Gigolo to The Stars Ch. 01

Jake Bryce sat in the bar at the New York Hilton at 20:30 on a Friday evening, thinking how much he loved his job. He knew he probably shouldn't, and that he should feel some semblance of shame from what he did, but he didn't.

Jake was a gigolo and proud of it.

He knew he was an attractive man, and his workout regiment had helped him maintain a svelte but muscled body on his 6'3 frame. If women wanted to fork out cash to spend an evening with him, who was he to deny them that?

He was sat, waiting for a client to arrive. He wore his usual attire of a dark blue suit with a black shirt. He'd been given the instructions by his agency to sit in a specific seat at a certain time.

Jake picked up the drink he'd ordered and was about to take a sip when he was approached by what was clearly a bike messenger.

"I believe you're waiting for someone, sir?" Said the man. "Umm, yes, I am" said Jake, somewhat confused "It's not you, is it?"

"No, someone asked my company to deliver a message to someone sitting in this seat at this time. Room 576." Said the messenger.

Jake seemed to understand what this meant. Sometimes, these things involved an element of secrecy or anonymity. "Oh, right, okay. Message received." He told the messenger, who turned and left, the other patrons eyes watching him as he did.

Jake finished his drink, settled his bill and left the bar. He walked to the elevator and rode it up to the corresponding floor.

He wandered the corridors, looking for Room 576. Once he found it, he knocked.

He looked down at his feet, and saw a keycard he slid under the door with a post-it note on it saying "30 seconds, then come in".

He picked up the keycard and looked at his watch. Once 30 seconds had passed, he unlocked the door and went inside.

Jake found himself in what appeared to be an empty room.

"Hello?" He asked, walking past the bathroom door further inside, now fully in the room. He looked and moved toward the window, unaware that the bathroom door had opened and someone had stepped out.

"Well, aren't you a strapping young chap?" Said a female voice with a British accent.

Jake turned around and his eyes widened in surprise.

Before him, in a lacy red two piece lingerie set was Emma Watson. Her long hair was down at her shoulders, slightly covering her breasts in the see through bra she wore.

"Wow" exclaimed Jake, once he'd found his words "I can't believe this. I'd never have thought someone like you would be doing this kind of thing."

"What, you don't think I know how to get dirty sometimes?" Said Emma, putting extra emphasis on the word 'dirty' as she moved toward Jake.

"No, it's not that, I just would've expected one of the most beautiful women in the world to not have to resort to hiring a man for the night. You could have any man you wanted." Explained Jake, the sight of the former Hermione in that lingerie causing his penis to slowly get harder and harder.

"You're right. I could just go down to that bar, walk up to the first man I see and tell him to fuck me senseless and he'd do it like that" said Emma, snapping her fingers "but that's not good press if it got out that Hermione Granger was strolling about looking for random cock, is it? No, I need something that would allow this whole evening to remain between ourselves so I can get what I'm so desperately craving. I've been at the UN all day and I have to cum soon. I need something that my fingers or a dildo can't give me. How about you, big boy," Emma asked, indicating the visible bulge in Jake's trousers "can you give me what I need?"

With that, Emma got onto her knees, and started to undo Jake's built, unzipping his fly and pulling his trousers down to his ankles. She felt his hard cock through his boxers, and pulled those down to free his throbbing erection. "Oh fuck, you ARE a big boy, aren't you?" Gasped Emma, moving her hand up to Jake's penis. "This has got to be what, 7, 8 inches at least?"

"About that" smirked Jake, who was already restraining his orgasm as Emma Watson slowly jerked him off.

The girthy penis twitched in Emma's hand as she rubbed up and down the shaft. The beautiful English actress smiled to herself, thinking how good this would feel inside her tight pussy, stretching her and filling her ever so well.

"Before we do this, just to check, you're clean right?" Asked Emma.

"Tested every month, all clear" responded Jake.

She moved her face closer to the thick cock of the man she just met, looked up at its owner and maintaining eye contact took it in her mouth.

"Oh fuck, that feels incredible!" Groaned Jake, as he watched Emma take more and more of his cock in her mouth, only pulling up to breath, then getting back to it, working the entire length into her mouth until her nose rested against his pelvis.

Emma reached up and grabbed Jake's hands, guiding them to the back of her head. Jake didn't need to be told twice.

He grabbed onto Emma's hair, and started to thrust himself back and forth, his cock pushing into her throat each time he thrust forward.

All Jake could hear were the wild gluck sounds coming from Emma, who had moved her hands down to grab at her breasts and play with her now dripping wet pussy.

Jake knew he'd not last much longer, so he started to ease off. Emma had other ideas, she grabbed Jake's ass and pulled him into her all the way. Her tongue licked the underside of Jake's cock as he lost control and emptied his balls deep in her throat. She kept him in her mouth until Jake confirmed he was finished, then she pulled herself off of Jake's penis, not letting one drop escape her mouth. She made a show of swallowing for Jake then showing her mouth was empty.

Eyes wide with lust, her makeup smudged and spit flowing out of her mouth from the frantic face fucking, Emma looked up at Jake. She went over to her bag on a nearby chair, and took out a pill bottle. She threw it at Jake.

"Take one, then round two. You're gonna fuck me with that big cock!" She demanded, moving to the bed, Jake watched her tight little ass swaying as she moved, the thong of her underwear nestled enticingly between her cheeks. He took out a pill and popped the it, then followed behind, shedding the rest of his clothes. Emma reached behind her, unclasped her bra and exposed her perfect, perky small breasts to Jake. He held Emma close, kissing her deeply. Their tongues danced, then Jake moved to latch his lips to Emma's nipple. He sucked and nibbled on one before moving to the other.

Jake's hands, meanwhile were occupied with Emma's lower half. One gripped the firm cheeks of her ass, while the other rubbed Emma's pussy through her panties, causing the English beauty to moan, her own hands running through Jake's hair, pulling at it as she felt the pleasure course through her.

Jake raised his head, kissed Emma again, then turned her around and pushed her onto all fours on the bed, he got on his knees behind her and pulled her panties aside in order to get at her drenched pussy.

His fingers ran along the length of her slit, collecting the gathering juices. Jake raised his fingers to his mouth, and he got his first taste of the British beauty. The sweet but tangy flavour hit his tastebuds and he immediately had to have more. Lowering to his own knees behind Emma, he started to lick at her pussy, causing the brunette to moan in pleasure.

"Fuuuuck yesssss, eat me, you fucking stud. Get my pussy wetter to take your cock inside." Emma groaned in pleasure.

Jake licked Emma's pussy, then moved slightly downward to suck on her swollen clit. He replaced his tongue with his fingers, rubbing her wet pink pussy lips, spreading them open then pushing two fingers inside.

"God, fuck, fucking finger my tight little cunt. Finger my twat till I come over your fingers. Feels so good, make me cum, I fucking need it. Make me cum then fuck me. Do what you want you fucker, making me feel fucking amazing!" Screamed Emma, drunk with ecstasy now.

"Customer's always right" thought Jake, who quickened the pace of his fingering of Emma's pussy with one hand while the other groped and grabbed her ass. His fingering pace actually quickening, his digits inside the gorgeous Harry Potter actress' pussy feeling around until they found her G-Spot. Jake curled his fingers and pressed against the spongy texture, causing Emma to go wild with lust. "Fuuuuck yes, you fucker! Shit, you're making this feel amazing." Groaned Emma, her orgasm getting closer.

Jake knew Emma was close, and knew how he wanted to push her over the edge.

"Reach back and spread your ass for me." Commanded Jake, Emma immediately obliging.

Jake gazed in wonder and awe as Emma Watson's puckered little asshole was exposed to him. It looked virtually untouched, but Jake figured if Emma Watson was able to take a throatpie without any hesitation, anal play was probably easy street for her. He moved forward, tongue out and took his first lick of Emma's little starfish.

"Oh God, yes, eat my ass. I love it. Fucking rim me while you finger my cunt. Oh god, I'm so close, shitfuck, yesssss" moaned Emma as she was pushed over the edge,, her orgasm coming thick and fast. She screamed in pleasure as she rode the waves of her ecstasy.

Jake kept up his actions through Emma's orgasm, tongue pressed into her asshole and fingers rapidly penetrating her pussy, his hand covered in her juices.

Emma's climax subsided, and she collapsed onto her front on the bed. Jake stood and stared at the beautiful woman trying to catch her breath. The pill Emma gave him was working and his cock was fully erect again. He moved over, and removed Emma's panties.

With Emma still lying on her front, Jake parted her legs, and positioned himself so his cock was rubbing at her entrance. He felt Emma shift her hips, as if trying to get the cock inside her.

Jake obliged, and pushed his full length slowly but surely into the actress's vagina.

"Fuuuuck, you're so tight" moaned Jake, beginning his thrust back and forth.

"Mmm, that's nothing, wait till you feel my ass!" said Emma, smiling dreamily as Jake started to fuck her harder. "Mmm, fuck, that feels so good, you're so deep!" Moaned Emma.

Jake moved his arms and wrapped them around Emma. He picked her up, turned around and fell to the bed, his penis remaining inside her.

Emma got the idea, and started to ride him, writhing her hips as she rode Jake in the reverse cowgirl position. Jake's hands moved up to cup Emma's modestly perky B cup breasts, pinching the nipples and making her squeal with pleasure.

Emma had one hand running through her own hair, the other behind her, resting on Jake's chest to stabilise herself.

Jake was enjoying his view, the gorgeous brunette's perfectly sculpted ass bouncing up and down on his pelvis. He moved his left hand to his mouth, and sucked on his thumb, then reached down between the tight cheeks of the former Hermione.

He ran his thumb down toward her little asshole and spread his saliva around, causing Emma to slightly tense, her pussy contracting wonderfully around Jake's cock.

Still bouncing on the penis filling her spectacularly, Emma Watson looked back at Jake.

She chuckled. "Already? Is my pussy not enough for you? My little English muffin not making this big cock feel good enough?" She asked, her voice dripping with arousal.

"No, no. it's perfect" replied Jake "Don't get me wrong. It's just, you have the most beautiful little asshole I've ever seen. I just have to do this." As he said this, he pushed his thumb inside.

Shit, that feels good" moaned Emma. She stopped riding and pulled herself off Jake's cock.

She threw herself back on the bed, and raised her legs in the air, then moved one hand to her pussy, and other to her asshole, and slid a finger inside both.

She motioned to a bedside table. "Top drawer, there's a bottle of lube, get it!" She instructed Jake.

Jake did as he was told. He got the bottle of lube, opened it and squeezed out a good amount into his hand, which he then rubbed onto his cock.

He moved back over to Emma, and squirted some more out onto her pussy, which she then rubbed into her pussy and down to her asshole, using two fingers to slide inside.

Jake positioned himself, the tip of his cock close to her hole. He watched for a minute as Emma went two then three fingers deep in her most taboo of holes, then she removed her digits nd grasped his cock. She pulled him closer, lining his cock up with her asshole.

"Do it, big boy" said Emma, through gritted teeth. Her hair a mess from sweat and makeup still running from her expert blowjob earlier, she looked unrecognisable from the prim and proper lady you'd have seen on the red carpet or at the UN giving a speech. Now, Emma Watson looked like any random pornstar after a long gonzo shoot.

Jake pushed forward, his hard cock entering Emma's forbidden hole. He barely got the first half inch in before he felt resistance, and he heard Emma whimper. He looked at her and she was grimacing slightly.

Jake thought about stopping, he remained still inside Emma, contemplating pulling out.

Emma sensed his hesitance. "It's okay. It's always like this. First part always hurts but keep going, I'll be alright," she said softly.

Jake started to thrust forward again slowly. With each thrust, he got a little more in each time, until he soon got his entire 8 inches inside the beautiful actress.

He remained still, allowing her to acclimate to his length inside her. He grabbed the lube bottle and emptied it more onto his cock, using his hand to rub more around her hole gripping his shaft.

Emma gave a slight nod, having adjusted to his cock inside her ass, and Jake started to fuck her tight asshole.

Jake was in heaven. He looked down at his cock entering the asshole of Emma Watson, then his eyes scanned upwards, and he looked at the angelic vision of Emma's breasts bouncing in time with his thrusts, then to her face, contorted in ecstasy. She had one hand at her mouth sucking on her fingers, the other hand rubbing along her stomach and breasts, which she then moved to start circling her clit with her fingers.

He watched her play with herself and kept up his pace, giving Emma the ass fucking she desperately wanted.

A couple of minutes went by like this, with Emma mostly moaning her enjoyment with no actual words, accompanied by Jake's groans as he felt himself getting close to his own orgasm which he held off.

"God yes, feels so good in my ass. You're gonna make me cum from fucking my tight little asshole." Screamed Emma.

Jake knew he was close to orgasm himself.

"I'm getting close" he warned Emma.

"Don't stop, just a bit more" moaned Emma, who slid two fingers into her pussy for extra stimulation. "Fuck, yes, please, fuck my ass, make it gape, please. Cum when I do, please. Fill my fucking ass with your load, make it drip out of me while I finger my fucking cunt." Begged Emma, now pistoning her fingers in and out of her pussy, having added a third.

Jake sped up his thrusts, knowing one last big push would finish both him and Emma.

"FUUUUCK, YOU HANDSOME FUCKER, POUND MY FUCKING ASS LIKE I'M SOME RANDOM SLUT" shouted Emma. Her floodgates broke and she came with a huge scream. "YEEEESSSS, I'M CUMMING!" she shouted as she squirted her orgasm right into Jake, whose own resistance gave way and he started to cum himself, his load shooting directly into Emma's asshole. "OH FUUUCK", he groaned as the actress' tight asshole squeezed every drop out of him.

As their respective orgasms subsided, Jake pulled his cock out of Emma's asshole. He watched as the stretched hole gaped for a brief moment, then closed up, slightly red from the hard fucking he had given it.

Jake collapsed on the bed next to Emma, who turned to him and rested her head on his chest.

After a couple of minutes in silence, she spoke first.

"You know, I've got some friends who'd just love you," she said.

Jake raised an eyebrow. "What?"

"I have friends. Hollywood friends, anyway, who are always on about needing a good shag. Maybe you should go private, exclusive clientele, you know" said Emma.

"Not through the agency?" Asked Jake.

"I mean like, get a dedicated number, a second phone or a burner, is that what they're called?" Said Emma, "and the number can only be given by someone who has it."

"And how would I get the number to someone in the first place?" Quizzed Jake.

"Tell it to me" said Emma, who rose and walked to a desk with stationary. She wrote something on a piece of paper and went and put it in Jake's jacket pocket.

"There, now when you go and get your burner or whatever, text me the number and I'll pass it on", explained Emma.

Jake chuckled. "So, are you my pimp now?" He joked.

Emma laughed. "No, I'm more an...intermediary, or a starter point. I'll give the number to one or two of my friends, and they can pass it on from there."

Jake thought on this for a minute, but he soon started to feel tired.

"I gotta go" he said, standing up from the bed and moving to his clothes. He gathered them up. "Can I use the bathroom quick?" He asked Emma

She smirked on the bed. "I need to take a shower" she said, as she rose from the bed herself. She walked past Jake, and knocked the clothes out of his hand as she did so. "Care to join me, Stranger?" asked Emma who then opened the bathroom door and leant on the doorframe, seductively.

Jake looked at the vision before him, and followed Emma into the bathroom. "Of course. And it's Jake, by the way."

*****

Jake awoke the next morning in the hotel room, alone.

He looked around and besides his own clothes bundled on the floor, there was no evidence of Emma having been here.

He rose and went to the bathroom, actually intending to shower this time without the distraction he had of Emma Watson sinking to her knees in front of him as the water poured down and deepthroating his cock for a second time before demanding he fuck her over the bathroom sink and finishing on her breasts.

He'd gone back to bed and went straight to sleep following that.

Jake showered, then put his clothes from last night on.

He checked his pockets that he had everything, and found the note Emma wrote to him. On it was a phone number and a message:

'Send me your private number'.

With the note, Jake also found in his pocket a Polaroid photograph he hadn't taken but Emma clearly had taken in the bathroom mirror, her body fully nude, her beautiful smile radiating and one hand rubbing at her pussy.

On the back was another message:

'For the memory. X'

Jake smiled and left the room, immediately heading to the nearest electronics shop and purchasing a prepaid cellphone. He text the number Emma had given him.

'It's Jake from last night, here's my new number'.

He went about his day, almost forgetting about his new second phone, until two alerts came through.

One was a reply from Emma, saying 'Thx for last night. Given number to friends. Until next time ;) x'

The other alert simply read 'Hotel Edison, Room 750, 19:30.

He text back 'Confirmed. Pay by cash, £500'.

===To Be Continued===