Working Girl

How I turn to selling it rather than giving it away.

Since being divorced from my husband of twenty-six years I have taken my time to get back into dating. Ok during the first year or so I 'saw' a couple of old flames and I had a brief fling with a young guy, but nothing serious or anything with any commitment. But then I didn't want either of those and after one marriage that had gone tits up, I wasn't looking for anything permanent and certainly I had no intention or desire to fall in love.

Things had changed a lot since I last dated. Now, men were more up front, more demanding and to the point.

"Come on love, you must be gagging for it," a married guy from the golf club muttered as he kissed me at a club dance.

"Well, I thought a nice dinner then back to your place," was an old flame's suggestion as we chatted in a supermarket of all places.

"Let's get into the back of the car," a guy suggested when I went on a first date with him.

"Well Jay it is our third date," another guy muttered sliding his hand up my skirt.

These all happened during the first year after my divorce. Sex was everywhere.

I guess people in middle age don't feel they have the time to take things slowly. Well men don't as they want it all and they want it now. But then why not and if we women are dumb enough to go along with them so be it.

But I couldn't.

I wasn't after love or commitment nor was I after sex that much. I had plenty of company, albeit electronic, in my bedside drawer and when I needed a little more there was always an old flame or a fwb to call on. I found out pretty quickly, however, that if you date as I did, then it's expected that you'll put out, that you'll let him do pretty much what he wants and that you'll end up in bed or nearly naked on the back seat of a married guy's car with your knickers off, tits out and your legs wrapped around him. The old tradition of kissing on the first date, tits played with on the second, hand up your skirt on the third and a fuck on the fourth had changed. The process had been squeezed, the time frame shortened and fourth had now become second and with some guys even first.

So, I didn't date much in that first year or so. It wasn't that I didn't want to go out just that the whole thing of getting to know someone, working out whether you fancied each other and then going through 'the process' became such a drag.

I did, though masturbate a lot but after a few months that became rather tedious. Lying naked on my bed in my lovely flat in Docklands with my hands roaming around my body, though titillating and usually, but not always, satisfying is also lonely. I often felt that I needed company when I did that and I found two types of that. One was using my literary skills to write erotic stories, usually naked or just wearing knickers, that provided the arousal to ensure my finger manipulations worked. And the second? Well, that was a little more extreme, I found chat rooms. I had briefly seen them some years ago when I found my husband had been using them, which ridiculously almost caused a divorce, but then as far as I was aware they were banned because of kids being seduced by them. I was wrong there were loads around and I quite quickly became hooked. That was not by the 'scintillating' conversation but as a means to aid masturbation.

From what I have learned from a number of sources men and women are quite different with their masturbating techniques, needs and outcomes. Most men seem able to jerk off to a full orgasm almost on demand and younger ones can do that several times a day. We can't or more accurately don't and we are different. Different to the point that we only masturbate about half as frequently as men, eight times a month to fifteen by them, and less of us reach orgasm, a survey showed that men of reasonable sexual age cum between 95 and 100 percent of the times they masturbate whereas with us it's more like 75 to 80!

So, I used chat rooms for two reasons connected with my masturbation. Firstly, it helped increase my desire and need to have sex with myself, secondly it was more enjoyable talking, either in writing or on the phone, as we both attended to our needs and thirdly it relieved the loneliness.

There were several methods of mutual masturbation in the chat rooms. The one favoured by most men and disliked by many women who I spoke to online was the man telling the woman what he was doing to her. I hated it. That was not just because of the sheer assumptiveness and insularity as he decided what was happening and assumed that his rarely dulcet tones were turning me on but also because rarely were they much good at it. I don't think I was ever made to cum that way.

The second and far more successful, though most men are not very good at it, are role plays. They work well if the guy has the writing ability, patience and sheer sexual nous to act out an agreed role that generally ends up with the couple fucking. If he is a reasonable wordsmith, as most are not, then as they write about seducing me and us fucking so, my arousal increases and I can start to fondle myself and move into my masturbation techniques.

The third which is sometimes an extension of a role-play is mutual masturbation. Probably more popular between online lovers than amongst newly met couples this is where each describes what they are doing to themselves. This was where I think I had most success and where my hit rate, the frequency with which I orgasmed, was the highest.

So, I used chat rooms quite a lot!

*

"I want to fuck you?" the fifty-something-year-old guy I had been chatting to for over an hour said one afternoon.

The conversation had ranged from the usual. 'How are you?' to. 'Are you married?' and onto the issues with his marriage that along with so many middle-aged guys in chat revolved around his wife going off sex as so many do as the kids fly the coop and the menopause sets in.

He was unusually lucid, interesting and clearly quite intelligent, a rare combination in chat rooms! As is usually the case the conversation turned sexual but in a rather grown up and chat room sophisticated way. It included us exchanging photos with him, thankfully not sending my pet hate a dick pic but a nice full-length shot of him fully dressed and me returning one of me in a dress that was a few inches above the knee and where I had forgotten to wear a bra. As it often does, that caused him to comment on my glasses, that men in chat rooms seem to find sexy, and on my D cup boobs and my clearly aroused nipples.

"Are they like that now?" he asked.

"Not sure."

"Well have a feel?" he replied adding. "If you'd like to, that is, would you?"

"Yes, I rather think I would," I said cupping my breasts that were bare inside the zip up track top I was wearing in preparation of going to the gym and my nipples were, indeed very hard.

"So, what are you wearing Jayne?" he asked.

I told him. "Gym gear," and he said.

"And what's that?"

"Yoga pants and a track top."

"What's under it?"

"Me."

"Just you?"

"Yes."

"No bra?"

"Not yet."

"And why's that?" he enquired nicely.

"Two reasons."

"And they are?"

"Well first, my sports bra is slightly too small for me and on the tight side so I'll only put that on just before I go."

"And second? By the way Jay I am loving this chat."

"Why's that?"

"It sounds so real and intimate talking about your clothing."

"Good, pleased you're enjoying it, I am too. So, you want to know the second?"

"Yes please, if you don't mind telling me?"

"No not at all Craig. It's so that I can easily slide the zip down and get to my boobs."

"Are you now?"

"Yes."

"Is it nice?"

"It's lovely. And you?"

"What about me, I'm hard."

"How hard?"

"Rigid."

"Are you hard enough to fuck?"

"Yes easily."

And that was when Craig said that he'd like to fuck me and for some bizarre and inexplicable reason I said.

"How much would you pay?"

Not surprisingly he was confused until I explained by saying.

"I'm a part time working girl Craig."

I was really just joking and that was said tongue in cheek but he took it seriously and I went along with it.

We went round the houses a bit as we discussed how to arrange it and where we would meet.

"Maybe we should talk about it on the phone."

And that's exactly what we did.

After reassuring him that the photos I had sent of me fully dressed, in underwear and topless were really of me, I took a selfie as we chatted and sent him that.

"How about you unzip that?" he rather cheekily asked but as I was aroused, I went along with it and slid it down. "Mmmm, nice cleavage but Jay there's more I'd like to see."

"Hmmmm I wonder what that is?" I smiled pulling the top open so I bared my breasts for him showing my arousal with the swollen nipples.

He returned the favour by sending a shot of him without a top and then just in his boxers. From that his arousal was quite obvious and interestingly large.

We discussed what we were doing to ourselves with me describing how I was fondling my tits and him telling me that he was now naked and starting to stroke himself. I told him that I had slid my yogas down and off and that I was now rubbing my clit.

"God, I wish I was there with you Jayne."

"Mmmm I can't think of anything I'd rather have right now than that cock in my hand and our naked bodies pressed together," I told him as I started to masturbate.

"I am starting to fuck you Jay," he groaned down the phone. "The fat head of my cock is pressed right against your wet lips," he went on.

"Then do it Craig, do me, fuck me go on."

And then, fuck it, that dreaded message 'Craig6969 is no longer online,' came up on my screen.

*

My divorce had been brutal. My ex and I had fallen out big time and the vicious side of his personality came out and fought me every inch of the financial route through the proceedings. Due to his deviousness, he was able to 'hide' most of his money in bank accounts in the middle east where he had managed to become domiciled for tax purposes and, of course, there's no tax there!

I ended up with the house which was mortgage free and a nice asset but, effectively no income. On top of that problem, I also had an ageing mother who we had been supporting financially for some years so she came and lived with me and we sold her small house.

These two situations were the prime movers in my interest in becoming a 'working girl!'

Craig, who was one of the more civilised guys I met in chat, gave me the idea. His reaction to my suggestion that I was a working girl started it and although he and I didn't go further it left something in me that came out a few times, albeit half-heartedly with guys I chatted to. What surprised, me, though, was the number that reacted positively and were up for meeting at a hotel to pay for sex with me.

The online chats, which were usually firstly in writing but later on the phone, went along the following lines. After I had ascertained that meeting was logistically possible due to locations, I steered the conversation around to sex and generally sent a photo of me scantily clad. Not too much, not a nude or topless but something that was risqué and enough to arouse him! A glimpse of bare legs, my D cup boobs or a hint of a nipple usually did the trick.

"So, you want sex do you?" I would ask.

"Yes, Jayne yes I do."

"You want to fuck me?"

"Yes."

"In real life?"

"Yes."

"Have you met any women before?" I would always as that's a good test of reliability I found.

"Yes, a couple."

We'd perhaps then chat about those meetings before getting down to the nitty gritty.

"How much do you charge Jayne?" they would usually ask.

"That depends on what you want."

"What do you offer."

"Anything and everything," I'd reply rather boastfully. "You name it."

"Sex as though we are lovers?"

"Yes of course."

"Kissing?"

"Love it."

"Oral?"

"Yes."

"Both ways?"

"Perfect."

"All night."

"Yes, if you want. I will be your lover for as long as we're together."

"Can I fuck you twice?"

"If you want to yes or more if you can."

Some asked for two hours some for all afternoon and a few for all night and I'd agree a package.

After often an exhaustive discussion/negotiation, which for many guys was all it would ever be as I think many got off on chatting to a woman about what sex they might have, occasionally I'd agree a package of services, a location and a time.

I had numerous such chats before I finalised one that was promising. We had agreed four hours at a hotel near Gatwick on an afternoon a week away. It was made on the understanding that he phoned me the day before which of course he didn't. That happened several times before a Melvyn did call. He lived in Cambridge and told me that he had used escorts like me several times which was reassuring. We agreed a hotel at Stansted where he said he had reserved a room. I checked that he had a reservation and he did and we chatted the morning of the date and spoke on our phones as we travelled to our meeting.

I was so nervous driving up to Stansted from London Docklands and sitting in the bar waiting his arrival, I nearly abandoned the idea. We'd agreed all afternoon, two until six or seven and that he could fuck me as many times as he wanted although not anal.

I was dressed fairly formally in a blue dress with a zip up the back that my ex used to like undoing and that made me think my punter would. As the hem was about six to eight inches above my knees, it was probably on the short side for a woman of my age particularly as I was wearing lacy top holds. They were complemented by all black underwear and strappy, killer heels. We'd agreed to meet in the bar for a no strings chat that either could walk away from if they wished or could go to the room. I knew that was risky from a business angle and that it could ruin my afternoon financially but I thought it was worth to reassure the clientele!

Mel looked like he had in his photos which made for a good start and his conversation was lively and personality seemed fine. As we finished our drinks my nerves had reduced and it was beginning to feel like a straight date.

Going up in the lift and walking to the room the nerves returned big time, though. The fact that I was going to be fucked and do God knows what else with a total stranger kept going through my mind. As we got into the rather small room, they got even worse and so much so that I forgot to ask him for the money, but the gentleman that he was he reminded me and gave me the three hundred pounds.

For several moments we stood silently looking at each other in the fairly narrow space between the foot of the bed and the dressing table

"So how do we do this?" Mel asked sounding a great deal more confident than I felt but then, I reconciled, he'd probably done this more times than I had.

Trying to sound assured and as if I knew what I was doing I smiled and said.

"How would you like to do it?"

"May I kiss you?" he asked.

"Yes of course," I replied feeling even more nervous now that the time had actually arrived.

As it turned out he was quite a good kisser and possibly, at first at least, better than me as I took time getting used to kissing a perfect stranger. The nearest I had ever come to that was a one night stand I had just before my separation, but I had been chatting and drinking with him for two or three hours.

However, with Mel's arms around me pulling me tightly against his firm body, his erection pressing into my stomach, my breasts squashed against his chest and his lips clamped against mine, I soon got used to it and kissed him back as fully as he was kissing me. Our tongues came into play quite quickly and were duelling together as his hand slid downwards to stroke, squeeze and then cup the cheeks of my bottom.

Quite soon I realised that I was enjoying it and that he was arousing me. The facts that we were strangers and I was doing this for money were cast from my mind and he felt as if he were my lover and not my punter. I ruffled the hair on the back of his neck and as he thrust his cock against me, I squirmed against it with genuine desire and pleasure. He writhed it and sort of humped me a little right on my pubic mound sending my clit crazy. I felt his hands sliding up and under my skirt at the back until both were on my bare cheeks that he fondled and squeezed. That was rather lovely, I was enjoying it and my mind was completely ignoring the facts of the matter so when I heard him say.

"May I?" it was as if from a distance. I wondered what he meant until I felt his fingers fiddling with the zip at the back of my dress.

Giggling a little, I replied.

"Mmmmm I thought you'd never ask," as I felt the dress loosening as the zip slid down.

I moved my hands from around his neck and held them by my sides so that he could slide the dress off which he did and it slid down my body and fell to the ground around my feet.

Bending down I said. "Just let me get that," as I picked the dress up and turning around, I went to the small wardrobe and put it on a hanger. As I did so he said.

"Oh, wow Jayne you look fantastic what a get up."

Turning back to face him, I smiled and said.

"So, you approve?"

"Oh my god yes," he gushed moving to me and taking me back in his arms again and kissing me.

We kissed for some time until he manoeuvred me towards the bed until the backs of my legs were pressed against it. Applying a little pressure on me to move backwards he asked.

"Ok?" as without giving me time to say yes or no, he then laid me down on the bed with him half on top of me.

His hand almost immediately went to my breast and caressed that firstly outside and then inside my bra before easing both boobs out of their cups. He spent an enjoyable ten minutes or so licking, kissing and sucking them focusing mostly on my nipples that felt as if they would explode. I sat up and said.

"Unclip it would you Mel please?"

"God yes please," he muttered doing so with clearly shaking fingers. I eased the black bra off each cup and removed it.

"Oh fuck, woops sorry," he gasped.

Laughing I told him not to worry about swearing or dirty talk as he went on. "They're great Jayne, may I?" he asked cupping one.

"Yes of course."

He spent another few minutes playing with them before sliding his hand down and cupping my mound outside the black thong which meant, of course, that his hand stimulated my clit. I was now really into this, possibly too much really as I was not looking at him as a client but more lover, silly really.

"Not to hurry you or anything Mel," I whispered pressing my hand on the bulge in his jeans as I went on. "Do you not feel a little overdressed?"

"Oh right sorry," he said getting off the bed and standing beside it as I moved fully onto it and lay flat in the middle.

He quickly had his polo shirt and jeans off and stood there in his grey CKs. It was almost as if he was posing for me as I looked up and down his trim, quite athletic body focusing on the shape of his erection rearing up his stomach as he slid his hands into the waist band and eased them down.

"Mmmmm very nice Mel, shall I do the same?"

"Why not?" he replied as I slipped my thong off.

"Mmmm, I love the bare look," he said tentatively stroking my shaved mound before finding and carefully rubbing my clit.

"Can we now?"

"What?" I rather stupidly asked.

"Have sex?"

"I rather thought we had been."

"I mean may I fuck you now?"

I agreed and he did. Overall, it was very nice as was the repeat a couple of hours later after we'd had a nice hamburger lunch.

*

"Once or twice a month," I told Mark, a new client when he asked about how many times I did it.

I went on to explain that it was extremely time-consuming finding clients in the chat rooms.