olivia wilde

Disclaimer: All right, this story is not real. NOT REAL! Not to be read by anyone under the age of 18/21 yadda yadda yadda! I’d love to hear some feedback as per usual. please feel free to leave me a comment in the COMMENT Box at the end of the page. You see those big empty stars too? Maybe bump those up to five full ones? We wouldn’t want them to be empty now would we? All alone like that? You’re not a monster are you?

This author would like to thank: TNP, Thee_Disciple, MaitreNuit and DarkLord Z for always being able to proof read my crap.

“No, no, no, no, no!” Nina scolded me as I selected a button-up light blue shirt.

“But I like this one!” I whined, sounding like a child in one of my classes.

“But it makes your hips look wide.” Nina said, selecting a standard white shirt with a red under shirt that hooped around the arm holes and the neck hole.

“Try this with this blazer.” She offered, passing me one of the three button blazers. I nodded and changed my shirt and slid the blazer on. Nina, was one of my closest friends and also one of my dearest fashion consultants. If I wanted to have sex, Nina was the person to go to. She had worked in fashion since we left Uni and knew what people wanted.

Satisfied with the look, I buttoned up the blazer and stepped outside. Giving a playful wolf-whistle, Nina nodded her head approvingly.

“That looks hot Noah!” She said, smiling and nodding her head.

“You think so?”

“She’ll be putty in your hands.” Nina said with a grin. My phone beeped to life in my pocket, fishing it out and fumbling with the touch screen.

“It’s from Paul, they’re about ten minutes away.” Clicking the keypad lock button, I slid the phone back into my pocket and felt the slightest tinge of anticipation. Jesus, I wasn’t nervous was I? It had been a while since I’d been on a date.

Putting on music, we got chatting and into a general party atmosphere. Several minutes passed and there was a knock on the door. My apartment wasn’t very large. I only had the one bedroom, to the side of the bedroom there was a large ish bath room and next to that was a ‘laundry room’. What wasn’t the lounge, was the kitchen. It had a large table, a fridge and a counter top in the corner of the kitchen.

Walking past our friends, I opened the door to find Sophie, Paul and Olivia standing there. Excited to see Paul again, I gave him a friendly hug as Sophie introduced her new single friend. She was dressed very smartly with her long brown hair draping over her shoulders. It was then I had a chance to admire her fully.

She had lusciously long brown hair, greenish blue eyes that seemed to shine whenever she stood in light, her lips had been painted with a peach-ey coloured lipstick and had applied a light shade of black eye shadow. Her body was firm and tight, she certainly enjoyed a run. Her legs were being shown off by a black skirt, under it, her legs were bare running down to her black boots. Taking off her coat, her breasts were revealed to me. They were very admirable, the type you could hold in your hands and they’d be a nice handful . Her cleavage was shown off nicely by the top she was wearing. It was a black number with plunging neckline that ran to the middle, neatly showing off some of her best assets.

Smiling, we shook hands and exchanged pleasantries.

It was close to eleven at night now and the party was starting to die down. Most of the group had gone home, leaving me, Sophie, Paul and Olivia. We were sitting on one of the sofa’s in the main room and were discussing all sorts of things.

“Oh hell!” Olivia cursed out loud, fishing out her cell. Looking at the time, she groaned and looked at Paul pleadingly.

“I’m going to miss my train. I need to get to the station quick!”

“What time’s your train?” Paul asked, sitting up from his slouched position.

“Eleven forty.”

“I can drive you if you’d like? I haven’t had anything to drink.” I said, picking myself up in a similar fashion to Paul.

“Could you? That would be great!”

“Sure. Let’s go.”

“Well, I think we’re going to go too. We’re heading back home to Oklahoma for Christmas. I’ll be driving so I need to sleep this off.” Paul announced as Sophie joined us standing up.

“Alright then, let’s go.” Sophie said with a grin. We all agreed and made our way out of my apartment building and towards the cars. Politely holding the door open for Olivia, she thanked me and sat down.

Walking in front of the car, I opened the driving door and slid in. Twisting the key in the ignition, we set off towards the airport.

“Right, quickest way is down Stewart’s Road.” I said aloud, talking to myself, but breaking the silence.

“Cool, thanks a lot for taking me. Especially as we’ve only just met this evening too!”

“Yeah, no problem! So why are you heading out? Christmas?” I said, looking out onto the darkened road.

“Yeah, I’ve got family in New York. We always meet up a few days before Christmas and spend most of the time together.”

“That’s nice. Very twee.” I said with a smile, quickly checking the time on my dashboard clock.

“Yeah, my mom loves it… You didn’t think it was weird tonight?”

“How do you mean? I suppose it was rather strange that most of the people left quite early, but… Christmas is coming, we’re not exactly students any more.” I said with a laugh at the end.

“Indeed. I was actually talking about me being here.” Olivia was avoiding eye contact with me, almost like she didn’t want to talk about this.

“Well… I suppose it did seem like a set up. Like when I was talking to Sophie, you came over and she left. Almost like she wanted us to talk.”

“That’s what I meant! God, you wouldn’t believe we were adults with the way she was setting us up!”

“Yeah, she likes that sort of stuff though. She always has.”

“How long have you known her? Since college?”

“No far longer than that. We were in kindergarten together and we always got lumped together, it was however, a matter of coincidence when we went to the same college. That was nice to have someone to hang onto with the first week of College.” I said, letting out another laugh as we turned closer to the train station.

“She can hold her ale can’t she?”

“Yep. So how about you? Did you meet at work?”

“Yeah, me and Sophie were on the same set and we’ve worked together ever since.”

I was about to say something else when a set of blue flashing lights appeared in front of us. Raising my eyebrows, we slowed to a stop in front of a police barricade. A police officer is a luminous green coat walked down to me and I rolled down the window.

“Good evening.” He said courteously.

“Evening, officer. What’s going on?”

“There’s been a gas leak in that office block over there.” He said, motioning with his torch. “We can’t let anyone pass until it’s safe.”

“We need to get to the train station. Can we not go around?”

“You should be able to. When’s the train?”

“Eleven forty.” Olivia piped up, looking up at the officer as well.

“It’ll be tight, but you can try. Head down Young Avenue and take a right on Blair Road. That’ll take you around and put you on the main road towards the station.”

“Right, cheers pal!”

“Take it easy now. Goodnight.” The officer said politely and made his way back to the barricade.

“Shit.” Olivia said aloud, looking at the time.


“We can make it.” I said confidently. I was a more than capable driver and reversed onto the road. Making our way down to the street, I drove at the legal limit, jumping over it on occasions.

“Are you ready to just hop out and go?” I asked as we made the turn onto the main street. It was 11:38 now and the train station wasn’t even in sight yet.

“Yeah, can you stay behind just in case it doesn’t get here?” Olivia asked, fishing out her ticket.

“Yeah, I’ll give it ten minutes. It shouldn’t be too busy tonight.”

11:40 flashed up on the clock just as we made it to the station.

“Go!” I shouted as she jumped out and ran towards the large doors.

Right, with a bit of luck she’s made it. I relaxed and rested in the seat, twisting the radio dial I settled into listening to the music on the radio.

My eyes flashed open, I must’ve fallen asleep. Glancing at the clock it was close to half past twelve so I was ready to go. Looking outside I saw Olivia running towards me waving her arms. Taking my hands off the wheel, she climbed back into the car.

“It went just as I got there and there’s no helpful staff awake.”

“Right, so a train first thing in the morning then?”

“It looks like it. Are there any decent hotels around here?” She asked, fishing out her cell phone.

“Not really. All the other places are going to be tourist traps and they’ll be shut by this time.” I said grimly.

“Great. I don’t suppose you’ve got a spare couch do you?” She said with a laugh.

“Actually I do, if you want to stay?” I said, looking over at her. Biting on her bottom lip she thought about it briefly.

“Ok then, sure.” She answered.

“Cool. Let’s head back then.” I said with a smile. We drove back and discussed various things as the rain started to come down.

I pulled up outside my block of apartments and we hopped out. Locking the car, we quickly made our way upstairs into the building. Fishing my keys out of my pocket, I opened the door and waved Olivia through. I grinned at finding myself not able to stop myself from eyeing her tight ass as she passed.

I stepped in and closed the door, locking it for the night. Walking in, she sort of stood aimlessly unsure of what to do.

“Please, have a seat” I said. She sat down and looked at me.

“Well, since you’re here for the night, should we finish off that last bottle of wine?”

“That sounds great!”

Nodding with a smile, I walked into the kitchen and fetched the wine with some glasses.

“So how did she rope you into this whole thing?” I asked, topping up my glass with the last of the wine.

“Ha! Well, I’m sitting down for make up and she sits down next to me and starts talking. Then she goes… ‘Right, I’ve got this single friend who I’d bet you’d just love.’ Next thing I know, her and Paul are picking me up for tonight!” She said as we shared a laugh about Sophie.

“So do you miss it? Life with a partner?” I asked, as she sipped at the wine.

“Well, there’s certainly an emptiness to my life at home now… But, it wasn’t really working in the relationship so we had to cut it loose.”

There was a silence that lingered in the air. I was fairly certain I’d dropped the ball and was about to apologize when I saw Olivia smile. Bringing the back of her hand up to her mouth, she stifled a yawn briefly.

“Goodness, I’m sorry but I think I’m going to call it a night.”

Matching her yawn, I agreed.

“Alright just gimme a sec” I said. She nodded and smiled as I walked out of the room.

Walking into the bedroom, I grabbed a blanket and walked back to the living room.

“My bedroom’s just through there, I’ll have this old thing out here.” I said, throwing the blanket down by the couch.

“Noah, No! I can’t intrude on you like that.” She said, standing up to take the blanket from me.

“No, no, no. I insist! You’re the guest, you have the bed. I’ll be fine here.”

“If you’re sure?” She said, standing up. I nodded and showed her to the bedroom.

“There you go, hope you find it comfy.” I said with a smile as I walked back into the front room.

“Thanks very much for putting me up like this.” She said from my shoulder. Looking to face her, I nodded and gave a smile. I stripped down to my boxers and my vest, straightening out the blanket I lay down on the sofa. Closing my eyes, I realised I couldn’t sleep. Fumbling on the desk, I found my iPod and put on a podcast. I typically use these to lull me to sleep as some of the voices are quite soothing. Turning on my back, facing the inside of my couch, I shut my eyes and let sleep take me.

My eyes flickered open and the same podcast had still been going on. I listened for another half an hour before I realised that I wasn’t getting any sleep. Mulling over my options, I decided to go to the bathroom and brush my teeth. Walking over, still listening to my iPod, I cast a glance to my bedroom, I saw that there was no light on, so Olivia must’ve been asleep. Wearily, I pushed the bathroom door open and searched for my toothbrush. It was orange so next exactly subtle, why wasn’t it standing out? Snapping my fingers in a ‘Noah! You idiot!’ motion I remembered that it was still in my bedroom from my travel bag.

Walking out, back into the front room I flipped the light off to make sure I didn’t wake Olivia up. I walked across to my bedroom and lightly opened the door. There I saw her.

She had her panties next to her on the bed and had two fingers deep insider her, her right hand was pawing at her breasts as she moaned at her own touch. She was moaning very quietly, presumably not to wake me up. Her fingers were working double time on her crotch as she bit her lip and gasped at her touch. Her hips were bouncing off of the bed as she rode herself to an orgasm. She let out a tiny squeak and came over her fingers. Grinning madly, she sighed content in her actions. Opening her eyes slowly, she then cast a look over at me, her eyes wide.

“Oh god! I’m so sorry!” I said in a fast paced voice, and backed out of the room into the hall. I leaned back against the wall and took a deep breath. I put my iPod away and collapsed on the couch, wondering what I would exactly say when I was inevitably going to face her.

A few minutes later she walked in with the bed sheets wrapped around her, that only just covered her nice ass. I started to apologize to her again but she cut me off.

“I’m sorry…” She started, that was pretty new. The one being caught apologizing?

“Don’t be. We’ve all got urges right?” I said with a smile, looking up at her before darting my eyes back down to the floor.

“Yeah… Yeah! It’s really great that you understand. And honestly? I’d rather it was you walk in on me that somebody else.” She said, making a joke out of the potentially awful situation.

“I saw the light was off in the bedroom and I thought you were asleep.” I said, still feeling exceptionally guilty.

“Really, it’s fine. Don’t worry about it. I’m fine with it.”

“Right… Right, why wouldn’t you?”

Well, this is awkward. After a few seconds of silence, I spoke up.

“Uh… I’m gonna…” I started, gesturing with my thumb towards the make-shift bed.

“Yeah… Yeah. Me too. I’ll see you tomorrow Noah. Good night.”

“Good night Olivia.” I replied with a smile, she tugged at the sheets and moved towards the bedroom door.

Sighing heavily, I closed my eyes and let sleep take me.

Halfway through a non-descript dream I felt a weight press against my chest. Then, a soft pressure was applied to my lips and woke me from my slumber. My eyes opened slowly and I saw the now naked Olivia Wilde straddling my chest and kissing my once sleeping body. Closing my eyes again, my mouth pressed back against hers as my arms wrapped around her body, hugging her tightly. The kiss was broken, and our eyes met each others.

“My, my. What do we have here?” She said with a smile. Her hands ran up and down my body as she smiled as she reached my lap. Almost on instinct, my hips lifted off of the couch and she tugged at my boxer shorts. She grinned and slid down my body towards my now rock hard dick. I kicked my boxer shorts off of my leg, sending them towards the corner of the room.

She eyed up my stiff dick hungrily as I slid off my shirt and tossed it to one side as her hands made their way back down to my groin. Cupping the member with her right hand, she lightly jerked it up and down watching with great admiration as the skin folded and straightened with each pump. She would occasionally swap and twist the skin when she hit the bottom of my shaft. Pushing the member up towards my chest, she put her tongue on the bottom of the dick, just above my balls and traced it up along the bottom. Running it along my thin vein, when she reached the head she simply followed it up over. Flicking her tongue against the shaft’s head she held the base of it steady as she did so.

She slowly moved her hands down to my balls and cupped the hairy testes in her hand as she started to suck on my cock. Her mouth had formed a tight seal around my member and she was steadily sucking on it. Covering about half of my eight inch member, she would moan whenever I put my hands on her head taking a hold of her hair.

She would look up at me and smile, her big green eyes lit up with lust with each drop she made. Moving her hands from my balls, she placed one on my backside and the other on my waist to steady herself. Increasing the bobbing rate, she started to produce more and more saliva making a glugging sound with each bob.

She pulled herself off of my shaft and made dives for it, letting the spit hit her on the cheek leaving a thin saliva trail. She smiled as my jaw dropped at her actions.

She continued to paint her face with her own spit while looking up at me with a sweet expression on her face.

“You like that don’t you Noah?” She asked with a grin as I simply nodded, dumbfounded.

“You’re such a dirty boy.” She said, smiling again. Spitting on my dick, she then started to suck it again. Covering nearly all of it, she was taking it like a champ and then she managed to deep throat it. Taking all of my shaft in her mouth, Olivia simply smiled up at me as she carried on sucking my dick. She continued with deep throating and then letting up for about five more minutes before I felt my nuts stirring.

“Olivia, if you keep this up I’m going to cum.” I warned her, as I ran my hands through her hair. She looked up at me and nodded her head. Lifting her head off of my shaft, she smiled and kissed the tip of it.

“Well, we’d better get to work then.” And with that she stood up and pounced on me. Holding her by her thighs I lifted her up as she jumped into my arms. She wrapped her arms around my neck and squeezed her legs around my waist. Stumbling on the spot for a while, we eventually fell forward and landed against a wall.

I had managed to pin her against it, and the way she was holding onto me, meant her massive breasts were pushed up against my chest. I removed one hand from her and took hold of my dick. Aiming it at her cunt, she groaned in a satisfactory manner and rolled her hips towards me.

Knowing better than to keep a lady waiting, I slid my dick inside her. She threw her head back and let out a loud moan as she was filled up by my meat. Starting out with a slow, steady rhythm I started to fuck her. Knowing where to hit her g-spot I let my dick grind against her clit making her moan almost cutely. Her warm breath was on my neck as we fucked. I had tired of the slow and steady rate and was ready to fuck her harder.

“Can I fuck you now?” I asked, looking at her. She had her eyes closed but she simply nodded. I then started to fuck her with short and swift strokes. With little care, I started to simply ram my rod deep inside her as her ass shook with each stroke banging against the wall.

I thought about my neighbors, but quickly realized I didn’t care. With each thrust inside her, Olivia’s back was arching more and more to meet each of my thrusts.

Her breathing soon got shorter and shorter before she threw her head back and let out a sharp, shrill scream. I felt a warm liquid start to gush all over my leg, she can’t have came all ready? Shrugging, I started to feel ready too. The brief break in between the oral and the fucking must have only just cooled me down.

“Olivia, I’m going to cum now!” I let out, sighing heavily as I did so. She looked up at me, her eyelids flickering in the post glow of the orgasm. Quickly coming back to her senses, she nodded and pushed me off of her. Letting her get to her knees, she took me in her mouth and started to suck lightly.

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.”

This is a follow up to my story “A Wilde Encounter” I would advise you read the previous chapter, which leads directly into this story. I hope you enjoy the story. Another chapter will follow.


Chapter 2

Olivia grabbed me and led me to the bathroom. Once inside she let go of my hand and swayed her ass to the shower door and opened it, she then switched on the shower and stepped inside. As she did that, I slipped off my pants and tossed it out the still wide open door.

The water began to flow over her body. Her body was wet as the water continued to flow over gorgeous curves. She then looked at me and curled her finger gesturing me to join her and naturally I obliged without any hesitation.

Once under the water I pulled her close to me and we embraced and then kissed, keeping our lips locked in a passionate lovers embrace. The water, the heat, and the lust we felt for one another, from our bodies all came together to unleash our sexual beasts as it were.

I then started to plant kisses along her body as she remained standing and I moved closer to her gorgeous pussy.I gestured her to spread her legs and she obliged. I started to rub the outside of her pussy and soon spread her pussy and buried my tongue as deep as I could go. Olivia gasped in pleasure as she seemed to appreciate my technique and as such I stuck with it. I kept going, flicked my tongue, darted it about her gorgeous pink flesh.

I had my hands grasped around her soft and tender ass, as I kept my face buried in her vagina. I explored the outside of her rather tight asshole as I probed it with my finger, which garnered a spirited response from Olivia.

I then withdrew my tongue from Olivia’s vagina and then began to finger fuck her. I started slowly then increased my pace to something simply mesmerising and Olivia seemed to be heading to orgasm and vocally expressed that rather clearly. I continued to move my fingers in out as fast as possible and Olivia could hold on only so long and eventually let her orgasm surge through her body.

Olivia then let the orgasm subside and then switched off the shower. We were clean but still oh so dirty. Olivia stepped out and led me along as she grasped my cock, she then instructed me on to the floor and I followed her instructions.

Olivia then straddled me and swung her gorgeous ass around for my viewing pleasure. Olivia then started to give my cock some tender loving care and affection. As I went for another round with her gorgeous pussy, she sucked on my cock, made it wet and taking my hard member all the way to the back of her throat.

I keep my tongue rampaging through her vagina while she kept my cock inside her mouth. Locked in a 69 we gave and received pleasure in equal amounts. Our wet bodies continued to drip water onto the floor and left quite the mess.

“I want that this in my pussy,” Olivia demanded.

“Well come and ride me like you did that horse,”

I responded.

“You’re a cheeky bastard,” Olivia replied as she straddled me and began to lower her pussy onto my cock and began taking it in. She fixed her gaze onto me and with her eyes seemingly gazed into my very soul. It made me lust for her even more and made my cock even harder, if that was possible at that point. Olivia placed both hands on my chest and steadied herself as she rode me like a bucking, fucking bronco.

“Fuck that feels good,” Olivia purred.

“Fuck yes it does,” I replied with gusto as we

began picking up the pace and wanting to reach another orgasm.

Olivia began to fuck faster and harder and I responded in order to keep up and get there with her. She sensed that as well, and her body responded. She fucked, I fucked and eventually we reached the tipping point and let our orgasms take control. It was beautiful and once the orgasm had resided, we laid on the tiled bathroom floor and staring at the ceiling catching our breath.

Olivia then gazed over at me and ran the back of her hand down my right shoulder. I looked toward her and without saying a word we both spoke volumes to one another in that moment. After a while we got up from the floor and began to dry one another off. Olivia moved the towel down my body, giving special attention to my cock.

I then returned the favour and paid careful attention to every part of her body. It may have been still like a dream, but for any other person on the planet the sensation would have been similar.

“Thank you, Bill,” Olivia said with beautiful smile adorning her face.

“Thank you Olivia that was beyond my wildest dreams, forgive me if that sounds a little cheesy,” I responded.

“Bill, you are an amazing man, showing such care, any woman would be lucky to have you like I just did.”

“Thank you.”

We both then stepped out of the bathroom; I found my pants where it landed and the rest of my clothes. I then got dressed as Olivia slipped on a rather simple, yet sexy, ensemble of a pair of blue skinny jeans, and a rather sexy top with a plunging neckline. I turned to Olivia again admiring her sexy form and gathering my thoughts.

“I guess this means we must part ways.”

“It would seem so, Bill.”

“Well Olivia, you are amazing, I’ll probably end up seeing you again on the big screen.”

“Maybe in person again, I would certainly like that.”

“You truly leave the world better than you found it.”

“Thank you, it’s a lifelong calling.”

“I respect you for that, you are changing the world.”

“I appreciate that.”

“So this is where we say goodbye.”

Olivia wrapped herself around me and we embraced once more. I then stepped out of the hotel room to find the bodyguard from yesterday resuming his post. He nodded, knowing what went on, on the other side of the door. I then walked off to the elevator and took it down to the lobby.

It seemed to sparkle even more, than it did yesterday. It would seem to Parisian air had me intoxicated to the fullest extent. I stepped through the doors of the hotel into the Parisian streets.

I felt in awe of the sights, the sky seemed bluer, air crisper, horns blared, birds chirped, but none of that compared to what had happened in that hotel room. I looked around at the people walking around and I knew that none of them had any idea what had just happened to me. I grabbed a taxi and made my way through Paris.

I did wonder if I would see her again, I deemed it unlikely, seemingly a singular occurrence which, would remain with me forever. Only time would tell if our paths would ever cross again. I knew then that I would have quite the tale to tell.

(Two Weeks Later)

I looked out the airplane window at the bustling

city in the distance. Morocco a place steeped in history. The plane made its final approach and soon it had landed. Once I had stepped out of the plane, there was a distinct scent that seemed to identify it as Morocco. I made my through the terminal and got into a taxi to a hotel. A rather fancy placed in the heart of Casablanca.

The hustle and bustle of the city loomed about; it was beginning to get dark as it had been a few hours since I had landed. I settled in and caught up on some sleep. The next morning I awoke a little earlier than usual and watched the sunrise as I sipped on some coffee.

I saw a beautiful sight as the sun rose into the North African sky. It made me think of Olivia, I thought it would be coincidental but still unbelievable if I had bumped into her again.

I eventually got dressed and made my way into the streets. I made my way around heading for the markets within the city. A lot of the ancient architecture remained intact, much of it for a few thousands of years. Most of the streets were narrow, the inevitable clash of ancient with the modern occurs in this region in just about every direction.

As I walked through the narrow streets, I listened to the bustle of the city. People went about their business. The city felt like it was alive, an organism, a being in its own right, it felt good, to experience something different yet familiar. We are all humans it would seem, sometimes circumstances have made us forget that, even though it should not be the case.

I walked among hordes of people each going about their business. I saw the faces so many people, amongst the throng of people I saw a face behind sunglasses, a familiar face, so I looked again and to my surprise it was Olivia. She soon was aware of my presence and made her way toward to me. She was dressed in a pair skinny blue jeans and a low cut white top.

“Well, well, we meet again.”

“Indeed we do, Olivia”

“So what brings you here?”

“Adventure and a history lesson.”

“Nostalgic much?”

“It’s a mystery, the ancient past, just getting a


“Interesting, a fascination of mine as well.”

“I’m assuming you are here saving world.”

“Why do you say that?”

“Well your philanthropic endeavours, you are

pretty much Wonder Woman.”

“Well, thank you.”

“So are you busy right now.”

“No just exploring the city like you, it would seem.”

“Any destination in particular?”

“Not really seeing where the wind takes me, and I’m enjoying where it has brought me.”

“I feel the same way.”

“Shall we?” I asked, whilst offering my arm.

“Let’s,” Olivia replied, whilst curling her arm around mine.

We wandered through the ancient streets and felt millennia of human history still lingering around. I looked toward her and she seemed happy in my company, glowing even. It was something that I noticed the entire morning. We continued our little journey, surprisingly unnoticed my most of the populace. We took it all in, like any other couple who might visit Morocco.

We eventually found ourselves back at my hotel.

“Well, it has been a wonderful morning, I’ve enjoyed our time together, it was amazing to meet you in Paris however, seeing you again leads me to believe that I am still dreaming.”

“Trust me; you are very much in the realm of reality.”

“Thank you, well this is my hotel, would you like to come up?”

“I thought you would never ask, of course.”

Olivia and I then made our way back up to my room. Once through the door, we sat and relaxed looking to enjoy one another’s company.

“It’s a beautiful city,” Olivia began.

“A classic beauty and very mysterious as well,” I responded.

“Are you talking about the city Bill?”

“Well Olivia what do you think?”

Olivia simply laughed in response rather naughtily, I might add.

“We haven’t gotten to know each other that well, I think we should.”

“I agree Olivia.”

“Why don’t you start?”

“Of course.”

Our banter continued for a few more hours and by the time the sun went down we had become more than acquainted with our respective origins. I had since opened the windows as the night was as hot and humid as the day. The bustling lights of Casablanca lay before us in the distance and we soaked up the sights and savoured the sounds coming from the streets below. We had since gotten rather frisky with one another.

Olivia stood up and then slowly and seductively began to strip away her clothes. She started with her top tugging, twirling and eventually pulling it over her head to reveal her white lace bra encasing her gorgeous breasts. Her jeans looked even sexier alongside her bare midriff. Olivia turned away from me and looked back me and with a curl of her finger lured me over to undo her bra and let it slip to the floor.

She turned to face me and with a firm hand led me back onto the couch and began to straddle me and further enticing me with a passionate kiss. I reciprocated and returned the gesture. This seemed to have driven Olivia wild as she vocalised her appreciation. All the while I had my hands all over her exposed upper body. Her breasts felt soft and tender as one would expect.

Olive then ripped my shirt open and began to move toward my crotch. Her hands swiftly unbuckled my pants and soon my erect member was standing at attention. Olivia licked her lips before wrapping them around my cock and taking it into her mouth. She rolled her eyes up to face mine and her green orbs were kept locked onto me as our eyes engaged in their own lustful dance, while she gave my cock tender loving care.

Olivia’s free hands were fondling my balls enhancing the sensation I felt at that moment. My mind was simply going crazy at that point. Sex with Olivia Wilde the first time around as unbelievable for lack of a better word, however meeting her again and seeing that was beyond my wildest dreams, and even beyond what happened in Paris.

After some time her sucking led me to an orgasm shooting my hot sticky load in her mouth.

I gestured Olivia to stand, once she had swallowed all my cum, after she did so I then undid her jeans pulled them down to her ankles. I then reached around and dipped my thumb into her gorgeous asshole and followed that with my tongue going to work on her shaved pussy.

Olivia kept her head tilted back as she uttered her appreciation for my actions. My tongue continued to dart about and stimulate her pussy, and to start getting her wet in her most sensitive of spots. It felt as though I was listening to Beethoven’s Ode to Joy only the orchestra was Olivia’s pussy and my tongue was the conductor’s baton.

After bringing more joy to both our lives, Olivia began to moan a little louder indicating an inevitable orgasm on its way. As the ‘orchestra’ had concluded Olivia let loose an orgasm and her pussy juices shot forth as I lapped them up savouring the taste, the smell, and where I was at that moment in time.

However Olivia wanted more, she pulled me up to my feet on pure sexual lust. She got me onto the couch and began to ride me like she was a cowgirl in a rodeo. She was enjoying reenergised cock inside her as she held onto me as I drilled my cock deep inside her. Were both one orgasm done but still wanted more, and we both obliged one another.

Olivia continued her riding, lustful moaning, and naughty grin. She bucked and gyrated going up down on my cock. I got a firm grasp on Olivia’s ass and kept it there she fucked the shit out of me.

We then both got off the couch and Olivia then bent over and placed two hands firmly on the heavy wooden coffee table front of the couch and wiggled her ass at me, indicating exactly what she wanted. I slid in behind her and Olivia then lifted a hand and pointed her index finger at her asshole.

I then moved my cock in front of her asshole and then slowly slide it in, Olivia let out moans as it made its way through. She was most likely wide eyed at that point. Her body, like mine was covered in sweat at that point, which the humid night simply added too.

As her asshole began to loosen up and accommodate my cock inside, I begun to build up momentum, increasing slowly so as to continually savour the moment as it happened. My pace soon quickened and I was sliding in an out of Olivia’s asshole with consummate ease. My grasp on her hips remained as touching her tender flesh was an aphrodisiac for me.

The flesh of a woman I had lusted for I don’t know how long was in my grasp and I was enjoying the moment as much as was humanly possible. Even though this was not the first time it was still unbelievably special. Was I in love, in lust, or both and I did not know at the time. Olivia was enjoying every bit of time that my cock was deep inside her asshole and I enjoyed having it inside her asshole.

We were at it for quite some time covered in sweat and bodily fluids however were not done yet. Olivia moved over to the large window placed her outstretched hands on the glass and spread her luscious legs apart and arched her back. I moved up behind her and grasped her thighs as my cock went back into her awaiting pussy and I fucked her, furiously.

Our bodies collided as my cock rapidly went in and out her our bodies still sweaty still dirty. It was sure send us both over the edge and after some time it was soon coming, and it seemed that our orgasms would be mutual. Just as the thought entered my mind, an orgasms entered our bodies.

Olivia’s pussy juices collided with my cock shooting its load and we both felt the effects and continued to fuck away until our orgasms had finally subsided. We both collapsed onto the floor exhausted beyond belief panting and trying to catch our breath.

May 2018
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