My name is Josie. Just like my name, I’m hella pretty. When I get really dressed up, I am killa, know what I mean?

I am a 16-rear-old girlish male. People tell me that I am beautiful and that I would, for real, make a beautiful girl. They are not wrong. I have long dark auburn hair and a toned, flexible body. Also, thanks to chemicals that my stepmom paid for, I have a new set of tits. They aren’t that big yet, but they will grow. I am shamelessly proud of them.

My stepmom, Donna, and I are close. She dotes on me and fuckin’ loves me like a fat boy loves cake!

Donna is a vice-president of New Business Development for a large global defense and aerospace corporation. A community college dropout, Donna comes from a blue-collar family. She is a socially liberal Republican. Blecch! She has buzz-saw ambition and work ethic, and she climbed the corporate ladder two rungs at a time, and her achievements are based on merit!

Donna is "mom" to me. I never refer to her as my stepmom. She is 5 ft 8 in, 132 pounds, with medium-length sandy brown hair and a killer body, especially in the ass department. She is a very capable, proactive woman, a real go-getter. She has a black belt in mixed martial arts. Usually, she is a sweet and kind person, but she does have a hot temper. Let me tell you something, YOU DO NOT WANT TO FUCK WITH DONNA!

The story opens with me in a flirtatious, attention-seeking mood.

It was a sunny Sunday morning. I was lying out on Donna's patio in a lounger, clad only in a sexy, skimpy black thong, a size too small, that revealed virtually all of my pretty teen ass, and stiletto heels. That was ALL I was wearing, dude. I am also wearing an expensive pair of slightly oversized designer sunglasses, a gift from Donna. I look like a fuckin’ snack! My end goal for this day is to give the world a hard-on.

Donna and I were the only ones at home. I was hoping she would appreciate me when she came out and saw me. I haven’t mentioned it yet, but I love Donna…more than a stepson should love his stepmom.

As the sun grew more insistent, so did my desire for attention. I shifted my hips, allowing my thong to glide against my smooth skin. A morning breeze played with my long auburn hair, which cascaded over my shoulders, brushing against my firm new breasts.

My thoughts grew more brazen as the heat of the day grew stronger. I knew that Donna would be out soon, and I couldn't help the thrill that shot through me at the thought of her eyes on my nearly naked form. Don’t get me wrong, Donna was a very proper stepmom, but her gaze held a certain power over me. But today, I was in the mood for pushing boundaries, to see just how far my proper stepmom would let this go.

The sound of the sliding glass door opening snapped me out of my daydream. I knew she would be dressed for the boardroom. The clack of her stilettos grew closer, and my pulse pounded in my ears. The click-clack of her heels echoed through the quiet morning, and I felt the heat of her body before I saw her. She walked out onto the patio; her silhouette framed wonderfully by the mid-morning light. "Josie," she called out, her voice a seductive purr that sent a shiver down my spine. "What on earth are you wearing?"

I opened my eyes and gave her a sultry smile, the kind that could melt a glacier. "Just catching some sun," I replied, my voice as smooth and sweet as honey. "Is there a problem?"

Donna paused, her hand resting on the back of the lounger, her eyes raking over me. I could feel her gaze on my bare flesh, and it made me squirm with naughtiness and nervousness. She took a deep breath, her nostrils flaring slightly. "No, darling," she murmured, her voice thick with something unspoken. "There’s no problem with you at all."

And with that, she leaned down and placed a kiss on my forehead that lingered just a little too long, her breath hot against my skin. Then she was gone, retreating into the house, leaving me trembling with excitement. I had her attention, and I was going to do everything in my power to keep it, to make this day one neither of us would ever forget.

The minutes ticked by, the sun growing hotter, and my need for more grew with it. I knew I had to be careful to tiptoe that fine line between innocence and seduction. So, I stood up, my legs shaking slightly from the thrill of the moment and sauntered over to the pool's edge. The cool water promised relief from the heat and the tension that had coiled in my soul.

As I dipped my toe in, the water washed over my right stiletto, and I couldn't resist the urge to kick it off, letting it clatter onto the patio. I watched as Donna, who had been engrossed in her paperwork inside, glanced up at the sound. She raised an eyebrow, and I could see the corner of her mouth twitch in amusement. Donna was always tolerant with me, but on this morning, I craved more than her amused indulgence. Slowly, I peeled off the thong, revealing my tight, bare ass to the world, or at least to the pool area. The fabric stuck to my skin briefly, and the sudden exposure to the air made me gasp.

With a dramatic flair, I tossed the thong aside and dived into the pool. As I surfaced, I slicked my hair back, the water running in rivulets down my body. My eyes locked with Donna's. She set her work aside and strode towards the pool, her heels clicking against the tiles.

My heart hammered in my chest as she reached the edge. She was dressed in a sleek business suit, looking every inch the corporate powerhouse. "I should be getting to work, but do you mind if I join you?" she asked, her voice low and husky. I nodded, my eyes never leaving hers, and she began to peel away her designer suit.

The water shimmered around us as she slid into the pool, her movements as graceful as a panther. We swam together, our bodies brushing against each other. I felt her hand on my waist, guiding me closer, and our legs intertwined under the surface. Our skin was slick with chlorinated water and sunscreen, making it easy for her to glide her palm over my hip, her thumb grazing my inner thigh.

The sensation was exquisite, sending bolts of pleasure straight to my little cock, which began to swell mightily despite its lack of size. I knew I was playing a dangerous game, but the thrill of it all was too much to resist. I leaned in, our mouths hovering just inches apart. The world around us seemed to melt away, leaving only the two of us and the promise of mutual surrender.

Her hand slid further up my thigh, reaching the juncture where it met my groin. Her eyes searched mine for any sign of hesitation, but all she found was desire. Did that desire mirror her own? Then with a gentle touch, she cupped my cock, her fingers wrapping around my smallness. A gasp escaped my lips as she began to stroke me, the water providing the perfect amount of lubrication.

Our breaths grew ragged, and she kissed me deeply. I thought I was gonna die! Her other hand found my ass, squeezing it firmly as she pulled me closer. I could feel her breath hot on my neck, her teeth grazing my earlobe as she whispered, "You're driving me crazy, little baby."

“I need you to be a little crazy,” I whispered.

The water splashed around us; our bodies entwined in a dance of building lust. I reached up, my hand sliding over her wet skin to cup her breast. Her nipple was hard. She groaned into my mouth, her hips bucking slightly against me.

The line between stepmother and stepson, between right and wrong, had been obliterated. All that mattered was the heat that threatened to consume us.

As Donna's hand imprisoned my cock, I felt my orgasm approaching, the sensation building in my belly like a storm. I broke the kiss, panting, and she took the opportunity to slide down on me. Way down. Then she wrapped her lips around my little pride and joy, her tongue flicking against the sensitive head.

I threw my head back, my eyes squeezed shut as pleasure shot through me. My body tensed, and I gushed in her mouth with a girly-boy cry.

For a moment, we just floated there, our breathing ragged and heavy. Then she pulled away, her eyes gleaming with a hunger that had nothing to do with breakfast. She leaned back against the edge of the pool, her legs spreading slightly, inviting me closer. I swam to her, my body reeling from the aftershocks of pleasure.

Her hand reached down, her fingers tracing the line of my jaw, guiding my mouth to her neck. I kissed her there, my tongue tasting her stepmom skin. She shivered, her hand moving down to the tie of her bikini top. With one quick pull, it came undone, and her breasts spilled out, full and heavy, the water lapping at the edges of her areolae. This had started to look like more than I could handle.

I took a breast in my mouth, the taste of her skin and the water mixing in a delicious cocktail. Her nipple was hard, and she moaned softly as I sucked on it. Her hand found its way back to my cock, which had already begun to recover from the accident in her mouth. She stroked me slowly, her thumb rubbing the sensitive spot just beneath the head.

The feeling was maddening, and I couldn't help but press my body closer to hers, my legs wrapping around her waist. She held onto the edge of the pool, her own legs spreading wider, giving me the perfect angle to grind against her. I felt her hand slip between my legs, her fingers sliding over my ass, and then she was pushing one inside me, the water making me slick and open.

Her eyes never left mine as she began to pump her finger in and out, her thumb circling my tight hole with an expertise that left me gasping. It was as if she knew every button to push, every spot to touch to make me squirm and beg for more. Where did my proper stepmom learn this shit? Her free hand roamed my body, tracing the curves, her nails digging in slightly as she pinched my nipples. The pain was delicious, making me arch into her touch.

I could feel myself losing control, my body responding to the two fingers that had found their way inside me. I reached down and grabbed her wrist, pushing them deeper inside me, the sensation of being filled by her sending me over the edge. She chuckled in a superior way and tightened her grip on me, her movements growing more forceful.

"That's it, baby," she murmured, her eyes dark with lust. "Take it all, you nasty little shit!"

With a sudden surge of power, Donna pushed me against the side of the pool, her hand pressing into the small of my back, holding me in place. She was no longer the sweet, nurturing stepmother; she had transformed into a lust-filled whore-mom, her strength making me gasp. She began to fuck me with her fingers, hard and fast, rough enough to shock me. I was hanging on for dear life! I had definitely bitten off more than I could chew!

Her other hand grabbed a fistful of my hair, yanking my head back as she claimed my mouth with hers, her tongue delving deep. Her kiss was bruising, demanding, and I gave in to it, meeting her passion with my own. Her teeth grazed my lower lip, sending sparks of pleasure through me. Her thumb continued to tease my asshole, pushing harder now, stretching me open, and I felt the beginnings of a second orgasm building. I belonged to Donna.

My own hands found their way to her shoulders, my nails digging into her skin as she worked me over. The water caressed our bodies as we moved together, the sound of our wet kisses and the slap of our flesh the only noise in the morning air. She broke away from my mouth, her breath hot and ragged in my ear. "Turn around," she growled, her voice a sexy snarl that sent a shiver down my spine.

I complied, my back arching as she spun me around. My palms flattened against the cool tiles, and I braced myself as she pulled my hips back towards her. The tip of her finger grazed my ass, sending a jolt through me. Then, with a firm push, she slipped it inside, her nail scraping against the sensitive flesh. I gasped, the feeling both painful and totally awesome.

Donna's strokes grew rougher as she fucked me with her hand. I could feel the head of my cock brushing against the tiles with every thrust. Her breathing grew heavier, her eyes hooded with desire as she watched my body react to her touch. "Is this what you want slut?" she panted, her voice thick with need. "Do you want to be my little slut?

“Forever,” I moaned in response, barely able to form coherent words. She leaned closer, her breath hot against my ear. "Tell me you want it," she demanded. "Beg for it, little bitch!"

The words spilled from my mouth before I could even think. "Yes, mom," I whimpered, the need in my voice unmistakable. "I want it. I want to be your slut. Only yours!"

With a smirk, she withdrew her finger and stood, the water cascading down her body as she stepped out of the pool. The sun caught the droplets, turning them into glittering jewels that danced across her skin. She walked over to a nearby lounge chair and picked up a towel, wrapping it around her waist, and then she grabbed my hand, pulling me out of the water. "Follow me," she said, her tone leaving no room for argument.

I stumbled after her, my legs wobbly from the morning’s events. We entered the house, the cool air a stark contrast to the heat of the poolside. She led me to her bedroom. I knew that shit was about to get real!

Donna dropped the towel, her eyes never leaving mine. She was like a predator. She sauntered over to her dresser, her hips swaying with a confidence that made my pulse race. She opened the top drawer and pulled out a large hairbrush. I swallowed hard, my heart thumping wildly in my chest. This was something new, something dark and exciting. I was about to get more than I had bargained for. Waaaaay more!

Turning to face me, she cracked the hairbrush against the palm of her hand, the sound echoing through the room. "On the bed," she ordered, her voice a seductive purr that sent fear and anticipation through me. I obeyed without question. I placed myself on all fours, my ass in the air, the frightening hairbrush now dangling from her fingertips.

Her hand caressed my back lightly, the leather a teasing promise of what was to come. "You've been a very naughty boy," she murmured, her voice low and gruff. I felt her straddle me, her knees pushing into the backs of my thighs, spreading them apart. "If you’re gonna be my little slut, I think it's time you learned your place."

The first strike of the brush was a rude surprise, a sharp sting that made me yelp like the little bitch she was turning me into. I had never seen this rough side of her before, but it made my cock throb. "Don't you dare move," she warned.

The second strike fell harder, across the tops of my thighs, and I felt the heat bloom across my backside. The pain was intense, but it only served to make my little cock harder. "Is this what you wanted?" she asked, her voice filled with amusement. "To be my little plaything? Do you think I’m playing?"

I was unable to speak, my eyes squeezed shut as she rained down blows across my ass and the backs of my thighs. Each smack of the hairbrush sent waves of pain and pleasure crashing through me, making me squirm and whimper.

Donna's breath was hot on my neck as she leaned down, the brush resting against my skin for a moment before she struck again. "You like this, don't you?" she whispered, her voice a mix of satisfaction and challenge. "You want me to mark you. I’ll mark you, but it will mark you as mine!"

The third strike was harder than the others, and I couldn't keep from crying. But with the pain came a rush of arousal that stole my breath away. No way was I going to plead with her to stop! I loved her too much to do that, and my cock was rock-hard.

"Good boy," Donna purred, her voice thick with satisfaction. "Now, let's see if you can handle more. You can show me how much you love me by handling more!" She moved the hairbrush to the small of my back. The anticipation almost broke my mind. Then, without warning, she brought it down across my ass with a crack that shook my little-bitch world.

I yelped like a little pup, the pain sharp and exquisite. But I didn't dare move. The sting grew until it was all I could feel, all I could think about. And yet, with each strike, I grew more determined to please her

Donna's breath grew ragged, her strokes growing more erratic. I...