[M/S]Transsexual Stepmom

All characters are over 18years of age, consenting adults with open minds and hearts.

Jerry has a new stepmother: Sherry, a tall, busty, gorgeous woman he's fantasized about since Dad started dating her. What he doesn't yet know is her biggest secret!

The very next week, Dad left for a week-long business trip to New York. Dad gave Sherry a passionate kiss on the doorstep and a manly hug to me, then he marched to the cab to LAX. Sherry curled a friendly arm around my waist and we both waved goodbye.

“Well, let me fix you some breakfast, baby,” Sherry said. She pulled her arm away and preceded me back into the house.

“Sure, Sherry.”

She threw a lovely smile over her shoulder and I followed her. “Please, call me, ‘Mom,’ okay?”

“Yes, Mom.”

My eyes couldn’t help following her heart-shaped ass and how the terrycloth shorts clung to them. She might be my stepmother but that wouldn’t stop me from beating off thinking about her. I decided I didn’t want to wait. Already the mental pictures formed.

Oh, her sexy asscheeks, juicy twat and yummy asshole…

“I think I’m going to take a shower first,” I said. My voice shook a little bit. I only hoped she didn’t see my boner pressing against my cut-off bluejeans.

“That sounds like a lovely idea, Jerry,” she said. “I think I’ll do the same. See you back out here in about fifteen minutes.”

I had stripped down and was starting toward the shower when I got a daring idea. If I snuck quietly into the master bedroom, I could get a look at her stripping down. I’d have a fully nude image of her to take into the shower.

I made the bold move of going on my peeping mission totally nude. If I was careful, she wouldn’t catch me! The door was wide open so I heard the sound of her turning the shower taps, the splash of water hitting the shower floor, and finally the sound of the shower door closing. This was it!

I tiptoed into the bedroom. All I had to do was clear the edge of the bed and I’d have a clear line of sight into the bathroom. I was so intent on the bathroom door it didn’t even occur to me to look elsewhere, so when she cleared her throat I shrieked. That was when I saw the closet door was open. She stood behind it.

“If you want to see me naked, why don’t you just ask?”

My apology cut off when she stepped into full view. I gasped twice. The first was one of awe at the sight of her perfect D-cup breasts, all firm and perky. The second gasp was of deep shock.

That thing must be a foot long!

“Y-y—you have a dick!” I whispered hoarsely.

She grinned. “Very observant.” She looked pointedly at my own cock, which was still hard in spite of my shock. “You have one too. And it’s hard.” She smiled seductively as she slinked over. “Did you get that thinking of me—your mom?” She chuckled. “What a sweet boy you are.”

Her seductive gaze riveted me to the spot, even when she got to her knees in front of me. I whimpered with embarrassed lust as she curled her soft, warm hand around my boner. She held my eyes as her mouth engulfed my erection. As I felt my cock slide into that hot, sucking wetness I momentarily forgot the surprise of seeing my new stepmother was a transsexual.

I surrendered my mind to the deep, intense erotic sensations swirling around my dick and making my nuts ache with deep satisfaction. I felt her throat close around the head of my cock and start swallowing—something none of the girls I’d ever fucked had been able to do. Then a part of me woozily remembered my stepmother was no ordinary girl. My new mom had a huge cock!

The reality of who was giving me a blowjob—and what she was—unleashed a storm of wild and delicious thoughts. I’d discovered TS porn as soon as I started browsing the internet. Then came fantasies of cheerleaders at school growing dicks, their wet pussies becoming massive dicks spurting fountains of cum on my face and hair, and in my mouth. They fucked me up the ass with two-foot-long boners and pumped me full of their hot jizz. But this was no fantasy now and this woman was not a cheerleader—

My mom is a T-Girl! Mom is sucking my dick and I want to suck her dick and I want her to fuck me up the ass and cum in my mouth and over and over…

I got so dizzy with lust my knees got weak. Sherry’s hands had cupped my ass, so she felt me wobble. She eased my cock from her mouth and looked up into my eyes with such wanton desire. I looked down and saw those eyes, that beautiful face, and her dick hard as could be. Her big, pretty shemale cock!

“Let’s get you to the bed before you fall down, baby,” she said.

“Yes, Sherry.”

“Won’t you please call me ‘Mom?’” She took my hand and led me to the bed. “I want to take care of you in all the ways a mom should and shouldn’t take care of her big, strong son.”

Quickly I got it. I looked across into her smoldering eyes and understood how hot it would be if we could turn this into actual incest… at least in our minds.

“Yes, Mom,” I breathed, returning her look of desire. “Can we hold each other on the bed for a bit before we do anymore?”

“Sure, baby.”

Being nine inches shorter than her, I easily cuddled into her body, tucking my face against her large, soft left breast. I heard the beating of her heart. Her soft hand gently stroked my hair. Her boner had not gone down and I could feel its heat and fullness against my thigh.

My stepmother’s cock!

“Is there anything you want to ask me, darling?”

“I guess… how did you meet my dad?”

“Sam was a regular from the very first time he called my escort ad. Every time he got in town he always managed to squeeze in at least two hours. He was in love.”

“Easy to see why. You’re like fashion model beautiful. Smoking hot body… And that’s a dick anybody would want to have… Mom.”

She bent down and kissed the side of my face. “Such a sweet boy you are.”

“Your sweet boy.” I kissed her back. “So, Dad was a regular.”

“Uh-huh. Eventually he asked me to marry him. I was doing well financially but I was getting ready to get out of it… and so few johns are as debonair or handsome as your dad. Even fewer have his money.”

I felt a little let down. “So… you married him for…” I bit off the question. I didn’t want to accuse her.

“No, Jerry. That wasn’t the real reason why I said yes. It was the same reason he asked me to marry him—you.”

“Me?”

“He feels so bad about leaving you all alone for so often. He wanted you to have someone to look after you. She tucked a finger under my chin and lifted my gaze to hers. “Someone to look after all of your needs.” She chuckled softly at my surprise. “He pays your credit card bills, Jerry. He knows you love trans girls. You go to the same porn sites he does.”

“Oh.” I blushed at knowing my dad knew all about my kinks.

She looked lovingly at me. “When he said he wanted me around for you, I was so moved. Then I saw your picture and I fell in love.”

My stepmother closed her lips over mine and slid her tongue into my mouth, loving and lustful. She and I clutched each other’s naked bodies, tender kisses intermingled with tongue fucking, hands caressing and groping, teasing each other’s hard dicks.

I broke away. “I can’t wait any longer, Mom!” I gasped.

I slid down until my face was just across from her throbbing tool, twelve inches of hard trans cock oozing precum. I had never sucked a dick before in my life and now nothing could stop me from taking hers into my mouth.

I want to drink her cum… take her up my ass!

I paused to take in the sight of her huge tranny tool. It was smooth and pinkish with subtle veins a little less thick than an average-sized banana and tapering into a circumcised, helmet-shaped heart purple with erection blood. A fat, clear drop of seminal fluid was welling up at the cumhole. I stuck my tongue out and lapped it up. It was sweet!

“Mmmm, that’s it, baby. Suck Mommy’s cock.”

Before I had discovered T-girls, in my most feverish fantasies I had fantasized about taking an androgynous guy’s cock in my mouth. TS porn expanded my fantasies to suck girl dick and getting fucked, but never until this moment did I think I’d ever go through with it. I was still surprised to learn my dad loved the same things!

Despite being rock hard and throbbing, my stepmom’s dick was soft and velvety smooth. It felt so wonderful on my lips I took the head into my mouth without any hesitation. The plump, hot crown of her dick felt so sexy resting on my tongue. The flavor was incredible. I slid it deeper into my mouth.

“Oh so good, baby! I love you being Mommy’s sweet little cocksucker. She has so much to teach you—cum-drinking and deep throat and ball licking—mmmmm. Suck it, baby.”

I’m sucking my stepmother’s dick!

Soon her twelve-inch cock ran a steady stream of precum into my mouth. I gulped it down as she lovingly stroked my head and called me “son” and “baby” over and over in a voice that got me rock hard.

“I can climax any time you want me to, Jerry. Do you want Mommy to cum in your mouth… son?”

“I… I just want to get your dick good and slippery… so…”

“So—what, baby?”

“So you can fuck me in the ass… Mom.”

“You’ve made me very happy, sweetie. Get on all fours and spread ‘em wide.”

My trans stepmother got behind me on the bed as I assumed the position. I shuddered at the feel of her hot breath on my anal cleft. I gasped at the hot, wet feel of her tongue bathing my puckered anus. My mom was rimming me! I felt it start to loosen up and get hungry for penetration.

***

I got excited when I felt the young man’s asshole loosen under my tongue, as if him willingly call me “Mom” over and over didn’t turn me on enough. His moans and whimpers filled my ears. I had to fuck my stepson’s ass right now! I told him so.

“Yes, please, Mommy,” he whined. “Fuck my slutty ass with your big shemale dick. Fuck your horny son real good!”

I knelt between my stepson’s spread legs and touched the fat tip of my throbbing boner to his saliva-covered hole. My dick was slippery in my fingers from his spit. I was so excited to be fucking my husband’s eighteen-year-old son that I pushed in my dick a little forcefully.

“Ow! Sherry!” he protested.

“Sorry, baby, sorry. I didn’t mean to hurt you. Push down on your rectal muscles like you’re trying to shit and see how easily Mommy goes up into you!”

A moment later all twelve inches of me slid easily up his butt. He groaned deeply with pleasure. My long cock was all the way up the boy’s ass and he was loving it. He began whining how good it felt in a girlish kind of voice. It turned me on to hear it, to hear my young stepson sounding like a sissy.

My plans are going perfectly!

“Oh, fuck me, Mommy! Fuck me, Mommy!” the teenager squealed.

It got me so horny to hear that. I would have to take me time but I knew that the big picture I had, ever since I married his father, would come to fruition soon enough. I thought I would try testing the waters a little bit even as I was fucking him.

“You sound like a sexy girl when you say it like that, baby!”

“Mmmmm! That’s ‘cause you’re fucking me like I’m a girl, Mom,” he panted. “I love feeling like your girl!”

Perfect! Only in my wildest dreams…

“It turns on Mommy to hear you say that,” I moaned, fucking him harder and harder. “I think I could cum right away it I tried.”

“Yes Mom! I want you to cum. It would make me so happy!”

“Do you want me to cum up your ass, baby? Or—”

“On my face and in my mouth,” my teenage stepson panted. “I want to taste your hot fucking cum!”

He’s making this too easy! “Lay down face up, baby.”

I pulled out of my stepson’s asshole and then straddled his chest when he lay down. His mouth and eyes were wide open as he looked up at me. I felt him beating off furiously as I pointed my slippery dick at his face and began pounding. I had purposefully not cum for two days, saving it up for this moment.

“I’m cumming, baby!” I gasped. “Get ready!”

“Give me your jizz, Mommy!”

My balls drew in on themselves, an intensely pleasurable ache that traveled from the pit of my groin and down the length of my cock. Even though I knew how much I could shoot, I was still astonished by the huge, white jet of spunk that arced through the air and splattered from his forehead to his chin to his cheeks. Most of my cum covered his lips and tongue.

He gulped it all down with ease, rapture on his face. He just barely got his mouth open again in time and I bent in and shot my second spurt all over his lips and into his mouth, half-filling it.

“Mmmm. Don’t swallow it, son,” I told him.

I plastered my mouth to his. I felt my third and fourth jets of cum spurt all over my hanging tits as I shared my cum with my stepson, our lips so sticky with cum meeting each other again and again as we shared the glob of semen like lovers, drinking it down together.

Ours may not be a typical incestuous family, but it's a very satisfied one!