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.
