Prostate Awakening

Prostate Awakening

Summary: Straight man discovers anal pleasure with two gay men and a bet.

Note 1: This is a 2022 Halloween Contest Story so please vote.

Note 2: Thanks to Tex Beethoven for editing this story.

Prostate Awakening

I was visiting Toronto for a business conference on Halloween of all days, and that night I found myself in a club near the hotel where I was staying ... hoping to get laid... since recently I'd had a bit of a dry spell.

I went with my long-time pal Joey (yeah I know about the movie; that's why I always call him my pal instead of my buddy) and another guy named Henry we'd met at the conference. It didn't take us long to realize this was a gay club. That said, I suggested we stick around for an hour or so... for a few reasons.

1. I was straight, but I always felt comfortable around gay men. I found all that testosterone buzzing around in most straight guys made them too competitive and aggressive to be any fun.

2. I'd been to gay bars before (on purpose) and found them a to be pretty good time. For one, the music was always wicked. For two, I liked the flattering attention I usually received from those guys... even though I knew it wouldn't lead anywhere. Gay guys very rarely disparage straight guys for being straight... unlike the other way around.

3. Joey was gay, and I figured I could let him have some fun before Henry and I switched to a straight club down the street.

Yet because we were having such a good time... and a few drinks... and a couple of joints... that hour stretched out to well past two hours.

I was hit on by a couple guys, whom I amicably declined... although like I said, I enjoyed the attention. It didn't hurt that I was dressed in a cop costume... with the front of the shirt wide open to show off my muscular chest... which it seemed was a bit of a gay man's magnet.

I was flattered to get hit on by even more gay men, who flatteringly told me gay men have the best taste, so I was certified as hotter than hot. And as soon as I changed sides...

I went to take a piss... finally breaking the seal... way later than I usually did... and entered the men's washroom. (Yes, they also had a ladies', but I'm guessing it was rarely used.)

The three urinals were all being used, so I went into a stall. As I was taking a piss, I noticed some open holes on either side of me. I'd heard of glory holes, so I knew what they were, but I'd never actually seen one before.

"Yeah, suck it," a voice said from the stall on my right.

As I pissed, I couldn't help being curious... I'd never seen any gay sex. So once I was done, I decided to sit down on the toilet seat and peek through the hole. I couldn't see much except for a white cock being sucked by a black man. (They weren't using a hole, but sharing the same stall.) I knew I should look away, but maybe because I was a bit drunk, or just because it was something I'd never seen before, I kept watching.

"Oh yeah, don't stop," the voice said (it was the white guy's), as the black man really bobbed on his cock.

I can't explain why, but it got me really hard... this black man sucking the white cock with eager hunger, depth and speed... which very few women could do with my seven-inch cock.

I kept watching... unable to take my eyes away from the gay act. I mean I've had quite a few blow jobs, but except for a woman twice my age (almost three times actually, since I was nineteen and she was in her fifties), no woman had ever sucked me with such eagerness.

"Oh yeah, I'm about to come," the white guy groaned as I slowly, thoughtfully, beat my meat.

The black guy kept sucking, not slowing down at all, and then without a hitch, he swallowed the other guy's load.

I remained transfixed, unable to stop watching, and still slowly stroking my cock.

A minute later, long after the white guy had finished shooting, the black guy pulled away, turned and looked right through the hole and into my face.

He offered, "Want a blow job?"

My eyes went wide, this turn of events greatly startling me. I quickly stood up, put my dick away as I pulled up my underwear and thin costume pants, and bolted out of there. No 'No thanks', not a single word of acknowledgement. I don't know when else in my life I've been that rude!

I returned to the bar horny and flustered, and I decided to go outside for some fresh air.

There was an outside section of the club contained by walls and open to the sky, with heat lamps, so it wasn't too cold on this last day of October, and it was packed.

I went to the bar out there, bought a drink, and tried to compose myself... my dick still hard.

I was adjusting myself... again... just as two guys, one dressed as a construction worker and the other as a biker, strolled up to me saying, "Looks like we found our cop."

"What?" I asked, confused and slightly panicking as I looked back at them.

"You're the cop we've been looking for," the construction worker elaborated. "To go with our other Village People costumes."

"Aaaaah, right," I chuckled, realizing they both did look like they could be in the Village People band in those costumes, except one of them lacked a mustache.

"Hey, how are you tonight?" the construction worker asked, looking to be around my age, late twenties, and pretty good looking. He didn't come across as gay, but neither did Joey, who'd briefly been a linebacker in the NFL.

"Not bad, thanks," I replied, acting friendly and casual.

"Nice. You from around here?" he asked.

"No, I'm from a small town near Edmonton."

"Ahhhh, nice," he nodded.

"Yeah, it's already snowed there, so this Toronto weather feels pretty nice," I said... although my thin costume with the open shirt did make the air a bit chilly.

"I imagine so," he chuckled.

I finished my drink and said, "I should get back inside."

"Wait, are you here alone?" he asked.

"Here with a couple buddies," I said.

"Straight?" he asked bluntly.

"Yeah," I nodded.

"Ever wondered?" he asked.

"Nope," I said, "I'm just here because I like being around you guys," not mentioning I'd just gotten hard from watching a guy get blown... and had briefly jerked off to the sight.

"Not even a little?" he pursued casually, not at all aggressively.

I couldn't get that blow job I'd just witnessed out of my head, and my resulting delay cost me. I responded a few seconds later than I should have, "No, not even a little."

"I noticed your hesitation," he noticed accurately .

"Yeah, well, I just saw a guy getting a blow job in the rest room," I said, figuring there was no reason to make shit up. I knew I was straight and this conversation wasn't leading me anywhere.

"Yeah, that happens around here. Did it turn you on?" he asked.

"Not really," I said.

"You sure?"

"Look, I don't want to be an asshole, but like I said, I enjoy being around gays, but I'm straight," I insisted.

"I'm not saying you're not," he said. "I'm just suggesting maybe you need some relief."

"Thanks, but no thanks."

"Look, want to make a bet?" he asked.

"What kind of bet?" I asked. I was a bit of a gambling man.

"I bet we can get you to beg my friend here to blow you," he offered.

This surprised me. "I don't think so," I said. I'm not going to lie... I was still kind of horny and woody from what I'd witnessed... but I had no intention of getting blown by any guy.

"I know so," he said with confidence.

"Yeah, not going to happen," I said, and turned to walk away... not comfortable with this conversation continuing any longer... my confidence suddenly feeling a little shaky.

"Come on, man. If you're so confident, you've got nothing to lose."

I stopped. I wasn't quite Marty from Back to the Future, but I didn't take getting challenged or an implication I was a coward very well. "You do have a point," I conceded. What are you proposing?"

"How about we go into one of the private rooms, so I can prove you wrong," he proposed.

"No, I don't think so, but thanks," I said, having noticed some stairs going upstairs and wondered where they went.

"Want to make it interesting?" he asked.

"How?"

"I'll bet you a hundred bucks," he said.

"A hundred bucks?"

"Yeah, you join us in a room for twenty minutes, and if your dick isn't in his mouth by then of your own accord, I'll give you a hundred bucks."

"Seriously?" I asked, thinking this'd be easy money.

"Yeah, I'm pretty confident."

"So am I."

"Then you've got nothing to lose and a hundred bucks to gain."

"You'd better not be playing me," I warned, noting we were about the same size physically... but the two of them together could easily mug me if they wanted to.

"No, no, no," he said. "This is all friendly and legit."

"I don't know," I said. "Why do you want to make this bet?"

"Truth?"

"Yeah, truth."

"Well, first you're fucking hot," he complimented.

"Uh, thanks," I said, kind of flattered by his compliment. I mean who doesn't like being called 'fucking hot', no matter who's telling him that?

"And second, I have a philosophy," he added.

"And what's that?"

"That all straight guys are gay curious," he asserted.

"I'm not," I denied.

"Did you get hard while you were watching that guy blow another guy?"

I shrugged, "Yeah, and I even watched them for a bit, but that doesn't mean anything."

"Maybe, maybe not," he said. "Do we have a bet?"

"Not quite yet, first I want to be clear. So I join you two in this room upstairs. We stay there for twenty minutes, and if I don't ask for a blow job, I get a hundred bucks?" I laid it out.

"Exactly," he said.

"And what are the rules while we're in there?"

"Only one," he said. "You have to be naked the entire time."

"Fuck no!"

"No one will touch your dick unless you ask," he assured me.

"Nobody?" I asked.

"Promise," he agreed.

"Fuck it, then let's go," I said, thinking again this would be an easy hundred bucks.

"Cool," he said, and he and his silent friend led me back into the club, up some stairs, down a short hallway, and into one of six rooms. It was pretty sparce in there: a king-sized bed with a pink fitted sheet and a few pillows, a card table a few feet from the bed with various sex toys strewn across it, a medium-sized threadbare rug, and a large flat-screen TV on the wall.

One we were inside with the door closed, and he told me, "Get undressed."

"Sure," I said, not at all nervous to get naked in front of a couple of guys. I played football most Saturday afternoons with my neighbors. I went to the gym. I was very comfortable with my body.

The guy introduced, "I'm James, and my friend here is Larry."

"I'm Jake," I said as I started stripping down.

James turned on the large screen television, and some porn instantly began playing. I'd expected it to be gay porn, but it was straight... a cheerleader getting fucked on a teacher's desk, assumedly by the teacher.

"Nice to meet you, Jake," James said.

"You too," I said as I reached total nudity... with my cock semi-erect.

"Oh yes, fuck me, Mr. Peters," the cheerleader begged.

"So how does this work?" I asked.

"You allow us to touch you, but not your cock."

"That's it?"

"Yeah, that's it," he agreed.

"But no kissing," I specified... that would be too aggressive.

"Fair enough. Agreed."

"Okay then, we may as well get this party started," I said, my cock hardening, since the cute cheerleader was really getting herself drilled.

"All right," he said, and Larry and he both approached me... James pouring some lotion he'd gotten from the table into his hand.

"You have a really nice cock, Jake," James complimented.

"Uh, yeah, thanks," I said. "I've haven't had many complaints."

"I bet not," he said, as he went behind me. I knew my seven inches was above average. It wasn't some monster porn cock, but it impressed the ladies, and I got some looks in my local gym's locker room.

"What are you doing?" I asked.

"Just giving you a massage," he said as his hands went to my ass.

"Hey, don't play with my ass," I protested.

"All we specified as off limits was your cock, and we mustn't kiss you," he said, "so I'm allowed to do whatever I want to your ass," as he continued rubbing it... which felt nice, actually... not that I'd admit that out loud.

"Okay, whatever," I said, confident I could control myself.

"Yeah, just relax and try not to resist the temptation," James teased, as his lubed finger slid into my ass.

"Oh my God!" I gasped; suddenly there was a finger in my ass. That had never happened before except in my doctor's office, and that wasn't recreational... And the recreational kind hadn't even happened while I was alone at home!

"Just relax," he advised, but my cock got instantly hard... betraying me... by flexing wildly.

Larry's lips were suddenly on my right nipple while his fingers played with my left one... which was my secret kryptonite.

The pleasure on my nipples and the weirdly odd sensation of his finger in my ass had my head in confusion... which got me even harder.

I let out an uncontrolled moan from the pleasure concentrating on both my front and back. I demanded, "Get your finger out of my ass!"

"Did you know men's most intense orgasms come from someone massaging our prostates?" James pointed out, ignoring my words, while his finger poked around inside my ass... which felt strangely pleasurable.

"Oh yes, give me that big fucking cock," the onscreen cheerleader begged, now bent over the desk and taking it in the ass.

"I'm not gay," I reiterated, as I allowed one guy to suck on my nipples and another one to rub my prostate.

"Enjoying a prostate rub isn't being gay at all," he said. "Actually, it takes a man who's confident in himself to let himself go and just enjoy it."

"Jesus," I said, his finger feeling really good in my ass... while my cock throbbed inexplicably.

"Yeah, praise His Name, you bet," he said. "Now just relax, and like He advised us to do, set aside any social norms and expectations, and be done with them. Be yourself, no matter who that is right now."

"I can't relax, this is too weird," I said, as I fell into watching the porn and didn't even attempt to stop what was happening to me. I blamed the alcohol somewhat, but the truth was that although I'd only had a few drinks, I wasn't remotely hammered, and I knew what I was doing... or in this case not doing... just allowing whatever to happen.

"Your body says it's loving this," he said, his hot breath on my neck also driving me wild... as did Larry sucking on my nipples. Strange fellow... so far he hadn't said a solitary word.

"I'm not gay," I repeated yet again, in a bit of a daze... confused by how quickly this encounter had turned surreal, and how I was allowing a guy to finger my ass... and... and... how good it felt! Obviously the alcohol had loosened my inhibitions, and apparently my ass too.

"Our fun and games together aren't about your being gay or not," he said, his finger working magic inside me, as was Larry on my nipples going back and forth... sucking and pinching.

"Yes, Mr. Peters, fuck my asshole," the cheerleader moaned, clearly enjoying his cock plunging into her ass.

Thus far in my life, I'd only fucked two girls in the ass... the first one didn't enjoy it at all and it only took about a minute before she told me to stop. And the other time was with a drunk MILF who took it happily, and she asked me to come in her ass. Unfortunately, most of the women I hooked up with weren't into anal sex... although I'd asked many of them.

"Does it feel good?" he asked.

"Yeah," I admitted weakly after taking a few seconds to think about it, while his finger slowly finger fucked my ass.

"Do you want me to stop?" James asked.

"No," I replied, a little shocked by my answer... but I rationalized I was in Toronto... a day and a half from home if I didn't stop to sleep... so nobody I knew would ever know what was happening, unless Joey found out and blabbed... and he of all people would approve, even if I completely switched sides, and he'd never tell anybody. But what I was doing right now wasn't gay at all. I wasn't sucking dick, I was just allowing my prostate to get massaged. I mean a finger in my butt happened at the doctor's office, and right now it felt so good... way different from anything else I'd ever experienced.

"Want me to really give you a prostate massage?" James asked.

"Yes please," I moaned, his finger driving me nuts... as if my ass were a pussy... I was feeling enormous pleasure in there, which seemed like it was connected directly to my throbbing, desperate cock.

"You sure?" he asked.

"Yes, yes please," I moaned, so he pulled his finger out of me, and suddenly I felt empty. I needed that finger back in my ass. "Put it back in my ass!" I yelped.

"Soon. Bend over the table," he said mildly.

"Uh, okay," I said, desperate to get my prostate massaged some more... that pleasure was unlike anything I'd ever experienced. I walked mindlessly the few feet to the table and bent over, willingly offering my ass to some more penetration by his finger.

I watched as Larry crouched underneath the table and began sucking on my balls. "Hey!" I protested, even though it felt good.

"Those aren't your dick either," James mentioned from somewhere behind me.

"I guess not," I had to agree, and then I felt his finger poke my ass and it slid back in... but this wasn't his finger... it was thicker... longer... because it was his hard cock! "What are you doing?" I moaned, but I didn't do a damned thing to stop him sodomizing me.

"You did take me up on my offer to really massage your prostate," he explained.

"I didn't mean you should fuck my ass!" I complained, stunned both because I had his dick in my ass, and it felt completely, unbelievably amazing.

"Trust me," James said as his dick began sliding in and out of me. "You'll soon love this!"

"Ohhhh," I moaned, wanting to turn around and punch him in the face, except it felt so damn good that I remained bent over, allowing this guy to fuck me.

"That's right, just relax," he encouraged as his cock gently slid in and out of me... there being literally no pain... just intense pleasure. But that was totally unnatural... how could there not be any pain?

"Oh God, but I'm not gay," I repeated, even as my cock throbbed while his dick slid in and out of me.

"No," he said, "you're just a cool straight guy enjoying a prostate fucking."

"I can't believe this," I said, literally stunned I was allowing this... and enjoying it! I was getting fucked in the ass by a gay guy who was dressed like a member of the Village People... so I sure seemed gay right now... this was straight out of some lame ass porn movie.

"Just let go of all your past judgements and reservations, and let yourself and your prostate enjoy getting fucked and stimulated," he coached.

"Oh God," I moaned, each thrust making my cock twitch... my head spin... and pleasure fill every aspect of my body. This was way more pleasurable than a blow job or fucking a woman. I know that sounds extreme, and I loved bow jobs and fucking women ... but this was an entirely different level of pleasure, which continued with each thrust inside me. Meanwhile, Larry's sucking my balls enhanced all these sensations.

"You like having my dick in your ass?" James asked after a dozen slow, deep strokes.

"Yeah," I admitted shamefacedly, embarrassed because I did like it.

"Then say so," he ordered as he pulled out.

"Yes! Yes, I love your cock in my ass," I said urgently, desperately wanting and needing that cock back inside my ass... nothing in my life had ever come close to the pleasure I'd been feeling just now. An orgasm lasted a few seconds... this fucking was like an everlasting orgasm... even if I hadn't even come yet.