Every Man Is A Little Bit Gay
- 4 years ago
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I Think I Am Gay free porn video
I certainly didn't feel any different, I just did what gay guys do, suck cock. Of a random guy they solicited off Craigslist, chiding myself for the thought. But it was one of many stereotypes that I found I wanted to fulfill. These thoughts mixed with memories of all the nuances of that first encounter: the surprising fullness of his cock in my mouth, or how hard he felt when I had my hand wrapped around him, or where my tongue was when his cum started shooting out. I had been good enough to get this guy to cum, it seemed at the time.
Sure enough, a repeat performance was requested. And another. OK, to be clear, I blew the guy like three days a week, similar place, similar time. I rationalized it at time as logical, I would have to do it again, and I knew this guy was OK. Almost friendly even, though there were never more than a handful of words exchanged. I never masturbated in front of him, but I did begin to learn about how to suck cock better. The smell actually did bother me, which on its' own was a real turn off that I'd have to learn to deal with. Every time, I left with a nice dose of semen in my stomach. I remember thinking, if anyone saw, they'd just think it was a couple of gay guys having sex.
At the same time, I created a fake Grindr profile. Wasn't ready for the real thing just yet, but I was able to browse my phone on and off while at work, and flipped through all sorts of gay men's ads. I was honestly shocked at the sheer variety in likes and tastes and looks. It had still been difficult at the time, and I was trying to make myself look at men in a different light. I'd see the picture of some guy who reminded me of a high school teacher who was at least 40, and try and see them instead as someone to fuck me. Needless to say I flipped through most men, unable to get there, it was just too different. That said, I did it many times throughout the day, and regardless, I was still using my free time to look at guys on Grinder, that had to count for something, right?
The nights I wasn't sucking his dick, I was hitting the gym, reading up on how to shape my body. All the gay sissy porn I'd be watching, the girly looking guys in lingerie, I wanted to be able to look like that, and that type of bubble butt that just pulls eyes. Except, while I might be slightly on the effeminate side of things, not nearly that much, I was and clearly am a guy. One thing however was absolutely clear to me: my newfound cock sucking experiences had emboldened me, and if I could suck a guy's cock, then I could do quite literally do anything. It was a freeing experience, realizing nothing was off limits. The only problem was while the cock sucking was great, I felt no need for it, my mind was part there and partly in my own world.
I'd say I jumped straight into getting fucked, but honestly, I had been deeply afraid of it, and I pushed that thought off for months. Life continued as normal, my daily work life was mundane and predictable, and even enjoyable, and time passed. By this point, I was intimately familiar with my partner's cock. Eventually I ended up licking his balls as well, when he pulled his pants down further than usual, and instead of ignoring them, I gave them attention. From that point out, his balls were licked regularly and enjoyed a good sucking as well. The scent had been overwhelming at first, but I was simply used to it after months of sucking on it. It wasn't pleasant exactly, but pungent, and would constantly make me think only gay guys got hard at that scent, and I was certainly hard each time.
One of the benefits of having free money is I could buy things. I certainly wasn't close to rich, simply had few expensive hobbies, and had sort of stumbled into some savings. That's how I ended up with several full sets of lingerie. Only one actually fit in any way, and it felt far too embarrassing to return, so when I started to order heels, I did my research first. I found several communities online for cross dressers, and got all the advice I could need for where to order, how to size myself, and more. I distinctly remember the thought popping into my head that I was writing and responding to men who liked to dress as women. I didn't have any particular care for it then, the clothing actually felt slightly humiliating and mostly silly to wear, but I would have to get used to it, all the basic sissy faggots did it.
My hair was nowhere near long, so I figured out where to get wigs, which ones were quality and not, maintenance and all that. Even the boring work of figuring these things out was exciting. My first was a casual dark brown, the kind that hangs down to your shoulders, curving inwards. There was no doubt I was a guy, even with it on, not that I'd thought it would totally change my appearance. Rather, I was clearly a guy in woman's wig. I didn't feel safe enough to go online with my pictures then, but I certainly felt safe enough to masturbate while cross dressed, though it was incredibly odd at first. It did, however make it easier to accept that after one look at myself in the mirror, there was no doubt what role I'd be taking in sex from now on. I couldn't imagine being the top - only being fucked. Those looks in the mirror were a reminder that I was making this reality, and that I would have to accept that I was the one to be fucked. It was hard to imagine women sexually when I had panties tugged down around my ankles so I could jerk off, and made it a lot easier to imagine being on the receiving end of anal sex.
That thought was one of the ones that kept me driven. It was difficult to imagine my ass being used for that purpose, let alone liking it. The idea of it? Even that was odd. I considered trying with my dildo and lube, but strangely enough, that felt wrong. The things we chose to care about, huh? I was going to be the one getting fucked, so I'd better learn to enjoy receiving anal sex. Despite being a somewhat experienced cocksucker, and quite enjoying it, I did not want to lose my virginity to him. No, I thought about it quite a bit. I spent quite a bit of time browsing dating sites, as I had been for a while, and I could easily look at their pictures, read their profiles and stats. I felt no need to meet any of them, but if I wanted to be gay, that meant liking guys. Like which type of guy did I want to take my virginity? It was still difficult to do at this point, but I found realizing that I was browsing for a man to have sex with as a regular activity turned me on to no end, and helped me focus on my self-appointed tasks.
I'd browsed through hundreds, far pickier than I'd ever thought I'd be. Plus, these were random men on dating sites, mostly straight when I had run out of the gay profiles to look at. In the end, it boiled down to one thing: sissy faggots don't say no. So with that in mind, I decided to post another ad on Craigslist, as obviously the first one had gotten me somewhere quite good. I wanted it to be anonymous, a one off encounter if only because I had decided that it would be first come, first served. It didn't really matter what he looked like, or his age, what mattered is that they were going to fuck, and I was going to get fucked. Sure, I could be picky if I had wanted to, though it was difficult to make any actual choice, that would mean I had some kind of preference, and in hindsight, that was too difficult to face at the time, much simpler to focus on the sissy captions I had just found, that told me a real sissy is grateful for any man to fuck them.
I didn't post right away however. After my orgasms, reality would slam home like a truck. I was sucking dick regularly now, a co-worker thought I was gay, and those things would never go away. Neither would the feeling of a cock pushing my anus open. I had made it this real, so far, and it was an exhilarating experience, but this would take things to a whole new level. A level that was helped by the fact that one of my co-workers mentioned their marijuana use. I had not been at the top of, or even truly in any social structures while in high school, so clearly I latched onto this opportunity as well, and she had been able to hook me up. My first few attempts, well, they didn't go that well, and the taste was unwelcoming. That said, I was intrigued enough that I kept trying, and quickly found that I was infinitely more relaxed. It also made my masturbation significantly more pleasurable at times. There was a mountain load of shame as I realized I could go through with it, and that it would mean I had lost my virginity through gay sex. I could change my mind at any time, but this fact would not change, and if I was successful, well... faggots don't have sex with women.
In the end, I spent time taking the best selfies that I could, just in my normal, male underwear. I wasn't ready to dress for others yet, or barely even myself, and while I was comfortable with the guy who's dick I was sucking, I was taking quite a while to warm up to men in general, so what better way than to accept any man who tried. My gym efforts were coming along slowly, and I attached pictures of it from several angles as well. I had a joint, and sat staring at the screen, wondering what I would put in that ad. In the end, it was entitled: "Looking to get laid." Basic, but it got the idea across, the one I wanted. I didn't want to scare anyone with me being a first timer, or do anything too crazy.
"Gay bottom looking to get laid tonight. Just straight up fucking, or I can suck you too. I'm not too picky, so first come first served!"
My fingers were actually shaking as I posted the ad. Who would be first? It could've been anyone really, and by this point I definitely was significantly more aware of what men looked like. Obviously I hadn't been unaware before, but my porn viewing had men of every age, class, ethnicity and whatever other differences you can imagine. What if he was like fifty years old? That was older than my mom was! Or it could be a gym bro, or just anyone. There were too many possibilities. Unsurprisingly, it didn't go that quickly. I got responses, plenty of them! Except the first one didn't respond back to me. Nor did the second or third. I realized this was a thing. The fourth, was almost my first! A man with a buzzcutt, and a bit of a grin. I was shocked he was willing to show his face in his response, and his body was... normal. A little overweight, but just a plain old body. His body hair was moderate, and he was clean shaven between his legs, and had what looked to be a normal, everyday six inch cock. He didn't mention his age, but I would've guessed him to be in his thirties. Unfortunately, he stopped responding fairly quickly as well.
The fifth ended up being the one to take my virginity, and completely not any of the things I had imagined, and I had tried very hard to imagine the best case and worst case scenarios. He was completely a shock to me, as he was eighteen, about eight years my junior. When I imagined guys who wanted to fuck other guys, they just tended to be my own age or higher. But he was able to prove he was over eighteen, and he could use a good suck before he would make me cum with his dick. He looked like any other white college k** from his picture, and had a six inch dick, which I clearly remember thinking was pretty nice. His hair a lighter black, a buzz cut and he was clean shaven, a face that was neither hard nor soft. Did I really want to give my first time to some cocky k**? Turns out I did, and as he didn't flake out, he was getting lucky. We exchanged a few e-mails, letting him know I would be happy to be fucked in any position, more than happy to swallow in any hole. Not much of a surprise that he was very receptive to all of this, and offered to pay for a hotel room nearby. The guy taking my virginity was still young enough to live with his parents, which was just somehow both humiliating in a way I hadn't expect and equally as exciting. It wasn't just that my first time could've literally been with anyone, it was that anyone was good enough, literally. I was going to be a gay faggot, like the sissies who couldn't keep their hands off a cock if they tried, so I made myself agree, holding back from masturbating further. Looking back, I was definitely right in thinking I could be spending a lot of my time in hotel rooms in the future.
It was definitely awkward preparing. I kept touching at my ass, which was not a natural action for me. He was going to bring some lube if needed, which it surely would be. I didn't have anything special to dress in, strictly jeans and a t-shirt, though I made sure I was freshly shaven everywhere, and stuck with plain old boxers. I was casual as I found the hotel, walking through as if I belonged there, down a hall of utterly regular and mundane, repetitive doors, evenly spaced apart. I knocked three times, and the door was open moments later, the guy from my e-mails. He even looked pretty much the same as his picture, perhaps a little heavier, but no more than a few pounds. He wasn't intimidating, even though he had a couple of inches on me as well.
I didn't get a good look right away, because I jumped in quickly, having no desire to be seen. Once the door was closed, I took him in quickly, heart pounding in my chest. He was slightly taller than me, but significantly wider, though still somewhat gangly, I guess. It was hard to look at him for more than a few moments, and I was achieving the level of anxiety that can only come from showing up to a hotel to have sex with another guy. I didn't know his name, nor did he know mine, and he asked if I'd get on my knees. There was carpet luckily, as I gave him a "Sure.", looking for a spot to kneel instantly. It was easier to look at him from the waist down anyways. He had been standing in front of the bed, and I could tell he was nervous too, though I hope not nearly as much as I was, so I was down on my knees quickly.
He asked me to take it out, and that's exactly what I did. Unbuckling a belt from the outside was a bit difficult, and I had to focus as my hands got closer to his genitals, but once I had the belt opened, it hung off to the side and I had to use both hands to get the button undone, and was extra careful pulling the zipper down when I felt it sort of bang into the top of my hand through the fabric of his underwear. I touched it softly, and he asked me to take them off too, so I hooked my fingers into the waist band of his underwear and shivered as his skin came in contact with mine, pulling it forward, over his hardening dick, then pulled them both down around his ankles. He stepped out of them, and shrugged out of a pair of socks he was wearing and now I was face first with the naked lower body of a man. He smelled different than my regular, but it was still that particular masculine scent that can only come from between a man's thighs. He was better groomed too, and I had my lips wrapped around his dick before he had to ask - that, and it was easier to suck than to talk.
I kept my attention focused on technique, I'd had plenty of practice so far, if only on just one guy, making sure my teeth didn't touch anywhere, just sucking him further and further. He was definitely receptive because less than a minute in he was muttering things under his breath, like "Holy shit" or "Keep doing that.", and when I managed to glance up with a mouthful of his cock I could see his head tilted back in pleasure. I was pulling my head back, when he looked down at me and said "Use your mouth on my balls." I wasn't in a position to refuse, and soon had my nose buried in between his dick and his scrotum, sucking on them. I could tell instantly what was too hard, and what made him keep muttering and the right spot could actually make him shake! I'd pause for a moment, mouth full of balls to touch myself. I hadn't even gotten out of my jeans, but I had managed to unbuckle myself, which made it a lot easier to get my hand in and start squeezing my dick, which was completely swollen at this point.
One of his hands found my head, tapping me gently then pointing at his cock. His hand stayed on my head, guiding me, and I had to stop touching myself or I would've blown my load right on the spot, and I had still had quite a ways to go. The way he was holding my hair in his fingers as I went down on him sent shivers down my sides: I had never let anyone do this, let alone a man and that contact was unexpected despite how many times I had watched sissies do the exact same thing. This guy definitely seemed to assume I loved the cock, though I couldn't blame him, and when his hand came loose from my hair, I sucked to the tip of his dick, then slowly guided it back in while tilting my head slightly upwards and back. The result was I was looking straight up into him with most of his cock pushing out obscenely from my cheek. He looked down at me for a moment, and his eyes looked deeply intense for someone just starting college. He pulled himself out, and I took a deep breath, breaking a line of saliva from his dick to my lips. He just looked at me for a moment, my hand busy in my pants.
He told me to get out of my clothes, because it was time to get on my hands and knees. I felt like I was keeping my calm on the outside, playing it casual as I pulled my shirt over my head, fixing my hair. I had seen his cock up close and personal, but this felt different, as I pulled my jeans down, followed by boxers. He took one look between my legs and chuckled, "You're one horny fuck, aren't you?" and I had blushed vividly: not only because it was true, but because while his cock was nice, his appearance did little for me except feed my humiliation: Some eighteen year old k** was happy with my blowjob, and I felt both pride and utter shame at my enjoyment of his praise.
I climbed on the hotel mattress, with those generic sheets they all seem to have. Being fucked like a bitch seemed appropriate for my first time - It was less personal, and demoralizing to be fucked like a bitch. Big up side? I wouldn't really seem him at all. Down side? I was about to be full of dick and suddenly felt as if I was about to cross a major line that I wasn't sure I wanted to. But my throbbing dick won out, and as I got on my hands and knees, I felt him pull me just a bit further back, positioning me. While I was getting in place, he had lubed himself generously. "You good?" he asked, not knowing he was about to take my virginity, and I nodded my head up and down so he could clearly see it was a yes.
It was a good things his hands were on my hip, the moment he started lining up his cock with my asshole, I felt the slick coolness of the lube and nearly jumped. Then he pushed a bit, and I felt a tickle above my anus then his cock pushing in. The sensation didn't last more than a few seconds as he fed me three fourths of his cock quickly and I squealed out loud. I hadn't squealed since I was a c***d! I felt like I was having a hammer shoved in there, and had to bite my lip to keep from crying out, and my fingers dug deeply into the bedsheets. Was this what gays liked? My own dick strained simply from the realization that I had cock in me, right then, right there. There was a sense of relief as he pulled back a bit, and over the next couple of minutes he built up a slow rhythm. My ass was almost instinctively clenching around him, and the pain lessened. It was pressure, then relief, then pressure. He would pause, burying himself all the way inside me, and if he hit just the right angle, I would get these jolts of pleasure.
The whole thing was bizarre on so many levels. There was no background noise, and neither of us were talking and it was strangely silent at first. Eventually he began to pick up his pace and I could feel the lubrication easing his thrusts, and I began to feel him push all the way in. Soon enough there was the reverberated sound of his warm thighs slapping into me from behind. There were moments of pleasure, but it was mostly a gut wrenching sensation that. I was keeping my eyes closed for some reason, and I had started to respond to his thrusts. Not as in that it was making me feel good, but that I had an instinctive reaction to squeeze my ass muscles and push back as he pulled out of me, and even though I couldn't see, I could tell it was having an effect on him.
He buried himself in me, catching his breath for a moment, squeezing my ass cheeks, "Man, you've got such a fucking tight ass, I'm going to cum inside you, OK?" His voice was different, more confident than the few words we'd already exchanged, and he suddenly seemed much more manly and mature that I was. It hit me hard in that moment, the reality of the situation I had put myself in: in a hotel room letting a stranger fuck me, praising my ass and I could barely stand being in the room with him, let alone fuck me, but here he was making me harder than I'd been in my life, which was its' own kind of delicious shame. I was doing it, my virginity now lost not at all how I'd imagined it, and instead to some horny k** off Craigslist in a hotel, each fuck making my guts twist in ways they never had before. And worst of all, just a few times, when his cock filled me in just the right away I had to squeeze my eyes extra tight due to how good it felt for just that moment: I was thoroughly and deeply in the middle of turning myself gay. It's a good thing he couldn't see as tears rolled down my eyes, I couldn't bring myself to even speak, to tell him it was ok to shoot his load into me. To hide my tears, I ended up leaning forward down, to hide my face in the blanket which made me push his cock further in due to how my back was arching, my ass and his thighs stuck together. I was squirming from the sensation, but damn did he like my ass shaking against him.
I spent the next few minutes holding back sobs and moans as he went to town on me. The way I had imagined myself fucking some woman, not too long ago. My own cock was swinging between my legs, but I couldn't risk using a hand to reach out to masturbate, he was simply fucking me far harder than I'd expected, but even during the brief slivers of pleasure I got, despite the lube, I was quite sore, though I didn't regret not having practiced with my dildo beforehand. I wanted the real deal, and I was getting it. His enthusiasm eventually ended with him pushing me deeper into the bed with his cock pulsing just once before I felt the oddest sensation in my life. It was more that I could tell by the tensing of his thighs and the noises he was making before he shot his load in me. It didn't feel like much of a "shot", more a quick splash that I could sense for a moment, then a couple more times. I had cock buried deeply in my ass spurting cum in me, but I was nowhere near being able to cum without touching myself, so I lay there as he took a few more strokes before pulling out of me. My ass instantly closed up, raw and sore, and felt different than it ever had in my life before, and noticeably more moist. I swallowed every time I'd suck that southern guy's dick, but it didn't feel the same. For one, it felt like liquid shame being pumped into me as no matter what, I had served as something to cum in.
He was looking at me, slightly curious as I rolled over on my back to relax my knees and arms, my penis embarrassingly hard. He wasn't looking away, and it clicked in my head as he nodded, he wanted to me to go ahead. His cock had softened and was still wet, and I was simply way beyond horny, and jerking off in front of him just seemed another gay thing I could do. It didn't take long, I just lay on my back and gripped my dick and tugged firmly, eyes closed and suddenly I blew my own load so high that it splattered when it landed back on my hairless crotch, several long ropes of cum landing in quick succession. When I had stopped and looked, his eyes were slightly wide open, "Damn." I couldn't help the blush, not the type you get when someone you like pays attention to you, but the one that covers your whole face because you know exactly how they see you. Within two minutes I was out, a moment to clean up my hands and dick, get my clothes on and get out. Before I left, he said "Thanks dude, you were a good fuck." I grinned on the outside, feeling my arousal return already, and "I'm going to be sore tomorrow, because of you." As I let myself out.
I wondered if the clerk had any thoughts as he saw me leave so quickly after arriving, as I made it to my car. Once inside, I took a deep breath before exhaling. I had been able to do it, able to have sex with another man. His cum was still inside me even, I hadn't wanted to spend too much time cleaning up, I had just wanted to get the hell out of there as fast as possible. What did this mean? I certainly had been attracted to his cock, but that had hurt way more than it had felt good. But the touch of his skin to mine felt wrong somehow, or feeling the hairs on his legs press into my thighs, and being utterly honest, at the time didn't find him sexually appealing at all. What had felt truly amazing was jerking myself off in front of him with his cum still dripping out of my ass, uncontrollably horny. Doing something that felt unnatural to me, that made me queasy turned me on to no end. Once I was home, I quickly got into the bathroom, pulling down my pants only to find there was gooey cumstain right under my ass. I got out of them and sat over the toilet and using toilet paper to clean up, realizing I had no real method of cleaning myself that way, just one of the new issues entering my life.
I checked my phone before going to sleep, and checked my e-mail. I had forgotten to take down my posting, and there were well over fifty messages in there. Despite the strength of my orgasm earlier, realizing that that many men had been interested in me, it occurred to me I could do this whenever I wanted. My ass had been too sore, period to want to jump back into it, and an odd sense of guilt for not replying to them. It had boosted my confidence. After all, the younger guy who fucked the shit out of me tonight had been more than happy with my performance too. I had to get out of bed to get off one more time, reliving the experience. My friend at work, Marie, could tell something was different, that I kept adjusting how I was sitting, and winked at me. I froze a moment before shrugging bashfully, then smiling. During a break, I did indeed confirm to her that I had gotten laid. She wasn't surprised, but didn't know I was seeing anyone. I had told her there wasn't anyone like that, and my further silence made my meaning clear. Instead, she asked me how it felt: her boyfriend had mentioned it a couple times, and suddenly I found myself giving advice on anal sex. I acted like an expert, but only had generalizations to give her: my experience had barely been physically pleasurable but emotionally had been another story.
Sure enough, a repeat performance was requested. And another. OK, to be clear, I blew the guy like three days a week, similar place, similar time. I rationalized it at time as logical, I would have to do it again, and I knew this guy was OK. Almost friendly even, though there were never more than a handful of words exchanged. I never masturbated in front of him, but I did begin to learn about how to suck cock better. The smell actually did bother me, which on its' own was a real turn off that I'd have to learn to deal with. Every time, I left with a nice dose of semen in my stomach. I remember thinking, if anyone saw, they'd just think it was a couple of gay guys having sex.
At the same time, I created a fake Grindr profile. Wasn't ready for the real thing just yet, but I was able to browse my phone on and off while at work, and flipped through all sorts of gay men's ads. I was honestly shocked at the sheer variety in likes and tastes and looks. It had still been difficult at the time, and I was trying to make myself look at men in a different light. I'd see the picture of some guy who reminded me of a high school teacher who was at least 40, and try and see them instead as someone to fuck me. Needless to say I flipped through most men, unable to get there, it was just too different. That said, I did it many times throughout the day, and regardless, I was still using my free time to look at guys on Grinder, that had to count for something, right?
The nights I wasn't sucking his dick, I was hitting the gym, reading up on how to shape my body. All the gay sissy porn I'd be watching, the girly looking guys in lingerie, I wanted to be able to look like that, and that type of bubble butt that just pulls eyes. Except, while I might be slightly on the effeminate side of things, not nearly that much, I was and clearly am a guy. One thing however was absolutely clear to me: my newfound cock sucking experiences had emboldened me, and if I could suck a guy's cock, then I could do quite literally do anything. It was a freeing experience, realizing nothing was off limits. The only problem was while the cock sucking was great, I felt no need for it, my mind was part there and partly in my own world.
I'd say I jumped straight into getting fucked, but honestly, I had been deeply afraid of it, and I pushed that thought off for months. Life continued as normal, my daily work life was mundane and predictable, and even enjoyable, and time passed. By this point, I was intimately familiar with my partner's cock. Eventually I ended up licking his balls as well, when he pulled his pants down further than usual, and instead of ignoring them, I gave them attention. From that point out, his balls were licked regularly and enjoyed a good sucking as well. The scent had been overwhelming at first, but I was simply used to it after months of sucking on it. It wasn't pleasant exactly, but pungent, and would constantly make me think only gay guys got hard at that scent, and I was certainly hard each time.
One of the benefits of having free money is I could buy things. I certainly wasn't close to rich, simply had few expensive hobbies, and had sort of stumbled into some savings. That's how I ended up with several full sets of lingerie. Only one actually fit in any way, and it felt far too embarrassing to return, so when I started to order heels, I did my research first. I found several communities online for cross dressers, and got all the advice I could need for where to order, how to size myself, and more. I distinctly remember the thought popping into my head that I was writing and responding to men who liked to dress as women. I didn't have any particular care for it then, the clothing actually felt slightly humiliating and mostly silly to wear, but I would have to get used to it, all the basic sissy faggots did it.
My hair was nowhere near long, so I figured out where to get wigs, which ones were quality and not, maintenance and all that. Even the boring work of figuring these things out was exciting. My first was a casual dark brown, the kind that hangs down to your shoulders, curving inwards. There was no doubt I was a guy, even with it on, not that I'd thought it would totally change my appearance. Rather, I was clearly a guy in woman's wig. I didn't feel safe enough to go online with my pictures then, but I certainly felt safe enough to masturbate while cross dressed, though it was incredibly odd at first. It did, however make it easier to accept that after one look at myself in the mirror, there was no doubt what role I'd be taking in sex from now on. I couldn't imagine being the top - only being fucked. Those looks in the mirror were a reminder that I was making this reality, and that I would have to accept that I was the one to be fucked. It was hard to imagine women sexually when I had panties tugged down around my ankles so I could jerk off, and made it a lot easier to imagine being on the receiving end of anal sex.
That thought was one of the ones that kept me driven. It was difficult to imagine my ass being used for that purpose, let alone liking it. The idea of it? Even that was odd. I considered trying with my dildo and lube, but strangely enough, that felt wrong. The things we chose to care about, huh? I was going to be the one getting fucked, so I'd better learn to enjoy receiving anal sex. Despite being a somewhat experienced cocksucker, and quite enjoying it, I did not want to lose my virginity to him. No, I thought about it quite a bit. I spent quite a bit of time browsing dating sites, as I had been for a while, and I could easily look at their pictures, read their profiles and stats. I felt no need to meet any of them, but if I wanted to be gay, that meant liking guys. Like which type of guy did I want to take my virginity? It was still difficult to do at this point, but I found realizing that I was browsing for a man to have sex with as a regular activity turned me on to no end, and helped me focus on my self-appointed tasks.
I'd browsed through hundreds, far pickier than I'd ever thought I'd be. Plus, these were random men on dating sites, mostly straight when I had run out of the gay profiles to look at. In the end, it boiled down to one thing: sissy faggots don't say no. So with that in mind, I decided to post another ad on Craigslist, as obviously the first one had gotten me somewhere quite good. I wanted it to be anonymous, a one off encounter if only because I had decided that it would be first come, first served. It didn't really matter what he looked like, or his age, what mattered is that they were going to fuck, and I was going to get fucked. Sure, I could be picky if I had wanted to, though it was difficult to make any actual choice, that would mean I had some kind of preference, and in hindsight, that was too difficult to face at the time, much simpler to focus on the sissy captions I had just found, that told me a real sissy is grateful for any man to fuck them.
I didn't post right away however. After my orgasms, reality would slam home like a truck. I was sucking dick regularly now, a co-worker thought I was gay, and those things would never go away. Neither would the feeling of a cock pushing my anus open. I had made it this real, so far, and it was an exhilarating experience, but this would take things to a whole new level. A level that was helped by the fact that one of my co-workers mentioned their marijuana use. I had not been at the top of, or even truly in any social structures while in high school, so clearly I latched onto this opportunity as well, and she had been able to hook me up. My first few attempts, well, they didn't go that well, and the taste was unwelcoming. That said, I was intrigued enough that I kept trying, and quickly found that I was infinitely more relaxed. It also made my masturbation significantly more pleasurable at times. There was a mountain load of shame as I realized I could go through with it, and that it would mean I had lost my virginity through gay sex. I could change my mind at any time, but this fact would not change, and if I was successful, well... faggots don't have sex with women.
In the end, I spent time taking the best selfies that I could, just in my normal, male underwear. I wasn't ready to dress for others yet, or barely even myself, and while I was comfortable with the guy who's dick I was sucking, I was taking quite a while to warm up to men in general, so what better way than to accept any man who tried. My gym efforts were coming along slowly, and I attached pictures of it from several angles as well. I had a joint, and sat staring at the screen, wondering what I would put in that ad. In the end, it was entitled: "Looking to get laid." Basic, but it got the idea across, the one I wanted. I didn't want to scare anyone with me being a first timer, or do anything too crazy.
"Gay bottom looking to get laid tonight. Just straight up fucking, or I can suck you too. I'm not too picky, so first come first served!"
My fingers were actually shaking as I posted the ad. Who would be first? It could've been anyone really, and by this point I definitely was significantly more aware of what men looked like. Obviously I hadn't been unaware before, but my porn viewing had men of every age, class, ethnicity and whatever other differences you can imagine. What if he was like fifty years old? That was older than my mom was! Or it could be a gym bro, or just anyone. There were too many possibilities. Unsurprisingly, it didn't go that quickly. I got responses, plenty of them! Except the first one didn't respond back to me. Nor did the second or third. I realized this was a thing. The fourth, was almost my first! A man with a buzzcutt, and a bit of a grin. I was shocked he was willing to show his face in his response, and his body was... normal. A little overweight, but just a plain old body. His body hair was moderate, and he was clean shaven between his legs, and had what looked to be a normal, everyday six inch cock. He didn't mention his age, but I would've guessed him to be in his thirties. Unfortunately, he stopped responding fairly quickly as well.
The fifth ended up being the one to take my virginity, and completely not any of the things I had imagined, and I had tried very hard to imagine the best case and worst case scenarios. He was completely a shock to me, as he was eighteen, about eight years my junior. When I imagined guys who wanted to fuck other guys, they just tended to be my own age or higher. But he was able to prove he was over eighteen, and he could use a good suck before he would make me cum with his dick. He looked like any other white college k** from his picture, and had a six inch dick, which I clearly remember thinking was pretty nice. His hair a lighter black, a buzz cut and he was clean shaven, a face that was neither hard nor soft. Did I really want to give my first time to some cocky k**? Turns out I did, and as he didn't flake out, he was getting lucky. We exchanged a few e-mails, letting him know I would be happy to be fucked in any position, more than happy to swallow in any hole. Not much of a surprise that he was very receptive to all of this, and offered to pay for a hotel room nearby. The guy taking my virginity was still young enough to live with his parents, which was just somehow both humiliating in a way I hadn't expect and equally as exciting. It wasn't just that my first time could've literally been with anyone, it was that anyone was good enough, literally. I was going to be a gay faggot, like the sissies who couldn't keep their hands off a cock if they tried, so I made myself agree, holding back from masturbating further. Looking back, I was definitely right in thinking I could be spending a lot of my time in hotel rooms in the future.
It was definitely awkward preparing. I kept touching at my ass, which was not a natural action for me. He was going to bring some lube if needed, which it surely would be. I didn't have anything special to dress in, strictly jeans and a t-shirt, though I made sure I was freshly shaven everywhere, and stuck with plain old boxers. I was casual as I found the hotel, walking through as if I belonged there, down a hall of utterly regular and mundane, repetitive doors, evenly spaced apart. I knocked three times, and the door was open moments later, the guy from my e-mails. He even looked pretty much the same as his picture, perhaps a little heavier, but no more than a few pounds. He wasn't intimidating, even though he had a couple of inches on me as well.
I didn't get a good look right away, because I jumped in quickly, having no desire to be seen. Once the door was closed, I took him in quickly, heart pounding in my chest. He was slightly taller than me, but significantly wider, though still somewhat gangly, I guess. It was hard to look at him for more than a few moments, and I was achieving the level of anxiety that can only come from showing up to a hotel to have sex with another guy. I didn't know his name, nor did he know mine, and he asked if I'd get on my knees. There was carpet luckily, as I gave him a "Sure.", looking for a spot to kneel instantly. It was easier to look at him from the waist down anyways. He had been standing in front of the bed, and I could tell he was nervous too, though I hope not nearly as much as I was, so I was down on my knees quickly.
He asked me to take it out, and that's exactly what I did. Unbuckling a belt from the outside was a bit difficult, and I had to focus as my hands got closer to his genitals, but once I had the belt opened, it hung off to the side and I had to use both hands to get the button undone, and was extra careful pulling the zipper down when I felt it sort of bang into the top of my hand through the fabric of his underwear. I touched it softly, and he asked me to take them off too, so I hooked my fingers into the waist band of his underwear and shivered as his skin came in contact with mine, pulling it forward, over his hardening dick, then pulled them both down around his ankles. He stepped out of them, and shrugged out of a pair of socks he was wearing and now I was face first with the naked lower body of a man. He smelled different than my regular, but it was still that particular masculine scent that can only come from between a man's thighs. He was better groomed too, and I had my lips wrapped around his dick before he had to ask - that, and it was easier to suck than to talk.
I kept my attention focused on technique, I'd had plenty of practice so far, if only on just one guy, making sure my teeth didn't touch anywhere, just sucking him further and further. He was definitely receptive because less than a minute in he was muttering things under his breath, like "Holy shit" or "Keep doing that.", and when I managed to glance up with a mouthful of his cock I could see his head tilted back in pleasure. I was pulling my head back, when he looked down at me and said "Use your mouth on my balls." I wasn't in a position to refuse, and soon had my nose buried in between his dick and his scrotum, sucking on them. I could tell instantly what was too hard, and what made him keep muttering and the right spot could actually make him shake! I'd pause for a moment, mouth full of balls to touch myself. I hadn't even gotten out of my jeans, but I had managed to unbuckle myself, which made it a lot easier to get my hand in and start squeezing my dick, which was completely swollen at this point.
One of his hands found my head, tapping me gently then pointing at his cock. His hand stayed on my head, guiding me, and I had to stop touching myself or I would've blown my load right on the spot, and I had still had quite a ways to go. The way he was holding my hair in his fingers as I went down on him sent shivers down my sides: I had never let anyone do this, let alone a man and that contact was unexpected despite how many times I had watched sissies do the exact same thing. This guy definitely seemed to assume I loved the cock, though I couldn't blame him, and when his hand came loose from my hair, I sucked to the tip of his dick, then slowly guided it back in while tilting my head slightly upwards and back. The result was I was looking straight up into him with most of his cock pushing out obscenely from my cheek. He looked down at me for a moment, and his eyes looked deeply intense for someone just starting college. He pulled himself out, and I took a deep breath, breaking a line of saliva from his dick to my lips. He just looked at me for a moment, my hand busy in my pants.
He told me to get out of my clothes, because it was time to get on my hands and knees. I felt like I was keeping my calm on the outside, playing it casual as I pulled my shirt over my head, fixing my hair. I had seen his cock up close and personal, but this felt different, as I pulled my jeans down, followed by boxers. He took one look between my legs and chuckled, "You're one horny fuck, aren't you?" and I had blushed vividly: not only because it was true, but because while his cock was nice, his appearance did little for me except feed my humiliation: Some eighteen year old k** was happy with my blowjob, and I felt both pride and utter shame at my enjoyment of his praise.
I climbed on the hotel mattress, with those generic sheets they all seem to have. Being fucked like a bitch seemed appropriate for my first time - It was less personal, and demoralizing to be fucked like a bitch. Big up side? I wouldn't really seem him at all. Down side? I was about to be full of dick and suddenly felt as if I was about to cross a major line that I wasn't sure I wanted to. But my throbbing dick won out, and as I got on my hands and knees, I felt him pull me just a bit further back, positioning me. While I was getting in place, he had lubed himself generously. "You good?" he asked, not knowing he was about to take my virginity, and I nodded my head up and down so he could clearly see it was a yes.
It was a good things his hands were on my hip, the moment he started lining up his cock with my asshole, I felt the slick coolness of the lube and nearly jumped. Then he pushed a bit, and I felt a tickle above my anus then his cock pushing in. The sensation didn't last more than a few seconds as he fed me three fourths of his cock quickly and I squealed out loud. I hadn't squealed since I was a c***d! I felt like I was having a hammer shoved in there, and had to bite my lip to keep from crying out, and my fingers dug deeply into the bedsheets. Was this what gays liked? My own dick strained simply from the realization that I had cock in me, right then, right there. There was a sense of relief as he pulled back a bit, and over the next couple of minutes he built up a slow rhythm. My ass was almost instinctively clenching around him, and the pain lessened. It was pressure, then relief, then pressure. He would pause, burying himself all the way inside me, and if he hit just the right angle, I would get these jolts of pleasure.
The whole thing was bizarre on so many levels. There was no background noise, and neither of us were talking and it was strangely silent at first. Eventually he began to pick up his pace and I could feel the lubrication easing his thrusts, and I began to feel him push all the way in. Soon enough there was the reverberated sound of his warm thighs slapping into me from behind. There were moments of pleasure, but it was mostly a gut wrenching sensation that. I was keeping my eyes closed for some reason, and I had started to respond to his thrusts. Not as in that it was making me feel good, but that I had an instinctive reaction to squeeze my ass muscles and push back as he pulled out of me, and even though I couldn't see, I could tell it was having an effect on him.
He buried himself in me, catching his breath for a moment, squeezing my ass cheeks, "Man, you've got such a fucking tight ass, I'm going to cum inside you, OK?" His voice was different, more confident than the few words we'd already exchanged, and he suddenly seemed much more manly and mature that I was. It hit me hard in that moment, the reality of the situation I had put myself in: in a hotel room letting a stranger fuck me, praising my ass and I could barely stand being in the room with him, let alone fuck me, but here he was making me harder than I'd been in my life, which was its' own kind of delicious shame. I was doing it, my virginity now lost not at all how I'd imagined it, and instead to some horny k** off Craigslist in a hotel, each fuck making my guts twist in ways they never had before. And worst of all, just a few times, when his cock filled me in just the right away I had to squeeze my eyes extra tight due to how good it felt for just that moment: I was thoroughly and deeply in the middle of turning myself gay. It's a good thing he couldn't see as tears rolled down my eyes, I couldn't bring myself to even speak, to tell him it was ok to shoot his load into me. To hide my tears, I ended up leaning forward down, to hide my face in the blanket which made me push his cock further in due to how my back was arching, my ass and his thighs stuck together. I was squirming from the sensation, but damn did he like my ass shaking against him.
I spent the next few minutes holding back sobs and moans as he went to town on me. The way I had imagined myself fucking some woman, not too long ago. My own cock was swinging between my legs, but I couldn't risk using a hand to reach out to masturbate, he was simply fucking me far harder than I'd expected, but even during the brief slivers of pleasure I got, despite the lube, I was quite sore, though I didn't regret not having practiced with my dildo beforehand. I wanted the real deal, and I was getting it. His enthusiasm eventually ended with him pushing me deeper into the bed with his cock pulsing just once before I felt the oddest sensation in my life. It was more that I could tell by the tensing of his thighs and the noises he was making before he shot his load in me. It didn't feel like much of a "shot", more a quick splash that I could sense for a moment, then a couple more times. I had cock buried deeply in my ass spurting cum in me, but I was nowhere near being able to cum without touching myself, so I lay there as he took a few more strokes before pulling out of me. My ass instantly closed up, raw and sore, and felt different than it ever had in my life before, and noticeably more moist. I swallowed every time I'd suck that southern guy's dick, but it didn't feel the same. For one, it felt like liquid shame being pumped into me as no matter what, I had served as something to cum in.
He was looking at me, slightly curious as I rolled over on my back to relax my knees and arms, my penis embarrassingly hard. He wasn't looking away, and it clicked in my head as he nodded, he wanted to me to go ahead. His cock had softened and was still wet, and I was simply way beyond horny, and jerking off in front of him just seemed another gay thing I could do. It didn't take long, I just lay on my back and gripped my dick and tugged firmly, eyes closed and suddenly I blew my own load so high that it splattered when it landed back on my hairless crotch, several long ropes of cum landing in quick succession. When I had stopped and looked, his eyes were slightly wide open, "Damn." I couldn't help the blush, not the type you get when someone you like pays attention to you, but the one that covers your whole face because you know exactly how they see you. Within two minutes I was out, a moment to clean up my hands and dick, get my clothes on and get out. Before I left, he said "Thanks dude, you were a good fuck." I grinned on the outside, feeling my arousal return already, and "I'm going to be sore tomorrow, because of you." As I let myself out.
I wondered if the clerk had any thoughts as he saw me leave so quickly after arriving, as I made it to my car. Once inside, I took a deep breath before exhaling. I had been able to do it, able to have sex with another man. His cum was still inside me even, I hadn't wanted to spend too much time cleaning up, I had just wanted to get the hell out of there as fast as possible. What did this mean? I certainly had been attracted to his cock, but that had hurt way more than it had felt good. But the touch of his skin to mine felt wrong somehow, or feeling the hairs on his legs press into my thighs, and being utterly honest, at the time didn't find him sexually appealing at all. What had felt truly amazing was jerking myself off in front of him with his cum still dripping out of my ass, uncontrollably horny. Doing something that felt unnatural to me, that made me queasy turned me on to no end. Once I was home, I quickly got into the bathroom, pulling down my pants only to find there was gooey cumstain right under my ass. I got out of them and sat over the toilet and using toilet paper to clean up, realizing I had no real method of cleaning myself that way, just one of the new issues entering my life.
I checked my phone before going to sleep, and checked my e-mail. I had forgotten to take down my posting, and there were well over fifty messages in there. Despite the strength of my orgasm earlier, realizing that that many men had been interested in me, it occurred to me I could do this whenever I wanted. My ass had been too sore, period to want to jump back into it, and an odd sense of guilt for not replying to them. It had boosted my confidence. After all, the younger guy who fucked the shit out of me tonight had been more than happy with my performance too. I had to get out of bed to get off one more time, reliving the experience. My friend at work, Marie, could tell something was different, that I kept adjusting how I was sitting, and winked at me. I froze a moment before shrugging bashfully, then smiling. During a break, I did indeed confirm to her that I had gotten laid. She wasn't surprised, but didn't know I was seeing anyone. I had told her there wasn't anyone like that, and my further silence made my meaning clear. Instead, she asked me how it felt: her boyfriend had mentioned it a couple times, and suddenly I found myself giving advice on anal sex. I acted like an expert, but only had generalizations to give her: my experience had barely been physically pleasurable but emotionally had been another story.
Trisha
- 25.03.2021
- 36
- 0
