The Holiday Hooker Erotic Story

by Angela Yii

  I reached round to my back and unzipped my dress. I let it slip down, stepped out of it and put it on the lounge next to us. Putting two fingers into the waistband of my thong I pulled them down and out them with the dress.

  I was naked expect for my heels, which is one of my favourite ways of dressing. James could now see my shaved pussy as well as my tits. As I'd expected my pussy was quite wet and looking forward to a nice cock in it.

  I opened the condom, placed it on James's still rock hard cock and rolled it down using my hand and mouth. I gave a few more sucks to make sure he was still hard.

  Once I was certain about that I stood up and straddled James as he looked at me. I took his cock in my hand and rubbed the head along the slit of my pussy a few times before positioning it at the opening.

  Lowing myself slowly I felt the head slowly penetrating me. James rolled his head back as he felt his cock enter me. Moving up and down I took more and more of his cock inside me until my clit was pressing on his pubic bone.

  I leant forward, my long hair falling over his face and my tits right in front of his face. I gave James a kiss on his neck then moved up and we had a full kiss. His tongue was into my mouth in a second and we pressed our tongues together.

  Breaking the kiss I started rocking my pussy over his cock then moving up and down it. James took one of my nipples in his mouth, sucking it and flicking it with his tongue. I love that and started to ride his cock even more.

  James took both my tits in his hands, massaging them and swapping his mouth between my nipples. I was getting wetter and riding his cock hard. I would press my clit into his pubic bone to make sure it was getting the attention it needed.

  I love being in control and being able to determine when I come. When I've ridden guys a couple have said it felt more like I fucked them rather than the other way around. Doesn't worry me if we both enjoy it.

  After a few minutes I could feel James was getting close to cumming. I started to ride harder to make sure I was going to enjoy it as well. His body started to stiffen and he arched his back. A few more strokes with my pussy and his cock started to pulsate inside me. I put a finger on my clit and pushed hard against his pubic bone. Combined with a cock pumping inside me I came a second after James let go inside me.

  James let out a big sigh. I keep rocking on his cock but at a slower pace.

  "OMG." He exclaims eventually. His cock still deep inside my pussy. "That was fantastic. Though I think it might take me awhile to recover."

  "Glad you enjoyed it. I should have said I'm worth every cent."

  "Yes you certainly are."

  Without taking his cock out of my pussy I reach around and pick up our glasses. I handed James his champagne.

  "Cheers." I said. James managed to weakly raise his glass. Maybe he's not as fit as I thought he was. I was ready for round two and didn't want to be disappointed.

  Sitting on top of James I started to massage his chest with my hands. He was athletic with good muscles. I leant forward and gave James another kiss. Using my pussy muscles to squeeze his cock I could feel it slowly getting smaller.

  I climbed off James, rolled the condom off his cock and wrapped it in some tissues I grabbed out of my bag.

  "Maybe we should go inside?" He suggested.

  I grabbed my dress and thong and walked inside drink in hand. James followed with his drink and the ice bucket, plus his clothes as well. I could feel him looking at me, particularly my arse.

  I dropped the tissues and used condom in the bin in the kitchen then walked round the suite in just my heels having a good look at things. I bent over a few times so James could get a good look at my pussy and arse. Eventually I made my way to the couch and sat down, crossing my legs as seductively as I could.

  James put the ice bucket down and almost collapsed in a chair.

  "Still recovering?" I asked.

  "Yes," Said James. "That was amazing."

  "Thank you." I replied.

  James took a mouthful of his champagne.

  "Now I do quite a bit of travelling for work." He began. "I'll admit I do spend some time with ... ummm ... 'working girls' ... but not all the time. Now I really don't think you are. Not that I'm not going to give you the $700 we agreed. But I'm guessing you don't do this often."

  I was wondering what to say but thought I'd be truthful.

  "No I'm not really a working girl. It was a bit of a spur of the moment decision."

  "I thought you were a bit different when I was watching you in the bar. That's why I spoke to you." James continued.

  I smiled and proceeded to tell James about the holiday, argument with boyfriend and the rest.

  "So you're effectively free for the next few days?" He asked once I'd finished.

  "I suppose I am. I hadn't really planned what to do, except enjoy myself."

  "Seems like you enjoyed yourself tonight?" James said smiling.

  I blushed a little. "Yes." Was all I managed in reply.

  "What do you do normally?" Asked James

  "Normal job? PR for a few clients. I have my own business registered."

  "Hmmmmm ...." said James, obviously thinking. I didn't interrupt him.

  After a few minutes he started "Now you said you could do with some money and haven't got any firm plans for the next few days?"

  "Yes ..." I replied wondering where this was going.

  "OK. I've got a proposition for you. I'm here for a conference but am doing some business deals as well. Quite big deals. I've been given a large expense account as I'm expected to provide food, drinks and entertainment to swing the deals. I could use a good PR assistant."

  "Oh? I'm a very good PR assistant. But what sort of entertainment?" I asked

  "Well providing company, making sure everyone is happy and ... ummm ... services like tonight."

  "OK ..." I said thinking

  James continued. "You would be compensated for your time. Might have to fine tune the details but how about a retainer of $1000 per day, $200 per hour for company, $300 when you're expected to provide the entertainment. All expenses covered for food, drinks, clothes etc."

  "Um ... tempting." I replied, mentally doing the sums in my head. "I'm assuming entertaining guys? How many?"

  "Probably 3-4 at a time. And yes, mainly guys. Though at least one of the clients has girls here as well as guys."

  "Ummm" I go again, thinking hard. "Give me some time to think about it."

  Looking at the clock on the wall, I say. "You've still got an hour to go ..."

  James smiled at me.

  Thinking a show might get him in the mood I reached down into my bag and got out the vibrator I always keep in it. Lying back on the couch I turn it on and ran it around my nipples. They quickly rose to the occasion.

  Spreading my legs I started rubbing the tip of the vibrator up and down my pussy slit. I was soon dripping wet.

  Putting the tip of the vibrator at the entrance to my pussy I twisted it around before pushing it slowly in. I licked a couple of fingers on my other hand and started to rub my clit as I moved the vibrator in and out of my pussy.

  I could soon feel the heat in my pussy climbing. I closed my eyes and concentrated on what my hands were doing.

  I felt someone near me and opened my eyes to see James standing next to me with his cock starting to rise. I put my head on the side and took his cock in my mouth. I sucked his growing cock as I worked my pussy. James's hands started to play with my tits.

  After a minute or so James was hard again. He pulled his cock out of my mouth, grabbed my legs and swung them around on the couch. Kneeling down he put both of my legs over his shoulders and positioned his cock at the entrance to my pussy.

  I was so wet he slid in with one push. He waited a few seconds and then started to pump my pussy. Slowly to start with then faster and harder. I was soon moaning loudly, hoping the suites had better sound proofing than the normal rooms.

  It didn't take me long to cum from the pounding of James'
s cock. He soon followed and filled my pussy with his cum. I'd forgotten about a condom this time. Too late now.

  James stopped with his cock deep inside me. He let my legs down and then pulled his cock out. He fell onto the couch next to me, both of us exhausted but satisfied.

  I rolled over and rested my head on his chest. We stayed like that for a few minutes.

  "OK I'll take up your offer. But if its more than one guy at a time the rate is per guy. And if it's more that straight sex we'll have to negotiate extra." I said

  Looking up I could see James smile. "Great ... and that should be fine" he said

  After a couple minutes I got up. "I better get going. Time's well and truely up. OK if I have a shower first?"

  "Sure" said James pointing to the bathroom off the bedroom.

  I grabbed my clothes. A nice shower later I emerged almost the same as I'd been in the bar a few hours earlier.

  James had put on a robe and was sitting at the table in front of a computer. When he saw me he got up and came up to me.

  "Here we go." He handed me the $700 and his card. Ring me around 8 in the morning and I'll give you details for the next couple of days.

  "OK" I smiled. I gave him a kiss. He led me to the door. I could feel him watching as I walked down the hall. I looked back, smiled and waved.

  I took the lift down to my floor. I got into my room, flopped onto the bed, and wondered what had just happened and what had I just agreed to.

  CHAPTER 2

  I woke up a bit after 7 wondering if last night had actually happened. I sat up in bed and saw James's card on the table next to the bed. I checked my purse and there was $700 in crisp new notes in it. Looks like it wasn't a dream.

  James had said ring at 8. I'd had a shower last night so didn't really need one now. I put on a robe, made a coffee and sat down on the small balcony of my room. I was wondering what to have for breakfast but wondering more what was going to happen over the next few days. James said he'd let me know when I spoke to him.

  I finished my coffee and thought I'd ring James even though it was a bit early. I punched his number into my phone. He picked it up after a couple of rings.

  "Hello"

  "Hi James. It's Robin." Luckily remembering my "working" name.

  "Hi. How are you? Sleep well?" I could almost hear him smiling.

  "Yeah fine. How about you?"

  "I slept like a log, but with a smile on my face. Thanks to you."

  "You're welcome." I said smiling. "You said you'd let me know about the next couple of days?"

  "Yeah. Right. I'm at the conference all day today. But it's the conference dinner tonight and I'd like you to accompany me. It's black tie. Do you have anything to wear?"

  "No. Not at all. I'd packed for a beach resort holiday. Not anything fancy."

  "OK. Not a worry. We'll organise something. Do you know where the shops are? Off the lobby?"

  "Yes I know where they are. I haven't had a look at them yet."

  "Great. I'll meet you there at, say, 8:30. OK?"

  "OK. See you then."

  "Bye for now."

  "Bye." I smiled as I hung up. He sounded as good over the phone as he did in real life.

  I got dressed and headed down to the café for a quick breakfast. 8:30 saw me in the lobby near the entrance to the shopping arcade. James arrived soon afterwards dressed immaculately. He made my tank top and shorts look quite out of place.

  "Hi." He said giving me a quick kiss on the cheek.

  "Come on." He said, taking my hand and leading me down to the shops.

  We went into one of the boutiques. The manageress greeted James like he was a long lost friend, even calling him "Mr Matheson". I was impressed.

  "Mathilda this is Robin." Introducing me. Mathilda extended her hand and we shook hands. She was probably mid 30s. Exquisitely dressed and made up. Brunette with a good figure. I'd say she was quite attractive.

  "Robin is accompanying me to the dinner tonight but needs a suitable gown. I'm sure you have something which will be suitable."

  "I'm certain we will." Said Mathilda smiling at James and then moving her look towards me. "Let's see. I'd say size 10, c cup, 36?" she asked walking around me. I nodded in response.

  "Yes we've got a lovely blue one which I think will be perfect." She went to a rack and pulled out a gorgeous blue silk evening gown. Halter top, backless and with a split up one leg. "Would Robin like to try it on?"

  I looked at James. He nodded. "Yes please I replied."

  Mathilda led me to a change room, hung the gown up on a hook and pulled the door closed. "I'll give you a hand to get into it. It can be a bit tricky."

  "Thanks." I said. I've never been worried about getting undressed in front of people, certainly not other girls. I took my top off. I hadn't worn a bra so that made it easy. My shorts soon followed, leaving just my thong. Mathilda helped me slip the gown over my head. The fabric sliding over my skin felt fantastic.

  The top looked a bit like a bikini top with quite a deep neckline. There was a strap just under my breasts and the neckline continued below that to about the middle of my chest. There were a couple of straps which went over my shoulders, crossed over my back and then down the sides to just below my breasts. Other than that it was backless and expose my skin to just below my waist. There was a split which came up my left leg to a bit above mid-thigh. There was some embroidery along the bottom of the dress and up the split. This continued up to where the split would have joined the waist, if it went that far. The gown was spectacular.

  Once Mathilda was happy she opened the door and I stepped out for James to see.

  His only response was "Wow."

  I laughed. "I assume you like it?"

  "You look lovely. We'll take it."

  "I don't think I've ever chosen the first dress I've tried on. It takes all the fun out of shopping." I said pouting. James and Mathilda both chuckled.

  "Mathilda is an expert at choosing what suits. I would trust her implicitly." Said James. "Now let me organise things with Mathilda."

  I looked at myself in the mirror while James and Mathilda had a quick conversation.

  "Ok all organised." Said James after they'd finished. "Mathilda thinks a couple of alterations will make the gown a bit better. The dinner is at 7. I'll organise to meet you at 6. The day's yours until then. Though I've organised with Mathilda for you to have a full spa treatment at 3 this afternoon."

  "Sounds great. You said you'd let me know about the next couple of days?"

  "Oh yeah. Tomorrow is the conference in the morning but I've organised a round of golf for the afternoon. I have to confirm things for the days after that. I'll let you know tonight."

  "Oh great. I love golf."

  James looked at me with a bit of a quizzical look.

  "Ummmm ... were you expecting me to be a caddy? I really do play golf." I said looking at him.

  "I hadn't really thought either way. No worries. I'll organise it. Now I better get going. The first talk is about to start. Mathilda here will look after your every need." He looked at Mathilda and smiled.

  "Certainly Mr Matheson." Said Mathilda smiling.

  James came up and gave me another kiss on the cheek. "See you at 6."

  "Bye for now."

  James headed out the door. Mathilda got out a tape measure and took some measurements, bust, waist, hips and hem length. She also took some photos from different angles with a digital camera. She then led me back to the change room. I got out of the gown and into my clothes. On the way out Mathilda gave me a card with my appointment for the spa. I smiled and thanked her.

  With most of the morning to myself I thought I would make full use of the resort facilities. I went up to my room, grabbed my gym gear and headed down to the gym for a workout. The gym was as well fitted out as the gym I usually go to. It wasn't crowded, probably half a dozen guys and a few more girls.

  I hit the treadmill for a while to warm up, then a few of the machines and some fr
ee weights. I was wearing a tight tank top, leggings and gym shoes. Like most of the other girls. I did notice a few of the guys looking at me and even some of the girls. Everyone there was in good shape and quite easy on the eye.

  I decided to use one of the bikes for a cool down when I'd finished my workout. Listening to some headphones I wasn't really taking any notice when someone hopped on the bike next to me. A "Hi" brought me out of my thoughts. I looked up. It took me a few seconds to recognise the face. It was Ruby from last night.