Inadequate Men
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Chapter 4 -- Reflections
Back at work on Monday, Jared wondered if it had all been a dream.
He and Tom had spent all of Sunday together, just having brunch, walking around the city, and then seeing a movie together and secretly holding hands the whole time. They parted ways on Sunday night, agreeing to see each other on Tuesday night, with both of them looking forward. They kissed for a long time at Jared's apartment but both agreed to leave another sexual encounter for their next time together.
He knew for sure that Tom was a good guy who wouldn't play with his heart, and that was a good starting place. At the same time, in a way, that fact made the prospect of a possible relationship all the more real, and that was so scary for Jared. And now, with Tom away for a few days, he had a chance to think through why that might be the case.
Jared had come out as gay during his sophomore year of college. During that time, he'd made many good friends, and because of his boy-next-door looks always attracted the interest of other guys. But despite this, he never really had a relationship of more than a month or two. They always started out good and ended disappointing, with Jared feeling sad and hurt that he had opened his heart in the first place.
Part of the problem was the whole top or bottom thing. Jared never felt that he fit either mold. He didn't really enjoy either position in either direction. In fact, while he knew it was sacrilege, he felt no particular attraction to another guy's ass. And if he'd been allowed to speak his mind freely, he would have said that far as he was concerned, a butthole was for letting something out, not something in.
When he thought about what he really wanted with a guy, it was always face to face. He liked kissing, and he loved stroking a guy's face, chest, and shoulders. He also loved feeling a man's whole body press against his. Jared liked nothing better than a make-out session that built very slowly and lasted a long time.
But more than that, what Jared really wanted was a gentle connection. Why was that so difficult to find? In college and then in his early 20s, he met so many guys who seemed like they wanted the same thing. Sweet, sensitive guys who seemed to want nothing more than a warm connection with a male partner. He went on date after date with guys who said they wanted this, only to find that when it came to sex, most guys craved a hot, sweaty encounter with a screaming orgasm at the end. And from time to time, Jared had to admit that this felt pretty good, which only added to his confusion.
But what he wanted, what he really wanted, had more to do with eye contact and soul connection than anything in the body. Part of this had to do with his fear of rejection that ran so very deeply. Because of his feeling of inadequacy about his small penis, he desperately longed to feel safe with a man, to just hold each other and let the physical aspect of sex unfold from a shared sense of intimacy and vulnerability.
So many times, he had found himself in bed with an attractive guy who said he wanted the same things as Jared did, only to find that this safety was missing. Maybe Jared would have been the same if he had been born as that kid who was showing off in front of his friends by swinging his dick around in circles that first day of gym showers. But instead, he was the one whose tiny prepubescent penis had made a bunch of normal 14-year-old boys point and stare and laugh and pity him.
And it wasn't even the incident itself, but more what it revealed about Jared to himself. Even if it hadn't happened in precisely that way, the truth was that he had an abnormally small penis. He had to face this truth in most of the sexual encounters that ever got far enough for him to strip down to his underwear. More than once during the lead-up to sex, a guy would reach down the front of his pants, size up the situation, and then suddenly remember that he had an early morning the next day and better be going home.
But it was maybe even worse with some of the guys who stayed. "Well, I guess I know now which one of us is the top," said one of them, being particularly honest. But more often than not, even when unspoken, Jared could read disappointment in the eyes of his partner. And each time, feeling shame to his core, he closed up just a little more. What was the point of opening up to a man who appeared to be trustworthy if, at the end of the day, Jared was just going to get rejected for his small penis, which was something he could do nothing about?
Law school provided Jared an excuse to avoid the whole issue. Plowed under with more work than any human could possibly complete, he threw himself into his studies 24-7. His friends during that period were exclusively other law students in his classes, all struggling to understand and master the massive amount of information being thrown at them on a daily basis. For that time, Jared's only sexual outlet was jacking off alone in the shower every morning. His fantasy hadn't changed -- a loving man gently accepting him as he was. And for two or three minutes a day, it was his reality, and that had to be enough.
This trend more or less continued as he finished school, studied for the Bar Exam, and then landed his current job. Through it all, his parents generously supported him as much as possible, so that he accumulated only a small hill rather than a mountain of debt. By the time he was 30, he felt secure enough in his career that he could begin to relax and enjoy life.
And that's when the lack of a partner or any real boyfriend experience really began to bother Jared. All around him, despite their busy schedules and demanding careers, people he knew -- gay, straight, male, female -- were pairing up. Gay marriage might have been a legal reality, but for Jared it was still a distant dream. His longest relationship to date was five months -- two of them spent apart in different cities!
And now, here was Tom, who seemed so different from any man Jared had ever met. He wanted desperately to believe that they might really have a connection that could lead someplace amazing. It seemed possible. At the same time, the thought of opening his heart again only to be rejected in the same old way was terrifying.
At the very least, his 24 hours with Tom had been galaxies apart from any dating experience that Jared had ever had. Perhaps, as another small guy, Tom could begin to understand Jared's anxiety and feelings of inadequacy, and seemed to share them to some extent. But there was one more thing that Jared hadn't expected.
All day long, as he and Tom had brunch, visited a park and had a boat ride together, and the whole time he sat through a movie that was only marginally entertaining, Jared found his mind returning over and over again to something that had truly sparked his interest: Tom's struggle and inability to avoid prematurely ejaculating.
Throughout the day, recollections of these moments kept returning to Jared and playing vividly in his mind. And each time, the memories gave him a rush of excitement that he couldn't quite explain.
The first time it happened, in the shower room, Jared remembered putting his hand on Tom's shoulder reassuringly and letting him know it was OK. That impulse within himself made him smile, because he had often wished that a boyfriend would offer him the same type of reassurance with his own sexual insecurity. Out of all those seemingly nice guys who claimed to want a life partner to share a home, career ups and downs, a dog, and maybe a white picket fence -- out of all those guys, none had ever said to Jared, Dude, it's OK -- the size of your dick doesn't matter to me. Because if one had ever said that and meant it, Jared would be living with him right now -- probably in a house with a white picket fence.
That impulse to reassure Tom seemed pretty basic, but core to who Jared was and what he wanted to share with another man. What he didn't expect was his sexual reaction. Sure, he was already turned on by Tom. It had started with that long handshake as they stood together in towels, the immediate warmth of the connection that both of them had felt and neither man wanted to let go of. Even as they held hands again in the dark movie theater, Jared still felt the intimacy of that connection, and imagined that he could live to be 100 years old and still want to experience that same intimacy with Tom.
And of course, there was the apprehension he'd felt about letting Tom see his small penis, followed by that heart-stopping rush of relief upon discovering that they were both small. Jared never knew that relief could feel so good, as his resulting erection made clear. In most situations, Jared was sexually very timid, and if he got an erection at all, it was only because he felt very safe and comfortable for a long time as the feeling built up. He very rarely just sprung a boner like that, especially with another man looking on. He just wasn't built that way and never had been.
But that feeling of relief as he and Tom stood naked together was something entirely new for Jared. Sure, he had hoped for it, dreamed of it, and jacked off to it as an ultimate fantasy that he'd never quite attained. He had imagined the joy of feeling completely accepted by a man in every way for everything that normally made him feel sexually inadequate. He just didn't know it could ever happen anywhere but in his mind, and never expected how relieved he could feel from the burden of feeling so isolated and alone for so many years.
Somehow, in Tom, Jared had found a man who had long carried this burden as well, and the two men had shared a kind of intimacy that neither had ever experienced. Jared's erection in that moment felt so natural, something he had been longing for all his life.
What had happened next, though, was what Jared's mind kept returning to: Tom's sudden urgent need to release, his desperate struggle to control this impulse, and the shame he clearly felt at being unable to master it. And then, as Jared gently let him know it was OK, the reluctant and resigned way that Tom took his thin penis in his hand and brought himself to the completion he could no longer prolong.
And then it happened again, when they were together in Jared's apartment. This time, they were naked together holding each other and talking about it as it was happening, which made Tom's struggle and inability to hold back even more exciting to Jared. That time, one of the things that most excited Jared was when Tom said, A man should be able to hold it. How long had Tom been suffering silently behind this secret wall of shame at his inability to do what every other man seems to manage? Every sexual fiber in Jared's being was on fire as he took Tom's small thin penis gently in his hand at that moment, felt how hard and overstrained it was, and understood how desperately Tom was trying to hold back and get control of something that was only moments away from overwhelming him.
Throughout the day, as they talked and walked and sat together, Jared's mind kept returning to these moments of Tom's desperation. And not just his mind. He could feel his heart pounding with sexual excitement, his respiration increased, his stomach full of butterflies, and his penis repeatedly waking up and stiffening in his pants. Before long, there was a wet spot in his underwear that Jarred worried might leak through to the outside.
Among all the good feelings of his quiet day shared with Tom, this secret source of excitement was completely unexpected. After the movie, he would have loved to bring Tom back to his place and have another opportunity to experience it firsthand. But the two of them talked it through and agreed that as fun as another night together would be, after a weekend so full of new feelings, it might make more sense to part ways, get back into work mode, and reconnect on Tuesday.
Back in his apartment by himself, Jared poured himself a glass of wine, turned on some music in his bedroom, and played and replayed these scenes over to himself as he lay on the bed. He knew that he needed a good jack off session to explore these fantasies further. Not to mention that after a full day with Tom only thinking about these things but not acting on them, his balls were full and aching in a way he was sure just wouldn't let up until, one way or another, he'd emptied them out onto his chest and stomach.
Jared gulped down the wine so its effect would be quicker, lowered the lights, and crawled out of his pants and shirt, then climbed under his comforter into the space that he had so recently shared with Tom. In fact, he could still smell Tom's subtle scent on his pillow, and this made him smile. Damn, he realized, I really like the guy a lot.
Then he remembered that about a month ago, a friend had shared half a joint with him, and then left him the other half. Jared had stashed it in the top drawer of his nightstand for later use. He rarely got stoned, or even wanted to, so he'd forgotten all about it. But tonight, he had a feeling it might be just the thing.
He sparked it up and took a small hit to get his lungs ready, then blew out, took a deeper hit, and held it. Usually, because he was such a lightweight, one good hit was all he needed. Tonight, though, Jared indulged. He held the flame up to the joint a second and breathed another deep, deep hit into his lungs, as much as he could take in, then closed his eyes and held it for almost a minute.
The resonant sound of his room behind the music came into foreground focus as he felt like he was floating away. As Jared held his breath, he could feel his heart beating rhythmically in his chest. Images from the previous night and day with Tom cascaded in his mind. He focused in on the moments that had brought him the most intense sexual pleasure, and both saw and felt them all at once in heightened focus. He was so fucking turned on he couldn't believe it, and his hand moved down to rub his dick through his boxer briefs.
Jared thought about Tom in each of those intense moment of struggle as he had tried not to cum, in the shower room and then in his living room. They both played back and forth in his mind, and Jared felt a wave of sexual excitement as his heart pounded and his dick sprung to life. Then something unexpected happened and it shattered him beyond anything he could have imagined.
A memory returned.
To be continued...
The response to this story has been amazing, so if you've already written to me about it, all I can say is thanks! If you're liking how the story is unfolding and have thought about writing, go ahead and say hi at judestjude2357@gmail.com. I promise to do my best to answer every email I can! Thanks again, TJ