This the story of my firsts sexual encounter with another guy. I was 19 years old at the time. I had had a girlfriend for some time by then and I identified as completely straight. Sometimes when jacking off to porn, I strayed from the regular hard core stuff to more unorthodox things like shemales and blowbangs. I have always been curious and open minded, and I had experimented with anal play myself before. One night while jacking off and looking for porn, I saw and looked up more and more blowjob porn, videos that make you want to suck dicks, high quality deepthroating porn, and so on. This became more and more of a fetish of mine, until after perhaps a year of fantasizing and masturbating, I decided I wanted to take it one step further. I looked for an adult meeting site in my area, eventually found one, and created an account. After several weeks of lurking and sending a few messages, one guy replied and we started emailing. He had never had any sex at all and was looking to get his dick sucked and maybe more than that. He did say he was quite fat, but he sent some pics of his dick, which was big enough to convince me to meet with him. We would meet up at a park near my apartment, and then go to my place.

On the night we were to meet I got myself pumped up by watching blowjob porn and jacking off while thinking about tonight. About 22:00 I took a prepared myself and took a shower, and at 22:25 I was at the meeting point. He would be there at 22:30, so I waited patiently for some minutes. After about a quarter of an hour I started getting annoyed and started walking around to see if maybe he had mistaken the exact meeting point. Around 23:00 I was about to go home when I decided to first check my email on my phone. I found a message from him saying his bike broke down and that he had to borrow another one, but he was on his way. I walked around for a bit because I felt creepy just standing there. After some time I saw someone matching his description and we greeted each other. We walked to my place making some awkward small talk mixed with silence.

We reached my place, a house shared with 4 other students, I had my own room with a desk, small kitchen, sink and bed. To my delight, none of my housemates saw us walking to my room. I locked the door and turned on the lights. We stared at each other for a second, I broke the silence by asking him if he wanted something to drink. I put two glasses of water on the desk. “So… How should we get started?” I asked nervously. He thought we should undress and maybe get into bed, which we both started doing right away. I had never seen another guy’s dick like this, not even in high school gym class or football or anything, so it was kind of weird and new to me. He hadn’t lied in his messages: he was really fat. I work out a lot and am very fit, because I think bodies like his are disgusting, so I was not sure if I was happy with the situation. He grabbed my balls and played with them for a bit, then we lied next to each other on the bed. More awkward conversation about what to do next followed. “You said you wanted to suck my dick right? How about you do that?” he said.

I hesitated on how to go about doing this. I sat up and brought my head to his waist, taking note of his big, fat belly on the way down. He motioned me to bring my knees over to his shoulders so we were in a 69 position. This was my first time seeing a dick so up close. It smelled clean and very sexual and in my hand it felt strange, like a dick, but not my own. I slowly jacked him off and brought my face closer to his balls, sticking my tongue out. His skin was colder than I expected and I licked his balls while jacking him off. Then I felt him doing the same to me, but my dick was still pretty soft. I tried getting both nuts in my mouth at the same time but failed constantly, so I brought my attention back to his penis, which had been swelling ever since I first touched it. I grabbed it by the base and held it upright. I smelled his dick and couldn’t resist a moment longer. My lips found the tip of his dick and slid over it, swallowing the tip in one motion. Instinctively I knew what to do, I had seen so many videos and thought so much about it, and started sucking his dick and bobbing my head up and down right away. Thinking of how much I wanted this I tried to experience it as intensely as possible, feeling his penis enter my mouth, tasting and smelling him and imprinting his dick in my memory.

When we had been going at it for a few minutes I realized that he had not been lying about the other thing he messaged me either. By now, his dick was completely erect and measured at least 8 inches and a lot thicker than mine. While sucking his dick and intermediately licking his balls and jacking him off I was pretty sure his dick was indeed enough to make up for his body. When I had gotten used to the idea of sucking cock and started doing my best to please him, I felt him adjust how he laid. Then his hands found my buttcheeks and spread them apart. We only explicitly discussed dick sucking, but being an anal enthusiast, I hoped that he was going to do what I thought he was. My hopes were rewarded, as I went down, sliding his penis into my mouth and sucking it, I felt him pressing his face into my ass. As soon as his tongue brushed my asshole a moan escaped my mouth, muffled by his dick. He started passionately licking my ass, massaging my butt and pushing his tongue into me. This turned me on even more and drove me to suck his dick harder, faster and take him deeper than ever. We 69’ed like this for several minutes, when his hands left my ass and one found my head, the other grabbed his dick. He played with it, rubbing it on my mouth and tongue and slapping me with it. He asked, with a hitn of shyness, “Can you try to take me a little deeper?”

I was already doing my best about as much as I could, but I didn’t want to disappoint of course. I said that I would try. I looked at his huge dick, now sloppy with precum and my spit, and went down on it. As deep as before, filling my entire mouth. I did this for a second when he asked me to try to get deeper. The next time I went down all the way, mouth full of cock, and pushed down even harder. It wouldn’t go any further. I took a breath and tried again. To no avail. On the third try, I took an even deeper breath, put my lips to his penis, and started going down. Inch by inch his penis went into my mouth, my lips were tight around his dick as I stopped. He wasn’t content yet. I felt him push my head down, forcing his dick deeper into me. It went a little further and into my throat and before I gagged he bucked his hips. I gagged and got up, breathing heavily. Without waiting I went down again and he forced his dick down my throat once more, even deeper this time. I swallowed and tried not to gag. We practiced for a while and soon I got used to this as well and got his dick more than halfway into my mouth. While I struggled to breathe and not throw up he fucked my eager mouth and I saw his hips moving, shoving him into my throat inch by inch. After probably fifteen minutes of this I wanted a pause and said so. He wanted one more go and I got myself ready. As I expected, he pushed down harder than before, I received his dick and concentrated on deepthroating him, and he push his hips up hard. His cock went even further than before, hurting and stretching my throat. He pushed down and made small, fast fucking motions. I opened my eyes, which were teared up by now, and saw his balls up close. At that moment, I thought about my situation: I was getting throatfucked by a dude who is 4 years my senior and about 50 pounds heavier, he has at least 7 inches of his dick in my mouth and down my throat. If my friends, parents or girlfriend even find out about this I am fucked. But for now, all I wanted was to suck dick and enjoy the moment.

He pulled my hair and pulled his wet, sloppy monster cock out of my mouth and I got off him. My dick was still soft. He played with himself and asked what more I would want to do. I told him I didn’t know, but asked him if he would lick my ass some more. I lied on my belly and he got in between my legs. Right away he spread my cheeks and got in there, tonguing me vigorously and making me moan softly. I pushed my hips in the air and spread my ass myself, enjoying every moment of it. This went on for only a few minutes, when he sat up on top of me, looking at my ass. “What do you think about having sex?” he asked. I said I’d never been fucked and imagine it to be painful. He kept on and convinced me he could try. I had a bottle of lube, which he grabbed and started rubbing on my ass and his dick. He grabbed me by the hips and pulled me into a doggy style position. His dick moved up and down along my ass, eventually centering on my butthole. He pushed his tip into me with some force, and I leaned forward and stopped him. “Could you first finger me to warm me up?” I asked. He seemed surprised but obliged. He lubed up his fingers, rubbed my ass a bit, and roughly shoved his index finger all the way into me. I shook a bit and told him to start slow. His finger went in and out very slowly at first, but within seconds he was fingerfucking me roughly and quite uncomfortably. I asked for another finger inside me and he obliged, first easing his two fingers in, then quickly reverting to clumsy and nervous fingerblasting. More because he was so impatient than because I felt I was ready, I said this was enough and that he could try to gently fuck me.

He did not hesitate a moment, relubed his dick, and put it on my ass. One hand he laid on my lower back, pushing me down slightly, and with the other he lead his hard dick. His tip went in slowly, stretching me slightly but making me moan. He moved it in and out of me a few times, masturbated with the tip inside me and more lube on his hands. Then I heard him breathe in. He pushed down on my back, leaned forward, and shoved his enormous penis into my tight, virgin asshole. As he penetrated me deeper and deeper I felt him stretch my ass wider than ever, pain filling me inch by inch. I knew I couldn’t take it and went forward to lie down, trying to get him out of me. Because he was leaning forward, his big fat body instead came down with me and soon I was lying flat on my belly, him on top of me, and what felt like his entire monster dick inside my asshole. I squirmed and told him he was hurting me. We quickly got up into doggy position again, his penis slid out of me quickly, but the pain was still there as my asshole now gaped at him. I was kind of pissed because it really hurt, but I didn’t want to ruin the experience and I did want to continue, so I told him to be more careful and continue.

When the pain in my ass had subsided and he had started his fingering again, I lied down flat and asked him to try again. He obliged, bringing his dick closer to my hole and playing with it, pushing the tip in and around it. I pushed my ass up and looked him in the eye, asking for his dick inside me. He carefully went a little deeper and deeper with every stroke, stretching me further and further for his penis. I was moaning audibly now and he was over halfway in

When the pain in my ass had subsided and he had started his fingering again, I lied down flat and asked him to try again. He obliged, bringing his dick closer to my hole and playing with it, pushing the tip in and around it. I pushed my ass up and looked him in the eye, asking for his dick inside me. He carefully went a little deeper and deeper with every stroke, stretching me further and further for his penis. I was moaning audibly now and he was over halfway in. I spread my cheeks and pulled them apart as wide as I could, inviting him to fuck me deeper. After adding a little more lube he continued his efforts until he was almost all the way inside of me. I was moaning and breathing heavily as he slowly started moving his hips, speeding up gently until he was fucking me at a steady pace and his dick felt comfortable in my ass.

Because of his weight and inexperience, he had to take breaks every minute or couple of minutes, which only left me more eager and willing. During one of these breaks he was reapplying lube and roughly shoved some fingers up my ass, which now easily accommodated them, and I once again reviewed the situation. Even though we had not discussed anal sex, I was always a fan of anal play. He told me he was a virgin and I believed him so I didn’t worry about STI’s or anything. As his fingers slid inside me I felt how loose I was compared to a few minutes ago, but the pain from his initial, hard penetration had turned to bliss and I even enjoyed what he was doing now. I looked at him and said “You can fuck me as hard as you want now, I think I can take it”.

He answered by teasing me with his tip, then sliding his cock back in and resuming a steady pace. Soon he sped up, I perked my ass up and felt him going deeper, I was sure he was all the way in now. He pushed his big cock all the way up my ass, pressing his balls against my body, pulled out, and started railing me harder than before. He grabbed my hips and fucked me, I moaned and tried to please him. This time he didn’t seem to need a break so quickly, he kept doing me from behind for minutes on end, fucking me into anal bliss.

Then he abruptly pulled out. I wasn’t expecting this and held my ass up and spread for him to get back in there, but instead he got off me. “Can we try it another way?” he asked. I said we could and asked how. He motioned for me to get on my back. I did so and he sat between my legs. I understood he wanted me to lift up my legs, so I did. He came closer and I grabbed his dick, jacking him off while giving him a horny look. He played with my soft dick and balls for a while, then put his tip on my ass again. I got ready and pulled my knees up as he thrust into me. I felt his huge penis come inside me again, every inch giving me pleasure.

He fucked me slowly at first, then soon became more enthusiastic. He sped up, I put one hand on his fat belly to slow him down somewhat, while guiding his dick with the other. Apparently, he was so turned on that he ignored me and fucked me even harder. His hands grabbed my legs and he put my feet over his shoulders, giving him an ideal angle to penetrate me. Once more he pushed himself all the way into my ass, his enormous cock filling me up and his balls between my ass cheeks. I moaned slightly in pain but mostly with joy as he railed my tight ass. For a couple of minutes, he ravaged me, until his strokes got very deep, quick, and short. He leaned on me, bending me double and filling my ass. With a few last, shocking movements he came, I could feel his cum coming out of his dick deep inside my ass. When he had come, he sat up, dick still in my ass. He slowly took his penis out of me, I focused on enjoying these last moments, and left my ass gaping. A few moments later he lied down next to me as a few drips of cum started dribbling out of me and down my crack.

As we got up and got dressed, we exchanged halfway shamed looked. He quickly drank some water and got up to leave. I followed him to the door and we said goodbye. I went back to my room right away and as soon as I got into bed my dick was hard. Thinking hard about what I just did I started masturbating and felt my orgasm come after a few strokes. My other hand went down between my legs, feeling the wet mess he left there. I immediately started feeling my asshole and rubbing it, fingering myself with the mixture of lube and cum in and around my butt. It took me less than a minute to cum, my ass twitching as I pushed my fingers in one last time when I squirted my own cum over my chest and belly…

Afterwards, I took a long shower, fapped once more, and went to sleep. The next day it seemed like a dream, but I remembered it was real. I didn’t regret it and I have seen him on a few more occasions since. I might just write about those in the future. On another note, I have had a medical check recently and am completely disease free, not to my surprise, but nice nonetheless.

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