The Boy and the Boss
by ChrisCross
Copyright© 2020 by ChrisCross
Erotica Sex Story: The Boss isn't a person. It's a commanding sex toy that sixteen-year-old UK Military Mentors Academy valet Michael uses to subdue and dominate fourteen-year-old military academy cadet Trevor.
Caution: This Erotica Sex Story contains strong sexual content, including Teenagers Consensual Reluctant Gay Fiction Military School MaleDom Light Bond Rough Anal Sex Analingus Cream Pie Oral Sex Sex Toys Size Teacher/Student .
“Ahhh, that were very nice,” I said with a deep, satisfied sigh, as I spilled my seed down Cedric’s chin. We were in the boathouse on the lower lake, here because Cedric had wanted me to fuck him. But now we’d have to sit and talk for a bit, listening to the racing shells grind against the dock outside in the bit of a squall that had come up over the Military Mentors Academy grounds. It would take me a few to recharge.
“Cig?” I asked, reaching into my pocket and pulling out a pack while the fourteen-year-old boy scrubbed at his face with a dirty handkerchief.
“Thanks,” he said, reaching out for the fag. He stood and turned, leaning back against the gunwale of the boat I was sitting on. “God, you are built hanging.”
“That’s what you came for, isn’t it?” I asked with a laugh. I was unbuckling his belt with one hand and moving the other down the small of his back and under this waistband, moving into his crack. I’d need time to be in form again, but there was no reason not to prepare him.
“Yes, you are a legend over at New College ... ugh!” I’d found his hole with my forefinger, and he was rising up on the balls of his feet in surprise. But with a shudder and a little moan, he settled back down on the finger. This is what he’d come here right after dark for. To check out the military academy legend for himself.
“And you’re over at Old College?” I asked. He groaned an assent as I pushed the trousers down off his thighs and reached for his dong. Not much more than ordinary, but thickening well. “Valeting for the cadets, are you?”
“Yes ... oh, shit, oh fuck.” I had three fingers in him now. He’d need to be real open for me. “Yes. And you? Over at New College.”
“The same.” At fourteen, Cedric was young for a cadet’s valet. They mostly were closer to my age of sixteen.
“Valet for that new cadet, Trevor Coleridge I hear. Father’s the big snot for the 6th D.C.O Lancers out in India on the North West Frontier.” Trevor was fourteen, like Cedric, but he was a student; Cedric was a servant.
“Yes, I do for him.”
“And does he enjoy that big cock of yours in him? Particular nice piece of arse that.”
“No,” I said and then laughed. “I don’t do for him that way—would like to, but no. The lad’s stiff as a board proper. Really up tight. A bit of the old man, I hear. A virgin.”
Cedric snorted. “Not a virgin, I hear. I hear he has a regular appointment with his tutor, Peter Hopewell.”
“Peter Hopewell?” I asked, incredulous. “Hopewell is almost as stick up the arse as young Coleridge is and puny as a beanpole. I can’t see them doing it.”
“Well, check it out for yourself. Tuesday afternoons at two, or so I heard. In Coleridge’s room. Faithful as clockwork.”
“I still don’t believe it. But here, you came to get a taste of this,” I waved my ready wand at him, and his eyes went wide. “and I don’t have all night. So, let’s get to it. Here. Hop up on the ledge of the gunwale. Here where it’s thickest.”
He did as I asked. He was trembling a bit, and he looked scared, his eyes constantly going to my cock, which was hardening up nice, and then looking away. I stripped off his trousers.
“On the small of your back. Yes, like that, roll your arse up to me and hold your thighs out yourself.” I let him watch me pull a rubber on, and then I went down on my knees between his legs and lifted his dick out of the way and squeezed it as my tongue went to his buttocks and the crevice between.
He was making little grunting and groaning sounds.
At length, when I thought he was open enough to take me just, I stood, rubbed my cock and his hole with cream, and, taking that big breath that all athletes take before making the big plunge, presented at the rim of his hole.
“Oh god, you’re huge,” he whined and went rigid as I got the rim of my bulb past his entrance. He had been gasping but now he was still and straining to take me, and his complexion was turning red.
“Here, now,” I said. “You’ve got to breathe. Breathe. Relax. You act like a first-time school girl. You’ve had it before, haven’t you?”
“Yess ... oh god, oh god ... but nothing as big as this. Oh fuckkkk.”
He’d come for it because it was big; he wanted it. So, I gave it all to him in one deep thrust.
“Oh, god! ... Oh GODDDDD!”
Turned out Cedric was right. The next time I was tidying up Trevor Coleridge’s room, I flipped open his appointment book and there it was, the notation at two on each Tuesday for “tutorial with Peter.”
The next Tuesday at two I made sure I was in the service back hall, with the valet’s door into Coleridge’s chambers open a crack. I heard voices and soft laughter down the service stairs behind where I was standing, and I went down to find the boys in service, Hugh and Cedric, crouched down on the turn of the stairs. Hugh, fifteen, was giving Cedric a blow job, and I stood there and watched for a while, pleased by the good, straightforward sex of it. Then I remembered why I was in the back hall and went back to the door into Coleridge’s room and pushed the door open to a wide crack.
They were already going at it, if you could call it that. I had to check myself from laughing out loud. They were side by side, close together, in overstuffed chairs, naked. Arms were extended over the chair arms, Peter’s hand working slowly on Trevor’s cock and Trevor’s hand pumping Peter languidly. Peter was reading poetry from a book. Trevor was a real beauty, tanned and slim, even at fourteen, from life on the Indian frontier. Cute as a teenage movie star.
Peter was another matter—an indoor scholar—all angles and height, concave chest, hairy as a dog, dark, and with a poor excuse for a cock. I could hardly see it encased there in Trevor’s hand. The only attraction that I could see must have involved seniority, the position as a tutor—but then, here at Military Mentors Academy, seniority was everything.
Call this fucking? Reading poetry and calmly jacking each other off. Gorsh. I’d say Trevor was still a virgin in any way that mattered. But it wasn’t all the fucking they did, and I decided that Trevor, technically couldn’t be called a virgin. Peter snapped the poetry book shut and stood up and pulled Trevor up as well. They moved over to the desk in front of the window. Peter gently pushed Trevor’s chest down onto the chair that was inserted into the desk hole, and as he did so, Trevor widened his stance.
A rolled-on rubber and a few minutes of rubbing cream in and Peter was pushing his small cock into Trevor’s arsehole. Trevor flinched a bit at the first breaching, but nothing significant or painful looking. Peter bottomed quickly and just held there, moaning softly, his head flung back in what passed for ecstasy for him, while, holding a washcloth over his tip, Trevor slowly beat his own cock to ejaculation and stared out of the leaded diamond windows of his bay window onto the parade grounds below. Peter was reciting poetry again, and the pace of his voice picked up and he became breathy. There was a slight lurch and a tightening of his thin buttocks, and then the ritual was all over.
It seemed so sad. Trevor looked like he was just marking a “to do” activity off his life’s experiences lists. His beautiful body and sensuous lips told me that he wanted so much more out of life. He had so much life ahead of him. I ached to help him through the fourteenth year of it.
They dressed in silence, there was one pecking kiss on the lips initiated by Peter, and then they settled down in the upholstered chairs and opened their books for the justifying tutorial session.
That was it? That was all? I thought. There hadn’t even been enough for me to take my meat out and beat it. Although I was hard. That was from watching Trevor. As Cedric said, he really was a nice piece of tail. He deserved better than Peter.
But then I guess that was the way in the British colonial army life. Attend a military school like Military Mentors Academy, as your father did and his father did; become imbued with the gentleman soldier’s training as your father did; become manned by a sensitive but consumptive upperclassman as your father did; find an appropriate bride from a suitable family to marry just before embarking for your colonial posting as your father had; produce sons as your father had—and pick out the best looking of your sepoys and fuck him for your only sense of self and rebellion as your father did.
I turned and crept back to the top of the stairs and did now take my meat out and beat it while watching Hugh splayed out on the stairs on his belly and Cedric crouched over him from behind and fucking him furiously, both of them grunting like pigs. Now that was fucking. A difference between upstairs and downstairs perhaps. I suddenly had a desire to find out.
I spent the next night trying to forget Trevor Coleridge—the beauty of his young, supple, slender, yet muscle-hardened tanned body—and not being able to do. I resolved to act and justified it by telling myself Trevor wanted more out of his male-male experience and ultimately would be grateful to me. It was a gamble, and it might lead to me being booted out of a pretty cush military academy job—but it wasn’t as if Trevor was repulsed by the idea of being fucked by another youth. All of the rationalization came down to the simple fact that I wanted to fuck the cadet from colonial India just to get my cock in him for my own pleasure, however.
So, in the still of the night, I threw some necessities and a couple of toys in a bag, and just in my sleeping briefs, I padded down from my attic room in the New College service area and crept up to the service door into Coleridge’s chambers.
All was dark inside, and I could hear him gently snoring. I crept through the door and silently shut it behind me and stood, still, for some minutes until my eyes had fully acclimated to the dark.
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