This is a story I've wanted to share for some time. I still hurts thinking about it even now, fifteen years later, but I think perhaps talking about it will help. I know my therapist says it will. I'll warn you now just this once - it's going to hurt. I really do hope it helps. I guess we'll see. And it's a bit long in the telling. I have a tendency to ramble on, my folks always gave me shit for it growing up.
I suppose a little bit about me is in order. I was born James William Kay. I'm forty years old, six feet tall and a little heavy at 250 pounds. Never really been able to push past that - I'll lose twenty pounds or gain twenty but it always ends up hovering around that. I was self conscious about it when I was younger but as I've gotten older and the hair atop my head decided to march down my back instead I've worried about it less and less. What hair I have left has gone to gray while my eyes have been as dark as a storm cloud from the day of my birth. I'm strong enough - I spent most of my twenties and thirties working construction for a company out in Alabama, we worked hard and played hard. Good times.
My older sister and I grew up together in southern California, thick as thieves even though she was five years older than me. I was never pushed around or treated like the little snot I was - Amanda (Mandy as I always called her) always took me with her when she wanted to go somewhere, first as kids to the playground, later to the movies and the mall and after she graduated to dinners at fancy restaurants.
She was the brains of the family - she'd had a head for academia almost as soon as she could read and her skills only grew. She graduated high school two years early, and managed to claw her way through college all the way to her Masters degree six years later before deciding she was tired of spending her days learning. Apparently teaching appealed to her more, she spent the next seven years working at one of the high schools in Mobile.
Mrs. Kay as I liked to call her in later years was tall - almost as tall as myself - and curvy in all the right places. She carried a bit of extra weight herself but it was never enough to leave her looking more than just a bit chubby. Her face was round without going too far - adorable and sweet, reflecting the woman inside. We have the same color eyes, though her natural chestnut hair didn't have a trace of gray or white to it. Her coworkers and students commented on how cute she was all the time while I was absolutely smitten.
You see, I'd been in love with her since before I could remember. When we were children together we were close - really close. All of our earliest sexual exploration was done together and we never really thought about it at the time - after all, we were just kids and we were just doing what kids do. As we grew older our activities began to curb - once she hit high school she was dating fairly regularly. I never told her at the time but I was physically ill the first time I saw her kissing another boy. I was only nine at the time but I remember it as clear as yesterday. Again, I didn't say anything but I think she knew. She was always more perceptive than I was when it came to reading someone. By the time my senior year rolled around she finally confronted me about it.
"C'mon Jim you've been giving me that look for years now," she said. We were sitting in my room together, listening to music and playing games on our computers as we did when the opportunity came. I'd just turned eighteen the week before, graduation was right around the corner and as a gift our parents had given me a thousand dollars to build whatever system I wanted to. I bought two instead so we could keep spending time together - hers was even older than mine had been beforehand.
"I'm sorry," I said, fidgeting in a way I never did with anyone else. "I really am, I just..." She looked me in the eyes and we remained silent for a moment. "But I really don't want to talk about it, it's too fucking embarrassing." She gave me a furrowed brow with a frown. "Honest."
"Can you even hear yourself talking?" she said, head tilting. I shook mine, averting my gaze, but she pulled it back with a light grasp on my chin. Her tone changed in an instant. "You know I love you Jim. What's the matter?" I didn't know whether to laugh or to cry. Perhaps both. I settled on the former, drawing another confused glance. "Did I make a joke that I missed?"
"Kinda," I said, still chuckling. I took a deep breath. "All right, all right. I saw you last year."
"Yeah?" she said.
"You and Dave."
"...yeah?"
"Doing... stuff." She blinked. "Sex stuff. You had your-"
"I get the picture," she said, hands in the air as she nodded slowly. "All right, so this is starting to make a little more sense. A little anyways. So you saw me going down on Dave. Big deal. Not the first time we've caught each other in the act."
"Maybe so but it's the first time I've jerked off watching you do it," I said, looking her in the eye again. To her credit she didn't flinch, but surprise definitely lit up her features.
"Huh," she said, pausing for a moment. Neither one of us seemed to know what to say. "How 'bout that." More silence. "Well. Uh, yeah. There's that." She took another deep breath. "You're an eighteen year old male. You've got eight million different chemical signals racing through your body telling you to fuck the brains out of the nearest female in stuffing range." At that I laughed loudly, choking - she always had a brash sense of humor, and the concept of boundaries was one that had never functionally existed between us.
"I'm really really sorry," I said, blushing and shaking my head. The thought of her being angry at me was more than I could bear.
"Jim," she said, catching me with her gaze again. "It's all right little brother. I'm not upset. Just kind of surprised, is all."
"I'll make it up to you, I swear," I said. "Honest promise."
"You don't..." she started to say before pausing. "Hmm. Make it up to me you say. All right." She looked at my computer. "Open your porn folder." I blinked. "Do it little bro."
"Porn?" I said.
"Yeah," she said with a stern glare, standing with fists on her hips. "You got to watch me, I want to watch you. Figured you could use the help." I spent what felt like a year dumbstruck, as if my head had simply fallen off my shoulders.
"I um, don't, uh, think I need the ah, help," I managed to say. I unzipped my fly and my seven inch hard on sprang forth like it had a mind of its own. I swear it was looking directly at her tits. I know I was, she had a lovely pair of C's, not too heavy and wonderful with just a little bit of droop to them. One hundred percent grade A au natural, you might say. She smiled at the sight.
"I guess not," she said. "Think you can cum for me?" Did I just die? Because it definitely felt like it. I couldn't say anything, couldn't move, couldn't will myself to breathe.
She must have sensed my hesitation because she slipped to her knees and had my cock buried down her throat in less time than you can say 'holy fucking buckets I'm gonna cum'. Pretty sure I lasted all of .05 seconds before exploding, gripping the edges of my bed and trying to growl without roaring. Didn't need my folks knowing what the hell was going on with their perverted son and daughter. I might have passed out if she hadn't stood up and placed both hands on my shoulder. I looked up to realize I couldn't see a mess. Holy hell she swallowed all of it. The world ended, and I'm sure I died and went to heaven.
"Holy fuck," I whispered. She smiled, chuckling. "Holy mother of fuck. Just... fuck. Fucking... fuck."
"That's five fucks in one breath," she said, sitting back down and patting my manhood before tucking him back in and zipping me up. "Better now?"
"Uh..." I said. Words still seemed to not be a part of my brain. She laughed again.
"That's priceless," she said. "The look on your face."
"You just..." I said. "You...:
"Blew you?" she said. I nodded feverishly. "Yeah, wanted to see how you'd react. You definitely didn't disappoint, little brother. That said don't go getting any ideas - I'm not your sex doll, after all. We're square now, capeish?" I summoned up my best old timey gangster.
"I guess youse could say that, dollface," I said. I blinked. "I swear I didn't mean that the way it sounded." She laughed again, shaking her head.
"Same old Jim," she said. "Insert foot in mouth." She stood. "Relax man. Now let's get going, we're gonna miss the start time if we hit traffic." The movie we'd been planning on seeing had been the furthest thing from my mind. In fact I'm not even sure my own existence was on my mind, other than the fact that the woman I'd been in love with all my life had just swallowed my load.
That night I spent hours trying to sleep to no avail. I couldn't stop thinking about what had happened that afternoon. She was the third girl to go down on me but the first one that let me cum in her mouth and the first one to swallow, all without saying a word. The feelings I'd had earlier that day had exploded into flames, love and lust twisting and turning, lighting up corners of my mind I didn't know existed. When the clock read two in the morning my door cracked open ever so slowly, a silhouetted figure padding quietly in and shutting it just as gently. Mandy slipped into bed next to me, our foreheads touching as they had the years we'd slept in the same bed as children.
"I wanted to apologize for earlier," she said quietly. I couldn't see her for the darkness but I could feel her breath on me, could feel the warmth of her bare skin pressing against me. There went the hormones again, completely out of control. "I realize you probably weren't expecting that, I didn't mean to surprise you like that. It's just that... well, I've got a bit of a confession. I've been watching you masturbate for the last three years."
"Do what now?" I said. She was silent for a moment.
"I caught you in the shower, you never saw me," she said. "I couldn't help but watch - you were having so much fun with it I figured you knew something I didn't. I couldn't help but think about when we were younger, and the games we used to play." I felt her hand slipping around my manhood and the breath left my chest.
"Oh?" I said, suffering the worlds worst case of drymouth. "Yeah?"
"Yeah," she said, voice husky. "And I touched myself too, just so you know. I can't help it. Every time I see you in the back yard doing chores, out in the garage working on your car or at the job site, I just want to take you somewhere quiet and fuck your brains out." Libido, we are cleared for launch. Her hand moved once and I shot a load, twitching and groaning as rope after rope splashed against her. She giggled. "That's all right, Jim, that'll make it easier when we get down to business."
"Business?" I said. She responded with a kiss that very quickly became frantic groping on both our parts. Neither of us said a word as hands roamed across skin, each of us stroking and moaning. After a minute or two I had enough hardness back for her to roll on top of me and slide me inside of her. Both of us moaned quietly and she leaned down over me to put a finger to my lips.
"We have to be quiet," she whispered. "Mom's not home but dad has to be up at six, don't want him hearing us."
"I'll try," I croaked as she started sliding up and down, back and forth, slowly at first, gently grinding her pelvis against mine as our parts merged, cock buried in her steaming wet snatch. I'd never felt anything like it before, never dreamed it would feel so good. I was disappointed when I could feel another orgasm building up. "Gonna cum again sis, sorry." She kissed me deeply.
"It's okay little brother," she said, hugging me tight as her hips continued to rock against me. "Cum inside me. I've been on the pill for years now, I want to feel you shoot little brother. Do it for your big sister, cum inside big sister's pussy." I could have died then and never wanted for anything else, and seconds later I was responded just as she asked, exploding hard for the third time that day. Where the fuck all of that cum came from I had no idea, but she seemed to have a knack for bringing it out of me. After waiting for a few moments she slid off of me and curled up against me. She took my hand and dipped it into her sopping wet cunt, bringing it up to her mouth and sucking my cum off of my fingers.
"Jesus fuck," I whispered. She giggled.
"Fair enough," she said. "Had to have another taste, it was so good this afternoon it's all I could think about."
"I can't tell you how long I've wanted to do that," I said. "Even if we never get to again, I love you sis."
"We will," she said. "Don't worry about that. And I love you too, dingus." I frowned, poking her in the rib and bringing a squeal that she suppressed.
"Dodo," I said. Dingus and Dodo's Traveling Circus, an old joke we'd had since I was about seven years old.
"I mean it though," she said, tone changing. "I do love you, Jim, more than anyone else I've ever known." She meant it, I knew it - she'd never been able to lie to me before.
"So..." I said, still struggling for actual whole sentences instead of cave-speak. "What do we, er, what are we... you know... right?"
"What does this mean for us?" she said. I nodded. "I don't rightly know yet. I've been thinking about it for a while but I haven't been able to decide just exactly how I want to go about it."
"So there is an 'us'," I said.
"There is most definitely an 'us'," she said, kissing me again. This time it was tender, gentle and brief. I could sit and kiss her for hours without complaining, she had the softest lips I've ever tasted. Not to mention the tightest pussy, was definitely looking forward to that again. "I've been waiting for you to turn eighteen, that part was step one. We got that out of the way. I also wanted to spend some time fucking you to see if it could work."
"You were worried it couldn't?" I said.
"Not really," she said. "I've known for a while now, but I had to be sure. You know me. Yeah. What do you think of Mobile?" That was a surprise.
"Alabama?" I said. "The hell?"
"There's a high school there that has a special education department that is looking for help," she said. Ah, so that's what's up. "I put in an application last week and this morning they said the job's mine if I want it. Even found a decent place nearby. It's only one bedroom, maybe five hundred square feet, but it sits on an acre of land a bit away from the nearest neighbor."
"So today..." I said.
"...was important," she said. "I wanted to ask you but I wanted to make sure you had fun first. If you said yes we've got a lifetime ahead of us... and if you said no at least we had a great memory to share." I could feel tears welling without even thinking about it and I had to choke down a lump in my throat.
"I love you," I said. "I could never leave you. I'd follow you into the Amazon hopping on one foot if I had to." She kissed me again, gentle at first and then more aggressively as we continued.
"Think you can get him up for one more roll in the hay before sleep?" she said. My cock came to life as if on cue and she chuckled. "Question answered. I'll take it slow this time, I'd like you to get more than a minute out of it and I'm pretty damn good at what I do. Just lay back, relax and let big sis take care of you."
That night was the single greatest night of my life up to that point, and even greater were still to come. What I didn't know was that night also set in motion the chain of events that would part us seven years later.