Career as a High Class Escort - My First Client

Cheryl got out of her car and had arrived at Tanya’s office, it was a dreary Tuesday Morning, she pressed the buzzer beside the door and a voice came over the intercom ‘Hello, how can I help you’, ‘I’m Cheryl, I’m starting here today’, she replied, ‘Oh yes, I’ve been expecting you’ said the intercom voice. Cheryl thought it sounded familiar as voice intercoms are not always great. The door opened and there was Tanya, dressed very business like. ‘Cheryl, sweetie, you’re here finally, come on in’ and opened the door further.

‘Hey Tanya, nice to see you again’, I said

‘Yes, how was your drive up, not too bad, I hope’, asked Cheryl

‘No, only about 90 minutes, traffic was good’, I replied.

‘Great, let's get down to business, come on over and lets get you started’ Tanya said and she ushered me to her desk, her office was very nice, she had a few girls in the office, all her arrangements came through her website, her clients, once vetted, were given a username and password to access the girls, this allowed total privacy and her girls were not plastered all over the internet for everyone to see.

So we went through the standard paperwork, address, bio details, bank details and details of what was off the table when it came to sex etc, such as scat, piss etc. Once we had completed the mundane stuff, she took through to another room, I saw lots of underwear and provocative clothing hung up on a rail to the side, she introduced me to her photographer, Kat, 

‘Kat photographs all my girls, she’s awesome with that camera, just follow her lead and you’ll be fine, go and pick some nice clothing over there and get changed, I’ll leave you in capable hands, come find me when you’re done’, Tanya said and headed back to her office.

I got changed multiple times and Kat got me to pose in all manner of ways to ensure they got the right shots, Once finished, I walked into Tanya’s office, ‘All done sweetie’, she said , I nodded and smiled, a fresh cup of coffee was waiting on the table, which I was ready for. 

‘OK, now we’ve got everything I need to get you setup, it will take me a couple of days to go through your pictures with Kat, I’ll also get your account setup, so can put in days you’re not available like holidays etc and who’s booked you, all your details will come through on here, there is also an app we created that also gives you access to your bookings with all details, so get that installed on your phone as soon as you can, Once we have your profile ready, I’ll call you and you can login to your account and check out your profile, see if you like it and if you do, i’ll make it active.

‘Sounds great’ I said and drank the last bit of my coffee. Tanya sat up and came round and I stood up and she gave me a hug, ‘So sweetie, we’ll speak in a few days’ she said. She ushered me to the door and off I went home . After the drive, I went into my apartment, locked the door behind me, walked into my bedroom and stripped down to my birthday suit and hopped into a hot shower, washing all the drive grime off me. I put on my favourite PJ’s and wrapped my hair in a towel, as I sat down I got a text from Tanya, which read, 

‘Great to see you today , here is the app I mentioned, your account details will be ready soon, Love Tanya XX’, and there was a link for the app, so I clicked it and the app began to install on my phone. I was smiling ear to ear, thinking of what could be if this venture goes well, what I could do with the money. So I got up and poured myself a drink, and watched some trashy film on tv and after a while I dried my hair and went to bed.

I woke up the next day about 9am, and my phone pinged and it was from Tanya and it read ‘Here are your account details’, which were my username and password, a link was also in the text for her website. So I got up and switched on my laptop and typed in the website address and logged in, and there was my profile, along with some very nice pictures of me wearing very little. Just then my phone rang, it was Tanya,

‘Hey sweetie, saw you logged into your account, how do you like it’, 

‘It’s great, love the pictures’ I replied

‘Fantastic, are you ok with me making it active then’ She asked

‘Yes, please do,’ I replied.

‘Ok hun, done, you’re now part of the team, Welcome, I’ll call you shortly, leave things with me and we’ll get you earning, bye for now’ and she hung up.

I was beaming ear to ear, hoping that this is going to pay off, so Cheryl got dressed and sat at her laptop, just checking her mails etc and about 30 minutes later , her phone rang, it was Tanya’s no, she answered and Tanya had good news for her.

‘Hey sweetie, I’ve got great news for you, I’ve got your first client for you, I’ve hand picked this one for you as it’s your first’

‘Oh wow, really, that is good news’ I said

‘Ok, the guy is after a weekender on his yacht , so 3 days work , he’s a really nice guy, been one of my customers for quite a while now and the girls love him, he’s called Philip, and he is very rich, handsome and will treat you very nicely and has stamina for the bedroom, so you’ll be fucked a lot’ She explained.

‘That is fantastic, can’t wait,’ I replied.

‘Good, now get some nice bathing suits, the skimpier the better, as you’ll not need much else, and just your usual girly stuff, details will come through on your app, any problems please call me, I’m available 24hrs, ok sweetie’ said Tanya and hung up. Within a few minutes, the details came through, I was to wait for him in the lobby of the Intercontinental Miami Hotel at 10am, which was not far from where I lived and was it was this Friday , only 2 days from now, so I headed straight out to my local clothing shop and bought some very skimpy swimwear as requested. I was excited about this. 

Friday came in a flash, I packed my bag the night before, and my pre-booked Uber arrived and I headed out, it didn’t take long and I arrived at 9.40am, plenty of time, I always like to be early just in case, I sat down in the lobby of the hotel and within 10 minutes a voice said ‘Cheyl’, I looked up and there was this older well dressed gentleman , handsome, ‘I’m Philip, it’s lovely to meet you’, I got up and he pulled me in and kissed me on the cheek before I could say anything, I smiled and said ‘Likewise’.

‘Please , let me take that for you and shall we head out’, he said and ushered me towards a waiting car. We got in and he said ‘We’ll take a boat out to my yacht and from there we’ll just cruise up and down the coast, take in the sunshine and relax. I might have to take a phone call or two, but other than that, it’s all about fun and relaxation.

‘Sounds divine’ , I said and rested my hand on his leg, he smiled as I did, I could already see the bulge in his trousers.

Philip then said ‘Tanya told me this is your first time, don’t worry I’ll look after you, if there is anything you need, please ask’ 

‘I will, thank you’ and gave him a big kiss.

We arrived at the Marina and headed to his boat, it wasn’t long before we arrived at his yacht, it was quite big, around 350ft in length, so we got onboard and Philip showed me to bedroom we’d be sharing, it was very stunning, a large king size bed at one end and cupboards, shower room at the other. I unpacked my very small bag into one of the cupboards, Philip said ‘I’ll just be upstairs fixing us a couple of drinks’ , ‘Thank you, I’ll be right up’ I said.

So I slipped out of my clothes and into a black thong and top, that just had enough material to cover my nipples and show off my ample cleavage, and I proceeded upstairs, I went into the lounge area, and from here I could see that there was also a Jacuzzi, which Philip was already in, I opened the door and Philip looked at me and said ‘Wow, you look amazing’, ‘Thank you, thought you’d like this one’, he then asked me to join him, which I did obviously and he handed me a drink, we sat there for a little while , I could see Philip unwinding, I took a few sips of my drink and went over to Philip and began to kiss him and rub his crotch, he was already very hard and a good size too.

He grabbed my ass and a handful of tit and we kissed passionately, lots of tongue, I pulled off his trunks and put them on the side, he pulled off my top , my tits out, I told him to sit on the side of the jacuzzi and I began to lovingly suck his throbbing cock, using my tongue up and down his shaft and around his tip, my other hand massaging his balls, which were quite full from the feel of it. Philip was moaning with pleasure, I sucked on his cock for ages, then giving it the occasional wank too.

It didn’t take long for Philip to blow his load deep down my throat. I felt his hot spurts of man juice hit the inside of my mouth and it was a big load too, I swallowed every drop and made sure I got every drop from his cock. Once he didn’t give me any more nut juice, I leaned back and smiled at him, he loved it and said ‘Christ, how did you know I needed that’, ‘Well you were already hard when we got in your car and knew you were horny for something, so I thought you’d enjoy blowing your wad down my throat as a starter. I said to him, He smiled and gave me a big kiss and we sat back down in the jacuzzi , enjoying the bubbles and scenery.

It was time to eat, so Philip ordered us a nice light lunch, I covered up my boobs with my top and Philip handed me a robe, soft to the touch, we sat down and within a few minutes our lunch arrived, chicken strips with a salad garnish and a drop of red wine. We began to eat , the chicken was extremely tender and moist, and I savoured every mouthful, and sipped at the wine. Once we had finished Philip asked about why I decided to become an escort, so I told him about my previous job, and how boring it was, stuck in a 9-5 job with not many prospects.

Philip nodded his head and said, sounds similar to me starting out, which I thought was unreal, as I just thought he was a rich kid who’d made more money off his parents estate etc, but it wasn’t true, he started out at the bottom of a firm who did exactly what he does now, which was to buy firms that have gone into administration and either sells off the assets or try to turn them around. He worked his way up through the firm and learned how they did this and was very good at it, but got tired of just getting a salary and the company reaping the big rewards.

So with 2 of his friends from the same firm, they decided to start they’re own company, and PSG Industries was born, made up of Philip, Steve (finance whizz) and Graham (Attorney law whizz), and in the 15 years they’ve been going, they have all become filthy rich and have quite a portfolio of companies under their belt they turned around. I thought not bad, he started at the bottom and worked hard for where he is, he then told me he works long hours though, around 80-90hrs a week 7 days a week, so he makes sure he gets 1 weekend a month off to relieve the stress, hence using Tanya and her girls for this, he didn’t want someone tied to him 24/7 like a normal relationship, Tanya’s business suited his needs.

He stood up and held out his hand and said ‘come with me’, I could see he had a bulge in his trunks, so I knew he wanted some action, so I grabbed his hand and followed him to the master bedroom, I walked in and was just looking at the room , taking in the decor, when I heard the door shut behind me and within seconds , Philip came up behind me and kissed my neck and his hands pulled open my robe, pulled aside my top and cupped each breast, I could feel his hard cock pressing into my ass cheeks, ‘someone’s horny I see’ I whispered to him as he was kissing my neck.

He pulled off my robe and it fell to the floor, then my top, then my briefs, all in a heap around my feet. I turned around and kissed him hard, my hands running through his hair and down his back, giving his tight bum a squeeze. Philip asked me to lie on the bed, which I did and he got on top of me and we kissed some more. He was a good kisser, not like a lot of guys, that just slobber all over you. He was very tender and loving, he began to kiss my neck again and worked his way down to my breasts, he sucked on each of them, paying attention to my now rock hard bullet nipples, he was enjoying them, he worked his way down my stomach, kissing my flesh as he proceeded down to my pussy.

When he reached my pussy, he began to kiss my outer lips, fingers probing my hole a little, I was very wet, his tongue licked my clit and I moaned with pleasure and he then took my clit in his mouth and flicked his tongue more, christ he knew was he was doing down there and I moaned even more. He pulled apart my lips and his tongue probed my inner fuck hole, I was soaking even more now, he spent ages moving from my clit to my pussy and it wasn’t long before I had a big orgasm , I grabbed his head and screamed as wave after wave came over me, it lasted for what seemed an age and once it stopped I sort of passed out, Philip moved on top of me again and began to kiss me tenderly and I started to come round and I smiled at him and we kissed, at that moment, he slid his rod into my hole and I put my arms around him and kissed him again.

I gasped as he pushed his cock balls deep into me, he groaned as he felt my pussy wrap around his throbbing cock, as we kissed he began to thrust his cock in and out of my pussy, slow movements out and fast in, every time he went in, his balls slapped my pussy and I moaned with pleasure, this guy was being attentive, loving and making sure I also had a good time whilst getting what he wants. I held him, my arms around his neck, kissing him, lots of tongue, I kissed his neck and he did the same and occasionally sucked my tits. I talked dirty to him in one ear, saying things like ‘how do you like my pussy, and ‘you want to come in that pussy don’t you’, he quite liked it and answered each time.

I moved my hands down to his ass and grabbed a cheek in each hand, I kissed him again, lovingly and tenderly, giving him the full works, and he began to moan and his cock started to swell and I knew he was at the point of explosion. So I gripped his cock very tightly and this did it, within seconds he shot thick streams of cum deep into me, I could feel the hot spurts, all warm, he moaned loudly and his body twitching with each spurt, once he finished, he lay on top of me and I hugged him, kissed him. After he recovered he got off me and we lay together on the bed, and I snuggled up to him, stroking his hair on his chest and he then said ‘mmmm, that was amazing’ , ‘so were you’ I replied and we kissed again.

We lay there for a while and Philip was the first to get up and he went to the bathroom and cleaned up, I could feel the cum oozing out of my pussy, so I reached for a nearby tissue and cleaned myself up a bit, got up and went into the bathroom as sat on the toilet, all his cum came flooding out of me , ‘Christ that was a big load you gave me’ I said to him and he just smiled and winked at me. We both got dressed and went back up top and I got on and lay on a sun lounger, catching a few rays before the day was over. Philip came over and offered to rub sun tanning oil on my body which I accepted of course, he began to oil my legs, which I spread for ease of application, his hands briefly touching my pussy on purpose ,then my stomach, once he got to my chest, I removed my top and he wasted no time in oiling my boobs up, paying a lot of attention to my nipples, I flung my arms above my head and let him oil me up, I turned over and again legs, ass, his fingers touching my poop hole, then onto my back and neck.

A couple of hours went by with us sunbathing, chatting and drinking the odd cocktail. When he asked what I'd like for supper, I said I was in the mood for a nice juicy steak, medium rare. He wanted that too, so picked up his phone and rang the kitchen and ordered his food. We got up and put on our robes, the sun was going down now and it was going a little darker now and we sat at the table, Philip poured me a drink and it didn’t take long for our food to arrive, the cabin staff put our food on our table along with a large bowl of delicious salad (us girls have to look after our figure you know). We ate our meal and drank our wine, and we chatted again for a little while. Philip asked if I fancied watching a movie in the bedroom, and that we could shower and wash all the oil off, which I thought, why not, it’s been a long day of having fun, eating food and drinking yummy cocktails. So off we went back into the master bedroom and we got in the shower and we washed each others bodies and he starting getting hard again ‘Oh like that is it’, he smiled, so I grabbed his cock and wanked him hard and fast, he began to moan and it didn’t take long to bring him to the edge where I stopped, I did that twice, he quite enjoyed it.

We finished showering and I dried my hair, Philip was lay on the bed and he picked up a remote and pressed a button on it and all of a sudden a TV began to rise up from the end of the bed, it was bloody huge, 60” at least, ‘What do you fancy for a movie’, he asked, ‘ohh I like action movies, so anything like that’, Philip found one and it began to play on the screen. I got in bed, naked of course like Philip and we just snuggled and watched the movie. Philip put his arm around me, he cupped my tit as we watched the movie and give it the occasional squeeze, so I put my hand round the base of his cock, my fingers round his still full nutsack, rubbing my finger up the muscle at the base.

The movie finished and we snuggled down to go to sleep and we spooned, his other hand came over and cupped my breast, I still had hold of his cock, his tip was soaking with precum and he was rock hard, I twisted my torso round and kissed him, then guided his fat wet cock to the entrance of my asshole and pushed back on him, his cock began to slide up my ass, lubed by the precum, he pushed even more into my ass and groaned as I took every inch up my bumhole. He began to fuck my ass slow and hard, my eyes rolled into the back of my head as his cock filled me up so much and it was lush. After a while he turned over, me still impaled with his rod, my back to him, I supported myself to ride him.

I began to slide up and down on his rod, his hands playing with each of my tits and one then moving down to my pussy, he inserted 2 fingers and began to finger me, my pussy wet with his cum from earlier and my juices, It didn’t take long before I had an orgasm from the anal fucking and began to grip his cock tightly as I came, this made Philip blow his wad in my ass and I felt the warmth of his man juice inside my ass, I lay back on him and he stuck his fingers he had up my pussy in my mouth and I greedily sucked on them. Philip’s cock was now limp and retracting from my ass, I tightened my ass hole up so as not to cover the sheets in man juice, I kissed him, got up and went to the bathroom to clean up, Philip followed behind me.

He smiled at me and leaned over and kissed me and said ‘Cheryl, you are one dirty lady’ I smiled and licked my lips at him and winked. He was certainly enjoying our time together, we got back in bed and both of us fell asleep very quickly into a deep sleep. That is pretty much what we did for the next 2 days, fuck, eat, drink ,sunbathe, more sex and so on, on the last fuck we had, he gave me a hot facial at the end, showering my whore face with his man juice, a good load considering he’d already fucked me 7 times before that. And then came the time to leave as the ship moored up, I put on my outfit I arrived in, Philip led me to the boat to take us ashore, we sat together at the back of the boat, watching ships pass us by, people waved at us as we waved back. My hair blowing in the breeze, Philip had his arm around me and my hand was resting on his thigh.

We came ashore and Philip asked how I was getting home and i said I’d call and Uber, he said he would have his driver take me home to ensure I got home safely, he pulled out his phone and dialled a number and spoke to someone and within minutes a large SUV type vehicle pulled up, he opened the door and I got in and he kissed me, ‘Just tell my driver the address and he’ll do the rest, thank you for a lovely weekend’ he said, I smiled and also thanked him for a wonderful time, ‘We’ll meet again, I promise you that’ said his goodbyes and closed the door. ‘Where too Ma’am’ The driver asked, I gave him my address and off we went. I took in the view on the drive back to my apartment, it didn’t seem very long before we pulled up outside my apartment block, the driver got out and opened my door and took my bag and walked me to my door. I thanked him for the drive and for walking me to my door and he replied ‘you’re welcome ma’am, have a good night’ and walked away.

I opened my door, walked in and closed and locked the door behind me, Ok I thought, time for a hot shower and a drink, so I undressed and left the clothes all of my floor and got in the shower, the hot water washing the day off me, I love having a hot shower before bed, put on my robe, wrapped my hair in a towel, poured my favourite drink into a glass, sat on the sofa and then my phone pinged , it was Tanya, ‘Hey sweetie, just had a call from Philip, he fucking loved you, he said you certainly destressed him over the weekend, well done for your first one, funds on the way’, I thanked Tanya for the feedback and we chatted a little longer and we said our goodbyes and hung up, I felt good, my first client was happy, which meant he'd definitely book me again. Just then my phone pinged, a text message from my bank, $20,000 deposited into my account.

I couldn’t believe it , I’d earned 6 months salary in 3 days. Compared to my old job, I could get used to this kind of money I thought. I decided to dry my hair and climb into bed, my Escort career was about to take off.