Trans School: A Teacher Seduced

Trans School: A Teacher Seduced

Summary: A teacher is oblivious to the sex secrets of her new school.

FOR STORY 700, I THOUGHT IT WOULD BE FUN TO DO A MASSIVE ILUSTRTAED STORY (In the end, we ended up doing two). A lengthy next chapter of BIG FAT COCK with fun possibilities for future chapters (released later this year) and a refresh of the original 'Shemale School: A teacher Seduced' story that is slightly more politically correct. This new version adds new plots, characters and we got so ambitious we have decided to make this a 20-plus-chapter series (PS we are already on Part 5 as we send this in). The first 5 chapters will be illustrated and at the end of this refresh of the original story is visual teases for the rest of the epic that will likely run into 2026.

DEDICATION: This story is dedicated to my long-term editor and illustrator, TEX BEETHOVEN, for this and many other stories who recently just past away.

Note 1 [Written in 2013]: I was asked by a fan if I would ever write a she-male story a couple of years ago. At the time I didn't put much thought into the idea as I focused on my lesbian, gay and incest stories and truthfully knew very little about transgendered people. Yet another fan sent me pictures of cartoon Dickgirls and it stimulated an idea and made me curious. I began reading transgender cartoons and stories and researching the different terms like transgender, trans woman, trans man, dickgirl, t-girl, she-male, intersex, and hermaphrodite. The more I read, the more intrigued I became, and soon a story idea was forming. The story was supposed to be a simple one about a bi-curious teacher who is seduced by a she-male, completely unaware of the student's uniqueness, thinking she is being seduced by a girl for a lesbian encounter. But, like many of my stories, the story took on a mind of its own. In the end, the story became a novella of sorts that refused to end, and I hope you enjoy. (PS: A decade plus later I've decided that a better term is 'trans', instead of the sometimes offensive 'she-male')

Note 2 [Written in 2013]: Deciding to have some fun with this story, I also made the narrator ME! (2024: I have done this quite a few times since LOL; but back in 2013 this was a novel new idea... ish). This version of me is pretty accurate (except I am still happily married... 2024: although I am just now going through empty nest syndrome) and I refer to many of my earlier stories. It is not necessary to have read any of my earlier works, but the references are fun winks at my writing past, and they do reveal some clues to the real me.

Note 3: Tex wants to thank Pawngame, a graphics artist from RenderHub, for her invaluable assistance in posing our trans students in this series.

Thank You's: As always thanks to MAB7991 for editing the original version of this story; I hope you are still doing well. Thanks to Tex Beethoven for his recent editing, and for his illustrations and rejuvenation of this story (parts 2 and 3 are already written). Lastly, thanks to Shuj and David for a last-minute edit.

PS: When I first wrote this over a decade ago I imagined it illustrated as it was inspired by the Innocent Dickgirls comics... now finally that vision has come true.

PSS: While this is a rewrite of the original story called Shemale School: A Teacher Seduced there is one fun new scene staring me and secretary Amanda.

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1. A PROLOGUE

After more than fifteen years of teaching in public school systems in Canada, I was offered a job at a reclusive private school in southern California. I was in desperate need of a change in my teaching career, having been no more than just existing in an exhausting and mind-numbing routine. I was sick of all the pressure just to pass everybody, regardless. I was sick of the entitlement issues of today's students, and truth be told, I was sick of the six months of winter (it really is depressing when there's already snow on the ground by mid-October).

At first I didn't even consider the job offer, but when the California school's Headmistress committed to paying all my relocation costs, and offered me a salary that was double my current one in Canada, I couldn't resist. Not to mention, southern California doesn't ever get snow, unless you go looking for it high in the Sierra-Nevada Mountains.

When the Headmistress of the school actually called me up about the job, I was quite surprised, since I'd never even applied, and I remember the phone call vividly:

"Hello, is this Ms. Jasmine Winston?" asked a friendly female voice.

"Yes it is," I answered, having just gotten home from work a few minutes earlier, after a rather exhausting day that had really taxed my patience.

"I'm Headmistress Alexis Carlton, and I run an all-girls' school in southern California," she introduced herself.

I assumed I was about to be invited to come and speak to her school staff, delivering one of my keynote presentations. Although I'm not an expert, I've written about teaching approaches that work, and have also spoken about bringing learning to people's lives. Last year, I won a teaching excellence award in Canada as one of the most innovative teachers in the country.

She continued, "After hearing you speak a few weeks ago, I found myself wishing I had someone just like you on my staff. You have such enthusiasm and passion for teaching! I went back to my school quite rejuvenated by your lecture. Then a couple of days ago while I was planning for next year's' school year, a thought popped into my head. If I want someone like you, why shouldn't I just reach out and recruit... you?"

I was listening only vaguely, tired from my long day, even though her flattery was cheering me up noticeably. And then her most recent sentence snagged me right into the conversation. "Pardon?"

"I'm calling to interview you for a position at my school, although I'm already confident I want to hire you," she informed me.

I was flattered and surprised. "Really?" I asked, still a bit dumbfounded by the call.

"I must have you," she said, her voice communicating her determination even over the phone.

We spent ten minutes on her questions and my answers and vise versa, before I agreed to get back to her in a couple of days to tell her whether I was interested in setting up a Skype interview for her to record and show to her associates.

Over the next couple of days I mused at length upon this opportunity. My youngest son was in grade twelve, and he'd already been accepted by a university on a football scholarship several hours away; my daughter was in her second year at a university in Toronto, over 30 hours away, and I'd already been worrying about empty nest syndrome. A new school with a new start would be a great distraction from being home alone without any kids anymore.

In addition, since I'd divorced my husband after he cheated on me with his secretary a couple of years ago... how cliché is that?... I'd already decided I wanted to start over somewhere else, and I'd been applying for jobs in other provinces... although California was in an entirely different country.

So if I hadn't been fed up with my current job and its lack of a strong educational system, or if my children were younger, or if my husband hadn't been a cheating bastard, I probably never would have even considered such an extreme move, but the stars were all aligned, and I decided what the fuck... why not?

Of course, I did my due diligence first, and researched the school extensively.

The school, called Chateau Johnson for Girls, was an invitation-only school for gifted girls. Located in rural southern California, the school was plonked in the middle of nowhere, so all the girls lived in the dorm at the school. The teachers also lived on campus, and besides our teaching duties, we'd also be expected to serve as dorm mothers. The more I read about the school, the more mixed my feelings became about this unique opportunity.

Whenever I'm considering an important decision, I like to write down my thoughts in lists. So here goes:

Reasons to take the job:

1. The idea of teaching only academically gifted girls, young women all, was really exciting, but all those teenage hormones would likely be exhausting.

2. I loved the idea of living in the fresh air of the southern California countryside, but I wasn't so keen on living in the vast emptiness where the school was located. The nearest town with any stores was forty minutes away.

3. The idea of being a dorm mother was quite interesting; in public school I'd taught more than 200 students in a year, and frankly, I only managed to achieve meaningful teacher-student relationships with a few of them. I spent so much time working with the kids who were failing, skipping classes, and so forth, that making any real connections with my students was rare. Contrarily, at Chateau Johnson for Girls the class size was capped at 18 (at my current school the cap was 28, but that was only a suggestion, and 35 students crammed into a room designed for a maximum of 30 was all too common).

4. I was thrilled that during any given year I'd be teaching the same group of girls all the subjects I love the most: English, World History, Creative Writing, and Drama. And I'd finally get the chance to teach creative writing. I'd always wanted to, but the Creative Writing teacher at every school I'd ever worked at was already entrenched in the position (and trust me, teaching staffs are just like high school society... full of cliques and impossible to change).

5. Free housing was included as part of my salary, thus saving me a ton of money on rent.

6. I was entitled to six free round-trip flights a year (with no restrictions on my destinations).

7. I also had 20% prep time for my classes (20% more than at my current school),

8. I'd be in charge of the drama club, the graduation ceremony, and would be the faculty advisor for the student council. I was excited about my additional duties as a dorm mother. It would give me lots of opportunities to interact with the students outside of the classroom.

9. Also, I was in awe of the many famous alumnae this small school had groomed. Politicians, lawyers, celebrities, doctors, and every other high profile job imaginable were present in the school's small but very elite alumnae.

10. Lastly, I was in awe of the Dress Code at the school. In every school I'd ever worked for, any dress code (if they even had one) was only a suggestion. If I had a dollar for every time I'd seen a girl's thong or a boy's underwear, I'd be rich. If I had another dollar for every skirt that was too short, or cleavage too obvious, I could feed a third-world country. Yet at this elite school, there wasn't a standard school uniform, but they had very clear rules the girls must follow:

-they must wear a blouse (only the top button could be undone) and/or a sweater

-they must wear one of three skirt choices (supplied to them by the school)

-they must wear pantyhose (also provided by the school)

I was fascinated that pantyhose were mandatory. (I'd never seen that before; some schools required tights or leggings if someone's skirt was too short, but even that had seldom been enforced.) If I saw a dozen girls wearing pantyhose in an entire school year, that would be a lot at my school... unlike in the eighties when I was in high school, and most girls wore them every day. I myself had been wearing pantyhose or thigh highs ever since college when my boyfriend at the time said I looked sexy in them. I've always loved the feel of silky nylon on my legs and felt they accentuate my strongest asset perfectly. I have small breasts, 34b, and a decent ass, but my legs are easily my best asset. Conversely, I've always noticed women in pantyhose and although I'm straight in practice, I often fantasize about being with a woman.

I'm a published writer with a few plays published, a book of poetry, and a few of my articles have been included in educational journals. But my most prolific writing has been under the pseudonym of Jasmine Walker. I love writing porn. I've posted almost 700 stories on a website called Literotica in a variety of genres and themes.

My themes are almost always about submission, seduction, humiliation, and (especially) stockings. My genres are varied, but my most common ones are lesbian, incest, group sex and gay. This was my dirty little secret in real life, I lived vicariously through my writing. My real life was a lot less riveting and exciting compared to my fictional world, so this career move would be a chance to rekindle the adventurous side of me that had never taken the risks my fictional characters did.

I wanted to be like my characters, and every story I write always contains pieces of the real me, but I'm much more conservative in real life (although I'm not a complete innocent either), although like many of my characters, I was just one temptation away from breaking free from the invisible chains society had shackled me with. Although, no one who knows me knew this, it was the naughty side of me simmering just below the surface... bubbling like a volcano long dormant, but like all volcanoes, they eventually erupt.

In the end, I decided the offer was too good to refuse, both financially and professionally, and after two Skype interviews, I was officially offered the job. I accepted, but due to an already-planned trip with a couple of girlfriends, I couldn't arrive till the day before school started. Not ideal, but the reality.

2. THE FIRST DAY

I arrived disheveled, exhausted and PMS-ing after a five-day drive (which should have taken four) that was one disaster after another, causing me to arrive a full day later than I'd anticipated.

Headmistress Alexis (she refused to allow anyone to call her by her last name... and I quickly learned that all the teachers allowed their students to call them by their first names as well), was so sweet and helpful when I arrived. She wasn't fazed at all when I phoned her enroute about my travel problems, and after I finally did arrive, she assigned some students to help me get settled in. I arrived just after 3:30 on the first day of school; I finally met Headmistress Alexis in person in her office, curious to see whether she was as commanding in person as she was on the phone and Skype.

Her secretary, a very pretty young woman who introduced herself as Amanda, welcomed me and said, "Headmistress Alexis will be with you in a moment, ma'am."

I smiled, "Please call me Jasmine."

"Of course, Ms. Jasmine" the blonde smiled back, before disappearing behind a door.

I waited a couple minutes before I finally came face to face with the woman who'd recently changed my life, and would soon change it even more drastically.

She strode directly up to me and surprised me by embracing me in a warm hug the moment we met. Breaking the hug, which seemed longer than usual non-family ones, she said cordially, "Jasmine, I'm so happy you made it here!"

"Sorry I'm late," I repeated my apology from a couple of my phone calls.

"No problem. I'm just happy you've agreed to become part of our family," she said, squeezing my arm with apparent affection... stressing the phrase 'our family'.

I'd thought she was very pretty during our Skype interview, but the Internet didn't do her justice. She was a black-haired beauty (like the ones you only see in fashion magazines or movies), dressed in a professional business suit, black pantyhose, and five-inch heels that had me feeling overwhelmed. She oozed a mixture of power and sex, something I'd always wished I had; I was instantly intimidated by her, even though she was soft-spoken, caring, and excessively touchy-feely. I felt even more inferior, since I was dressed in jeans and a t-shirt, perfect for driving, but not for meeting my well-dressed boss for the first time.

"I'm thrilled that you're offering me this opportunity," I replied, as she sat on her desk and crossed her pantyhose-clad legs. Her legs captivated my eyes briefly, the pantyhose seeming to literally be shining.

Embarrassingly, she noticed me looking and smiled, as if she knew about my secret fascination for pantyhose and my secret fantasies of submitting to a woman. "They're Wolfords."

"What are?" I asked, confused.

"My pantyhose," she said. Apparently she'd noticed my staring at her legs.

"Okay," I said blushing, but trying to be casual about it.

"Go ahead and feel them," she offered, her voice soft and inviting.

"Pardon?" I asked.

"You need to feel how soft and luxurious they are," she said, her heel dangling from her foot.

"Okay," I said, nervous and yet curious. I came closer to her and touched near her knee. I'd worn silky smooth pantyhose my entire adult life, but I'd never felt anything so outrageously soft and sensual. "Oh my," I murmured. In many ways, this felt like a scene out of one of my stories: female seduction by nylons.

She agreed, "I know. They're what all our students wear too. I believe that for our school to be the very best, we must be the best in everything. We recruit the best students, we hire the best teachers, we have the best technology, and we dress the best as well."

"Wow," I gasped. I'd been so used to making do with outdated laptops, worn-out textbooks, and fellow teachers who hated their jobs.

She continued, "The skirts the girls wear are Ralph Lauren and the pantyhose Wolford, I considered making the tops all uniform too, but I wanted the students to have it all."

"How so?" I asked, impressed and curious.

"Well, the skirt and pantyhose promote conformity, family... because we consider ourselves one... and team spirit," she explained, "but choosing their own blouse or sweater gives them a chance to display their individuality."

"Wow! You're giving them the semblance of choice while still controlling everything," I assessed... impressed.

"That's right, it's a mirage," she smiled back.

"Ahhhh, and you're the puppet master," I joked.

Her smile widened. "I control everything that happens here, Jasmine."

"So it seems," I replied, amazed by how manipulative and yet brilliant this Headmistress was.

She pressed her intercom and said, "Amanda, please bring in Jasmine's pantyhose."

"I've always believed that if one dresses well, it commands a certain respect that's almost never questioned," she explained, her shoe slipping from her foot and dropping silently to the plushily carpeted floor.

I noticed her toenails were ruby red, and the pantyhose were sandalfoot, the same style I always wore... toes showing through nylons are perhaps the sexiest part of a feminine body.

"I totally agree," I said, before adding, "I would have preferred to meet you in person dressed more professionally than I am today."

She laughed. "I don't always dress like this either."