Breakfast at 16-year-old Kota's house was always a little unusual. Kota’s mom, Lara, the epitome of a modern MILF, age 36, with her auburn hair pulled back in a messy bun and an apron hugging her curvy figure, bustled about, serving up breakfast for her children. Her sweet, nurturing smile never wavered, even when the conversation took a rather... intimate turn.
"So, Kota," she began, placing a stack of fluffy pancakes in front of me with a slightly knowing glint in her eye, "I found your... outfit stuffed under your bed. The one with the very short hemline?"
I felt the heat rise to my cheeks, my heart thumping in a mix of embarrassment and arousal. Brianna, Bri for short, my bitchy, yet beautiful 19-year-old sister, looked up from her phone, a smug smirk playing on her lips as she took in my discomfort. She had always been aware of my secret penchant for crossdressing, and she took every opportunity to poke fun at me for it.
"Oh, you mean his 'girl clothes'? I've seen those! What a weirdo!" Brianna giggled, her voice a sultry mix of tease and mockery. She took a sip of orange juice, her eyes sparkling with mischief as she looked at me over the rim of her glass.
Lara chuckled, the sound a delightful blend of amusement and understanding. "Well, honey," she said, placing a gentle hand on my shoulder, "if it makes you happy, then who am I to judge?"
Her acceptance, however tinged with humor, sent a thrill through my body, and I couldn't help but feel my cock stiffen in response. The fabric of my loose sweatpants stretched, creating a telltale bulge that I hoped would go unnoticed.
"Come on, Mom," Brianna scoffed, rolling her eyes dramatically, "you can't be serious. He looks ridiculous in that getup!"
Mom's hand remained on my shoulder, her touch a silent show of support amidst the teasing. "Brianna, honey, let your brother be himself," she said firmly, though the corners of her mouth twitched with the effort of not laughing.
The tension in the room was palpable, a delicate dance of acceptance and ridicule, but the warmth from Mom's hand was grounding. The smell of the breakfast spread grew stronger. The sight of the syrup cascading over the pancakes made me think of something else entirely, something thick and sticky and sweet. The way I always imagined Bri was down there.
Bri's laughter grew louder, a musical sound that seemed to echo through my body, making my hard-on throb with every giggle. I felt a strange mix of embarrassment and exhilaration, my body responding to the humiliation in a way I couldn't quite comprehend.
"Maybe you should join in, Bri. You know, help me out a little," I retorted, trying to regain some semblance of dignity. "You might like it."
Her eyes widened, a look of feigned horror crossing her face. "I'll pass, Kota. I'd rather keep my dignity, thanks," she said, stifling another giggle. “You’re so weird!”
The conversation continued, a blend of jibes and jokes, but Mom's touch remained constant, a reminder that amidst the teasing, she was still on my side. The air was thick with a mix of emotions—desire, humiliation, and love. And as I took a bite of my pancake, I couldn't help but wonder what it would be like to serve breakfast to both of them as the girl I truly wished to be.
Mom's hand slid away from my shoulder, and she returned to her own plate, her eyes lingering on me with an intensity that sent shivers down my spine. "You know, Kota," she began, her voice dropping to a whisper that seemed to carry through the room, "I think you really would make a pretty girl."
"Oh my God, Mom. Nothing in the world could ever make me happier than that. I wish I could look just like Bri. Everyone loves her. Boys want to fuck her. Girls want to fuck her. And she’s just like ‘ho hum’ like it's just normal and it's no biggie."
Lara took a sip of her coffee, her gaze lingering on me over the rim of her mug. "Well, honey," she said, her voice a smooth purr, "you do have a certain... je ne sais quoi. A delicate beauty that could be quite alluring with the right makeup and wardrobe."
I said, "When I try, I can never get it the way it should be. I wind up looking like a dumbass in his mom's dress!"
Mom leaned over, her breasts brushing against my arm, sending a jolt of electricity through me. "You just need the right guidance," she murmured, her breath warm against my ear. "Let me help you, Kota. I think you'd be absolutely stunning."
Bri, who had been silently watching the exchange, finally chimed in, her voice dripping with sarcasm. "Yeah, Kota," she said, her eyes dancing with amusement, "Mom could totally turn you into a hot little slut."
I shot back, "I would love for Mom to help. She's beautiful, and she could make me beautiful. Mostly, I’d like to look like a slut more than be beautiful. But you're the one with the slut know-how, Bri. You're the fuckin' expert at that."
Bri rolled her eyes again but put down her phone and took a more deliberate sip of her orange juice, the ice cubes clinking against the glass. "Fine," she said with a dramatic sigh, "I'll show you how to be a slut. But you gotta promise to leave me alone about it after that."
"You know I could never leave you alone about anything, Bri. If I bothered you it would just make you bitch at me. That's the only attention I can get from you," I said.
Mom chuckled, standing up from her chair, wiping her hands on her apron. "Alright you two, let's not get ahead of ourselves. Kota, I'd love to help you feel more comfortable in your own skin, but we should maybe start with something simple. How about I help you with makeup and clothes?"
Bri leaned back in her chair, her smug grin turning into a slightly more serious expression as she studied me. "Yeah, Kota. Maybe Mom can teach you to be pretty, but I'll teach you to be a slut. You're going to need it if you want to get the kind of attention I do."
I exclaimed, "I would give anything for that!"
Brianna's eyes gleamed with a newfound interest, the mocking tone in her voice replaced by something more... curious. "What do you say, Mom?" she asked, turning to Lara with a grin. "Want to give your baby boy a makeover? We can take turns getting the whole thing on video!"
Lara raised an eyebrow at her daughter's enthusiasm, but there was a spark in her eye that suggested she was intrigued by the idea. "Brianna, let's keep it respectful, okay?" she said firmly, though she couldn't hide the smile that played on her lips. "Kota, if you're serious about this, I'll help you, but we need to do it with dignity."
Without another word, the two of them sprang into action. Brianna rushed to her room, returning with an armful of clothes and makeup, while Lara cleared the table with surprising efficiency. My heart pounded in anticipation, a strange mix of excitement and dread coursing through me. I had always longed for this moment, but the reality was more intense than any of my secret fantasies.
Mom led me to the bathroom, her hand a comforting presence on my lower back. She opened the vanity and began rummaging through the contents, pulling out various brushes, lipsticks, and eyeshadows. The smell of her perfume, a delicate blend of jasmine and vanilla, filled the room, making me feel both safe and incredibly aroused.
"Now, Kota," she began, her voice soothing, "I want you to sit down and relax. We're going to start with the basics: foundation, blush, and some mascara."
Her gentle touch was like a whisper against my skin as she began to apply the makeup. Each stroke of the brush sent waves of pleasure through me, and I couldn't help but lean into her, my body responding to the intimacy of the moment. Her eyes met mine in the mirror, and for a brief second, I saw something in her gaze that went beyond motherly care.
Brianna, on the other hand, was less subtle with her intentions. She hovered in the doorway, watching us with a predatory smile. "Mom, don't forget to make him look like a total slut," she called out, her voice dripping with glee.
The first touch of the mascara wand against my lashes was surprisingly sensual, and I found myself leaning into the touch, my breath hitching slightly. Mom's eyes met mine again in the mirror, and she winked before saying, "Don't worry, Bri, I'll make sure Kota's transformation is... thorough."
Her fingers were deft as they painted my lips a glossy shade of red that made me feel both vulnerable and powerful. I watched in amazement as she transformed me into a reflection of herself, her own beauty reflected in my eyes. When she was done, she stepped back and surveyed her work, a proud smile on her face.
"Wow, Kota," she breathed, her hand resting lightly on my shoulder, "you really are beautiful."
Brianna's voice grew impatient from the doorway. "Come on, Mom, let's get to the good part," she said, her voice thick with suggestion. "I want to teach him how to be a real slut."
The air in the room grew charged as I stood up, the silky fabric of the dress Mom had chosen for me brushing against my legs. The feeling was alien and exhilarating, my cock straining against the fabric of the panties I had borrowed from Bri. I could feel their eyes on me, assessing and planning, and I knew that I was about to embark on a journey that would change me forever.
Mom took a step back, her hand sliding down to cup my ass-cheek. "You're going to be the prettiest daughter anyone has ever seen," she whispered, her thumb tracing a line of gloss across my bottom lip. "And Brianna will show you how to make sure everyone knows it."
Their eyes locked in the mirror, and I knew that I was their new project, a canvas for their desires and whims. I felt a thrill of excitement mingled with fear, my body responding to their attentions in ways I had never allowed it to before. I was no longer just Kota, the shy and awkward boy, but a creature of beauty and temptation, ready to be shaped by the hands of the two most important women in my life.
As Brianna stepped closer, her hand sliding down my back to give my ass a playful squeeze, I knew that I was about to discover a side of myself that I had only ever dared to dream about. And as she whispered in my ear, her breath hot against my skin, I felt a rush of anticipation that left me trembling.
"Ready to be the slut of the family?" she asked, her voice a seductive purr.
"I could never outdo you, Bri. But I could be the junior slut! I could be your sidekick!"
Her eyes glinted with excitement at the prospect, and she took over from Mom, her movements more aggressive, more possessive. She had me step into a pair of high heels that were definitely not made for walking, let alone my tiny feet. They pinched, but the pain only added to the thrill, making me feel like I was truly giving in to their whims.
"Now, let's show off those legs," she said, her voice a low growl. She bent down and began to roll up the hem of the dress, exposing my smooth, shaved thighs. The fabric tightened around my waist, highlighting the swell of my hips and the bulge that was becoming increasingly difficult to ignore.
Mom watched with a smile that was both proud and a little... hungry. Her eyes roamed my body, lingering on my chest, which she had stuffed with her own silicone pads to mimic the curves of a woman. The weight of her gaze was like a caress, and I found myself pushing my chest out, eager for more of her attention.
With a flourish, Brianna produced a short, lacy skirt that she had obviously picked out for herself. "This will do," she murmured, slipping it over my hips and adjusting it so that it barely covered my ass. I could feel the cool fabric brushing against my skin, and I knew that the slightest breeze would leave me exposed.
Mom stepped aside, allowing Bri to take the lead. She grabbed my hand and pulled me towards the living room, where the sun had moved to cast a soft, warm light that highlighted the new me. "Let's get some practice in," she said, her eyes gleaming. "You need to learn how to walk, talk, and act like the slut you want to be."
The floorboards creaked as I took tentative steps in the heels, the skirt riding up with every step. My cock strained against the fabric of the panties, begging for release. The sensation was both terrifying and exhilarating, and my cock, a little small for a boy my age, was hard as a brick.
Brianna positioned me in front of the floor-length mirror, her hand resting possessively on my hip. "Look at yourself," she said, her voice a soft command. "You're going to be the hottest thing on two legs."
I stared at the reflection, hardly recognizing the creature that stared back at me. The makeup was flawless, turning my features into a softer, more feminine version of myself. The dress clung to my body, the skirt portion riding up to reveal the tops of my stockings. And the heels... oh, the heels. They made me feel tall, powerful, and utterly at their mercy. They were knock-me-down-and-fuck-me pumps!
"Now, Kota," she said, her eyes dark with lust, "let's see if you can handle this." She reached down and began to rub my cock through the fabric, her movements slow and deliberate. "You're going to be everyone's little fucktoy. You're going to beg for it, and you're going to love every second of it."
Her hand grew bolder, her grip tightening as she worked me closer to the edge. My breath came in ragged gasps, my body responding to her touch in ways I had never allowed before. The pleasure was intense, a heady mix of humiliation and desire that made me feel like I was floating.
"Mom," I gasped, my voice high and needy, "Bri's hand... "
Lara stepped closer, her hand reaching out to trace the outline of my cock, her touch feather-light. "Go ahead, baby," she whispered, her voice filled with a warmth that seemed to come from somewhere deep within her. "Let it go for us."
The words were barely out of her mouth before I came, the orgasm ripping through me like a storm, leaving me trembling and gasping for air. The warmth of Brianna's hand never left me, her nails digging into my hip as she watched me with a mix of amusement and pure mischief.
Mom stepped back, a knowing smile on her face as she surveyed the mess I had made in the panties. "Well," she said with a laugh, "it looks like we have a natural. You made quite a puddle, Kota."
The warmth of embarrassment flushed through me, but the look in Brianna's eyes was pure fire. "Looks like you're going to need a change," she said, her voice a sultry purr that seemed to resonate through my entire being. "But I think you should wear those just the way they are. You stole them from me, and Mom jerked you off in them. Now you can wear them. You can walk around in them right here in the house in front of me and Mom until they dry!"
My face burned with a mix of embarrassment and arousal, but I couldn't deny the thrill of her words.
"But Bri, they're all sticky," I protested.
Brianna just laughed, her eyes sparkling with amusement. "That's the point, Kota. It's all part of being a slut. You're going to get used to wearing cum-stained panties. It's like a badge of honor." She says it with a straight face, but the glint in her eyes gives away her mischief.
Mom watched us, her expression unreadable. Then she surprised me by speaking up, "Brianna's right, Kota. If you want to be treated like a slut, you're going to have to get used to feeling like one." Her voice was gentle, but there was a firmness to it that told me she was serious. And the way she said "slut" wasn't like it was a bad word, but more like it was a title I should aspire to.
Then I whine, "But Mom, they're all sticky. This is so embarrassing for me for you to see me like this! These panties are cute, but they're nasty!"
Mom's sweet demeanor shifted ever so slightly, the corners of her mouth tightening into a line of impatience. "Kota," she said, her voice a bit more stern, "I know this is all new to you, but you're going to have to get over your whiny nature if you want to truly explore this side of yourself. Being a slut isn't just about looking the part; it's about embracing it fully."
At the risk of making my pretty mom mad at me, I ask, "But walking around in sticky panties, Mom?"
Mom gets a little angry and says, "Kota, don't be a whiny little bitch. You do know that pretty little sluts get spanked sometimes!"
Brianna laughed, a delighted sound that sent a shiver down my spine. She sauntered over, her own body a study in feminine power. "Here," she said, her voice a whisper, "Let me help you." She slid them down my legs, her eyes never leaving mine, and I stepped out of them, feeling the sticky mess between my thighs. Then Bri held the damp fabric to my face, and the scent...