Trans Summer

Summary: Trans woman and ex-student share a night of great sex.

Note 1: The idea for this story came from the real Lucy.

Note 2: This is a Summer 2021 Contest Story so please vote.

Note 3: Thanks for Tex Beethoven for editing this story.

Trans Summer

Following a brutal year of teaching at an upscale high school in Boston during COVID, Lucy Reid was excited to take a break from her country and travel to central Mexico for a two-week getaway.

The recent few months had sucked away all of her energy as she'd gone head to head against the school board chair Annabeth Lee Chase (seriously... who needs to throw two first names in everyone's face) over starting a LGTBQ-plus club at her school. It wasn't her idea, but when she'd been asked to be the faculty advisor for the club by a couple of students, she happily agreed.

It was a fortuitous coincidence... or perhaps serendipity... since her students had no idea that Lucy had begun her life as Luke. Or that Luke had struggled through a very difficult time in high school. He'd been an effeminate boy, so of course he was bullied by his peers and never fit in. ('Of course' not because he deserved any such treatment, but because kids... and many other people actually... could often be insufferably cruel.) His Dad could never figure him out, since he didn't care about sports or trophy cars or anything else manly, but preferred to read and watch movies and so forth. His caring and perceptive Mom figured him out much more quickly, especially when she discovered some panties and pantyhose stored in his room... something he secretly liked to wear whenever he could. She never mentioned her discovery to anyone, but she did quietly begin fetching them from their hiding place and including them in her normal laundry duties. And once Luke realized she was doing it, he began routinely tossing them into his hamper with the rest of his laundry, although he never said anything either.

Truth was, Luke found woman's clothing sexy. He loved the silky panties, and he really loved pantyhose. He loved the sheer softness of the hose, and how it made his legs look. He hated that due to societal expectations, especially in the South where he was being brought up, he could never wear them in public without being harassed or even beaten up... and those things happened often enough without his going out of his way to invite them.

The very day after his eighteenth birthday, he announced to his parents his intention to undergo gender affirming hormonal procedures. His Dad resisted the idea ferociously, as if his was the manhood being cast aside with such disrespect, and he took his son's decision to transition into a female badly, although after a few months, he simmered down and accepted his son's 'betrayal of his God-given gender', if only sullenly. That he accepted it at all was primarily thanks to Luke's mother's embracing her son->daughter's desire for happiness, and she was steadfastly there for him->her through those tough early days when almost all of his (now her) friends and relatives were outraged.

Ten years later, Luke, now Lucy, now twenty-eight, had flowered into an incredibly cute but plucky woman. A brunette, with perky B cup tits (from the hormones), and long legs always encased in nylons. Almost no one would suspect that underneath her cute attire slumbered a seven-inch cock.

She taught English, ran the yearbook, and in this crazy COVID year mothered the school's LGTBQ-plus club. A club that was sorely needed in this rich, overly pretentious community. Although perceived by her students and her colleagues as a sweet teacher to all her students, she wasn't anyone to be pushed around. After her early years of being bullied and never fitting in (having claimed for herself the feminine pronoun, along with the accompanying appearance, the very day she graduated from high school), she could rear up and become a real mama bear, and she was an outspoken advocate for any student who didn't receive the support he/she/they needed. She would stand up to administration, homophobic bigots, insensitive teachers, and cluelessly radical parents. She never set out to rock the boat... but if that boat got rocked inappropriately by someone else... well... she glared in their face and rocked it right back.

Unfortunately, she was currently facing in her biggest rumble yet...Annabeth Lee Chase... the aforementioned school board chair... and the wife of a browbeating pastor who preached like a throwback to the Salem witch hunt era. The pastor claimed to preach the word of God. Lucy stated that the God she knew would never issue such hateful and destructive pronouncements.

Annabeth Lee was perceived by many as an ice-cold alpha bitch. Lucy even mused that if anyone should have a penis hiding underneath her dress pants (the woman never wore dresses) it should be her. She was a pastor's daughter, and now a pastor's wife, and she believed in true Christian morals. She, like her husband and her father before him, followed the Old Testament... not the New one, with all its forgiveness twiddle twaddle.

Although Annabeth Lee was indeed a tyrant in public, someone you didn't want to fuck with, she was a complete submissive in the bedroom. Her husband was a dominant man, and he behaved very un-Christianly with her whenever the doors were closed and the blinds went down.

Annabeth Lee sucked cock daily... it was how she woke up her husband... always swallowing the load.

But no... Annabeth Lee always sucked cock at least twice a day... since she'd also visit him in his office at church so she could crawl under his desk to slowly worship his fat member, sometimes for over an hour, before he rolled back his chair, stood up, and issued forth her daily dose of organic facial cream, that she believed kept her looking young.

Annabeth Lee was never fucked in the pussy... not since they decided to stop having kids. Her husband considered artificial birth control a horrible sin, and he definitely didn't want any more children. So Annabeth Lee righteously took it in the ass... a lot. Occasionally he would just demand a blow job, or would roughly fuck her mouth while he watched porn (oddly, mostly gay porn), but usually he roughly plugged her ass and deposited his load in her butt. One couldn't get more righteous than that, could one?

Annabeth Lee also on a couple of dozen occasions, more frequently in the past couple years, had been spit-roasted. Her husband enjoyed sharing her with fellow men of the cloth. She hated herself for how much she loved taking cocks in her ass and mouth simultaneously.

Oddly... she loved all of it. She loved being used as a cheap slut. Portraying the ice queen all day in public was exhausting (even though she loved that too), so being told what to do, serving as a cum bucket for her husband and thus for the Lord (she'd been trained by her husband and subconsciously by her equally overbearing father that part of a woman's duty was to serve first her father (although not sexually) and then her husband (definitely sexually but in many other ways too), because they'd been sent to her as stand ins for the Lord).

All of this, of course, made her rampages about sexuality, gender identity, and pretty much anything else her church (read: her pastor husband) was against, rather ironic.

Even though she was such a secret slut, she presented herself as very prim and proper in public, and she was outspoken about many morally corrupt things (in her estimation), such as a strip club in her district that she led a successful crusade to shut down, and a violent movie that she argued the city council into insisting it be made in a different city. And her current mission: to censure out of any visibility the growth of the LGTBQ-plus community... and thus protecting her (read: everyone's) children from being attracted by such sexual blasphemies.

.....

Enter a third principal into this story. Maddy Chase, the eldest child in her churchgoing family, who hadn't yet come out to her parents as bisexual. In fact Annabel Lee and her husband believed she was still a virgin.

But the truth was Maddy was quite the slut. She was a year older than her peers, and had already turned eighteen by the time she began her senior year. She lost her virginity to the minister of a church (and a close friend/colleague of her father's) in a nearby town. She was gangbanged on her prom night. She fucked a different guy every single night (and thus they were all both strangers and one night stands) on her three-week Europe trip this past summer... as well as enjoying her first girl-girl encounter in Paris.

Thus her sex life was a complete rebellion against her parents, the church, and the patriarchy. (Hardly anyone called it the patriarchy, it was simply understood by almost everyone... without any discussion... that men were in charge of everything because of Divine Right.)

Then during her first year of college she really dove into exploring the pleasures of same sex play. She loved eating pussy, discovered that women ate her pussy way better than guys, that tribbing was incredibly hot, and wearing a strap-on and doing the fucking was pretty damn hot too.

So she preferred a woman going down on her to a man.

She preferred a real cock to a strap-on... although either one could get her off.

She enjoyed sucking cock and eating pussy equally... and she enjoyed swallowing cum and pussy juice equally... although if she had to choose, a gooey load of semen always went down smoothly. She always had liked salty things.

She loved fucking a pussy, and on a couple of occasions an ass... she loved being the top sometimes... it was such a wonderfully complete role reversal. Although, of course, she also loved getting fucked.

In an ideal world, she'd have a girlfriend with a cock.

Maddy, wanting to piss off her mother and father, especially her mother, came home from college looking a lot different from her perky long blonde hair cheerleader look of high school. She now had a shorter, punky haircut... one with mismatching spikes spearing into the air... one that screamed how Maddy was flying her freak flag high.

.....

All of which explains the backgrounds of these three women... Lucy née Luke, Annabeth Lee Chase, and her daughter Maddy Chase... whose lives would all collide, intertwine and change forever when the secretly transsexual Lucy encountered the secretly slutty mother and daughter on a reclusive resort island off the Pacific coast of Mexico.

Lucy was tanning, nursing a cocktail (her third of the day actually), enjoying the sun and silence, when a voice barked out, instantly sending an unpleasant chill up her back. "You've got to be kidding me!"

Lucy looked up to spy Mrs. Chase and her daughter standing before her. One of the women looked like she'd just discovered fire ants in her bed, while the other smiled warmly at her.

"Ms. Reid, it's great to see you," Maddy squealed, thrilled to happen upon her favourite teacher from her senior year.

"Just on a holiday," Lucy said, as Maddy (to her mother's silent horror) bent down and hugged her.

"How did you even afford this place?" The always pretentious and happy to take a shot Annabeth Lee asked.

"All my hard work teaching and lending my support to other people's kids," Lucy replied, not at all intimidated by the bitch.

"Since we're all here, we should go for a drink," Maddy said, excited to see Ms. Reid, and knowing it would really piss of her mother only added to why it was a delightful idea.

"I don't think so," Mrs. Chase said disparagingly, not even trying to hide her repugnance at the presence of a teacher, and even worse, the teacher who was promoting filth in her community, at this high-end resort.

"That would be lovely," Lucy smiled extra wide, all the while staring down (even while looking upwards) the bitch Mom. "It would be great to catch up with such a delightful former student and her charming mother.

"And I love what you've done with your hair," she added to Maddy, confident that the mother hated it.

"You were my favourite teacher, Ms. Reid," Maddy gushed, enjoying the sight of her Mom's cheeks going ruby red.

"Why thank you very much," Lucy smiled, turning her full attention to the very pretty nineteen-year-old.

"Let's go, Madelyn Heloise Chase," the mother said tersely, using her daughter's full name as a clear warning that she was in trouble.

"Yeah, yeah, Mother," Maddy responded, her emphasis on the word 'mother' the same she'd apply to 'whatever'. "We're just checking in, Ms. Reid. Why don't you meet me at seven at La Sangria Sabroso?"

"Sounds good," the teacher agreed, smiling widely at the peeved mother and the friendly daughter.

Mrs. Chase stalked away fuming, as Maddy waved adiós to her teacher...a teacher she not only admired, but somewhat imitated her style.

Lucy waved back as she resumed sipping on her mai tai.

.....

Lucy arrived at the cantina a few minutes before seven, since she hated being late.

Maddy arrived a couple minutes after seven, following a fight with her Mom a couple hours ago, and another one as she was preparing to leave. Of course Maddy was an adult now, which she reminded her mother about a few times, had moved away from her childhood home, and now made all her own decisions... and if those decisions annoyed her mother, all the better.

Both women wore light colourful sundresses, and because it was summer and 99° F. Lucy wasn't wearing her trademark nylons... although she'd brought a couple pairs along.

Maddy pointed that out as Lucy rose to great her. "No nylons? Aren't they your style?"

"I brought some, but it's crazy hot here," Lucy said, flattered that Maddy had noticed, and had even remembered her in such detail. "And besides, they'd be impractical, since I'm spending all of my time here barefoot."

"I guess," Maddy said, who wore them most days herself, but hadn't brought any to this remote island. "It's a little warmer here than Boston, and you're right: I'm not wearing any shoes either."

"I did bring along a couple pairs," Lucy said, then wondered why she'd made a point of repeating that. It wasn't like there'd be any possibility of fucking an ex-student... although her seven-inch cock was hard in her panties as she admired the pretty coed.

"Good to know," Maddy said, sitting down. She'd always found Ms. Reid sexy, and that was even before she'd discovered her love of girls, and she'd sensed back in high school that Ms. Reid might be a lesbian, a notion that was reinforced when she went head-to-head with her mother over the LGBQT-plus club.

Lucy was a little flustered by the teen's tone and response, as she too sat down. She couldn't explain why, but she felt Maddy's demeanor was rather flirtatious.

They ordered drinks and food, then reminisced about when Maddy was still attending high school, and compared notes about their crazy COVID lives, and Lucy learned that Mr. Chase and the two sixteen-year-old twin Chase girls wouldn't be arriving for three more days, since the girls' baseball team had advanced to the state finals... much to everyone's surprise.

Maddy then introduced a new topic by saying, "So I guess you know my Mom really, really hates you."

"Yes, I am aware of that. I'm not her biggest fan either," Lucy shrugged, sensing Maddy's inherent approval of her attitude.

"I wouldn't worry about it," Maddy said. "She hates anyone who questions her judgement, especially if they're in a lower task bracket."

"That isn't very Christian of her," Lucy joked.

"My mother is the least Christian Christian imaginable," Maddy responded with sharp bitterness. Although they lived in a large house, larger than most people who earned their living from the church, this summer she'd discovered the vent to her parents' room had a direct connection with the guest room in the basement, where she was staying this summer. So in the past month she'd heard everything. Her Dad's verbal sexual abuse. Her mother begging to be ass fucked. Both her minister father and her prim and proper mother using a lot of very inappropriate words.

"That's often the case," Lucy sighed, noticing the bitterness in Maddy's words, and having learned from her many years of suffering from other kids' abuse in high school, and more recently from ten years of advocating for the rights of sexual minorities, that the majority of people claiming moral higher ground than queer people had their own closets full of skeletons. Church-speak was very often a cover for acting morally upright (read: uptight and judgemental) in public, yet being morally corrupt in private. The irony was ridiculous, and it would be hilarious if it weren't so sad.

"Tell me about it," Maddy said, "they tell me what not to do, and then they go and do it themselves. They're both hypocrites, especially my mother. She had no right to wage war against the LGBTQ-plus club."

"Change isn't easy for many people, especially religious types," Lucy said, since almost all her fights were against religious people who were stuck in a different decade, and even perhaps a former century.

"That's been my experience too," Maddy agreed.

"So," Lucy said, wishing to lighten this somewhat boring and depressing conversation, "Tell me something you learned in college this year."

"May I be frank with you?" Maddy asked. "Even if it isn't something academic?"

"Of course," Lucy said. "Do you mean a life-changing experience?"

"Exactly! I discovered I like girls just as much as I like boys." Maddy revealed, deciding to throw it out there, along with a not so subtle ulterior motive.

Lucy choked on her drink, some of it even dribbling down her chin.

Maddy, loving the look of surprise on her former teacher's pretty face, aggressively stuck her bare foot between Lucy's legs to surprise her even further, but was herself surprised.

Lucy felt the teen's bare foot pressing against her cock. Her hard cock. Yes, it was certainly a surprise. Yet she felt more compelled to explain things than to push the foot away. "In case it isn't obvious what your foot is feeling. I'm trans."

"You certainly are," Maddy said, her foot still resting against her ex-teacher's hard cock... which surprised her at first, but that emotion quickly shifted to excitement because of the possibilities... since as has been said, a hot woman equipped with a living cock was her fantasy fuck.

"I initiated my transitioning a single day after I turned eighteen," Lucy explained, noticing Maddy wasn't disturbed or repelled by the discovery. In fact her foot was still pressed against her cock, which was still hard.

"So you've always had a penis?" Maddy asked, completely fascinated by this secret she'd just accidentally discovered. She'd been hoping to seduce her ex-teacher and enjoy some hot lesbian fun... but now the possible enjoyment had increased exponentially... while her foot still remained resting against the hard cock.

"Since the day I was born, and likely for a while longer," Lucy said, "although I'm not sure about the details since I'm not a biologist," enjoying the pressure on her cock, although Maddy's foot hadn't begun moving since it had discovered her secret, and she hoped it would.

"Well, that is very intriguing," Maddy said, granting the unspoken wish by slowly beginning to rub her foot up and down the hard cock.

"I don't think your mother would approve of what you're doing," Lucy smiled playfully.

"I don't think the hypocritical bitch would approve of what I'm about to do next either," Maddy added, as she pushed firmly against Lucy's surprise cock before drawing her foot away. She briefly looked around, saw no one was looking their way, and quickly crawled under the table.