The Massage

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Sister massages more than he anticipated.
4.3k words
4.13
226.9k
92

Part 1 of the 2 part series

Updated 06/07/2023
Created 06/23/2015
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Warning: this story consists of the following (in no particular order): incest, anal, fingering, massaging, and oral. It's a short story that I spent maybe 5hrs writing and editing: okay I edited it multiple times. All characters in this story are over 18. The characters are real people with their names changed for obvious reasons. It's up to you to figure out what you feel is real and what is not. Also, no copy is to be made of this story without the direct approval of the author which is me: LIVE4THEBJ. Now onto the story.

***

I grew up in a household with 2 sisters that couldn't be more different from each other, a mother, and a father that really wasn't much of a father. He was not really worth mentioning but between things he has said, done, and the box of condoms he kept in his vehicle and how condoms were missing past what I took for my own purposes I at least knew I got my sexuality from my father.

My mother was not a sexual person, or at least did not put out sexuality. Always wearing pants, mostly black and at times went months if not years not shaving her legs. But I loved her just the same. Then again arousing events have taken place with her whether she meant it or not.

Then there was my oldest sister Lisa whom much was much like mom in many ways aside from shaving her legs. Lisa was 10 years my senior and helped raised me during those times my mom was sick. So it's safe to say she was more like a second mother than a sister. She eventually grew up and went to live her own life first as a corporate woman and later a housewife raising 3 girls.

Lastly there was Sandy which was 6 years my senior whom was like me in many ways but when we grew up I didn't know it yet. She was the black sheep of the family; tried modeling, got into drugs, the wrong crowd you know the typical story. The one thing that girl knew more than anything is she didn't want to be under my parents rule or under anyone's rule as well as no longer living in that house. Once she reached the age of adulthood she got a van, a camper, and with her boyfriend of the time plus her best friend set off to California.

Not to bore you the details so I will summarize for the story is about me and Sandy many years later. Not sure if I was in my 20's or my 30's when this took place for it's still fuzzy during those times in my life. But Sandy was again a wild child. Started her life as a hippie in California for 10 years, then came home for several years, got married, then got divorced, and at some point in all of this went to a college taught by hippies the art of massage therapy.

It's all legit, she is completely certified in our home state as well as the great state of California and made a really nice living from it. I had to assume at the time she was good at what she did for most of her clients were rich people with more money than they needed, and even some were very famous actors and actresses. All clients she acquired were from word of mouth.

While Sandy lived here I helped her out when I could whenever she requested it; more times than not it was with computer issues which is what I do for a living. Granted in technical terms you could call me a geek, however Sandy called me a genius. The fact is if I was a genius I would be doing something else than fixing other people's screw-ups. But I was good at what I do and it pays quite well especially when you are a field tech. Plus with having a mortgage and a kid you do what you have to do to pay the bills and live what life you can. Not everyone was smart enough to chase their dreams when they had the chance.

Her payments for my services were IOU's which she promised massages. Now while I read, and get-off on incest stories the thought of my sister massaging me at the time didn't appeal to me. Don't get me wrong, like I said she tried modeling just didn't work out but she has the look. Blonde, thin, decent height, all that jazz. She even has a nice rack which I was lucky enough to see when I visited her in California where her and others did a lot of things naked. Hell I even walked in on her riding her man one morning. That was cool to see for she was going so hard at it I thought she was going to break his dick. I am not kidding, that really happened.

But focusing on what this is all about, I have major back issue that was due to a birth defect that surgery can't rectify. It's not so much of a problem if I keep my core strong and the weight off. But with me leaving the martial arts the focus on my core wasn't there as much as it should have been and because of that pain started to occur. The pain got to the point I decided to cash in one of her many IOU's to which she was more than happy to do so.

There wasn't anything sexual about this at least it didn't start that way. She did have me get completely naked, and get on the table and cover my ass with a towel while laying face down which anyone that has been in this situation it's easier said than done without help. But I pulled it off and then yelled to her that I am ready.

Being my typical sister she decided to fuck with me at first, she lit up some sage using a lighter by her side and doing some new age chant. Thinking to myself how typical, and told her to knock it off and get to the rubbing. She naturally giggled and started to do her thing.

I have to tell you for a skinny blonde she had some strong hands; I am no small guy mind you. I built up a nice physique between physical sports mostly martial arts and lifting weights for I just love working out. It's one of my many hobbies but it's the only one that I been doing since I was a teenager and it shows. But this skinny minny was putting some pain into me and she eventually noticed.

"Let me know when I go to hard. This is supposed to be enjoyable not painful." Sandy said.

I nodded and she resumed. We finally found a grip and pressure that was to my liking and I just let my body relax and enjoyed it. As time went on she proceeded to massage each part 3 to 4 times before going to the next part. During this time I was admiring her legs with my head facing through the headrest and how smooth, shiny and tan they are.

What I need you to understand while I have many turn-ons especially tits and asses it's a sexy pair of legs that will do me in. It's one of my biggest vices: always have and always will. I discovered this all throughout my life from teachers, to my mom's friends, the MILFs in church and so on. It never has changed; a woman can be ugly as fuck but if she has the gams to die for, I am hard. All I can picture is my head between those legs licking her pussy, and manipulating her with my tongue.

So it's only natural with my sister being a skinny woman with sexy legs, this appealed to me. My mind doesn't distinguish between right and wrong when it comes to what turns me on, it just knows what it likes and I accepted that. For where is the harm in looking even if it's relative regardless of what society says.

With my focus completely on her legs watching the tension leave and return as she flexed her foot one way and another, I was starting to get a little bit turned on. Note I wasn't expecting this; I always knew she has nice legs and a perfect size rack but never really affected me. But it is now, and considering I am naked and the only thing covering my reaction is the massage table I am laying on, I might be in trouble.

Between trying not to fuck the table, and enjoying the massage, Sandy eventually found her way to my lower back where I needed the most attention but it's also where things got interesting. As she was working the lower back the area right before you get to the butt with her thumbs the pain began to finally start to subside. But with the pain dissipating my level of arousal began to increase.

The sensation were slowly going from my lower back to my butt, and really feeling it in my ass. Unfortunately for me this is one of my sensitive areas. Learning during my marriage that I have a fondness for anal play. Not just giving but receiving too. I am not gay mind you not that there is anything wrong with that, I just love my asshole licked, fingered, or even fucked with a toy of a size that I can handle, and this is something Sandy doesn't know, at least not yet: or so I thought.

We have openly talked about our sex lives. To things we done, need, want and so on. Like I said my sister and aren't much different when it comes to that, and it's part of the reason we are so close. We truly understand one another. Sex is something we love, and it's something we both need much like how people need food. I still remember years ago when she and I were alone in the living room many years ago out of the blue said "I am horny". Man if I knew then what I know now I would have done something about it. But I didn't, and now we are back into the present time and we yet to ever cross that line.

So as I was saying Sandy continued forward with her massage, she stopped the thumb method and proceeded to rub/push method from the middle of my back down to my lower back and then eventually it went further to my butt. My initial thought as she did that "Oh boy, now we are in trouble" for it flicked my arousal from a 6 to 10 just like that. Not only that, I naturally said "oh god" as natural as a fart in the wind. I didn't mean to say it, just came out.

Sandy's reaction, well she paused for a few moments, and then did it again...and again...and again. My response, was a natural one and physical, my hips started to gyrate. It doesn't happen often with me, but when it does it's beyond my control. Once you hit those spots the rest is nature taking it's course. So I had no other choice but to lay there and let it all happen.

However, looking back at it I have to wonder I am not the only client having this reaction. Think about It, you are naked, and I know just on the Literotica Forums alone many get aroused by such things, and then take how she looks plus my love for incest, it only makes sense I would respond to It.

Well anyway, bringing you back to the action between all the rubs and pushes, and squeezing of my ass, she paused for moment to get more massage cream which was warm and had a euphoric sent to it. To this day I do not know what she was using, but it was having the desired effect as well as affecting me in other ways not exactly planned. But it gets better, I was not only picking up the scent of the cream, but I was picking the scent of her pussy. With her positioned where my head was, and the pushing and sliding of her hands her crotch was getting awfully close to my nose. While my nose was facing the floor it did not stop the smells reaching my senses. Yum! I just love the scent of an aroused female.

Even though I never smelled it from my sister before, there was no doubt in my mind my sister was getting wet. In fact, knowing what I know about her, I wouldn't be shocked if she did not have any panties underneath that short summer dress of hers. With her being as much of a slut as I am a male whore I can see my sister wearing the summer dress without the use of panties as a quick easy access to her nether regions for release when the need comes: whether with a partner or self-inflicted. We both have shared our history of needing this, and just come to accept we are very sexual people and there is nothing wrong with that.

Of course, I didn't acknowledge the scent I picked up on, but I knew, and I am willing to bet she knew that I knew. But we are close, very close, and due to the recent situation we are even closer now than ever. To be perfectly honest, at this point if she had me roll over so she could sit on my face I would have done it without hesitation.

Anyway, here I am naked and my sister is massaging and working my ass over and over again and I am just responding to it with all the positive signs; sexual or not there was no doubt I was liking what she was doing, but it got even better. After she got more cream she really started to work the butt with more attention on the cheeks and working more towards my crack. It's during one of these rubs where her finger swipe past my sphincter and my reaction couldn't be helped, I moaned and jerked back naturally without any thought to it.

Not missing a beat she did it again and again using one finger with lots of lube, and the other was lubing and gently rubbing my balls. Clearly the massage went past the norm of what is acceptable but I sure as hell wasn't going to complain. Would you complain if your sister was getting you all worked up and started to rub/touch your erogenous zones? If the answer is no, then why are you reading this?

Going back to that day I remember the pleasures I was experiencing was truly beyond words, and I didn't want it to end. Lucky for me they didn't end, in fact things went a tad further than what anyone would have expected.

To understand what happened next you have to realize I have and continue to masturbate on a frequent basis, but with masturbation I am known to use toys to myself. To be a bit more specific I am talking about anal toys and I have a nice collection. My all time favorites is a cross between one toy that you enter and use your anal muscles to move around and the other would be my vibrating buttplug that I just love to use while alone in the shower when no one is home. In fact, it's the anal vibrating butt plug that resulted in my very first prostate orgasm.

Prostate orgasms I have read people trying to explain them, and you really can't. It's an orgasm hard or soft you will cum. A prostate orgasm if it happens when you are standing I guarantee you that your knees will give out. Hell I barely kept standing when it happened and man when it happened it took every ounce of my strength to continue to stand. I almost hit the floor but didn't, and that my friends is a prostate orgasm.

Why am I telling you this? Well to understand the next part you have to realize anyone that does anal play no matter how small or big the object that goes in helps relax and loosens the anal muscles. Not that it's bad thing unless you are one of those people that put insane objects in their butt, it's actually make the daily duties that much easier. Sorry didn't mean to gross you out but you have to understand that to understand the next part of the story. I promise you it does NOT involve feces so relax.

So as I was saying, Sandy was rubbing and rubbing the inside of my butt crack and it felt amazing. Take that plus my love for anal play plus me responding to her touch naturally my sphincter began to open a little. Because of that during one of swipes of the finger much like a tire hitting a pothole, her finger sort of just fell into the small opening my backdoor made for her. This didn't stop her though, oh no she didn't stop there, but she did pause and rubbed around the area a little and I just started to moan even louder, and was pushing back even harder.

But like typical Sandy as I remember she was also a tease. Teasing me like when we were kids but in a different sort of way, she resumed her swiping and rubbing of my entire back crack and all I could think about is if she would just put her finger in my hole at least once. God bless her little heart she did just that. during one of her passes her finger slipped in slightly with little resistance and then she just stopped going in the direction was headed for, and instead was pushing straight in. That is where I started to lose it.

My breathing was quickening, my hips were shaking, and of course I was pushing back to try to get her even deeper. Each push she would either let her hand go back with the push, or push forward and allow her finger to enter her baby brother's butt.

To think about how many times I had girls finger, and fuck my ass, and now my sister is fingering it, I was now ready to die a happy man. But I was wondering what was her thoughts, how much of this is having an effect on her past what I smelled with my senses. Where do we go from here? Then she spoke.

"Do you like that?"

"Sand you have no idea."

"Oh actually I do my little brother. Don't forget we both get our hormones from our father, and you and I have many times talked about our sex life. I still remember that time you and I were at that bar and you got hammered and told me about that prostate orgasms you had with that vibrating butt plug." She continues to say "Do you still have that?"

"Wait? When did I share that with you? I thought you never knew that side of me?"

"Oh my little silly brother, you forget how hard it is for you to keep a secret when I flirt with you have after you had one to many drinks. Oh the things I can get out of you, and now look at you, naked on my massage table getting fingered by your big sister." Then I heard her moan followed with her saying "now where do we go from here? That is the big question where do we go from here...hmmmmm?"

Then there was silence except for our heavy breathing and some slight sloshy noise from her well lubed finger going in and out of my ass, rubbing this way and that way almost like she was trying to find my...then she found it...my prostate. Thank you lord she found the male g-spot. But oh no, she didn't stop there.

Sandy remained silent, working her finger further and further into my ass till I felt her palming my butt and continually just rubbing that sponge area that I just love. Then all of a sudden she just pauses; not stop but paused. For if she was stopping I would assume she would be taking that finger out of my rear. Nope she did just the opposite.

Then I heard her say, "roll over gently brother"

Not thinking of how to do it not to mention with my body in euphoria I wasn't sure the best approach till I felt her other hand on my leg and pulling me in the direction she wanted me to go. Going with it I started to roll over to my side with my ass facing her and then her taking control of the leg so she could work with me and help me so I would end up on my back without her finger leaving my ass.

So here I am, towel fell off and on the floor, I am on my back and her finger still lodged into my ass while pressed firmly against my g-spot. Any other time what happened next would seem like a common direction for this to go, but I never expected her to do it, at the very least to me but she did. I am not kidding when I tell you Sandy reached out with her free hand grasping my iron rod and pulling it away from my body, leaned forward and in one brief motion engulfed my cock so far her lips were pressed to my trimmed pubes.

There was no hesitation, no kissing, no licking, no slow sucking. My sister went from holding my cock to swallowing my cock and one swift move. To say I was shocked was an understatement. I had my cock deepthroated but usually the woman would work up to that, I never had a woman just open her mouth and swallow my cock whole like it was an everyday thing; that is till now. Not only that, but at that very moment I felt her press even harder and rub faster on my prostate and I just lost it!!

Screaming and gyrating and basically about to blow my load, words that never really made it to my brain but instead went from my senses straight out of my mouth which from what I can remember and might not be 100% accurate but may have sounded something like this: "OH JESUS CHRIST...OH MY FUCKING GOD...OOOO GOD...OOOO SHIT SAN I AM GOING TO POP...OH...IT'S..." And then nothing.

Just there with my mouth open, trying to get words out not even thinking of what I am saying or meant to say and yet I remain silent. Just making this ridiculous "O" face I am sure and just I couldn't finish my sentence well if you can call it a sentence. Why? Because I burst forth the biggest orgasm in my entire life of orgasms and I had many. Not only was the orgasm intense but so was the actions of my sister for her she is having an above average size cock deep in her throat, and at the same time I can feel her sucking and swallowing every ounce of cum that I was shooting out went right down my sister's gullet.

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