Wingman
This is the second part to my first story; “helping a friend.”
So this whole situation with my friend Fred, started because he was in a bit of a dry spell. So I helped him out a few nights back and gave him head on a beach. Then it happened again in his car. 😬😬
A few nights later, we went out for some beers. I told him I would help him out, and be his wingman.
We went to a local hotspot that had a pool table, and some ping pong in the back patio. I’ve hooked up with a few girls here myself, everyone here is looking for some.
We sat at the bar watching the Rangers game and staking out the crowd. He spotted a girl across the room playing pool with a small group of people. She was pretty hot. Black skirt, and deep V blue shirt that pushed her tits up and out. She bet over the pool table to hit the ball, and the lower part of her ass hung out a bit. We both locked in. I noticed a few guys with her, didn’t appreciate our looking.
“I think she’s taken by one of them. They don’t like the way we’re looking at her.” I said leaning close to him.
“No way man.” He said taking a swig of his beer. “She hasn’t leaned on either of them. She’s single as fuck, and they’re probably gay.”
“How do you know that?”
“Because they’re not checking her ass out as she bends over to hit a ball.” He said confidently.
I think he was just hoping. We ordered new drinks an walked over to them. I put a dollar on the pool table.
“We get winner?” I said
The girl looked at us. Then looked at the two guys she was with.
“Three on two doesn’t sound fair.” She said as she hit one of the balls in the corner pocket.
“Are you afraid you’re gonna loose?” Fred said.
“No, I just want to play the game with a challenge.” She said as another ball went in.
Her two friends looked at each other and chuckled.
“Well, what if my buddy here plays winner, and I’ll by a round for the ones not playing.” I negotiated.
She looked at me, then at Fred. Her two friends looked at each other and shared a glance with her.
“Fine.” She hit the eight ball in and demanded Fred to rack them.
I asked what drinks they wanted and went back to the bar hoping they would follow, and give Fred some space. They didn’t. They just stood close and watched. As I waited for the drinks, I noticed them looking at Fred, more like checking him out. I can’t believe he clocked that. Now I have to be a good wingman, and try to get with one of them.
I’ve never actually flirted with a guy to pick up. I’m still not convinced I’m fully gay, I was kind of hoping we both found girls, but looks like I gotta take one for the team.
I walked back and placed the beers on a table near the pool table, but far enough to give Fred space. They walked over to me and grabbed the beers.
“You guys from around here? I asked
“No. Few towns over.” One of them said.
“We’re just here supporting our friend through a brake up.” The other said.
“Oh damn. I’m sorry…those suck.”
They shared a look. “We’re not sorry. He was a fucking loser.” They both chuckled.
“You guys seem cool. I’m Dan, and that’s Fred.”I said
“I’m Kevin, and this is Gary, our girl over there is Claire.”
“Nice to meet you.” I held up my beer for a cheers. They both clinked my glass.
We talked for about twenty minutes. It seemed like Claire and Fred were hitting it off, so we kept talking. We made our way to the back patio for some air. After about twenty minutes, Kevin got a text from Claire.
Claire: “we’re going to his car to makeout.”
They both laughed.
“This wasn’t supposed to be a hook up night, but there she goes.” Gary said.
I took a sip of my beer. Kevin and Gary shared a look. The look that says; “I’ve got a wild idea…”
“Are you gay?” Kevin asked.
“What? I mean…not really?” I hadn’t really been asked that question before.
“That wasn’t a no.” Gary said smiling.
“I mean. I think I’m going through some things, but I still like women.” I said
“Gary and I are her BFFs. Sometimes we help her out when she’s down and single. We thought tonight was one of those nights, but your friend seemed to swoop in and get her first!” Kevin said.
“I’m sorry..I.”
“Don’t be sorry!” Kevin interrupted. “We were just wondering if you wanted to fool around a bit.
I sat there unsure what to say. Gary stood up. “I’m gonna pay the bill.”
Kevin stood up as well. “What do you say?”
He had such a trusting look in his eyes. What am I really getting myself into? I shrugged and stood up, then followed him out the back entrance of the patio.
We walked a few minutes in silence and approached a larger SUV. Kevin opened the back door and got in. I followed his lead. I shut the door behind me, and when I turned around his dick was already out.
It was a nice looking dick, I’d say average size, and cut. Without hesitation, I moved in and wrapped my hand around it and started jerking him off.
“Get it wet first.” He said moaning.
I leaned over and spit on the tip and moved my hand around, I spit some more and was able to slide it in my hand. He moaned some more. “That’s nice.” He said.
The door flung open, I let go of Kevin’s cock, startled. It was Gary. “What the hell? You get started without me?” He complained.
“Come on in.” Kevin said. “You can keep going.” He grabbed my hand and placed it back on his cock.
Gary started rubbing my leg and made his way up my thigh and grabbed my already hard cock through my pants. I felt him unbuttoning my jeans. I sat up and let him pull out my dick, has I kept stroking Kevin with my left hand. I felt off, but I was trying. Kevin seemed flustered for a moment.
“Hold on. I have an idea.” Kevin said.
Gary let go of my dick, slide my pants down. Kevin moved from the seat and laid me down on my back. He moved his leg over my chest, kneeling, with his cock inches from my face.
“This will be much better.” He said grabbing the back of my head, and skidding is warm cock in my mouth.
I couldn’t really move the way I was positioned, but he controlled my head movement. I then felt my cock getting wet and warm. Gary was sucking me. I couldn’t really concentrate on everything, but it was amazing. Kevin started to push his cock further into my mouth and face fuck me. I was so turns on. He started moaning and grunting. I started to feel myself about to cum. I tried to warn Gary, but I was just gagging on Kevin’s cock. Then it happened.
Kevin picked up the pace, and so did Gary. Kevin’s cock started to swell, as he shot his first string of cum into my throat, I burst in Gary’s mouth. He sucked harder as I came, and Kevin kept fucking face as he came. His hot cum dripping down my chin. He pulled his cock out and I licked the remaining cum.
“Wow. That was…wow.” Kevin said. He unstraddled my check, I sat up as Gary cleaned his mouth. Gary sat next to me and pulled out his cock. It was bigger than Kevin’s. Uncut. He moved his foreskin back revealing a nice mushroom tip.
“My turn.” He said grabbing the back of my head.
I leaned over and shoved him in my mouth as deep as he could go. I started bobbing my head slowly and stroking him. I felt Kevin grab my legs and pull me up to the seat in a kneeling position. I felt warm breath on my hole, then I could feel him kissing it.
“Is this okay?” He asked
“Mmhmm.” I answered with Gary’s cock filling my mouth.
I’ve never had my asshole licked, I’ve had a finger in it, but that’s it. I still can’t describe the feeling, but it made me hard again. He was slobbering and spitting, then I felt his finger start to breach. I let out moan, an pulled Gary’s cock out of my mouth.
“Oh my god.” I said taking deep breaths.
Gary shoved his cock back in my mouth. Kevin then slid another finger in. I let out another moan, a little high pitch.
“You’re so tight..” Kevin said.
I heard a snapping noise, like a bottle. The felt a cooling liquid drip down my crack. I pulls Gary’s cock out and looked back, Kevin’s waist was up to my ass.
“Wait…I’ve never…” before I could finish my sentence, Kevin was already sliding his cock into my ass. I went to let out a groan, then Gary shoved my head back onto his cock.
“Keep it in your mouth.” He demanded.
Kevin slowly pushed in, and slid out, getting my ass ready for a pounding. I kept sucking and stroking as best as I could. Gary didn’t seem pleased. He pulled out of my mouth and got on his knees, leaning back on the car door.
“You’re about to get fucked in both ends.” Gary said.
They both slowly got into sync, sliding in and out of my mouth and ass. It was amazing. I was doing nothing, just being used. One set of hands grasping my hips, pumping in and out so hard his balls clapped mine. The other set of hands holding my head, and thrusting his cock into my throat. I gagged, I moaned I wanted it all.
Gary started to tense up and groaned. His cock swelled up, his pace quickened. He pulled his cock out of my mouth and said, “I wanna paint your face!” He jerked off and the first string of cum shot across my face. I kept my mouth open wide, trying to catch as much as I could. I was moving all over the place because of Kevin’s thrusting.
“Oh yeah, take all his I’m while I fuck you!” He yelled.
Kevin picked up his pace. He announced he was about to cum. Gary sat back down, his cock getting soft.
Kevin shoved into me causing me to fall on my stomach, and face onto Garys wet lap. His soft cock in my face. I opened my mouth for it again.
“This guy is cock hungry!” Gary said laughing.
Kevin pumped harder and harder. My ass started to hurt from his thrusting. He let out a loud groan, and pushed his cock deep inside and held it. I could feel his warm liquid filling me up. My own cock began to explode between the seat and my stomach. He thrusted back and forth a few more times until he was empty.
When he pulled out, I could feel his cum dripping from my hole. It was a mess. I was filled with these guys cum.
The clean up was long, we exchanged numbers and I started walking. I got back to the bar, still filled with cum, and saw Fred sitting alone. I walked up to him.
“How was it?” I asked
“We made out, then she cried about her ex. Then left to walk home. Where have you been?
“I was just distracting her friend for you to make a move.” I smiled
“You fucker.” He smirked “at least one of us got laid.” He added.
We left. I got home and showered. Then was a good friend, and sucked him off.
It was a win, win, win….win.