New Shemale Stepmom

Editor's note: this story contains scenes of incest or incest content.

Summary: Stepmom teaches her new son a valuable life lesson.

Note 1: Thanks to Breezy for suggesting this wicked story idea.

Note 2: Thanks to Tex Beethoven for editing.

Fátima and Mitch first encountered each other in a casino during a high stakes poker tournament. Mitch had been divorced for a few years, and although he'd been on a few dates and had fucked a couple of women since, he'd never been in a relationship that was remotely serious.

Then he met Fátima.

All throughout the poker game, he couldn't take her eyes off of her, nor her him... although he wasn't sure if it was because she was interested in him, or because she was playing him...it wouldn't be the first time flirtation had been employed as a tactic in a poker match.

Neither of them had spoken a word to each other during the game, although there were a plethora of almost undetectable facial expressions speaking far more than words... until Fátima won the tournament.

Not being a sore loser, and curious to know more about this gorgeous Latina, he'd offered to buy her a drink. Mitch had always had a thing for big-bootied women... at least ever since he'd divorced his white as white, flat assed, hoity toity ex. They'd only married because she got pregnant with their son Kyle, and they'd stayed together for about fifteen years because the sex was great. But it wasn't love, and eventually it wasn't enough.

Fátima accepted the drink, and they chatted.

Eventually Fátima invited him up to her room for a nightcap.

Fátima seemed a perfect fit for him: she was at least as accomplished at poker as he was, and he was no slouch; she had amazingly big tits; she was wearing nylons, a fetish of his, something few women wore anymore; she had an amazing big booty; and to top it off, she just seemed so warm and genuine.

They chatted about wine (they both loved a good cabernet), his divorce a few years ago, their careers, and then after some kissing and gentle petting, Fátima decided to reveal her core truth.

"There's something about me you should know," she said, really turned on by this sexy, strong man, but needing him to know who... and what... she was before things became too intimate and potentially complicated.

"What is it?" Mitch asked, hoping she wasn't married. He hadn't felt a connection like this in years!

"I wasn't born a woman," she revealed, knowing this fact was often an immediate deal breaker in a fresh relationship... although it hadn't been problematic for one night encounters, where some men and women were intrigued to see a shemale up close, to suck her cock, and to get fucked or to fuck her. But she sensed something special in Mitch... something real... and she hoped he would feel the same. They say love at first sight is a myth, yet there was just something about this man that was getting her heart all flustered, and of course, her cock hard.

"Oh," Mitch said, processing. This revelation was a surprise, but not a deal breaker, since he'd always had a thing for shemale porn (if a shemale was what she was), although he'd never fathomed meeting one in real life. There was just something so exotically intriguing about a woman with a dick.

"And now I'm a transsexual," she continued.

"So you have a penis?" Mitch asked.

"I do, but we needn't be so formal; in the vernacular, I'm 'A Chick with a Dick'," she replied, a little relieved he hadn't immediately gotten up and left. He hadn't overreacted. He hadn't freaked out. Although he did seem to be taking a little while to process the information, which was fair enough.

"Understood. But you're otherwise female?"

"Yes," she nodded.

He placed his hand on her nylon-clad leg. "Thanks for trusting me enough to tell me this right up front."

"You're welcome. You appear to be taking it fairly well."

"I am. And your legs are amazing," he complimented her.

"Thanks," she said, her cock hardening at his touch.

"But one thing that still might be a deal breaker: I expect my woman always to wear nylons," he said as he reached his hand under her dress, and daringly squeezed her cock.

"Then I'm your girl, because I love wearing nylons," she moaned, a rush of sexual adrenaline coursing through her at the possibility this night could lead to something special.

"Wow, what a wonderfully huge cock!" he said.

"Everything about me is big," she said as he rubbed her cock through her pantyhose and panties.

"May I see it?" he asked, curious to see her cock. He wasn't gay, actually he was pretty much the prototype for an alpha male, but a cock on a woman intrigued him.

"Sure," she said, standing up and lifting her dress... knowing her nine-and-a-half-inch cock awed most people.

"Fuck," he said, as he pulled her pantyhose and panties down, and stared at her mammoth cock.

"May I see yours?" she asked, hoping he had a nice cock too, and somehow knowing he did.

"Sure," he said, standing up, and then didn't need to take any further action except for watching, as she dropped to her knees, pulled down his pants, and unveiled his seven-inch curved cock. It wasn't as large as hers, but the curve of his cock always drove women wild.

"What a great cock!" she enthused as she stroked it, loving the pronounced curve, which she knew would feel amazing slamming asymmetrically into her backdoor.

"Go ahead sexy, suck my cock," he ordered, his natural alpha male persona leaping to the fore, and correctly reading Fátima's natural submissiveness. "Get it nice and wet, so I can fuck you."

"You want to fuck me?" she asked sultrily as she stroked his cock.

"Certainly. I already know I want to do everything with you," he said, as he slid his cock between her pretty pink lips.

"Mmmmmmm," she moaned, as she began sucking his cock. She was an amazing cock sucker... having been sucking dick since she was eighteen, even before she began her transition. She'd get all dolled up, go to a gloryhole in town, and suck cock after cock after cock, without anyone guessing she was still a guy.

"Fuck yes," Mitch moaned as she deep throated his cock, something very few women could do, or would even attempt to do.

"Mmmmmm," she repeated, her cock always rock hard whenever she was sucking someone else's. She loved getting fucked and she enjoyed doing the fucking, but nothing stimulated her more than being on her knees sucking a cock... and this was a great cock!

Mitch had never been with a shemale, but he'd fucked a few guys. During the last few years when he needed to get laid or get head, he'd found back when Craigslist was still a thing it was easy to have a guy invite him over to get sucked, or he might even arrive to find the guy already bent over on his bed, ass up, already lubed and waiting to be fucked.

But a woman with a dick was very intriguing and particularly erotic, and although he didn't think he'd ever want to get fucked, the idea of sucking Fátima was rather captivating.

"Shit, I need to fuck you right now," he said (we're back to their first night together), not wishing to blow his load too quickly, even though she had an amazing mouth.

"Just take me," she said, as he led her to a window overlooking the city. "You'll find some lube in my suitcase."

Mitch went to her suitcase, found the lube as well as seeing some sexy lingerie, and returned to her. He lubed his cock while she climbed out of her dress, unclasped her bra, and slipped out of her pantyhose and panties.

"Wow, what an impressive pair of tits," he admired.

"40DDs," she said, cupping them for him.

"You're so beautiful," he said, admiring her body... her wide hips, her big tits, and her huge cock. Somehow her overall package came together in a way that wouldn't make much sense if you tried to explain why it worked.

"Why are you still dressed?" she asked, as she vamped over and unbuttoned his shirt. She then rubbed her hands down his chest as she knelt down to help him out of his pants and socks.

"Lean against the window," he ordered, being a bit of an exhibitionist.

"Mmmmmmm," she said, as she leaned over and offered him her big ass.

"Fuck, what an ass," he said, as he squeezed her big butt.

"Wait until you're inside it," she purred, knowing her ass was naturally tight, but she was able to tighten it further, to milk a cock like no ordinary woman could ever manage.

"You're one sexy woman," he said as he positioned his cock at her ass/pussy.

"Just slide it in, baby," she said, "I want to feel that big cock inside me."

"As you wish," he said, as he pushed forward and slid his cock inside her.

"Oh, yes," she moaned, as his dick filled her. She'd sucked some cock recently, and had even fucked a pretty hotel maid, but she hadn't been fucked in weeks. It felt so good, and it made her cock twitch.

"Such a tight pussy," he moaned, treating her as all woman.

"Such a big cock," she moaned, as he leaned against her, pushing her tits against the window glass as he began really fucking her. "Oh yes, fuck me, fuck me hard!"

Mitch and his ex-wife had lasted so long not because of love, not even because they had a son, no, the truth was that Julie loved his cock, loved how hard he fucked her and his dominant persona in the bedroom... which almost overcame the drawback that he was only a plumber... so eventually she needed to rejoin her own uppity friends.

Over the next few minutes Mitch slammed into this new hot woman, whispering into her ear how beautiful she was, how much he loved fucking her, and as her moans increased, he reached around and stroked her cock while he fucked her... causing her to explode a load all over the inside of the window.

Seconds later Mitch warned her he was about to come, and Fátima begged him to fill her pussy right up, which he gladly did.

They spent the night together asleep... but also cuddling very affectionately.

In the morning Mitch sucked a cock for the first time... loving the sound of her moans... before he fucked her again in a marathon morning session.

After that, they were inseparable.

Fátima loved that she'd finally met a man who invariably treated her like a lady whenever appropriate, but also fucked her like a whore... it was the combo she'd always longed for.

Mitch loved her beauty, her personality and her body (cock and all).

Two years later they were married.

Kyle was happy for his father, and was his best man at the wedding.

Then one day Mitch sat down with his son for an earnest chat.

Kyle's father shared with him the complete truth about Fátima. Kyle was surprised, since except in porn he'd never before knowingly encountered a shemale. The idea of a woman with a cock intrigued Kyle, who jerked off to almost every variety of porn: lesbian, group, interracial, shemale, mind control, and even gay. He didn't see himself as gay at all, he just loved to watch people getting off.

Her always wearing nylons also turned Kyle on, since just like his dad, he had a nylon fetish... a trait he'd learned they shared when they had a long talk about the birds and the bees back. What he didn't know even now was that Fátima wore them partly because she liked them and the way they showcased her feet and legs so well, but also because her dominant man expected her to wear them at all times. And the pantyhose she'd once worn were a relic of the past; only garter-belt and stockings or thigh high stockings were allowed, since as Mitch put it, "I expect quick access to my hot lady's pussy at all times."

He'd reinforced that demand by fucking her in a wide range of locales since their first encounter, including twice on planes, a few times in Ubers, in more than one bathroom stall (sometimes in posh locations, but also in sleazy ones), in a busy park (not right out in the open of course, but that small grove of trees wasn't all that concealing), at a nude beach (right out in the open that time, with about a dozen people watching), on the occasion of the wedding of her niece, and more. They loved each other, and they still fucked as frequently and with as much enthusiasm as if they'd just met. Their fire was still burning with hot flames.

Kyle's only problem with Fátima was she acted as if she were his actual mother, but much more sternly. His real mom paid her maid to clean up after him, but whenever he was at his dad's, she refused to clean up after him or take any shit from him. He was pretty sure that was because of her masculine side.

Kyle and his dad loved watching NASCAR, and while Fátima would pamper his dad, fetch him beers and clean up after him, she wouldn't do that for Kyle. Which annoyed the hell out of him. Kyle recognized he was a bit, perhaps a lot, spoiled, but he'd take pains to point out Fátima's double standard even while he admired her sexy legs... still in awe she'd once been a man.

His dad would always counter with, "Hey, she's MY wife, not yours. If you want a beautiful woman to wait on you hand and foot, find your own wife. But until then, you'll do whatever she says while you're living in our house."

Fátima would always say, "Thanks, honey," while bending over to kiss him, allowing her skirt to rise up enough to showcase her entire stockings... she'd long ago learned the power of being sexy, and teasing her stepson was fun.

Of course Kyle knew better than to challenge his father, so he let it go... but it still annoyed him.

Kyle arrived one day to watch NASCAR with his dad, and was surprised when only Fátima was home.

She said in her sexy voice (it was the only one she had), "I'm sorry sweetie, but your father is attending a bachelor party tonight, and he won't be back until very late, or maybe even tomorrow."

Kyle sighed; he didn't really want to spend his time here with Fátima telling him what to do, but his dad's eighty-inch television was way better than any of his mom's six televisions (in this case size mattered), "Is it okay if I hang out here anyway and watch the race?"

"Sure," Fátima agreed, "just pick up after yourself."

"Yes Mom," Kyle said in a very sarcastic tone.

Fátima didn't respond. Instead, she left him alone and went to finish the laundry.

Kyle watched the race, but Fátima's big tits and her sexy nylon legs had him horny, so he pulled out his phone and pulled up some shemale porn. He hadn't seen her in an hour, so he assumed she'd gone shopping, or was taking a nap or whatever.

He was in mid-stroke, watching a shemale getting railed by another shemale, when he heard her startled voice, "What the fuck, Kyle?"

"Calm down," he replied arrogantly, not really caring what she thought. "Everyone does it."

"But not where other people can see. I'm going to need you to leave my house right now!" Fátima barked, as she took note of his impressive, even larger than his dad's, cock.

Kyle wanted to make his point, and right now not stuck with his dad defending her said, while still openly stroking his cock, "First of all, this is my father's house. Second, this is my house too."

"Get the hell out before I call your father," Fátima said, "he won't be happy about coming home to deal with you, but he'll do it for me, and take it out on you. Is that what you want?" She was pissed he'd disrespect her like this. She'd been treated poorly by almost everyone during her entire life because of who she was, but in Mitch she'd finally found a man who respected her (except while they were having sex, which definitely wasn't an issue), and treated her like a princess.

Kyle, who knew his big dick usually made women swoon, it was kind of the male equivalent of having big tits, since it gave you an automatic advantage, stood up but didn't bother to pull his pants up as he said, "Look, babe. You're acting like a real bitch right now."

"Did you just call me a bitch?" she asked, stunned by this blatant disrespect. There'd always been some tension between them, and she knew his mother hated her, but this arrogance was a totally unexpected extreme even for him.

Kyle, seeing she was rattled, and knowing most women couldn't resist his big cock, said smugly, "I think you just need to get laid. Don't think I didn't notice you checking out my big cock."

Fátima knew exactly the game Kyle was playing. Yes, he had a big cock. Yes, it was quite impressive. But she'd seen big dicks before... and of course hers was bigger than his. She scoffed, "Trust me, I get laid as much as I could ever need by your father. He's more of a man than you'll ever be!"

Kyle had met resistance before; for instance he recalled how Mrs. Walker had recently denied interest in his cock for several days before she'd finally broken down, bent over her desk and begged him to shove it into her married pussy. So he remained confident as he reminded her of his point. "So you claim. Nevertheless, you were definitely checking out my cock."

Fátima was getting pissed off and really needed to put this man-bitch in his place. "Your cock? Huh! Hell, my cock is bigger than that tiny thing you're waving around. I should fuck you and make you my bitch!"

"Sure it is," he scoffed, assuming any guy who wanted to become a girl would have a pathetic mini-dick. "Please, I could fuck you into next week."

"Is that right?" Fátima demanded, heading towards him.

Kyle, sensing he'd won since she was coming to him, nodded, "Yeah, that's right, I'm a beast between the sheets."

"I'm sure you think you are," she said, knowing that no young inexperienced man could properly satisfy a woman.

"I've never had any complaints," he said, as she now stood directly in front of him.

"Care to make a wager, mister well-hung complaint-free man?" she asked, her tone subtly sarcastic.

"Maybe. What kind of wager?"

"You want to fuck me, right?" she asked, knowing that almost every guy wanted to fuck a shemale... for a variety of reasons, but one of them being a shemale was an intriguing curiosity.

"Fuck yeah," he blustered like the nineteen-year-old novice he was.

Playing him like a fiddle, she said, "You'd be very sorry if you tried. You couldn't last five minutes fucking this juicy, 'bootyful' Latina ass."

"Wrong. I can go all night," Kyle assured her, having a very quick reload time, a blessing of his youth.

"Perhaps," Fátima continued reeling him in, smiling sexily, "but are you willing to bet your sweet virgin ass on it?"

"What?" Kyle asked, surprised by the question, yet feeling confident he could win any bet, "I might. What are the terms?"

"Simple," Fátima said, as she reached out for his dick and stroked it slowly. "If you can last five minutes, I'll let you fuck me. But if you can't, then I get to fuck you."

"Exactly what am I supposed to last five minutes at doing?" he asked, desperately wanting to fuck her... just to pound the living shit out of her... to put the uppity bitch in her fucking place.

Fátima thought he'd back down once her deal was offered, but suggested it anyway. "We'll have five one-minute rounds. One of us will suck the other's cock for one minute, then stop. Then the second one will suck the first one's cock for one minute and stop. Whoever cums first loses. Then the winner claims their prize right here, right now. No condoms, just lube and raw anal fucking. What do you say sport, are you game?"

"I've never sucked a cock before, but I'll get you off all right," Kyle said, so focused on this chance of fucking her, he was willing to suck her cock. Secretly having watched a lot more shemale porn since discovering his dad had married one, the idea of sucking a shemale had entered his mind on more than one occasion. He didn't tell her that of course, but said instead, "So yes, I'm game. I just hope you're well rested, because I'm about to hate-fuck you so hard!"