The Wingman E8 | Fucking my first gay guy

Everyone is over the age of 18

Continued directly from the last story

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“I'm starting to think you're a little into it,” Kyle looks down at the blanket covering my crotch again. 

Into it? 

“Tonight?” I ask. Will I even be able to get hard for a guy’s ass? I mean a mouth is a mouth. If I'm not looking, it feels just like a girl. If I'm fucking him, I'd be looking directly at him. 

“Yeah, tonight. He went home to rest a bit and he said he'd come back later.” Kyle nods. “So, are you down?” 

To fuck your date? I thought you were angry about it just earlier. 

“About this morning,” I start, suddenly feeling extremely guilty.

Kyle looks away and shakes his head. “It’s fine. We didn't have any of those boundaries set and it's not like you two haven't done that already.”

Gay relationships are fucking weird. 

“But I want this to be over, okay? Just finish this last thing so he can move on.” Kyle looks back at me. “I really like him, Curtis.” 

“If you're sure,” I say, searching in his eyes. He seems genuine about his request. 

Kyle’s face relaxed into a smile. “Thanks man. Last thing, I promise. Just give him a good show.” 

“I've cummed twice today. It’s not going to be easy.” 

“Wait, twice?” Kyle raises his eyebrows inquisitively. The first one he saw go down Warren's throat. The second one… I was listening to them angry fuck. 

“I needed some help settling into my nap,” I say and then move on quickly. “Should we do it tomorrow instead?”

Kyle thought about it for a moment and then shook his head. “No, let's get it over with.” 

The nerves kicked in as the day went by. It felt weird. Some moments were just us, long time buddies, shooting the shit. Other moments, I thought about how he's going to watch me put my dick into the same hole he's been pounding. The feeling paralyzed me.

When Warren came over, I was already exhausted worrying about it all day. He sat on the couch, with his blond hair perfectly coiffed and his skin almost glowing. 

It was awkward. Like real fucking awkward. Kyle didn't help either. He sat beside Warren, holding his hand and not saying much to facilitate the situation. 

“Well…uh…” Warren looks shyly at me. I think I broke eye contact first. 

“Y’all are acting like you weren't sucking each other's dicks this morning,” Kyle says finally.

“Hey!” I protest. I ain't ever sucked a dick in my life. I catch Kyle smirking at me, and I realize he's just trying to get me to be more comfortable. 

“Maybe we can start with that.” Kyle squeezes Warren’s lap. “Easy. Already done before.” Warren nods excitedly. I look around to see where I should go. 

“Just stay there,” Warren says, pulling a cushion from the couch and bringing it with him. He kneeled down on it next to the kitchen stool that I was sitting on. 

I'm about to fuck a guy for the first time. 

I swallow my nerves as he gropes me through my pants. The nervous feeling slowly transformed into excitement as my dick responded to his touch. I slid my pants down for him and he reached up the leg hole of my boxers. 

“Mm…” I let out as his cold hand wraps around my thickening shaft. 

“Sorry,” Warren whispers, looking up at me with his blue eyes. The eye contact made my cock firm up all the way. He shuffles the fabric and pulls out my cock through the same hole, and then sucks on the tip.

His mouth is burning hot compared to his fingers.

I exhale out loudly as he dives into my crotch, enveloping my shaft with the hot and wet feeling.  I wonder how an ass feels compared to this. Tighter for sure, and maybe even hotter? Probably not as wet. 

The nerves wrack through my body again. I’m really about to fuck a guy, and what’s more -  in front of my best friend. My dick limpens at the thought and I see Warren work extra hard to try to get it back up. 

After 10 or so minutes of this, it was clear that it was going nowhere. There were moments where the blond boy’s persistence got me in the mood and I fucked his willing mouth, but as soon as the realization that I have to put it in his ass hits again, it’s like my dick just deflates. It was extra embarrassing when Warren let go to take a breather and my cock was hella soft and small. 

“I told you. Already blew two loads today.” I made an excuse. My record is actually more like 4-5 times a day, but it probably isn’t helping that the tanks aren’t as full. Warren spat on my cock and stroked it, not willing to give up. 

“Come sit on the couch. It’s more comfy,” Kyle says. When I stand up, Warren slides my boxers down. I walk over to the couch and sit down where Kyle was, feeling his body warmth on my bare asscheeks. 

“Should we put on some straight porn or something?” Warren asks Kyle. Kyle looks at me and I shake my head. It’s not a bad idea actually but I really just want the conversation to go away from me not being able to get it up. 

Warren gets back to sucking my limp cock and I close my eyes to picture other things. My mind is running a million miles a minute, and I’m not that successful in focusing until Warren’s lips hummed on my shaft. 

“MmmmMm…” The vibrations surrounded my cock. I opened my eyes and saw Warren’s eyes closed, with his nose in my pubes. Further back, Kyle was on his knees too, nose deep into Warren’s crack. 

“You suck him baby,” Kyle murmurs as he licks. “I’m going to prepare your hole.” 

“Mm!” Warren moans. Kyle spreads his cheeks and digs in deeper. The passion of the scene unfolding in front of me catches my attention and I feel the blood go back into my cock. Warren notices right away and starts sucking hard and fast.

“Oh…Oh…..Oh…” Kyle moans as he eats Warren out. He’s clearly enjoying it, and that enjoyment…is making me enjoy it. I stiffen up to Warren kissing the underside of my shaft and worshiping the tip. It began to feel better and better, and I got hard enough for Warren to wrap his fist around the base to add to the experience. 

“I wanna get fucked…” Warren says between sucks, “...so badly.” 

“I’m not quite done here,” Kyle spits into his crack and then goes in to lick again. “Fuck, this ass is so good.”

The eroticism and passion was keeping me hard now. Another two or three minutes later, Warren flipped around, pulling down Kyle’s pants and excitedly wolfed him down while presenting me with his plump ass. 

With my dick now bone-hard and slick with his spit, I pressed into the hole in front of him. I didn’t expect it to be so loose, and I slipped in accidentally. 

“Oh..”

“MMMM…”

“Fuck, baby…” Kyle moans back and looks up at me. I sink into his moaning man. His hole was as hot as I expected. I pushed until a high pitched squeal came out of him. “That feel good, baby?” Kyle strokes the blond hair that’s on his crotch. 

Then, Kyle looks up at me. Me, deep inside his date. 

“Fuck him. Fuck him really hard.”

Warren, impatient, starts to fuck himself on me as Kyle and I stared at each other. 

“Fuck him,” Kyle repeated. I lifted up my shirt to watch Warren’s bubble butt work to take in my cock. 

I’m fucking a guy.