He contacted me online because I'm one of the only guys my age who openly states his willingness to fuck with older men in his profile. Still, every time we spoke to each other over the Fourth of July weekend, he asked me if his age was an issue. I sort of became sick of his constant questioning and replied curtly, "You're forty-eight. I just fucked a guy who was sixty-two. Clearly this isn't an issue. So why bring it up?" Honestly, I think he was lying about his age (he looked over fifty and never sent me a recent picture) and was trying to figure out how angry I would be. I figured him out quickly but honestly don't care about age, so I brushed it off.
Another thing he harped on a lot in emails was this role-play fantasy he had of me playing his son and greeting him at the door wearing only a thong. I didn't have any problem with that, and he was hardly the first older man who wanted to be my "Daddy" and probably won't be the last. But he kept going on and on about the fantasy. We went back and forth on it so much that I pretty much had the entire encounter scripted out in my head before we got a chance to even work with it. I like knowing what is expected of me, but I also like to improvise with my role-play. It makes it more fun.
On top of that, the guy was a little worried about bottoming for me. Apparently he had only bottomed once before and the guy had not warmed his ass up enough before pushing in, making for a very bad experience. I did my best to calm his worries via email, telling him of all the other guys I've broken in before. But he didn't seem to be very sure. He also kept bugging me about taking my load, and being worried about contracting an HIV. I never forced him to take it, just told him my usual, "If you won't go bare, than bring your own condom." At first I figured it was because he was married (a lot of married bottoms fret about HIV exposure being what outs them to their wives), but he told me that his wife doesn't fuck him any more. Not sure why he told me that, I didn't ask and I didn't care. But it went beyond simply asking and accepting my answer. I finally had to promise him to show my papers proving my status as negative. I had no intention of doing that, but I said I would.
And finally, I wasn't getting a feeling that he was committed to actually showing up. So I sent him an email saying, "Tomorrow or never" and, to my surprise, he said he'd be there. We talked on the phone and made arrangements and the next day he was at my door. I dutifully answered in nothing but a thong.
He didn't disappoint me with his looks, though he was a bit more pasty-looking than I had anticipated (kind of like someone had painted on his skin and not let it dry well). No, this "Daddy" wannabee disappointed me in so many other ways.
The first was his kissing. I love kissing, and when he asked if I was OK with making out, I told him I was fine. I pride myself on how good of a kisser I am. This man has no idea how to kiss. None. His idea of hot making out was to shove his wide tongue fully into my mouth and wiggle it around a bit so that it felt like I was gagging. His breath wasn't great and the taste of his tongue and skin bugged me. So much that I was worried it would stink up my sheets. And he wouldn't kiss any other part of me except my ear. It got to the point where I would try to kiss other parts of his body simply so that I wouldn't have to make out with him, but he would attempt some sort of power play and say, "Give Daddy a kiss."
Now, I'm not sure about any experiences other people may have had, but I have to say that it was hard to play this man's son when I was clearly more sexually experienced than him, and clearly more dominant, and clearly going to be shooting my load of cum up his ass. It just felt awkward. There were moments where I caught myself about to call him "boy," which is the term I favor for submissive bottoms, and I had to stop myself. It was honestly an effort to call this man, "Daddy." It isn't a father issue thing either. I've called plenty men "Daddy" before with no problem. I called Rob "Daddy" one of the times he came in me. I've been calling guys "Daddy" since my days with Paul. This man simply didn't deserve the title.
Finally, after what felt like hours of him trying to cuddle me when I didn't want to, it was time to fuck him. I worked his ass and he opened like a flower, making me stop and ask if it was really only his second time. I know I'm good with asses, but I'm not usually THAT good. Annoyingly he told me that he had taken a pill the night before to make him have a bowel movement to clean out. Really not something you should say to a man who is currently licking your ass. His hole had the same off taste as the rest of him so I didn't spend much time before I began really fingering, eventually getting five fingers in. He made me keep going because he was worried about my cock being too big, but the way he took my stretching, he needn't have worried much.
Then came time to press in. I went slowly, but firmly. Not giving him time to chicken out or ask me to put a condom on. To his credit, he didn't bring the condom up at all, though at times he had mentioned making sure I was clean (what an ass). I decided that I didn't want to have him stay much longer so I fucked him a bit harder than I would have liked. Even then, there were a few times that I started to go soft in his ass. I just was not really into this fuck. Not as much as him. He was getting off on his "son" fucking his ass and was loving every moment I was in him.
When I came it was like a religious moment for him. His head whipped up and I could see from behind him that his eyes were wide open as he felt me fire load after load of cum in him. "Do you feel that cum?" I asked him savagely. "Do you feel your son's cum in you? Do you feel that DNA mixing inside of you, filling you up?" He only moaned in reply as I kept fucking his sloppy hole. In spite of my lack of interest, I had really shot a lot of cum into him. And I was angrily pounding it deep into him. Letting his body absorb my negative cum, hoping he felt it.
He finished off in a lack-luster performance, shooting his load over my chest and face like he had asked for in the fantasy. He leaned over me after, as if to kiss me, and scooped up some of his cum. For a moment I thought he was going to feed me, or himself, but he just wiped it off and we both went to the bathroom to clean off. Once again, leaving me disappointed.
Once he was clean he started talking about STDs again. I couldn't hold my tongue any longer and said, "You know, I'm really only a top at this point in my life, haven't bottomed in more than two years except for with a man who tested negative as well." Yeah, I left off the part about taking Rob's cum, but he didn't need to know. "And the thing is, as a top I really can't get HIV. So stop worrying and start living a bit." He stopped talking about my status but still didn't seem convinced on bareback sex, though he did say he'd always take my load bare. Well, he said his "son's" load, but we know what he meant.
When he was finally out my door and driving away, I stripped my bed and threw my sheets in the washer. Then I took a very long and warm shower. It wasn't that I felt gross after having sex with him. I just didn't feel like I had done anything worth while. And honestly, I'm not sure that it was so bad I'd never fuck him again. But I am sure that I don't want to kiss him much any more. And the next time he brings up the subject of HIV, I'm kicking him out whether I've come or not.