The Ruby
Copyright© 2026 by Jehoram
Chapter 1
Erotica Sex Story: Chapter 1 - The first chapter of this story follows the progress of Edgar, a school-boy, from the time his cock up is oiled up to a public climax for the first time by a masseuse, leading to his first public cum, to the day when he's given the ultimate fuck of his life, from the Courtesan Prime Herself, on the weekend he loses his virginity at the Royal Palace. The second chapter describes how he's able to introduce virgin girls to the delights of sex, and finds a fuckmate who can match him cum for cum.
Caution: This Erotica Sex Story contains strong sexual content, including mt/ft mt/Fa Teenagers Consensual BiSexual Fiction Interracial Black Male White Male White Female Masturbation Oral Sex Safe Sex Tit-Fucking Nudism
My name is Edgar, but people usually call me “Eddie” or just “Ed.” Four months ago, I was a virgin. But now that I’ve been a member of the Order of the Ruby, I’ve fucked six virgin girls and thirty-six almost-virgin girls, along with about twenty adult women. I’ve been one of the boys who go out in teams to deflower young ladies and fuck their Advisors, and it’s one of our jobs ... or their perks, frankly. I’ll tell you about that by and by, but first let me give you my own history.
I go to the Pickett Academy for Boys. On my first day at gym, we boys only wore jock straps. And those had to come off after class, when we went to our massage sessions right after working out. Even then, I had a cock of slightly larger size. I’m half white, half black, and my dad used to joke that it was my “black” genes that gave me that kind of cock. But I’ve had a chance to compare cocks with hundreds of boys, and I’m not much bigger than average.
But, even more than most boys, it would go hard in an instant. I was only fourteen, you know. So when I saw all those naked men and women at the massage tables ... the first naked adults I’d ever seen ... I started to get a boner. And when Trisha, one of the masseuses, rubbed me down and got my cock all oily, the boner was all there, and leaking pre-cum. I couldn’t help it. She had saggy tits with big brown nipples, and the sight of them swinging as she rubbed me down was all it took. She gave my boner a few strokes. “I think I’m gonna cum,” I said.
“It’s all right. I can’t give you a real hand job here, but you can finish it yourself. It’s expected. Your body is your own, and you can do what you want with it as long as it doesn’t offend others. And you won’t be offending me if you want to wank.”
So I did. I had no control in those days, so it only took a few strokes to trigger the jizz. It spurted out of me, some of it landing on my face and the rest on my body. She smeared it over my skin, mixing it in with the oil. I was shaking from the force of it, but relaxed as she finished the massage.
Most of the other boys did, too. You’d see them go off to the showers with jizz on their chests or dripping from their now flaccid cocks. It got to be a normal thing, although I was secretly proud of the fact that mine stayed semi-hard even after cumming.
From that day on, I finished each massage with an orgasm. Besides that wank, I was masturbating about two or three times every day. In the morning, when I got off class, and when I went to bed. There were a lot of erotic videos on the school server that anybody could download to wank to. My favorite one was a GIF of a red-haired girl my age with a slim figure and hardly any titties. She did this erotic dance, starting out clothed and ending up nude and masturbating to a climax, her sea-green eyes locked on the camera the whole time. The end of it was when she squatted, spread her legs, and pulled back her labia to expose her pink hole. That was when I tried to time my orgasm for that moment. The video was titled “Fiona” and had been downloaded more times than any other video, so I figured that I had a lot of company.
And, when I joined the Apollo Club, I’d jizz as soon as I got there and at least once more during the three-hour meetings. You already know about the club, and what it did. The first day I went, an upperclassman with a ruby ring greeted me and gave me the first blow-job I ever got. And then I returned the favor, and got the first taste of sperm that wasn’t mine.
Then Trisha, who was also one of the attendants, gave us a lecture on her cunt, explaining all the parts and their function. I gave her some head as she coached me. Some of the other boys were sucking her nipples, and I witnessed the first orgasm from a woman. That made me hard again, so she oiled up her boobs and gave me a tit job, another first for me. At the next session, she gave me the hand-job I’d always lusted for. “I’ve been wanting to do that ever since I first saw your cock,” she said. “And now I get the chance to!”
Well, they trained me to edge, delaying my own orgasm, and I learned about how to please women with my tongue and fingers. Sometimes they’d show movies of the Courtesan Prime demonstrating the various sex positions with one of the Palace Courtiers, usually a blond guy with a big dick and hairy chest. She was the most beautiful woman I’d ever seen, with long curly red hair, full breasts with the longest nipples I’d ever seen on a woman, and long legs. I swear, I could cum just watching her fuck for the camera.
I recognized her as Fiona, the same girl I’d been jizzing off to since I arrived at school. She had hardly any tits then, and no hair on her pubes, but now she had a woman’s form and a neatly trimmed thatch of red hair, and she was still the hottest thing I could imagine.
Usually the session would end with us in a circle jerk, watching girls our age in their erotic dances, showing no shame at all. The idea was to time our ejaculations to go exactly when the film ended. At first I blew too early, but got the hang of it. There was one girl I remembered from those videos, with dark skin, frizzy hair, and long nipples. It was hard to take my eyes off her as she danced.
Well, it became natural for me to get off with other boys, and it wasn’t long before I was introduced to anal sex, both giving and receiving. There was no shame involved, because everybody was doing it. And we made sure to wash ourselves afterward. We’d often sleep in each other’s beds in the dorm, but I didn’t have a steady boyfriend. As I was fucking some guy in the ass, or just jerking off, I wondered what it would be like to fuck a woman’s cunt. But most of our sex was just mutual masturbation and 69.
After a year after joining the club, two things happened. First, I was invited to a session on a Saturday, when we didn’t have classes. It was an all-day affair, and I had to cum as many times as I could. There were all sorts of toys there and all the porn we could watch. I managed to get off eight times over the course of the day, instead of the five or six times the other guys did. Every time, I had a rubber on, and they’d take the rubber after I came and weigh it to see how much cum was in it. I didn’t know it at the time, but it was part of the screening process for determining which kids would be inducted into the Order of the Ruby. The guys who came the most or jizzed the most or recharged the fastest were the ones they were looking for.
I guess I passed, because I got an invitation to the Office of Sexual Gratification in the federal building in our town. The “office” was really a bedroom. I was met by a young woman in a sort of armless, legless leotard that covered her torso with a semi-transparent fabric, so I could see her tits and cunt. I saw a ring on the pinky of her right hand that bore a ruby and a diamond. She had dark hair and brown eyes, and looked to be about twenty. “Hi,” she said. “I’m Louise, and I’m one of the traveling Courtesans. Take off your clothes and let me have a look at you.”
So I did. It was the first time I’d actually seen a Courtesan in the flesh, and she was everything people told me she’d be. Everything about her said “fuck me” ... her smile, her shape, her posture. I was hard even before I dropped my shorts. She saw my cock and smiled. “Let me see you cum,” she said. “Take your time!” She laid me on the bed, and I wanked for her, using some oil she’d given me. She pulled the fabric that covered her cunt aside, and finger-fucked herself as I watched. I was able to last for a half an hour before I jizzed. She licked it off my chest and said, “Not bad!”
Then she took off her leotard completely and joined me on the bed. “Kiss my cunt now,” she said. So I did, and smelled the perfume of a woman’s sexual arousal. “Eat me,” she said. I did that, too, as well as I could. when I added some fingers and began to finger-fuck her, she slipped into an orgasm as easily as a guy does. I reached up with my free hand and grasped a breast. Her nipple was rock-hard. “Squeeze it!” she breathed. I gave it a pinch, and she gasped as another orgasm hit her.
After her climax, we snuggled for a while. She asked me about school and what sort of music I liked, and I told her about being on the tennis team and the chess club. She was fondling my dick the whole time. “I’m not going to fuck you,” she said. “You have to stay a virgin for a little while longer. But you’re getting hard again. Do you want me to blow you or give you a tit job?”
“It’s up to you,” I said.
“Good answer! It shows that you care about your partner. You get points for that. Why not let me tit-fuck you? I get off more that way. I love to feel a hard cock between my boobs!”
So she oiled up those full breasts of hers and got to work, those rock-hard nipples stroking my belly. To my amazement, she had me hard again after less than an hour after my last jizz. She sure knew her job, and despite my holding on for another half an hour, I finally went over the edge, spewing cum all over her chin. She wiped it off with her fingers and then licked them clean. “You do taste pretty good,” she said. Of course, I thought. She must have blown hundreds of guys, and knew exactly what cum tasted like.
Then the session was over. I dressed again and she gave me a hug and a kiss before sending me off. That was my admittance test for the Ruby. I found out later that they had been recording us boys as we watched some of the porn videos at the Apollo Club sessions, to see which ones last the longest and cum the most. The Queen watched these videos and selected the ones she wanted interviewed. I was one of only six boys to be sent off to the Palace this year.
What a night that was! I was accompanied by Stefani, another Courtier who had brown skin, black kinky hair, and a leotard whose neckline plunged to display a cleavage that barely covered her nipples. She looked a lot like that girl I noticed in the erotic dance videos, but wasn’t the same girl. She shaved my pubes until I was as bare as a baby’s, and cuddled with me but wouldn’t let me fuck her, because I had to be a virgin so my first fuck would be special. And it was!
I got to jizz into a woman for the first time, and it was the Queen herself! She was in her late forties, but she still had a good figure. I and five other boys from my school jizzed onto her naked body and then licked it all off of her as she orgasmed. After, that, all six of us got to fuck her, one after another. She’d deflowered literally hundreds and hundreds of boy by that time, so it was no big thing for her. “All that little-boy cum in me keeps me youthful!” she told us. “That’s my secret!” And then Stefani led me to another room, where she took off her uniform, threw me on the bed, and fucked me silly. She was even better at fucking than the Queen was, doing things with her vagina muscles that I’d felt only when finger-fucking Louise or Trisha or the other ladies. But this time, it was on my cock!
The next morning, after another glorious morning fuck with Stefani, she took me to breakfast where I and my pals got to meet six girls who’d also been deflowered the night before. They were hot, with pubes shaved bare as bare as mine and tits of various sizes, from barely there to a good handful. We were all led to a room with a heated indoor pool big enough to do laps in, and a Sybian machine for the girls to play with.
One of the girls, named Lily, was the first one to use it and, when she rode it, her grey eyes were on my hardening dick and I, in turn, was facinated by her long-nippled boobs as they bounced. “She’s that girl in the video!” I thought. But then she was called for duty. She wanted to have a quick swim first, so I took her hand as she mounted the ladder into the pool. As her head was at the level of my crotch, she leaned over, grabbed my cock, and gave the cap a quick lick and kiss, followed by a wide toothy smile that made my cock jump a little. And then I was called for duty. She turned out to be so much in demand that I hardly saw her at all for the next couple of days, but I really hoped to fuck her at some point during the week to come. That really would be a wet dream come true!
That room was pretty much our home base for the next week. We’d hang around the pool while waiting to be assigned to some government worker or dignitary. Our job would be to fuck them on their breaks or for evenings. We’d be sent to bedrooms on the second floor of the Palace, which would have mirrors on every wall and the ceiling, and a king-size bed. There would be a partner, almost always of the opposite sex, waiting for us. These encounters were called “trysts” and would last an hour or so, except when we’d stay with them overnight. I like those, because we could usually fuck the woman two or three times instead of once.
We guys usually had an hour or two to get our boners back, as our clients insisted that we come with our cocks hard and ready. Twice, I had the privilege of Lily getting me hard again with her hands and mouth. But the girls didn’t have that problem, and sometimes they’d only have enough time for a quick bite or a lap in the pool before they were summoned for their next tryst.
Most of the women I fucked were older women who worked at the Palace. Janice was typical of the bunch; she worked in the Office of the Budget. She was in her forties. When I got to the Tryst Room I was assigned to, she was waiting for me naked on the bed, playing with her heavy breasts with small pink nipples. “I don’t have a lot of time,” she said as she extracted a vibrator from her quim. “Just fuck me.” I gave her about fifteen minutes of pumping before I came. “That’s fine. That’ll do!” Then she got up and quickly dressed, kissed me, and left. So that’s what people do on a half-hour break, I thought. Grab an orgasm, go back to work with a clear head. Not a bad way to run a government, I thought.
A few of the workers I fucked would be Courtesans, and they were the best fucks, because they were always teaching me things. I mean, it’s one thing to watch a reverse cow-girl, but quite another to actually do it, but the Courtesans would show us every detail of any sexual position we were interested in. They’d describe what turned them on, what they were getting out of the fuck, and how women differed in their experiences. They’d fucked hundreds of men (and women, too!) and knew what I had to learn.
All of us guys got in at least six cums every day. The girls got in even more, because they were always on call and would spend time on the Sybian when they weren’t fucking, just to stay aroused. The girls were always in demand, because there were more horny men in the government than women. But it all worked out, because we guys could only cum six or seven times in a day, but the girls could get fucked twice as many times. And we guys would only get called up four or five times a day, so the rest of our cums were for the girls, usually in late afternoon when the government workers were going home. I got to fuck all of them at least once, including Lily, but I’ll tell you about that later.
I guess that the word had gotten around that I was a competent fuck-mate, because on Thursday evening, just as I was getting ready to have dinner, I was assigned to fuck one of the Courtesans. Those were my favorite trysts, since they’re the best fucks and I’d get to spend the night with them, learning all kinds of stuff about female sexual desire. They were usually the women I got to sleep with, because all the other government workers went home to their husbands or lovers at quitting time. While their main job was screwing important people in the government or in society, they loved to screw us young boys, too.
But the room they sent me to this time was on a higher floor than the other Tryst Rooms. It not only had those mirrors all over the place but was three times the size of the other tryst rooms, and had a six-person shower, a dining area, and a huge bed in the main room. And when I got there, the woman in the bed was the red-head I’d seen in all the videos illustrating sexual positions. She was buck-naked, with a hairy quim and long, fat nipples. I saw the diamond ring that every Courtesan wore, except that hers had three diamonds. That’s when it hit me: it was Courtesan Prime herself!
I can’t tell you how nervous I was when I saw her. This was the woman I’d seen fucking in every sort of position in the videos, the woman whose image was on nearly every boy’s computer doing her strip-tease as a virgin, the woman whose lovers numbered in the thousands, the personal favorite of the King himself. And I’d be fucking her!
But all that tension eased when she smiled at me. “Hi!” she said. “You must be Edgar.” Her voice was a breathy purr that went straight to my cock.
“Um, yes. But most people call me Eddie or just Ed.”
“Which do you prefer?”