Sometimes it just goes wrong

[PigBoyDallas]

Its been hot as shit here in Dallas and when Caleb, a fuck bud, offered me the opportunity to come swim in the pool at his place I took him up on it. Caleb's one of the cute Anglo boys I've been messing around with who just graduated high school and has nothing to do while his parents are at work. He didn't get a summer job and instead is doing whatever he wants all day long. Sometimes that's me coming over to get fucked and I'm down. He's been all top with me, not that I mind as he's really hot and has a nice sized dick. I have no idea whether he's gay, straight, or bi, and honestly don't care. That he's fucking me probably means he's at least bi, maybe gay. He's never mentioned a girlfriend, or for that matter a boyfriend, so hard to know. He did admit he's been with guys from school before and its clear from fucking me that he's probably been fucking some of them too. But he's never asked me to fuck him and I pretty much just let him take the lead. I got to his house already wearing my swimsuit and before we're even out to the pool he's pulled me into his bedroom and fucked a load into me. We shower off after together and he made fun of me for wearing a bathing suit saying he had no plan on wearing one and that I shouldn't either. I have a raging hard on as he didn't get me off when we fucked and I could only guess maybe he was planning to play in the pool. We grabbed some towels and headed out to the pool naked and jumped in.

I was kind of worried that they might have cameras out in the back by the pool and he laughed saying he'd turned them off and does that when he swims as he likes to go naked. He admitted he preferred to swim naked and we were messing around in the water, kissing and playing with each others dicks. It was nice to be in some reasonably cool water as it's into the 90s here and a heat index over 100. At one point we stopped messing around and he started kissing me, deeply and intensely as he was stroking my cock and I was stroking his. It seemed like we were about to do more and honestly, I was down for him fucking me in the pool. I'd done that before at Spring Break and it was pretty hot. Caleb suggested getting out of the pool and laying in the sun a bit and as I did he said he needed to go in the house for a moment and said he'd be right back. He came back with two beers and his bottle of lube. It was a little early for having a beer but I didn't care and as for fucking outside I'm always down. He handed me a beer and we clinked our bottles and he smiled at me and we laid back on our chairs sunning ourselves. He was quiet for a while then said he had a confession to make. He'd been at a party a week before and hooked up with a guy who wanted to fuck him. Caleb admitted he'd never been fucked before but was curious but kind of scared as he didn't really know the guy. He'd gone to his place and messed around and wanted the guy to fuck him, but found it was too painful and he was kind of scared as he didn't really know the guy and admitted he isn't on Prep. The guy wound up cumming on Caleb's ass and fingering his load inside Caleb, but Caleb admitted he didn't enjoy that. He admitted he wanted to get fucked but didn't want it like that. I asked what he meant and he said not with a stranger, but with someone he knew and trusted, someone who would be gentle and take it easy. I said I understood and that was how my first time was. He laughed and said he knew that I would get him and understand. And I got what he meant. He wanted me to fuck him and be his first. And now I got why he brought the lube out with him. I was kind of amazed this hot boy wanted his first time outdoors and was kind of shocked as he admitted to not being on Prep. That he didn't bring any condoms with it was clear he wanted it raw too. I pushed our chairs together and got back on, leaning in to him and started kissing him, shifting my body so that I was pressed up against him and he could feel my hard cock grinding on him. He was saying nothing and neither was I, I didn't want to disrupt what was going on. He paused for a moment to look in my eyes and said that he wanted me to fuck him, wanted me to be the first guy to fuck him, and that he trusted me and wanted it from me. I hardly knew what to say. I was flattered but wanted to breed him bad I could scream.

Caleb laughed and leaned back and I realized it was to grab the lube from beside his chair and hand it to me. "What would be easiest" he asked me and it seemed he genuinely didn't know how he wanted this to go down. I said it would probably be easiest for him to ride my dick so he could control how much entered him and what felt good. I laid my chair flat and rolled on my back and he lubed up my dick and started doing the same to his ass facing me with a look of fear on his face. He slowly lowered his ass down on my cock and I was fighting every urge to orgasm just looking at him. This was truly a fantasy coming to life and I was hoping he wasn't wanting his first time to "special" like some of the first-timer's I've been with. I could tell from his face it was a mix of pleasant and scary feelings that he enjoyed but which hurt. I remembered my first time and how I felt and started telling Caleb that it was cool, he was doing great, and asking if it hurt and also felt good. He admitted both were true and I told him to keep going. I was almost balls deep inside his ass and struggling desperately not to cum. Once I was all the way inside him I told him again he was doing good and to slowly start riding my dick. He did as he was told and I could feel my whole body shudder and I knew I was going to cum. Caleb looked stunned at what was happening and his eyes opened wide asking me if I'd cum. I said I did and apologized saying I'd gotten way too excited. He was still riding me gasping for breath and I noticed tears were slowly streaming from his eyes. I asked if he was OK and he said was, but didn't know what to expect but it was so different. I leaned up to pull him towards me and he collapsed on top of me, my cock softening and slowly slipping out of his ass.

I always feel bad with first timers as they have expectations that never match reality. Probably no one could have given Caleb what he wanted or expected, but maybe his first time wasn't so bad. He wasn't saying anything and honestly I was scared to ask questions, but he pulled me closer and tighter and thanked me. Honestly, I liked having his weight on top of me. I didn't feel at all guilty that I was the first guy to breed his ass. I'd wanted to from the first time we met. I'm glad my seed is deep inside him. I hope its all he can think about. But I'm not an asshole. Caleb isn't some "thing". I do like him and if he wanted to date I would be down for it. But I'm probably just some piece of ass to him, to use, fuck, and breed. We live in very different worlds. Caleb slowly seemed to recover and kissed me, thanking me, and it seemed genuine. He said we should get back in the pool and we did, even though we were slick with sweat, cum, and lube. We were swimming around again but not as close as before. But we drifted together again and he pulled me in to him and turned me to face the wall of the pool. I could feel him enter my ass and was eagerly begging for him to fuck me and cum inside me. He was on fire and pounding me hard, but saying nothing. I didn't care as I wanted his load in me and loved that we were doing it in the pool, out in the open. He blasted his load in me and said we should go inside, and we grabbed up the empty beer bottles, lube, and towels and headed back to his room.

Once there we headed to the shower to wash up, kissing deeply and intensely as we did. I apologized for getting too excited and cumming too quickly and said we could do it again. I regretted it almost immediately. He was apologetic, saying he was kind of freaked out but really enjoyed it and wanted to do it again. More than anything I wanted to fuck him there in the shower or go back to his bed and breed him again, but I knew that was just too much. I pulled him in and was kissing him, saying how hot he was and asking him if he was OK. He said he was OK but admitted he needed some time to process it all. I said I understood and admitted I felt bad as I didn't want him to be wierded out or hate me because of what we did. He said he didn't blame me and admitted he wanted it and knew what he was doing. I told him I cared about him but was only going to leave if I knew he was OK. He said he was and I left without saying more. Sometimes first times go great and sometimes you never know what went wrong. I feel like this is one that just went wrong.

[ErosWired]

1 hour ago, PigBoyDallas said:

I feel like this is one that just went wrong.

There’s wrong and there’s unexpected. I’m not sure that sounds so much wrong to me, based on your narrative. Wrong could have resulted in him clamming up, asking you to go, and never seeing you again, but that didn’t happen. He Topped you afterward. Plus, he said he needed to ‘process’, so the question is, what is he processing? The sensations he felt, his reaction to them, or both? Did he suddenly realize a switch had been flipped in him that told him he was gay for sure? Did you cumming in him force an examination of his definition of his masculinity? Is it simply a realization of what he has been doing to all the other guys he’s Topped and seeded, now that he’s had it done to him? In any of these cases, I think it’s only a fuck gone ‘wrong’ because there’s no way it could have gone ‘right’.

The young guy who came to me to learn to Top had a similar stunned reaction his first time he seeded me. He lay on me quivering for a while, then pulled away, visibly shaken. I asked if he was okay, and he said it had been the strongest orgasm he’d ever had in his entire life (at 21 he didn’t have much frame of reference, to be fair), but it was something he was going to need to process. He processed it, and returned for more practice.

[PozToxVersPig]

I dunno man - this whole thing reads super respectful and thoughtful, which is part of what someone might want for their first time.  I'd give yourself a path on the back here!  Given it was his first and you weren't just going to defile him, that's the best possible approach and it sounds like you stuck the landing.

[BlindRawFucker1]

“You” had nothing to do with anything going wrong—if anything actually went wrong.

 

He took the initiative, bringing out the lube and telling you what he wanted.

 

You let him take charge by riding your dick and allowing him to take you at his pace.  He totally took you, with apparently the expected amount of pain/pleasure.

 

Did you cum quickly?  Of course you did.  You are young.  I’m sure he cums quickly also.

 

In the shower, you talked to him and made sure he was okay.  Hopefully, after he thinks about things, he’ll text or call you.  You could also text and say “hello,” and see if he responds.

 

But, as others have said, he got into his head and has to think about some possible new realities about himself.

 

Let us know about any new developments.

 

Take care.