first tasted her. She was grabbing my head and covering her mouth before I was really doing anything. I just wanted a taste but was down there for a few minutes. I took my boxers off and said I was ready. She did okay with my guidance. I was teased bad enough where I wasn’t going to last long. I went under the covers with my light. My sister looked under the covers to watch. I didn’t say anything to her. Grace was so cute with her big lips sucking my dick. I wanted to see her reaction when I came. Surprisingly, she sucked, she swallowed and she moaned. Not a drop went to waste. She spent the next night swallowing my cum too.

My sister really did become a good wingman over the years, especially in the beginning. It’s like she had a new friend over all the time for me or something. I think she secretly liked it. Watching us, hearing her friends please her brother. Two in particular were my favorites, Laura and Amber. Laura was like a mature woman in a girls body. She was flirty, dirty and had multiple orgasms. She was the first of her friends that I made cum and it was stupid easy. She got into my bed and I spooned her with my hand up her shirt. She had nice handfuls, more than some my age. When I rubbed her pussy, I played with one of her nipples and she had this intense orgasm where she was shaking. She had another. Then two more when I went down on her. After she sucked my dick I had her grind on my dick before I came. She came again while on top of me. When she started shaking, I came all over myself. Amber was a great one. She was in gymnastics and had a body on her. This ass was so big and toned, I wanted her for a while. My sister came in to ask and I was still awake, of course I said yes. She said she was okay to suck my dick but didn’t want cum in her mouth. Right there I was thinking she was going to be boring. Hell no, she was all over me kissing, got naked right away, yanked my dick out jacking it off. She was another one who had an orgasm when I went down on her. She started sucking me slow but out of nowhere was gagging on my dick. I assumed this wasn’t her first blowjob. I tried getting her to go all the way down but she couldn’t do it. She didn’t disappoint when she put my hand on her head. I jammed my whole dick down her throat. She came up to breathe and had drool from my dick to my mouth and it was so hot. When she spooned with me again, she asked where I wanted to cum. She was rubbing her ass on my dick and I got an idea. I had her face down, ass up. I ate her ass and pussy good covering them with so much spit. I got back on my side and my dick between her ass cheeks and pointed to her pussy. It was so warm and slippery. She moved her ass on it and I pretended I was fucking her. When I came, it got everywhere. Sheets, her, me. What a wonderful mess.

I’m sure someone is wondering if I actually had sex with any of them. As we got older I did with a few. During that time, I took two virginities. Grace and Amber. Grace and I had hooked up a few times. My sister came in as usual asking for Grace to come in. She said she was really horny today. We did our usual routine. This time I wanted her to grind the cum out of my dick. It must’ve got her extra horny. She whispered to me to put it in. I told her no but got on top. My dick was sliding between her slit and she was moving all over not like usual. She reached down to try putting it in her but it wasn’t far enough down. I wanted it too so I asked if she was sure and then took her virginity. For me being ready to cum, it wasn’t long but I think that was good for her. She just wanted to experience it. Amber was a bit different. We really went at it. We could touch and make out for hours. I loved her ass so much, I could keep my dick between her cheeks for the whole time and be satisfied. She was much more wet than usual and we were hornier than usual. I spit on my dick and rubbed her holes. She pushed her ass back and I felt a tight grip on my dick. I asked if she was sure. She wanted it bad so I began to push just past the tip. She said it hurt too much and I was in her ass. I laughed so hard at the fact that she didn’t know the difference. It was cute. Put it in its proper place and it was much better. I lasted long enough for her to enjoy it at least. She turned around for me. I wanted to see her perfect ass on my dick. She spread so I could see my dick pulsate inside her when I came a bunch of sticky cum In Her.

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