The Courtier and the Ruby
by Jehoram
Copyright© 2025 by Jehoram
Erotica Sex Story: A Courtier, a skilled lover from the Ministry of Sexual Gratification, interviews a girl selected to be deflowered at the Royal Palace. He meets her again when she accompanies six experienced teenagers to a Deflowering where he's chaperoning six virgin boys. Finally, he is summoned to the Palace for an annual review and finds that the reviewer is the same girl.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa mt/ft Ma/ft Consensual Heterosexual Fiction Group Sex Anal Sex Nudism .
I’ve been a Courtier four three years now. I lost my virginity while participating in a Virgin Week at the Palace, where I fucked the Queen and a bunch of girls who’d just lost their virginities to the King or some other important political figure. These girls were all members of the Artemis Club and had been selected for their abilities to achieve orgasms. I also fucked a few Courtesans and other staff members of the Palace who felt the need for a little young cock from time to time. It was a great way to lose my cherry, and I was inducted to the Order of the Ruby at the end of the week.
After that, I participated in a number of Deflowerings, where “Ruby boys” like me fucked virgin girls and gave them their first taste of heterosex. I guess I did well at that, because my application for the position of Courtier was accepted. One of the perks of that was that I was called back to the Palace and get fucked by the Courtesan Prime. That was the best fuck of my life. Crystal was extraordinarily talented as a fuck-mate, and I was invested as a Courtier the same day, with a nice diamond ring on my pinky to accompany the ruby one I wore.
But my job as a Courtier didn’t include many visits to the Palace. Instead, I was a “traveling Courtier” whose job was two-fold. First, I accompanied the Ruby boys of a particular school to the Deflowerings where they introduced virgin girls to the joys of sex, as I had done when I was in high school. I didn’t fuck those girls, though. Instead, I fucked the Artemis Club Advisor who chaperoned them. The Advisors were pretty talented fuck-mates, as they had to be since we Courtiers were fucking them twelve times in the course of a weekend. Their sex was almost always vanilla, though ... missionary and cowgirl. It was my job to be a good lover to them, and I left them satisfied.
The other part of the job was interviewing the virgins of a female secondary school who were being considered for the Order of the Ruby, which entailed participation in the Virgin Week where their cherries were to be taken by the King and other dignitaries, after which they’d be living at the Palace for a week as sexual servants for anybody who wanted to fuck them. I’d go to a school and spend a week interviewing the dozen girls or so who’d been selected by the school. They’d give me a strip-tease show, masturbate for me and show the skills they’d acquired in giving hand jobs or blow jobs.
I’m going to tell you about the best girl I ever interviewed. Her name was Fiona, and she came from the Pleasant Valley Academy for Girls. I could see right away that she had potential, with her arresting smile and total self-confidence. When she stripped bare for me, she showed a complete lack of embarrassment or body shame. She had small but distinct titties, and orange-red hair just beginning to grow around her pussy, matching the hair on her head. She lay on her back on the bed and smiled invitingly as she pulled her inner pussy lips apart to display her fuck hole. And when she began to masturbate, she slid into an orgasm almost immediately. I couldn’t help but match her passion as I spewed a load onto her belly.
After that, she brought me back to hardness with an astonishing skill in arousing me with her hands and mouth. I was supposed to similarly arouse her with my own fingers and mouth, but found that she was already in a state of near-climax, as if her original orgasm was still going on. That was rare in a girl of sixteen. Her second climax lasted for five minutes, after which she gave my cock a series of artful strokes and then latched her mouth onto its tip, swallowing the sperm that rocketed from me as I came. That was also unusual. She smiled at me and said, “I love the taste of cum! I almost never get it from my meetings with the teachers and masseurs at the Artemis Club! Thank you so much for letting me do this!”
Well, I’d already decided that the was going to Virgin Week, if I had anything to say about it. But I was curious to find out how early this sexual energy had manifested itself. I found the answer when I read her files. It turned out that when she was given her first massage after gym class in her freshman year, she readily parted her legs to receive the masseur’s hands, and orgasmed after only a few strokes on her pussy. She was obviously masturbating regularly by then, and the act of exercising nude in class in front of naked men and women had already aroused her to a high pitch, which needed only a little attention to her cunt to put her over the edge. She was inducted into the Artemis Club, where the club Advisor (who was also the principal of the school) decided that her only task was to teach Fiona how to extend the orgasms she was so readily manifesting.
I learned that Ms. Reynolds, who was a lesbian, had made comments that Fiona displayed a bisexuality, being stimulated by both male and female nudity. Fiona was actually helping other girls to develop their sexual drives, acting as an assistant to the Advisor and the teachers. Her youth had been a great asset in reaching girls of a similar age, helping them overcome any shyness or embarrassment they might have had when they came to the Club.
Of course, I gave her a glowing review, and was not surprised to find that her name had been included in the Virgin Week roster. Sadly, I was not able to be at the Palace at that time.
But I saw Fiona again, the next year. I was chaperoning six boys to a weekend Deflowering, where they were doing what I’d been doing as a member of the Order of the Ruby: inducting virgin girls to sex. The girls happened to be students at Pleasant Valley. To my surprise, she was there chaperoning them, a task that was usually assigned to the schools Artemis Club Advisor. I was delighted to see her again, with the prospect of fucking her silly that weekend.
“How did you end up here?” I asked as we showered. “Where’s your advisor?”
“Well, she isn’t really into guys, and she was feeling a bit off anyway. She told me to go in her place, Since I’ve got the Ruby, I’ve been acting as her assistant at the Artemis Club meetings. But aren’t you the guy I auditioned for? Ever since that day, your cock been in my mind when I wanked. I wanted to do more than suck it, and now I have the chance!”
“It’s my honor to do so. You’re the hottest girl I’ve ever met! To be honest, I’ve fucked four dozen virgins when I was doing my duty as a Ruby, but none of them aroused me like you did when I interviewed you. Whoever took your cherry must be the luckiest guy around!”
She smiled. “It was the King himself! He ended up fucking me three times that week. And I was in the Queen’s bed a couple of times, too.”
“And your principal’s a lesbian, too.”
“That’s right. As soon as I got home after getting the Ruby, I laid her. She said it was a dream come true. We’ve been sleeping together at least once a week. Cathy ... the physics teacher ... is her usual partner, but she knows the bond I have with Imelda, and doesn’t tamper with it. I’m still trying to convince her to make it a threesome, but she says she’s not ready for that yet.”
When the shower was over, the kids paired off and claimed the mattresses to begin their fucks. I hoped the boys remembered the usual speech I gave them on the bus ride over, about making sure that the girls’ first experience would be a good one and they had to be super sensitive about their partner’s needs. That same advice was ringing in my head as I led Fiona to the last mattress, which was sitting on a pedestal so that it was a little higher than the others.
But I needn’t have worried. She was already nine-tenths of the way to a climax, simply from showering and seeing me and the twelve naked children in the shower, and remembering her own trysts with virgin boys during the Deflowerings she’d attended as a Ruby. “Gimme cock,” she said. I slid my hard cock into her wet tunnel and felt its muscles clenching me, signaling the tempo she wanted. She was clearly more experienced than any of the Advisors I’d fucked. I did my best to last, but it was only a short time after all the other boys had cum than I’d released my load into Fiona. She, of course, was orgasming the moment I entered her, which didn’t help.
We stood up and hugged each of the children, welcoming the girls into womanhood. Fiona was a striking figure, bathed in sweat and radiating a sexual glow that brightened the room. I thought that, even with her small breasts, she was the epitome of female beauty.
And for our next two fucks that day, she showed a desire for more than vanilla sex. We did doggy and Amazon as the kids watched after their own climaxes. I’m happy to say that the display helped them to their next arousals, and some of the girls even insisting on trying them, which was unusual in my short experience as a Chaperone. If they wanted anal, I knew that the Ruby boys would be careful to wash themselves well afterwards, so that their next partners would be safe.
Because she sweated profusely during our fucks, we found ourselves in the shower after each one. When I addressed her as “Fiona,” she said that she preferred to be called “Ginger.” It was the nickname the King had given her, and she felt that it was a badge of her induction into womanhood.
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