Clarissa's New Job Pt. 03

You should read parts 1 and 2 first or this won't make much sense xx

*****

Emma!

My eyes stared at the open private chat window for several minutes. I'd managed to type a rather unimaginative, 'Hi, I'm in Chicago too' as my opening message and, so far, no reply from Emma. Obviously, I thought, she clearly just thinks I was an idiot and was ignoring me. Leaving the laptop for a moment, I went to get a cup of coffee. Deciding that I needed some peace and quiet for a few hours, I switched off my cell. Just as I was getting ready to look for a new woman to talk to, my computer pinged and I saw the words 'Hi Hun' appear in the window.

My mind went black as I stared at the screen, what was I supposed to say now? I managed a pathetic, 'How r u?' Hitting enter, I realised that I was unprepared for this conversation. Emma replied quickly telling me that she had looked at my profile, then followed up with 'Hot pic, you're cute!' I thanked her and we entered into a little small talk, complimenting each other on our bodies and our pictures.

Out of the blue, Emma typed 'So hun, what is it you really want?' I decided to go for it.

'I'm a newbie at this and I was hoping for a little advice.' I typed into the chat window.

After a short pause, Emma replied, 'Yeah! OK, I can see from ur profile that ur new, and, you're kinda cute, so yeah, I'll help you.' I thank her and I was just about to ask my first question when Emma said 'Wanna meet?' Looking at her message, I felt surprised that she would have wanted to meet in person but I figured there was nothing wrong with that. I agreed and thank her again. We arranged to meet in the park the following morning so we could walk and talk in private. I felt comfortable with our plan and I was intrigued to meet another escort in person.

That afternoon I showered slowly and got dressed up. I thought about not turning my phone on and taking the day off, but I felt compelled to meet someone else that day, and, at least I would have something more to talk about with Emma the next day. It was not even dark when my phone bleeped and I quickly picked it up to read a short SMS. 'Hey, I wanna c u 2nite, u do anal?' I looked down in slight shock, I had been clear on my profile that I didn't offer anal sex. I had done it before with a guy or 2, it was never horrible but I didn't feel like I needed to have clients butt-fucking me. I decided to say no. I was slightly sorry that I didn't hear back from the guy.

I thought about for some time and was confident that I really didn't want to offer anal, at least for the time being. Another hour passed before my next message. This one seemed more hopeful. 'Hi, I'm Calvin, Is it OK to come and see you tonight, at 8pm?' Polite and friendly. I said yes straight away and gave him my address.

Calvin had arrived bang on time and I'd let him in. He was really tall and had a suntan. I guess about 40 with shoulder length hair. He was very chatty and seemed relaxed. I noticed a tattoo poking out from under his shirt sleeve. It looked like the tail of a snake. He had an element of a rocker about him. I asked him if he wanted a drink and he very politely declined.

I looked at him as we spoke and he kind of ran out of things to say. "This way" I said with my biggest smile and I reached out, took his hand and led him into the guest room, which was, really now a bedroom! I sensed that Calvin was a little nervous so asked him to sit on the bed. He looked up at me as I stood in front of him, slowly unbuttoning my shirt. I opened it up and exposed my red, lace bra as I let the shirt slip of my shoulders and fall to the floor. Reaching behind me, I expertly unclasped my bra and saw him staring at my chest as I let the lace bra slip from my breasts, leaving them in full view.

Calvin took the hint and began to unbutton his shirt, kicking off his trainers at the same time. Grabbing Calvin's hand I stood him up. "Let's get these off," I said quietly as I pulled his jeans down. Calvin immediately started to take off his boxer shorts. I let him finish before I turned my back to him and unzipped my tight, short black skirt. I bent forward and wiggled out of it, lingering a little so he could see my ass with just the thin strip of red lace between my ass cheeks.

After just a moment, Calvin reached out and put his hand on my ass. I felt him massaging it and running his fingers down over the lace before he grabbed the top of my panties and really slowly pulled them down. I felt them pulling free of my ass and pussy as they then slipping down my thighs and legs.

As Calvin seemed to be enjoying my ass, I bent forward a little more and he began to rub his finger over my pussy lips. I was starting to feel good and was starting to quite get wet. I really enjoyed feeling him spreading my slippery juices all around. Pretty soon I felt him push his finger inside me and I spread my legs and squatted a little to make it easier. I had soon become dripping wet with the attention of his finger.

Standing up as he slid his finger out, I turned around slowly, and knelt between his knees. My fingers curled around his dick and I felt it in my hand, it was fairly big and was quite hard. Bending over, settling on my knees, I held his cock and began to kiss it, my lips pressing into the hardening flesh of his cock head. Letting my tongue slip out, my kisses turned into long licks as I swirled around his cock. Calvin said softly "Fuck! Yeah baby, mmmhmmm." I felt him tense up a little as I opened my mouth and slid my head down his cock as far as I could. "God, Oh fuck that's good," I heard from above.

Calvin was really getting into my cock-sucking and I was pleased with myself that I seemed to be making such a good job of it. His cock felt like it was fully hard and the head had swollen into a mushroom shape which I felt bumping over my lips.

I pulled my mouth away and kissed his dick again as I pulled out a rubber and began to cover up his lovely cock. "How do you want it baby?" I ask him.

Calvin replied by gently putting his hands on my shoulders and pushing me back. I lay down on the bed and as Calvin knelt between my legs, I pulled my thighs up putting my hands on my knees. Calvin leant forward and his head came towards mine. In a matter of seconds, I felt his cock prodding at my pussy as he got himself into position. I looked him in the eyes as I slid my right down from my knee and along my thigh until it dropped between my legs. Managing to hold his cock, I moved it into the right spot and as it began to slip inside, I threw my head back and put both my hands on his butt, pulling him down on me.

The big cock filled my pussy up so nicely. It slid inside in one smooth thrust and I let out a long moan, as did Calvin. I felt myself being fucked just the way I liked it. Calvin fucked me firmly and deeply and I was just beginning to relish the feeling of his big cock when he suddenly grunted and went silent as I felt his dick pumping its sperm into the condom. A wave of disappointment passed over me briefly as he slumped down on me and I put my arms around his shoulders. I could feel his cock shrink in my pussy.

Calvin let his cock slip out and I did the usual clean up. We made small talk and he got dressed before he thanked me and left, just like that, it was over. I was happy that I had obviously pleased him but it was over too quick for me once I was enjoying it. That was just going to be a part of this job, it wasn't about me. I made it to the shower and and after clearing up my working bedroom, I climbed into my bed. Briefly, I thought about getting one of my vibrators out and having some quality 'me' time, but I quickly put the thought out of my head and darkness swept over me as I fell asleep.

I awoke with a start that morning and realised that I'd overslept. The excitement of the last few days had caught up with me I think. I was just getting out of bed when I remembered... I had to meet Emma in an hour. "Fuck!" I said out loud to nobody as I raced into the bathroom. Twenty sweaty minuets later and I was drying my hair. I pulled on my nicest jeans and a shirt and rushed out of my apartment, down the street, making it to our arrange meeting place, near the soldier statue in the park in the nick of time.

Looking around as I caught my breath, Emma wasn't there. I sat myself on a bench a few feet away and watched the people passing me, I looked for Emma but there was no sign of her. Eventually, I got distracted as I watched a couple walking towards me holding hands. I though that they looked happy but at this time, I had no desire to be in a relationship. I jumped as I heard a voice next to me say, "Clarissa?"

"Emma, urr, Hi!" I managed as I looked around.

I stood up and Emma leaned in and kissed my cheek, I breathed in and could smell her sweet perfume which lingered in my senses as she moved away.

"It's good to meet you." She said as we both sat down on the bench.

I was fumbling in my head with my words but I just decided to be honest, I was certain that I wouldn't be able to hide much from this woman and why would I need to? "I don't know what to say now, apart from thank you for meeting me."

Emma smiled sweety at me, she looked so much better in person than in her pictures, you could tell that she was in her 40s, but only just. She clearly kept herself in excellent shape and she had a really big smile that was, in some deep way, really warm and disarming.

"I get it honey, I was new at this once. Pretty confusing right?" Emma patted my thigh. "Let's walk," she said.

We stood and began to slowly walk around the park. She listened as I told her how I had lost my job, became so worried about money at the same time I stumbled over an escort website. Emma told me about her first experience, for her, she had been a dancer and due to a lack of work, she ended up in a strip joint and slipped into escorting.

"With over 15 years at this, I'm glad I'm an escort. I have money, friends and a nice home." Her perspective was interesting. "I travel when I want to. Sure, I have to see dodgy men sometimes but fuck it! Who cares if they pay right?"

I had to admit that she had a point.

"How many punters have you seen?" Emma asked me.

I told her in detail about the 4 men and in particular, about the differences and how I had actually really enjoyed one of them.

"Sounds about right for a $200 girl." Emma said as she looked at me.

I wasn't sure what she meant and I was just about to ask her when she continued. "Why do you only charge $200, I mean, a cute little thing like you?"

I explained my reasoning and that I wasn't comfortable with anything other the vanilla sex. Emma stopped and turned to me, checking over her shoulders to make sure no one was in earshot. "Look, this is my advice. If you wanna win at this life, you gotta up your game girl. Get your head around giving the rich men what they need and cater for the kinks. Anal, girl-girl, toys, parties, orgies, group. That's when you can charge the big money. Otherwise, you can keep seeing the Johns in your room and scrape the bottom but I promise, you'll give it up, they all do."

I looked at her, "I don't know if I can do all that stuff or even if I want to."

"Of course you can," Emma continued. "If you can let a random man cum on your face without saying a word then you can do it, you know it."

Before I could say anything else. Emma said, "Look babe, I gotta go, meet me for a drink at Largo's Bar over the town at 9 ish, we'll carry on...you free?"

I nodded, "OK, thank you, I'd love to."

"Good!" Emma replied, "I am going to make you my new project!"

I wasn't sure what she meant by that but I liked her and was already looking forward to our drink. Emma kissed me again and we said goodbye as we went our different ways. I turned and looked at her as she walked away from me. I admired her ass as it wiggled from side to side. Emma walked with confidence. I liked her a lot and I was really looking forward to seeing her that night. I smiled to myself and wandered off.

Lunchtime had passed but I sat in a coffee shop and ate a sandwich. I was looking out of the window at the people walking by but my mind was thinking through what Emma had said. There were a lot of things to consider and I wasn't sure this was the path for me. On the one hand, Emma was very successful but she seemed to take it all in her stride. I felt unsure. It didn't feel the time to make a decision was right now, I would let fate have a hand in things.

What I needed was the rest of the day off. I decided not to switch on my phone that day and I really needed some time to myself. Unusually, I went to an afternoon movie, a really easy romantic comedy which I enjoyed. It felt great to enjoy some simple pleasures and not have to worry about my next client.

Evening arrived and I found myself at home, getting read for my night out with Emma. I searched my drawers and my wardrobes in search of the perfect outfit. I really had the urge to make an effort. In truth, I wanted to impress her. Pulling out most of my clothes in a huge mess, I settled on white, satin panties and bra, a light yellow vest top and my tight black miniskirt. I felt really sexy and I looked great as I finished off my ensemble with knee length black boots.

I walked across town and amused myself catching the guys looking at me as I moved past them, it always gave me a kick. I arrived at Largo's Bar right on time. I went inside and looked around. It was a modern, bright bar with big windows looking out on the street. The décor was a tasteful blend of white and deep purple. No sooner as I finished my look around, I felt an arm slide around my shoulder.

"Hello baby." Said Emma as she kissed my cheek.

I looked around and there stood Emma wearing a dark red dress which clung to her body all the way down to just above her knees. Black nylon covered her legs until they reached her sexy, red shoes. I could barely take my eyes off her.

"Hey there," I replied, feeling happy that Emma had actually turned up "What can I get you?"

Deciding that we would drink wine, we chose a bottle that we both liked and sat down. I did mention to Emma that I didn't hold my drink well but she just laughed so I figured, what the fuck! Enjoy yourself.

We found a table in the corner, the bar was quiet and we would be able to talk without interruption and sat down. Emma spoke first. "You're looking fucking hot tonight girl!"

I think I blushed, but managed to repay the compliment. "Like you then, Oh my God, look at you!"

Emma laughed hard. "Well two hot girls on a night out then!" She lifted her glass and we began on our wine. So followed a fantastic night out, I think!

A few hours later and I was drunk, there was no getting around it. It didn't matter, Emma was drunk too. We were laughing and giggling and generally being stupid. I really can't even recall what we talked about. I am fairly sure we started on the practicalities of being a high class escort but we ended the time in the bar contemplating the merits of different colour street lamps and descending into hysterical laughter with every other word.

Emma leaned towards me, "Let's the fuck out of here babe." she slurred at me.

"Yup, let's goooo." I managed.

We must have looked like a pair of idiots and we got to our feet and wobbled out of the bar. The cold air hit me and made me feel light headed but I was still just about able to walk. Emma, slipped her arm into mine and shoulder to shoulder was started to walk. We were singing, I think, probably, that part is a bit of a blur.

What I remember next is being lost. I suddenly had no idea where I was.

"Shit, Emma, I'm nowhere near my apartment." I remember saying.

"Oh, yeah, I didn't think of that." Said Emma as she wobbled on her feet.

I was looking around trying to get my bearings among the tall buildings when Emma grabbed my arm. "We're nearly at my place, crash there babe."

I was so drunk, I knew I needed to lie down and soon. Bed was all I could think about. My last logical thought through the fog of alcohol told me to lie flat and sleep as soon as possible!

"You sure?" I ask.

"Yeah, why not? Come on, it'll be fun." Emma said with a laugh and she grabbed my hand and pulled me as I staggered behind her.

I was having trouble focussing my eyes but we made it up the front steps of Emma's building and she let us in the door. I vaguely noticed that it was a smart and expensive looking apartment block. Emma punched the button for the elevator and we both started laughing when the doors opened. We stepped inside and I asked Emma why we were laughing at the elevator. "Because, we are totally fucking drunk." We laughed, hard, again until the elevator doors opened onto the landing of the top floor.

I looked at Emma fumbling for her keys and then struggling to get the key in the lock of her door as she swore at it. After what seemed hours but was really seconds, she swung open the door and we entered her home. I only took in the fact that it was huge and not much else.

Emma staggered past me and opened a door, she motioned for me to follow her and we went into a big bedroom and I felt so relieved to see the biggest, most comfortable looking bed of my life. "You can sleep here babe, this OK?" Emma asked.

"It's fucking amazing." Thank you. "Where's your room?" I ask.

"Here! I only have one bedroom babe, there's lots of room."

I looked at Emma and we both burst out in laughter yet again.

"Go on, let's get undressed and get some sleep." Emma said as her head began to sway a little.

"Yeah! Great idea, I need sleep real bad!"

I had sat on the end of the bed but I got up and leant over to take off my boots and then I felt dizzy. I fell over in a heap on the ground and, stunned, I looked up as Emma stood over me grinning. I laughed as she unzipped my boots for me, I crawled back to the bed and managed to stand again. I was finding everything very funny.

I managed to pull my boots off, successfully this time. I pretty much ripped off my top and unzipped my skirt, leaving just my panties and bra on. I wasn't even aware at the time but now I remember Emma looking at me as I got undressed. Emma pulled back the sheets, "Here you go babe." I sat on the bed and swung my legs in, Emma covered me up. I lay back and felt the soft pillows envelope my head and the cool sheets felt fresh as they clung to my body.

I watched Emma sit on the other side of the bed and remove her shoes. She managed to get to her feet and lift off her dress revealing her deep red bra and thong. I couldn't take my eyes off her body as she bent forward to slide off her stockings, I had a lovely view of her cute butt. I wish I had been sober enough to properly enjoy it.

I felt uncomfortable in my bra and sat up and took it off while still covered in the sheet. Emma noticed and shrugged her shoulders. She reached behind her and unclasped her bra too, pulling it off her arms and letting her breasts fall free. They looked wonderful, a perfect teardrop shape with large nipples. I can't be sure but I think she saw me staring at her. I put my head back down.

Emma turned out the light and the room was plunged into darkness. I heard her shuffle back to the bed and then I felt it move as she climbed in. "Such a great night Emma, thank you." I said quietly.

I felt her move and she had turned towards me, I could feel her breath on my face. "You gonna kiss me goodnight babe?" she said quietly. If I hadn't been drunk, right now I would be thinking about the implications, but then, I probably would not have been in a strange woman's bed either.

I reached out in the darkness and my hand touched her arm. Emma wriggled towards me. My hand ran a little way up her arm and I put my head forward, I felt our foreheads touch in the dark and I placed my lips to hers. I felt her kiss me and the next thing I knew was her hand sliding up my neck and behind my head. Despite my drunkenness, I wanted her badly. I savoured the lingering kiss and then Emma pushed her tongue into my mouth at the same time she moaned through her nose. I relaxed my mouth and enjoyed the feeling of her exploring me in that way and I felt every nerve in my body respond.