The Wingman E9 | My best friend helps me seed my first ass

Everyone is over the age of 18

Continued directly from the last story…

I'd recommend going from the beginning of this week and getting the full experience...

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My shirt kept getting in the way of my view of Warren’s ass, so I took it off. The sight of my cock stretching out his hole was actually breathtaking. I won't toot my own horn but I don't have a small tool and it looks almost inhuman the way his ring stretches to accommodate me. 

“You like his big dick?” Kyle strokes Warren's long blond hair. His mouth is too busy sucking dick to respond but his ass pushes back onto me as an answer.  Kyle looks to me and says again, “Fuck him.” 

I don't know where to put my hands. Normally I would grab a chick’s waist, but that doesn't seem right. I let my hands hover awkwardly at my sides while I tentatively try my first couple thrusts. 

“MmmMmmm,” Warren moans with satisfaction, his mouth full of my best friend’s cock. The movement inside him was smooth and the tightness didn't stop the fluidity. 

“He can take it hard,” Kyle says, watching me roll my hips into his lover. “A lot harder than that.” 

“I don't know where…” I hold my hands up. My knees are starting to hurt from this position. It was hard to get any leverage for fucking just from my core strength. 

“Just pretend he's one of the girls you bring home,” Kyle says impatiently. His face tightens up with pleasure as Warren deepthroats him. Throughout our conversation, I stopped thrusting and Warren took over the rhythm rocking back into me again. 

He really does want it. 

I grab his hips like I would with a girl and pull him in towards me. His hole swallows me up fully and the feeling of being deep inside a warm hole makes me close my eyes. 

“OHhHh!!!” Warren’s loud cry makes me let go of him. I pull out slightly and he backs himself fully on to me. 

“That was a good sound,” Kyle reassures me. A good sound…like I'm doing a good job fucking a man. 

Oh Jesus, I'm a fucking a dude’s ass. 

“I don't think I can do this.” My throat is scratchy and dry. I was deflating as I thought about the reality of what's happening. 

“You're already doing it. A couple more minutes and he'll be done.” 

I nod. I said I would do this for Kyle and I'm a man of my word. I can't stay in this position any longer though, because my knees are killing my boner further. 

Kyle read my mind and moved from his position. Warren lays his upper body flat on the floor and arches his butt up. I was worried that if I pulled out, I wouldn't have the hardness to go back in. So, I pushed into him as I stretched my legs out behind me. I placed my palms on both sides of him to balance my weight.

So much better. 

“Just drill him until you cum. He can take it. And he'll like it.” Kyle kneels besides us, rubbing his hard on. “Isn't that right, baby?” 

“Yeah…” I start fucking him. It's a lot easier to fuck in this position. “Oh yeah! Oh yeah! Give it to me!” 

I use his hole to harden back up. It's impressive how he can take it. Basically no matter what I did, it seemed to get a positive response out of him. I wasn't totally hard but I was at a comfortable fucking stiffness. 

“Mmm!! Mmm!! Mmm!” Warren turns his head to watch me drilling him. His normally pale skin is flushed red. “Oh fuck!” He lays his face back on the floor. 

“Give it to him.” Kyle says, jerking himself quickly. He strokes Warren’s hair again. I pound him hard, making his whole body vibrate with my impacts. 

“Oh fu- oh god! Oh god!” 

“Oh…” I feel the pleasure pick up. It didn't matter how hard I fucked him, he took it with no complaints. 

“Wow,” Kyle says, looking down at my moving hips. His own thick dick protruded straight out. “Are you going to cum in him?” 

“Cum in me! Please!” Warren says, breaking my attention. The pleasure dips down and I feel the blood leaving my shaft. 

I've never cummed in an ass before. And now I'm really acutely aware that they both want me to. I kept fucking, trying to get it back up but it became hard to thrust with my cock half soft. 

“I'll get him off,” Kyle says, understanding the situation. I pull out and Kyle pulls Warren to the couch. Putting his face flat into the couch cushions, Warren’s perky ass opens up. His hole looks beaten and swollen. “You did a number on him,” Kyle says while inspecting closely. The hole winked at us as we both looked.

I started getting harder again, realizing how well Warren was taking my pounding. I could go on for a lot longer and he would love it. Now I’m sure he’d love it even if I left him walking funny later. 

“You ready?” 

“Yeah,” I whispered. I get closer and aim my cock head at the beaten hole. It slides in easily and Warren lets out a pained gasp. 

“He's fine,” Kyle reassures me. His face is right next to my cock and his lover’s hole. He reaches under Warren to stroke him. 

“Oh god… oh god…”

“Fuck him and finish him off.” Kyle looks up at me. I bite my lower lip and start pounding the sweet ass. 

“Oh GOD! OH GOD!!!”

THWACK!

THWACK!

THWACK!

“I'm cumming! Oh god! Oh my god!!!” Warren buries his face in the cushion. “MMMMMmmMMMMMm I’m CUMMING!”

“Oh yeah baby!” Kyle has a big smile on his face. “Fuck him, Curtis! Oh baby, such a big load.”

“Cum in me!” Warren wails. I'm close enough this time to make it happen. I pound him at my speed, using him as my orifice to finish. 

THWACK!

THWACK!

THWACK!

I was dripping sweat from how hard I was trying but I couldn't seem to push myself through the edge. But I was 

So

CLOSE!

THWACK!

THWACK!

THWACK!

“You don’t have to if you don't want to,” Kyle says. 

The thing is though? 

I want to cum. If only he could be a little tighter…I'm sure he has no control of that muscle anymore. 

THWACK!

THWACK!

THWACK!

“Can I help you?” Kyle says. 

“Oh…” I moan as I finally get a little closer. “Yeah. I'm getting there.” 

Kyle ducks out of my eyesight and I look forward to focus on thrusting. I'm almost out of energy, but I think I can push through to finish this. Hopefully whatever Kyle is about do will–

“WHOA!” I jerk at the sensation at my balls. It's wet and warm and– “Oh shit!” 

The pleasure surges suddenly and I find myself backing up as the need to cum overwhelms me.

I'm going to cum!

In an ass!

Oh God! 

Warren’s ass backs up on me. 

“I'm going to cum!” I shout. “OH! OHHHHhHhH!” Warren’s ass milks me and the contractions take over my body. I naturally start thrusting again hard into his hole, slamming my body weight into him as I release my seed into him. “Ohh..ohHh…Ohhh…” Kyle's tongue swishes around my pulsating balls. “...oh….”

“My turn.” 

I wasn’t ready to pull out yet but I did. Kyle replaced me and Warren let out another whine. 

“Oh you're so loose now. God, you are such a slut! Oh you fucking god damn SLUT!!!” Kyle lasts just a couple seconds inside the destroyed hole. He pulls out afterwards and we both watch cum leak out of the twitching hole. 

“Thanks.” Kyle turns to me, his face flushed from his orgasm. 

I stare at the cum dripping from Warren’s hole onto his nuts.