Stepdaddy Issues Ch. 02

Story Info
The oblivious duo arranges a meeting.
5.4k words
4.79
16.1k
43

Part 2 of the 3 part series

Updated 06/11/2023
Created 06/06/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It was already very late at night and the house was silent. Barry was just getting back home from the library. His schoolwork was crazy lately and he needed to spend full evenings researching information for the upcoming essay. But despite the stress and amount of work to be done, he had a smile on his face - the reason why the research took him so much time was also because he spent a long time sexting the mysterious stranger he met online a couple days ago.

The situation was perfect for him. The two of them haven't even exchanged names, but what they did share was amazing sexual chemistry. The fact that they didn't know each other only made it hotter, and that was the reason none of them wanted to break that. Throughout the day, they kept sending each other dick pics and dirty texts but throughout the night, they would have surprisingly deep conversations. Barry was always careful not to disclose any personal information or anything that could personally identify him - in case he was wrong about this man. And his mystery stranger seemed to share the same reservations.

That didn't mean that they couldn't connect with each other though. Sometimes Barry would talk about how lonely it felt to be gay in a small town, how overwhelmed he felt at school and generally he reached out every time he was in a bad mood because talking to the stranger always made him feel better. The stranger was less keen on being open, but Barry could tell he wasn't really happy with his dating life, that his work was starting to get on his nerves and that he had a somewhat distant relationship with his kid. He didn't know whether it was a son or a daughter, and the stranger didn't really get deep into this topic - Barry had a feeling that it was because the stranger didn't want to make himself look too old in front of Barry by mentioning his children too much.

Barry opened the door slowly and saw that there was no light inside. Not wanting to wake up his stepdad, he stepped lightly and headed for the stairs.

"Sneaking back from a party, huh?" a teasing voice sounded from the darkness. Barry yelped and almost lost balance - he had to hold onto the stairwell railing to stop himself from falling.

"Stavros!" he sighed, "God, you startled me... you know I wasn't at a party."

"Yeah, I know," Stavros emerged from the shadows, dressed only in his shorts, giving Barry a nice view of his impressive, hairy chest in the moonlight coming from the window, "I'm just giving you a hard time, kid. I know how hard you are working at school and I appreciate it."

Barry looked down and blushed. He knew that his stepdad was making an effort to be nice, but every conversation they had just made Barry feel terrible about the secret he was keeping from him - that he liked men. The fact that lately, Barry started feeling attracted to Stavros, didn't make things easier for him.

Stavros was the only family he had left - Barry couldn't risk coming out to him, so he just suffered in silence. He hated himself for it and he knew it was hurting his stepdad, but he just couldn't find the strength to do anything about it.

"Thanks..." Barry said, eager to just end the conversation and get into his bedroom.

"By the way," Stavros said, "I noticed you're on your phone more than usual lately."

His stepdad smirked at him, trying to make a personal connection. It was so hard to talk to his stepson, so he caught onto every opportunity to start a conversation with him. And Barry never had a girlfriend - Stavros was sure that if that had changed, he would be excited to talk about it.

"Is it someone you like, maybe?"

Barry smirked for a second, smiling at his stepdad coyly.

"Maybe. Yeah. It's probably nothing though. I don't think it's going to go anywhere. But it's nice."

Stavros nodded, feeling excited that his stepson was opening up, and decided to push the topic a little further.

"Just playing around then, huh? Well, you never know, kid. I really hope it works out for you. What's her name? Perhaps, if you want, you could bring her home for dinner or something."

The smile started slowly fading away from Barry's face. It was not a "she", obviously, and it was by no means anyone he could ever bring home to meet Stavros. The conversation only reminded him of the fact that he didn't find enough strength to come out to his stepfather yet.

"Um, yeah. I'll see about that. Probably not, though," Barry said, promptly ending the conversation before turning around and heading upstairs, "I'll go take a shower and sleep, I'm so beat from today. Good night, Stavros!"

Stavros stood there for a minute longer and sighed. He loved Barry and he knew he would never give up on him... but moments like that hurt. He decided not to think about it too much and headed for the kitchen to pour himself a glass of water.

As he filled up the glass, he felt a slight vibration in his right pocket. His eyes lit up and he quickly reached inside to pull out his old work phone. The mystery guy he was chatting with sent him a message.

New message from "Guy From Online": hope u had a gr8 day stud!!!

Stavros smiled. Despite the atrocious grammar the boy used to express himself over text, messaging him was the only thing that brought Stavros joy lately. He still couldn't believe he was sexting a guy... and a rather young one, at that. That part made him feel strange and a little bit ashamed at times - this guy was nineteen - young enough to be his son. But he would be lying if he said it also didn't turn him on like crazy. The daddy/boy dynamic that they incorporated into their sexting was something Stavros didn't know he enjoyed before. But now that he got a taste for it, it was everything he wanted to do.

They had this strange relationship of not sharing much personal information and yet they shared so many intimate details over those texts. An observer would probably think that it's crazy to talk so deeply with someone you don't even know, but Stavros didn't care what anyone else thought. In the last couple of years of his dating life, this was as close as he ever came to a connection with someone, and he wasn't going to give up on it.

He started typing away a response, while he felt his dick twitch in his shorts - that happened often to him when texting this stranger.

New message from "Internet Daddy": What's my boy doing up so late? Shouldn't you be in bed?

Barry snickered to himself as he saw the response. He was laying in his bed, with the light off - so Stavros wouldn't suspect anything and ask more questions - and staring into his phone. He felt at ease every time he talked to this stranger. He felt like he could ignore everything else that was happening in his life and just focus on this harmless, virtual fling. He started typing away a response.

Composing message: the boi was doing sum serious studying ;))) just got back home cuz i had 2 go all the way 2 rockville library just to get this one book!!!

His fingers were typing a little too fast for his own good. He sent the message before he realized what he did. His smile faded away as soon as he realized it.

The location. He just practically said where he lived!

It wasn't that he was afraid of this stranger. It was more about the unspoken boundaries they set with each other. The real-life identity wasn't important and keeping it hidden made it less real. And keeping it less real meant that it could just be a comfortable outlet.

But now Barry put that in jeopardy. Maybe the stranger wouldn't notice it? Barry bit his nails nervously as he waited for the stranger's response.

New message from "Internet Daddy": Oh, you live close to Rockville? That's cool. I actually live super close to Rockville too.

Barry started feeling nervous. Now was the moment, where the man would surely insist on meeting him, and this all would just turn sour, too real, too...

A chime indicated a new message.

New message from "Internet Daddy": No worries. I know you probably didn't mean to share that info. It's ok, I won't pry. You know I will respect your privacy boy ;)

A part of Barry felt an intense relief as he read that - but, for some reason, another part of him felt silly. Why did sharing such a small detail feel so threatening? And what exactly was he scared of? He didn't like to overthink things this hard and he felt a little ashamed of his emotions.

It was at that point he decided that maybe he was willing to risk it to go a little further with this stranger...

Composing message: glad i finally taught u 2 use basic emojis ;) :P i know ill get u 2 talk normally one day LOL!!! and yea i didnt mean to type dat. but now that i did and now dat we know we live close im thinking what do we do about it ... ;)

Stavros leaned against the kitchen counter. He completely forgot about the glass of water that he poured for himself and was now completely invested in the conversation on the phone. He had the same dilemma as Barry did. This texting thing was hot and easy, but he wasn't sure how he felt about an actual meeting. He knew from experience how real relationships can get very fast. And with such an age difference between them, Stavros was feeling very antsy about the idea - especially since he had a stepson the exact same age. How would that even work?

New message from "Internet Daddy": I know what you're hinting at. I don't want you to misunderstand me - I would love to see you. But it's been ages since I've gone out with someone like that. And it usually doesn't end well when I do. Not sure if it's a good idea.

He slammed his phone on the table after writing that message, frustrated with himself. He felt like a coward. Sure, it was probably a responsible thing to turn down a date with a nineteen-year-old, but he also felt that his fear of ruining the only good thing in his life - these conversations.

He wasn't expecting the stranger to reply after that. He certainly wasn't expecting the reply to come within seconds.

New message from "Guy From Online": dats cool. i totally get that. im a little scared too and i understand

It only took a couple of seconds before the new message. Stavros was always surprised by this whenever they were texting. How was this young generation so quick at typing on the phone?!

New message from "Guy From Online": it doesnt hav 2 b a date that ur used to tho ... it can b just about sum fun ;) dat way we can keep things exactly the way they r right now ... ;) ;)

Barry couldn't believe what he was saying - he was usually so timid and careful about everything - and now he was proposing to hook up with this stranger? He knew that a bit of a distance was good - that way, they wouldn't have a chance to break the mystery element of their relationship. There was one way to meet up while keeping that distance. A very dirty, but also very hot kind of way to do it.

Composing message: i heard of this small public toilet right @ the edge of rockville u know. one of the stalls has a hole in the wall ...

Stavros looked at the phone for a couple of seconds. He slowly felt a smile appearing on his face and his cock twitched again in his shorts.

Composing message: Oh, the boy has some dirty ideas, doesn't he... Tell me more.

***

"Going somewhere?" Stavros asked his stepson, as he saw him leaving the house. It was a beautiful, sunny Sunday afternoon - the day he had his hookup scheduled with the mystery guy. He was a little surprised to see Barry leave the house - usually, the boy kept to his room on Sundays playing video games.

Barry looked at Stavros and tried not to show the panic in his eyes. He wasn't good at lying - especially to Stavros. But he knew that if he wanted to have this sexual experience with the amazing hot daddy he was looking forward to for almost a week, he would have to play it cool.

"Um, yeah," he said nonchalantly, as he adjusted his empty backpack - he only took it with him so Stavros wouldn't get suspicious about his fake plans, "I'm going to my classmate's for a bit, we're going to do some studying together."

"Oh, okay," Stavros shrugged, "You didn't mention that. Are you gonna be back for dinner? I was planning to cook tonight."

"Sure, yeah, I'll be back for dinner... Probably," Barry answered, feeling a little bad again about the lack of communication with his stepdad, "Sorry about not telling you about my afternoon plans in advance. Did you want to do something this afternoon?"

Stavros responded with a chuckle.

"With you? I gave up a long time ago, mister! Your stepdad actually has some plans of his own today, would you believe that?"

He said that with a cheerful tone and added a wink, so Barry knew he was only teasing. He knew Barry could be sensitive to these kinds of things, but this time it landed. His stepson cracked a small smile.

"Heh... that's great. I'm glad to hear that. Enjoy your plans then."

"Likewise," Stavros smiled back and waved goodbye, "Have fun studying, kid."

Barry left the house promptly, hoping to avoid more questions that could blow his cover. He left the house and headed straight for the bus station. He had to take the bus - they only had one car that belonged to Stavros, and he was extremely protective of it. The few times Barry wanted to borrow it, Stavros would ask a million questions about where he was going to take it, and that wasn't the kind of attention Barry needed right now.

The bus to Rockville went every thirty minutes, and Barry was lucky to catch it at the last possible moment. It was almost empty, but it didn't matter very much, since it was going to be a short ride anyway. Barry sat on a seat next to a window and looked out absent-mindedly as the bus slowly took off.

He was nervous - but the good kind of nervous. He had never given a blowjob before. Hell, he had never been alone with another guy naked! For a second, he wondered if this was the right way to have his first experience - at a glory hole with someone he didn't even know by name. Barry wasn't dumb - he knew that it was a risky idea. He relied solely on the comfortable feeling he had from this mysterious stranger. But then he thought that's probably what every serial killer victim thinks before they get themselves murdered...

He took a deep breath and calmed himself down. The excitement of the situation kept him going. He was supposed to meet the man at a public restroom next to Rockville in forty-five minutes. The thought alone made him uncomfortably hard for the whole time on the bus.

***

Stavros pulled over in the deserted parking lot next to a small hut with a sign that said "Restrooms" above the entrance, looking around. Not a single person in sight - just empty fields, some woods in the distance, and the deserted road. A strange place to have his first experience with a man for sure... But he was already committed.

He spent some time in the car, even though he was already running a bit late for his meeting. He felt his palms growing sweaty on the steering wheel while he was grabbing it. The sexting has been incredibly hot, but this was another level. This was real, very real. Perhaps too real?

Stavros was close to just starting the car and driving off. The pressure was strong, but the curiosity was stronger. He had been hard the entire day just thinking about his meetup with the mystery boy. And it had been so long since he last got a blowjob...

What was the worst thing that could happen? A bad blowjob? Awkward conversation over text later?

Fuck it. Stavros got out of the car and slammed the door shut. He stepped up to the bathrooms and look at the building before going in. It was basically a big, old metal container repurposed as a highway stop for truckers to take a leak in peace. It was covered in rust and dirt - so much so, that even the sign that said "Restrooms" was barely readable. It was apparently functional, though, and they had someone to do some basic cleaning regularly.

Well, "cleaning" might have been a strong word...

He entered into a dim walkway that branched off to two sides - men on the left and women on the right. As he turned left, he saw a long room that reeked of sweat, piss, and bleach. Everything was very old and it was maintained terribly, but at least it wasn't completely dirty. The sinks were on the left, urinals were on the right and the far side of the room had three stalls.

Stavros's heartbeat quickened when he saw a shadow from the crevice under the door of the third stall. He cleared his throat to let the guy know of his presence in the room.

Meanwhile, Barry was just sitting on the toilet with his pants up, playing on his phone. His "date" was late, but he figured he would give it some time before he gave up waiting. As he heard the cough, he sprang to attention. What did people usually do in this situation? He coughed back awkwardly and immediately felt embarrassed. Was he supposed to say anything?

The tension was high. Both of them were nervous and neither one of them could find it in them to break the awkward silence. It was just too real.

Then, Barry's phone vibrated, signaling a new message.

New message from "Internet Daddy": Nervous?

Barry stared into the phone and then into the stall door in front of him, knowing the stranger was there, standing and waiting. It felt strange to be texting when they were just inches away from each other, only separated by a thin divider - but it also felt comforting. They were used to texting.

He started typing a response.

Composing message: yea ... a bit. but i also really want it

He hesitated before he typed another message:

Composing message: come in. second stall

Then, he heard the heavy footsteps again, heading for the stall right next to him. He felt probably the most excited that he's ever been in his life! He sat on the toilet, his eyes glued to the small hole into the wooden divider that was probably cut ages ago by someone who also really wanted to suck a dick and waited. Even seconds felt like years to him at that point.

Stavros opened the door and checked the inside of the stall. An old, but luckily empty and clean toilet, an empty roll of toilet paper in the holder on the side, and a small window - high up so nobody could peek from the outside - that provided some light. And then he finally found what he was looking for - a hole in the wall on the right, lined up with duct tape to protect the skin of its "customers" from any cuts. He took a deep breath and stepped closer.

Barry's view was much dimmer because he didn't have a window in his stall, but he did have a clear view of the stranger's bulge. He breathed out in excitement - it was really happening. He has been fantasizing about something like this for so long. He wasn't a big romantic, this dirty and gritty environment was perfect. To some people, it might seem weird but to Barry, it was a huge turn-on. Sucking off somebody he didn't even know by name in a dirty old public toilet.

He leaned closer as the stranger played around with his belt. Then, he heard the sound of the zipper being undone and saw the jeans open and reveal a bulging pair of boxer briefs. White, tenting, and carrying a brand that Barry recognized. It was the same brand of underwear his stepdad used. What a strange coincidence.

Barry didn't really think about it twice - it was a very common brand of underwear. In fact, it only turned him on more. He fantasized about sucking off his stepfather so many times in the past and the thought of this stranger wearing similar underwear only made him more impatient to get his first cock in his mouth.

Then, the moment came. The hand pulled the waistband down and revealed a thick bush of dark hair. And then the shaft. Barry, of course, already saw the stranger's cock in various pictures and angles on the photos they exchanged, but seeing it in real life was something else. The thick base, the fat, branching vein in the middle, the purple tip... All the details were what made it perfect. The stranger's cock was semi-hard at that point, and the tip was shiny from the precum - the stranger must have also been excited about Barry's mouth. Slowly, the whole package pushed through the glory hole, closer and closer to Barry's face.

12