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The straight family friend drilled me in my own room... twice
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Part one is here

I was not expecting some random lucky encounter to get this much attention. You guys really wanted to know more, and I did say I've had two more encounters with James since that first one, so I guess I should talk about the next one.

I say that as if it was a chore but I actually find it very cathartic to share this, even if it's with a bunch of strangers on the internet. I've been keeping this for months and it's felt so surreal.

I have a few close friends that I consider trustworthy enough to keep stuff I tell them to themselves. I'm obviously talking about those friends I'm sure most of us have that know about me being gay and have known for a while. They even know about my absolutely crazy body count of four. Well, I guess five now, but they don't know about that. And yes, it's still five. This is really silly but I deleted Grindr a little while ago out of a sense of some twisted loyalty, I guess. Don't ask me, I don't even know myself what's up with my brain.

All I know is that until this absolute unit of a thirty-something-year-old man decides to stop having adventures with me, my ass, or boypussy, I guess, belongs to him.

But yeah, for the part you guys actually want to read about. I promise to try to keep my rambling to a minimum.

After that surreal first time, I was shaken to my core. My mom asked me about the locked door and I almost fainted, but you know, half-truths are more believable than outright lies. So, I told her James was the one that closed the door behind him and he probably locked it accidentally because he wasn't familiar with it. It was utter bullshit and I'm sure if I would've said that about a girl my age, my mom would've whacked me over the head, but in this case, she didn't question it.

I darted to my room after that and I swear I used so many tissues that night, I'm responsible for half of the Amazon's deforestation.

James didn't text, call or visit until the next Sunday. I was really anxious about it, even though it made perfect sense. Why would he have my number? He didn't ask me for it and it would be kinda weird for him to ask around for an eighteen-year-old's phone number.

Thankfully, I did see him that Sunday at church. He and his wife were sitting a few rows ahead of my parents and me. And thank the good Lord they were because if he gave me one of his smirks for staring at him like a madman, I would not have been able to answer for my actions.

I don't remember what he was wearing that day, but I know he always uses those shirts that cinch a little bit at the waist, always untucked over jeans. I spend way too much time looking at him, I know, sue me. Point is that it was making his back look massive, even his arm looked ginormous as he rested it on the back of the bench so he could hug lucky pregnant Lindsey with it.

So, I spent the entire service having sinful thoughts about those arms, and that back, and the owner of them, and the owner of me; which meant by the time it was done, I couldn't get up. I got a good scolding from my mom for being anti-social and not getting up to do the usual round of socials at the end of every church visit. Yes, I know I'm eighteen, but she's a religious, conservative mother. Trust me, it annoys me too.

I would love to say he approached me that day and whispered something into my ear and we ended the day having passionate sex in a church restroom stall, but unfortunately what happened was that he took one look at me and I started to shake like I was about to pass out, I'm pretty sure I became pale too and I tried to smile at him but it was probably more of a stroke-victim kind of look.

That was the whole extent of our interaction that day. Real-life stories can be a bit of a bummer sometimes, but I'm mentioning this because it's important for later when we did do naughty things.

I was very hopeful that my parents would talk to him and Lindsey and invite them to our house again, but my parents had been a little fuzzy about her "not feeling well" the last time they visited us and they didn't want to bother them.

That meant another whole week of feeling anxious about the situation, though I have to say, by the end of it I was starting to doubt it would ever happen again. Like maybe it was a one-time thing, he needed to blow off steam, or cum, and I was clearly there, thirsty and available. It was already mind-numbingly lucky that I got to have him that one time anyway.

Then another Sunday went by. This time he did give me a short smile, but no interactions. At least before he used to shake my hand, but nothing. I started thinking maybe he felt guilty, which wouldn't be that weird if you consider we met at church.

Then my dad's birthday came around. He turned sixty, which was a mildly big occasion. And with that I mean they invited half the town over for a barbeque that lasted far too long because who would've thought cooking for more than twenty people on a regular grill would take like five hours?

James was there. And he looked so good. Like, so good. I keep going on about clothes, but you guys need to understand that clothes adore this guy and his perfect inverted triangle body. He was wearing a leather jacket over a plain white T-shirt. I don't think I need to say more.

When they arrived at the house, he did shake my hand, and maybe it was my hopeful delusions but I think he lingered just a couple seconds longer than usual. He flashed me his signature smirk while I tried to compose myself after looking at him for the first time that day. I didn't compose myself. The reason being, he said:

"I have something to show you later."

My mind started racing so fast I don't know how it didn't break my skull from the inside. He said that out loud, in front of a bunch of people, next to his wife, who was looking at me with affection, as if she was so proud of me for taking her husband's cock up my ass like a champ and I was about to do it again.

I was confused, excited, paranoid, and nervous as hell, but I just nodded along.

A few hours went by and I kept trying to find him with my eyes without being too obvious. He was always with the other dads, talking about football, or basket, or baseball, or something, I don't know anything about sports. He did look back a couple times and nodded at me. I'm not sure what that's supposed to mean, but I nod back just in case.

There was a birthday cake, I died of cringe as everyone sang happy birthday to my dad, who is a goof and loves that kind of stuff. But after all that, it finally, finally happened.

"Hey bud, I got some more Pokemon cards for us to open. Let's go," he said with a decent crowd around us to hear, and, to my surprise, he pulled out a couple of packs from his pocket. If there are any Pokemon fans out there, they were Silver Tempest packs, I checked, but nothing of value, unless you count the hunk they came attached to.

"Mason, leave James alone. He needs to take care of Lindsey," my adorable, Jesus-loving, Bible-thumping mom chimed in.

"Oh, it's okay, Mrs. White. I'll go chat with the girls for a while. He's been saving those packs for like a week to open them with Mason."

My soul left my body when I heard that. There were only two possible options in my head. Actually, to this day, I still think there were only ever two options.

Either he legitimately felt bad for wrecking my ass and bought me cards as a way to apologize, or he was about to give me a second core memory that would brand me for life as one of the luckiest gays in the world.

Just like last time, I guided him to my room. Just like last time, we didn't say anything on the way there. Just like last time, he locked the door behind him. Not like last time, he didn't start taking his clothes off.

I stood in the middle of the room looking at him awkwardly. It was a cloudy day and well past noon. I remember because I have dark curtains in my room that make it pitch black on days like this, and it was lowkey kinda hard to see his expression. Not my fault that the window also faces the backyard, where all the yelling, laughing, and talking could be heard pretty clearly.

"You okay?" He finally asked.

"Yeah, s--sure," I wasn't sure what he meant.

"Today's the first time you don't look like you're about to have a heart attack," he scoffed, but his tone was friendly as usual.

"Sorry."

"Don't apologize. I wanted to talk to you alone to make sure you're okay with what we did."

I opened my mouth to tell him I'd be okay with anything we ever did, always and forever, but I have this deep paranoid feeling that I could say something stupid any second and he'll walk away; so instead I just nodded again.

"I want to do it again, but you have to be more discreet, understood?"

Would you blame me if I said I heard all of that but only processed the first part? Because I did. I'm honestly not sure whether or not I said anything or nodded back, but I must've, because next, he said:

"Take your clothes off."

It was just like last time, but he wasn't shirtless. He didn't have his jacket on, though, he'd taken it off a while ago, but he didn't make any moves to do the same with his T-shirt, even as I finished taking my boxer briefs off and throwing them on my chair to make sure I could find them fast afterward.

"Go lean on that drawer," he ordered while walking towards my bedside to pick up the lube, and I obeyed. "Bend forward as much as you can and spread your legs."

I knew what was coming and I wasn't ready. I mean, I kinda was. Even though I was starting to lose hope, I'd been cleaning myself every time I knew I was about to see him. It payed off big time.

I felt his hands close on my skinny ass before I felt his breath on my hole. It made me weak and I almost forgot there was only one layer of glass between us and a backyard full of Christians. I bit down on my arm to stop myself from moaning too loud, adding another battle scar to the one on my shoulder, which was almost faded by this point.

This was the very first time anyone had ever eaten me out. Since this is an actual experience, I'll say it's not everything it's made out to be in my opinion, unless it's done to you by an actual Greek god. In which case, the knowledge that this straight, married, gorgeous guy was on his knees behind me sliding his tongue in, out, and around my entrance was making me delirious. He went at it for a while and my legs were starting to feel tired.

I wondered for a second how he would react if I asked to sit on his face instead, but I forgot about it pretty quickly when I heard the distinct sound of a belt being undone and a zipper being opened.

It made me noisier for some reason. Like knowing he wanted to touch himself because he was enjoying me that much made me hornier.

He stopped, and I remember feeling cold from his breath when he said:

"I haven't had pussy in a while."

There were so many things I wanted to say to him, and I'm sure you would've preferred me to be more verbal as well, but I said it before and I'll say it again, I'm very paranoid that I'll scare him away somehow. Regardless, he squirted some lube out and applied it to my wet hole. I'm sure it was a total mess, but he didn't seem to mind. I could hear him jerking himself off, which made me hard as a rock too, which in time helped when he started using a finger to open me up. He found my spot almost immediately and I was starting to struggle really hard not to be too loud.

"You getting tired?" he said after a few minutes.

I didn't dare uncover my mouth so I just lied by shaking my head.

"We'll go to the bed soon," he promised, not making my situation any easier.

A second finger went in and I think I lost my sense of awareness for a while because next thing I remember was him telling me to walk to the bed and assume the same position I had two weeks ago.

I’ll admit it took me longer than I would’ve liked to make it there. My legs felt sore and weak, my ass was practically dripping and I was shaking with anxiety again.

As I laid down to offer myself up to him, I noticed he was finally taking his clothes off. Thank god my eyes had gotten more adjusted to the light, because if I wasn’t turned on before, and trust me, I was, I think my dick took on a life of its own at the sight of this. Like it’s one thing to see this man shirtless with his open jeans and thick cock ready for me, but to actually be able to look at his naked body in all its glory there’s just no words I can use.

I love how big his pecs are, and his tanned skin gives his abs a certain pop that I don’t know how to describe, but it makes me want to just lay on them all day to feel the texture. Not to mention those massive legs that legitimately made me wish he would’ve sat down for me to suck him off just so I could grab onto those massive things for support and be scared that he would crash my head with his monster thighs.

Seriously, I know most people would probably not find him as attractive as I do, but I just can’t help myself.

I know he noticed me looking at him with my unquenchable thirst and I think he might’ve taken just a little too long to climb onto the bed. My heart started to beat its way out of my chest as soon as the mattress sunk and I felt his skin against mine.

“Open,” he said after laying on top of me like last time.

I spread my legs. Thankfully, we had a lot more time than we had two weeks ago. The noise outside hadn’t gone down at all, which meant the party was still in full force. Everyone was having a good time while I was in my room feeling this man slide his cock inside of me.

It was so much easier this time. I didn’t need to focus so hard on relaxing and could instead listen to his breathing, the way he held his breath when he tried to push deeper, the exhale any time he gained another inch inside of me.

I think I was unconsciously moving my ear closer to him, because when he spoke I felt like his voice resonated inside me.

“You have such a tight boypussy,” he said. And I have this words seared in my brain, so you can trust me when I tell you these were the exact words he said to me next: “We should keep doing this, yeah?”

“Yes,” my voice was hoarse. I hadn’t said anything in a while other than moaning. That wasn’t gonna stop me from agreeing to the offer of a lifetime.

After that, I felt his entire weight lowering on top of me. He wasn’t lifting himself using his enormous arms anymore because instead, he wrapped them around my skinny torso in a morbid embrace that allowed him to sunk deeper than last time.

He felt so big. Even with all the prep it was still slightly painful, but at the same time I was in heaven. I was completely surrounded by his warmth, his smell and his muscles. This beautiful married man was now swaying his sculptural body up and down to fuck my hole and I couldn’t hold back anymore.

“Shhh,” he whispered to me but he didn’t stop and biting the pillow wasn’t enough. I wanted to scream my lungs out.

“Next time we’ll go somewhere else,” he made another promise while covering my whimpering mouth.

This man was in complete control of me, and I swear I just got lost in the moment.

At some point we turned to the side and we were spoon-fucking, or so I call it. He grabbed my thigh with his free hand to keep it over his leg while he thrusted into me back and forth.

In my eighteen years of life I have never felt so absurdly lucky. This was literally a dream. I was being fucked by a hunk in my own bed. Not just fucked, but owned by him. And he kept telling me how much he liked my boycunt while his wife had cake and tea downstairs.

When he came close to his climax, he pressed his mouth against my neck. Thankfully he didn’t bite, but he also didn’t kiss. He just groaned against me while my entire body rocked back and forth due to the sheer strength of his thrusts. I can’t lie, I wish we would’ve made out. I can’t stop wondering what he would taste like. At least I got to keep all of his cream inside me again.

After it was over we laid in bed a bit longer in silence. I still remember his thumb rubbing my stomach, where his hand rested.

“You sure you wanna keep doing this?” He asked.

“Definitely,” I said and I’ve never been more confident about anything else in my life.

Not much happened after that. We just put our clothes back on and walked downstairs, pretending absolutely nothing had happened.

The next encounter we had was a little different but I've written enough for today.

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