The Ruby
Copyright© 2026 by Jehoram
Chapter 2
Erotica Sex Story: Chapter 2 - 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
Still in a daze from the screwing I got from Fiona, I was led down to the cafeteria by the pool to rejoin my fellow “virgins.” I had breakfast and brushed my teeth, and Courtney, my Courtesan escort, took me over to the Courtesan who oversaw the assignments. “I’ve got Edgar for his next tryst,” she announced.
“No, you can’t do that. I have to wait for requests for assignments, you know.”
“New priority for Edgar. Check your texts.”
The Courtesan checked her phone. “Just got a new one. From Ginger. Fast track. OK, you can go.”
Courtney led me directly to one of the tryst rooms. On the way, I asked her, “What is this ‘fast track’ about?”
“It means that you’re off the usual routine assignments. From now on, you’re to screw only your virgin friends and Courtesans who are specialized in one of the sexual acts. I guess it means that the Baroness feels that you could use all the experience you can get. It’s really an honor. She thinks that you have greater potential as a fuck-mate than the other boys. That doesn’t happen very often.”
“And the girls, too? What am I supposed to learn from that?”
“You’ll learn what it’s like to give girls their first screw. It’s a big part of any Ruby boy’s job. It’s obvious that none of the girls here are true virgins anymore, but they’re still new to the sex act, and can teach you something of what that’s like for women ... where they need reassurance and praise.”
“And what’s your specialty?”
“Tantric sex.”
“I’ve only read about it. It’s not one of the things on the videos.”
“That’s because you can’t really capture it on video. Well, here we are.” She closed the door and stripped off her leotard. Her tits were small and her dark brown bush was trimmed. There was a butterfly tattoo just under her navel. And I saw the string of a vibrator protruding from her cleft.
“First, let’s get you hard,” she said. “I hope the Baroness left me some cum!” I was already most of the way down that road, and a little cock-sucking got me the rest of the way. “Now sit on the bed and lean your body against the headboard, and spread your legs.” She removed the vibrator from her snatch, positioned herself over me, and guided my hard cock into her vagina in one easy sweep as she sat on my lap.
“Just sit there, very still, and feel my cunt on your cock.” Her vaginal muscles massaged my cock and I felt it swell to its hardest. The massage continued until I erupted in an orgasm and dumped my load into her womb.
“Stay still. Don’t pull out. Your cock will get soft inside me, and stay soft there. Just don’t move.”
“Can we kiss?”
“For first time, sure. But usually we just sit perfectly still when we’re doing this.”
And that’s what I did. I kissed her, but she didn’t really kiss back. She was slipping into a sort of trance state. It felt really strange to have my soft cock inside her, with her vadge muscles squeezing me gently. She was breathing slowly but heavily, and I followed suit. It took an hour or so of us in that position, and I could swear I was feeling sexual energy being transferred from her to me. And then I was hard again, even harder than before, it seemed to me. She began to sweat heavily, but didn’t move a muscle.
The second orgasm seemed to float me up gently into the air, like a balloon ride. It lasted longer than any cum I’d experienced before. It wasn’t quite as thundering as the one I got from Fiona, but I could savor the moment better. And I felt a new connection to Courtney, almost on a psychic level.
“Did you cum?” I asked.
“I’ve been cumming since your first orgasm. That’s one of the benefits for women ... we can just cum and cum and cum. Your orgasm lasted longer than usual, right? That’s what a woman’s orgasm often feels like. You’ve just connected with your feminine side.”
The session was over. It took a little longer for me to get harder again this time. Courtney took me back to the pool room, dropped me on one of the chaise longues there, and gave me a great massage, paying lots of attention to my cock. After a swim and a bite to eat, I was hard again and ready for more screwing. Elaine, one of the virgins, had just come back. “Fuck her,” Courtney told me.
“Let me rest and swim first,” Elaine said. “The last guy didn’t get me off, so there’s a lot of libido left for you!” And she was right. We fucked right there on the chaise longue, and was able to give her a nice hard shag with a boner that lasted an hour. Another swim, some lunch, and I was ready for more, this time in a Tryst Room with a Courtesan who specialized in cock and ball torture ... light at first, but gradually putting me right on the edge of pain. She wrapped a cord around my balls and pushed them downward. Then she began to slap my boner and balls, and I watched them bounce in the mirrors. I didn’t know how closely pain was linked with pleasure, but she was an excellent teacher, and had me cumming at the cusp of my pain, my cock spewing cum onto her belly. She then untied me and took me back to the pool room, wearing my cum proudly.
I got a big surprise on Thursday. I’d spent the night with Diana, a Courtesan who showed me how to fuck her as we spooned. She took me down to the pool room for breakfast the next morning, When I was ready for my first assignment, I was told to go up to a certain Tryst Room, and when I got there, I saw Lily, sitting on the bed, legs wide open, and smiling at me!
“I was expecting another Courtier!” she said.
“And I was expecting another Courtesan! That’s all I’ve been getting the last couple of days ... one of you girls in the pool room, or a Courtesan here in a tryst room.”
“That’s all I’ve been getting, too ... Courtiers in the tryst room or one of you guys at the pool. What’s going on?”
“I found out I was getting fast-tracked ... only virgins and Courtesans. I bet you are, too. I can see why ... you’re the prettiest of the new girls.” And she was, too. Long legs, dark skin, slim figure, gray eyes and long, frizzy black hair. But the most remarkable things were her boobs. Not very big, but with dark “bullet nips” that stood out an inch and begged to be sucked. And a cunt that showed a lot of meat and a clittie poking out of her slit like a miniature cock.
She had the same sexual aura as Baroness Fiona, not as mature but with the same easy confidence and ability to get me hard. Most of the other women I’d fucked up to that point were like, “I’d sure like to fuck you,” but with Lily it was “I’ve really got to fuck you.”
“I didn’t see you at breakfast,” I said.
“That’s because I slept with the King and had breakfast with him. I think he likes long nips, like Baroness Fiona’s. The virgin he fucked on my first night had nips that were even longer than mine, so he took her cherry instead of mine. But I got the next fuck with him.”
“You must mean Rainne. Her nips are freakish! But you’ve got them, in spades. May I suck on them?”
“Oh, God, yes! Let’s get going!” She lay me on the bed and thrust one of them into my mouth. I knew what I was doing, because that was one of the sure ways of getting Trisha off. Lily was cumming in no time. “That’s one of the first things I learned at the Artemis Club,” she said. “I could cum from nipple play alone.” And that was all she said as I sucked and played with those stiff nipples.
“Get inside me,” she breathed as she crouched over me and guided my rod into her cunt. She was already wet ... whether from her own juices or the King’s jizz I didn’t know, and didn’t care. “Let me try something. I want to time my vaginal squeezes with your pumping. That’s something Mark was teaching me.”
“Mark? I think I met him yesterday.”
“The Senior Courtier. The blond guy you probably saw fucking the Courtesan Prime on those videos, if you guys were seeing the same ones we did.”
“When did you do him?”
“Day before yesterday.”
“Was he good?”
“Well, he’s Baroness Fiona’s favorite fuck. And the Queen’s, too. That should tell you something!”
“If you impressed him, it’s no wonder you got fast-tracked.”
And then we were overcome by our mutual lusts, and our conversation turned into energetic, sweaty sex. She was a hellion in bed. What little she lacked in experience from the Courtesans was made up for by her enthusiasm. It was as if she was getting the same rush I’d been getting in the discoveries of what true sex was all about, and what adventures lay ahead of us.
She was bouncing up and down furiously on my dick, plunging it into her and squeezing it mercilessly in time with the plunges. As she bounced, I grabbed and pinched her nipples, mimicking the squeezes I felt on my cock. “Oh, yeah,” she breathed. “Do that. Harder!” I yanked harder, and she suddenly shook as her climax heightened.
But soon I started to feel that sense of being close to the edge. “I’m gonna cum, girl.”
“I’m cumming already. Just let it go. Wait ... wait ... let me see if I can do this...” With that, she lowered herself completely, driving my dick into her depths.
And when I felt my cock finally spurt my jizz into her, each spurt was answered by a clench of her Kegels, only a split second behind. It inspired me thrust myself even deeper into her, lifting her off the bed.
“Damn, girl! That was great!”
“I did OK? I really wanted to. Especially with you. I remember staring at your cock on the first morning we were here, when I was on the Sybian. I wanted that cock right away!”
She continued to squeeze my rod with her vagina as it softened, while she nuzzled my lower lip. What a hot girl, I thought. She’ll go far. We talked for a while, and I discovered that she was indeed the girl in the video whose dance captivated me. We finally got up and went down to the pool room for a quick swim, while the Courtesan on duty searched the schedule for our next fucks.
And that’s how the next couple of days went, coupling with the last three virgins I hadn’t already fucked, and being introduced to all sorts of kinky sex. I had a last fuck with the Queen, too, who wanted to see how I was coming along in my education. “If you ever want to consider a Courtier job here, just let me know. I’ll make it happen. I’ve already talked to Ginger about it.” Ginger. Baroness Fiona. The Courtesan Prime. It was like we were already on a first-name basis.
When the week ended, we were inducted into the Order of the Ruby, which meant two things. First, the ruby rings allow us to fuck any of the school staff or teachers, and arrange to meet them at bedrooms in a bulding next to the dorms. We’d call it “Fuck Hall” and we could reserve a room for the night for our trysts. Those rooms were set up just like the Tryst rooms in the Palace, with mirrors everywhere, but instead of a private shower area, there was a big communal one where men and women showered together.
Just before I left, a package was delivered to me. It was a jewel box. Inside was a golden cock ring with a ruby mounted on it ... a special parting gift from the Courtesan Prime. “Only one boy in fifty gets one of these,” a card read. “As you get older, your cock will get thicker, so send it back to the Palace when you need it adjusted.”
My first tryst when I got back to the school was with Trisha, because I’d been wanting to fuck her every since my first encounter with her. When she saw the ruby ring on my pinky at the next massage session, she smiled and whispered “How about a little fuck tonight after the club meeting?” It was another dream come true!
She was a pretty good fuck, too, and I already knew about her arousal patterns from the Apollo Club sessions. In fact, she was the first person I’d fucked that I’d already known as friend for a long time. She told me that fucking kids like me was one of the perks of her job, and she almost never spent the night alone, with so many boys who are members of the Ruby or the Emerald at our school. Not to mention the teachers, masseurs, and office staff here. “But I like the young boys the best, because I’ve trained them! And their cum is the tastiest!”
We did cowgirl, because that’s what she wanted. I played with her nipples as her breasts bounced up and down, and brought her to a quick climax when I began to pinch them hard. She was cumming so heavy that I don’t think she noticed when my cock started throbbing with the release of my jizz.
After I ejaculated, she slumped over me and gave me a long kiss. When my soft dick slid out of her, she lay on her side and we cuddled and chatted for a while.