Disclaimer: User-Generated Content with Erotic Material
The following story was submitted by a user and contains erotic content. It represents a personal fantasy or experience as told by the author. Tom Rocket’s explicitly distances itself from the content of this story and does not endorse or adopt any of the views or actions described. This publication is intended solely for the purpose of free expression and entertainment within the framework of our community guidelines.
I thought long and hard about whether I should share my experiences with the public, with the community. Talking about your first time is pretty intimate, after all. But after talking to lots of wonderful queer people and learning how afraid many of them are of this sexual practice, I decided to go for it. I can tell you right off the bat that I was literally shitting my pants. My ass had always been just an exit for me, and the thought of being penetrated was both foreign and hot to me. When your lover is a lucky find Even though I’m no longer with my lover from back then, I still have fond memories of him. He was two years older than me and felt like he had 20 years more experience. He just knew so much about sex, while I had only just come out. I had already given blowjobs and given a few handjobs in the bathroom at the disco, but I had never had anal sex. Not even actively, although I had had a few offers. Somehow, I always knew that I wanted to be the passive partner when fucking. Strange, isn’t it? I know that many people switch roles or only realize late in life that they prefer to be active or passive. It was different for me; I knew from the start that I wanted to be fucked. For the sake of simplicity, I’ll call him Till, although that wasn’t his real name. He did everything right from the very first moment. We were together for maybe nine months in total, but during that time he was always completely attentive to me. Maybe that was because I had been open with him about my anal virginity and my fears. We made out, we jerked off, I sucked him, he sucked me, but I didn’t let him touch my back door during the first few weeks of our relationship. That was okay with him, we had fun and he never pressured me. But the more sexual experience I gained with him, the greater my curiosity became. Somehow I had the desire to just do it. I wanted Till to deflower me because I trusted him and because he never expected it from me. One evening, after a bottle (or was it two?) of wine, I confessed my thoughts to him. Instead of laughing at me or jumping on me, we first talked very matter-of-factly about the dos and don’ts. Training with an extra dose of satisfaction Although I was an anal virgin, Till gave me very clear instructions. He expected me to say stop at any time if I didn’t like something, to prepare myself together with him, and to decide when I was ready. Of course, I agreed. Our first official act was to equip ourselves with sex toys. Till was the experienced one and I was the absolute beginner, so he chose various plugs in different sizes. Pretty clever, as I now realize. I don’t want to keep you in suspense for too long – the next time I went to bed, there was a plug next to the bed and my heart was pounding in my throat. Till first explained to me in a very matter-of-fact way how such a toy works and why it can make anal sex easier for me. He offered to let me try it alone, but I didn’t want to. After promising him that I would say stop immediately if I needed to, he first pampered me with an ass massage, then treated me to his tongue around my little door, and then rubbed me with lube. When I felt the warm silicone on my rosebud, I was nervous and scared shitless. Till stopped, gave me some space, and we changed positions. I had always thought that all anal practices would only work in doggy style. After I lay down on my back, I learned better. The plug slid into me almost by itself because I couldn’t tense up anymore. And surprisingly, it felt very, very good. Well, that could also be due to the cock massage Till gave me while I was wearing it. I wore the plug, let myself be pampered, and got used to the feeling. In the days that followed, we continued to practice. The plug got bigger and bigger, I got hornier and hornier, and every practice session ended with an orgasm for both of us. Spontaneous is often best. I’m the type of person who doesn’t like to leave anything to chance. So, of course, I did my research and got information about hygiene. I was always really afraid that my bush would turn him off when he plowed between them with his penis. So I did something I regret to this day! I signed up for waxing. Really – not a good idea! Maybe I’m just a wimp, but after every single hair was ripped from my ass, I wanted to sit in a tub of ice cubes. I was smooth, but red as a baboon. Many men tell me today that they’re afraid of poop in bed. Sorry for being so blunt, but that has never happened to me. Not the first time, nor any of the countless times after that. Sure, your butt doesn’t smell like rose water, and yes, you might fart or be a little smelly, but it’s extremely rare for your bowel movement to be waiting right at the exit for the next trip to the toilet. If it’s already reached the place where the penis goes, then you’ve long since had to go to the toilet. And for any leftovers, I recommend an anal douche. Fortunately, I was never a beginner with these, as I already enjoyed using them for cleaning. But now back to my big evening. It was actually the evening when I had painfully lost my hair during a waxing session at lunchtime. The plan in my head was actually quite different. I had ordered special bedding and decided to seduce Till over the weekend (but it was only Tuesday) and ask him to “stab” me. On the day in question, he came to my apartment in the evening and wondered why I was constantly changing my sitting position. He had no idea why my buttocks were burning so much. When I finally confessed where I had been at lunchtime, he laughed so hard he couldn’t breathe. At first I was a little offended, but then I had to laugh myself, and when he offered me a gentle ice cube massage, I naturally said yes. So there I was, lying face down on my unfolded sofa, holding my burning buttocks up in the air and enjoying the tender hands and the coldness of ice cubes on my cheeks. It felt really good, a real fizzing effect, my skin was so hot and red. While Till was nursing my butt, he kissed my neck, my back, and whispered in my ear that my ass was just as hot to him with hair as without. The feeling of pleasing him turned me on incredibly at that moment, and I knew that I wanted it now. I turned onto my back, kissed him, and ignored the brief burning pain on my butt. I asked him to excuse me for a moment and scurried into the bathroom. I washed myself thoroughly with soap and water and then fetched condoms and lubricant from the bedroom. I had already decided that it should happen on the sofa. Just pleasure and no pain. When I came back and squeezed the gel into Till’s hand, he wanted to say something. I still don’t know what, because I put my finger on his mouth and crawled back to him on the sofa. Of course, not without squeaking, because my butt was burning. Apparently, I had clearly signaled to him that it was the right moment, because he didn’t say anything either. We kissed and touched each other all over our bodies – just like we usually did. I lay on my back, he was on top of me, and after a while he slid down my body. My heart was pounding, but I opened my legs a little more and let him massage my rosebud with his tongue. He had done this before and knew how much I enjoyed the feeling. When I heard the click of the lubricant, I knew that in a short time I would no longer be a virgin. I felt the coolness of the gel on my skin and it felt good. His fingertip circled my anus and although I was excited, my body didn’t tense up, but became more and more relaxed. I closed my eyes and surrendered to the feeling of his finger, which was still circling me and finally slid into me bit by bit. Today I use gloves for anal fingering, but back then neither of us thought of that. Till because he didn’t see the moment coming and me because I had no idea. He took his time, massaging my prostate with one finger at first, then adding a second. It was me who finally lost patience and grabbed his curly hair with my fingers. I demanded in a hoarse voice that he finally fuck me, and apparently my wish was his command. He went to the bathroom to get naked and came back shortly after with a condom on his cock. Somehow his cock seemed even harder than usual, but there was no turning back for me now. I wanted it, and when he finally lay on top of me, I wrapped my legs around his back and made way for his cock. It burned briefly when his thickest part slid into me, but his slow pace allowed my body to adjust wonderfully. Again, it was me who suddenly demanded more speed. I pushed myself towards him and pressed my hands against his ass to feel him deeper and faster. When he realized that I wasn’t in pain, but only felt pleasure, he became more active. Till knew exactly how to take me. His glans kept hitting my prostate and I swear to you that my cock had never been as hard as it was at that moment. I thought I was going to come without even touching myself. That didn’t happen, but when I realized he was about to come, I grabbed my cock and jerked it off with every thrust. We came almost simultaneously—like in one of those cheesy romantic movies. Anal sex always remains exciting. For me, it was truly the most formative experience. I also remember how we stood in the shower afterwards and I giggled like a fool the whole time. Somehow it felt like my first time made me truly gay. That’s nonsense, of course; there are lots of gay men who don’t practice anal sex at all and are still 100% gay. But back then, it was all new to me and that wow moment lasted for a few days. Theoretically, I could have just told you about the penetration, but I wanted to give you a little background. My point is that the first time can’t always be planned and it doesn’t have to be perfect. In hindsight, I wouldn’t have waxed my hair, because my ass was burning for three days afterwards. Despite everything, I’ll never forget the experience, and I can tell you one thing: even though my body count is now in double digits and I’ve had anal sex with many men, it’s still always exciting. It’s just something really intimate, and I’m one of those men who enjoy moments like that, who literally soak them up and love them.
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