Ashley is the appetizer

'Fuck that milf'

'Fuck she's so HOT!'

'10/10 would fuck her brains out'

You show Ashley the type of comments that are continuously pouring in, some too fast for to even read as new comments asking you to fuck her brains out keep coming in.

"That's some fan base you got there" Ashley muttered as she read the live-stream comments.

"Wasn't the whole point of the video was to get an influencer to see the 'back of the house' of Slut House?" You chimed.

"What better way than to start with your office?" Ashley smirked at your light-hearted comment, shifting her hips to the side as if deciding what to do. You reminded her earlier than she said whatever requests from the VIP would be fulfilled to the best of her ability and finally enough, she cracked.

"Alrightt...just a quick one in my office. Anal or mouth only...and make sure to film the theme park on the way to the office understood" You nodded your head enthusiastically.

"Guess the back door is only for VIP's huh? But who gets the front door?" You asked jokingly as Ashley showed you the way to her office.

"That would be my husband" She smiled.

"Lucky guy" It took about a 7-minute walk before the crowds started to thin out as you walked to a rather secluded building at the corner of the theme park. It didn't take long for Ashley to fiddle with some keys before opening the door to the office, revealing a rather crammed open-concept office that was currently occupied by women in office wear. If you had to guess, the ladies were roughly the same age as Ashley, or as one commenter in your live stream put it...'A room full of MILFS'.

"Everyone, please meet Mr. Brooks, he's a social media influencer who we're hosting today" Ashley introduced you to the group of MILFS.

"Really Ashley? Another guy? You can't keep bringing VIP's in here" A redhead milf groaned.

"It will be a quick one, just give me the room for 10 minutes" Ashley shot back. You felt you deserved a bit more courtesy than 10 minutes but you kept quiet as the office MILFS slowly marched out the office, one of them wishing you to have fun.

"Right...sorry bout that...anal or just my mouth for you today Mr. Brooks?" You quickly placed your camera on Ashley's desk, positioning it such that your crotch can be seen. Naturally, you instructed Ashley to get on her knees to lube your cock, something she naturally complied with, almost too naturally.

"Oddly convenient that you have a bottle of lube on your desk huh Ashley?"

"Oh please, you think you're the first VIP I've served? Now relax and let me take care of yo-?" Ashley's voice was stunted as she pulled down your boxers, revealing a semi-erect monstrous cock mere inches from her face.

"It's not gonna be too big for you right Ashley?"

"Oh please, I've had bigger" She sounded unconvincing even to herself as she started to rub your throbbing cock with a generous amount of extra oily lube.

"Your wedding ring is still on. Sure you want to show that to your husband while you rub my cock?" This earned you a smile and a light chuckle from Ashley as she looked to the camera, her fingers naturally caressing every crevice of your cock with sticky lube.

"Oh please, he was the one who was crazy about you fucking me. My husband watches your videos all the time"

"Cuckolding huh, I can do that" You smirk as you start to undress what very little Ashley's lingerie managed to cover. It didn't take long for your cock to be all lubed up and within seconds, you lifted the blonde milf off her feet and onto her desk, ass first. Naturally, you enjoyed seeing the surprised look on Ashley's face as you lifted her, hands on her ass.

"Huh...strong aren't you"

"You'll see" You smirk as you lubed two fingers from your left hand before casually inserting them inside Ashley's cute, pink fleshed asshole. Surprisingly, you faced resistance as her ass walls tightened around your fingers.

"Ohhhh-fuccck" Ashley made no effort at all to hide her moans as you probe her back door until you were knuckles deep.

"Tell your husband to loosen you up a bit, it's fucking tight here" Not that you were complaining anyways.

"Hear that honey? You don't use me enough he says" Ashley spoke to your camera as if she knew without a shred of doubt her husband was watching her being probed by some random influencer. You curled your fingers in an upwards motion, poking her anus as you probed for her weak spot.

"Heeekk-kkk" Ashley blurted, her ass tightening further as you poked a particular spot in her asshole nearing the right side. Satisfied, you pulled your fingers out before placing the tip of your cock at the entrance of her asshole.

"Wait...wait...just give me a mi-NUTTEEEE" Ashley moaned out like a pig as you slammed your cock deep in her anus, the plentiful lube working it's magic as you feel every rim of her asshole contract on your pulsing cock. Without waiting for her to recover, you started to pump your hips as you slowly, in and out of her asshole like clockwork.

"Okayy fuckk...you're bigg....you're FUCKING BIG" Ashley groaned to herself, her neck cramming downwards to see your cock slowly churning her asshole into paste.

"I thought you had bigger" You joked as you pushed her legs closer to her chest, similar to a piledriver position, her pussy entrance flailing with each thrust of her asshole.

"Not even close...orhh-h..."

"Smile to the camera" You say as you grab your camera to switch to a point of view mode, Ashley somehow finding the energy to flash a smile while you tear her asshole apart. Until you realized the smile was more of her clenching her teeth from the pain.

"Guess I'm bigger than your husband huh?"

"Fuck so much bigger...Jacob...he's so much bigger than youuuu-heeeekk" You wasted no time as you started to pump your hips faster, the sound of your cock slapping against her asshole essentially fills the office like a loudspeaker. To her credit, Ashley held her ground, her arms desperately clinging to the edge of her desk, not that it helped much as you were rocking the desk with each powerful thrust.

In an act of pride, Ashley was biting her lips in a poor attempt to conceal her moans from you, your viewers and her husband watching behind his screen.

"Hiding your moans from me? That's Cute"

You smack Ashley's round breast with the palm of your hand, as if there was a mosquito on her nipple, the shock-wave so strong it left a palm sized red mark on her right breast.

"HEEE-KKKK" The blonde milf blurted out, some spit and saliva flying from her lips as she yelped at the pain.

"Much better, whores shouldn't keep their mouths shut, I'm sure your husband prefers hearing you moan from being fucked by my cock"

"ahhh-hh...he DOES!" If anything, her asshole tightened when you mentioned her husband at all.

"Just ditch that loser, I can make you much happier than that cuck ever could" Ashley's asshole tightened again at the mere thought of divorcing her husband for you/

"N-No....I-l-love him...I j-just love..y-your c-cock i-is all"

"Try saying that without moaning on my dick huh?' You smirk, casually leaning over as you stole a kiss from the blonde milf, a kiss that quickly turned into a french kiss as your tongue violated her mouth.

"Mhmmm...n-no...s-slurp...p...no-k-kis-sses" A defiant Ashley protested.

"What...don't tell me kisses is for your husband only? Can you believe this chat?" You chuckle as you ignore her pleas and continue mouth fucking her with your tongue, naturally, as you lean over, your cock probes her asshole deeper as you continue your thrusting. It didn't take long for all her defenses to be broken down as she happily succumbed to your advances, in fact, soon she was the one was kissing you deeply.

"F-FUCK...I love your c-cock...I l-love i-tt so F-FUCKING MUCH"

"Hmph, I'll write my number on your ass later, ask your husband to read it for you and call me whenever that cuck of yours can't satisfy you huh?"

"I will! I Will...you hear that h-honey?" Ashley pretty much lost it as you were nearing the edge. In the heat of the moment, she agreed to be your fuck buddy with no strings attached, all while moaning on your cock in a live-stream while her husband watches her from behind a screen. No doubt pleasuring himself while his wife is being fucked like a dog in heat.

"Come here whore!" You grunted, pulling your cock out and violently turning Ashley in a doggy style position, her hands desperately clutching her desk as you continued to pound her ass from behind.

"You really look like a dog from this angle you know that? In fact, why don't you bark for me like a good little doggy"

"HEE--EEKK...WOOF....WOOF" The milf blonde obediently complied, even bothering to stick her tongue out like a dog in heat when you didn't even told her too.

"Fucking hell, guess you really are hopeless huh?" You give Ashley a few hard slaps on her rear ass, barking to hear that you were nearing your limit and that you were going to cum in her stomach.

"F..FUCK...c-cum inside m-me...cum inside my ass p-pleasee"

"Honey...Jacob honey...please watch as another man cums inside me! Please watch as my ass gets plugged by someone else's cock!!"

"CUMMING!"

You grabbed Ashley's head by her hair, pulling it backwards firmly, your hand glued on her ass as you pump your cock deeper and faster inside her asshole, the tip of your cock poking Ashley's sensitive spot you found earlier. In a flash, Ashley's tight asshole was flooded with wave after wave of your warm, thick semen as you pour it deep in her anus. ****

"HEEEKKK...IT'S FILLING ME UP...YOUR CUM IS FILLING ME UP!" Ashley howled as her back naturally arched, her asshole unwittingly accepting every ounce of cum your cock pumps out. Soon enough, Ashley's arms and legs gave out on her as she collapses face first on her desk, all while you were still shooting the last splurges of your cum. ****

"That's a good girl...take it all in. Take all my semen in" You kept your cock sealed and intact inside her ass, the only thing keeping all your semen from gushing out of her asshole.

"Jacob...h-honey...did you c-cum from seeing another man fill me up?" Ashley asked the chat, though she couldn't be bothered to raise her head to look at your camera. ****

"I'm pulling out my cock, show your cuck husband and chat what your asshole looks like with all my cum in it"

"No wait...ahhhorhh" Ashley's protest turned a soft moan as you pulled out your cock, unsurprisingly a wave of cum and semen came gushing out of her asshole and down her thighs. You bark at Ashley to spread her ass cheeks apart and sure enough, even more semen came flooding out. ****

"Hey cuck, I bet you're seeing this huh? Seeing your wife filled with my cum, does it turn you on another man fucks your wife?"

"N-Nooo..h-honey don't look at me" Ashley moaned, suddenly embarrassed with her ass leaking your semen, clearly making a mess on her own immaculate desk. ****

"I'm writing my number on your ass like promised, get your cuck husband to read it for you okay?" You borrowed a permanent marker from Ashley's desk, writing out your digits on the part of her ass not stained by your cum.

"I-I will...the t-tour...rest of the tour" Ashley moaned out, almost as if she was passing out from the anal sex.

"I'll be fine on my own...just get your ass in my hotel room at night, you know where I stay right?" Ashley slowly nodded her head.****

"Good, maybe I'll try your pussy later" ****

"You can't...I'll get pregnant" You ignore Ashley as you wipe your stained cock on her blonde hair before setting off. Just as you were about to end your live-stream, a notification popped up.

'Jacob Conway donated $5,000'