Straight(ish) Vol. 01

Thanks for reading. The craziest element of this story is that it really happened to me, and it was the one truly pornworthy experience of my life. I relive it all the time, and I think it's worth sharing. If you're reading this because it's close to your fantasy, I suggest you live it at least once. It's so worth it.

I was a straight white guy in my late 20s, not terrible looking, and built nicely, at 6'1, 200 pounds. Okay, I was mostly straight. I would go through phases sometimes, where I'd find myself jacking to gay or sissy porn. And every once in a while, I'd slide a single finger gently in my ass while I did. These orgasms were always incredibly intense, and the sluttier the porn, the greater the intensity. My routine eventually escalated, and I found myself looking at Craigslist posts (I know, super outdated but this experience occurred in that era). I was never going to respond, but the mere fantasy of responding was so hot. Along the line, I realized that there was no real harm in responding to some of the ads for anonymous teasing and flirting purposes. It was always older men - preferably much older and out of shape. Sometimes I wonder if I always knew where the escalation would take me.

The frustrating thing was that you never knew what you would get when responding to ads, and so it made much more sense for me to simply post an ad myself. That way, the responses would be targeted to the innocent flirting that I was looking for. I simply would say my stats and that I wanted a no strings daddy dick. The responses were always hit or miss - often I would attract older men, but based on my size and looks, they were on the bottom end of the spectrum, which was not my fantasy. I still wasn't ready to admit to myself that I was looking for this, but the daddy dick genre was all I read on Literotica. All kinds of stories about straight younger men, inevitably treated like useless whores by average looking, average-dicked older men.

And then one day it happened, "out of the blue" (like it hadn't been building to this moment for years). There was a response to one of my ads by a 55-year old, short, chubby, hairy man who sounded confident and was looking to "change the life" of a younger, inexperienced boi. He was bold over email and he lived close by. He didn't want small talk or to fall in love - he just wanted to "turn me out," whatever that meant. He also seemed normal, not creepy. The only thing that made me hesitate was that he mentioned bareback multiple times. I didn't agree to it, and he suggested that he would be respectful of my limits. So despite myself, I agreed to come over the next day, though I was surely not going to go through with it.

In my mind, I was still not going through with this, even as I got in my car, drove to his house, and walked up to his door. I found myself knocking, and he opened the door a creak, letting me slip inside the house. He was exactly as advertised, and I panicked. I started to back down and leave, but he knew me better than I knew myself. He put my hand immediately on his dick, told me to take my clothes off and lay down on the bed. He put on some old 70s/80s rock music, and he lubed me up while staring at me. He made me stare him in the eyes the entire time while he stuck one and then two fingers in my tight virgin pussy. It was the eye contact that sent me over the line. Involuntarily, I started gyrating on his fingers and softly cooing. He knew that I was ready to fuck. He took his clothes off, revealing a hairy, sweaty and chubby body. His dick was perfect. It was only slightly bigger than 6 inches, nice and hairy, and most importantly rock hard. His build up was perfect - he had me so hot and bothered that I started grabbing at his dick. It was at that point that he respectfully handed me an unopened condom and asked me to open it and put it on for him. As I started to tear open the packaging, he informed me that he was going to slide the tip in until the condom was ready, just so he didn't lose his erection. That seemed perfectly reasonable in the moment, and I didn't protest strongly enough (Did I protest at all? Did my eyes betray me? Did he know the whole time?), so he went for it. He slowly inserted the tip, as we had tacitly agreed upon. Then he pushed an inch or two forward. I'm sure it was an accident! Or maybe I pushed towards him an inch? It's hard to say, looking back. But it happened, and all of a sudden, just like the sissy porn gifs I had watched (and assumed were major exaggerations), my eyes immediately rolled back in my head, and I started to lose control of myself. Without thinking, I tossed the still unopened condom next to me on the bed, and he pushed further inside me until his balls were resting against my body. I was nervous, but he assured me he'd put on protection before finishing, or at the very least he would pull out.

Less than three minutes later, we had settled into a nice rhythm. He broke me in nicely and was fucking me at a medium pace in the missionary position, bareback and rhythmic, my legs over his shoulders, my cock untouched and incredibly hard. Something was happening to me - I knew this was the hottest experience I'd ever had. I knew what a sissygasm was from porn, but I didn't really believe in it, because I had never been able to achieve it by myself. To cum without touching your cock seems impossible. Yet here I was on the verge. As if timed perfectly, he chose this moment to tell me that I was the tightest, most eager little bitch he had ever fucked. Fulfilling his promise, he told me that he was close to cumming, and so if I wanted to put the condom on, I better open it soon.

As he said this, he continued to fuck me like he owned me, and he made me continue to look him straight in the eyes. I peeked over at the condom, then glanced back at his average body, connected to that beautiful cock that was about to send me over the edge, and then I looked back into his eyes. The hottest part about the entire experience, as I said before, was the eye contact. His eyes said so much, and most importantly they expressed the truth - I was the one making the decision, but he knew exactly what decision I was going to make. In retrospect, he probably knew the whole time, ever since he casually dropped the word "bareback" in our email conversations. I was annoyed because he had so much power of me, and yet I was powerless - I desperately needed him to own me in the most complete way possible.

I wrapped my legs around him, pulled him toward me, and finally admitted to him (and I think to myself) that I was about to cum like a total whore and that I wouldn't let him pull out, even if he tried to (which he didn't). That was all he needed to hear. He picked up the pace, grunting ferally and pounding me harder, insisting that I beg for his daddy dick to breed me. I obliged. Anything it took to get his daddy cum inside me, I was going to do. I begged. I pleaded, and when he asked if he could videotape the rest on his cell phone, I nodded in heat. He started recording, making me repeat all of the dirty whorish things that I had already said to him, which I did. He made sure I understood that once he bred me, he would always own my ass, and I begged for him to own me forever, as we both built to a final climax. Finally, he slammed his cock into me and shoved his tongue down my throat - this was another slight divergence from our initial agreement, which was that I didn't want to kiss another man. However, I couldn't deny the electricity of the moment, and so I received the kiss like the defeated slut that I was. Breaking the kiss, he whispered in my ear: "You're going to be my personal whore forever." He grunted, kissed me again, and shuddered as he came like a fire hose deep inside of me, as my legs were still wrapped around his waist and my pussy clamped around his cock.

The animalistic feeling of being taken so completely sent me over the edge. Having an out of body experience, I could hear myself screaming "I'm cumming daddy!" as I had the first of three sissygasms I'd ever have in life (all three with this man). If you've not experienced this, believe me when I tell you that there is nothing more intense than the feeling of cumming from a dick stroking your prostate. The stories you read on Literotica are not exaggerating when they say that it's hard to come back from that feeling. It changes your brain chemistry. Once you reveal yourself to be such a whore, you can never truly return to your simple, straight life.

As I lay there like a ragdoll and he lay there collapsed on top of me, sweating profusely, he asked if I had a lot of sex with women. I answered honestly that I did, and that I tended to be in the controlling dynamic. He was so turned on by this, that he was turning out a bigger, stronger, younger guy, that he forced me to get on all fours on his bed, and he fucked me again, using his own cum (and some of mine) as lube. It was a true doggystyle fucking, which was always the position I fantasized about the most, and so I played the part, though I wasn't acting at all. He smacked my ass and abused me verbally, making me talk about some of my sexual conquests with women as he took me from behind, while he told me another obvious truth - I was as much of a bitch in heat as they were, if not more. He made me look in the mirror at myself while we fucked, so I could see what I had become. Somehow that made it even more real. And this time, there was no question - he never asked to put on a condom, and the thought never crossed my mind. All I could think about was making sure I made him happy and didn't waste his cum. He aggressively came inside me, and afterwards he made me crawl across the bed on all fours to his dick, and once more, to look him in the eyes as I cleaned him off with my mouth, greedily licking up the excess drops of cum leaking from his softening dick, not caring at all where it had just been.

Twice more after this experience, I found myself reaching back out to my owner, almost like a crack addict searching for his next fix. I'll get into more detail in part 2 of this story, but the hottest ever experience involved him fucking me over a desk, as I demanded he impregnate me and slammed my ass back on his dick. They say you're truly a sissy whore when you find yourself doing the work with your ass, and they're not wrong. That time, when he came, I wrapped my legs around him from the doggy position, and held him inside until every last drop had entered my body. In one of the proudest moments of my sexual life, he told me that I was the dirtiest and most desperate slut that he'd ever been with.

I lost touch with him soon after - he wanted to have a relationship and that's not what I was looking for, but I wish I could find him. To this day, I have never taken another dick, but years later, it's still what I want the most - an older man's hard, experienced cock inside me. I want him to make love to me, to fuck my brains out, even to lend me out to friends if he wants or to make me serve as the entertainment at a party. I'd do anything for him to stare into my soul again as he breeds me, body and mind. I just can't believe he had so much intuition about my desires - how did he know the whole time that he'd make me his bitch for life with only one dicking? Does he know how often I still think about it and jack off, and how much I simply want to feel that feeling again? Is he aware that he still owns me? Will he read this, remember the experience, and reach back out to me? If not, will I find another older man to take his place?