I am Sanjay, a guy living in Hyderabad with my recently divorced mother, Hansika. My father and mother recently ended their 24-year marriage. There had been a lot of arguing over the past four years, and they finally decided to go through with the divorce. We are still living in Hyderabad, so almost none of my relatives have visited us. I am part of a family and a culture where divorce is still frowned upon. My father recently got a new job in Australia, and he shifted there. I was given the responsibility to visit his mother once every four to six months, to make sure she is okay and that all the chores in the house are well met. That was the only connection I had to my father's side of the family. My mother's side isn't great either; I wasn't close with most of them before the divorce anyway. My mother's sisters invite us occasionally and visit us rarely.
Divorcing her husband, with her elder son away for studies in the USA and isolation from all the relatives, made my mom feel very, very lonely. My mother was a beautiful woman, 5'5", with a thick lower body, an ass to die for, cute tits, B-cup, I think, and some tummy, a typical beautiful middle-aged woman.
About me, I was, at 5'7", the shortest man in the family. My brother and father were both over six feet, and I was always teased for being short. Also, I had thick thighs and an ass that was more similar to what women would have than men would. I had long dark hair till my shoulders, but the facial hair and body hair was very less, well, next to nothing. I didn't have any muscles; I had very small arms and fingers, but I did have some belly fat that would be considered cute on girls. Let's not fool ourselves; I've just described myself as a feminine guy, but this might change that opinion: I had a 7-inch girthy cock.
Something that no one knew about me was that I loved to crossdress. I loved to try my mother's clothes on when she wasn't home. I was turned on by wearing her underwear, her slips, her panties, her bras. I especially loved them even more if they were worn underwear. The fact that I was wearing the used panties that my mother wore gave me some of the best orgasms I had.
But my mom never had many sexy clothes to wear. She had many cotton panties, some bras with lace, some padded, some half slips, some camisoles, many sarees, many kurta sets, and some full slips that were very sexy. Compared to sexy clothes I've read about in stories and watched women wear, safe to say, I am disappointed with the clothes I had to work with. The fact that they were my mother's was doing the job.
I found myself pretty dug into an internet hole of crossdressing, bisexual, trans, and incest porn. Yes, you've read that right. Although I was a virgin, I wanted to have sex with both men and women and also had sexual thoughts of my family members, well, my mom in particular. I loved to read crossdressing stories, the ones where his mom finds out, and so on.
My kinky dream was to confess my crossdressing habit to my mom, and she accepts and helps me crossdress in her clothes, and I make love to her in lingerie. My current situation presented a great opportunity to make it possible.
As I said before, my mom becoming lonely made her feel vulnerable, and we have been spending more time together. I was worried she was going into depression; she stopped taking care of herself as much and was just getting through the days without any motivation and very little human interaction.
That is when I had this crazy and very risky idea that satisfies my needs and also helps cheer her up, but it depended on a very big "if." The "if"? We'll get into it now.
It was a week before my mom's birthday, and I wanted to give her a gift. Sure, the alimony money, thanks to my dad's new job, is even more than agreed upon at the time of the divorce, enough to buy her a gift, but I wanted to do something together, to break her out of her gloomy mood. So, I wanted to tell her my crossdressing secret, well, not directly, but make it look like I was doing it to cheer her up, and then later tell her.
So, it was the day before her birthday, and I decided to do it.
My mom was in the living room, watching a TV soap opera. Then I took the remote control and put the TV on mute, sat on the couch beside her, taking her hands into mine, and said, "Mom, tomorrow's your birthday. Tell me what I can do for you to make you happy?"
She responded with a weak smile, "You're so sweet, Sanju, but I'm not sure any gift can make me feel better with the year I've been having."
I said, "Come on, don't always be so sad. Let's brainstorm some ideas."
She said, "There really isn't anything I want. I just want to spend time with you, because you are everything I have left."
I replied, "Oh, Mom, please don't talk like that. Okay, if it isn't a gift you want, I have a crazy idea."
I continued, "You know you always were saying you missed not having a daughter. Well, to make you happy, and some fun for the both of us..." I paused.
I could see it in her eyes that she was excited, something about her daughter.
I said, "Let us have a girls' day."
She responded, "How can we have a girls' day?"
I replied, "Well, I will be your daughter for tomorrow. I'm not happy about doing it, I can't believe I even said that, but to make you happy, Mom, I would love to be your daughter for your birthday."
She was emotional, with a tear in her eye, and said, "You would really do that for me, Sanju? I love you."
She then hugged me, and I could already feel she was getting out of that sad mood.
I said, "Let's make it more fun. Let's start planning what we will do for tomorrow now, so the fun can start from now."
She wiped her eyes and said, "I would love that. Thank you so much, Sanju, for this."
I said, "I will dress as a girl, act as a girl, do everything as a girl for tomorrow. I will be your daughter tomorrow, but only inside the house." To make it look like I wasn't comfortable with crossdressing.
I added, "I want to dress in your clothes only, Mommy. I want this to be our personal secret. We will do what mothers and daughters do, we will do all the chores together, we will do our makeup together. Not that I know how to, but you'll teach me, right, Mommy?"
Mom hesitated for a moment, her eyes widening slightly as she processed my suggestion.
She pulled back from the hug, looking at me with a mix of surprise and uncertainty. "Sanju, are you sure about this? Dressing up as a girl in my clothes? It sounds fun, but I don't want you to feel uncomfortable or forced into it. You're my son, and I love you just as you are. Maybe we can think of something else?"
I shook my head quickly, trying to act reluctant while pushing forward. "No, Mom, really, it's okay. I mean, I'm not thrilled about it, who would be, right? Wearing dresses and all that stuff isn't exactly my thing. But if it cheers you up and makes your birthday special, I'll do it. Just for one day. Think of it as a silly game to make you smile."
She bit her lip, still unsure, glancing away for a second before meeting my eyes again. "Well, if you're absolutely certain. I do miss having those mother-daughter moments I always dreamed about. But promise me you'll tell me if it gets too weird for you?"
"I promise," I said, forcing a sheepish grin to hide my inner excitement. "Now, let's plan this out properly."
We spent the rest of the evening brainstorming, and Mom's mood lifted visibly as we talked. She suggested we start by picking out outfits from her wardrobe, insisting that if I was going to be her daughter, I had to do it right, from the inside out. "You can't just throw on a saree over your regular clothes, Sanju," she said with a playful scold. "If you're committing to this, you need to wear proper women's underwear. It won't feel authentic otherwise."
I pretended to groan, rolling my eyes dramatically. "Mom, really? Underwear too? That's embarrassing. Do I have to?"
She laughed softly, the first genuine laugh I'd heard from her in weeks. "Yes, you have to! Come on, it'll be part of the fun. Let's go to my room and see what we can find."
We headed to her bedroom, where she opened her closet and drawers, pulling out various items. First, she held up a pair of soft cotton panties in light pink, with delicate lace trim around the edges. "These are comfortable," she said. "Not too fancy, but they'll fit you nicely I hope" I blushed for real, acting mortified as I took them from her.
Next came the bras. She rummaged through her collection, selecting a white lace bra with subtle padding. "This one has a bit of support," she explained. "We can stuff it with socks to give you some shape. And here's a matching camisole, silky white, with thin straps. It'll go under whatever we choose on top."
She didn't stop there, pulling out half slips in smooth nylon, one in beige that reached mid-thigh, and a full slip in soft satin, black with lace detailing at the hem and bust. "These will make everything drape better," she said knowingly. "You can't wear a saree without a slip underneath; it'll bunch up otherwise."
We tried on different outer clothes too. Mom had me slip into a simple kurta set first, a light blue cotton kurta with embroidered patterns along the neckline, paired with matching leggings. "See how it feels," she urged. I changed in the bathroom, coming out awkwardly, tugging at the fabric. "This is weird, Mom. The leggings are so tight."
She giggled. "That's how they're supposed to be! Now, try this saree." She draped a soft chiffon saree in pastel green over me, teaching me how to pleat it. It felt light and flowing, the material whispering against my skin. We experimented with a few more: a red silk saree that was heavier and more luxurious, clinging in all the right places, and a cotton one in yellow for something casual.
But Mom wasn't done. "If you're going to be a proper girl, you need to shave your whole body," she declared firmly. "Those little hairs you have will show through the fabrics, and it won't look right. Come on, I'll teach you how."
I feigned hesitation again. "Shave everything? Like, legs and arms? Mom, that's a lot. Can't I skip that?"
"No skipping," she insisted, leading me to the bathroom. She showed me how to use her razor carefully, starting with my legs.
"Lather up with soap first, then go against the grain gently. Do your arms, chest, everything below the neck." It took time, but as I followed her instructions, my skin emerged smooth and soft, heightening my secret thrill. She even helped with the hard-to-reach spots on my back, her touch innocent but sending sparks through me.
By the time we finished planning, it was late. "Tomorrow we'll wake up early," Mom said, excited now. "We'll both take head baths, get me ready in my net saree, and then transform you into my beautiful daughter."
The next morning, we both woke up at dawn, the air fresh with anticipation. Mom and I took our head baths separately, the warm water cascading over us as we prepared for the day. She emerged first, her hair wet and draped in a towel. I watched as she got ready, selecting an elegant black net saree with silver embroidery that sparkled subtly. She paired it with a matching blouse that hugged her figure, the net material sheer enough to hint at her curves without being overt. She draped the saree expertly, the pleats falling perfectly, and added a simple gold necklace and bangles. Her makeup was light, kohl-lined eyes, a touch of lipstick in soft pink, and her hair tied in a loose bun. She looked radiant, the loneliness fading from her face.
"Now, your turn, my daughter-to-be," she said with a wink. We went back to her room, where she had laid out everything. First, the wig: she had an old one from a costume party, long black waves that reached my shoulders, similar to my own hair but fuller. She pinned it securely, brushing it out until it framed my face softly.
Dressing started from the basics. "Panties first," she instructed, handing me a pair of white cotton ones with floral lace borders. They were soft, slightly worn from use, which secretly thrilled me. I slipped them on in the bathroom, feeling the fabric hug my skin, my cock stirring despite my efforts to stay calm. Next, the bra, a beige padded one with underwire for shape. Mom showed me how to clasp it from the front and spin it around. "Now, for the fillings," she said, grabbing a pair of rolled-up socks and stuffing them into the cups, creating modest B-cup mounds that mirrored her own.
Over that, a white camisole in smooth satin, the straps thin and the material cool against my freshly shaved chest. Then a half slip, ivory nylon, knee-length, with a lacy hem that swished as I moved. "This will prevent the saree from sticking," she explained.
For the outer layer, we chose a vibrant pink saree in georgette fabric, light and airy with golden zari work along the borders. Mom helped me into the petticoat first, a matching pink cotton one that tied at the waist, then the blouse, a short-sleeved pink piece with hooks down the back. She draped the saree meticulously, tucking the pallu over my shoulder, adjusting the pleats until they fanned out neatly. I got hard during the process, the intimacy of her hands on me, the feel of her clothes enveloping my body, it was almost my fantasy come true. I shifted awkwardly, hiding the bulge under the layers, pretending it was just discomfort.
"Look at you," Mom said, stepping back with tears of joy. "My beautiful daughter. What should we call you? Sanjay doesn't fit anymore."
I thought for a moment, heart racing. "How about Saanvi? It sounds nice."
"Saanvi it is," she agreed, hugging me gently. "My sweet Saanvi."
We spent the morning doing chores together, just like mothers and daughters. First, the kitchen: Mom taught me how to chop vegetables for breakfast, calling me "beta" but quickly correcting to "beti" with a laugh. "Saanvi, hand me the spices," she'd say, her voice warm. We made idlis and chutney, the steam filling the air as we worked side by side, her net saree brushing against my pink one.
Then, laundry: folding clothes from the line, her showing me how to iron a saree without creasing it. "Careful, Saanvi, don't burn the fabric," she advised, treating me fully as her daughter. Sweeping the floors came next, the broom in my hands feeling natural under her guidance. We dusted the shelves, cleaned the windows, all while chatting about silly things, old family stories, her favorite soaps, what "girls" like us should do for fun.
By lunchtime, we were tired but happy. We prepared a simple meal of rice, dal, and sabzi, eating together at the table. Mom kept glancing at me, smiling. "This is the best birthday gift, Saanvi. Thank you for being my daughter today."
After lunch, Mom yawned. "I think I'll take a short nap, dear. All this excitement has worn me out." She headed to her room, leaving me alone.
I wandered to my own room, closing the door behind me. Standing in front of the full-length mirror, I stared at my reflection. There I was, dressed as Saanvi in my mother's pink georgette saree, the golden zari glittering under the light. The wig cascaded in soft waves, framing my smooth, shaved face. The padded bra gave me subtle curves, the camisole peeking slightly at the neckline, and the half slip rustled faintly as I shifted. It was surreal, my mother's clothes on my body, her knowing about it, even encouraging it. The panties hugged me tightly, a reminder of the intimacy.
A wave of arousal hit me hard. My cock, already semi-hard from the morning's touches, throbbed insistently under the layers. Seeing myself like this, feminine and desired in my own eyes, living out the fantasy I'd hidden for so long, it was overwhelming. I reached down, my hand slipping under the saree's pleats, stroking through the fabric at first. The georgette was soft, sliding against my skin as I traced the outline of my erection, hidden beneath the pink petticoat.
But I didn't want to risk staining the panties, they were hers, after all, worn and special. Carefully, I hiked up the saree and petticoat, the materials bunching around my waist in a cascade of pink and gold. I slid the white cotton panties down my smooth thighs, letting them pool at my ankles. My 7-inch girthy cock sprang free, hard and veined, contrasting sharply with the feminine attire above and below.
I stepped out of the panties, kicking them aside gently, and faced the mirror again. Now, with my cock exposed, the sight was even more erotic: Saanvi in her saree, but with this masculine secret jutting out, demanding attention. I wrapped my hand around it, the grip firm, starting with slow, deliberate strokes. The skin was sensitive from the day's build-up, each pull sending shivers up my spine.
My mind wandered to forbidden places. I imagined my mom, Hansika, beautiful in her black net saree, discovering me like this. Not as her son, but as her daughter turned lover. In my fantasy, she enters the room quietly, her eyes widening at the sight of me pleasuring myself. But instead of shock, there's desire. "Saanvi," she whispers, her voice husky, stepping closer. Her hands, the ones that draped me earlier, now undo her own saree, the net fabric falling away to reveal her thick lower body, that ass to die for, her B-cup tits in a lacy bra.
I stroked faster, my breath quickening. In the dream, she presses against me, our sarees tangling as she kisses me deeply, her tongue exploring. "You've been such a good daughter," she murmurs, her hand replacing mine on my cock, pumping it with expert care. I picture her guiding me to the bed, pushing me down gently, her body hovering over mine. She lifts her saree, no panties underneath, her wetness evident as she lowers herself onto me, my girthy length filling her completely.
The mirror reflected my flushed face, the wig slightly disheveled now from my movements. I squeezed harder, twisting at the head, pre-cum beading at the tip and lubricating the strokes. Fantasy deepened: we're in lingerie now, her in a full black satin slip, me in the white camisole and half slip. She rides me slowly at first, her tummy pressing against mine, her cute tits bouncing in rhythm. "Make love to me, Saanvi," she moans, even though I'm the one penetrating her. The roles blur, I'm her daughter, her lover, crossdressed and claimed.
My free hand roamed, cupping the sock-filled bra, imagining they were real, hers to touch. I pinched a "nipple" through the fabric, gasping. In my mind, she's on her knees now, that ass presented, begging me to take her from behind. I thrust into the air slightly, my hand mimicking the motion, faster, slicker. Her moans echo in my head, "Yes, harder, my sweet girl." The incestuous thrill peaks, the taboo of it all fueling the fire. She's lonely no more, filled by me, her body writhing under mine.
Sweat beads on my forehead, the saree clinging damply. I slow for a moment, edging myself, wanting to prolong the ecstasy. The mirror shows Saanvi in heat, cock in hand, panties discarded like a secret shed. Back to the fantasy: we switch, her teaching me more "girl" things, but twisted, her fingers exploring my ass, preparing me as if I were truly feminine. But no, I reclaim, flipping her, pounding into her with all my girth, her walls clenching around me.
The climax builds uncontrollably now. My strokes are frantic, hand blurring, balls tightening. In the vision, she cums first, screaming my girl name, her body shuddering. That pushes me over, hot ropes of cum erupt, splattering the mirror in thick spurts, some landing on the saree's hem. I groan loudly, knees weakening, milking every drop as waves of pleasure crash through me.
Panting, I lean against the wall, cum dripping down the glass, marking my reflection. The afterglow settles, reality creeping back. I've climaxed to the thought of making love to her, dressed in her clothes, her knowing me as Saanvi. It's the best orgasm yet, but guilt mixes with satisfaction. I clean up quickly, careful not to stain more, tucking everything back into place before Mom wakes.