This is my first time publishing a story. I decided to take a detailed approach to my first time doing anything with another guy. It's not the most fast-paced story on the site, but that was intentional, as the story took some time to unfold and continues to unfold. Hope you enjoy.
I always knew my brother-in-law was…different. I had been in his life since he was 5, having met his sister when we were both 20. When Shawn (the brother-in-law) was a little kid, he wasn’t interested in the stereotypical “boy” things. As his friends got a little older and started playing sports, riding dirt bikes, and spending all of their time outside, Shawn stayed inside painting, and for a time in his early teens, he became enamored with knitting. The way he spoke, his mannerisms, and everything else gave him away.
It never bothered me, nor did it bother my wife. He was a great kid, very respectful, and had a huge heart. As for me, I have always been attracted to other guys, but I never let it get very far. Sure, when I was young, I had a friend who I would watch porn with, and we jacked off together, but there was never any touching. I wanted to, but was too afraid to approach the topic with him. No one ever knew about the things in my mind, and for years, that was fine with me.
At 16, Shawn confided in me that he was bisexual. I was cool with it, as I had known he wasn’t straight since he was a child. I was more shocked that he was interested in girls at all.
For the next year, he occasionally talked to me about people he was interested in, male and female. I always lent a listening ear, but the next year brought some other changes. Shawn was growing up. His shoulders were slightly broader, but he was still a pretty skinny kid. He couldn’t grow facial hair, even though he wanted to have a beard like mine. His brown hair grew longer and hit the bottom of his neck. Skinny, but getting progressively more attractive. No wonder he was bi; with his looks, he was going to be able to get anyone he wanted, male or female.
While I noticed that he was turning into a great looking young man, I certainly never acted on it. He was a minor and I was married to his sister.
A couple of days after his 18th birthday, Shawn confided in me once again. His parents had no interest in hearing about his personal life, as they weren’t on board with his lifestyle. I’ll never forget the text message:
“Hey Tommy. Can you give me some advice on something?”
“Of course. What’s up?”
“There’s a girl I’ve been talking to. She wants to mess around. I need protection, but I’m not sure what kind to get. Sorry if this is weird.”
It wasn’t weird at all. Honestly, I was glad that he was asking someone for advice. He certainly wasn’t ready to be a father, and I had no interest in raising his kid. I didn’t want to put my response in writing, as my wife would freak out about her little brother getting laid. She didn’t mind him being attracted to males and females, but she wasn’t ready for a conversation about him acting on it.
“Swing by the house next time you’re out. I may have something you can use.”
“Be there in 10.”
I knew what I was thinking, but the question revolved around if I would have the courage to act on it, and how Shawn would respond. He walked in without knocking like always. I played it cool and sat on my couch. I work remote and set my own schedule, while my wife works almost an hour from home. I had the house to myself, which couldn’t have been a better scenario.
We made small talk for a few minutes and I decided to see how I could broach the subject.
“So, are you asking me what brand you need or what size?”
“Both. I’ve never gotten anything other than a blow job. The girl said I was big, but I mean…she could’ve just been saying that.”
“As far as brands, I’ve been counting on Trojan since I was younger than you. They haven’t failed me yet. But I mean, to help you pick the right size, I gotta know…how big are you?”
He thought for a moment and held his fingers up. By the looks of things, he was saying six inches. Dammit; I didn’t want to see his fingers. I wanted to see what he had.
“Well, that’s…that’s something. Listen, you asked me this because you trust me. So I’m gonna ask you something. Have you sent anyone a pic of it when you’re…you know…hard? I kinda need to see it to tell you what size you should get.”
“I’ve done some stuff on snap, but I don’t save pics of it. Sorry.”
“Well hell. Let me think…”
I knew exactly what I was thinking, but I had to make it look like I hadn’t been thinking about this for a while.
“Shawn, if you’re long and thick you’ll need a different size than if you’re long and skinny. Also, you saying you’re long doesn’t mean you’re long. We’re guys…we lie.”
We both shared a chuckle.
“I’m not sure if you’re comfortable with me…seeing you or anything. But I also don’t wanna tell you to get the wrong thing. You wanna look at some stuff on your phone and get it up? It’s probably the only way for me to really know what you need.”
“I mean, I don’t care for you to see it. You go to the gym and stuff. I’m sure you’ve seen them before. I’ll go in the bathroom or something and take a pic for you.”
“Cool.”
I’d be lying if I said I wasn’t a little disappointed. In my mind, he was going to whip his cock out in front of me and I was going to get to see it for myself. He wasn’t the smartest kid in the world, and I was thinking I may be able to trick him into doing things my way. Still, I figured a picture was better than nothing.
He went into the guest bathroom and I sat awkwardly on the couch, knowing what was happening on the other side of the door. I had to work to hide the bulge in my gym shorts, as I didn’t need to appear too obvious. Maybe this was all for nothing. I was starting to think that I would just have to go back to those secret fantasies about him when I jacked off.
The door squeaked a bit as it opened. I heard him clear his throat.
“My phone died while I was in there.”
My jaw nearly hit the floor. There he stood in front of me, with nothing on but his t-shirt. His rock hard cock stood at attention, shooting straight from his body. A thick black bush surrounded it, and covered his balls.
“Oh shit.”
It was all I could muster.
“Yea. I went to take the pic and my phone died, but I’m supposed to go out with this girl this weekend, so I need to know now. What do you think?”
I motioned for him to raise his shirt a bit, but that was just so I could get a better look. The hair on his crotch stopped at his smooth stomach. He appeared to be smooth from there. I couldn’t take my eyes off his throbbing member for a bit. It wasn’t thick, but it had to be between six and seven inches long if it weren’t for the hair. Somebody needed to talk to this guy about shaving.
I think I know the perfect person.
Perhaps it was instinct, but he put his hand around his shaft and gave it a slow tug as I continued to gawk, hiding the ever-growing boner in my shorts.
“Well, you’re definitely long enough to get the job done, but it’s not super thick or anything. I think the standard pack should work for you. I don’t have any here, but next time you’re out, grab a box. Stay away from anything that says Magnum. Look for a light orange box.”
“Ok. Man I appreciate it. I would’ve asked Dad, but we both know he would have made some joke about me fucking a guy.”
“He’s kind of an ass to you about all that. I’m sorry. You don’t deserve it.”
“Well, at least I’ve got you. Alright. I’m gonna get dressed and take off. I may text you tomorrow if I have more questions.”
“You know you can text me any time, buddy.”
He turned around and walked back to the bathroom, and I couldn’t help but stare at his cute, smooth ass. For a guy who had so much hair on his junk, every other part of him appeared smooth.
I walked him to the door, the image of his mostly-naked body still fresh in my mind.
“One thing, Shawn. Your sister really doesn’t ever need to know about this. Me telling you what to get and you know…seeing you like that.”
“Man, I’m not saying a word to her about it. This is all between us. I promise.”
I believed him; he had never given me a reason not to.
As soon as he got in his truck, I laid across my bed and started massaging my own cock. I thought about Shawn, what I had seen, and the things that I wished I had been able to do. It didn’t take long for me to cum. I cleaned myself up, and went to sit on the couch. The rest of the evening, I found myself sort of zoning out, thinking about earlier in the day.
That night, I wanted to check in with Shawn, just to make sure that none of it had made him uncomfortable. He was an adult now, but there was still something about what had transpired. It was also painfully obvious that he was quite innocent and naive, despite his looks and age.
“Hey man. Quick question.”
“Go ahead Tommy.”
“We’re good, right? Nothing weird about earlier?”
“Hell yeah we’re fine. I need the help. I’ll get with you tomorrow if that’s OK. I have other questions.”
“I’ll be here all day. Your sister leaves for work at 7:30. All between us.”
I hoped that this was the beginning of something new, something forbidden. But if not, I at least had the mental image of his hard dick to get me through.
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