“No plan survives first contact with the enemy.”
It’s a military thing that, more often than not, proves itself to be true. Why? Simply, you can’t really plan for what an “opponent” is going to do while you’re making plans that hopes to get them to do what you want them to do.
I was thinking about a time when I was sitting with a guy who was looking for his first experience. We’re sitting in his bedroom, on the bed, naked from the waist up and he’s so nervous that if I had shouted, “Boo!” he might have had a heart attack or something. I had learned not to plan for anything in this situation because (1) a guy’s first experience isn’t about me or what I want to do and (2) because I used to do that, well, such plans didn’t survive that “first contact.”
He kept asking me what I wanted to do and I calmly kept telling him that it’s not about what I want to do; what I want to do is whatever he wanted to do even if what he wanted to do was nothing more than the two of us sitting there and talking. After a couple of minutes of silence – and he’s less nervous at this point – I’m sitting and watching him and saw the moment when he decided on what he wanted to do even though I had no idea what that would be.
I had also learned to be prepared for anything. He said that he wanted to start slowly with this and by jerking off in front of each other. I said that was fine with me; we finished getting undressed and stretched out on the bed and we’re stroking ourselves and… I “knew” what would be next; at some point, he was going to suggest that we jerk each other off and that was also fine with me. A minute or two later, he asked if I’d be okay with giving him a hand and I said that I was and reached over and, well, gave him a hand; I wasn’t surprised that not even thirty seconds later, he was fisting my boner and, in my mind, I thought, “Let’s see how long this lasts.”
I almost punched him when he suddenly jumped up and started going down on me. Okay. In my experiences, this was known to happen and it’s not so much of a plan or an expectation but an understanding how things can escalate and also understanding that, sometimes, they don’t. He’s learning how to suck dick and I’m feeling a little silly because his sudden movement had surprised me but, focus.
Back in the negotiation phase, he had said that he didn’t think that he’d be interested in sucking dick but he was very interested in being sucked off by a guy; I had said that it was fine by me but I’m also thinking about the many times I’ve heard a guy say this and that’s not how things took place. He’s figured it out and I’m genuinely into what he’s doing; he shifts his position to lie beside me, his boner actually poking me in the cheek, and I didn’t hesitate to take him in and “show him how it’s done.”
I… “hate” being sucked by someone who had never done it before because their inexperience, for some reason, tends to make cum in a hurry and I had no idea why (and I still don’t know so don’t ask) but things are getting hotter and heavier and I feel his prick get harder in my mouth and he cums and it must have been pretty powerful because he kinda started to bite down on me and the only thing I could do – and while focusing on not gagging or choking on all the cum being put into my mouth was to stroke his face and that had him ease up on me.
Jesus. Amazing how a first-timer can cum from being blown and there’s a lot of cum and as the torrent starts to ease and he begins to soften, I’m thinking that he’ll probably tell me that he’s never cum like that before – but that’s for later because my dick is still in his mouth and it’s so warm and wet and, damn it, I gotta cum. I remove him from my mouth and give The Warning and as I had promised I would during our negotiations and in answer to his questions, you know, if he were to change his mind and suck my dick and hypthetically speaking. I’m lying there and feeling my impending release quickly approaching and I’m repeating The Warning and I hear him go, “Hmm-hmm…” which I know means that he not only heard me but for me to go ahead and cum.
I give into it and I’m cumming; I hear him go, “urp” and I’m dimly aware that this is literally a seminal moment for a guy; he’s either going to “acquire the taste” or he isn’t but I’m somewhat “beyond caring” in this moment as my release is beating me like a red-headed stepchild and… I can see that he’s okay even though he’s got this look on his face that I’ll probably ask him about later. Maybe. He releases me and we’re both lying there doing the usual gasping for breath and a couple of years later he finds his voice and asks, “Why did I do that when it wasn’t what I wanted to do?”
Okay… here we go. It’s not the first time a guy had “gone off script” and has asked this question so I gather my thoughts and do my best to explain it to him and how something in a guy’s head just says, “Fuck it – just go for it and worry about it later…” and they find themselves doing something that they hadn’t planned on doing. Trying to explain “being in the moment” isn’t an easy thing to do but I’m doing my best and keeping a close eye on him because he’s in a very vulnerable and fragile moment and experiencing some emotional lability.
He’s listening to me but I can almost guess exactly what’s going on in his head – he’s now trying to reconcile and internally justify his behavior and he’s kinda struggling with it, so I stop talking and ask, “How are you feeling?” He starts talking about how he’s feeling and it’s between feeling great and feeling seriously guilty along with being miffed with himself because he did something that he formerly thought he had no interest in and wasn’t going to do and as he’s telling me this, oh, boy, he’s at a moment where what’s going in his head is going to make his body react… badly.
How many times have I had a guy throw up after swallowing cum for the first time? Too many to count. The bad part is that if he’s going to barf, there’s not much I can do about it other than to “sneak in” a suggestion to just breathe normally; I sneak this in on him and he nods and takes some nice deep breaths and he asks – again – how all of this happened and I say, “Things don’t always go the way we want them to.”
“We can say that I want to do this or I’m not going to do that and sometimes, things go according to plan and… yeah, sometimes, things can go in another direction. And that’s fine and you have to know that it’s fine; shit, I don’t know how many times that’s happened to me, and I’ve been doing this for a while.”
He nods and I can see in his eyes that he’s understanding this, but he’s got some more work to do in his head. He asks, “So now what?” which is “code” for “What are we gonna do now?” And it’s like… backpedaling but I say, “That depends on you. We can stop right here or…” I don’t really have to finish the sentence because he knows that he’s got a decision to make. In my own mind, I’m thinking that we’re either going to call it quits at this point or he’s going to want to do it again or – and as I’d experienced – something else might happen like somebody’s dick winding up in somebody’s ass.
Now it’s just a matter of what he’s going to say next. Strangely, there’s a… pattern to this and one I had noticed a few years back and I’d learned that even when I could see the pattern following form, there’s still no telling what’s going to happen so trying to “plan” for it is futile. The programmer in me is thinking, “If, then, else…” and now it’s all about the parameters that’s going to determine what, if anything, happens next.
He laughs and says, “You probably didn’t plan on this happening, did you?” and I say that I have learned not to plan or expect anything because things can either change or they won’t, and you just never know what’s going to happen until it does. I laugh and say that he obviously hadn’t planned on things going the way they did – and to “prove” that what I had just said was right.
And now we’re back to the beginning and him asking me what I want to do and me telling him that it’s still not about what I want to do and I say, “This is your experience and unless you have something in mind that I could say no to, it’s about what you want to do.”
Was I surprised that he wanted us to suck each other off again? No, not really. It’s not a plan or an expectation but an understanding about how things can go; I’d been in this situation and moment so many times and have seen guys respond in so many different ways that you can’t “plan” for what’s going to happen next, and it makes no sense to try to.
It takes longer for both of us to cum and his second time sucking dick was more… refined? Not sure that’s the right word but he was better at it than he initially was but, in my mind, – and as I’m taking him deep and holding him there – this isn’t that hard to figure out. Some guys are “a natural” at this and some guys have to figure it out and sometimes they do and sometimes they don’t.
He’s fucking into my mouth and I know he’s about to cum; he buries himself deep in my mouth and throat and for a split second, I’m thinking, “Uh oh…” and prepare for not really swallowing his cum and… he cums and I let my body handle it as his cock is pumping strongly. I do get a “chance” to swallow when he backs off enough – and I’m thankful because now it’s a bit easier for me to breathe. He “shifts” from cumming to furiously sucking my dick and a moment later, I cum and he’s “laughing” as he’s swallowing and how I can tell that is something I can’t really explain but I know what that feels like.
We separate and he… apologizes for “ramming” his dick down my throat and I wave it off and tell him that it’s no big deal and it’s not like I’ve never had a guy do that to me before. He asks me if I’m okay and I give him my “do I look like I’m not okay” look and he nods… and now he’s back inside his own head about what he’s done – again. I tell him that it’s okay and for him not to worry about it. I tell him that, sure, things didn’t go the way he had thought they would, but they don’t always do – you get into a flow of things and whatever happens, happens.
He asks me what I would have done if he had wanted to fuck me, and I said that I would have gotten fucked… because that’s what he wanted to do. What would I have done if he had wanted to be fucked was his next – and not unexpected – question and I said that I would have asked him if he was sure that he wanted to do this and if he really was, um, he would’ve gotten fucked because it’s what he wanted – and all of this was all about what he wanted to do more than anything else.
Things don’t always go according to plan and even when both guys are experienced at this. I just do not know how many times I’ve gone into a sexual situation with a guy and with a “plan” in my head about how things were going to go and… things don’t go according to plan. Or they do. Or, sometimes, you know that the plan has to be abandoned and that’s a weird one because I’ve been with a guy, things went according to plan but both of us somehow knew that something else was supposed to happen but didn’t.
So I learned not to plan for anything. Whatever happens, happens even if what happens is… nothing. Okay. At least inside my head, that “if, or, then, else” thing is always going on and it’s like planning but not really and it’s hard to explain. It’s like what am I gonna do if this happens or that happens and if this, then that, or else, this or that and it sounds crazy trying to write this down but it’s not that crazy in my head because, well, it’s the way I think. It’s about… probability. Cause and effect. A lot of known and unknown variables and that’s just about me and not “considering” the other guy because I know what he said but what I don’t and can’t know is whether or not he’s going to throw out his own plan – and our “plans” get chucked because being in the moment calls for it.
The two of us had talked about fucking and I was ambivalent about it; it didn’t matter to me if we did or not because this wasn’t about me… but I had showed up prepared for it and just in case and that, too, is a lesson learned. You “plan” for everything you think could be possible while not expecting things to go the way things were agreed upon. They usually do. And they sometimes don’t.
We didn’t fuck but went for sucking each other off for a third time and that only “worked” because we had taken a long enough break to rehydrate, get a bite to eat, and to hit the bathroom. It took longer for both of us to cum but we both managed it and he let me know that he was quite satisfied with how everything went and “praised” me for being a good sport and allowing him to do things the way he wanted them to while being surprised that he wanted to do what he’d done.
I waved it off and once more reminded him that this – all of this – was 100% about what he wanted to do, and it was the only thing I had really planned on – I just didn’t know what was going to happen. I didn’t tell him that I wasn’t surprised at how things escalated from jerking off to sucking each other off because I’d seen this happen too many times to be surprised by it. There’s a “predictable” pattern to this that is also quite unpredictable because you really can’t know what the other guy is going to do or how the flow of the moment is going to play out. I’ve been happily sucking a guy and being sucked and… one of us winds up with a dick in our ass… and that wasn’t the plan.
So, in a very weird way, you plan for things not going to plan. Yes, things usually go according to what was negotiated and nothing more than what was negotiated… and not so much sometimes. The best thing to do is to be prepared for… anything. Or nothing. You can have it in your head what you want to do and… it goes according to plan, or it doesn’t. Or it does… kinda. At least for me, it’s all about being in the moment and going with the flow of it and with the understanding that you can’t really know how that’s going to go. You can “plan” for it to go a certain way and sometimes it does. Sometimes. How many times have I surprised myself and the other guy when I’ve blurted out, “Put it in my ass and fuck me!” and, yep, I’m wonder why the hell I said that because it’s not what I planned for and not what we agreed to.
Or he’s the one who’s gone off-script and I had to learn not to get… discombobulated when the “plan” goes flying out the window and now, hmm, how are things going to play out now? Sometimes, it goes well and sometimes not so much and even then there’s no telling or planning for what could happen but with a first timer, I have to plan for what I’m doing to do and/or say if some damage control is called for and understanding that even planning for this might go by the wayside because it proves to be not needed or, shit, sometimes, it’s ineffective or partially so or, shit, let’s not really call it a plan but it’s just being prepared for… probable stuff.
This moment went well for the guy and, well, that was the plan I had in mind. What I wanted to do was for this to go well for him. I did eventually tell him that I had kinda/sorta expected things to go the way they did and assured him that he wasn’t predictable but there’s a pattern to this that, again and for you guys, isn’t easy to explain but you just know it. I explained to him that you can start off like we did and jerking each other off. Okay. This is… okay. But then, hmm, doing this to each other sounds like a great idea – and for a lot of reasons that you just can’t put into words. He nodded at this point and admitted that when he suggested that we jerk each other, he was thinking about what my dick would feel like in his and and all that and why the hell not.
We’re both laughing over that. I then said, “At some point – and I really don’t know why – you’re stroking the other guy and, like we did, we’re watching it happening and then it just… pops into your head that you want to suck the dick you’re stroking and even though you had said that you weren’t interested in that but now you are and you start doing it and you’re wondering why you’re doing something you said you didn’t want to do and didn’t plan on doing it… and did he see what goes on with this?
He said that he did and how weird it is because that’s kinda what he was thinking… and impressed that I knew what he was thinking and how did I know that? Well, that’s because I’ve had those same moments myself and if I can recognize it in myself, it’s not all that hard to recognize it in someone else and more so when you get chances to see it and as many times as I’ve had.
You… hope for the best but expect the worse. You… plan for things while expecting for things to not go according to plan because you just learn that you can never really know what’s going to happen until it does. There’s what you want to do and then there’s what could happen that’s unexpected because you have this… idea in your head about how something is going to go, and some guys get blindsided when the unexpected happens… and they’re the one who flushed the plan down the toilet.
It’s… complicated to write down and as you can probably tell. You plan for the plan not going according to plan… and going according to the plan. Crazy, huh?