Chapter 1

About the story...

Jessica is a 52 year old woman, who takes us back in time to when she was 42. Life hadn't been easy for her; her husband had abandoned her and her son early in life ... for a younger model of course.

Darren was her son, she would do anything for him ... she doted on him. One thing she was certain was, he was going to get a good education ... make something of himself, he was clever and intelligent and had secured a scholarship at university ... it was expensive, but she was determined to see to it his fees were always paid for, but things start to get bad. She loses the job she had, and at 42, was finding it difficult to find work and to make ends meet ... but by chance, she over hears some students talking at a coffee shop, at first the idea that pops into her head is absurd ... but is it, and more important ... can she?

I was now fifty two years of age ... It was ten years ago that I decided on a "Career" change ... well if you could call being a prostitute a career change ... ten years ago that made me forty-two.

It wasn't that I up one day and said ... hey I'm gona be a prostitute ... nothing like that. In fact it took me a long time to make the decision and go for it.

So why did you? I hear you ask.

Well this is my story, and my decision. Now I know some out there will say, it was never a good reason to do it, there were other ways to fix the problem. Well at the time I could not see any, and things had become desperate ... and desperate times called for desperate measures ... it wasn't as if I was gona kill someone.

I was forty-two years of age, a mother with a son, and a husband who had abandoned us for the inevitable younger woman, he just came in one day, said sorry, but he had found someone else, someone he loved ... and needed her in his life. Now that was rather funny, he had said those same words to me some twenty odd years ago. Now we had ... or rather I had an eighteen year son at university, Brad had up and off, leaving me with a house mortgaged up to the hilt ... and numerous other debts, one of which was university fees for Darren ... and Darren was my top priority ... he was a good kid, intelligent and doing well, he worked hard at study and working jobs as well to help with the fees which were necessary for his continued education ... I was determined no matter what, to see that he ran the course.

I could see from the start that I was on a loosing battle, a slow downward spiral, struggling to make every hundred bucks stretch to two hundred bucks.

First the bank foreclosed on the house. I took with me as much furniture as I could and settled into a one bedroom flat, that had seen better times ... it gave me breathing space and no more. Fate dealt me another blow when a faltering economy found me being laid off my only source of income ... having to rely on a government subsidy.

I just had to find another job ... but at forty-two it wasn't that easy ... even some more experienced and academic people were finding difficulty ... so what chance me?

It happened one morning, I was in "Grannies" coffee bar, a coffee bar that was well frequented because of it fine coffee, and huge muffins and scones. It had been a daily practice of mine to go there, grab a coffee and a muffin. Open the local paper at situations vacant, and as I sipped coffee and munched on a muffin I'd circle the ones I thought would be suitable.

There were three young college students in the booth next to mine, I wasn't really taking in with what they were saying ... most of it was girly talk, and lessons at school, but something made my ears prick up, an exclamation.

"You what ... you didn't ... did you?"

"Shhhh" said one of the girls keep it down.

They huddled around the table, trying to close out the conversation, and chatting in hushed voices ... but it was still loud enough for me to hear.

"So what you're saying Elisha is that you actually did it ... did it for money ... right?"

"Yes ... yes that's right I did it for money"

"But ... but ... that makes you a prostitute ... I mean sex and money is equal to prostitution ... isn't it" Replied one of the others.

"Yeah so, we do it on campus with the guys for free ... why not take a guys money ... I mean if he's willing to pay for it ... and besides I need the cash, got all these school fee's to find" Elisha's response

"Whow, so what ... I mean how ... where ... god I don't believe it?"

"Oh it's not that bad ... it's not like I'm full time at it ... just a little here and there ... I'm not going to make a career out of it"

"I go to the red light district ... you know down by the dock area ... ships, and seamen ... horny pricks looking for a quick shag, and prepared to pay for it"

"Yeah but shit, it must be kinda dangerous down there?"

Elisha gave it some thought, then said "Well I guess it could be ... but there are lots of other women around who would come to help you if need be I suppose"

"There are quite a few from campus do it, I'm not the only one you know ... Heather Purdy put me on to it ... she does it ... along with some of the others"

"And what you just go on down there and hang around until a guy taps you up?"

"Yeah pretty much so"

"And where do you go to ... um ... you know ... er do the business?"

"Well if he doesn't have a car, we use little back alleys, or one of the shop doorways ... it's pretty dark away from the main area, and a shop doorway is ideal ... I mean we are only talking quickies ... longest I ever had was fifteen minutes ... you know in, out ... ca-ching, money in the till"

"You do wear protection don't you Elisha?" said another quite concerned

"Nah I just let the guy cum there ... of course I wear protection silly ... I'm not that stupid"

The conversation continued to roll on, and my thoughts began to drift. What if that was me. I tried to put myself in her situation ... short skirt and all, the guy approaching, we go to that shop door ... I'm lifting my skirt ... pulling down my pants ... he's ... he's.

Oh god no ... god no, I just couldn't do it.

I gave myself a mental slap, get back to job hunting Jessica, and find a proper job.

The girls had finished their coffee and also their ... um very interesting conversation. They gathered up their school books, hugging them to their chest and began to leave.

I watched as they passed my booth, I'm not sure if they were aware that I had been privy to their conversation ... now which one was Elisha.

I returned to my situations vacant

I circled ten that looked promising ... I rang them all for an appointment and managed to get two, two out of ten

I really thought I'd stuck gold with one of them, it seemed I was a dead cert for the position ... they were already talking as if I was working for them. The bomb shell came later when they rang, said how sorry they were, but the girl after me just ... and they emphasised the just ... had a slightly higher qualifications, but they would like to retain my name and details for future reference.

Great yes, but that didn't solve my present problems. Now it looked like I was back here tomorrow.

Three more days of the same thing ... nothing, not a sausage ... even sausage on the menu was looking good ... the edible ones you dirty minded buggers.

Now I was worried, Darren's school fees were coming up fast and I just didn't have the money in my account to cover them ... my mind went back a few days ... that college student ... what was her name Elisha ... the time had come.

I needed to see the area for myself, and that night I jumped into my trusty old Honda and did a slow drive by. Oh there were girl's alright ... short skirts ... low tops. All the gear that oozed sex, shouting out I'm for sale ... I'm for sale come buy my wares.

I found a parking spot near by, and observed the proceedings ... how they all dressed, and how they reacted. They certainly seemed a friendly bunch, chatting with each other, the occasional, laugh, whistling and shouting at any guy who passed by.

The big question was could I ... could I fit in, doing what they do ... I just wasn't sure.

When I got home the first thing I did was check out my wardrobe ... what did I have that was sexy ... answer, nothing ... it was all middle age dowdy. Not that there is anything wrong with dowdy ... but hey, I was going into competition here ... I needed something ... sexy.

Naturally, money was the thing, and buying a new and different wardrobe was going to cost, but fortunately we had a cheap store for all that, yeah second hand maybe, but if you dug deep there was some good bargains in there.

Now my bank balance was right on the border ... as they say "Shit or bust"

I'd always been a tall leggy blond ... I still was, but perhaps a little more of me compared to twenty years ago ... but my height carried the day, I was still in proportion.

I stripped naked and started to build ... I fitted into everything, no problem, but what I did find hard was seeing myself in the mirror ... showing all that leg ... and breasts bursting to get out of the push up bra I had purchased ... well if nothing else I looked the part ... I would fit in well down on the street ... god I hope none of my neighbours see me. The thing was I wanted to keep pulling the hem of my skirt further down ... I felt I was showing far too much leg ... any further up and Id be showing my knickers ... but isn't that what the guys wanted to see ... my knickers ... hmm and the rest of course ... the outfit did show of my assets, and the curved contours of my shapely body ... looking in the mirror I felt quite proud of myself ... I still looked good ... well I thought I did ... it was a question of would the guys ... or do you call them clients, I seem to remember somewhere the word john was used ... well would the john's think so?

Going down there and actually dong it wasn't as easy as I thought. First night I was all dressed and ready to go, but I just could not bring myself to do it ... tomorrow I'd go tomorrow, perhaps a job offer would come up in the mean time ... it was the same the second and third night ... at least on the third night I got as far as my car, sat in it, then lost my nerve and dashed back inside.

Well this was the fourth night, if I did not go tonight, I might as well give up, I was never going to do it ... the spur of course was the looming college bill. I downed a couple of brandies, Dutch courage, and made a firm decision, this was it, don't think about it Jessica, just go, just do, do what needs to be done.

To say I was nervous about all this, would be an understatement ... I was trembling and felt physically sick. As I drove there I wasn't really concentrating on the road ... I was honked at by a few motorists and almost ran a red light ... how about that a red one ... quite appropriate don't you think?

I found a spot some distance from the red light area, and would walk the rest of the way. I locked the car and with jelly like legs I set off. My heart was thumping something terrible.

Now let me give you an idea of the lay out. The red light district had started up some years ago. In those early days only a few hookers trolled the area for johns, it was really an ideal place, right next to the dock area, ships coming and going, plenty of randy sailors, all eager to dip their wick, and get rid of that pent up frustration they had accumulated during the voyage.

On one side of the road there ran a wall, which encircled the dock and wharves. On the other side, the then bustling shops which had deteriorated over the years ... on the other hand the port had prospered, and I could see the cranes and ships derricks, the lights, and hear the noises of the ships being unloaded. The area became notorious for its red light district, and where there had been but a few prostitutes in the early days ... now, well let's just say the numbers had swelled a little

The nearer I got, the more activity was going on. As I passed by one shop door, set back in the shadows was a couple. I took a quick glance, all I could see was a girl or woman with her back against the door, her legs spread apart ... a glimpse of her right and left thighs, and between them was a guy, his ass humping her fast and furious. He was grunting and groaning, whilst she moaned and gasped ... I suspected it was all show from her. I kept on walking.

Now I was insight of the others, women sashaying, back and forth, striking sexy poses, for the benefit of the johns, who were viewing which one to latch on to ... god they seemed young ... made me feel like the oldie ... Truth be known I probably was.

"Hey there hun ... haven't seen you down here before" It was the voice of another er ... hooker, standing with hands on hips. One good thing, she wasn't as young as some of the others ... I didn't feel quite as bad. Somehow it seemed a relief to be talking to her, I felt at ease.

She was tall, leggy, a very attractive brunette ... with a friendly welcoming smile ... I bet she was real good at this game.

I tried my best to look the part, hips swaying as I closed the gap toward her.

"Nah just come in from up north ... been living and working up there ... my friend Debbie told me about this spot ... said it got busy" I lied ... god how easy it was to make up stories on the run.

"Well I'm Sharon ... know pretty much everything that goes on in the street ... like to keep and eye on things" she said taking in a lung full of smoke from the cigarette, and blowing it all out again

"Well I'm Jessica ... and it's good to meet you, always nice to know someone when you first move in"

"Yeah well things have been changing somewhat over the last year ... lota kids starting to move in" she said, indicating to some of the other girls loitering in the area.

When I looked at them, to me they did seem like kids ... no doubt a few from the university, doing it to help their bank balance.

Sharon took a moment to stroll over to a cruising car that had stopped and beckoned her over.

When she bent to speak to the passenger, I could see her panties quite clearly. She turned her head toward me for a moment, and then back to the guy ... a few brief words then she pushed away, telling them to keep driving.

"Bloody wankers" she said when she returned.

"He and his mate wanted both of us for $175 ... told him where to go... $250 or get lost ... he got lost" she said laughing

"Er just what do we charge around here ... don't want to go undercutting anyone" I asked ... hoping to find out what to charge.

"Well some of the young ones charge whatever ... might as well give it away ... but first I don't do hand jobs ... waist of time ... while you're wanking him off, you could miss out on a bigger fish ... I start with blow jobs"

Oh god I hadn't thought about that ... I'd have to get down on my knees and put some guys cock in my mouth ... I'd certainly make sure he was wearing a condom for that ... the thought of him cumming in my mouth ... yuk.

"I charge $75 for a blow job ... a straight fuck is $100, and if he wants to put it up my ass..."

Oh god a second time, again I hadn't given any thought to having it put up my ass ... god I'd never ever done anal sex ... it would be a first ... I guess it was still virgin territory.

"I charge $200 if they want to stick there dicks there" she said.

God this was all new to me ... I was learning on the run ... there was, obviously a lot I had to learn.

The whole area was now abuzz with activity. Cars were slowly driving by, guys were shouting to girls, and the girls would shout back, some abusive, some good natured.

Sharon was taking it all in her stride. I now realised I'd set myself up as the prey, the predators being the guys looking to pick one of the prey up. It was like a market place, and the goods we had to sell were sex. I was starting to feel a little panicky, and giving consideration to quietly walking away and just getting the hell out of it.

Sharon, between shouting at the guys, and trying to strike up deals, kept me in conversation. I was about to excuse myself; make some excuse I had to go. She was looking over my left shoulder, when she said.

"Oh, oh ... I think we have ourselves a couple of guys honey"

Oh shit.

"The guys coming up behind you have been eyeing us up for a while and here they come"

"Well, well now aren't you two the pick of the bunch ... Denny and I were just saying ... what a couple beauts you were"

I turned to face them, and glad to see they were of a similar age ... I was stuck for words, but not Sharon.

"Yeah of course we are, and you guys have a discerning eye for beauty and talent". She replied with a friendly smile.

"I think you deserve the best ... and I'm certain we won't disappoint you ... will we Jess?"

Jess ... ok so I'm now Jess.

I agreed with her, assuring them we were the best and they wouldn't be disappointed. Oh god

They each eyed us up, top to bottom, surveying the goods on offer.

"Ok Denny ... which one do you want?"

"I'll take this one Greg ... like the look of those tits mate" he replied, pointing to me.

"Fair enough ... then it looks like you and me Sharon"

Sharon pushed away from the lamp post she had been leaning against, stuck her arm through his and said. "This way hero" walking toward the shadowed area.

Denny followed suit, putting his arm through mine, and bid us follow.

Oh god ... oh gee this was it. I tried to get into the part ... oh sure I looked the part, the difficult bit was trying to be natural ... I'd never done this before, and if I wasn't so desperate for money, probably wouldn't be here at all.

Denny was already getting fired up, his hand slipping to my ass, giving it a pat and a squeeze. "Hmmm nice ... very nice" he commented.

I snuggled up to him, kissing him on the cheek. "Now, now lover boy just wait ... don't get ahead of yourself"

"How much is it gona cost me anyhow ... we never asked"

I cringed inwardly as I said "Blow job or straight fuck?"

"Straight fuck" his reply

"In that case it's $100" I said

He didn't seem to baulk at the price so we continued on.

The well lit area was now well behind us, dark and hidden areas were just ahead.

Sharon stopped at a shop doorway.

"Here you guys ... this is a good spot for you ... Greg and I will use the basement stairwell" she said, indicating the areas.

Denny steered me into the shadow of the shop door, placing my back against it.

He stood close, placing his arms around my waist, drawing and pressing me hard against his body. I could feel his already hard cock.

"Urrrrrr god you feel good" he growled, fully squeezing my ass.

"Aren't you forgetting something love?" I asked "Like money?"

"Oh yes ... yes of course, as he broke away, took out his wallet and peeled of two fifty dollar bills, and handing them to me.

"Thanks love" my reply, stuffing them into my shoulder purse.

"You gota condom" he asked

"Sure ... sure" my reply as I searched my purse for one.

"Here I'll unwrap it ... you get ready ... pull your knickers down and spread those lovely legs of yours.

Oh god ... oh my god

I hitched up my skirt, took hold of my panties and pulled them down as far as I thought would suffice, before spreading my legs as far as I could ... the cool night air wafting between them. He had taken off the wrapper for the condom, and I watched as he undid his fly and produced a very hard, and what to me seemed a very big cock.

"Oh god" I murmured

"He, he" he laughed "You like that love?" He asked

"I'm impressed ... yes" My reply

As he pulled on the condom, it dawned on me that in the next moment or so it was going to be put inside me.

"Here give me tour hand" he said, and taking it placed it on his cock.

Now I can't speak for all women ... but me, oh yes I love the feel a man's hard cock in my hand ... much the same as a guy likes the feel of a female pussy, in the palm of his hand.

God it felt good, it had been quite some time since I'd been with a bloke, and right now I was enjoying it, as I worked the hard shaft back and forth.

"Oh yes ... oh yes, that feels great love ... ohhhhhhh" sighing with satisfaction.

He quickly reciprocated and thrust his hand between my legs, palming my warm cunt, before thrusting a finger or fingers into it.

"Ohhhhhhh mmmmm" I purred "That feels good"

"Ok hun ... put it in for me" he said

Oh god this was it ... the moment of truth.

I rose up a little on my toes, placed his erection between my legs and as I lowered myself on to it, at the same time he thrust upward, I felt the head enter, quickly followed by the hard shaft.

It really did make me gasp ... almost bringing water to my eyes ... it took my breath away.

"Awwwwww geeeezzzzzeeee" I screamed, hoping my exclamation didn't sound too loud. My fingers closed on his arms, gripping him tight ... if he felt them, he didn't say or shout out ... but hell did I grip him.

He just laughed and continued to hump up and down, thrusting and pushing me against the shop door.

What I had witnessed as I had approached the area ... the two in the shop doorway, was now me, a glimpse of left and right thigh, and a guy, in between humping the living daylights out of me.

He slid his hands to my ass, squeezing my buttocks hard, and pulling himself even deeper inside me.

"Awwwwww that is a great ass babe ... a fucking great ass" he growled, a compliment ... or was it just the lust that was talking? I hoped it was a compliment.

He must have been at it for around five minutes, and then he said.

"I'm gona turn you around hun ... take you from the rear"

I hope he wasn't thinking about sticking it ... well you know where ... if he did I wanted more money.

He stopped shagging me, removed his dick and spun me around, now facing the door.

Taking a strong grip on my hips he pulled me a back a couple of feet, so that I had to reach out and use the door for support.

"I'm just gona pull my pants down love ... I want to feel that hot ass of yours against my thighs."

I waited until he had unbuckled his belt, undid his jeans and pulled them down ... no sooner done than I felt the fullness of his hard cock being thrust back in.

He kept a tight grip on my hips, holding them in place, like a vice. His thrusts were just as strong, hard and deep, his ass swaying back and forth, pushing thrusting.

"Oh god ... oh shit yes ... yes"

"Ohhhh this is so good ... so good" he kept telling me perhaps I should have charged more.

It was another five or so minutes of pounding, the sound of flesh smacking against flesh slap, slap, slap, and then came the release and the relief for him. I felt his cum as it streamed inside me ... hold on ... feel his cum ... but he was wearing a condom, wasn't he, surely I should not be feeling his cum.

"Ohhhhhhh fuck yeah, ohhhhhhh fuck that was so good" he said, as the last of his cum drained into me.

I quickly stood, and as I did, pulled my panties up, and straightened my skirt.

"Where's the condom" I demanded "What have you done with it?"

"Oh you mean this?" he casually replied holding up an empty condom.

"Yes, yes that one ... you're supposed the wear it ... It's ... it's for protection you asshole" I screamed at him

"Awww hey I prefer bareback ... I love cumming inside a woman love" his reply.

"A fuck feels so much better without one" he continued

"Yeah and what if you have some sort of disease ... what then smart arse"

"Well I don't have any ... do you ... do I need to start worrying?"

"No ... I'm clean ... that's not..."

"Then we don't have a problem do we"

God I felt so mad ... it wasn't only that he might have some sort of disease, but I was still capable of getting pregnant ... something I certainly didn't want to do.

By now we were joined by Sharon and Greg ... there were the customary thanks, and see you later maybe, and then the two guys headed off, Sharon linking her arm in mine as we headed back to the arena.

"Bastard removed the condom" I said to Sharon.

She took a moment to reply ... thinking

"Did he by any chance, screw you from the front first, then from the rear?"

My reply of course was yes

"You're new at this game aren't you love?"

I took a moment ... then replied "Oh god, yes ... yes I am"

"Mmmmm I thought so ... from the start I knew somehow you weren't the usual ... I can sense it ... I've been in the business a long while"

"Yes ... my first time" my reply

"Well that is the oldest trick in the book ... an experienced pro would have known that ... turn you around, and as he does, takes off the condom ... risky for both I agree, but some guys are like that"

Well I'd learned the hard way; I just hoped I didn't live to regret it.

Sharon was great to me after that, my mentor you might say. First she set me up with another john she knew well. Then the guys in the car returned, this time they paid full price, we went with them to some spare ground. I got done on the back seat, while Sharon got shagged over the bonnet, we laughed when she said "It's bloody hot on your tits, when you're stretched over the hot bonnet of a car".

After the fourth guy I decided to call it a night, if I thought this was the end of the night I was wrong, Sharon insisted we go to the "Anchor Hotel" I guess it was appropriately named, being situated near the docks and all, just for a quick drink before we finished for the night, she said, as we walked arm in arm.

"Better tell you love ... there's a pimp operating the area ... trying to move in ... we've never needed pimps before ... always freelance ... but this guy wants to take over the area ... sees a good potential, drugs and prostitution ... thinks he owns the place" adding "And all the girls" Name of Victor Alexandrov ... So keep an eye out.

"So what you saying, I have to have him as a pimp ... and be one of his girls"

"No, no ... well not yet anyway ... we've been trying to keep him out, resisting his efforts ... but he applies stand over tactics ... he's picking us off one by one"

"Oh I see ... doesn't sound good ... anyway I hope this is just a temporary measure for me"

She smiled, chuckled then shuck her head "Yeah we'll see love ... we'll see, I've heard that a thousand times" her reply as we continued on toward the Anchor.

The "Anchor" had been situated in the same area for years and years. Nothing had really changed, apart from the odd update. Perhaps some of it's attraction was the nostalgia, but some how I think not, more the "Boy meets girl", in this case hooker links up with client. The place was packed, my short skirt and low cut top was definitely not out of place, more like a uniform, a walking add board, and everyone knew what everyone was. Sharon was known by most already in the pub, as they shouted her name, and she theirs.

"Ok love, follow me" she said, pushing through the throng of people. As a majority of the patrons thus far were male, hands were making a grab for my ass, as I followed Sharon to the bar, getting all het up and indignant about it would be a waist of time. Ass grabbing was all part of the sport in here, just wear it.

Sharon ordered two bourbons and coke, and I, or we, found ourselves the centre of attention, now being surrounded by guys, who were hugging he bar.

Sharon of course was in her element, quick with the witty replies and repartee, flirting all the time, egging them on. Whilst my conversation was friendly and restricted to replying to the questions asked ... but then she had been at this a long, long time. She was a good sort at heart, and one you would want in your corner ... I hoped she was in mine.

The bourbons and coke seemed to go down real well, perhaps it was the heat in here allowing them to evaporate ... hmmm I don't think so. The guys were quick to have another one ready just as soon as your glass was empty.

As the night wore on, Sharon and I seemed to get further and further apart, I guess she was that sort of girl, sociable and liked to mix and mingle. I was now isolated and in conversation with two guys in particular.

I'd learned that the tall black guy was called Andy ... And the white chubby one Derrick, I likewise told them I was Jess ... the name given me by Sharon.

I also learned they were seamen ... no not semen ... seamen, sailors, you know the type that go to sea ... god you guys ... keep it above the waist line, and that they were from the "Manchester Harvester", a ship being unloaded at present. They were due to sail mid morning tomorrow

I had a feeling of someone watching me ... you know the feeling ... some sort of sixth sense. I turned slightly to my right, and yes, a guy ... a well dressed guy, accompanied by two ... big brawny types ... over at the corner table ... he seemed out of place here, he was definitely, staring at me ... I shrugged it off and returned my attention to the two guys, Andy and Derrick