Holiday Hooker Ch. 01

It was supposed to be a holiday to enjoy and get things back on track. Instead after two days it had all gone wrong. My boyfriend, Dave, and I had been going through a rough patch. The idea was to spend a couple of weeks away from everyday pressures and sort things out. Well that was the idea but on the second day we had a big argument after he wanted to watch the football on TV rather than go out and do something. Next thing I know my now ex-boyfriend packed his bags and left on the first flight home.

The room was paid for, I'd organised time off work and the flight home wasn't until next week. So I thought I may as well stay and enjoy myself as much as I could. I'd just have to make sure I had enough money to pay for extras.

So here I am sitting in the bar at the resort by myself having a drink. The resort had a few bars. I'd picked the upmarket one to indulge myself. I'd put on a shortish black cocktail dress and medium heels. Halter top with a low back which meant I couldn't wear a bra. A black lace thong, gold chain necklace and earrings completed the outfit. Black suits most girls and it certainly makes the most of my long blonde hair and light tan.

I'd been in the bar maybe 45 minutes and was just finishing my first drink. I hadn't taken a great deal of notice of who else was in the bar. It certainly wasn't crowded. A couple of guys in their 50s had sat next to me and tried talking but I wasn't really up for it and they'd left after a while.

I finished my drink and ordered another. I was starting to relax a bit and started to look around at the rest of the crowd. There were two groups of guys, some couples, two groups of four and one or two single guys. But what seemed a little strange was that there were a number of other girls sitting by themselves, just like me.

I looked at a blonde on the other side of the bar. She would have been early 20s. Nice figure, good makeup and well dressed, though a bit more revealing than I would have thought appropriate. A guy sat down next to her. They chatted for a couple of minutes then quickly finished their drinks and headed off to the lobby together.

It suddenly struck me. I looked around at the other girls and noticed at least a couple had come and gone since I'd been here. OMG at least some of the single girls were "working girls", hookers or whatever you wanted to call them. No wonder the conversation with those two guys had been a bit strange.

A brunette about 25 sat on the seat next to me and ordered a drink. She was wearing a halter top and short skirt. There was quite a bit of midriff showing with a lovely belly button piercing. Nice figure and long shapely legs. About 5' 4" so a bit shorter than my 5' 6". And a bit smaller, probably a B cup to my C.

"Hi. I'm Ruby." she said.

"Hi. Stephanie." I replied.

"Are you new here? I haven't seen you around."

"I'm staying at the resort for a couple of weeks."

"Oh? OK. Though some of the new girls say that."

"Look I really am." I replied and gave a quick summary of boyfriend, argument etc.

"Oh. So sorry." She said. "I thought you were a new working girl."

I smiled "Don't worry. I probably look like it. I didn't realise when I came down for a drink. I assume you are?"

"Yes." She said. "Been here on and off for a year now. There's a conference here this week. They always attract extra girls. I thought that's why you were here. Some of the local girls get a bit upset about extra competition. Usually the ones who are getting a bit older and starting to have trouble getting customers. They don't like younger girls coming in. Doesn't worry me though."

"OK. I see." I said looking around. I did notice a couple of the other girls looking at me.

"Do you enjoy working here?" I asked curiously.

"Yeah I do. The money is easy and I enjoy sex. Though I choose who I go with. They have to be reasonably attractive and not too old. Unless its been a quiet night."

"What sort of money?" I asked still curious.

"Usually $400 an hour. $3000 overnight. If I reckon the guy is loaded I might say $500 an hour."

"Wow! And that's just for sex?"

"Well generally a blow job and sex in a few positions. I usually do a nice strip for them first as it takes less time to get them hard. Makes for less work later on. If you know what I mean."

I smiled. "Yeah I could imagine."

I'm not sure how many drinks she had had but she was getting a bit more chatty. "Guys will often ask for extras. They're negotiable, depending on my mood and the guy. Like anal is an extra $200 if he's OK."

"Wow."

"Then you get a couple of guys, or maybe three of them who all want to play. They all have to pay the same. So great money."

"Wow! Do you mind more than one?" thinking back to the few threesomes and two gangbangs I'd had, and enjoyed immensely.

"Love them. It's great being the centre of attention. Though I make them know if I say stop they need to stop straight away. I've only had to do that once. Plus I make sure they're not drunk."

"Wow. Sorry for saying Wow all the time. Sounds like you like your work?"

"I do. I love sex. But this is only for a couple of years. I'm only doing this to set myself up for later. I'm not into drugs or anything. Not like a few of the girls. What I make goes into the bank or investments."

"Oh OK."

"OK. I better get back to work." She smiled. "Thanks for the chat. Hope the rest of your holiday is better than the start."

"Thanks. Nice chatting. See you later."

She wandered off in the direction of a single guy. I started to think about what she'd said. Maybe this was a way to get some spending money? After all I'm only here for a couple of weeks. And nobody knows me here.

I was jolted out of my thoughts by a guy sitting on the seat next to me.

"Hi! I'm John" He said.

"Hi. I'm Robin." Thinking quickly to come up with a "working name". I suppressed a laugh at "John" remembering all the stories about the names guys give to hookers. I smiled politely while checking him out. Late 40s. Wearing a collar and tie but with the top button undone and the tie loose. Not that good looking and obviously had had a few drinks.

"What's a nice girl like you doing here?" He was slurring his words a bit.

"Just having a drink. What about you?" I said, still trying to be polite.

"Yeah. A couple of drinks. How about you and me go somewhere a bit quieter?"

I was wondering how to get out of this. He wasn't the sort of guy I'd go out with normally. Certainly not when he's had too much to drink.

"If you make it worth my while." I replied thinking I may as well play along.

"What would that be?" He asked a bit unsteady on the seat.

Thinking if I make it a lot he will either go or I could put up with it for the money. "$600 an hour or $4000 overnight."

He looked a bit shocked and sat up a bit straighter. "That's a bit steep. The other girls only charge $300."

"I'm not the other girls." I replied. "Take it or leave it."

He looked at me for a minute. I looked back at him blankly.

"Nah leave it." He said and slightly staggered off towards another girl.

I was thinking if I brushed a few guys off the other girls might not be as resentful.

"Hi."

I jumped a little as another guy sat next to me.

"Hi." I replied

"James" He said extending a hand.

"Robin" I replied shaking his hand.

Now James here was a bit more my type. Late 30s / early 40s. Well dressed. Quite tall, probably around 6ft and nice to look at.

"Much happening tonight?" He asked.

"Oh a bit quiet." I replied.

"I had noticed a couple of guys chatting to you. Not interested?"

"Hmmm ... One was a bit drunk and the others didn't really interest me."

"A bit picky are you?" He asked.

"More a case of being careful" I replied.

"Ah ok." He replied. "So are you looking for an interesting evening? Or just having a drink?"

"Well I always like interesting things. It depends what's on offer?" I leant towards him to expose a bit of cleavage.

"Hmmm ... Maybe a drink, some good conversation, a bite to eat, possibly a bit more ..." He responded.

"Sounds quite nice. You prepared to make it worth my while?" I said while running a finger upwards along his leg.

"And what is your while worth?" He asked smiling.

"$400 an hour. $3000 overnight." I responded

"Not sure about overnight. How about a couple of hours?"

Thinking quickly. "$700" I replied.

"OK." He said. "What do you like drinking? Champagne?"

"Champagne's fine."

He ordered a bottle of champagne to take with us while we finished our drinks. Then we headed off to the lobby. On the way out I saw Ruby wink at me and raise her glass. A couple of other girls looked at me as if they were mentally throwing daggers at me.

We stopped at the lifts and waited for one to come down. I was starting to get a bit nervous with what I've just done. But he was quite nice. I could easily have a one night stand with him. I thought that's effectively what I'm doing, but I'm getting paid for it.

Would I be able to pull off being a "working girl"? At 25 I was a long way from being a virgin. I'd had a couple of boyfriends, some casual relationships and more than a few one night stands. I'd been told I give great head and more than once been complimented on "being a good fuck". So I thought nothing to worry about there.

Then I started to think about the logistics. Did I have a condom? I was pretty sure there was at least one in my bag. Then I thought if necessary there should be some in the bathroom along with the shampoo and soaps. Probably no lube, but I usually get more than wet enough.

The lift arrived. We got in and he pressed the button for the suite level. I was impressed. James smiled at me and I smiled back.

Holding the champagne up he said "There should be glasses and an ice bucket in the room."

"Great." I replied.

We stopped at the third to top floor. Only the penthouses above us. The carpet and paint on the walls showed this was a cut above the floor my room was on. We headed down the hall. James stopped at one of the rooms and swiped his card. He went in first then held the door open for me.

"Thanks." I said.

Walking into the suite was more like walking into an apartment. There was a lounge with a small kitchen off to one side. A bedroom off to the other side and a large balcony looking over the ocean.

"Head out onto the balcony Robin." Said James and he headed into the kitchen. "I'll organise some ice and glasses."

"No worries." I replied heading for the balcony. It was a warm night so it was very pleasant outside. I could hear the waves breaking gently on the beach below us and some soft music from the pool bar. I sat down on one of the lounges on the balcony.

Presently James appeared with the champagne in an ice bucket and two glasses. He put them down on the table near the lounges. He opened the champagne with a slight "pop" and poured two glasses, handing me one.

"Cheers" we said simultaneously, then laughed.

James sat down on the lounge next to mine.

"What brings you here?" I asked.

"Conference and Business." He replied. "What about you?"

"Oh just visiting." I replied truthfully.

We both took a sip of our drinks.

James got up. "Do you mind if I change? A collar and tie has its limits." He asked.

"Fine by me. I'm not going anywhere." I replied smiling.

James returned in a few minutes in shorts and a polo shirt. He had quite an athletic build. I smiled almost unconsciously.

"That's better." He said.

"More comfortable?"

"Yes it is." James replied. "Can I suggest anything to make you more comfortable?"

"Hmmmm ..." I was thinking there was nothing I could change into and I wasn't wearing a great deal in any case. "Well the champagne is great but I do love a nice neck rub."

James was still standing and he moved around behind my lounge. I flicked my hair round over one shoulder so my neck was clear. James put his drink down and started to rub his thumbs and fingers on the back of my neck, then down onto my shoulders. I pushed back against him. A slight moan escaped my lips. I love a nice massage.

I managed to take a few sips of the champagne while James gave me a nice neck and shoulder massage.

James moved a bit closer. A couple of times when he stopped the pressure with his hands my head went back and I felt a bulge in his shorts.

I was getting more than a little turned on by this so I thought I would start to give James what he was paying for. I reached round and undid the halter top behind my neck. The top of my dress fell down exposing my 36c tits to the evening air. It wasn't cold but my nipples instantly hardened with being exposed.

It didn't take long before the neck and shoulder massage had become more of a tit massage. James's hands were under my breast and his fingers rolling and massaging my nipples. I'm quite proud of my tits as they're all natural and quite firm. My nipples are pert. I've been told they're a perfect bite size.

After a few minutes of my tits and chest having a lovely massage I sat up a bit more and swung my legs round to the side of the lounge. I took one of James's hands and brought him round in front of me.

I looked up smiling as I started to rub my hand over the large bulge in his shorts. I gave it a nice lick upwards with my tongue. Putting a couple of fingers into the waist band of his shorts I started to pull them down. I was greeted with a lovely 7 inch cock well on its way to being hard right in front of my face.

I took it in my hand and started to give it a slow stroke. I pushed it to one side and moved my mouth forward so my tongue could start exploring his balls. James moved his legs slightly apart and I heard a low moan as I took one of his balls into my mouth and ran my tongue around it while stroking his cock a bit harder with my hand.

Giving both his balls the attention of my mouth and tongue I soon had a rock hard cock in my hand.

Starting at the base of his cock I licked up to the head with the tip of my tongue. Giving a flick at the top I repeated this a few times. Looking up I could see James looking intently as I worked on his cock.

Taking the base of his cock in my hand I put my lips around the head of his lovely cock. I ran my tongue around the head, flicking the tip of my tongue over the slit at the top.

I've been told my lips were made to wrap around a cock, particularly when they've got deep red lipstick on them. I moved my mouth further down his cock, then pulled back a bit, then taking it deeper again. As took him in my mouth I pressed my tongue under his cock and pushed it against the roof of my mouth. I was greeted with more moans from James.

Moving up and down his cock I was taking it deeper and deeper into my mouth. I took my hand off the base of his cock and started to tickle his balls gently with my fingernails. After a little while I had him all in my mouth with my nose pressing against his pubic bone.

I've never had a problem taking cocks in my mouth. I don't think I have a gag reflex. So James at around 7 inches was no problem.

After bobbing up and down a few times I took all of his cock and kept it in my mouth. I started to make swallowing motions with my mouth and tongue. I've been told by guys this feels like their cock is being massaged by my mouth.

James moaned louder then gently put his hands on my head and pulled his cock out of my mouth. I looked at him a bit surprised

"Shit." He said. "That was the best blow job I've ever had. But it was starting to get a bit too good. I'd like to see what else you have to offer before cumming."

"OK" I said. I stood up and indicated for him to sit down on the lounge. I reached into my bag and grabbed the condom I'd checked was in there. I pulled James's shorts all the way down once he was on the lounge.

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."