She-Male School: A Teacher Seducedbysilkstockingslover©
Summary: A new teacher is oblivious to the sex secrets of the school.
Note 1: 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 formed. The story was supposed to be a simple story 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 wouldn't end and I hope you enjoy.
Note 2: Deciding to have some fun with this story, I also made the narrator ME! This version of me is pretty accurate (except I am still happily married and my children are much younger) and refers too 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 do give some clues to the real me.
Thank You's: As always thanks to MAB7991 for editing.
Warning: Please note that the story has a VERY lengthy set-up before any real sex occurs. If you are looking for a stroke story I hope you like a lot of foreplay, innuendo and teasing first...I mean a lot...but once the sex begins....
SHE-MALE SCHOOL: A Teacher Seduced
1. A PROLOGUE
After over 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 living an exhaustive mind-numbing routine. I was sick of the pressure to just pass everybody, 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 is snow on the ground by mid-October).
At first, I balked at the job offer, but when the school's Headmistress committed to paying all my relocation costs and offered a salary that was double my current salary in Canada, I couldn't resist. Not to mention, southern California doesn't get snow.
When the Headmistress of the school called me about the job, I was quite surprised since I never actually applied, but I remember the phone call vividly:
"Hi, 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 tested my patience.
"My name is Headmistress Alexis Carleton and I am in charge of 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 about one of my keynote presentations. Although not an expert, I have written about teaching assessments that work and also spoke on bringing learning to life. Last year, I won a teaching excellence award in Canada as one of the most innovative teachers in the country.
She continued, "After seeing you speak a few weeks ago, I found myself wishing I had someone like you on my staff with such enthusiasm and such passion for teaching. I went back to my school rejuvenated by your lecture. Then a couple of days ago as I was planning for next years' school year a thought popped into my head. If I want someone like you, why not just go out and get you."
I listened vaguely, tired from the day, even though her flattery was cheering me up slightly. Yet, her last sentence pulled me right into the conversation. "Pardon?"
"I want to interview you for a position at my school, although I am 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 showing a determination even over the phone.
We spent ten more minutes on the phone before I agreed I would get back to her in a couple of days with an answer if I was interested in setting up a Skype interview.
Over the next couple of days I considered the opportunity. My youngest son was in grade twelve and was already accepted to a university playing football hours away, my daughter was in second year university in Toronto, over 30 hours away and I was already worried about empty nest syndrome. A new school, a new start would be a great distraction from being home alone without kids.
Secondly, since I divorced my husband after he cheated on me with his secretary a couple of years ago, how cliché is that, I had wanted to start over and had already been applying for jobs in other provinces...although California was in a whole other country.
So, if I hadn't been bitter with my current job and lack of a strong education system, if my children were younger or if my husband hadn't been a cheating bastard I probably never would have 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, Chateau Johnson for Girls, was a by invitation only school for gifted girls. Located in southern California, the school was in the middle of nowhere and all the girls lived in dorms at the school. The teachers also lived on campus and besides teaching duties were expected to be dorm mothers. The more I read the more mixed were my feelings about this unique opportunity.
Reasons to take the job:
1. The idea of teaching only strong academic girls, young women, was really exciting, but all those hormones would also be exhausting.
2. I loved the idea of living in the fresh air of southern California, but wasn't so keen on living in the vast emptiness the school was located. The nearest town was forty minutes away.
3. The thought of being a dorm mother was also quite interesting; in public school I had over 200 students a year and truthfully only made real teacher-student relationships with a few. I spent so much time working with kids failing, skipping class and so forth, that making real connections with students was rare. Yet, at Chateau Johnson for Girls class size was capped at 18 (at my current school the cap was 28, but that was only a suggestion and 35 students in a room made for 30 maximum was very common).
4. I was thrilled I would be teaching the same girls all the classes I love: English, World History, Creative Writing, and Drama. I would finally get to teach creative writing. I had always wanted to but the Creative Writing teacher at every school I had ever worked at was already entrenched in the position (and trust me teaching staffs are like high school, full of cliques and hard to change).
5. Free housing was included as part of my salary thus saving me a ton of money on rent.
6. I would get six free round trip flights a year (with no restrictions to where I went).
7. I also had 20 percent preparation time (20 percent more than I had at my last school),
8. I would be in charge of the drama club, the graduation ceremony and would be the faculty advisor for the student council. I was excited by the additional duties as a dorm mother that would afford me the chance to interact with the students outside the classroom environment.
9. Also, I was in awe of the many famous alumni that this small school had. Politicians, lawyers, celebrities, doctors and every other high profile job was represented by the school's small, but seemingly elite, alumni.
10. Lastly, I was in awe with the dress code of the school. In every school I had ever worked at the dress code was just a suggestion. If I got a dollar for every time I saw a girl's thong or a boy's underwear I would be rich; if I got another dollar for every skirt that was too short, or cleavage too low I could feed a third world country. Yet, at the elite school there wasn't a complete school uniform but very clear rules the girls must follow:
-they must wear a blouse (only one button could be undone) or sweater
-they must wear one of three skirt choices (given to them by the school)
-they must wear pantyhose (also given by the school)
I was fascinated by the fact that pantyhose were mandatory (I had never seen that before; some schools required tights if the skirt was too short or leggings, but that had seldom been enforced). If I saw a dozen girls in pantyhose in a whole year that would be a lot at my school, unlike the eighties when I was in high school and they were worn every day. I had been wearing pantyhose or thigh highs since college when my boyfriend of the time liked me in them. I have 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 always noticed women in pantyhose and although I am straight, I often fantasize about being with a woman.
I am a published writer with a few plays published, a book of poetry, and a few articles on education. Yet, my most prolific writing was under the pseudonym Jasmine Walker. I love writing porn. I have written more than eighty stories on a website called Literotica, the majority of them rather popular.
My themes are almost always about submission, seduction, humiliation, and stockings. My genres are varied, but my most common are lesbian, incest, group sex and gay. This was my dirty little secret, I lived vicariously through my writing. My real life being a lot less riveting and exciting in comparison to my fictional world, thus this move was a chance to rekindle the adventurous part of me that had never really taken the risks my characters took.
I wanted to be like my characters, and every story always has pieces of the real me, yet I am much more conservative in real life (although I am 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 put on me. 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, 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 could not 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 that was one disaster after another and had me arriving a day later than anticipated.
Headmistress Alexis, she refused to allow anyone to refer to 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 called her about my travel problems and after I finally did arrive she had students help me get settled in. I arrived just after 3:30 of the first day of school; I ended up finally meeting Headmistress Alexis in person at her office, curious if she was as commanding in person as she was on the phone and on Skype.
Her secretary, a very pretty young woman, greeted me, "Headmistress Alexis, will be with you in a moment, ma'am."
I smiled, "Please call me Jasmine."
"Of course, Ms. Jasmine" the blonde smiled, before disappearing behind the door.
I waited a couple of minutes before I was finally face to face with the woman who changed my life and would change it even more later.
She walked directly 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 hugs she said, "Jasmine, I am so happy you made it here."
"Sorry, I am late," I repeated my apology from a couple previous phone calls.
"No problem, I am just so happy you have agreed to be a part of our family," she said, squeezing my arm.
I thought she was very pretty during our Skype interview, but the Internet did not 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 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 as I was dressed in jeans and a t-shirt, perfect for driving but not for meeting your well-dressed boss.
"I am very thrilled to have been offered this opportunity," I replied, as she sat on her desk and crossed her pantyhose clad legs. My eyes watched her legs briefly, the pantyhose seeming to literally shine.
Unfortunately, she noticed me looking and smiled, as if she knew of my secret fascination for pantyhose and my secret fantasies of submitting to a woman. "They are Wolffords."
"What is?" I asked, confused.
"My pantyhose," she said, seemingly noticing I was staring at her legs.
"Ok," I said blushing, but trying to be casual about it.
"Feel them," she offered, her voice soft and inviting.
"Pardon?" I asked.
"You need to feel how soft they are," she said, her heel dangling from her foot.
"Ok," I said, nervous and yet curious. I moved to her and touched near her knee. I had worn silky smooth pantyhose my whole life, but I had never felt anything so outrageously soft. "Oh my," I said out loud.
She agreed, "I know. They are what all the students wear too. I believe that for our school to be the 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 must dress the best as well."
"Wow," I said, so used to getting by with outdated computers, worn out textbooks, and teachers who hated their jobs.
She continued, "The skirts the girls wear are Ralph Lauren and the pantyhose Wolford, I considered making the shirts all uniform too but I wanted the students to have it all."
"How so?" I asked, impressed but curious.
"Well the skirt and pantyhose implies conformity, family and team," she explained, before adding, "yet, choosing their own blouse or sweater gives them a chance to show their individuality."
"Wow giving the resemblance of choice while still controlling it," I assessed impressed.
"It's a mirage," she smiled back.
"Ahhhh, with you being the puppet master," I joked back.
Her smile widened, "I control everything that happens here, Jasmine."
"So it seems," I replied, amazed by just how manipulative and yet brilliant the Headmistress was.
She pressed her intercom and said, "Amanda, please bring in the pantyhose."
"I have always believed how you dress commands a certain respect that is almost never questioned," she explained, her shoe slipping from her foot and dropping to the floor.
I noticed her toenails were ruby red and the pantyhose were sandlefoot, the same kind I always wear.
"I agree," I said, before adding, "I would have liked to meet you in person dressed more professionally than I am today."
She laughed. "I don't always dress like this either."
Amanda entered and I noticed she was wearing the same shiny type of pantyhose, although hers were a mocha color, the kind I liked the most (it made the pale me look like I have a tan). "Here you go, Headmistress."
"Thank you Amanda," the Headmistress said, taking a small bag.
I watched as Amanda silently knelt down, picked up Alexis's shoe and slipped it back on her foot.
"Good girl," Alexis said, as if she was speaking to a child and Amanda left the room without a word.
I must have looked as perplexed as I felt as the Headmistress explained, "Amanda used to be quite a handful, but through constant discipline she has learned to be very obedient."
In retrospect, this was the second oddity that should have set off alarms in my head (the first was letting me touch her leg), but I was so in awe of her confidence and unexplainable allure I missed the clues completely.
I nodded, "I wish students at my old schools were so obedient."
"Oh here, you will learn the students are very well-behaved," she said, yet her tone implied she wasn't talking about school. Again, In retrospect there were so many clues as to what was underneath the surface (pun intended), but I was so taken with her confidence, beauty and intelligence that it never occurred to me that I was being pulled into a web of sin, being groomed for a position much different than what I was hired for.
"I think I am going to like it here," I smiled. "I have never felt I had the support of my administration at any of my old schools. Oh sure they talked the talk, but they tripped anytime they tried to walk."
She laughed, before her tone got serious, "That is funny. But here, I back up everything I say."
I stammered, not wanting to imply I was doubting her, "I-I-I didn't mean to imply I was questioning you."
"I know, dear," she smiled warmly. Being called 'dear' was odd considering I was no doubt a few years older than her. She handed me the bag and said, "Here are a dozen pair of Wolfford pantyhose for you in a variety of colors."
Taking the bag, I replied, my face showing my surprise at such an odd gift, "Thank you."
"You are welcome, Ms. Walker," she replied.
My face went beet red. No one knew my secret erotica identity.
She instantly corrected herself, "I mean, Ms. Winston. Sorry, I was just on the phone with a Mrs. Walker about a coaching opportunity at our school.
I let out a sigh of relief, feeling my secret was still safe, completely oblivious to the reality that it wasn't an error and that the labyrinth of innuendo and seduction was underway.
Again, in retrospect it was so obvious....
"Go have a shower and dress up, Jasmine, we have a faculty supper we delayed a day so you could meet the rest of the staff," she instructed.
Happy to have a shower and present myself respectively, I didn't notice her words were an order and not a suggestion. "Ok, I definitely could use a long hot shower."
"I will have Amanda come and get you at ten to seven," Alexis said.
"Sounds good, I don't think I would be able to find anything around here on my own," I joked.
Alexis smiled, "Don't worry my dear, we will look after you here."
An hour later I had been shown my fully furnished apartment (it was nearly as luxurious as a Penthouse of a hotel), I unpacked a few dresses and clean undergarments and had a nice, long, hot shower. Deciding to try to impress the immaculate Headmistress, I choose a dress rather glamorous for a faculty supper, a red dress that I had only worn once at a wedding and I pulled out a pair of mocha pantyhose, identical to the ones Amanda was wearing earlier, and put them on. As I slid them on my legs I felt rich and decadent. It was like the time I was upgraded to first class and was treated like royalty. The nylon was so soft I got myself slightly damp touching my own legs. I resisted the temptation to masturbate even though I had not had an orgasm for a few days (the long days of driving exhausting me past the point of my usual daily self-exploration and I was just finishing my period). Instead, I did my make-up and hair and tried to look my best.