Clarissa's New Job Pt. 01

Down But Not Out.

My name is Clarissa. My story begins a few weeks after my 25th birthday. In fact, I'll start my story from when I was running, early in the morning, on a hot spring day because this is where my new journey started, this is the day that I first began to question myself.

I like to keep myself in shape, I have no desire to be skinny, but I don't want to be overweight either and I definitely want to be fit and healthy. I had taken up running because I could no longer afford the gym membership fee. Earlier that year, I had lost my job when my company closed down and I was struggling to get another one that paid a reasonable salary. I had worked hard to become a manager at the chain of clothes shops where I had worked since leaving school and I had become used to having money when I needed it. I lived in a nice apartment, full of lovely things. As I ran that morning, I was, again, worrying that I would have to leave my home and sell my things if I didn't find a job soon. Running each day was about the only thing keeping me sane.

Of course, it wasn't that I was on the breadline as such, but rather, I liked my lifestyle and I wasn't ready to give it up. Only 2 years ago, I had received a promotion and moved to Chicago, all of my family and friends lived back home in Florida. I had been working so hard, that I hadn't really made many friends and certainly no close ones. I felt pretty alone that morning as I ran around through the gateway to the park.

I was working up a sweat as I ran through the park, enjoying being among the trees. I had been feeling so down that morning was still working through all the negative aspects of my current situation when I was confronted by a man and woman, about my age, holding hands, walking along the path towards me. My next dark thought reminded me that it had been three years since my last proper relationship. I had left my boyfriend to focus on my work and since then, I had little more than one night stands and fuck buddies to fill the void in my life. I am bisexual, I have the entire population to chose from and yet, I am still single. I really felt like things couldn't get worse. This had been my darkest day yet, since I lost my job. I was certainly feeling sorry for myself.

I ran out of the park, and sprinted a few blocks back to my building, hoping a last surge of energy would lift my mood. I was dripping in sweat and completely out of breath as I climbed the stairs to my front door. Letting myself in, I made my way to the kitchen and retrieved a bottle of chilled water from the fridge and enjoyed a cool drink before heading to the bathroom.

Stripping my running clothes off, I turned on the shower and stepped in. I enjoyed the feeling of the cool water as I washed myself and after twenty relaxing minutes or so, I turned off the water and stepped out, grabbing a towel and wrapping myself in it. I had nowhere to be that day, just like all of them at the moment but my habits were well formed. I dried my hair and moisturised my whole body before applying a little make up. I chose some tight jeans and a red vest top, then dressed and returned to my living room, almost slumping into my sofa, I turned on the TV and hopped between shit morning chat shows for a couple of hours. Boredom washed over me like a black cloud.

I dragged myself away from the sofa to prepare some lunch in the kitchen. I toasted a bagel and made a pot of coffee before sitting at my table. I instinctively opened my laptop and began to read the new headlines, all of which were even more depressing. Closing the page, I opened my search engine and began looking for job sites, a now-daily activity that had, so far, yielded nothing. I finished lunch and returned to the sofa, taking my laptop with me. I surfed the web for a while, looking at some of my favourite websites, until a pop-up advert appeared in the centre of my screen. I jumped a little as it was unexpected. The image on the advert was a cute woman, bare-breasted, grinning at me from the screen and flashing red letters spelled out 'High Class Escorts in Your Area Now!' I raised my eyebrows and closed the advert, wondering who would ever be stupid enough to click on it.

Afternoon turned to night and another day of boredom ended. I had watched three movies on TV and finally, decided to head for bed. As I lay in bed, trying to clear my mind so that I could drift off, the image of the women in the escort advert popped into my head. I found myself wondering what it would be like to sleep with men for money? I put the thought out of my head and eventually, managed to drift off to sleep.

The following morning was bright, I awoke and began my usual routine before I headed out for my run. Running gave me time to think and recently, that had been a depressing experience, but this morning, I wasn't feeling sorry for myself, I was thinking about the escort advert again. I don't think I was really considering it seriously, more that I was interested in how much money these women made and, obviously, how many men they would have to sleep with. My mind made the leap to wonder how many of those men would be abusive or generally just gross. I couldn't shake the subject from my conciousness as I completed my run. In truth, I think I was glad to have a distraction from the boredom so I decided to conduct my own online research.

Rushing through my shower, I dragged on clean jogging pants and a top. Making myself a coffee, I sat and opened my laptop to begin my research. The first thing that I discovered were that there were thousands of escorts in Chicago, some seemed to work alone and other were part of agencies. There were also lots of small brothels dotted around if you knew where to look and hundreds of websites provided contact information, listings and even reviews of the girls. I had no idea that there was such a huge sex industry out there. I easily found out that prices ranged from $50 to $300 per hour, or sometimes even more. Most girls had a menu of services with some charging extra for all kinds of strange kinks. I realised that I had been on the computer for hours and that most of the day had flown by.

I felt tired from sitting in a chair all day and moved myself to my sofa, still armed with my laptop. I found a site that offered videos and some girls had uploaded short films of themselves and even some with their clients. I was assuming that the clients had consented to that. I was also surprised that on the surface, there were respectable, professional women, running their escort business in full view of anyone wanting to see, it didn't seem to be hidden away or that anyone was really trying to hide behind very much anonymity. I clicked on one of the videos belonging to a girl named Chantel, who's bio said that she was 27 and seemed to like, regular sex and not much else. Chantel charged $200 per hour, she was very sexy, olive skinned and had very large, enhanced breasts. I noted that they were far bigger than my 34C natural breasts.

The video began to play, I felt a little strange to be honest, while I was definitely a lover of sex, porn had not really been my thing other than the occasional drunken night with someone. The film began with a slightly overweight man, with a mask across his eyes walking in front of the camera, as he moved to the side, there was a bed in shot and Chantel was kneeling on the bed, looking back at the camera. The masked man got nearer to her and I could see that he was hard already and was pulling on a condom.

Chantel, leant forward, put her hand between her legs and I could see her rub her pussy a little. The man just climbed behind her and in one slow action, grabbed his dick, put it between her legs and pushed himself deep into her. I couldn't see detail on the video but Chantel's back arched and he just fucked the shit out of her, in that position, for about three minutes before he grunted and obviously came in the condom. Chantel had been moaning the whole time. There was nothing romantic about this, but it did feel a bit more primal. Deep down, something resonated in me.

I became a little obsessed and watched a few more videos. They were all similar in tone, meant to be highly erotic for the man with little or no romance. I finally ended up watching a threesome with a man and two escorts who seemed to work together. This film was a lot more erotic and I felt myself beginning to become aroused. The familiar warm tingling feeling was spreading through my abdomen and between my legs and my nipples became a lot more sensitive.

What the hell? I thought as I turned and put the laptop on the coffee table then turned on my side. I slid my hand slowly into my jogging bottoms and across my neatly trimmed, short, bush. I watched as the women took it in turns to suck the guy's rapidly swelling cock. I let my fingers brush over my lips. I hadn't had sex in months and not masturbated for a couple of weeks and I was really into the idea right now. It felt amazing as I pushed my fingers between my wet pussy lips and dragged my juices up to my clit where I began to rub it sideways.

One woman held the cock upright as the other squatted over him, as she slid down on the dick, she moaned out as her friend started to rub her clit as she slid up and down on the cock. I pushed my fingers into my slippery pussy and gasped as I started to fuck myself. God, I needed it. I managed to push a third finger into my pussy and as I felt myself stretching a little, the feeling pushed me over the edge and I could feel the inevitable orgasm creeping up on me. I kept fucking myself and urgently pushed my other hand down my pants and used it to furiously rub my clit. I felt my legs begin to uncontrollably shake as I cried out and I felt every muscle tense in my body and my pussy spasm on my fingers.

I sank back into the cushions on my sofa and slid my hands out of my pants as I caught my breath. Wow! I thought to myself, I felt so much better. I hadn't even seen the end of the video but I felt like I had enough excitement for one day and I took a long shower before climbing into bed and falling straight asleep.

I opened my eyes the following morning and the very first thing that I thought of was the escort videos. In the cold light of day, I felt a little ashamed of my apparent obsession the previous afternoon and evening. I decided to go for a longer run that usual to clear my head. I did a few chores around my apartment, cleaned the kitchen and washed the laundry before heading out on a long run. My usual routine followed my run, a shower, make up then lunch. It was then I made my first mistake. I decided to open a bottle of wine. I didn't usually drink alcohol other than at special occasions but I figured that a glass or two wouldn't do any harm. I was wrong, I got quickly drunk and spent the afternoon drawn back to the escort videos on my laptop and the inevitable sexual release that followed.

The idea came to me later that afternoon. I tried to push it away but I kept giving it head space. What if I worked as an escort? It revolted me and fascinated me all at once. Having sex with strangers was no problem, over the years, I had met dozen of men and women in clubs. It was advertising myself and being paid for it that made it seem sleazy and having no choice about who fucked me made it seem gross. The question was, could I stand it? One thing was certain, if I didn't get some money soon, things would start falling apart. This could tide me over until I could find a job.

That evening, I came up with my second bad idea. I decided that I could create an advert on one of the escort sites and just try it once, if it didn't work out then I never had to do it again. I thought that I could live with that. I resolved to get a good nights rest, take a morning off my usual run and spend the day dealing with the practicalities if I really was going to try, and I was almost convinced that I would talk myself out of it before I went to far.

I hardly slept that night and got up early. About 75% of me really wanted to try this out, I started to fixate on needing the money and that urged me on. The first issue to deal with was where would I operate from? I didn't mind using my place but I didn't want strangers in my bed. I had a guest room and I spent the morning making up the double bed and cleaning the room within an inch of its life. I put some fairy lights up around the curtain pole and and an air freshener got plugged in. The room was comfortable and looked nice. I could use this space if I needed to. I took a lingering look at the bed before I changed into my jeans and a tee shirt and headed out to take care of the next item on my list.

I walked a few blocks to the closest drug store, I needed a box of condoms, there was no way, that if I went through with this, I would be taking any risks. I picked up a box of three before changing my mind and grabbing a larger box of ten. I Told myself it was better to have too many than not enough and some could get damaged. I was about to pay when I spotted some lubricant and picked up a bottle. I figured I'd almost certainly need it. The older woman at the checkout smiled at me as I paid, I felt a little weird, I had not bought condoms very often in my life but soon I was on my way back to my apartment.

I felt very unsettled as I got home and put the condoms in a drawer in the guest bedroom. I decided that I needed a break so I made a coffee and sat on my sofa, and put on some music. After about half an hour, my phone bleeped and there was an email from my bank, my account was running low on money. I immediately panicked, I had some savings but once they were gone I was going to be in real trouble. I made my mind up right there that I would give it a try. Grabbing my laptop, I found the site that I had earmarked for my advert and I set about writing my profile.

I kept it simple and didn't divulge any personal information apart from using my real first name, I knew that most women made one up but that last thing I wanted was to try and remember two names. It came to the list of services that I would provide and again, I wanted this to be very basic. I offered, massage, oral sex, hand jobs, vaginal intercourse and blow job. There were dozens of other options but no way would I consider anything else for my first time. My services would be $200 for an hour, that seemed right to me but I had nothing really to base my assumption on. Lastly, I needed a picture. Most women seemed to have a picture in underwear.

I went through my clothes and pulled on some white lace top hold-up stockings with a matching white thong and bra. I liked this set and they made me feel very sexy when I wore them. After many abortive attempts, I managed a nice picture, taken with the aid of my bedroom mirror. I was kneeling on the bed, with one hand just under my left breast and blowing a kiss to the camera. I was impressed that I looked great but this was my first semi-nude picture which made me feel nervous.

I uploaded the image and after adding my phone number, clicked 'save and go live' on the profile. I settled down for the evening, figuring that it would be days before anyone contacted me. I took a shower, then did up my hair again before I cooked supper. I drank another glass of the wine as I reflected on the day and decided that I would put the escort advert right out of my mind until the next day. Maybe no one would ever call.

At the end of a very relaxed evening, thanks to the wine, I figured that, as it was 11pm, I would start to get ready for bed. I turned to walk to the bathroom and my phone bleeped and flashed with an SMS. It didn't occur to me that it would be anything other than a marketing message but I felt immediate butterflies in my stomach when I read 'Hey, R U up 4 a mtg 2nite?' I froze with the phone in my hand. What would I do now?

If I had not drunk that glass of wine then my response may well have been different. I sent a reply saying 'Yes $200 for hour, come at midnight to Carson Avenue" I was going to have to go through with it. I was, by now, regretting sending the message and feeling exceptionally nervous. What the hell was I doing? I had no idea who this was, he could be a killer! My mind raced through every shit scenario before I managed to calm myself down. I took a deep breath and began to think clearly.

I had less that an hour so, I needed to get ready, that was first. I wondered what the etiquette was for clothes? Apart from the nerves, I was feeling ill-prepared. I decided on some nice panties and a bra and then just to wear my silk robe. I selected a nice black satin thong and matching bra, then pulled on my red robe and looked at myself in the mirror. I felt and looked sexy but I was really terrified. I had about 20 mins before he was due to arrive and I wondered what he would look and even smell like. I had started pacing when my door buzzer rang...he was early! I could ignore it, but then, he had my number and knew where I lived so that seemed like a bad idea.

I picked up the intercom and said hello, trying to sound calm. "Hi, it's me," said the deep voice.

"Come on up to the fourth floor," I said quietly. I realised that the voice sounded nervous too, I hadn't considered that, but then, I felt like I hadn't considered any of it properly but it was too late now.

I heard the footsteps on the wooden stairway getting louder and then the inevitable knock on my door. My heart was pounding as I slowly opened my door, for a moment, I thought I would faint. Even though I had no idea what to expect, I was still surprised. The man at the door was, I guess in his early 40s, quite handsome, with a shaved head. His eyes looked me up and down quickly and he said "Hi, I'm Steve" and he stuck his hand out to shake my hand! I knew then that Steve was as nervous as I was. I couldn't help laughing as I shook his hand.

"Hello Steve, come in, I'm Clarissa." I replied as I took his hand and pulled him a little until he stepped into the door which he closed behind him.

"How are you?" I ask, uncomfortably.

Steve coughs and looks embarrassed as he replies "OK, a little horny."

I was trying to think of something to say to break up the awkwardness when Steve rustled around in his jeans pocket and pulled out a handful of crushed bills. "200 right?" he says as he hands me the cash.

I took it an nodded. I had forgotten all about the money and I guess I should have counted it but I just put it on my coffee table. I knew I needed to take control of this situation. "Steve, would you like to come through?" I say to him as I stand in the doorway to the guest room.

Steve nodded and walked towards me as I entered the room, he was just a step or two behind me. Without turning around, I untied my robe and slowly let it fall to the floor. "Hot" said Steve and I was shocked as he grabbed my ass cheek and squeezed it. It felt so odd to let this man touch me like I was his toy.

I turned around and Steve began stripping his clothes off. I watched him sit on the bed and remove his shoes and socks, before he stood and took off his shirt. He kept looking at me without saying a word as he unzipped his jeans and slid them down. He was quite overweight but I didn't find him unattractive physically, although, obviously, we had hardly spoken more than a couple of sentences to each other before we found ourselves undressing.

Steve pulled his boxer shorts off and his cock sprang out, he was pretty hard already. It wasn't very big but looked nice. I walked towards him and put my hands on his chest and around his neck before pulling myself close to him. I was now making it up as I went along. I felt his hard dick pressing into my skin. Steve responded by putting his hands behind me and grabbing my ass cheeks again, pulling me closer, quite roughly.