Holiday Hooker Ch. 02

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 free 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.

"Oh Hi. I didn't notice you. Sorry. How are you?" I half stammered.

"Good and you?" She asked.

"Yeah good. Making use of the resort's facilities while I'm here."

"I do as well, even though I'm not really staying here. I sneak in." Said Ruby, whispering the last part.

I smiled at her. "How was your night?" I asked.

"Pretty good. A few customers so I did alright. How was your's?"

"Good. Enjoyable." I replied, wondering how much I should say.

"Oh come on." Ruby exclaimed. "I saw you heading off. I know what it looks like when a girl's just picked up a client. Don't bullshit me."

"Umm ... yeah ... well sort of. It wasn't planned." I stammered.

"I thought you said you weren't working here?"

"I'm not. I never intended ..." I tried to say but broke off.

Ruby just looked at me.

"OK. Here's what happened ..." I started off and ended up giving Ruby a complete run down of last night.

"Lucky you." Said Ruby after I'd finished. After a pause she added. "So you're playing Julia Roberts to his Richard Gere?"

I looked at Ruby blankly.

"You know ... 'Pretty Woman' ... the movie. All that stuff." Ruby continued.

It suddenly hit me. "OMG. I'd never even thought of that." I burst out laughing. Ruby joined in.

"I don't think so. It's just for a few days. He said it was because I'm an 'amateur' he made the offer. Like a job for a few days." I said.

"So what's the job entail?" Ruby asked.

"Well a conference dinner tonight. I get the impression entertaining some of his clients. Golf tomorrow. That's all I know so far. The rest of the time is mine."

"Sounds lovely." I wasn't sure if Ruby was jealous or not.

I was getting a bit tired and was thinking it was time for a shower. I started to slow down on the bike.

"I think I'm done. Time for a shower." I said.

"Hmmm likewise I think." Said Ruby.

We both grabbed our towels and headed to the change room.

It turned out our lockers were close to each other. Both of us got undressed and headed to the showers.

I wet my hair, washed myself and then closed my eyes, stood under the shower letting the water wash over me to relax.

"Let me wash your back." Said Ruby. I didn't take much notice but felt her go over my back with a bath sponge. It felt great. The next thing I knew she'd put her arms around me, pressed herself against my back and was giving me a kiss on the neck.

A little shocked I pulled away and turned round to face her. I was just about to say something when she put a hand behind my neck, pulled me close and kissed me on the lips. I'm no stranger to girl on girl action and truth be told I lost my virginity to a girl not a guy. But I was still a little shocked at Ruby being so forward. Even so I soon found myself melting and returning her kiss. Our tongues playing between our locked lips.

Eventually we broke the kiss, mainly to get a breather more than wanting it to end.

"Well that was a bit of a surprise." I managed to say.

"Sorry. Did you mind?" Asked Ruby.

"No not at all. I just wasn't expecting it."

"Hmmm well it's not something you can really ask at times. Sometimes I reckon its easier to just go for it and see what the reaction is. I had a feeling you wouldn't complain." Ruby explained.

"No complaints at all. Just surprised."

Ruby smiled. She stepped forward and started another kiss. This time I could feel one of her hands on the cheeks of my arse. I put my arms around her and held her close. After a little while I felt a hand moving round and starting to explore my pussy. I shifted the weight on my legs to give her better access. I was rewarded with a finger exploring my slit and then settling on my clit. A moan escaped my lips when she started to press on it.

After a little while we broke the kiss. "We should probably get out of the shower." I suggested.

We dried off and headed back to the lockers. Ruby caught up with me, spun me around and landed another kiss on my welcoming lips. Holding each other we broke the kiss after a while.

"I would have thought you wouldn't indulge in things like this in your off time. Not enough sex?" I asked a bit curious.

"Work is with guys. Time with girls is for relaxing. I don't get to do it too often but I couldn't resist with you. Actually that's one of the reasons I had a chat with you last night. I had a feeling you were bi."

"Yeah I am. But I haven't been with a girl for a while."

"Well we better make up for lost time then." Said Ruby, kissing me again and pulling me close. Our breasts pushing against each other. Ruby's hands were exploring my arse cheeks again, including teasing my arse itself.

After a little while Ruby broke the kiss but moved her lips onto my neck, then slowly down my chest to my nipples. She sucked one into her mouth and started to flick it with her tongue while she massaged both my tits with her hands.

I had a sudden thought. "What if someone comes in?" I exclaimed.

"Don't worry." Said Ruby still massaging my tits. "We're all adults here. No one will care."

She went back to sucking my nipples and gently sat me down on one of the benches. Her fingers found my pussy again and she started to lie me back on the bench. I was enjoying the attention so much I didn't resist.

I felt a couple of fingers enter my pussy as her thumb worked on my clit. My eyes closed with enjoyment. My pussy was more than wet from the attention it was receiving. I opened my eyes briefly and could see Ruby obviously enjoying playing with me.

I closed my eyes again and changed position to be a bit more comfortable. Ruby had slipped another finger into my pussy, stretching it as she moved them in and out. I was trying my best not to moan or make a sound as I was sure it would draw attention to us.

Ruby changed her hand again and I felt four fingers go into my pussy. I arched my back in response and let out a little gasp. Ruby had moved her other hand off my tits and was using that to rub my clit as she worked her hand in and out of my pussy. She slowed for a moment and I felt my pussy being stretched more. She had put her thumb in with her fingers and was pushing her entire hand into my pussy. Ruby was moving it gently in and out but putting pressure on it as she pushed. I felt my pussy stretch a fraction more and her hand entered my pussy fully. I couldn't help giving a gasp. I was breathing heavily.

Ruby started to work her hand in my pussy. Moving it in and out as well as twisting it. With the attention of her other hand on my clit I thought I was approaching heaven.

I could feel her fingers exploring deep inside me. Ruby started to flex her hand inside me. It seemed like it was getting bigger. Then I realised. She was making a fist inside my pussy. My pussy started getting wetter if that was physically possible.

Ruby twisted her fist and pushed it further into me. I could feel my pussy lips way past her wrist.

My body was starting to shake. The combination of a fist in my pussy and fingers on my clit was taking me to an immense orgasm. I could feel the fire in my pussy reaching a crescendo. Stifling a scream I arched my back and held my breath as I came. It felt like I held my breath for a minute as I waited for the pleasure to wash over me.

Ruby slowed down her hands but kept gently stroking me. I started breathing again and collapsed back onto the bench. I was still trying to recover when Ruby slowly pulled her fist out of my pussy. I gasped and it felt like another little orgasm as she did.

I hadn't managed to fully regain my breath or say anything when I felt something pushing against my sodden, swollen pussy. I looked up and saw that Ruby had put on a strap on which was now pointed at the entrance to my pussy.

Ruby looked and me with a bit smile. She lifted my legs up, pushed and the plastic cock slipped easily into my pussy.

"Fuck." I said softly.

"Exactly. Time to get fucked." Said Ruby as she started to rock her hips.

She soon built up a good rhythm with the cock sliding in and out of my pussy. I looked up and could see she was enjoying fucking me. Obviously the strap on was pushing against her pussy and clit. Plus the domination of fucking another girl.

I could soon feel another orgasm building inside me. I started to rock my hips to meet Ruby's thrusts. My breathing was getting quicker and quicker. I took a deep breath and held it as I came again in the space of minutes. Ruby gave a couple of extra thrusts and I could tell she was cumming as well.

Ruby continued to rock her plastic cock inside me but slower and less forcefully. We both started to come down from our climaxes. Eventually Ruby stopped. She leant forward and we had another long kiss. Ruby lying on top of me with the cock still buried in my pussy.

Again after quite a while we broke the kiss. "I think I need another shower." I said smiling up and Ruby.

"Likewise." Ruby responded.

We extracted ourselves. Ruby put the strap on back in her bag. We both headed back to the shower and quickly rinsed ourselves off. Drying ourselves off we headed back to the lockers.

"Do you do that often?" I asked Ruby.

"Not as often as I like. But I do when I get the chance. I think we should catch up again before you go home."

"Now that sounds like a good idea." I said laughing. "Hopefully when you're not too busy."

"My days are usually quiet. Evenings are for work." Ruby looked in her bag and pulled out a business card. Handing it over she said "Give me a ring tomorrow if you're free."

"No worries." I replied putting the card in the pocket of my gym bag.

We both dressed quickly. I looked at the time and realised it was getting late. I had time to grab something to eat and then head to my spa booking.

I grabbed my bag and started for the door. As I passed Ruby I put my hand behind her neck and gave her one last passionate kiss.

"Until tomorrow." I smiled and headed out the door.

I grabbed a quick bite to eat at the café in the lobby then headed to the spa. I walked in and was greeted by the receptionist, a blonde about 18. I told her I was here for my appointment. She found it and then said she had to get the manager. She disappeared around a corner and came back with Mathilda from this morning.

I must have looked a bit startled as Mathilda said "Good Afternoon Miss Robin. Don't be surprised. I'm the manager for all the shops and I personally look after our most important customers. Mr Matheson had asked for the boutique to be opened specially this morning. That's why I served you."

"Oh ok."

"Please follow me Miss Robin." Said Mathilda leading the way behind a curtain. We stopped at a changing cubicle. Mathilda motioned for me to enter.

"There is a robe for you Miss Robin. Please undress completely. I expect you will go straight from here to meet Mr Matheson so we will arrange for your clothes and bag to be taken to your room."

"Thank you." I said entering the cubicle. After a minute I push the curtain back dressed in a lovely silk robe which reached down almost to my knees.

Mathilda was outside waiting. "Ahh Miss Robin. Please follow me. We will get the less pleasant part of your session over first."

I followed Mathilda into a small room with a padded bench in it. This was obviously where the waxing was done.

"A full wax for you today Miss Robin. Although like all blondes you don't have too much of a problem. I am jealous at times. If we had a longer appointment we could use the IPL or laser but we don't want the possibility of reddened skin with the dinner tonight. I'll leave you with Louise."

Louise was about 20 with raven hair. Again quite attractive. All the staff wore uniforms buttoned down the front with the skirt finished about mid-thigh.

Louise had me lie down on the bench. It was quite comfortable. I was soon being attacked by wax and strips. Full leg wax, Brazillian, including arse and underarm. Louise checked my eyebrows and upper lip.

"I think we won't need to do them." She said. "Unless you want to? I think your eyebrows only need a couple of hairs plucked. They can be done when we do your makeup."

"Fine by me." I replied

"OK. Massage is next on the agenda. Please follow me Miss Robin."

I got up, put my robe back on and followed Louise from one room to another. This one had a padded massage table in it. There was a scent in the air and the background music was a little louder in this room.

"Please take off your robe and lie down on the table. Kate will be with you soon." Louise said and then left the room, pulling the door to on the way out.

I put the robe on a hook, lay down on the table and flicked a small towel over my bottom.

After less than a minute there was a knock on the door. "Come in." I said.

Another girl came in. Kate I assumed. A blonde about 20 as well. Everyone in here seemed quite attractive.