I'm A Bad Wingman (Patreon)

I had just left an interview at a major network to start freelancing in their news division. I was 25 and had been freelancing for about a year and it wasn't easy, so this was kind of a big deal for me, even though it was just the interview it was still a big deal at this point.

This was a Wednesday night and most of my friends had regular 9 to 5 jobs so they wanted to celebrate my milestone on the weekend, but I was too excited to just go home. Since I was already dressed nice for the interview I hit up my cousin who works at a fancy bar in one of those high-rise restaurants with a view of the city. He said he had to work until closing but I should come by and he’d hook me up.

That's exactly what he did. He introduced me to the Vesper Martini, which is the actual James Bond Martini because it’s the only Martini that is supposed to be shaken and not stirred. The thing is, it’s delicious, but it’s 100% alcohol. So after two of them, I was pretty tipsy.

Two of the guys at the bar noticed I was close with the bartender and were quick to drag me into their conversation. I didn’t find them particularly interesting but their energy was great and they were fun to fuck with while my cousin was helping other customers. When they would ask me about myself I would just make something up, and practice my improv skills, I didn't care, I would never see either of them again. They worked together at the hospital a few blocks away. Some sort of lab technicians or research techs, couldn’t really tell because I kept joking that they were doctors and they got off on it.

I asked them what they were doing out, the more talkative guy said he was celebrating a promotion and that his buddy was trying to get laid. I think it was a joke but his buddy nearly choked on his drink and I couldn’t help but laugh.

“Well that shouldn’t be too hard here,” I gestured to the nearly all-male clientele of older professional men.

Martin, the more talkative of the two, explained that he was married and would otherwise be “tearing it up” with the “hotties” at the other end of the bar. Then he went on to explain that Owen, his taller friend, is “recently single and ready to mingle.”

“Well damn Martin, you’ve got that big dick energy, why don’t you wing those women in for Owen?” I asked as a bit of a joke but also wanted to bring dicks into the conversation.

He laughed, “Nah, my energy is compensating,” he joked, “Owen keeps his big dick a secret that’s why he’s so quiet,” he laughed.

Owen’s body language shifted.

“Oh really, you’ve got all the inches huh?” I asked.

He shyly shrugged, “I do okay,” he took a sip of his drink.

Owen was a little older than me, probably 30, about 6 foot, thin, his clothes were too big on him so I was getting very straight vibes from him. I couldn’t read his eyes though, he barely made eye contact and the small frames of his glasses helped hide his eyes.

“Oh, ok, well how many inches are you talking about?” I pressed.

He shrugged again, Martin, on the other hand, was too drunk to care either way, “I’ve seen it, it’s like a third leg,” he laughed and pulled Owen into a side-shoulder bro-hug.

I lowered my voice a little, “Oh you guys are more than friends?”

Martin giggled, “No, no, no, I’m married, but if I were gay I would go for Owen,” he joked. “Maybe I am bi for Owen,” he seemed to ponder more seriously than it was supposed to sound.

“That’s not how it works, as a bi guy myself, you either are bi or you’re not,” I said louder than I intended and then quickly looked to make sure I didn't just out myself to my cousin. He was at the other end of the bar talking with another customer.

“So, Owen, are you bi for Martin?” I asked.

He laughed, “No, no, ah…no.”

My cousin returned and asked if we needed anything. I held up my empty glass and he laughed, “One more, and you’re cut off.”

“One more for us too,” Martin chimed in.

We drank another and the only information I was able to get from these guys was that Martin is 5” uncut and wears boxers, whereas Owen is a boxer briefs guy and is cut. When my drink was empty I went to the bathroom to pee, then back at the bar it was just Owen.

“Where’s Martin,” I asked.

“You must have passed him, he just went to the bathroom,” he laughed.

“Are you guys heading out?” I asked and took a sip of the water my cousin brought me.

“Yeah, well we have to work in the morning, and Martin has kids to get off to school at like 7 am,” he laughed again.

“Dang, I feel like we were not good wingmen for you tonight,” I said with false sincerity.

“It’s alright, we were just here to have a drink to celebrate, and…well now we’ve been cut off,” he joked.

“I was here to celebrate too, but I guess I’ll have to call it a night now that I’m cut off,” I laughed.

“You boys ready to head out?” Martin appeared out of nowhere.

“Yeah, one sec,” I walked over to the other end of the bar where my cousin was making a drink for someone.

“Hey, I’m heading out, thanks for the drinks man, you’re the best!” I gave him a fist bump.

He laughed, “Anytime dude, congrats again!”

When I turned back both Martin and Owen were gone. Which was oddly disappointing.

I took the elevator down and when I was out on the street I saw Owen hug Martin and Martin turned and walked away. Owen saw me and walked toward me with a smile.

“He’s fucked, he somehow missed like eight calls from his wife,” he laughed.

“Oh damn, yeah, definitely fucked, and not in the good way,” I joked and Owen laughed harder than I expected.

“I don’t suppose you’re up for one more drink?” He asked.

I looked at my watch, “I guess I could, don’t you need to be up in the morning?”

“I do, so…maybe a drink at my place? I’m only 3 blocks east.”

I couldn’t help but notice the smile tugging at the corner of his mouth.

“Wait, are you suggesting I come to your place for a drink or a drink?” My eyebrows raised dramatically.

“Well…I have a bottle of 12-year-old McCallan and an 8.5-inch dick, so…” he shrugged and smiled a cocky grin.

“Oh wow, I love a good McCallan,” I gave an uncontrollable fishhook-grin back.

We walked quickly to his place in the brisk night air. It was a decent-sized studio apartment with a nice view. His queen-sized bed was arranged nicely along with some other furniture, but I sat on the end of the bed while he got us some drinks.

He handed me a glass with a knuckle of scotch, “I hope you like it,” he winked.

“It’s been a while since I’ve had it, so…” I took a sip and savored the flavor and my clever double entendre.

He did the same. Then he started to pull his too-big dress shirt out of his pants. He slowly unbuttoned revealing a white t-shirt that clung to his tight body. Not muscular, just tight and skinny.

I put my drink on the coffee table, “Let me help you with these.” I reached out for his belt, pulling it dramatically out of its loops. His pants immediately dropped about three inches revealing the top of his green and gray striped GAP boxer briefs, his growing dick the only thing holding the pants up. I looked up at him, his smile was huge, so I gave a gentle tug to the pants and they fell to his ankles. His boxer briefs clung to his body, his dick was already straining to be released. The dick print leaves little to the imagination.

I stood up and kissed him gently to test the water and he was into it. He let out a soft moan, so I wrapped my arms around his neck while he tugged at my dress shirt, pulling it up over my head along with my undershirt, I was trapped by the buttoned cuffs around my wrists but he just tugged harder and I pulled backward until I sprang free and fell back onto the bed.

We both laughed. I sat up on my elbows and watched as he went for my pants, he struggled to get those off too because of the inside button, but he was determined and pulled the pants and my briefs off with one good yank. My dick flew up, hard as fuck as he tossed my pants onto the floor with a loud clank from the belt buckle.

He dove on my dick like he was starving for it, his skill level was middle of the road, but I was too horny to care, I just wanted to get off so I started to immediately thrust into his mouth and take control. He gagged a little but continued to try and it felt pretty good.

After a few minutes, he stood back up and slipped his underwear off, releasing his big dick which hung out in the air as though gravity was pulling on it but his horniness was fighting the gravity. His body was mostly hairless, but he had a decent patch that circled his dick and a light dusting on his balls. He climbed up on the bed, pulling me on top of him and we kissed as we grind our dicks together. His cock was leaking an impressive amount of precum, so I grabbed some of it between my fingers and brought it to his lips and he hesitated but then licked it off. That’s not something I’m really into, but in that moment it turned me on to know this guy, Owen, was not afraid to be himself with me right here and right now.

I kissed him, tasting the precum on his tongue, and we both moaned. He rolled me onto my back, spreading my legs with his longer legs. He leaned over the bed and pulled a little wooden box out from under the bed, setting it on his nightstand that was just a small table with a lamp. He pulled a small bottle of lube out, it was nearly empty but he shook it and got a good glob out of it with a squirt sound. He used most of it to cover his cock but saved some for my hole.

I was getting a little nervous, I might be drunk but this is a big dick and I might have talked a big game back at the bar, but that was when I thought he was straight. He inserted a finger into my hole, then kissed me some more as he gently moved the second finger into position. Fuck, I was so horny that I was going to try to take his cock, I just need to relax.

He scooted up between my legs so the head of his dick could tap my hole.

“Not such a bad wingman after all,” he joked, rubbing the head on my hole, his precum adding a little more lube.

“I wouldn’t want Martin to be disappointed,” I joked and gently rocked my hips in a circular motion as I tried to let my hole relax.

He shift his weight a little and went from tapping his cock on my hole to adding pressure and trying to push in.

“Do you have a condom?” I smiled, one eyebrow cocked up.

“Oh, yeah, of course,” he said as if that was always his plan. He reached over, and dug through the little wooden box for a smaller box of condoms, “last one,” he pulled out a magnum and tossed the cardboard to the floor.

He quickly put it on his dick and tried to get more lube out of the bottle, with very little success but then added some spit to help. He put his head to my hole and started to push gently.

I tried to relax, but the head was fat and blunt, when it popped in it was a bit too much, “Oh fuck, wait, wait, wait,” I begged and he held it there for a couple of seconds while that sting shot all the way their my body, and then he tried to push some more and his dick slipped out.

He stroked himself a little, added more spit, and tried again, this time the head popped in easier, and about two inches went in.

“Holy shit, you’re really tight,” he said as if this was hard for him.

Straining to take another inch of his monster, “Yeah, it’s been a while…and you’re…ungh… really big,” I almost laughed.

“You want some poppers?” He asked.

“Yes, please,” I sounded desperate.

He reached into his bin and pulled out a little brown bottle, took a hit, and then handed it to me. I took a deep hit, and then another. He took that as his cue and started to push in and holy fuck I felt my asshole stretch. He pushed about halfway in and then held it there.

He leaned in for a kiss, I wrapped my arms and legs around him and took his kiss as his dick held me in place beneath him. He gently rocked his hips as we continued to let our tongues dance. Then he rolled us both so that he was on his back and I was on top.

“There, now you can take it at your own pace,” he smiled and handed me the poppers again.

Again I took a deep hit, feeling my muscles relax and his dick slipped a little deeper into me. He groaned as I felt his little bush of pubes tickle my ass. He rocked his hips and his dick pushed even deeper.

“Oh fuck,” I threw my head back and almost launched off his dick, but maintained control.

“So fucking tight man,” he rocked his hips again and grinned.

I took another hit of poppers, and another, my head spinning. Now I felt relaxed and let myself slide that last inch down so that I didn’t have to hold myself up anymore. I leaned down and kissed him again. He put his arms around my back and held me tight, rocking his cock in and out.

“You feel so good,” he whispered.

“Yeah, your dick feels good,” I whispered and rocked my hips to meet his thrusting and it did feel better now.

“You feel really good,” he said, rocking his hips harder into me.

This turned me on, his lust for me was hot, but that combined with the massive stretching my ass was getting, fuck I was mentally having an orgasm that my body was jealous of. I put my hands on his small pecs and rocked even harder on his dick to meet his thrusts, groaning in pleasure, I could feel his dick sliding easier in and out of my chute now, and fuck did it feel good.

“God your dick feels good,” I groaned and rode him the best I could, holding on as he fucked up into me.

“Fuck your hole feels good, so good,” he moaned, fucking me as hard as he could in that position.

He gripped my waist and rocked up into me hard and fast and then let me ride, then fucked into me hard and fast and then let me ride.

“So…fucking…good,” he mumbled and I felt his dick get a little girthier. Then he wrapped his arms around me, pulling me down deep into his cock and back in for a tight kiss as he rolled me back onto my back. We kissed and he grated his hips, as we found our pleasure spots in this position.

He sat up, pushing my legs up by my knees, and gave me a couple of deep thrusts, “oh fuck,” he moaned.

“Fuck yeah,” I groaned, feeling him hit my prostate and then slide all of his inches out of me.

“No, the condom broke,” he said looking down at his dick, gently dropping my legs to his sides and sitting up on his knees so I could see the broken rubber pushed all the way down his slick shaft to create a collar at the base of his big dick.

“Oh shit,” I said in a clearly concerned tone.

“You don’t have to worry, I don’t have anything,” he quickly reassured me, looking into my eyes to make sure I didn’t panic.

I nodded my head, “do you have another one?”

He flopped down on the bed next to me, “I don’t, but that’s ok, it was fucking hot while it lasted,” he smiled and gave me a quick kiss.

“Yeah,” I said, still catching my breath a little.

“Your ass was too tight,” he laughed, which of course made me laugh.

“That extra man-lube must have been what made it start to feel so good,” I joked about his precum.

“For sure, I only changed positions because I was already getting close to cumming,” he laughed. “I wanted it to last a little longer.”

“Yeah, I felt you getting bigger, I thought you were going to cum while I was riding you,” I looked over at him.

“I almost did, but I didn’t want to disappoint you and cum in you so soon,” he laughed, “but you were only going to get another minute out of me anyway…your ass felt even better when we switched positions,” he kissed me quickly and we both laughed.

“FuuUuck…” I sighed in a sing-song tone.

He took a deep breath, “yeah,” he started slowly stroking his slick dick.

I started to stroke my dick as I watched him stroke. Fuck that dick felt so good. We made eye contact as we both were jerking harder now, he smiled, then he reached for the poppers and took a deep hit on both nostrils, capped it, and handed it to me. He got back up between my legs and started stroking himself harder.

“I want to cum on your hole,” he said.

I kept stroking myself, watching this sexy guy stroking his huge dick, I rocked my hips trying to get myself closer to orgasm. I took the poppers and took a big hit, then another, letting the rush take over my body, and slowly continued stroking myself.

Owen slowed his stroking, “You know…” he started to say.

My eyes tried to focus on his eyes, then glanced at his dick then back to his eyes, “yeah?”

He grinned, "Technically I was already in you bare,” his smile got huge, “I think I was in you bare longer than I was with the condom in place, it felt so good too,” he was stroking a little faster now.

I moaned, beating my dick faster, getting closer to cumming, “Yeah, fuck it felt good.”

“Can I…do you want more?” he asked, pushing my legs back up onto his shoulders, he kissed my calf, and his dick naturally hung long enough that the head caught my hole.

“Oh fuck…ungh, I don’t know,” I tried to think if this was a good idea. I was so horny and wanted more dick, still jerking my dick I felt his poke my hole.

“Just a few strokes?” He said, then added some spit to his head and let it push into my hole.

I quickly grabbed the poppers and took another hit on each nostril, his dick still waiting for an answer, I just looked at him, grabbed my dick, started stroking, and nodded for him to continue. Or at least I think I did, and I felt his dick slowly push all the way back in. We both moaned and I felt full again.

“Oh…mmmm, fuck,” I mumble through the pleasure waves.

I flexed my leg muscles and stroked my cock, the rush of the poppers, the heat coming off his big dick inside me, I was in heaven and moaned like a bitch.

“Fuck that feels good,” he started long dicking me again, nice and slow, but increasing with each thrust. “Fuck that feels really good,” he smiled at me.

I stroked faster, “fuck it does, don’t stop,” I told him as I pumped myself closer to orgasm.

“I’m not gonna last long,” he started to twitch, slamming his pelvis into me a few times, “fuck I’m gonna, ughhhhhh,” his body clenched and his hips jammed into me, I felt his dick swell and the amazing feeling of my insides getting coated with warm cum sent me over the edge.

“Oh shit, I’m cumming, I’m cumming,” I groaned and clamped down on his hard cock, my toes curled, pushing myself over the edge, cum shooting out of my dick onto my chest and abs, I twitched and jerked as rope after rope made splats onto my hand and dribbled into my pubes. “Oh…fu..ck..” I twitched one last time and then completely relaxed onto the bed breathless.

“Oh shit man,” he slowly pulled out all of his inches, making me twitch as the ridges of his cock stimulated my prostate a little more. “Fuck, I…I didn’t mean to cum in you, I’ve never had good control with that kind of thing,” he half chuckled, “fucking felt good though.” He sat on his feet, his half-hard cock still bobbing against gravity, coated in his cum and lube as it glistened in the lamplight.

I took a deep breath, “shit, that felt…so good,” I was still reeling from the orgasmic high and the poppers and alcohol, it all just felt so euphoric.

After a few minutes of catching our breath, I decided it was time to leave. I quickly dressed and was out the door. I was on the hour-long subway ride home in no time. It wasn’t until I felt some of his cum drip into my briefs about halfway home that I realized I didn’t get his contact info. Oh well, I guess I’m a terrible wingman after all.