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The Bet

Category: Gay Male
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It was a Friday night, early and nice out; just nice enough for a trip down South Street by’ myself. I loved coming down here in general but it was almost’ always so much better when I was alone. Sometimes, I would walk around for a bit, and then take a trip down to the river and sit there for a while.

Instead, tonight I was thinking of stopping in a bar to have a few drinks before getting on the Frankford-Market line to make my way home.

I stopped in a few places; most of them were’ packed though. After three different bars all of which were so full of people I couldn’t’ find a seat, I made my way down towards 15th street and wandered into a place called Petes.

By this point, I just wanted a seat and a drink, so I ignored the crowd and made my way to the bar. I sat down and a female bartender approached me with a nice smile on her face. “How can I help you?”

“I’ll take a Coors Light please,”

“No problem,”

She returned a few moments later and handed me the beer. I paid her for it, then took a swig and savored the taste sitting it down on the counter and looking back up at her.

“So; is this your first time in a place like this?”

I wasn’t’ so sure what she meant by “a place like this,” and chuckled taking another swig of my beer.

“What do you mean?” I asked.

“A gay bar,” she replied in a very nonchalant manner. “You did realize this was a gay bar…didn’t you?”

I thought she was joking at first. She had to be joking, right; why the’ hell would I have knowingly walked into a gay club. But’ when I looked around at my surrounding’s I suddenly saw it as though I had been blind.

There were practically no women here; the ones that were women looked like your typical butch lesbian. All of the men were either flamboyant enough to tell they were gay, or still gave it away by the fact that they were dancing with other men.

Some were even making out; how could I have been so stupid?

“So it is a gay bar,” I said laughing nervously.

“You’re kidding right; you really didn’t notice?”

“No,” I replied laughing harder now.

“It’s okay; I’m here. Might as well stick around a bit and finish my beer.”

She smiled at me noticing I was almost done and grabbed me another one, setting it down in front of me. I reached into my pocket for my wallet but she shook her head and motioned for me to put it away. “It’s on me,” she said happily.

“Not many straight guys would be so calm in a situation like this. I have to respect that about you; so, put your wallet away. It’s on me,”

“Thanks,” I smiled.

We started up a nice conversation. I learned that her name was Michelle; she’d’ been working here about five years and she was thirty years old now. She was also a lesbian and was dating an older woman who was actually’ related to the owner of this club. That was apparently how she had gotten this job in the first place. I told her my name was Brian and that I was twenty’ eight years old and currently single…and very lonely.

We talked about past relationships and offered each other listening ears and before I knew it, I had been here drinking and talking with her for well over an hour; it was almost 11:30 at night.

I’d’ had at least five beers but I wasn’t’ quite feeling it yet, which was fine. I was not really looking to get’ wasted anyway.

“I’ll be right back,” I said standing up and stretching.

“Have to go relieve the bladder,”

She laughed as I walked away and made my way towards the men’s room. I returned just five minutes later and sat back down to notice a sort of nervous look on Michelle’s face.

“You okay?” I asked concerned.

“Yeah,” she laughed slightly. “You might want to head on home though.”

“Nah, nights still young and I’m enjoying myself.”

“Okay,” she said leaning in close. “Then I should probably warn you before you find it out for yourself. See those two guys over there,”

She pointed past me and I turned slightly to follow the direction she was pointing in; across the room, I could see two men about my age. One of them wore a white t-shirt and a pair of fitted jeans. He had blonde hair that came down to his eyes and a big smile.

The other had short spiky brown hair and wore a black t-shirt that said “Kiss me, I’m horny,” and a pair of gray denim jeans.

“What about them,” I asked not seeing anything that stood out about them except they were obviously not shy about their sexualities.

“The blonde is James and the brown haired guy is Chris. Their locals here at this club, and they have a sort of…track record I guess you can say.”

“Track record huh? What do you mean by that?”

“Well you see,” she said popping open a fresh beer and handing it to me.

“James and Chris…they are a couple. Not exactly boyfriends though, their more like friends with benefits. Their very open sexually and they like to invite other people into the bedroom sometimes. Mainly straight men like yourself who wander in here from time to time.”

I laughed, not really taking her seriously despite the look of sincerity on her face.

“C’mon,” I said. “What straight guy…besides me…would wander in here willingly?”

“Curious folks sometimes here just to have fun with their friends, sometimes they come in big crowds…sometimes they get lost like you,” she laughed. “The point is…James and Chris have’ a habit of seducing most of these straight guys. Seems to work every time, believe it’ or not. Now I’m not doubting’ your sexuality or your confidence in it, but I’m telling you whatever trick these two have, their damn good at getting in a straight guys pants.”

I still was not taking Michelle seriously and’ laughed her off taking a swig of my beer. She got the point and sighed defeated, changing the subject but I could tell she kept looking over at James and Chris as though she were hoping they’d’ keep to themselves.

Eventually, Michelle perked her head up, eyes slightly wide and sighed looking at me a few seconds later.

“Alright, get ready their coming over here now,” she warned me. I laughed and paid it no attention until I felt a hand on my shoulder and turned around to look up into the blue eyes of the blonde’ whose name was James.

“Hey there cutie,” he said. “My names James,”

I looked at Michelle and she gave me a look that said be’ careful what you say, but I shrugged it off and she went about serving other customers for the time being.

“Names’ Brian,” I said introducing myself. We shook hands and James smiled over at his friend.

“This is my friend Chris,”

“Nice to meet you both,” I said shaking Chris’ hand as well. James pulled out one bar stool on the left side of me and sat down while Chris took a seat on the other stool to the right of me.

“So tell me,” James said.

“What’s someone as hot as you doing in a place like this all alone?”

“Oh…I actually didn’t realize this was a gay club until after I came in. I was just looking for a place to have a few beers.”

“So you’re a straight boy,” Chris asked. Michelle glanced over at me as if to tell me with her eyes, not to give too much information away. Partly wanting to prove to her that she was just being overly paranoid, I smiled and nodded my head.

“Yeah, I’m straight as an arrow.”

“Awe, what a disappointment,” James said smiling.

“You have a girlfriend? I bet the ladies must be all over someone as cute as you.”

“Not currently,” I admitted. “We broke up a few months back. I’ve’ been single ever since, by choice really. I’m just not ready to move on yet,”

We continued talking for a few minutes and honestly, everything really did seem completely normal to me. I could not see anything in either of these’ two men that told me that anything Michelle had said was true. Maybe she had just been playing around with me, trying to freak the straight boy out a little.

I did notice how playful James seemed and how he kept flirting quite obviously with me; I also noticed how Chris did not seemed bothered by this at all. In fact, he wore the same bright smile the entire conversation.

Just as I started to think Michelle was crazy, the situation began to change.

“So,” James said. “Has Michelle told you about Chris and me at all?”

I looked over at Michelle who was now leaning against the counter smiling and taking a sip of her’ own beer.

“What do you mean,” I asked trying to play it off.

I didn’t want to outright say yes because I wasn’t trying to make them angry at her or anything like that; so I acted as clueless as I could.

“About our track record,” Chris said.

I looked at Michelle again and she rolled her eyes and gave me a look saying just to tell them; she didn’t’ seem to care much.

“Oh, that track record; yeah, she may have mentioned something about it.”

“Really now,” James said. “So you know that we’re quite fond of straight boys like yourself then. And’ you still seem so comfortable around us.”

“I’m not an asshole,” I said. “I’m completely comfortable with my sexuality. So as long as I have nothing to worry about, why would I have any problems hanging out with you two and talking as friends? If I had a problem with any of this, I’d’ have left this club before you two even noticed me over here.”

“Well, I can see you’re not like most straight boys,” Chris said.

“What do you mean?”

“We can always win them over,” James said. “But their usually rude and ignorant until after we’re done with them,” he laughed. I chuckled and shook my head hoping this conversation would go in another direction…away from them so openly flirting with me.

“So, have you ever been with a guy before,” James asked. I guess my hopes of them drifting away from this topic were not going to be’ answered any time soon.

“No. I’ve always been straight; no interest in guys what so ever.”

I was surprised even myself at how calm I was in this conversation, I was not irritated or anything. In fact, I almost found the entire thing to be quite humorous, and still’ they continued pushing, flirting, making moves and taking random shots at me every few minutes or so. Michelle just stood shaking her head and silently laughing as well; she seemed to know the whole time where this was going though.

“So how do you know you’re not interested in men if you’ve never been with one,” Chris asked.

“See, it’s a lot like vegetables,” James said.

“You’ll never know if you’d like them, until you try them. Dick is sort of the same way…so be a good boy, and eat’ your dick…or, in a more’ straight forward way, my dick,”

Chris started laughing and James just sat there smiling at me the whole time and honestly I could not help but laugh myself; that really was quite a corny one he had just spewed out there.

“You guys are really nice,” I said finally. “But’ I’m really not interested; I wouldn’t mind being friends or anything, but as far as my sexuality is concerned I’m strictly pussy.”

“Oh c’mon,” James continued pressing. “Just give us one shot; I guarantee you won’t be disappointed. I know at least ten other guys who use to say they were straight before they met us, and they can all back my word.”

I sighed and shook my head. “Look…I’m really not-”

“Not interested right,” Chris finished my sentence.

“Look, just one chance is all we’re asking for. Tell you what; how about we make you a bet.”

“A bet,” I asked.

“Yeah…a bet,” James said. “I bet you…that I can give you a boner.”

I laughed and nodded my head, seriously thinking he was trying to joke around with me now. There was no way he could be serious in the least bit. This was just getting stupid now.

“What if I lose?”

“Well hold on now, we’ll get to that,” Chris said.

“Here are the rules; this is a game we play from time to time with guys that really swear they don’t like guys. The rules are as follow; James has three minutes to do whatever he wants to get your dick hard. If he wins, you have to come home with us and let us have our way with you. If by some chance you win, then we back off and leave you alone. Or, we could be friends if your still not feeling to’ awkward about that after we’re done with you.”

That had to be the stupidest idea I had ever heard in my entire fucking life, and yet I could tell just how serious they were both being about it just by looking at them.

They weren’t’ joking at all and I was amazed at how far they were willing to go to get me into bed with them as soon as possible. I didn’t’ know why, maybe it was the urge to prove them wrong, or maybe it was curiosity, curiosity of whether or not they really had seduced those straight men and if they had, then how.

Whatever it was, I found myself speaking my reply without even thinking about it beforehand.


Michelle popped her head up and I jumped at my own voice looking over at her, she was surprised at me and I was surprised at myself. James and Chris smiled and James stood up, taking me by the hand.

“Follow me,” he said. “Let’s go outside and find a place that’s a little more….private.”

I slid off the bar stool, Chris slipped Michelle enough money to cover my tab. They were both so’ confident as they led me across the bar and towards the exit. Michelle shook her head watching as the three of us left, and she sighed putting the money Chris left her in the cash register.

“There goes another one,” she muttered to herself.

When we got outside, James led me around into an alleyway between the club and another building. We moved as deep down the alley as we could until we were far enough out of sight that he could do…whatever he was planning to do to me, without being’ seen. He pushed me up against the wall and the next thing I knew he was rubbing his whole body up against mine while Chris leaned against the opposite wall watching us.

“Start the timer Chris,” he said softly.

Upon finishing that last sentence, James leaned in close and kissed me on the lips. I was shocked at how soft his lips were against my own, and more shocked when I felt his tongue rubbing against my lips begging me for permission to enter my mouth.

I opened my mouth for him and he slid his tongue inside, entwining it with my own and passionately kissing me. As he did this, he continued rubbing his entire body up against mine and squeezing my cock through the fabric of my pants. He eventually broke the kiss and started licking, sucking and biting my neck.

“Shit,” I thought to myself. He had found my weak spot; that was a cheat move. Anyone could get me turned on by kissing me on the neck, especially sucking my neck. It was an instant hard-on for me, I tried my best to ignore the sensations flowing through me, but he was so persistent about it that it just wasn’t’ that easy.

He slid his hands up under my shirt and started teasing my nipples with them while still sucking on my neck; I was certain he was going to leave one big ass hickey that probably would be impossible to hide.

I could feel my cock starting to grow in my pants, and started to feel confused and distraught; what the fuck was happening to me? Why was this so easy for him to turn me on? I was certain it was only because he had found my weakness in my neck. But’ at the same time, I couldn’t’ get over how soft his lips felt against mine.

Maybe I was not as sure of my sexuality as I had thought that I was.

Then it came; I let it out before I could even stop myself. A soft and low but’ loud enough to hear moan, that caught the attention of both men as soon as it left my lips.

“Oh, did you hear that,” Chris asked. “He just moaned…I think he likes it,”

“Yes, I’m pretty sure he does,” James agreed.

But’ he wasn’t’ done with me yet apparently, as he continued practically ravaging me.

He slid my shirt up higher now and leaned in close tracing his tongue around my left nipple for a few seconds before gently biting it and then sucking on it for a few moments. Then he switched to the right one and started licking and sucking that one, while still rubbing the left, which was still wet with his saliva.

I was twitching and jumping each and’ every time that I felt the suction of his lips around my nipple. He had me; I had lost. I had no idea how I had lost this bet that I was so sure I could win, but part of me wondered if somewhere in the back of my head I knew the whole time I would lose. Maybe it had been curiosity when I said that I accepted the deal,

“Okay, okay,” I caved and James pulled away smiling up at me. If he continued on, I swore he was going to make me cum in my pants without ever even’ having to take my pants off.

“Well that was easy,”

“You sure don’t seem very straight to me anymore Brian,” James teased me.

I sighed, defeated; he was right. It’s’ not like I was completely fascinated with how good it felt. But’ I could admit that it was not at all’ what I had expected. I had not thought for a moment that making out with another guy’ and having him ravage me would feel as good as it had. But’ still, they had my attention now, and I was starting to regret not listening to Michelle.

“Well it looks like we won,” Chris said. “Now…let’s head back to our place. You have to hold up your end of the bargain after all,”

We arrived at James and Chris’ apartment twenty minutes after we left the alleyway outside of the bar. When we got there, I was impressed; it wasn’t’ a very big place, just a small apartment with one bedroom, a kitchen and a nice living room included. James and I went straight to the bedroom while Chris went to relieve his bladder and’ also to the kitchen to get us a few drinks.

When we got into the room, James shoved me onto the mattress and pulled his shirt over his head.

“You sure did seem to like when I kissed you,” he said climbing into the bed with me. He crawled over top of me, such ferocity in his eyes the entire time.

His lips met with mine, and his tongue slid into my mouth and I kissed him back with equal passion. He pulled me up into a sitting position and pulled my shirt off tossing it to the floor before pushing me back down and then undoing my belt. He unzipped my pants and seconds later, my cock was free and his lips were’ wrapped around it, sucking me off like a champion.

I moaned, leaning my head back and grabbing the headboard behind me with both hands as James sucked my cock vigorously while running his hands up my chest and rubbing my nipples. As he did this, I tensed up, lifting my ass up off the bed and shoving my cock deeper down his throat.

He started tugging at my pants, pulling them off and tossing them to the floor before taking my cock right back into his mouth again. As he sucked my cock, Chris entered the room and started laughing sitting the drinks down on the table next to the bed.

“Couldn’t wait to start without me, could you James?”

He did not reply, simply continued sucking my cock.

“Well, since you’ve both already gotten out of your clothes and down to business, don’t mind if I join you.”

He removed his shirt, kicked off his shoes and quickly started moving to the side of the bed so he was standing over me.

“Well, go on,” he said motioning down towards his crotch. I got the point quite easily; he wanted me to undo them for him and suck his dick while James was sucking mine. Nervously, I obliged and started to unzip his pants and unbutton them before he slid them down around his ankle.

His cock was right over me now, already hard as a rock but as he stroked it, it started getting harder. He was around six and a half inches long but the harder he got the bigger he seemed to get.

Next thing I knew, he grabbed me by the hair and pulled my mouth towards him, shoving his cock right down my throat. He certainly wasn’t’ shy about it and I gagged and choked a little at first. I could taste piss on his shaft; he had after all just gone to the bathroom.

I got over it though, and’ also started adjusting within a few moments.

“Mm,” he groaned. “Natural cock sucker here; you sure you never did this before?”

James released my cock from his mouth and laughed, watching as Chris shoved his down my throat.

“He certainly does look like a natural,” he complimented me.

“Well, move over Chris, I want some too.”

James started to remove his pants and boxers and as Chris pulled away from me I got a look at James’ dick which was maybe around the same size as Chris, but a lot thicker than his and with more veins popping out.

He moved over me and sat on my chest, his cock inches from my lips and slid forward shoving it into my mouth. I sucked and’ gagged and made all the slurping noises that I was use to hearing girls make when they would go down on me. And’ I was really enjoying it; I couldn’t’ believe it, but I was.

Eventually, they turned me around so that I was leaning off the edge of the bed while James stood in front of me still throat fucking me. In the mean time, Chris got behind me and I jumped in surprise when I felt something hot and wet on my asshole; it was Chris’ mouth.

He had his face buried between my ass cheeks, giving me a rim job as though he were eating out a girl’s pussy. It felt strange, yet surprisingly good, and as he slid in a finger, I groaned over James’ cock and felt my own dick starting to leak pre-cum,

Chris continued his rim job and started finger fucking my asshole at the same time and I continued sucking James’ cock. Soon, I knew what would happen…soon, I knew, Chris was going to have his dick buried up to the balls inside of me and I wondered how I was going to react to that.

“I think he’s ready now,” Chris remarked and it was only then that I realized he had three fingers up to the knuckles deep inside of my asshole.

James pulled away from me so his cock slid out of my mouth and I gasped for air, drool running down my chin. I wiped it off on my arm and gasped again as Chris pulled his fingers out of my asshole and poured some lube on me. It was cold and wet and he rubbed it in making sure my asshole was soaked.

He applied an extra amount to his cock, stroking it and rubbing it all over his hard shaft before grabbing me by the hips and pulling me up onto my hands and knees. I could feel his hard cock probing at me now, poking and probing as he rubbed it against my ass crack. James sat down on a chair in the corner of the room and started jerking off and watching.

I tensed up and gripped the bed sheets tight as I felt Chris’ cock pushing into my tight asshole, pushing all the way deep down inside of me and I cried out in a mix of pain and pleasure.

I felt sick as he started pounding me with long hard strokes, fucking me nice and hard. I bit my lip grunting each time that he thrust into me. It hurt at first, I’m’ not going to lie; it felt like he was shoving a fucking pipe up there. Slowly though, my asshole began to accommodate his size; he had obviously done a fair enough job preparing me for this.

As I started’ warming up the pain began to subside and soon enough he was able to fuck me even harder. I started moaning now, breathing heavier to and my cock started swelling up and leaking pre-cum’ from the tip.

My eyes were blurry with tears, but not tears of pain or emotional pain, it’s’ just that he was fucking me so hard that was how I was reacting. My moaning started to change from moaning to screams of pleasure and soon I was begging him to fuck me.

I watched James from across the room as he stroked his cock to the sight of me getting’ plowed by his lover from behind. Chris pulled out suddenly and’ lay back on the bed, pulling me onto his lap and his cock slid right back into my asshole again so that now I could ride him in reverse cowgirl style.

I bounced up and down on his cock, the sound of flesh slapping against flesh echoed through the room and the musky aroma of sweat and sex filled the air.

James started moaning as he continued jerking off and suddenly, he was standing up and coming over to the side of the bed.

He grabbed my head and shoved his cock into my mouth again. I only got’ to suck him for about two minutes before he cried out in pleasure and shot his load all over my face.

I licked my lips, tasting his salty cum; it wasn’t’ half bad I thought.

Chris was starting to get rather vocal as well, and I could feel his cock swelling up inside of me.

I knew what was coming; he was coming.

Moments after that realization dawned on me, I felt him digging his nails into my thighs and I felt something warm and wet flowing deep inside of me as his cock started to pulsate inside of me. I cried out in pleasure as my own cock started pulsating and I shot my own load all over my chest while Chris filled me with his cum,

When it was over, I collapsed back against him and we stayed that way a few seconds before he pulled out from underneath of me and I rolled over onto my stomach trying to catch my breath. They weren’t’ done with me yet though; James was hard again already and I knew what that meant.

He climbed onto the bed behind me and I felt his cock against my asshole, which was still wide open and leaking cum from Chris’ orgasm. He slid right into me with ease since I was so loose from Chris and started fucking me hard.

I was sweating, my body was trembling and my muscles were involuntarily twitching each and’ every time that he thrust into me.

He pulled out briefly and flipped me over onto my back, lifting my legs up and pushing his cock right back into me. This was a better position I quickly found as I could feel his throbbing cock running right up against my prostate gland and every time it did my own’ erection would twitch and my entire body would jump in surprise.

Within five minutes, James was pumping my ass full of his cum and he pulled out once he had finished and wrapped his lips around my cock sucking me to my second orgasm of the night.

When it was over, we both collapsed on the bed next to each other. Chris was already half asleep, exhausted. We all were beat; I was’ squeezed in between the both of them staring up at the ceiling above me. I couldn’t’ believe it but Michelle had been right the whole time. Oh, how fucking right she had been.

And’ now here I was sandwiched in between two naked gay men. What a night.

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