The Straight Family Friend

This was the third encounter I've had with James. Even though I have a couple more recent ones, I have to say this one has been my favorite one. You'll see why.

It happened a little while after the last encounter. I can't remember exactly how long, but I know it was more than a week because I remember our interactions at church on Sundays went back to normal after he kinda scolded me for being so obvious. Doesn't mean I ever stopped checking him out, though, I just practiced a bit more self-control.

Though, seriously, who can have any self-control when a super hot straight guy decides to fuck you repeatedly in your room while your entire family and his wife are in the same house? There's something so morbidly twisted in that situation, something so utterly abhorrent, morally speaking, that it causes me to have a rush of adrenaline every time I close my eyes to think about his naked body on top of mine and the effort I had to go through not to leave my throat raw from screaming.

Lindsey had her baby two weeks ago from the time that I'm posting this update, meaning that by the time this third encounter happened, we were very close to the due date. Which was making me very anxious. If you recall, the very first time we did the devil's tango, James mentioned he was looking for something to fuck because his wife couldn't. So, if she went back to normal, that would probably mean I'd be out of the picture. Spoiler alert, we're still going at it, thankfully.

It wasn't an entirely irrational fear, I don't think. Even though he did say during the second time that he wanted to keep doing this, everyone says stuff when they're horny as fuck.

But anyway, to the juicy bits.

This time it happened pretty unexpectedly, and I don't think it was actually planned by James. I'm not sure if it's his straightness, his cautiousness, or that he just doesn't have that high of a sex drive, but apparently, he has no issues going a week or two without my ass. I do, though.

I came home from one of my friend's house and, as soon as I opened the door, I was greeted by my dad, who had clearly been given a script from my mom to read to me.

"Hey Maze, your mom heard from Lindsey Brown they're planning on painting the baby's room this week. Why don't you head over and give them a hand?"

It didn't sound super promising if the wife was gonna be there, but at this point, I was so desperate to find at least one more chance before the stupid baby was born, that I just said yes. You know, just in case.

Later that week, my dad dropped me off at their house. It was fairly modest. Honestly, it was practically the same as every other house in the neighborhood. That's how the suburbs work, anyway. I'm sure you're not all that interested in the architecture of the hunk's house.

I knocked on the door and, of course, he opened it. There were clear signs that he'd been painting already, which caught my eye but I wasn't gonna say anything about it. He greeted me with the usual handshake and then waved to my dad, who cheerily honked before driving away after leaving his son with the man that was routinely fucking me.

"Come in," he said once we were in the clear.

I followed him inside the house with curiosity. Here's where I'd say you can know a man by the way his house looks or some random bullshit like that, but honestly, I was just looking around. There were plenty of pictures of him and his wife. Especially on their wedding day.

He led me into the living room, where he sat on a big couch, looking like an absolute god expecting the worship he knew I would willingly provide.

"I told Lindsey she should go to her mom's because of the paint fumes and I already painted the room. We have the rest of the day to ourselves. What do you wanna do?"

Don't get me wrong, this guy is absolutely gorgeous, but maybe he lacks a little in the brains department if he was asking a question like that. So, since I couldn't call him a moron for implying I would want anything but his body on mine, I took longer than a regular person would to answer his question, ironically looking like a dumbass in front of my... lover? owner? daddy?

"I wanna ask you some questions," he stated after a few seconds. "But I want you on your knees first."

As soon as he said that I was scrambling to break my knees on the floor at full speed so I could shove my head between his legs. I swear I saw a smirk as a reaction to that, but it was gone way too fast. I sure hoped the questions would be along the lines of "How long do you think you can stare at every inch of my bare body for?"

Since this isn't a porno, unfortunately, I didn't get to unzip his pants with my lips and lower his underwear with the sheer strength of my tongue. He did it for me.

And he was already hard. My heart was beating so fast, I'm sure he must've heard it. This was the first time I could see his bare member under the bright light of day. I have no clue how many inches it is, but I know it's about average. It's fairly thick, which my ass can testify to. And also cut, with a bright pink head. It has that smooth quality that some dicks have, I'm not sure how to explain it, it's just very pleasant to look at. And it's even more pleasant to hold it in my hands while it's fully hard waiting for my mouth.

"How long have you known you like guys?" he asked before I had the chance.

"Umm, all my life, I guess," I responded sincerely.

"And how many guys have you been with?"

Thankfully, I had lost the ability to feel anything but arousal while stroking this man's beautiful cock, otherwise I would've been really annoyed at the constant interruptions keeping me from shoving all that meat down my throat.

"Four," I said.

"Did all of them fuck your pussy?"

I was really hoping he wouldn't ask that. Exposing my inexperience to him felt somehow more embarrassing than anything we'd done together up to that point. Still, I figured lying in this situation would be too risky. I did not want him to catch me on a lie and get mad at me.

"Just two," I finally mumbled, half-pretending to be too entranced by his cock's wet sounds as I picked up the pace.

"Hold on," he said, causing me to stop, but honestly hoping he wouldn't shoot any more questions. I needed him to shoot something else at me.

He lifted his massive body just enough to take his shirt off and throw it to the side, exposing my favorite piece of art in the entire world. Again, this was the first time I actually got to see his bare torso under decent light. Especially from the angle I was looking up from, this felt unreal. I won't describe him yet though, you'll see why.

Suffice it to say the sight of his shirtless body with his spread legs and thick cock exposed made me thirstier than if I had been walking in the sun for the past three years.

"Don't stop 'til I cream your mouth. Got it?"

I honestly wish I could say I responded something like "Yes, sir", or "Yes, daddy", but this isn't a cheesy fifty-shades fantasy. I didn't have to say anything, I just needed to open my mouth as wide as I could and slide his dick on my tongue.

We were alone this time. There was no risk of anyone catching our abhorrently immoral act. We could be as degenerate as our hearts desired. James didn't hold back. His grunts and moans were loud but deep. They somehow seemed to vibrate inside my chest even though I was quiet, focused on my task of attempting to get his meat as deep as it could go. But those sounds were masculine too, primal, like a hunter enjoying the sight of innocent prey begging for the prize of his own life. It made me shiver to think I was in the presence of a real man, on my knees, worshipping with my mouth.

And you can bet I was sucking like my life depended on it. I was obviously no expert, though not for lack of trying. I'd push my head down as far as I could until my eyes started to get teary and then I would pull back, sliding slowly, taking my time to get to the head that I would kiss and lick like a worthy prize. And then I would go down again, focusing hard to relax my throat.

I must've done that at least three or four times before I felt his hand on my head. This man doesn't need to say a word to make me feel completely under his control, utterly dominated. I get so hopelessly lost in my desire to please him, I was about to hold back a whimper but decided against it. We were alone after all.

I hope it sounded sexy, I couldn't really tell. What I could tell was that I was holding on to his thigh for support because my back was hurting and I immediately felt that leg tense up as soon as I had released that sound. Honestly, I choose to believe that was a good sign.

He didn't try to force me deeper down his girthy cock, nor did he pull me back like the first time I'd had the absolute pleasure of tasting him. Instead, he did something I wasn't expecting.

You know sometimes when you lay your head on your friend's lap and close your eyes while they slide their hand on your hair and scratch you softly and it's the most amazing, relaxing feeling in the world? Yeah, that's exactly what he did. No, I'm not kidding.

Would you judge me if I said I fell in love with this man at that moment? Like, yeah, I'm sure it's partly because I'm inexperienced and everything feels new and amazing to me, but c'mon! At the very least I'm infatuated.

I opened my eyes just for a second to look at his body and receive the last bit of inspiration I needed to plant his cock nicely within the depths of my throat. My hands were itching to slide on his marble abs, but I needed to hold on to him and I also wanted to push him over the edge already.

I could feel him slightly twitching for as long as I managed to keep his dick as deep as it was, and the hand on my hair suddenly stopped moving. That had to mean he was close.

Thankfully, I did have the barest bit of experience. Enough to know if he was gonna cum, we couldn't do it like this or it would end up... not nicely. That's a story for another day.

So I pulled back enough to make sure I could still breathe and swallow, and only then did I use the hand that had been wrapped around his girth to look for his balls instead. I found them easily, they felt warm and heavy on my palm as I fondled them.

I started sucking harder and bobbing my head up and down minimally, too. I was so eager for this that I think I even let out a moan or two. James was lost in grunting, his hand had gone stiff on my head.

It was an explosion. I felt his cock throb in my mouth and before I could prepare I was having thick ropes of cum shooting straight on my tongue. I swallowed as much as I could but it was a lot. Like, a lot a lot. As I write this I realize that probably makes sense if he's not one to jerk off on his own. His wife wasn't putting out and we hadn't had fun in a while, so of course he'd be loaded.

My mouth filled pretty quickly and things got a little messy, but thankfully it stopped before I had to start coughing. He tasted very salty, and the consistency was thick as actual cream.

I was so desperately horny after that, I could feel my underwear soaked from how much I'd been leaking. And the fact that he'd just cum in my mouth made me all the more eager. I was entranced as I finally took his dick out and used my hands to help me lick his cock clean. I was like a starving man clinging to the last breadcrumbs on the planet. It just put me in such a surreal state of mind. I was desperate for more.

What happened next is something that I still struggle to come to terms with. I know everything I've told you guys already is more than enough to make anyone reasonably accuse me of being unreasonably lucky. And if I could feel guilty about life choosing to shower me with this gift of fortune, I promise I would. Alas, I can't, so I don't, and you'll have to live, just as I do, with the fact that this happened to me.

"Let's go," he said in his gruff, post-orgasm voice once I was done cleaning.

James got up and headed up the stairs. In an ironic twist of fate, it was now my turn to follow him into his room.

I had just sucked this gorgeous man off and swallowed his thick load in front of a bunch of pictures of his smiling wife in her wedding dress, and now I was in their room. I don't think abhorrently immoral covered it anymore.

"Wait here," he said and suddenly ran out of their room only to come back with a dirty sheet full of paint smudges.

I looked at him with curiosity as he made covered the massive bed with that sheet, making sure the clean side was facing down so it wouldn't paint the bedspread.

"We can't leave the bed smelling of sex," he explained while making sure the paint was already dry.

God, I could watch this man be a meticulous cheater with his majestic bare torso for the rest of my life and die happy.

Finally, he sat at the edge of the bed and indicated I should approach. Don't get me wrong, I wanted nothing more, but I still hesitated:

"Do you- uh, do you want to take my clothes...?" I trailed off.

"No, come here," he commanded.

Confused as to this man's intentions, I approached him slowly. He put his hands on my waist, and I got dangerously close to passing out. Of course, his dragging me even closer until I had no choice but to straddle him on his lap did not help whatsoever.

I was so close to his face that I'm sure my brain was malfunctioning. I didn't know what to do or say. I had my own hands on his shoulders for support, and I think that was the very first time I ever touched any part of his torso. My blood had been replaced by adrenaline at this point.

"Hold on to me," he said redundantly. I was not about to let go.

He smelled so good. I mean he always did, but my mind was desperately trying to grasp onto something, and the smell of his cologne was the strongest thing assaulting my senses, after my sight, of course.

His hands were moving. They were moving and my breathing became erratic. He slid them under my shirt and toward my back, hooking the edge of my sweatpants with his thumbs and pulling them down until my ass was freed. When he pressed his palms against my nearly-non-existant-ass-cheeks, I moaned. And he smiled at me.

I could've cum there. I swear I was fully aware of the possibility. I could've busted a massive load right then and there, but if I ruined the moment I would never forgive myself for not finding out what was next.

"I gotta prep your pussy for me," he said. "And I was thinking..."

While he explained, he pulled a small bottle from his pocket and squirted what I assume was lube on his fingers, looking for my entrance with them.

"...maybe you'd like to have a look up close."

It was so difficult to process what he was saying while the first phalange of his finger slid into me. Thankfully he was fairly understanding.

He let go of me with the hand he wasn't using to finger my eager hole and slid it on his abs, up to his massive chest. I followed it with eyes and, if this was a cartoon, I would've actively started drooling.

"You wanna get a feel?"

More than fucking, eating me out, or even sucking his juicy cock, this is the most deliriously sexy offer he'd ever extended to me. I was visibly shaking as my fingertips slid down from his giant shoulders to his chest. This is the part where I will describe him as best as I can because this memory lives rent-free in my head and in every single one of my self-love sessions.

I've mentioned it before, but James has a tanned color that gives him that exotic look that makes him just that much sexier. His pecs are big and prominent, they're not so massive that they look like a pair of hard tits, but they do pop off his body with considerable volume. His nipples are a darker color, not too big, and placed on the lower side of each pec. I brushed my fingers lightly against them to see if there was a reaction but didn't notice anything.

At this point, I remember him sliding his finger much deeper, and I particularly remember being annoyed by the deafening silence around us. It made it that much more obvious how needy I was feeling when we could both hear my irregular breathing so clearly.

I kept going down to his abs while a second finger started to poke its way in. His abs aren't perfectly symmetrical, they are slightly offset by about half an inch, but he has eight of them. It's very clear. Some guys have the last two very faded and hard to see, but not James. Although that might be because he was sitting.

I whimpered when the two fingers started to push deeper. He was staring at me intensely the whole time but I couldn't return the gesture. Nor did I feel like it while my hands traveled back up to feel his chest again. It was at this point that he flexed his arm for me.

My mouth had gotten completely dry from the excruciating thirst I was feeling. If I wasn't awfully scared to push things too far, or if I had a smidge more confidence I would've uses my lips and tongue to explore him instead. Still, using my hands to squeeze his massively bulging bicep is a core memory for me. There were so many veins coming up from his forearm too. I was losing my mind.

I felt like I was ready to take him. Two fingers were enough. I wanted him now. My dick was physically hurting under the fabric. He'd only uncovered my ass, leaving me unable to touch myself.

I waited a few more seconds but he isn't a mind reader and, for once, I used my mouth to ask for what I wanted:

"Can we fuck?" I said, and he chuckled.

"Alright," he slid his fingers off and I hadn't realized how much I'd been enjoying that feeling.

"Take your clothes off," he finally, finally commanded.

I got up a little bit awkwardly and hastily took everything off while he did the same with his pants. I wish I would've gotten to touch those massive thighs too, but it might just be my own greed saying that.

"Here," he said, putting a small pillow on the edge of the bed where he'd been sitting before. "Lay face up with your lower back on the pillow."

I did as he said and for a few seconds, the only sound in the room was the rustling of fabrics against my skin. It was an incredibly uncomfortable position for a while since my legs were kind of just dangling there, but he made quick work of them, putting them on his shoulders.

Without uttering another word, he took what I think were his boxer briefs and gently covered my soaking dick with it so he couldn't see it. I blushed at the gesture, but he is a straight man after all. Makes sense that he wouldn't want to see a dick while fucking my "pussy".

He squirted lube on his cock, which apparently was hard as a rock again, and moved my legs so they were hugging his waist instead while he lined his girthy member against my ass.

This was a much better setup. I could see things from here that I couldn't see before, like the sharp v-lines on his hips, sprinkled with prominent veins. And the absolutely glorious build of this Greek god loomed on top of me as he started to sink into me.

That day there was no risk of anyone hearing our sinful acts, but I still tried to hold back my moans out of embarrassment. Or at least I did until he managed to push the head in, making my hole spread wider and filling me with even more adrenaline.

"Love how tight you are every time," he said with a breathless tone.

I moaned for him because it hurt, because he was so fucking hot, and because I needed to after biting down on my pleasure for so long.

Using his full weight, he helped himself slide deeper, inch by inch. It took a while but we had all the time in the world. With every bit of progress, he managed to make, my legs tightened around his hard body, begging him for more. I was grabbing onto the sheets with all my might to withstand the initial pain, waiting for the inevitable reward once I managed to loosen up and he could find my spot.