I’d gotten home from my community college class and taken a shower so I wouldn’t leave my smell on her lingerie. My stepmother, Cheryl, who insisted I call her “Mom,” was working this afternoon. I could safely dress up in her undies, watch porn and jack off for several hours, maybe cum twice.

I didn’t have to worry about my dad catching me; two months ago he called to say he’d met the perfect woman and was staying in Spain to live with her—a business trip he never returned from. It had been just Mom and me all this time.

With all his money and lawyers he was able to keep most of his money by giving Cheryl the house and a $20,000 check every month, plus another $5000 to support me. This is why I had no job and, at nineteen, I was just treading water in college. Why work?

Cheryl was a little taller than me and we had the same size feet, but so far I’d stuck to panties and high heels. I’d fantasized about going all the way with a full ensemble and makeup—my hair was already just past my shoulders—but part of me was afraid to go too far. I wasn’t a sissy or a shemale or anything. That’d be too freaky.

The see-thru pink panties! The matching bra this time too!

Cheryl retired from porn and dominatrix work when she married my dad—he was uptight about that stuff—but since he left, Mom returned to sex work. At thirty-three, Cheryl was still hot enough!

I put on the panties and bra, plus some of her stripper platforms. As a final touch I moussed my hair and styled it like a porn star slut—a shemale’s hair. The finishing touch was a condom so not even pre-cum could stain her panties.

Imagine being one of those shemale webcam sluts!

I didn’t dare to get on her bed, so I lay on the floor in front of the big mirror and teased my boner through her panties, imagining myself as a shemale slut who fucked girls. I started with girls from high school—cheerleaders Lindsay and Jessie and the other sexpots—and quickly graduated to Cheryl’s stripper friends.

I teased my cock through the panties and checked out my ass in the mirror—my round, girly butt! A sudden fantasy of Cheryl fucking that butt with a strap-on dildo made my cock almost painfully hard.

Fuck it. You can cum right now and you still got the rest of the afternoon to play with it and jerk off a second one!

I got up and sashayed right out into the hallway. It was exhilarating to walk around the house in Mom’s sexy underwear and in high heels. I left my bedroom door open and went to my bed. My laptop lay right there, still on a shemale website.

I pulled my cock out, still wrapped up in latex, and began going at it hard to cum quickly. I was close to cumming when I heard the most terrifying thing imaginable: my stepmom’s voice at my bedroom door.

“Pink isn’t your color, baby,” Cheryl said. “Let Mommy help.”

She was shooting me with her phone. I screamed. Like a girl.

* * *

I’d known for weeks he’d been going into my lingerie drawers and suspected he might be trying on my panties, but the bra and heels spoke volumes about him… or should it be “her” now?

“M-mom! I… it’s not what it looks like!” he babbled as he tucked his cock back into my sheer pink panties.

I stopped filming. “Tell me what it is then, Teddy. You’ve raided my lingerie and shoes like a sissy. I know you like looking at them, so maybe this is like a cry for Mommy’s help?” I chuckled at his shocked expression. “I’ve been on your laptop.”

He turned indignant. “What gives you the right to do that?”

“As your mother it’s my duty to make sure you’re not getting off to sick shit—rape, torture… kids.” I said the last word with all the distaste I had for it. “If you were I’d get you some help. I’m glad to see you’re just watching normal stuff.”

“Shemales. Trans. BDSM. Normal?”

“Yes, normal. I was in the sex business long before I married your father. You’d be surprised how many men and women are into those things. It’s clear you are!”

“It’s just an experiment. I’m not really into it. I swear I won’t do it again, I promise, Cheryl!”

“Mom!” I snapped. Then I turned motherly. “Honey, I know you’re afraid of your desires. I’ve known so many who were. If you are trans there is nothing you can do to shut off the feelings. So I’m going to help you figure out yourself.”

“I don’t need your help!”

“Oh yes you do. The best way to see what you are is for you to try things, so Mommy is here to teach you all she knows.”

“What if I don’t want to?” He crossed his arms in defiance. It was so cute: him a portrait of a submissive sissy and yet acting “tough.”

“Then I’ll send this video to your father,” I said calmly.

All the blood drained from Teddy’s face. The $5000 his father sent for his expenses was contingent upon him being in college and “having good moral character.” The Prius it leased for him, his food, his pot and spending money would all be gone.

“Please don’t” he whimpered.

“Of course,” I continued, “you’d need to start paying rent too. Seeing you’re my son—maybe—I’d only charge $2000 a month.”

The tears in his eyes and his quivering lower lip meant I would have my way with him. His browser history showed an obsession with shemales, and his personality was so like the many sissies and potential shemales I’d encountered as a dominatrix.

He wiped his eyes. “I’ll do anything you want me to… Mom.”

I’m glad you’re not my real son, because I’m so horny, baby!

I sat him in my makeup chair, leaving on the pink lingerie for now. Still wearing only my panties I sat on my vanity and faced him. I took a pair of tweezers and plucked his eyebrows. Fortunately for him they weren’t too thick, so I quickly sculpted feminine arches.

His dick stayed hard the whole time.

Then I got out my frilliest, laciest see-thru ensemble I used for my best crossdresser clients and slipped in $100 breast forms. Five-inch heels made him sexiest and also made it hard for him to walk. He’d be a pro in them by next week.

He gasped in awe as I stood him in front of my dressing mirror. “I look so beautiful, Mommy! Can I please wear some makeup?”

“We’ll get to makeup. And work on your girl voice. But first things first…” I smiled. “You’ve been lifting my panties out of the laundry and sniffing haven’t you? Don’t worry, Mommy isn’t mad.”

He turned red blushing. “Yes, Mom.”

“You love how Mommy’s pussy and ass smells, don’t you?”

“Yes, Mom.”

I stood eye to eye with him. “You fantasized about being lesbians with me too, haven’t you baby?”

He bit his lip, eyes filled with desire. “Yes, Mom.”

“Then it’s time to turn you into a girl. What’s the best sexy girl name you can think of?”

His shuddering exhale made me realize I’d been right about him. He licked his lips and said,

“Heather.”

I snickered. “Too classy for a sissy slut. I think you are… Amber. It’s perfect. I shot porno scenes with an Amber, a real sex maniac. She lived to get fucked with my strap-on, eat my pussy. Maybe I’ll let you do that if you’re good… Okay, take out your sissy clit to show me.”

Shyly he pulled out his hardening cock. When I saw the condom I realized how careful and clever he’d been. For all I knew he’d been trying on my panties for weeks or months!

“I put this on so you wouldn’t get mad, Mom.”

“That’s very good of you, baby,” I said. I stripped it off and was pleased at how much precum had collected. “You won’t need this anymore. Mommy’s going to let you blow your first load in her sexy panties.” I winked. “Then you’re licking them clean.”

“Oh my god!”

“Let’s go to the bathroom so Momma can clean you out.”

“The bathroom, Mom?” he worried, suddenly shy.

“You want your sissyhole to be clean for Mommy, don’t you?”

He turned bright red and his boner started doing pushups in my panties. That was when I realized that, deep down, I’d not only been right about my stepson all along but I was also so horny for him.

* * *

While she began filling the tub, Mom hung up the enema bag high over the toilet so the water would rush harder into my sissy ass. She commanded me to strip. When the tub had filled halfway, she had me get in and handed me a razor.

“Good girls don’t have hairy bodies,” she instructed

My boner throbbed while I sat in that perfumed water and shaved my legs and forearms and the peach fuzz on my chest.

My near-naked mom went to work with a fresh razor until my face was smoother than it had ever been. She filled the enema bag with warm water and red wine—she said it would give me a nice buzz and lower my inhibitions for what came next.

Suddenly I was worried I couldn’t handle living out my sissy fantasies. “Please, Cheryl! I don’t want that. I’m not a siss—”

She slapped me moderately hard, filling my eyes with tears. “You may call me Mom, Mommy or Mistress, Amber. Understand? Now kneel on the floor and stick your ass in the air.”

I nodded meekly and got into position. I turned red with humiliation as she smeared lube around my tight anus. I moaned from the feeling of her finger easing up my asshole. When my cries reached a crescendo, she slid the thick nozzle deep up into my sissyhole. I whimpered in pain as the water and wine rushed in and filled me up.

I saw her triumph at my helplessness as my guts began cramping. The worst of it was my boner got even harder both from the humiliation and the pain. Why I was so excited by my own degradation as Mom stood there for ten minutes until I couldn’t hold it any longer.

“Must you watch this, Mom?” I asked as I got on the toilet.

“You’re now my sissy and you have no privacy or rights of any kind. You’ll learn to turn your shame into pride for being willing to do whatever makes Mommy happy.” She kissed me lightly. “You should be feeling that wine pretty soon. Relax and let go, baby.”

::: ::: :::

Fifteen minutes later she led me to her large dressing mirror, fully made up, my hair styled and wearing her sheer, sexy lingerie. My cock pressed hard against the sheer panties, leaking precum.

“How do you like yourself, Amber?” Mom asked as she stood next to me at the mirror. She teased my pulsing meat in my panties. “Do you like being Mommy’s bitch?”

“Yes, Mommy! Very much!” I made my voice higher, more like a girl’s because I knew it would please her.

“Very good, baby. We’ll sit you down with some voice lessons tonight. Now beg for Mommy to make you a girl.”

As I begged her, I wondered how she’d do that. I got my answer soon: Cheryl strapped on foot-long dildo as thick as a plantain banana. My tummy fluttered with nervous excitement. I’d fantasized about something like this ever since I started watching trans porn. Now that it was coming true part of me was scared and the rest of me...

“Please, Mommy! I want to be your slutty girl!”

“Lay your palms flat on the makeup vanity and bend over so you can watch me fuck you and look yourself in the eyes, baby.”

The polished wood was cool to my touch, but that wasn’t the cause of my pleasurable shivers. I shuddered from my beautiful girl face and naughty lingerie with breasts! And then the sight of my naked stepmother coming up behind me wearing that big dildo she would fuck me with. Her look was as much of love as hungry desire.

“You’re so beautiful… Mistress,” I whispered.

She exhaled in excitement. Her eyes shone with joy. I moaned as she gently stroked my ass through the filmy panties. Then she cut a long slit in the nylon along the crack of my ass.

“Are you ready to give yourself to your Mistress?”

“Oh please, oh please!”

Soon her slippery finger began gently sliding up my excited asshole, making me moan softly like a girl. Mom picked up speed and added a second finger a minute later. The embarrassed pleasure of my stepmom standing naked beside me, wearing a dildo harness and violating my ass with two—now three—fingers made my cock throb with an impending orgasm.

“I’m going to cum real soon, Mommy!”

“Rub your sissy-cock and cum in your panties,” she hissed. She added a fourth finger and began battering my rectal cunt with fiery passion. “Cum hard for Mommy!”

I hunched over the vanity and touched my aching dick trapped in Mom’s panties, while Cheryl did all but fist my burning sissyhole. I moaned and prayed she’d tuck in her thumb and fist my ass like I seen sissies take in femdom videos.

“You’d like Mommy to fist you, wouldn’t you?”

“Yes, Mommy!” I yelped. “I’m going to spurt!”

“Maybe I’ll fist you later, but cum for me now.”

Crazy with lust at the thought of Mom’s fist deep up my ass, my knotting balls clenched and I spurted a thick, white puddle into my stepmom’s undies. I squeezed the last few drops out of my aching dick into the sticky mess and let go of my still throbbing boner.

“Take of your panties, baby. Look at all your sissy cream.”

“Yes, Mommy!” I whimpered all girly, carefully stripping them off. So dearly I hoped she’d order me to lick it up.

Her hot breath filled my ears as she brought her ruby lips close. “You want to lick that up, don’t you baby?”

“Yes, Mommy,” I shuddered.

Cheryl took my aching, sticky dick in hand, so hugely sensitive after just spurting. She stroked it softly but the electric sensations made me shiver helplessly, torturing me sexually. My balls knotted again as she told me she can jack me off until the feeling gets so strong I’ll badly need to cum.

“But you just came, so you won’t be able to,” she purred.

“I think I can, Mommy.”

“Very well, baby. Lick up all your nasty sissy spunk while I try to make you cum again. Lick up every drop!”

I watched in the mirror as I licked up the hot, sticky mess in the panties. Seeing me do this and the sight of me as sissy with my nude stepmother jacking me off, it got my cock fully hard again.

My sensitive dick shot nearly painful ecstasy into my balls while it pushed me toward a second orgasm. I ate up my own semen from the pink panties while she hotly encouraged me to lick it all up for her.

“Oh yes, Mommy! Oh yes!” I gasped in between licks. “I know I can cum again, Mommy!”

She released my cock. “Get up on the bed on all fours,” she ordered. “It’s time to make you my bitch!”

I did as she said while she slipped into a dildo harness and fit on a thick, twelve-inch brown rubber dick. I looked at myself in the big mirror on the sliding closet door. For a moment I could barely breathe I was so horny. I was my mom’s sissy slave. I had a raging boner. I was waiting for my mom to fully take my anal virginity.

I whimpered as she climbed up behind me, got between my spread legs and eased the slippery dildo to my twitching asshole. It made me feel so full. I felt owned by her. “I love you, Mommy!”

“I love you too, baby,” she cooed. “I love you this much!”

“Oh Mommy! Oh mommy!” I wept with joy as she humped me.

She paused her thrusting. Her face leaned beside mine. “You’re the sissy I always knew you were. I’ve wanted to play with you like this since I imagined how you’d look in my underwear.”

I turned my face to hers and we kissed deeply, our tongues wild with passion, intertwined. She resumed fucking me while we kissed. The massive sex toy sent lightning bolts into my prostate and heading me toward yet another orgasm.

I broke the kiss, moaning how much I loved her and promising to do anything she told me to do. “I want to be your playtoy, Mistress,” I gasped. “Anything you want no matter how perverted!”

“I love you so much, Amber. We’ll have such fun together!”

“I… I’m going to cum again, Mom!”

“Then cum for me. Pump your sissy load into Mommy’s hand.”

Her hands went underneath, one encircling my cock and the other cupping the head. She easily jacked me off into another huge, shattering orgasm. Then she fed it to me while she fucked me. 

* * *

 That night my new stepdaughter and I slept in my bed, cuddled together like newlywed lovers. I’d fallen in love with Teddy when I’d married his dad. How could I not love such a girlish boy with long, thick hair, the kind of boy I’d always fantasized of transforming.

My sissy stepdaughter came hard when I took her anal virginity. Afterwards we’d snuggled and talked like lovers. Eventually she and I showered together and then I cooked us dinner, teaching her step by step so that she could soon be my personal cook and maid.

I took her to bed with me after dinner, where she licked my pussy like she was starved for it. Then I mounted and rode her young, rigid cock until we both came again. I’d never been so happy.

We lay there after our incest-ish fucking, sweaty and panting, looking into each other’s eyes. I looked back at her with motherly love and gently cupped her cheek as I spoke.

“I think you want this as much as I do, Amber,” I gently said to her, “but if you think it would be too weird or you aren’t ready to dive deep into the lives I want for us, then let me know and you can go back to being Teddy. We can still have dress-up fun once in a while instead.”

She leaned in and kissed me. “After tonight I wouldn’t want to be anything but your Amber.” She bit her lip. “I trust you. I do.”

Like all good mommies, Cheryl wants so much more for her new girl, especially testing the boundaries of her lust for humiliation. Wouldn't you?