“A Shemale Submission”: A Lust Story

Summary: Author Jasmine falls for a hot new teacher with a big cock.

Note: Thanks to hfernandez1983 for the many pictures used in this story. He spent weeks getting these perfect for the many different scenes I requested. If you like the pictures in this story, please feel free to read the multi-chaptered series Cheerleader Mom and/or read hfernandez1983’s own illustrated stories.

Note 2: Thanks to Robert, goamz86, Wayne and cuckdynasty for editing this story.

Note 3: This is a 2016 Valentine’s Day Contest Story, so please vote. And although it is indeed an unorthodox and complex love story, it’s a love story nonetheless.

Note 4: All fantasies will be done in bold to separate them from Jasmine’s much less riveting reality.

Warning: This story is also very, very long (At just over 40,000 words and over 180 pictures)! It is a lengthy story of one of my fantasies, mixed with even more fantasies.

Author’s Note in advance on multi-plot story and somewhat pretentious self-indulgence:

Many fans ask me often about my personal life, my writing philosophy and so forth. So I thought I would write a story that embeds one of my BIGGEST fantasies – to be taken by a shemale – and mix it with who I am as a writer and a teacher.

So I apologize in advance if this story at times comes off as pretentious… but it was a chance to write a very complex story, work with many of my fantasies, and also give some insight into my mind as I write.

Jasmine January 2016

“A Shemale Submission”: A Lust Story

I have lived a dual life for years… since April 20th, 2010 to be exact. That was the day I released my first two erotic stories on Literotica: ‘The Complete Submission’ and ‘The Perfect Fall’. Looking back at those two now, I cringe at my writing: my lack of character development, my vague semblance of a plot, and my ‘by the numbers’ sex scenes.

The persona people see is pretty simplistic. I teach English at a high school in a small town in Canada. I am a mother of two, a twenty year old son and an eighteen year old girl. My husband died a couple of years ago in an oilfield accident and I have been a single parent ever since. I have not dated at all since, and even if I did, I’m not sure it would be with a man. However, I wasn’t ready to tell my children I might be a lesbian. Besides teaching, grading and coaching volleyball, I also take my son to football and my daughter to dance. I’m also a caring sibling. Both my sisters have been going through hard times and I have been there the best I can be. I’m also a concerned daughter who is always checking in on my aging parents. I am, without a doubt, the glue that keeps my family together.

My serious look:

The secret persona that no one, I mean no one (not even my late husband or my siblings) knows, is the erotica writer. I have been for years. And over the past five years, I have published over 200 stories in a few different sexual categories. Not to be pretentious, because that’s not who I am, but my stories are read by thousands of people daily and I have stories with over a million reads (four of them). I started writing because I was bored at home one summer, when the kids were much younger and wanted to explore some of my fantasies (mostly lesbian) through writing. I didn’t originally have any intention of releasing them online, but on a whim one day I created an account on Literotica, a new email address, and submitted my first two stories.

I had no idea that whim would forever change my life. I felt a rush when I saw them published; I felt a rush when I saw the stats (score, votes and reads); and I felt a rush when the stories received comments on the website or in an e-mail.

Sure, some were super negative, but the majority were positive and flattering.

I had no idea what an ‘H’ meant beside a story. I had no idea that readers could favourite stories or favourite authors. I also had no idea that it would stir a need in me to write more and to satisfy a need for recognition by strangers.

I started writing sequels to those stories and although they did okay, it was ‘Bedding the Babysitter’ that convinced me to write and publish regularly. The story took off and I have received hundreds of emails from fellow women, teenagers, and college girls sharing similar feelings with the protagonist Jenny. I learned I wasn’t the only woman who questioned her sexuality. This story seemed to push curious girls to experiment, in the closet girls to accept who they were, and older women to explore their own lesbian sexual fantasies.

Learning that my stories impacted people flattered me, and I have been writing ever since… attempting to release a story a week.

Anyways, the point of this meandering ramble was that I had done a great job of keeping my two opposite personas separate.

Although it took months to become the submissive slut I often wrote about, in retrospect, it probably started the first day of a new school year.

Both of the other English teachers in our small department were gone (one retired and the other was on maternity leave). This threw me a bit as we had worked as a threesome (the non-sexual version of the term) for the past five years.

My school look… serious and professional… but sexy… and, like my username, always in stockings:

At school, I was a woman of habit and didn’t like change. I had grown accustomed to how well we worked together and dreaded the thought of training two new first year teachers: it was obvious this would mean more work for me as I had to mentor both of them.

Now I probably sound like a bitch, but I’m not. I just hate training the new generation of teachers which are, for the most part, lazier than my generation.

Most of these worries faded when I actually met the new teachers I had prejudged without actually meeting them.

The male was a witty young man with a drama background, and wanted to perform a musical in the spring, something I had wanted to do for years, but couldn’t pull off alone.

The female, Annabelle, I instantly knew was trouble. A redhead (my weakness), green eyes (my weakness), and legs clad in mocha coloured pantyhose (my ultimate weakness in both the nylons and the colour).

Although I had plenty of moments of temptation over the years, I had resisted taking a bite out of the apple of sin… at least when it came to my students… But a teacher on my staff? Well… that wasn’t out of the realm of possibility.

I have been with a few women, including teachers, but always when I was out of town at conferences. Besides being a teacher, I also have a Masters Degree in Assessment and was often asked to keynote at conferences or do full days of school professional development.

I had travelled to all ten Canadian provinces and two territories, twenty-four American states, and this past year did my first European gigs hitting England, Belgium and Norway (I had my first Norwegian, as well as my first British woman during that trip). Those gigs had me already hired for a week-long tour in 2016 during my spring break where I was doing five keynotes in Italy. Much of my ancestry is there. I had already booked off a second week so I could travel Italy before ending in Paris so I could see The Louvre.

Again, off topic.

Anyways, I was instantly intrigued by the red haired, green eyed, young British woman, especially as I had often fantasized about wild nights in London with an older British woman who dominated me in ways I had only dreamed of. At twenty-five, Annabelle was much younger than me, yet she spoke as if much older.

She had travelled extensively and was really excited about this one year exchange.

Over the first month, I noticed a few things:

Like me, she wore nylons every day.

Like me, that even included casual Fridays where she wore pantyhose and heels with her jeans.

Like me, she kept her fingers and toes perfectly manicured.

She was a very touchy feely woman, unlike me, often touching my hand or arm when we were working together, which was often because we were assigned a period every second day to work together, along with the new guy, Mike.

She had a sexy English accent that somehow made everything she said sound sexy to me, just like the older woman back in London… who never did tell me her name… other than Mistress.

I was completely intoxicated by her and spent many nights imagining that she seduced me and made me her pet.

Annabelle had become my newest late night fantasy. My daughter in bed, marking was done, and I am in story mode for the evening, fantasy. I usually write for a couple hours before bed and then, when my writing gets me horny, I either put on some porn, usually lesbian, or fantasize about submissive to a dominant female.

Sometimes it was to students.

Sometimes it was to parents of students.

Sometimes it was to colleagues.

Sometimes it was to celebrities, especially younger pop stars who wore nylons like Taylor Swift or Selena Gomez, who both had turned into lovely, sexy women. Like seriously, Swift has to be a domme, Gomez a submissive (maybe a story I should write one day).

Sometimes it was to my two sisters… like I wrote about in the ‘Three Sisters’ story.

Sometimes it was to a couple of my friends.

But more times than not, it was to our second year principal… Ms. Rose. She was a beautiful, big breasted young woman, already principal at age twenty-eight, with a no-nonsense attitude.

Most of my fantasies had her coming to my room to have me lick her pussy whenever she needed to get off. The idea of being just a pussy pleaser (similar to many of my gay male stories where they were just cocksuckers) was a major turn-on. Just giving and not receiving… just being a good submissive (like so many of my protagonists… so many characters are based on my wide range of fantasies).

Here is one such fantasy I had played repeatedly for months before the arrival of Annabelle:

Parent teacher interviews are done. The last one was an exhausting one with a tiger mom who believed her child should have a 100. She was so intense that I had Ms. Rose join me for the interview since the parent had been a problem for all the teachers and the administration.

After almost an hour, the meeting ended, with no real conclusion or agreement with our assessment procedures, and she threatened to go to the board.

As soon as the parent left, Ms. Rose sighed, “Well, that was fun.”

I laughed, “Yes, it was almost orgasmic.”

Rose looked at me with a sly smile. “Interesting choice of words, Mrs. Walker.”

“Sorry, Ms. Rose,” I apologized, although truth be told, the way the mother treated me like a child both pissed me off and turned me on. More than once during the interview I had checked out the Asian woman’s nylon-clad legs and imagined her taking me then and there, forcing me to give her child better grades.

“Your cheeks are all red,” Ms. Rose noticed.

“It’s hot in here,” I said, even though the room was chilly.

“Oh, it can be,” Ms. Rose quipped, as she walked over to me and asked, “Did the tiger bitch turn you on too?”

“What? No!” I lied.

“She did,” Ms. Rose smiled, now directly in front of me.

“It’s just, I, um, well,” I was completely flustered. I found Ms. Rose incredibly attractive and she had been the focus of many of my dildo fucking sessions.

“You’re a submissive, aren’t you, Jasmine?” she asked.

“What? No, I….” I tried to defend.

“The bitch has me horny as hell,” Ms. Rose revealed. “I wanted to throw her on the desk and shut her up my grinding my cunt on her pretentious face.”

“You did?” I asked, as my panties instantly dampened.

“I did, and I think I plan to role play that exact situation with you,” Ms. Rose shocked me. “Get on your desk, you fucking dumb bitch.”

I gasped. “Ms. Rose, I ….”

“Now, you fucking bitch! You think you’re a tiger mom? I’ll show you where your place really should be,” Ms. Rose roared.

Startled and shocked, yet equally turned on, I nervously got onto my desk.

“Lie down, bitch,” she demanded, as she took off her skirt, to reveal she was wearing a garter-belt and stockings.

My pussy gushed again.

Now deciding to say ‘fuck it’, to go along with the role play, I protested, “Ma’am, this is highly inappropriate.”

Ms. Rose smirked, “How you treated me and Mrs. Walker was incredibly inappropriate. Now it is time for you to return to your natural position in society… as a submissive.”

I watched her get on my desk, straddle me, and lower her pussy to my face.

I was in awe. Her pussy was so inviting. My mouth watered as she grabbed my head and lifted it into her wetness.

“Get licking, you pretentious slut,” Ms. Rose ordered, “it’s time to eat some crow.”

And I did.

I was also intoxicated by her. Even her pussy hair seemed to perfectly capture the exotic scent that only women have.

As I was swarmed by the intense scent and sweet taste, Ms. Rose kept talking.

“Lick my cunt, bitch,” she ordered, roughly moving her pussy on my face. “This is the position you should always be in. Either on your back munching cunt or on your knees munching cunt.”

“Yes, ma’am,” I replied, between licks, trying to roleplay the typical subservient Asian as well as my usual submissive self… this crazy encounter a dream cum (wording on purpose.. LOL) true.

“About time you addressed me properly,” Ms. Rose said. “Although the proper term is ‘Mistress’ and you are slave, pet, slut, bitch, twit, cunt-muncher, whore, and bimbo.”

Each word sent chills through my body as I loved name calling. It always turned me on to be treated like a simple slut for another’s pleasure.

“Yes, Mistress,” I moaned.

“Yes, Mistress, what?” she asked, as she kept grinding her pussy on my face.

“Yes, Mistress, I’m just a stupid bimbo mother slut who should never have disrespected or questioned a superior woman like yourself,” I answered, talking from the point of view of the tiger mom, but meaning every word.

“Such a fucking slut,” she moaned, as she let go of my head and cupped her voluptuous breasts.

“How obedient of a slut, are you, bitch?” Ms. Rose asked a couple of minutes later.

“I’m your bimbo slave,” I answered, speaking for me now and not the fictional tiger mom.

She stood up, turned herself around and squatted over me again. “Eat my asshole.”

“But, ma’am,” I feigned in role play mode.

“No buts, slut,” Ms. Rose snapped, slapping both my tits. “Do as you’re fucking told. Now get that tongue up my asshole.”

“Yes, Mistress,” I obeyed, as I craned my head up slightly to reach her puckered rosebud, another unique scent and taste hitting my senses.

“That’s it, bitch,” she moaned. “You came in here to put us in our place, and now you are being put in your place.”

“Yes, Mistress,” I agreed.

“I’ve wanted to do this all year,” she said.

“Me too,” I answered, no longer the tiger mom, but the submissive sex writing teacher who had long fantasized about this type of submission.

“I bet you have,” she purred.

I licked her asshole for a couple more minutes until she got off of me and said, “My knees are getting sore, come finish me off over here.”

“Yes, Mistress,” I obeyed, following her to a nearby table.

She sat on it, spread her legs and smiled, “The other position bitches like you should always be in is… on their knees.

“Yes, Mistress,” I eagerly nodded, as I dropped down onto my knees, moved between her nylon-clad legs, and buried my face in her sweetness.

“Such an eager bitch,” she moaned. “You may actually earn yourself an A yet.”

I purred, “I want to earn an ‘A’ plus, Mistress.”

“Then you’d better show me just how good a submissive little cunt munching whore you really are,” she responded.

“Yes, Mistress,” I obeyed, exploring every crevice of her pussy, wanting to give her the best orgasm she had ever experienced.

“Oh yes, slut,” she moaned, as she leaned back. “Use that wicked tongue of yours for good for once.”

I kept licking, exploring, and teasing, wanting to get her revved up before I moved to her swollen clit.

“That’s it, bitch,” Ms. Rose moaned, before adding, surprising me, “I think I’ll have your little nerd daughter earn her grade this way too.”

“What, ma’am?” I asked, acting surprised in my role play.

“Your daughter is a dyke, just like you,” Ms. Rose continued. “She has been munching on cheerleader pussy all semester.”

“What? No!” I gasped, looking up at her.

Ms. Rose laughed. “Your daughter doesn’t tutor the cheerleaders. No she is being tutored in how to be a pussy pleasing rug munching whore… just like her mother.”

“No,” I said, looking defeated.

“Like mother, like daughter,” she shrugged, grabbing my head and pulling me deeper in. “Now stop talking and keep licking, slut.”

I obeyed, really enjoying the twisted wickedness of the role play. As I licked, I imagined sweet, nerdy Jung in between the legs of some of the cheerleaders, especially Robyn who was one of the most beautiful girls I had ever taught and knew it.

“Stop fucking teasing me, bitch. Suck on my fucking clit,” she demanded.

I obeyed. This made her legs twitch.

A few flicks and then some concentrated pressure was all it took as Ms. Rose’s orgasm was close.”Don’t stop, bitch,” she demanded, her breathing getting erratic.

I took her clit into my mouth.

“Oh yes, if your daughter wants to be Valedictorian I’m going to use my strap-on and fuck your daughter’s ass in my office,” Ms. Rose declared.

“Use the bitch as you wish,” I replied, as I continued the aggressive attention on her clit.

“You want me to ass fuck your daughter, slut?” she questioned.

“Like mother, like daughter,” I responded, the idea of her using my eighteen year old daughter suddenly popping into my head.

“You want it in the ass too?” she asked.

“Yes,” I admitted, just as she came.

“Yesssss, you whore, I’m coming,” she screamed.

I eagerly lapped up her cum as she kept my face buried in her pussy.

As you can see, I’m a twisted woman.

The idea of being dominated, forced to serve other women, especially younger girls, legal of course, kept me wet at school, horny at night, and stimulated my creative juices as I wrote story after story… releasing at least one a week (not to mention the fact I usually had between 5-15 stories in the can for release).

As I already mentioned, although I look prim and proper on the outside, my fantasies are all of being used like a dirty slut.

I want to be dominated.

I want to be used by other women.

I even have started fantasizing about my own eighteen year old daughter, Tori.

I have written many incest stories throughout the years, mostly son and mom, but a few daughter and mom. At the time, I wasn’t thinking at all about my daughter… but now… these feelings emerged.

Tori was incredibly fit, being an athlete who was a starter on both the volleyball and basketball team, as well as being a runner in track & field.

Tori was intense and hated to lose when on the court or field, but otherwise was a sweetheart.

Actually, she was one of the sweetest young ladies you could ever meet. She volunteered at an old folks’ home, coached younger kids at basketball, and was a youth group leader.

The fact that I sometimes fantasized about her was so wrong… but my pussy and naughty mind didn’t care about that when revved up.

Now, even though I had begun to have my daughter show up in my submissive fantasies, I had no intention of ever doing anything about it.

It was just a fantasy… like all my others.