My name is Alice Tooney, and I’ve really fallen down the rabbit hole. Now I’m naked and standing in a room with two dozen schoolboys, all equally naked, oiled, and jerking off. I’m seeing their jism spurt as I fondle my bare breasts and smile at them. And tonight, I’ll probably be sleeping with one of them, like I do nearly every night.

But not this boy. His name is Miguel. He’s fifteen years old, a sophomore and a virgin, in the first day of his first year here. His nearly hairless crotch has only a small, slender dick and tight undescended balls. He’s just come in from gym class, where he exercised in the nude. He’s sweaty and already has half a hard-on, ever since he saw me standing naked next to the massage table. “He’s on a hair trigger,” I think. “It won’t be long.”

When I get to his genitals, I work the oil into the area around them before I actually touch them. His cock is already getting fully hard as he watches my bare breasts swing. As I trace a line down his oily shaft from the base to the frenum, I can see it twitch. I can feel his pulse as I squeeze it lightly. I’m not allowed to stroke him to an orgasm, but he’s free to do it if he wants to.

Today, he wants to. “Can I cum?” he asks me.

“Your penis is your own. You know that you can do whatever you want with it, as long as the sight doesn’t offend anybody.”

“Will it offend you, Ms. Tooney?”

“Not at all. And thanks for asking! It shows that you’re a polite boy. Go ahead. I like to watch!” That’s not a lie. It’s part of the pleasure I take from the job.

So I watch him jack off. His slender cock can’t take more than a few strokes of his hand before it squirts out a teaspoonful of thin, clear cum. I mix the cum with the oil on his hairless chest, and then I send him off to shower. The room is full of the sounds of all these boys groaning as they blow their wads. Once, I would think it was weird. Now it’s music to my ears.

I am one of the masseuses employed at the Trinity Preparatory School for Boys. My main job is to give massages to all the boys as they leave their Physical Education classes. They arrive all naked and sweaty, aged from fifteen to eighteen, and I rub them down to ease their sore muscles.

But there’s another component to this job: I work naked as well, and monitor their level of erotic stimulation. As I work on the boys, with my bare breasts hanging freely over them, I gauge their interest in what they see. And when I massage their penises, I take note of how fast they become erect. For no boy of that age is able to endure the sensation of skilled, oily hands fondling their cocks without becoming at least a little hard. More often, they become hard almost immediately. I’m not allowed to masturbate them to an ejaculation at these sessions, but they are free to cum as they wank themselves, and I am also to note how much ejaculate they produce. And most of them do wank, especially Miguel and the other younger ones who have not been trained to “edge” their libidos and keep them in check.

I must confess that at the sight of all those beautiful bodies with their erections, I become a bit horny myself. If I want to wank myself casually during the massages, I’m certainly allowed to do so. Some of the boys are more attractive than others, of course, but they are all beautiful in their own way.

If I get really horny by the end of the sessions, I can almost always get a screw from one of the masseurs right there on the massage table after the boys leave. A lot of them get really aroused by the sight of naked young boners, but are afraid to express it sexually. So they plant their stiff rods in a real naked woman instead. It’s just a five-minute “quickie” until the next group of boys comes in. There’s nothing in it but a rapidly satisfied lust, an “off the shelf” orgasm. There’s an older masseur named Gus who almost always has a hard-on after two or three sessions every day, and I’m happy to have that cock pumping his sperm into me.

I noticed when I started working that some of the older boys wore rings on their little fingers, with either red or green stones. It was explained that these boys, all upperclassmen, were not virgins like the rest of the boys. If the ring bore an emerald, it was a sign that they had been taken away to a Deflowering Center and given their first sex from skilled girls their own age, and from a representative of the Palace called a “Courtesan” who had been assigned to the group by the Courtesan Prime, a court baroness who supervised the entire division of Sexual Gratification. These women had had literally hundreds of sexual partners, I was told. There was little they did not know about pleasing a man, or a woman for that matter.

The other boys, the ones with the ruby rings, were of a different status. They had been taken as virgins to the Palace where they were deflowered by the Queen herself, and then assigned a Courtesan who would entertain them that evening. After spending the night with these women, they would join a pool of five of their companions, along with six girls who had also lost their virginity the previous evening.

These twelve children would be on hand at the Palace for the next week, called upon to satisfy the sexual needs of the Palace staff, administration officials, and certain honored guests. Each boy would also have fucked at least five more Courtesans, along with six girls their age who had lost their virginities that same week. At the end, they would have had almost three dozen partners and would be admitted to the elite Order of the Ruby.

And then, every third weekend or so, the “Rubies” would be sent, in groups of six, to a Deflowering Center where they would introduce six virgins to the joys of sex, with each boy fucking each girl twice, unless there was a Courtesan who wished to have sex with them (and these usually did).

Once the boys had earned their ruby or emerald rings, they were allowed to have sex with any consenting adult they pleased at the school. So it was a shock to me when, on my third day at work here, a boy with a ruby ring asked to fuck me. His name was Nathan, and had a cock that was thick although a little shorter than normal. When I began to massage his front, his cock became hard almost immediately, and he smiled as he used his strong hands to bring himself to an orgasm right there on the table, spewing his load onto his chest.

“Thank you for letting me look at your beautiful breasts,” he said. “Ms. Tooney, I have to say that you’re very beautiful and sexy, and I was hoping that you would allow me to fuck you tonight.”

“Do I have to say Yes?” I replied. “I mean, I think you’re beautiful, too, and you have a lovely cock. But we don’t even know each other.”

“Of course you don’t have to say ‘Yes.’ It’s always your call. But around here, the only thing that matters is whether I am lusting for you, and you for me. That’s what the whole arrangement is about.”

I considered the invitation for a minute. What the hell, I thought. I had no lover at the moment, and he was cute, and I was horny. He’d supposedly had dozens of women, what with his Virgin Week and all the deflowerings he’d done after that. He’d have fucked more women than I had fucked men. He couldn’t be a total loss, would he?

“All right,” I said. “But how do we work this? I mean, do they let you off campus to do that?”

“No, we do it here. There are some rooms set aside for it in the dormitory. I’ll reserve one for us. Just go to the desk and give them my name, and they’ll give you a room number and a key.”

And that’s the way we did it, my first fuck with a student. I opened the door to find a bedroom with a king-size bed, and mirrors on the ceiling and on every wall. The room had its own bath. And there was Nathan, in his school uniform, his blazer already unbuttoned.

“Thanks for coming,” he said as he offered me a bottle of sparkling water. “May I have the honor of undressing you?”

“Well, sure...”

“Or would you like to undress me first? I mean, we’ve already seen each other naked, right? It wouldn’t be anything new.”

I smiled. “Okay. Let’s do you first.” And I slipped off his blazer and, with trembling hands, unbuttoned his shirt front. I was about to fuck a sixteen-year-old boy, a boy two-thirds my age.

His shirt came off, and then his trousers after I unbuckled his belt and unzipped his fly. He kicked off his shoes, and I slipped off his socks. Pulling up his undershirt, I ran my fingers across his chest and felt the soft brown hairs I’d so often massaged.

And then his briefs. His cock sprang free, already thickening, like it always did at the massage. He stood nude before me and said, “My turn.”

I gave him a quick smile and nodded. He unbuttoned my blouse and kissed the bare skin under my bra line. Then he lovingly pulled down my skirt, and it fell to the floor. I stepped out of my shoes and kicked them away, along with my skirt. Except for my bra and panties, I was naked. Well, he’d seen me in the altogether at the massage sessions. As he said, it wouldn’t be anything new to us. But last time, sex wasn’t on the table. Now, it was to be the main course.

Kneeling before me, he slipped down my panties and kissed my mound, with its trimmed bush. Then he stood, his stiff rod grazing my cunt lips, and reached behind me to undo the clasp of my bra. He slipped off the shoulder straps and it fell down, my tits suddenly dropping free. He lifted them appraisingly, let them drop again, and then smiled at me.

We hugged, bare skin to bare skin. His hands danced across my body, caressing my ass and back as he kissed my neck. My libido rose. This kid knew what he was doing.

“Would you like to take a shower now?” he said. “I did before I came.”

“I did, too.”

“Then lie on the bed and spread your legs, please. I’ve been looking at that delicious cunt of yours and wanting a taste.”

I did as I was told. He was instantly at my crotch, his hands stroking my inner thighs as he breathed lightly on my cunt. Then his tongue came out, licking the outer lips, seeking their fold. I felt them separating, and his tongue was on my inner lips, gliding up and down. As it found my clit, it lingered and pressed on it, and then slid back downward to my hole. He knew what he was doing, all right!

I was breathing heavily. I felt a finger press against my entrance. “May I?” he breathed.

“Oh, yes,” I said. And I felt it probe my vagina. The fingertip explored its front surface. He was looking for my G-spot. I played cold-warm-hot with him, helping him locate it, and then I felt him pressing on it while tonguing my clit. My libido flared. “Two fingers, please,” I gasped.

I felt a second finger sliding in, stretching my hole. They separated, stroking the two sides of my vagina. “More,” I said. A third finger, stretching me more. and then I felt the orgasm start in me, and swell, and overcome me. He felt it, too, and began savagely thrusting his fingers in and out. I grabbed my tits and squeezed them. Hard. My nipples were like hard rubber. And then I felt his teeth on my clit, nipping at it gently. ratcheting the climax up another notch.

After it crested and broke, my whole torso was flushed, and my skin was covered in sweat. His eyes shone as he looked into my face.

“So that’s what you learned at the Red Ruby School,” I managed to stammer.