Learning Curves

As I slipped a second finger into my sister’s asshole, I could hardly believe we were doing this, much less that she seemed to be enjoying it as much as I was. It started with Jess acting weird. When I asked her what was wrong, she told me her boyfriend wanted to have anal sex, but that she was too afraid. I told her that I’d tried it before and how it could be good if you know how to do it right. This got her even more freaked out and she begged me to tell her what exactly that meant. I explained the mistakes I’d made and what I’d do differently if I had it to do over. She had a million questions and only got more stressed when I couldn’t give her the exact details in a way she could understand. Finally, out of frustration, I blurted, “Do you just want me to show you?” I didn’t really mean it, but when she said yes, it turned me on in a way I hadn’t expected.

Me and Jess shared a room ever since we were little. We were naked in front of each other all the time and it was no big deal. When I started sprouting hair down there and my boobs began to come in, Jess was very curious and I’d let her inspect the changes my body was going through. Only a year later, I was inspecting her development, and we often compared ourselves without any reservation. Not long after that, my little sister heard me masturbating in the dark when I thought she was asleep. She asked me what I was doing and I showed her the wonderful new trick that I’d discovered. After that it wasn’t unusual for us to masturbate around each other, and we often did it together either side-by-side or face-to-face. Sometimes we would cuddle together in bed at night when it was cold or during a scary storm. Usually we just hugged and snuggled, but sometimes I would tickle her nipples or she would rub my butt. That was about as sexual as we ever got together.

Before I had a chance to tell my sister I wasn’t serious about my offer, Jess had her pants and panties off before I knew it and was lying on my bed with her butt in the air. It seemed weird, but also perfectly natural. I spread her butt cheeks and spit on her perfect little virgin asshole. She squealed in fear as I gently worked a finger into her. She was so tight! I couldn’t imagine a cock fitting in there. I slowly worked my sister’s hole while she moaned. I was surprised when she asked for me to stick another finger in there. I could tell this hurt her a little, but she made me keep going. My surprise turned to shock when she began masturbating while if fingered her ass. Watching each other was one thing, but this was something else.

It felt so cool when Jess made herself cum and I could feel her ring of muscles tighten and spasm around my fingers. She said it was one of the best orgasms she’d ever had. She was all giddy and silly after that and said she wanted to do it to me. I said no way, but she wrestled me down onto the bed and after a couple minutes of screaming, struggling, and hair pulling she managed to rip my panties down and get a finger shoved into my asshole. I gave in at that point and let myself enjoy the sensation of my little sister butt fucking me. I wasn’t able to resist playing with my pussy like she had, and soon I was having my own mind-blowing orgasm.

After lying around like a couple of limp noodles and talking more about the ins and outs of anal sex, we got in the shower together. Once we were all lathered up, it was inevitable that we’d end up in a naked hug, each of us reaching around behind the other and inserting a soapy finger so we could enjoy the new trick we’d discovered together. We rubbed our slippery tits and sudsy mounds together as we violated one another’s backside holes. I had three more orgasms during that shower, and my sister had at least that many. I was pretty sure we’d be cuddling together in the same bed later that night, but not because it was cold or there being a scary storm. I couldn’t wait to find out what we discovered next!

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12 thoughts on “Learning Curves

  1. Nice little quickie! I also really like your new “I made my pussy cum to this” features. Its fun jacking to what you’re jilling to.

  2. Rachel, great short story and the perfect pic. I did wonder if this was a fantasy involving you or one you have for a younger generation.

  3. Fun little story. Would like to see a followup where they’re caught stealing a dildo from their parents’ bedroom by Mommy and forced to explain what they were going to use it for, which would end up with Mommy training both of their assholes properly.

  4. A great little story Rach, has me all sudsy and teasing my little brown hole. Was extra special for me given one of my daughters names is Jessie :-)

  5. Great little story. I agree with Saul, would make for a great follow up story with Mom catching them and after some conversation and consoling, joining them. Makes me think of my daughters playing and me walking in on them………………….what would I do? And the pic you chose is so perfect, so Hot! How I love your dirty mind!

  6. First off I’m a huge fan of your stories! I loved this one so much and my biggest fantasy is sisters, mom’s, aunts that enjoy anal and know how to make it pleasurable. Incest and anal is a double taboo in one. There are so few anal incest videos so stories really are my outlet. I would love to see more stories of women who love it and not always first time trying it out so they can get wild. Also a sister and mom that teach a son how to do it (with perhaps them using a strap on him) so he can fill their taboo needs without getting pregnant and because dad (boyfriends are Vanilla when it comes to sex. I would love to hear and talk more and I really enjoy incest captioning photos…. especially with my above mentioned sex act. Feel free to email me any thoughts, thanks, photos, advice, and ideas. Hugs and thank you for being the naughty mommy to us all.

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