Stepdaddy Issues Ch. 01

SingleDad51: So that's what you look for in a guy, huh? Not judging, just curious. A little older, a little authoritative? What do you like about that?

Barry didn't really know how to answer that question with anything else but "everything". It took him a while to answer that.

hornyboi123: hard 2 answer. its just hot. makes me feel good, u kno? like an older, bigger guy just makes me feel comfortable and fuzzy. and who maybe talks dirty 2 me and stuff. makes me want to just service him, do whatever he asks of me. i dont even care bout my own needs tho, just want to get him off

Reading that message felt strange to Stavros. If a girl told him something like that, it would make him as hard as a rock. Reading these words, which themselves could belong to a girl or a guy, made him feel intrigued. He shifted in his seat absentmindedly, feeling that the way he was sitting was now uncomfortable for some reason.

SingleDad51: Damn! With the way you talk about sex, you could have fooled me into thinking you weren't a virgin.

Barry chuckled. He got that a lot. His fingers started typing an answer while his cock started twitching in his comfortable sweatpants. Even though they weren't exactly talking dirty, chatting with this particular stranger started to turn him on... a lot.

hornyboi123: what can i say ... i know what i like :pp and i feel like i would be good @ sex. or at least pleasuring the other

Stavros didn't know how to continue. Something urged him to ask the young man about more details, but he didn't want to look like a pervert. And why did he even want to hear this stuff anyway? What some strange man on the internet would like to do with another guy. And yet, the strange feeling of curiosity was there.

Luckily for him, he didn't need to decide on an answer, because a new message arrived on the screen.

hornyboi123: just talking about this stuff makes me hard

Barry wasn't sure why he said that. After he sent that, he started to come to terms with the fact that the conversation was probably over. It was getting a little too raunchy, and no straight guy would be down with that - no matter how polite he was. He rubbed his cock through his sweatpants and just as he was starting to think about just closing the chat and beating off to some porn, he got another message.

SingleDad51: I have to confess... I'm getting a little hard too.

Stavros' heart was beating fast. This was uncharted territory for him. He didn't know why his cock started pushing against the cloth of his tight, white briefs - this conversation wasn't anywhere near close to what he usually jerked off to. The main stars of his imagination, or his porn of choice, were always women. And yet, now he was confessing to another guy that he was making him hard. It was scaring him a little bit.

He felt ridiculous - why was he feeling on the edge of his seat, his heart beating like he was about to take an exam or go to a job interview, when it was a normal night, with him safe and sound in his bedroom?

His fingers started tapping on the keyboard again.

SingleDad51: Sorry. I hope you don't think I'm weird.

Barry adjusted himself on the bed and pulled his laptop closer. His erection started getting in the way a little bit. He was now fully hard at the thought of this straight daddy getting hard because of what he said. He knew he had to tread lightly - he didn't want to scare the guy off.

hornyboi123: why wud i think dat? its a hot convo. nothing to be ashamed of

Stavros pulled onto his manhood through the cloth of the briefs. He wasn't exactly sure what he was after, but he knew he wanted more.

SingleDad51: Would you like to tell me more about what you would do to a man?

Barry fished out his cock out of his shorts - he started getting really horny and didn't want to stain his clothes. He started typing only with one hand as his other one rubbed his manhood slowly.

hornyboi123: well first i wud kiss him ... like a lot and everywhere. i would go slow and tender and i wud whisper that he cud ask me to do anything he wanted from me, that im only there 2 make him feel gud. and then i wud slowly strip him, make everything real slow ... and then succ on his cock while looking in2 his eyes

Stavros felt the heat of his dick in his hand as he slowly started stroking the erection that was growing more and more in his briefs. He knew he could imagine a woman saying these things to him... but he didn't want to. No, this was just fine.

SingleDad51: And then what?

Barry smirked, as he stroked his throbbing cock slowly. Whoever this guy was on the other end, he wanted it badly. He wondered how far he could get with this guy.

hornyboi123: then i wud succ his fat cock slowly and moan like a little bitch and suck up all of his precum, get dat slick stuff all over my mouth and make him watch me play with it wit my tongue

Stavros let out a quiet moan. He couldn't keep it in his pants anymore - his uncut seven-inch cock got pushed a little bit too far and could no longer comfortably fit into his tight briefs, so he just let it out. He looked down at his throbbing cock and paused for a while. Was he really ready to do this with another guy?

Another message. His eyes jumped back to the screen.

hornyboi123: ofc it wud help my imagination if i saw the cock i wud be sucking on

I should log off - that was the first thought that entered Stavros' mind. But it didn't last there for very long. No matter how strange and alien it felt, he wanted to do it, he wanted to expose himself to this stranger on the internet. It was all so dirty, new, and exciting. His shaky hand grabbed his cock and positioned it as he opened his legs. He had never taken a dick pic before. Part of him felt stupid, he felt like he was some kind of a horny teenager, but part of him was just exhilarated at the thought of someone being so interested in looking at his cock.

He felt a bit embarrassed at how long it took him before he settled on a picture that he was satisfied with. When he finally had it - a picture of his shaft, with a glimpse of his hairy balls, legs, and a neutral background - he sent it. He felt self-conscious about it immediately after.

SilverDad51 sent you 1 photo - Download - Discard

Barry was so impatient, that it took him three clicks before he managed to hit the correct button to download and view the photo. After he saw it, he groaned with excitement and his cock leaked out a big bead of precum. Then, another message appeared.

SilverDad51: Sorry, it's probably not very good. Some girls I've been with were kind of weirded out because they're not used to uncut guys.

Barry was quick to answer, his typing hand working hard to reassure this man.

hornyboi123: well sorry 2 break it to u but those girls had shit taste then. this pic is makin me so fukkin hard .........

Stavros blushed, even though he was in the room alone.

SilverDad51: You really like it, then?

Barry started stroking himself faster, using his free hand to type. He had the picture open in one window and the chat with the stranger in the other, so he could look at both at the same time. His mind was completely focused on this hot stranger.

hornyboi123: i would be succing on that thing so hard daddy

Stavros felt something run through his body as he read that word. No girl he ever slept with had ever called him "daddy" before. He never thought he would be into that kind of dirty talk - when he saw other people talking about it and making fun of it, he also always thought it was kind of weird. But there he was, feeling exhilarated at being called that word, only eager to lean into it and hear more from this mystery guy.

SilverDad51: You're making daddy very happy right now...

Barry kept stroking his raging hard shaft, making him hornier and hornier. As he imagined sucking this man, an image started to form in his head. Hefty but nicely formed body covered in hair, with a few gray hairs here and there, deep voice, eyes both strict and gentle at the same time...

As usual, the image in his head came somewhat close to what his stepfather looked like.

The young man grabbed his phone and positioned it down. Usually, he was too shy to take pictures of his body, especially in an erotic setup, but something about this stranger just made him so horny he couldn't resist. But he knew it wouldn't be safe to include his face in the picture and just send it out. He made sure only his erect cock - not as big as the one of the stranger, but equally hard - and his asshole - tight and shaven, as Barry liked to keep it - were in the picture. Then, he quickly transferred the picture to his computer and promptly sent it to the stranger.

hornyboi123 sent you 1 photo - Download - Discard

Stavros stroked his cock, feeling strangely excited as he opened the attachment. Sure, he would occasionally check out other men in locker rooms or public showers, but that was just for a quick, innocent comparison. And yeah, he could definitely appreciate another man's body on a certain level, just like one would appreciate a nice picture or a statue. He never really pictured it as something that could turn him on though.

But the picture he was staring at that moment was hot. So fucking hot. The boy sure knew how to take care of himself, keeping the whole area nicely groomed. Stavros was surprised at how much he liked everything that he was seeing - the juicy-looking throbbing cock and the incredibly tight-looking hole under it. He had never tried anal, but suddenly, he found himself asking why.

SilverDad51: You're giving me ideas that you shouldn't with that picture, boy.

Barry had trouble typing, with his hand stroking himself furiously and with his mouth moaning softly. He had to be careful with the noise, his stepfather's bedroom wasn't that far and the walls were thin as paper.

hornyboi123: i wanna hear all ur ideas, daddy

Stavros was never that big on dirty talk - so he was surprised at how easily the nasty words started coming out of his fingers and onto the glowing screen in front of him.

SilverDad51: I would spread your legs softly, and play with that hole of yours with my tongue. I would make it really nice and wet and fucked you with my tongue until you begged me for more.

Barry followed the incredibly detailed fantasy he was reading off of his screen and spit on his hand to lube up his finger. He started pressing it against his hole and looked at the chat and the dick pic next to it, imagining it was the stranger's cock entering him instead of his finger. He was surprised to see how dirty the stranger suddenly got, but he wasn't complaining.

hornyboi123: ur makin me so fukkin hard... what would you do after dat daddy

Stavros knew that he wasn't going to last much longer at this tempo. But chatting with this guy was so much fun - he wanted to see how far he could push it.

SilverDad51: Then I would take my cock and make sure you're not a virgin anymore.

That was too much for Barry. He yelped out before covering his mouth with his free hand. He felt a wave of an orgasm starting deep inside him and slowly pushing through his entire body. He let out a couple silent yelps as his cock started shooting hands free, covering his entire chest with hot, sticky cum. His fingers tried to keep up with the messages but failed.

hornyboi123: im cummjxsfarewwhsgxgtyty

Stavros couldn't hold back anymore either. This random guy was making him feel like a woman hadn't for a very long time. He wanted to be there with him, personally making sure this guy cum hard for him. The image of having someone so eager to be with him, riding his cock, begging for more, and calling him "daddy"...

"Oh fuck..." he grunted, slamming his hand onto the mattress as his other hand brought him to a climax. Usually, cum only trickled out when he was jerking off, but this time it was a full-on cumshot, splashing onto his chin and his entire body as his cock kept shooting and shooting.

Both men brought each other to a powerful orgasm at almost the same time, not knowing that they were only a few feet away from one another.

Barry panted heavily. He reached for the wet wipes he kept close to his bed and started cleaning his hands. The bliss of the orgasm kept pulsing through his head as he did. Then, a new message on the screen caught his attention.

SilverDad51: I can't remember the last time someone made me cum this hard.

Barry grinned to himself. His slowly softening cock was proof of how much he enjoyed that too.

hornyboi123: first time another guy made u cum?

Stavros lazily wiped his sticky hands on the sides of his black t-shirt - it was covered in cum anyway. He was surprised that he didn't feel shameful or weird after doing this. His shaky hands went back to the keyboard to answer.

SilverDad51: Yeah. I've never done anything with a guy before. I can't help but think about what all this would be like in real life.

Barry looked at that message for a long time. It almost seemed like the guy was hinting at something. His profile said that he was also from North Dakota... Would it be crazy to suggest going a bit further than just an online conversation?

He had never done anything like that before. Most guys on that website gave him the creeps and he would never think of going any further than a quick, jerk-off chat. But with this guy... he was so hot - at least from what he described on his profile - and so polite. But of course, he could be lying...

His heart was beating hard as he reached for the one-use phone that he bought a couple months ago - he was posting an ad online about selling his old bike and didn't want to put his actual phone number. He figured that not giving a real phone number would be a good safety precaution.

hornyboi123: maybe it wud be good in real life ;))) we shud talk about it sum more

hornyboi123 shared a phone contact - View - Dismiss

Stavros paused as he saw the message. He didn't know how to react to that. Sure, online fun was one thing, but it was something else to take that to the real world. He wasn't sure how he felt about talking to a guy outside of this anonymous online environment...

On the other hand, the images of this guy doing the stuff that he described to him were still running through his head.

Eventually, he decided. He got out of bed and walked to his desk. He opened a drawer and took one of his old work phones. The last one still worked. He looked back at the computer hesitantly as he waited for the old, clunky phone to start up. This was all so new to him.

Meanwhile, Barry kept staring into his phone screen. He didn't know why it felt so important to him to get a message from this guy. His mind was racing. Was he too forward? Should he have suggested swapping emails or something instead? Phone numbers were still a very personal thing for a lot of people. Perhaps it was too much too quickly.

When he didn't get a message in a couple minutes, he sighed and dropped his phone on the bed. He got up, feeling the sticky load covering his entire body, which made him feel uncomfortable. He needed to take a shower. Hopefully, his stepfather was asleep already - it was late, and he didn't want to attract any unnecessary attention.

As he was heading for the door, a chime stopped him in his tracks. He turned around to see a new message notification on his phone. The screen informed him about a new message coming from an unknown number. The boy smiled, forgetting about the shower as his fingers started typing back.