Raw and Real: My First Time Losing My Virginity on a Desk


Master Napoli did things to me that I didn’t know could be done. I experienced sensations which blew my mind and entirely changed the way that I perceive myself. Sadly, what we did was never spoken of again. In fact, Master Napoli barely acknowledged me when our paths crossed. My mind started oscillating wildly between feeling excited about what had happened and experiencing a huge amount of guilt about it. I wondered if I’d pushed Master Napoli into an uncomfortable space, or whether, by not challenging or refusing him, I’d failed the first test. To make matters worse, for the longest time afterwards, it felt like my training had ground to a halt. There were no one-to-one meetings with the Masters, no talk about the next stage of my apprenticeship. I knuckled down, attending classes and reading everything I could, but, the longer it went on, the more I became convinced I’d blown it. Then I received notification of my Calling. My heart leapt with joy. The Calling is the first major ceremony here. When you’re called up, you’re received into The Order. It’s a massive honor and a huge step forward which definitely means you’re doing something right. Of course, I instantly read everything I could about the ritual but the whole thing is shrouded in complete mystery. Those who’ve experienced it, say nothing about it afterwards. So, as I walked through the complex to the allotted room, I couldn’t decide if I was terrified or utterly exhilarated. No one could tell me anything about Master Patrick, who was the one to lead the ceremony. The only thing anyone seemed to know about him was that he was new. No one could tell me what he looked like or whether he was friendly or stern. I took a deep breath and knocked on the door of his office. He called me in and instructed me to sit down at a huge desk which seemed to fill the space somewhat unnecessarily. I found myself immediately attracted to him. He’s very dark-haired like Napoli but his skin is pale. He was dressed in a black suit, which looked very expensive, with a yellow-and-gray-striped tie and a white shirt. To be honest, he was so well-groomed that I immediately felt really shabby. I’d struggled to get the knot of my tie up into my collar and it didn’t seem to matter how much I ironed my shirt because it always looked creased. I was completely disarmed by Master Patrick’s first question. He asked if I still submitted that I was not attracted to men. Plainly what had happened with Master Napoli had blown that particular belief entirely out of the water, but I felt pretty sure that it was not something he’d have wanted me to discuss with anyone, and furthermore that any form of same-sex activity could well be frowned upon by the Order, so I lied and told Master Patrick that I was straight. To be honest, he seemed a little bored by my answer and, rather wearily, instructed me to stand up. The next few minutes went by in something of a blur. I felt entirely overwhelmed. One moment, I was drinking from some sort of ornate glass vessel and the next he was running his hands all over my body, undoing my tie and unbuttoning my shirt while my dick quadrupled in size. My heart was pounding in my mouth. My skin was suddenly covered in a million goosebumps. Master Patrick’s touch was intimate, soft, thorough… I kept looking at his lips. For some reason I felt an intense desire to kiss them, but I also knew that that level of boldness would be very much frowned upon. Master Patrick rather speedily unbuckled my belt and was soon standing behind me, his body pressed into me, unzipping my fly and allowing my pants to drop to the floor—all the while he carefully massaged the bulge in my underpants. He then ordered me to climb onto the desk and present myself to him on all fours, like some sort of livestock at a county show. It should have felt a little humiliating, but all I could think about was how much I wanted to please him. He walked around the desk, surveying every inch of me while loosening his belt and tie and rolling up his shirt sleeves. He started to touch me again. It was as though his fingers were melting into my body. He worked his way down my back and then, all of a sudden, he started to kiss my butt cheeks. That was surprising enough, but when he pushed his tongue into my hole, I was astonished. The sensation of it wriggling around down there was a weird mixture of ticklish and incredibly erotic. I could hear him stripping more of his clothes off and all sorts of crazy thoughts started to fill my brain about where this encounter was heading. At that very moment, I think I’d have done anything in the world that he asked me to do. The thought of losing my virginity to a man had occurred to me from time-to-time in the past, but since Master Napoli had his way with me I’ve basically thought about very little else. In every single sordid fantasy, I’ve imagined being the dominant one, however, but as Master Patrick continued, I began to wonder whether there was some expectation for me to be the receiver. I genuinely couldn’t process how that thought made me feel. He stood me up again and leaned against the wall, guiding my hand onto the bulge in his pants and encouraging me to explore it with my fingers. It felt surprisingly large and I experienced a sudden, overwhelming desire to put it in my mouth. I fell to my knees, shocked by the unbelievable brazenness of my own behavior. Of course, once down there, I didn’t have the slightest clue what to do next. His pants dropped to the floor. His beautiful dick was bulging in his underpants, hard as steel and twitching. I let my tongue dance over the mound for a moment before pulling his trunks down and marveling as it burst majestically into the open, like a free diver coming up for air. The sheer size of it took my breath away. For a moment I contemplated apologetically explaining that I’d never done anything like this before and asking for some pointers, but in the end, I simply took a deep breath and wrapped my lips around it. Judging by the pleasure-laden noises he instantly started to make, I was doing pretty well, so I guess I just kept at it; sucking and licking, allowing my lips to glide up and down the shaft, continually looking up at his face for clues. I ran my fingers over his balls which were incredibly low-hanging. Everything was perfect. Then he pulled me to my feet again and pushed me against the table and I knew instinctively that the moment had arrived. Losing one’s virginity is a pretty big deal and I guess we all have these fantasies about the circumstances in which it’s all going to happen. It didn’t occur to me that it could happen anywhere other than in a bed, but there I was, leaning over a wooden desk, for a man with an enormous penis I’d met for the first time less than fifteen minutes earlier. And then he penetrated me. Just like that. And, just like that, I was no longer a virgin. He slid the entire length of his dick into me in one very long stroke. I can’t begin to explain the sensation. It felt like I was being torn apart. It felt like someone was forcing a baseball bat into my body. Each time I thought he must be fully inside me, he’d push it in another inch or so. I entered a state of pure shock, I think, but genuinely, the most enduring emotion was one of desire. I wanted him. I wanted to please him. I wanted to feel like I was part of him. He started to groan as he pulled it in and out of me and I suddenly felt my body beginning to relax. From then on it was magical. He started to vary the pace and depth of his strokes. Just as I felt myself getting used to one rhythm, he’d change things up so I was constantly kept on my toes. I started to push back on him. The thought that he was inside me, entirely raw, made me incredibly horny—as did the thought that I’d now lost my virginity. I felt like a true man, somehow. I kept looking back at Master Patrick to see the look on his face. He was smiling like the arrogant cat that had gotten the cream, no doubt more than a little pleased with himself that he’d managed to pop my cherry without any complaints from me. I guess I knew he was using me for his own carnal pleasure and that he’d taken something precious from me in the process, but I didn’t care. I’d have done anything to see that look on his face. He threw me onto my back and continued to pump himself into me, then turned me onto my side and banged me so hard I felt sure his dick would somehow reappear up my throat. He seemed to have an infinite capacity to fuck me harder and faster every time I’d convinced myself he was going at full tilt. It was almost like he was showing off; demonstrating his immense sexual prowess, almost mocking me for daring to fantasize about being the top partner during my first, or, frankly, any subsequent encounter. He pulled out and started to jerk himself and then suddenly his enormous dick was spraying vast quantities of semen all over my ass cheeks and onto the table and the carpet. Then he slid himself back into me and finally kissed my lips. I felt truly alive.

Date: April 7, 2024

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