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 My routine eventually escalated, and I found myself looking at Craigslist posts (I know, super outdated but this experience occurred in that era).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.
