Comforting My Little Sister

I set the pillow in my arms behind me. I said softly, "Michelle."

"Yes."

"I want to hold someone. Could you scooch over this way a little bit?"

"Sure."

She moved over until she was resting her head on a pillow in the crook of my right elbow. She was lying on her stomach and facing away from me. I put my left hand on the small of her back. I lay there for a little bit and then had second thoughts. It was one thing to share a bed with my sister while we were clothed. It was another thing to actually sleep with her. I removed my hand and said, "You can move back."

Michelle said, "No." She reached out and grabbed my hand while continuing to lie on her stomach and face away from me. "Keep your hand where it was."

"Michelle...We shouldn't."

"It's late and we need to go to sleep. You comforted me when I needed it. It's time for me to comfort you when you need it. It's important to me that I do so. So put your hand back where it was."

"All right." I didn't feel like arguing with her. She sounded determined that we sleep this way.

I put my hand once again on the small of her back. Michelle wiggled a little bit to get it exactly where she wanted it. It was comforting to feel her so close to me. To be touching someone I knew cared for me. I soon fell asleep.

* * * *

When we woke up the next morning, Michelle said to me after she did her usual stretch, "I liked sleeping like that."

I still felt torn about it. I had enjoyed it but felt it wasn't right. I wanted to talk to Michelle about why it was so important to her that she comfort me, but we had to get downstairs for breakfast before Mom and Dad decided to find out what was taking us so long.

Last day of classes. I thought at one point about trying to get the phone number of a few people I had chatted with occasionally during the semester but decided to give it up. I'd spend the summer working and hanging with Michelle.

I didn't go to Gina's work after closing up. I went home feeling deflated. Mom, Dad, Michelle, and I watched a movie. It had been a while since we had done that. When it was over, Michelle and I headed up the stairs. When Michelle came into my bedroom, she stopped before getting on the bed and said, "Let me be in charge tonight, okay?"

I was surprised, but said, "Okay."

"Do you think you can sleep on your other side?"

"I guess. I can try."

"Great. I want to be on your left side tonight."

I moved to the other side of the bed to give Michelle room. She lay down on the covers as always. I asked, "So why the change?"

"I'll tell you later. For now, I just want backstrokes."

"Okay."

I was curious but decided to go along. Was this a good sign or a bad sign? Was Michelle unhappy with how we slept together so she was changing it up? Or was this a sign that she felt comfortable enough with our relationship to make a few changes?

Michelle was on my left side now and I had to reach across my body to stroke her back. I wound up lying on my side with some pillows underneath me to comfortably reach her back. We didn't say anything as I stroked her back. After five minutes, Michelle got up to get under the covers.

"No Great Ass check?" I asked.

"Not yet. Push down your pillows."

I pushed most of my pillows off the bed. Michelle positioned one for me to put my head on. When I put my head on it, I stuck out my left arm. She put her pillow in the crook of my left arm and said, "Now it's time for the Great Ass check."

I reached down with my right hand and put it on Michelle's ass. Normally, I felt it through her nightshirt but she had her nightshirt pulled up so I was feeling her ass through her panties. She pressed her ass into my hand and said, "You don't know how much this means to me." I moved my hand up and down as she wiggled her ass into it. "Jared spent a year destroying my self-esteem. It'll take a long time coming back."

"Still a great ass," I said as I removed my hand.

"No. Don't stop. Keep going. I wasn't done yet."

I was shocked by this. I had always kept the time I felt Michelle's ass to a minimum. I knew as her brother, I shouldn't be touching it at all. Now, she wanted me to touch it for who knows how long.

Michelle said, "It's important to me. I'll explain in a little bit. Please put it back and keep checking."

"Okay. If you want."

I slowly replaced my hand on her ass. She gave her ass a little wiggle to get me to move my hand. Soon I was running my hand over it. Her ass felt so smooth. I could feel it a lot better through only her panties.

Michelle said, "When I first broke up with Jared, I felt so ugly. Scrawny, flat-chested and plain. You said I was pretty and had a nice ass. I didn't believe you. You tried to use logic to convince me I was attractive, but Jared had convinced me I wasn't."

I continued moving my hand, giving her ass an occasional squeeze. It was firm and the right size for my hand to cup.

Michelle continued, "The next day, I went braless. And your eyes lit up when you realized I wasn't wearing a bra. Was it because you thought my bare tits were sexy? Or was it you were embarrassed to be seen with me without a bra on? I thought it was because you thought my bare tits were sexy, but I wasn't sure."

Michelle continued wiggling her ass into my hand, apparently wanting me to continue to grope her. I didn't know what to think of what we were doing now, but I was enjoying it. My cock was hard in an uncomfortable position. I brought my hand up and straightened my cock. When I did, Michelle stopped talking. When I resumed rubbing my hand over her ass, she resumed talking.

"And then you did the Great Ass check. You acted like you were just being silly, but I could tell you liked feeling my ass. My own brother enjoyed feeling my ass. I thought 'I really must have a great ass'. That was when I took your words seriously. That was when I started believing you liked seeing me braless even though my tits are small. I even began suspecting that I might be pretty."

Michelle was pressing her ass into my hand and shaking it harder than ever. I was rock hard now. I was panting. Michelle had me very turned on.

"That's why I asked for Great Ass checks." Michelle was panting lightly as she talked. "To remind me that you find me attractive. To build a positive body image." Michelle stopped wiggling her ass. "I think that was a long enough of a check tonight." She reached back, grabbed my hand, and put it in the small of her back. Michelle panted lightly for a few moments and then said, "To rebuild my self-esteem, I need to feel sexy; that I have a nice body. And you're the only guy I feel comfortable being sexy around. I'm afraid other guys will take it the wrong way. So you're very important to me right now. That's why I was so glad to snuggle with you last night. It helped my self-esteem to be able to comfort someone so important to me."

"Michelle..." She made it seem so reasonable. I was glad that I was so important to her. I did want to continue to build her self-esteem and positive body image. And I enjoyed doing it. I loved the feel of her ass in my hand. It felt good sleeping with her close by. But...

Michelle said, "I think it's okay as long as I face away from you. If I'm facing away from you, you're comforting me or I'm comforting you. If I faced you, then we'd be doing something besides comforting, something we shouldn't be doing."

It seemed like a mighty fine distinction. But why not? We both had clothes on. It was obviously consensual. We both enjoyed it. With a brother and a sister, there was always a line that you shouldn't cross. Michelle had decided to draw it in a different place. What we were doing may be tough to explain if Mom or Dad caught us, but it was basically harmless.

"Okay." I added, "I can't run my fingers through your hair this way."

"That's okay. I like this a lot more. I like knowing you're close. I feel safe with you."

That made me feel warm all over. I said, "Good night."

"Good night."

* * * *

The next morning was Saturday. After breakfast, I spread my notes, past tests, and such all over the dining room table and started studying for my first final. It was hard to study as I spent a lot of time thinking about what Michelle had said last night. She apparently wanted us to sleep together every night. I had slept with Gina once. Long ago, my parents had laid down the rule that if I wanted to live at their house, I had to spend every night at their house. I had used the "too drunk to drive" excuse to sleep over at Gina's that one time. Dad had been so pissed off about my underage drinking that I had never used it again. Gina and I had slept in a much different position then. And we had slept naked. I had been sleeping with Michelle for over a month now. Was the new position with Michelle that different from what we had been doing before? And we still had our clothes on.

But what was very different was that Michelle apparently wanted me to feel her ass every night. To rub my hand over it until one of us couldn't take it anymore. She did have a great ass. I enjoyed feeling it much more than I had enjoyed feeling Gina's. It had the right size, the right firmness, and the right curves. I was rock hard again thinking about it. In a little while, I planned on going upstairs and jacking off. I knew that I'd blow a big load.

Why did Michelle want me to feel her up? One obvious reason was that she enjoyed it; that my rubbing and squeezing her ass gave her a lot of pleasure. It gave me a lot of pleasure. But I decided the bigger reason was that she wanted me to make her feel sexy. She had said last night that to rebuild her self-esteem she needed to feel sexy and that I was the only guy she trusted being sexy around. I could see that. She wasn't going to get involved with another guy any time soon. Once bitten, twice shy. I would be the only one to see her sexy side in the near future.

And what did I think of all this? Part of me was "Yahoo! I get to feel up a great ass every night! Get so worked up that I blow a huge load the next day! Hallelujah!" Part of me was "This is so wrong. So very, very wrong. I shouldn't be touching my sister like this. The fact that she wants me to doesn't change that it's wrong. If anyone finds out, I'll be in such deep shit." The part of me that won out was "This is just a phase Michelle is going through. She wants me to tell her that she's sexy and I wasn't doing that when I was giving her a quick check. As her self-esteem grows, she'll move past this." I swore to myself that the next time I rubbed her ass, I'd do everything I could to convince her that she was sexy. Hot as hell. Had a nice body that any guy would love to touch. Jared had spent a year tearing her down. I'd spend the summer building her back up.

* * * *

Later that day, I got a big shock at work. I was reorganizing a section and looked up to see Jared walking into the store. I was strongly tempted to yell, "Hey, asshole! Get out of my store!" But if that got back to my manager, I could be fired for it. Instead, I watched him as he walked around. I hoped he do something stupid like shoplift so I could call the cops on him. Had he come to see me? Had he come shopping and didn't realize I'd be here?

Jared was looking down at the few items he was carrying when he entered my aisle. Then he looked up and saw me. "Hey, Chris."

"Hey, Jared." I had so badly wanted to say, "Hey, asshole." Not a good example to set for my co-workers.

Jared asked, "How's Michelle doing?" He had asked that a little eagerly, like he badly wanted news about her.

I said nonchalantly, "Doing well. Getting ready for finals and graduation."A hell of a lot better now that you aren't in her life.

"Has she found a new guy yet?"

"No. She's not looking. She's focused on school right now."

"I've found another woman. Terry has a nice body. Big tits. Great in bed."

What an asshole. "Good for you," I said blandly. I hope she whacks you over the head with a frying pan.

"How much does Michelle miss me?"

"Miss you?" Time for some revenge on the asshole. "She doesn't miss you at all. I can't think of the last time she mentioned you."

That pissed him off.

Jared said with some heat, "Yeah, well breaking up with the scrawny ass bitch was the best thing that's happened to me."

I tried to sound bored as I said, "Best thing that's happened to her, too."

That pissed him off even more.

Jared said, "She does have a scrawny body. I've got proof." I shrugged my shoulders and went back to work. "She's got no tits and a bony ass."

I realized the folly of pissing Jared off. He had to win the argument. Now he was going to run Michelle down to push himself up. "She's my sister. I think she's really neat."

"You think she's neat? You should see some of the pictures I have of her. She's a total slut. She'd do anything for me. Anything."

I had enough of Jared. "I need to finish this up. The cashier will ring you up." I turned my back to Jared.

I heard him leave. I was glad I scored a few points for Michelle. I hoped he wouldn't do anything stupid because I had pissed him off.

* * * *

When I got home, I had a bad case of nerves. Had I misunderstood Michelle last night? Would she change her mind? Or would I once again get to run my hand over and over her wonderful ass?

Mom and Dad wanted to talk for some reason and we spent an hour discussing my upcoming finals and my plans beyond that. Dad wanted me to paint some rooms. Last free slave labor before I moved off to college. Michelle was upstairs already. I kept thinking about what was going to happen when I went to bed.

Finally, my parents had their say, and I went upstairs. I quickly got ready for bed. When I came back into my bedroom from the bathroom, Michelle was waiting on my bed. She smiled at me. I decided to not tell her about seeing Jared. I didn't want to spoil the mood.

We did backstrokes like we had done the night before. Michelle got under the covers and lay down on my arm. My hand went immediately to her panty-covered ass.

"You have such a great ass, Michelle."

Michelle made a sound that was like a cross between a moan and a purr.

"And you have nice legs too. May I touch your legs?"

Michelle was silent for a moment and then said, "Yes."

I ran my hand down her leg from her ass to above her knee. "Such smooth skin. You have nice skin. And very firm legs. Do you walk a lot at work?"

Michelle was slow to respond. Instead, she pushed her leg into my hand as I ran it slowly up and down. Finally, she said, "Yes."

I brought my hand back up to her panties. "But I like your ass the best." I softly moved my hand in a big circle over her ass. "What are the panties made of? Cotton?"

Michelle wiggled her ass within my hand for a little bit then said, "Yes."

"I like the feel of the material."

Michelle buried her face in the pillow and pushed her ass up. I continued to explore every curve of her ass. Was she moaning into her pillow?

Michelle turned her head and asked, "You don't think they're too practical?"

"They're practical for my rubbing your ass. But do you have any sexier panties?"

"Yes."

"Wear one of them tomorrow night. I'll tell you how I like them compared to these."

Michelle buried her head into the pillow again. I noticed she was gripping the pillow tightly with both hands. My rubbing her ass was obviously exciting her. It was exciting me - my hard dick was straining against my running shorts. I wondered how long she'd let me keep touching her like this.

I asked, "Can I put my hand under your shirt?"

Michelle nodded her head up and down.

I slipped my hand under her nightshirt and moved it slowly upward. "Nice, smooth skin. I like your back. It's the perfect size and shape for your body type." I was silent for a while as I explored.

Michelle turned her head to the side and said, "I like this. It's very soothing."

"Good." I continued working slowly upwards. Michelle continued facing away from me. My stroking her back wasn't as exciting for her as my stroking her ass. Same for me. But it was a nice interlude. I reached up to her shoulder blades, went back and forth a few times, and eventually slowly worked my way down again.

When I slipped my hand out of her nightshirt, I said, "I'm going to stroke your ass just a little bit more and then it'll be time for sleep. Okay?"

"Okay."

Michelle buried her face in the pillow again as I worked her ass. She vigorously rocked it from side to side so I barely had to move my hand to reach all of her ass. I tried to stay away from the area close to her pussy but sometimes I brushed there as she moved her ass around.

I got to the point where I had to stop or I'd do something more than Michelle had given me permission to do. I gave her bottom a slight swat and said, "Time for sleep."

We shifted into our sleep positions with my hand on the small of Michelle's back. She said, "That was really good. You made me feel very sexy. Thanks."

"You are very sexy. And you're welcome."

* * * *

Sunday morning was my time to sleep in. Mom and Dad didn't care when I came down on Sundays. I felt Michelle wake up and get out of bed, but I continued lying in bed. I listened intently and heard her going down the stairs a few minutes later. Time to jack off.

I got out of bed and went over to my computer. I got naked and sat down in my chair. I opened my desk drawer and pulled out my bottle of lotion. I took a tissue out of the box I kept on my desk. I had an email, and I decided to see what it was before hitting the porn sites.

To my surprise, the email was from Jared. I remembered sending him a birthday e-card back when I thought he was a nice guy. The title of the email was "Check out your slut sister". I opened the email and it had two lines - the first was a link to a "Michelle" folder on a cloud drive and the second said, "Password Bony_Ass". I clicked on the link and entered the password Jared sent me. The folder was 74 pictures. The first one was "Aaaah 01". I clicked on it. It was a picture of Michelle's face covered with cum. A cock was touching her lips. Michelle had a big smile on her face.

I closed the picture and opened the next, which was "Anal 01". I opened that. It was a picture of what I took was Michelle's ass with cock buried in her asshole. There were eight more "Anal" pictures. I scrolled down. There were a dozen "Blow job" pictures. Four "Cum on tits" pictures. I opened one. Michelle was lying on a couch smiling with cum all over her tits. Thirteen "Doggie style" pictures. I opened one. Michelle was on a bed with her head down low and her ass in the air. She was looking back at the camera. She appeared to be panting. Her face was full of lust.

Michelle had said that Jared had some pictures of her naked. Now I knew he had 74 pictures of her having sex. I tried deleting them. I had read-only access to the directory. I created a new folder on my computer and started downloading them. That way if Jared ended my access to the cloud drive, I could still show Michelle the pictures he had of her.

Jared had sent me the link to convince me Michelle was a slut. That had failed. Michelle wasn't a slut. She had been a good girlfriend - make that a great girlfriend - who had badly wanted to make Jared happy. Jared had been right when he said she had been willing to do anything for him. And he hadn't appreciated how good he had had it.

By this time, I had downloaded through the "Doggie style" pictures. I opened the first one. Doggie-style was my favorite position to fuck in. Gina hadn't cared for it. She wanted to fuck in missionary all the time and I had to practically beg her to do any other position. Michelle looked so sexy in the picture. Without thinking, my right hand began stroking my cock. I clicked the arrow to see the next picture. Michelle was bent over the arm of a couch while getting fucked. I had never fucked Gina anywhere besides on the bed. I clicked the arrow to see the next picture. Michelle was getting fucked while lying on a picnic table in what looked like a park with her legs on the bench. Without thinking, I put some lotion on my hand and continued stroking. I looked at four more pictures before blowing a huge load.