Giving My Little Sister a Massage

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The following story has extreme sexual content. All the characters depicted are at least 18 years old.

Message to the reader, as of Feb 2012 there has been some re-working of this story, I edited it a little and re-posted it here. This version is a little bit shorter.

A reader contacted me and asked if he could play editor and trim the story down a little. I happily agreed, and he later sent me the story you see posted below. This versions is pretty much the same, just edited down some. I need to say thank you to this mystery person, you know who you are.

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I was all alone in my room and I could hear my little sister and I could tell she was on the phone, I could hear her through the wall. She was in her room, right next to mine. I lying on my bed, listened to her voice - all hushed and muffled.

My sister's name is Crissy, and she can get really emotional. As her big brother, I'm careful about Crissy's privacy. It was impossible to hear much, so I wasn't able to listen closely, but I could tell that it was something serious. I didn't know what she was saying, but she had been talking on the phone for a long time. And it was getting pretty late. My guess was that she was probably talking to her friend Elizabeth, they talk together all the time.

My sister and I were all alone in the house. Mom and Dad were away for two weeks, and they trusted us to take care of ourselves. Both of us are really good kids, we don't have any desire for a party or staying out late. She's a little bookish and quiet compared to some of the other girls at school.

Crissy is just a little over a year younger than I am, and she's even though she's 18 years old, she's still in that awkward teenager phase. I feel like I know her really well, and sometimes she can get so nervous, and I try to be kind in a way that is supportive. We are really close and it's really nice, I really love her and I know she loves me.

It's funny, we are a lot the same. We are both just so emotional about stuff. Crissy is emotional about herself, she is insecure and vulnerable. And I'm emotional about wanting to help others, I sympathize in a way that can overwhelm me, I'm really concerned about others and their feelings.

Next month I'll finally be leaving the house and going away to college. This is after a whole year of taking classes and getting credits from the local community college right here in town. So these next few weeks are probably the last time we'll ever live in the house together. Moving away and being apart from her is something that makes me feel really sad.

Suddenly, I couldn't hear anything through the wall, the phone call must have ended. It was quiet for a few minutes. Then I heard my sister - and it sounded a little like she was crying, but I wasn't sure. I stayed still on my bed and listened. As her older brother, I feel so concerned for her. Then, I heard a muffled sob and realized my beautiful little sister was crying about something. Without any hesitation, I got up and quickly walked out of my room and into the hall.

I knocked on Crissy's door, and I heard her say, "Go away."

I said, "Crissy, it's me Michael, I'm your brother - and I'm not going to go away. I'm going to come in - please, let me help."

Then I opened her door. She was on her bed, lying on her stomach, sobbing into her pillow. She had on her normal sleeping outfit, a big oversized t-shirt and a pair of boy's cotton boxer shorts. I always thought that simple outfit made her look amazingly cute, especially the way her butt looked in those little shorts.

She looked up at me with tears in her eyes, and said, "Oh Michael..."

Everybody calls me Mike, but Crissy called me Michael, and right then, she sounded emotional and sad.

I sat on the edge of bed right next to her and said, "Oh Baby, what's wrong?"

Crissy cried for a little bit and finally whispered, "I feel so awful."

I gently rubbed her back as she cried. Even though my sister is sort of tiny, her back is strong and wide from all her years on the swim team.

My little sister has straight red hair, and she always keeps it pulled back in a pony tail. She has these adorable freckles that I just love. She has big eyes and incredibly pale skin. All of this makes her look younger than she is, and I've always thought she was really cute. And her shy personality adds to her uniqueness in such a sweet way.

I encouraged her, "C'mon Crissy, it's okay. You can tell me."

"It was Elizabeth, she - she..."

I asked, "Were you on the phone with Elizabeth just now?"

"Yeah..."

"What happened, what did she say to you?"

"She was - I don't know - she said stuff that made me feel so - scared."

I could hear it in her voice, my vulnerable little sister was really upset. I want to comfort her, so climbed all the way on the bed, and sat next to her.

I asked, "I know you two are such close friends. What did she say?"

"I don't understand why I'm crying like this."

I could see how scared she was, so I moved closer and I put my arm around her.

I told her, "It's okay, don't worry."

She responded by immediately squirming toward me me and snuggling in close.

Crissy said, "This afternoon, after swim practice, Elizabeth and I were in the locker room showering. And she was acting really excited, and she told me she was going to call me tonight, she needed to tell me something."

Elizabeth and Crissy have been friends since they were little kids, and they've both swam on the school team together since they were freshmen. Elizabeth is sort of cute and perky and that's really different from my sister, who can be so serious.

My little sister went on, "When she called just now, she talked about her boyfriend, and what she's been doing with him..."

I kissed the top of her forehead and whispered, "It's okay, you can tell me..."

And then Crissy went on to explain what Elizabeth had told her, "She and her boyfriend are getting pretty serious, and - well, during the phone call, she explained everything that they did last night, and she was really explicit. She just went on and on and on..."

My little sister can get so emotional about simple things. I was surprised at how much it seemed to upset her. She is so sensitive and vulnerable, and I'm just so worried about her.

I asked if she was troubled hearing Elizabeth talk about intimate things.

She nervously replied, "No - Maybe - I'm not sure, maybe I am upset about the sex thing. I mean, it just seems SO scary to me. I'm just really worried about getting pregnant."

And then she went on. I sat and listened to my little sister, and I stroked her hair as she talked. She explained how frustrated she was with Elizabeth and how explicit she had been on the phone.

I whispered, "It's all okay."

Crissy looked at me with her big sad eyes and said, "You know I've never had a boyfriend - and I don't know if I ever will!"

"Oh c'mon, you're smart and pretty, any boy in the world would be lucky to be with you."

"But..."

And I interrupted, "Crissy, you're wonderful - don't worry."

She replied nervously, "But Elizabeth has such a cute little body, and - and - and such a - well - such a tiny little bottom..."

I smiled and said, "Listen, you have a beautiful body. I've seen you in your swim suit so I know."

Then Crissy sat up, looked me straight in the eye and nervously asked, "But - I mean, what about my big bottom?"

"Oh Crissy, Shhhhhh... Your bottom is NOT big."

She seemed so sad as she asked, "But Michael, why am I so ashamed about my - my bottom?"

It made me feel so heartbroken to hear my sister so upset about her body, she is just so beautiful, and for some reason she just doesn't let herself believe what's true - that she is pretty, and her butt isn't big, it's seems perfect.

"Please, don't even think that, you have a perfectly beautiful bottom."

"I worry about it, a lot. I can't help it..."

She seemed so sad and I needed to compliment her, so I whispered, "Do you have any idea how cute you look from behind in your bathing suit? Your bottom is so cute, especially when it's wet!"

She nervously said, "But I'm worried. I mean, Elizabeth has such a tiny little bottom, and I'm really jealous - It's so awful how much I worry about it - I'm just so mixed up - and I don't have anyone to talk to."

"You can always talk with me."

She paused and looked away, she seemed so unhappy, and I felt powerless to help.

After a moment, she spoke, "I don't know why I cried after talking with Elizabeth. It's been so hard. I mean - I really like her, she's a great friend, and she really tries to comfort me."

"Go on, I want to help."

Crissy spoke in a shaky voice, "What really upset me - well, I guess it got me all freaked-out was - that..." And she just trailed off.

I could tell this was something really serious, and I softly said, "Please don't worry, your my little sister, and you know how much I love you."

Crissy replied with a shaky voice, "I know - and I love you too, I really do. But I just feel funny, I'm scared, and I feel like I really need to talk about it."

"I want to help - please tell me."

"Can you keep this a secret?"

"Of course, I won't tell anyone."

"Just now, on the phone, Elizabeth told me - well - exactly what she did last night."

"Go on..."

"She really loves her boy friend. And she said she really wants to - well - to make love - but she is really scared about getting pregnant - do you understand?"

"Yes, I think so."

"And, well - she convinced him that they should - well - the way she told it, she sort of begged him..."

She paused and looked at me, and I could tell she was scared.

I whispered, "It's okay, you can tell me."

And Crissy spoke in a really embarrassed tone, "Oh God, she and her boyfriend - they actually did it together, and instead of - well - the regular way, she asked him to..."

"Go on..."

And after a long pause, my sister nervously whispered, "She asked him to put his - his penis inside her - her anus."

Oh my God, Hearing this really surprised me, and I tried to make sense of what my sister had just said. Her friend Elizabeth was having anal sex? That seemed shocking.

I cautiously asked, "Did she like it?"

My sister eagerly replied, "Oh my God - she LOVED it, she went on and on and on about how good it felt."

I was overwhelmed and I asked, "Really? She did?"

Crissy sounded excited as she spoke, "She told me that she - was excited - because she could let her boyfriend - actually - cum inside her - and she didn't have to worry."

I asked, "Did it - well - did she say if it hurt or anything?"

Crissy said, "No - She said at first it wouldn't fit in - she was worried it was too tight - but when it happened, when he pushed harder and he was inside - she LOVED it."

I know her friend Elizabeth really well, I mean, her and Crissy have been friends since they were little girls. She's really sweet and cute, so it just seems hard to believe that she would - well, that she would even think about anal sex, let alone actually doing it.

Crissy continued, "Elizabeth kept saying how much she loved it. And hearing her sound so excited, I don't know, it just got me all freaked-out."

And then we were both quiet, it was like she had just said TOO much. But - I could tell it was helpful for Crissy to share this with me, that it calmed her down, especially after being so upset after the phone call with Elizabeth.

I couldn't help myself, I had to ask, "Well, what else did she say about it?"

"You really want to know?"

"Yes, I'm curious."

It felt funny to ask, I thought Crissy might get angry at me, but she seemed really enthusiastic to tell me the details, "Okay, she said it wouldn't go in at first, but they used some baby oil, to help make it - well, to make it slide in easier."

When she said that, my mind flashed to all the massages I've given Crissy, and how I used baby oil on her back. She would get so tense before swim meets, and my back rubs with baby oil really helped her relax.

I cautiously asked, "And did Elizabeth say the baby oil helped?"

Crissy whispered nervously, "Oh God, she said it helped a lot, she told me it felt amazing. She said she LOVED it."

"I just can't imagine little Elizabeth doing that..."

My sister sounded so shaky as she told me even more, "And - she told me - how she said she had a - she had a - really amazing orgasm, when he was - cumming inside her..."

There was such an intensity to my sister when she said that, all I could do was whisper, "Oh God..."

"Oh Michael, thank you - for being such a good listener," And she snuggled in close and kissed me on my cheek.

We were lying on her bed, all snuggled up together in a tender embrace. We stayed like that, in silence for a long time. I thought to myself about what she had just confided with me. She sounded so distressed, and it was hard for me to understand.

Finally, she broke the silence, "Michael, why am I so FIXATED about how big my bottom is? I don't understand, I'm just so obsessed about it."

It broke my heart to know that Crissy could feel so insecure. She has swam competitively since she was a tiny little girl, and she has an amazingly beautiful body, especially her bottom. But, for some reason, she just doesn't realize how pretty she is.

I tried to say something nice, "Crissy, please believe me, your bottom is beautiful - I like it - I really do."

In a need voice she asked, "Really? Do you mean that?"

I whispered to her, "Yes, I really mean that, you are so lovely. And your bottom is perfect, it's just the right size, and I love it, I really love it. I think it's cute."

She took a deep breath, and replied, "That feels so good for me to hear. Thank you."

A haunting emotion seemed to overwhelm me. I just felt so desperate to HELP my little sister. She seemed so lost, and all I wanted to do was make her feel better.

I was lying there with my arms wrapped around my beautiful little sister. She was snug up against me on her tummy, and I could look down, and see her bottom. It was cute and perfect.

She whispered, "Is it - I don't know - is it weird that we are talking about this, I mean about my butt?"

"No, I love telling you how beautiful you are. Listen to me. Crissy, your butt is perfect and adorable."

She sighed with relief and said, "Oh Michael, you have no idea how much I need to hear you say that."

Then she sort of sat up and looked at me with a sad and haunted expression. I had never seen her look so helpless. She was obviously overwhelmed by everything Elizabeth told her.

It was a strange and awkward moment. I know she needed to me be honest, but maybe I was TOO honest. I mean, I had just given her such heartfelt compliments about her butt. I felt embarrassed, and I thought maybe Crissy needed to be alone.

I nervously whispered, "Well, I think maybe - I should back to my room."

And I got up off the bed and walked toward her door.

Then Crissy said, "Wait!"

My sister jumped up from the bed, ran towards me and hugged me. Her embrace was tight and emotional.

She gasped nervously, "Michael - thank you - really."

She kept on holding me - really tight. I was surprised at how intense she was acting.

I felt a little bit self conscious when I said, "Crissy, you're my little sister, and you know I love you, it's good that we can talk like this."

After a little bit, she eased up on the tight embrace. She smiled nervously and kissed me on the cheek. Just as I was about to walk out the door she stopped me again.

"Michael - Please - just a second - I mean..."

I turned to face her and asked, "What is it?"

And then Crissy looked at me, and she seemed so ashamed and upset, and I felt like it was my fault for being so open and honest. I felt a weird embarrassment, and a sort of sinking nervousness.

Crissy said, "I don't know what's wrong with me - something seems scary, I feel so tense."

"What is it - how do you feel?"

"Oh God - I feel super anxious, I don't know, all of this kind of - it just scares me - you know me, how I can be. I just feel so - uptight, and I hate feeling like this."

"Can I help?"

"I don't know, this feels like when I got so worried and freaked out just before the swim meet finals. I was so nervous, and I feel like that now."

I said, "Remember before some of your swim meets last season, I would gave you a back rub - and you said it helped."

"Yes, it did help - a lot."

"Do you want a back rub? I can if you want..."

"Oh - I don't know..."

"Listen, I want to help - You know I love giving you back rubs, and I would be happy to try and soothe things for you."

"Thank you, but no - not now."

I smiled and tried to let know I understood, "Please, don't worry about anything..."

"I'll try."

"I'm going to go to my room, okay?"

"Okay."

As I stepped away, I was stuck by how vulnerable she looked. She seemed so frightened the way she stood there. And at the same time she seemed so cute in her little boy boxer shorts and her big sleeping t-shirt. My little sister has tiny breasts and right then I could tell she wasn't wearing a bra, I felt like maybe I was staring.

And then she kissed me, sweetly on my cheek.

She said, "Thanks for being such a good brother, and - and..." she trailed off into silence.

"What?"

She cautiously said, "Michael, it makes me so happy to know that you - you like my - my bottom."

I smiled and caressed her shoulder, "I love your bottom. You're beautiful. Really and truly."

Crissy looked up at me and smiled meekly and said, "I love you."

I suddenly felt a little less worried and said, "I love you too."

And then I stepped out into the hall. I closed the door behind me. I felt bad, Crissy looked so worried and vulnerable. I walked into my room and closed my door - but I didn't lock it. I sort of collapsed onto my on my bed, and I tried to make sense of a crazy avalanche of emotions. What was happening? I wanted so badly to help my little sister, she seemed so sad and tense.

I love her SO much, I really do, but I worry she can get so emotional. All the talk about such intimate stuff got me sort of freaked out, and really concerned for her.

I mean, it was totally shocking when she told me her friend Elizabeth had anal sex! I had never heard my sister talk about anything like that, and to see how panicky it made her really bothered me.

And when she said that Elizabeth had a huge orgasm while being fucked in the ass. Oh God, it was so weird to even think about that. And my little sister sounded so anxious about it, and I felt such a deep need to make all those sad feelings go away.

And I just stared up at the ceiling there on the bed, wondering about my little sister. Oh my God, what I was feeling?

I didn't know what was happening - I just felt SO concerned about her. Right then - I really wanted to know was what she was doing, I actually though about sneaking into the hall and trying to peak through her door.

I got up and searched through the drawer next to my bed. I grabbed an old pair of pajama bottoms and put them on. Sometimes I sleep naked, but right then, after talking with Crissy, especially all that talk about her body, it just felt funny. All I was wearing was these pajama bottoms, and I climbed back into my bed.

Oh God, my little sister is so impressionable and shy. And, I felt so bad - It felt like I maybe I should have complimenter her even more, because of her deep insecurities about her bottom. I thought maybe I should have praised her, I should have repeatedly told her how much I adore her exquisitely beautiful ass.

I so dearly love my little sister, but why was I so worried? I was confused. I mean, it felt really good that I could tell her - in such loving way - that her bottom was beautiful. She seemed to encourage me, and I couldn't help myself. It just felt so honest to say it to her.