Chapter 1 – Chapter 1

"So I finally got the details about Tom's bachelor party."

"Let me guess…Vegas," my wife responded as she poured more wine into her glass.

"Where else?" I chuckled. My older brother Tom never grew out of his party phase, so we were all surprised when he announced that he and Brandi – that's Brandi, with an "i" – were going to tie the knot. She certainly seemed to be smitten by him, we just couldn't imagine him ever settling down. When the topic of people's sex lives would crop up, he would often blurt out the same lame joke: "I'm trissexual…I'll try anything." The rumor and gossip mills kicked into overtime: some saying that they have an open relationship, some saying she's a trust fund kid and he's marrying her for the money. Whatever the reason, we were happy for them. And Vegas definitely was a no-brainer.

"All the way across the country…Is Jim going?" Julia asked.

We met Jim and his wife Jaquie a little over ten years ago when my wife Julia and I moved in next door, and we quickly became the closest of friends. They were our age and, like us, had no kids. Jaquie and I both worked from home and would go out to lunch together often, and the four of us would occasionally take vacations together. The only thing about Jim, though, was he had to be the cheapest person we've ever met. I loved the guy, but goddamn, break out the wallet every now and then! According to Jaquie they were doing well financially, he just hated to spend money. Whenever the topic of Jim being a tightwad came up, Julia would shrug and suggest that that might be why they have so much money. She had a point.

"Not only is Jim going," I answered, taking the bottle of wine from Julia and pouring some into my glass. "But he offered to make our travel arrangements.

"Oh. I'm sorry," Julia giggled, taking a sip from her glass. "How bad is it?"

"Well, we're flying the red eye, of course. And our accommodations are at the world famous Circus Circus. Where we're sharing a room. With one king bed." Julia practically spit out her wine.

"Sharing a bed?" she chuckled. "I seem to recall you poking fun at us girls when we do that on our trips. I am so not letting you live this one down."

"Thanks," I said, finishing off my glass. "You're all heart."

***

The Uber driver loaded our suitcases in his trunk as we said goodbye to Jaquie and Julia. They both looked amazing, perhaps trying to remind us what we have waiting for us when we got home. Julia was wearing one of her short plaid skirts with a push-up bra and a white button down blouse that was unbuttoned enough that you could see the cups of her bra. Julia was sporting a lululemon yoga outfit on her petite body. She had her red hair pulled into pigtails, and her stretch top made her full C cups appear to defy gravity. The Uber driver was certainly checking them out, and I'm sure they both felt my hard-on when I hugged them goodbye.

"You two behave yourselves," they said in unison as we got into the car. I waved at them as we pulled away, and spent the red eye to Vegas imagining a foursome when we returned.

***

Jim and I left the bachelor party early by Vegas standards. Tom had hired half a dozen strippers for his party, which he was hosting in his penthouse suite. They were all ridiculously hot, and they put on a fantastic show. There were lap dances for all, and a few of the guys had to rush off to the bathroom to clean the cum out of their boxers. Jim and I received our lap dances as we sat next to each other on the couch – his from a curvy blonde with DD cups, and mine from a brunette with perky little tits and the cutest round ass. We fortunately kept it together and didn't blow a load in our pants.

We knew it was time to go when Tom was leading three of the strippers back to his bedroom. We wanted to have plausible deniability if asked whether or not Tom had sex while in Vegas. We were 99.99% sure that Mr. Try Anything blew his load on or in at least one of them, but if we weren't there when it didn't happen, we could fall back onto that 0.01%. At least that was our theory.

Our room was tiny and in desperate need of a makeover. To be fair, the entire hotel needed a makeover. The air conditioner barely worked, so the room felt like it was in the 80s. We pulled the sheets down, stripped down to our boxers, and got into bed.

"See you in the morning," Tom said as he crossed his arms across his bare chest and closed his eyes.

"Yeah, see you in the morning."

Falling asleep was a challenge. I hadn't had that much alcohol in a long time, so the bed was spinning, and that brunette's round ass had my cock wide awake. I thought about going into the bathroom to rub one out to see if that would help, but I figured with how small the room was, Jim would hear the fap-fap-fap of my hand working over my dick. I decided to just lay there, listening to Jim's heavy breathing, and wait for the room to settle down. After what felt like an eternity, I fell asleep.

***

The creak of the bathroom door stirred me awake. I heard Jim approach the bed and stop. I kept my eyes partially closed and glanced at him from the corner of my eyes. He was just standing at the side of the bed.

"What the hell is he doing?" I wondered. His hands reached up to the waistband of his boxers and pulled them down, his semi-hard cock bouncing up and down as it was freed from its confines. My heart unexpectedly started to race. I've seen a lot of porn. I mean, A LOT of porn, so I fashioned myself to be a bit of a cock aficionado. The cock that was a few feet away from me and growing hard was nothing short of spectacular. Large, smooth racquetball-sized balls hung below an eight-inch, wonderfully thick shaft. His cock head was perfectly proportioned, the ridge of the helmet nicely pronounced. He climbed back into bed and slid close to me – not so close that our bodies were touching, but closer than we had been earlier.

My heart rate climbed even higher and my cock started to wake up. Did he know I wasn't sleeping? Did he want me to do something? I was equal parts confused and turned on. While I'd never been with a man, I did jerk off to cocks on porn, and my wide variety of tastes in porn included gay porn and trans porn. Here I was, laying next to a porn star-quality dick…do I dare? As I was weighing the pros and cons of making a move, I felt Jim's hand rest on the back of mine. My heart skipped a beat as he held it there for a moment, then gently lifted it and placed it on his cock.

The feeling of Jim's now fully erect cock gave me goosebumps. I slowly rubbed my hand up and down the underside of his shaft, his thick meat pressed against my palm. I slid my hand up to his head and applied gentle pressure against it, my palm moving in circles. I moved my palm down his shaft to his balls, taking his nut sacks into my hand, massaging them with my fingers. Jim let out a gentle moan as I fondled his balls, his hard shaft twitching in the air.

I rolled on my side, facing Jim, so I could get a better hold on his cock. I wrapped my fingers around him, his girth so thick I could barely get my fingers around him. I started stroking at the top of the shaft, just below his head, my hand rubbing across the ridge of his helmet with each stroke. His cock was oozing precum, pouring that warm, salty liquid all over his head and my hand. My strokes started out slow, but then the pace intensified, my fingers passing across the ridge of his head faster and faster, his precum serving as the perfect lubricant. He was just about to cum, and I jerked faster, his orgasm almost there…

…and I stopped. I took my hand off his dick and watched it jerk and throb, denied the orgasm it thought it was about to have. I stared at his cock as it bounced up and down, waiting for it to settle down. Once it did, I wrapped my fingers around it and stroked the head again, my hand twisting as it moved up and down, slowly at first but then quickening the pace. I sensed his orgasm building, his body stiffening and his legs trembling. He was just about to cum…

…and I stopped, taking my hand of his dick.

"Ohhh fuck!" he moaned as his cock twitched in the air. I gently ran the tip of my fingers up and down his cock, from the base to the head and back again.

"Do you want to cum?" I asked as my fingers continued to pet his throbbing dick. He nodded.

"Tell me you want to cum."

"Fuck, please, make me cum…jerk me off and make me fucking cum!" I smiled and took his cock back in my hand and stroked, his balls aching from the two denied orgasms. I jerked faster and faster, spitting on his shaft to keep it nice and lubricated.

"Oh fucking yes! FUCK YES!!!" he shouted as his cock exploded like a cum volcano. His orgasm was so intense that the first few ropes of cum splattered all over his face, then across his chest, and finally forming a deep pool of jizz on his stomach. I rolled over on my back, a huge smile on my face as I listened to him try to catch his breath.

"Holy shit! I've never cum so fucking hard in my life!" he exclaimed. "Fuck!" I had to admit, I felt a bit proud that the first hand job I gave garnered that reaction. Tim rolled over towards me, his cum dripping off his face and running across his body.

"Now it's your turn," he said with a smile. I settled in, waiting for my own hand job, but Jim had other ideas. He pulled my boxers off and used his hands to spread my legs open. He reached forward and rubbed my hard cock.

"Mmmm, you've got a really nice fucking cock," he said as he moved his hand to my balls. "And I love that you shave," he grinned before he lowered his head between my legs.

"Oh god yes," I moaned as I felt his tongue dance all over my balls. His tongue felt absolutely magical as it licked and flicked my smooth nut sack.

"Yes!" I groaned louder as I felt him suck them into his mouth. I could feel my precum dripping onto my stomach as he licked and sucked on my balls like he had a hunger only they could quench. He popped them out of his mouth and looked up at me.

"I want you to cum in my mouth," he said as he grabbed the base of my cock. He held it upright, pointed at the ceiling, before he lowered his mouth on it. And lowered it. And lowered it. His mouth kept sliding down until I felt my cock press against the back of his throat before sliding down it. His lips pressed against the base of my shaft, my cock fully inside of him. He held his head there, letting me feel the sensation of my head down his throat, before slowly moving his mouth back up.

I thought he was going to edge and torture me as payback for my orgasm denying hand job, but he didn't. When he said he wanted me to cum in his mouth, he meant it. He bobbed up and down, taking the full length of my dick in each time. Looking down at Jim, seeing my cock slide in and out of his mouth, was all it took to send me over the edge. I gripped the sheets of the bed tightly and arched my back as I started to cum, shooting my load into his mouth. Jim swallowed each spurt, sucking on my dick even as it went soft, making sure he got every last drop.

He crawled up my body and collapsed on me, and we finally fell to sleep.

***

The air conditioning wasn't the only thing that didn't work in this room: The curtains did a shit job of keeping the sunlight out. It was already 10 am, but I still didn't feel like waking up yet. Jim was laying on his back and I was on my side facing him. Earlier this morning seemed like a dream, but as I looked down his body at that magnificent cock, I knew it had really happened.

"Oooh!" I cooed softly as I saw Jim start to get morning wood. He rubbed the sleep out of his eyes and smiled at me.

"Let me take care of that for you," I said as I moved down his body. I grabbed his cock by the base and rubbed the head across my face and lips. "You have a fucking amazing cock," I told him honestly. "Jaquie must love fucking this all the time." I kissed and licked his head before slipping it into my mouth.

"Mmmmm…she'd love fucking your cock, too," he moaned as I swirled my tongue around his purple helmet.

"I want to see this dick in Julia. We'll have to swap," I said, briefly taking his head out of my mouth to pitch the idea.

"Fuck yeah, and then have a bi-fucking orgy!" he countered, laying his head back as I wrapped my lips around his head again. While I had lusted after Jaquie for ages, the thought of our wives watching Jim and I make each other cum made my cock twitch. I was about to move my mouth down his shaft when we heard his phone ringing.

"Oh shit," Jim groaned. "Speak of the fucking devil. It's Jaquie wanting to FaceTime." I pulled his cock out of my mouth and playfully smacked it against my face.

"Answer it."

"Seriously?!"

"I want to suck your cock while you're talking to her," I said as I slid his cock back in my mouth. Jim answered the call as I moved my head up and down. I'd never sucked cock before, so I was channeling the hours of porn I'd watched to help with my technique.

"Yeah, the party was…ohhhhh….it was….good…yeah, we're having…mmmm…brunch with Tom in a little bit…"

I massaged his balls with my hand as I sucked harder, tasting another man's precum for the first time. My dick was rock hard, so turned on by Jim's manhood.

"Are you ok?" she asked.

"Yeah, sorry….just….hung…over…" The more he tried to keep his moans at bay, the more I licked and sucked. I could tell from his body language that he was almost there.

"Where's Mike?" she asked. I smiled and thought, "if she only knew!"

"He went down to get something to eat," he said quickly, his breathing getting heavier.

"Well, I'll let you go. Love you," she said as my mouth brought Jim to orgasm.

"Oh god…I love you!" he said, ending the call and dropping the phone to the floor. His cock flooded my mouth with his warm, thick, salty load. I felt so sexy taking a load in my mouth, and I instinctively gulped it all down, relishing the feeling of his dick in my mouth as it grew soft. I crawled up his body on all fours, my raging hard on hovering above his cock. He reached down and grabbed my shaft.

"We'll take care of this later…we better get ready for brunch."

***

Tom invited us back to his penthouse suite after we finished eating. The hotel staff had managed to clean the room while we were at the restaurant, so there was no evidence of the debauchery that happened there last night.

"So, did you have fun at the party?" I asked my brother as we looked out over downtown Vegas.

"Oh yeah, definitely," Tom said. "There's still more fun to be had, though." He and Jim looked at each other and smiled.

"Yeah, it is Vegas, after all," I responded, not quite following what he was saying. He hadn't mentioned any other parties; it was billed as a night of strippers. I excused myself to the restroom while Tom poured some drinks.

***

"Jim, you've got to see that bathroom – the Jacuzzi tub is so massive it's like a swimming…." I came to a complete standstill as I saw Tom and Jim in the living space, They were both naked, and Tom was standing with a drink in his hand while Jim was on his knees in front of him, sucking his cock. My brother took a sip of his drink and placed his free hand behind Jim's head, moving it up and down.

"It's OK, you can come closer if you want," Tom said, waving his drink towards them. I was like a deer in headlights as I watched Tom slide his cock in and out of Jim's mouth. I also felt my cock growing, pushing against my shorts, trying to break free. Jim pulled his mouth off my brother's cock and grabbed it by the shaft, almost as if he was showing it off. It wasn't as impressive as Jim's member, but it was still pretty damn nice.

"Come over, you know you want to," Jim said as he stared at the massive tent forming in my shorts. My erection was a dead giveaway, and he was right. I wanted to cum with Jim this morning, and that desire built throughout the day. The whole time during brunch I was fantasizing about Jim deepthroating me again. I shed my clothes as I walked over to them. Jim had resumed his boss-level blow job on Tom. I knelt behind Jim and pressed my body against his; my shaft pressed against our bodies, settling in between his cheeks, my stomach resting on his back, my chin on his shoulder. I reached around and grabbed Jim's cock and started to stroke him. I missed how his dick felt in my hand, so thick, so warm. I stroked up and down, twisting my hand, squeezing gently.

I ground my hips against Jim, dry humping his crack with my cock. With my chin still resting on Jim's shoulder, I watched as Tom's cock pushed in and out of Jim's mouth. I felt a little jealous because I knew exactly what my brother was feeling. Jim's mouth was incredibly gifted. I started to jerk faster as Tom's dick disappeared down Jim's throat. Jim neared orgasm, his body tensing up, and I denied him again.

"Oh fuck, you playful bitch," Jim said, holding Tom's cock with his hand. Jim stroked it, his spit dripping off the head and onto the floor. He pulled Tom closer and pressed the head of his cock against my lips. Jim rubbed Tom's head across them, and I didn't resist. I was so turned on that there was only one thing I could do.

I opened my mouth.

I practically came when my brother's cock slid inside of my mouth. Jim moved off to the side and watched as I worked more and more of Tom into my mouth. I gagged when his cock head reached the back of my throat, and he pulled back. I grabbed his hips and pulled them towards me, his head hitting the back of my throat again. This time I was prepared, and suppressed my gag reflex the best I could. I started to moan as he gently fucked my mouth, my lips wrapped tightly around his shaft. Was this what Jim meant this morning when he said they would take care of my hard on later? Had they planned this?

Whether or not this was an impromptu session didn't matter, really. All that mattered at the moment was giving good head. I was so focused on sucking Tom's dick that I didn't realize Jim had left to get a bottle of lube; he grabbed me by the shoulder and pulled my away, my brother's hard cock leaving my mouth with a pop. Jim poured lube all over my head and shaft, drenching it, before he turned around and got on all fours. I smiled and moved forward, pushing my head against his hole. He thrust his hips back, taking the full length of my cock in him.

"Fuck!" I groaned, his ass feeling nice and tight around my shaft. I grabbed his hips and started to fuck him. I would later learn that Jaquie pegged him regularly, so his ass was used to getting a workout. My hips slapped against his ass cheeks as I thrust in and out of him. Tom walked over beside me and placed his hand on my chin. He turned my head towards him, his cock slick with Jim's and my spit. I opened my mouth wide and stuck my tongue out playfully, inviting him in.

He accepted the invitation enthusiastically. He fucked my mouth with the same intensity that I was fucking Jim's ass, our balls swaying as we moved back and forth. I sensed his orgasm was close, so I fucked Jim faster, wanting the two of us to cum at the same time. Tom yelled out, arching his back, as I groaned loudly, his cock firmly in my mouth. Feeling his delicious cum shoot into my mouth sent my own cock pulsing, spurting out my load inside of Jim. I swallowed each burst of thick jizz, gulping down my brother's sweet-tasting load. We both sat on the floor, feeling spent and satisfied.

There was one person who wasn't satisfied yet: Jim got to his feet and turned towards us, his cock fully erect and leaking precum. Tom and I looked at each other and then moved in on Jim. Both of our mouths worked over that magnificent cock of his, licking his shaft and head together, sucking his balls, We took turns sucking him off, bringing him to the edge of orgasm, then turning his aching dick over to the other. Back and forth we went until finally Jim couldn't take it anymore: He pulled his cock out of Tom's mouth, stroked his shaft with a vengeance, and shot his load over both of our faces.

We all moved to the nearby couch and collapsed, utterly exhausted. I looked at the clock: it was 3 pm, and our red eye flight didn't leave until tomorrow evening…