Family Reunion: Mother's Day

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Mom unknowingly befriends long lost son who's now a shemale.
  • July 2020 monthly contest
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Family Reunion: Mother's Day

Summary: Mom unknowingly befriends long lost son who's now a shemale.

Note 1: This story is dedicated to TX and BABY GIRL for requesting this story... something a little different for me.

Note 2: Thanks to Tex Beethoven and Robert for editing.

Note 3: All characters are at least 18 years of age.

Family Reunion: Mother's Day

Zach had always lived two very different but parallel lives.

One of them was what everyone around him was aware of: a steady churchgoer (he had no choice about that, since his Dad was the Pastor), outgoing, funny, smart and athletic. He was also a bit of a charmer, and many of the cutest girls in the community had crushes on him. He played his part of a good looking, good boy (mostly) quite well. He even dated a few girls occasionally, apparently (but also sincerely) loving everything about the female body.

On the other hand, behind the façade everyone saw, lurked a secret truth he had struggled to deal with for years: he didn't just love and admire everything about the female body, he longed to actually be a woman.

He loved everything about the feminine half of the world:

-their smooth, soft skin, which was so much nicer than the coarseness of his own skin... especially his hands and face

-that they could augment their faces with a wide variety of cosmetics

-that for variety they could arrange their hair in so many different ways, and could even wear it long (yes, guys could wear it long too, but in his heavily South-influenced region of Kentucky not so much, and a definite no-no in church).

-that that they could have big breasts, something he'd always been fascinated with... even though his own chiseled masculine chest was admired by many girls, and many gay boys.

-those of the feminine persuasion had the opportunity to indulge in such variety in their clothing: dresses and skirts seemed so much fresher than his own ubiquitous dress pants (his father refused to allow him even to own a pair of jeans)

-the greatly desired privilege of wearing nylons... the apparel that turned him on the most. Partly because his Mom and all the church ladies had worn them every day ever since he could remember... he had been noticing stocking-clad feet for his entire life... way more than he saw bare feet inside the women's shoes. He loved how each shade and colour of their stockings could completely complement an outfit and/or accentuate a pair of legs. Lastly, once he felt how soft they were (during many clandestine visits to his mother's bureau), he was completely captivated by them, and wondered what they would feel like on himself... on his ass... on his legs... snugged up against his impressive nine-inch cock.

Now Zach wasn't gay, he'd actually fucked a few girls, even two of them together once, and he enjoyed eating pussy; and he most certainly didn't want to kiss, or to suck or get fucked by guys... although the idea of him being the one fucking some specific guy, especially one who was a homophobe or asshole, did pop into his fantasies on occasion.

No, he definitely wasn't gay. Zach simply craved the opportunity to dress as a woman... or better yet, to actually become a woman... but being the son of the Pastor at the largest mega church in Oklahoma made this an impossibility, and he'd been programmed for his entire life, through bellowed Scripture and impassioned lectures, that being gay was a horrible sin, and being transgendered in any way, shape or fashion, was far worse... it was an abomination. (To be perfectly clear, to dip even his big toe into either of those poisonous waters would not only be a sin against God, but a crime against Nature)

Yet after years of openly denying who he really was and inwardly feeling guilty about it, now in his senior year at almost nineteen (his birthday in December and he'd begun school a year late after spending a year in Africa with his missionary parents, when otherwise he would have been attending kindergarten), he decided his feelings of guilt stemmed more from a sense of duty than from anything heartfelt, and that he was no longer going to live in a façade of lies as he started to secretly, slyly, explore his feminine side.

He slyly used his mother's specialty skin care products to give his hands softer skin, and also his face, and his shaved legs and chest. Being a competitive swimmer, having a completely shaved body was an expectation, so no one wondered about his being completely hairless except for his head... nor did anyone realize that was the principal reason he'd joined the swim team in the first place, even though he was awfully good at it.

He loved not only the softness of the moisturizing skin products, but also their fruity aromas

As his senior year progressed, he began collecting feminine garments. After fucking a nerd girl in her garage (she was a large girl, slightly larger than he), he claimed her panties as a trophy... feeling slightly bad that he'd fucked her primarily because they had a similar waist size, not because he actually liked her. That said, she'd turned out to be a good fuck, and a sweet girl, and they ended up secretly fucking for a couple of months, she allowing him to walk away with her panties each time (she thought it was because he loved her scent of arousal, not so he could wear them when he was home alone, or secretly in his bed each night).

Zach also ended up fucking the mother of one of his friends, and thus he carried away her pantyhose as his trophy, not willing to buy some at a store where someone might recognize him. He fucked this woman every Sunday afternoon while her husband and son were golfing... she loved that he paid so much attention to her legs in pantyhose, that she would wear them without panties all day, and rub herself to an orgasm in the morning so they'd be nicely soiled for her secret young stud with the big cock.

So in the final semester of his senior year, he began wearing panties and pantyhose in his bedroom, and even occasionally out in public... which he found to be a huge rush... but then would become annoyed at having to keep secret something he dearly wanted to do, the only thing that made him feel like himself. He hated that he couldn't just openly be himself in public.

It was the week before prom, when he was in panties and pantyhose and nothing else, neither of his parents home, examining his mother's high heels in her bedroom (curious what it would be like to wear them), when his mother walked in on him, having forgotten her purse.

Emma, his mother, was stunned; but being a traditional and therefore very submissive wife of a Pastor, she simply grabbed her purse and walked out again without saying a word.

At first, Zach was humiliated... mortified at being caught, but as he considered this seemingly disastrous encounter, he realized it had been a blessing in surprise, to coin a new phrase. He was now, finally, being forced to do something he'd been longing to do forever, to come out and tell his parents he didn't feel he was a male... but a female. And even that he wanted to look into transitioning... well, partly transitioning anyway... he had no intention of giving away his big dick... and he wanted, in the simplest terms, to become a shemale.

So when his parents came home fifteen minutes later, his mother obviously outing him, Zach just threw out the truth he wanted to live, the truth he'd long been living secretly, to his parents.

Not surprisingly, it didn't go too well... especially as Zach was still wearing the panties and pantyhose, which served as a continual reminder to his parents that their son was an abomination. Where did we go wrong? Why is he doing this to us? To US?

Pastor Richard (Dick), and man, he could be a dick, freaked out at great Biblical length and volume, while his wife adhered to the Scriptures by wailing and gnashing her teeth uncontrollably.

In fact, Zach received Scriptures galore amidst the fire and brimstone end-of-the-world lecture from his enraged father.

Which was followed by dire portents of their own reputations being shattered in the community, and Dad's career jeopardized completely, if his very own son couldn't even adhere to something as basic to respectable society as walking with Jesus.

Zach, whom his father had always assumed would follow in his footsteps, knew the Bible by heart himself, and he countered, "John 13. I give unto you, That ye love one another; as I have loved you, that ye also love one another. By this shall all men know that ye are my disciples, if ye have love one to another."

Pastor Richard was furious with his apparently gay son (no way he could conceivably comprehend the concept of anyone being transgender... because in his mind that wasn't even a thing. If you were born with a penis you were male, if you began life with a vagina you were female... gender was as simple as that, no exceptions). He countered by using Scripture right back to his wayward son, summoning a litany of Scriptural passages:

Ephesians 6:1 Children, obey your parents in the Lord, for this is right.

Exodus 20:12 Honor your father and your mother, that your days may be long in the land that the Lord your God is giving you.

Proverbs 1:8 Hear, my son, your father's instruction, and forsake not your mother's teaching,

Ephesians 6:4 Fathers, do not provoke your children to anger, but bring them up in the discipline and instruction of the Lord.

It ended with Pastor Richard forbidding Zach to be gay, even though Zach stressed over and over that he wasn't gay, he was transsexual.

The Pastor finally lost it and snapped, "That isn't EVEN a fucking thing!" before storming out.

Emma pleaded, desperate for peace between her husband and her son, "Please, Zach, if only for me, no more of this nonsense."

Hearing those words really hurt Zach, who'd never truly gotten along with his father, but had always loved and obeyed his mother. Reluctantly he agreed, knowing he'd be moving out at the end of summer nineteen hours away to UCLA in Los Angeles, where he had waiting for him full scholarships in both academics and swimming.

Things were tense but livable through May, June and July, as they all simply never mentioned Zach's sexual identity ever again... something quite common in certain religious families... if you simply don't talk about something, it isn't real.

Zach continued secretly wearing panties and pantyhose and using his mother's lotions... although he was now far more careful, as he counted down the days until he could move out west and be himself (or preferably herself).

The final straw broke apart the family's false peace in early August. Zach was doing what he did every Tuesday night while his Dad was leading a Bible study, he was fucking one of the four guys he was banging that summer, the secretly gay Carter... a mid-twenties junior minister who couldn't get enough of Zach's big dick, especially whenever he was wearing nylons, which made their sex seem less gay. Zach wasn't gay at all... he just liked to fuck, and he found that guys were less exhausting and carried around less drama baggage than girls. Men just wanted to suck his dick and get fucked. No talking, no wooing, no flowers, no emotional attachment, just Zach depositing a load in one of their two holes, and 'Bye! Thanks a lot!' Carter was his fourth bottom of the summer; he just loved pounding a guy from behind, and loved hearing his moans. This being a sin that would really piss of his Dad was just an added bonus.

Should they have been fucking in the church basement in the first place? Probably not. But it was a very private place, one that was generally never frequented.

It was a beautiful summer's evening, and the Pastor had ended the Bible study early, allowing his parishioners to go forth and enjoy a delightful evening. He was locking up, when he noticed a light on down in the basement. He'd been down there earlier in the day looking for a file, so he figured he'd left it on. The Pastor opened the door and heard a rather feminine voice... and it was moaning! He instantly became furious... some damned souls were having SEX down there! So he stormed downstairs to catch whoever it was in the act.

As he followed the sounds into an office that was used for the rare meeting, typically only if it needed to be very confidential, such as a politician who didn't want to be seen going in and out of the church (don't you dare ask why, because I won't dare to answer, but this was the principal reason why the church had built a secluded back entrance) or for some of his meetings with investors that were under the table, he saw someone bent over his desk while his son, wearing lingerie consisting of a bra, garter and stockings, and also heels, was fucking the person.

The Pastor roared, his fire and brimstone voice in full effect, "What IN HEAVEN'S NAME is going on here?!"

Zach was startled, and he turned around without thinking, thus pointing his big, hard dick directly at his stunned and red-faced father. "D-D-Dad!"

"Pastor!" Minister Carter gasped, as he bolted upright and yanked up his pants, hiding his gaping asshole.

"You're committing sodomy in the Lord's sacred place of worship?!" Pastor Richard demanded. "In His very HOME?"

Zach was annoyed at being caught, but he wasn't ashamed, especially since he knew that some rather questionable dealings happened in this very room. (He hadn't had to ask; he was smart, and he noticed things.) He said, knowing it would only make things worse, "This room is hardly a sacred place." He realized after saying it, that his Dad would think he meant the entire church.

"So you're gay?" Pastor Richard bellowed, even though it appeared rather obvious.

"No, I just like fucking guys," Zach answered before adding, kind of enjoying to infuriate his Dad, "I don't suck dick or anything, although Minister Carter does."

"Out," Pastor Richard yelled, as he looked at his smug son and noticed his penis was a lot bigger than his. "Both of you, out."

Zach grabbed his pants and put them on, as Minister Carter, his face burning red, scurried out with his head hung down in shame.

Zach exhibited no such shame. "Don't be too hard on him," he urged his father, "he's a good guy."

Pastor Richard ignored the irrelevant advice and quoth, "You need to leave forthwith, young man. We can't have you going around besmirching my good name, my wife's, the church's, or the community's."

"Excuse me?"

"You heard me; you're no longer my son," the Pastor said, and turned to stride piously out (for a very limited definition of the word 'pious').

Zach was shocked... hurt... and angered. "Whatever happened to forgiveness?"

"Forgiveness has its limits, and you have crossed the line," the Pastor growled.

"Where does the Bible even fucking say that?" Zach demanded of his father's back, adding the 'fucking' because he was so pissed at his father's flexible use of the Bible's teachings.

"Just get out!" the Pastor snapped, returning a raising a hand to smite his former son.

"Go ahead," Zach dared, wanting his Dad to hit him. Wanting to see his self-righteous Dad commit a sin.

"Out," the Pastor snarled, managing to control at least the physical side of his violent anger.

That night Zach slept at a friend's... knowing he really had to talk to his Mom.

Next morning, he went home... and found both his parents waiting for him immediately inside the front door, with two suitcases already packed.

The Pastor handed him a cheque (in the amount of a shocking $250,000!) and intoned coldly as if he were quoting the liturgy for an exorcism, "You sir, are a disgrace to our family name, an unwelcome sinner who formerly attended our church, an embarrassment to your mother and to me, and we never wish to suffer the sight of you again."

Zach looked to his mother, but she immediately broke eye contact, even though he could see tears in her eyes. Zach wanted to hear his mother confirm his father's sentence... to agree with or to deny his harsh words... but he was confident his Dad wouldn't allow that to happen.

And sure enough, she didn't speak... didn't even look up again... just looked down at the threshold to the front door and bawled. They hadn't even allowed him to set foot in the house he'd grown up in!

Zach, who'd already planned to leave for college in a week anyway, and who was more angry than hurt, took the enormous amount of money (why the fuck not?), grabbed his suitcases and said, sarcasm dripping from every word, "In that case, God bless you two Christian folk."

Zach got in his car, drove straight through to Los Angeles, arrived before dawn totally exhausted, lodged in a nice hotel for the week (using the church's credit card until it was cancelled a couple weeks later), before he was allowed to move into the dorm, and went shopping... buying a variety of sexy lingerie... all the things he'd wanted to buy back when he was living in his small town hell but never had (again, all on the church's credit card his Dad had given him a while ago to pick up items for the church... usually from Costco... the church items had been from Costco, not the lingerie).

He also, now he was away from the shadow of his father and the ridiculous moral code of his southern community, went to a doctor and initiated the process of his transitioning.

The years went by, and by the time he had earned his degree (with honours), he had become a she, Zach had become Sasha, and she (get used to the adaptable pronouns because they're the new reality) had become a complete knockout. Long blonde hair, blue eyes, nice medium-sized 34B tits, long legs that went all the way up to here, although she still sported her big, fat nine-inch cock. Hair no longer grew on her face, and her voice was now sexy and feminine... Sasha had become exactly who she had always fantasized about being... a beautiful, confident young woman. And yes, she had legally changed her name way back at the beginning, and she would have changed her legal gender, except search as she might, there was no official vehicle for accomplishing that.

Her best friend who he (try to keep up) had met just a couple weeks after arriving, a Latino guy named Jose, had also transitioned, and she was now a hot Latina named Jasmine.

The two girls had a lot of fun using their dicks to spit-roast both guys and girls during their senior year... enjoying their frequent double-team seductions the most. And of course they invariably loved the shocked looks on their preys' faces when their big cocks emerged from underneath their cute little dresses. They both took full advantage of the way straight men would willingly suck their dicks and take it in the ass, since the owner of said dick was a knockout blonde, or a sexy Latina who had tits. Girls also loved getting spit-roasted and double penetrated by them. They had a wild senior year.

Receiving her degree in business management, and Jasmine hers in marketing, they decided to leave California and relocate to Dallas... a two hundred mile drive from his original hometown where her parents still lived (she assumed), who had disowned him (as he'd been then) just under five years ago. They chose Dallas because the business plan they wished to follow was a dime a dozen in liberated Los Angeles, yet it would be seen as edgy and controversial in Dallas. And of course controversy, among other things, served as wonderful free advertising!