CUMSLOPPY STORY || Bossy Little Bottom

Story via The Invisibleman

Just a few minutes ago my Filipino boy left. We both needed a maintenance visit, so he came by late this afternoon. He’s nice, but our encounters are usually pretty primal and task oriented. When he arrives we make out and strip, but it’s almost like following an instruction manual: first he puts my cock under his balls as we make out; then he drops to his knees to suck me; then he tells me to sit on the edge of the bed so that he can suck me and keep one leg up on the bed as he strokes his cock while sucking me.

As it just unfolded I was struck by a couple of things, though for the most part I enjoyed it and played along.

First, I am just amazed by how small he is: about 5′ 6″ or 5′ 7″ and probably weighs 120 lb. As he started to suck my cock it registered how big my cock was in comparison to his head and his ass. I was recognizing relative to his frame how big I am and how incredibly I must stretch him when I push into him. It must feel like taking a telephone pole for him.

Treasure Island Media, TIMFuck

But second, as we went through the ritual, it struck me that he was giving all the direction. I guess if I was going to take something that big I’d want to call the shots as well. However, I am the one usually calling the shots.

He calls me his daddy and refers to himself as my boy, and says I own his ass (the exercise is for me to mark it as mine again) and once in, he says it’s all about making me feel good. But for the most part there are a lot of yellow lights and stop signs as we move along with him being the traffic cop.

I started to think about it when, after he’d just directed me to lie back so he could suck me, he next told me to lie back so that I could eat his ass, which was then in my face as he straddled me. Typically I am the one who decides when and if I am going to eat the bottom’s hole (almost always, lol) but I feel like that’s a call I should make since I am doing the rimming. Being told to do it kind of throws me off my game.

Now it’s all great. He has a super clean ass, and moans with appreciation, and wants to make out immediately after I tongue him, but it seems almost like a role reversal. Not quite a power bottom, as I usually think of a power bottom as a guy who fucks you with his ass and demonstrates amazing muscle control squeezing you with his guts. With this “boy” (the guy is in his mid 30s) he decides when I am going into him, and is fierce about wanting you to take your time until his ring voluntarily dialates and pulls you inside him. It takes a long time for him to adjust to it and it’s a very gradual process getting his body to gradually relax so that I can get balls deep — like a l o n g time.

Treasure Island Media, TIMFuck

Tonight he straddled me. He didn’t have poppers (for which I was glad; I understand why bottoms use poppers but I can’t stand them; during a hook up a month ago the guy spilled them all over the bed and I got a headache from the stench) so it took quite awhile for his body to allow entry and for him to take it: rather than inch by inch it was like millimeter by millimeter. However, that also added to the experience as I could feel it as he gradually opened, as my cockhead gradually popped in and then as he very gradually took one inch, two inches, three inches… The intimacy was enhanced by seeing his determination as he grimaced and then hungrily bent down to repeatedly make out with me as he forced more of my cock into him. He told me that I was the last one to fuck him, so he was really tight and needed me to take it easy (that seems to be an echo in my encounters, as of late…)

When I finally got balls deep, he was okay with my thrusting up and said yes when I asked if he was ready for me to fuck him; he was almost ready for me to take over. Almost. He wanted to be on his back. As we separated and he started to lie on his back I wondered how long before we’d get me all the way back in: when I first entered him he grimaced and hissed, but then he said “fuck me daddy! My ass is yours daddy. I want you to use it to make you feel good; it’s all about you feeling good!”

However, he was now really enjoying it. At first he said “you like it slow, don’t you? That’s fine; however daddy likes it!” But then he wanted to me to pound it into him. At first he had his hand stroking his cock (which makes me want to swat it away: let me cum first dude, then we’ll worry about your dick!) but he pulled his hand away and submitted totally to focus on being fucked.

Treasure Island Media, TIMFuck

His ass does fit around my cock like a glove. There was no question he was going to get my load; the question only seemed to be how long. As I was now fucking him with no reservations he was rooting me on and invited me to fuck him twice (the usual pre-orgasm “eyes are bigger than your stomach” mentality. Once he came he was done, but so was I.) It felt really nice: smooth, warm, tight. I decided to just go with it when I felt the first wave. As in the past, he got really excited when he realized I was cumming and asked me to keep fucking him while he stroked off. I was good with that and kept going, fucking my load deep up into him. And then he started to cum: like most little guys I have played with he shoots long streams of cum across his stomach (this time he didn’t hit the wall.)

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