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I fell into a trifecta, a convergence of circumstances which, at the time seemed insignificant until I found myself living it. Allow me to start at the beginning.
I am a carpenter and am always doing some work on weekends for extra income. When my sister, Deanne asked me to do some work for her, I cringed. One, never do work for family members. Two, never do work for this family member. We are a blue collar family, tradesmen and cops. But Deanne married rich and became someone different. All her upper crust shit may have worked in the multi million dollar neighborhood, but she was still one of us, and her attitude would need a reminder constantly that I wasn’t some servant. She also watched home improvement shows, which is all a housewife needs to see to start telling you how to do it while looking over your shoulder. I love that, my 25+ years on the job, and I could have learned on a tv show. I always got the job done she needed but not without taking twice as long as with other customers. Sister or not, she is a customer from hell.
Now with all that aside my sis has some wonderful qualities which I do love her dearly for. One is she is my older sis, by 12 years and always, from when I was a baby, mothered me. Overprotective and smothering, she at times mothered me more then my mom. In a way that was not weird but she had issues with my mom and I was treated to her spoiling me. We come from a good family, financially solid middle class. She has one daughter and overdid it with her. Baby class this and that, she even went to massage school, the real deal that took a semester or two. Just to massage the baby, and no doubt hubby. Since Deanne hasn’t had to work so much marrying rich, her time is into activities for her kid, and with the other snobs. The massage school really wasn’t a surprise as her crowd is not the plastic surgery, Gucci crowd, but more like the yoga, holistic, self enlightenment crowd. Ex hippies mostly, but wealthy.
Now Deanne is her late forties, with straight thick brown hair. Sensual, the body of years of yoga and the such, not rock hard but curvy and smooth. In shape and them some but with a sensuality and gracefulness that years of intense yoga brings. Beautiful shaped tits, all her life she has had tits that make men gape. Really they slope like a ski jump with the nipple at the point. They are still hot, but no doubt helped with the right bra nowadays. She is about 5′ 9 or 10″ and very leggy. My masturbation sessions have many times had me thinking of her lowering those scrumptious tits over my face as she swung her legs over me, her hair all over my face.
Now even as an adult she would spoil me or rather look out for me. Tell me not to work so hard, foods I should eat, exercises I should do for my sporadic lower back problems.
The work I was to do was easy. More labor than skill, mindless work and going smoothly since not much Deanne could say or change. Redo some floors with expensive tiles, and I do a lot so I have all the commercial equipment that makes the job a breeze. This was the first part of why this day became so great, they pay more then I would charge friends or family, and had the money to do it. Usually I didn’t mind because she is such a pain when I do work for them. This time I would make a lot of money doing easy work and hardly have to concentrate, doing this is like riding a bike.
The house was empty and I ventured out a few times to my truck for stuff, and ran into Deanne as I was coming down the stairs one of those times.
“You’re back, my god your bent over!” she was coming over to see me.
“I’m laying tile, it will be fine when I get home and stretch and get off it.” I shrugged.
“Nonsense, take a break, Get to a point where you can stop and have lunch. I’m getting ready for yoga and will make us something to eat when I get changed.” She has a room built off the living room for working out, really nice and her own massage table for when her spa lady comes in for her nails, hair, massage, blah, blah. I worked for ten more minutes then came down to the kitchen. My sis was dressed in work out shorts, short but what was so hot was how they are like a second skin, I could see a complete camel toe and her ass was bouncy, cushy looking and with no obvious panty lines. Her shirt was a sports bra more or less of matching material and did not push or mold her tits, but rather molded around her form. My eyes caught every glance I could and not be caught. I was getting hard, and two weeks of no sex since my girl was fucking crazy and I ended that had my mind racing.
“Tim won’t make it home tonight, he’ll fly back tomorrow and Rita is at her friends tonight, so stay for dinner when you finish and I’ll get takeout.” As she said this she had spilled a piece of food on her cleavage and took her pinky finger and scooped it up and into her mouth. My mind was picturing my tongue doing that halkalı escort and when I looked up she was staring at me. She said nothing and got up. My back was sore and I mentioned that I wanted to fix it at home.
“Nonsense, you can get in the whirlpool tub in the master bath and since you are getting this way working here I’ll give you a massage. “As she said this Deanne was at the sink and her ass was bouncing as she scrubbed something.
“Really?” I said suspiciously, as she never gives anybody a massage at all anymore..
“Yea, it’ll be no problem, and I know your back hurts. You won’t complain but I can tell.” She was heading to her workout room as she was talking.
So, circumstances are this. I am alone with my hot sister in her house. A job for her is finally going easy, She wants to give me a massage after I soak in the bath next to her bed, she is dressed in cute, form fitting stretch workout clothes, what little there is of them. Nobody will be home until at least morning and it is lunchtime now. I haven’t been fucked in weeks and have been thinking of nothing but sex all day. You know when your body tells you it needs pussy, well mine was in overdrive. I put this all together in a few seconds, and can tell you my sis did not. Nothing unusual had happened or been implied and we never have had any sexual interaction or even a hint of it. The most is the few times she would catch me looking at her hot body, lost in lust for a few seconds, but she never scolded me or encouraged it. I didn’t really know what I wanted nor did I expect anything to happen, but this was a massage and a bath so clothes will come off. Yes, I was getting aroused.
I grabbed my sandwich and went to the living room. Pervert little bro wanted to see his sis do yoga. If you have not been introduced to this it is highly erotic as a spectator sport, but I would never do it. Deanne was on her knees facing me and bending over, her ass high. She was into it and didn’t notice me. Stretching, bending, arching and holding poses, I was thinking how I would like to fuck her in those poses but I would need to stretch first. She is limber and those poses would test me with a back not sore from work. I was now hard enough to have to adjust, and I went back to work.
An hour later Deanne came up having just finished. she came over and admired the new tile. She commented on my back when I groaned, But I sent her away so I could work. I did no work and stared as her ass and those never ending legs walked away. Her ass has some bounce to it and those legs are thick but shapely, with no cottage cheese starting or sag to those buns. Work progressed and another hour later she came out of her room, and dressed in her mid thigh terry cloth robe, came walking over.
“You are done for today,” she said sternly, as she turned my radio off. “leave it for the next day. I have a bath ready for you to soak in and then a massage, then dinner. You hurting bad?” she asked, as I was stretching my back after standing back up.
“No, I’m just stiff. I’ll take you up on that bath, and double up whatever food you were going to get, I’m starving!”
Deanne was watching me stretch and grimace and reached out as we got in her bedroom. “Take off your shirt and I’ll work that big kink out a little first. Don’t get on my bed all filthy, but lay face down on the floor.” I did and much to my surprise she put a foot over me and squatted down straddling my thighs. I could feel her warmth as she kneaded my back. I was wondering what color panties were seated on my leg. All to soon she got up and told me to get in the bath. I was eager and closed the bathroom door as she stayed in the bedroom. The tub was all bubbles, and scented, and although not my usual style, I undressed quickly wanting to get in and soak my back. Naked and still lowering my body into the tub Deanne just walked right in. I plopped down, and my balls didn’t respond well, causing my back muscles to tighten and causing a loud moan of discomfort to come out.
“I brought you a robe to wear, but you look like you are aching.” She was gathering some stuff out of a cup board, and I was wondering why the hell she was in here with her brother in the tub. I said nothing, But quickly started washing.
“Soak for a while, and I’ll come and get you in a little bit. You want Nancy’s pizza tonight?” she asked walking out.
“Sure, they have good food.” I told her, settling back and enjoying my hand rubbing my cock in the water slowly.
I awoke with her hands on my shoulder, rubbing me, almost petting me. One hand rubbed up my neck when she sensed I awoke and finger nails raked my scalp massaging my head. I smelled pizza and looked over.
“Go ahead and eat a slice but wait until after the massage for the rest.” Deanne said softly not trying to wake me. My cock was completely awake and responding harbiye escort well to the fingers teasing my other head. I was completely relaxed and grabbed the slice, wanting to get to the massage I had almost forgotten about in the warmth of the tub. As I ate it her two fingers pressed hard in my spine and followed down my back into the water going to the top of my ass. I was in heaven as she asked “Did the soak help?” “Oh, yeah, I’m less stressed now for sure.”
“Good , get up and put this robe on.” She held it up and was standing there, waiting for me to get up. “I want your body wet for your rub down.” She never called it that but I liked the sound. So I stood and gave her what she asked for, my naked bubble covered body with a hard cock standing up and facing her to grab the robe. Almost clinically she gave it to me and said “follow me”. She still had her robe on and led me a very short way to her bedroom which had everything needed for a massage on the bed. I was really surprised as she had the massage table downstairs, but before I could speak she said “Take off the robe and lay down. On your stomach.” I would have expected a towel from a spa or shorts for my sister, but she just told me to strip and get on her bed. She was humming and setting ocean sounds on the recorder, keeping a feel of a real spa setting and not sexual in the least. I disrobed and climbed up adjusting my cock as I laid on my stomach.
Deanne climbed on the bed next to me, her legs under her, and really gave me a good massage. Hands finding knots in my back and painfully working them out. Then rubbing and soothing touches, with a very soft agonizingly tender scraping of fingernails just after finishing an area. her hands ventured south a couple times to my ass and felt good, but by the time my back, arms neck and head were done, I was nearly asleep. Deanne was humming softly and twisted so she was facing my lower half, still sitting on her bent legs. As she started at my feet she had to lean a little putting her on her knees. Her robe was thigh length and my head was turned her way, giving me a decent leg shot as she worked my feet and calves. As she lightly raked those nails up my left calf, my cock jumped and the table was getting uncomfortable and I had to separate my legs a little to adjust so my cock was not smashed under me. This did not go unnoticed by Deanne, and she asked if I was ok. My response was a low moan, followed by “It feels great.” She started to work the thigh closest to her and my ass. Her hands were dangerously close to my crotch, rubbing and squeezing my muscles. Her fingers worked my ass , rubbing hard then fingernail scraping, sending me up off the bed with my butt up, on my knees a little when her nails scraped near my asshole.
” I see someone is sensitive!” she joked as her hand pushed my ass back to the bed. I was so hard I had to keep a leg kicked way out. “Careful, I am still your brother!” I said. She continued but working my ass and legs actually was so exciting that my whole body was tensing back up from her touch.
“This isn’t working” she said as she suddenly stopped. ‘Your not relaxing, and your back is tensed up again.” I craned my neck to look at her and she was deep in thought. Suddenly her hand rubbed my thigh and slowly her nails came in contact with my balls. “Your sexual tension is not letting you relax, you really need some relief, don’t you?” she whispered to my ear as she rubbed three fingers up and down my sac. I said nothing and as an answer moved my hand which was at my side onto her bent knee feeling my way under her robe.
“Well, I don’t know about that, but turn over and we can do what it takes to finish this massage.” I couldn’t believe this but eagerly turned over, not being shy about showing my hard cock to my hot sister, who was looking right at it.
Slowly, methodically Deanne lubed and stroked my cock while I stroked her legs, trying to move the robe higher each time. She broke the silence. “I know that sometimes verbal and visual stimuli can help this go faster. should I talk dirty?” She cooed. “Oh, yes Deanne, talk dirty to your little brother!” I hissed, enjoying this scene and her hand expertly massaging my cock and balls.
“Mmmm, you like this don’t you, your sister making you cum, beating you off, is this turning you on?”
“Mm-hmm, my older sis taking good care of me, just like when we were young, you always spoiled me.” Her hand slid south and toyed my ass, making me lift my legs more.
“Sometimes you were more like a mom then mom was, and now this, ohhh- mmmm, You’re so good to me!” My eyes closed and my hand went high in Deanne’s robe, finding panties and her ass, feeling her up. She sat up a little to give me better access. My hands wanted to feel her pussy and I stroked her inner thigh, rubbing along her crotch.
“Oh, little brother!! Watch your hand ikitelli escort .”she gasped. I reached out to untie her robe and Deanne stopped suddenly, grabbing her robe to keep it closed. I was afraid this was over. I looked at her and told her it would help to see her, I wouldn’t last long.
” I’ve also wanted to see your tits since I was about twelve, so come on, pleeeasse.” I was trying to sound that old again. She blushed and took my hand, putting it onto the tie of her robe and both of us untied it. She did not open it, just went back to playing with my cock.
Slowly I peeled back the robe and exposed one tit. It was gorgeous. Age had done little to her. I lightly touched it, getting a reaction from Deanne. Her nipple burst out from the touch, and she put her second hand to my crotch, touching me everywhere. I got bold, and realized my time was limited with her skilled work on my hard shaft. So I wrapped my hand around her back and gently but firmly pulled her so that she was next to me, but leaning over me with her tits dangling above my face.
” Mmmm, do you want these?” she wiggled her chest as I lifted my head up to suck a nipple.
“do you wanna cum sucking on these, do you like my tits?
“Yes” I was joking when I said to her ” you like mothering me, so let your little boy feed on you!”
This did something to her, because next thing I know she is going at my cock, finger rubbing my ass, pushing her tit into my face, almost screaming ” That’s it, suck Mommy’s titties, let Mommy make little boy cum!” My mouth was occupied but not one hand, so I explored Deanne’s ass, moving around to push into her panties. My greatest surprise came when I realized her pussy was waxed. This had an effect on me, as I LOOOve bald pussy. She gasped when my hand went down, and she talked so filthy. “Thats it, finger mommy’s pussy, you dirty boy, what are you gonna do, do you want to fuck me?” Her words freaked me out a little, although something about my sister doing this mommy thing had me fucking turned on.
“Is that what you want, to fuck your little bro?” I was seeing how much was dirty talk and how much serious. All the while I was fingering her pussy, her cunt muscles grabbing my finger and her hips swaying.
She moved her head to my ear and nibbled it before saying through clenched teeth, ” I’m going to make little boy cum right up inside Mommy!” As she finished this she swung around, and in one fluid motion moved her panties and sucked in my cock. I was beyond turned on and drove my dick in and out, making her put her hands on the headboard to steady herself. “oh, fuck yesss, fuck me, suck mommy’s titties as you cum in me!!” she was bucking and looking into my eyes, saying the nastiest things, telling me she always wanted this, how ever since I was thirteen and she walked in on me jacking off how she wanted my cock, alternating between me being her bro, and the next sentence would be to spank or bite mommy.
I grabbed her tits and explored them, sucking and biting, while fucking her. Deanne was going like a jackhammer, up and down, rotating and mashing her clit into my pelvis. It was all too much and I knew I would cum soon.
I played along and said “Do you want baby boy’s cum in you, I’m gonna cum, do you want to feel it inside you?”
“Cum in my pussy, fill mommy up!” She reached around and squeezed my balls.
I pulled her back to my face , looked into her eyes and hissed, “I’m cumming inside of you, take my cum”, then kissed her. I twisted tongue with her as I shot jet after jet right into her, Deanne moaning in my mouth each time she felt a spurt in her. As we came down and touched each other lightly all over, I said ” You don’t have to finish the massage, I feel much better now!”
Laughing, we both looked at each other. Deanne spoke “Are you ok with this?” she asked
“Oh yea!”, as my cock twitched inside her still hard. “the mommy stuff was unexpected but hot!”
“Good, because I love to role play and my husband does not.” Then her face got playful, and she pouted, “will you play with me?”
I played along. “What does my naughty sister want to play?” I said, egging her on and seeing where she would take this.
” Oh my god, I can’t believe I’m saying this to my brother, but since I can feel you throbbing in me..” we both laughed. I stroked her back and encouraged her to tell me her roleplay fantasy.
“Well, there is more than one and I want to do them all but first one is nastiest.” she moved up and down my shaft as she spoke.
“Sex has always been so proper and confined to the bedroom, and Tim is predictable…”
She was stalling. “Spit it out, I’ll do whatever you want , don’t be embarrassed!”
She thought a minute and looked at me.
” Leave , go away and leave. I’ll go about my day, and whenever you want come back in the house. Pretend you don’t know me , and rape me. Make me do everything you even thought of doing to someone. Use me anyway you want.” She was still riding my cock and starting to orgasm as she said all this.
This was turning into such a strange day. A wonderful, perverted, strange day.
To be continued
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