The Hollywood Gigolo Ch. 01

You might not realize it, but the celebrity escort business is actually a pretty big racket here in Hollywood.

And with good reason, since it gives us "regular" guys a chance to get paid to hook up with celebrities, many of which (okay, ALL of which), would be deemed out of our league under normal circumstances.

And the busiest nights are usually the awards nights, since every celebrity wants to be seen on the red carpet, but not all of them want to be seen alone, and even if they do, almost all of them would rather go home with someone at the end of the night then spend it alone.

That's where I, and others like me, come in.

My first night as a celebrity escort happened to be Oscar night, since the escort business was in need of some extra bodies, so to speak, to handle all of the celebrities that were going to be looking for a hook-up after the show.

I had placed and ad with the people that handle this sort of thing and wasn't really expecting anyone to answer, since I was the new guy in town, but not only did someone answer, but I was floored by who ended up answering.

Because it turned out to be Anna Kendrick.

"Is this John? It's Anna Kendrick. Look, I know it might come as a surprise to you that I'm calling you, but despite my reputation, I have done this sort of thing before," Anna told me, before telling me how she was single and tired of going to awards shows alone and was seeking my employment to be her date for the night.

"And maybe if I get drunk enough...you'll get to say you fucked a celebrity on your first night on the job," she teased me right before she hung up, letting those words linger in my mind right up until Oscar night.

When the night of the big show arrived, I had the limo pick Anna up at her house and saw her come bounding out in a strapless blue dress that just screamed someone was going to get lucky that night, and by the time we actually arrived at the show, it felt like we already had a strong connection.

"Time to show you off big boy," Anna huskily whispered in my ear as we got out of the limo and walked the red carpet hand-in-hand as the flashbulbs went off around us.

"I can't wait to get inside and start drinking," she whispered to me as we rushed off to find our seats after all of the preshow stuff was over with, and from that moment on, Anna either had a glass in her hand or my hand on her thigh as things started to heat up between us as we enjoyed the show, Anna getting noticeably more drunker as the night went along.

"MMM...I am so horny..." she nonchalantly whispered a few hours later as we were mingling at the after-party, Anna introducing me to all of her friends as her hook-up for the night, which never failed to make me blush.

"If you're that horny Anna, why don't we head back to the hotel and fuck," I told her, half-joking, since she had told me earlier in the night that she had never actually gone all the way with any of the escorts she had borrowed for a night yet.

"It might be the whiskey talking, or the fact that I am strangely attracted to you, but you're on," she whispered, squeezing my arm as I called for the limo to take us back to the hotel.

"You really shouldn't tease me like this if you're not gonna go all the way with me Anna," I told her on the ride back to the hotel, my hand resting on Anna's thigh as I started to creep it further up her leg and leaned in to kiss her.

"MMM..." she moaned into my mouth as we started to swap spit in the back of the limo, one thing leading to another until I was on top of her in the limo naked, removing her dress and sucking on her tits as I fingered her pussy.

"Not...now...I...think...we're...here..." she moaned through her ragged breaths right as I was about to push her panties away and slide my dick into her pussy.

"Okay...but the first thing I'm gonna do when we get in that room is fuck you hard," I told her as we got dressed and rushed up to her hotel room, not even stopping to acknowledge any of her fans as we did.

"Take me right here and right now," she softly whispered as soon as we were inside the room, locking the door behind her as she jumped into my arms and let me pin her to the wall, not even waiting for me to get her on the bed before she started to undress me.

"You ever been fucked good and hard up against a wall before Anna?" I teased her as I removed her dress once again and ripped her panties away as I lined my dick up with her pussy and slid into her.

"UH...you feel so damn good John..." Anna moaned as I grabbed her hips and started thrusting in and out of her, throwing her head back against the wall as I pumped her pussy.

"You ain't felt nothing yet Anna, you sexy little bitch," I teased her as I started mauling her tits with my mouth as she wrapped her legs around my waist and pulled me deeper inside of her.

"OHGOD...YES...fuck me John..." she purred, placing her hands on the back of my head as I licked and sucked on her tits while my dick tore up her tight cunt.

"OHGOD...there...fuck...me...there...gonna cum..." she shouted, throwing her head back against the wall and arching her back as I bottomed out inside of her and felt her cunt start squeezing down on my dick.

"Anna...gonna cum baby...can I cum inside you?" I asked her as she drove her hips into mine, wrapping herself around me as my dick started to kiss her cervix, her juices shooting out all over it as she came for me.

"FUCK...YES...give it to me...cum in this sexy bitch's hot little pussy..." she cooed right as I gave her one last thrust and shot my wad into her, large gobs of my cum shooting out into her pussy and sticking to her walls as she pushed her hips into mine, finally releasing her grip on me when I shot the last of my load into her and allowing me to pull out of her.

"Get down there and suck it clean for me so we can continue our night," I told her as I pushed her to her knees, Anna looking up at me and winking as she wrapped her lips around my dick and started to suck on it.

"MMM...don't mind if I do..." she whispered as she went to work on it, her hands cupping my balls and holding my dick in place as she worked me over.

"SHIT...suck it Anna baby...you're gonna make me cum soon..." I hissed as I started to fuck her face, her eyes closing as she once again moaned around my dick, her hands running along the base of it as I snaked it to the back of her throat and held it there.

"Here it comes, you sexy bitch," I warned her as I grabbed her by the back of the head and guided her onto the full length of my dick right as I unloaded my cum down her throat, her hands holding my dick in place as she sucked away on it and greedily drank down every last drop of my cum before letting me back it out of her warm mouth.

"Let's get you on the bed," I softly whispered to her as we made out against the wall, Anna throwing her legs around me, grabbing my dick and leading back to her pussy.

"But I want you right now..." she playfully pouted, letting me wrap her up in my arms and carry her to the bed, making out with me the whole time.

"UH...lick...me..." she moaned as I drove my head between her legs and darted my tongue into her, her back arching as I thrust my tongue in and out of her just like I would soon be once again thrusting my dick in and out of her.

"It's a shame no one's giving this pussy the attention it deserves Anna," I whispered to her as I pounded on her cunt with my tongue, giving her the kind of oral pleasure she probably hadn't received in a very long time as she arched her back and writhed under me.

"Whenever you want something a little bigger to fuck, just tell me," I softly said to her as I drove my tongue in and out of her, her eyes beginning to roll back in her head as she softly came all over my face.

"OHGOD...fuck me...stick it in me and fuck me John..." she begged me as I lapped away at her juices, drinking them down as I lined my dick up with her pussy and slid into her again.

"UH...I'm not usually like this..." she whispered as I began to thrust in and out of her again, her back arching as she threw her head back and let me have my way with her again.

"Blame it on the alcohol baby," I teased her as I drove my dick in and out of her, her walls wrapping tightly around it as I pummeled her cunt walls with it, feeling them stretch out to take me even deeper inside of her as I placed her legs up on my shoulders.

"UH...UH...UH...OHGOD...you're gonna make me fucking cum all over your dick again..." she hissed as she arched her back and threw her head back, her eyes rolling back into her head as she threw her legs around my waist, her cunt walls opening up a little more for me as I bottomed out inside of her.

"Come on Anna...cum all over this dick for me..." I told her as she arched her back one last time and shoved her hips into mine, her body going limp as she shot a load of her cunt cream all over it.

"Here it comes baby," I told her as I grabbed her hips, pulled them forward and thrust into her a few more times, spraying my sticky seed all over her insides as her pussy clamped down on my dick, drawing every last drop of my cum deep into her womb before I finally pulled out of her.

"UH...that was so hot," she softly moaned as we made out on the bed, pushing me away as she got up and bent over it, presenting her ass to me, "but I do have one more hole for you to fuck, baby."

"Don't mind if I do Anna," I teased her as I ran my dick along her ass cheeks and slid it into her, her back arching as I began to fuck her tight ass.

"OHGOD...fuck...my...ass...it hurts so good..." she moaned as I pounded on her back door, her anal ring wrapping tightly around my dick as I tore up her ass just as I had her pussy.

"Gonna make you cum for me again, then I'm gonna cum in this tight ass," I told her matter-of-factly as I grabbed her hips and pulled them backward into mine, her tight sphincter muscles clamping down even more on my dick as I buried myself in her ass and felt her start to cum for me again.

"FUCK...OHGOD...cumming...YES..." she hissed as I drove into her ass one last time, her cum trickling down her legs as I pushed my hips into hers and came deep in her ass, filling her bowels to the brim with cum just as I had done to her womb twice before.

"MMM...you wore me out big boy..." she whispered as I pulled out of her ass and started to make out with her on the bed, her head resting on my chest as we cuddled each other and gathered our strength.

"You weren't so bad yourself Anna," I teased her as we made out some more, neither one of us really wanting to night to end just yet.

"I feel sorry for all the sluts you're gonna hook up with after me," she teased me as I started to gather my things to leave, "because I'm sure they're not going to be able to live up to the experience I just gave you baby."

"We should do this again sometime then Anna," I told her as she gave me one last kiss and let me head for the door, rubbing her satisfied cunt.

"We'll see," she teased me, quickly drifting off to sleep on the bed as I sneaked away from her hotel room, not sure that my first night as a Hollywood Gigolo could've have ever gone any better, and hungry for another night with one of Hollywood's hottest women.