Wilde Debut
Author: Robertdoc
Celebrity: Olivia Wilde
Warnings: M/M/F, M/F, cons, anal, oral, blowjob, handjob, cunnilingus, analingus, facial, fingering, male prostitution, sixty-nine

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.

Tom breathed an exhale of relief – then exhaled far differently when Olivia sucked his balls one at a time. After finishing, she returned to his cock head and Tom went back to fucking her, just as I truly slammed into her.

"Fuck, I'm gonna cum, you fucking make me cum!" Olivia got out rapidly. She then sucked Tom all the way down and I put myself all the way in, inspiring us to pump hard all at once. The sensation made her cum all around me and take her mouth off Tom, yet she held his shaft as she laid down and let her orgasm wash over her.

Olivia wiggled her hips as she came down, then slowly unwrapped her legs and took her pussy off of me. The rest of her body stayed still as she kept holding Tom's dick, and we waited for our next orders.

Eventually, Olivia got herself up, walked over to me and stated, "On your back now." Deciding it best not to question her, I got on the bed and laid down, then stayed there as Olivia laid herself down onto me.

She didn't kiss me or try to put me back into her, as she just relaxed on my body. Taking advantage while I could, I put my arms on her and let myself savor her silky form on top of me. My hand then went up to her hair, stroking the soft brunette locks, unlike the last time I had my hand in them.

"Tom? Get back there and start licking," Olivia told him. I reluctantly looked away from Olivia to see Tom get behind us, kneel down in front of the bed and start licking her. Olivia put her face on my neck, groaning for a bit before adding, "Higher."

It was easy to figure out Tom was licking her ass again. It was less clear what I was supposed to do in the meantime. Having Olivia lie on me, and having my cock pressed against her stomach, wasn't bad while I waited. Yet it didn't seem fair that Tom got more of it right now, or would soon, if I suspected correctly.

My suspicions seemed ready to come true as Olivia lifted her body up. She straddled me right below my cock, while sticking her now lubricated ass out for Tom to penetrate. He got up and stood behind her, wrapping his arms around her as he lined his cock up. As for me, I could only lie back and watch for the moment.

Olivia stiffened up as Tom entered her ass, then laid her hands on my stomach for balance. She rocked herself on me after a while, as it helped her rock back against Tom's cock. Mine was still sticking out, bare, erect and untouched – like Olivia's pussy in a couple of ways.

Given that she just came, letting Tom fuck her ass bought her time while her pussy recovered. After a few more moments passed, I started playing my part to get it ready again. My left hand reached out to her snatch, brushing it before putting two fingertips against it. Yet they did push in as Tom grinded himself deeper on Olivia's backside.

Technically, Olivia was now being DP'd, although this was a mere warm up. But as Olivia went to stroke my cock while bucking back on the one in her ass, it was clear practice was almost over.

Olivia herself put my head onto her opening, yet I saw Tom start backing out of her ass as well. When he had only a little bit in, I figured it safe to start filling her up myself. I merely put the head in and let Olivia adjust to this deeper DP, then we both slid another inch in to make it deeper.

"Come on, a little more," Olivia dared us. Taking the hint, I pushed myself all the way in before Tom could go further. Olivia exhaled as I put my hands on her upper legs, then pulled back just as Tom inserted himself all the way into her ass.

Our ill-timed rhythm went on like this for a while, but Olivia didn't seem to mind. I even threw both my forefingers into the mix onto her pussy. Yet eventually, me and Tom matched up and fucked her holes in unison.

Olivia threw her body back and put her right hand on the back of Tom's head. I could only keep my fingers on her pussy while she grinded all of herself on him. "Fuck, that's so good," Tom predictably uttered.

"I know," Olivia bragged/praised him. But she quickly looked down at me again after that, then leaned down and got on all fours above me. "Didn't forget about you, though," she assured me.

"Thanks," was the much less effective answer I had. Still, she stayed on her hands and knees, pushed her hips down on both of us, and generally looked like a sexy human shaped cat. So I didn't blow it that much – especially when I grasped her dangling breasts and bounced them around.

Olivia was really doing a lot of the work now, or at least her crotch was. We each kept thrusting into her, but she only seemed to be riding us faster with time. It was one thing to start losing energy, but her gaining it only made us look worse – and at least one of us was a professional.

It was harder to be annoyed when Olivia completely laid her body on top of me again. Her hands slid onto the back of my head and she laid her head down next to my ear. I saw Tom grasping her thighs as he fucked her in a doggy style position – yet my position let her put her lips on my ear and groan quietly. So mine had some benefits too.

"Mmm….this feels like my money's worth," Olivia whispered. "Missing something though," she added, then took her lips off my ear and called out, "Tom? Lie down on me."

"What?" was all he had, too distracted for obvious reasons.

"Put your hands on the bed and lie on me. Make us into a sandwich," she visualized.

"So you're the creamy, gooey middle, eh?" Tom interpreted. "Or at least you will be."

I tried not to roll my eyes, since Tom was about to lean right over me too – and since I'd likely roll my eyes for hotter reasons later. In any case, he put his hands on the bed right between us, leaned down and pressed down on Olivia as much as he could – making her the middle of a big sandwich indeed.

"Ah, perfect," Olivia praised, then quickly backed herself up on our cocks again. We resumed thrusting up, but she drove down on us even faster. The little break seemed to give her even more of a second wind, so I gathered myself up for either my second or third.

I pushed myself all the way into her pussy, then took a breath and pumped in and out as fast as possible. My face rested on her shoulder, then I peeked up and saw Tom laying his face against her hair as he thrust harder. Olivia moaned and praised us both, and yet her thighs still gyrated enough to keep up.

"That's it, give it to me," Olivia pleaded. "A few thousand dollars for a few hot, wet loads of cum in me. I can cum on those hard cocks and pay you that way too….oh, fuck, I want to pay you that way. Make me pay before you pay inside me…."

My payment was still a little ways off, but Tom seemed to think he was closer, given how hard he pulled out and thrust back into her ass. I didn't have as much room to do that, yet I furiously pounded away below while preserving my breath. However, Olivia rode our quickening hips in between with much less visible effort.

She still sounded pretty worked up, calling out, "Fuck me, fuck me! Put every last drop in me! Drain those fucking pricks!"

I didn't want to be the first one drained out, but her gyrations and demands weren't helping. I couldn't help myself from pumping hard and rapidly either way, despite how I should have savored this moment more. However, I wanted to savor the feeling of cumming in Olivia Wilde more.

Without even the courtesy of trying to make her cum again first, or hold out longer than Tom, I ravaged her pussy until I shot first. I threw my head back and groaned, yet I heard Olivia groan and purr in approval too. At that point I began slowing down, but I felt and heard Tom going even harder.

I then felt Olivia and myself being crushed by Tom, as he went so hard his hands and arms gave out. He wound up rolling onto the bed and taking Olivia with him – making her slide off me in the process. When I took stock, I saw them lying on their sides, as Tom was out of control trying to finish himself in Olivia's ass.

Soon it became clear he succeeded, as Olivia screamed and kept moving her thighs. She probably hadn't cum yet, and now she wouldn't do it on my deflating cock. But in a stroke of luck, I was able to remember another place she could come on now.

Without caring how close I was to Tom's privates, or how my own cum was still sloshing in Olivia, I rolled over and quickly put my face on her free pussy. It came at just the right time, as she finally went over the edge along with us, exploding right on my lips. I ate, swallowed and licked away at Olivia's release, completing the last step of this remarkable but suddenly exhausting saga.

After licking her clean as much as I could, I pulled myself away and laid next to Olivia and Tom, needing to catch my breath. I heard them breathing hard too, then the first words I heard were, "Come here," from Olivia.

I got an idea of what "here" was when she reached out and pulled our faces to her chest. She positioned her nipples right at our lips, and I couldn't help but take a suckle. I heard kisses from right next to me too, as we both nursed on Olivia's firm tits.

"Very nice," Olivia said quietly. "We should be ready again in no time."

"Come again?" I broke from her breast to ask.

"That's the idea. I know you guys should have one more in you. I got a few to spare," Olivia stated.

"You're still raring to go?" Tom now said. "I don't know how much more you expect from us."

"I said at least one more," Olivia repeated. "Come on, you're the veteran, right? You should know how to get one last load going."

"They usually don't let me stay that long. They're usually satisfied enough by now," Tom answered.

"Well, that's the amount of satisfaction they paid for. I paid for something more….epic," Olivia actually said with a straight face.

"And this hasn't been it?" Tom said incredulously. "What does that mean, exactly?"

"It means I don't want to be done yet. I know you don't want to be either," Olivia answered, which was true enough.

"I don't want to be. I'm sure he doesn't either," Tom remembered to acknowledge me. "But biology's another matter," he pointed to his nearly worn out cock.

"Fine. If you still need time, fine. You don't really need to move at all, then," Olivia reasoned. "But until you do…."

Olivia got further away from me and straddled herself right over Tom's face. She came down on his mouth and humped against it, until Tom got the message and held onto her thighs. He began licking her out, not needing to move the rest of his body at all – yet I felt even more useless.

I was nowhere near recovery myself, but I had to be useful and remind her there was someone else to have a final round with. With Tom working on her pussy and Olivia riding his face, there wasn't really much I could do. Except for one option.

Olivia's perky ass was in full view of me, open for experimentation. As she put her hands on the wall and bucked on Tom's face, I reached over to touch her ass and glide my fingers between her cheeks. This finally made Olivia turn to see me, and she answered with, "Okay, now we're talking."

My left forefinger went up and down her crack while she put her right hand on Tom's head, keeping her left on the wall for balance. Tom seemed to dig deeper into her pussy, so I had to start working on the other hole. Before I got too far into her ass, I took my finger out and licked the tip, then put it right up against Olivia's asshole.

Instead of going in, I teased the hole and made it wetter, while Tom made her wetter in front as well. "Oh yeah, that's it, fuck," Olivia praised. "I am more than ready," she filled us in, then turned her head to see Tom's semi-erection. "Now for you two."

Olivia backed away from Tom's mouth, signaling that I needed to get out of her ass too – for now. As I backed up to give them room, Olivia kept Tom still and turned around, only to put her crotch back in his face. This time, her face was back in Tom's as well, as she settled into the 69 position.

Her ass was still sticking out and clear for another shot, even as Tom ate her out right below. I watched Olivia suck him off to make him fully hard again, and it was clear it wouldn't take long. Even after all the punishment and loads it had been through, Olivia knew how to at least make it hard in no time. Good to know.

I probably didn't have much time before she fucked him and left me alone. So I inserted my finger right back in her ass, working it like Tom's tongue worked her pussy. I tried to wiggle my part in unison with Tom wiggling his, but Olivia pushed herself back against us either way.

She did this as she sucked Tom's cock louder and harder, until she popped off and saw it was fully erect again. This made me look down and see I was coming along – but Olivia saw it too.

"Your turn," Olivia said, then took herself off my finger and Tom's mouth again. I backed away as Olivia got off Tom, leaving him alone and hanging. I laid down on my back, with Olivia settling next to me right on cue – then she planted a kiss right on my lips.

It was the first time she actually kissed any of us, at least while I was here. And she was giving it to me….right after she had another man's cock in her mouth. That was probably the appeal to her, yet I wasn't so sure.

However, this was still Olivia Wilde kissing me. And she was slowly and seductively sliding her tongue and lips over mine – probably the best way to block out what they'd been on moments ago. In addition, she settled her whole body on top of mine, then cupped my face and gave me a few more steamy pecks.

Once she stopped and I saw her heart-stopping face an inch away from me, smiling the sexiest smile imaginable, I forgot Tom was even here. "That was….wow, more than you gave him," I blurted without thinking.

"You don't know what we did before you got here. Yet," Olivia answered. "I had to settle him down before he got going….just like this…." She showed me by sliding down my body and kissing down my chest, licking it every so often.

"This is really your first time on the job?" Olivia double checked. After I nodded dumbly, she added, "Your place has a good eye for new talent. Maybe I'll cast you as the veteran next year," then dipped her tongue into my bellybutton.

"Whatever you have available," I tried to play along. Olivia's way of playing with my cock was much smoother, however. She dabbled her tongue on my slit as my shaft got more erect, then kept it on as her mouth slid almost all the way down my rod.

After a few deep sucks, I couldn't help but say, "You like sucking cock, don't you?" With all the evidence I had of it, I figured I wasn't too over the line.

"I have a few tastes for it," she responded.

"Thank God. That fucking gorgeous face and mouth filled with cock and cum….oh, fuck," was really all there was to say. Especially when Olivia took me down and shook her head while she swallowed and licked, then did the same with my balls.

"I want to be filled everywhere else. Lube my ass up," Olivia ordered, before getting back on the bed and back on all fours. "Get behind me and lick me," she told me, and I couldn't help but obey.

Olivia's face was hovering over Tom's, then she leaned down to kiss him despite just having my cock and balls in her mouth. In case Tom wouldn't let her have enough, I went down and circled my tongue around her backdoor. Tom didn't pull away, though, and I wound up kissing her ass in tandem with him kissing her mouth.

After Frenching and licking her from behind long enough, I removed my face and sat up to put my cock in its place. Olivia left Tom's mouth as I entered her ass, gently thrusting the first few inches in and out. But Olivia backed the next inch in herself, so I filled in the rest right there.

My strength and stamina was still questionable, leaving me to try and go deep without going too fast. To help Olivia out anyway, I went down to her pussy and did some rapid work with my fingers. By the time I got a second one in, I was ready for a quick, hard series of thrusts. Olivia met me with each one and kept up the pace faster than I could.

Before I started breathing too heavy, Olivia kept her ass still and said, "You should lie down. And you should give Tom room to play too. He looks ready enough."

Taking her word for it, I exited her ass and laid down on the middle of the bed. Olivia crawled back to me, but then turned around and laid her back onto my chest. I instinctively put my arms around her waist so she wouldn't fall off, and when she settled, she reached down to line my cock back up with her ass.

Getting the idea, I put my head in and held onto Olivia as she adjusted. Her head rested on my left shoulder as her body laid onto me and her legs spread wider. In this position, her pussy was free and clear for Tom to use while I occupied her ass below.

"Eat up first," Olivia said. Tom went over and got his head between her legs, as I started pushing deeper into her ass. It wasn't the easiest position to thrust into her, but I rocked my body enough to do the job, with Olivia doing the rest. Once Tom got started, she was being fucked and eaten out at the same time, which helped her if not us.

My hips did most of my work and I was resting on a bed, so this helped me not to tire out. Still, we both probably wouldn't come for a while, if we had one more spurt in us. Even Olivia had to be running thin, although her usual bucking against my ass and Tom's mouth looked standard.

"How the fuck are you still doing this?" Tom asked into Olivia's pussy.

"Lots of practice….fuck, what do you think?" Olivia groaned. "I work non-stop, and I still do it like a Kenyan runner. Oh shit….and I don't even fuck for a living! What about you?"

Tom didn't answer with words, or even more oral. Instead, he got up on his knees, put his erection on her – while trying to stay between me and Olivia's legs – and started jackhammering away. I had to hold on tight to Olivia as she shook above me, while trying and probably failing to make my thrusts affect her too.

"Fuck yes! Come on!" Olivia ordered. Tom kept going as fast as possible, but I could tell he would tire himself out. As for me, I bid my time and got my own strength up while fucking her ass slowly. But when I was set and when Tom was close to slowing down, I took my shot and fucked her like a piston.

For a few moments, both me and Tom were fucking Olivia at our fastest. She threw her head back and groaned incoherently, and right next to my ear. I then turned my head to her ear and whispered, "Cum for us. Give us one more so we can give you one more too."

Those were all the words I could say as I pumped away and tried to stave off my exhaust. Yet my words seemed to make Olivia fuck us back and balance it out. Tom was breathing pretty heavily, but Olivia was only regaining her strength, if she ever lost it.

"Come on, cum all over us," I panted, trying to inspire her faster. "You wanna suck your cum and ass off our cocks? That'd make us cum so hard…."

"Uh huh," was all Tom could say.

"That's right," I added. "Come on Olivia….leave here with three sets of cum in your mouth…."

"Yes! Yes!" Olivia yelled, which was all she really needed to say. All she really needed to do was cum before we did – and in any other scenario, that would have been impossible. Yet now that we were only close, Olivia could batten down and cum hard without making us go.

Olivia squeezed onto me so hard, it took some effort not to go off or pass out. I could only imagine how Tom was holding off too. However, he stayed on his knees and only fell on his back once Olivia took herself off him. On that cue, I released her from my arms and let her roll off me.

As if nothing had happened, Olivia got herself on her feet in no time, then asked, "On your feet one more time. It'll work better that way, trust me."

I was almost too comfortable to leave the bed, yet I used one last bit of reserve energy to get up. I figured I might have to help Tom get up too, but he did it all on his own. As he did, I walked over to Olivia and she immediately got on her knees, then signaled Tom to stand next to me.

The second he got there, Olivia deep throated his cock and licked whatever cum was left over on it. When she got it all, she went to my cock and licked it all over, despite where it had been. Afterwards, she merely put her hands on our shafts and started pumping, with her own saliva as an effective lube.

"So where are my other sets of cum?" Olivia asked softly. "I want them in me so bad.…and on me." To help us, she sucked me off wetly and loudly while jacking Tom off, then sucked him and jacked me. She then rubbed our heads on her high cheekbones, before putting them on her lips – while smiling a helpful seductive smile and letting those incredible eyes twinkle.

Olivia kept smiling and humming her encouragement as she jacked us off, and it was still more than enough. I might have normally tried to hold out longer than Tom, but that really didn't cross my mind then. I needed to cum before I short circuited, and Olivia needed it too – and the customer is always right in any business.

So I willed myself to let Olivia's soft hand, eyes, lips and face push me over the edge – and explode all over them one last time. Technically, it just got on her lips and below her eyes before she took me in her mouth. And when she let me go, Tom let himself go as well.

He shot onto Olivia's cheek as she finished sucking me off, then she turned her head to swallow him down as well. She came off just as I finished on her neck, and she let him finish on her face and chest as well. By the end of it, her upper body was pretty drenched – to say nothing of her mouth, which contained a fair load from both of us.

Olivia made sure to show that off very clearly, as we saw her mix our cum together in her mouth. After she swallowed it down, she stayed on her knees for a few seconds before finally getting up – which was our cue to finally stumble and fall into bed.

It took some effort not to fall asleep, as the sounds of Tom's breathing and Olivia using the bathroom sink gave me something else to focus on. But by the time I could focus, I saw a clean Olivia getting herself dressed, while me and Tom were still lying naked.

I got an all too brief final look at her naked parts before she buttoned herself back up. She then stood over us and pulled out two clips of money, lying them on the table nearby. "I'll let you decide who gets what clip. There's $1500 in them either way," Olivia said.

I tried to make a comment, but I was speechless for a few reasons. Yet Olivia – the one who was hopefully rocked harder – effortlessly walked over to us. "It goes without saying you can't tell anyone I was here. It'll make things and future visits much easier," she told us.

All I did was nod, yet it was enough for Olivia to bend down, take my spent cock and give it a kind of goodbye kiss and lick. She quickly went over to Tom and did the same to him, then her cock-tinged lips gave us a final smile before she left the room.

Although me and Tom were all alone and both still naked, none of us moved away from the bed. Ultimately, Tom stated, "Its all downhill from here, man."

While this was my first night, I found it hard to disagree with him. But what a hill to start going down from.