Dirty Buddies E15 | He's got questions about bottoming and I'm the expert

Everyone is over the age of 18

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“Hey, do you stay hard when you have something up your ass?” 

I choke on my cup of tea. I was watching a video on my phone and didn't even hear Jordan come out of his room. 

“Mornin’ to you too,” I cough. 

He pats me roughly on the back as he passes, then sits across the table from me. 

“Well?” Jordan takes a piece of bacon from my plate. 

“You could test it out and see for yourself.” I wink, and then cough again from the tea stuck in my throat. 

“Seriously, mate.  Just answer the question.” He reaches for my last piece of bacon and I slap his hand away. 

“I'm not usually the one doing the receiving,” I say as I shove the strip in my mouth before he tries to steal it again. “Make your own, cunt.” 

“Okay,” Jordan says as he sits back. “Fine.” He taps his fingers on the wooden table impatiently.

He got finger fucked again by his girl, didn't he? And it's making him question things. 

I drank my tea calmly as I waited for him to unravel. We don't have any other gays in our friend group. So if he has questions about assplay, there's no one else to ask. 

“Alright, Stacy and I have been trying something…downstairs…” His fingers stop moving on the table. “But…”

“You can't finish.” My groin starts to burn as we enter the topic. 

“Right,” Jordan says with a brief look at me.

“Do you like it, mate?” 

“What does that have to do with anything?” His fingers close into a fist in tension. 

“Well, if you don’t like it, you're not going to squirt,” I say calmly, trying not to scare him off. “Does it feel good?”

His fist relaxes again and Jordan takes a deep breath. It's like he's trying to get it off his chest but a part of him is holding back. 

“It feels…” He starts while adjusting his hat. “She wants it.” 

“Yeah, I got that, mate.” I decide to try another angle. “So she wants you to cum while fingering you.” 

His jaw tightens but he nods. While he's not looking, I adjust my crotch so my cock can grow. 

“It depends on the lad,” I say, picturing him on all fours with a finger in his hole. “And the position.” 

“So sometimes they don't cum?” Jordan looks up at me again.

“Oh, they always cum,” I say confidently and stare at him in his dark eyes. “Just sometimes, it's not so linear. Have to find the right balance.” 

“What do you mean?” He holds the eye contact with me. 

“My tool seems to work best when we're doing missionary.” My cock twitches. “But some lads finish best getting pounded in doggy.” 

“Ah,” he says in contemplation. I know he's thinking about what he's tried with his girlfriend so I push the conversation further. 

“What have you tried?” 

“On my back, my legs up in the air.” It's like the words just flowed out of him like air out of a balloon. 

I thought about it for a couple seconds before responding. “If you're used to topping.” I noticed his eyebrows rise in intrigue. “I mean, if you're usually the one doing the fucking, being in that position is probably unfamiliar to your body.” 

Jordan frowns as he considers what I'm saying. Then, he says, “What else could we be doing?” 

So much, I say in my head. With my voice, I say, “I’d start you off in a sitting blowie position.”

“You're getting off to this again.” Jordan narrows his dark brown eyebrows at me. 

“Am I not supposed to?” I shrug with no shame and openly touch myself across the table. “I think that'd be the best position for you to start.” 

“How is she going to…” He looks down at his crotch and lifts his legs, banging them against the underside of the table. 

“Not here. On a couch.” I stand up, boner tenting my boxers, and wave to him to follow me. He does, and sits down on the couch. “Have her be on her knees in front of you.” I kneel down between his legs, and pretend to flip my imaginary long hair.

“Fuck off, mate,” he laughs. 

“A blowie loosens you up. If you want to cum with something in you, you have to be comfortable.” I lean my head into his groin, and it doesn't disappoint with the manly musk he always has. He doesn't stop me, so I sniff him until the tip of my nose touches his package. 

Meaty

Hard

Manly. 

He did say he couldn't finish, so it makes sense if his body is ready for some release. I rub my nose along the shape of his growing shaft, kissing his covered ball sack at the base. 

“You two still have that deal where you have a free pass as long as it's with a bloke?” I murmur while feeding his boner with little sensations. 

“Yeah,” Jordan says simply. I touch his hairy calves and massage up his legs until I slide my hands under his boxers’ leg holes. His skin is toasty warm, and his fur is soft to the touch. 

“Want to see if this position works for you? I could help you experiment before you try it again with her.” With my lips, I pull at his hard shaft above the fabric. 

“Yeah, alright.” he says quietly, and we work together to pull his underwear down. 

His rigid shaft is already wet, and I grip it with a tight fist. It pulses back at my initiative, and precum drools down to the side of my index finger.

“You're horny, mate.” I move his foreskin to rub his pre-ejaculate on his head. 

“We didn’...” His mouth forms a tight O shape. “I didn't cum last night.” 

I wasted no time after that. Taking a first taste at his tip, I quickly dove down on his hard cock. 

“Fuck…” he whispers and his hand lands on my shoulder. His erection arches beautifully in my mouth, making it delicious to suck. “That’s good like that.” 

“Mmm…” I hum with his juicy cock in my mouth. We both advance at the same time, with him lifting his legs up and me pushing the back of his knees forward. I keep the blowjob going, because I want him to be rock-hard for the entry. 

“Ah…” His member flexes in my mouth as I graze his crack with my fingers. Satisfied with how wet his cock is, I pop off and stroke it with my left hand so I can spit on his hole. 

PTUI! My saliva coats his pink hole lined with a strip of curly hair. What a fucking beautiful ass. I spread the spit around, and his ring clenches whenever I press too hard. 

“You have to relax if you want to cum,” I say and then put the tip of his shaft back in my lips. He's softened a little, but not enough to call it quits. 

“I'm trying.” Jordan bites his bottom lip. I dive back down on his cock, giving him a lot of suction to keep the blood in his organ. “Mmm…” It works, and I feel him relaxing back into getting serviced. 

With just my thumb, I stroke his ring. I mostly focus on the blowjob, varying the angle and rhythm until I succeed in getting him steel hard again. What's working the best, is when I have my body turned to the left, so my shoulder supports his leg while I devour him. 

“Oh yeah…fuck…oh yeah…” 

Slurp…slurp…. The spit is getting all over my facial hair but I didn't care. I concentrate on stroking his hole gently while sucking him. Slurp… slurp… 

It's working…

He's relaxing…

His ring is loosening…

It's working…

“Oh…” I change to stroking him with my middle finger and it slips into him with no resistance. I moan at the pleasure of his warm tightness around me. Instead of softening, his cock gets harder in my mouth. 

My finger sinks naturally inside his beefy ass, and his hole clenched around me as I hit the maximum depth. 

“Mate…” 

“Are you alright?” I take a breather on his stomach and rub his dick tip on my lips. 

“I want to finish,” Jordan says in a ragged voice. I finger him lightly, trying to find his prostate. Nothing seems to give him a particular reaction. I worry about him going soft again, so I rapidly try different things. 

Flicking just my finger tip….

Going in slow and deep…

Should I put another finger in?

“Oh!” His stomach tightens beneath my face as my thumb grazes his taint. “Suck me!” 

I was in his crotch before I knew it. His grip on the back of my head guided me, pushing me up and down his throbbing hard-on. I keep my middle finger deep in him, moving only my thumb on his taint. 

“Ah! Fuck! I'm going to squirt in your mouth! I'm going to fucking squirt!” Jordan bounces my head hard on his crotch. “AHHH!”

“GUHHHH!” I gag at his cock holding my throat open. With another stroke of my thumb on his taint, his ring starts throbbing on my middle finger. 

“You ready?! Ahh! Fuck!” It feels like both his forearms are on the back on my head to hold it down. At the same time, his hips thrusts upwards, even though there's no more room for his dick to go in. 

His cum hits the middle of my throat, and gravity makes it drip back out into my mouth. Jordan fucks his load back in, and I choke on his jizz, feeling it going up my nose and blocking my breathing. 

But I have a job. I stroke his taint. I swallow his load. I keep my finger in him.

Until the end.

Until the very end!

“Ah! Fuck!” The weight of my head is lifted and the couch creaks as he sits back. His ring tightens around my finger again. I attempt to lift off and a firm hand on the back of my head commands me not to. “Not yet… holy fuck…swallow it…” 

Jordan shivers as I stroke his taint. 

“Shit…” 

I have to fuck him. 

I have to find a way to fuck him.