Caroline Finds Out

If you are a man, you understand the feeling that I soon expected myself to have.

I was alone in a hotel room and I was at the same time confused and aroused. I started to piece together what I thought I knew. I saw her toys, so I knew that at a minimum she was a very sexual woman. I saw her note, so I knew that she knew I used her panties to masturbate but I didn't allow myself to determine whether she knew I wore them or anything of hers for that matter. I knew she had something in mind because she deliberately took a pair of my underwear, but what that was I wasn't sure. That's all I knew. Anything else I would just be making up. And that was what intrigued me.

I was alone in a hotel room and I got ready for bed. I lay there thinking about what I didn't know. I started to picture her boyfriends, her ex-husband - the men in her life I never knew, and I wondered about the things she did with them. I started to picture them doing the things men like to do with women when they're intimate. I pictured them hard for her, admiring her body, kissing her, their cocks in her mouth, her pussy, her ass. I thought about the things she may have tried and never shared with anyone. I was hard, and my thoughts kept bouncing to different scenes and guys and began to realize something, maybe more acknowledge something that I think any of us with siblings realize, that our brother or our sister is probably in a lot of ways like any of the men or women in our lives and she probably enjoys many of the things I've done with the women in my life.

That night was the first time I thought of being with her. As my thoughts drifted to fantasy, I was suddenly overcome with this curiosity - a very specific curiosity - that I would not be able to shake. I wondered if my sister swallowed. Just like that. And no longer was I thinking about boyfriends or her ex-husband, I was thinking about me. I was thinking about my sister's mouth on my cock, in bed, giving me head and I wondered if when I came she would pull her mouth off of me and masturbate me through my orgasm and make me cum on my chest and tummy. . .or if she would hear me tell her I was about to cum and let me finish in her mouth and swallow. That's when I came. There was no answer.

The feeling I expected to have was one that I have experienced before. There have been times when I have been on tumblr chasing images and finding myself deeper down the rabbit hole than I imagined I would go and felt a bit of shame or guilt at the thought that made me cum. There have been times where my play has involved toys or acts that lead very much to that same feeling. I would clean up right after and do my best to put what just happened out of my head. Not this time. Laying there in that bed, that night, I felt no guilt, no shame, making myself cum thinking about my sister's mouth on my cock. In fact it felt a bit, well, right.

As I drifted to sleep, those men were replaced by thoughts of me. Off and on through the night I would allow myself to think of her in ways I'd never thought of before. I awoke the next morning less nervous about what had happened. It was as if a night away, and the travel and the anonymity of being in a hotel had put more distance behind this whole thing than may actually be true. I believed that maybe because I had these thoughts, these feelings, that maybe she did too. I got butterflies when that thought came to my head. The thought of my sister in bed touching herself thinking about me had me hard again. And for the second time in less than eight hours, I'd cum thinking about her again.

I sent a text to let her know I'd made it safely to Vancouver and thanking her for letting me stay over. I got in the shower. I checked my phone and there was no reply. I dressed and went to the conference. I checked from time-to-time hoping for something, but she didn't reply. I ate alone that night and went back to my room, exhausted as much from the day as the thoughts that kept my mind more active than it needed to be; about why she wasn't texting, about the feelings I was having, about whether she enjoyed being fucked in the ass. My thoughts were never empathetic. They were never about her not texting because she was offended that I masturbated with her panties or she suddenly realized I had a crush on her. It was always something else. She was out with friends. Her battery was low.

I went to bed that night and thought about her. I thought about my sister Caroline in bed with me, on her hands and knees while I took her from behind. I thought about what she sounded like when she came, and wanted to make that happen. I didn't think about what got us to that point. In some ways over the past day and a half I already felt in some ways like we were together. That we'd always been intimate in some ways with all that we'd been through and the times we'd been there for each other. Of course we were in bed together like that. It was only natural.

I let these thoughts take over even more strongly when I woke up the next morning to a message from her.

"Glad you made it safely. Let me know if you need to stay over on your way back."

I suddenly needed to stay over on my way back.