A New Career, An Old Profession

I paced around my apartment with my cell in my hand, my mind spinning out of control. It was 11:10pm and just as I decided that this guy was a time waster when the sound of my door buzzer almost made me drop my phone. Fuck. I was going to have to deal with this.

I picked up the intercom. "Hey." I said.

"It's urr, Gary, we have an appointment." Came the deep voice on the other end.

Great! I thought. My first client is called Gary!

"OK," I replied. "Apartment 2, black door to the left of the stairs at the top. Come on up."

I pressed the door release and hung up the intercom and began to panic. Shit, what was I doing? I was about to be fucked by a total stranger. I had less than thirty seconds to get my shit together.

The thirty seconds ran out and I had no time to think any more because I soon heard footsteps coming up the concrete stairs. I waited until I heard them reach the top and approach my door and I took a big breath and opened my door a crack, peering out, making sure my neighbour couldn't see me open the door to a man in my underwear. The silhouette of a tall man approached the door.

"Come in." I said as I opened the door enough for him to step inside. Once he passed me, I quickly closed the door and turned to face him.

I had no idea what to expect of course and I was faced with a tall guy, probably in his 40s. He was dressed in a plain white shirt, black trousers and a leather jacket. He had a kind face, greying brown hair and was perfectly clean shaven.

"Hi." He said, slightly awkwardly as he looked me up and down.

For a moment, I wondered why he wasn't looking at my face and then of course, I remembered that I was dressed in 'fuck me' lingerie and that's exactly why he was here.

"Hi, Gary. It's nice to meet you. Are you OK?" I asked, desperately searching my head for the correct formalities in such a situation.

"Yeah, I'm good, thanks. I was staying in a hotel and, you know, felt horny and so, well, here I am."

"Oh, well, I think I can help you with that." I said, surprised at the swiftness of my reply.

He looked me up and down again and raised his eyebrows. "Yeah, I'm sure you can. You're really hot!"

"Thank you." I replied, "Would you like a drink of anything? I have water, juice or even a little wine?" As soon as the words left my mouth, I cursed myself, I offered him a drink? He wasn't there for that.

"Oh, urm, no, thanks, Cara, I'm fine." He replied. "Oh but, ur, I have this for you." he pulled his hand from his pocket and handed me five new $20 bills which had clearly just come from an ATM.

I took them and thanked him, then put the money on top of the bookcase near the door. It would only be later that I understood the significance of that moment, when I took that money from Gary, because then, he had bought me, at that moment, I was no longer unemployed, no longer a TV assistant, no, I was a prostitute and I'd joined the world's oldest profession.

There was nothing else to do except offer the service that I'd been paid for. I sort of zoned out a bit.

"Come with me, Gary, we can go somewhere more comfortable."

I walked towards my spare room and opened the door. I held it open for him as we went inside, and I closed it behind him. Gary looked around and kicked off his sneakers, then hung his jacket on the hook on the back of the door. I watched him take off his shirt and then he turned to face me, and I let instinct kick in. I suddenly became aware of my heart thumping in my chest and took a few discreet, deep breaths and managed to regain my composure.

I took a step towards him. "Let me help you with that." I said as I grabbed the waistband of his pants, undid the button and then unzipped the fly. As his pants began to fall, I pushed them down to his feet. Having no idea what I was really doing and feeling totally out of my depth, I went with what felt right and I knelt in front of him and pulled the front of his grey boxers' forwards and slid them down to his feet. When I looked up, in front of my face dangled his semi-erect cock. It was shocking to see it this close, a stranger's cock, in front of my face and soon, it would cement my employment as a prostitute.

It was an average sized cock, from my own limited experience and he'd been circumcised so it looked smooth and neat, the opening on the end seemed larger than I was expecting.

Instinctively, I slid my hands up his thighs and back down to his knees a few times and even that light touch made his cock rise up slightly higher, then I stood up, running my hands up his hairy chest as I did so.

"Why don't you sit on the bed?" I suggested.

Given the enormity of what was happening to me, there was a part of me inside that was so happy to see Gary bend down and take his socks off. Can you imagine, having sex with man who still has his socks on? Eww!

Gary sat on the bed naked, and I walked around to stand in front of him. Smiling, I reached behind my back and unhooked the bra and slowly dropped it over my chest, exposing my small breasts for him to enjoy. Then I hooked my fingers in the sides of my thong and turned my back to him, like I'd seen in films, and stuck my butt out towards him as I pulled my thong down to my ankles.

Before I could straighten up, I felt Gary's hands grab my butt cheeks. He let out a long breath as he massaged them, he pulled them apart and held them for a moment which felt like he was looking at my ass, which was a little weird, but weird was the new normal! After a minute of him enjoying my butt, I turned to face him and knelt. He grabbed both my titties straight away and awkwardly fondled them. He pulled gently on my nipples a few times which felt OK and then grinned at me, shuffled back on the bed and lay back. His cock now pointed vertically to the ceiling. I looked at it and I knew in a few minutes; I'd be sitting on that cock.

Crawling my way up onto the bed next to him, I got on all fours and turned so my butt faced him and then wrapped my fingers around his dick. It felt so strange to touch a strangers cock like this. He groaned a little as I touched it and then I felt his hand on my ass but this time, he slid between my legs, and I felt him stroking my pussy lips. Immediately, my own juices, mixed with the lube, coated his fingers and he spread the slippery mixture around my pussy. That gave me confidence that I was wet enough for him. Touching my pussy was enough to make him fully hard and I decided to get it over with.

I turned around and reached into the nightstand and pulled out one of the condoms and turned back to him. He put his arms by his sides and watched me rip the little packet open and pull out the thin rubber ring. Carefully, I turned it the right way up, leant forwards and placed it gently on top of his cock and unrolled it down the length of his shaft. Then I leant down and opened my mouth and sucked him. The rubber did not taste good, but I wanted to make the condom wet, so it went in easily.

Gary groaned as I bobbed my head up and down a few times and then, I sat back up and, suddenly feeling very nervous, rushed to finish my work. I straddled him and felt his cock pressing between my legs. He put his hands on my knees and watched me reach down and between my legs. Pushing myself up a little, I gently lifted his cock, so it was pointing upwards and found my wet opening. Closing my eyes and taking a couple of breaths, I sank down and gasped as I felt my first client's cock, penetrate into my pussy. I'd done it, he was inside me.

Gary pressed his head back and moaned as he felt his cock slide into my warmth. I began my work of riding him slowly, rolling my hips forwards and backwards, working him in and out. He began to thrust up a little as I moved, and I started softly grunting each time his cock went in. Picking up the rhythm, I pushed down a little harder each time and began to massage my own tits and roll my head around as if I was being seriously pleasured. In my head, I figured this would take ages but in fact. Gary began to thrust upwards quickly and started grunting. Fuck! I thought, he's going to cum already.

A few more thrusts and I felt him get harder, so I pushed down as he pushed up and he held me in place while he ground himself into me.

"Fuuuckkk!" He said as I felt his cock throb inside me and he came, filling the condom with his cum.

I gasped loudly for a few seconds. Just like that it was done, I'd helped him cum, it was over. Well almost. I reached between my legs and held the condom in place while I lifted myself off him and quickly checked to make sure all the cum was contained, which it was. I got off him and off the bed and over to the nightstand to get the baby wipes and towel. I unrolled the now-warm condom and wrapped it in a tissue and then discarded it into the bin and used a wipe to clean off his dick and the surrounding area.

When I was finished, he sat up.

"Thank you." he said. "That was amazing."

"You're welcome, any time." I replied. Gary quickly got dressed while I put my thong and bra back on and no sooner than he was dressed, he said he had to leave.

I walked him to the door and gave him a hug and he left.

I expected to cry, or throw up, or both after my first one but in truth, I felt fine which was strange in and of itself. Gary had been friendly, clean, felt fine and lay there while I rode him. It didn't hurt, nothing had gone wrong, and I just earned the easiest $100 of my life. The only physical evidence of the liaison was a wet feeling between my legs and a condom full of sperm in the bin. In fact, Gary had been in my apartment for just 20 minutes. But the fact remained that I was now a prostitute, and I definitely felt a bit dirty if I'm honest, even ashamed when I really thought about it. I had to tell myself that this was something I'd chosen and not been forced into. The feeling passed and that night, I managed to sleep deeply.

The Saturday morning passed by in a haze. I'd showered the night before, washed the sheets from the spare room, the lingerie I wore and emptied the trash to remove any trace of my encounter with Gary. Although it was an extreme step in my life and undoubtedly weird, I still felt kind of fine about it and I decided, in an instant to treat this like any other work I did and to remove the emotion from it. I would do a good job, work hard and face the world. That's it. I logged into the escort site and double checked that my page would become live at midday. Then I showered, fixed my makeup and hair, just in case I got a client with short notice. I wouldn't be caught out again.

In my head, I imagined that my Saturday afternoon and evening would be a constant stream of messages and visitors and I mentally prepared myself for that. In all reality, I was bored all afternoon with no calls at all and I began to wonder if my client the day before was a fluke and this really was another waste of time, but I was new to this and I would soon learn that nightfall brings out the horny men. I never knew the name of my second client. He didn't say and I didn't ask, figuring if he wanted me to know, he'd have told me. Mr Mystery sent an SMS at about 8pm asking for a meeting for sex right then as he was in the area. I followed the same method as with Gary the night before, although, I was far more nervous as I waited for him to arrive but, like the night before, I made up my mind to be professional and do a good job. Pretty soon, I opened the door to tall, skinny, silver haired man who was probably 70 years old, or thereabouts. He was clearly nervous as he greeted me and immediately thrust a handful of screwed up bills in my hand.

I was about to get a lesson in not making assumptions about clients. I had it planned out of course, I knew what I'd done with Gary the night before and I would do exactly the same with this man, he'd enjoy it, cum and leave happy. But no, that's not what happened at all. My Mystery seemed to be a little less relaxed as we went into the spare room and, to help him relax, I took his jacket off and hung it on the hook for him, then I pushed myself close to his right side and began to unbutton his shirt. The guy never tried to touch me, he just stood still while I took off his shirt. I felt bad for him as he was obviously nervous and I figured, once I got him undressed, I'd lay him on the bed and massage him maybe, stroke him, or something to help him get in the mood.

Dropping to my knees, I unbuttoned his black trousers and realised that he was rock hard already. Pulling down his boxers, I was presented with a fully hard, below average size dick, pointing to the sky. Still, he had not laid a finger on me and when I looked up to make eye contact, he was staring up at the ceiling. Still not really understanding what was going on, I pushed on with my work and intended to tease him a little bit and slid my hand up his thigh, allowed my hand to slide around his cock shaft, eased it a little more horizontal and then opened my mouth. I was really only going to suck him for a few seconds anyway but, as I slid my mouth over his cock head, the man made a quiet squealing noise and before I'd slid him all the way into my mouth, he shot out a jet of hot, salty cum which took me by surprise as it hit the back of my throat, making me choke and pull my mouth off his dick which then splattered the remainder of its load over my neck and chest. Rapidly followed by the mouthful of cum which spilled out of my gasping, coughing mouth.

"I'm, sorry about that." The man said as he bent forward and pulled his boxers and trousers up, tucking his flaccid, cum dribbling cock back into place before I could even offer him a towel.

"Hey, don't worry, Baby." I said as I got to my feet, feeling his cum dripping down my cleavage and wiping my mouth with the back of my hand.

In a matter of seconds, his shirt was buttoned, his jacked on and he thanked me, walked out my spare room, out the front door and was gone. He had been in my place less than 10 minutes. Obviously, the poor guy had a premature ejaculation problem but I wish he'd told me so we could have taken it slower. I made a mental decision to try and tailor my approach to men, if I could figure out what they needed, which seemed like a big task. I thought of it while standing at the bathroom sink washing the cum from my brand-new bra before taking another shower and returning to find two new messages asking for bookings. I arranged one for 10pm and another for 11:15pm and got dressed into another set of underwear.

Mark, a younger guy in his thirties, quite good looking actually, which was yet another aspect of the work that I'd not considered, was my 10pm and he arrived right on time in my apartment and was quite chatty as he paid me and accepted a glass of water. He was the first guy to engage in a conversation with me and asked me if I was a native of Chicago and seemed relaxed. He also complimented me on my hair, said I was cute and also sexy. We started off like the other two and soon, he was nice and hard in my mouth but as I sat on the bed, he pushed me back until I lay flat with my feet on the floor, and he knelt between my legs. I soon felt him pull my white thong to one side and then he proceeded to lick my pussy lips before repeatedly pushing his tongue in my hole.

So, this was new, a strange guy eating me out. It did feel nice, made me a little tingly down there but his technique lacked, and he was too fast, too rough and totally ignored my clit. I moaned for him and bucked my hips a little bit as he lashed his tongue around. Soon, he stood up and I rolled over, grabbed a condom and then sat in front of him as he stood and rolled the condom down the shaft of his hard cock.

Mark smiled down and said. "Can you get on all fours?"

I nodded, turned myself as I got fully onto the bed, crawled forward and pushed my ass up in the air for him. Mark got onto the bed behind me, pulled my thong even further to the side and then, with great care, rubbed his cock along my pussy lips until he was perfectly lined up and then, with a little moan, very slowly sank himself all the way in.

"Oh, fuck, Baby!" I groaned as he bottomed out.

Mark grabbed my hips, right on the waistband of my thong and began to fuck me, slowly at first but quickly picking up his pace until his balls slapped my clit and our bodies smashed together with that satisfying slapping sound. Doing my best to let him enjoy it, I moaned and pushed my ass back to meet his thrusts as he used his hands to pull my hips towards him, leading to a nice rhythm and a deep fuck which went on for about ten minutes until he sped up for a few thrusts and then, with a huge grunt and a loud... "Oh Fuck!" He slammed his dick in one last time as he forced himself in as deep as possible and held still, repeating, "fuck, fuck, fuck," as his dick twitched and pulsed as he came into the condom. I felt him grab the condom and pull his cock out almost immediately and I swung around to see him red faced and catching his breath.

"Hey, lay down and take a rest." I said and he lay flat on the bed with his arms at his side.

"Fuck. That was really good. I totally needed that." He replied.

I giggled and grabbed a tissue and the cleaning wipes, knelt next to him and removed the condom, then cleaned his cock, squeezing out the last of his semen and making sure he no cum had leaked onto him in the process.

We said our goodbyes and he left. Again, not a bad client, quite cute and I found the sex easy. I'd never thought of sex as a big deal and never had emotional attachment to it with men if I was honest. I enjoyed it, sure, sometimes a fucking lot but I had now had sex with 2 strange men, and another had blown in my mouth, all in the last day or two and I surprised myself how fine I was with it. With only fifteen minutes until my 11:15pm, I freshened myself up and was ready to greet John when he arrived.

Pretty sure that John was a fake name which made me laugh to myself. It was something about the way he said it. I didn't mind but I would have never outed a client, so he was safe with me, even if he didn't know it. Once in the spare room, John had a particular request, another first for my new career. He explained that he was addicted to porn and wanted me to suck him off while he watched porn on his cell.

And soon, John was laying naked on the bed, watching some girl-on-girl action while I knelt next to him and sucked his small cock while massaging his balls. Learning my lesson from earlier in the evening, I wouldn't be caught out, or surprised when John came. He lasted quite a while though and it was almost a full 20 minutes before I felt his cock head swelling and then, he started to shake and grunt as I slowed down a little and sucked him hard. He didn't cum with a huge force, rather, I felt his cock pulse and my mouth suddenly filled with his warm, slippery cum, which I allowed to drool out on his cock as I continued to suck, and his cock refilled my mouth with diminishing amounts until he was spent. He put his phone down on the bed and lay there while I cleaned him up and then, with a simple thanks and bye, he was gone.

Sunday went much the same way, but I only saw two guys but, when I woke on Monday, I decided to take the day off and take stock of how I felt. That much sex does make you tired and my abdominal muscles felt like I'd been working out all weekend. Emotionally, I felt fine, perhaps a little bit anxious at the ease with which I'd had sexual encounters with so many men, plus, I had earned $800 which was more than I'd have earned in a regular week. This made me feel even better, like I was in control of my own destiny. There was no doubt in my mind that I would carry on with this line of work for now and that meant some more practical considerations and I hit the laptop. I would clearly need more condoms, a lot more and I found a site to buy them in bulk and soon, 200 were on their way to me. That made me pause for thought, 200 different guys fucking me! Next, I figures that I was also going to get through more underwear. If I got them covered in cum, then I would need a change between clients and the panties would be betting very wet and so, I bought several new sets of sexy lingerie. I quite enjoyed imagining myself wearing them all with clients. I was also going to need to stay fit and with some money now coming in, I renewed my gym membership and vowed to run every day I could.