Wilde Debut

This was the right apartment number. For the room where I would be paid for sex for the first time.

For my own sake and performance, I put off reflecting on how it got this far. Instead, I knocked on the door and waited to see who I would serve first. The only detail I got from the service was to come here at this time, so I didn't know who was behind that door.

If anyone was behind that door. After another minute and several more knocks, I had my doubts. Maybe this was a first day initiation prank or something. Yet when I put my hand on the doorknob and found it unlocked, I figured I might as well get it over with.

I came in and didn't see a group of people laughing at me. Rather, I saw a regular apartment room with a kitchen, couch, TV and everything. Everything except people – although someone had to have opened that bedroom door nearby.

And someone had to be making noises coming from that room. Maybe two people, from the sound of it.

It was indeed two people, as I saw when I went inside the bedroom. Two naked people. One naked woman on the lap of a naked man on the right side of the bed, to be honest. I was taken aback, but when they finally noticed me, they didn't stop bouncing. At least the woman didn't.

"Is that my client?" I asked impulsively. "Are you from the service? Was there some miscommunication or something?" I wanted to know. But the woman answered for me.

"You're the new guy, aren't you?" she asked, to my confusion. When I gave a nod while trying to think of words, she said, "Then they got it right. So no, this isn't on them."

Got what right? What didn't they tell me, and what wasn't she....she....hold on a minute. I started looking at the naked bodies for the first time – well, the naked woman, mainly. And there was a lot to look at.

Even with her legs wrapped around this....possible co-worker, it was obvious she was tall, thin and had the body of a supermodel. The parts of her breasts that I could see looked somewhat small but firm, and her ass stuck out just enough to be meaty. But however small some of her parts were, she seemed to radiate sex – and that was before studying her chestnut hair and what may have been the sexiest blue/green eyes I'd ever seen.

Eyes I think I'd seen before....even if not in person....

"You look like...." I didn't finish out loud yet, as I remembered this woman's voice and the voice of....the person I was thinking of. When I was ready to admit they matched – along with other parts – I nearly jumped back and stated, "You're Olivia Wilde?!"

"Good, they didn't give it away early. The last service wasn't that professional," a naked Olivia Wilde said as she stopped riding a naked male prostitute. How the fuck could I see and think that with a straight head again?

"Hang on, this doesn't make sense," I nitpicked. "Why would Olivia Wilde need to....she's got a guy! And she's one of the most gorgeous women alive! She doesn't need to pay for sex!" I pointed out.

"I only do it once a year," the so-called Olivia answered. "Jason understands. At least he did when I promised our own show tomorrow. He can give me that any night for free, but tonight, I want to pay top dollar for something....deeper."

That made me twitch in my pants, which I surprisingly hadn't done already. It continued as "Olivia" wiggled her hips and did some light riding on my.....still silent counterpart while continuing, "My fantasy this year was....mmmm, to get warmed up by a nice, hard veteran of....your new profession. Then a rookie would come in and we'd both learn something. Over and over for hours...."

Olivia gave a low, sultry purr and a sinful smile – if that made me tighten up, who knew how the other guy was doing? But I got a clear visual when she actually got up and went to her feet, leaving the man and his throbbing cock in the clear.

The clearly frustrated man tried to cover himself, yet Olivia said, "There'll be no need for that. Believe me." I wondered exactly what that meant as she told me, "Oh, this is Tom, by the way. He's been with your agency for three years, and it really shows. You'll have a high bar to climb after this, that's for sure. But you don't have to be perfect off the bat."

I heard and saw Tom give a wave and a hello, but he really wasn't my focus now. Now that I began to believe this was Olivia Wilde – a naked Olivia Wilde walking over after saying she paid for sex with me – Tom truly wasn't my concern. I backed out of the bedroom to get some space, but Olivia strutted towards me without losing a beat.

"I just want to break you in right now. And I can pay to put you back together when we're done. Not bad for a first night," Olivia said. "I really should let Tom finish first. God knows I wanna give him a big finish. But I can give you a big beginning too. Or vice versa."

Olivia's seductive eyes dropped down to my crotch, then the rest of her dropped to her hands and knees. She only needed to crawl a few teasing steps towards me, and I could see Tom behind her in the corner of my eye. I noticed him a more when he inserted himself behind Olivia and started fucking her – while her face was in front of my groin.

She pressed her face against my pants and groaned as Tom picked up the pace. I was the only still one, although my cock could have ripped free if Olivia kissed its shape any longer. Mercifully, she took her hands off the floor to unzip me, grabbing my side with her left hand while fishing my cock out with her right.

Once it was free, Olivia went back on all fours, pushing her ass back against Tom's hips. She then bobbled her head down on my cock, in a logical bit of balance. After she pulled back and my heart started beating again, she put her open mouth over my head and licked it all up.

"You want to fuck me like he's fucking me?" Olivia asked. I assumed that was coming later, but assuming anything was a lost cause right now. Instead of waiting any longer for an answer, Olivia sucked my cock as Tom thrust harder into her, then popped right off. With each thrust, she sucked me and then came off, making each suckle far too short.

Yet while this wasn't fast enough for me, it was Tom who did something about it. As he pumped into Olivia, he reached over to grasp the back of her head and push it down my shaft.

Her eyes widened as she had to take more of me in, but she suckled me hard before I could show concern. By the time I could make a sound, Tom was fully guiding her head up and down myself while he fucked her.

"You're welcome," Tom said, although I was in no shape to answer. I let them do their work for me, but eventually realized I should do some of it myself. It was part of my new job.

"Can I take over?" I made sure to ask Tom. His answer was to take his hand off Olivia's head, allowing her to finally pull away. Tom's hands rested on Olivia's hips as he kept going hard, looking unlikely to last much longer. If he could last this long already....well, I did have a lot to learn.

Olivia gritted her teeth as she looked close herself, so I didn't have much time. I put my hand through her hair and asked, "You ready?" just to be sure. She nodded and moaned, then I slipped my erection back between her lips, in time for her to vibrate her groans on me.

Making sure to be careful, I began fucking her mouth at a steady pace, in contrast to Tom's fast work behind her. I hoped it would balance out, or at least make it less likely for her to bite my cock off. Yet Olivia did brush her teeth against my underside, so I let her pull back then. As she caught her breath, I put my head against her soft lips and rubbed them back and forth, without going into her mouth.

"Mmm.....ugh, not bad," Olivia complimented.

"I'm new at getting paid for sex, not sex itself," I filled her in before filling her back up. I pumped faster in her mouth as Tom got ready to fill her pussy, while Olivia moaned a few "Fucks" on my cock. As I saw Tom struggle to hold it, I pulled back and just left my head in Olivia's mouth, allowing her to lick and suck away.

"Fuck, fuck, I'm gonna cum! Cum with me," I assumed Tom said to Olivia. In any case, I took that chance to thrust the rest of my shaft into Olivia, then pump away as Tom finished himself off into her. She moaned so deeply I thought I might go myself, so I pulled back and merely let her groan on my head.

After a second-and-a-half, I took myself out and let Olivia finish moaning freely. Tom held onto her as she came on his likely deflating shaft, while I stayed erect and visible. The fact I didn't come before two people who already had a long head start was a victory right there.

Finally, Tom took himself out of Olivia's pussy, yet he wasn't done back there. He went onto his hands and knees behind Olivia and started licking her clean -- even though his cum was probably on there too. The things I had to learn....

"He's getting a taste. I paid for one too," Olivia reminded. On that score, she took half of me into her mouth and swirled her tongue all around my staff. She then stretched it out as far as she could and pulled back very slowly, only to put her lips on my balls in short order. But she all too quickly glided her lips and tongue up my cock before backing off.

"I've been doing most of the work. You wanna finish this first load, you do it. You are on my dime...." Olivia said before trailing off. Tom was doing his share by eating her -- and not just on her pussy. She pushed her ass back against his face as hers locked on mine and said, "Come on, pop your escort cherry all over me."

I appreciated her using the word escort, and I appreciated the rest of this sight. Indeed, it shouldn't have been too hard to finish myself with this. So I took myself in my hand and began fucking it, as if I was fucking Olivia's mouth again. It wasn't as warm and wet and mind blowing, yet the thought of making Olivia wetter was making me warmer.

"Oh....oh, that's it. I want the best cum money can buy. You think I'm worth it?" Olivia dared me to answer.

"Fuck, of course I do," I said truthfully, studying her face and feeling even more certain of it.

"He does too, I can feel it....I wanna feel you too," Olivia pleaded. Despite how I was supposed to do the work, the way she opened her mouth and showed me that erotic tinkle in her eyes was a big assist. But to add my own touch to it, I pumped myself and rested my head on her lips again. She didn't close them around me, despite her coos as Tom played with her ass and pussy.

While I still could, I took my cock and rubbed it against her cheek, as the softness almost brought me overboard. I held on as I brushed my cock head on her other cheek and her chin, then settled for just masturbating at the end. As it turned out, the sight of her sultry face and the fresh memory of how it felt on my shaft was the right finishing touch.

My first two spurts landed on her lips, but Olivia went down to swallow the rest. She suckled my cum down and licked my erection while it was still present, as Tom finally stopped to see. When I was done, Olivia kept my head on her tongue as she swallowed, but released it once she was done.

"Goddamn...." I let out, then reminded myself not to look too overwhelmed. I was already a rookie prostitute bought by one of the most desired women in Hollywood – I had to keep looking like I somehow belonged. No matter how much longer this was for.

"Is that it?" the last part made me ask. Olivia said something about hours earlier, but that was too big a show for just the first act.

"For you guys for a while. You've got time to kill before one part of you can get back in there," Olivia reminded. "Guess you'll have to use other parts."

Olivia got up on her two feet, her bare form reminding me I was the only one who still had clothes on. I tried fixing that as soon as possible, and when I was done, she came right up to me and put her hands on my shoulders. As I began thinking about going forward, she thought faster and got me to go down on my knees.

Now a few things about that "using other parts" line were getting clearer, particularly with her pussy in my face. "Tom should have licked it clean enough. Can't say the same about the other hole yet, though. Tom?" Olivia requested.

It soon dawned on me what we were trying – a unique kind of DP. As Tom got down on his knees behind Olivia's ass, I decided to get the head start this time. I put my tongue next to her pussy and circled around, then brushed my tongue tip against her lips before plunging inside.

"Ugh, yeah, perfect," Olivia praised. "You owe me for my mouth....get this right and I'll owe you again. More than I already do."

"Sounds like a deal," I pretended to sound like a pro. Then again, most pros must not get treats like this after years of work. But who knew what other Hollywood secrets like this were out there. For my part, I had better things to be buried in right now.

I took the next step of touching Olivia's body for the first time, placing my hands on her waist as my tongue lapped away at her. This helped me avoid Tom's hands, which were above her hips while his face was against her ass. I couldn't see if he got to the center yet, although that was obviously his destination.

Yet I soon saw Olivia's crotch pull back, since Tom's mouth clearly reached her asshole. Therefore, I didn't waste time getting my mouth back on her pussy, or getting my tongue back in there. Soon enough, we were eating out both of Olivia's holes like she clearly wanted.

Olivia groaned and exhaled, putting her right hand on my head to push me deeper. From the corner of my eye, I saw her reach her left hand back to touch Tom. Her hips wiggled and our tongues tried to keep up, though I added my lips as well.

I had a wider area and a likely more delicious one to work with, so I suckled, nibbled and drank down her pussy as loudly and passionately as I could. Tom might have had way more experience, but I chose to think rookies had the enthusiasm that counted. Especially on a woman like this.

There was way more of this woman to touch for added mutual pleasure as well. I slid my hands up and down her smooth, perfect waist, then reached up to flick her erect nipples. After putting my palms over Olivia's tits, I took my hands down to rub her deliciously long legs.

"Mmm hmm, yeah....don't forget my pussy," Olivia said. A few side to side licks on her took care of that, yet I soon heard her get even louder than expected. "Fuck, that's so good on my ass," Olivia revealed, as it was clear Tom upped his game.

I didn't want to waste time competing with him, when I could be focused on Olivia. I suppose since Tom seemed to be hyped as an experienced stud – and had some time to prove it before I got here – he didn't want to be upstaged by a newcomer. Then again, since we were on Olivia's dollar and whim, who knew how long he'd have to stop me?

Olivia just came and so did we, so she could keep us down here a while. The way my cock was starting to stir, it might not be long – and I chose just to imagine how Tom was stirring. If I had an uncertain amount of time on her pussy, I would savor it, Tom or no.

I started by giving her deep, wet kisses, then sliding my tongue up and down her lips. I slid deeper inside with each lick, ultimately just wiggling myself around in there. After a few seconds, I went out and tasted Olivia on my tongue, before using it to coat the rest of her pussy. Once I blew on it, she pushed herself harder onto my face.

"Oh yes, fuck....I want to be wet again," Olivia requested. She called the shots, so I came through for her. I put more and more saliva on her genitals before licking and blowing, and her pussy thrust against my face in the meantime. It pressed on particularly hard before I felt Tom's hands brushing mine on her hips, as it seemed he was pressing his face and tongue deeper into her ass too.

"Fuck me all over with those tongues. Then I want those cocks," Olivia ordered next. I couldn't help but look down and check my once-again erect cock – then saw Tom's across from mine. It might have looked an inch or two bigger, but this was no time to double check.

My tongue slid all over Olivia as I moaned into her opening, like she moaned onto me. It seemed to have the same erotic effect, seeing as Olivia gyrated herself on my face and not Tom's. In fact, she put both hands on my head and outright fucked my face, although she then backed her ass up for Tom in short order.

"Okay, okay, stand up already," Olivia said, somewhat short of breath. I gave her a final deep lick and got up, getting my breath back as well. "Stand next to each other," she told me and Tom.

Tom made the move to walk over and stand side by side with me, which Olivia responded to by getting back on her knees. "Don't make some crossing swords joke, okay? It'll be worth it, trust me," she assured.

"Wait, hold on," Tom started. But it was too late as Olivia grabbed our cocks, then pressed our heads against each other. Our....multi-layered reaction to that was soon pushed aside, however, once Olivia got both our heads into her mouth and started sucking and licking. Well, at least my reaction was brushed aside.

"Jesus," I thought I heard Tom backtrack, before Olivia went over to just suckle my head. She soon went back to Tom's and kept stroking both of us at the same time, then went back to sucking both our tips. She moaned extra hard as she looked up at us and rapidly slid her tongue over our heads.

"Enough of that," Olivia said when she popped off, and I agreed, likely for different reasons. Nevertheless, my cock didn't get much more relief when Olivia got up, kept holding both our shafts and led us back into the bedroom.

"Now this time, you fuck me while I suck you," Olivia announced, seemingly referring to me first and Tom second. As I thought that over, she laid down on the right edge of the bed, so I would have to stand in front. Tom went over to the side and Olivia quickly grabbed his shaft, while relaxing and waiting for mine to enter her.

Despite having fucked one hole already, this was the big task. This was the real 'pop my escort cherry' achievement. But I sucked it up, hoped all that sucking wouldn't make this too brief, and slid myself into a woman's pussy for the first time as a prostitute.

After fitting myself in, Olivia turned her head and reached out to suck Tom off. She started bobbling on him at the same pace I was fucking her, though I didn't know what she was more focused on. To help her decide, I took a breath and started a faster, harder series of thrusts.

I laid my hands on her waist and slid them up her perfect body, stopping at her tits as I pumped more rapidly. I let my palms rub her nipples and kept my right hand on her chest, while my left went down to her filled pussy. As Olivia put her legs around me and broke from Tom's cock, my left fingers rubbed and teased her pussy while my right did the same to her nipple.

"Oh, Goddammit, fucking harder," Olivia wanted, moaning deeper until she put Tom back in her mouth. He started to go in and out of her, repeating the pattern of us fucking both holes at once, only with me in back now.

"Pound me good. Both of you," Olivia requested. Once Tom and I exchanged a look, we both stepped it up.

But while all Tom did was fuck her mouth more, I fucked her pussy while digging a finger into it and tweaking her nipples. For added stimulation, I took my left finger and licked it clean, then licked my left thumb and had both wet fingers play with Olivia's left nipple. After that, the right hand did the same to her other nub

Olivia bucked back hard on me while I made her pussy and nipples wetter. Combined with the added hard fucking in her mouth, she was probably close. Yet she needed a breath and took her mouth off Tom, then headed for his balls – but my next thrust made Olivia clench her teeth an inch away from Tom's sack.