A New Career, An Old Profession Ch. 04

Part 4 -- The Stars Align

Life had been great for a while, I got used to Hanna being away and I'd settled into my new life, working on three or four days each week. A steady stream of men came to my place and enjoyed my services, and with each one, I learned more and more how to really give a man what he needed. A few more weeks passed and, just when everything seemed to be working out for the best, Hanna's aunt became terminally ill, and she would be staying in Florida for the foreseeable future. This really upset me. Selfishly, I wanted her back with me and now, I had no idea how long it would before I saw her again and I started to think it was probably over for good. Letting my misery take over, I took a whole week off work and spent it feeling sorry for myself as is my tradition when things upset me.

In the end, bills had to be paid and I made my escort profile live on Friday morning. That day was pretty regular. Four clients visited, one came in my hand rather earlier in the proceedings than he would have wished, and the others all filled their condoms after enjoying my pussy for a while. That Friday marked another milestone though, one which would have been unthinkable a few months ago. I opened my second pack of two hundred condoms, in the few months I'd been doing this, over two hundred different penises had entered my body. It was both sobering and impressive, looking at the new box, and the empty old one next to each other, I wasn't sure whether I should be crying or buying myself a beer.

Saturday was unusually quiet and there were no clients by the evening. Eventually, I received an email from a guy called Danny, who explained that he was staying at a hotel and had been let down by his regular escort and would I be interested in visiting him at eleven that night. He was offering me five hundred dollars, which was way more than my usual fee and was tempting. Guys offered me extra money all the time, from an extra ten bucks for anal or, various amounts of cash to forget the condom. I always declined these offers.

I had decided at the start of this new job only to entertain men in my apartment where I felt safe and in control but what was the harm in visiting a hotel? Deciding that agreeing to new things had so far, worked out pretty well, I replied and said that I would. We made the arrangements, and I booked a cab for later. I had no idea how significant this night would turn out to be and what a huge impact it would have.

There would need to be different preparations this time and once I was showered and had my lingerie on, I chose a smart black cocktail dress, a white coat and my shoulder bag, in which I discreetly packed condoms, wipes, a small bottle of lube and a spare pair of panties. I was already on the street in the dark when the cab arrived and I took the twenty-minute journey to the hotel, arriving ten minutes early. I messaged the guy, as arranged to let him know I was at the hotel and he quickly replied inviting me up to his room, number 1104.

I felt super self-conscious waking past the concierge who held the door open and then across the lobby to the elevator, the clacking of my high heels, I was sure was attracting attention. I felt like everyone was looking at me and knew why I was there. The hotel was five star and way out of my league. The inside of the elevator was better decorated that most places I'd been in my life. I'd gotten used to my work but as the elevator reached the eleventh floor, I felt nervous, which was unusual. Maybe it was because I wasn't in the safety of my own home. Stepping out into the marble and brass adorned corridor on the eleventh floor, I made my way to room 1104 and knocked on the cream-coloured door.

Footsteps soon approached and the door was opened by a tall and fit looking man in his forties, dressed in a black robe, perfectly groomed and clean shaven with jet black hair and brown eyes. My first impression of him in those seconds was that he was a professional man and very confident. Most of my clients were what I would describe as regular guys, who came in varying degrees of ages and sizes, with a variety of personal hygiene standards. I'm non-judgemental and respected my clients in my own way but this man struck me as being of a different league.

"Come on in, Cara." He said warmly and stood back from door.

Smiling, I entered, and he closed the door. The room was like a Hollywood movie set to me, it was like a palace, a giant white, four poster bed, huge windows looking out on the cityscape and plush green carpet. Paintings adorned the walls and a door led to a bathroom that, from the outside, looked like it was solid marble.

"May I take your coat?" Danny said.

"Oh, Yes, thank you." I replied as I put my bag on the floor and he took the coat from my shoulders, then hung it on the hook near the door. I picked up my bag.

"It's good to meet you." I said. "Wow, this is such a lovely hotel."

"I like to stay here when I'm in Chicago on business." He explained, then he turned and picked up an envelope which he handed to me. "Speaking of business, shall we get this out of the way?"

"Thank you." I said and slipped the envelope into my bag.

The guy seemed OK to me, and I was starting to feel more comfortable.

"Shall we sit?" Danny asked.

"Sure." I replied and followed him over to one of two armchairs and sat, crossing my legs and enjoyed the unusual comfort of the expensive leather chair.

Danny pulled a bottle from a chiller next to his chair and poured two glasses, handing me one of them. "Champagne?" He said.

I thanked him, took the glass and resisted telling him that I was more of a bar and beer girl, but I did like the occasional glass of champagne and given that I was in such a cool hotel and earning a whole days pay from just one client, I was in no rush. Also, there was no doubt that this would be an expensive bottle, so, why not enjoy it? This was already very different to my usual clients.

"So where are you from? Where's home?" I asked him.

"I'm based in New York, but I travel a lot." He explained. "I visit Chicago often."

"What do you do?" I enquired.

He smiled and his answer was a little vague and cagey. "Oh, I work in security for a large organisation."

I was thinking that he really didn't do that job and that Danny probably wasn't his name but hell, who cares, I mean, Cara wasn't my name!

He asked me about myself, and I explained most of my story, leaving out the personal bits and my choices for being an escort. He was quite good company; conversation was easy, and we chatted for about half an hour or two glasses of champagne. He was now focussing more on my chest and legs as the conversation was progressing and so, I suggested that I use the bathroom to freshen up.

The bathroom was as impressive as the rest of the room and I took off my dress, made some adjustments to my hair and then checked my make up. I completed my usual trick of putting a small amount of lube in my pussy and finally, was ready.

Danny was still sitting in the armchair when I returned from the bathroom and he looked around to watch me, slowly walking towards him, in my black lace bra, suspender belt, stockings, with a G string over the top and high heels to finish the look. Making my way across the room, I walked back to the chair and sat, this time, I sat upright and kept my legs slightly apart. He didn't notice that I was holding a condom in my hand, I slipped it discreetly behind me on the chair.

"Oh, damn!" Danny said. "You're fucking hot!"

"Thank you." I replied. "I'm also, all yours to play with."

"I like your approach." He said, standing up.

He walked the couple of steps towards me until he was in front of my knees, and I looked up at him as he stared back, untying the belt of his robe and letting it fall to the ground. When I looked down, my breath was slightly taken away. The cock that hung between his legs was enormous. It wasn't even semi hard, and it was giant. By far, the biggest one that I'd seen with my own eyes.

I looked back up at him and the look on my face must have betrayed my feelings on the subject.

"It's big, right!" He laughed.

"Oh yeah!" I answered. "No question."

There was no way of backing out anyway so I would have to accommodate the huge dick, although I was genuinely worried that it wouldn't be able to fit in my pussy, or that it would hurt. For now, though, Danny got to his knees and pushed my legs apart. Having learnt to just go with what I feel like the guy wants, I also slid my butt towards to the edge of the seat, lifted my feet and hooked them over the arms of the chair, spreading my lace-covered pussy in front of him.

Danny spent a while stroking my stocking clad legs before focussing his attention on the place where most guys end up very quickly, that small, wet place that brings them pleasure. He began to gently rub my pussy through my panties and actually managed to hit my clit as he stroked, which felt nice.

"Does that feel nice?" I whispered.

"Yeah." He replied simply, acting like he didn't want to be distracted in any way from that area between my legs.

I was surprised to find that his expert stroking was actually making me a little wet and soon, there was not getting away from the fact my pussy was up for the action. Danny finally rendered my panties fluid soaked and pulled my G string to the left of my pussy and looked at my exposed labia. Then, he continued his stroking, his finger quickly coated in lube mixed with my pussy juice. I was surprised to find myself genuinely softly moaning as he worked his finger around my clit but let out a loud groan as he sank his long finger into my pussy.

He smiled and still remain silent as he began to finger fuck me. He knew exactly what he was doing and swivelled his finger around to find my G spot while I began to pant as he pleasured me. Once he put his head forwards and began licking my clit as his finger continued its work inside me, I came to the realisation that if he continued for too much longer, I was probably going to cum and there would be nothing to be done about it. Continue, he did, and before long, he wriggled a second finger into my pussy, and I squealed, surprised at the pleasure I was experiencing.

By now, I was bucking my hips and fast approaching the peak and he knew it, he carried on licking my clit which was working me into a frenzy.

"I think I'm gonna cum if you keep doing that." I panted.

He didn't stop what he was focussed on and didn't speed up, just kept going, pushing me closer and closer. Another minute and all doubts were gone, I was actually about to cum with this man and I warned him. "I squirt when I cum!"

He didn't slow down or speed up, he just carried on. The orgasm started gently, I felt it creeping up from a firm tingle deep in my pussy to the start of the clamping and spasms of my muscles that signals the peak of the event.

"Oh Fuck, I'm cumming!" I managed to blurt out before falling silent and feeling my whole body go into spasm and shaking with the delightful burning sensation between my legs. Every muscle in my body tensed up, a feeling that, as was usual for me, was released only as the gush of fluid was expelled between my legs, leaving me in a trembling heap.

Danny stopped licking but kept his fingers inside me as I came down from the spasms. I'd squirted into his hand and felt my own fluid dripping from my thighs.

"Wow, you really did cum!" He said, sounding surprised.

"Fuck, Danny!" I said. "Yeah, you really made me cum good."

That was true, he really had. That was one hell of an orgasm that he spent around twenty minutes giving me and my first with a male client. In fact, the amount of orgasms that men had given me in my life could be counted on two hands. I wasn't complaining, I was being paid and got to cum, what could be better than that?

Danny stood up to reveal that his giant cock was now semi-erect. It was time for me to repay the favour. Putting my legs down on the floor and sliding forwards, he stepped towards me, and I took his thick cock in my hand and for a moment, gently stroked it, feeling its size, weight and power. Holding it towards me, I opened my mouth wide and slid the end in. No way would I be able to deep throat this guy, but I did suck his cock head while stroking his shaft, making sure to swirl my tongue around his manhood as I felt it start to swell in my mouth.

My technique began to work and slowly, I felt him hardening in my hand and mouth. I love the feeling of a cock getting hard because of me but I took my time, taking around ten minutes to bring him to a full, rigid, erection. Danny groaned and moved his hips as I worked on him and at one point, I thought he might just give in and cum in my mouth, which would have been fine with me, but, once he was fully hard, he stepped back and I got a good look at the twelve-inch, thick dick that stood ready to penetrate me.

"You wanna fuck me now?" I asked.

"Think you can take it?" He asked with a cheeky grin.

"Only one way to find out!" I replied and reached behind me, found the condom and tore open the packet. Danny moved forward and allowed me to roll the condom down his cock, it was hard to get in on a dick that was so big, but I managed it and then sucked him over the condom, ensuring it was slippery. Once I was happy that it was on properly, I lay back and put my legs over the arms of the chair and Danny knelt in front of me, the height of the chair was perfect.

Dropping my hand between my legs, I rubbed my pussy, smearing my own slippery juices all around my pussy as he watched. Finally, I used both hands to spread open my labia, so he could see my pussy opening and said. "You wanna put that huge cock in here?"

Danny needed no further encouragement and held his cock in his hand, slowly stroking it. Pressing it forwards, he gently slapped my clit with it, making me grunt as the little shots of pleasure ripped through me. Spending a little time rubbing is cock head around my labia, as if he were really enjoying the feeling of spreading more of my juices around, he soon put the end of his dick in my pussy opening and held it there.

"Stretch me slowly, baby." I whispered. "I wanna feel it open me up."

He did as I asked and gently pressed. I released my pussy lips from my fingers and gripped the chair while letting out a soft squeal as his cock head penetrated me. It was easily the biggest thing that had been in there and it really did open me up, I felt every contour on his cock head as it pushed its way inside.

"Oh, my fucking God! You're massive!" I wailed as he continued to enter me slowly, his cock creeping its way in, pushing open my tunnel as it went until, with me almost screaming, his balls touched my ass as his cock head reached the deepest part of my pussy."

"Oh fuck, I can't believe you got that thing inside me!" I whimpered.

Now, he did what I was there for, he started fucking me. And oh, shit, he really did fuck me. Using slow strokes to start with, he took me, sliding that cock in and out, each time, stretching my opening for him. His cock hit every single sensitive place inside my pussy and I soon I was begging him to fuck me harder. He needed little encouragement, and his cock was slamming in and out of me as I gripped the chair and met his thrusts. I usually didn't cum from penetration until some clit action was included but now, I experienced a small, fast orgasm as he fucked me, I didn't squirt but I felt my pussy clamping down on him. It happened three times.

I must have been so tight on his cock that I was convinced this would be over quickly and I prepared myself for his imminent cum, but no. Danny was in full control and grunting lightly as he fucked me with significant power for another minute until he suddenly pulled out, grabbed my hand and pulled me up. He sat in the chair, and I quickly turned my back to him, squatted over him and guided his cock back inside me. He went in even deeper like this and I used the arms of the chair to steady myself and rode him hard and deep, squealing as his cock bottomed out. Danny had been inside me for some time, way longer than an average client and he showed no signs of cumming. I rode him for several minutes, having another of those satisfying vaginal orgasms as I did my work.

Danny again, lifted me off his dick and asked me to bend over in the chair, which I was happy to do for him. He forcefully buried his cock back in my dripping pussy, this time, showing no mercy, he grabbed my hips and fucked my pussy hard making me squeal with every thrust. He began groaning and fucking me so hard that his balls slapped my clit, but then, I began to feel that tell-tale sensation of his cock getting harder and the head swelling up just a little. I was used to experiencing this very often as men approached their impending ejaculation.

He managed about ten more hard thrusts, which increased in force but reduced in speed and began to grunt hard, then, after one hard, deep final thrust which he held inside me for a couple of seconds, he pulled his cock out and urgently told me to kneel.

As I spun around to face him and dropped to my knees, he was ripping the condom off and began jerking his cock in front of my face. Precum was draining from the little hole in his cock head, and I leaned my head back, looked up at him with my eyes wide, moved my head in front of his dick and opened my mouth.

Danny began to grunt and then yelled out as he came. A long rope of cum splattered over my face and hair, the second went right in my open mouth and the third and remaining deliveries, slithered out and landed on my chest, right between my breasts. Grabbing his dick, I slid my mouth over the head and sucked hard, receiving a mouthful of his remaining sperm. Once I felt him start to go soft, I withdrew his dick, kissed the tip and let Danny sit.

"Fuck!" He exclaimed. "That was amazing. I'm so happy Ella couldn't make it. Fuck, Cara, you are one of the best!"

I was still kneeling but rubbed his leg as he sat. "You're welcome, I'm glad you enjoyed me and my God, you have an amazing cock! I really enjoyed that too."

Quickly, I excused myself to go to the bathroom, taking the condom with me.

Needing a moment to recover, I sat on the chair and used my wipes to clean the sperm out of my hair as best I could, and then I cleaned the rest of me, got as much of the cum out of my bra as possible, changed my panties for the clean and dry ones and put my dress back on.

By the time I went back into the room, Danny was dressed in his gown again and we said goodbye. He promised to call me the next time he was in the city. I left the hotel and this time, when the concierge opened the door for me to leave, I realised that he really would know why I was there. He had let me in late at night and I'd been there for just a couple of hours. Why else would I be there?

A short cab ride later and I was in my shower and soon in bed. My pussy ached a little from the next level fucking it had just taken but it had been an enjoyable experience and I felt pleased with myself for pushing my boundaries.

I guess at this stage you're wondering why that night was significant. You could surmise that it was because Danny had the biggest cock I'd managed to take, or that he was the first male client to make me cum but, you'd be wrong. What actually made it so significant is what happened the following day.

Sunday was supposed to be a day off but when I woke, I discovered that I'd forgotten to change my profile settings on the escort site and I was showing as available. I'd also gotten a message from a guy asking to visit me as soon as I was free. I could have declined but I agreed to see him and, just before lunchtime, I was letting him in to my apartment.

John was a short but intense man, large but muscular, didn't say much and was soon naked and laying on the bed. After a short massage, I was kneeling between his legs, with his below average dick in my mouth and he was steadily getting hard. It wasn't very long before he was throbbing in my mouth and bucking his hips upwards. I found that slowing down, and sucking more firmly did the trick at this stage and maybe twenty more sucks had the guy on the edge. As he began to grunt, I felt him tense up and I held my head still, awaiting his climax but I'd inadvertently stopped too soon and when he kept grunting and straining, I sucked him up and down once more, hoping that would be enough to push him over. He definitely seemed happy to finish in my mouth and hadn't asked to fuck me.