Guys I’d like to blow right now/4.
15A: I AM JACK’S BRAIN…AT WORK
My very first thought when I finished reading John and Jack’s long text chat was: ‘Holy fucking shit.’ The first thing I did when I finished reading was to pretend that I was still reading for a couple of more minutes so I could let soak in before I discussed it with John, who was plainly ready to talk about it - and then, I assumed, immediately begin putting to good use some of Jack’s tips on how get John’s big cock all the way up my ass in the shortest amount of time and the least amount of fuss. Trust-building exercise, my ass. I was well familiar with the “trust test” Jack had described and recommended to John, though Jack and I had called it the “knob-in-the-hole.” The fact that Jack was talking to John about it at all was a big flapping red flag.
John was still sitting on the sofa flipping channels and I was close by in my favorite reading chair. What was clear to me after what had been a fairly quick reading of the whole conversation was that Jack was operating on multiple levels, exactly how many I wasn’t quite sure. I couldn’t begin to peel back all the layers of Jack’s big fat onion without giving it a lot more thought, so I needed to step carefully through this potential minefield until I had a clearer picture of the entire game Jack was actually playing. Apart from the obvious (to me but not John) knob-in-the-hole instructions Jack had given John, I spotted a couple of other land mines he had laid. But these were likely just the most obvious ones - those that were very much intended to be seen, and to be seen by me, not John. I wondered how many other traps I might have totally missed.
On the very first level, and leaving aside his motivations, Jack was in fact trying to be helpful to John. There were no lies or misinformation that I saw on first reading and, to the extent I knew anything about fucking another guy in the ass, Jack’s advice seemed sound. But Jack was also playing a variant of the manipulation games he and I had been playing most of our lives - and it looked at first blush to be a masterful fucking game he was playing.
The knob-in-the-hole alone was a fucking masterstroke. And making that play had clearly been Jack’s main objective, but there were indications (primarily Jack’s liberal sprinkling throughout the chat of several of our “twinspeak” code words and other references that only I would get) that more was in play. But I knew all too well that with Jack’s games, appearances often deceived. The question I had then was whether knob-in-the-hole was THE play and the other sprinkled code words were just fluff, window dressing, to make me THINK there were multiple scams underway, or were there really multiple scams underway?
Here’s a good example of why I was in a quandary: near the end of the chat Jack had described his and my garage apartment at home as “the perfect setup for illicit romance.” Which it in fact was. But “the perfect setup” was also twinspeak signaling that a major perfect game was afoot…so at a minimum Jack was brazenly announcing that his devilish mind was at work - telling me that he was fucking with me and I couldn’t do a thing to stop him. But it was more nuanced than that. When Jack or I used the twinspeak phrase “illicit romance” its usual meaning was strictly limited to our own acts of brotherly love…Jack was probably just having fun at John’s expense by inviting him to drive over from Dallas to fuck me in the ass in the same cum-stained room where he and I had spent so much quality time together. Or was he signaling that there was a separate “perfect setup” in the works? Oh, and if I haven’t already mentioned this, although Jack’s hidden messages to me were embedded in his text chat with John, he had made fucking certain in the same conversation that John would hand his phone over to me to read it all…and start worrying.
Jack’s primary objective was to get my ass thoroughly fucked by John before I left St. Louis (and likely that very night) and could get home where, from Jack’s point of view, there was some risk that he would yield to my blandishments and fuck me in the ass before John would have another opportunity to go first. To accomplish that he could not have deployed a more perfect setup than knob-in-the-hole.
It was so perfect that it almost felt unfair - because Jack had designed the knob-in-the-hole “trust test” that he so unselfishly shared with John based on intimate inside knowledge of how I was likely to react to having just the head of a cock parked in my asshole. John was certainly going to insist on fully establishing my trust in him as so helpfully suggested by Jack, of that I had no doubt. But of course John didn’t know that Jack and I had played that very same “game” - one time - when we were 17. Nor did he know how cravenly I had folded with about an inch-and-a-half of Jack penetrating my inner sanctum while he sucked my nipples and expertly played with the head of my dick. After a scant three or four minutes of that treatment, I had literally pleaded with Jack to fuck me, to push all the way in and “fuck the shit out of me!”
Jack hadn’t fucked me, of course, and I had never let Jack’s knob near my bunghole again. Under Jack’s rules - and the revised rules he sent to John - he could not fuck me then since I had “released” him from his promise not to fuck while he still had his inch-and-a-half in my hole, not even with me begging him to plunge ahead, because he had promised me he would not fuck me even if I begged him to. But five (nearly) years earlier, Jack had not attempted to renegotiate the deal upon his withdrawal of the head of his dick from my sphincter, I assume because at the time he believed that would still have been a violation of my trust and his promise. I know for a fact that he believed we’d fuck soon enough anyway, because he was knocking on the same door the next night. But when Jack tried to collect the fuck he believed he richly deserved after having passed the test with such flying colors, I said, “No.” He asked to fuck me in the ass a few more times after that and I always refused. He accused me of breaking “an implicit promise” to let him fuck me in the ass if he passed the test by not fucking me when I had begged for it, and then went looking elsewhere.
Jack had since clarified the ambiguity in his rules that had cost him a full piece of my ass when we were 17. The rules of the trust test he handed down to John had been revised to ensure that I would not be able to wiggle off of John’s big mushroom head - if I asked for it this time, I would get the full eight inches. In that day’s text version of the rules, I had read that once the test has been passed and the cock head has been withdrawn, immediate agreement should be followed immediately by full-fledged buttfucking. Jack had even greenlighted John to fuck the rules and fuck full speed ahead if I asked for it - although he did observe that John would better secure my trust by first withdrawing and then plunging back in.
Jack and I had also had very different takeaways concerning my sexual nature from that exercise - though within five years it appeared that Jack had been right and I had been wrong. His test, of course, had been the origin of Jack’s certainty that I have the soul of a bottom. As he said at the time, I was “destined to have great things…up [my] ass.” But my takeaway, after my initial fuck-fever had passed and Jack had stroked me to orgasm (another youthful mistake - he should have fucked me before granting me that release!) was that I hated (sort of) being without any control over whether that cock pushed forward or pulled out. So I had made up my mind to be the guy behind the cock and not the one in front of it. I suddenly wondered who Jack had learned his little trick from when he was only 17 years old - it seemed more like ‘advanced buttfucking’ to me than mere beginner’s stuff, but what did I really know about any of it?
The reasons for what you might consider my duplicitous behavior in trying to get Jack’s seven inches all the way up my ass before my boyfriend’s eight inches became its cock-in-residence were as convoluted and shifting as they were unconvincing, and for the most part they have already been discussed. The main reason at first was that I simply wanted Jack to be the first to plow my ass, mostly due to the welter of tangled emotions and often-frustrated sexual history between us. But the explanation I had given Jack for asking him to fuck me in the ass first was that I was concerned about the size of John’s cock coupled with his (and my) total lack of experience and, as I had flattered Jack, I wanted him, with his considerable experience and unmatched expertise, to more gently break me in, as well as teach me how to be a more responsive fuckee for John. I saw Jack as blazing the trail John would follow, but mostly I just wanted Jack to fuck me. Period.
The pretext I had offered Jack now threatened to be the undoing of my Christmas wish, because if John managed to fuck me in the ass before I could get out of town and home for the holidays, my whole basis for asking/begging Jack to fuck me in the ass FIRST would disappear. On the other hand, IF I could escape St. Louis with my anal virginity intact (or as intact as it still was then, if having the head of my brother’s hard dick an inch or two inside my brown eye counted as a technical loss of virginity), I liked my chances of success in seducing Jack. There was zero doubt in my mind that we’d greet each other for the first time privately (not in front of Mom & Dad!) with our tongues in each other’s mouth and our hands in each other’s pants, and we’d be sharing the same bed and shower, as well. I knew that because that’s the way we had parted in August and it’s what we always did when we were together. We each shared a hunger for the other, and we had never been apart from each other for as long as we had this semester, four months, almost to the day.
During our first three years of college, with me in St. Louis and Jack in New Orleans, we had usually managed to get together two or three times a semester. For a variety of reasons, none important, it just hadn’t worked out this time. So I knew we would be in intimate proximity, hungry for illicit romance, with alcohol flowing and lots of opportunities to make bad decisions. Granted, holding Jack’s cock in my hand (a given) did not ensure that the next place he would put it would be up my ass, but he’d already told me (basically) that was where he most wanted to put it. He was struggling to hold that desire in check, to be sure, even valiantly, but he had not yet had to contend with me present on the same premises and actively engaged in undermining his attempts to do “the right thing.”
But Jack knew all of that as well as I did, so he had made yet another masterful move, in order to protect what passes for his virtue from my evil designs and to shield himself from the ever-present temptation to choose the path that leads straight to intoxication and orgasm, preferably in that order. And I must admit I didn’t see his curveball coming. In the unlikely event that I didn’t get fucked in the ass before the coming Wednesday, Jack’s “off-handed” invitation to John to come visit us in Mississippi early in the holiday season was a stroke of pure genius that had severely restricted my room to maneuver, to say the least. I figured that I would have, at most, two or three days (and nights) before John arrived and the question of Jack ever fucking me likely joined VHS videotapes on the scrap heap of history.
Jack’s resistance to my text advances had naturally intensified my resolve, such that I wanted EVEN MORE for Jack to be first one all the way inside me simply because he did not want to be. Recognizing the danger of rekindling our on-again, off-again (essentially) masturbatory relationship, and indeed taking it to a far different level, basically on my whim, Jack was stiff-arming my Christmas-fuck overture, big time, by texting John, encouraging him to fuck me immediately, and telling him how to accomplish that. While Jack had finally agreed to think about porking me, the time between his and my text chat earlier in the day (in which he had reluctantly admitted to a deep temptation to accept my fucking invitation) and Jack’s first out-of-the blue t/m to John was only 12 minutes. So it didn’t look like Jack had thought about it for very long after our chat ended.
It suddenly occurred to me that there might also be a slightly more subtle message (or messages) in Jack imparting his knob-in-the-hole instructions to John. Jack was right that if John and I did both try and pass this seemingly small test, we would emerge with greater sexual trust - but as I learned on the point of Jack’s cock, it is no small thing to turn back when you are already past the point of no return. Jack was also, he believed, giving John the keys to my anal kingdom - he certainly didn’t think we’d pass this test. So this part of their chat was plain old gloating or taunting - though, again, directed at me, not John: “Look! See what I just did!” But I also wondered if Jack might not also have been telling me, in effect, “Too bad, baby bro, you should have let me fuck you in the ass when I asked and you refused me.” Was he manipulating John to achieve a revenge fuck by proxy? Then I thought, ‘Christ, just listen to yourself, you paranoid fuck.’