A regular.

On Saturday, I met up with one of my regular daddies. He's in his late 50s/early 60s, but he's in excellent shape. He's from out of state but he comes to NYC weekly, usually. We don't get together every time he comes into the city, but sometimes we do. He called to tell me that he was hosting a small group in his hotel room this time. Every time we've hooked up in the past, it's just been us. He said there were two other daddies and two other boys coming. I know not to expect all parties to show up at a group event like this, so I took what he said with a grain of salt.

Lo and behold, when I show up at the room ten minutes late, I'm the first one there. One of the other daddies canceled and another one is AWOL; he never returned Daddy's calls. The other two boys should be showing up sometime soon. So, Daddy and I play around for a little bit. He's wearing a shirt and white boxer-briefs. We start making out and touching each other, grabbing each other's asses and hardening cocks. I get on my knees for a taste of his dripping cock.

A few minutes later, one of the boys shows up. I realize that Daddy clearly has a type; this boy looks just like me! Of course, he's even slimmer and has a better body, but whatever. Instead of me being bitter, I'm intimidated. He's cuter than me and he's in better shape. But he's in his mid-20s, so I automatically win in my mind. We say hello, then they begin kissing for a while. The boy decides to go freshen up. During this period, Daddy comes back to me and we start fooling around on the couch. He takes off my jeans and I'm left in my sweater and my cute little American Apparel briefs. He pulls them down just enough so only my butt is out, then pushes my legs up over my head and starts to rim me. I absolutely love when he does this. The boy comes back and is just watching. Daddy and I kiss some more, then he goes back to my butt. Eventually, Daddy sits back on the couch next to me and I take off my briefs. The boy undoes his pants and comes over. He gets on his knees and starts blowing Daddy. I play with Daddy's nipples while he's getting blown.

We decide to migrate to the bed. The boy doesn't seem very interested in me. I don't think it's personal; I just think he's more into daddies than younger guys. I have no problem with that. But he and I kiss a little bit and suck each other for a short while anyway. Daddy begins to eat his ass out and they boy asks him, "Can you fuck tonight?" Daddy replies affirmatively and the boy asks him to get a condom. This stood out to me because this daddy and I usually fuck bare, and I didn't realize that he didn't mind using condoms. Daddy wrapped it up and got himself and the boy lubed, put the boy's legs on his shoulders and pushed himself into the boy in one go. The boy was loving it. They fucked like that for a minute until the boy decided he wanted to ride it. He got on top and rode Daddy's cock like it was going out of style. After a few minutes, he shot his load all over his leg and Daddy's stomach. He went to go clean up, but Daddy and I were still ready for more.

Daddy and I kissed and he went and ate out my ass some more. Somewhere in this period, the other boy left! We had no idea that he left, but that was okay... More for me! Daddy was ready to fuck some more, so I asked him to get a condom. He got one, and before he opened the package, he decided to tease me a little, so he put my legs on his shoulders and started rubbing his cockhead on my hole. I couldn't resist, so I pushed my ass against him and let the head slip in. I have a tendency of doing this; letting guys fuck me bare for a few seconds before they put on the condom. I don't know why. Well, once he was inside me, it felt too good to pass up, so I told him to forget the condom. I don't know what it is about this daddy, but he is a ridiculously good fuck. He's not very big at all, but he knows how to work an ass... and it takes him FOREVER to cum.

I've never been fucked for such a long time. He fucked me in various positions at various intensities at various speeds for at least an hour and a half straight. Occasionally, he'd pull out for a bit, but he would make sure that my hole was occupied by his fingers, usually one or two. By the end of the night, he had three fingers slipping in and out of me with such ease that I didn't even bat an eye. This was a bit startling to me, considering I'm quite tight and two fingers is usually a bit of a difficulty. My ass was so stretched out compared to its usual state. He had me grabbing the sheets, biting the pillows, screaming my head off, and literally begging for his cock. Sometimes when I'm getting fucked, I like to play up the aspect of being a cockwhore, you know? I really do want it, but I like to play it up just a tad so the guy that's fucking me gets really into it because he sees how much I'm enjoying it. There was no pretense here. I was a legit cockwhore. I felt like an addict that needed more and more and more of my drug. I've never been such an aggressive bottom, pulling him deeper into me, not allowing him to pull out of me when he needed a break, grunting and sweating and NEEDING cock inside of me. I was possessed. And I loved every moment.

It wasn't until the end of the hour and a half that I started to ride him and that set me over the edge. I shot a crazy load all over his chest and stomach and my legs were shaking like an earthquake. I came so hard and screamed so loud that I am positive the people staying next door heard me. Well, they probably heard me screaming and the bed banging against the wall for the entire hour and a half. I got off of Daddy's cock and we cuddled for a few minutes before I attempted to walk and hop into the shower. Then I realized: Daddy still hadn't cum! I apologized and he assured me that there were no worries. "It takes me forever to cum," he said.

I left the hotel with Jell-O legs. My ass was incredibly sore, but that's just the sign of a good fuck.

I wonder when Daddy's coming back into town...