The Headmistress
by Jehoram
Copyright© 2026 by Jehoram
Erotica Sex Story: A middle-aged woman takes a job at a college prep school where she can fuck a highly trained Royal Courtier and six young men, sixteen years old but already sexually experienced, and help six girls of that age experience their first cock. And then do it again and again at three weekend intervals.
Caution: This Erotica Sex Story contains strong sexual content, including mt/ft Ma/ft mt/Fa ft/ft Fa/ft Teenagers Consensual BiSexual Heterosexual Masturbation Safe Sex Small Breasts Nudism .
I got a call from an old school chum last fall, and it changed my life.
“Katya, this is Imelda. Remember when we talked last month about how bored you were with your job?”
“I sure do. It’s no different now. Running a community college isn’t as rewarding as it used to be.”
“Yeah, and that other part about your sex life?”
“That hasn’t changed, either.”
“Well, what if I told you that there’s a job where you can have all the cock you like, every night? And every third weekend or so, you get to fuck six young men, along with six fucks with a guy that really knows his stuff? What would you say?”
“How young are these men?”
“All fifteen years old and up.”
“I’d say, ‘too good to be true.’ Are you putting me on?”
“No, Katie. I’m dead serious. The headmistress of the Valleyview Academy for Girls is retiring. You should apply. You’ve got the qualifications already.”
“Jeez, Imelda! What do I have to do for that? Take a cut in pay?”
No, the pay is better. You know about the program for Sexual Gratification that the government is running?”
“I’ve heard of it. Something like training young boys and girls to be sexual servants at the Royal Palace, right? I’m not sure I could get behind that.”
“Hey, it’s consensual. Here at Pleasant Valley, the girls are begging for the opportunity. And when they come back, they’re the happiest kids in the world. As headmistress, you’ll also be running the Artemis Club if you want to ... that’s where the girls are trained to be orgasmic. And when they go to the Deflowerings, you’ll go along with them as an escort. That’s where you get do do all that fucking I talked about.”
“I didn’t know you were all that enthusiastic about cock, Imelda.”
“I’m still not. Young girls are my thing, and when the kids come back from the Palace and the Deflowerings, I’ve got all the pussy I can handle. I’m in heaven! And now I usually send one of my most advanced students as a chaperon for the Deflowerings in my place.”
“That’ll work for you, but not for me.”
“You, too! Hanging around a bunch of climaxing girls will bring out the lesbian in you, believe me. And there’s still plenty of cock at the school ... the male teachers, the masseurs...”
“Masseurs?”
“Masseurs. Masseuses, too. All trained in the art of bringing a woman to an orgasm, and giving you the best orgasms you’ve ever had. Katie, this is the opportunity of a lifetime!”
And that’s how I became the headmistress of the Valleyview Academy for Girls.
I’m thirty-five years old, mixed race, with breasts that are beginning to sag a little. One is a little bigger than the other ... the left one is a B and the right one is a C, which is only really noticeable when the bra comes off. They sport dark brown nipples that are small but sensitive. You usually can’t see the clitoris or inner lips of my trimmed cunt until I’m aroused. The only reason I’m telling you all this is that since I started to work at Valleyview, my sex life has exploded and I’ve become fascinated by the erotic parts of my body, and I’m no longer bashful about showing it to others or telling you about it.
It’s Valleyview’s first year of participating in the Kingdom’s regimen for grooming children for sex, which has been explained by others. At first, I thought of the program as simply a way for the Palace to be stocked with virgin children to be used as playthings for the government, solely for the benefit of the government. But I came to see the entire program for what it was: the best possible way for children to be developed as human beings with sexual appetites that can best be appeased by the process of regarding sex as not something dirty of furtive, learned from ignorant peers or Puritanical adults, but as something honored and valued, taught by those skilled in the art.
Here’s the way my thinking was changed.
I must confess that when I took the position of headmistress, I had a fairly conventional sex life. I’d had ten lovers, which was not a lot for the sybaritic society we now live in. They were introduced to sex the way I was, learning from each other as we went along. All that changed after I was hired. I found that it was entirely expected that any of the staff could be available for sex, and promiscuity was the rule rather than the exception. But at the school, I was soon sleeping with all the male teachers and the masseurs who are hired to give massages to the girls after their physical education classes. I found that these latter males were especially talented in giving me orgasms beyond count. My favorite one is Jared, a tall, lanky phys ed teacher with ginger hair and a cock that never seems to go entirely soft.
You already know about the massage sessions each girl experiences, after their phys ed classes. The massage staff is nude, as are the girls, so the girls can see male and female bodies as they should be. The lesson is that we should experience not the slightest sense of shame from displaying our nude bodies, or seeing other nude bodies. A penis, flaccid or erect, should be as familiar sight as a pencil, and a nipple as ordinary as a light switch. And if a girl becomes sexually aroused during their massage, they’re told that this is entirely normal and something to look forward to rather than to hide.
I learned that if the girls indeed showed any signs of sexual stimulation during those massage sessions, they were invited to join the Artemis Club, where the massages were sex-oriented and orgasms were the goal. And, as Advisor to the club, it would be my honor to introduce these girls to the full joys of sexual arousal.
I still remember the first time I looked in on a massage session. The masseur’s job was to see if Heather, a freshman, was ready for that first experience with real sex. She lay on the massage table, ready for it. Her breasts almost non-existent. Her brown hair was shoulder-length, and her eyes were green. She looked beautiful. At fifteen, she was the youngest girl in the class and, indeed, in the school.
The masseur was Tomaso, a tall Latino with a cock that was at half mast and slick with oil. We were both naked, since that was the required state of clothing in the massage room. Was that half-erection for the girl, or for me? I made a mental note to ask him if he wanted to fuck me some evening.
“You can take over the massage for Denise,” he told me.
“Open your legs, dear,” I said. “Let me see your beautiful pussy.” And it was a beautiful pussy, as all pussies are on girls that age ... sensitive, and unexplored.
She spread her legs, revealing inner lips just starting to blossom. I dripped some oil on them and began to caress them, slowly dragging my fingers along the length of her slit. She shivered. That was the response I was looking for ... the awakening of her body to the joys of lust. She was ready for her first session as a member of the Artemis club.
“Did you see that little shiver?” Tomaso said. “She is, I think, not far from being orgasmic.”
“That young?” I asked.
“Oh, yes. Some of the girls look forward to it. And I’ve been told that the Courtesan Prime, when she was a little older than this girl’s age, was orgasming from her very first massage session.”
“You’re kidding!”
“I’m not! A masseur from the Pleasant Valley school told me that. It’s true that her libido, even then, was through the roof. That’s exceptional, but nearly every girl you see around us will be cumming before too long.”
“What happens then?”
“They’re ready for the Artemis Club.”
And, as Tomaso had predicted, within two months she was given the invitation to attend. As usual, the club meeting started with a massage, but this massage was intended to arouse her sexually. I was her masseuse.
“Do you like that?” I asked as I stroked the outer lips of her cunt.
She nodded.
“Do you like touch yourself like that?”
She nodded again.
“I’m glad to hear that. Every girl should touch herself like that. I touch my pussy all the time! What part of your pussy do you like the most?”
She spread her pussy lips to expose a tiny clitoris. “I like to play with this.”
“Very good! May I play with it, too?”
She smiled. I made circles around it and she giggled. Then I put a finger against her hole.
“Do you sometime put a finger up there?” I asked.
“A little bit,” she said. “Is that OK?”
“It’s fine! Will you let me put mine up there, just a little bit?”
She nodded, so I pushed and gently eased into her hole, taking care not to damage her hymen. Then I began to tongue her clittie, lightly licking at it.
“Oh, Ms. Smith, that feels good!”
“Before long, you’ll be having all your classmates licking your clit, and you’ll be licking all of theirs as well. And that’s only the start of the games we’ll be playing!”
By this time, Tomaso was fully erect, with a drop of pre-cum welling up from its tip. But he made no effort to hide it. In fact, he took Denise’s small hand and laid it on his cock.
“I’ve seen you looking at it during the massage sessions,” he told her. “Now you can play with it.” She grasped it and squeezed it. “I like the way that feels. Ms. Smith, would you like to show Denise how a woman plays with a man’s cock?”
My own hand joined hers on his shaft, and I showed her how to stroke and milk it. She was fascinated by its warmth and hardness. “Play with his balls,” I said. I looked at Tomaso’s face. He smiled and nodded.
“Would you like to see what happens when a man cums, Denise?”
“What’s cumming?”
“It’s when a man releases his sperm from his cock. You have to be careful with his sperm until you’re on birth control, which will be a school requirement next year. But we can play with it. Let me show you how...” And with that, I oiled his shaft and began to stroke it rapidly. He bent over the table. I aimed his cock at Denise’s oiled body and he and shot his load onto her titties. She laughed in delight.
I scooped up some of the cum with my finger and sampled it. Denise wanted a taste, too, so I let her have some. “Now watch what I do to please a man after he cums.” I knelt down, took his softening cock into my mouth, and softly sucked him as he groaned with pleasure. And that was Denise’s introduction to male sex, as delightful an experience for them both as I could contrive.
Well, Heather was off to a good start. By the end of her third session, I was putting his finger into her cunt almost up to the second joint and stroking her G-spot as I licked her clittie. Without any prompting, she began to knead her breasts and pinch her nipples to heighten the sensation. And by the end of her fifth session, my finger was in her all the way. And she had her first real orgasm, sending her body into spasms of ecstasy. When I broke her maidenhead, she winced once but then succumbed once more to her climax. I inserted another finger and felt her cunt grip them as she trembled. The other girls came over and kissed her, welcoming her into the joys of womanhood.
She also learned how to masturbate a man’s cock, fellate him to orgasm, and swallow his cum. She was a quick learner, and soon had sucked off every one of the masseurs and male teachers.
As Heather learned several ways to masturbate herself or another girl, she was introduced to toys of all sizes and shapes. Again, she was taught, as all the girls were, that her cunt was beautiful and that giving or receiving pleasure is nothing to be ashamed of. That’s the real value of the program. It started out simply as a conduit for orgasmic young people to be used by the state, but it’s resulted in a culture of lust for lust’s sake, with every child encouraged to seek sexual pleasure and realize that their body is beautiful if it is the focus of lust, no matter what its color or shape. No make-up is permitted at our school, because we want the girls to believe that they don’t need it.
In time, Heather was able to masturbate herself to a climax at will, and to wank her classmates and me adroitly. But she was learning all about the male component of sex as well. The masseurs and male teachers let each girl handle their erections and explained and demonstrated the physiology of male arousal, up to and including ejaculation. When Mr. Masumoto is with us, he usually takes some sort of erection persistence drug like Viagra and puts a condom on his penis. Then the girls practice “pussy sliding” on him, getting the sensation of their clitties grinding into the underside of his cock. When he cums, the condom contains the sperm so it doesn’t touch the girls’ vaginal orifice. And when the condom comes off, I encourage the girls to taste his sperm, since I myself am fond of it, having tasted it fresh from his cock in our love-making.
So the girls aren’t really exposed to a strict dichotomy of gender. By their reaction to a man’s sexual heat, I could tell that most of them would prefer fucking men to fucking women. But because they were so used to bringing each other to orgasms at the Club meetings, they were by no means reluctant to get it on with girls or older women. Their bisexuality would be baked into them from the beginning. I gather that this is also true of boys in the Apollo Club, the counterpart to the Artemis Club in the boy’s prep schools. After a year of being jacked off by their upperclassmates, they are happy to get sex from another man when there’s no cunt around.
Taking the job of Advisor of the Artemis Club was the best decision of my life. I was learning the limits of sexual arousal along with the girls, and every meeting of the club ended up with an orgasm induced by cunnilingus and finger-fucking. It was there that I first saw these virgin girls of mine playing with a variety of the hard cocks of the male participants, and learning how to tease them immercifully, and I was learning right along with them. The sight of all those men in the throes of their climaxes aroused me, and I vowed to have all these cocks inside me. And eventually, I did. After every session, I took the male of my choice to my bedroom for a night of sport.
And I found that Imelda was right. Just seeing these girls practicing erotic dance in their PE classes and writhing in ecstatic climaxes at the Artemis Club sessions went straight to my cunt. It re-awakened my sexual attraction to girls, something I thought I’d left behind with my teenage slumber parties. The girls in the “Gemstone Orders” became available as sexual partners and I was often invited to their beds. And I always accepted the invite. It was their way of thanking me for helping them to full womanhood, and it would have been wrong to refuse, wouldn’t it?
At the Artemis Club, we would show the girls videos of how fucking was done, in all of its various positions, to remove any secrecy for the process. It would usually be the Courtesan Prime herself as the female partner, with one of the Courtiers servicing her. Heather used to like to lean against my breasts as we watched the erotic videos of men and women copulating. I’d play with her titties as she stroked my cunt, and we’d often guide each other to orgasms as we watched.
And we’d show videos of naked boys masturbating to the videos they were shown of our female students dancing erotically in the nude, a practice that was taught in their gym classes. And that was something else I didn’t expect ... the sight of all those teenage boys jerking off. I was fascinated and stimulated by the spectacle, and would find myself fantasizing to their urgent lust and their spewing dicks as I masturbated. One of the school counselors told me that this was an entirely normal fantasy and I wasn’t to be ashamed of it at all.
As you know, every year the female prep schools in the kingdom send six of its most sexually gifted girls to the Palace for a week where they are deflowered and used as sexual servants, thereby assuring the peace of the Kingdom. This is usually after the girl turns sixteen. Every girl must provide the consent of themselves and their parents, and I have heard no complaints from other schools about this practice. We sent our six students a month ago. They came back fully satisfied sexually, since they’d been fucked by the King and several Courtiers as well as those bureaucrats, parliamentarians, ambassadors, and business executive whom the King wished to please or reward. It was common for the girls to be fucked up to eight times a day during their “Virgin Week.” I had no idea how much the prospect of fucking a virgin or near-virgin adolescent could turn a man on and persuade him to make treaties or trade agreements that he never would have done otherwise.
The girls were now entitled to wear a ring signifying that they were now members of the Order of the Ruby, granting them permission to have sex with any willing members of our staff. And believe me, after that week they’re out for all the cock and cunt they can get! There are rooms in the dorm dedicated to that purpose which the girls call the “Bordello,” and the girls invite their teachers and masseurs for an evening of exuberant sex and with all the cocks they’ve played with now spurting seed into them. And the masseuses and female faculty, myself included, are at their disposal if they desire lesbian sex.
Of course, with only six girls chosen for Virgin Week each year, there are many members of our Artemis Club are left unsatisfied and virginal. Every third weekend, six of these girls are invited to join the Order of the Emerald in a ceremony, held in a room of the Hall of Pleasure in a nearby town, where they give their virginity to male members of the Order of the Ruby. These boys had been deflowered by the Queen herself, after which they were made available to anybody for a week, as our girls were. These boys, although the same age as the girls, had been highly trained to give sexual pleasure as part of their participation in their school’s Apollo Club, so the experiences are always gratifying. That’s the real goal of the Artemis Club: to make all these girls as capable at extracting sexual pleasure from their bodies as they can be, in the company of boys their own age.
As Advisor to the Artemis Club, I was called upon to chaperon my girls to the city’s Hall of Pleasure for their Deflowering Ceremony. I was given to understand that the “Ruby” boys would be chaperoned by a Courtier, one of the male sexual servants of the Palace. He would be my sex partner for the weekend, and I could use him any way I pleased. Although I was sexually experienced by this time, having had relations with all the male members of my staff, I was understandably nervous about being partnered with someone who had such advanced training in the art of sex.
But when our bus arrived at the Hall, my worries vanished. The Courtier, whose name was Andrew, put me at ease immediately with his smile and sunny disposition. We all proceeded to the locker room, where we all stripped naked. I had seen all my girls naked, of course, and had even induced orgasms in them countless times. But when Andrew and the boys stripped off their clothes and stood before us in the nude, I felt a flush of lust at my first look at half a dozen naked boys accompanied by a male Adonis. And every one had a boner.
I confess that the sight of many hard juvenile cocks always aroused me. At the Artemis Club with my girls, I’d watched many of those “audition” video where the boys would be masturbating while watching videos of an erotic performance and all ejaculating at the same time, a dozen hard cocks squirting cum onto the floor. But this was my first time seeing several adolescent erections in the flesh, so to speak. And these were all beautiful, as they were selected for their shape and size by the Queen and Courtesan Prime themselves. My first impulse was to take each of those young, hard cocks and suck the sperm from them. But I knew that their sperm was destined for another orifice ... the virgin vaginas of my girls.
And Andrew’s was the most beautiful I’d penis ever seen. He’d lost his virginity to the Queen herself, I recognized him as one of the Courtesan Prime’s partners in the instructional videos. He was slightly above average height, with a well-muscled chest covered with brown hair. But what the girls and I noticed was his penis, eight inches long, nicely veined, and already at “half-mast” with the biggest cap I’d ever seen on a penis. His balls hung low, one higher than the other.
When he and his boys examined my girls in their nude state, their cocks all went fully hard. As I said, I’d had plenty of experience with men, but to see seven young hard cocks all at once in the same room was a most arousing sight! It was my fantasy come true, and I suddenly became weak in the knees. And when we entered the shower area, I was delighted to see that all the shower nozzles were detachable, allowing the bather to direct any part of the stream onto whatever body part pleased them most.
Any residual shyness of my party was washed away as the children began washing each other, the girls stroking the boys’ erections as the boys fondled the girls’ breasts and pussies. And as part of my introduction to Andrew and the boys, I fondled each of those cocks there in the shower.
My girls had all fondled penises before in the Artemis sessions, of course, and held them as the teachers or masseurs ejaculated. They’d all tasted cum, too, sometimes as it flowed directly from the cock. But this was different, as these boys were the same age as they were. And the girls knew that those penises would soon be inside them! Already they were fondling themselves, their hands stroking their titties or clefts, partially as a show to get the boys excited but also an indication of their own flaring libidos. Although I had seen the girls naked every week at the Artemis Club sessions, they now exuded a sort of beauty I’d never seen before. Some of the girls had shaved what little pubic hair they had, in order to make them look younger, I suppose.
That was when the reality of the Sexual Gratification program really hit me. This is how I should have been introduced to sex. No modesty, no shame, only friendliness and lust. Girls going confidently to their first experience with coitus, boys giving them the ultimate in respect and consideration.
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