This story is a sequel. Please read Part 1 before reading this one. All characters are 18 or older. This story is about gay male sex, including acts that are somewhat nonconsensual. Reader discretion is advised.
My heart was pounding as Craig walked into the room where Grayson, my boss, and the subject of my fantasies, had just finished giving me the fuck of a lifetime. Craig looked dumbfounded by the scene he’d walked in. I was sitting naked on Grayson’s lap, my legs straddling him, with his naked, muscular, manly body beneath me. The air was thick with the smell of sex. It was obvious to Craig that Grayson and I had just fucked.
What wasn’t obvious to Craig was that I’d set Grayson up. The fact that Grayson and I were tied to each other and to a chair suggested that there was something deeper than just sex going on, as it would have been impossible for us to have put ourselves into that position. I wondered if Craig realized that, or if he was too gobsmacked by the (sexy as hell) image of me impaled on Grayson.
Unfortunately, Grayson had me figured out. I’d unwittingly said something to tip Grayson off that I’d been in on the plan all along. I’d set out to make Grayson my latest conquest and hired a hobo named Buddy to pull a gun on us. To my surprise, over the course of the night, I’d realized that my feelings for Grayson ran deeper than simple lust; just moments before Craig walked into the room, I had confessed my love to Grayson and sworn I’d never try to manipulate a straight man into my bed ever again.
From that moment on, I knew I belonged to Grayson. My body, my heart, my desire were all fully his; I’d been conquered. Part and parcel to being the conquered instead of the conqueror, I resolved that I’d let him decide for himself whether or not he wanted to be with me.
The tension in the room was thick, and I knew it was up to me to break the silence. “Craig - boy are you a sight for sore eyes. Come untie us, big guy.”
“It’s not what it looks like,” Grayson mumbled weakly in a daze. I looked over at him. He didn’t seem to be angry. He looked withdrawn, defeated, and scared – a man coming to grips with what he’d just done, and wondering if there was any way to go back to his life and pretend that it had never happened. A new player joining the mix certainly didn’t help. That was one more witness to Grayson’s infidelity and homosexual conduct, and, as the dumbfounded expression on Craig’s face made clear, he wasn’t my co-conspirator as Buddy had been; he was a mere accidental observer. In other words, Craig could talk about the scene he’d come upon without fear of going to jail, and Grayson knew it.
Grayson wasn’t making eye contact with me. I rubbed his chest reassuringly. He looked up, but I don’t think he actually saw me. It felt like his gaze was going right through me. He clenched his jaw stoically. He’d been almost fatherly to me in the moments leading up to Craig’s arrival, but that had been replaced by the chill of indifference. It hurt, but I tried not to take it personally. For all he knew, he’d go to church Sunday and be greeted by whispers of everyone discussing his dalliance, where he’d been caught tied up with the gay naked office twink. Considering what could happen, he was actually handling this remarkably well.
There was something that turned me on about Grayson’s ability to go in such quick succession from my respected boss, to my intimate lover, to my father figure, to a cold stranger. It was utterly impossible for me to pin down the true Grayson. This fascinated me and made me even more enamored of him.
“Yeah, it’s really not what it looks like,” I said to Craig, trying to keep the mood light while also subtly indicating to Grayson that I was going to try my best to keep this all under wraps for his sake. “Now come untie us, you big lug.”
It took Craig a few minutes to work the knots, and I relished the attention. I’m an exhibitionist, so being seen by another man after I’d been freshly fucked - with Grayson’s creamy load still seeping out of my ass, mind you - was a huge turn on. It was especially hot because I knew that Craig had been wanting to fuck me for a while, and there I was, naked, with my beautiful twink form pressed against the ultimate DILF hunk Grayson. I wondered if Craig was getting turned on by seeing me like that, and if he was jealous. I also wondered if, perhaps somewhere deep down, Grayson was proud that he’d been the one to fuck me and Craig hadn’t. There was something primal about the way Grayson had just mated with me and claimed me as his property with his hot daddy sperm.
While working the ropes, Craig brushed up against my skin a couple of times. I barely suppressed a moan when Craig’s strong hand rubbed against my soft, squeezable butt. I was sure Grayson was humiliated beyond belief and counting every second that his nightmare continued, but if I’d had my druthers, it would have taken Craig hours to untie our naked bodies.
I actually caught Craig sneaking a few peeks at both Grayson’s dick and mine. I had no reason at that point to believe that Craig was anything but straight, so I figured it was simple curiosity – not quite rubbernecking a car crash, but something like it. While Grayson’s dick wasn’t hard as it had been earlier when he’d fucked me silly, it also hadn’t gone fully soft.
I hadn’t yet fully processed what I’d done, so I wasn’t thinking about the guilt or anything like that. All I knew was that I was on cloud nine, with Grayson’s freshly deposited sperm inside of my beautiful twink body. I felt no shame; the other shoe hadn’t dropped yet.
As for Grayson, I had no idea what to think. His dick sure as hell wasn’t flaccid. Sporting a semi in front of Craig and me, however, didn’t necessarily mean he was having a good time. I didn’t want to think too deeply about what he was feeling, because I wasn’t ready to process the guilt yet. I can see now that he was probably suffering through extreme humiliation, but all I cared about in that moment was that two straight jocks were so focused on my naked body.
“Got it!” Craig exclaimed, finally untying the big knot that would make untying the rest easier. The end was in sight. I looked at Grayson, hoping he’d meet my glance and make eye contact with me just one more time before we parted ways, but he wouldn’t. Whatever special moment had passed between us had clearly ended for Grayson the second Craig walked into the room.
After Craig untied us, Grayson quickly got dressed; he was fully dressed while I was still pulling up my underwear.
“Thanks for your help, Craig,” Grayson said plainly. “I’ll see you on Monday.” Then he left the building out the same door that Buddy had used to gain entry.
He didn’t say goodbye to me.
After all we’d endured together, it felt shitty. Grayson had said right before Craig had arrived that he’d forgiven me, but now it seemed like Grayson wanted absolutely nothing to do with me. I kinda couldn’t blame him for that. After all, I’d hired a man to force him at gunpoint to fuck me. It was starting to occur to me a little more that he had every reason in the world not to trust me or ever want to see me again.
Craig suddenly seemed to remember something, and spoke up. “Do you mind if I just step outside for a minute? I’ll be right back to make sure you’re OK.”
Craig left for a few minutes to say goodnight to Tiffany and to call her an Uber; I knew that he’d planned on taking her back to his place to fuck, and I appreciated that he was willing to change his plans for me.
When Craig left the room, I grabbed the mug that was still utterly replete with that most precious of natural resources: Grayson’s cum. Luckily, Buddy had forced me to spit Grayson’s cum into a mug after I fellated Grayson to completion earlier that evening. He’d then let Grayson use his own cum to lube up my eager asshole, but there was still plenty of cum left over, and I’d been hungrily eyeing it all night.
I put a lid on it and put it in the freezer; I planned to come back for it the next day when it was frozen. That way I’d have my own freezer pop of Grayson’s cum so I could take a lick and taste him any time I wanted to. I mean, I arrogantly “knew” deep down that someday I’d have a taste of Grayson’s fresh cum again, but I didn’t know how long that would take. I told myself I needed something to hold me over in the meantime.
I shut the freezer and cleaned up some of the evidence Grayson and I had left behind. When I was satisfied that the office was reasonably back in order, I sat down at my desk and reflected on the events of the evening.
I’d felt like my entire life had been building up to tonight. I’d been feeling the euphoria that comes from being fucked by the man of my dreams. But with Grayson gone, my happy feeling was starting to fade, and an extremely dark void was coming upon me.
I was a thousand miles away, searching deep inside my mind, trying to get back to that feeling of pure joy when Craig re-entered the room.
“I’m sorry that I ruined your date,” I said.
“Date?” he stammered. I could tell he was embarrassed that I’d heard his conversation with Tiffany, and that I knew that he was sexually and/or romantically involved with the office fat chick. “I was just giving her a ride home. She likes me, but I’m not interested.”
Uh-huh. Straight guys and their egos. Still, he was helping me out of a jam, so I played along. “Ah, OK. Would you mind giving me a ride home? I’m in no condition to drive.”
“Sure!” Craig said, perhaps a little too eagerly.
In his car on the way home, we didn’t talk much, which I was thankful for as I had a lot to think about. I wondered about what Grayson was doing just then. Did he run straight home and fuck his wife, hoping that would wipe away the incredible night of sex he just had with another man? If he had, I didn’t think it would work. I’m not big and muscular like Grayson, but I am a strong and athletic twink. I imagined him trying to fuck his matronly wife the way he’d just fucked me. No way. She’d never be able to handle it, and there’s no going back for him.
And yet… there was still the issue of his damn morality. It had taken a gun pointed at him to get him to fuck me the first time. In other words, I hadn’t morally corrupted him. I knew that even if Grayson acknowledged how much he’d enjoyed fucking me, it could be very difficult to get him to do it again.
It began to dawn on me that I might be in for a very long wait. For years, I’d had no problem going out and being able to get a straight guy whenever I wanted one. Even right then, in Craig’s car, I was fairly confident I could lean over and give him road head, and that he’d be happy as a clam. The idea of being alone was new, and I couldn’t deal with it.
I was already missing Grayson, so I started looking for some social media, just so I could have some part of me with him that night. But there was nothing.
“Craig, would you mind if I spent the night at your place? I really don’t want to be alone tonight.”
“Sure!” Craig said energetically.
Oh, God, I thought to myself. Poor guy thinks he’s gonna fuck me tonight. That wasn’t the plan, honestly. I was just scared of going back to my place.
My fear wasn’t just about confronting what it would mean to be alone. I was also having regrets about the way things had gone down. I wished I could have found a way to get what I’d wanted without involving Buddy. It bothered me that Buddy knew where I lived. He had clearly demonstrated his mental illness over the course of the evening. He had simply been too convincing for his performance to have just been acting. There was definitely something there, perhaps a case of extreme substance abuse. I was quite sure I never wanted to see him again, but I had no idea where he was or how long he would stay gone… or when he might rear his head again. I had a sinking feeling that, as much as I wanted to be done with him, he wasn’t done with me.
What if he shows up at my apartment? What if he wants more money? What if he tries to rape me? There had been a couple of times that night I’d felt lucky that Buddy hadn’t done exactly that. He’d seemed unhinged, like he had been fueled by testosterone and rage instead of merely incentivized by money. At times, it had seemed like he’d really wanted to violate my fragile, beautiful asshole. Perversely enough, I’d been lucky that Grayson had been there to protect me – or, rather, that Grayson had stepped up. In a strange twist of fate, I’d learned that Grayson was turned on by the idea of being the hero to a dainty damsel in distress. I believed that Grayson getting so horny about being my protector was part of what had made our lovemaking so intense and cathartic.
The knowledge that Grayson was sexually aroused by the idea of defending me was something that let me put my guard down with him. And it had been life changing for me to see how beautiful and intimate sex could be when it wasn’t not some kind of contest or competition. I had finally experienced complete submission to someone I loved, and I knew that was the way sex was meant to be.
“We’re here!” Craig said, pulling up to his building and expertly parallel parking his car. Even from the outside, I had the sense that I was about to walk into a tragic straight-guy bachelor pad, but I was too tired to care. I was sure Craig would ask me to sleep in his bed with him, and that he was planning on his dick accidentally falling into my ass, but I had no interest whatsoever in that. My plan was to actually get some rest, even if that meant sleeping on some cheap, beer-stained Walmart futon (a piece of furniture that, from my experience and expertise, seems to be standard issue for a certain type of straight guy.)
As we walked from the car to Craig’s apartment, my thoughts returned to Buddy. I wondered how the events of the evening had affected him. Is he getting gay-curious now? Will he look for a twink of his very own? Wait a second, why do I even care? Well, there is a certain simian quality to him that’s just dripping with blue-collar masculinity.
Just as I was about to imagine what a sexual encounter with Buddy would look like, I returned to sanity and remembered the video. Buddy had recorded my liaison with Grayson on his phone. For all I knew, Buddy was watching it and jerking off to Grayson fucking me – or even posting it to a porn site. The idea that I could walk into the office Monday and every single coworker and client could be watching a video of me getting fucked by Grayson, and that there was nothing I could do to stop the whole world from seeing it, was such a huge turn on. Buddy was like a stick of dynamite in this entire situation, and there was no telling when he’d go off. There was something simultaneously terrifying and thrilling about that.
Craig opened the door to his apartment, and it was actually a nicer place than I’d thought it would be. There were no cans of Natty Light strewn across the floor, no sink full of dirty dishes, and no empty pizza boxes from months ago. I was impressed. Then I remembered that Craig had been planning to bring a girl back there that night, and everything made a little more sense. Of course, that girl had been Tiffany, so I was surprised Craig hadn’t stocked up on Doritos and Twinkies.
Craig didn’t waste any time. He stripped down to his boxers right in front of me, as if it was what he always did when he got home. It was obvious to me he was trying to seduce me – and he looked good. He really was a handsome guy. I wasn’t even remotely interested, though, and it was hard not to laugh at his attempts to play mental checkers with me, a mental-chess grandmaster.
“Can I get you a beer?” he asked. I assumed he wanted to get me drunk, thinking I’d lose my inhibitions and at least give him a blow job.
“No thanks,” I said. “I’m really exhausted. Would you mind just getting me a comforter and a pillow and I’ll sleep right here on the couch? I’m gonna pass right out in a minute or two.”
Craig seemed to accept that he wasn’t getting any that night, and he was actually being pretty gracious about it. I think he knew that I had a lot on my mind. “Sure, buddy,” he said, patting me on my shoulder.
He set me up on the couch, and we said goodnight to each other. He gave me a friendly hug as he headed to his own room with a beer (to my surprise, not a cheap domestic one.)
I thought about Grayson. Is he asleep right now? If not, is he thinking about me?
He was a married man. I’d promised myself that I would give him space – that I wouldn’t use my usual seduction tactics and trickery on him – but the man had just given me the best fuck of my life. My asshole yearned for more of him. Grayson had only fucked me one time, and yet I was confident I could accurately describe his dick to a police sketch artist if I had to.
There has to be some way to just see some pictures of him. I need him so much. Maybe his son. He’s 18. He has to at least have an Instagram. He has one of those weird white people names. What was it again? Krabby or something? Cress? Oh! His name is Krell! Krell Nash! I managed to find Krell’s Instagram, but it was set to private. I shamelessly added him as a friend. But I’d have to wait for him to confirm me. Considering he’d never met me, I thought the chances were probably low. But damn it, I needed some part of Grayson to get me through the night.
Maybe there’s a way I can get Grayson to talk to me.
So now I started typing out pathetic, emotional text messages to him, then deleting them before I could send them. I’d always prided myself on how cool and collected I stayed around the straight men I pursued. It was my secret weapon. With Grayson, I was losing my cool completely. Every text message I typed out sounded more desperate than the last. Grayson’s dick had pounded my cute ass, but it had actually also penetrated my soul.
I never would have guessed that Grayson’s magic dick would domesticate me, yet there I was. Dickmatized, and badly. My rationality had completely disappeared.
It wasn’t just his dick I was into, either. I kept replaying in my mind the moment that Grayson had finally kissed me: the way his blue eyes had twinkled at me for a moment after as he’d paused and looked in my eyes. I thought of how dominant his kiss had been, and how I’d been so perfectly submissive. We had communicated so many unsaid things to each other in that brief embrace. His manliness had assuaged and re-assured me all night long, but with that kiss, he’d provided a healing balm for a lifetime of being a disappointed twink ragefully acting out revenge fantasies by conquering straight jocks. Grayson had made it safe for me to submit. I reasoned that maybe what I’d been searching for all those years was a man who deserved my unconditional submission.
He has to love me. He just has to.
It was quite a mindfuck going from the supreme level of intimacy I’d experienced with Grayson that evening to knowing that I wouldn’t see him again for two days – and I hadn’t even begun to plan for the reality that when I did see Grayson again, I’d have to pretend the whole experience had never happened. I’d have to deny the whole complicated web of feelings we’d spun during our lovemaking and try to go back to a platonic boss/employee relationship. How am I even going to get any work done with all the sexual tension between us? So much was weighing on me; I was physically spent and emotionally exhausted, but my mind was racing and I had no idea how to get it to stop. I was absolutely obsessed with Grayson; I knew it was unhealthy, but I didn’t care.
Whereas earlier I’d been thinking about the inevitability of another sexual encounter with Grayson, I was beginning to think the opposite. What if that was it? What if I spend the rest of my life without being fucked again? I knew that now that I’d had Grayson, no other man could ever satisfy me. It was Grayson or nothing, and it was unbearable to imagine my life without him in it.
Think about how Grayson feels, you fucking selfish prick. I’d been at least somewhat prepared to have a gun pulled on me. Grayson had been taken completely by surprise. I’d been single. Grayson had been forced to commit adultery – a serious sin in his religion. Then he’d found out that it had all been orchestrated by somebody he thought he could trust. Yesterday morning I was Nathaniel, Grayson’s star employee. But I was starting to realize that I had become… Nathaniel, the narcissist, the… rapist? I wondered whether that was even the right word to use when you get someone to fuck you by trickery.
You’re not a rapist. You didn’t force him to fuck you, you just forced him to admit that he wanted to. I didn’t see myself as a rapist, but I realized Grayson might. And if he did, I’d owe it to him to stay out of his life.
Sloppy, sloppy, sloppy. I scolded myself for coming up with the plan in the first place.
He’d been so decent about forgiving me. In fact, he’d forgiven me much too quickly. It was almost like his subconscious had forced him to prematurely forgive me in an effort to protect himself from having to confront the horrible thing I’d done to him. He has a whole weekend to think about what you made him do. You’re lucky if he doesn’t punch you Monday, let alone fire you.
For the first time in my life, I was confronted with a very dark side to myself that I’d never really acknowledged. And I didn’t like it.
I had just one trump card to play. Grayson had enjoyed fucking me, and I knew it. In spite of the fucked up situation that had led us there, our coupling had been mindshattering and life-altering for both of us.
I’m ashamed to say it now, but by this point I was spiraling badly. I desperately wanted to get Grayson’s attention, to pour my soul out to him.
I need to be bold. I need to strike while the iron’s still hot, before he forgets how good it felt for him to fuck his cum up into me.
I typed out, «I love you Grayson. I need your big fat dick back inside me again. Please come pump me full of your daddy jizz.» Then I just stared at my phone for a moment.
You’d think I’d be blushing as I was forced to observe the level of desperation I’d sunk to, but in my fucked up state of mind, it all made sense to me. I figured some long love letter would just scare him away. So I’d convinced myself that Grayson just needed a reminder of the pleasure that only I could give him.
Do I dare?
I consoled myself with the fact that I at least had Grayson’s sperm in the office freezer as my insurance policy. If he told me to shove off, I could grab that and keep it the rest of my life to remember him by – to have a taste of him whenever I needed it.
I pressed ‘send.’ The message showed as ‘delivered.’ No going back now.
I looked at the clock on Craig’s microwave. It was only 9:30 PM. Come on, Grayson. I know you’re still awake.
I checked back obsessively for about half an hour. Unfortunately, the message stayed in ‘delivered’ status. He probably blocked your number, you fucking stalker.
Craig’s door opened and he walked back into the living room. He was still shirtless, wearing nothing but his boxers. I couldn’t help it – my eyes darted to the dark happy trail on his abs, and I traced down to his package. He looked damn good. Almost tantalizing, even. I felt bad for ruining his chances with Tiffany earlier. It was entirely possible I’d cockblocked him – probably even left him with blue balls. Maybe…
“I can’t sleep,” he said.
“Me either,” I said. “I thought I’d pass out, but… I can’t stop thinking about Grayson.”
“You really care about him?”
“I love him,” I admitted.
“Man… he doesn’t deserve you. You’re such a great guy – and he’s married. Why don’t you find a single guy?”
“It’s a lot more complex than you think,” I said. “Grayson didn’t cheat on his wife. Not really.”
Craig raised his eyebrow at me. “Are you sure? Because it certainly looked like it.”
I laughed at the absurdity. Craig was a decent guy; I even thought for a second of telling him so, but I didn’t want to do anything he might misconstrue as flirting or romantic interest. I didn’t want to add humiliating him to my list of sins – and I didn’t want him to kick me out. My apartment - the location of my original sin of recruiting Buddy to my sick plan - was the last place I wanted to be. Even if my feelings for Craig were strictly platonic, I really hoped he would find someone special. For some reason, it suddenly occurred to me that I wasn’t sure if it was a man or woman he was looking for.
I can tell when a straight man likes me, but Craig’s interest in me was a little more than what I’m used to. I could see Craig being bi, at the very least.
“Wanna order a pizza or something?” he asked.
“Sure,” I said.
So Craig joined me on the couch and put on a movie with Aaron Taylor-Johnson. Normally I’m entranced by the man’s absolutely pendulous fucking dong, but that night I just couldn’t focus. My eyes were glued to my phone.
The message still read as ‘delivered’ instead of ‘read.’
Damn it, Grayson! I thought to myself; I was lucky I didn’t blurt it out loud. He has to be thinking about me, right?
I certainly couldn’t stop thinking about him. There was so much more that Grayson and I still needed to explore together. After that mindblowing fuck and the magical way his hot, hard dick fit into my asshole, I wanted to have him stick it into every orifice of my body at every angle, speed, and position possible – and on every surface possible. I wanted him to make love to me in my house, the office conference room, my car… and, fuck, wherever else we might have the pleasure of doing it. Which airline has the best toilets for joining the mile high club? I didn’t know, but I wanted us to find out together.
It actually got to be too much, and I excused myself to the bathroom. I needed to jerk off.
Grayson hadn’t touched my dick at all during our encounter – but believe it or not, that’s what I like. I’ve always been a total bottom. I’m actually turned off when my lovers want me to fuck them. I know, it’s weird.
I went to Instagram… and was glad to see that Grayson’s son Krell had added me! I hoped he’d have some pictures of his dad.
Krell himself was quite good looking, but not really my type. Instead of Grayson’s tall, broad shouldered, athletic frame, Krell was about 5’8” and skinny. He didn’t have a tight fade cut like Grayson did, but flowing blonde hair parted down the middle - kind of like the 90s mushroom cut look that was coming back in style. Krell was an absolutely gorgeous guy; if there were a citywide “Best Twink” contest, he would be pretty stiff competition for me. His face resembled Grayson’s - he’d inherited his father’s good looks, but there was something more cherubic about Krell. He had a sweetness and vulnerability that Grayson didn’t. He still had kindness in his eyes, but somehow a different kindness than Grayson - a more submissive kindness. I was into daddies, but if I wanted a twink, Krell was pretty irresistible.
I spent 10 minutes trolling through that Instagram, careful not to accidentally “like” any pictures that would let Krell know I was Instagram stalking him. Unfortunately, there were no pictures of Grayson.
So I had to use my imagination. It had been a long time since I’d masturbated. Anytime I was horny, I was used to finding some muscular straight guy to fuck me. Luckily, because of the evening’s events, I had some A+ material in my spankbank. I closed my eyes and pictured the intense experience I’d just had with Grayson. I was beating of furiously as I remembered what his lips felt like on mine, his manly scent, his grunts as he pounded my adorable twink ass. Grayson had demonstrated his caveman instincts to fuck his dick as far into my asshole as fast and as hard as he could. The normally mild-mannered, polite, stoic Grayson had been driven wild with animalistic lust by my sweet, submissive, helpless twink personality and beautiful hole.
I was close to cumming.
“Oh, shit! Sorry!” I heard. I opened my eyes, and there was Craig, who’d walked in on me.
“Craig, what the fuck?!” I asked. “Are you that fucking desperate?”
“What are you talking about?”
“You’ve been trying to fuck me since the moment I walked into your apartment tonight! Can’t you get a clue that it’s not going to happen?” I know now I was being a dick. Unfortunately, as I lashed out and just let out all the venom I had inside me, I didn’t realize how absolutely shitty I was being to Craig, who’d been nothing but nice to me.
“Dude, you are a fucking narcissist, Nathaniel. Do you just assume that *everyone* wants to fuck you? I have news for you, I don’t. I’ve been trying to be your friend. That’s it! Friendship, Nathaniel. Maybe something you could learn a little bit about yourself.”
Having given me a well-deserved scolding, Craig slammed the bathroom door behind him. Now I felt like shit. Dick deflated, I washed my hands and walked into Craig’s living room with my tail between my legs.
I sat down on the couch next to Craig.
“I’m sorry, Craig. You’ve been a good friend. I shouldn’t have said what I said.”
“You know you’re a good-looking guy, Nathaniel. But I’m not a scumbag like that. I wouldn’t try to seduce you when I can tell you’re not yourself,” Craig said. It struck me as an incredibly bizarre response; I was surprised that he hadn’t invoked heterosexuality as his reason. Curiosity got the best of me, and I had to know.
“Are you… are you gay, Craig?”
He laughed. “I’m definitely not gay. I mean, I love women. But maybe I’m… a little curious,” he admitted.
“You should try it some time. I mean, look at Grayson. He went, what, 45 years without ever trying it? And I think he just discovered a whole new side of himself tonight,” I said, grinning.
At the invocation of Grayson’s name, Craig suddenly looked a little sullen.
“Man, I can’t believe the boss is fucking you. Why, Nathaniel? You deserve better,” Craig said again. “Grayson actually fooled me. These Bible-thumper guys always turn out to be cheating on their wives or embezzling money or something like that, but I thought Grayson was actually for real – that he practiced what he preached. Turns out he’s a scumbag just like all the others.”
I felt guilty. For a second, I considered letting Craig in on the story of what had happened with me hiring Buddy to set up Grayson. After all, Craig’s sense of decency was being all turned around because of everything he didn’t know about the situation. That seed of guilt forced me to see things through his eyes – through decent eyes. Craig already had the wrong idea, and was blaming Grayson for a situation that I’d set up. If anyone else found out, like if Buddy decided to post the video of Grayson and me on the internet, I worried that people would think that Grayson was the bad guy.
“Craig, really,” I said, “it’s not what you think. Please don’t judge Grayson as some kind of hypocrite.” You saw the ropes, dude. Doesn’t that indicate that what happened was kinda sorta against Grayson’s will? But I decided against telling Craig anything.
Craig was a friend, and I couldn’t risk alienating him. I’d already acted like a total asshole by suggesting to Craig that he’d been trying to fuck me, and I didn’t want to give Craig further reasons to be angry with me. I’d realized how empty my life was, and it was a huge gut punch. For years, I’d surrounded myself with a revolving cast of straight men to seduce. I’d been using them as substitutes for actual connections and friendships. Here was Craig, offering me the olive branch of genuine friendship, and I need to take it. It was time for me to learn that there were reasons to talk to attractive men aside from getting them to fuck me. I had to learn to base my self-esteem on something other than sex, and accept that I was worthy of friendship.
“I’m confused,” Craig said, after a long pause to try to figure out what he could have possibly misinterpreted about the situation he’d walked in on. “When I walked in, you guys were naked. You obviously had sex. How do you figure that doesn’t count as cheating?”
“Somebody forced us to do it,” I said. It was technically true, even if I’d omitted the fact that I was the one who set it all in motion. “Look, I can’t really talk about it. It was something that I wanted to happen, and it did. Just not in the way I’d hoped.” Again, technically true.
“Nathaniel, come on. You expect me to buy that… what, some burglar forced Grayson and you to fuck?”
“Yes. Please don’t tell anybody, Nathaniel. I know Grayson is really scared about people finding out. Do you promise you won’t tell anyone?”
“I promise,” said Craig. “But, Nathaniel… if somebody forced him, he’s not gonna want to do it again. It’s probably a really painful memory for him. Don’t you think you’re wasting your time pining over him like this?”
“Maybe. Hell, probably. But I can’t help feeling the way I feel.”
Feeling dejected, I looked down at my phone. My text message to Grayson was labeled as ‘read.’ My heart jumped.
If there had been any question before, Grayson knew I wanted him to fuck me like a bitch in heat again. All my guilt and rumination vanished in an instant, replaced by hope and lust. Some part of him has to be considering it, right? No red-blooded male can resist my hot twink body and fuckable bubble butt.
I couldn’t pay attention to the rest of the movie. If Aaron Taylor-Johnson dropped trou, I was totally unaware of it (a sentence I’d never thought I’d write.) I sat glued to my phone waiting for Grayson to respond… but he didn’t. The dude just left me on ‘read.’
I dozed off at some point, and before I knew it, I was in some kind of alternate version of my senior year of high school where I was eighteen again. I kept seeing myself dancing around in a sexy, shoulderless black dress, interspersed with moments of bonding with my dad, like some kind of movie montage.
Then I started seeing Grayson, but he was different. Instead of the buttoned up, suited, wealthy, family-man Grayson that I knew, he was a working-class, early-twenties man who evoked danger and grit. He kept sneaking sly, sexy smiles at me. I was attracted to him, but scared of him at the same time. My fantasy version of Grayson reminded me of a time before I knew I could seduce straight guys. He made me remember the alpha jocks I’d always wanted to get to know but had been much too afraid of to approach. I’d just known all my life that I’d be rejected by them as not good enough, so I’d never even tried.
In my fantasy, Grayson and I were making out in the backseat of a beat up car, the kind an 18 year old would have as his first carl. I was such a gentle and delicate creature, and I was so frightened by the strong figure of maleness that Grayson encompassed, but also turned on by the promise and potential represented by the hardness I could feel in his jeans. He didn’t ask for my virginity; he just took it, but he assuaged my fears and promised me that whatever happened, he would always take care of me. My fear of Grayson disappeared as he dominated me and made me his.
Grayson used such sweet words, calling me all sorts of pet names during our lovemaking. I turned to mush in his arms; I felt no pain at all even though he was jackhammering me deep. The waves of ecstasy flowing through every inch of my body let me know that I was exactly where I was supposed to be. I knew I was born to be a perfect, sweet cum receptacle for an alpha jock like Grayson. He was the one to finally take advantage of my willing compliance. Submission was my destiny in life.
The dream was everything that I should have had in high school. I’d always been such a goody two shoes. If only I’d met Grayson then. He would have made the path for me so much clearer; I could have avoided the years of self-destruction I’d subjected myself to. My whole life, I’d been chasing the sweaty romp with a dangerous jock that I’d been deprived of in high school, when I’d needed it most. I felt full when Grayson released his warm love into me.
Next I was getting all kinds of visions and fantasies of myself pregnant with Grayson’s baby, and how frightening and also exciting it would be to tell my daddy that Grayson had knocked me up – that another man had made a baby inside of his perfect little angel. My daddy would be forced to accept - through incontrovertible proof - that a big, strong, dangerous man like Grayson had made love to me, his son.
I pictured myself at the office of the family doctor. He was examining me with my legs in stirrups. He lubed up his gloved hand and reached far up my butthole, feeling around as my dad sat in the room, observing, a blank and yet somehow betrayed expression on his face. I held my penis out of the way, which was good, as I was able to hide from the doctor the throbbing erection his search of my butthole had induced. The kind, gingerly old man who had been my doctor my entire life made eye contact with me as he professionally examined my anal cavity. I felt ashamed but also excited. Finally, after a few minutes of spelunking, the doctor bewilderedly announced to me and my dad that somehow I had fallen pregnant.
I was almost uncomfortable with how aroused the situation made me. I didn’t dare remove my hand from my penis until my arousal subsided at least a little; I felt like a complete freak being so turned on by my doctor and my dad being so focused on my anus.
I wondered how the doctor had felt knowing that his eighteen-year-old male patient had somehow gotten pregnant. Was there even a small part of him that was jealous he hadn’t been the one to impregnate me himself? As he had explored my anal cavity with his gloved hand, had there been even a slight increase of blood flow to his own penis? He wasn’t just a professional. He was a living, breathing human male. I wondered how sexually exciting my pregnancy would be to other males I knew.
I wasn’t just thinking about the doctor, who’d never ceased making eye contact with me as he’d explored my anal cavity. My dad had just been sitting close by, witness to everything. I wondered what thoughts had run through his mind.
All of those strange images - bonding with dad, dating a dangerous version of Grayson, dancing in a sexy black dress, having my asshole examined by the family doctor - were randomly interspersed with me traipsing along the river against the New York City skyline. I had a short blond pixie cut. I was still a boy, but a very feminine one. It was the strangest, most vivid fantasy I’d ever had; somehow it all felt so real to me.
My dad was furious at me for getting pregnant as an unwed eighteen-year-old high school student, but instead of yelling at me, he just turned completely cold. I felt desperate and alone. My dad had abandoned me when I’d needed him most.
And then, like a knight in shining armor, came Grayson. It was still the working-class, early-twenties version of Grayson. He told me he was going to marry me and take care of me and our baby. He smiled and put his hand on my belly and kissed me. I felt myself creaming my pants a little as the rebellious, kinda scary version of Grayson promised to make an honest twink out of me.
“Dude, what the fuck?!” Craig said.
I crashed back to reality. I woke up and realized I’d been having a strange dream where I’d been the main character in Madonna’s Papa Don’t Preach music video. Of course, I knew that it was not physically possible for Grayson to get me pregnant, but damn if it hadn’t been a titillating fantasy. In the real world, he had unloaded a huge, fertile load right up my anus only a few hours ago. If only by some miracle he could make me pregnant. Of course, I knew it was ridiculous.
I felt a pang of emptiness and longing. I envied women for their ability to carry the baby of a man they loved, and wished I could do the same for Grayson.
I looked down and realized that, while sleeping on Craig’s couch, I’d had a wet dream and ejaculated in my pants. The front of my pants and bottom of my shirt were all sticky and wet and jizzy now. I never would have known I could cum so many times in one day.
“Oh, shit,” I said, blushing.
“Uh, I guess that’s my fault for walking in on you before,” Craig said.
“I didn’t know blue balls could cause a wet dream,” I replied honestly.
“I don’t think they can, dude,” Craig said, laughing. “Fuck, I guess the old boss must really be a chad.”
Oh, Craig, you have no idea!
“I’m gonna take a shower. Do you have any clothes I can change into?”
“Uh, sure,” he said. While Craig went to his room to grab me something to change into, I grabbed my phone to see if Grayson had replied.
There was no reply. Underneath my message, it still said, ‘read.’ Fucking bastard!
Craig handed me a white towel, a white v-neck shirt, boxers, and a pair of shorts.
“Thanks,” I said. I walked into the bathroom and locked the door behind me this time.
I had a moment of stark self-awareness just then: I was stripping down to take a shower in Craig’s apartment past midnight on a Friday night after cumming all over myself on his couch. If you’d told me that even the previous night, I would have thought that that meant Craig and I were fucking.
It was amazing how much Grayson’s big daddy dick had changed my world.
It felt nice to take a shower, although, sadly, it meant finally cleaning the last remnants of Grayson’s sticky load from the inside of my butt cheeks. As I parted them to let my soapy hand in, my body briefly remembered the feeling of Grayson’s dick excitedly pistoning in and out. I wondered if Grayson had thought about it, too. I was confident that, if he had gone home and fucked his wife in desperation as I was assuming, he wouldn’t have been able to stop thinking about me instead – he’d be fucking her, but imagining my superior asshole instead of her gross, basic-bitch, middle-aged pussy.
I probably spent too much time in the shower, as my mind kept wandering back to Grayson. I had a moment of clarity where I could almost feel that Grayson was simultaneously thinking about me – almost as if through some kind of cosmic connection, our minds were linked for a brief nanosecond of time. It could have been wishful thinking, or perhaps the mental rantings of a twink who had been driven mad by dickmatization, but I could swear I was linked to Grayson’s thoughts for a moment, and that he wanted my beautiful butthole as much as I wanted his delightful dick. It was as if a force beyond either of our comprehension had crafted my butthole to be the exact right shape and size for Grayson’s cock, and both of us were aware of the other realizing it.
I’d been in the shower for half an hour at that point. Finally, I turned off the water. I had a squeaky clean butthole (as any self-respecting total bottom should strive to have); of course, I mourned the loss of Grayson’s sperm from my anal cavity and hoped he’d inject me with another generous portion of it in short order.
I dried myself off and put on the undershirt, boxers, and shorts that Craig had given me. My heart skipped a beat as I picked up my phone. Some kind of intuition told me Grayson had responded, and I was right. Anxiously, I opened our text thread to see his response.
I re-read my message to Grayson from 3 hours ago: «I love you Grayson. I need your big fat dick back inside me again. Please come pump me full of your daddy jizz.» I blushed. I wished I could have restrained myself and not sounded like such an obsessed stalker. Oh well. I braced myself, knowing his response could be different than what I wanted to hear.
Grayson’s reply read, «I need to see you.»
TO BE CONTINUED. . .
Thank you to neuroparenthetical for editing this story.
