Ch. 04 - Vegas Vacation Gary's Secret

"12:15 am." Gary notices as he looks down at his phone. "Shit I'm running out of time." He thought as he sat at the automated roulette wheel, bouncing between gambling and surfing dating apps for a woman.

Gary's wife, Eve, had texted a few hours earlier that she wanted to spend the night alone with her new female friend Katie. The two had been having a blast together and Eve was having the best sex of her life. Eve told Gary to get another room and that he was free to hook up with whoever he wanted if he agreed to give her and Katie the night alone. Gary jumped at the chance to have some fun, after all, he already had a spare room to use with his sister-in-law Melissa.

Gary started his hookup search with the typical dating apps that he already had setup. After an hour of swiping, he wasn't getting matches, being a Sunday night didn't help.

Unbeknownst to Eve, or at least Gary thought she didn't know, Gary was bi, well bi-ish. He and his ex-girlfriend regularly had bi threesomes when they were together. Gary had even hooked up one on one with a couple of guys over the years prior to meeting Eve. Once in awhile Gary would have the urge to play with cock. Typically some porn or sex chat with a guy was enough to get him off and squash the urge for a while.

Since Gary was striking out finding a woman to hook up with, he thought he would check Grindr, a gay hookup app, just to see who was on. Gary's interest in playing with guys was primarily limited to threesomes. He wasn't attracted to guys so to speak, but rather just their junk and really needed a woman present to keep in the mood. He thought it was worth checking the app just to see if by some strange chance he might stumble on a guy he would be open to. Unfortunately, as per usual no luck. He just wasn't feeling it with any of the guys. There were a couple of trans women on the app, but his messages went unanswered.

As the night continued, Gary was getting more and more antsy. He was horny and he couldn't stop thinking about the creampies his wife and Melissa had given him over the past few days. Gary had a cum fetish, and he didn't really try to hide it. He decided to check Grindr again, cock was sounding kind of good to him at the moment. After another half hour, unable to find anyone he thought he could keep it up with and that he was sexually compatible with position wise he decided it was time to hire an escort.

Gary pulled up an escort site he had previously found, it was like amazon but for escorts. As he scrolled through the pictures, he immediately went to the short blondes. Since he was married to his "type," a red head he tended to gravitate to blondes. As he looked at a very attractive, very petite blonde all he could think about was eating a creampie out of her.

The thought of eating a creampie out of the blonde escort led his mind to wander further. "Hmm it would be kind of hot if she had a cock." He thought.

Gary had a thing for trans women, after all, they were a perfect balance for his attraction to women and cock. Without thinking Gary flipped the filter on the site from women to trans.

"Fuck it." He thinks to himself. "I've always wanted to have sex with one, when in Vegas as they say."

Gary scrolled through the profiles and found one he liked. Her name was Courtney, she was a bit taller than Gary at 5'8." Courtney had light brown hair, perky D cup breasts, a nice plump but firm ass and a 7" cock. Best of all Courtney was versatile, she liked to top and bottom.

Gary followed the directions and contacted Courtney through the site. About fifteen minutes later he received a text. "Hey Gary, this is Courtney. I received your appointment request, when are you looking to meet up?" The message read.

"Hi Courtney, as soon as possible!" Gary replies.

"Great, which hotel are you at?"

"I'm at the Venetian." Gary replies.

"Cool, I can be there in 30 minutes if that works for you?"

"Perfect, where should we meet?" Gary replies.

"Let's meet in the casino by the Gran Lux Café, wait at one of the slot machines but out of view from the restaurant. Send me a quick selfie so I know what you look like." Courtney responds.

Gary rushes up to his spare room, 905, and takes a quick shower to freshen up. He changes into fresh clothes he had snuck in the other day for just this type of situation.

He rushes back down to the casino and plants himself in front of a slot machine as Courtney had directed. To help calm his nerves he decides to try his luck at the slot machine.

After a few minutes, he feels a hand on his right shoulder and hears a sultry voice say, "Hey baby, how's it going?"

It was Courtney, he recognized her from her pictures. She was dressed to impress, a nice short, tight-fitting dress that was sexy but not over the top slutty. Looking up at her he gazed at her perfect figure, she was gorgeous and with her huge puppy dog eyes she looked too innocent to be an escort.

"Hi! Wow, you look amazing!" Gary replies.

"Aww, thanks sweetie. Do you want to hang out here for a bit or head up to your room so we can get better acquainted?" Courtney replies.

"Uh, room, yea lets go up to my room." Gary stammers as he gets up to lead her to the elevators, unable to stop staring at her.

The two ride up the elevator in silence, Courtney just smiles, blushing at Gary's gaze. The elevator dings as the doors open, it startles Gary, causing Courtney to giggle. The two walk down the hallway to the room, Gary clearly with a hurried step.

They reach the room, Gary inserts the keycard, unlocks the room and steps in turning on the light. "Right this way." He directs.

Gary nervously stands in the center of the room. "Have a seat." He offers.

Courtney sits on the foot of the bed, patting the bed next to her inviting Gary to sit next to her.

"So just to confirm, an hour, correct?" Courtney asks.

"Yes, that should work." Gary replies.

"Ok, if it runs over, not to worry I'm flexible." Courtney adds.

With that Courtney leans into Gary, and gently kisses his lips. Gary leans in and slides his tongue into Courtney's mouth searching for her tongue. When he finds it, he begins caressing it, sliding his tongue deeper with each caress.

Courtney breaks the kiss, "Lay back." She says softly.

Gary lays back, as Courtney stands up. Slowly and erotically, Courtney unzips her dress, slowly lowering it to the floor.

"Holy Shit!" Gary stammers as Courtney stands there in nothing but her black sheer panties and bra.

Gary can't help but stare at her stiffening cock barely covered by her sheer panties.

Courtney leans down and unbuttons Gary's pants. Slowly she unzips his zipper. Grabbing his pants and boxers by the waist band she slides them off exposing his fully erect, shaven 7" cock.

"Mmmm!" She moans. "That's nice!"

Courtney climbs on the bed and works her way to Gary's erect cock. Erotically she slides it in her mouth, slowly she deep throats it. She pulls her mouth off his cock and begins to lick down his shaft to his balls. Gently she caresses Gary's balls with her soft tongue.

"UGH! FUCK! FUCK YEA!" Gary moans out gently.

Courtney licks her way back up his shaft and wraps her lips around the tip of his cock then laps her tongue around the tip. Slowly she slides her mouth down his shaft, once again deep throating Gary's cock. Up and down, up and down Courtney bobs her head on Gary's shaft.

"UGH! UGH! YES! FUCK!" Gary says louder and louder with each moan.

Gary can tell he will cum quick if she keeps this up. He reaches down, grabbing her arms and pulls her up towards his face. Once they are face to face Gary gently pushes her on her back.

"Mmm, someone knows what he wants." Courtney says deviously.

"Hmm Mmm." Gary replies as he kneels in front of her, looking down intently at Courtney's erect 7" cock behind her sheer panties.

"FUCK THAT'S HOT!" He says mesmerized by Courtney's perfect body. "I want your cock!" Gary exclaims as he reaches down and pulls off Courtney's panties, fully exposing her hard cock.

Gary drops down, planting his face right in front of her cock, wraps his right hand around her thick, throbbing shaft then lowers his lips around the head. Gary plunges down on her shaft as deep as he can, gaging a bit at first. After a few bobs up and down to get his own fix he brings his lips to the tip of Courtney's cock and laps the head with his tongue just as she had done to him. After a few swirls he slides his tongue down her shaft, to her large balls.

As Gary strokes Courtney's cock with his right hand, he caresses her balls with his tongue, teasing up her shaft a bit then he works his way down towards her ass hole. He licks his way up again taking her cock in his mouth when he reaches the tip.

"MMM! FUCK BABY! UGH! UGH! YEA BABY, FUCK!" Courtney moans as Gary continues sucking her throbbing cock.

Gary slows his pace, then let Courtney's cock flop out of his mouth and on her stomach. Gary sits up. "Roll over, I want that ass." He says.

Courtney rolls over onto her knees, hikes up her ass and gives it a little shake as she looks back at Gary with a devious smile. Gary positions himself behind her, spreads her ass cheeks, exposing her smooth ass crack. He bends down, gently licking from the bottom of her balls, up her ass crack. Gary repeats this motion a few times, slowing more and more on her perky hole with each lick. On the final lick he stops and slowly teases her hole with his tongue.

"UGH! UGH! FUCK BABY!" Courtney moans.

Gary sits up, positions his cock behind her ass and picks up the bottle of lube. He slathers it all over Courtney's ass crack and his shaft. Slowly he starts to press his cock into Courtney's tight little ass hole. Courtney is eager to feel Gary inside her, she starts to push her ass back towards his cock. Slowly they press against one another edging Gary's cock deeper and deeper with each gentle thrust. Finally, Gary presses a bit harder and slides right in Courtney's ass.

"OH FUCK! FUCK YES!" Courtney moans.

Slowly Gary starts thrusting in and out, in and out of Courtney. "FUCK BABY! YES! FUCK YES!" She moans and Gary pumps her thick ass. "Mmm! Mmm yes baby! Fuck my little fuck hole!" Courtney moans in a slutty voice.

Gary starts to pick up speed, faster and faster he slides his cock in and out of Courtney, adding lube every couple of minutes.

"Roll over." Gary directs. "I want to see you face when I cum in your ass."

"Mmm, you got it baby!"

Courtney rolls over on her back, hikes her legs up and with a come hither looks says to Gary, "Come fuck me baby. Come pound my little slut ass."

Gary slides between Courtney's firm legs, grabs her ankles to help hold her legs up. Courtney reaches down grasping Gary's cock with one hand and the bottle of lube with the other. Slowly she strokes his cock as she lathers it with lube. Gary leans forward sliding his cock in Courtney's ass. As Gary releases her ankles, Courtney grabs her thighs. Gary bends further down to get face to face with her, pressing his lips against hers. Faster and faster Gary pounds Courtney's ass.

"MMM! MMM! MMM!" The two moan in harmony as their lips barely touch.

Without breaking the slight contact between their lips Gary whispers, "Your ass feels amazing! You're so fucking hot! I'm going to fill your ass. You want my cum baby?"

In a sultry voice Courtney responds, "Fuck yes baby. Cum in me! FILL ME UP! GIVE ME THAT COCK!" she demands.

Gary thrusts a few more times, plants his lips firmly on Courtney's and passionately kisses her as he cums deep in her ass, completely filling her up.

The two continue to kiss for several minutes, before Gary decides he's ready for more. He looks down at Courtney with pure lust in his eyes. "I want you to fuck me." He says to her in a yearning lustful tone.

Gary climbs off Courtney, as Courtney sits up, she looks at Gary sternly. "On your knees!" She commands.

Gary gets on his knees and hikes his ass in the air. Courtney gets behind Gary, lowers her face to Gary's ass, spreads his ass cheeks and beings rimming his ass.

"OH FUCK!" Gary exclaims. "FUCK YES! OH MY GOD THAT FEELS AMAZING! FUCK!"

Faster, Courtney toys with his ass as Gary starts grinding back on her face.

"You want my dick baby?" Courtney asks.

"FUCK YES! FUCK ME!" Gary moans loudly.

Courtney picks up her bottle of lube, covers Gary's ass crack and her finger with lube, then slowly begins teasing his hole with her finger. Gently she begins to penetrate his ass with her pointer.

"JUST FUCK ME! I WANT YOUR COCK! I WANT IT NOW!" Gary says eagerly.

"REALLY?" Courtney says in an excited tone.

She covers her cock with the lube then quirts some more Gary's ass hole as she positions her cock against his eager hole.

"Are you sure baby? You sure you don't need to work up to it?" She asks.

"YES POUND ME! POUND MY ASS!"

Courtney pushes her cock forward slowly, to her surprise it slides right in with minimal resistance.

"DAMN!" She says. "Fuck you took that like a pro."

Gary chuckles, "Now fuck me! Fuck me HARD! He exclaims.

Courtney starts thrusting in and out of Gary's ass. Picking up speed and force with each thrust.

"UGH! UGH! UGH! YES! YES! YES! YES BABY FUCK ME!" Gary and Courtney moan in unison.

"Fuck I'm close you want me to pull out?" Courtney asks.

"No, but hold on I want it on my back." Gary replies.

Courtney slowly pulls out and within a blink Gary rolls over on his back and pulls his legs up. "Stick it in, quick! Come on fuck me baby!"

Courtney slides between Gary's legs. "UGH FUCK!" Courtney moans as she slides her cock in Gary's ass.

"MMMM!" Gary moans. "Yes baby pound me!"

Courtney starts thrusting faster and faster, she leans in to kiss Gary. As she does Gary grabs her face and pulls her face into his. "Fuck me baby! Fuck me! YES! YES!" He says with their lips touching, then he pulls her in for a full-on kiss.

"UGH! UGH! UGH!" She grunts. "I'M GOING TO CUM!" She exclaims.

"CUM IN ME! I WANT YOUR CUM BABY!" Gary shouts as his aggressively kisses her.

Courtney begins to shake, then she cums depositing a massive load in Gary's ass.

As Courtney goes to climb off, Gary embraces her and pulls her back on top of him. "NO! I want you on top of me! I want you to stay in me!" He exclaims.

The two laid there, Courtney's semi firm cock buried deep in Gary's cum filled ass as the two vigorously make out.

After a few minutes Gary can feel Courtney getting fully hard again, he breaks the kiss and without moving away from her lips' whispers. "Fuck me again!"

Courtney resumes the aggressive make out session as she starts to thrust in and out of Gary's ass again. Faster and faster Courtney thrusts, all of the cum creating plenty of lube.

"MMM! MMM! YES! YES! FUCK! YES! YES! FUCK ME! FUCK MY ASS! FUCK IT! Gary shouts.

Within minutes Courtney cums again.

As Courtney pull her cock out, cum leaks out of Gary's ass and down to his balls.

"Mmmm that felt amazing." Gary says. "Now I want to fuck you."

Courtney gets on her knees, crawls up toward the headboard, grabbing the top of it. She wiggles her ass at Gary as an invitation. Gary gets behind Courtney, lubes his cock and starts thrusting into her ass.

As Gary picks up speed and force Courtney's cock can be heard slapping her stomach.

With every slap Courtney squeals. "OH! OH! OH!" Over and over again.

Gary reaches around with his left hand, grasps her left breast and gives it a firm squeeze. Simultaneously he reaches around with his right hand and starts to stroke her cock.

"UGH! UGH! UGH!" Gary grunts and he picks up speed.

Within minutes Gary his cums in her ass. The two collapse on the bed and kiss.

"That was fucking amazing!" Courtney says.

As the two clean up Gary hands Courtney an envelope for her time. Courtney leans in and kisses Gary. "That was incredible baby!" She says.

The two kiss again and Courtney makes her way to the elevator.

Gary climbed back into bed and laid there reliving what just happened. "Oh my god that was better than I could have imagined." He thought to himself.

Before long Gary was starting to get stiff again. "Shit, I knew I should have booked her for the night." He said to himself.

As he continued to get worked up again, he pulled up his phone thinking he'd pull up some porn and jerk off before going to bed. As he did, He noticed he had a missed notification on Grindr, as he opened the app he saw he had a new message that came in about 15 minutes ago.

The message was from a guy named Chris.

"Hi." The message started. "27 yo 5'7" vers, 5.5" cock." The message read.

Below the message were a few photos. The first picture was a full on body shot of Chris completely naked, striking a pose. He was Asian and very fit. Six pack abs, slight muscles and totally smooth. He was the one type of guy Gary found attractive, the one type Gary could actually get hard up over.

Gary scrolled down to the next pic, "Mmm. Nice!" he thought to himself as he looked at the picture of Chris' cock. It wasn't big but it was shaven and cut. Gary could feel his cock stirring. Chris also appeared to have a cute bubble but. Normally with guys Gary is pretty much just a bottom but with fit Asian twinks and with trans women, he is versatile so this looked promising.

As Gary read Chris' stats and looked at his photos another message came in from Chris. "Staying at the Venetian and really horny."

As Gary read the new message, he couldn't deny it sounded fun and since he was in the same hotel it was easy.

"Fuck it." He thought. "I'm still horny and more dick sounds good."

"Hey, cool, I'm vers too. Want to come to my room?" Gary replies.

Ding. Gary's phone notifies him of a new message. "YES!" It reads.

Gary replies. "Room 905, how soon can you be here?"

"2 minutes." Chris replies.

Gary's cock is now hard as a rock once again. He is a little nervous since it's been years since he had all out sex with a guy. About two minutes later he hears a gentle tap on the door. Gary opens the door and there stands Chris.

"Damn, he's even better looking in person." Gary thinks.

"Hi, I'm Chris."

"Hi." Gary replies.

The two walk into the bedroom, Gary stops and turns to Chris. "So, how would you like to start." Gary asks nervously.

Chris suddenly leans in to Gary and plants a kiss squarely on his lips. "Mmm." Gary moans.

Gary begins to kiss back, the two embrace and start feverishly searching for one another's tongues. Within minutes Gary can't wait, he needs Chris' cock in his mouth.

Gary drops to his knees, rapidly unbuckles his belt, and in a flash has Chris' pants and boxers down at his ankles. Gary takes Chris' cock in his mouth and starts bobbing back and forth sliding Chris' cock in and out of his mouth. Faster and faster Gary moves, impatiently trying to milk the cum out of his cock.

"Lets 69 I want to suck your cock too." Chris says.

Gary stands up and starts to strip, as Chris takes off his shirt and steps out of his pants. Chris lays on his back and Gary climbs on top in the 69 positions. The two start vigorously sucking one another's cock, and toying with each other's balls. Chris slowly starts to work one hand onto Gary's ass and begins massaging Gary's ass hole. Gary slides a bottle of lube back to Chris. Chris lubes his fingers and starts working a finger in and out of Gary's ass.

Gary momentarily stops sucking Chris' cock. "More." Gary faintly directs

Chris doesn't hesitate, immediately sliding in a second, then a third.

"FUCK! I want your cock in me!" Gary exclaims as he rolls off Chris.

Gary lays on his back and holds up his legs. "Fuck me!" Gary says in a devious voice.

Chris climbs between Gary's legs, lathers his cock with lube and slides it in Gary's ass. Due to Gary's fucking less than an hour ago and from a bigger cock, Chris' cock slips right in.