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To my mutual humiliation and arousal, the next morning at work, Marie could instantly tell. Truth was, I could see why: Nathan had fucked me three god damn times, and I my ass was sore as hell. Sure, he’d been tender as well at times, but one look at me and she knew. She just rolled her eyes at me, causing me to blush. She wanted to know what he looked like, so I found her his Grindr profile. She flipped through it, looked at me, looked back at my phone, and looked back up at me, eyes slightly wide. She had been impressed! Maybe even jealous. I felt an intense sense of pride at being able to snag a man that would make a woman jealous, similar to how I felt when I blew guys. That sense of pride quickly turned to shame as I realized that while I felt I was good at sex… it was with men. Well, I wanted to be gay, so being good in the sack wasn’t going to hurt.
I was not anywhere near ready for another experience like the one I had had with Nathan, and though I did find a random older Hispanic man to blow, I only picked up a handful of men. I wasn’t having any luck getting one of the anal orgasms I kept reading about, but it was rarely too painful and becoming almost pleasurable. Instead, I found myself focused more and more on gay sissy porn. I would dress up, slip on some heels and edge for hours. I began ordering more wigs, and moving away from just the lingerie. I ended up with dresses, skirts and blouses. They did seem to make my ass and thighs look better, especially in heels, but I was still undeniably a male in a woman’s dress. I’d post pictures of me in a cute pink number or a nice pair of panties with my penis clearly poking out. I got quite a bit of positive commentary from the internet, which just spurred me on further: I bought quite a bit of jewelry, rings, necklaces and clip-on earrings. I saw plenty of sissies online, and while many were in chastity, it didn’t truly entice me: I liked masturbating, and intended to keep doing it as much as I could. Thankfully you can order make-up online too, and there are more tutorials than I could’ve possibly imagined teaching me how to apply it properly. The feelings I got from looking at myself in the mirror, imagining myself being railed with my skirt pulled up over my hips ended up fueling many erections. It was significantly gayer to me than the fuckings I’d experienced so far in some way. A guy who likes getting fucked while crossdressing? That’s the kind of faggy gay sissy I wanted to force myself to become.
That’s when I started using the dildo to pleasure myself. I figured if the men I’d slept with so far had been able to make me feel kind of good, beyond the shame and humiliation that is, but gay bottoms loved taking it up the butt, they got off on it, literally. My appreciation of Nathan’s cock was still fresh in my mind then. He had been truly large, compared to the rest, and while he hadn’t been able to get me off, I enjoyed his cock in my mouth. I had enjoyed servicing him orally, it had felt good to suck on his dick. Or more clearly, it had felt right. I could smell it as I lay in his lap, sometimes having it brush my lips, and instead of thinking about how I was supposed to like pussy, I was thinking about how soon I could get it back between my lips, so I could get back to sucking on it. I needed to have at least that level of pleasure from being fucked in the ass, which resulted in quite a lot of practice and a metric fuckton of lube and little success.
In part, I was recovering from my experience with Nathan and my activity wasn’t so much limited, as I needed time. But not enough that I stopped my anonymous encounters. Dildo practiced helped, and I found I could sometimes angle myself in such a way that gave easier access to make things less painful and more pleasurable. Combining that with the utter and complete shame I felt each time a cock slipped into me, and adding another casual gay sexual encounter was just the icing on the cake. I had read that most people have less than five partners in their life, and I was already past that.
And while I was somehow not ready to dress up for anyone, I wanted something more. Posting my own ads, I had many more flakes but responding to others had been a different story. I opened up Craigslist, browsing. Some folks had some odd kinks, but literally, who was I to judge? Of course, by now I’m rarely surprised by anything, hell, I’ve done most of it. One posting in particular caught my eye.
I clicked on it, and found a Daddy in his late forties who wanted to fuck the living shit out of a twink. I had probably qualified before, but my gym efforts didn’t hurt either. I had not been overly picky with most of my partners, I had little preference. This guy was different. He listed his stats as six foot four and three hundred pounds. I didn’t need to imagine, because he had attached several pictures: He was huge. He had what could only be described as a large domed belly covered in a mix of light brown and grey hair, tangled, going up his chest. His thighs were wide and meaty, and his cock was thick as hell. He definitely looked his age, his head shaved, kağıthane escort with a short beard. He was not conventionally attractive, he was huge massive. I didn’t want to have sex with him at all, which in turn made my penis incredibly hard. It was like the more I didn’t want to have sex with him, the more I knew I had to try.
I had plenty of pictures of myself by then, but it felt different. I wanted to make sure he responded, make sure he said yes.I chose one, a full body shot including my face. Then I took another, of how hard I was at the time, and attached them in a response. The first to show him my body, the second to show him how hard he made me, and how I was very open to whatever he wanted. We exchanged e-mails for a bit, where I did my best convince him I was open to whatever he wanted, as long as I could get my hands on his cock. I’m proud to say, even back then, I got my man.
In one way, that encounter had been like any other, some guy a met once, had sex with, and never met again. In another, it was a major step in how far I’d come, and how far I’d go. His cock had been the thickest yet, and the smell between his hairy thighs was overwhelming, but I was able to endure it, even welcome it as he was the first to verbal. Not just the occasional moan or grunt I’d get, but he’d tell me when to slow down, or have me swallow while telling me what a good little cock sucker I was. I couldn’t say anything with a mouthful of cock and all my effort going to repress my gag reflex, not that I had anything to say, I was savoring the girth of his cock with my lips and getting his pubic hair on my tongue.
But that hadn’t been it. We’d both been completely naked, and like most so far, he’d wanted to fuck me from behind. I should’ve been more nervous when I saw him lube up generously. He had the cock you’d imagine belonged on a man his size, with great big balls to match. I had never felt like a slouch before in that department just like I had never felt a level of emasculation that intense as he just split me open. I’d been fucked, but not by anything like this, he had to really work himself in at first. I felt incredibly full when he was all the way in, and it wasn’t sore just yet, but I knew I was going to be later. Once he started pumping me for real, I felt it instantly. To my shame, I didn’t even last a minute and had my first anal orgasm. It was different. I had been hard at the time, but it wasn’t that instant spurt, that moment of intense gratification. I just began dropping out semen, a steady leak, followed by another. It was blissful, and lengthy, but the guy just kept on going at it. I had trouble controlling my limbs, too much shaking for far too many reasons, and I collapsed onto my chest and suddenly he was on top of me, his palms pressed into the bed around my head, his full weight with every thrust as I bucked uncontrollably. Even though I’d thought I was done leaking, he just kept pounding away at my ass, and I could feel the pressure of his belly against my back with each thrust. My knees had collapsed, and it was like he was rutting in me, like some kind of beast. I did the whole “Fuck me, Daddy!” thing, because it was in the moment, and the gayest thing I could think of to say in the moment. I’d like to say I was more creative, but I just repeated it a bunch, but it seemed to work and had my second anal orgasm, just minutes later. He finished in my ass not long after, panting and out of breath, the smell of him all over me.
That was the last I saw of him, like most of my encounters. I had gotten dressed, even thanked him for the fuck and left. Nothing changed in the following days in any significant way, but there were thought I was trying to not deal with. Pesky ones. To be gay, I had to enjoy anal sex, so having an anal orgasm was a great step forward, wasn’t it? But he had basically just stuck it in and I had blown almost right away it had felt so good. Every single one of the other men I’d slept with by any objective standard had been more attractive, in better shape, but it had been him who managed to make me cum? He was only a few years shy of being twice my age! Hell, twice my weight too! But I couldn’t deny it, the physical sensations had all been overwhelming, the way he had fucked me when I was begging for his cock, the sheer presence of him he had me pinned down was only matched by how degraded I had felt. I had actually kicked myself, and when I tried to get a response from his e-mail, none came.
That made things sink in deeper. I was regularly sleeping with random men, cock sucking was a thing I hapilly looked forward to, I had ordered hundreds of dollars of women’s clothes and lingerie, the few people who knew me knew me, knew me as gay, and I spent way too much time looking at cocks. Sure, it wasn’t easy getting to this point, but in that moment I couldn’t imagine having sex with a woman. And if I could have sexual experiences like my last partner, then I certainly was sexually compatible with men. It’s just that I wasn’t one, I had made sure I couldn’t be one. It was like my experience etiler escort with him had smashed my heterosexuality to bits, and with it went traces of masculinity. I wanted to be reduced to the least masculine thing I could become, an absolutely gay sissy faggot. Or, realistically, a bigger gay sissy faggot than I already was. At the time, I couldn’t tell if I was just pretending to be one, or actually was one. Did it make a difference?
There was still plenty of work to be done, but that part made the rest easier. Men were truly the only option for me now, whether I wanted sex, or friendship, or romance, and if you’ve only got one option, then you might as well indulge. I had kept that big bear of a man’s pictures from his posting, imagining what it’d be like to be fucked by him daily. He had obviously done something for me, and I wondered if this would be my type? What would a relationship with him have been like? What if I had introduced him to Marie as my boyfriend? To have my Daddy pick me up from work, and kiss outside in front of anyone? I imagined him making passionate gay love to me, being smothered underneath him. These thoughts were more frightening, my self-conditioning was working, and the thought bloomed in my mind that while my current feelings weren’t exactly positive, I knew it wasn’t an impossibility.
That said, it wasn’t an easy thing to do. Every time I masturbated to thoughts like that, I had powerful orgasms that left me thinking I could stop at any time and of course all the shameful feelings as well. I had seen plenty of sissies in cages, and decided it was time to try it out. The thought of not being able to jerk off was a foreign concept, but I was more interested in what I’d read many sissies talk about, how it made them hornier, how they would need something in their ass to get off, and a whole lot more. I was more curious than anything. I made it all of three days my first time locked up. It felt odd, and painful if I grew hard, but after a day or so it almost felt normal. I tried to reproduce that anal orgasm, but had no luck, though the feeling of my anus stretching was becoming both familiar and pleasurable. I only ever got to the point of having precum, and my penis wasn’t growing fully, but it definitely felt like I was trapped when I got too horny. I wasn’t in a rush for anyone to see me in it, but I did wore it when I hooked up with my most current dick to suck. Normally I’d play with myself, but being locked up made that impossible. I was learning to control myself, though I didn’t realize it at the time. I didn’t want the pain from growing erect inside, to what extent was possible, but it felt good enough for few moments before becoming painful and forcing myself to calm down. Which, was pretty difficult with a cock in my mouth and my nose full of the latest manly smell. The difference now was that I couldn’t just get off right away, and I was still very, very horny. Something about servicing a man with my mouth and not being able to relieve myself was extremely erotic. When I finally unlocked myself, the orgasms were unbelievably strong.
And of course, I kept trying to achieve an anal orgasm with my dildo, while locked up. It’s embarrassing almost, to say how long it took me to get that down. It was frustrating, and despite all the information I could find online, I wasn’t having any luck, I was barely even growing as erect as my cage would let me. I found very quickly the longer I went without cumming kept me in a very frequent state of arousal. I was constantly thinking about sex, but the lack of relief kept my balls swollen and my mind focused on the tasks at hand. Can’t feel too shameful or humiliated after cumming if you don’t cum.
I found all types of sissies online to use as role models. Ones dressed up in frilly pink dresses with lots of lace and ruffles, or in latex or every type of slutty female clothing you could imagine. I’d get there, eventually was my thinking at the time, but for now I had to get used to it more, not just dressing up and masturbating, then putting my things away after. It was a Sunday, the day each week I shaved myself of any body hair to keep myself as smooth as possible. Frankly, I was quite enjoying being that smooth, even though I still felt silly when I cross-dressed. So, I decided to stay dressed all day with the help from my friend marijuana. I went about my day at home as normal, which felt unnatural and far chillier than I imagined as I spent into in the sexiest lingerie I owned and a pair of two inch heels. When I walked about, I would catch myself in front of a mirror, which just turned me on further, and I even tried to mince, just another gay sissy. I kept on one of my blonde wigs as well, the longer one, so I could feel the hair lying against my back, and I’d often have to brush it aside.
The marijuana made sure I was pleasantly relaxed as I put on my make-up – eye liner was especially frustrating to do well, and I didn’t have long lashes to begin with. I spent the morning watching tutorials on doing my nails and finally got to do my nails. No, not beyoğlu escort my fingers, as that wasn’t something I wanted seen at work, but my toe nails? Pretty and pink and polished to a gleam. I had to angle my legs just right, and the cold steel of my chastity cage would rest against my thighs as I focused, getting more aroused the whole time, occasionally swelling in the cage before I was able to calm down. I tried to lounge about, watching TV, browsing the Internet, but would invariably be reminded by brushing my hair from my wig aside, my bra strap cutting into my shoulder for a moment, or the constant presence of my caged dick. I tried my dildo, lubricating it more than was needed but it wasn’t quite the same. I was becoming used to and even welcoming the stretching out my rectum was getting, and while not unpleasant, I couldn’t get a rhythm going and would cramp up even sometimes. I spent the evening searching for new nail polish, in different colors and shades while browsing gay dating profiles. My will power faded quickly as the night continued, and I had to uncage myself and masturbate, it had simply been too long at only a few days, but after being horny all day, I simply didn’t care.
Once I was done, I put myself right back in chastity. Once I had cum, I decided even then that I’d go to sleep still dressed, I wanted this to become comfortable, and that would take practice. I vowed to myself to make it a full week before I got to do that again: If a day of being horny had been that good, a week would be even better! I took advantage of the fact that my latest dick to suck never saw me without my pants off, and it was a new perverse thrill to suck cock without even getting to rub one out myself and not even being able to truly get hard? I’d say it was torture, but the fact was that I enjoyed it. I had looked forward to it, the uncomfortable pain as my cock tried swell in its cage, willing it not to get hard despite how horny I was I sucked on a strangers cock. What I hadn’t accounted for was that it had been… I don’t remember how long it had been without cumming in seven days. By the fourth day, after I’d sucked some dick, I was taking cold showers every night, sometimes twice a night. My scrotum was full and sore, and I was in a semi constant state of arousal.
Even though I knew I wouldn’t be able to get off on until Sunday if I wanted to stay the whole week, I knew I could’ve tried to focus on other things. I could’ve gone out, seen a show, anything really, to keep my mind occupied and away from sex. But I was often too aroused to care, and I’d find myself staring at pictures of cock, or seeing who was nearby on Grindr. I didn’t watch any porn, which freed up a lot of time, but mostly when I got too aroused, or when I noticed how full my balls were, I couldn’t help but seek out a stimulus. I tried my dildo several more times, in various positions, but all I got was a contentment from being filled up, and I would leak a bit, but no orgasm of any kind. By Sunday morning, I was quite ready to explode. I had it down to the minute when I’d be let out. When the week had started, I imagined that I’d unlock and masturbate as quickly as possible, the need too strong. But by Sunday, my mind had plenty of time to think, and I wanted a man.
Damn, did I ever want a man. It was all I could think about. I wanted that anal orgasm again, desperately. So far, most of the ads or profiles I’d responded to had just been for fucking, and I wasn’t sure how they’d react to me being locked, and I definitely wanted to be unlocked, so that wasn’t a problem. Frustratingly, people were flaking out on me, which left me genuinely unhappy. For some reason, this time it took hours and hours to find a guy willing to fuck me, a middle-aged potbellied man with a nice thick cock. I orgasmed about ten seconds after he slid into me the first time, and he couldn’t have taken more than ten minutes with me in his hotel room, but I had cum three times, my dick rock hard and semen spilling out of me as he pounded into me. That time I didn’t make the same mistake, and made sure to keep his contact information, and let him know I’d be available in the future. Good orgasms from being buttfucked were something I wanted easy access to.
It was around this time that I noticed men around the office treating me somewhat differently. Not a lot, just… differently. I hadn’t overtly changed my appearance in any way. Turns out Marie’s friend had let it be known that I had been with them on that trip to the gay bar, and so there were quite a few assumptions going around. Occasionally someone would bring it up, had I been to that gay strip club with them, on a girl’s night out? Of course I had, but I left no room for doubt that I was included as one of the girls as subtly as I could. It’s funny how quickly I became “the gay guy” in the office, though no one treated me that differently. At night, it made me unbearably hard: for all intents and purposes, to the majority of people I knew, I was gay. And they were partially right, I quite honestly enjoyed sucking on cock, looked forward to it, hell just looked at cocks because I genuinely liked them. My anal orgasms had felt great, and I knew I’d want more, if I could enjoy the fuckings as much as I liked sucking on cock, that’d be good enough, I had thought. Because the desire for more gay sex was helping push me to the next step: dating.
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