The Advisor
by Jehoram
Copyright© 2025 by Jehoram
Erotica Sex Story: The advisor of a boy's club escorts six virgin boys to their "deflowering weekend" where they'll have sex with six experienced girls their age. And he'll be paired with the sexiest woman he's ever met. By the end of the weekend, he'll also have had sex with all six of the girls she's escorted to the camp.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft Teenagers Consensual Heterosexual Fiction Interracial Nudism .
What was the best weekend of my life? I’ll tell you. It was the weekend I got to have six fucks with a goddess, but have a fuck apiece with five teenagers and two fucks with a sixth one, too!
I am the Advisor of the Apollo Club at Exeter Academy, my all-male high school, where I teach chemistry. The Apollo Club, as you may know, is a club where the boys learn about sexual pleasure. We have after-school sessions where they get naked and masturbate with each other, and learn to wank each other. But the important thing is that they’re also taught how to edge, and learn that their opportunity to lose their virginity is linked to their expertise in that art. We figure that until they master that skill, they’d be no good as lovers to women. I’d always been good at edging. And after a while, I’d be proud to see them holding their arousals for up to half an hour before the cum spewed in unison from their young cocks.
The usual routine was to start a meeting with the boys getting naked and jacking or sucking each other off. If there happened to be an odd number of boys due to sickness or whatever, I’d take the unpaired boy and let him play with my cock as I played with his. It was a thrill to feel his virgin cock pulse as he shot his load onto his chest. And sometimes I’d blow him and get a taste of his sperm as he sucked the cum out of my dick.
That’s one of the perks of this job. I’m as hetero as they come in most respects, but I love seeing naked young boys jizz, and I love to see them watching me as I cum. It’s a real bonding experience when I can oil up a boy’s penis and bring him from limpness to ejaculation, and have them do the same to me. I know that most of those boys will end up being mainly hetero, but they will always have the fond memories of gay sex as I prepare them for cunt. And when they finally learn how to edge, that’s when we bring them to the next step in sex.
After our first orgasms of the night, there would be the “sex education” part of the meeting, when we’d do one of two things. On Mondays and Wednesdays, one of the female teachers or masseuses would show the boys her private parts and demonstrate how she liked to masturbate, and the boys would either give her head or finger-fuck her until she orgasmed. Tilly, who taught History, loved to have her long fat nipples sucked as well, with a boy at each breast while a third ate her out. She was one of my regular sex partners, and she’d be a monster in bed afterwards.
On Tuesdays and Thursdays, we’d watch “pornos” so the kids would learn the variety of sexual positions and techniques. These usually weren’t pornos in the usual sense, with hokey plots and faked orgasms. Instead, we’d be seeing the Courtesan Prime herself conducting the demonstration with one of her Courtiers, explaining to the boys exactly what the benefits and drawbacks of each technique were. I sure wish I had that kind of porn around when I was growing up. The Courtesan Prime was the King’s mistress, you know, and generally regarded as the ideal sex partner.
After the Sex Education segment, all the boys would be hard again. So every meeting would conclude with a circle jerk, where the boys demonstrated their proficiency at edging. The idea was for them to all be hard for a half an hour and then cum at the same time, a dozen or so boys shooting their sperm simultaneously. We’d record those sessions and send them off to the Courtesan Prime, who found the recordings invaluable when selecting boys for Virgin Week.
When the boys are ready for their first experience with girls, a few of them are selected to be deflowered at the Royal Palace. That’s what “Virgin Weeks” are ... the boys are deflowered by the Queen herself, after which they’re available as sexual partners for anybody who wants them. Some of those partners would be Courtesans, who were members of a select Palace staff of women that were on call by the State to provide sexual services. The rest would be government guests or officials, male or female, who wanted a bit of young cock. After that week, the boys are members of the Order of the Ruby. Only six are selected each year from our school. It’s an honor, because they’ll go on to deflower girls their own age and introduce them to sex, as well as have license to fuck any willing teacher or masseuse at the school.
As for those boys who don’t make that cut, we take them in groups of six to a weekend “Deflowering camp” set up by the state for that purpose. They are met by six girls who have not only lost their virginity, but have attended a Virgin Week at the Royal Palace, where they were used as sexual partners for anybody who wanted them, from the King on down to government officials and visitors. The girls often take as many as thirty partners in the course of a week. At the end of the week, they are inducted to the “Order of the Ruby.”
So they have had considerable experience in sex. As members of the “Order of the Ruby,” they have been recognized for their ability to orgasm and to please a male partner. When my boys attend the “deflowering camp, their first experience with girls will be pleasurable as possible. Over the weekend, the lads would be able to fuck each girl twice. That way, they’ll also not be fixated on the girl who took their virginity ... it will be six girls!
And each time, the girls would be accompanied by a Courtesan. Not all of these women were members of the Order of the Ruby. A few had been members of the “Order of the Emerald” after they’d participated in the same sort of weekend retreat that my boys had experienced, but with male members of the Order of the Ruby. This woman would be my sex partner for the weekend, while the kids were fucking.
I myself had been awarded my emerald ring after my Deflowering weekend, and I was overwhelmed by the expertise shown by those young “Ruby” girls, themselves virgins only a few months before. As for the Courtesans, they were always splendid fucks, the best I’d ever had. That’s why they’re Courtesans.
On the weekend I recall most fondly, I arrived at the camp with six boys ready for their first coitus. We met up with six girls who wore the ruby ring. I was told that this lot had already deflowered four groups of boys before this one, so they’d had plenty of experience with virgin boys. Accompanying them was a Courtesan who was easily the most beautiful woman I had ever seen. She was had red-orange hair and a figure that was perfection itself, with wide hips, a narrow waist, and nipples that pushed through the light knit top she wore. Her wide thigh-gap and camel-toe showed prominently through her yoga pants. And her smile, with its gleaming teeth and fuck-me lips, went straight to my crotch.
Upon arrival at the camp, everybody stripped naked. Nudity would be the rule for the weekend, with the participants storing their clothes in a locker. Then came our usual communal shower, the first of many. I always liked the sight of those naked teenagers, both male and female (although the naked boys were quite familiar to me from the club meetings). The girls were showing all their adolescent allure, with titties ranging from “barely there” to prominent on their frames, perched high on their chests as all girls’ titties do before the inevitable sag begins. Their skin colors ranged from pale pink to dark brown, and some had tan lines that accentuated their breasts and nearly hairless pussies. It would take no time at all for my boys and me to have hard-ons.
From the way they regarded the naked boys (as well as myself), it was clear that they were looking forward to a great weekend of sex and were already sizing up the boys, admiring our boners. My only regret was that I would not be one of their sexual partners, like the ones I’d imagined as I watched the “Audition Videos” of girls like them as they stripped, danced, and wanked before the camera. I watched those videos along with the boys when the “reaction videos” were made as part of the selection process for possible Palace visits, where a lucky few of the boys would be deflowered by the Queen herself. And as a teacher, I was allowed to borrow the videos and masturbate to my heart’s content on those nights when I didn’t have a fuck-mate.
Instead, I would be fucking their sponsor, the Courtesan. But the beauty of that woman, when she fully revealed her nude body, took my breath away. Her breasts, not large but fully mature, had not a trace of a sag, and sported nipples that were long, dark pink, and fat, begging to be sucked. They were even a good half-inch longer than Tilly’s were, which I didn’t think was even possible.
The red-orange hair on her crotch was neatly trimmed, and did nothing to conceal the clit that protruded from the top of her slit and the inner lips that hung down an inch. She had blue eyes with a trace of green. She smiled at me as she soaped up, lifting her breasts and flicking her nipples with her thumbs as if presenting them to me, and my cock immediately became harder than it had ever been in my life. She was clearly more experienced at sex than anybody I’d met before, even the Courtesans of earlier trips. I knew that as soon as I entered her, I’d blow my load. I knew from previous experiences with Courtesans that I was capable of six ejaculations a day, just like the boys, but how could I ever hope to satisfy this woman twelve times in the course of the weekend?
As we showered, I heard some of the boys pointing to her and saying, “That’s her!” or “That’s gotta be her!” When I asked Freddy about it, he said that there was a GIF that was on practically all their computers of a virgin girl stripping, dancing and masturbating ... a clip from one of the Audition Videos. She looked just like that girl, he assured me, although her boobs were bigger than the ones in the clip. I hadn’t seen the GIF, but it wouldn’t surprise me that a video of her when she was pubescent would be a sensation.
By the time our shower was finished, the boys were as hard as I was at the sight of all those naked ladies, the Courtesan foremost among them. We proceeded to the main room, which had seven mattresses set up for us, one of them on a pedestal. That one was for me and the Courtesan. We lined the lads up, and she assigned them numbers. The girls were lined up facing them. It was the usual procedure. The girl would take the boy facing her for the first round and lead him to one of the lower mattresses, which would be hers for the weekend. For the second round, the girl would fuck the boy standing next to the first one. For succeeding rounds, they’d follow that pattern until each girl had fucked each boy, in two-hour intervals broken only by meals, showers, and sleep. After lunch on the following day, the cycle would resume for the boys’ second “trysts” with the girls.
And all this time, I’d be fucking the Courtesan. “My name is Fiona,” she said. “But everybody calls me Ginger.”
“I’m so glad to meet you! My name is Damian. My only question right now is about me being able to fuck you twelve times in the course of the weekend.”
“Six fucks a day? Don’t worry about that, dear. It’s my job. I’ve done it before. For me, it’s all in a day’s work! It looks like you have a healthy libido!” she said as she squeezed my hard cock. And with that, she told the children to start fucking each other, which they commenced with vigor. Each girl escorted her boy to a mattress and spread her legs. I was proud to see my boys giving the girls some oral or finger-fucking beforehand, although the girls were already in a state of arousal. But the whole purpose of the weekend was to get cocks into cunts, and it wasn’t long before the kids were locked together in lust, my boys ejaculating into a girl’s vagina for the first time.
How do we get started?”
“Like this,” she said. She led me to the last vacant mattress, lay on her back, and spread her legs, exposing a cunt open, ringed with red hair, and very wet. “No foreplay! Just fuck me!”
And so I did. It was magnificent! She showed a control of her Kegels that far surpassed that of any of the thirty women I’d fucked. And she knew when I was just about to blow, and backed me off until the urge passed. To my astonishment, I was able to last about twenty minutes before I came, which happened to be double the interval that most of the other boys had been able to manage until they ejaculated into the cunts of their first partners, despite all their training at edging. Ginger also came, her torso flushing pink, and her wetness making her vagina even more slippery.
She was in no hurry to get up after our climaxes. Instead, she played with my limp dick and chatted. She said that she was nineteen, attending the Royal College, and was studying business management, with a minor in sexology. As a Courtesan, she was on call at the Palace two or three nights a week, and attended to the kids and the dignitaries during the Virgin Weeks at the Palace. At her own Deflowering, her first fuck was with the King himself, who became a regular bed-mate.
“I love to see those young boys doing their first fucks,” she said. I asked her how many boys had given her their virginity. Fourteen, she said. “Twelve of them when I was doing these weekends with the Order of the Ruby, like this one, and two more at the Palace. One of them was with one of the princes at my own Virgin Week, and the last one was with the son of an ambassador who was visiting a few months ago. That was fun! I had them both in the same bed, and the kid watched me as I fucked her father, and then he was next.”
What an image of that episode formed itself in my mind ... a boy cumming into a cunt already awash with his father’s jism! “How many teenage boys have you fucked altogether, then?”
“Well the twelve virgins from the weekends, and sixty more at that time whose virginity had already been taken by another Ruby girl. And six from my own virgin week, and twenty-four from the Virgin Weeks I’d assisted at as Courtesan. The princes fuck me when they’re home from school. And that kid I just mentioned.”
“I have to ask: how many people have you fucked?”
“Oh, hundreds and hundreds. I stopped counting after five hundred or so. I’m a favorite of the king ... I’ve fucked him dozens of times, both at my Virgin Week and as a Courtesan.”
“You’re not the Courtesan Prime, are you?”
“Oh, no. That’s Crystal. She’s the best fuck in the Kingdom!”
When I asked her about the GIF that the boys were talking about, she blushed and smiled. “That’s me, all right! I guess I’m a sort of celebrity now. I’ll send you a copy!”
Between fucks, we’d shower, and the girls would let me soap them up and fondle their titties and nearly hairless snatches, while Ginger would hug the boys and stroke their limp dicks. I always treasured those moments when I attended those weekends. The memories of lathering up those naked pubescent forms would never fail to arouse me. And Crystal would approach a girl and boy at a shower-head and invite them to suck her nipples as she pulled on her clit. With that amount of nipple play, it was no longer a wonder that here nips were so long and fat.
After the first round was over, drinks and snacks were served and we mixed with the crowd until the boys’ libidos recharged. Some of us took showers during the breaks before partner-switching. (Ginger showered after every fuck, since she sweated buckets during our trysts.) The boys were obviously impressed with the experience of their first fucks, and some of them were still half-hard. The girls would chat about their school and the guys they’d fucked as members of the Ruby. The sight of their naked bodies, complete with the cum that was oozing from their slits, was enough to get me aroused enough for the second round.
“Let’s do something different,” Ginger told me as the second round began. “This time, me on top.”
That was fine with me, since I got a chance to see her tits bounce as we fucked. She gripped her clit with her fingers and squeezed it in time with her bounces. I was just a sex toy to her as she plunged my tool in and out of herself, sometimes doing a sort of hula, gyrating her hips. My cock became the center of my world, with every other sensation receding into nothingness. Every inch of her sheath was stroked by the cap of my cock ... front, back, sides, from “barely in” to fully penetrated. She squeezed it with her Kegels and I could actually feel her cunt sucking my cock as she stared at me with eyes hazy with lust.
Again, she seemed to know when I was approaching that “tipping point,” and eased up on her motion. I saw a lot of the kids looking at us with amusement or appreciation after they’d experienced their own climaxes. I lasted a bit longer this time, about a half an hour, before I spewed my second load of cum into Ginger’s wet snatch. The children finished before us, the boys’ endurance succumbing to the new sensation of a different girl’s vagina, and they watched my tryst with interest.
For the next round, after dinner, we did “doggy” at her suggestion, although she offered me the possibility of any of the other positions I wanted. She made sure that her breasts were off the mattress so the boys could see them swinging, her long nipples grazing the surface of the mattress. She knew that the children’s trysts wouldn’t be as long as ours, and they appreciated the spectacle as they recovered from their orgasms.
I had fucked her three times before bed-time, when we were paired for the night. When I came to the “Courtesan’s Bedroom” (which became the “Courtier’s Bedroom” when the genders of the participants was switched at the next weekend) I found that a hot tub had been installed. “This is new!” I said.
“It was just installed. We figured that after a day of fucking somebody three time in a row, a soak was just what we needed.” She pointed out some nozzles and hoses. “Those are for play as well as relaxation. Let me show you...” As she lowered herself into the water, she grabbed one of the hoses and directed a pulsating stream at her engorged clit. Then she lowered herself further, until her breasts were floating upward in the water, her nipples just above the surface. She now directed the stream on each nipple, and gave the now familiar sigh of her orgasm.
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