stepsistress
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Stepsistress

Stepsistress

by peccantroo
20 min read
4.08 (20700 views)
adultfiction
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The great love of my life has been my stepmother, Melinda. Over a few days shortly after my 18th birthday, she initiated me into manhood. She also humiliated me, feminized me, and degraded me in ways that were even more important in binding me to her. Years later, after my father passed, she would come back into my life to assume absolute control over it.

Between those poles of my life, only one other woman ever came close to bringing me to the heights - and depths - that Melinda has. That was her daughter, my stepsister, Catherine. Catherine had been both catalyst for, and participant in, Melinda's initial seduction of me. My tryst with Melinda was triggered when she discovered me on Catherine's bed clad in nothing but a pair of my stepsister's panties. And, among the beautiful indignities visited upon me in the following days was being dressed like a French maid to serve high tea to Melinda and Catherine. Catherine indulged as well in verbal, and some slight corporal, punishment.

That day, Catherine had stopped home briefly on her way back to college from some weekend trip. At the time, it was not clear that Catherine fully understood the sexual component of my punishment. However, events in the following months suggested that she had at least deduced, if not been filled in upon by Melinda, the fuller dimensions of Melinda's treatment of me.

***

In the wake of our tryst, Melinda had returned to treating me with the same disdain that had marked our relationship previously. Similarly, when Catherine returned home that summer from her freshman year in college, she did her best to ignore me, except when it amused her to mock me.

As was typical, I was out of step with the rest of the household that summer. Except for one or two trips away together, our parents were fully absorbed by their businesses, leaving the house early and typically returning long after I had made myself dinner. Catherine was working as a track coach at a local athletic club and was usually out the door before I woke up as well. In contrast, I typically worked afternoon or evening shifts stocking shelves at a pharmacy. Thus, the house was usually empty when I arose, and I had the place to myself for a few hours before I went to work. If I was working a later shift, I might luck into still being around the house when Catherine came home.

Red-haired, blue-eyed, and a year older than me, I was enthralled with Catherine throughout junior high and high school. In those days, she had an almost comic-book voluptuous figure with full breasts and a round ass 0n an otherwise girlish frame. Her freshman year at college transformed her into a different, but no less stunning figure. In high school, she had enjoyed soccer, track, and cheerleading. But, in college, she began training in earnest for track and crew. Although she still kept her feminine curves, her limbs, frame, and buttocks thickened with muscle, while a late growth spurt pushed her to nearly six feet tall. Under different circumstances, she could have easily been taken for a model. But, when I would catch a glimpse that summer of her toned, tanned legs disappearing into her high running shorts, her tight athletic top straining to constrain her breasts, and her hair pulled back in a serious ponytail, the effect was altogether Amazonian.

One morning late that summer, I wandered out of my room midmorning to a characteristically quiet house. The door to Catherine's bedroom was open, as she always left it when she departed for work. I went into the bathroom that we shared, started the shower, and climbed in.

As I slowly began to wake up fully under the warm water, my mind drifted to thoughts, as it often did that summer, of Catherine in her running gear. Just a couple of days earlier, I had nearly gasped at the sight of her in a pair of tight racing shorts that rode up over the bottom of her cheeks before plunging between them.

As my cock rose at the memory, I lowered myself to my knees. I took some shampoo from the shower caddy, squeezed a generous dollop into my palm, and within seconds, had my rock hard shaft covered in suds. I closed my eyes and began pumping my stick, fantasizing about being on my knees behind Catherine, squeezing and planting kisses all over her magnificent ass.

The shower curtain flew back. I had not heard her enter. For a second or two, I heard her vocalizing the

Psycho

theme, and when I looked over my shoulder in a panic, I saw her pantomiming a stabbing motion. Then I watched it register on Catherine's face what she had come upon me doing. Her hands flew to her mouth, but they did not contain the familiar peels of dismissive laughter she emitted as she doubled over and backed slightly away.

"Get out!" I screamed struggling to my feet and pulling the shower curtain closed again.

Her laughter began to abate, and I said, half in anger, half in defeat, "Please, just go."

I heard her take a step and the door closing. But, something stayed amiss. I was still not alone. There was a muffled sound that must have been her robe dropping to the floor. Before I could say anything, Catherine eased open the curtain and stepped into the shower behind me.

"I-."

"Shh," she said. "It's all right."

She hugged me from behind and began running her fingers up and down my stomach and chest. Several inches taller than my 5' 8", I could feel her breasts and erect nipples pressed high on my back and shoulders. As she leaned slightly over me, I could feel her breath caressing my ear and cheek.

"It's all right," she whispered again, as she wrapped the long, strong fingers of her right hand around my cock. With her left hand, she began fondling my balls. As she began pumping my shaft, her left hand drifted up my torso to pinch my nipples. I moaned softly and leaned my head back against her shoulder. She laughed softly and, for once, warmly.

She began to stroke my shaft faster and brought her left hand down to catch some of the lather that she was working off the end of my cock. She brought her left hand around, slipped a finger between my cheeks, and began massaging my asshole. I almost immediately began rising to orgasm.

"That's it, baby, give me all you got."

I shot a long rope of cum hard against the shower wall, and Catherine plunged her finger deep into my ass. She seized the base of my cock and gently squeezed, seeming to tame my orgasm mildly. But still, I jerked and twitched and shot load after load against the wall. I was practically leaning all of my weight against her when she released me and slipped her finger out of my ass. She reached around me to wash off her hands beneath the shower's stream.

Catherine kissed me on the side of the neck.

"Been saving that for someone?" she laughed lightly. In a heartbeat she was gone, and for a moment, I half-expected to wake up from a dream.

***

Things changed with Catherine after our encounter in the shower. Nothing more happened between us as the last days of that summer passed. But, she did not retreat to her former icy reserve like her mother had. Rather, Catherine seemed more bemused by me than openly scornful. This was despite the fact that I started rather conspicuously asking after her schedule and our parents', in what she no doubt understood was my hope that we might end up alone together in the house again. I was far too self-conscious and inexperienced to even fantasize about spending time with her away from our home.

Catherine went back to college soon after our encounter, and over the next three months or so, she was never home for more than a few hours to pick up a few things or catch up with her mother. I overheard enough to understand that she had a boyfriend, which made me burn with jealousy. The brief thrill of those visits were the highlight of laboring drably through my final year of high school as a 19-year-old senior, having been kept back a year in grammar school when I first moved in with my father, Melinda, and Catherine.

I next saw Catherine for any length of time at Thanksgiving. For the first time in our lives, she was friendly to me. She surprised me with a hug when she came home that Tuesday night. It was all I could do to disengage and slip away while she caught up with Melinda, before they took note of my erection.

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The real exquisite torture began on the holiday itself. From breakfast to helping set the table and in the kitchen through dinner and clearing the table, Catherine was laughing and touching my arm or flipping her hair or bumping into me. At one point, as we passed in the narrow hall between the kitchen and the dining room, I pressed myself against the wall, while she leaned forward so that her breasts, redolent of flowers, passed within a centimeter of my lips.

To anyone who did not know us, we might have seemed just a normal pair of siblings. If our parents detected anything untoward, they did not bring it up in front of their friends who joined us for dinner. But, my head was spinning half the day. More than once throughout the day, when Melinda asked me to perform one chore or another, I pretended not to hear her at first, in order to give my swollen penis a chance to relax before I stood up. Under normal circumstances, I would have never dared such impudence, knowing all too well that Melinda's phone contained images of me in heels, stockings, a sexy black dress, and full makeup, while under a cherry red wig, and believing all too fully she would carry out her threats to share the images with my father and my classmates should I ever displease her.

Mercifully, after dinner, our parents and their friends headed downtown to a performance of

The Nutcracker

. I sat exhausted on the sofa, vaguely hoping that Catherine would be off to see friends so that I could masturbate furiously and break, at least for a little while, the erotic spell under which I had suffered for hours.

Instead, Catherine came to the archway separating the dining and living rooms. She held over her head in one hand a bottle of vodka and, in the other, a pair of glasses.

"Alone at last," she said, before - swinging her hips rhythmically - she sauntered into the living room, put down the glasses on the coffee table, and filled each halfway. She picked up the glasses and offered one to me.

"Come on, sunshine," she smiled. "Drink up."

I took the glass and a small sip of the liquor. Catherine chuckled when I cringed at the burning in my throat.

"Why so glum?" she asked. "We can do whatever we want for hours."

I shrugged, not quite understanding my subdued demeanor. Catherine forged ahead.

"So, what would you like to do?"

I shrugged again.

"Come on," she chided. "There must be something you'd like to do with the house to ourselves?"

I do not know exactly why - I had always found Catherine more attractive in her running togs or soccer kit - but to my mind sprang memories of football games and Catherine being tossed in the air, with her pleated cheerleader skirt flaring.

Unable even to raise my eyes to look at her, I muttered, "I might not mind seeing your old cheerleading uniform again."

"Really?" she said. "I'll tell you what. Why don't you wait right here, and I'll be back before you know it."

Catherine splashed more vodka in my glass, before spinning on her heel and bouncing upstairs, the vodka bottle in one hand and her glass in the other.

The sight of her thick bottom constrained by her denim skirt, and thoughts of what was to come dancing in my head, immediately thickened my cock inside my jeans. When Catherine did not return almost immediately, I began sipping at the vodka. I had never drunk much, so even on a full stomach it did not take much liquor for my head to begin reeling even more than it had been under just Catherine's attentions.

It began to seem to me as if she was gone a long time, although I was too addled to think to confirm that with a glance at the clock. I began wondering if Catherine had just been teasing me and wracked my brain trying to think of some way to turn such a rebuke on her. Perhaps, I thought, I could feign disinterest by slipping off to visit my own friends for the night. But, that plan foundered on my lack of friends.

As I was trying to puzzle it all out, I heard Catherine upon the stairs. When she turned the corner into the living room, my jaw literally dropped.

She wore gleaming, leather pumps of dark green with at least a three-inch heel. The heels accentuated her muscular, but shapely, legs, clad in gossamer green stockings topped with a dark band of material at the stop. There was a break of an inch or two between the stockings and her hunter-green panties, and a thin bit of pale skin visible under the matching corset that held up her magnificent breasts. Her red hair was now swept up on top of her head. Long, jade earrings caressed her graceful neck. She wore little make-up, which only made her blood-red lips appear even more alluring.

She cocked her hip and rested a fist against it. In her other hand, she held up her old cheerleading uniform, still on the hanger.

"You know, I don't think this really fits me anymore," she said. She strode across the room. I nearly recoiled before her regal appearance. She tossed the uniform onto the sofa cushion next to me.

"Why don't you try it on?" she as much as commanded.

I was paralyzed as she turned and began to exit the living room. Without turning or breaking stride, she added, "Don't keep me waiting."

I began to breathe quickly, then deeply so as not to hyperventilate. I thought again of fleeing, but immediately I realized how foolish that would have been. In my heart, I knew that there was nothing I wanted more in that moment than to be in Catherine's clothes, beneath her sway.

Springing to my feet, I quickly undressed. Given how curvy Catherine had been in high school, I had no difficulty slipping into her uniform skirt and sweater. Her ample form had so stretched the latter that, looking down, it appeared as if I had a notable bosom myself. The only pause I had was hesitating to think of a way to make the erection pushing up the pleats on the front of the skirt less noticeable.

"Are you coming, or not?" Catherine called from the top of the stairwell, a decided edge in her voice. I scurried upstairs.

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She had already withdrawn to her room, leaving the door half-open. I approached cautiously, not sure where exactly she had gone, as I edged into the room. Catherine reached around the door, took me by the arm with one hand and pulled me into her room, while she closed the door with her other hand.

"Oh, darling, look at you," she said, stepping right up against me. In her heels, she towered several inches above me. Seizing my nearly shoulder-length hair in one hand, she pulled back my head and then bent down to kiss me deeply, parting my willing lips with her tongue. I nearly went limp in her arms.

She broke the kiss to ask softly, "Oh, angel, you're all grown up now, aren't you?"

She resumed probing my mouth with her tongue and began maneuvering me backward toward the bed. I became aware of something hard between us pressing against my stomach. When she pulled my head to her breast and began tonguing my ear and kissing my neck, I was able to steal a glance down. It was then that I perceived the pink strap-on curving up from her up pussy. Before that arresting image fully registered, I felt the bed against my calves and knees. Catherine pushed me down on the mattress.

Unsmiling, but not cruel, she looked at me beneath half-lowered eyelids. "I always wanted a little sister. Is that what you want to be?"

I bit my lip and nodded. I felt like a coquette.

"Mmm," Catherine moaned, taking one step toward her vanity. Reaching, she picked up a tube of lubricant, and drawing herself to her full height before me, began slicking up her cock.

"You're going to be a good little sister, aren't you?" she said. I nodded again.

When her cock was dripping lubricant, she squeezed a big dollop into her hand and tossed aside the tube. I closed my eyes in delight, as she forced the cool gel deep between my ass cheeks. I wrapped my legs around her waist as Catherine lowered herself to slip her dildo between my buttocks. She began thrusting, then stopped for her fingers to probe for my asshole. After some more thrusts, the tip of Catherine's cock found my anus. She plunged into me.

"Oh, fuck!" I gasped.

To my surprise, she stopped to ask, "Are you okay, baby?"

I began to nod, opened my eyes, and turned to look into hers. "Fuck me, mommy," I pleaded. "Fuck me."

Now it was Catherine who exclaimed, "Oh, fuck," as she began plowing my ass. I closed my eyes and turned my head again, but soon felt her leaning over me and her hot, liquored breath on my face. I looked to see that her magnificent breasts had slipped free of her corset. Her erect nipples rubbed back and forth across my own. When I turned to her, we began kissing furiously, passionately.

Her thrusting started pushing me toward the center of the bed, and she climbed onto the mattress herself. Taking hold of my hips, she rolled slowly onto her back, careful to keep her shaft in my ass, and guiding me so that I was straddling her.

"Ride me, bitch," she said evenly.

I immediately began gyrating my hips, working the stick snaking from her pussy into my ass.

"Oooh, yeah," she encouraged. I began bucking my hips back and forth, which seemed to please her more. I leaned forward to steady myself with my arms against the mattress and began sliding my ass up and down on her shaft.

"Yeah, slut," she yelled, slapping my ass. "Yeah!"

I resolved to ride her as hard and fast as my ass could take. I was pleased to see her close her eyes in delight and lick her lips. She reached between her legs with one hand to keep the dildo in place. With the other, she began to rhythmically slap my ass.

Several times I verged on exploding. But, through a slight change in position or sheer will, I suppressed the rising tide as long as I could. Eventually, though, the look of sublime pleasure on Catherine's face overwhelmed me. A rope of hot cum arced into the air between us before splashing across her breasts, neck, and cheek.

"Oh, shit!" I cried, nearly coming to a halt on top of her.

Catherine's eyes sprang open, and she said fiercely, "Don't stop, bitch. Don't stop."

I began impaling myself furiously on her shaft again, while my cock was still spurting hot cum across her corset and between her tits. She kept her eyes open now and glared at me hard. "Yeah. Yeah. Work that pussy. Work it, you fucking slut whore." Her back arched.

"OH, FUCK!"

Catherine seized my hips to stop my motion as I heard her shoot a long stream out of her pussy, then its warm, dewy drops misting up across my ass. She shot two more hard bursts of ejaculate before she eased her grip on my hips and guided me up off of her cock.

She threw an arm across her eyes. "Jesus Christ," she seemed to sob. I rolled onto my back next to her, the mattress soaked in her pussy juices.

We laid like that for at least a quarter of an hour. Eventually, she got to her feet wearily, pulled up her corset, and tottered on her heels out of the room. I heard the water running in the bathroom and began to drift into a half-sleep. When Catherine returned to the bedroom, after perhaps another quarter hour, she was carrying her heels in one hand and strap-on in the other, having let her hair down.

She stared at me for a moment, then started to smile with one side of her mouth.

"Want to have some fun?"

The question left me speechless, which only prompted her to laughter. She dropped her shoes and dildo, scooped up her phone off the dresser, and held her hand out to me. When I got to my feet and took her hand, she led me running down the hall to our parents' room. I do not know if Catherine appreciated that, some weeks earlier, one of my rare visits to that chamber had ended in my cruelest humiliation at Melinda's hands. But, at that moment, I did not dwell upon it. I had started to become aroused again as soon as Catherine had taken my hand.

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