Who's Your Daddy?

You remember how I said, just a few posts back, that nobody calls me "Daddy" except my kids?

Well, it turns out that I lied. There are (at least until I can think of some more) three possible explanations:

a. My children have started calling me "Dad" as they get older, so "Daddy" is freed up for the use of hot younger men.

b. "Daddy" is actually a Norwegian term meaning "respected bearish man of immense sexual prowess, who is, in fact, no more than ten years older than I, and who could not be my biological father, but who could conceivably have adopted me, strictly for the purposes of getting around immigration barriers, and whom I want to take me in a way that is not at all pseudo-incestuous." It's pretty cold in Norway, and the language evolved during a time when people needed to conserve energy, so they pack a lot of meaning into single words.

c. The strength of my convictions is inversely proportional to one or more of the following: my fatigue level, the hotness of the "boy," how long it's been since I've had any outside action, and how far down his throat my cock is. The exact equation is fairly complex and is left as an exercise for the reader. Please show your work for partial credit.

Anyway, I was exceedingly tired and exceedingly horny yesterday, in part because on Thursday, I'd seen the following ad on craigslist (the Maryland section, obviously):

Young boy, horny looking for older - 24

I'm young, cute and horny; looking for an older daddy. I'm straight, but been with daddys before. I love to please, am submissive. Available in Bethesda until 6PM today. Can host. I am skinny, attractive and uncut. Love to roleplay, love a masc. daddy.

Normally, I wouldn't give such an ad a second look (unless there was a picture, in which case I'd ogle a bit) because, in general, I don't much go for twenty-four year olds, straight men, or role play. Furthermore, although I have achieved my forties, I think the phrase "older daddy" applies to someone at least ten years older than I. I don't really think of myself as older (You may laugh, but do so quietly: you don't destroy my delusions, and I won't destroy yours, ok? OF COURSE you're masculine. Really.) at all, but, hell, if the guy's twenty-four, then I'm older, right? And the guy did sound kind of hot, and, well, he wanted it pretty much right then, and horny, horny, horny.

So I emailed him. His ad hadn't been up long, but it was already after 4:30 (4:37 -- I went back and checked) when I emailed, so I knew that even if I was what he was looking for, getting done by 6 was going to be a stretch. And, in fact, he didn't reply right away, and when he did (4:57, so actually it was relatively fast), he suggested the weekend. I (5:19) said I was driving to Ohio on Saturday. He (7:06) suggested Friday, and sent a picture (it's the picture at the top of the post; I have edited it slightly; can you tell where?), and I said, oh hell yes.

It was clear from our exchange that I needed to be authoritative and dominant with this guy. Dominance to me is a lot like boning a chicken¹: removing the bones from a whole chicken is not the first (or second) thing I'd choose to do in the kitchen, but I can do it well and efficiently, I certainly don't mind doing it, and I'm very pleased with what I can do with the product. So I emailed him the next (i.e., yesterday) late morning and said I wanted to play and told him he needed to be able to follow directions, and the rest was just working out the time and location.

Since he had said he wanted roleplay, and since I wanted to avoid any situation like that one that joe.my.god wrote about in his "Worst Sex Ever" entry (sorry, it's blocked at work, so I can't link to it, but you know the one I'm talking about), I set him up with a relatively simple roleplay. I told him that I'd be getting home from work, and he'd be getting dried off from the shower, and he'd come and give Daddy a hug, and then things would get hot. He wrote me back to say that he might be a little bit late and that as a result he'd deserve a spanking, so I wrote back and said that I would just come a little later and that I almost always found that my boys (apparently I have boys; who knew?) had done something that required punishment, so he could be on time and have an opportunity to get nice and clean for Daddy. (Kink? Sure. Dirty, smelly, etc? No thank you!)

As it happened, I got lost on the way to his place. It's really not that far from my office, so getting lost required some effort. He'd said he didn't have any condoms or lube, and I had the latter but not the former in the car, so I had to stop on the way, and then I couldn't find the road I was supposed to be on. I don't ever go to that part of Bethesda. But I was so incredibly horned up that I actually pulled over, rolled down the passenger window, and asked² a passer by where the road was. She told me, and ten minutes later (I had managed to get spectacularly lost in a very short amount of time. Go me!) I was pulling up to his house.


So, let's get this out of the way. I generally don't think it's polite to post a picture that a guy's sent me over email, even after some, um, subtle editing, without explicit permission. And I wouldn't have posted this one if it had been the guy's actual picture. When I first saw him, I thought, well, maybe it's just his picture from the summer of 1998, but upon further reflection, I'm pretty sure that he just sent me a picture of what he considered to be a hot twenty-four year old.

As soon as I got to the address, I knew that twenty-four was unlikely. Single family homes in Bethesda are not cheap, so unless this guy was a very highly paid escort (unlikely since he never mentioned money³) or had inherited substantial wealth, he wasn't affording this place (not palatial by any means, but still nice, and still probably $800,000 right now) at twenty-four. (There was a "for sale by owner" sign in the front yard, with a website. I'm not linking to the website because that would be invasive, but if you're looking for some Bethesda real estate, email me, and I'll give you the URL. The asking price wasn't listed, though.)

Anyway, I knocked on the door, and he opened it, wearing only a towel. Not 24. Probably 34. Thinner and less built than in the picture. Somewhat hairier, and with decidedly smaller nipples and paler skin than in the picture. Also, as I soon discovered, a considerably larger cock, though the apparent smallness of the cock (which you may not be able to see, oops) in the picture could be due to the camera angle. He was both cute and hot, though, and given that I much prefer thirty-somethings to twenty-somethings, I was very pleased.

I stepped in, and he hugged me, as per the script, and I started to kiss him and removed the towel. Then I asked him if he'd been a good boy, and he said that he had. So I asked him if he'd done anything bad, and he hung his head and said yes. So I asked him what he'd done, and he said, "I touched myself."

Now look. I want you all to understand that I had a great time with this guy and that I am in no way complaining about his behavior. And, certainly, compared to the role play that joe.my.god had to endure, our session was terrific. But listen up, submissives: it is time to exercise a little creativity! "I touched myself"? Come on. Is there any submissive anywhere who doesn't default to that confession when he's asked whether he's been bad? I know that you've touched yourself, and, given time, I'll get around to asking that question explicitly, perhaps when I'm yanking your hands away from your cock and telling you not to touch yourself while you're blowing me because I said so and that's all the reason you need, boy. Just one time, before I'm really old, I would LOVE to have the following conversation with a submissive:

Have you been bad, boy?

Yes, sir.

And what did you do, boy?

I shot a man in Reno, sir.

Why, boy?

Just to watch him die, sir.

Also, for future reference, if you want a real pounding, you could do a lot worse than putting Live from Folsom Prison in your CD player. I'm just saying.

Anyway, since he'd been touching himself, I had to spank him. I will spare you the inane Daddy-Son dialogue. You can imagine it for yourself. As it happens, as much as I love words, I am not particularly verbal during sex. If you're doing the dom-sub thing, though, you have to be verbal, so I put the dialog on auto-pilot. The subs never seem to mind, and it doesn't alter my enjoyment.

I put him on his knees and bent him over the bed. I looked around for his belt, but I didn't see it, so I pulled off my belt and administered the spankings (with requisite inane commentary). That got him really hard, and he was rubbing his cock against the bed. So I spanked him some more, and he started to moan. Then I pulled him up and told him that when he needed to be touched, he needed to come to me. Then I unbuttoned my jeans, and told him that I'd had a tough day and that he needed to make me feel better. He pulled down my jeans and briefs and started to suck my cock.

After a bit of that, I pushed him onto the bed, and we snogged for a while (nice lips, nice technique, no real hunger, but pretty good overall), then I put him back on my cock and started to play with his ass. He was very hairy from the waist down, which I find particularly hot on a slender man, and I ate his ass for a bit while he went down on me.

After a few minutes, I felt the intensity lessening, so I blindfolded him with his towel, and that made him more alert. Then I pulled his hands behind his back and wrapped my belt around them several times, and that made him really hard. Then I pushed him down on the bed and spread his cheeks with my hand and ate him more thoroughly. Lots of moaning from him.

I was on a tight schedule since b&c and I had tickets to a play later in the evening, so I had to move things along more quickly than I would have liked. I'd have eaten his ass for a half hour, but I couldn't, so I lay on top of him and sucked on his ears while I pushed my cock up near his asshole and simulated fucking him. Then I went for the lube and worked a finger and then two into his ass. I gloved up while he was still blindfolded and bound and tried to fuck him.

Some day I'll learn. Two fingers just wasn't enough. I really needed to go for the third finger and possibly the fourth before trying to stick my cock into him because he just couldn't take the girth. And, believe me, I tried and he tried, and we both wanted it. I got maybe two inches into him once, but no further. While he was bound, I tried with him on his stomach, then with him with his legs spread wider, then with him on his side. Then I pulled the rubber off and unbound him and told him to suck me some more, and I played with his ass a little more.

I told him to put another rubber on me, and he did, and I told him to sit on my cock, and he did, but, again, he couldn't get me all the way in. He tried facing me, and he tried facing the other way. No dice. Then I put him on his back and pushed his legs up and started to shove in. And, I'm sure that I could have shoved in, but, well, you know, that's just mean. He's gotta open up and accept it. After a while, I said, "You're not going to be able to take this, are you?" and he said no. Oh well. It is a thick cock, and he is a thin guy, and it was a tight hole, and there were alternatives.

So I told him to suck me off, and he did that like a champ. He had me really close for a long while, and I was loving it, but I was starting to worry about the time, and he wasn't quite pulling the trigger, so eventually I told him to back off for a minute, and I wanked a bit and then told him to finish me off. He grabbed and stroked, and tongued the side of my cockhead, and the first shot out of me flew past my shoulder. I'd expected him to swallow, but he clearly wasn't into that because shortly after I came, he ran to the bathroom to rinse his mouth out. I asked him if he wanted to jerk off with my cum (he had a really big foreskin; I'd wanted to hold it closed while he came so that the cum would make it balloon up), but he was pretty clearly done. He went instantly from being completely into it to not being able to look at me.

But I guess that's a part of straight boy submission, right? Oh, the shame, the shame! It's pointless, but it's not something you can worry that much about when you've just had a really intense ejaculation. I was totally relaxed and feeling great, so I went to the bathroom and rinsed off. I looked in the mirror, and I thought, "Damn, Teddy, you need to get some sleep." I did look pretty old right then, and I thought I finally understood what "rode hard and put away wet" really looks like. It doesn't look good, but fuck it: at the end of March, I'm supposed to look like I've been through hell. At least I felt good, and I'll look a lot better in a month.

We both got dressed, but he still wasn't looking at me. He'd put on some moss-colored cords, and I wondered whether he was trying to look like a graduate student, but I think that he's some sort of IT nerd (which I love, by the way), and that's just how he dresses.

I got a "Thank you, Daddy" email this morning, so I think there's a pretty good chance that I was sufficiently dominant and that at some point soon his hunger will again overcome his shame. If there's another session, I'm going to make sure that I have more than an hour to play, and I'm going to bring my toys, and I'm going to get all the way into that ass.

The play (The Pillowman) last night was pretty good, and I managed to stay awake through both acts. My mood is much better today, and that's hardly a surprise. I'm still exhausted, but whatever.

There probably won't be much Internet access over the weekend, so there probably won't be any more entries for a few days, but I'll be back. Also, at some point, I promise to edit more and ramble less, but, don't hold your breath on that one, ok?


¹For the love of God, please appreciate the utter brilliance of this simile and how well it works on multiple levels. Also, I'm not lying or bragging here: I really can remove all the bones from a chicken and leave it in one piece.

²This is how you know that I'm really masculine. It takes the threat of losing a fine piece of ass to make me ask for directions. To avoid this situation, I'd gotten directions from Google maps, but then I hadn't followed them, because I'm just that butch.

³In case you're wondering, no, I have never hired an escort. Not that there's anything wrong with that: I intend to start when I'm in my fifties.