stepmistress
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Stepmistress

Stepmistress

by peccantroo
19 min read
4.27 (13000 views)
adultfiction
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Approaching my 40th birthday, I had no real relationship with my father or his wife, my stepmother Melinda. I have maintained to my wife, to my friends, to the extent appropriate with my young children that it is because I had no use for my father or his wife. It is an explanation readily accepted by anyone who has witnessed any of my interactions with my parents. At our most cordial, the conversations were stilted. More frequently, they were openly hostile.

The explanation for the estrangement was also very true of my father. A stern, domineering man, he made no attempt to hide his displeasure when my mother's inability to remain sober and mental health issues resulted in me moving in when I was about ten with him, Melinda, and Melinda's daughter, Catherine.

Melinda hardly showed me any more kindness or compassion than my father did. But it is something very far from disdain that compelled me to keep my distance from Melinda all those years. Melinda was my first, for many things my only. For just a handful of days 20 years ago, she thawed toward me. In many ways those precious hours did more to form my character than all the years before or since. For two decades, I have sought to return to that place.

***

I was very much the outsider in the house. I do not think anyone would have called Melinda warm, but she doted in her own way on Catherine. A popular honor student, athlete, and cheerleader, it was easy enough for Melinda to heap praise on Catherine and reward her many achievements. Likewise, my father was always ready to boast about his "daughter" - never stepdaughter.

Mostly though, my father and Melinda were passionate about each other. Both owned their own businesses - him a textile plant, her a realtorship - to which they devoted enormous energy. Their workaholic lifestyle was interrupted periodically by winging off to elaborate vacations together. Moreover, both were attractive and athletic, and Melinda had the added allure of being a decade younger than my father. If I had had any friends at school, I am sure they would have teased me about having such a young, attractive stepmother. As it was, those who tormented me were happy to make the point in less jovial fashion.

I was very much the misfit in what would have otherwise been a model family. On the shorter side - only about 5' 8", no taller than my stepmother and stepsister - and rail thin, I had no physical gifts to speak of. Nor was I much of a student in those days. In fact, the year I went to live with my father, it was all I could do not to spend my days hiding in the school bathroom crying, and I was held back a year. Adding to the embarrassment, Melinda had had her daughter at a very young age. Thus, although Melinda was considerably younger than my father, Catherine was a year older than me - and two years ahead of me in school. Which meant two arduous years of high school in her shadow.

Making matters worse, it was Catherine for whom I carried a torch in those years. She had flaming red hair, blue eyes that shone from a lightly-freckled face, and one of those perfect, youthful bodies with a wasp waist and an almost boyish frame that somehow supported stupendous breasts and a round, muscular bottom.

Naturally, she would literally not give me the time of day, a ride to school, the courtesy of a "good morning,"

etc

. I worshiped her from the bedroom next door. That devotion would lead my world to change.

***

In due course, Catherine went off to college on scholarship, of course. In some ways, her absence relieved some of the tension in the house. I did not have to try in vain to hide my attraction to her, and my father and Melinda could simply ignore me to the extent possible, rather than comparing me with disdain to Catherine. As my 18th birthday passed and the end of my junior - what should have been my senior - year approached, I was quite content to be left on my own most of the time, while my father and Melinda redoubled their efforts to grow their respective businesses.

The day everything changed, my father was on some sort of business trip. Catherine was at college. I had scarcely seen Melinda since my father had left two days before. It was a lazy Thursday afternoon in spring. I was, as customary, alone in the house. Bored with my books and music and television, I wandered, as I not infrequently did in her absence, into Catherine's bedroom.

Seemingly untouched since her departure, it had an air of a shrine to her. But, I was not there for anything holy. I went to her dresser and opened her top drawer. Neatly stacked inside were her panties and brassieres. My young cock became aroused merely looking at them. I had gazed on them many times before, but this time, I noticed another silky roll at the back of the drawer. I started to unravel them and realized that it was a pair of thigh-high stockings.

I ineptly rolled up the stockings and shoved them back into place. But, I could not help but start caressing my swollen dick through my jeans. Then imagining my cock sliding against Catherine's silky undergarments. And how good it would feel to be on top of her. And if I could not lay my cock atop her panties....

In a moment's inspiration, I slipped off my jeans and undershorts. Then, lifting a pair of cream panties from the drawer, I stepped into them and eased them over my raging erection. I loved the way my at-best average-sized penis strained against the silky material. Almost immediately, my precum began to soak through the undergarment. Just running my fingers along my cock, through the panties, felt heavenly. I tossed off my t-shirt and threw myself face down on Catherine's bed.

The comforter felt silky and cool against my cheek, as my pelvis began to grind against the mattress. I delighted in feeling my hard shaft and tight balls shifting inside Catherine's panties. I knew I could not dare to come right there, but I could not help and raise my buttocks into the air and begin humping the mattress. I remember thinking if only Catherine, or anyone, could have been beneath me.

"What. Do you think. You are doing?"

Melinda's icy words stabbed into me, halting me in mid-thrust. For a split second, I kept my eyes slammed shut. She was not due home for hours. I prayed that, when I opened my eyes, I would awake from a terrible dream. But it was not so.

"Answer me," she demanded.

Opening my eyes, I slowly got up and sat hunched on the corner of the bed with my eyes to the floor, unable to speak.

"Do you want me to tell your father what a little sissy his 'son' is?" Melinda asked.

"No, ma'am," I said anxiously, fear filling my chest. I was very afraid of my father in those days.

"If you don't want me to tell him, then you are going to do exactly as I say."

"Yes, ma'am."

"Stand up when you speak to me."

But, I was afraid to stand up. For all the terror coursing through me, it had done nothing to arrest my erection. If anything, my cock was straining even harder against Catherine's panties. Not helping was the fact that Melinda always took care to dress professionally, but alluringly, for her clients. As always, she was in heels just shy of being overly provocative in height. Stockings disappeared into a tight, above-the-knee skirt. From the skirt rose a form fitting blouse partly obscured by a short, tight jacket. Her dark, wavy hair was pulled back. Her normally cool blue eyes seemed to project both fire and ice my way.

"That's it," said Melinda. "I'm calling your father."

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"No," I pleaded, springing to my feet and trying to hide my excitement with my hands. But I could hide nothing from her.

"Oh, my God. Is this what you like? You like being a girl?"

I shrugged as tears began to stream down my face. Melinda approached, plucking one of Catherine's bras from the drawer.

"Here, put this on," she said.

I slowly put the straps over my arms, now openly sobbing. Melinda crossed behind me and cinched the bra across my back. Then she opened the closet and began going through Catherine's things.

"Put this on," Melinda said, tossing a pleated, plaid skirt onto the bed. "And this," she added when a white blouse followed.

Because of Catherine's voluptuous figure, I was able to fit into her things with ease. I gingerly stepped into the skirt and fastened its side clasps, then put on and buttoned her blouse. As I dressed, Melinda began going through Catherine's dresser.

"These, too," she said, handing me a pair of white, cotton knee socks.

Melinda brought a pair of shoes from Catherine's closet, but it was clear that my feet would not fit them. When I was through dressing, Melinda unbuttoned the top three buttons of the blouse and tied the tails off mid-abdomen, so some midriff was exposed above the skirt.

"Is this what you like?" she asked again. "You like to be a girl?" Melinda reached under the skirt and seized my still rigid cock. "Oh my God, you do. You really want to be a girl, don't you?"

Melinda pointed to the vanity next to Catherine's bed and told me to have a seat. As I walked gingerly across the room sniveling, I saw in the mirror Melinda take off her jacket and hang it on a post of the bed. She undid the top button or two of her blouse, and shook her head. When she looked up and saw me watching her in the mirror, Melinda moved quickly behind me, seized me under the chin, and pulled me back against her.

"You want to be a girl?" she asked, leaning over my shoulder to turn on the lights surrounding the vanity mirror and to pick up a container of hair gel.

Melinda took large gobs of gel in each hand and slicked back my nearly shoulder-length hair toward the nape of my neck. Coming around to face me, she applied shadow across my eyelids. Then, she teased out my naturally long lashes with mascara. Finally, she seized my cheeks to pucker my lips and drew a tube of dark, red lipstick across them.

"There," she said standing up, providing the first full look via the mirror at what she had done. Under the touch of her hand, I had stopped crying. I grew calmer with each wisp of her powdery scent. Even though her touch was harsh, each bit of contact felt like a caress for which I never knew I had longed. Now, when I saw myself in the mirror, I almost burst into tears again, but this time of joy. For the first time in my life, I felt attractive, desirable.

"Is this what you want?" asked Melinda yet again. "Stand up."

I complied, and Melinda again reached under my skirt and squeezed my aching erection.

"It is. Isn't it? You want to be a girl? You want to be a girl?"

My mouth formed, "Yes," but in my ecstasy, no sound came out of me.

"Get on the bed," Melinda directed.

I crawled up on the bed obediently. Melinda flipped the skirt up onto my lower back and began running her hand over my panty-clad bottom. I felt her nails dig into my buttocks.

"Nnn," I involuntarily moaned.

"Such a dirty girl," Melinda commented, before spanking each of my cheeks. Then she repeated herself, punctuating each word with a spank to my bottom. It was all I could do not to explode with each blow. I heard a dresser drawer opening behind me, and Melinda going through it. A second later, the leather of one of Catherine's belts was stinging my cheeks. I let out a louder moan.

"Oh, my God, you're such a dirty little thing, aren't you?" commented Melinda, her voice now low and slightly hoarse.

"Yes," I gasped.

She reached under me again to ascertain that I was still fully erect. Melinda pushed me forward and climbed on the bed behind me on her knees. Grabbing my waist, she began thrusting her pelvis against my ass and balls and grinding against them. "Is this what you want? To be treated like a girl?"

Momentarily speechless, I could only nod my assent.

"Stay right here and don't move," she commanded.

She was gone for a minute or two, during which time my arms and legs began to tremble in anticipation. But I could have never foreseen what was about to come. Melinda returned to the bedroom having loosed her dark hair and shed her skirt. From between the tails of her blouse protruded a thin black strap-on.

I gave out a short cry of fear, which only seemed to egg her on. Seizing the tub of hair gel from the vanity, she resumed her position behind me on the bed. "Now you're going to learn what it means to really be a girl," Melinda said as she slathered a thick dollop of gel between my cheeks. Then she began rubbing the gel all over her rubber cock. With her left hand, Melinda grabbed my waist, while with her right hand she targeted her cock at my rectum. As soon as the tip of her shaft began to part my virgin asshole, she grabbed my waist with her right hand as well. With little mercy, she plunged her cock into me.

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I cried out, falling to my elbows. But as uncomfortable as having my hole stretched was, my tears were as much for the tingling I felt all up and down my torso at the touch of Melinda's hands.

"Oh, my God," she cried. "I can't believe my son is such a dirty girl. Such... a... dirty... GIRRRRRL!"

Melinda was so aroused herself that, after only a few rude thrusts, she was coming. She collapsed onto my back and wrapped her arms around me. Her hand found my aching cock straining against my panties. Just one or two pumps and I was shooting ropes of cum straight through the panties and onto the comforter. Melinda squeezed my balls until the last bit of my cum dribbled out. When at long last Melinda released my testicles, she kissed me once on the back and slid off the bed. I turned around to see her putting on the heels she must have kicked off before fucking me, sodomizing me. With this she seemed to regain her characteristic composure.

"Clean this mess up," she said, in the same slightly disdainful tone she always addressed me and left the room.

I collapsed on the bed with but one thought filling my head, "She called me 'son.'"

***

Melinda and I avoided each other for the rest of the afternoon and all evening. She withdrew to her room while I cleaned up and went downstairs to make myself something to eat. Then I retreated to my room. I heard her about in the house briefly before I fell asleep. But, I was too intimidated to leave my own room, even to use the bathroom, until I heard the door to her room close behind her.

The next morning, I got up early and slipped into the bathroom, hoping to avoid Melinda before I left for school. But she had other ideas. In the shower, my head was spinning so that I did not even hear her enter the room. Rather, the shower curtain simply flew back, and the cold, unfeeling eyes of my stepmother stared at me, utterly indifferent to my nudity. I looked away.

"You're not going to school today," Melinda informed me. "I've already informed them that you're ill. Sick." She pointed to the corner of the vanity nearest the shower. There sat a razor, a bottle of liquid depilatory, and a bottle of lotion. "Make sure you remove any body hair - such as it is," she said, looking with seeming disgust up and down my nearly hairless body, "and use plenty of lotion when you're done."

She closed the curtain and left the room. My teeth began chattering as I awkwardly alternated between razor and depilatory, trying to remove every hair I could find on my body. Stepping out of the shower, shivering, I shaved my face as closely as I could. Then I began to slowly apply lotion to my body. Although it felt odd at first, the process began to calm me as a pleasant, jasmine scent was released from the lotion by the heat of my body.

When I was through, I stepped cautiously into the hall and went swiftly to my room. There on the bed was laid an outfit similar to the one in which Melinda had dressed me the previous day: white, knee-high stockings, a pleated, plaid skirt, and one of Catherine's white blouses. There was also a silky slip and panties and an old blazer I had nearly outgrown. My dress shoes were on the floor in front of the ensemble.

"Hurry up," Melinda called before I had even begun to dress. "We don't want to be late."

My heart began thudding wondering what she had in store. I quickly put on the outfit, my cock thickening against the panties as I did so. When I was through, I gave myself a quick, satisfied look in the mirror.

Melinda was waiting impatiently outside my bedroom door in her business attire. As soon as I opened the door, she grabbed my hand. "Come," she said, leading me back to Catherine's room. There, Melinda had me sit in front of the vanity, doing my hair and make-up, including some rouge, more carefully than she had the day before.

When she was through, she grabbed my face and forced me to look into the mirror. "Do you think you can be a good girl today?" she asked.

"Yes," I said softly. "Yes, ma'am."

"Let's go then."

Melinda strutted from the room. I cautiously followed her downstairs and found her waiting by the open front door. I approached slowly, but hesitated on the threshold of the house.

"Get in the car," she said flatly.

I stepped meekly onto the porch with my eyes down, but looking frantically back and forth to see if any of the neighbors were looking on. Surely this was a humiliation I would never live down if it ever made its way back to school. Melinda seemed completely unperturbed.

As she locked up the house, I moved swiftly to the car. My cheeks burned as I waited in the cool morning air for her to unlock the car, although I would hardly be less conspicuous in the vehicle. But, for all the fear and shame I was experiencing, as I got into the car, I struggled to hide the full blown erection beneath my skirt.

"There's just one thing you have to do today," Melinda informed me as she got in the car. "Pay very close attention."

Forty minutes later, we were being seated in the tea room of one of the most venerated hotels downtown. I had been so excited during the ride that I feared that a bump in the road might cause me to orgasm and incur Melinda's wrath. Only crossing the lobby, imagining all eyes upon me, abated my erection.

My cheeks began to burn again, and I grew lightheaded, whenever our waiter approached. This was long before the days of gender fluidity, and he seemed to sense that something was amiss. But, with Melinda ordering decisively with barely a glance at the menu, he served us our tea and sandwiches and cakes efficiently and without comment.

When the waiter was not at our table, Melinda did most of the talking, chatting amiably about her business and problem clients, as I imagined she would with Catherine. I hung on her every word. Periodically, she would stop and ask if I liked the course she had ordered. Each time, I hurriedly assured her that I did. At one point, I even relaxed enough to sit back and cross my legs.

After about 45 minutes, Melinda excused herself to use the restroom. She was gone long enough that I began to worry she might leave me there, cashless, to deal with the bill. But when she returned, she held out her hand to me, "Come on."

Hand-in-hand, Melinda led me back to the lobby. I began to become aroused again at her touch. That arousal grew when, instead of heading back to the parking garage, she led me to the elevators, and we took one up several floors. With my free hand, I adjusted my skirt to try and make my erection less conspicuous.

"Stop it," Melinda hissed. "Act like a lady."

When we reached our floor, Melinda pulled me by the hand off the elevator and down the hall. She opened the door to one of the rooms and pulled me inside.

"All right, missy," she said, tossing her purse onto a chair. "Let's see what's got you so hot and bothered. With her hands, Melissa gestured for me to lift up my skirt. I complied and looked away with tears welling up in my eyes.

From the corner of my eye, I saw Melinda step to me. Then, to my surprise, she sank to her knees in front of me. In a clinical voice, she observed, "I see. Your clit is very swollen isn't it?"

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