I haven’t posted any stories of my exploits in quite a while, but on reading them back today realised that, even though I had written it, I must have forgotten to post it. This is a true tales of when I was an 18 year old student and had begun a relationship with one of my lecturers, Mr West. I might need to go back and number the stories so they can be read chronologically, but for now and for those of you who have read my other posts, this took place a couple of weeks before I went with Mr West to meet the two guys with a pub and a porn collection, Mal & Mark. We had been enjoying our meetings and I loved what we had done so far. I had found that I loved performing oral, and especially swallowing cum. Mr West loved me going down on him to completion too, and his rimming of me made my cock want to explode with pleasure at the first touch. Although he usually fingered me and sometimes used a dildo he was reluctant to actually put his cock inside me. When he was fingering me I did occasionally blurt out a plea for him to fuck me, but he never followed through and as we always had so many other fun things to do I didn’t push him. He had also made it clear that he did not want to be touched there, which also meant my experience of rimming was very one-sided . It was his personal choice and I had to respect that, but I made no secret that I was very much intrigued and excited at the though of anal sex, and often tried to imagine that, when I masturbated at home, the dildo I had in my arse was actually a hot, glistening cock. We had been talking about us meeting up with a couple he knew, but this was proving difficult for various reasons. It was frustrating for us both but especially for me, as I was certain that it was going to be my chance to have a man fuck me. I tried not to go on about it too much, but Mr West must have picked up on this though. One summer evening I arrived at his flat as arranged. After being buzzed in and climbing the stairs to the top floor I found the door open as usual, but could hear voices from inside. Going in I found Mr West sitting in the living room with another man. As I walked in they both stood and Mr West came and gave me a kiss, before introducing his guest as his friend John. John was, I would guess, in his early 30’s. He was moderately tall and quite a slim build. He was a handsome-ish in a nerdy sort of way, emphasised by his glasses and a neatly trimmed beard. I was a little puzzled about him being there, and very surprised by the kiss, as Mr. West was usually careful not to make any show of affection in public. It became even more confusing Though, as John came forward, put his hand on my shoulder and gave me a kiss on the lips! Although unexpected his lips were very soft, and tasted faintly of peppermint and I enjoyed the moment. They were both smiling at my puzzled expression, but I quickly forgot about that when Mr West lent in and kissed me again, this time opening his mouth and sliding his tongue into mine. I had been buzzing with excitement all day at the thought of seeing him, so the taste of his mouth and the press of his body against mine had me hard in seconds. Mr West must have felt my erection digging into him, as he eventually broke off our kiss and whispered in my ear that I had to strip., before he and the stranger stepped back a couple of paces to watch me with hungry eyes. Knowing now that something new and exciting was happening I happily pulled my t shirt over my head and kicked off my trainers before unbuckling my belt and pulling down jeans and underwear in one action. As I kicked them away and stood up my cock, now free, was thrust straight out, rigid and throbbing with lust. In a second John was standing next to me, reaching out to run his fingers down my chest and stomach, only stopping once his hand touched my pubic hair, where he lingered for a moment before stroking back up. He now had his hand on my chest and was stroking me, his fingers tracing around my pecs and drawing circles on my nipples as he murmured compliments in a husky whisper. I loved having my nipples played with and I let out an involuntary groan of pleasure at his touch. John responded by leaning forward and lowering his head to kiss my chest and lick at my now hard nipples. At the first touch of his wet tongue I let out a louder gasp, and continued as he first kissed and licked, then sucked on one, then the other. “You can be rougher than that” I suddenly heard Mr West say, realising that, in the excitement I had forgotten about him! “John has my permission to bite you Tony”. John was clearly excited and in response lips were replaced with teeth and I exploded with pleasure at the delicious pain. He obviously liked hearing me gasp out in pain, as the first tentative nips were soon Increased to full on biting, pulling and twisting. Mr West had punished my nipples many times, and even put me over his knee and spanked me on more than one occasion so we both knew I liked some pain mixed in with my pleasure. However as John was a stranger, my not knowing what his intentions or limits were made the pain seem more dangerous and thrilling. My legs were about to buckle under me when he finally broke off from the torture and commenced feverishly kissing. His tongue was in my mouth as his lips pressed hard against mine. I responded and soon our arms were wrapped around each other, clawing at skin as we shared saliva. We finally broke for air as Mr West told John to take me to the bedroom. I looked over and, reassured that he was fine with this, let John pull me by the hand into the bedroom. Once in there John ordered me to lie on the bed whilst he stripped off. Mr West had followed us into the room didn’t join me on the bed or undress, but instead sat down on the chair that stood in the corner at his desk. I didn’t have time to question this any further as a now naked John climbed onto the bed and pulled me hard against his hot body, kissing me as his hands roamed over my flesh. As we kissed he rolled back, pulling me over so that I was on top. Finally I was able to see him naked and I was not disappointed. His penis was an average size and thickness, but with a slight upward bend much like my own. Like the rest of his body though he was entirely hairless and this made it seem bigger. When I reached down to squeeze his shaft his foreskin rolled back to reveal that he was already wet with his juices, and his plump helmet was glistening, red and tempting. Without a word John lay back and pushed my head down, making clear what he wanted. I shifted on the bed so that I could grasp the rock hard shaft whilst getting my tongue into his every crevice before licking his balls, sucking each one into my mouth. He was clearly enjoying this as he began to moan and cry out almost immediately. As this was a new cock for me I took my time, making sure I savoured every taste, texture and scent, and also used every trick Mr West had taught me before I even touched the helmet of his prick. This also seemed to work, as by the time I had licked the creases of his crotch, kissed and bitten his thighs and rubbed my lips up and down his shaft he was ordering me to go down on him. Once I had had my fun I finally took him in my mouth, enjoying the musky, salty taste of him. I wrapped my lips around the base of his glans and, sucking, rubbed my tongue all over and around the helmet, savouring the taste and texture before taking him all the way in and starting to blow him. We continued like this for a while and, whilst I was very much concentrating on enjoying myself, I occasionally glanced over to Mr West. He was sitting in the chair, watching us intently but with a smile on his lips. When we made eye contact he didn’t say anything but instead just nodded encouragingly. Eventually John pulled away and dragged me back up to his mouth for more kissing and licking. Now it was his turn to push me onto my back before kissing his way down to my rampant cock. I shuddered with pleasure as he wrapped his fist around my shaft and gave me a few strokes, before lowering his head to take me fully into his mouth. I am not small but he was able to very quickly take me all the way down his throat, pushing his nose into my trimmed pubes. The sensation was incredible and intense and I let him know just how good it was. In response he began to pull and squeeze my balls as he worked my cock, and the combination of pain and pleasure was almost unbearably good. After more of this he finally pulled my cock out of his throat, a long trail of spittle stretching for a moment from his lips to my cock before collapsing. He now pushed me over onto my side and made me lift one leg up, hugging it to my chest with my arm. In this new position he was able to snuggle up tight against me, his mouth next to my ear, kissing and biting me as his fingers stoked my arse. He stopped for a moment to reach over to the bedside table, and when his fingers returned they were slick with some sort of cool lube. He applied this gel to my arsehole, running the tip of his finger over and then pushing in. I had been using my dildo diligently and so there was only some slight discomfort as his finger worked deeper inside me. Once he knew I was comfortable he started to thrust in and out whilst also rotating. This was an incredible sensation, the feeling of the pressure and pushing against my insides sending me to new heights of pleasure. Even though I had been penetrated many times, the sensation of warm living skin was so different from the rigid toys I had used. After a moment he introduced another finger and, whilst this was painful at first, I was so lost in the moment that I managed to cope until it subsided. We continued like this for a few more moments, then his fingers were withdrawn. Still in this spooning position I felt him apply more gel to my hole and then to himself. He Was whispering in my ear to relax, breath deeply and, when he told me, to push back against him. I was still not sure if it was actually happening but soon realised it was all too real when I felt the pressure of his cock against my hole. Having already taken two fingers I hoped I was stretched enough that I would be able to take him easily, but it was a whole different sensation, and the pain was very real and enough to make me cry out. I heard Mr West from far away saying to relax, let it happen, as John whispered the same. He didn’t push any further in, just held his cock there until I was able to relax enough to let the pain subside. John now told me to push back against him, and go as quickly as I wanted to. I had assumed that he had his whole cock inside me, but as I tentatively pushed it was clear there was still more to come. Now however it was not as painful but still hurt. Nevertheless through the pain I was also thrilled and turned on at the thought of finally being fucked, so pushed back until, almost with a pop, he was fully inside me. We remained frozen like this for a moment, before John whispered to me that he was inside me now. He then looked over to Mr West and asked if he could take my virginity. Mr West was looking flushed with excitement as he just nodded his head. With permission given John began to gently move his hips. The sensation was of fullness, far more intense and satisfying than any fingers or dildo. I would swear that I could feel the warmth and the throbbing of his swollen cock as he pushed further into me. Soon he was fucking me, and with each thrust I let out a gasp of pleasure. We were in this position for several minutes before he had me release my leg, allowing my arse to tighten around his cock, now buried fully inside me. We continued fucking like this for a couple more minutes before he stopped and withdrew. As his cock slipped out of my hole I felt the emptiness like an electric shock but he quickly pulled me up so that I was kneeling on all fours. More gel was applied to my arse and his cock before he pushed back into me. There was still discomfort this time, but that was soon overtaken with pleasure, as in this new position it seemed he was able to get deeper into me, and my hole felt more stretched and tighter than ever. He now began to fuck me with real purpose, his hands on my hips, him grunting with each thrust. I was amazed that this was even more an intense feeling and really began to cry out, making meaningless yelps with every jerk of my body. We were in this position for only a couple of minutes before there was a pulse of pressure and suddenly, as he cried out, I felt a warm feeling of fullness as he shot his load into my arse. He pushed his cock hard into me as he filled me up with his cum, grabbing tight on my hips to force every last inch inside me. Only when he was fully spend did he resume moving his hips a little to work his softening cock back and forth, slowly withdrawing until he finally pulled out fully. I now realised just how exhausted I was and that my arms were trembling holding myself up, so i flopped forward onto the bed with relief. I was in too much of a post fuck afterglow to really pay much attention as John climbed off the bed, collected his clothes and walked out of the room with Mr West, and I was still lying there when Mr West returned a few minutes later, stripped off and climbed onto the bed with me. He lay next to me, propped up on one arm, stroking my back as he asked me how that had been. I had to tell him truthfully that it had been the most amazing, horny experience I had ever had. Not only had I been fucked at last, but it was with a total stranger (another of my fantasies) and whist we were being watched (another recurring fantasy). He admitted that he got a huge thrill from watching me with another man without joining in. As he told me this he was playing with his very erect prick, but he could not resist and pushed my head down, roughly forcing me to fuck him with my mouth until he shot his load, filling my mouth with his delicious spunk. It was noticeable that he was rougher and more forceful than he had ever been before, and I must admit I found it thrilling. That was the first time I ever met John, and I would not see him again until I started attending the sex parties that he and Mr West were part of. Whenever we met though he always told everyone that he was the one who took my anal cherry, so anyone who fucked me owed him!